# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Ovadia Lev' 'Andrei Churakov' 'Judith Howard' 'Petr V. Prikhodchenko' _publ_contact_author_name 'Ovadia Lev' _publ_contact_author_email OVADIA@VMS.HUJI.AC.IL _publ_section_title ; Glycine and L-serine crystalline perhydrates ; # Attachment 'comb.cif' data_s _database_code_depnum_ccdc_archive 'CCDC 726697' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 H7 N O3, H2 O2' _chemical_formula_sum 'C3 H9 N O5' _chemical_formula_weight 139.11 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.8616(6) _cell_length_b 9.1187(11) _cell_length_c 13.2712(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 588.33(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4771 _cell_measurement_theta_min 2.710 _cell_measurement_theta_max 22.992 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9561 _exptl_absorpt_correction_T_max 0.9733 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 SMART APEX' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6747 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0107 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 28.00 _reflns_number_total 860 _reflns_number_gt 852 _reflns_threshold_expression I>2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0519P)^2^+0.0989P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixid _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 860 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0782 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_restrained_S_all 1.130 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration syn 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 0.7517(3) 0.59450(14) 0.49538(9) 0.0271(3) Uani 1 1 d . . . O2 O 1.0070(2) 0.51709(15) 0.47226(9) 0.0247(3) Uani 1 1 d . . . H1 H 0.658(5) 0.567(3) 0.4464(18) 0.033(6) Uiso 1 1 d . . . H2 H 0.999(5) 0.454(2) 0.5192(15) 0.024(5) Uiso 1 1 d . . . N1 N 0.7063(3) 0.77818(13) 0.67076(9) 0.0139(3) Uani 1 1 d . . . O3 O 0.9029(3) 0.80827(13) 0.88822(8) 0.0200(3) Uani 1 1 d . . . O4 O 0.7836(2) 1.12831(12) 0.79720(8) 0.0164(3) Uani 1 1 d . . . O5 O 1.0066(2) 1.02480(12) 0.66924(8) 0.0188(3) Uani 1 1 d . . . C1 C 0.8237(3) 1.02561(15) 0.73621(10) 0.0130(3) Uani 1 1 d . . . C2 C 0.6312(3) 0.89365(15) 0.74564(10) 0.0127(3) Uani 1 1 d . . . H2A H 0.4406 0.9277 0.7298 0.015 Uiso 1 1 calc R . . C3 C 0.6305(3) 0.83387(16) 0.85269(11) 0.0157(3) Uani 1 1 d . . . H3A H 0.5376 0.9048 0.8978 0.019 Uiso 1 1 calc R . . H3B H 0.5254 0.7409 0.8545 0.019 Uiso 1 1 calc R . . H13 H 0.877(5) 0.740(3) 0.6810(16) 0.021(5) Uiso 1 1 d . . . H3 H 0.948(6) 0.721(3) 0.8708(17) 0.040(7) Uiso 1 1 d . . . H12 H 0.580(5) 0.710(3) 0.6713(16) 0.024(5) Uiso 1 1 d . . . H11 H 0.717(4) 0.816(2) 0.6072(14) 0.015(4) Uiso 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 O1 0.0318(7) 0.0266(6) 0.0229(6) -0.0077(5) -0.0060(5) 0.0065(5) O2 0.0215(6) 0.0306(6) 0.0220(5) 0.0096(5) 0.0001(5) 0.0005(6) N1 0.0144(6) 0.0117(5) 0.0156(6) -0.0006(4) 0.0010(5) -0.0015(5) O3 0.0236(6) 0.0162(5) 0.0202(5) -0.0030(4) -0.0067(4) 0.0049(5) O4 0.0158(5) 0.0130(5) 0.0205(5) -0.0033(4) 0.0004(4) 0.0000(4) O5 0.0177(5) 0.0159(5) 0.0227(5) -0.0023(4) 0.0058(5) -0.0023(5) C1 0.0120(6) 0.0113(5) 0.0158(6) 0.0011(5) -0.0026(5) 0.0002(5) C2 0.0110(6) 0.0116(6) 0.0155(6) -0.0009(5) 0.0004(5) 0.0001(5) C3 0.0169(7) 0.0148(6) 0.0153(6) 0.0003(5) 0.0014(5) -0.0008(6) _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 O2 1.4607(18) . ? O1 H1 0.83(3) . ? O2 H2 0.85(2) . ? N1 C2 1.4931(17) . ? N1 H13 0.91(2) . ? N1 H12 0.87(2) . ? N1 H11 0.913(19) . ? O3 C3 1.4247(19) . ? O3 H3 0.86(3) . ? O4 C1 1.2531(17) . ? O5 C1 1.2573(18) . ? C1 C2 1.529(2) . ? C2 C3 1.5216(19) . ? C2 H2A 1.0000 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? 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 O2 O1 H1 98.9(18) . . ? O1 O2 H2 97.6(15) . . ? C2 N1 H13 113.2(14) . . ? C2 N1 H12 109.1(14) . . ? H13 N1 H12 111(2) . . ? C2 N1 H11 111.3(12) . . ? H13 N1 H11 103.5(18) . . ? H12 N1 H11 108.3(18) . . ? C3 O3 H3 107.6(19) . . ? O4 C1 O5 124.83(13) . . ? O4 C1 C2 116.09(12) . . ? O5 C1 C2 119.08(12) . . ? N1 C2 C3 111.67(11) . . ? N1 C2 C1 110.54(11) . . ? C3 C2 C1 111.08(11) . . ? N1 C2 H2A 107.8 . . ? C3 C2 H2A 107.8 . . ? C1 C2 H2A 107.8 . . ? O3 C3 C2 111.44(12) . . ? O3 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? O3 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? 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 H1 O1 O2 H2 -109(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O5 0.83(3) 1.90(3) 2.7159(17) 168(3) 4_466 O2 H2 O3 0.85(2) 1.87(2) 2.6919(16) 162(2) 3_746 N1 H11 O2 0.913(19) 2.11(2) 2.8331(17) 135.0(17) 4_466 N1 H11 O1 0.913(19) 2.512(18) 2.8760(17) 104.3(14) . N1 H12 O4 0.87(2) 1.96(3) 2.7785(17) 155(2) 3_646 N1 H13 O4 0.91(2) 1.96(2) 2.8634(17) 171(2) 3_746 O3 H3 O5 0.86(3) 1.88(3) 2.7306(17) 172(3) 3_746 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.328 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.046 #===END data_z _database_code_depnum_ccdc_archive 'CCDC 726698' _audit_creation_method SHELXL-97 _chemical_name_systematic ; glycine hydrogen peroxide sesquisolvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C2 H5 N O2), 3(H2 O2)' _chemical_formula_sum 'C4 H16 N2 O10' _chemical_formula_weight 252.19 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2854(4) _cell_length_b 8.0045(5) _cell_length_c 9.6698(6) _cell_angle_alpha 79.485(1) _cell_angle_beta 72.238(1) _cell_angle_gamma 87.275(1) _cell_volume 527.99(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4072 _cell_measurement_theta_min 2.247 _cell_measurement_theta_max 30.502 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.159 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9391 _exptl_absorpt_correction_T_max 0.9689 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'SMART APEX II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5439 _diffrn_reflns_av_R_equivalents 0.0126 _diffrn_reflns_av_sigmaI/netI 0.0155 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2543 _reflns_number_gt 2334 _reflns_threshold_expression I>2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0479P)^2^+0.1293P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2543 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0828 _refine_ls_wR_factor_gt 0.0812 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.42992(13) 0.37457(10) 0.84045(10) 0.01863(18) Uani 1 1 d . . . C11 C 0.31051(14) 0.23349(11) 0.94539(10) 0.01661(19) Uani 1 1 d . . . C12 C 0.36527(13) 0.06423(11) 0.89402(10) 0.01429(18) Uani 1 1 d . . . O11 O 0.46957(10) 0.06565(8) 0.76509(7) 0.01856(16) Uani 1 1 d . . . O12 O 0.29675(10) -0.06600(8) 0.98847(7) 0.01886(16) Uani 1 1 d . . . N2 N 0.23946(13) 0.85815(10) 0.52496(9) 0.01811(18) Uani 1 1 d . . . C21 C 0.10950(14) 0.72080(12) 0.62464(11) 0.0180(2) Uani 1 1 d . . . C22 C 0.17579(13) 0.54768(11) 0.58598(10) 0.01589(19) Uani 1 1 d . . . O21 O 0.29915(12) 0.54065(9) 0.46605(8) 0.02522(18) Uani 1 1 d . . . O22 O 0.09907(12) 0.42217(9) 0.68275(9) 0.02601(18) Uani 1 1 d . . . O1 O 0.61594(11) 0.77971(9) 0.55983(8) 0.02176(17) Uani 1 1 d . . . O2 O 0.51095(13) 0.74552(10) 0.71801(8) 0.0300(2) Uani 1 1 d . . . O3 O -0.08139(10) 0.91647(9) 0.27792(8) 0.02102(16) Uani 1 1 d . . . O4 O 0.11985(11) 0.93957(10) 0.26946(8) 0.02295(17) Uani 1 1 d . . . O5 O 0.22459(11) 0.54767(9) 0.10524(8) 0.02179(17) Uani 1 1 d . . . O6 O 0.18010(11) 0.63367(9) -0.02805(8) 0.02219(17) Uani 1 1 d . . . H11B H 0.326(2) 0.2310(17) 1.0410(16) 0.024(3) Uiso 1 1 d . . . H21A H 0.104(2) 0.7230(18) 0.7284(17) 0.031(4) Uiso 1 1 d . . . H21B H -0.021(2) 0.7394(17) 0.6196(15) 0.026(3) Uiso 1 1 d . . . H11A H 0.177(2) 0.2542(18) 0.9508(16) 0.028(3) Uiso 1 1 d . . . H1C H 0.546(2) 0.3846(19) 0.8586(17) 0.035(4) Uiso 1 1 d . . . H1B H 0.367(2) 0.476(2) 0.8502(18) 0.040(4) Uiso 1 1 d . . . H1A H 0.457(2) 0.359(2) 0.744(2) 0.045(4) Uiso 1 1 d . . . H2A H 0.362(2) 0.8292(18) 0.5212(16) 0.031(4) Uiso 1 1 d . . . H5 H 0.123(2) 0.5575(18) 0.1683(18) 0.031(4) Uiso 1 1 d . . . H2 H 0.503(2) 0.846(2) 0.7342(19) 0.041(4) Uiso 1 1 d . . . H4 H 0.174(2) 0.943(2) 0.1778(19) 0.040(4) Uiso 1 1 d . . . H2C H 0.209(2) 0.956(2) 0.5650(17) 0.037(4) Uiso 1 1 d . . . H6 H 0.226(2) 0.735(2) -0.0361(18) 0.037(4) Uiso 1 1 d . . . H2B H 0.228(2) 0.8753(18) 0.4334(17) 0.027(3) Uiso 1 1 d . . . H1 H 0.649(2) 0.672(2) 0.5504(18) 0.042(4) Uiso 1 1 d . . . H3 H -0.097(3) 0.801(2) 0.3053(19) 0.046(5) Uiso 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 0.0253(4) 0.0120(4) 0.0169(4) -0.0023(3) -0.0038(3) -0.0011(3) C11 0.0189(4) 0.0122(4) 0.0160(4) -0.0028(3) -0.0010(3) 0.0001(3) C12 0.0152(4) 0.0129(4) 0.0151(4) -0.0036(3) -0.0044(3) 0.0004(3) O11 0.0224(3) 0.0161(3) 0.0145(3) -0.0042(2) -0.0006(3) -0.0010(3) O12 0.0248(4) 0.0136(3) 0.0153(3) -0.0015(2) -0.0019(3) -0.0033(3) N2 0.0246(4) 0.0118(4) 0.0156(4) -0.0019(3) -0.0030(3) 0.0000(3) C21 0.0212(5) 0.0123(4) 0.0166(4) -0.0028(3) -0.0002(3) 0.0003(3) C22 0.0185(4) 0.0128(4) 0.0163(4) -0.0035(3) -0.0047(3) 0.0005(3) O21 0.0325(4) 0.0154(3) 0.0198(4) -0.0046(3) 0.0045(3) 0.0012(3) O22 0.0330(4) 0.0139(3) 0.0224(4) -0.0019(3) 0.0042(3) -0.0029(3) O1 0.0296(4) 0.0148(3) 0.0138(3) -0.0032(3) 0.0044(3) -0.0007(3) O2 0.0490(5) 0.0160(4) 0.0139(4) -0.0031(3) 0.0071(3) -0.0018(3) O3 0.0177(3) 0.0184(3) 0.0255(4) -0.0061(3) -0.0028(3) -0.0012(3) O4 0.0193(4) 0.0318(4) 0.0168(4) -0.0046(3) -0.0032(3) -0.0042(3) O5 0.0233(4) 0.0188(3) 0.0187(4) -0.0002(3) -0.0012(3) -0.0004(3) O6 0.0295(4) 0.0172(3) 0.0186(4) -0.0025(3) -0.0051(3) -0.0043(3) _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 C11 1.4827(12) . ? N1 H1C 0.927(17) . ? N1 H1B 0.918(17) . ? N1 H1A 0.923(18) . ? C11 C12 1.5214(12) . ? C11 H11B 0.962(14) . ? C11 H11A 0.968(15) . ? C12 O11 1.2448(11) . ? C12 O12 1.2625(11) . ? N2 C21 1.4798(12) . ? N2 H2A 0.901(16) . ? N2 H2C 0.923(16) . ? N2 H2B 0.900(15) . ? C21 C22 1.5194(12) . ? C21 H21A 0.995(15) . ? C21 H21B 0.970(15) . ? C22 O21 1.2405(12) . ? C22 O22 1.2604(12) . ? O1 O2 1.4673(10) . ? O1 H1 0.897(17) . ? O2 H2 0.846(17) . ? O3 O4 1.4620(10) . ? O3 H3 0.915(18) . ? O4 H4 0.849(18) . ? O5 O6 1.4663(10) . ? O5 H5 0.812(16) . ? O6 H6 0.870(17) . ? 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 C11 N1 H1C 111.6(10) . . ? C11 N1 H1B 110.1(10) . . ? H1C N1 H1B 106.9(14) . . ? C11 N1 H1A 111.5(11) . . ? H1C N1 H1A 107.7(14) . . ? H1B N1 H1A 108.9(14) . . ? N1 C11 C12 111.32(8) . . ? N1 C11 H11B 108.4(8) . . ? C12 C11 H11B 111.0(8) . . ? N1 C11 H11A 108.8(8) . . ? C12 C11 H11A 107.7(8) . . ? H11B C11 H11A 109.5(11) . . ? O11 C12 O12 126.15(8) . . ? O11 C12 C11 118.33(8) . . ? O12 C12 C11 115.51(8) . . ? C21 N2 H2A 108.4(9) . . ? C21 N2 H2C 107.9(10) . . ? H2A N2 H2C 108.9(13) . . ? C21 N2 H2B 111.7(9) . . ? H2A N2 H2B 109.6(13) . . ? H2C N2 H2B 110.3(13) . . ? N2 C21 C22 111.50(8) . . ? N2 C21 H21A 109.3(9) . . ? C22 C21 H21A 110.0(8) . . ? N2 C21 H21B 110.5(8) . . ? C22 C21 H21B 108.9(8) . . ? H21A C21 H21B 106.5(12) . . ? O21 C22 O22 125.83(9) . . ? O21 C22 C21 118.83(8) . . ? O22 C22 C21 115.34(8) . . ? O2 O1 H1 97.0(11) . . ? O1 O2 H2 98.7(12) . . ? O4 O3 H3 102.3(11) . . ? O3 O4 H4 100.4(11) . . ? O6 O5 H5 101.2(11) . . ? O5 O6 H6 100.2(11) . . ? 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 N1 C11 C12 O11 -13.17(12) . . . . ? N2 C21 C22 O21 -13.67(13) . . . . ? H1 O1 O2 H2 166.5(16) . . . . ? H3 O3 O4 H4 96.2(16) . . . . ? H5 O5 O6 H6 95.3(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2B O4 0.900(15) 1.955(15) 2.8213(12) 161.1(13) . N2 H2A O1 0.901(16) 2.007(16) 2.8903(12) 166.6(14) . N2 H2C O3 0.923(16) 1.958(16) 2.8165(11) 153.9(14) 2_576 N1 H1A O21 0.923(18) 2.297(18) 2.9941(11) 132.0(14) 2_666 N1 H1A O11 0.923(18) 2.318(17) 2.6815(10) 103.1(12) . N1 H1C O5 0.927(17) 1.927(17) 2.8414(12) 168.7(14) 2_666 O1 H1 O21 0.897(17) 1.752(17) 2.6477(10) 177.2(16) 2_666 N1 H1B O6 0.918(17) 2.058(17) 2.9021(11) 152.2(14) 1_556 O2 H2 O11 0.846(17) 1.826(18) 2.6707(10) 175.9(17) 1_565 O3 H3 O22 0.915(18) 1.771(18) 2.6713(10) 167.4(17) 2_566 O5 H5 O22 0.812(16) 1.834(17) 2.6454(11) 177.3(16) 2_566 O4 H4 O12 0.849(18) 1.789(18) 2.6358(10) 175.3(16) 1_564 O6 H6 O12 0.870(17) 1.779(17) 2.6352(10) 167.9(16) 1_564 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.389 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.048