# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2000 # CCDC Number: 440/217 data_global #======================================================================== # SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Pr. Roger Guilard, LIMSAG, CNRS UMR 5633, Universite de Bourgogne, Faculte des Sciences, 6 boulevard Gabriel, 21100 Dijon, France ; _publ_contact_author_phone '+33 3 80 39 61 11' _publ_contact_author_fax '+33 3 80 39 61 17' _publ_contact_author_email Roger.Guilard@u-bourgogne.fr _publ_requested_journal 'New Journal of Chemistry' #====================================================================== # TITLE _publ_section_title ; Synthesis, characterization and X-ray crystal structures of cyclam derivatives. Part IV. 1,4,8,11-Tetraazacyclotetradecane-5,12-dione and its diprotonated forms. ; #======================================================================== data_L _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H20 N4 O2,2(H2 O)' _chemical_formula_sum 'C10 H24 N4 O4' _chemical_formula_weight 264.33 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.559(2) _cell_length_b 4.997(2) _cell_length_c 10.293(2) _cell_angle_alpha 116.96(3) _cell_angle_beta 91.55(3) _cell_angle_gamma 100.31(3) _cell_volume 338.34(18) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 9.5 _cell_measurement_theta_max 10.5 _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 144 _exptl_absorpt_coefficient_mu 0.100 _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 293(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 'Stoe AED2' _diffrn_measurement_method \w-\Q-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% ? _diffrn_reflns_number 1163 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0118 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1163 _reflns_number_gt 1063 _reflns_threshold_expression >2sigma(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^)+(0.0507P)^2^+0.0915P] 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 1163 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0956 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 O1 O 0.76783(16) 0.0161(2) 0.05547(12) 0.0437(3) Uani 1 1 d . . . N1 N 0.69717(15) 0.3677(3) -0.01086(13) 0.0315(3) Uani 1 1 d . . . H1 H 0.701(2) 0.557(5) 0.0171(19) 0.043(5) Uiso 1 1 d . . . N2 N 0.87485(15) 0.4440(3) -0.25694(13) 0.0302(3) Uani 1 1 d . . . H2 H 0.885(2) 0.610(4) -0.1671(19) 0.035(4) Uiso 1 1 d . . . C1 C 0.74990(17) 0.2857(3) 0.08896(15) 0.0284(3) Uani 1 1 d . . . C2 C 0.65938(19) 0.1491(3) -0.16614(16) 0.0339(4) Uani 1 1 d . . . H2A H 0.562(2) 0.203(4) -0.2077(19) 0.045(5) Uiso 1 1 d . . . H2B H 0.617(2) -0.061(4) -0.1772(18) 0.038(4) Uiso 1 1 d . . . C3 C 0.82456(19) 0.1525(3) -0.24489(16) 0.0325(4) Uani 1 1 d . . . H3A H 0.920(2) 0.120(4) -0.1890(18) 0.039(4) Uiso 1 1 d . . . H3B H 0.796(2) -0.034(4) -0.3471(18) 0.035(4) Uiso 1 1 d . . . C4 C 1.0411(2) 0.4681(3) -0.32399(15) 0.0329(4) Uani 1 1 d . . . H4A H 1.064(2) 0.666(4) -0.3290(18) 0.040(4) Uiso 1 1 d . . . H4B H 1.022(2) 0.294(4) -0.4244(19) 0.039(4) Uiso 1 1 d . . . C5 C 0.78699(19) 0.5401(3) 0.24581(16) 0.0324(3) Uani 1 1 d . . . H5A H 0.689(3) 0.503(4) 0.2961(19) 0.047(5) Uiso 1 1 d . . . H5B H 0.789(2) 0.739(4) 0.2485(18) 0.039(4) Uiso 1 1 d . . . O3 O 0.5922(2) 0.2890(4) -0.48607(18) 0.0652(5) Uani 1 1 d . . . H6 H 0.650(3) 0.351(5) -0.427(2) 0.056(7) 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 0.0613(7) 0.0251(6) 0.0466(7) 0.0185(5) -0.0010(5) 0.0101(5) N1 0.0351(7) 0.0249(7) 0.0372(7) 0.0162(5) 0.0035(5) 0.0085(5) N2 0.0338(6) 0.0258(6) 0.0311(6) 0.0134(5) 0.0008(5) 0.0071(5) C1 0.0239(6) 0.0251(7) 0.0392(8) 0.0182(6) 0.0046(5) 0.0032(5) C2 0.0308(7) 0.0331(8) 0.0370(8) 0.0172(6) -0.0016(6) 0.0034(6) C3 0.0354(8) 0.0262(7) 0.0361(8) 0.0148(6) 0.0024(6) 0.0068(6) C4 0.0416(8) 0.0311(8) 0.0284(7) 0.0158(6) 0.0051(6) 0.0082(6) C5 0.0332(7) 0.0307(8) 0.0366(8) 0.0175(6) 0.0097(6) 0.0090(6) O3 0.0598(9) 0.0715(10) 0.0607(9) 0.0353(8) -0.0225(7) -0.0026(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 C1 1.2644(17) . ? N1 C1 1.3420(18) . ? N1 C2 1.453(2) . ? N2 C4 1.4625(19) . ? N2 C3 1.4998(19) . ? C1 C5 1.513(2) . ? C2 C3 1.509(2) . ? C4 C5 1.526(2) 2_765 ? C5 C4 1.526(2) 2_765 ? 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 C1 N1 C2 121.36(12) . . ? C4 N2 C3 113.57(11) . . ? O1 C1 N1 122.89(13) . . ? O1 C1 C5 121.98(13) . . ? N1 C1 C5 115.13(12) . . ? N1 C2 C3 112.09(12) . . ? N2 C3 C2 111.30(12) . . ? N2 C4 C5 116.44(11) . 2_765 ? C1 C5 C4 110.84(12) . 2_765 ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.246 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.037 #===END data_H2LBr2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H22 N4 O2,Br2' _chemical_formula_sum 'C10 H22 Br2 N4 O2' _chemical_formula_weight 390.14 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' 'Br' 'Br' -0.2901 2.4595 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2851(2) _cell_length_b 8.0718(4) _cell_length_c 9.5424(5) _cell_angle_alpha 109.126(3) _cell_angle_beta 104.189(3) _cell_angle_gamma 97.989(3) _cell_volume 362.03(3) _cell_formula_units_Z 1 _cell_measurement_temperature 112(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.789 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 5.600 _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 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2142 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1619 _reflns_number_gt 1550 _reflns_threshold_expression >2sigma(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^)+(0.0285P)^2^+0.4758P] 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 0.029(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1619 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0271 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0682 _refine_ls_wR_factor_gt 0.0670 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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 O1 O 0.3900(4) 0.3529(3) 0.0477(2) 0.0193(4) Uani 1 1 d . . . N1 N -0.0197(4) 0.2623(3) 0.0663(3) 0.0135(4) Uani 1 1 d . . . HN1 H -0.110(6) 0.258(4) 0.130(4) 0.016 Uiso 1 1 d . . . N2 N -0.4582(4) 0.2541(3) -0.2268(3) 0.0123(4) Uani 1 1 d . . . HN2 H -0.468(6) 0.317(4) -0.138(4) 0.015 Uiso 1 1 d . . . HN3 H -0.580(6) 0.150(5) -0.258(4) 0.015 Uiso 1 1 d . . . C1 C 0.2361(5) 0.3592(3) 0.1268(3) 0.0125(5) Uani 1 1 d . . . C2 C -0.1172(5) 0.1273(3) -0.0923(3) 0.0148(5) Uani 1 1 d . . . H2A H -0.2736 0.0403 -0.1024 0.014(3) Uiso 1 1 calc R . . H2B H 0.0208 0.0632 -0.1111 0.014(3) Uiso 1 1 calc R . . C3 C -0.1921(5) 0.2084(3) -0.2154(3) 0.0145(5) Uani 1 1 d . . . H3A H -0.0555 0.3168 -0.1891 0.014(3) Uiso 1 1 calc R . . H3B H -0.1980 0.1230 -0.3158 0.014(3) Uiso 1 1 calc R . . C4 C -0.5394(5) 0.3507(3) -0.3345(3) 0.0141(5) Uani 1 1 d . . . H4A H -0.7076 0.3824 -0.3273 0.014(3) Uiso 1 1 calc R . . H4B H -0.5700 0.2697 -0.4410 0.014(3) Uiso 1 1 calc R . . C5 C 0.3300(5) 0.4787(3) 0.2980(3) 0.0130(5) Uani 1 1 d . . . H5A H 0.4059 0.4115 0.3585 0.014(3) Uiso 1 1 calc R . . H5B H 0.1768 0.5120 0.3289 0.014(3) Uiso 1 1 calc R . . Br1 Br 0.78961(4) 0.16479(3) 0.35859(3) 0.01510(12) 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 O1 0.0221(9) 0.0178(9) 0.0182(9) 0.0037(8) 0.0124(7) 0.0018(7) N1 0.0169(10) 0.0115(10) 0.0138(10) 0.0049(8) 0.0079(8) 0.0031(8) N2 0.0153(10) 0.0092(9) 0.0125(10) 0.0026(8) 0.0072(8) 0.0017(8) C1 0.0180(12) 0.0074(10) 0.0154(12) 0.0061(9) 0.0073(9) 0.0051(9) C2 0.0195(12) 0.0093(11) 0.0150(12) 0.0043(9) 0.0052(9) 0.0030(9) C3 0.0170(12) 0.0122(11) 0.0172(12) 0.0052(9) 0.0096(9) 0.0051(9) C4 0.0151(11) 0.0140(11) 0.0132(11) 0.0056(9) 0.0041(9) 0.0029(9) C5 0.0173(11) 0.0110(11) 0.0123(11) 0.0050(9) 0.0066(9) 0.0033(9) Br1 0.01765(17) 0.01022(16) 0.01682(17) 0.00342(11) 0.00792(10) 0.00094(10) _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 C1 1.233(3) . ? N1 C1 1.342(3) . ? N1 C2 1.458(3) . ? N2 C3 1.490(3) . ? N2 C4 1.501(3) . ? C1 C5 1.511(3) . ? C2 C3 1.521(3) . ? C4 C5 1.522(3) 2_565 ? C5 C4 1.522(3) 2_565 ? 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 C1 N1 C2 120.5(2) . . ? C3 N2 C4 115.50(19) . . ? O1 C1 N1 122.3(2) . . ? O1 C1 C5 120.7(2) . . ? N1 C1 C5 117.0(2) . . ? N1 C2 C3 113.0(2) . . ? N2 C3 C2 111.29(19) . . ? N2 C4 C5 113.0(2) . 2_565 ? C1 C5 C4 112.3(2) . 2_565 ? 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 C2 N1 C1 O1 7.7(4) . . . . ? C2 N1 C1 C5 -172.4(2) . . . . ? C1 N1 C2 C3 -81.2(3) . . . . ? C4 N2 C3 C2 174.6(2) . . . . ? N1 C2 C3 N2 -77.7(3) . . . . ? C3 N2 C4 C5 -54.3(3) . . . 2_565 ? O1 C1 C5 C4 32.2(3) . . . 2_565 ? N1 C1 C5 C4 -147.7(2) . . . 2_565 ? 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 N1 HN1 Br1 0.87(3) 2.67(3) 3.466(2) 153(3) 1_455 N2 HN2 O1 0.85(3) 2.04(3) 2.825(3) 153(3) 1_455 N2 HN2 O1 0.85(3) 2.46(3) 2.990(3) 121(3) 2_565 N2 HN3 Br1 0.89(3) 2.39(3) 3.251(2) 162(3) 2 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.612 _refine_diff_density_min -0.787 _refine_diff_density_rms 0.101 #===END data_H2L(ClO4)2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H22 O2 N4,2(Cl1 O4)' _chemical_formula_sum 'C10 H22 Cl2 N4 O10' _chemical_formula_weight 429.22 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 'P 21/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 10.2700(2) _cell_length_b 16.1690(4) _cell_length_c 10.8995(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.900(1) _cell_angle_gamma 90.00 _cell_volume 1731.76(6) _cell_formula_units_Z 4 _cell_measurement_temperature 112(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description 'Prism' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.436 _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 112(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7487 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 30.03 _reflns_number_total 4881 _reflns_number_gt 4493 _reflns_threshold_expression >2sigma(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^)+(0.0301P)^2^+1.1613P] 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 0.0166(18) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4881 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0812 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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 O1A O 0.46382(9) 0.05327(6) 0.87663(8) 0.01816(18) Uani 1 1 d . . . N1A N 0.44654(13) 0.14998(7) 1.02085(11) 0.0213(2) Uani 1 1 d . . . HN1A H 0.4895(19) 0.1862(12) 1.0778(18) 0.026 Uiso 1 1 d . . . N2A N 0.28757(11) 0.01535(8) 1.09312(10) 0.0194(2) Uani 1 1 d . . . HN2A H 0.3792(19) 0.0141(11) 1.1227(17) 0.023 Uiso 1 1 d . . . HN3A H 0.2590(18) -0.0061(12) 1.1562(18) 0.023 Uiso 1 1 d . . . C1A C 0.51831(14) 0.10493(7) 0.96006(11) 0.0176(2) Uani 1 1 d . . . C2A C 0.29853(16) 0.14977(9) 0.98090(13) 0.0253(3) Uani 1 1 d . . . H2A1 H 0.2656 0.1248 0.8944 0.0259(11) Uiso 1 1 calc R . . H2A2 H 0.2657 0.2076 0.9747 0.0259(11) Uiso 1 1 calc R . . C3A C 0.23823(14) 0.10258(10) 1.07160(13) 0.0254(3) Uani 1 1 d . . . H3A1 H 0.2615 0.1317 1.1551 0.0259(11) Uiso 1 1 calc R . . H3A2 H 0.1379 0.1023 1.0363 0.0259(11) Uiso 1 1 calc R . . C4A C 0.24655(14) -0.04083(9) 0.97901(12) 0.0222(3) Uani 1 1 d . . . H4A1 H 0.2606 -0.0123 0.9035 0.0259(11) Uiso 1 1 calc R . . H4A2 H 0.1487 -0.0544 0.9597 0.0259(11) Uiso 1 1 calc R . . C5A C 0.67025(15) 0.12005(9) 0.99556(13) 0.0232(3) Uani 1 1 d . . . H5A1 H 0.6974 0.1552 1.0732 0.0259(11) Uiso 1 1 calc R . . H5A2 H 0.6914 0.1507 0.9251 0.0259(11) Uiso 1 1 calc R . . O1B O 0.42926(9) 0.04809(6) 0.35448(9) 0.01766(18) Uani 1 1 d . . . N1B N 0.62338(11) 0.11961(6) 0.44232(10) 0.01417(19) Uani 1 1 d . . . HN1B H 0.6599(18) 0.1563(11) 0.4889(17) 0.017 Uiso 1 1 d . . . N2B N 0.75210(11) -0.04348(7) 0.50288(10) 0.01490(19) Uani 1 1 d . . . HN2B H 0.7153(17) -0.0195(11) 0.5585(17) 0.018 Uiso 1 1 d . . . HN3B H 0.8234(18) -0.0729(11) 0.5503(16) 0.018 Uiso 1 1 d . . . C1B C 0.49232(12) 0.10274(7) 0.42824(11) 0.0134(2) Uani 1 1 d . . . C2B C 0.69907(12) 0.08233(7) 0.36206(11) 0.0150(2) Uani 1 1 d . . . H2B1 H 0.7429 0.1267 0.3256 0.0259(11) Uiso 1 1 calc R . . H2B2 H 0.6345 0.0531 0.2898 0.0259(11) Uiso 1 1 calc R . . C3B C 0.80802(12) 0.02156(8) 0.43448(12) 0.0157(2) Uani 1 1 d . . . H3B1 H 0.8492 -0.0054 0.3732 0.0259(11) Uiso 1 1 calc R . . H3B2 H 0.8807 0.0523 0.4976 0.0259(11) Uiso 1 1 calc R . . C4B C 0.65075(13) -0.10106(7) 0.41782(12) 0.0164(2) Uani 1 1 d . . . H4B1 H 0.6979 -0.1374 0.3713 0.0259(11) Uiso 1 1 calc R . . H4B2 H 0.5821 -0.0684 0.3535 0.0259(11) Uiso 1 1 calc R . . C5B C 0.42079(13) 0.15422(7) 0.50544(12) 0.0159(2) Uani 1 1 d . . . H5B1 H 0.3529 0.1904 0.4465 0.0259(11) Uiso 1 1 calc R . . H5B2 H 0.4883 0.1902 0.5651 0.0259(11) Uiso 1 1 calc R . . Cl1 Cl 0.02268(3) 0.187029(17) 0.28166(3) 0.01342(8) Uani 1 1 d . . . O2 O 0.11254(10) 0.23303(6) 0.22729(10) 0.0225(2) Uani 1 1 d . . . O3 O -0.11050(9) 0.22361(7) 0.24073(10) 0.0264(2) Uani 1 1 d . . . O4 O 0.07371(11) 0.18951(6) 0.42016(9) 0.0254(2) Uani 1 1 d . . . O5 O 0.01803(12) 0.10170(6) 0.24264(11) 0.0291(2) Uani 1 1 d . . . Cl2 Cl 0.40209(3) 0.355077(19) 0.74920(3) 0.01922(9) Uani 1 1 d . . . O6 O 0.32488(16) 0.29151(8) 0.66957(13) 0.0481(4) Uani 1 1 d . . . O7 O 0.43546(12) 0.33118(8) 0.88151(10) 0.0310(2) Uani 1 1 d . . . O8 O 0.52306(14) 0.37143(12) 0.71391(15) 0.0586(5) Uani 1 1 d . . . O9 O 0.31984(13) 0.42949(6) 0.72873(10) 0.0294(2) 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 O1A 0.0219(4) 0.0174(4) 0.0144(4) -0.0033(3) 0.0041(3) -0.0008(3) N1A 0.0320(6) 0.0130(5) 0.0187(5) -0.0036(4) 0.0070(5) 0.0008(4) N2A 0.0162(5) 0.0286(6) 0.0135(5) -0.0039(4) 0.0046(4) -0.0026(4) C1A 0.0268(6) 0.0131(5) 0.0132(5) 0.0005(4) 0.0063(5) -0.0026(5) C2A 0.0302(7) 0.0228(6) 0.0197(6) -0.0016(5) 0.0021(5) 0.0128(6) C3A 0.0197(6) 0.0366(8) 0.0189(6) -0.0060(5) 0.0042(5) 0.0113(6) C4A 0.0189(6) 0.0315(7) 0.0159(5) -0.0066(5) 0.0047(5) -0.0088(5) C5A 0.0295(7) 0.0219(6) 0.0202(6) -0.0064(5) 0.0102(5) -0.0133(5) O1B 0.0161(4) 0.0204(4) 0.0164(4) -0.0047(3) 0.0046(3) -0.0028(3) N1B 0.0143(4) 0.0118(4) 0.0162(4) -0.0010(4) 0.0041(4) -0.0008(4) N2B 0.0144(4) 0.0159(5) 0.0143(4) 0.0039(4) 0.0040(4) 0.0024(4) C1B 0.0145(5) 0.0127(5) 0.0126(5) 0.0030(4) 0.0034(4) 0.0017(4) C2B 0.0152(5) 0.0154(5) 0.0155(5) 0.0033(4) 0.0063(4) 0.0010(4) C3B 0.0132(5) 0.0169(5) 0.0181(5) 0.0033(4) 0.0065(4) 0.0007(4) C4B 0.0209(6) 0.0138(5) 0.0158(5) -0.0006(4) 0.0077(4) 0.0000(4) C5B 0.0187(5) 0.0127(5) 0.0183(5) -0.0001(4) 0.0082(4) 0.0016(4) Cl1 0.01210(13) 0.01232(13) 0.01538(13) 0.00153(9) 0.00330(10) 0.00038(9) O2 0.0195(4) 0.0209(4) 0.0314(5) 0.0041(4) 0.0144(4) -0.0011(4) O3 0.0119(4) 0.0322(5) 0.0336(5) 0.0110(4) 0.0042(4) 0.0050(4) O4 0.0339(5) 0.0253(5) 0.0143(4) 0.0025(4) 0.0030(4) 0.0108(4) O5 0.0404(6) 0.0124(4) 0.0311(5) -0.0039(4) 0.0051(5) -0.0032(4) Cl2 0.01878(15) 0.02124(15) 0.01676(14) -0.00116(10) 0.00378(11) 0.00346(11) O6 0.0616(9) 0.0213(5) 0.0423(7) -0.0130(5) -0.0151(6) 0.0072(6) O7 0.0338(6) 0.0373(6) 0.0200(5) 0.0084(4) 0.0047(4) 0.0030(5) O8 0.0286(6) 0.1041(14) 0.0495(8) 0.0291(9) 0.0214(6) 0.0121(8) O9 0.0469(7) 0.0191(5) 0.0225(5) -0.0006(4) 0.0108(5) 0.0113(5) _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 O1A C1A 1.2417(15) . ? N1A C1A 1.3405(16) . ? N1A C2A 1.454(2) . ? N2A C3A 1.4940(19) . ? N2A C4A 1.4983(17) . ? C1A C5A 1.5144(19) . ? C2A C3A 1.516(2) . ? C4A C5A 1.520(2) 3_657 ? C5A C4A 1.520(2) 3_657 ? O1B C1B 1.2426(15) . ? N1B C1B 1.3377(15) . ? N1B C2B 1.4589(15) . ? N2B C3B 1.4969(15) . ? N2B C4B 1.4995(16) . ? C1B C5B 1.5166(16) . ? C2B C3B 1.5255(17) . ? C4B C5B 1.5283(16) 3_656 ? C5B C4B 1.5283(16) 3_656 ? Cl1 O3 1.4369(10) . ? Cl1 O2 1.4402(9) . ? Cl1 O5 1.4405(10) . ? Cl1 O4 1.4475(10) . ? Cl2 O6 1.4276(13) . ? Cl2 O8 1.4280(13) . ? Cl2 O7 1.4350(11) . ? Cl2 O9 1.4496(10) . ? 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 C1A N1A C2A 121.85(12) . . ? C3A N2A C4A 116.19(11) . . ? O1A C1A N1A 122.14(13) . . ? O1A C1A C5A 120.49(11) . . ? N1A C1A C5A 117.37(11) . . ? N1A C2A C3A 113.29(11) . . ? N2A C3A C2A 113.16(10) . . ? N2A C4A C5A 110.62(11) . 3_657 ? C1A C5A C4A 113.17(11) . 3_657 ? C1B N1B C2B 122.73(10) . . ? C3B N2B C4B 115.22(10) . . ? O1B C1B N1B 122.48(11) . . ? O1B C1B C5B 120.26(11) . . ? N1B C1B C5B 117.25(10) . . ? N1B C2B C3B 113.23(9) . . ? N2B C3B C2B 112.35(9) . . ? N2B C4B C5B 111.63(10) . 3_656 ? C1B C5B C4B 112.48(10) . 3_656 ? O3 Cl1 O2 109.00(6) . . ? O3 Cl1 O5 110.84(7) . . ? O2 Cl1 O5 110.08(6) . . ? O3 Cl1 O4 109.62(6) . . ? O2 Cl1 O4 109.50(7) . . ? O5 Cl1 O4 107.78(6) . . ? O6 Cl2 O8 110.03(11) . . ? O6 Cl2 O7 110.20(8) . . ? O8 Cl2 O7 110.38(8) . . ? O6 Cl2 O9 107.95(7) . . ? O8 Cl2 O9 108.58(9) . . ? O7 Cl2 O9 109.66(7) . . ? 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 C2A N1A C1A O1A -8.74(19) . . . . ? C2A N1A C1A C5A 170.43(12) . . . . ? C1A N1A C2A C3A 106.97(14) . . . . ? C4A N2A C3A C2A -65.65(15) . . . . ? N1A C2A C3A N2A -55.56(15) . . . . ? C3A N2A C4A C5A 166.29(11) . . . 3_657 ? O1A C1A C5A C4A -48.68(16) . . . 3_657 ? N1A C1A C5A C4A 132.13(12) . . . 3_657 ? C2B N1B C1B O1B 7.31(18) . . . . ? C2B N1B C1B C5B -171.91(10) . . . . ? C1B N1B C2B C3B -111.00(13) . . . . ? C4B N2B C3B C2B 64.90(13) . . . . ? N1B C2B C3B N2B 53.38(14) . . . . ? C3B N2B C4B C5B -169.11(10) . . . 3_656 ? O1B C1B C5B C4B 52.87(15) . . . 3_656 ? N1B C1B C5B C4B -127.90(12) . . . 3_656 ? 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 N1A HN1A O2 0.87(2) 2.18(2) 3.0524(16) 174.1(17) 4_666 N1B HN1B O6 0.800(18) 2.349(18) 3.0827(17) 152.7(16) 4_665 N2B HN2B O9 0.891(17) 2.357(17) 2.9909(15) 128.2(14) 4_665 N2A HN2A O1A 0.902(19) 1.944(18) 2.7147(15) 142.3(16) 3_657 N2A HN3A O9 0.892(18) 1.976(19) 2.8565(15) 168.9(17) 2_547 N2B HN2B O1B 0.891(17) 2.034(17) 2.7523(13) 136.9(15) 3_656 N2B HN3B O4 0.900(18) 2.139(18) 2.9337(14) 146.7(15) 3_656 N2B HN3B O5 0.900(18) 2.413(18) 3.2165(16) 148.7(14) 3_656 _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.463 _refine_diff_density_min -0.518 _refine_diff_density_rms 0.054