# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_manuscript _audit_block_code ? _audit_creation_method SHELXL-97 _audit_creation_date ; 'Fri Jul 20 13:22:22 2012' ; _audit_update_record ? _chemical_name_systematic 3-Nitro-5-(5-Nitrimino-1,2,4-triazol-3-yl)-1,2,4-1H-triazole _chemical_compound_source ? _chemical_name_common NNBT _chemical_formula_moiety 'C4 H3 N9 O4, 4(H2 O)' _chemical_formula_sum 'C4 H11 N9 O8' _chemical_formula_weight 313.186 _diffrn_ambient_temperature 173(2) _diffrn_source_type 'Spellman generator' _diffrn_source_power ? _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method omega-scan _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 3194 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.15 _diffrn_reflns_theta_max 25.68 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.989 _reflns_number_total 2373 _reflns_number_gt 1743 _reflns_threshold_expression >2\s(I) _diffrn_orient_matrix_UB_11 -0.0282573000 _diffrn_orient_matrix_UB_12 0.0494500000 _diffrn_orient_matrix_UB_13 0.0503538000 _diffrn_orient_matrix_UB_21 -0.0622655000 _diffrn_orient_matrix_UB_22 -0.0716221000 _diffrn_orient_matrix_UB_23 0.0010667000 _diffrn_orient_matrix_UB_31 0.0932688000 _diffrn_orient_matrix_UB_32 -0.0167942000 _diffrn_orient_matrix_UB_33 0.0340294000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -1.00 103.00 1.0000 18.0000 omega____ theta____ kappa____ phi______ frames - 32.0000 79.0000 0.0000 104 #__ type_ start__ end____ width___ exp.time_ 2 omega -1.00 103.00 1.0000 18.0000 omega____ theta____ kappa____ phi______ frames - 32.0000 79.0000 120.0000 104 #__ type_ start__ end____ width___ exp.time_ 3 omega -65.00 39.00 1.0000 18.0000 omega____ theta____ kappa____ phi______ frames - -32.0000 80.0000 250.0000 104 ; _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number ? _symmetry_space_group_name_Hall '-P 1 ' 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3329(9) _cell_length_b 8.5362(11) _cell_length_c 12.685(2) _cell_angle_alpha 108.636(13) _cell_angle_beta 101.777(13) _cell_angle_gamma 94.022(11) _cell_volume 629.27(16) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 895 _cell_measurement_theta_min 4.1417 _cell_measurement_theta_max 33.5024 _cell_special_details ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.6529(4) _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.70769 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.544 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.065 _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _refine_special_details ? _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^)+(0.0875P)^2^+0.1155P] 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_extinction_expression ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2373 _refine_ls_number_parameters 234 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1537 _refine_ls_wR_factor_gt 0.1344 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.029 _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 O5 O 0.2346(4) 0.1786(3) 0.08396(18) 0.0353(5) Uani 1 1 d D . . O6 O 0.2581(4) 0.6703(3) 0.67244(18) 0.0377(5) Uani 1 1 d D . . O7 O 0.3449(4) 0.6541(3) 0.8895(2) 0.0460(6) Uani 1 1 d D . . O8 O 0.1682(4) 0.8409(3) 0.06513(19) 0.0412(6) Uani 1 1 d D . . H6B H 0.276(4) 0.797(3) 0.695(2) 0.010(6) Uiso 1 1 d . . . H6A H 0.283(5) 0.670(4) 0.7398(11) 0.028(8) Uiso 1 1 d D . . H7 H 0.256(5) 0.521(5) 0.556(3) 0.052(10) Uiso 1 1 d . . . H5B H 0.121(7) 0.178(5) 0.030(4) 0.063(12) Uiso 1 1 d . . . H5A H 0.346(5) 0.212(6) 0.066(4) 0.102(18) Uiso 1 1 d D . . H5 H 0.220(5) 0.298(4) 0.210(3) 0.043(9) Uiso 1 1 d . . . H8B H 0.207(8) 0.944(7) 0.078(5) 0.093(17) Uiso 1 1 d . . . H H 0.252(4) -0.056(4) 0.450(3) 0.028(8) Uiso 1 1 d . . . H7A H 0.272(9) 0.705(7) 0.935(5) 0.15(3) Uiso 1 1 d D . . H7B H 0.363(9) 0.560(3) 0.895(5) 0.11(2) Uiso 1 1 d D . . H8A H 0.184(6) 0.817(5) 0.1252(19) 0.065(12) Uiso 1 1 d D . . N7 N 0.2435(3) 0.4359(3) 0.48138(19) 0.0223(5) Uani 1 1 d . . . O4 O 0.2175(3) 0.8038(2) 0.29127(16) 0.0315(5) Uani 1 1 d . . . N3 N 0.2679(4) 0.2612(3) 0.64757(18) 0.0258(5) Uani 1 1 d . . . N2 N 0.2668(4) -0.0178(3) 0.61037(18) 0.0257(5) Uani 1 1 d . . . N1 N 0.2547(3) 0.0193(3) 0.5139(2) 0.0240(5) Uani 1 1 d . . . N8 N 0.2309(4) 0.6283(3) 0.38546(18) 0.0269(5) Uani 1 1 d . . . N9 N 0.2135(4) 0.6522(3) 0.28607(18) 0.0269(5) Uani 1 1 d . . . O3 O 0.1957(4) 0.5390(2) 0.19411(16) 0.0409(6) Uani 1 1 d . . . N6 N 0.2298(4) 0.1934(3) 0.34478(18) 0.0264(5) Uani 1 1 d . . . C4 C 0.2299(4) 0.4678(3) 0.3820(2) 0.0214(5) Uani 1 1 d . . . C2 C 0.2551(4) 0.1848(3) 0.5376(2) 0.0231(6) Uani 1 1 d . . . O2 O 0.2953(4) 0.2897(3) 0.87213(19) 0.0493(6) Uani 1 1 d . . . C3 C 0.2422(4) 0.2676(3) 0.4532(2) 0.0236(6) Uani 1 1 d . . . N5 N 0.2221(4) 0.3214(3) 0.30059(19) 0.0255(5) Uani 1 1 d . . . C1 C 0.2738(4) 0.1307(3) 0.6858(2) 0.0240(6) Uani 1 1 d . . . O1 O 0.2944(4) 0.0215(3) 0.83017(19) 0.0530(7) Uani 1 1 d . . . N4 N 0.2891(4) 0.1489(3) 0.8042(2) 0.0362(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O5 0.0495(15) 0.0335(11) 0.0245(11) 0.0097(9) 0.0130(10) 0.0057(10) O6 0.0538(14) 0.0269(12) 0.0281(12) 0.0034(9) 0.0102(10) 0.0051(9) O7 0.0593(16) 0.0400(14) 0.0381(13) 0.0107(11) 0.0154(11) 0.0062(11) O8 0.0587(15) 0.0382(14) 0.0312(13) 0.0161(10) 0.0137(10) 0.0072(11) N7 0.0278(12) 0.0225(11) 0.0176(11) 0.0077(9) 0.0057(8) 0.0041(8) O4 0.0496(12) 0.0201(10) 0.0278(11) 0.0117(8) 0.0096(8) 0.0064(8) N3 0.0332(12) 0.0264(12) 0.0210(12) 0.0110(9) 0.0080(9) 0.0062(9) N2 0.0321(12) 0.0263(12) 0.0207(12) 0.0108(9) 0.0065(9) 0.0042(9) N1 0.0307(13) 0.0230(12) 0.0204(12) 0.0081(10) 0.0094(9) 0.0043(9) N8 0.0378(13) 0.0240(12) 0.0220(12) 0.0111(9) 0.0082(9) 0.0052(9) N9 0.0381(13) 0.0215(11) 0.0216(12) 0.0073(9) 0.0079(9) 0.0046(9) O3 0.0723(15) 0.0289(11) 0.0206(11) 0.0077(9) 0.0107(9) 0.0067(10) N6 0.0353(13) 0.0256(12) 0.0235(12) 0.0123(9) 0.0115(9) 0.0074(9) C4 0.0225(13) 0.0231(13) 0.0204(13) 0.0093(10) 0.0061(10) 0.0035(10) C2 0.0244(13) 0.0252(14) 0.0208(13) 0.0090(10) 0.0056(10) 0.0043(10) O2 0.0846(18) 0.0320(13) 0.0308(12) 0.0091(10) 0.0157(11) 0.0082(11) C3 0.0237(13) 0.0252(14) 0.0225(14) 0.0083(11) 0.0066(10) 0.0034(10) N5 0.0323(12) 0.0238(12) 0.0248(12) 0.0128(9) 0.0091(9) 0.0052(9) C1 0.0269(14) 0.0269(14) 0.0200(13) 0.0102(11) 0.0061(10) 0.0035(10) O1 0.0890(18) 0.0460(14) 0.0319(13) 0.0232(11) 0.0157(12) 0.0103(12) N4 0.0543(16) 0.0318(14) 0.0255(13) 0.0140(11) 0.0090(11) 0.0075(11) 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 O5 H5B 0.88(4) . ? O5 H5A 0.842(7) . ? O6 H6B 1.02(3) . ? O6 H6A 0.837(7) . ? O7 H7A 0.839(10) . ? O7 H7B 0.846(10) . ? O8 H8B 0.85(5) . ? O8 H8A 0.837(7) . ? N7 C4 1.360(3) . ? N7 C3 1.364(3) . ? N7 H7 0.97(4) . ? O4 N9 1.273(3) . ? N3 C2 1.320(3) . ? N3 C1 1.350(3) . ? N2 C1 1.313(3) . ? N2 N1 1.348(3) . ? N1 C2 1.347(3) . ? N1 H 0.85(3) . ? N8 N9 1.324(3) . ? N8 C4 1.356(3) . ? N9 O3 1.232(3) . ? N6 C3 1.300(3) . ? N6 N5 1.378(3) . ? C4 N5 1.333(3) . ? C2 C3 1.452(4) . ? O2 N4 1.228(3) . ? N5 H5 1.10(3) . ? C1 N4 1.441(4) . ? O1 N4 1.234(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H5B O5 H5A 107(4) . . ? H6B O6 H6A 95(2) . . ? H7A O7 H7B 111(6) . . ? H8B O8 H8A 113(4) . . ? C4 N7 C3 105.8(2) . . ? C4 N7 H7 124(2) . . ? C3 N7 H7 130(2) . . ? C2 N3 C1 100.8(2) . . ? C1 N2 N1 101.2(2) . . ? C2 N1 N2 109.7(2) . . ? C2 N1 H 129(2) . . ? N2 N1 H 122(2) . . ? N9 N8 C4 115.9(2) . . ? O3 N9 O4 121.0(2) . . ? O3 N9 N8 124.0(2) . . ? O4 N9 N8 115.0(2) . . ? C3 N6 N5 103.9(2) . . ? N5 C4 N8 135.1(2) . . ? N5 C4 N7 106.5(2) . . ? N8 C4 N7 118.3(2) . . ? N3 C2 N1 110.9(2) . . ? N3 C2 C3 124.7(2) . . ? N1 C2 C3 124.4(2) . . ? N6 C3 N7 112.7(2) . . ? N6 C3 C2 125.0(2) . . ? N7 C3 C2 122.3(2) . . ? C4 N5 N6 111.2(2) . . ? C4 N5 H5 127.7(16) . . ? N6 N5 H5 121.0(16) . . ? N2 C1 N3 117.3(2) . . ? N2 C1 N4 119.8(2) . . ? N3 C1 N4 122.9(2) . . ? O2 N4 O1 124.5(2) . . ? O2 N4 C1 117.9(2) . . ? O1 N4 C1 117.7(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N2 N1 C2 -0.1(3) . . . . ? C4 N8 N9 O3 0.5(4) . . . . ? C4 N8 N9 O4 -179.1(2) . . . . ? N9 N8 C4 N5 2.6(4) . . . . ? N9 N8 C4 N7 -178.9(2) . . . . ? C3 N7 C4 N5 -0.2(3) . . . . ? C3 N7 C4 N8 -179.2(2) . . . . ? C1 N3 C2 N1 -0.3(3) . . . . ? C1 N3 C2 C3 179.5(2) . . . . ? N2 N1 C2 N3 0.3(3) . . . . ? N2 N1 C2 C3 -179.5(2) . . . . ? N5 N6 C3 N7 -0.2(3) . . . . ? N5 N6 C3 C2 -179.7(2) . . . . ? C4 N7 C3 N6 0.3(3) . . . . ? C4 N7 C3 C2 179.8(2) . . . . ? N3 C2 C3 N6 179.9(2) . . . . ? N1 C2 C3 N6 -0.3(4) . . . . ? N3 C2 C3 N7 0.4(4) . . . . ? N1 C2 C3 N7 -179.9(2) . . . . ? N8 C4 N5 N6 178.8(3) . . . . ? N7 C4 N5 N6 0.1(3) . . . . ? C3 N6 N5 C4 0.0(3) . . . . ? N1 N2 C1 N3 -0.1(3) . . . . ? N1 N2 C1 N4 -179.6(2) . . . . ? C2 N3 C1 N2 0.3(3) . . . . ? C2 N3 C1 N4 179.7(2) . . . . ? N2 C1 N4 O2 180.0(3) . . . . ? N3 C1 N4 O2 0.5(4) . . . . ? N2 C1 N4 O1 -0.2(4) . . . . ? N3 C1 N4 O1 -179.7(3) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 935564' ####################################################################### # # 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_manuscript2 #TrackingRef 'web_deposit_cif_file_1_AlexanderDippold_1366724607.ix139 - AzNBT_publ.cif' _audit_creation_method SHELXL-97 _audit_creation_date ; 'Sat Mar 23 11:05:01 2013' ; _audit_update_record ? _chemical_name_systematic 5-(5-azido-1H-1,2,4-triazol-3-yl)-3-nitro-1H-1,2,4-triazole _chemical_compound_source ? _chemical_name_common AzNBT _chemical_formula_moiety 'C4 H2 N10 O2, 2(H2 O)' _chemical_formula_sum 'C4 H6 N10 O4' _chemical_formula_weight 258.155 _diffrn_ambient_temperature 100(2) _diffrn_source_type 'Spellman generator' _diffrn_source_power ? _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method omega-scan _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 5013 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 25.49 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.989 _reflns_number_total 3732 _reflns_number_gt 2554 _reflns_threshold_expression >2\s(I) _diffrn_orient_matrix_UB_11 0.0879695000 _diffrn_orient_matrix_UB_12 0.0324556000 _diffrn_orient_matrix_UB_13 -0.0165792000 _diffrn_orient_matrix_UB_21 -0.0438115000 _diffrn_orient_matrix_UB_22 0.0361525000 _diffrn_orient_matrix_UB_23 -0.0251875000 _diffrn_orient_matrix_UB_31 0.0153385000 _diffrn_orient_matrix_UB_32 0.0407888000 _diffrn_orient_matrix_UB_33 0.0511536000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -1.00 103.00 1.0000 95.0000 omega____ theta____ kappa____ phi______ frames - 32.0000 79.0000 0.0000 104 #__ type_ start__ end____ width___ exp.time_ 2 omega -1.00 103.00 1.0000 95.0000 omega____ theta____ kappa____ phi______ frames - 32.0000 79.0000 120.0000 104 #__ type_ start__ end____ width___ exp.time_ 3 omega -65.00 39.00 1.0000 95.0000 omega____ theta____ kappa____ phi______ frames - -32.0000 80.0000 250.0000 104 ; _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number ? _symmetry_space_group_name_Hall '-P 1' 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4790(7) _cell_length_b 11.8671(12) _cell_length_c 12.1234(12) _cell_angle_alpha 98.918(8) _cell_angle_beta 91.332(8) _cell_angle_gamma 107.056(9) _cell_volume 1013.55(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1278 _cell_measurement_theta_min 4.5420 _cell_measurement_theta_max 31.4300 _cell_special_details ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.6918(3) _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.148 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.49696 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.372 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.076 _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _refine_special_details ? _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^)+(0.0698P)^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_extinction_expression ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3732 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0935 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1612 _refine_ls_wR_factor_gt 0.1357 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 -0.2056(3) 0.5235(2) 0.03208(19) 0.0341(6) Uani 1 1 d . . . O2 O -0.2608(3) 0.6302(2) 0.18382(18) 0.0311(6) Uani 1 1 d . . . N1 N 0.1379(4) 0.8336(2) -0.0212(2) 0.0233(6) Uani 1 1 d . . . N2 N 0.0355(4) 0.7177(2) -0.0255(2) 0.0239(6) Uani 1 1 d . . . N3 N -0.0060(3) 0.8306(2) 0.1353(2) 0.0223(6) Uani 1 1 d . . . N4 N -0.1795(4) 0.6170(2) 0.0972(2) 0.0262(6) Uani 1 1 d . . . N5 N 0.2881(4) 1.2059(2) 0.1831(2) 0.0248(6) Uani 1 1 d . . . N6 N 0.1847(4) 1.0951(2) 0.1970(2) 0.0247(6) Uani 1 1 d . . . N7 N 0.3086(3) 1.0887(2) 0.0268(2) 0.0237(6) Uani 1 1 d . . . N8 N 0.4711(4) 1.3034(2) 0.0487(2) 0.0319(7) Uani 1 1 d . . . N9 N 0.5362(4) 1.2838(2) -0.0445(2) 0.0273(6) Uani 1 1 d . . . N10 N 0.6057(4) 1.2829(3) -0.1261(2) 0.0351(7) Uani 1 1 d . . . C1 C -0.0462(4) 0.7235(3) 0.0701(3) 0.0223(7) Uani 1 1 d . . . C2 C 0.1128(4) 0.8999(3) 0.0749(2) 0.0223(7) Uani 1 1 d . . . C3 C 0.2014(4) 1.0281(3) 0.1013(2) 0.0226(7) Uani 1 1 d . . . C4 C 0.3610(4) 1.1988(3) 0.0820(3) 0.0233(7) Uani 1 1 d . . . O3 O 0.4924(3) 0.8519(2) 0.5585(2) 0.0349(6) Uani 1 1 d . . . O4 O 0.5510(3) 0.7406(2) 0.41113(18) 0.0296(6) Uani 1 1 d . . . N11 N 0.1730(4) 0.5423(2) 0.6296(2) 0.0226(6) Uani 1 1 d . . . N12 N 0.2726(3) 0.6581(2) 0.6303(2) 0.0226(6) Uani 1 1 d . . . N13 N 0.3229(3) 0.5407(2) 0.4743(2) 0.0215(6) Uani 1 1 d . . . N14 N 0.4753(4) 0.7551(2) 0.4995(2) 0.0253(6) Uani 1 1 d . . . N15 N 0.0432(4) 0.1690(2) 0.4224(2) 0.0245(6) Uani 1 1 d . . . N16 N 0.1519(4) 0.2815(2) 0.4154(2) 0.0238(6) Uani 1 1 d . . . N17 N -0.0091(3) 0.2822(2) 0.5726(2) 0.0216(6) Uani 1 1 d . . . N18 N -0.1682(4) 0.0666(2) 0.5416(2) 0.0274(6) Uani 1 1 d . . . N19 N -0.2628(4) 0.0854(2) 0.6240(2) 0.0237(6) Uani 1 1 d . . . N20 N -0.3561(4) 0.0874(2) 0.6941(2) 0.0322(7) Uani 1 1 d . . . C5 C 0.3579(4) 0.6497(3) 0.5360(2) 0.0215(7) Uani 1 1 d . . . C6 C 0.2033(4) 0.4738(3) 0.5363(2) 0.0214(7) Uani 1 1 d . . . C7 C 0.1161(4) 0.3446(3) 0.5075(2) 0.0221(7) Uani 1 1 d . . . C8 C -0.0493(4) 0.1725(3) 0.5159(2) 0.0231(7) Uani 1 1 d . . . O5 O 0.6828(3) 0.1178(2) 0.20043(19) 0.0303(6) Uani 1 1 d . . . O6 O 0.2001(3) 0.0535(2) 0.7045(2) 0.0329(6) Uani 1 1 d . . . O7 O 0.0491(3) 0.4913(2) 0.2060(2) 0.0302(6) Uani 1 1 d . . . O8 O 0.3987(3) 0.4573(2) 0.2572(2) 0.0316(6) Uani 1 1 d . . . H1 H 0.209(5) 0.848(3) -0.090(3) 0.038 Uiso 1 1 d . . . H5 H 0.314(5) 1.271(3) 0.229(3) 0.038 Uiso 1 1 d . . . H11 H 0.087(5) 0.518(3) 0.683(3) 0.038 Uiso 1 1 d . . . H15 H 0.032(5) 0.106(3) 0.369(3) 0.038 Uiso 1 1 d . . . H5A H 0.709(5) 0.058(4) 0.231(3) 0.047 Uiso 1 1 d . . . H5B H 0.701(6) 0.169(4) 0.252(4) 0.047 Uiso 1 1 d . . . H6A H 0.157(6) 0.100(4) 0.746(3) 0.047 Uiso 1 1 d . . . H6B H 0.272(6) 0.107(4) 0.672(3) 0.047 Uiso 1 1 d . . . H7A H 0.002(6) 0.426(4) 0.161(3) 0.047 Uiso 1 1 d . . . H7B H 0.154(6) 0.486(4) 0.218(3) 0.047 Uiso 1 1 d . . . H8A H 0.405(5) 0.496(4) 0.319(4) 0.047 Uiso 1 1 d . . . H8B H 0.494(6) 0.497(4) 0.227(3) 0.047 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0384(14) 0.0251(13) 0.0329(14) -0.0027(11) 0.0065(11) 0.0042(11) O2 0.0323(13) 0.0353(14) 0.0260(13) 0.0043(10) 0.0126(10) 0.0102(11) N1 0.0274(14) 0.0232(15) 0.0168(14) -0.0009(11) 0.0030(11) 0.0060(12) N2 0.0274(14) 0.0219(14) 0.0198(14) -0.0004(11) 0.0040(11) 0.0052(12) N3 0.0229(13) 0.0222(14) 0.0223(14) 0.0017(11) 0.0069(11) 0.0080(12) N4 0.0263(14) 0.0297(16) 0.0233(15) 0.0023(12) 0.0059(11) 0.0104(13) N5 0.0287(15) 0.0215(15) 0.0215(15) -0.0015(11) 0.0068(11) 0.0055(13) N6 0.0276(14) 0.0234(14) 0.0225(14) 0.0018(11) 0.0065(11) 0.0074(12) N7 0.0246(14) 0.0223(14) 0.0229(14) 0.0010(11) 0.0047(11) 0.0061(12) N8 0.0375(16) 0.0295(16) 0.0276(16) 0.0031(12) 0.0156(13) 0.0083(14) N9 0.0249(14) 0.0250(15) 0.0303(17) 0.0024(12) 0.0089(12) 0.0057(12) N10 0.0374(17) 0.0365(18) 0.0314(17) 0.0047(13) 0.0119(14) 0.0110(15) C1 0.0219(16) 0.0248(17) 0.0209(16) 0.0025(13) 0.0045(12) 0.0086(14) C2 0.0246(16) 0.0248(17) 0.0170(16) -0.0011(13) 0.0016(12) 0.0093(14) C3 0.0229(16) 0.0269(17) 0.0195(16) 0.0007(13) 0.0020(12) 0.0116(14) C4 0.0240(16) 0.0242(17) 0.0223(17) 0.0031(13) 0.0049(13) 0.0084(14) O3 0.0385(14) 0.0235(13) 0.0370(14) -0.0043(10) 0.0122(11) 0.0047(11) O4 0.0314(12) 0.0341(13) 0.0247(12) 0.0055(10) 0.0109(10) 0.0108(11) N11 0.0217(13) 0.0240(15) 0.0207(14) -0.0005(11) 0.0067(11) 0.0066(12) N12 0.0214(13) 0.0231(14) 0.0219(14) 0.0002(11) 0.0015(11) 0.0065(12) N13 0.0225(13) 0.0228(14) 0.0188(14) 0.0005(11) 0.0044(10) 0.0076(12) N14 0.0262(14) 0.0244(15) 0.0249(15) 0.0003(12) 0.0037(11) 0.0090(12) N15 0.0263(14) 0.0218(14) 0.0227(14) -0.0028(11) 0.0065(11) 0.0060(12) N16 0.0269(14) 0.0200(14) 0.0239(14) 0.0013(11) 0.0072(11) 0.0069(12) N17 0.0240(14) 0.0236(14) 0.0178(13) 0.0015(11) 0.0052(10) 0.0086(12) N18 0.0282(15) 0.0254(15) 0.0274(15) 0.0001(11) 0.0112(12) 0.0079(13) N19 0.0242(14) 0.0210(14) 0.0247(15) 0.0024(11) 0.0019(12) 0.0059(12) N20 0.0359(16) 0.0286(16) 0.0293(17) 0.0003(12) 0.0101(14) 0.0073(14) C5 0.0221(16) 0.0233(17) 0.0195(16) 0.0015(13) 0.0049(12) 0.0083(14) C6 0.0211(16) 0.0255(17) 0.0174(16) -0.0014(13) -0.0001(12) 0.0096(14) C7 0.0213(16) 0.0240(17) 0.0206(16) -0.0026(13) 0.0014(12) 0.0093(14) C8 0.0226(16) 0.0262(17) 0.0204(16) 0.0022(13) 0.0048(13) 0.0079(14) O5 0.0394(14) 0.0326(14) 0.0178(12) -0.0017(10) 0.0090(10) 0.0119(12) O6 0.0368(14) 0.0296(14) 0.0318(14) 0.0017(11) 0.0145(11) 0.0098(12) O7 0.0303(13) 0.0343(14) 0.0234(13) -0.0039(10) 0.0076(10) 0.0097(12) O8 0.0353(14) 0.0325(14) 0.0240(13) -0.0029(10) 0.0128(11) 0.0086(12) 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 1.220(3) . ? O2 N4 1.238(3) . ? N1 C2 1.350(4) . ? N1 N2 1.356(3) . ? N1 H1 1.01(3) . ? N2 C1 1.325(4) . ? N3 C1 1.335(4) . ? N3 C2 1.339(4) . ? N4 C1 1.451(4) . ? N5 C4 1.353(4) . ? N5 N6 1.354(4) . ? N5 H5 0.84(4) . ? N6 C3 1.332(4) . ? N7 C4 1.313(4) . ? N7 C3 1.368(4) . ? N8 N9 1.255(4) . ? N8 C4 1.398(4) . ? N9 N10 1.129(3) . ? C2 C3 1.451(4) . ? O3 N14 1.226(3) . ? O4 N14 1.235(3) . ? N11 C6 1.351(4) . ? N11 N12 1.356(3) . ? N11 H11 0.94(4) . ? N12 C5 1.326(4) . ? N13 C5 1.339(4) . ? N13 C6 1.340(4) . ? N14 C5 1.440(4) . ? N15 C8 1.343(4) . ? N15 N16 1.362(3) . ? N15 H15 0.89(4) . ? N16 C7 1.323(4) . ? N17 C8 1.320(4) . ? N17 C7 1.362(4) . ? N18 N19 1.267(3) . ? N18 C8 1.395(4) . ? N19 N20 1.114(3) . ? C6 C7 1.462(4) . ? O5 H5A 0.92(4) . ? O5 H5B 0.78(4) . ? O6 H6A 0.83(4) . ? O6 H6B 0.86(4) . ? O7 H7A 0.85(4) . ? O7 H7B 0.82(4) . ? O8 H8A 0.81(4) . ? O8 H8B 0.85(4) . ? 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 C2 N1 N2 109.9(2) . . ? C2 N1 H1 137(2) . . ? N2 N1 H1 113(2) . . ? C1 N2 N1 101.2(2) . . ? C1 N3 C2 101.7(2) . . ? O1 N4 O2 125.6(3) . . ? O1 N4 C1 117.9(2) . . ? O2 N4 C1 116.5(2) . . ? C4 N5 N6 109.1(2) . . ? C4 N5 H5 122(2) . . ? N6 N5 H5 128(2) . . ? C3 N6 N5 102.3(2) . . ? C4 N7 C3 101.7(2) . . ? N9 N8 C4 112.6(3) . . ? N10 N9 N8 170.4(3) . . ? N2 C1 N3 117.2(3) . . ? N2 C1 N4 119.7(3) . . ? N3 C1 N4 123.1(3) . . ? N3 C2 N1 110.0(3) . . ? N3 C2 C3 127.6(3) . . ? N1 C2 C3 122.3(3) . . ? N6 C3 N7 115.3(3) . . ? N6 C3 C2 123.6(3) . . ? N7 C3 C2 121.0(3) . . ? N7 C4 N5 111.7(3) . . ? N7 C4 N8 129.2(3) . . ? N5 C4 N8 119.1(3) . . ? C6 N11 N12 109.5(2) . . ? C6 N11 H11 127(2) . . ? N12 N11 H11 123(2) . . ? C5 N12 N11 101.4(2) . . ? C5 N13 C6 101.1(2) . . ? O3 N14 O4 125.1(3) . . ? O3 N14 C5 117.6(2) . . ? O4 N14 C5 117.3(2) . . ? C8 N15 N16 109.1(3) . . ? C8 N15 H15 128(2) . . ? N16 N15 H15 123(2) . . ? C7 N16 N15 101.9(2) . . ? C8 N17 C7 101.2(2) . . ? N19 N18 C8 112.2(2) . . ? N20 N19 N18 171.5(3) . . ? N12 C5 N13 117.3(3) . . ? N12 C5 N14 120.8(3) . . ? N13 C5 N14 121.9(3) . . ? N13 C6 N11 110.7(3) . . ? N13 C6 C7 125.0(3) . . ? N11 C6 C7 124.3(3) . . ? N16 C7 N17 116.1(3) . . ? N16 C7 C6 121.8(3) . . ? N17 C7 C6 122.1(3) . . ? N17 C8 N15 111.8(3) . . ? N17 C8 N18 128.9(3) . . ? N15 C8 N18 119.4(3) . . ? H5A O5 H5B 102(4) . . ? H6A O6 H6B 96(4) . . ? H7A O7 H7B 99(4) . . ? H8A O8 H8B 104(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 C2 N1 N2 C1 0.4(3) . . . . ? C4 N5 N6 C3 -0.6(3) . . . . ? N1 N2 C1 N3 -0.3(4) . . . . ? N1 N2 C1 N4 176.9(3) . . . . ? C2 N3 C1 N2 0.1(4) . . . . ? C2 N3 C1 N4 -176.9(3) . . . . ? O1 N4 C1 N2 3.2(4) . . . . ? O2 N4 C1 N2 -174.9(3) . . . . ? O1 N4 C1 N3 -179.8(3) . . . . ? O2 N4 C1 N3 2.1(4) . . . . ? C1 N3 C2 N1 0.1(3) . . . . ? C1 N3 C2 C3 178.0(3) . . . . ? N2 N1 C2 N3 -0.3(4) . . . . ? N2 N1 C2 C3 -178.4(3) . . . . ? N5 N6 C3 N7 -0.1(3) . . . . ? N5 N6 C3 C2 -179.6(3) . . . . ? C4 N7 C3 N6 0.7(4) . . . . ? C4 N7 C3 C2 -179.7(3) . . . . ? N3 C2 C3 N6 4.9(5) . . . . ? N1 C2 C3 N6 -177.5(3) . . . . ? N3 C2 C3 N7 -174.7(3) . . . . ? N1 C2 C3 N7 3.0(5) . . . . ? C3 N7 C4 N5 -1.0(3) . . . . ? C3 N7 C4 N8 -178.6(3) . . . . ? N6 N5 C4 N7 1.1(4) . . . . ? N6 N5 C4 N8 179.0(3) . . . . ? N9 N8 C4 N7 -5.3(5) . . . . ? N9 N8 C4 N5 177.2(3) . . . . ? C6 N11 N12 C5 -0.5(3) . . . . ? C8 N15 N16 C7 0.4(3) . . . . ? N11 N12 C5 N13 0.3(4) . . . . ? N11 N12 C5 N14 177.2(3) . . . . ? C6 N13 C5 N12 0.0(4) . . . . ? C6 N13 C5 N14 -176.8(3) . . . . ? O3 N14 C5 N12 -0.3(4) . . . . ? O4 N14 C5 N12 179.7(3) . . . . ? O3 N14 C5 N13 176.5(3) . . . . ? O4 N14 C5 N13 -3.6(4) . . . . ? C5 N13 C6 N11 -0.4(3) . . . . ? C5 N13 C6 C7 179.3(3) . . . . ? N12 N11 C6 N13 0.6(3) . . . . ? N12 N11 C6 C7 -179.1(3) . . . . ? N15 N16 C7 N17 -0.9(3) . . . . ? N15 N16 C7 C6 -179.9(3) . . . . ? C8 N17 C7 N16 1.0(4) . . . . ? C8 N17 C7 C6 180.0(3) . . . . ? N13 C6 C7 N16 0.9(5) . . . . ? N11 C6 C7 N16 -179.4(3) . . . . ? N13 C6 C7 N17 -177.9(3) . . . . ? N11 C6 C7 N17 1.7(5) . . . . ? C7 N17 C8 N15 -0.7(3) . . . . ? C7 N17 C8 N18 178.5(3) . . . . ? N16 N15 C8 N17 0.2(4) . . . . ? N16 N15 C8 N18 -179.1(3) . . . . ? N19 N18 C8 N17 9.0(5) . . . . ? N19 N18 C8 N15 -171.8(3) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 935565'