# Supplementary Material (ESI) for Green Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _journal_year 2011 _journal_volume 13 _journal_page_first 2107 _publ_contact_author_email guigen.li@ttu.edu _publ_contact_author_name ' Li, Guigen' loop_ _publ_author_name 'Chuang Cheng' 'Bo Jiang' 'Shujiang Tu' 'Guigen Li' data_101104a _database_code_depnum_ccdc_archive 'CCDC 814811' #TrackingRef '- 6e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H7 Cl N2 O' _chemical_formula_weight 266.68 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' Cl Cl 0.1484 0.1585 '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)/n 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 13.4701(15) _cell_length_b 3.8350(5) _cell_length_c 25.500(2) _cell_angle_alpha 90.00 _cell_angle_beta 117.940(2) _cell_angle_gamma 90.00 _cell_volume 1163.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 615 _cell_measurement_theta_min 3.019 _cell_measurement_theta_max 26.329 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.318 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8699 _exptl_absorpt_correction_T_max 0.9843 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 5292 _diffrn_reflns_av_R_equivalents 0.0988 _diffrn_reflns_av_sigmaI/netI 0.1136 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2018 _reflns_number_gt 956 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0996P)^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 2018 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1814 _refine_ls_R_factor_gt 0.1056 _refine_ls_wR_factor_ref 0.2515 _refine_ls_wR_factor_gt 0.2202 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 Cl1 Cl 0.89070(15) 0.7072(6) 0.20050(9) 0.0716(8) Uani 1 1 d . . . N1 N 0.4274(5) 0.2241(16) 0.0513(2) 0.0528(15) Uani 1 1 d . . . N2 N 0.4881(4) 0.5640(15) 0.1636(2) 0.0444(14) Uani 1 1 d . . . O1 O 0.1795(4) 0.0630(15) -0.0049(2) 0.0697(16) Uani 1 1 d . . . C1 C 0.2335(6) 0.2116(18) 0.0431(3) 0.0478(17) Uani 1 1 d . . . C2 C 0.3589(5) 0.2870(17) 0.0722(3) 0.0409(16) Uani 1 1 d . . . C3 C 0.3865(5) 0.4612(17) 0.1274(3) 0.0442(17) Uani 1 1 d . . . C4 C 0.2837(5) 0.4923(18) 0.1334(3) 0.0463(18) Uani 1 1 d . . . C5 C 0.1936(6) 0.3473(18) 0.0838(3) 0.0497(18) Uani 1 1 d . . . C6 C 0.0860(6) 0.347(2) 0.0792(3) 0.060(2) Uani 1 1 d . . . H6 H 0.0248 0.2544 0.0462 0.072 Uiso 1 1 calc R . . C7 C 0.0744(7) 0.493(3) 0.1262(4) 0.074(3) Uani 1 1 d . . . H7 H 0.0037 0.4951 0.1243 0.089 Uiso 1 1 calc R . . C8 C 0.1615(7) 0.629(2) 0.1741(4) 0.074(2) Uani 1 1 d . . . H8 H 0.1504 0.7271 0.2043 0.089 Uiso 1 1 calc R . . C9 C 0.2684(6) 0.6242(19) 0.1787(3) 0.054(2) Uani 1 1 d . . . H9 H 0.3293 0.7106 0.2126 0.065 Uiso 1 1 calc R . . C10 C 0.5333(6) 0.3350(18) 0.0872(3) 0.0461(17) Uani 1 1 d . . . C11 C 0.5643(6) 0.5042(19) 0.1425(3) 0.0543(19) Uani 1 1 d . . . C12 C 0.6773(6) 0.6157(18) 0.1784(3) 0.0516(19) Uani 1 1 d . . . H12 H 0.6984 0.7255 0.2146 0.062 Uiso 1 1 calc R . . C13 C 0.7533(6) 0.5587(18) 0.1588(3) 0.0524(18) Uani 1 1 d . . . C14 C 0.7258(6) 0.3953(19) 0.1037(3) 0.055(2) Uani 1 1 d . . . H14 H 0.7794 0.3639 0.0909 0.065 Uiso 1 1 calc R . . C15 C 0.6164(5) 0.2847(19) 0.0700(3) 0.0498(18) Uani 1 1 d . . . H15 H 0.5973 0.1718 0.0343 0.060 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 Cl1 0.0474(11) 0.0766(16) 0.0770(14) -0.0074(12) 0.0177(10) -0.0041(11) N1 0.057(4) 0.049(4) 0.048(3) 0.000(3) 0.021(3) 0.000(3) N2 0.051(3) 0.037(3) 0.043(3) -0.003(3) 0.020(3) -0.004(3) O1 0.063(3) 0.087(4) 0.054(3) -0.025(3) 0.022(3) -0.023(3) C1 0.056(4) 0.035(4) 0.048(4) 0.004(4) 0.021(4) -0.005(4) C2 0.046(4) 0.035(4) 0.034(3) -0.001(3) 0.012(3) 0.000(3) C3 0.044(4) 0.032(4) 0.053(4) 0.012(3) 0.019(3) 0.002(3) C4 0.058(4) 0.043(4) 0.039(4) 0.002(3) 0.024(3) 0.007(4) C5 0.057(4) 0.047(5) 0.037(4) -0.005(3) 0.015(3) -0.007(4) C6 0.046(4) 0.065(6) 0.058(5) 0.005(4) 0.016(4) -0.007(4) C7 0.070(6) 0.094(7) 0.072(6) 0.016(5) 0.046(5) 0.009(5) C8 0.085(6) 0.064(6) 0.061(5) 0.016(5) 0.024(5) 0.003(5) C9 0.056(5) 0.047(5) 0.051(4) 0.004(3) 0.017(4) -0.001(4) C10 0.062(5) 0.043(4) 0.035(4) 0.006(3) 0.024(3) 0.002(4) C11 0.062(5) 0.041(5) 0.048(4) 0.005(3) 0.015(4) 0.001(4) C12 0.054(4) 0.045(5) 0.044(4) 0.007(3) 0.014(4) -0.003(4) C13 0.050(4) 0.042(4) 0.055(4) 0.003(4) 0.017(4) 0.002(4) C14 0.051(4) 0.051(5) 0.056(5) -0.002(4) 0.020(4) -0.002(4) C15 0.048(4) 0.054(5) 0.037(4) -0.008(4) 0.012(3) 0.005(4) _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 Cl1 C13 1.742(7) . ? N1 C2 1.286(8) . ? N1 C10 1.353(8) . ? N2 C3 1.302(7) . ? N2 C11 1.383(8) . ? O1 C1 1.231(8) . ? C1 C5 1.471(9) . ? C1 C2 1.521(9) . ? C2 C3 1.441(9) . ? C3 C4 1.469(9) . ? C4 C9 1.361(9) . ? C4 C5 1.395(9) . ? C5 C6 1.398(9) . ? C6 C7 1.396(11) . ? C6 H6 0.9300 . ? C7 C8 1.341(11) . ? C7 H7 0.9300 . ? C8 C9 1.389(10) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.394(8) . ? C10 C11 1.425(9) . ? C11 C12 1.426(9) . ? C12 C13 1.351(9) . ? C12 H12 0.9300 . ? C13 C14 1.418(9) . ? C14 C15 1.380(8) . ? C14 H14 0.9300 . ? C15 H15 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 C2 N1 C10 113.2(6) . . ? C3 N2 C11 113.5(6) . . ? O1 C1 C5 128.6(6) . . ? O1 C1 C2 125.2(6) . . ? C5 C1 C2 106.2(6) . . ? N1 C2 C3 125.8(6) . . ? N1 C2 C1 127.6(6) . . ? C3 C2 C1 106.5(6) . . ? N2 C3 C2 122.5(6) . . ? N2 C3 C4 129.1(6) . . ? C2 C3 C4 108.4(6) . . ? C9 C4 C5 120.3(6) . . ? C9 C4 C3 130.1(6) . . ? C5 C4 C3 109.6(6) . . ? C4 C5 C6 120.2(6) . . ? C4 C5 C1 109.3(6) . . ? C6 C5 C1 130.4(6) . . ? C7 C6 C5 117.2(7) . . ? C7 C6 H6 121.4 . . ? C5 C6 H6 121.4 . . ? C8 C7 C6 122.3(8) . . ? C8 C7 H7 118.8 . . ? C6 C7 H7 118.8 . . ? C7 C8 C9 120.1(8) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C4 C9 C8 119.7(7) . . ? C4 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? N1 C10 C15 119.4(6) . . ? N1 C10 C11 122.7(6) . . ? C15 C10 C11 117.9(7) . . ? N2 C11 C10 122.2(6) . . ? N2 C11 C12 117.7(6) . . ? C10 C11 C12 120.1(7) . . ? C13 C12 C11 118.8(7) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C12 C13 C14 123.1(7) . . ? C12 C13 Cl1 119.6(6) . . ? C14 C13 Cl1 117.3(6) . . ? C15 C14 C13 117.4(6) . . ? C15 C14 H14 121.3 . . ? C13 C14 H14 121.3 . . ? C14 C15 C10 122.9(6) . . ? C14 C15 H15 118.6 . . ? C10 C15 H15 118.6 . . ? 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 C10 N1 C2 C3 0.9(10) . . . . ? C10 N1 C2 C1 177.6(6) . . . . ? O1 C1 C2 N1 3.1(12) . . . . ? C5 C1 C2 N1 -177.4(7) . . . . ? O1 C1 C2 C3 -179.7(7) . . . . ? C5 C1 C2 C3 -0.2(7) . . . . ? C11 N2 C3 C2 2.8(9) . . . . ? C11 N2 C3 C4 -177.6(7) . . . . ? N1 C2 C3 N2 -2.6(11) . . . . ? C1 C2 C3 N2 -179.8(6) . . . . ? N1 C2 C3 C4 177.8(7) . . . . ? C1 C2 C3 C4 0.5(7) . . . . ? N2 C3 C4 C9 -2.5(12) . . . . ? C2 C3 C4 C9 177.2(7) . . . . ? N2 C3 C4 C5 179.7(7) . . . . ? C2 C3 C4 C5 -0.6(8) . . . . ? C9 C4 C5 C6 2.3(11) . . . . ? C3 C4 C5 C6 -179.7(6) . . . . ? C9 C4 C5 C1 -177.6(6) . . . . ? C3 C4 C5 C1 0.4(8) . . . . ? O1 C1 C5 C4 179.3(7) . . . . ? C2 C1 C5 C4 -0.1(8) . . . . ? O1 C1 C5 C6 -0.5(13) . . . . ? C2 C1 C5 C6 -179.9(7) . . . . ? C4 C5 C6 C7 -0.8(11) . . . . ? C1 C5 C6 C7 179.0(7) . . . . ? C5 C6 C7 C8 0.2(12) . . . . ? C6 C7 C8 C9 -1.0(13) . . . . ? C5 C4 C9 C8 -3.1(11) . . . . ? C3 C4 C9 C8 179.4(7) . . . . ? C7 C8 C9 C4 2.5(12) . . . . ? C2 N1 C10 C15 -179.8(6) . . . . ? C2 N1 C10 C11 0.0(10) . . . . ? C3 N2 C11 C10 -2.0(9) . . . . ? C3 N2 C11 C12 178.5(6) . . . . ? N1 C10 C11 N2 0.6(10) . . . . ? C15 C10 C11 N2 -179.6(6) . . . . ? N1 C10 C11 C12 -179.9(6) . . . . ? C15 C10 C11 C12 -0.1(10) . . . . ? N2 C11 C12 C13 179.7(6) . . . . ? C10 C11 C12 C13 0.2(10) . . . . ? C11 C12 C13 C14 0.6(11) . . . . ? C11 C12 C13 Cl1 177.6(5) . . . . ? C12 C13 C14 C15 -1.5(11) . . . . ? Cl1 C13 C14 C15 -178.6(5) . . . . ? C13 C14 C15 C10 1.6(11) . . . . ? N1 C10 C15 C14 178.9(6) . . . . ? C11 C10 C15 C14 -0.8(11) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.587 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.130 # Attachment '7a.cif' data_091012a _database_code_depnum_ccdc_archive 'CCDC 814812' #TrackingRef '7a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 N2 O8' _chemical_formula_weight 440.40 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' O O 0.0106 0.0060 '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' _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 14.9522(15) _cell_length_b 18.8553(19) _cell_length_c 7.6472(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.114(2) _cell_angle_gamma 90.00 _cell_volume 2108.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1099 _cell_measurement_theta_min 2.571 _cell_measurement_theta_max 25.189 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9097 _exptl_absorpt_correction_T_max 0.9873 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 10607 _diffrn_reflns_av_R_equivalents 0.1026 _diffrn_reflns_av_sigmaI/netI 0.1298 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3698 _reflns_number_gt 1524 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0039P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3698 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1602 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.0828 _refine_ls_wR_factor_gt 0.0705 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.001 _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 N1 N 0.6275(2) 0.33841(13) 0.5518(3) 0.0455(8) Uani 1 1 d . . . H1 H 0.6168 0.3189 0.4478 0.055 Uiso 1 1 calc R . . N2 N 0.67586(19) 0.20044(14) 0.6611(3) 0.0606(9) Uani 1 1 d . . . H2A H 0.6902 0.1574 0.6918 0.073 Uiso 1 1 calc R . . H2B H 0.6229 0.2099 0.5962 0.073 Uiso 1 1 calc R . . O1 O 0.48534(17) 0.45229(11) 0.7581(3) 0.0534(7) Uani 1 1 d . . . O2 O 0.35410(18) 0.46483(13) 0.5567(3) 0.0730(9) Uani 1 1 d . . . O3 O 0.49309(18) 0.24544(11) 0.3103(3) 0.0616(8) Uani 1 1 d . . . O4 O 0.49272(16) 0.38637(11) 0.1795(3) 0.0559(7) Uani 1 1 d . . . H4 H 0.4972 0.4296 0.1747 0.084 Uiso 1 1 calc R . . O5 O 0.31021(17) 0.44159(12) 0.1515(3) 0.0725(9) Uani 1 1 d . . . O6 O 0.90282(17) 0.48537(13) 0.8504(3) 0.0736(9) Uani 1 1 d . . . O7 O 1.00097(17) 0.40685(13) 1.0019(3) 0.0835(10) Uani 1 1 d . . . H7 H 1.0304 0.4434 1.0290 0.125 Uiso 1 1 calc R . . O8 O 0.2664(2) 0.56045(14) 0.7327(5) 0.1092(12) Uani 1 1 d . . . H8 H 0.2943 0.5338 0.6784 0.164 Uiso 1 1 calc R . . C1 C 0.4305(3) 0.43844(19) 0.5924(5) 0.0504(11) Uani 1 1 d . . . C2 C 0.4772(2) 0.39388(17) 0.4902(5) 0.0399(10) Uani 1 1 d . . . C3 C 0.5614(3) 0.37908(16) 0.5927(4) 0.0379(9) Uani 1 1 d . . . C4 C 0.5705(2) 0.41414(17) 0.7701(4) 0.0499(11) Uani 1 1 d . . . H4A H 0.5787 0.3792 0.8654 0.060 Uiso 1 1 calc R . . H4B H 0.6221 0.4465 0.7924 0.060 Uiso 1 1 calc R . . C5 C 0.4301(3) 0.28652(18) 0.3086(4) 0.0449(10) Uani 1 1 d . . . C6 C 0.4379(2) 0.36824(17) 0.3032(5) 0.0417(10) Uani 1 1 d . . . C7 C 0.3366(3) 0.3898(2) 0.2395(5) 0.0522(11) Uani 1 1 d . . . C8 C 0.2808(3) 0.3304(2) 0.2843(5) 0.0529(11) Uani 1 1 d . . . C9 C 0.3348(3) 0.2697(2) 0.3161(4) 0.0501(11) Uani 1 1 d . . . C10 C 0.2964(3) 0.2041(2) 0.3405(5) 0.0660(13) Uani 1 1 d . . . H10 H 0.3321 0.1633 0.3595 0.079 Uiso 1 1 calc R . . C11 C 0.2041(4) 0.2014(3) 0.3358(5) 0.0857(16) Uani 1 1 d . . . H11 H 0.1772 0.1580 0.3515 0.103 Uiso 1 1 calc R . . C12 C 0.1496(3) 0.2622(3) 0.3081(6) 0.0880(16) Uani 1 1 d . . . H12 H 0.0875 0.2590 0.3080 0.106 Uiso 1 1 calc R . . C13 C 0.1875(3) 0.3274(2) 0.2809(5) 0.0731(14) Uani 1 1 d . . . H13 H 0.1515 0.3680 0.2609 0.088 Uiso 1 1 calc R . . C14 C 0.7151(2) 0.32463(18) 0.6671(4) 0.0418(10) Uani 1 1 d . . . C15 C 0.7372(3) 0.25375(19) 0.7154(4) 0.0422(10) Uani 1 1 d . . . C16 C 0.8237(3) 0.24001(18) 0.8209(4) 0.0502(11) Uani 1 1 d . . . H16 H 0.8405 0.1935 0.8526 0.060 Uiso 1 1 calc R . . C17 C 0.8839(3) 0.29391(19) 0.8781(4) 0.0527(11) Uani 1 1 d . . . H17 H 0.9406 0.2834 0.9500 0.063 Uiso 1 1 calc R . . C18 C 0.8622(2) 0.36407(19) 0.8312(5) 0.0488(10) Uani 1 1 d . . . C19 C 0.7764(2) 0.37782(17) 0.7228(4) 0.0479(10) Uani 1 1 d . . . H19 H 0.7607 0.4242 0.6880 0.057 Uiso 1 1 calc R . . C20 C 0.9250(3) 0.4218(2) 0.8959(5) 0.0589(12) Uani 1 1 d . . . C21 C 0.1942(5) 0.5263(3) 0.7705(8) 0.149(2) Uani 1 1 d . . . H21A H 0.1645 0.5590 0.8381 0.178 Uiso 1 1 calc R . . H21B H 0.2181 0.4878 0.8508 0.178 Uiso 1 1 calc R . . C22 C 0.1225(4) 0.4962(4) 0.6304(8) 0.217(4) Uani 1 1 d . . . H22A H 0.0814 0.5332 0.5775 0.325 Uiso 1 1 calc R . . H22B H 0.0892 0.4610 0.6815 0.325 Uiso 1 1 calc R . . H22C H 0.1497 0.4748 0.5404 0.325 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 N1 0.047(2) 0.0439(18) 0.0424(19) -0.0059(16) 0.0024(16) 0.0008(17) N2 0.051(2) 0.0417(18) 0.082(2) 0.0045(17) -0.0036(18) -0.0007(17) O1 0.0609(18) 0.0505(16) 0.0476(17) -0.0074(13) 0.0087(15) 0.0075(15) O2 0.0552(19) 0.0701(19) 0.090(2) -0.0176(16) 0.0071(17) 0.0156(17) O3 0.061(2) 0.0425(16) 0.076(2) -0.0100(14) 0.0030(16) 0.0120(15) O4 0.0639(19) 0.0491(16) 0.0543(17) 0.0003(13) 0.0118(14) -0.0026(14) O5 0.067(2) 0.0501(17) 0.087(2) 0.0130(15) -0.0147(15) 0.0089(16) O6 0.059(2) 0.0576(17) 0.091(2) 0.0026(16) -0.0157(15) -0.0048(16) O7 0.0557(19) 0.0609(17) 0.115(2) 0.0018(16) -0.0245(17) -0.0080(15) O8 0.107(3) 0.069(2) 0.170(3) -0.035(2) 0.070(2) -0.011(2) C1 0.052(3) 0.040(2) 0.057(3) -0.001(2) 0.008(3) -0.003(2) C2 0.041(3) 0.032(2) 0.044(2) 0.0032(19) 0.004(2) 0.0036(19) C3 0.044(3) 0.028(2) 0.041(2) 0.0029(18) 0.008(2) -0.0055(19) C4 0.057(3) 0.044(2) 0.045(3) -0.0019(19) 0.003(2) -0.001(2) C5 0.049(3) 0.041(2) 0.042(2) -0.0034(19) 0.002(2) 0.003(2) C6 0.042(3) 0.037(2) 0.043(2) 0.0005(19) 0.002(2) 0.001(2) C7 0.053(3) 0.048(3) 0.051(3) -0.005(2) -0.003(2) 0.005(2) C8 0.041(3) 0.062(3) 0.051(3) -0.004(2) -0.002(2) -0.002(3) C9 0.053(3) 0.053(3) 0.040(2) -0.002(2) 0.001(2) -0.008(3) C10 0.070(4) 0.066(3) 0.059(3) 0.001(2) 0.006(3) -0.018(3) C11 0.089(4) 0.095(4) 0.069(3) 0.007(3) 0.006(3) -0.040(4) C12 0.060(4) 0.122(4) 0.080(4) 0.005(4) 0.011(3) -0.032(4) C13 0.053(3) 0.095(4) 0.068(3) -0.001(3) 0.005(3) 0.003(3) C14 0.034(2) 0.047(2) 0.041(2) -0.0021(19) -0.0001(19) -0.001(2) C15 0.039(3) 0.046(2) 0.042(2) 0.001(2) 0.008(2) 0.001(2) C16 0.046(3) 0.042(2) 0.059(3) 0.007(2) 0.004(2) 0.006(2) C17 0.043(3) 0.055(3) 0.056(3) 0.000(2) 0.001(2) 0.003(2) C18 0.041(3) 0.048(2) 0.054(3) -0.004(2) 0.001(2) -0.006(2) C19 0.047(3) 0.044(2) 0.049(2) -0.0005(19) 0.001(2) -0.001(2) C20 0.045(3) 0.057(3) 0.067(3) 0.001(2) -0.007(2) 0.001(2) C21 0.181(8) 0.135(6) 0.160(6) -0.004(5) 0.103(6) -0.011(5) C22 0.155(7) 0.318(10) 0.170(6) -0.015(7) 0.020(5) -0.087(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 N1 C3 1.340(4) . ? N1 C14 1.440(4) . ? N1 H1 0.8600 . ? N2 C15 1.365(4) . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? O1 C1 1.382(4) . ? O1 C4 1.448(3) . ? O2 C1 1.224(4) . ? O3 C5 1.217(4) . ? O4 C6 1.418(4) . ? O4 H4 0.8200 . ? O5 C7 1.204(3) . ? O6 C20 1.274(4) . ? O7 C20 1.281(3) . ? O7 H7 0.8200 . ? O8 C21 1.339(5) . ? O8 H8 0.8200 . ? C1 C2 1.426(4) . ? C2 C3 1.365(4) . ? C2 C6 1.507(4) . ? C3 C4 1.490(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C9 1.473(5) . ? C5 C6 1.546(4) . ? C6 C7 1.545(4) . ? C7 C8 1.479(5) . ? C8 C9 1.392(4) . ? C8 C13 1.392(5) . ? C9 C10 1.394(4) . ? C10 C11 1.374(5) . ? C10 H10 0.9300 . ? C11 C12 1.396(6) . ? C11 H11 0.9300 . ? C12 C13 1.388(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C19 1.365(4) . ? C14 C15 1.407(4) . ? C15 C16 1.397(4) . ? C16 C17 1.367(4) . ? C16 H16 0.9300 . ? C17 C18 1.391(4) . ? C17 H17 0.9300 . ? C18 C19 1.398(4) . ? C18 C20 1.454(4) . ? C19 H19 0.9300 . ? C21 C22 1.461(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C3 N1 C14 125.5(3) . . ? C3 N1 H1 117.2 . . ? C14 N1 H1 117.2 . . ? C15 N2 H2A 120.0 . . ? C15 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C1 O1 C4 108.0(3) . . ? C6 O4 H4 109.5 . . ? C20 O7 H7 109.5 . . ? C21 O8 H8 109.5 . . ? O2 C1 O1 118.3(4) . . ? O2 C1 C2 131.2(4) . . ? O1 C1 C2 110.5(3) . . ? C3 C2 C1 107.7(3) . . ? C3 C2 C6 127.5(3) . . ? C1 C2 C6 124.9(3) . . ? N1 C3 C2 128.3(3) . . ? N1 C3 C4 122.4(3) . . ? C2 C3 C4 109.2(3) . . ? O1 C4 C3 104.5(3) . . ? O1 C4 H4A 110.8 . . ? C3 C4 H4A 110.8 . . ? O1 C4 H4B 110.8 . . ? C3 C4 H4B 110.8 . . ? H4A C4 H4B 108.9 . . ? O3 C5 C9 128.0(3) . . ? O3 C5 C6 124.9(4) . . ? C9 C5 C6 107.1(3) . . ? O4 C6 C2 113.0(3) . . ? O4 C6 C7 113.1(3) . . ? C2 C6 C7 112.0(3) . . ? O4 C6 C5 108.4(3) . . ? C2 C6 C5 108.1(3) . . ? C7 C6 C5 101.4(3) . . ? O5 C7 C8 127.6(4) . . ? O5 C7 C6 125.0(4) . . ? C8 C7 C6 106.9(3) . . ? C9 C8 C13 120.9(4) . . ? C9 C8 C7 109.2(4) . . ? C13 C8 C7 129.6(4) . . ? C8 C9 C10 120.9(4) . . ? C8 C9 C5 110.3(4) . . ? C10 C9 C5 128.8(4) . . ? C11 C10 C9 118.0(4) . . ? C11 C10 H10 121.0 . . ? C9 C10 H10 121.0 . . ? C10 C11 C12 121.6(5) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C13 C12 C11 120.5(5) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C8 118.2(4) . . ? C12 C13 H13 120.9 . . ? C8 C13 H13 120.9 . . ? C19 C14 C15 120.7(3) . . ? C19 C14 N1 121.5(3) . . ? C15 C14 N1 117.7(3) . . ? N2 C15 C16 121.4(3) . . ? N2 C15 C14 120.9(3) . . ? C16 C15 C14 117.7(3) . . ? C17 C16 C15 121.0(3) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C18 121.5(3) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C17 C18 C19 117.7(3) . . ? C17 C18 C20 121.7(3) . . ? C19 C18 C20 120.6(3) . . ? C14 C19 C18 121.4(3) . . ? C14 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? O6 C20 O7 121.7(4) . . ? O6 C20 C18 120.0(3) . . ? O7 C20 C18 118.3(3) . . ? O8 C21 C22 122.0(6) . . ? O8 C21 H21A 106.8 . . ? C22 C21 H21A 106.8 . . ? O8 C21 H21B 106.8 . . ? C22 C21 H21B 106.8 . . ? H21A C21 H21B 106.7 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 C4 O1 C1 O2 178.6(3) . . . . ? C4 O1 C1 C2 -1.8(4) . . . . ? O2 C1 C2 C3 -179.9(4) . . . . ? O1 C1 C2 C3 0.6(4) . . . . ? O2 C1 C2 C6 -0.4(6) . . . . ? O1 C1 C2 C6 -179.9(3) . . . . ? C14 N1 C3 C2 -179.6(3) . . . . ? C14 N1 C3 C4 -1.8(5) . . . . ? C1 C2 C3 N1 179.0(3) . . . . ? C6 C2 C3 N1 -0.5(6) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? C6 C2 C3 C4 -178.6(3) . . . . ? C1 O1 C4 C3 2.2(3) . . . . ? N1 C3 C4 O1 179.9(3) . . . . ? C2 C3 C4 O1 -1.9(4) . . . . ? C3 C2 C6 O4 -57.0(4) . . . . ? C1 C2 C6 O4 123.6(3) . . . . ? C3 C2 C6 C7 173.8(3) . . . . ? C1 C2 C6 C7 -5.6(5) . . . . ? C3 C2 C6 C5 63.0(5) . . . . ? C1 C2 C6 C5 -116.4(4) . . . . ? O3 C5 C6 O4 42.4(4) . . . . ? C9 C5 C6 O4 -139.1(3) . . . . ? O3 C5 C6 C2 -80.4(5) . . . . ? C9 C5 C6 C2 98.1(3) . . . . ? O3 C5 C6 C7 161.7(3) . . . . ? C9 C5 C6 C7 -19.8(4) . . . . ? O4 C6 C7 O5 -33.7(5) . . . . ? C2 C6 C7 O5 95.4(4) . . . . ? C5 C6 C7 O5 -149.6(4) . . . . ? O4 C6 C7 C8 138.2(3) . . . . ? C2 C6 C7 C8 -92.6(3) . . . . ? C5 C6 C7 C8 22.4(4) . . . . ? O5 C7 C8 C9 154.1(4) . . . . ? C6 C7 C8 C9 -17.6(4) . . . . ? O5 C7 C8 C13 -19.4(7) . . . . ? C6 C7 C8 C13 168.9(4) . . . . ? C13 C8 C9 C10 1.8(6) . . . . ? C7 C8 C9 C10 -172.4(3) . . . . ? C13 C8 C9 C5 178.6(3) . . . . ? C7 C8 C9 C5 4.5(4) . . . . ? O3 C5 C9 C8 -171.1(4) . . . . ? C6 C5 C9 C8 10.4(4) . . . . ? O3 C5 C9 C10 5.4(6) . . . . ? C6 C5 C9 C10 -173.0(3) . . . . ? C8 C9 C10 C11 -1.3(6) . . . . ? C5 C9 C10 C11 -177.5(4) . . . . ? C9 C10 C11 C12 -0.2(6) . . . . ? C10 C11 C12 C13 1.3(7) . . . . ? C11 C12 C13 C8 -0.8(6) . . . . ? C9 C8 C13 C12 -0.7(6) . . . . ? C7 C8 C13 C12 172.2(4) . . . . ? C3 N1 C14 C19 -62.8(5) . . . . ? C3 N1 C14 C15 119.6(4) . . . . ? C19 C14 C15 N2 179.5(3) . . . . ? N1 C14 C15 N2 -2.9(5) . . . . ? C19 C14 C15 C16 -0.3(5) . . . . ? N1 C14 C15 C16 177.3(3) . . . . ? N2 C15 C16 C17 -178.5(3) . . . . ? C14 C15 C16 C17 1.4(5) . . . . ? C15 C16 C17 C18 -1.2(6) . . . . ? C16 C17 C18 C19 -0.1(6) . . . . ? C16 C17 C18 C20 178.2(4) . . . . ? C15 C14 C19 C18 -0.9(5) . . . . ? N1 C14 C19 C18 -178.4(3) . . . . ? C17 C18 C19 C14 1.1(5) . . . . ? C20 C18 C19 C14 -177.2(3) . . . . ? C17 C18 C20 O6 -179.9(4) . . . . ? C19 C18 C20 O6 -1.7(6) . . . . ? C17 C18 C20 O7 -1.6(6) . . . . ? C19 C18 C20 O7 176.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.161 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.041