# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #TrackingRef 'shrv220-final.cif' #=========================================================================== _audit_creation_date 2012-12-20 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _audit_update_record ; ; #========================================================================== data_shrv220 #TrackingRef 'shrv220-final.cif' _audit_creation_date 2012-12-20 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 4,5-dinitro-N-(2,2,2-trinitroethyl)-1H-imidazol-1-amine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H4 N8 O10' _chemical_formula_sum 'C5 H4 N8 O10' _chemical_formula_weight 336.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.3893(5) _cell_length_b 10.0156(6) _cell_length_c 14.3147(8) _cell_angle_alpha 90.00 _cell_angle_beta 103.532(2) _cell_angle_gamma 90.00 _cell_volume 1169.39(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.909 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.185 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9163 _exptl_absorpt_correction_T_max 0.9980 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10968 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 26.39 _reflns_number_total 2396 _reflns_number_gt 2121 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _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^)+(0.0407P)^2^+0.4058P] 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 2396 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0337 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0779 _refine_ls_wR_factor_gt 0.0750 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.12769(12) 0.57470(10) 0.71942(7) 0.0147(2) Uani 1 1 d . . . C2 C -0.17657(15) 0.68405(13) 0.76065(9) 0.0176(3) Uani 1 1 d . . . H2 H -0.1355 0.7085 0.8260 0.021 Uiso 1 1 calc R . . N3 N -0.28832(13) 0.75267(11) 0.69906(8) 0.0182(2) Uani 1 1 d . . . C4 C -0.31085(15) 0.68456(12) 0.61526(9) 0.0154(3) Uani 1 1 d . . . C5 C -0.21390(15) 0.57354(12) 0.62473(9) 0.0149(3) Uani 1 1 d . . . N6 N -0.00859(13) 0.48605(11) 0.76930(8) 0.0156(2) Uani 1 1 d . . . H6 H -0.0555(19) 0.4085(16) 0.7725(11) 0.019 Uiso 1 1 d . . . C7 C 0.13740(15) 0.48011(12) 0.73056(9) 0.0159(3) Uani 1 1 d . . . H7A H 0.1444 0.5612 0.6922 0.019 Uiso 1 1 calc R . . H7B H 0.1318 0.4013 0.6882 0.019 Uiso 1 1 calc R . . C8 C 0.28716(15) 0.47048(12) 0.81370(9) 0.0158(3) Uani 1 1 d . . . N9 N 0.31365(13) 0.32874(11) 0.85256(8) 0.0183(2) Uani 1 1 d . . . O10 O 0.45353(12) 0.29404(10) 0.88823(8) 0.0295(3) Uani 1 1 d . . . O11 O 0.19032(12) 0.26092(9) 0.84242(7) 0.0248(2) Uani 1 1 d . . . N12 N 0.44411(13) 0.50744(11) 0.78388(8) 0.0200(3) Uani 1 1 d . . . O13 O 0.53724(13) 0.58448(11) 0.83408(8) 0.0340(3) Uani 1 1 d . . . O14 O 0.46052(12) 0.45285(11) 0.71097(8) 0.0314(3) Uani 1 1 d . . . N15 N 0.27454(13) 0.56156(11) 0.89617(8) 0.0206(2) Uani 1 1 d . . . O16 O 0.29982(13) 0.51330(11) 0.97568(7) 0.0314(3) Uani 1 1 d . . . O17 O 0.23906(13) 0.67676(10) 0.87252(8) 0.0307(3) Uani 1 1 d . . . N18 N -0.43320(13) 0.72921(11) 0.53178(8) 0.0184(2) Uani 1 1 d . . . O19 O -0.47713(13) 0.84542(10) 0.53039(8) 0.0291(2) Uani 1 1 d . . . O20 O -0.48406(12) 0.64676(10) 0.46886(7) 0.0256(2) Uani 1 1 d . . . N21 N -0.18409(13) 0.47441(11) 0.55801(8) 0.0181(2) Uani 1 1 d . . . O22 O -0.15046(12) 0.36111(9) 0.58921(7) 0.0254(2) Uani 1 1 d . . . O23 O -0.19168(13) 0.51068(11) 0.47575(7) 0.0286(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0136(5) 0.0154(5) 0.0147(5) 0.0018(4) 0.0024(4) 0.0003(4) C2 0.0158(6) 0.0192(6) 0.0176(6) -0.0029(5) 0.0039(5) -0.0008(5) N3 0.0173(5) 0.0181(5) 0.0192(6) -0.0011(4) 0.0045(4) 0.0012(4) C4 0.0141(6) 0.0166(6) 0.0156(6) 0.0017(5) 0.0035(5) -0.0008(5) C5 0.0141(6) 0.0161(6) 0.0142(6) 0.0007(5) 0.0026(5) -0.0015(4) N6 0.0132(5) 0.0150(5) 0.0182(6) 0.0052(4) 0.0027(4) 0.0014(4) C7 0.0154(6) 0.0168(6) 0.0155(6) 0.0014(5) 0.0032(5) 0.0004(5) C8 0.0153(6) 0.0146(6) 0.0179(7) 0.0002(5) 0.0044(5) 0.0008(5) N9 0.0184(5) 0.0179(5) 0.0186(6) 0.0021(4) 0.0042(4) 0.0032(4) O10 0.0197(5) 0.0288(5) 0.0372(6) 0.0092(5) 0.0007(4) 0.0077(4) O11 0.0222(5) 0.0181(5) 0.0342(6) 0.0037(4) 0.0073(4) -0.0024(4) N12 0.0153(5) 0.0222(6) 0.0225(6) 0.0039(5) 0.0043(5) 0.0008(4) O13 0.0236(5) 0.0382(6) 0.0403(7) -0.0062(5) 0.0077(5) -0.0141(5) O14 0.0253(5) 0.0442(6) 0.0282(6) -0.0048(5) 0.0129(4) 0.0019(5) N15 0.0164(5) 0.0220(6) 0.0228(6) -0.0059(5) 0.0029(4) -0.0018(4) O16 0.0322(6) 0.0429(6) 0.0176(5) -0.0046(5) 0.0031(4) 0.0034(5) O17 0.0328(6) 0.0170(5) 0.0433(7) -0.0070(4) 0.0108(5) 0.0004(4) N18 0.0157(5) 0.0222(6) 0.0178(6) 0.0040(5) 0.0051(4) 0.0027(4) O19 0.0348(6) 0.0243(5) 0.0283(6) 0.0072(4) 0.0075(4) 0.0141(4) O20 0.0232(5) 0.0299(5) 0.0200(5) -0.0006(4) -0.0022(4) -0.0017(4) N21 0.0161(5) 0.0195(6) 0.0177(6) -0.0022(4) 0.0015(4) 0.0007(4) O22 0.0295(5) 0.0164(5) 0.0272(5) -0.0022(4) 0.0002(4) 0.0045(4) O23 0.0370(6) 0.0346(6) 0.0151(5) 0.0001(4) 0.0076(4) 0.0064(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.3525(16) . ? N1 C5 1.3790(16) . ? N1 N6 1.4010(14) . ? C2 N3 1.3197(17) . ? C2 H2 0.9500 . ? N3 C4 1.3543(17) . ? C4 C5 1.3656(18) . ? C4 N18 1.4517(16) . ? C5 N21 1.4396(16) . ? N6 C7 1.4591(16) . ? N6 H6 0.877(16) . ? C7 C8 1.5180(18) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N15 1.5152(16) . ? C8 N12 1.5218(16) . ? C8 N9 1.5220(16) . ? N9 O10 1.2158(14) . ? N9 O11 1.2176(14) . ? N12 O13 1.2081(15) . ? N12 O14 1.2143(15) . ? N15 O16 1.2088(15) . ? N15 O17 1.2195(15) . ? N18 O19 1.2196(15) . ? N18 O20 1.2229(14) . ? N21 O23 1.2196(15) . ? N21 O22 1.2279(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 107.03(10) . . ? C2 N1 N6 122.94(10) . . ? C5 N1 N6 130.02(10) . . ? N3 C2 N1 111.76(11) . . ? N3 C2 H2 124.1 . . ? N1 C2 H2 124.1 . . ? C2 N3 C4 105.04(11) . . ? N3 C4 C5 111.45(11) . . ? N3 C4 N18 119.95(11) . . ? C5 C4 N18 128.51(12) . . ? C4 C5 N1 104.71(11) . . ? C4 C5 N21 133.44(12) . . ? N1 C5 N21 121.70(11) . . ? N1 N6 C7 113.21(10) . . ? N1 N6 H6 108.3(10) . . ? C7 N6 H6 114.3(10) . . ? N6 C7 C8 108.60(10) . . ? N6 C7 H7A 110.0 . . ? C8 C7 H7A 110.0 . . ? N6 C7 H7B 110.0 . . ? C8 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? N15 C8 C7 112.13(10) . . ? N15 C8 N12 107.15(9) . . ? C7 C8 N12 112.11(10) . . ? N15 C8 N9 107.92(10) . . ? C7 C8 N9 111.66(10) . . ? N12 C8 N9 105.52(9) . . ? O10 N9 O11 126.90(11) . . ? O10 N9 C8 117.65(10) . . ? O11 N9 C8 115.43(10) . . ? O13 N12 O14 127.68(12) . . ? O13 N12 C8 118.04(11) . . ? O14 N12 C8 114.27(11) . . ? O16 N15 O17 128.13(12) . . ? O16 N15 C8 117.65(11) . . ? O17 N15 C8 114.22(11) . . ? O19 N18 O20 125.48(11) . . ? O19 N18 C4 117.40(11) . . ? O20 N18 C4 117.12(10) . . ? O23 N21 O22 125.60(11) . . ? O23 N21 C5 117.21(11) . . ? O22 N21 C5 117.18(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C2 N3 0.19(14) . . . . ? N6 N1 C2 N3 179.27(11) . . . . ? N1 C2 N3 C4 -0.27(14) . . . . ? C2 N3 C4 C5 0.25(14) . . . . ? C2 N3 C4 N18 177.03(11) . . . . ? N3 C4 C5 N1 -0.14(14) . . . . ? N18 C4 C5 N1 -176.57(11) . . . . ? N3 C4 C5 N21 -175.53(12) . . . . ? N18 C4 C5 N21 8.0(2) . . . . ? C2 N1 C5 C4 -0.02(13) . . . . ? N6 N1 C5 C4 -179.01(11) . . . . ? C2 N1 C5 N21 176.05(11) . . . . ? N6 N1 C5 N21 -2.94(19) . . . . ? C2 N1 N6 C7 -117.13(12) . . . . ? C5 N1 N6 C7 61.72(16) . . . . ? N1 N6 C7 C8 140.78(10) . . . . ? N6 C7 C8 N15 -41.38(13) . . . . ? N6 C7 C8 N12 -161.96(10) . . . . ? N6 C7 C8 N9 79.87(12) . . . . ? N15 C8 N9 O10 -85.82(13) . . . . ? C7 C8 N9 O10 150.51(11) . . . . ? N12 C8 N9 O10 28.47(14) . . . . ? N15 C8 N9 O11 95.62(12) . . . . ? C7 C8 N9 O11 -28.04(14) . . . . ? N12 C8 N9 O11 -150.09(11) . . . . ? N15 C8 N12 O13 8.87(15) . . . . ? C7 C8 N12 O13 132.29(12) . . . . ? N9 C8 N12 O13 -105.96(13) . . . . ? N15 C8 N12 O14 -171.85(11) . . . . ? C7 C8 N12 O14 -48.42(15) . . . . ? N9 C8 N12 O14 73.33(13) . . . . ? C7 C8 N15 O16 129.27(12) . . . . ? N12 C8 N15 O16 -107.31(12) . . . . ? N9 C8 N15 O16 5.90(14) . . . . ? C7 C8 N15 O17 -50.64(14) . . . . ? N12 C8 N15 O17 72.78(13) . . . . ? N9 C8 N15 O17 -174.02(10) . . . . ? N3 C4 N18 O19 21.25(17) . . . . ? C5 C4 N18 O19 -162.58(12) . . . . ? N3 C4 N18 O20 -158.46(11) . . . . ? C5 C4 N18 O20 17.71(19) . . . . ? C4 C5 N21 O23 31.9(2) . . . . ? N1 C5 N21 O23 -142.85(12) . . . . ? C4 C5 N21 O22 -149.29(14) . . . . ? N1 C5 N21 O22 35.94(16) . . . . ? 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 N6 H6 N3 0.877(16) 2.137(16) 2.9887(15) 163.7(14) 2_446 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.286 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 927838' ####################################################################### # # 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_global #TrackingRef 'shrv220-final.cif' #=========================================================================== _audit_creation_date 2012-12-20 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _audit_update_record ; ; # Attachment 'shrv230-final.cif' #========================================================================== data_shrv230 #TrackingRef 'shrv230-final.cif' _audit_creation_date 2013-02-25 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 2,4-dinitro-N-(2,2,2-trinitroethyl)-1H-imidazol-1-amine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H4 N8 O10' _chemical_formula_sum 'C5 H4 N8 O10' _chemical_formula_weight 336.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 11.1074(7) _cell_length_b 9.5233(6) _cell_length_c 10.9770(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1161.14(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.923 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9158 _exptl_absorpt_correction_T_max 0.9566 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7852 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 26.40 _reflns_number_total 2270 _reflns_number_gt 2129 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _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^)+(0.0653P)^2^+0.5105P] 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 -0.4(15) _refine_ls_number_reflns 2270 _refine_ls_number_parameters 208 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.1071 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.20432(17) 1.0959(2) 0.8398(2) 0.0200(4) Uani 1 1 d . . . C2 C 0.1367(2) 1.1924(3) 0.7760(2) 0.0197(5) Uani 1 1 d . . . N3 N 0.02419(18) 1.1928(2) 0.8089(2) 0.0215(5) Uani 1 1 d . . . C4 C 0.0194(2) 1.0943(3) 0.8963(2) 0.0220(5) Uani 1 1 d . . . C5 C 0.1289(2) 1.0320(3) 0.9199(3) 0.0235(5) Uani 1 1 d . . . H5 H 0.1472 0.9614 0.9782 0.028 Uiso 1 1 calc R . . N6 N 0.32873(17) 1.0686(2) 0.8373(2) 0.0218(5) Uani 1 1 d . . . H6 H 0.3782 1.0941 0.8959 0.026 Uiso 1 1 calc R . . C7 C 0.3676(2) 0.9942(3) 0.7288(2) 0.0230(5) Uani 1 1 d . . . H7A H 0.4211 1.0554 0.6799 0.028 Uiso 1 1 calc R . . H7B H 0.2967 0.9700 0.6783 0.028 Uiso 1 1 calc R . . C8 C 0.4349(2) 0.8600(3) 0.7643(2) 0.0236(6) Uani 1 1 d . . . N9 N 0.5193(2) 0.8788(3) 0.8740(2) 0.0289(5) Uani 1 1 d . . . O11 O 0.5247(2) 0.7838(3) 0.9468(2) 0.0471(6) Uani 1 1 d . . . O12 O 0.5766(2) 0.9867(3) 0.8736(2) 0.0419(6) Uani 1 1 d . . . N12 N 0.5138(2) 0.8127(3) 0.6606(2) 0.0320(6) Uani 1 1 d . . . O13 O 0.6114(2) 0.7617(4) 0.6840(3) 0.0629(9) Uani 1 1 d . . . O14 O 0.4698(3) 0.8261(3) 0.56028(19) 0.0463(6) Uani 1 1 d . . . N15 N 0.3545(2) 0.7384(2) 0.7960(2) 0.0300(5) Uani 1 1 d . . . O16 O 0.3705(3) 0.6275(3) 0.7432(3) 0.0491(6) Uani 1 1 d . . . O17 O 0.2789(2) 0.7629(2) 0.8735(2) 0.0418(6) Uani 1 1 d . . . N18 N 0.1853(2) 1.2837(3) 0.6828(2) 0.0241(5) Uani 1 1 d . . . O19 O 0.1194(2) 1.3732(3) 0.6415(2) 0.0432(6) Uani 1 1 d . . . O20 O 0.28920(17) 1.2656(2) 0.6510(2) 0.0311(5) Uani 1 1 d . . . N21 N -0.09128(19) 1.0668(2) 0.9610(2) 0.0251(5) Uani 1 1 d . . . O22 O -0.18109(16) 1.1336(2) 0.9320(2) 0.0306(5) Uani 1 1 d . . . O23 O -0.08700(19) 0.9807(2) 1.0436(2) 0.0366(5) 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 N1 0.0162(9) 0.0175(11) 0.0262(10) -0.0002(9) -0.0015(8) 0.0013(8) C2 0.0213(12) 0.0180(13) 0.0199(11) -0.0008(9) -0.0025(10) 0.0027(10) N3 0.0189(10) 0.0216(12) 0.0238(10) -0.0002(9) -0.0012(8) 0.0035(8) C4 0.0213(12) 0.0178(13) 0.0270(13) -0.0021(10) 0.0008(10) 0.0008(9) C5 0.0235(12) 0.0174(13) 0.0295(13) 0.0008(10) 0.0011(11) 0.0018(9) N6 0.0119(9) 0.0239(12) 0.0295(11) -0.0027(9) -0.0058(8) 0.0022(7) C7 0.0187(12) 0.0215(13) 0.0289(12) 0.0024(11) -0.0004(10) 0.0022(9) C8 0.0206(12) 0.0227(15) 0.0274(13) -0.0040(10) -0.0028(10) 0.0015(10) N9 0.0255(11) 0.0324(14) 0.0288(12) -0.0057(11) -0.0032(9) 0.0111(10) O11 0.0453(14) 0.0520(15) 0.0442(14) 0.0071(12) -0.0109(11) 0.0097(11) O12 0.0347(12) 0.0342(13) 0.0566(14) -0.0136(11) -0.0159(11) 0.0015(9) N12 0.0328(13) 0.0303(14) 0.0329(13) -0.0082(11) 0.0009(11) 0.0028(10) O13 0.0362(13) 0.097(2) 0.0557(15) -0.0370(16) -0.0068(12) 0.0300(13) O14 0.0639(16) 0.0453(15) 0.0297(13) -0.0070(11) 0.0005(11) 0.0179(12) N15 0.0289(12) 0.0208(13) 0.0404(13) -0.0012(11) -0.0044(11) 0.0018(9) O16 0.0622(16) 0.0234(13) 0.0617(16) -0.0069(11) 0.0011(13) -0.0007(10) O17 0.0349(12) 0.0359(13) 0.0547(14) 0.0025(11) 0.0071(11) -0.0043(9) N18 0.0253(11) 0.0246(13) 0.0222(10) 0.0013(9) 0.0004(9) 0.0052(9) O19 0.0346(12) 0.0521(15) 0.0429(13) 0.0250(12) 0.0120(10) 0.0212(10) O20 0.0189(9) 0.0369(12) 0.0375(11) 0.0088(9) 0.0071(8) 0.0038(7) N21 0.0240(11) 0.0188(12) 0.0324(11) -0.0019(10) 0.0045(9) -0.0010(9) O22 0.0187(9) 0.0306(11) 0.0424(11) 0.0027(9) 0.0013(8) 0.0018(7) O23 0.0358(11) 0.0269(11) 0.0470(13) 0.0125(10) 0.0113(9) 0.0014(8) _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 C5 1.359(3) . ? N1 C2 1.378(3) . ? N1 N6 1.406(3) . ? C2 N3 1.301(3) . ? C2 N18 1.447(4) . ? N3 C4 1.343(3) . ? C4 C5 1.378(4) . ? C4 N21 1.443(3) . ? C5 H5 0.9500 . ? N6 C7 1.452(3) . ? N6 H6 0.8800 . ? C7 C8 1.532(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N15 1.503(4) . ? C8 N12 1.506(4) . ? C8 N9 1.536(3) . ? N9 O12 1.209(3) . ? N9 O11 1.209(4) . ? N12 O14 1.211(3) . ? N12 O13 1.216(4) . ? N15 O17 1.218(3) . ? N15 O16 1.218(3) . ? N18 O19 1.211(3) . ? N18 O20 1.218(3) . ? N21 O23 1.223(3) . ? N21 O22 1.225(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 C5 N1 C2 106.9(2) . . ? C5 N1 N6 122.4(2) . . ? C2 N1 N6 130.5(2) . . ? N3 C2 N1 112.6(2) . . ? N3 C2 N18 123.6(2) . . ? N1 C2 N18 123.8(2) . . ? C2 N3 C4 103.6(2) . . ? N3 C4 C5 113.6(2) . . ? N3 C4 N21 120.8(2) . . ? C5 C4 N21 125.5(2) . . ? N1 C5 C4 103.3(2) . . ? N1 C5 H5 128.3 . . ? C4 C5 H5 128.3 . . ? N1 N6 C7 113.5(2) . . ? N1 N6 H6 123.3 . . ? C7 N6 H6 123.3 . . ? N6 C7 C8 110.1(2) . . ? N6 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? N6 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.2 . . ? N15 C8 N12 106.9(2) . . ? N15 C8 C7 114.3(2) . . ? N12 C8 C7 109.9(2) . . ? N15 C8 N9 105.8(2) . . ? N12 C8 N9 105.8(2) . . ? C7 C8 N9 113.6(2) . . ? O12 N9 O11 127.7(3) . . ? O12 N9 C8 114.7(2) . . ? O11 N9 C8 117.5(2) . . ? O14 N12 O13 126.5(3) . . ? O14 N12 C8 114.9(2) . . ? O13 N12 C8 118.5(3) . . ? O17 N15 O16 126.7(3) . . ? O17 N15 C8 115.1(2) . . ? O16 N15 C8 118.1(3) . . ? O19 N18 O20 124.4(2) . . ? O19 N18 C2 117.5(2) . . ? O20 N18 C2 118.1(2) . . ? O23 N21 O22 124.9(2) . . ? O23 N21 C4 116.9(2) . . ? O22 N21 C4 118.1(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 C5 N1 C2 N3 -0.8(3) . . . . ? N6 N1 C2 N3 -175.7(2) . . . . ? C5 N1 C2 N18 179.0(2) . . . . ? N6 N1 C2 N18 4.1(4) . . . . ? N1 C2 N3 C4 0.2(3) . . . . ? N18 C2 N3 C4 -179.7(2) . . . . ? C2 N3 C4 C5 0.5(3) . . . . ? C2 N3 C4 N21 177.2(2) . . . . ? C2 N1 C5 C4 1.0(3) . . . . ? N6 N1 C5 C4 176.4(2) . . . . ? N3 C4 C5 N1 -1.0(3) . . . . ? N21 C4 C5 N1 -177.4(2) . . . . ? C5 N1 N6 C7 111.4(3) . . . . ? C2 N1 N6 C7 -74.3(3) . . . . ? N1 N6 C7 C8 -124.9(2) . . . . ? N6 C7 C8 N15 81.1(3) . . . . ? N6 C7 C8 N12 -158.7(2) . . . . ? N6 C7 C8 N9 -40.4(3) . . . . ? N15 C8 N9 O12 -167.9(2) . . . . ? N12 C8 N9 O12 78.9(3) . . . . ? C7 C8 N9 O12 -41.8(3) . . . . ? N15 C8 N9 O11 15.0(3) . . . . ? N12 C8 N9 O11 -98.2(3) . . . . ? C7 C8 N9 O11 141.1(3) . . . . ? N15 C8 N12 O14 85.3(3) . . . . ? C7 C8 N12 O14 -39.3(3) . . . . ? N9 C8 N12 O14 -162.3(3) . . . . ? N15 C8 N12 O13 -92.4(3) . . . . ? C7 C8 N12 O13 143.1(3) . . . . ? N9 C8 N12 O13 20.0(4) . . . . ? N12 C8 N15 O17 -175.2(2) . . . . ? C7 C8 N15 O17 -53.4(3) . . . . ? N9 C8 N15 O17 72.3(3) . . . . ? N12 C8 N15 O16 4.9(3) . . . . ? C7 C8 N15 O16 126.7(3) . . . . ? N9 C8 N15 O16 -107.6(3) . . . . ? N3 C2 N18 O19 6.7(4) . . . . ? N1 C2 N18 O19 -173.1(3) . . . . ? N3 C2 N18 O20 -173.2(3) . . . . ? N1 C2 N18 O20 7.0(4) . . . . ? N3 C4 N21 O23 -176.3(2) . . . . ? C5 C4 N21 O23 -0.1(4) . . . . ? N3 C4 N21 O22 1.6(4) . . . . ? C5 C4 N21 O22 177.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.424 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 927839'