# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_bo1433 _database_code_depnum_ccdc_archive 'CCDC 902813' #TrackingRef 'BO1433.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C H5 Cl N6' _chemical_formula_weight 136.56 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' 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+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.838(2) _cell_length_b 23.956(10) _cell_length_c 4.936(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.152(6) _cell_angle_gamma 90.00 _cell_volume 546.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1854 _cell_measurement_theta_min 3.402 _cell_measurement_theta_max 30.996 _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.593 _exptl_absorpt_correction_type Multi-scans _exptl_absorpt_correction_T_min 0.8225 _exptl_absorpt_correction_T_max 0.9464 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5721 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 30.97 _reflns_number_total 1708 _reflns_number_gt 1431 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0409P)^2^+0.1860P] 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 X,Y,Z,Ueq _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1708 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0832 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.002 _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 -0.07624(7) 0.698023(14) 0.16520(7) 0.01848(11) Uani 1 1 d . . . N1 N 0.7174(3) 0.55107(5) 0.9090(3) 0.0158(2) Uani 1 1 d . . . N2 N 0.8417(3) 0.52756(5) 0.7244(3) 0.0184(3) Uani 1 1 d . . . N3 N 0.7379(3) 0.55340(5) 0.4879(3) 0.0188(3) Uani 1 1 d . . . N4 N 0.5447(3) 0.59376(5) 0.5071(3) 0.0177(3) Uani 1 1 d . . . N5 N 0.3554(3) 0.62059(5) 0.8872(3) 0.0155(2) Uani 1 1 d . . . N6 N 0.2993(3) 0.67611(5) 0.7804(3) 0.0160(2) Uani 1 1 d . . . C1 C 0.5368(3) 0.59108(5) 0.7721(3) 0.0139(3) Uani 1 1 d . . . H6A H 0.446(5) 0.6971(8) 0.817(5) 0.028(5) Uiso 1 1 d . . . H5N H 0.404(4) 0.6203(7) 1.074(4) 0.023(5) Uiso 1 1 d . . . H6B H 0.205(5) 0.6780(9) 0.592(5) 0.030(5) Uiso 1 1 d . . . H1N H 0.770(5) 0.5433(8) 1.080(5) 0.032(6) Uiso 1 1 d . . . H6C H 0.185(5) 0.6911(8) 0.867(5) 0.029(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 Cl1 0.01578(17) 0.02180(18) 0.01520(18) -0.00230(12) 0.00043(12) 0.00306(11) N1 0.0216(6) 0.0165(5) 0.0094(5) 0.0019(4) 0.0047(4) 0.0044(4) N2 0.0244(6) 0.0193(5) 0.0121(5) 0.0015(4) 0.0063(5) 0.0047(4) N3 0.0246(6) 0.0196(6) 0.0127(6) 0.0023(5) 0.0061(5) 0.0066(5) N4 0.0227(6) 0.0191(6) 0.0119(6) 0.0021(4) 0.0059(5) 0.0056(4) N5 0.0206(6) 0.0142(5) 0.0124(6) 0.0010(4) 0.0059(4) 0.0021(4) N6 0.0169(6) 0.0152(5) 0.0145(6) 0.0011(4) 0.0024(5) 0.0034(4) C1 0.0161(6) 0.0134(6) 0.0118(6) 0.0005(5) 0.0033(5) 0.0002(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 N1 C1 1.3380(18) . ? N1 N2 1.3537(17) . ? N1 H1N 0.83(2) . ? N2 N3 1.2853(17) . ? N3 N4 1.3675(17) . ? N4 C1 1.3213(19) . ? N5 C1 1.3736(18) . ? N5 N6 1.4269(17) . ? N5 H5N 0.88(2) . ? N6 H6A 0.85(2) . ? N6 H6B 0.91(2) . ? N6 H6C 0.87(2) . ? 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 N2 108.13(12) . . ? C1 N1 H1N 129.4(14) . . ? N2 N1 H1N 122.0(15) . . ? N3 N2 N1 106.20(12) . . ? N2 N3 N4 111.69(12) . . ? C1 N4 N3 104.70(11) . . ? C1 N5 N6 113.72(11) . . ? C1 N5 H5N 114.9(13) . . ? N6 N5 H5N 110.9(12) . . ? N5 N6 H6A 114.8(14) . . ? N5 N6 H6B 114.0(13) . . ? H6A N6 H6B 109.0(19) . . ? N5 N6 H6C 106.3(13) . . ? H6A N6 H6C 105.3(19) . . ? H6B N6 H6C 106.6(19) . . ? N4 C1 N1 109.27(12) . . ? N4 C1 N5 126.35(13) . . ? N1 C1 N5 124.14(12) . . ? 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 C1 N1 N2 N3 0.43(16) . . . . ? N1 N2 N3 N4 -0.34(16) . . . . ? N2 N3 N4 C1 0.12(17) . . . . ? N3 N4 C1 N1 0.16(16) . . . . ? N3 N4 C1 N5 -174.39(13) . . . . ? N2 N1 C1 N4 -0.37(16) . . . . ? N2 N1 C1 N5 174.32(13) . . . . ? N6 N5 C1 N4 -36.66(19) . . . . ? N6 N5 C1 N1 149.57(13) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 30.97 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.361 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.068 data_bo1561 _database_code_depnum_ccdc_archive 'CCDC 902814' #TrackingRef 'BO1561.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C H5 N7 O3' _chemical_formula_weight 163.12 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 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 11.907(5) _cell_length_b 5.0089(19) _cell_length_c 9.905(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.211(6) _cell_angle_gamma 90.00 _cell_volume 590.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1303 _cell_measurement_theta_min 2.056 _cell_measurement_theta_max 30.152 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.834 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_type Multi-scans _exptl_absorpt_correction_T_min 0.9056 _exptl_absorpt_correction_T_max 0.9866 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4593 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 30.00 _reflns_number_total 1675 _reflns_number_gt 1358 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0406P)^2^+0.1560P] 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 X,Y,Z,Ueq _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0035(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1675 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0881 _refine_ls_wR_factor_gt 0.0840 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 O1 O 0.08680(8) 1.38426(19) 0.89946(9) 0.0250(2) Uani 1 1 d . . . O2 O 0.06905(8) 0.97253(18) 0.83765(9) 0.0237(2) Uani 1 1 d . . . O3 O 0.17115(8) 1.2398(2) 0.71989(9) 0.0270(2) Uani 1 1 d . . . N1 N 0.32041(8) 0.3852(2) 0.47220(9) 0.0176(2) Uani 1 1 d . . . N2 N 0.39966(9) 0.3047(2) 0.38144(10) 0.0199(2) Uani 1 1 d . . . N3 N 0.44867(9) 0.5057(2) 0.32587(10) 0.0211(2) Uani 1 1 d . . . N4 N 0.40113(9) 0.7267(2) 0.37923(10) 0.0184(2) Uani 1 1 d . . . N5 N 0.26531(9) 0.8167(2) 0.55154(10) 0.0175(2) Uani 1 1 d . . . N6 N 0.15716(9) 0.7191(2) 0.59078(10) 0.0167(2) Uani 1 1 d . . . N7 N 0.10827(8) 1.2033(2) 0.82051(9) 0.0160(2) Uani 1 1 d . . . C1 C 0.32389(9) 0.6484(2) 0.46892(11) 0.0149(2) Uani 1 1 d . . . H4 H 0.4249(16) 0.901(4) 0.3514(19) 0.047(5) Uiso 1 1 d . . . H5 H 0.2633(15) 0.985(3) 0.5303(16) 0.033(5) Uiso 1 1 d . . . H6B H 0.1609(15) 0.558(4) 0.6290(18) 0.035(5) Uiso 1 1 d . . . H6A H 0.1064(14) 0.700(3) 0.5156(17) 0.033(4) Uiso 1 1 d . . . H6C H 0.1254(15) 0.850(4) 0.6541(18) 0.038(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 O1 0.0269(5) 0.0226(5) 0.0255(4) -0.0119(4) 0.0007(3) 0.0036(4) O2 0.0320(5) 0.0169(5) 0.0223(4) 0.0027(3) -0.0030(3) -0.0067(4) O3 0.0307(5) 0.0277(6) 0.0226(4) 0.0080(4) 0.0136(4) 0.0080(4) N1 0.0178(5) 0.0146(5) 0.0204(4) -0.0004(4) 0.0060(3) 0.0002(4) N2 0.0192(5) 0.0155(5) 0.0252(5) 0.0001(4) 0.0084(4) -0.0004(4) N3 0.0219(5) 0.0147(6) 0.0269(5) 0.0000(4) 0.0089(4) 0.0002(4) N4 0.0192(5) 0.0122(5) 0.0237(5) 0.0010(4) 0.0066(4) -0.0002(4) N5 0.0166(5) 0.0129(5) 0.0230(5) -0.0016(4) 0.0047(4) -0.0002(4) N6 0.0161(5) 0.0161(6) 0.0179(4) -0.0018(4) 0.0045(3) 0.0000(4) N7 0.0181(5) 0.0158(5) 0.0142(4) 0.0002(4) 0.0009(3) 0.0025(4) C1 0.0135(5) 0.0145(6) 0.0167(5) 0.0001(4) 0.0011(4) 0.0006(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 O1 N7 1.2249(13) . ? O2 N7 1.2582(14) . ? O3 N7 1.2621(13) . ? N1 C1 1.3194(17) . ? N1 N2 1.3665(14) . ? N2 N3 1.2881(15) . ? N3 N4 1.3518(15) . ? N4 C1 1.3397(15) . ? N4 H4 0.96(2) . ? N5 C1 1.3681(15) . ? N5 N6 1.4326(15) . ? N5 H5 0.871(17) . ? N6 H6B 0.890(19) . ? N6 H6A 0.962(17) . ? N6 H6C 0.985(19) . ? 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 N2 104.87(9) . . ? N3 N2 N1 111.45(10) . . ? N2 N3 N4 106.37(10) . . ? C1 N4 N3 108.00(10) . . ? C1 N4 H4 131.4(12) . . ? N3 N4 H4 120.6(12) . . ? C1 N5 N6 114.37(10) . . ? C1 N5 H5 117.8(12) . . ? N6 N5 H5 111.9(12) . . ? N5 N6 H6B 112.3(12) . . ? N5 N6 H6A 112.8(10) . . ? H6B N6 H6A 105.7(15) . . ? N5 N6 H6C 107.0(10) . . ? H6B N6 H6C 110.6(15) . . ? H6A N6 H6C 108.4(14) . . ? O1 N7 O2 121.01(10) . . ? O1 N7 O3 121.52(11) . . ? O2 N7 O3 117.47(10) . . ? N1 C1 N4 109.30(10) . . ? N1 C1 N5 125.81(10) . . ? N4 C1 N5 124.67(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 C1 N1 N2 N3 -0.04(13) . . . . ? N1 N2 N3 N4 -0.47(13) . . . . ? N2 N3 N4 C1 0.79(12) . . . . ? N2 N1 C1 N4 0.53(12) . . . . ? N2 N1 C1 N5 -174.35(11) . . . . ? N3 N4 C1 N1 -0.83(13) . . . . ? N3 N4 C1 N5 174.12(10) . . . . ? N6 N5 C1 N1 -33.27(16) . . . . ? N6 N5 C1 N4 152.60(11) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.253 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.050 data_bo1547 _database_code_depnum_ccdc_archive 'CCDC 902815' #TrackingRef 'BO1547.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H5 N11 O2' _chemical_formula_weight 215.17 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 7.108(2) _cell_length_b 7.3045(19) _cell_length_c 8.780(2) _cell_angle_alpha 68.351(7) _cell_angle_beta 86.953(11) _cell_angle_gamma 80.308(10) _cell_volume 417.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1526 _cell_measurement_theta_min 2.496 _cell_measurement_theta_max 30.184 _exptl_crystal_description Chip _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.711 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.147 _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 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4780 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _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 3.04 _diffrn_reflns_theta_max 30.02 _reflns_number_total 2377 _reflns_number_gt 1964 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0229P)^2^+0.1190P] 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 X,Y,Z,Ueq _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2377 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0809 _refine_ls_wR_factor_gt 0.0774 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 0.51126(13) -0.09978(13) 0.19965(12) 0.0276(2) Uani 1 1 d . . . O2 O 0.70505(14) 0.11662(15) 0.14865(13) 0.0346(2) Uani 1 1 d . . . N1 N 0.88683(13) 0.56858(14) 0.26809(11) 0.0170(2) Uani 1 1 d . . . N2 N 0.76717(14) 0.54447(14) 0.16639(12) 0.0182(2) Uani 1 1 d . . . N3 N 0.77292(15) 0.66534(14) 0.01432(12) 0.0207(2) Uani 1 1 d . . . N4 N 0.90378(14) 0.77780(14) 0.00835(12) 0.0190(2) Uani 1 1 d . . . N5 N 1.11294(14) 0.79495(15) 0.20467(11) 0.0183(2) Uani 1 1 d . . . N6 N 1.13431(14) 0.74397(14) 0.37769(11) 0.01596(19) Uani 1 1 d . . . N7 N 0.47684(14) 0.31283(14) 0.31654(12) 0.0174(2) Uani 1 1 d . . . N8 N 0.33618(14) 0.35165(14) 0.41324(12) 0.0198(2) Uani 1 1 d . . . N9 N 0.22671(14) 0.21121(14) 0.45450(12) 0.0188(2) Uani 1 1 d . . . N10 N 0.29253(13) 0.07738(13) 0.38514(11) 0.01583(19) Uani 1 1 d . . . N11 N 0.56161(14) 0.04756(15) 0.20962(12) 0.0201(2) Uani 1 1 d . . . C1 C 0.96895(15) 0.71550(15) 0.16379(13) 0.0155(2) Uani 1 1 d . . . C2 C 0.44279(15) 0.14690(15) 0.30324(13) 0.0149(2) Uani 1 1 d . . . H2 H 0.678(2) 0.460(2) 0.201(2) 0.041(5) Uiso 1 1 d . . . H5 H 1.105(2) 0.931(2) 0.150(2) 0.042(5) Uiso 1 1 d . . . H6A H 1.209(2) 0.615(2) 0.421(2) 0.036(4) Uiso 1 1 d . . . H6B H 1.015(2) 0.747(2) 0.4309(19) 0.029(4) Uiso 1 1 d . . . H6C H 1.201(2) 0.843(2) 0.3909(18) 0.032(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 0.0290(5) 0.0241(4) 0.0370(5) -0.0188(4) 0.0031(4) -0.0070(4) O2 0.0282(5) 0.0385(5) 0.0450(6) -0.0222(5) 0.0205(4) -0.0164(4) N1 0.0181(5) 0.0166(4) 0.0164(4) -0.0043(4) -0.0003(4) -0.0073(4) N2 0.0210(5) 0.0174(4) 0.0172(4) -0.0049(4) -0.0006(4) -0.0091(4) N3 0.0248(5) 0.0199(5) 0.0175(5) -0.0043(4) -0.0003(4) -0.0098(4) N4 0.0220(5) 0.0192(4) 0.0158(4) -0.0039(4) -0.0005(4) -0.0086(4) N5 0.0222(5) 0.0189(4) 0.0136(4) -0.0025(4) -0.0001(4) -0.0107(4) N6 0.0188(5) 0.0155(4) 0.0147(4) -0.0054(3) 0.0008(4) -0.0061(4) N7 0.0181(5) 0.0159(4) 0.0189(4) -0.0062(4) 0.0014(4) -0.0058(4) N8 0.0206(5) 0.0172(4) 0.0223(5) -0.0076(4) 0.0042(4) -0.0059(4) N9 0.0199(5) 0.0169(4) 0.0202(5) -0.0068(4) 0.0030(4) -0.0054(4) N10 0.0162(5) 0.0157(4) 0.0160(4) -0.0053(3) 0.0007(3) -0.0049(3) N11 0.0193(5) 0.0207(5) 0.0213(5) -0.0084(4) 0.0027(4) -0.0046(4) C1 0.0160(5) 0.0145(5) 0.0158(5) -0.0046(4) 0.0015(4) -0.0046(4) C2 0.0150(5) 0.0149(5) 0.0148(5) -0.0046(4) 0.0002(4) -0.0040(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 O1 N11 1.2234(13) . ? O2 N11 1.2233(13) . ? N1 C1 1.3266(14) . ? N1 N2 1.3412(14) . ? N2 N3 1.3040(13) . ? N2 H2 0.921(17) . ? N3 N4 1.3278(14) . ? N4 C1 1.3499(14) . ? N5 C1 1.3805(15) . ? N5 N6 1.4344(13) . ? N5 H5 0.926(17) . ? N6 H6A 0.947(16) . ? N6 H6B 0.944(16) . ? N6 H6C 0.972(16) . ? N7 C2 1.3219(14) . ? N7 N8 1.3389(13) . ? N8 N9 1.3243(14) . ? N9 N10 1.3417(13) . ? N10 C2 1.3218(14) . ? N11 C2 1.4406(14) . ? 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 N2 100.33(9) . . ? N3 N2 N1 114.62(10) . . ? N3 N2 H2 121.6(11) . . ? N1 N2 H2 123.4(11) . . ? N2 N3 N4 106.42(9) . . ? N3 N4 C1 105.10(9) . . ? C1 N5 N6 113.73(9) . . ? C1 N5 H5 113.8(10) . . ? N6 N5 H5 110.5(10) . . ? N5 N6 H6A 108.0(10) . . ? N5 N6 H6B 112.2(9) . . ? H6A N6 H6B 110.9(13) . . ? N5 N6 H6C 106.5(9) . . ? H6A N6 H6C 110.4(13) . . ? H6B N6 H6C 108.8(12) . . ? C2 N7 N8 103.23(9) . . ? N9 N8 N7 109.52(9) . . ? N8 N9 N10 109.72(9) . . ? C2 N10 N9 102.97(9) . . ? O2 N11 O1 125.75(10) . . ? O2 N11 C2 117.14(10) . . ? O1 N11 C2 117.10(10) . . ? N1 C1 N4 113.53(10) . . ? N1 C1 N5 124.63(10) . . ? N4 C1 N5 121.79(10) . . ? N10 C2 N7 114.56(10) . . ? N10 C2 N11 122.60(10) . . ? N7 C2 N11 122.83(10) . . ? 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 C1 N1 N2 N3 -0.52(12) . . . . ? N1 N2 N3 N4 0.73(13) . . . . ? N2 N3 N4 C1 -0.59(12) . . . . ? C2 N7 N8 N9 0.48(12) . . . . ? N7 N8 N9 N10 -0.29(12) . . . . ? N8 N9 N10 C2 -0.03(12) . . . . ? N2 N1 C1 N4 0.12(12) . . . . ? N2 N1 C1 N5 -177.34(10) . . . . ? N3 N4 C1 N1 0.30(13) . . . . ? N3 N4 C1 N5 177.83(10) . . . . ? N6 N5 C1 N1 -15.79(15) . . . . ? N6 N5 C1 N4 166.95(10) . . . . ? N9 N10 C2 N7 0.36(13) . . . . ? N9 N10 C2 N11 179.27(10) . . . . ? N8 N7 C2 N10 -0.52(13) . . . . ? N8 N7 C2 N11 -179.43(10) . . . . ? O2 N11 C2 N10 -174.68(11) . . . . ? O1 N11 C2 N10 4.52(16) . . . . ? O2 N11 C2 N7 4.14(16) . . . . ? O1 N11 C2 N7 -176.65(10) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.244 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.052 data_bo1883 _database_code_depnum_ccdc_archive 'CCDC 902816' #TrackingRef 'bo1883.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C H5 Cl N6 O4' _chemical_formula_weight 200.56 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 Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 7.762(2) _cell_length_b 9.400(3) _cell_length_c 17.653(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1288.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 5084 _cell_measurement_theta_min 2.307 _cell_measurement_theta_max 31.502 _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.068 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.584 _exptl_absorpt_correction_type Multi-scans _exptl_absorpt_correction_T_min 0.7301 _exptl_absorpt_correction_T_max 0.9742 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9712 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 30.00 _reflns_number_total 1873 _reflns_number_gt 1820 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0683P)^2^+0.9600P] 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 X,Y,Z,Ueq _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0033(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1873 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 Cl1 Cl 0.24366(4) 0.50106(3) 0.576671(19) 0.01176(14) Uani 1 1 d . . . O1 O 0.17917(15) 0.56265(13) 0.50572(6) 0.0165(3) Uani 1 1 d . . . O2 O 0.15894(16) 0.57008(13) 0.63866(7) 0.0193(3) Uani 1 1 d . . . O3 O 0.2067(2) 0.35098(14) 0.57677(7) 0.0251(3) Uani 1 1 d . . . O4 O 0.42668(17) 0.52343(16) 0.58085(7) 0.0236(3) Uani 1 1 d . . . N1 N 0.17374(16) 0.61048(14) 0.32696(7) 0.0119(3) Uani 1 1 d . . . N2 N 0.07260(17) 0.58966(14) 0.26438(7) 0.0140(3) Uani 1 1 d . . . N3 N 0.01573(18) 0.70849(15) 0.23819(7) 0.0155(3) Uani 1 1 d . . . N4 N 0.07797(17) 0.81194(14) 0.28365(7) 0.0138(3) Uani 1 1 d . . . N5 N 0.25679(16) 0.82451(14) 0.39344(7) 0.0128(3) Uani 1 1 d . . . N6 N 0.39852(18) 0.74892(14) 0.42624(8) 0.0125(3) Uani 1 1 d . . . C1 C 0.17450(19) 0.75013(15) 0.33706(8) 0.0110(3) Uani 1 1 d . . . H4 H 0.051(3) 0.899(3) 0.2738(15) 0.034(7) Uiso 1 1 d . . . H5 H 0.288(3) 0.909(3) 0.3811(14) 0.031(6) Uiso 1 1 d . . . H6A H 0.468(3) 0.725(2) 0.3956(14) 0.019(5) Uiso 1 1 d . . . H6B H 0.449(3) 0.800(2) 0.4551(13) 0.020(5) Uiso 1 1 d . . . H6C H 0.358(3) 0.677(3) 0.4506(14) 0.026(6) 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 Cl1 0.0138(2) 0.0098(2) 0.0118(2) -0.00027(10) 0.00067(11) 0.00095(11) O1 0.0187(6) 0.0170(6) 0.0137(5) 0.0029(4) -0.0020(4) 0.0003(4) O2 0.0250(6) 0.0177(6) 0.0153(5) -0.0009(4) 0.0073(4) 0.0038(5) O3 0.0420(8) 0.0086(5) 0.0246(6) 0.0014(4) -0.0016(5) -0.0025(6) O4 0.0126(6) 0.0325(7) 0.0256(7) -0.0037(5) -0.0015(4) 0.0036(5) N1 0.0133(6) 0.0096(6) 0.0129(5) -0.0008(4) -0.0010(4) -0.0018(4) N2 0.0170(6) 0.0129(6) 0.0122(6) -0.0005(4) -0.0003(4) -0.0031(5) N3 0.0193(6) 0.0130(6) 0.0144(6) -0.0002(5) -0.0034(5) -0.0041(5) N4 0.0181(6) 0.0100(6) 0.0134(6) 0.0006(4) -0.0044(5) -0.0003(5) N5 0.0143(6) 0.0096(6) 0.0146(6) -0.0005(4) -0.0030(4) 0.0005(4) N6 0.0117(6) 0.0134(7) 0.0125(6) -0.0002(4) -0.0021(5) -0.0007(5) C1 0.0118(6) 0.0101(7) 0.0110(6) 0.0011(4) 0.0010(5) -0.0006(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 Cl1 O2 1.4320(12) . ? Cl1 O4 1.4380(14) . ? Cl1 O3 1.4397(14) . ? Cl1 O1 1.4678(12) . ? N1 C1 1.3249(19) . ? N1 N2 1.3693(17) . ? N2 N3 1.2871(19) . ? N3 N4 1.3503(18) . ? N4 C1 1.3372(19) . ? N4 H4 0.86(3) . ? N5 C1 1.3739(19) . ? N5 N6 1.4320(18) . ? N5 H5 0.86(3) . ? N6 H6A 0.79(3) . ? N6 H6B 0.80(2) . ? N6 H6C 0.86(3) . ? 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 Cl1 O4 110.38(8) . . ? O2 Cl1 O3 110.58(8) . . ? O4 Cl1 O3 109.88(9) . . ? O2 Cl1 O1 108.47(8) . . ? O4 Cl1 O1 108.85(8) . . ? O3 Cl1 O1 108.64(8) . . ? C1 N1 N2 104.64(12) . . ? N3 N2 N1 111.25(12) . . ? N2 N3 N4 106.78(12) . . ? C1 N4 N3 107.86(13) . . ? C1 N4 H4 133.8(18) . . ? N3 N4 H4 118.3(18) . . ? C1 N5 N6 113.43(12) . . ? C1 N5 H5 114.7(17) . . ? N6 N5 H5 110.4(18) . . ? N5 N6 H6A 112.5(17) . . ? N5 N6 H6B 109.8(16) . . ? H6A N6 H6B 105(2) . . ? N5 N6 H6C 108.0(16) . . ? H6A N6 H6C 112(2) . . ? H6B N6 H6C 109(2) . . ? N1 C1 N4 109.46(13) . . ? N1 C1 N5 127.14(14) . . ? N4 C1 N5 123.38(13) . . ? 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 C1 N1 N2 N3 0.01(17) . . . . ? N1 N2 N3 N4 -0.33(17) . . . . ? N2 N3 N4 C1 0.52(17) . . . . ? N2 N1 C1 N4 0.31(16) . . . . ? N2 N1 C1 N5 179.19(14) . . . . ? N3 N4 C1 N1 -0.52(17) . . . . ? N3 N4 C1 N5 -179.45(14) . . . . ? N6 N5 C1 N1 22.9(2) . . . . ? N6 N5 C1 N4 -158.42(14) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.299 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.064