# Electronic Supplementary Material (ESI) for RSC Advances # 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_cait85 #TrackingRef 'Hudry et al_Communication_RSC Advances 2013_Structure_only for reviewing process.cif' _audit_update_record ; 2013-03-25 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'H3 N Np0.50 O5.50' _chemical_formula_sum 'H3 N Np0.50 O5.50' _chemical_formula_weight 223.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Np Np -11.4937 4.1493 '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 5.6973(3) _cell_length_b 6.4675(4) _cell_length_c 7.0094(4) _cell_angle_alpha 109.9610(10) _cell_angle_beta 98.4810(10) _cell_angle_gamma 109.1920(10) _cell_volume 219.24(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description quader _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 201 _exptl_absorpt_coefficient_mu 11.905 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1401 _exptl_absorpt_correction_T_max 0.2771 _exptl_absorpt_process_details sadabs _exptl_special_details ? _diffrn_ambient_temperature 173(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 Apex II Quazar' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8643 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 38.58 _reflns_number_total 2408 _reflns_number_gt 2408 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II (Bruker, 2007)' _computing_cell_refinement 'APEX II (Bruker, 2007)' _computing_data_reduction 'APEX II (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XPMA (Zsolnai, 1996), ORTEP (Farrugia, 1997)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0935P)^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 2408 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1327 _refine_ls_wR_factor_gt 0.1327 _refine_ls_goodness_of_fit_ref 1.297 _refine_ls_restrained_S_all 1.297 _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 Np1 Np 0.0000 0.0000 0.0000 0.00457(9) Uani 1 2 d S . . O1 O 0.250(3) -0.070(2) 0.097(2) 0.0160(18) Uani 0.50 1 d P . . O2 O 0.3006(19) 0.141(3) 0.1835(19) 0.019(2) Uani 0.50 1 d P . . N1 N 0.273(2) 0.4940(19) 0.3255(17) 0.0096(15) Uani 0.50 1 d P . . O11 O 0.106(2) 0.328(2) 0.3502(19) 0.0150(17) Uani 0.50 1 d P . . O12 O 0.327(2) 0.4331(19) 0.1505(19) 0.0146(17) Uani 0.50 1 d P . . O13 O 0.384(3) 0.700(2) 0.466(2) 0.022(3) Uani 0.50 1 d P . . N2 N 0.189(3) 0.280(2) -0.243(2) 0.016(2) Uani 0.50 1 d P . . O21 O 0.2255(16) 0.0981(13) -0.2518(12) 0.0212(11) Uani 1 1 d . . . O22 O 0.081(4) 0.346(3) -0.097(2) 0.024(3) Uani 0.50 1 d P . . O23 O 0.251(3) 0.387(3) -0.352(3) 0.024(3) Uani 0.50 1 d P . . O3 O -0.117(3) 0.317(2) 0.209(2) 0.0174(19) Uani 0.50 1 d P . . O4 O 0.298(3) 0.761(2) 0.435(2) 0.0168(18) Uani 0.50 1 d P . . 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 Np1 0.00640(12) 0.00461(12) 0.00262(12) 0.00079(8) 0.00190(8) 0.00265(8) O1 0.021(5) 0.020(4) 0.017(4) 0.012(4) 0.005(4) 0.016(4) O2 0.004(3) 0.025(5) 0.012(4) 0.001(4) -0.008(3) -0.001(3) N1 0.013(4) 0.008(3) 0.005(3) 0.001(3) 0.002(3) 0.002(3) O11 0.018(4) 0.012(4) 0.012(4) 0.006(3) 0.009(3) 0.001(3) O12 0.017(4) 0.009(3) 0.014(4) 0.001(3) 0.011(3) 0.002(3) O13 0.027(6) 0.009(4) 0.020(5) -0.002(4) 0.012(5) 0.001(4) N2 0.018(5) 0.014(4) 0.020(5) 0.009(4) 0.007(4) 0.009(4) O21 0.029(3) 0.019(2) 0.023(3) 0.013(2) 0.018(2) 0.011(2) O22 0.046(8) 0.031(6) 0.020(5) 0.020(5) 0.026(6) 0.028(6) O23 0.031(6) 0.026(6) 0.028(7) 0.020(6) 0.016(6) 0.014(5) O3 0.023(5) 0.014(4) 0.018(5) 0.004(4) 0.011(4) 0.010(4) O4 0.018(4) 0.019(4) 0.015(4) 0.008(4) 0.006(4) 0.008(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 Np1 O2 1.715(9) 2 ? Np1 O2 1.715(9) . ? Np1 O1 1.746(11) . ? Np1 O1 1.746(11) 2 ? Np1 O3 2.436(12) 2 ? Np1 O3 2.436(12) . ? Np1 O11 2.460(12) 2 ? Np1 O11 2.460(12) . ? Np1 O21 2.463(6) 2 ? Np1 O21 2.463(6) . ? Np1 O22 2.475(13) 2 ? Np1 O22 2.475(13) . ? O1 O2 1.202(19) . ? N1 O13 1.230(16) . ? N1 O11 1.262(15) . ? N1 O12 1.271(16) . ? N1 O4 1.580(17) . ? O11 O3 1.46(2) . ? O13 O4 0.77(2) . ? N2 O23 1.21(2) . ? N2 O21 1.244(15) . ? N2 O22 1.291(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Np1 O2 179.999(1) 2 . ? O2 Np1 O1 139.4(7) 2 . ? O2 Np1 O1 40.6(7) . . ? O2 Np1 O1 40.6(7) 2 2 ? O2 Np1 O1 139.4(7) . 2 ? O1 Np1 O1 179.999(1) . 2 ? O2 Np1 O3 89.1(6) 2 2 ? O2 Np1 O3 90.9(6) . 2 ? O1 Np1 O3 55.2(5) . 2 ? O1 Np1 O3 124.9(5) 2 2 ? O2 Np1 O3 90.9(6) 2 . ? O2 Np1 O3 89.1(6) . . ? O1 Np1 O3 124.8(5) . . ? O1 Np1 O3 55.1(5) 2 . ? O3 Np1 O3 179.999(1) 2 . ? O2 Np1 O11 56.6(6) 2 2 ? O2 Np1 O11 123.4(6) . 2 ? O1 Np1 O11 89.7(5) . 2 ? O1 Np1 O11 90.3(5) 2 2 ? O3 Np1 O11 34.6(5) 2 2 ? O3 Np1 O11 145.4(5) . 2 ? O2 Np1 O11 123.4(6) 2 . ? O2 Np1 O11 56.6(6) . . ? O1 Np1 O11 90.3(5) . . ? O1 Np1 O11 89.7(5) 2 . ? O3 Np1 O11 145.4(5) 2 . ? O3 Np1 O11 34.6(5) . . ? O11 Np1 O11 179.999(1) 2 . ? O2 Np1 O21 86.7(5) 2 2 ? O2 Np1 O21 93.3(5) . 2 ? O1 Np1 O21 90.8(5) . 2 ? O1 Np1 O21 89.2(5) 2 2 ? O3 Np1 O21 113.6(4) 2 2 ? O3 Np1 O21 66.4(4) . 2 ? O11 Np1 O21 117.5(3) 2 2 ? O11 Np1 O21 62.5(3) . 2 ? O2 Np1 O21 93.3(5) 2 . ? O2 Np1 O21 86.7(5) . . ? O1 Np1 O21 89.2(5) . . ? O1 Np1 O21 90.8(5) 2 . ? O3 Np1 O21 66.4(4) 2 . ? O3 Np1 O21 113.6(4) . . ? O11 Np1 O21 62.5(3) 2 . ? O11 Np1 O21 117.5(3) . . ? O21 Np1 O21 180.000(1) 2 . ? O2 Np1 O22 91.7(7) 2 2 ? O2 Np1 O22 88.3(7) . 2 ? O1 Np1 O22 57.4(6) . 2 ? O1 Np1 O22 122.6(6) 2 2 ? O3 Np1 O22 63.9(4) 2 2 ? O3 Np1 O22 116.1(4) . 2 ? O11 Np1 O22 79.6(4) 2 2 ? O11 Np1 O22 100.4(4) . 2 ? O21 Np1 O22 50.1(3) 2 2 ? O21 Np1 O22 129.9(3) . 2 ? O2 Np1 O22 88.3(7) 2 . ? O2 Np1 O22 91.7(7) . . ? O1 Np1 O22 122.6(6) . . ? O1 Np1 O22 57.4(6) 2 . ? O3 Np1 O22 116.1(4) 2 . ? O3 Np1 O22 63.9(4) . . ? O11 Np1 O22 100.4(4) 2 . ? O11 Np1 O22 79.6(4) . . ? O21 Np1 O22 129.9(3) 2 . ? O21 Np1 O22 50.1(3) . . ? O22 Np1 O22 180.000(1) 2 . ? O2 O1 Np1 68.3(7) . . ? O1 O2 Np1 71.1(7) . . ? O13 N1 O11 121.9(12) . . ? O13 N1 O12 122.1(12) . . ? O11 N1 O12 115.9(11) . . ? O13 N1 O4 28.6(10) . . ? O11 N1 O4 119.8(11) . . ? O12 N1 O4 117.1(10) . . ? O13 N1 Np1 178.3(10) . . ? O11 N1 Np1 56.4(7) . . ? O12 N1 Np1 59.6(6) . . ? O4 N1 Np1 151.5(8) . . ? N1 O11 O3 95.4(11) . . ? N1 O11 Np1 98.3(8) . . ? O3 O11 Np1 71.8(6) . . ? N1 O12 Np1 94.7(7) . . ? O4 O13 N1 101.8(19) . . ? O23 N2 O21 125.0(15) . . ? O23 N2 O22 123.9(14) . . ? O21 N2 O22 111.0(13) . . ? O23 N2 Np1 175.9(13) . . ? O21 N2 Np1 55.3(6) . . ? O22 N2 Np1 56.1(8) . . ? N2 O21 Np1 100.2(8) . . ? N2 O22 Np1 98.2(9) . . ? O11 O3 Np1 73.6(7) . . ? O13 O4 N1 49.7(13) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.089 _refine_diff_density_min -14.869 _refine_diff_density_rms 1.125 _database_code_depnum_ccdc_archive 'CCDC 932455'