# Electronic Supplementary Material (ESI) for CrystEngComm # 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_complex1 _database_code_depnum_ccdc_archive 'CCDC 922198' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N3, 2(Cl)' _chemical_formula_sum 'C11 H13 Cl2 N3' _chemical_formula_weight 258.14 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' 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 'P ca21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 10.0145(4) _cell_length_b 8.8239(3) _cell_length_c 13.7249(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1212.82(10) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2803 _cell_measurement_theta_min 3.42 _cell_measurement_theta_max 27.47 _exptl_crystal_description prism _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.511 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8915 _exptl_absorpt_correction_T_max 0.9136 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2812 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 27.54 _reflns_number_total 2778 _reflns_number_gt 1605 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'ORTEP-II (Johnson, 1976)' _computing_molecular_graphics SHELXL-97 _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^)+(0.0347P)^2^+0.1137P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.12(9) _refine_ls_number_reflns 2778 _refine_ls_number_parameters 154 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0837 _refine_ls_wR_factor_gt 0.0790 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.030 _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 0.16418(7) 1.41587(8) 0.83981(8) 0.0464(2) Uani 1 1 d . . . Cl2 Cl 0.14784(7) 0.99605(9) 0.58019(7) 0.0509(2) Uani 1 1 d . . . N1 N 0.0419(2) 1.1013(3) 0.8332(3) 0.0372(6) Uani 1 1 d D . . H1N H 0.063(3) 1.1956(15) 0.828(3) 0.056 Uiso 1 1 d D . . N2 N -0.1294(3) 1.1299(3) 0.7198(2) 0.0409(7) Uani 1 1 d D . . H2N H -0.189(3) 1.090(4) 0.683(2) 0.061 Uiso 1 1 d D . . N3 N 0.0319(3) 1.3133(3) 0.6014(2) 0.0371(6) Uani 1 1 d D . . H3N H 0.044(3) 1.2161(13) 0.604(3) 0.056 Uiso 1 1 d D . . C1 C -0.0548(3) 1.0416(4) 0.7771(3) 0.0341(7) Uani 1 1 d . . . C2 C -0.0733(3) 0.8844(4) 0.7801(3) 0.0418(8) Uani 1 1 d . . . H2A H -0.1412 0.8400 0.7438 0.050 Uiso 1 1 calc R . . C3 C 0.0070(3) 0.7970(3) 0.8356(3) 0.0493(8) Uani 1 1 d . . . H3A H -0.0041 0.6923 0.8356 0.059 Uiso 1 1 calc R . . C4 C 0.1066(4) 0.8624(5) 0.8929(3) 0.0489(10) Uani 1 1 d . . . H4A H 0.1613 0.8027 0.9319 0.059 Uiso 1 1 calc R . . C5 C 0.1216(4) 1.0142(5) 0.8903(3) 0.0465(9) Uani 1 1 d . . . H5A H 0.1874 1.0598 0.9281 0.056 Uiso 1 1 calc R . . C6 C -0.1429(3) 1.2932(4) 0.7274(3) 0.0402(8) Uani 1 1 d . . . H6A H -0.1172 1.3239 0.7926 0.048 Uiso 1 1 calc R . . H6B H -0.2361 1.3196 0.7187 0.048 Uiso 1 1 calc R . . C7 C -0.0612(3) 1.3813(4) 0.6553(3) 0.0348(7) Uani 1 1 d . . . C8 C -0.0788(3) 1.5359(4) 0.6454(3) 0.0427(9) Uani 1 1 d . . . H8A H -0.1439 1.5854 0.6817 0.051 Uiso 1 1 calc R . . C9 C 0.0004(3) 1.6163(4) 0.5818(3) 0.0528(10) Uani 1 1 d . . . H9A H -0.0105 1.7205 0.5751 0.063 Uiso 1 1 calc R . . C10 C 0.0956(4) 1.5414(5) 0.5282(3) 0.0531(10) Uani 1 1 d . . . H10A H 0.1498 1.5944 0.4851 0.064 Uiso 1 1 calc R . . C11 C 0.1102(4) 1.3877(5) 0.5389(3) 0.0460(9) Uani 1 1 d . . . H11A H 0.1742 1.3358 0.5028 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0453(4) 0.0383(4) 0.0558(5) 0.0032(5) -0.0055(5) -0.0084(3) Cl2 0.0491(4) 0.0518(5) 0.0519(5) 0.0074(5) 0.0057(5) 0.0141(4) N1 0.0360(12) 0.0324(12) 0.0432(16) 0.0004(16) 0.0012(16) -0.0053(11) N2 0.0407(15) 0.0367(14) 0.0455(18) -0.0008(14) -0.0019(14) -0.0043(12) N3 0.0360(12) 0.0380(13) 0.0373(16) -0.0012(15) -0.0003(12) 0.0013(12) C1 0.0304(14) 0.0348(16) 0.0370(19) 0.0005(15) 0.0068(15) -0.0022(14) C2 0.0461(18) 0.0320(16) 0.047(2) -0.0009(17) 0.0087(18) -0.0044(14) C3 0.065(2) 0.0325(15) 0.051(2) -0.001(2) 0.015(2) 0.0026(15) C4 0.053(2) 0.047(2) 0.046(2) 0.0148(19) 0.0068(18) 0.0103(17) C5 0.0413(19) 0.060(3) 0.039(2) 0.0043(19) -0.0012(16) 0.0002(17) C6 0.0371(15) 0.0367(15) 0.047(2) -0.0029(17) 0.0055(17) 0.0041(14) C7 0.0353(17) 0.0352(16) 0.0340(18) -0.0026(15) -0.0075(15) 0.0025(14) C8 0.049(2) 0.0343(17) 0.045(2) -0.0041(18) -0.0037(18) 0.0018(17) C9 0.070(2) 0.0357(16) 0.053(2) 0.006(2) -0.014(2) -0.0044(16) C10 0.054(2) 0.057(2) 0.048(2) 0.006(2) 0.001(2) -0.017(2) C11 0.0417(18) 0.057(2) 0.039(2) -0.0033(19) 0.0002(16) -0.0027(16) _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 1.345(4) . ? N1 C5 1.358(5) . ? N1 H1N 0.86(2) . ? N2 C1 1.335(4) . ? N2 C6 1.451(4) . ? N2 H2N 0.86(2) . ? N3 C7 1.333(4) . ? N3 C11 1.336(4) . ? N3 H3N 0.86(2) . ? C1 C2 1.400(4) . ? C2 C3 1.349(5) . ? C2 H2A 0.9300 . ? C3 C4 1.395(5) . ? C3 H3A 0.9300 . ? C4 C5 1.348(5) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.501(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.382(5) . ? C8 C9 1.377(5) . ? C8 H8A 0.9300 . ? C9 C10 1.374(5) . ? C9 H9A 0.9300 . ? C10 C11 1.371(5) . ? C10 H10A 0.9300 . ? C11 H11A 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 C1 N1 C5 122.2(3) . . ? C1 N1 H1N 121(3) . . ? C5 N1 H1N 117(3) . . ? C1 N2 C6 126.1(3) . . ? C1 N2 H2N 119(2) . . ? C6 N2 H2N 113(2) . . ? C7 N3 C11 123.1(3) . . ? C7 N3 H3N 121(2) . . ? C11 N3 H3N 116(2) . . ? N2 C1 N1 120.7(3) . . ? N2 C1 C2 121.5(3) . . ? N1 C1 C2 117.8(3) . . ? C3 C2 C1 120.3(3) . . ? C3 C2 H2A 119.8 . . ? C1 C2 H2A 119.8 . . ? C2 C3 C4 120.5(3) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C5 C4 C3 118.5(3) . . ? C5 C4 H4A 120.8 . . ? C3 C4 H4A 120.8 . . ? C4 C5 N1 120.8(4) . . ? C4 C5 H5A 119.6 . . ? N1 C5 H5A 119.6 . . ? N2 C6 C7 114.6(3) . . ? N2 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? N2 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? N3 C7 C8 118.6(3) . . ? N3 C7 C6 120.9(3) . . ? C8 C7 C6 120.4(3) . . ? C9 C8 C7 119.9(3) . . ? C9 C8 H8A 120.1 . . ? C7 C8 H8A 120.1 . . ? C10 C9 C8 119.4(3) . . ? C10 C9 H9A 120.3 . . ? C8 C9 H9A 120.3 . . ? C11 C10 C9 119.5(4) . . ? C11 C10 H10A 120.2 . . ? C9 C10 H10A 120.2 . . ? N3 C11 C10 119.5(4) . . ? N3 C11 H11A 120.3 . . ? C10 C11 H11A 120.3 . . ? 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 C6 N2 C1 N1 -16.8(5) . . . . ? C6 N2 C1 C2 163.9(3) . . . . ? C5 N1 C1 N2 -178.3(3) . . . . ? C5 N1 C1 C2 1.1(5) . . . . ? N2 C1 C2 C3 177.3(4) . . . . ? N1 C1 C2 C3 -2.1(5) . . . . ? C1 C2 C3 C4 2.0(6) . . . . ? C2 C3 C4 C5 -0.9(6) . . . . ? C3 C4 C5 N1 -0.1(5) . . . . ? C1 N1 C5 C4 0.0(6) . . . . ? C1 N2 C6 C7 101.0(4) . . . . ? C11 N3 C7 C8 0.7(5) . . . . ? C11 N3 C7 C6 -177.5(3) . . . . ? N2 C6 C7 N3 -10.9(5) . . . . ? N2 C6 C7 C8 170.9(3) . . . . ? N3 C7 C8 C9 -0.8(5) . . . . ? C6 C7 C8 C9 177.4(3) . . . . ? C7 C8 C9 C10 0.4(6) . . . . ? C8 C9 C10 C11 0.1(6) . . . . ? C7 N3 C11 C10 -0.2(5) . . . . ? C9 C10 C11 N3 -0.2(6) . . . . ? 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 H1N Cl1 0.86(2) 2.197(15) 3.036(2) 164(4) . N2 H2N Cl2 0.86(2) 2.286(11) 3.144(3) 175(3) 4_475 N3 H3N Cl2 0.86(2) 2.227(16) 3.044(3) 157(3) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.328 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.042 data_complex2 _database_code_depnum_ccdc_archive 'CCDC 922199' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N3, 2(Cl)' _chemical_formula_sum 'C11 H13 Cl2 N3' _chemical_formula_weight 258.14 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' 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/n' _symmetry_space_group_name_Hall '-P 2yn' 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 10.0153(5) _cell_length_b 9.8465(5) _cell_length_c 12.7219(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.535(5) _cell_angle_gamma 90.00 _cell_volume 1233.44(11) _cell_formula_units_Z 4 _cell_measurement_temperature 275(2) _cell_measurement_reflns_used 3963 _cell_measurement_theta_min 3.53 _cell_measurement_theta_max 27.49 _exptl_crystal_description prism _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.502 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9018 _exptl_absorpt_correction_T_max 0.9330 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 275(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4536 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 27.56 _reflns_number_total 2815 _reflns_number_gt 2014 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'ORTEP-II (Johnson, 1976)' _computing_molecular_graphics SHELXL-97 _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^)+(0.0421P)^2^+0.1963P] 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 2815 _refine_ls_number_parameters 154 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1130 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.48013(6) 0.04370(6) 0.78154(4) 0.04839(18) Uani 1 1 d . . . Cl2 Cl 0.98422(7) -0.07305(7) 0.28434(5) 0.0607(2) Uani 1 1 d . . . N1 N 0.68445(19) -0.16690(18) 0.90069(13) 0.0420(4) Uani 1 1 d D . . H1N H 0.638(2) -0.1101(19) 0.8569(15) 0.063 Uiso 1 1 d D . . N2 N 0.8057(2) -0.2432(2) 0.77299(14) 0.0467(5) Uani 1 1 d D . . H2N H 0.867(2) -0.298(2) 0.758(2) 0.070 Uiso 1 1 d D . . N3 N 0.8127(2) -0.2211(2) 0.41675(15) 0.0547(5) Uani 1 1 d D . . H3N H 0.863(2) -0.177(2) 0.3803(19) 0.082 Uiso 1 1 d D . . C1 C 0.7806(2) -0.2469(2) 0.87216(15) 0.0396(5) Uani 1 1 d . . . C2 C 0.8529(2) -0.3340(2) 0.95017(17) 0.0488(6) Uani 1 1 d . . . H2A H 0.9228 -0.3878 0.9341 0.059 Uiso 1 1 calc R . . C3 C 0.8198(3) -0.3393(3) 1.04935(19) 0.0610(7) Uani 1 1 d . . . H3A H 0.8668 -0.3972 1.1009 0.073 Uiso 1 1 calc R . . C4 C 0.7150(3) -0.2574(3) 1.07379(19) 0.0633(7) Uani 1 1 d . . . H4A H 0.6909 -0.2617 1.1409 0.076 Uiso 1 1 calc R . . C5 C 0.6505(3) -0.1734(2) 0.99928(17) 0.0511(6) Uani 1 1 d . . . H5A H 0.5813 -0.1183 1.0150 0.061 Uiso 1 1 calc R . . C6 C 0.7344(3) -0.1580(2) 0.68817(16) 0.0500(6) Uani 1 1 d . . . H6A H 0.7766 -0.0690 0.6920 0.060 Uiso 1 1 calc R . . H6B H 0.6409 -0.1465 0.6972 0.060 Uiso 1 1 calc R . . C7 C 0.8145(2) -0.1654(2) 0.51338(17) 0.0474(5) Uani 1 1 d . . . H7A H 0.8680 -0.0895 0.5343 0.057 Uiso 1 1 calc R . . C8 C 0.7373(2) -0.2205(2) 0.58098(16) 0.0401(5) Uani 1 1 d . . . C9 C 0.6604(2) -0.3339(2) 0.54693(18) 0.0502(6) Uani 1 1 d . . . H9A H 0.6075 -0.3735 0.5916 0.060 Uiso 1 1 calc R . . C10 C 0.6610(3) -0.3888(3) 0.44798(19) 0.0596(7) Uani 1 1 d . . . H10A H 0.6092 -0.4653 0.4254 0.072 Uiso 1 1 calc R . . C11 C 0.7382(3) -0.3301(3) 0.38357(18) 0.0608(7) Uani 1 1 d . . . H11A H 0.7392 -0.3660 0.3161 0.073 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0490(3) 0.0520(3) 0.0476(3) -0.0019(2) 0.0179(3) -0.0013(3) Cl2 0.0604(4) 0.0728(4) 0.0503(4) 0.0154(3) 0.0137(3) 0.0026(3) N1 0.0478(11) 0.0453(10) 0.0336(9) -0.0031(8) 0.0093(8) -0.0009(9) N2 0.0488(11) 0.0560(12) 0.0369(10) 0.0005(9) 0.0123(8) 0.0093(10) N3 0.0595(13) 0.0705(14) 0.0399(11) 0.0128(10) 0.0243(9) 0.0147(12) C1 0.0422(12) 0.0419(11) 0.0338(11) -0.0047(9) 0.0045(9) -0.0056(10) C2 0.0498(13) 0.0538(13) 0.0406(12) -0.0027(10) 0.0021(10) 0.0039(11) C3 0.0730(18) 0.0663(16) 0.0384(12) 0.0070(12) -0.0042(12) -0.0002(14) C4 0.0767(19) 0.0826(18) 0.0324(12) 0.0014(12) 0.0147(12) -0.0006(16) C5 0.0576(15) 0.0617(14) 0.0361(12) -0.0115(11) 0.0143(10) -0.0020(12) C6 0.0631(15) 0.0534(13) 0.0354(11) 0.0007(10) 0.0138(10) 0.0113(12) C7 0.0486(13) 0.0515(13) 0.0434(12) 0.0052(10) 0.0117(10) 0.0042(11) C8 0.0428(12) 0.0460(12) 0.0327(10) 0.0033(9) 0.0100(9) 0.0089(10) C9 0.0520(14) 0.0555(14) 0.0447(12) 0.0040(11) 0.0130(10) -0.0016(12) C10 0.0651(17) 0.0602(15) 0.0502(14) -0.0070(12) 0.0015(12) -0.0020(13) C11 0.0766(18) 0.0715(17) 0.0328(12) -0.0064(12) 0.0063(12) 0.0226(16) _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 1.345(3) . ? N1 C5 1.360(3) . ? N1 H1N 0.86(2) . ? N2 C1 1.331(3) . ? N2 C6 1.448(3) . ? N2 H2N 0.86(2) . ? N3 C11 1.332(3) . ? N3 C7 1.343(3) . ? N3 H3N 0.86(2) . ? C1 C2 1.408(3) . ? C2 C3 1.363(3) . ? C2 H2A 0.9300 . ? C3 C4 1.403(4) . ? C3 H3A 0.9300 . ? C4 C5 1.333(3) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C8 1.501(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.369(3) . ? C7 H7A 0.9300 . ? C8 C9 1.381(3) . ? C9 C10 1.371(3) . ? C9 H9A 0.9300 . ? C10 C11 1.355(4) . ? C10 H10A 0.9300 . ? C11 H11A 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 C1 N1 C5 122.26(19) . . ? C1 N1 H1N 122.3(16) . . ? C5 N1 H1N 115.4(16) . . ? C1 N2 C6 124.70(19) . . ? C1 N2 H2N 117.0(18) . . ? C6 N2 H2N 118.3(18) . . ? C11 N3 C7 122.1(2) . . ? C11 N3 H3N 125.9(19) . . ? C7 N3 H3N 112.0(19) . . ? N2 C1 N1 120.55(19) . . ? N2 C1 C2 121.5(2) . . ? N1 C1 C2 117.90(19) . . ? C3 C2 C1 119.7(2) . . ? C3 C2 H2A 120.2 . . ? C1 C2 H2A 120.2 . . ? C2 C3 C4 120.1(2) . . ? C2 C3 H3A 119.9 . . ? C4 C3 H3A 119.9 . . ? C5 C4 C3 118.9(2) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C4 C5 N1 121.0(2) . . ? C4 C5 H5A 119.5 . . ? N1 C5 H5A 119.5 . . ? N2 C6 C8 110.50(18) . . ? N2 C6 H6A 109.6 . . ? C8 C6 H6A 109.6 . . ? N2 C6 H6B 109.6 . . ? C8 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? N3 C7 C8 119.9(2) . . ? N3 C7 H7A 120.0 . . ? C8 C7 H7A 120.0 . . ? C7 C8 C9 118.0(2) . . ? C7 C8 C6 121.0(2) . . ? C9 C8 C6 120.9(2) . . ? C10 C9 C8 120.7(2) . . ? C10 C9 H9A 119.6 . . ? C8 C9 H9A 119.6 . . ? C11 C10 C9 119.1(2) . . ? C11 C10 H10A 120.5 . . ? C9 C10 H10A 120.5 . . ? N3 C11 C10 120.1(2) . . ? N3 C11 H11A 120.0 . . ? C10 C11 H11A 120.0 . . ? 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 C6 N2 C1 N1 -0.9(3) . . . . ? C6 N2 C1 C2 179.0(2) . . . . ? C5 N1 C1 N2 176.1(2) . . . . ? C5 N1 C1 C2 -3.8(3) . . . . ? N2 C1 C2 C3 -177.0(2) . . . . ? N1 C1 C2 C3 2.9(3) . . . . ? C1 C2 C3 C4 -0.5(4) . . . . ? C2 C3 C4 C5 -1.2(4) . . . . ? C3 C4 C5 N1 0.4(4) . . . . ? C1 N1 C5 C4 2.2(4) . . . . ? C1 N2 C6 C8 -153.4(2) . . . . ? C11 N3 C7 C8 -0.4(3) . . . . ? N3 C7 C8 C9 0.6(3) . . . . ? N3 C7 C8 C6 -178.3(2) . . . . ? N2 C6 C8 C7 -108.8(2) . . . . ? N2 C6 C8 C9 72.3(3) . . . . ? C7 C8 C9 C10 -0.4(3) . . . . ? C6 C8 C9 C10 178.5(2) . . . . ? C8 C9 C10 C11 -0.1(4) . . . . ? C7 N3 C11 C10 -0.1(4) . . . . ? C9 C10 C11 N3 0.4(4) . . . . ? 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 H1N Cl1 0.86(2) 2.271(12) 3.107(2) 163(2) . N2 H2N Cl1 0.86(2) 2.309(10) 3.167(2) 176(2) 2_646 N3 H3N Cl2 0.86(2) 2.133(10) 2.995(2) 177(3) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.283 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.045 data_complex3 _database_code_depnum_ccdc_archive 'CCDC 922200' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N3, 2(Cl)' _chemical_formula_sum 'C11 H13 Cl2 N3' _chemical_formula_weight 258.14 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' 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/n' _symmetry_space_group_name_Hall '-P 2yn' 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 8.9165(5) _cell_length_b 13.8016(8) _cell_length_c 10.3354(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.248(5) _cell_angle_gamma 90.00 _cell_volume 1242.95(12) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3910 _cell_measurement_theta_min 3.40 _cell_measurement_theta_max 27.49 _exptl_crystal_description prism _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.499 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8982 _exptl_absorpt_correction_T_max 0.9200 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4627 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0742 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 27.56 _reflns_number_total 2865 _reflns_number_gt 1630 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'ORTEP-II (Johnson, 1976)' _computing_molecular_graphics SHELXL-97 _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^)+(0.0354P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2865 _refine_ls_number_parameters 154 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.1254 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.67409(9) 0.60362(6) 0.88964(7) 0.0532(3) Uani 1 1 d . . . Cl2 Cl 0.81003(11) 1.08553(8) 1.07249(8) 0.0828(4) Uani 1 1 d . . . N1 N 0.3290(3) 0.63359(19) 0.7783(2) 0.0454(6) Uani 1 1 d D . . H1N H 0.4280(12) 0.634(2) 0.794(3) 0.068 Uiso 1 1 d D . . N2 N 0.3106(3) 0.7359(2) 0.5968(2) 0.0517(7) Uani 1 1 d D . . H2N H 0.250(3) 0.771(2) 0.539(2) 0.078 Uiso 1 1 d D . . N3 N 0.7489(6) 0.9315(3) 0.8538(4) 0.1002(16) Uani 1 1 d D . . H3N H 0.775(6) 0.977(2) 0.911(3) 0.150 Uiso 1 1 d D . . C1 C 0.2443(4) 0.6868(2) 0.6814(3) 0.0423(7) Uani 1 1 d . . . C2 C 0.0854(4) 0.6881(2) 0.6705(3) 0.0548(8) Uani 1 1 d . . . H2A H 0.0235 0.7238 0.6035 0.066 Uiso 1 1 calc R . . C3 C 0.0211(4) 0.6375(2) 0.7570(3) 0.0608(9) Uani 1 1 d . . . H3A H -0.0845 0.6395 0.7504 0.073 Uiso 1 1 calc R . . C4 C 0.1130(5) 0.5826(3) 0.8558(3) 0.0644(10) Uani 1 1 d . . . H4A H 0.0697 0.5475 0.9155 0.077 Uiso 1 1 calc R . . C5 C 0.2658(5) 0.5809(2) 0.8638(3) 0.0579(9) Uani 1 1 d . . . H5A H 0.3283 0.5434 0.9283 0.069 Uiso 1 1 calc R . . C6 C 0.4716(4) 0.7355(2) 0.5953(3) 0.0502(8) Uani 1 1 d . . . H6A H 0.4833 0.7496 0.5060 0.060 Uiso 1 1 calc R . . H6B H 0.5115 0.6708 0.6175 0.060 Uiso 1 1 calc R . . C7 C 0.8075(5) 0.8826(4) 0.7653(5) 0.0936(15) Uani 1 1 d . . . H7A H 0.9095 0.8913 0.7601 0.112 Uiso 1 1 calc R . . C8 C 0.7173(4) 0.8202(3) 0.6830(3) 0.0650(10) Uani 1 1 d . . . H8A H 0.7582 0.7859 0.6212 0.078 Uiso 1 1 calc R . . C9 C 0.5673(4) 0.8066(2) 0.6889(3) 0.0461(8) Uani 1 1 d . . . C10 C 0.5081(4) 0.8585(2) 0.7795(3) 0.0584(9) Uani 1 1 d . . . H10A H 0.4058 0.8514 0.7846 0.070 Uiso 1 1 calc R . . C11 C 0.6020(7) 0.9206(3) 0.8621(3) 0.0851(14) Uani 1 1 d . . . H11A H 0.5636 0.9558 0.9247 0.102 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0484(5) 0.0514(5) 0.0547(4) 0.0027(4) -0.0004(3) -0.0027(4) Cl2 0.0642(7) 0.1156(9) 0.0691(6) -0.0113(5) 0.0156(5) -0.0376(6) N1 0.0390(15) 0.0485(16) 0.0465(13) 0.0018(12) 0.0047(12) -0.0013(14) N2 0.0384(17) 0.0647(19) 0.0501(15) 0.0104(13) 0.0048(12) 0.0000(15) N3 0.126(4) 0.068(3) 0.078(3) 0.032(2) -0.043(3) -0.044(3) C1 0.0364(18) 0.0450(18) 0.0437(15) -0.0028(14) 0.0042(13) 0.0002(15) C2 0.041(2) 0.062(2) 0.0590(19) -0.0030(17) 0.0059(15) -0.0003(18) C3 0.047(2) 0.063(2) 0.077(2) -0.0136(19) 0.0240(18) -0.0109(19) C4 0.072(3) 0.062(2) 0.064(2) -0.0005(18) 0.0268(19) -0.019(2) C5 0.073(3) 0.051(2) 0.0481(18) 0.0060(15) 0.0110(17) -0.006(2) C6 0.049(2) 0.052(2) 0.0525(17) 0.0067(15) 0.0157(15) 0.0011(17) C7 0.058(3) 0.095(4) 0.111(4) 0.054(3) -0.019(3) -0.025(3) C8 0.044(2) 0.064(2) 0.084(2) 0.025(2) 0.0065(19) -0.0018(19) C9 0.041(2) 0.0445(19) 0.0496(17) 0.0153(15) 0.0014(14) 0.0003(16) C10 0.069(3) 0.049(2) 0.0551(19) 0.0010(16) 0.0065(17) -0.0009(19) C11 0.134(5) 0.053(3) 0.059(2) 0.0070(18) 0.001(3) -0.011(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 C1 1.338(3) . ? N1 C5 1.356(4) . ? N1 H1N 0.86(3) . ? N2 C1 1.339(4) . ? N2 C6 1.439(4) . ? N2 H2N 0.86(3) . ? N3 C7 1.330(6) . ? N3 C11 1.339(6) . ? N3 H3N 0.86(3) . ? C1 C2 1.398(4) . ? C2 C3 1.354(4) . ? C2 H2A 0.9300 . ? C3 C4 1.390(5) . ? C3 H3A 0.9300 . ? C4 C5 1.347(5) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C9 1.509(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.348(5) . ? C7 H7A 0.9300 . ? C8 C9 1.365(4) . ? C8 H8A 0.9300 . ? C9 C10 1.370(4) . ? C10 C11 1.364(5) . ? C10 H10A 0.9300 . ? C11 H11A 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 C1 N1 C5 122.4(3) . . ? C1 N1 H1N 122(2) . . ? C5 N1 H1N 115(2) . . ? C1 N2 C6 125.7(3) . . ? C1 N2 H2N 116(2) . . ? C6 N2 H2N 119(2) . . ? C7 N3 C11 121.3(4) . . ? C7 N3 H3N 139(4) . . ? C11 N3 H3N 99(4) . . ? N1 C1 N2 120.7(3) . . ? N1 C1 C2 117.9(3) . . ? N2 C1 C2 121.4(3) . . ? C3 C2 C1 120.3(3) . . ? C3 C2 H2A 119.9 . . ? C1 C2 H2A 119.9 . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C5 C4 C3 119.0(3) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C4 C5 N1 120.4(3) . . ? C4 C5 H5A 119.8 . . ? N1 C5 H5A 119.8 . . ? N2 C6 C9 114.8(3) . . ? N2 C6 H6A 108.6 . . ? C9 C6 H6A 108.6 . . ? N2 C6 H6B 108.6 . . ? C9 C6 H6B 108.6 . . ? H6A C6 H6B 107.5 . . ? N3 C7 C8 119.2(5) . . ? N3 C7 H7A 120.4 . . ? C8 C7 H7A 120.4 . . ? C7 C8 C9 121.3(4) . . ? C7 C8 H8A 119.4 . . ? C9 C8 H8A 119.4 . . ? C8 C9 C10 118.8(3) . . ? C8 C9 C6 119.2(3) . . ? C10 C9 C6 122.1(3) . . ? C11 C10 C9 118.8(4) . . ? C11 C10 H10A 120.6 . . ? C9 C10 H10A 120.6 . . ? N3 C11 C10 120.6(4) . . ? N3 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? 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 C5 N1 C1 N2 -178.3(3) . . . . ? C5 N1 C1 C2 0.8(4) . . . . ? C6 N2 C1 N1 2.3(5) . . . . ? C6 N2 C1 C2 -176.7(3) . . . . ? N1 C1 C2 C3 0.7(4) . . . . ? N2 C1 C2 C3 179.8(3) . . . . ? C1 C2 C3 C4 -1.2(5) . . . . ? C2 C3 C4 C5 0.2(5) . . . . ? C3 C4 C5 N1 1.3(5) . . . . ? C1 N1 C5 C4 -1.8(5) . . . . ? C1 N2 C6 C9 -84.8(4) . . . . ? C11 N3 C7 C8 -0.6(6) . . . . ? N3 C7 C8 C9 0.1(5) . . . . ? C7 C8 C9 C10 0.7(5) . . . . ? C7 C8 C9 C6 -179.5(3) . . . . ? N2 C6 C9 C8 -171.9(3) . . . . ? N2 C6 C9 C10 7.8(4) . . . . ? C8 C9 C10 C11 -1.1(4) . . . . ? C6 C9 C10 C11 179.2(3) . . . . ? C7 N3 C11 C10 0.2(6) . . . . ? C9 C10 C11 N3 0.7(5) . . . . ? 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 H1N Cl1 0.86(3) 2.246(14) 3.076(3) 161(3) . N2 H2N Cl1 0.86(3) 2.322(16) 3.140(3) 158(3) 4_575 N3 H3N Cl2 0.86(3) 2.215(13) 3.067(4) 171(5) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.268 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.048 data_complex4 _database_code_depnum_ccdc_archive 'CCDC 922201' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N3, 2(N O3)' _chemical_formula_sum 'C11 H13 N5 O6' _chemical_formula_weight 311.26 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' 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' H H 0.0000 0.0000 '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/n' _symmetry_space_group_name_Hall '-P 2yn' 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 9.4912(6) _cell_length_b 14.4740(8) _cell_length_c 10.4976(10) _cell_angle_alpha 90.00 _cell_angle_beta 104.455(8) _cell_angle_gamma 90.00 _cell_volume 1396.46(18) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1025 _cell_measurement_theta_min 3.35 _cell_measurement_theta_max 25.87 _exptl_crystal_description prism _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9736 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4249 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2723 _reflns_number_gt 2191 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'ORTEP-II (Johnson, 1976)' _computing_molecular_graphics SHELXL-97 _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^)+(0.0487P)^2^+0.0997P] 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 2723 _refine_ls_number_parameters 208 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1390 _refine_ls_wR_factor_gt 0.1168 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.7733(4) 0.38004(18) 0.5103(3) 0.1270(12) Uani 1 1 d . . . O2 O 0.6454(3) 0.3482(3) 0.3222(3) 0.1373(12) Uani 1 1 d . . . O3 O 0.8602(2) 0.39768(17) 0.3447(2) 0.0904(8) Uani 1 1 d . . . O4 O 0.8405(2) 0.33021(15) 0.8248(2) 0.0758(6) Uani 1 1 d . . . O5 O 0.8487(3) 0.47607(18) 0.8456(3) 0.1083(9) Uani 1 1 d . . . O6 O 0.6439(2) 0.40964(16) 0.7609(2) 0.0823(7) Uani 1 1 d . . . N1 N 0.6410(2) 0.11851(16) 0.4417(2) 0.0563(6) Uani 1 1 d D . . H1N H 0.5488(13) 0.117(2) 0.436(3) 0.085 Uiso 1 1 d D . . N2 N 0.6636(2) 0.21093(16) 0.6277(2) 0.0545(6) Uani 1 1 d D . . H2N H 0.721(3) 0.2498(16) 0.677(2) 0.082 Uiso 1 1 d D . . N3 N 0.4505(2) 0.33556(16) 0.4993(2) 0.0529(6) Uani 1 1 d D . . H3N H 0.5381(15) 0.334(2) 0.492(3) 0.079 Uiso 1 1 d D . . N4 N 0.7597(3) 0.37634(18) 0.3918(3) 0.0682(7) Uani 1 1 d . . . N5 N 0.7759(3) 0.40609(19) 0.8117(2) 0.0597(6) Uani 1 1 d . . . C1 C 0.7233(3) 0.16559(17) 0.5430(3) 0.0474(6) Uani 1 1 d . . . C2 C 0.8735(3) 0.16618(19) 0.5554(3) 0.0608(8) Uani 1 1 d . . . H2A H 0.9344 0.1997 0.6226 0.073 Uiso 1 1 calc R . . C3 C 0.9297(3) 0.1182(2) 0.4700(4) 0.0755(9) Uani 1 1 d . . . H3A H 1.0296 0.1193 0.4788 0.091 Uiso 1 1 calc R . . C4 C 0.8421(4) 0.0672(2) 0.3694(4) 0.0820(10) Uani 1 1 d . . . H4A H 0.8818 0.0330 0.3118 0.098 Uiso 1 1 calc R . . C5 C 0.6977(4) 0.0688(2) 0.3576(3) 0.0737(9) Uani 1 1 d . . . H5A H 0.6361 0.0353 0.2907 0.088 Uiso 1 1 calc R . . C6 C 0.5173(3) 0.20032(19) 0.6407(3) 0.0572(7) Uani 1 1 d . . . H6A H 0.5200 0.1995 0.7337 0.069 Uiso 1 1 calc R . . H6B H 0.4813 0.1407 0.6047 0.069 Uiso 1 1 calc R . . C7 C 0.4108(3) 0.27273(18) 0.5756(2) 0.0479(6) Uani 1 1 d . . . C8 C 0.2723(3) 0.2765(2) 0.5922(3) 0.0605(8) Uani 1 1 d . . . H8A H 0.2429 0.2341 0.6468 0.073 Uiso 1 1 calc R . . C9 C 0.1777(3) 0.3421(2) 0.5289(3) 0.0718(9) Uani 1 1 d . . . H9A H 0.0836 0.3442 0.5401 0.086 Uiso 1 1 calc R . . C10 C 0.2212(3) 0.4053(2) 0.4482(3) 0.0672(8) Uani 1 1 d . . . H10A H 0.1569 0.4499 0.4037 0.081 Uiso 1 1 calc R . . C11 C 0.3600(3) 0.40104(19) 0.4351(3) 0.0635(8) Uani 1 1 d . . . H11A H 0.3921 0.4434 0.3819 0.076 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.230(4) 0.0859(18) 0.088(2) -0.0044(15) 0.083(2) -0.013(2) O2 0.0605(15) 0.206(4) 0.142(3) -0.017(2) 0.0184(17) -0.0200(18) O3 0.0636(13) 0.124(2) 0.0934(18) 0.0274(15) 0.0388(13) 0.0087(13) O4 0.0725(13) 0.0616(14) 0.0763(15) 0.0098(12) -0.0131(11) 0.0054(11) O5 0.0901(16) 0.0805(17) 0.141(2) -0.0498(17) 0.0030(15) -0.0091(14) O6 0.0495(12) 0.1143(19) 0.0803(16) -0.0034(13) 0.0111(11) 0.0079(11) N1 0.0492(12) 0.0576(14) 0.0613(15) -0.0009(12) 0.0120(13) -0.0053(12) N2 0.0432(12) 0.0541(15) 0.0637(16) -0.0025(12) 0.0088(11) -0.0019(10) N3 0.0441(12) 0.0544(14) 0.0587(15) -0.0035(12) 0.0100(12) -0.0022(12) N4 0.0686(17) 0.0681(17) 0.075(2) 0.0087(15) 0.0318(16) 0.0079(14) N5 0.0574(15) 0.0698(18) 0.0486(14) -0.0101(13) 0.0070(12) -0.0039(14) C1 0.0446(14) 0.0417(14) 0.0536(16) 0.0040(13) 0.0080(13) -0.0002(12) C2 0.0463(15) 0.0644(19) 0.070(2) 0.0004(16) 0.0107(15) 0.0021(14) C3 0.0482(16) 0.084(2) 0.096(3) 0.006(2) 0.0211(18) 0.0088(17) C4 0.089(2) 0.083(2) 0.081(3) -0.004(2) 0.036(2) 0.011(2) C5 0.085(2) 0.070(2) 0.068(2) -0.0093(17) 0.0230(19) -0.0073(18) C6 0.0519(16) 0.0614(18) 0.0584(18) 0.0063(15) 0.0141(14) 0.0006(14) C7 0.0511(15) 0.0501(16) 0.0413(15) -0.0052(13) 0.0093(12) -0.0072(12) C8 0.0468(16) 0.078(2) 0.0573(18) -0.0002(16) 0.0148(14) -0.0042(15) C9 0.0487(16) 0.086(2) 0.077(2) -0.0062(19) 0.0090(16) 0.0039(16) C10 0.0576(18) 0.059(2) 0.075(2) -0.0100(17) -0.0024(16) 0.0093(15) C11 0.0680(19) 0.0524(18) 0.063(2) 0.0042(15) 0.0035(16) -0.0031(15) _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 N4 1.219(3) . ? O2 N4 1.217(4) . ? O3 N4 1.219(3) . ? O4 N5 1.249(3) . ? O5 N5 1.228(3) . ? O6 N5 1.234(3) . ? N1 C1 1.338(3) . ? N1 C5 1.350(4) . ? N1 H1N 0.86(3) . ? N2 C1 1.339(3) . ? N2 C6 1.437(3) . ? N2 H2N 0.86(3) . ? N3 C7 1.327(3) . ? N3 C11 1.342(3) . ? N3 H3N 0.86(3) . ? C1 C2 1.399(3) . ? C2 C3 1.345(4) . ? C2 H2A 0.9300 . ? C3 C4 1.382(4) . ? C3 H3A 0.9300 . ? C4 C5 1.346(4) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.497(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.369(3) . ? C8 C9 1.360(4) . ? C8 H8A 0.9300 . ? C9 C10 1.379(4) . ? C9 H9A 0.9300 . ? C10 C11 1.360(4) . ? C10 H10A 0.9300 . ? C11 H11A 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 C1 N1 C5 122.9(2) . . ? C1 N1 H1N 117(2) . . ? C5 N1 H1N 120(2) . . ? C1 N2 C6 126.1(2) . . ? C1 N2 H2N 115(2) . . ? C6 N2 H2N 119(2) . . ? C7 N3 C11 123.0(2) . . ? C7 N3 H3N 117(2) . . ? C11 N3 H3N 120(2) . . ? O2 N4 O3 120.8(3) . . ? O2 N4 O1 118.6(3) . . ? O3 N4 O1 120.6(3) . . ? O5 N5 O6 121.9(3) . . ? O5 N5 O4 117.9(3) . . ? O6 N5 O4 120.1(3) . . ? N1 C1 N2 121.2(2) . . ? N1 C1 C2 117.1(2) . . ? N2 C1 C2 121.7(3) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C2 C3 C4 121.5(3) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 117.7(3) . . ? C5 C4 H4A 121.1 . . ? C3 C4 H4A 121.1 . . ? C4 C5 N1 120.8(3) . . ? C4 C5 H5A 119.6 . . ? N1 C5 H5A 119.6 . . ? N2 C6 C7 116.1(2) . . ? N2 C6 H6A 108.3 . . ? C7 C6 H6A 108.3 . . ? N2 C6 H6B 108.3 . . ? C7 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? N3 C7 C8 118.3(3) . . ? N3 C7 C6 119.6(2) . . ? C8 C7 C6 122.0(2) . . ? C9 C8 C7 120.3(3) . . ? C9 C8 H8A 119.9 . . ? C7 C8 H8A 119.9 . . ? C8 C9 C10 120.0(3) . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C11 C10 C9 118.6(3) . . ? C11 C10 H10A 120.7 . . ? C9 C10 H10A 120.7 . . ? N3 C11 C10 119.7(3) . . ? N3 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? 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 C5 N1 C1 N2 -177.2(3) . . . . ? C5 N1 C1 C2 3.6(4) . . . . ? C6 N2 C1 N1 14.2(4) . . . . ? C6 N2 C1 C2 -166.6(3) . . . . ? N1 C1 C2 C3 -2.2(4) . . . . ? N2 C1 C2 C3 178.6(3) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C2 C3 C4 C5 1.5(5) . . . . ? C3 C4 C5 N1 -0.1(5) . . . . ? C1 N1 C5 C4 -2.5(5) . . . . ? C1 N2 C6 C7 -100.3(3) . . . . ? C11 N3 C7 C8 -1.7(4) . . . . ? C11 N3 C7 C6 178.3(2) . . . . ? N2 C6 C7 N3 7.2(4) . . . . ? N2 C6 C7 C8 -172.8(2) . . . . ? N3 C7 C8 C9 1.5(4) . . . . ? C6 C7 C8 C9 -178.5(3) . . . . ? C7 C8 C9 C10 -0.3(5) . . . . ? C8 C9 C10 C11 -0.8(5) . . . . ? C7 N3 C11 C10 0.6(4) . . . . ? C9 C10 C11 N3 0.6(4) . . . . ? 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 H1N O4 0.86(3) 2.17(2) 2.906(3) 143(3) 4_565 N1 H1N O5 0.86(3) 2.32(2) 3.032(3) 139(3) 4_565 N2 H2N O4 0.86(3) 2.041(12) 2.889(3) 168(3) . N2 H2N O6 0.86(3) 2.64(2) 3.224(3) 126(2) . N3 H3N O2 0.86(3) 2.27(2) 2.938(4) 135(3) . N3 H3N O1 0.86(3) 2.292(15) 3.105(4) 159(3) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.162 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.035 data_complex5 _database_code_depnum_ccdc_archive 'CCDC 922202' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N3, 2(N O3)' _chemical_formula_sum 'C11 H13 N5 O6' _chemical_formula_weight 311.26 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 5.6882(11) _cell_length_b 7.1254(10) _cell_length_c 18.859(3) _cell_angle_alpha 93.019(12) _cell_angle_beta 93.569(14) _cell_angle_gamma 112.646(15) _cell_volume 701.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 656 _cell_measurement_theta_min 3.41 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9737 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3370 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2462 _reflns_number_gt 2099 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'ORTEP-II (Johnson, 1976)' _computing_molecular_graphics SHELXL-97 _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^)+(0.0866P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2462 _refine_ls_number_parameters 208 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0975 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.1663 _refine_ls_wR_factor_gt 0.1457 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 0.4466(5) 1.0962(4) 0.33006(14) 0.0910(8) Uani 1 1 d . . . O2 O 0.6869(4) 1.0796(3) 0.42022(12) 0.0670(6) Uani 1 1 d . . . O3 O 0.4703(6) 1.2643(5) 0.43041(16) 0.1003(9) Uani 1 1 d . . . O4 O 1.6903(5) 1.1518(4) 0.05604(12) 0.0884(9) Uani 1 1 d . . . O5 O 1.7412(5) 1.2385(4) 0.16701(12) 0.0842(8) Uani 1 1 d . . . O6 O 2.0557(4) 1.3577(4) 0.10329(14) 0.0916(9) Uani 1 1 d . . . N1 N 0.9886(6) 0.7824(4) 0.41025(15) 0.0706(8) Uani 1 1 d D . . H1N H 0.964(8) 0.887(4) 0.430(2) 0.106 Uiso 1 1 d D . . N2 N 0.7281(5) 0.7835(4) 0.30703(13) 0.0602(7) Uani 1 1 d D . . H2N H 0.703(7) 0.888(4) 0.323(2) 0.090 Uiso 1 1 d D . . N3 N 1.1508(6) 0.9218(5) 0.12515(19) 0.0789(9) Uani 1 1 d D . . H3N H 1.304(4) 1.018(5) 0.127(3) 0.118 Uiso 1 1 d D . . N4 N 0.5325(5) 1.1472(4) 0.39247(15) 0.0607(7) Uani 1 1 d . . . N5 N 1.8274(5) 1.2506(4) 0.10877(14) 0.0593(7) Uani 1 1 d . . . C1 C 0.8793(5) 0.7034(4) 0.34202(13) 0.0439(6) Uani 1 1 d . . . C2 C 0.9374(6) 0.5425(4) 0.31264(16) 0.0554(8) Uani 1 1 d . . . H2A H 0.8669 0.4819 0.2673 0.066 Uiso 1 1 calc R . . C3 C 1.0986(6) 0.4748(4) 0.35111(18) 0.0611(8) Uani 1 1 d . . . H3A H 1.1355 0.3675 0.3319 0.073 Uiso 1 1 calc R . . C4 C 1.2041(6) 0.5649(5) 0.41737(19) 0.0646(9) Uani 1 1 d . . . H4A H 1.3171 0.5225 0.4431 0.078 Uiso 1 1 calc R . . C5 C 1.1436(5) 0.7126(4) 0.44431(13) 0.0391(6) Uani 1 1 d . . . H5A H 1.2140 0.7710 0.4899 0.047 Uiso 1 1 calc R . . C6 C 0.5959(6) 0.7033(6) 0.23862(15) 0.0669(9) Uani 1 1 d . . . H6A H 0.4629 0.7556 0.2309 0.080 Uiso 1 1 calc R . . H6B H 0.5129 0.5562 0.2386 0.080 Uiso 1 1 calc R . . C7 C 1.0124(5) 0.8886(4) 0.18399(16) 0.0526(7) Uani 1 1 d . . . H7A H 1.0883 0.9577 0.2280 0.063 Uiso 1 1 calc R . . C8 C 0.7606(5) 0.7523(4) 0.17726(14) 0.0482(7) Uani 1 1 d . . . C9 C 0.6615(6) 0.6573(6) 0.11104(18) 0.0799(11) Uani 1 1 d . . . H9A H 0.4915 0.5664 0.1041 0.096 Uiso 1 1 calc R . . C10 C 0.8064(8) 0.6935(7) 0.05565(19) 0.0928(13) Uani 1 1 d . . . H10A H 0.7356 0.6247 0.0113 0.111 Uiso 1 1 calc R . . C11 C 1.0437(5) 0.8229(4) 0.06281(14) 0.0486(7) Uani 1 1 d . . . H11A H 1.1390 0.8458 0.0235 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0809(18) 0.112(2) 0.0557(16) 0.0018(14) -0.0184(13) 0.0156(15) O2 0.0731(15) 0.0743(14) 0.0648(14) -0.0046(11) -0.0052(11) 0.0441(12) O3 0.119(2) 0.113(2) 0.099(2) -0.0147(17) -0.0041(17) 0.083(2) O4 0.0590(15) 0.1170(19) 0.0439(14) -0.0257(13) 0.0101(11) -0.0123(13) O5 0.0781(17) 0.0950(17) 0.0510(15) -0.0176(12) 0.0197(12) 0.0033(13) O6 0.0470(14) 0.1134(19) 0.0757(18) -0.0092(14) 0.0125(12) -0.0100(13) N1 0.081(2) 0.0739(18) 0.0530(17) -0.0007(14) 0.0099(15) 0.0258(16) N2 0.0655(17) 0.0865(19) 0.0369(14) -0.0042(12) 0.0050(12) 0.0398(15) N3 0.0549(17) 0.081(2) 0.096(3) 0.0238(18) 0.0152(18) 0.0174(15) N4 0.0557(16) 0.0590(16) 0.0609(18) 0.0067(13) 0.0070(14) 0.0148(13) N5 0.0524(16) 0.0612(15) 0.0479(16) -0.0074(12) 0.0110(13) 0.0045(12) C1 0.0426(15) 0.0535(16) 0.0331(14) -0.0027(12) 0.0071(12) 0.0161(13) C2 0.0615(19) 0.0525(16) 0.0437(17) -0.0063(13) 0.0146(14) 0.0128(15) C3 0.067(2) 0.0478(16) 0.073(2) 0.0121(15) 0.0272(17) 0.0236(15) C4 0.063(2) 0.069(2) 0.062(2) 0.0185(17) 0.0102(17) 0.0239(17) C5 0.0446(15) 0.0404(14) 0.0334(14) 0.0041(11) -0.0028(11) 0.0184(12) C6 0.0414(17) 0.116(3) 0.0380(17) 0.0047(16) 0.0052(13) 0.0255(17) C7 0.0400(16) 0.0602(17) 0.0491(18) 0.0009(13) 0.0009(13) 0.0110(13) C8 0.0367(15) 0.0649(17) 0.0383(15) 0.0020(12) 0.0025(12) 0.0150(13) C9 0.0434(18) 0.116(3) 0.0445(19) -0.0111(18) -0.0020(15) -0.0043(18) C10 0.073(3) 0.128(3) 0.040(2) -0.0168(19) 0.0085(17) 0.000(2) C11 0.0448(17) 0.0633(17) 0.0314(15) 0.0042(12) 0.0124(12) 0.0128(14) _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 N4 1.226(3) . ? O2 N4 1.253(3) . ? O3 N4 1.237(3) . ? O4 N5 1.225(3) . ? O5 N5 1.224(3) . ? O6 N5 1.241(3) . ? N1 C5 1.318(4) . ? N1 C1 1.383(4) . ? N1 H1N 0.87(3) . ? N2 C1 1.359(4) . ? N2 C6 1.424(4) . ? N2 H2N 0.86(3) . ? N3 C11 1.320(4) . ? N3 C7 1.378(4) . ? N3 H3N 0.87(3) . ? C1 C2 1.407(4) . ? C2 C3 1.376(4) . ? C2 H2A 0.9300 . ? C3 C4 1.363(5) . ? C3 H3A 0.9300 . ? C4 C5 1.315(4) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C8 1.505(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.380(4) . ? C7 H7A 0.9300 . ? C8 C9 1.366(4) . ? C9 C10 1.345(5) . ? C9 H9A 0.9300 . ? C10 C11 1.302(5) . ? C10 H10A 0.9300 . ? C11 H11A 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 C5 N1 C1 121.1(3) . . ? C5 N1 H1N 119(3) . . ? C1 N1 H1N 120(3) . . ? C1 N2 C6 123.5(3) . . ? C1 N2 H2N 124(3) . . ? C6 N2 H2N 113(3) . . ? C11 N3 C7 120.2(3) . . ? C11 N3 H3N 118(3) . . ? C7 N3 H3N 121(3) . . ? O1 N4 O3 122.0(3) . . ? O1 N4 O2 120.4(3) . . ? O3 N4 O2 117.6(3) . . ? O4 N5 O5 120.0(3) . . ? O4 N5 O6 119.8(3) . . ? O5 N5 O6 120.2(3) . . ? N2 C1 N1 119.9(2) . . ? N2 C1 C2 123.8(3) . . ? N1 C1 C2 116.3(3) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C4 C3 C2 120.1(3) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C5 C4 C3 118.9(3) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? C4 C5 N1 123.6(3) . . ? C4 C5 H5A 118.2 . . ? N1 C5 H5A 118.2 . . ? N2 C6 C8 115.0(3) . . ? N2 C6 H6A 108.5 . . ? C8 C6 H6A 108.5 . . ? N2 C6 H6B 108.5 . . ? C8 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? N3 C7 C8 119.6(3) . . ? N3 C7 H7A 120.2 . . ? C8 C7 H7A 120.2 . . ? C9 C8 C7 117.0(3) . . ? C9 C8 C6 119.6(3) . . ? C7 C8 C6 123.4(3) . . ? C10 C9 C8 120.9(3) . . ? C10 C9 H9A 119.5 . . ? C8 C9 H9A 119.5 . . ? C11 C10 C9 121.4(3) . . ? C11 C10 H10A 119.3 . . ? C9 C10 H10A 119.3 . . ? C10 C11 N3 120.9(3) . . ? C10 C11 H11A 119.6 . . ? N3 C11 H11A 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N2 C1 N1 -176.0(3) . . . . ? C6 N2 C1 C2 4.9(4) . . . . ? C5 N1 C1 N2 -177.4(2) . . . . ? C5 N1 C1 C2 1.8(4) . . . . ? N2 C1 C2 C3 178.1(3) . . . . ? N1 C1 C2 C3 -1.1(4) . . . . ? C1 C2 C3 C4 -0.7(4) . . . . ? C2 C3 C4 C5 1.9(4) . . . . ? C3 C4 C5 N1 -1.3(4) . . . . ? C1 N1 C5 C4 -0.6(4) . . . . ? C1 N2 C6 C8 -75.5(4) . . . . ? C11 N3 C7 C8 -0.4(4) . . . . ? N3 C7 C8 C9 -0.4(4) . . . . ? N3 C7 C8 C6 178.9(3) . . . . ? N2 C6 C8 C9 169.9(3) . . . . ? N2 C6 C8 C7 -9.3(4) . . . . ? C7 C8 C9 C10 1.3(6) . . . . ? C6 C8 C9 C10 -178.0(4) . . . . ? C8 C9 C10 C11 -1.4(7) . . . . ? C9 C10 C11 N3 0.6(6) . . . . ? C7 N3 C11 C10 0.3(5) . . . . ? 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 H1N O2 0.87(3) 2.46(3) 3.204(4) 143(4) . N2 H2N O2 0.86(3) 2.25(2) 3.005(3) 147(4) . N2 H2N O1 0.86(3) 2.45(2) 3.233(4) 152(4) . N3 H3N O5 0.87(3) 2.418(17) 3.262(4) 162(4) . N3 H3N O4 0.87(3) 2.53(3) 3.264(4) 142(4) . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.252 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.048 data_complex6 _database_code_depnum_ccdc_archive 'CCDC 922203' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N3, 2(N O3)' _chemical_formula_sum 'C11 H13 N5 O6' _chemical_formula_weight 311.26 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 9.3186(19) _cell_length_b 13.311(3) _cell_length_c 11.444(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.92(3) _cell_angle_gamma 90.00 _cell_volume 1411.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 5875 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 27.39 _exptl_crystal_description prism _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9715 _exptl_absorpt_correction_T_max 0.9821 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13341 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.42 _reflns_number_total 3195 _reflns_number_gt 2192 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'ORTEP-II (Johnson, 1976)' _computing_molecular_graphics SHELXL-97 _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^)+(0.0660P)^2^+0.2099P] 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 3195 _refine_ls_number_parameters 208 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0920 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1601 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 0.12098(17) -0.03199(11) -0.05266(14) 0.0672(5) Uani 1 1 d . . . O2 O 0.3327(2) -0.09967(14) -0.00577(17) 0.0875(6) Uani 1 1 d . . . O3 O 0.1958(2) -0.15358(16) -0.15360(19) 0.1040(8) Uani 1 1 d . . . O4 O 0.3356(2) 0.42160(13) 0.19755(15) 0.0831(6) Uani 1 1 d . . . O5 O 0.3795(2) 0.36133(15) 0.03100(17) 0.0935(6) Uani 1 1 d . . . O6 O 0.1603(2) 0.39489(18) 0.06264(18) 0.1073(7) Uani 1 1 d . . . N1 N 0.6374(2) 0.38170(14) 0.23357(17) 0.0614(5) Uani 1 1 d D . . H1N H 0.5436(11) 0.382(2) 0.223(2) 0.092 Uiso 1 1 d D . . N2 N 0.6351(2) 0.26589(14) 0.38552(16) 0.0612(5) Uani 1 1 d D . . H2N H 0.686(3) 0.2217(15) 0.427(2) 0.092 Uiso 1 1 d D . . N3 N 0.2175(3) 0.09455(14) 0.14192(19) 0.0710(6) Uani 1 1 d D . . H3N H 0.172(3) 0.0544(18) 0.090(2) 0.106 Uiso 1 1 d D . . N4 N 0.2181(2) -0.09503(13) -0.07169(17) 0.0588(5) Uani 1 1 d . . . N5 N 0.2916(3) 0.39273(14) 0.09651(19) 0.0672(6) Uani 1 1 d . . . C1 C 0.7089(3) 0.44046(19) 0.1614(2) 0.0750(7) Uani 1 1 d . . . H1 H 0.6563 0.4800 0.1053 0.090 Uiso 1 1 calc R . . C2 C 0.8560(3) 0.44275(19) 0.1694(2) 0.0785(7) Uani 1 1 d . . . H2 H 0.9032 0.4820 0.1181 0.094 Uiso 1 1 calc R . . C3 C 0.9347(3) 0.38506(17) 0.2560(2) 0.0704(7) Uani 1 1 d . . . H3 H 1.0350 0.3869 0.2641 0.085 Uiso 1 1 calc R . . C4 C 0.8635(2) 0.32656(17) 0.3280(2) 0.0608(6) Uani 1 1 d . . . H4 H 0.9156 0.2880 0.3855 0.073 Uiso 1 1 calc R . . C5 C 0.7090(2) 0.32341(15) 0.31657(18) 0.0541(5) Uani 1 1 d . . . C6 C 0.4782(2) 0.26745(16) 0.39282(19) 0.0590(6) Uani 1 1 d . . . H6A H 0.4454 0.3365 0.3851 0.071 Uiso 1 1 calc R . . H6B H 0.4602 0.2445 0.4704 0.071 Uiso 1 1 calc R . . C7 C 0.3878(2) 0.20463(14) 0.30270(18) 0.0522(5) Uani 1 1 d . . . C8 C 0.2386(3) 0.19520(17) 0.3100(2) 0.0663(6) Uani 1 1 d . . . H8 H 0.1966 0.2267 0.3705 0.080 Uiso 1 1 calc R . . C9 C 0.1539(3) 0.13904(18) 0.2271(3) 0.0749(7) Uani 1 1 d . . . H9 H 0.0552 0.1326 0.2310 0.090 Uiso 1 1 calc R . . C10 C 0.3596(3) 0.10189(16) 0.1329(2) 0.0702(7) Uani 1 1 d . . . H10 H 0.3989 0.0690 0.0720 0.084 Uiso 1 1 calc R . . C11 C 0.4476(3) 0.15710(15) 0.21210(19) 0.0609(6) Uani 1 1 d . . . H11 H 0.5458 0.1624 0.2049 0.073 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0658(11) 0.0655(9) 0.0697(11) -0.0112(8) 0.0049(8) 0.0070(8) O2 0.0699(12) 0.0987(13) 0.0894(13) -0.0251(10) -0.0129(10) 0.0146(10) O3 0.0697(13) 0.1216(16) 0.1191(16) -0.0762(14) 0.0016(11) 0.0002(11) O4 0.0912(13) 0.0829(12) 0.0703(11) -0.0206(9) -0.0158(10) 0.0097(10) O5 0.0943(15) 0.1080(15) 0.0768(12) -0.0178(11) 0.0014(11) 0.0188(11) O6 0.0694(14) 0.161(2) 0.0875(14) -0.0062(13) -0.0121(11) -0.0030(13) N1 0.0607(12) 0.0611(11) 0.0596(11) -0.0014(9) -0.0062(10) 0.0015(10) N2 0.0552(12) 0.0676(12) 0.0585(11) 0.0017(9) -0.0057(9) -0.0005(9) N3 0.0913(18) 0.0505(11) 0.0662(13) 0.0041(10) -0.0158(12) -0.0107(11) N4 0.0566(12) 0.0575(10) 0.0630(12) -0.0117(9) 0.0101(9) -0.0066(9) N5 0.0716(15) 0.0619(12) 0.0645(13) 0.0028(10) -0.0101(12) 0.0010(10) C1 0.0818(19) 0.0673(15) 0.0739(17) 0.0116(13) -0.0017(14) 0.0006(14) C2 0.080(2) 0.0728(15) 0.0823(18) 0.0107(14) 0.0058(15) -0.0131(14) C3 0.0600(15) 0.0703(14) 0.0798(17) -0.0083(13) 0.0013(13) -0.0092(12) C4 0.0579(15) 0.0620(13) 0.0602(13) -0.0077(11) -0.0050(11) -0.0007(11) C5 0.0585(14) 0.0527(11) 0.0493(12) -0.0088(10) -0.0034(10) -0.0010(10) C6 0.0566(14) 0.0670(13) 0.0526(12) -0.0083(10) 0.0020(10) 0.0003(11) C7 0.0557(13) 0.0481(11) 0.0516(12) 0.0007(9) 0.0002(10) 0.0028(9) C8 0.0573(15) 0.0640(13) 0.0765(16) -0.0083(12) 0.0022(12) 0.0025(11) C9 0.0583(15) 0.0661(14) 0.097(2) 0.0113(14) -0.0090(15) -0.0044(12) C10 0.095(2) 0.0543(13) 0.0595(14) -0.0059(11) -0.0004(14) -0.0058(13) C11 0.0683(15) 0.0567(12) 0.0571(13) -0.0069(10) 0.0036(11) 0.0020(11) _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 N4 1.269(2) . ? O2 N4 1.244(2) . ? O3 N4 1.220(2) . ? O4 N5 1.247(2) . ? O5 N5 1.238(3) . ? O6 N5 1.245(3) . ? N1 C5 1.348(3) . ? N1 C1 1.361(3) . ? N1 H1N 0.87(3) . ? N2 C5 1.340(3) . ? N2 C6 1.473(3) . ? N2 H2N 0.87(3) . ? N3 C9 1.331(4) . ? N3 C10 1.343(3) . ? N3 H3N 0.87(3) . ? C1 C2 1.364(4) . ? C1 H1 0.9300 . ? C2 C3 1.400(4) . ? C2 H2 0.9300 . ? C3 C4 1.356(3) . ? C3 H3 0.9300 . ? C4 C5 1.434(3) . ? C4 H4 0.9300 . ? C6 C7 1.514(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C11 1.380(3) . ? C7 C8 1.407(3) . ? C8 C9 1.388(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.372(3) . ? C10 H10 0.9300 . ? C11 H11 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 C5 N1 C1 121.4(2) . . ? C5 N1 H1N 121.6(19) . . ? C1 N1 H1N 117.0(19) . . ? C5 N2 C6 126.77(19) . . ? C5 N2 H2N 115.4(19) . . ? C6 N2 H2N 117.7(19) . . ? C9 N3 C10 122.7(2) . . ? C9 N3 H3N 123(2) . . ? C10 N3 H3N 114(2) . . ? O3 N4 O2 120.1(2) . . ? O3 N4 O1 119.1(2) . . ? O2 N4 O1 120.77(18) . . ? O5 N5 O6 120.6(2) . . ? O5 N5 O4 119.4(2) . . ? O6 N5 O4 120.0(2) . . ? N1 C1 C2 121.6(2) . . ? N1 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? C1 C2 C3 119.0(3) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 119.5(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 120.8(2) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? N2 C5 N1 119.8(2) . . ? N2 C5 C4 122.4(2) . . ? N1 C5 C4 117.8(2) . . ? N2 C6 C7 116.06(19) . . ? N2 C6 H6A 108.3 . . ? C7 C6 H6A 108.3 . . ? N2 C6 H6B 108.3 . . ? C7 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C11 C7 C8 118.8(2) . . ? C11 C7 C6 121.7(2) . . ? C8 C7 C6 119.5(2) . . ? C9 C8 C7 120.2(2) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? N3 C9 C8 118.4(2) . . ? N3 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? N3 C10 C11 121.1(2) . . ? N3 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C10 C11 C7 118.8(2) . . ? C10 C11 H11 120.6 . . ? C7 C11 H11 120.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 0.3(4) . . . . ? N1 C1 C2 C3 -1.6(4) . . . . ? C1 C2 C3 C4 1.6(4) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C6 N2 C5 N1 -8.7(3) . . . . ? C6 N2 C5 C4 170.73(19) . . . . ? C1 N1 C5 N2 -179.5(2) . . . . ? C1 N1 C5 C4 1.1(3) . . . . ? C3 C4 C5 N2 179.5(2) . . . . ? C3 C4 C5 N1 -1.1(3) . . . . ? C5 N2 C6 C7 84.8(3) . . . . ? N2 C6 C7 C11 -6.3(3) . . . . ? N2 C6 C7 C8 174.56(19) . . . . ? C11 C7 C8 C9 -0.1(3) . . . . ? C6 C7 C8 C9 179.1(2) . . . . ? C10 N3 C9 C8 -0.1(4) . . . . ? C7 C8 C9 N3 0.3(3) . . . . ? C9 N3 C10 C11 -0.4(4) . . . . ? N3 C10 C11 C7 0.6(3) . . . . ? C8 C7 C11 C10 -0.4(3) . . . . ? C6 C7 C11 C10 -179.54(19) . . . . ? 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 H1N O4 0.87(3) 1.999(12) 2.850(3) 166(3) . N2 H2N O6 0.87(3) 2.22(2) 2.940(3) 140(3) 4_666 N3 H3N O1 0.87(3) 2.018(14) 2.862(3) 163(3) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.201 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.045 data_complex7 _database_code_depnum_ccdc_archive 'CCDC 922204' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N3, 2(Cl O4)' _chemical_formula_sum 'C11 H13 Cl2 N3 O8' _chemical_formula_weight 386.14 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' 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' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.2576(13) _cell_length_b 14.176(3) _cell_length_c 9.4606(19) _cell_angle_alpha 90.00 _cell_angle_beta 107.55(3) _cell_angle_gamma 90.00 _cell_volume 800.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4412 _cell_measurement_theta_min 3.42 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.603 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.452 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8688 _exptl_absorpt_correction_T_max 0.9353 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6081 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_sigmaI/netI 0.0685 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2809 _reflns_number_gt 2352 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'ORTEP-II (Johnson, 1976)' _computing_molecular_graphics SHELXL-97 _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^)+(0.0794P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.42(11) _refine_ls_number_reflns 2809 _refine_ls_number_parameters 227 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0952 _refine_ls_R_factor_gt 0.0623 _refine_ls_wR_factor_ref 0.1542 _refine_ls_wR_factor_gt 0.1382 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 1.2274(2) 0.56459(9) 0.56015(19) 0.0745(5) Uani 1 1 d . . . Cl2 Cl 0.1374(3) 0.85555(12) 0.03145(18) 0.0787(5) Uani 1 1 d . . . O1 O 1.0984(17) 0.5778(9) 0.4146(8) 0.230(6) Uani 1 1 d . . . O2 O 1.1450(9) 0.6338(5) 0.6425(7) 0.127(2) Uani 1 1 d . . . O3 O 1.2078(12) 0.4780(4) 0.6206(12) 0.178(4) Uani 1 1 d . . . O4 O 1.4600(8) 0.5768(5) 0.5832(9) 0.156(3) Uani 1 1 d . . . O5 O 0.3706(7) 0.8657(5) 0.1118(6) 0.130(2) Uani 1 1 d . . . O6 O -0.0024(11) 0.8693(6) 0.1182(8) 0.155(3) Uani 1 1 d . . . O7 O 0.0863(10) 0.9183(5) -0.0879(7) 0.127(2) Uani 1 1 d . . . O8 O 0.1214(15) 0.7661(5) -0.0289(12) 0.199(4) Uani 1 1 d . . . N1 N 0.4840(8) 0.6246(3) 0.2483(5) 0.0683(13) Uani 1 1 d D . . H1N H 0.460(12) 0.627(6) 0.333(4) 0.102 Uiso 1 1 d D . . N2 N 0.7647(8) 0.7417(4) 0.4732(5) 0.0677(13) Uani 1 1 d D . . H2N H 0.884(7) 0.727(5) 0.542(6) 0.102 Uiso 1 1 d D . . N3 N 0.4499(7) 0.8402(3) 0.4354(5) 0.0614(11) Uani 1 1 d D . . H3N H 0.402(10) 0.834(5) 0.3402(16) 0.092 Uiso 1 1 d D . . C1 C 0.3530(10) 0.5637(5) 0.1505(8) 0.0739(15) Uani 1 1 d . . . H1A H 0.2437 0.5294 0.1763 0.089 Uiso 1 1 calc R . . C2 C 0.3795(12) 0.5523(5) 0.0163(9) 0.0867(19) Uani 1 1 d . . . H2A H 0.2851 0.5128 -0.0537 0.104 Uiso 1 1 calc R . . C3 C 0.5467(15) 0.5997(6) -0.0146(9) 0.096(2) Uani 1 1 d . . . H3A H 0.5748 0.5901 -0.1046 0.115 Uiso 1 1 calc R . . C4 C 0.6754(10) 0.6621(4) 0.0866(7) 0.0659(15) Uani 1 1 d . . . H4A H 0.7882 0.6953 0.0630 0.079 Uiso 1 1 calc R . . C5 C 0.6439(8) 0.6760(3) 0.2144(7) 0.0566(13) Uani 1 1 d . . . C6 C 0.7807(9) 0.7490(4) 0.3235(6) 0.0615(13) Uani 1 1 d . . . H6A H 0.9369 0.7427 0.3277 0.074 Uiso 1 1 calc R . . H6B H 0.7317 0.8115 0.2855 0.074 Uiso 1 1 calc R . . C7 C 0.6184(8) 0.7892(3) 0.5262(6) 0.0512(12) Uani 1 1 d . . . C8 C 0.6345(11) 0.7863(4) 0.6772(7) 0.0694(15) Uani 1 1 d . . . H8A H 0.7495 0.7525 0.7431 0.083 Uiso 1 1 calc R . . C9 C 0.4823(13) 0.8328(5) 0.7268(7) 0.086(2) Uani 1 1 d . . . H9A H 0.4947 0.8308 0.8273 0.103 Uiso 1 1 calc R . . C10 C 0.3082(12) 0.8832(4) 0.6313(8) 0.0782(17) Uani 1 1 d . . . H10A H 0.2004 0.9127 0.6652 0.094 Uiso 1 1 calc R . . C11 C 0.3005(10) 0.8878(4) 0.4919(8) 0.0692(15) Uani 1 1 d . . . H11A H 0.1900 0.9247 0.4280 0.083 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0732(9) 0.0548(7) 0.0923(12) 0.0025(7) 0.0199(8) 0.0028(7) Cl2 0.0719(9) 0.0871(10) 0.0742(10) 0.0104(9) 0.0176(7) 0.0084(8) O1 0.293(11) 0.304(12) 0.104(5) 0.051(7) 0.075(6) 0.190(11) O2 0.105(4) 0.150(5) 0.121(4) -0.016(4) 0.025(3) 0.045(4) O3 0.128(5) 0.072(3) 0.345(11) 0.054(5) 0.090(6) 0.011(3) O4 0.079(3) 0.116(4) 0.284(9) -0.059(5) 0.069(4) -0.034(3) O5 0.086(3) 0.171(6) 0.118(4) 0.052(4) 0.006(3) -0.012(4) O6 0.143(5) 0.206(7) 0.150(5) 0.008(5) 0.095(5) -0.013(5) O7 0.111(4) 0.172(5) 0.089(4) 0.047(4) 0.017(3) 0.026(4) O8 0.205(9) 0.086(4) 0.250(10) -0.027(5) -0.016(7) 0.030(5) N1 0.078(3) 0.054(3) 0.073(3) -0.004(2) 0.024(3) -0.010(2) N2 0.061(3) 0.074(3) 0.059(3) 0.003(2) 0.005(2) 0.007(2) N3 0.054(2) 0.058(3) 0.069(3) 0.001(3) 0.015(2) 0.000(2) C1 0.081(4) 0.056(3) 0.084(4) 0.004(3) 0.024(3) 0.004(3) C2 0.110(5) 0.059(4) 0.089(5) -0.006(3) 0.026(4) 0.003(4) C3 0.126(6) 0.098(5) 0.070(5) -0.003(4) 0.038(4) 0.005(5) C4 0.074(4) 0.055(3) 0.078(4) 0.002(3) 0.038(3) -0.009(3) C5 0.053(3) 0.045(2) 0.070(4) 0.008(2) 0.016(3) 0.002(2) C6 0.060(3) 0.061(3) 0.064(4) 0.002(3) 0.018(3) -0.001(3) C7 0.053(3) 0.041(2) 0.057(3) -0.002(2) 0.014(2) -0.001(2) C8 0.087(4) 0.054(3) 0.059(4) -0.003(3) 0.010(3) -0.001(3) C9 0.127(6) 0.077(4) 0.059(4) -0.016(3) 0.037(4) -0.012(4) C10 0.084(4) 0.064(3) 0.091(5) -0.002(3) 0.032(4) 0.016(3) C11 0.063(3) 0.065(3) 0.078(4) 0.001(3) 0.019(3) 0.008(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 Cl1 O3 1.375(6) . ? Cl1 O1 1.383(7) . ? Cl1 O4 1.416(5) . ? Cl1 O2 1.441(6) . ? Cl2 O8 1.382(7) . ? Cl2 O6 1.382(6) . ? Cl2 O7 1.396(6) . ? Cl2 O5 1.435(5) . ? N1 C1 1.348(8) . ? N1 C5 1.352(7) . ? N1 H1N 0.86(3) . ? N2 C7 1.349(7) . ? N2 C6 1.454(7) . ? N2 H2N 0.86(3) . ? N3 C7 1.351(7) . ? N3 C11 1.384(7) . ? N3 H3N 0.86(3) . ? C1 C2 1.339(10) . ? C1 H1A 0.9300 . ? C2 C3 1.348(11) . ? C2 H2A 0.9300 . ? C3 C4 1.373(10) . ? C3 H3A 0.9300 . ? C4 C5 1.297(8) . ? C4 H4A 0.9300 . ? C5 C6 1.528(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.402(8) . ? C8 C9 1.354(8) . ? C8 H8A 0.9300 . ? C9 C10 1.386(9) . ? C9 H9A 0.9300 . ? C10 C11 1.306(9) . ? C10 H10A 0.9300 . ? C11 H11A 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 O3 Cl1 O1 115.9(8) . . ? O3 Cl1 O4 105.2(4) . . ? O1 Cl1 O4 113.6(6) . . ? O3 Cl1 O2 106.9(5) . . ? O1 Cl1 O2 104.5(4) . . ? O4 Cl1 O2 110.6(4) . . ? O8 Cl2 O6 113.3(6) . . ? O8 Cl2 O7 106.3(5) . . ? O6 Cl2 O7 111.0(4) . . ? O8 Cl2 O5 104.2(5) . . ? O6 Cl2 O5 113.4(4) . . ? O7 Cl2 O5 108.2(4) . . ? C1 N1 C5 121.5(5) . . ? C1 N1 H1N 115(5) . . ? C5 N1 H1N 123(5) . . ? C7 N2 C6 125.5(5) . . ? C7 N2 H2N 112(5) . . ? C6 N2 H2N 117(5) . . ? C7 N3 C11 120.3(5) . . ? C7 N3 H3N 124(5) . . ? C11 N3 H3N 113(5) . . ? C2 C1 N1 120.3(6) . . ? C2 C1 H1A 119.8 . . ? N1 C1 H1A 119.8 . . ? C1 C2 C3 118.2(7) . . ? C1 C2 H2A 120.9 . . ? C3 C2 H2A 120.9 . . ? C2 C3 C4 120.0(6) . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C5 C4 C3 121.7(6) . . ? C5 C4 H4A 119.1 . . ? C3 C4 H4A 119.1 . . ? C4 C5 N1 118.1(5) . . ? C4 C5 C6 121.3(5) . . ? N1 C5 C6 120.6(5) . . ? N2 C6 C5 114.9(5) . . ? N2 C6 H6A 108.6 . . ? C5 C6 H6A 108.6 . . ? N2 C6 H6B 108.6 . . ? C5 C6 H6B 108.6 . . ? H6A C6 H6B 107.5 . . ? N2 C7 N3 121.2(5) . . ? N2 C7 C8 121.1(5) . . ? N3 C7 C8 117.8(5) . . ? C9 C8 C7 119.8(6) . . ? C9 C8 H8A 120.1 . . ? C7 C8 H8A 120.1 . . ? C8 C9 C10 121.4(6) . . ? C8 C9 H9A 119.3 . . ? C10 C9 H9A 119.3 . . ? C11 C10 C9 117.9(6) . . ? C11 C10 H10A 121.1 . . ? C9 C10 H10A 121.1 . . ? C10 C11 N3 122.8(6) . . ? C10 C11 H11A 118.6 . . ? N3 C11 H11A 118.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 0.3(9) . . . . ? N1 C1 C2 C3 3.2(10) . . . . ? C1 C2 C3 C4 -4.0(11) . . . . ? C2 C3 C4 C5 1.3(10) . . . . ? C3 C4 C5 N1 2.2(9) . . . . ? C3 C4 C5 C6 -177.1(6) . . . . ? C1 N1 C5 C4 -3.1(8) . . . . ? C1 N1 C5 C6 176.2(5) . . . . ? C7 N2 C6 C5 -93.1(7) . . . . ? C4 C5 C6 N2 -166.4(5) . . . . ? N1 C5 C6 N2 14.3(7) . . . . ? C6 N2 C7 N3 8.8(8) . . . . ? C6 N2 C7 C8 -172.0(5) . . . . ? C11 N3 C7 N2 179.5(5) . . . . ? C11 N3 C7 C8 0.3(7) . . . . ? N2 C7 C8 C9 -178.4(6) . . . . ? N3 C7 C8 C9 0.8(7) . . . . ? C7 C8 C9 C10 0.4(9) . . . . ? C8 C9 C10 C11 -2.8(10) . . . . ? C9 C10 C11 N3 4.0(9) . . . . ? C7 N3 C11 C10 -2.8(8) . . . . ? 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 H1N O4 0.86(3) 2.47(3) 3.288(10) 158(7) 1_455 N2 H2N O2 0.86(3) 2.09(4) 2.877(7) 152(7) . N3 H3N O5 0.86(3) 2.16(3) 2.973(8) 157(7) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.346 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.063 data_complex8 _database_code_depnum_ccdc_archive 'CCDC 922205' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N3, 2(Cl O4)' _chemical_formula_sum 'C11 H13 Cl2 N3 O8' _chemical_formula_weight 386.14 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' 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/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.059(3) _cell_length_b 5.0058(10) _cell_length_c 21.608(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.23(3) _cell_angle_gamma 90.00 _cell_volume 1514.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 6721 _cell_measurement_theta_min 3.32 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.478 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8778 _exptl_absorpt_correction_T_max 0.9318 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11097 _diffrn_reflns_av_R_equivalents 0.0543 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2647 _reflns_number_gt 1846 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'ORTEP-II (Johnson, 1976)' _computing_molecular_graphics SHELXL-97 _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^)+(0.1226P)^2^+0.3289P] 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 2647 _refine_ls_number_parameters 226 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0874 _refine_ls_R_factor_gt 0.0650 _refine_ls_wR_factor_ref 0.2053 _refine_ls_wR_factor_gt 0.1848 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.46305(8) 1.0686(2) 0.39335(5) 0.0623(4) Uani 1 1 d . . . Cl2 Cl 0.02584(7) 0.31741(19) 0.86115(4) 0.0500(4) Uani 1 1 d . . . O1 O 0.4646(3) 0.7836(7) 0.4022(2) 0.1033(14) Uani 1 1 d . . . O2 O 0.3699(4) 1.1438(9) 0.3990(3) 0.160(2) Uani 1 1 d . . . O3 O 0.4791(5) 1.1462(11) 0.3347(2) 0.159(2) Uani 1 1 d . . . O4 O 0.5249(6) 1.1880(11) 0.4355(3) 0.238(5) Uani 1 1 d . . . O5 O -0.0250(3) 0.4289(7) 0.90940(16) 0.0844(11) Uani 1 1 d . . . O6 O 0.1265(2) 0.3524(7) 0.87534(15) 0.0739(10) Uani 1 1 d . . . O7 O 0.0050(2) 0.0381(6) 0.85464(14) 0.0642(9) Uani 1 1 d . . . O8 O -0.0037(2) 0.4524(6) 0.80363(13) 0.0643(9) Uani 1 1 d . . . N1 N 0.3183(3) 0.5914(8) 0.48191(18) 0.0647(10) Uani 1 1 d D . . H1N H 0.368(2) 0.628(10) 0.463(2) 0.097 Uiso 1 1 d D . . N2 N 0.1962(3) 0.2717(8) 0.66269(16) 0.0572(9) Uani 1 1 d D . . H2N H 0.1355(10) 0.246(11) 0.659(2) 0.086 Uiso 1 1 d D . . N3 N 0.1709(2) 0.5708(7) 0.74021(16) 0.0552(9) Uani 1 1 d D . . H3N H 0.1159(18) 0.497(10) 0.739(2) 0.083 Uiso 1 1 d D . . C1 C 0.3224(3) 0.4218(9) 0.5299(2) 0.0625(12) Uani 1 1 d . . . H1 H 0.3807 0.3469 0.5446 0.075 Uiso 1 1 calc R . . C2 C 0.2434(3) 0.3582(7) 0.55730(17) 0.0473(9) Uani 1 1 d . . . C3 C 0.1578(3) 0.4738(9) 0.53349(19) 0.0577(11) Uani 1 1 d . . . H3 H 0.1016 0.4334 0.5511 0.069 Uiso 1 1 calc R . . C4 C 0.1557(3) 0.6478(9) 0.4840(2) 0.0633(12) Uani 1 1 d . . . H4 H 0.0985 0.7244 0.4679 0.076 Uiso 1 1 calc R . . C5 C 0.2392(3) 0.7060(9) 0.45907(19) 0.0560(11) Uani 1 1 d . . . H5 H 0.2397 0.8258 0.4262 0.067 Uiso 1 1 calc R . . C6 C 0.2467(3) 0.1709(8) 0.61221(19) 0.0586(11) Uani 1 1 d . . . H6A H 0.2192 0.0007 0.5986 0.070 Uiso 1 1 calc R . . H6B H 0.3129 0.1398 0.6273 0.070 Uiso 1 1 calc R . . C7 C 0.2296(3) 0.4698(8) 0.70101(17) 0.0487(10) Uani 1 1 d . . . C8 C 0.3217(3) 0.5738(9) 0.7038(2) 0.0589(11) Uani 1 1 d . . . H8 H 0.3649 0.5105 0.6771 0.071 Uiso 1 1 calc R . . C9 C 0.3483(3) 0.7701(10) 0.7461(2) 0.0664(13) Uani 1 1 d . . . H9 H 0.4102 0.8374 0.7486 0.080 Uiso 1 1 calc R . . C10 C 0.2839(4) 0.8694(9) 0.7853(2) 0.0678(13) Uani 1 1 d . . . H10 H 0.3017 1.0033 0.8139 0.081 Uiso 1 1 calc R . . C11 C 0.1959(3) 0.7687(9) 0.78116(19) 0.0596(11) Uani 1 1 d . . . H11 H 0.1514 0.8347 0.8065 0.071 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0588(7) 0.0570(7) 0.0692(7) 0.0045(5) -0.0047(5) 0.0013(5) Cl2 0.0508(6) 0.0460(6) 0.0536(6) -0.0045(4) 0.0067(4) -0.0069(4) O1 0.093(3) 0.054(2) 0.159(4) 0.007(2) -0.007(3) 0.0066(19) O2 0.124(4) 0.101(3) 0.271(7) 0.027(4) 0.101(5) 0.027(3) O3 0.224(6) 0.155(5) 0.110(4) -0.002(3) 0.086(4) -0.064(4) O4 0.343(10) 0.104(4) 0.224(6) 0.044(4) -0.206(7) -0.088(5) O5 0.102(3) 0.077(2) 0.080(2) -0.0163(19) 0.0453(19) -0.001(2) O6 0.055(2) 0.084(2) 0.080(2) 0.0046(17) -0.0089(16) -0.0203(16) O7 0.065(2) 0.0397(16) 0.087(2) -0.0038(14) 0.0023(16) -0.0068(13) O8 0.0600(19) 0.069(2) 0.0629(18) 0.0113(15) -0.0022(14) -0.0059(15) N1 0.055(2) 0.076(3) 0.065(2) 0.017(2) 0.0126(18) 0.006(2) N2 0.056(2) 0.062(2) 0.052(2) 0.0086(18) 0.0017(18) -0.0026(18) N3 0.042(2) 0.069(2) 0.055(2) 0.0114(19) 0.0063(17) -0.0011(17) C1 0.049(3) 0.071(3) 0.066(3) 0.010(2) 0.003(2) 0.012(2) C2 0.051(2) 0.044(2) 0.046(2) -0.0011(17) 0.0026(18) 0.0021(17) C3 0.050(2) 0.062(3) 0.060(3) 0.003(2) 0.004(2) 0.003(2) C4 0.060(3) 0.073(3) 0.054(2) 0.006(2) -0.011(2) 0.012(2) C5 0.063(3) 0.060(3) 0.044(2) 0.0050(19) 0.001(2) 0.000(2) C6 0.067(3) 0.049(2) 0.060(3) 0.0050(19) 0.005(2) 0.003(2) C7 0.049(2) 0.051(2) 0.046(2) 0.0193(19) 0.0017(18) 0.0048(19) C8 0.047(2) 0.075(3) 0.055(2) 0.010(2) 0.0052(19) -0.004(2) C9 0.054(3) 0.084(3) 0.061(3) 0.015(3) 0.002(2) -0.014(2) C10 0.084(4) 0.066(3) 0.052(3) 0.009(2) -0.007(2) -0.013(3) C11 0.066(3) 0.062(3) 0.051(2) 0.010(2) 0.004(2) 0.009(2) _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 O4 1.342(4) . ? Cl1 O3 1.363(5) . ? Cl1 O2 1.379(5) . ? Cl1 O1 1.439(4) . ? Cl2 O5 1.430(3) . ? Cl2 O6 1.431(3) . ? Cl2 O7 1.433(3) . ? Cl2 O8 1.442(3) . ? N1 C5 1.308(6) . ? N1 C1 1.338(6) . ? N1 H1N 0.86(4) . ? N2 C7 1.349(5) . ? N2 C6 1.446(6) . ? N2 H2N 0.86(4) . ? N3 C7 1.335(5) . ? N3 C11 1.353(6) . ? N3 H3N 0.86(4) . ? C1 C2 1.344(6) . ? C1 H1 0.9300 . ? C2 C3 1.390(5) . ? C2 C6 1.510(5) . ? C3 C4 1.377(6) . ? C3 H3 0.9300 . ? C4 C5 1.367(6) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.392(5) . ? C8 C9 1.372(7) . ? C8 H8 0.9300 . ? C9 C10 1.388(7) . ? C9 H9 0.9300 . ? C10 C11 1.331(6) . ? C10 H10 0.9300 . ? C11 H11 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 O4 Cl1 O3 110.7(4) . . ? O4 Cl1 O2 112.4(5) . . ? O3 Cl1 O2 104.1(4) . . ? O4 Cl1 O1 110.5(3) . . ? O3 Cl1 O1 113.9(3) . . ? O2 Cl1 O1 105.2(3) . . ? O5 Cl2 O6 110.2(2) . . ? O5 Cl2 O7 109.9(2) . . ? O6 Cl2 O7 109.3(2) . . ? O5 Cl2 O8 108.8(2) . . ? O6 Cl2 O8 109.20(19) . . ? O7 Cl2 O8 109.40(18) . . ? C5 N1 C1 123.1(4) . . ? C5 N1 H1N 116(4) . . ? C1 N1 H1N 121(4) . . ? C7 N2 C6 123.6(4) . . ? C7 N2 H2N 117(4) . . ? C6 N2 H2N 116(4) . . ? C7 N3 C11 123.6(4) . . ? C7 N3 H3N 115(4) . . ? C11 N3 H3N 121(4) . . ? N1 C1 C2 120.9(4) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C1 C2 C3 117.4(4) . . ? C1 C2 C6 121.7(4) . . ? C3 C2 C6 120.9(4) . . ? C4 C3 C2 120.5(4) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 118.8(4) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 119.3(4) . . ? N1 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? N2 C6 C2 113.2(3) . . ? N2 C6 H6A 108.9 . . ? C2 C6 H6A 108.9 . . ? N2 C6 H6B 108.9 . . ? C2 C6 H6B 108.9 . . ? H6A C6 H6B 107.8 . . ? N3 C7 N2 117.9(4) . . ? N3 C7 C8 117.3(4) . . ? N2 C7 C8 124.9(4) . . ? C9 C8 C7 119.5(4) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 120.7(4) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 118.5(5) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? C10 C11 N3 120.4(5) . . ? C10 C11 H11 119.8 . . ? N3 C11 H11 119.8 . . ? 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 C5 N1 C1 C2 0.5(7) . . . . ? N1 C1 C2 C3 0.4(7) . . . . ? N1 C1 C2 C6 -178.9(4) . . . . ? C1 C2 C3 C4 -0.4(6) . . . . ? C6 C2 C3 C4 178.9(4) . . . . ? C2 C3 C4 C5 -0.4(7) . . . . ? C1 N1 C5 C4 -1.4(7) . . . . ? C3 C4 C5 N1 1.3(7) . . . . ? C7 N2 C6 C2 -74.3(5) . . . . ? C1 C2 C6 N2 132.2(4) . . . . ? C3 C2 C6 N2 -47.2(5) . . . . ? C11 N3 C7 N2 179.6(3) . . . . ? C11 N3 C7 C8 1.0(6) . . . . ? C6 N2 C7 N3 170.8(3) . . . . ? C6 N2 C7 C8 -10.6(6) . . . . ? N3 C7 C8 C9 0.5(6) . . . . ? N2 C7 C8 C9 -178.0(4) . . . . ? C7 C8 C9 C10 -1.2(7) . . . . ? C8 C9 C10 C11 0.4(7) . . . . ? C9 C10 C11 N3 1.1(6) . . . . ? C7 N3 C11 C10 -1.9(6) . . . . ? 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 H1N O1 0.86(4) 2.127(18) 2.960(6) 164(5) . N2 H2N O7 0.86(4) 2.45(4) 3.118(5) 135(5) 2_556 N3 H3N O8 0.86(4) 2.30(4) 2.978(5) 137(4) . N3 H3N O7 0.86(4) 2.53(4) 3.068(5) 122(4) 2_556 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.595 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.083 data_complex9 _database_code_depnum_ccdc_archive 'CCDC 922206' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N3, 2(Cl O4)' _chemical_formula_sum 'C11 H13 Cl2 N3 O8' _chemical_formula_weight 386.14 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' Cl Cl 0.1484 0.1585 '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 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.0703(13) _cell_length_b 14.175(3) _cell_length_c 9.5289(19) _cell_angle_alpha 90.00 _cell_angle_beta 105.04(3) _cell_angle_gamma 90.00 _cell_volume 791.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 6099 _cell_measurement_theta_min 3.48 _cell_measurement_theta_max 25.86 _exptl_crystal_description prism _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.457 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8943 _exptl_absorpt_correction_T_max 0.9263 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6592 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.0719 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3093 _reflns_number_gt 2511 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'ORTEP-II (Johnson, 1976)' _computing_molecular_graphics SHELXL-97 _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^)+(0.1011P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(11) _refine_ls_number_reflns 3093 _refine_ls_number_parameters 226 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0991 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1774 _refine_ls_wR_factor_gt 0.1525 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.1429(2) 0.70137(11) 0.01595(16) 0.0598(4) Uani 1 1 d . . . Cl2 Cl 1.2273(2) 0.39161(10) 0.58467(17) 0.0617(4) Uani 1 1 d . . . O1 O 0.3705(9) 0.7087(5) 0.1048(6) 0.1007(19) Uani 1 1 d . . . O2 O 0.1265(9) 0.7597(5) -0.1081(5) 0.0892(16) Uani 1 1 d . . . O3 O -0.0208(12) 0.7284(5) 0.0885(8) 0.122(3) Uani 1 1 d . . . O4 O 0.1071(11) 0.6053(4) -0.0326(9) 0.123(2) Uani 1 1 d . . . O5 O 1.2014(9) 0.3116(4) 0.6673(7) 0.0952(18) Uani 1 1 d . . . O6 O 1.1462(10) 0.4718(5) 0.6484(8) 0.113(2) Uani 1 1 d . . . O7 O 1.1040(11) 0.3835(6) 0.4401(6) 0.119(2) Uani 1 1 d . . . O8 O 1.4664(8) 0.4051(5) 0.5989(6) 0.0887(16) Uani 1 1 d . . . N1 N 0.4602(8) 0.6673(3) 0.4153(5) 0.0522(11) Uani 1 1 d D . . H1N H 0.446(12) 0.670(5) 0.3232(18) 0.078 Uiso 1 1 d D . . N2 N 0.7818(8) 0.5738(4) 0.4467(5) 0.0559(13) Uani 1 1 d D . . H2N H 0.869(11) 0.541(5) 0.515(6) 0.084 Uiso 1 1 d D . . N3 N 0.3605(10) 0.3852(5) 0.0084(8) 0.0736(16) Uani 1 1 d D . . H3N H 0.252(11) 0.380(8) -0.070(6) 0.110 Uiso 1 1 d D . . C1 C 0.3064(10) 0.7159(5) 0.4692(8) 0.0641(17) Uani 1 1 d . . . H1 H 0.1956 0.7523 0.4068 0.077 Uiso 1 1 calc R . . C2 C 0.3123(12) 0.7121(5) 0.6098(8) 0.0701(18) Uani 1 1 d . . . H2 H 0.1991 0.7413 0.6437 0.084 Uiso 1 1 calc R . . C3 C 0.4866(11) 0.6646(5) 0.7044(7) 0.0646(17) Uani 1 1 d . . . H3 H 0.4941 0.6627 0.8031 0.078 Uiso 1 1 calc R . . C4 C 0.6491(11) 0.6201(4) 0.6520(7) 0.0583(15) Uani 1 1 d . . . H4 H 0.7706 0.5902 0.7164 0.070 Uiso 1 1 calc R . . C5 C 0.6354(9) 0.6189(4) 0.5038(7) 0.0503(14) Uani 1 1 d . . . C6 C 0.7923(11) 0.5745(5) 0.2978(7) 0.0583(15) Uani 1 1 d . . . H6A H 0.9483 0.5617 0.2953 0.070 Uiso 1 1 calc R . . H6B H 0.7540 0.6373 0.2587 0.070 Uiso 1 1 calc R . . C7 C 0.3380(11) 0.3923(5) 0.1425(9) 0.0670(16) Uani 1 1 d . . . H7 H 0.2256 0.3575 0.1695 0.080 Uiso 1 1 calc R . . C8 C 0.4794(10) 0.4506(4) 0.2427(7) 0.0581(15) Uani 1 1 d . . . H8 H 0.4675 0.4534 0.3380 0.070 Uiso 1 1 calc R . . C9 C 0.6372(9) 0.5043(4) 0.1997(6) 0.0464(13) Uani 1 1 d . . . C10 C 0.6538(11) 0.4947(5) 0.0566(7) 0.0567(15) Uani 1 1 d . . . H10 H 0.7612 0.5301 0.0253 0.068 Uiso 1 1 calc R . . C11 C 0.5165(12) 0.4349(5) -0.0367(8) 0.073(2) Uani 1 1 d . . . H11 H 0.5300 0.4283 -0.1312 0.087 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0587(7) 0.0662(9) 0.0552(9) 0.0077(7) 0.0160(6) 0.0044(7) Cl2 0.0681(9) 0.0548(8) 0.0614(9) 0.0052(7) 0.0157(7) 0.0001(8) O1 0.091(3) 0.108(4) 0.083(4) 0.024(3) -0.013(3) -0.025(3) O2 0.094(3) 0.127(4) 0.050(3) 0.025(3) 0.024(2) 0.010(3) O3 0.148(5) 0.138(6) 0.114(5) 0.050(4) 0.093(5) 0.067(5) O4 0.115(5) 0.070(4) 0.163(6) -0.022(4) -0.001(4) 0.001(3) O5 0.091(4) 0.073(3) 0.126(5) 0.034(3) 0.037(4) -0.004(3) O6 0.102(4) 0.096(4) 0.124(5) -0.027(4) -0.001(4) 0.049(4) O7 0.128(5) 0.162(6) 0.060(3) -0.008(4) 0.015(3) -0.029(5) O8 0.061(3) 0.112(4) 0.097(4) -0.014(3) 0.029(2) -0.003(3) N1 0.056(2) 0.053(3) 0.050(3) -0.001(2) 0.018(2) 0.003(2) N2 0.057(3) 0.062(3) 0.046(3) -0.001(2) 0.010(2) 0.012(3) N3 0.071(4) 0.057(3) 0.084(5) -0.011(3) 0.005(3) 0.001(3) C1 0.055(3) 0.066(4) 0.070(4) 0.004(3) 0.013(3) 0.018(3) C2 0.072(4) 0.066(4) 0.080(5) -0.015(4) 0.033(4) -0.005(4) C3 0.079(4) 0.059(4) 0.059(4) -0.006(3) 0.024(3) -0.004(3) C4 0.070(4) 0.059(3) 0.042(3) -0.002(3) 0.008(3) 0.003(3) C5 0.050(3) 0.041(3) 0.058(4) 0.001(2) 0.010(3) -0.004(2) C6 0.061(3) 0.057(3) 0.056(4) -0.004(3) 0.014(3) -0.002(3) C7 0.068(4) 0.058(3) 0.075(4) -0.003(4) 0.018(3) -0.006(4) C8 0.069(4) 0.054(4) 0.056(3) -0.004(3) 0.024(3) -0.004(3) C9 0.048(3) 0.040(3) 0.051(3) 0.003(2) 0.014(2) 0.002(2) C10 0.060(3) 0.063(4) 0.050(3) -0.001(3) 0.020(3) -0.007(3) C11 0.070(4) 0.083(5) 0.067(5) -0.018(4) 0.020(4) 0.007(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 O3 1.404(5) . ? Cl1 O1 1.425(5) . ? Cl1 O2 1.425(5) . ? Cl1 O4 1.436(6) . ? Cl2 O7 1.392(6) . ? Cl2 O5 1.413(5) . ? Cl2 O6 1.434(6) . ? Cl2 O8 1.435(5) . ? N1 C5 1.360(8) . ? N1 C1 1.363(8) . ? N1 H1N 0.86(2) . ? N2 C5 1.321(7) . ? N2 C6 1.437(8) . ? N2 H2N 0.86(2) . ? N3 C7 1.323(10) . ? N3 C11 1.337(10) . ? N3 H3N 0.86(2) . ? C1 C2 1.332(10) . ? C1 H1 0.9300 . ? C2 C3 1.375(10) . ? C2 H2 0.9300 . ? C3 C4 1.370(9) . ? C3 H3 0.9300 . ? C4 C5 1.393(8) . ? C4 H4 0.9300 . ? C6 C9 1.514(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.381(10) . ? C7 H7 0.9300 . ? C8 C9 1.367(8) . ? C8 H8 0.9300 . ? C9 C10 1.400(8) . ? C10 C11 1.349(10) . ? C10 H10 0.9300 . ? C11 H11 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 O3 Cl1 O1 112.9(5) . . ? O3 Cl1 O2 110.1(4) . . ? O1 Cl1 O2 107.4(3) . . ? O3 Cl1 O4 110.5(5) . . ? O1 Cl1 O4 107.6(4) . . ? O2 Cl1 O4 108.1(5) . . ? O7 Cl2 O5 112.1(4) . . ? O7 Cl2 O6 109.2(4) . . ? O5 Cl2 O6 107.5(4) . . ? O7 Cl2 O8 112.1(4) . . ? O5 Cl2 O8 108.1(4) . . ? O6 Cl2 O8 107.7(4) . . ? C5 N1 C1 121.5(5) . . ? C5 N1 H1N 121(5) . . ? C1 N1 H1N 117(5) . . ? C5 N2 C6 127.6(5) . . ? C5 N2 H2N 107(5) . . ? C6 N2 H2N 125(6) . . ? C7 N3 C11 122.0(6) . . ? C7 N3 H3N 126(6) . . ? C11 N3 H3N 102(7) . . ? C2 C1 N1 121.1(6) . . ? C2 C1 H1 119.5 . . ? N1 C1 H1 119.5 . . ? C1 C2 C3 119.7(6) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 119.4(6) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 121.1(6) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? N2 C5 N1 119.4(6) . . ? N2 C5 C4 123.6(6) . . ? N1 C5 C4 117.0(6) . . ? N2 C6 C9 115.2(5) . . ? N2 C6 H6A 108.5 . . ? C9 C6 H6A 108.5 . . ? N2 C6 H6B 108.5 . . ? C9 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? N3 C7 C8 120.7(7) . . ? N3 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C9 C8 C7 119.0(6) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C10 118.1(5) . . ? C8 C9 C6 123.5(5) . . ? C10 C9 C6 118.4(5) . . ? C11 C10 C9 121.0(6) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? N3 C11 C10 119.2(7) . . ? N3 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? 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 C5 N1 C1 C2 -5.0(10) . . . . ? N1 C1 C2 C3 5.2(11) . . . . ? C1 C2 C3 C4 -1.5(10) . . . . ? C2 C3 C4 C5 -2.6(10) . . . . ? C6 N2 C5 N1 5.3(9) . . . . ? C6 N2 C5 C4 -174.7(6) . . . . ? C1 N1 C5 N2 -179.2(6) . . . . ? C1 N1 C5 C4 0.8(9) . . . . ? C3 C4 C5 N2 -177.1(6) . . . . ? C3 C4 C5 N1 2.9(9) . . . . ? C5 N2 C6 C9 -84.8(7) . . . . ? C11 N3 C7 C8 -1.2(10) . . . . ? N3 C7 C8 C9 2.8(10) . . . . ? C7 C8 C9 C10 -2.5(9) . . . . ? C7 C8 C9 C6 176.7(6) . . . . ? N2 C6 C9 C8 6.8(8) . . . . ? N2 C6 C9 C10 -174.1(5) . . . . ? C8 C9 C10 C11 0.7(9) . . . . ? C6 C9 C10 C11 -178.5(6) . . . . ? C7 N3 C11 C10 -0.6(10) . . . . ? C9 C10 C11 N3 0.9(10) . . . . ? 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 H1N O1 0.86(2) 2.08(2) 2.925(7) 166(7) . N2 H2N O6 0.86(2) 2.08(3) 2.911(7) 164(8) . N3 H3N O3 0.86(2) 2.55(10) 3.009(8) 114(8) 2_545 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.606 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.109 data_complex10 _database_code_depnum_ccdc_archive 'CCDC 922207' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 N3, F6 P' _chemical_formula_sum 'C11 H12 F6 N3 P' _chemical_formula_weight 331.21 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 10.0830(4) _cell_length_b 13.1064(5) _cell_length_c 23.2914(13) _cell_angle_alpha 90.00 _cell_angle_beta 103.232(4) _cell_angle_gamma 90.00 _cell_volume 2996.3(2) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4546 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 27.49 _exptl_crystal_description prism _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9484 _exptl_absorpt_correction_T_max 0.9644 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5401 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.55 _reflns_number_total 3433 _reflns_number_gt 2401 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'ORTEP-II (Johnson, 1976)' _computing_molecular_graphics SHELXL-97 _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^)+(0.0851P)^2^+0.5140P] 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 3433 _refine_ls_number_parameters 199 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1660 _refine_ls_wR_factor_gt 0.1519 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 P1 P 0.52776(7) 0.63382(5) 0.40536(3) 0.0377(2) Uani 1 1 d . . . F1 F 0.51150(16) 0.61072(13) 0.47456(7) 0.0498(4) Uani 1 1 d . . . F2 F 0.35722(14) 0.61715(12) 0.37962(7) 0.0441(4) Uani 1 1 d . . . F3 F 0.54193(17) 0.65545(12) 0.33520(7) 0.0488(4) Uani 1 1 d . . . F4 F 0.69495(15) 0.64868(13) 0.42938(8) 0.0544(5) Uani 1 1 d . . . F5 F 0.54810(16) 0.50784(11) 0.39648(8) 0.0539(5) Uani 1 1 d . . . F6 F 0.50275(16) 0.75819(11) 0.41338(7) 0.0452(4) Uani 1 1 d . . . N1 N 0.2556(2) 0.5188(2) 0.48167(11) 0.0479(6) Uani 1 1 d D . . H1N H 0.334(4) 0.496(5) 0.501(3) 0.072 Uiso 0.50 1 d PD . . N2 N 0.2052(3) 0.34424(18) 0.35514(11) 0.0464(6) Uani 1 1 d D . . H2N H 0.143(3) 0.2981(19) 0.3498(16) 0.070 Uiso 1 1 d D . . N3 N 0.2968(2) 0.46231(18) 0.30071(10) 0.0437(6) Uani 1 1 d D . . H3N H 0.325(6) 0.501(4) 0.3311(18) 0.065 Uiso 0.50 1 d PD . . C1 C 0.1990(4) 0.5971(3) 0.50393(16) 0.0659(9) Uani 1 1 d . . . H1A H 0.2467 0.6285 0.5383 0.079 Uiso 1 1 calc R . . C2 C 0.0753(4) 0.6311(3) 0.47774(19) 0.0769(12) Uani 1 1 d . . . H2A H 0.0361 0.6852 0.4938 0.092 Uiso 1 1 calc R . . C3 C 0.0070(4) 0.5849(3) 0.4269(2) 0.0777(11) Uani 1 1 d . . . H3A H -0.0788 0.6084 0.4077 0.093 Uiso 1 1 calc R . . C4 C 0.0641(3) 0.5047(3) 0.40420(16) 0.0605(9) Uani 1 1 d . . . H4 H 0.0168 0.4725 0.3701 0.073 Uiso 1 1 calc R . . C5 C 0.1915(3) 0.4718(2) 0.43188(12) 0.0404(6) Uani 1 1 d . . . C6 C 0.2684(3) 0.3849(2) 0.41241(12) 0.0422(6) Uani 1 1 d . . . H6A H 0.3593 0.4082 0.4117 0.051 Uiso 1 1 calc R . . H6B H 0.2775 0.3305 0.4413 0.051 Uiso 1 1 calc R . . C7 C 0.2266(3) 0.37550(19) 0.30358(12) 0.0375(6) Uani 1 1 d . . . C8 C 0.1772(3) 0.3218(2) 0.25102(14) 0.0464(7) Uani 1 1 d . . . H8 H 0.1259 0.2629 0.2512 0.056 Uiso 1 1 calc R . . C9 C 0.2040(3) 0.3555(3) 0.20018(14) 0.0571(8) Uani 1 1 d . . . H9 H 0.1724 0.3186 0.1657 0.069 Uiso 1 1 calc R . . C10 C 0.2788(3) 0.4454(3) 0.19833(15) 0.0640(9) Uani 1 1 d . . . H10 H 0.2965 0.4689 0.1632 0.077 Uiso 1 1 calc R . . C11 C 0.3238(3) 0.4961(2) 0.24928(15) 0.0572(8) Uani 1 1 d . . . H11 H 0.3744 0.5555 0.2494 0.069 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0409(4) 0.0341(4) 0.0393(4) 0.0031(3) 0.0116(3) -0.0066(3) F1 0.0549(10) 0.0608(10) 0.0345(9) 0.0101(8) 0.0118(7) -0.0065(8) F2 0.0380(8) 0.0474(9) 0.0453(10) -0.0019(7) 0.0066(7) -0.0093(7) F3 0.0646(10) 0.0488(9) 0.0385(9) 0.0003(7) 0.0233(8) -0.0105(8) F4 0.0374(9) 0.0554(10) 0.0693(13) 0.0119(9) 0.0101(8) -0.0069(7) F5 0.0619(11) 0.0313(8) 0.0733(13) 0.0017(8) 0.0253(9) -0.0015(7) F6 0.0571(10) 0.0324(8) 0.0462(10) -0.0032(7) 0.0121(8) -0.0041(7) N1 0.0574(15) 0.0533(15) 0.0352(13) 0.0016(11) 0.0151(11) -0.0049(12) N2 0.0565(15) 0.0418(13) 0.0444(14) -0.0034(11) 0.0188(12) -0.0196(11) N3 0.0485(13) 0.0432(13) 0.0384(14) 0.0000(10) 0.0083(11) -0.0175(10) C1 0.089(3) 0.066(2) 0.0455(19) -0.0096(17) 0.0225(18) -0.007(2) C2 0.089(3) 0.072(3) 0.082(3) -0.002(2) 0.046(2) 0.022(2) C3 0.057(2) 0.090(3) 0.087(3) -0.008(2) 0.019(2) 0.018(2) C4 0.0423(16) 0.073(2) 0.064(2) -0.0098(18) 0.0091(15) -0.0018(16) C5 0.0424(14) 0.0441(14) 0.0384(15) 0.0042(12) 0.0165(12) -0.0098(12) C6 0.0443(15) 0.0440(15) 0.0400(16) 0.0026(12) 0.0135(12) -0.0090(12) C7 0.0350(13) 0.0371(13) 0.0418(15) -0.0020(11) 0.0115(11) -0.0094(11) C8 0.0424(15) 0.0447(15) 0.0517(18) -0.0097(14) 0.0098(13) -0.0129(12) C9 0.0541(18) 0.072(2) 0.0424(18) -0.0123(16) 0.0045(14) -0.0144(16) C10 0.066(2) 0.087(3) 0.0388(18) 0.0083(17) 0.0117(15) -0.0191(18) C11 0.0599(19) 0.061(2) 0.0512(19) 0.0069(16) 0.0143(15) -0.0257(15) _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 P1 F4 1.6616(17) . ? P1 F6 1.6665(16) . ? P1 F5 1.6823(16) . ? P1 F1 1.6844(16) . ? P1 F3 1.6966(17) . ? P1 F2 1.7007(16) . ? N1 C1 1.336(4) . ? N1 C5 1.342(4) . ? N1 H1N 0.86(3) . ? N2 C7 1.332(4) . ? N2 C6 1.442(4) . ? N2 H2N 0.86(3) . ? N3 C7 1.350(3) . ? N3 C11 1.362(4) . ? N3 H3N 0.86(3) . ? C1 C2 1.333(5) . ? C1 H1A 0.9300 . ? C2 C3 1.368(6) . ? C2 H2A 0.9300 . ? C3 C4 1.362(5) . ? C3 H3A 0.9300 . ? C4 C5 1.369(4) . ? C4 H4 0.9300 . ? C5 C6 1.504(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.401(4) . ? C8 C9 1.348(4) . ? C8 H8 0.9300 . ? C9 C10 1.404(5) . ? C9 H9 0.9300 . ? C10 C11 1.346(5) . ? C10 H10 0.9300 . ? C11 H11 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 F4 P1 F6 90.89(9) . . ? F4 P1 F5 90.78(9) . . ? F6 P1 F5 178.33(9) . . ? F4 P1 F1 90.71(9) . . ? F6 P1 F1 91.04(9) . . ? F5 P1 F1 89.00(9) . . ? F4 P1 F3 90.12(9) . . ? F6 P1 F3 89.59(8) . . ? F5 P1 F3 90.35(9) . . ? F1 P1 F3 178.95(9) . . ? F4 P1 F2 178.84(10) . . ? F6 P1 F2 89.91(8) . . ? F5 P1 F2 88.42(8) . . ? F1 P1 F2 90.12(8) . . ? F3 P1 F2 89.04(9) . . ? C1 N1 C5 121.7(3) . . ? C1 N1 H1N 119(5) . . ? C5 N1 H1N 119(5) . . ? C7 N2 C6 126.3(2) . . ? C7 N2 H2N 110(2) . . ? C6 N2 H2N 123(2) . . ? C7 N3 C11 122.0(2) . . ? C7 N3 H3N 122(4) . . ? C11 N3 H3N 115(4) . . ? C2 C1 N1 121.2(3) . . ? C2 C1 H1A 119.4 . . ? N1 C1 H1A 119.4 . . ? C1 C2 C3 118.7(4) . . ? C1 C2 H2A 120.6 . . ? C3 C2 H2A 120.6 . . ? C4 C3 C2 120.3(4) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C3 C4 C5 119.7(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? N1 C5 C4 118.4(3) . . ? N1 C5 C6 115.4(2) . . ? C4 C5 C6 126.1(3) . . ? N2 C6 C5 114.1(2) . . ? N2 C6 H6A 108.7 . . ? C5 C6 H6A 108.7 . . ? N2 C6 H6B 108.7 . . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? N2 C7 N3 119.9(2) . . ? N2 C7 C8 122.3(2) . . ? N3 C7 C8 117.8(3) . . ? C9 C8 C7 120.0(3) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 121.3(3) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C11 C10 C9 117.6(3) . . ? C11 C10 H10 121.2 . . ? C9 C10 H10 121.2 . . ? C10 C11 N3 121.3(3) . . ? C10 C11 H11 119.3 . . ? N3 C11 H11 119.3 . . ? 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 C5 N1 C1 C2 0.7(5) . . . . ? N1 C1 C2 C3 -0.7(6) . . . . ? C1 C2 C3 C4 1.0(6) . . . . ? C2 C3 C4 C5 -1.3(6) . . . . ? C1 N1 C5 C4 -1.0(4) . . . . ? C1 N1 C5 C6 180.0(3) . . . . ? C3 C4 C5 N1 1.3(5) . . . . ? C3 C4 C5 C6 -179.8(3) . . . . ? C7 N2 C6 C5 89.9(3) . . . . ? N1 C5 C6 N2 -172.5(2) . . . . ? C4 C5 C6 N2 8.5(4) . . . . ? C6 N2 C7 N3 -10.8(4) . . . . ? C6 N2 C7 C8 169.9(3) . . . . ? C11 N3 C7 N2 178.5(3) . . . . ? C11 N3 C7 C8 -2.2(4) . . . . ? N2 C7 C8 C9 -178.6(3) . . . . ? N3 C7 C8 C9 2.1(4) . . . . ? C7 C8 C9 C10 -1.3(5) . . . . ? C8 C9 C10 C11 0.6(5) . . . . ? C9 C10 C11 N3 -0.7(6) . . . . ? C7 N3 C11 C10 1.5(5) . . . . ? 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 H1N F1 0.86(3) 2.08(3) 2.888(3) 156(7) 5_666 N1 H1N F4 0.86(3) 2.56(7) 2.981(3) 111(5) 5_666 N2 H2N F3 0.86(3) 2.122(14) 2.949(3) 163(3) 3_445 N2 H2N F6 0.86(3) 2.33(3) 2.923(3) 127(3) 3_445 N3 H3N F2 0.86(3) 1.88(2) 2.712(3) 161(6) . N3 H3N F5 0.86(3) 2.41(5) 3.027(3) 129(5) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.249 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.061 data_complex11 _database_code_depnum_ccdc_archive 'CCDC 922208' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 N3, F6 P' _chemical_formula_sum 'C11 H12 F6 N3 P' _chemical_formula_weight 331.21 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' F F 0.0171 0.0103 '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' P P 0.1023 0.0942 '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/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.3681(15) _cell_length_b 12.231(2) _cell_length_c 15.253(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.31(3) _cell_angle_gamma 90.00 _cell_volume 1360.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 6232 _cell_measurement_theta_min 3.17 _cell_measurement_theta_max 25.92 _exptl_crystal_description prism _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.268 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9384 _exptl_absorpt_correction_T_max 0.9558 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11132 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2667 _reflns_number_gt 1966 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'ORTEP-II (Johnson, 1976)' _computing_molecular_graphics SHELXL-97 _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^)+(0.1444P)^2^+0.3500P] 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 2667 _refine_ls_number_parameters 196 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0681 _refine_ls_wR_factor_ref 0.2261 _refine_ls_wR_factor_gt 0.2058 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 P1 P 0.44245(12) 0.14006(7) 0.69558(6) 0.0556(4) Uani 1 1 d . . . F1 F 0.6618(3) 0.14487(19) 0.70768(16) 0.0754(7) Uani 1 1 d . . . F2 F 0.2254(3) 0.1326(2) 0.68483(17) 0.0905(8) Uani 1 1 d . . . F3 F 0.4442(3) 0.2044(2) 0.78617(15) 0.0843(8) Uani 1 1 d . . . F4 F 0.4572(4) 0.0291(2) 0.75079(18) 0.0875(8) Uani 1 1 d . . . F5 F 0.4418(4) 0.0735(3) 0.60648(16) 0.0972(9) Uani 1 1 d . . . F6 F 0.4313(5) 0.2494(3) 0.6417(2) 0.1236(12) Uani 1 1 d . . . N1 N 0.7307(4) 0.4087(3) 0.4532(2) 0.0672(8) Uani 1 1 d D . . H1N H 0.708(7) 0.365(3) 0.407(2) 0.101 Uiso 1 1 d D . . N2 N 0.8078(5) 0.2561(2) 0.55205(19) 0.0654(8) Uani 1 1 d D . . H2N H 0.826(6) 0.227(4) 0.6041(15) 0.098 Uiso 1 1 d D . . N3 N 0.9524(5) 0.1263(2) 0.27688(18) 0.0591(8) Uani 1 1 d . . . C1 C 0.7121(5) 0.5204(3) 0.4455(2) 0.0610(9) Uani 1 1 d . . . H1A H 0.6728 0.5507 0.3901 0.073 Uiso 1 1 calc R . . C2 C 0.7501(5) 0.5882(3) 0.5175(3) 0.0642(9) Uani 1 1 d . . . H2A H 0.7372 0.6636 0.5117 0.077 Uiso 1 1 calc R . . C3 C 0.8075(5) 0.5412(3) 0.5978(2) 0.0640(10) Uani 1 1 d . . . H3A H 0.8345 0.5855 0.6475 0.077 Uiso 1 1 calc R . . C4 C 0.8257(4) 0.4321(2) 0.60639(17) 0.0423(7) Uani 1 1 d . . . H4A H 0.8658 0.4032 0.6622 0.051 Uiso 1 1 calc R . . C5 C 0.7882(4) 0.3635(3) 0.5374(2) 0.0489(8) Uani 1 1 d . . . C6 C 0.7497(6) 0.1741(3) 0.4857(3) 0.0653(10) Uani 1 1 d . . . H6A H 0.6365 0.1979 0.4504 0.078 Uiso 1 1 calc R . . H6B H 0.7244 0.1066 0.5150 0.078 Uiso 1 1 calc R . . C7 C 0.8378(5) 0.1473(2) 0.3345(2) 0.0540(8) Uani 1 1 d . . . H7A H 0.7150 0.1597 0.3126 0.065 Uiso 1 1 calc R . . C8 C 0.8905(5) 0.1519(2) 0.4249(2) 0.0491(7) Uani 1 1 d . . . C9 C 1.0715(5) 0.1303(3) 0.4563(2) 0.0594(9) Uani 1 1 d . . . H9A H 1.1124 0.1314 0.5169 0.071 Uiso 1 1 calc R . . C10 C 1.1912(5) 0.1073(3) 0.3982(3) 0.0682(10) Uani 1 1 d . . . H10A H 1.3135 0.0917 0.4187 0.082 Uiso 1 1 calc R . . C11 C 1.1282(6) 0.1077(3) 0.3095(3) 0.0660(9) Uani 1 1 d . . . H11A H 1.2109 0.0945 0.2701 0.079 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0573(6) 0.0663(6) 0.0420(5) 0.0054(4) 0.0030(4) 0.0011(4) F1 0.0603(14) 0.0885(16) 0.0768(16) 0.0056(11) 0.0082(11) -0.0042(10) F2 0.0594(15) 0.140(2) 0.0688(16) -0.0050(14) -0.0012(11) 0.0057(12) F3 0.0834(16) 0.0969(18) 0.0721(15) -0.0229(13) 0.0096(12) -0.0023(13) F4 0.0980(18) 0.0776(16) 0.0860(18) 0.0209(13) 0.0095(14) -0.0102(12) F5 0.0885(18) 0.146(3) 0.0560(14) -0.0248(15) 0.0049(12) 0.0081(16) F6 0.137(3) 0.107(2) 0.131(3) 0.071(2) 0.034(2) 0.0339(19) N1 0.0706(19) 0.082(2) 0.0486(17) -0.0008(15) 0.0070(14) -0.0028(16) N2 0.101(2) 0.0581(18) 0.0394(15) 0.0040(12) 0.0193(15) 0.0046(15) N3 0.074(2) 0.0649(17) 0.0383(14) 0.0003(12) 0.0064(13) 0.0026(14) C1 0.062(2) 0.066(2) 0.054(2) 0.0121(16) 0.0061(16) 0.0052(16) C2 0.070(2) 0.057(2) 0.066(2) 0.0005(17) 0.0123(18) -0.0020(17) C3 0.062(2) 0.078(2) 0.054(2) -0.0188(18) 0.0164(16) -0.0073(17) C4 0.0484(16) 0.0554(17) 0.0238(12) -0.0015(11) 0.0075(11) 0.0015(13) C5 0.0509(17) 0.0611(19) 0.0363(15) -0.0003(13) 0.0124(13) -0.0025(13) C6 0.081(2) 0.0553(19) 0.064(2) 0.0003(17) 0.0259(19) -0.0089(18) C7 0.0560(19) 0.0538(18) 0.0491(18) 0.0041(14) -0.0027(15) 0.0007(14) C8 0.0605(19) 0.0424(16) 0.0438(17) 0.0005(12) 0.0054(14) -0.0042(13) C9 0.067(2) 0.061(2) 0.0456(18) 0.0014(14) -0.0077(16) -0.0045(15) C10 0.053(2) 0.073(2) 0.076(3) -0.005(2) 0.0007(18) 0.0008(17) C11 0.076(2) 0.064(2) 0.061(2) -0.0044(17) 0.0197(18) -0.0003(18) _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 P1 F6 1.566(3) . ? P1 F5 1.584(2) . ? P1 F2 1.586(3) . ? P1 F3 1.588(2) . ? P1 F4 1.593(2) . ? P1 F1 1.601(2) . ? N1 C1 1.377(5) . ? N1 C5 1.406(4) . ? N1 H1N 0.88(3) . ? N2 C5 1.338(4) . ? N2 C6 1.445(5) . ? N2 H2N 0.86(3) . ? N3 C7 1.329(4) . ? N3 C11 1.338(5) . ? C1 C2 1.372(5) . ? C1 H1A 0.9300 . ? C2 C3 1.363(5) . ? C2 H2A 0.9300 . ? C3 C4 1.346(5) . ? C3 H3A 0.9300 . ? C4 C5 1.344(4) . ? C4 H4A 0.9300 . ? C6 C8 1.512(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.379(4) . ? C7 H7A 0.9300 . ? C8 C9 1.376(5) . ? C9 C10 1.367(5) . ? C9 H9A 0.9300 . ? C10 C11 1.365(6) . ? C10 H10A 0.9300 . ? C11 H11A 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 F6 P1 F5 89.77(18) . . ? F6 P1 F2 91.09(17) . . ? F5 P1 F2 90.20(14) . . ? F6 P1 F3 91.50(18) . . ? F5 P1 F3 178.71(16) . . ? F2 P1 F3 89.97(14) . . ? F6 P1 F4 179.09(17) . . ? F5 P1 F4 90.39(16) . . ? F2 P1 F4 89.80(14) . . ? F3 P1 F4 88.33(14) . . ? F6 P1 F1 90.27(16) . . ? F5 P1 F1 89.76(14) . . ? F2 P1 F1 178.64(15) . . ? F3 P1 F1 90.04(13) . . ? F4 P1 F1 88.84(14) . . ? C1 N1 C5 118.7(3) . . ? C1 N1 H1N 122(3) . . ? C5 N1 H1N 120(3) . . ? C5 N2 C6 123.4(3) . . ? C5 N2 H2N 124(3) . . ? C6 N2 H2N 110(3) . . ? C7 N3 C11 117.4(3) . . ? C2 C1 N1 121.7(3) . . ? C2 C1 H1A 119.2 . . ? N1 C1 H1A 119.2 . . ? C3 C2 C1 117.7(3) . . ? C3 C2 H2A 121.1 . . ? C1 C2 H2A 121.1 . . ? C4 C3 C2 121.3(3) . . ? C4 C3 H3A 119.3 . . ? C2 C3 H3A 119.3 . . ? C5 C4 C3 122.4(3) . . ? C5 C4 H4A 118.8 . . ? C3 C4 H4A 118.8 . . ? N2 C5 C4 118.5(3) . . ? N2 C5 N1 123.4(3) . . ? C4 C5 N1 118.1(3) . . ? N2 C6 C8 113.2(3) . . ? N2 C6 H6A 108.9 . . ? C8 C6 H6A 108.9 . . ? N2 C6 H6B 108.9 . . ? C8 C6 H6B 108.9 . . ? H6A C6 H6B 107.8 . . ? N3 C7 C8 123.7(3) . . ? N3 C7 H7A 118.1 . . ? C8 C7 H7A 118.1 . . ? C9 C8 C7 117.3(3) . . ? C9 C8 C6 122.5(3) . . ? C7 C8 C6 120.1(3) . . ? C10 C9 C8 119.9(3) . . ? C10 C9 H9A 120.1 . . ? C8 C9 H9A 120.1 . . ? C11 C10 C9 118.9(4) . . ? C11 C10 H10A 120.6 . . ? C9 C10 H10A 120.6 . . ? N3 C11 C10 122.8(4) . . ? N3 C11 H11A 118.6 . . ? C10 C11 H11A 118.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 0.7(5) . . . . ? N1 C1 C2 C3 0.0(5) . . . . ? C1 C2 C3 C4 -0.2(5) . . . . ? C2 C3 C4 C5 -0.3(5) . . . . ? C6 N2 C5 C4 171.8(3) . . . . ? C6 N2 C5 N1 -8.3(5) . . . . ? C3 C4 C5 N2 -179.1(3) . . . . ? C3 C4 C5 N1 1.0(4) . . . . ? C1 N1 C5 N2 179.0(3) . . . . ? C1 N1 C5 C4 -1.2(5) . . . . ? C5 N2 C6 C8 84.3(4) . . . . ? C11 N3 C7 C8 0.6(5) . . . . ? N3 C7 C8 C9 -1.8(5) . . . . ? N3 C7 C8 C6 -178.8(3) . . . . ? N2 C6 C8 C9 50.1(4) . . . . ? N2 C6 C8 C7 -133.1(3) . . . . ? C7 C8 C9 C10 1.0(5) . . . . ? C6 C8 C9 C10 177.9(3) . . . . ? C8 C9 C10 C11 0.9(5) . . . . ? C7 N3 C11 C10 1.4(5) . . . . ? C9 C10 C11 N3 -2.2(6) . . . . ? 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 H1N F3 0.88(3) 2.62(3) 3.362(4) 143(4) 4_565 N2 H2N F1 0.86(3) 2.35(3) 3.063(4) 140(4) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.621 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.144 data_complex12 _database_code_depnum_ccdc_archive 'CCDC 922209' #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 N3, C11 H13 N3, 3(F6 P)' _chemical_formula_sum 'C22 H25 F18 N6 P3' _chemical_formula_weight 808.39 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0000 '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 c' _symmetry_space_group_name_Hall 'P -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 6.3859(2) _cell_length_b 13.0144(5) _cell_length_c 18.0253(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.581(4) _cell_angle_gamma 90.00 _cell_volume 1481.29(9) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 8042 _cell_measurement_theta_min 3.23 _cell_measurement_theta_max 27.43 _exptl_crystal_description prism _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.812 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 812 _exptl_absorpt_coefficient_mu 0.343 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9314 _exptl_absorpt_correction_T_max 0.9471 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9409 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6752 _reflns_number_gt 4351 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'ORTEP-II (Johnson, 1976)' _computing_molecular_graphics SHELXL-97 _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^)+(0.0870P)^2^+0.6699P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 6752 _refine_ls_number_parameters 436 _refine_ls_number_restraints 147 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1538 _refine_ls_wR_factor_gt 0.1329 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.080 _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 P1 P 0.5011(8) 0.2505(3) 0.5002(2) 0.0356(3) Uani 1 1 d . . . P2 P 0.5454(4) 0.7451(2) 0.67105(14) 0.0357(7) Uani 1 1 d . . . P3 P 0.4547(4) 0.2449(2) 0.82950(14) 0.0389(8) Uani 1 1 d . . . F4 F 0.5184(11) 0.3671(5) 0.5421(4) 0.0462(16) Uani 1 1 d U . . F5 F 0.4844(13) 0.1916(5) 0.5840(3) 0.0551(19) Uani 1 1 d U . . F2 F 0.4778(10) 0.1371(5) 0.4583(3) 0.0397(14) Uani 1 1 d U . . F6 F 0.5146(12) 0.3078(6) 0.4178(3) 0.0551(19) Uani 1 1 d U . . F3 F 0.2347(12) 0.2611(6) 0.4866(4) 0.053(2) Uani 1 1 d U . . F1 F 0.7673(13) 0.2381(6) 0.5159(4) 0.052(2) Uani 1 1 d U . . F7 F 0.571(2) 0.7284(9) 0.7585(5) 0.115(4) Uani 1 1 d U . . F8 F 0.5126(13) 0.8682(5) 0.6735(5) 0.073(2) Uani 1 1 d U . . F9 F 0.5168(16) 0.7565(7) 0.5844(4) 0.080(3) Uani 1 1 d U . . F10 F 0.5573(15) 0.6244(6) 0.6530(6) 0.096(3) Uani 1 1 d U . . F11 F 0.2932(12) 0.7325(6) 0.6675(5) 0.064(2) Uani 1 1 d U . . F12 F 0.7951(13) 0.7573(6) 0.6762(5) 0.068(2) Uani 1 1 d U . . F13 F 0.4229(19) 0.2385(8) 0.7419(4) 0.096(3) Uani 1 1 d U . . F14 F 0.4131(13) 0.1276(5) 0.8286(5) 0.086(2) Uani 1 1 d U . . F15 F 0.4766(18) 0.2605(8) 0.9175(5) 0.090(3) Uani 1 1 d U . . F16 F 0.4680(13) 0.3622(6) 0.8160(5) 0.079(2) Uani 1 1 d U . . F17 F 0.6965(14) 0.2314(6) 0.8316(5) 0.068(2) Uani 1 1 d U . . F18 F 0.2052(11) 0.2593(5) 0.8262(4) 0.054(2) Uani 1 1 d U . . N2 N 0.9108(17) 0.5860(7) 0.8490(4) 0.044(2) Uani 1 1 d D . . H2N H 0.8164 0.6335 0.8467 0.066 Uiso 0.50 1 calc PR A 1 H2N' H 0.7972 0.6252 0.8427 0.066 Uiso 0.50 1 d PR A 2 N3 N 0.9728(16) 0.3522(6) 0.6330(4) 0.040(2) Uani 1 1 d . B . H3N H 0.9530 0.3069 0.5979 0.059 Uiso 1 1 calc R . . N4 N 0.2119(12) 0.0208(6) 0.5471(4) 0.041(2) Uani 1 1 d . . . H4N H 0.3131 0.0649 0.5551 0.062 Uiso 1 1 calc R . . N5 N 0.0886(17) 0.0856(7) 0.6511(5) 0.044(2) Uani 1 1 d . . . H5N H 0.1934 0.1278 0.6561 0.066 Uiso 1 1 calc R . . C12 C 0.1423(16) -0.0695(8) 0.7681(6) 0.038(2) Uani 1 1 d . . . H12 H 0.2407 -0.0645 0.7351 0.057 Uiso 1 1 calc R . . C2 C 0.980(3) 0.3893(17) 1.0315(9) 0.037(4) Uani 0.50 1 d PGU B 1 H2A H 1.0011 0.3477 1.0739 0.044 Uiso 0.50 1 calc PR B 1 C1 C 0.802(3) 0.452(2) 1.0182(11) 0.042(3) Uani 0.50 1 d PGU B 1 H1 H 0.7049 0.4527 1.0517 0.050 Uiso 0.50 1 calc PR B 1 N1 N 0.771(3) 0.5145(18) 0.9548(13) 0.036(3) Uani 0.50 1 d PGU B 1 C5 C 0.917(4) 0.5137(18) 0.9048(11) 0.030(3) Uani 0.50 1 d PGDU B 1 C4 C 1.094(4) 0.451(2) 0.9181(11) 0.036(3) Uani 0.50 1 d PGU B 1 H4A H 1.1916 0.4503 0.8846 0.043 Uiso 0.50 1 calc PR B 1 C3 C 1.126(3) 0.3886(18) 0.9814(12) 0.040(3) Uani 0.50 1 d PGU B 1 H3A H 1.2445 0.3465 0.9903 0.048 Uiso 0.50 1 calc PR B 1 C2' C 0.924(3) 0.3858(17) 1.0267(11) 0.037(4) Uani 0.50 1 d PG B 2 H2'A H 0.9145 0.3396 1.0653 0.044 Uiso 0.50 1 calc PR B 2 C1' C 0.767(3) 0.4590(19) 1.0078(12) 0.042(3) Uani 0.50 1 d PG B 2 H1' H 0.6516 0.4617 1.0339 0.050 Uiso 0.50 1 calc PR B 2 N1' N 0.781(4) 0.5282(17) 0.9500(14) 0.036(3) Uani 0.50 1 d PG B 2 C5' C 0.953(4) 0.5241(18) 0.9111(11) 0.030(3) Uani 0.50 1 d PGD B 2 C4' C 1.111(3) 0.451(2) 0.9299(11) 0.036(3) Uani 0.50 1 d PG B 2 H4' H 1.2259 0.4482 0.9039 0.043 Uiso 0.50 1 calc PR B 2 C3' C 1.096(3) 0.3818(17) 0.9877(13) 0.040(3) Uani 0.50 1 d PG B 2 H3' H 1.2016 0.3328 1.0003 0.048 Uiso 0.50 1 calc PR B 2 C6 C 1.1449(19) 0.4102(9) 0.6376(6) 0.044(3) Uani 1 1 d . . . H6 H 1.2412 0.4003 0.6043 0.053 Uiso 1 1 calc R . . C7 C 1.1801(18) 0.4844(9) 0.6915(6) 0.043(3) Uani 1 1 d . B . H7 H 1.3023 0.5243 0.6974 0.051 Uiso 1 1 calc R . . C8 C 1.0229(16) 0.4979(8) 0.7379(5) 0.0283(19) Uani 1 1 d . . . C9 C 0.8509(18) 0.4365(8) 0.7319(5) 0.036(2) Uani 1 1 d . B . H9 H 0.7483 0.4455 0.7629 0.043 Uiso 1 1 calc R . . C10 C 0.8319(19) 0.3593(7) 0.6778(6) 0.042(3) Uani 1 1 d . . . H10 H 0.7193 0.3133 0.6737 0.050 Uiso 1 1 calc R B . C11 C 1.054(2) 0.5873(7) 0.7935(6) 0.039(2) Uani 1 1 d . B . H11A H 1.1986 0.5858 0.8194 0.047 Uiso 1 1 calc R . . H11B H 1.0350 0.6513 0.7658 0.047 Uiso 1 1 calc R . . C13 C 0.1691(19) -0.1417(8) 0.8221(5) 0.043(3) Uani 1 1 d . . . H13 H 0.2890 -0.1832 0.8275 0.052 Uiso 1 1 calc R . . N6 N 0.0243(17) -0.1547(7) 0.8686(5) 0.047(2) Uani 1 1 d . . . H6N H 0.0419 -0.2015 0.9027 0.057 Uiso 1 1 calc R . . C14 C -0.147(2) -0.0943(10) 0.8614(6) 0.051(3) Uani 1 1 d . . . H14 H -0.2484 -0.1038 0.8928 0.061 Uiso 1 1 calc R . . C15 C -0.1740(18) -0.0184(8) 0.8080(6) 0.039(2) Uani 1 1 d . . . H15 H -0.2942 0.0228 0.8043 0.046 Uiso 1 1 calc R . . C16 C -0.0318(16) -0.0011(7) 0.7603(6) 0.035(2) Uani 1 1 d . . . C17 C 0.0672(13) 0.0221(6) 0.5930(4) 0.034(2) Uani 1 1 d . . . C18 C -0.1005(14) -0.0478(7) 0.5753(5) 0.043(3) Uani 1 1 d . . . H18 H -0.2100 -0.0502 0.6040 0.051 Uiso 1 1 calc R . . C19 C -0.1006(16) -0.1114(7) 0.5163(5) 0.047(3) Uani 1 1 d . . . H19 H -0.2132 -0.1568 0.5048 0.056 Uiso 1 1 calc R . . C20 C 0.0589(16) -0.1125(7) 0.4718(5) 0.045(3) Uani 1 1 d . . . H20 H 0.0586 -0.1583 0.4321 0.053 Uiso 1 1 calc R . . C21 C 0.2121(14) -0.0438(7) 0.4896(5) 0.046(3) Uani 1 1 d . . . H21 H 0.3223 -0.0407 0.4613 0.055 Uiso 1 1 calc R . . C22 C -0.052(2) 0.0883(9) 0.7060(6) 0.046(3) Uani 1 1 d . . . H22A H -0.1960 0.0905 0.6801 0.056 Uiso 1 1 calc R . . H22B H -0.0264 0.1514 0.7345 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0326(6) 0.0427(7) 0.0333(6) -0.0094(5) 0.0103(5) -0.0117(5) P2 0.0311(16) 0.0392(15) 0.0383(16) -0.0030(12) 0.0101(17) -0.0025(12) P3 0.0379(17) 0.0428(17) 0.0381(17) 0.0003(12) 0.0122(18) 0.0026(12) F4 0.050(3) 0.038(3) 0.054(3) -0.017(3) 0.018(3) -0.008(3) F5 0.082(5) 0.049(3) 0.037(3) -0.007(3) 0.017(3) -0.030(3) F2 0.040(3) 0.042(3) 0.037(3) -0.013(3) 0.007(2) -0.014(3) F6 0.064(4) 0.075(4) 0.027(3) -0.004(3) 0.009(3) -0.018(4) F3 0.027(3) 0.061(4) 0.070(5) -0.025(3) 0.007(3) -0.005(3) F1 0.032(4) 0.067(4) 0.057(4) -0.028(3) 0.009(3) -0.011(3) F7 0.095(7) 0.201(8) 0.052(4) 0.044(5) 0.023(5) 0.018(6) F8 0.064(4) 0.047(3) 0.114(5) 0.018(3) 0.033(4) 0.005(3) F9 0.073(5) 0.133(7) 0.036(3) -0.014(4) 0.009(3) -0.005(5) F10 0.107(6) 0.048(4) 0.154(6) -0.024(4) 0.086(5) -0.020(3) F11 0.033(4) 0.075(5) 0.088(5) -0.004(4) 0.019(4) -0.011(4) F12 0.041(4) 0.085(5) 0.081(5) 0.002(4) 0.017(4) -0.006(4) F13 0.094(6) 0.151(7) 0.047(4) -0.005(4) 0.025(4) 0.006(5) F14 0.064(4) 0.036(3) 0.162(6) -0.002(4) 0.028(4) 0.003(3) F15 0.087(6) 0.123(7) 0.059(4) -0.011(4) 0.006(4) 0.020(5) F16 0.066(4) 0.067(4) 0.110(5) 0.045(4) 0.031(4) 0.005(3) F17 0.045(4) 0.066(4) 0.094(5) 0.006(4) 0.016(4) 0.005(4) F18 0.033(4) 0.063(4) 0.068(4) -0.014(3) 0.010(3) -0.003(3) N2 0.061(6) 0.040(5) 0.031(5) -0.002(4) 0.006(4) 0.023(5) N3 0.065(6) 0.024(4) 0.025(4) -0.004(3) -0.010(4) -0.003(4) N4 0.043(5) 0.038(4) 0.045(5) 0.013(4) 0.012(4) -0.013(4) N5 0.052(6) 0.036(5) 0.044(5) -0.003(4) 0.006(5) -0.008(5) C12 0.027(5) 0.040(5) 0.046(6) -0.008(5) 0.003(4) 0.007(4) C2 0.037(7) 0.036(5) 0.037(5) 0.000(4) 0.005(4) 0.001(5) C1 0.041(6) 0.045(5) 0.041(5) 0.001(4) 0.008(4) 0.000(4) N1 0.036(4) 0.036(5) 0.036(4) -0.002(3) 0.007(3) -0.001(4) C5 0.027(6) 0.032(5) 0.033(5) -0.009(4) 0.008(4) 0.000(4) C4 0.036(5) 0.037(4) 0.034(5) -0.002(4) 0.005(4) 0.007(4) C3 0.039(5) 0.040(5) 0.042(5) 0.001(4) 0.009(4) 0.003(4) C2' 0.037(7) 0.036(5) 0.037(5) 0.000(4) 0.005(4) 0.001(5) C1' 0.041(6) 0.045(5) 0.041(5) 0.001(4) 0.008(4) 0.000(4) N1' 0.036(4) 0.036(5) 0.036(4) -0.002(3) 0.007(3) -0.001(4) C5' 0.027(6) 0.032(5) 0.033(5) -0.009(4) 0.008(4) 0.000(4) C4' 0.036(5) 0.037(4) 0.034(5) -0.002(4) 0.005(4) 0.007(4) C3' 0.039(5) 0.040(5) 0.042(5) 0.001(4) 0.009(4) 0.003(4) C6 0.054(7) 0.043(6) 0.041(6) 0.006(5) 0.023(5) -0.003(5) C7 0.035(5) 0.058(7) 0.035(5) 0.006(5) 0.004(5) -0.005(5) C8 0.032(5) 0.036(4) 0.016(4) -0.001(4) 0.001(4) 0.005(4) C9 0.045(6) 0.036(5) 0.029(5) -0.005(4) 0.010(4) -0.004(4) C10 0.045(6) 0.024(5) 0.053(6) 0.003(5) -0.006(5) 0.003(4) C11 0.051(6) 0.024(5) 0.043(6) 0.005(4) 0.011(5) -0.004(5) C13 0.049(6) 0.051(6) 0.027(5) -0.003(5) -0.005(5) 0.024(5) N6 0.063(6) 0.035(5) 0.043(5) 0.007(4) 0.004(5) -0.009(5) C14 0.055(7) 0.057(7) 0.039(6) -0.001(5) 0.001(5) -0.024(6) C15 0.039(5) 0.031(5) 0.048(6) -0.007(4) 0.012(5) 0.008(4) C16 0.039(6) 0.021(4) 0.043(5) -0.016(4) -0.005(5) 0.008(4) C17 0.043(5) 0.023(4) 0.031(4) 0.010(4) -0.007(4) -0.002(4) C18 0.054(5) 0.043(5) 0.033(5) 0.002(4) 0.013(4) -0.017(5) C19 0.060(6) 0.036(5) 0.040(5) -0.005(4) -0.003(5) -0.020(5) C20 0.057(6) 0.037(5) 0.040(5) 0.003(4) 0.006(5) 0.006(5) C21 0.058(6) 0.042(6) 0.040(5) 0.015(4) 0.020(5) 0.003(5) C22 0.060(7) 0.042(6) 0.034(5) 0.005(5) -0.003(5) 0.009(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 P1 F2 1.654(7) . ? P1 F6 1.676(7) . ? P1 F3 1.688(7) . ? P1 F1 1.689(8) . ? P1 F4 1.692(7) . ? P1 F5 1.712(7) . ? P2 F9 1.551(7) . ? P2 F7 1.575(9) . ? P2 F12 1.592(9) . ? P2 F10 1.608(8) . ? P2 F11 1.611(8) . ? P2 F8 1.617(7) . ? P3 F14 1.549(7) . ? P3 F17 1.549(9) . ? P3 F16 1.550(8) . ? P3 F13 1.563(8) . ? P3 F15 1.585(9) . ? P3 F18 1.597(8) . ? N2 C5' 1.373(11) . ? N2 C5 1.374(11) . ? N2 C11 1.452(14) . ? N2 H2N 0.8600 . ? N2 H2N' 0.8800 . ? N3 C10 1.299(15) . ? N3 C6 1.325(14) . ? N3 H3N 0.8600 . ? N4 C17 1.329(8) . ? N4 C21 1.335(9) . ? N4 H4N 0.8600 . ? N5 C17 1.325(11) . ? N5 C22 1.431(15) . ? N5 H5N 0.8600 . ? C12 C13 1.345(15) . ? C12 C16 1.415(13) . ? C12 H12 0.9300 . ? C2 C1 1.3900 . ? C2 C3 1.3900 . ? C2 H2A 0.9300 . ? C1 N1 1.3900 . ? C1 H1 0.9300 . ? N1 C5 1.3900 . ? C5 C4 1.3900 . ? C4 C3 1.3900 . ? C4 H4A 0.9300 . ? C3 H3A 0.9300 . ? C2' C1' 1.3900 . ? C2' C3' 1.3900 . ? C2' H2'A 0.9300 . ? C1' N1' 1.3900 . ? C1' H1' 0.9300 . ? N1' C5' 1.3900 . ? C5' C4' 1.3900 . ? C4' C3' 1.3900 . ? C4' H4' 0.9300 . ? C3' H3' 0.9300 . ? C6 C7 1.365(15) . ? C6 H6 0.9300 . ? C7 C8 1.410(13) . ? C7 H7 0.9300 . ? C8 C9 1.350(14) . ? C8 C11 1.529(13) . ? C9 C10 1.394(14) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C13 N6 1.348(14) . ? C13 H13 0.9300 . ? N6 C14 1.337(17) . ? N6 H6N 0.8600 . ? C14 C15 1.372(15) . ? C14 H14 0.9300 . ? C15 C16 1.359(13) . ? C15 H15 0.9300 . ? C16 C22 1.514(14) . ? C17 C18 1.405(9) . ? C18 C19 1.348(9) . ? C18 H18 0.9300 . ? C19 C20 1.387(11) . ? C19 H19 0.9300 . ? C20 C21 1.329(10) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? 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 F2 P1 F6 90.3(4) . . ? F2 P1 F3 89.2(4) . . ? F6 P1 F3 91.1(5) . . ? F2 P1 F1 90.7(4) . . ? F6 P1 F1 90.4(5) . . ? F3 P1 F1 178.5(6) . . ? F2 P1 F4 178.5(6) . . ? F6 P1 F4 89.3(4) . . ? F3 P1 F4 89.4(4) . . ? F1 P1 F4 90.8(4) . . ? F2 P1 F5 89.4(4) . . ? F6 P1 F5 179.4(6) . . ? F3 P1 F5 88.3(5) . . ? F1 P1 F5 90.2(5) . . ? F4 P1 F5 90.9(4) . . ? F9 P2 F7 177.4(6) . . ? F9 P2 F12 90.9(5) . . ? F7 P2 F12 90.0(6) . . ? F9 P2 F10 83.8(5) . . ? F7 P2 F10 93.8(6) . . ? F12 P2 F10 91.8(4) . . ? F9 P2 F11 90.2(5) . . ? F7 P2 F11 88.9(6) . . ? F12 P2 F11 178.9(5) . . ? F10 P2 F11 88.2(4) . . ? F9 P2 F8 86.4(5) . . ? F7 P2 F8 95.9(6) . . ? F12 P2 F8 91.8(4) . . ? F10 P2 F8 169.6(6) . . ? F11 P2 F8 88.3(4) . . ? F14 P3 F17 93.3(4) . . ? F14 P3 F16 169.2(5) . . ? F17 P3 F16 92.2(4) . . ? F14 P3 F13 86.6(6) . . ? F17 P3 F13 89.9(6) . . ? F16 P3 F13 84.0(5) . . ? F14 P3 F15 97.2(5) . . ? F17 P3 F15 93.0(5) . . ? F16 P3 F15 91.8(5) . . ? F13 P3 F15 175.1(6) . . ? F14 P3 F18 86.9(4) . . ? F17 P3 F18 179.2(5) . . ? F16 P3 F18 87.5(4) . . ? F13 P3 F18 89.4(5) . . ? F15 P3 F18 87.8(5) . . ? C5' N2 C11 120.0(13) . . ? C5 N2 C11 124.1(14) . . ? C5' N2 H2N 120.8 . . ? C5 N2 H2N 117.9 . . ? C11 N2 H2N 117.9 . . ? C5' N2 H2N' 120.2 . . ? C5 N2 H2N' 114.9 . . ? C11 N2 H2N' 119.8 . . ? C10 N3 C6 124.4(9) . . ? C10 N3 H3N 117.8 . . ? C6 N3 H3N 117.8 . . ? C17 N4 C21 124.9(6) . . ? C17 N4 H4N 117.5 . . ? C21 N4 H4N 117.5 . . ? C17 N5 C22 124.1(9) . . ? C17 N5 H5N 118.0 . . ? C22 N5 H5N 118.0 . . ? C13 C12 C16 121.6(10) . . ? C13 C12 H12 119.2 . . ? C16 C12 H12 119.2 . . ? C1 C2 C3 120.0 . . ? C1 C2 H2A 120.0 . . ? C3 C2 H2A 120.0 . . ? C2 C1 N1 120.0 . . ? C2 C1 H1 120.0 . . ? N1 C1 H1 120.0 . . ? C5 N1 C1 120.0 . . ? N2 C5 N1 121.6(17) . . ? N2 C5 C4 117.5(17) . . ? N1 C5 C4 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C1' C2' C3' 120.0 . . ? C1' C2' H2'A 120.0 . . ? C3' C2' H2'A 120.0 . . ? C2' C1' N1' 120.0 . . ? C2' C1' H1' 120.0 . . ? N1' C1' H1' 120.0 . . ? C1' N1' C5' 120.0 . . ? N2 C5' C4' 130.4(17) . . ? N2 C5' N1' 108.4(16) . . ? C4' C5' N1' 120.0 . . ? C5' C4' C3' 120.0 . . ? C5' C4' H4' 120.0 . . ? C3' C4' H4' 120.0 . . ? C4' C3' C2' 120.0 . . ? C4' C3' H3' 120.0 . . ? C2' C3' H3' 120.0 . . ? N3 C6 C7 119.7(10) . . ? N3 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C8 117.0(10) . . ? C6 C7 H7 121.5 . . ? C8 C7 H7 121.5 . . ? C9 C8 C7 121.4(9) . . ? C9 C8 C11 121.9(8) . . ? C7 C8 C11 116.7(9) . . ? C8 C9 C10 117.9(9) . . ? C8 C9 H9 121.0 . . ? C10 C9 H9 121.0 . . ? N3 C10 C9 119.4(10) . . ? N3 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? N2 C11 C8 114.1(9) . . ? N2 C11 H11A 108.7 . . ? C8 C11 H11A 108.7 . . ? N2 C11 H11B 108.7 . . ? C8 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C12 C13 N6 120.8(10) . . ? C12 C13 H13 119.6 . . ? N6 C13 H13 119.6 . . ? C14 N6 C13 119.5(10) . . ? C14 N6 H6N 120.2 . . ? C13 N6 H6N 120.2 . . ? N6 C14 C15 120.5(11) . . ? N6 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 122.4(10) . . ? C16 C15 H15 118.8 . . ? C14 C15 H15 118.8 . . ? C15 C16 C12 115.0(10) . . ? C15 C16 C22 122.5(9) . . ? C12 C16 C22 122.4(9) . . ? N5 C17 N4 120.0(8) . . ? N5 C17 C18 124.7(8) . . ? N4 C17 C18 115.3(6) . . ? C19 C18 C17 119.1(6) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 123.3(7) . . ? C18 C19 H19 118.3 . . ? C20 C19 H19 118.3 . . ? C21 C20 C19 115.5(6) . . ? C21 C20 H20 122.3 . . ? C19 C20 H20 122.3 . . ? C20 C21 N4 121.7(6) . . ? C20 C21 H21 119.1 . . ? N4 C21 H21 119.1 . . ? N5 C22 C16 115.4(9) . . ? N5 C22 H22A 108.4 . . ? C16 C22 H22A 108.4 . . ? N5 C22 H22B 108.4 . . ? C16 C22 H22B 108.4 . . ? H22A C22 H22B 107.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C2 C1 N1 0.0 . . . . ? C2 C1 N1 C5 0.0 . . . . ? C5' N2 C5 N1 109(12) . . . . ? C11 N2 C5 N1 -177.9(14) . . . . ? C5' N2 C5 C4 -60(11) . . . . ? C11 N2 C5 C4 13(2) . . . . ? C1 N1 C5 N2 -169(2) . . . . ? C1 N1 C5 C4 0.0 . . . . ? N2 C5 C4 C3 169(2) . . . . ? N1 C5 C4 C3 0.0 . . . . ? C5 C4 C3 C2 0.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? C3' C2' C1' N1' 0.0 . . . . ? C2' C1' N1' C5' 0.0 . . . . ? C5 N2 C5' C4' 108(12) . . . . ? C11 N2 C5' C4' -6(3) . . . . ? C5 N2 C5' N1' -59(11) . . . . ? C11 N2 C5' N1' -173.2(12) . . . . ? C1' N1' C5' N2 169(2) . . . . ? C1' N1' C5' C4' 0.0 . . . . ? N2 C5' C4' C3' -166(3) . . . . ? N1' C5' C4' C3' 0.0 . . . . ? C5' C4' C3' C2' 0.0 . . . . ? C1' C2' C3' C4' 0.0 . . . . ? C10 N3 C6 C7 -1.3(17) . . . . ? N3 C6 C7 C8 -2.6(16) . . . . ? C6 C7 C8 C9 3.4(15) . . . . ? C6 C7 C8 C11 -174.8(10) . . . . ? C7 C8 C9 C10 -0.5(15) . . . . ? C11 C8 C9 C10 177.7(9) . . . . ? C6 N3 C10 C9 4.4(16) . . . . ? C8 C9 C10 N3 -3.4(15) . . . . ? C5' N2 C11 C8 80.9(18) . . . . ? C5 N2 C11 C8 68.0(19) . . . . ? C9 C8 C11 N2 12.8(14) . . . . ? C7 C8 C11 N2 -169.0(9) . . . . ? C16 C12 C13 N6 3.4(17) . . . . ? C12 C13 N6 C14 -0.7(16) . . . . ? C13 N6 C14 C15 -1.1(17) . . . . ? N6 C14 C15 C16 0.3(17) . . . . ? C14 C15 C16 C12 2.1(15) . . . . ? C14 C15 C16 C22 -174.6(10) . . . . ? C13 C12 C16 C15 -3.9(15) . . . . ? C13 C12 C16 C22 172.8(10) . . . . ? C22 N5 C17 N4 -176.1(8) . . . . ? C22 N5 C17 C18 3.0(14) . . . . ? C21 N4 C17 N5 176.1(9) . . . . ? C21 N4 C17 C18 -3.1(9) . . . . ? N5 C17 C18 C19 -177.4(9) . . . . ? N4 C17 C18 C19 1.7(9) . . . . ? C17 C18 C19 C20 0.7(11) . . . . ? C18 C19 C20 C21 -1.9(11) . . . . ? C19 C20 C21 N4 0.7(10) . . . . ? C17 N4 C21 C20 1.9(10) . . . . ? C17 N5 C22 C16 73.0(13) . . . . ? C15 C16 C22 N5 -169.6(10) . . . . ? C12 C16 C22 N5 14.0(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 H2N' F7 0.88 2.35 3.121(14) 145.8 . N2 H2N F6 0.86 2.58 3.285(11) 139.3 2_565 N3 H3N F1 0.86 1.97 2.748(11) 150.5 . N4 H4N F5 0.86 2.00 2.840(9) 163.7 . N4 H4N F2 0.86 2.36 2.923(9) 123.2 . N5 H5N F13 0.86 2.44 3.187(15) 146.0 . N5 H5N F5 0.86 2.56 3.265(12) 140.0 . N6 H6N F3 0.86 1.96 2.719(13) 146.1 2 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.689 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.067