# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Alexander Briceno' _publ_contact_author_email ABRICENO@IVIC.VE _publ_section_title ; Concomitant [2+2] cycloaddition solid state reactions from organic co-crystals self-assembled via mechanochemistry ; loop_ _publ_author_name A.Briceno 'Carlos Avendano' # Attachment 'SHELXLEC2.CIF' data_c2c-p _database_code_depnum_ccdc_archive 'CCDC 704338' #========================================================================== _audit_creation_method SHELXL-97 _audit_creation_date '20 August 2008' #========================================================================== _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2, C4 H4 O4' _chemical_formula_sum 'C16 H14 N2 O4' _chemical_formula_weight 298.29 _chemical_compound_source Synthesis 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 C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.911(11) _cell_length_b 3.9313(15) _cell_length_c 18.607(9) _cell_angle_alpha 90.00 _cell_angle_beta 119.067(10) _cell_angle_gamma 90.00 _cell_volume 1464.9(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 837 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 26.10 _exptl_crystal_description Prism _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type 'Multi Scan' _exptl_absorpt_correction_T_min 0.913 _exptl_absorpt_correction_T_max 0.946 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method '\w ' _diffrn_radiation_detector CCD _diffrn_measurement_device 'Mercury (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7548 _diffrn_reflns_av_R_equivalents 0.0594 _diffrn_reflns_av_sigmaI/netI 0.0637 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.13 _reflns_number_total 1457 _reflns_number_gt 962 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _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^)+(0.0741P)^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 SHELXL _refine_ls_extinction_coef 0.011(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1457 _refine_ls_number_parameters 105 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0888 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1566 _refine_ls_wR_factor_gt 0.1326 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 N1 N 0.13095(8) 0.4271(4) 0.35922(9) 0.0499(5) Uani 1 1 d . . . O1 O 0.12888(8) 0.3319(4) 0.55240(8) 0.0775(6) Uani 1 1 d . . . O2 O 0.05758(7) 0.1931(4) 0.42318(9) 0.0690(5) Uani 1 1 d . . . HOH H 0.0898(12) 0.294(5) 0.4056(14) 0.101(8) Uiso 1 1 d . . . C1 C 0.07685(10) 0.2144(5) 0.50192(13) 0.0517(6) Uani 1 1 d . . . C2 C 0.02744(9) 0.0787(4) 0.52486(11) 0.0512(6) Uani 1 1 d . . . H2 H 0.0366 0.1088 0.5789 0.061 Uiso 1 1 calc R . . C3 C 0.09929(10) 0.3566(4) 0.27883(12) 0.0556(6) Uani 1 1 d . . . H3 H 0.0587 0.2426 0.2571 0.067 Uiso 1 1 calc R . . C4 C 0.12311(11) 0.4421(5) 0.22661(11) 0.0560(6) Uani 1 1 d . . . H4 H 0.0989 0.3909 0.1709 0.067 Uiso 1 1 calc R . . C5 C 0.18360(11) 0.6056(4) 0.25847(11) 0.0544(6) Uani 1 1 d . . . H5 H 0.2011 0.6669 0.2245 0.065 Uiso 1 1 calc R . . C6 C 0.21779(10) 0.6772(4) 0.34096(11) 0.0502(6) Uani 1 1 d . . . H6 H 0.2592 0.7834 0.3637 0.060 Uiso 1 1 calc R . . C7 C 0.22157(8) 0.6665(4) 0.47836(10) 0.0466(5) Uani 1 1 d . . . H7 H 0.1998 0.5914 0.5065 0.056 Uiso 1 1 calc R . . C8 C 0.19001(9) 0.5896(4) 0.39076(10) 0.0422(5) Uani 1 1 d . . . 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 0.0437(11) 0.0646(11) 0.0412(10) -0.0036(6) 0.0204(8) -0.0082(7) O1 0.0570(11) 0.1249(14) 0.0516(11) -0.0090(7) 0.0273(9) -0.0324(8) O2 0.0580(11) 0.1050(12) 0.0481(10) -0.0051(7) 0.0291(8) -0.0285(8) C1 0.0483(13) 0.0649(13) 0.0447(13) 0.0016(8) 0.0247(11) -0.0062(9) C2 0.0507(14) 0.0615(13) 0.0438(13) 0.0018(8) 0.0249(10) -0.0044(8) C3 0.0457(13) 0.0696(13) 0.0458(13) -0.0065(9) 0.0176(10) -0.0103(9) C4 0.0583(15) 0.0694(13) 0.0355(12) -0.0020(8) 0.0190(10) -0.0007(10) C5 0.0621(15) 0.0646(13) 0.0435(13) 0.0027(8) 0.0312(11) -0.0001(9) C6 0.0481(13) 0.0624(12) 0.0445(13) 0.0006(8) 0.0259(10) -0.0073(9) C7 0.0424(12) 0.0636(12) 0.0372(12) 0.0001(7) 0.0221(10) -0.0077(8) C8 0.0373(11) 0.0508(12) 0.0379(11) 0.0011(7) 0.0178(9) -0.0031(8) _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 1.336(2) . ? N1 C8 1.346(2) . ? O1 C1 1.195(2) . ? O2 C1 1.311(2) . ? O2 HOH 1.02(3) . ? C1 C2 1.489(3) . ? C2 C2 1.300(3) 5_556 ? C2 H2 0.9300 . ? C3 C4 1.368(3) . ? C3 H3 0.9300 . ? C4 C5 1.373(3) . ? C4 H4 0.9300 . ? C5 C6 1.371(2) . ? C5 H5 0.9300 . ? C6 C8 1.398(3) . ? C6 H6 0.9300 . ? C7 C7 1.326(3) 7_566 ? C7 C8 1.458(2) . ? C7 H7 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 C3 N1 C8 118.07(16) . . ? C1 O2 HOH 115.4(12) . . ? O1 C1 O2 124.66(19) . . ? O1 C1 C2 121.33(19) . . ? O2 C1 C2 114.01(18) . . ? C2 C2 C1 125.0(2) 5_556 . ? C2 C2 H2 117.5 5_556 . ? C1 C2 H2 117.5 . . ? N1 C3 C4 123.86(19) . . ? N1 C3 H3 118.1 . . ? C4 C3 H3 118.1 . . ? C3 C4 C5 118.40(18) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? C6 C5 C4 119.14(18) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C8 119.67(18) . . ? C5 C6 H6 120.2 . . ? C8 C6 H6 120.2 . . ? C7 C7 C8 126.1(2) 7_566 . ? C7 C7 H7 116.9 7_566 . ? C8 C7 H7 116.9 . . ? N1 C8 C6 120.84(16) . . ? N1 C8 C7 115.69(15) . . ? C6 C8 C7 123.47(17) . . ? _diffrn_measured_fraction_theta_max 0.815 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.284 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.060 # End of CIF ============================================================ # Attachment 'SHELXLEC1.CIF' data_shelxle _database_code_depnum_ccdc_archive 'CCDC 704339' #========================================================================== _audit_creation_method SHELXL-97 _audit_creation_date '20 August 2008' #========================================================================== _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2, C5 H6 O4, H2 O' _chemical_formula_sum 'C17 H18 N2 O5' _chemical_formula_weight 330.33 _chemical_compound_source Synthesis 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 C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.841(8) _cell_length_b 11.394(5) _cell_length_c 14.637(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.423(13) _cell_angle_gamma 90.00 _cell_volume 3303(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1272 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 26.30 _exptl_crystal_description Prism _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type 'Multi Scan' _exptl_absorpt_correction_T_min 0.959 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method '\w ' _diffrn_radiation_detector CCD _diffrn_measurement_device 'Mercury (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18144 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.13 _reflns_number_total 3205 _reflns_number_gt 1958 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _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^)+(0.1031P)^2^+3.0139P] 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 SHELXL _refine_ls_extinction_coef 0.0022(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3205 _refine_ls_number_parameters 266 _refine_ls_number_restraints 266 _refine_ls_R_factor_all 0.1225 _refine_ls_R_factor_gt 0.0748 _refine_ls_wR_factor_ref 0.2293 _refine_ls_wR_factor_gt 0.1954 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.038 _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 O1W O 0.31807(14) -0.7614(3) 0.5434(2) 0.0836(9) Uani 1 1 d . . . H1W1 H 0.335(2) -0.693(4) 0.544(3) 0.107(16) Uiso 1 1 d . . . H2W1 H 0.294(3) -0.766(7) 0.489(5) 0.23(4) Uiso 1 1 d . . . O3 O 0.39007(12) 0.0585(2) 0.6023(2) 0.0936(9) Uani 1 1 d . . . H1O3 H 0.3674 0.1204 0.5899 0.112 Uiso 1 1 d R . . O2 O 0.55795(12) -0.2317(2) 0.6638(2) 0.0926(9) Uani 1 1 d . . . H2O2 H 0.5791 -0.2964 0.6695 0.111 Uiso 1 1 d R . . O4 O 0.47494(14) 0.1827(2) 0.6101(3) 0.1145(11) Uani 1 1 d . . . O1 O 0.65789(14) -0.1520(3) 0.6468(3) 0.1258(13) Uani 1 1 d . . . N1 N 0.35552(11) -0.5225(2) 0.54574(16) 0.0554(7) Uani 1 1 d . . . C1 C 0.59706(17) -0.1425(3) 0.6522(2) 0.0701(9) Uani 1 1 d . . . C2 C 0.56236(15) -0.0266(3) 0.6362(2) 0.0618(8) Uani 1 1 d . . . C3 C 0.49589(15) -0.0224(3) 0.6312(2) 0.0619(8) Uani 1 1 d . . . H3 H 0.4731 -0.0926 0.6393 0.074 Uiso 1 1 calc R . . C4 C 0.45429(17) 0.0839(3) 0.6139(2) 0.0674(9) Uani 1 1 d . . . C5 C 0.60934(19) 0.0749(3) 0.6270(3) 0.0966(13) Uani 1 1 d . . . H5A H 0.5836 0.1457 0.6176 0.145 Uiso 1 1 calc R . . H5B H 0.6364 0.0621 0.5756 0.145 Uiso 1 1 calc R . . H5C H 0.6382 0.0820 0.6817 0.145 Uiso 1 1 calc R . . C6 C 0.47090(13) -0.5229(3) 0.51097(18) 0.0515(7) Uani 1 1 d . . . H6 H 0.4680 -0.6044 0.5119 0.062 Uiso 1 1 calc R . . C7 C 0.41064(13) -0.4576(3) 0.53382(17) 0.0494(7) Uani 1 1 d . . . C8 C 0.29869(14) -0.4667(3) 0.5670(2) 0.0613(8) Uani 1 1 d . . . H8 H 0.2602 -0.5114 0.5746 0.074 Uiso 1 1 calc R . . C9 C 0.29461(16) -0.3477(3) 0.5782(2) 0.0650(9) Uani 1 1 d . . . H9 H 0.2544 -0.3124 0.5927 0.078 Uiso 1 1 calc R . . C10 C 0.35092(18) -0.2823(3) 0.5674(2) 0.0730(10) Uani 1 1 d . . . H10 H 0.3497 -0.2013 0.5750 0.088 Uiso 1 1 calc R . . C11 C 0.40975(15) -0.3367(3) 0.5451(2) 0.0637(9) Uani 1 1 d . . . H11 H 0.4486 -0.2928 0.5378 0.076 Uiso 1 1 calc R . . C12 C 0.4753(2) -0.5667(8) 0.7577(4) 0.056(2) Uani 0.492(10) 1 d PDU . 1 H12 H 0.4787 -0.6379 0.7887 0.067 Uiso 0.50 1 calc PR . 1 C13 C 0.4039(2) -0.5520(8) 0.7735(6) 0.058(2) Uani 0.492(10) 1 d PGDU . 1 N2 N 0.3827(4) -0.4405(7) 0.7977(7) 0.049(2) Uani 0.492(10) 1 d PGU . 1 C14 C 0.3152(4) -0.4206(5) 0.8134(8) 0.053(2) Uani 0.492(10) 1 d PGU . 1 H14 H 0.3011 -0.3461 0.8296 0.064 Uiso 0.492(10) 1 calc PR . 1 C15 C 0.2690(3) -0.5122(8) 0.8050(9) 0.062(3) Uani 0.492(10) 1 d PGU . 1 H15 H 0.2239 -0.4989 0.8155 0.074 Uiso 0.492(10) 1 calc PR . 1 C16 C 0.2902(3) -0.6236(6) 0.7808(7) 0.071(2) Uani 0.492(10) 1 d PGU . 1 H16 H 0.2592 -0.6849 0.7751 0.085 Uiso 0.492(10) 1 calc PR . 1 C17 C 0.3576(4) -0.6435(6) 0.7651(6) 0.060(2) Uani 0.492(10) 1 d PGU . 1 H17 H 0.3718 -0.7181 0.7489 0.072 Uiso 0.492(10) 1 calc PR . 1 C12A C 0.4805(2) -0.4841(8) 0.7545(5) 0.052(2) Uani 0.508(10) 1 d PDU . 2 H12A H 0.4747 -0.4037 0.7468 0.062 Uiso 0.50 1 calc PR . 2 C13A C 0.4105(2) -0.5085(7) 0.7735(6) 0.0480(18) Uani 0.508(10) 1 d PGDU . 2 N2A N 0.3741(4) -0.4175(5) 0.8103(7) 0.059(2) Uani 0.508(10) 1 d PGU . 2 C14A C 0.3070(4) -0.4344(6) 0.8295(8) 0.056(2) Uani 0.508(10) 1 d PGU . 2 H14A H 0.2827 -0.3734 0.8541 0.067 Uiso 0.508(10) 1 calc PR . 2 C15A C 0.2763(3) -0.5423(8) 0.8119(8) 0.058(2) Uani 0.508(10) 1 d PGU . 2 H15A H 0.2314 -0.5536 0.8248 0.070 Uiso 0.508(10) 1 calc PR . 2 C16A C 0.3127(4) -0.6333(6) 0.7752(7) 0.064(2) Uani 0.508(10) 1 d PGU . 2 H16A H 0.2921 -0.7056 0.7634 0.076 Uiso 0.508(10) 1 calc PR . 2 C17A C 0.3797(4) -0.6165(6) 0.7560(5) 0.060(2) Uani 0.508(10) 1 d PGU . 2 H17A H 0.4040 -0.6774 0.7314 0.072 Uiso 0.508(10) 1 calc PR . 2 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 O1W 0.0556(15) 0.0562(16) 0.138(3) 0.0011(15) -0.0063(14) 0.0031(12) O3 0.0512(15) 0.0707(17) 0.159(3) 0.0215(16) 0.0063(14) 0.0092(12) O2 0.0587(16) 0.0696(17) 0.151(3) 0.0242(15) 0.0148(15) 0.0167(13) O4 0.0729(19) 0.0594(17) 0.210(3) -0.0007(19) -0.0024(19) 0.0068(15) O1 0.0545(18) 0.082(2) 0.239(4) 0.000(2) -0.0059(19) 0.0110(14) N1 0.0416(14) 0.0596(16) 0.0656(15) 0.0018(11) 0.0079(10) -0.0009(12) C1 0.052(2) 0.066(2) 0.092(2) -0.0055(18) -0.0018(16) 0.0056(17) C2 0.058(2) 0.062(2) 0.0646(18) -0.0028(15) 0.0046(14) 0.0048(16) C3 0.0541(19) 0.058(2) 0.074(2) -0.0001(15) 0.0064(14) 0.0067(15) C4 0.059(2) 0.056(2) 0.088(2) -0.0020(16) 0.0082(16) 0.0049(17) C5 0.064(2) 0.070(3) 0.156(4) 0.005(2) 0.008(2) -0.007(2) C6 0.0445(16) 0.0521(17) 0.0581(17) 0.0026(13) 0.0040(12) 0.0032(13) C7 0.0414(16) 0.0541(18) 0.0525(16) 0.0043(12) 0.0023(11) 0.0032(13) C8 0.0416(17) 0.070(2) 0.073(2) 0.0053(16) 0.0111(14) -0.0016(15) C9 0.054(2) 0.068(2) 0.074(2) 0.0000(16) 0.0135(14) 0.0123(17) C10 0.065(2) 0.062(2) 0.094(2) -0.0001(17) 0.0156(17) 0.0079(17) C11 0.0477(18) 0.057(2) 0.087(2) 0.0019(16) 0.0104(15) 0.0023(15) C12 0.061(4) 0.052(5) 0.054(3) 0.007(3) 0.002(3) -0.004(3) C13 0.059(4) 0.052(5) 0.060(4) 0.009(4) -0.003(3) -0.009(3) N2 0.046(4) 0.056(4) 0.045(3) -0.010(3) 0.001(3) -0.015(3) C14 0.044(4) 0.063(4) 0.053(4) 0.005(4) 0.019(3) -0.012(3) C15 0.057(4) 0.057(5) 0.071(5) 0.014(4) 0.001(4) -0.008(4) C16 0.057(4) 0.076(5) 0.079(4) 0.005(4) 0.009(4) -0.003(4) C17 0.047(5) 0.063(4) 0.070(4) 0.000(3) 0.010(4) -0.017(4) C12A 0.049(4) 0.050(4) 0.057(3) 0.002(3) 0.004(4) 0.002(3) C13A 0.055(4) 0.042(4) 0.046(3) -0.007(3) -0.004(3) 0.000(3) N2A 0.052(4) 0.067(4) 0.058(4) -0.006(3) 0.011(3) 0.008(3) C14A 0.048(4) 0.061(4) 0.059(5) 0.015(3) 0.006(3) -0.013(3) C15A 0.054(4) 0.054(5) 0.066(4) 0.015(4) 0.003(3) -0.011(3) C16A 0.057(5) 0.056(4) 0.078(4) 0.000(3) 0.008(4) -0.012(4) C17A 0.049(4) 0.058(4) 0.074(4) 0.002(3) 0.009(4) -0.023(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 O1W H1W1 0.84(5) . ? O1W H2W1 0.90(8) . ? O3 C4 1.308(4) . ? O3 H1O3 0.8501 . ? O2 C1 1.296(4) . ? O2 H2O2 0.8500 . ? O4 C4 1.201(4) . ? O1 C1 1.219(4) . ? N1 C7 1.340(3) . ? N1 C8 1.347(4) . ? C1 C2 1.501(5) . ? C2 C3 1.317(4) . ? C2 C5 1.497(5) . ? C3 C4 1.478(5) . ? C3 H3 0.9300 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C6 1.324(5) 5_646 ? C6 C7 1.464(4) . ? C6 H6 0.9300 . ? C7 C11 1.388(4) . ? C8 C9 1.369(5) . ? C8 H8 0.9300 . ? C9 C10 1.360(5) . ? C9 H9 0.9300 . ? C10 C11 1.378(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C12 1.018(8) 2_656 ? C12 C13 1.459(2) . ? C12 H12 0.9300 . ? C13 N2 1.3900 . ? C13 C17 1.3900 . ? N2 C14 1.3900 . ? C14 C15 1.3900 . ? C14 H14 0.9300 . ? C15 C16 1.3900 . ? C15 H15 0.9300 . ? C16 C17 1.3900 . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C12A C12A 0.791(8) 2_656 ? C12A C13A 1.460(2) . ? C12A H12A 0.9300 . ? C13A N2A 1.3900 . ? C13A C17A 1.3900 . ? N2A C14A 1.3900 . ? C14A C15A 1.3900 . ? C14A H14A 0.9300 . ? C15A C16A 1.3900 . ? C15A H15A 0.9300 . ? C16A C17A 1.3900 . ? C16A H16A 0.9300 . ? C17A H17A 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 H1W1 O1W H2W1 104(5) . . ? C4 O3 H1O3 110.0 . . ? C1 O2 H2O2 113.4 . . ? C7 N1 C8 118.1(3) . . ? O1 C1 O2 122.8(3) . . ? O1 C1 C2 121.0(3) . . ? O2 C1 C2 115.9(3) . . ? C3 C2 C5 126.4(3) . . ? C3 C2 C1 119.3(3) . . ? C5 C2 C1 114.3(3) . . ? C2 C3 C4 125.9(3) . . ? C2 C3 H3 117.1 . . ? C4 C3 H3 117.1 . . ? O4 C4 O3 122.3(3) . . ? O4 C4 C3 126.0(3) . . ? O3 C4 C3 111.8(3) . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C6 C6 C7 126.2(4) 5_646 . ? C6 C6 H6 116.9 5_646 . ? C7 C6 H6 116.9 . . ? N1 C7 C11 121.0(3) . . ? N1 C7 C6 115.7(3) . . ? C11 C7 C6 123.2(3) . . ? N1 C8 C9 123.4(3) . . ? N1 C8 H8 118.3 . . ? C9 C8 H8 118.3 . . ? C10 C9 C8 118.3(3) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? C9 C10 C11 119.6(3) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C7 119.5(3) . . ? C10 C11 H11 120.3 . . ? C7 C11 H11 120.3 . . ? C12 C12 C13 172.4(6) 2_656 . ? C12 C12 H12 93.8 2_656 . ? C13 C12 H12 93.8 . . ? N2 C13 C17 120.0 . . ? N2 C13 C12 117.2(6) . . ? C17 C13 C12 122.8(6) . . ? C13 N2 C14 120.0 . . ? N2 C14 C15 120.0 . . ? N2 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.0 . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 120.0 . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C13 120.0 . . ? C16 C17 H17 120.0 . . ? C13 C17 H17 120.0 . . ? C12A C12A C13A 168.9(4) 2_656 . ? C12A C12A H12A 95.5 2_656 . ? C13A C12A H12A 95.5 . . ? N2A C13A C17A 120.0 . . ? N2A C13A C12A 117.0(5) . . ? C17A C13A C12A 123.0(5) . . ? C13A N2A C14A 120.0 . . ? C15A C14A N2A 120.0 . . ? C15A C14A H14A 120.0 . . ? N2A C14A H14A 120.0 . . ? C14A C15A C16A 120.0 . . ? C14A C15A H15A 120.0 . . ? C16A C15A H15A 120.0 . . ? C17A C16A C15A 120.0 . . ? C17A C16A H16A 120.0 . . ? C15A C16A H16A 120.0 . . ? C16A C17A C13A 120.0 . . ? C16A C17A H17A 120.0 . . ? C13A C17A H17A 120.0 . . ? _diffrn_measured_fraction_theta_max 0.794 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.478 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.045