# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_1_1_K_crown_IV _database_code_depnum_ccdc_archive 'CCDC 868625' #TrackingRef '13948_web_deposit_cif_file_0_ColinSeaton_1347541186.Complied_cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (1,4,7,10,13,16-hexaoxacyclooctadecane)potassium 3,5-dinitrobenzoate ; _chemical_name_common ;(1,4,7,10,13,16-hexaoxacyclooctadecane)potassium 3,5- dinitrobenzoate ; _chemical_melting_point ? _chemical_formula_moiety 'C12 H24 K O6, C7 H3 N2 O6' _chemical_formula_sum 'C19 H27 K N2 O12' _chemical_formula_weight 514.53 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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _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 11.4037(3) _cell_length_b 8.1964(2) _cell_length_c 25.3329(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.066(2) _cell_angle_gamma 90.00 _cell_volume 2366.31(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9784 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 32.51 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.290 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8279 _exptl_absorpt_correction_T_max 0.9744 _exptl_absorpt_process_details 'Bruker SAINT' _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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 96861 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 35.39 _reflns_number_total 10022 _reflns_number_gt 7338 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.5372P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10022 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1052 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 K1 K 0.286780(17) 0.21181(3) 0.170628(8) 0.01909(5) Uani 1 1 d . . . C5 C 0.06187(8) -0.25660(12) -0.03002(4) 0.01886(17) Uani 1 1 d . . . C2 C -0.03937(8) -0.16076(12) 0.06191(3) 0.01785(17) Uani 1 1 d . . . C3 C -0.09707(8) -0.26358(12) 0.02618(4) 0.01740(16) Uani 1 1 d . . . C7 C 0.13902(8) 0.00859(12) 0.08936(4) 0.01926(17) Uani 1 1 d . . . C6 C 0.12432(8) -0.15543(12) 0.00461(4) 0.01850(17) Uani 1 1 d . . . C4 C -0.04885(8) -0.31572(12) -0.02027(4) 0.01848(17) Uani 1 1 d . . . C1 C 0.07374(8) -0.10784(11) 0.05135(3) 0.01659(16) Uani 1 1 d . . . O1 O 0.23626(7) 0.05846(11) 0.07517(3) 0.03045(18) Uani 1 1 d . . . O2 O 0.08865(8) 0.04395(11) 0.13076(3) 0.03315(19) Uani 1 1 d . . . O4 O -0.25117(7) -0.44540(11) 0.01604(4) 0.03414(19) Uani 1 1 d . . . O3 O -0.27521(8) -0.23340(13) 0.06550(4) 0.0401(2) Uani 1 1 d . . . O5 O 0.06694(8) -0.41253(12) -0.10574(4) 0.0372(2) Uani 1 1 d . . . O6 O 0.19842(9) -0.22419(14) -0.09432(4) 0.0452(3) Uani 1 1 d . . . N1 N -0.21673(7) -0.31839(12) 0.03674(3) 0.02373(18) Uani 1 1 d . . . N2 N 0.11307(8) -0.30069(12) -0.08044(4) 0.02733(19) Uani 1 1 d . . . O4A O 0.16045(7) 0.27118(10) 0.26469(3) 0.02707(16) Uani 1 1 d . . . O5A O 0.33878(7) 0.03455(9) 0.27142(3) 0.02519(15) Uani 1 1 d . . . O1A O 0.50181(7) 0.22718(10) 0.11087(3) 0.02529(15) Uani 1 1 d . . . O6A O 0.46686(6) -0.02469(10) 0.18253(3) 0.02463(15) Uani 1 1 d . . . O3A O 0.20946(7) 0.53984(10) 0.20052(3) 0.02728(16) Uani 1 1 d . . . O2A O 0.34419(7) 0.49050(10) 0.11027(3) 0.02883(17) Uani 1 1 d . . . C5A C 0.10051(10) 0.52156(17) 0.22580(5) 0.0324(2) Uani 1 1 d . . . C7A C 0.18469(10) 0.17891(16) 0.31123(4) 0.0273(2) Uani 1 1 d . . . C11A C 0.56026(9) -0.02579(16) 0.14677(5) 0.0295(2) Uani 1 1 d . . . C10A C 0.50182(10) -0.09179(15) 0.23242(5) 0.0288(2) Uani 1 1 d . . . C12A C 0.52288(10) 0.06207(15) 0.09725(4) 0.0275(2) Uani 1 1 d . . . C9A C 0.39467(11) -0.11848(14) 0.26356(5) 0.0292(2) Uani 1 1 d . . . C6A C 0.12073(10) 0.43081(16) 0.27662(5) 0.0299(2) Uani 1 1 d . . . C1A C 0.47931(12) 0.32543(17) 0.06547(5) 0.0341(3) Uani 1 1 d . . . C8A C 0.23067(11) 0.01436(16) 0.29665(5) 0.0317(2) Uani 1 1 d . . . C4A C 0.19599(12) 0.63605(16) 0.15393(5) 0.0340(3) Uani 1 1 d . . . C2A C 0.45155(12) 0.49425(17) 0.08353(5) 0.0354(3) Uani 1 1 d . . . C3A C 0.31154(13) 0.64770(15) 0.12819(5) 0.0341(3) Uani 1 1 d . . . H2 H -0.0753(12) -0.1242(17) 0.0933(6) 0.026(3) Uiso 1 1 d . . . H6 H 0.1965(13) -0.1183(18) -0.0029(6) 0.028(3) Uiso 1 1 d . . . H10A H 0.5564(13) -0.0173(18) 0.2511(6) 0.027(3) Uiso 1 1 d . . . H7AA H 0.2406(13) 0.2393(18) 0.3339(6) 0.027(3) Uiso 1 1 d . . . H7AB H 0.1144(14) 0.169(2) 0.3303(6) 0.036(4) Uiso 1 1 d . . . H12A H 0.4506(12) 0.0145(17) 0.0822(5) 0.025(3) Uiso 1 1 d . . . H4 H -0.0911(11) -0.3819(16) -0.0456(5) 0.021(3) Uiso 1 1 d . . . H5AA H 0.0430(14) 0.4655(19) 0.2008(6) 0.037(4) Uiso 1 1 d . . . H9AA H 0.3383(13) -0.1916(18) 0.2456(6) 0.030(4) Uiso 1 1 d . . . H8AA H 0.1738(15) -0.042(2) 0.2719(7) 0.041(4) Uiso 1 1 d . . . H6AA H 0.1794(13) 0.4876(19) 0.2997(6) 0.032(4) Uiso 1 1 d . . . H5AB H 0.0679(14) 0.628(2) 0.2337(7) 0.041(4) Uiso 1 1 d . . . H1AA H 0.4138(14) 0.2805(19) 0.0454(6) 0.034(4) Uiso 1 1 d . . . H11A H 0.6294(14) 0.0283(18) 0.1639(6) 0.032(4) Uiso 1 1 d . . . H10B H 0.5398(15) -0.195(2) 0.2292(7) 0.041(4) Uiso 1 1 d . . . H6AB H 0.0498(14) 0.425(2) 0.2951(6) 0.037(4) Uiso 1 1 d . . . H4AA H 0.1351(15) 0.585(2) 0.1278(7) 0.045(4) Uiso 1 1 d . . . H12B H 0.5849(13) 0.0546(18) 0.0723(6) 0.033(4) Uiso 1 1 d . . . H4AB H 0.1711(15) 0.745(2) 0.1634(7) 0.041(4) Uiso 1 1 d . . . H3AA H 0.3050(15) 0.723(2) 0.0993(7) 0.043(4) Uiso 1 1 d . . . H8AB H 0.2410(15) -0.054(2) 0.3289(7) 0.044(4) Uiso 1 1 d . . . H3AB H 0.3733(14) 0.686(2) 0.1511(7) 0.037(4) Uiso 1 1 d . . . H9AB H 0.4169(13) -0.1664(19) 0.2979(6) 0.035(4) Uiso 1 1 d . . . H2AA H 0.5148(15) 0.538(2) 0.1083(7) 0.042(4) Uiso 1 1 d . . . H11B H 0.5829(14) -0.136(2) 0.1381(6) 0.040(4) Uiso 1 1 d . . . H1AB H 0.5464(16) 0.329(2) 0.0445(7) 0.049(5) Uiso 1 1 d . . . H2AB H 0.4432(15) 0.565(2) 0.0529(7) 0.047(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 K1 0.01953(9) 0.01935(10) 0.01827(9) -0.00109(7) -0.00089(6) 0.00000(7) C5 0.0206(4) 0.0176(4) 0.0185(4) -0.0040(3) 0.0029(3) 0.0023(3) C2 0.0206(4) 0.0181(4) 0.0148(4) 0.0005(3) 0.0000(3) 0.0012(3) C3 0.0166(4) 0.0182(4) 0.0174(4) 0.0013(3) 0.0004(3) 0.0000(3) C7 0.0217(4) 0.0171(4) 0.0185(4) -0.0009(3) -0.0051(3) 0.0012(3) C6 0.0174(4) 0.0173(4) 0.0208(4) -0.0014(3) 0.0005(3) 0.0012(3) C4 0.0203(4) 0.0161(4) 0.0189(4) -0.0019(3) -0.0009(3) 0.0004(3) C1 0.0188(4) 0.0147(4) 0.0161(4) 0.0007(3) -0.0022(3) 0.0012(3) O1 0.0224(3) 0.0386(5) 0.0302(4) -0.0100(3) -0.0004(3) -0.0080(3) O2 0.0339(4) 0.0416(5) 0.0241(4) -0.0132(3) 0.0045(3) -0.0109(4) O4 0.0268(4) 0.0324(5) 0.0430(5) -0.0030(4) -0.0020(3) -0.0106(3) O3 0.0250(4) 0.0597(6) 0.0363(5) -0.0143(4) 0.0111(3) -0.0035(4) O5 0.0384(4) 0.0408(5) 0.0330(4) -0.0217(4) 0.0086(4) -0.0057(4) O6 0.0396(5) 0.0573(6) 0.0401(5) -0.0196(5) 0.0222(4) -0.0185(5) N1 0.0193(4) 0.0310(5) 0.0208(4) 0.0025(3) -0.0003(3) -0.0031(3) N2 0.0264(4) 0.0303(5) 0.0257(4) -0.0103(4) 0.0071(3) -0.0005(4) O4A 0.0285(4) 0.0324(4) 0.0205(3) -0.0033(3) 0.0040(3) 0.0010(3) O5A 0.0271(3) 0.0218(4) 0.0271(4) 0.0050(3) 0.0058(3) -0.0026(3) O1A 0.0268(4) 0.0283(4) 0.0209(3) -0.0003(3) 0.0024(3) 0.0008(3) O6A 0.0199(3) 0.0272(4) 0.0267(3) 0.0038(3) 0.0013(3) 0.0076(3) O3A 0.0237(3) 0.0275(4) 0.0305(4) 0.0035(3) -0.0015(3) 0.0066(3) O2A 0.0358(4) 0.0204(4) 0.0305(4) 0.0026(3) 0.0039(3) -0.0023(3) C5A 0.0221(5) 0.0381(7) 0.0370(6) -0.0040(5) -0.0002(4) 0.0110(5) C7A 0.0249(5) 0.0369(6) 0.0205(4) 0.0000(4) 0.0060(4) -0.0082(4) C11A 0.0201(4) 0.0307(6) 0.0383(6) -0.0012(5) 0.0063(4) 0.0085(4) C10A 0.0298(5) 0.0248(5) 0.0312(5) 0.0031(4) -0.0060(4) 0.0089(4) C12A 0.0227(4) 0.0318(6) 0.0283(5) -0.0057(4) 0.0071(4) 0.0024(4) C9A 0.0392(6) 0.0212(5) 0.0269(5) 0.0069(4) -0.0020(4) 0.0017(4) C6A 0.0227(5) 0.0388(7) 0.0285(5) -0.0073(5) 0.0044(4) 0.0050(4) C1A 0.0394(6) 0.0420(7) 0.0214(5) 0.0068(5) 0.0083(4) 0.0028(5) C8A 0.0314(5) 0.0318(6) 0.0326(5) 0.0054(5) 0.0103(4) -0.0099(5) C4A 0.0411(6) 0.0250(6) 0.0356(6) 0.0059(5) -0.0041(5) 0.0108(5) C2A 0.0407(6) 0.0324(6) 0.0336(6) 0.0120(5) 0.0084(5) -0.0047(5) C3A 0.0479(7) 0.0183(5) 0.0361(6) 0.0053(4) -0.0008(5) -0.0007(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 K1 O1 2.7675(8) . ? K1 O2 2.8025(8) . ? K1 O6A 2.8322(7) . ? K1 O2A 2.8384(8) . ? K1 O4A 2.8702(8) . ? K1 O1A 2.9305(8) . ? K1 O3A 2.9373(8) . ? K1 O5A 2.9788(8) . ? K1 C7 3.0986(10) . ? C5 C4 1.3829(13) . ? C5 C6 1.3854(14) . ? C5 N2 1.4685(12) . ? C2 C3 1.3855(13) . ? C2 C1 1.3959(13) . ? C2 H2 0.956(14) . ? C3 C4 1.3842(13) . ? C3 N1 1.4703(12) . ? C7 O1 1.2468(12) . ? C7 O2 1.2478(12) . ? C7 C1 1.5300(13) . ? C6 C1 1.3913(13) . ? C6 H6 0.904(14) . ? C4 H4 0.957(13) . ? O4 N1 1.2240(13) . ? O3 N1 1.2230(13) . ? O5 N2 1.2262(13) . ? O6 N2 1.2203(13) . ? O4A C7A 1.4195(14) . ? O4A C6A 1.4206(15) . ? O5A C8A 1.4186(13) . ? O5A C9A 1.4242(14) . ? O1A C1A 1.4198(14) . ? O1A C12A 1.4192(14) . ? O6A C10A 1.4222(13) . ? O6A C11A 1.4229(13) . ? O3A C4A 1.4232(14) . ? O3A C5A 1.4261(14) . ? O2A C2A 1.4207(15) . ? O2A C3A 1.4202(15) . ? C5A C6A 1.4974(18) . ? C5A H5AA 1.006(17) . ? C5A H5AB 0.972(17) . ? C7A C8A 1.4981(18) . ? C7A H7AA 0.977(15) . ? C7A H7AB 0.954(16) . ? C11A C12A 1.4951(17) . ? C11A H11A 0.990(16) . ? C11A H11B 0.965(17) . ? C10A C9A 1.4942(17) . ? C10A H10A 0.982(15) . ? C10A H10B 0.959(17) . ? C12A H12A 0.977(14) . ? C12A H12B 0.967(15) . ? C9A H9AA 0.978(16) . ? C9A H9AB 0.980(16) . ? C6A H6AA 0.989(16) . ? C6A H6AB 0.950(16) . ? C1A C2A 1.495(2) . ? C1A H1AA 0.961(17) . ? C1A H1AB 0.947(18) . ? C8A H8AA 0.997(17) . ? C8A H8AB 0.996(18) . ? C4A C3A 1.4942(19) . ? C4A H4AA 1.030(18) . ? C4A H4AB 0.967(17) . ? C2A H2AA 1.005(17) . ? C2A H2AB 0.970(18) . ? C3A H3AA 0.958(18) . ? C3A H3AB 0.951(17) . ? 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 O1 K1 O2 47.34(2) . . ? O1 K1 O6A 84.80(3) . . ? O2 K1 O6A 105.93(3) . . ? O1 K1 O2A 86.54(3) . . ? O2 K1 O2A 113.55(3) . . ? O6A K1 O2A 115.32(2) . . ? O1 K1 O4A 135.04(2) . . ? O2 K1 O4A 87.72(2) . . ? O6A K1 O4A 114.29(2) . . ? O2A K1 O4A 116.31(2) . . ? O1 K1 O1A 73.73(2) . . ? O2 K1 O1A 120.91(2) . . ? O6A K1 O1A 57.82(2) . . ? O2A K1 O1A 58.24(2) . . ? O4A K1 O1A 151.16(2) . . ? O1 K1 O3A 125.88(3) . . ? O2 K1 O3A 107.26(3) . . ? O6A K1 O3A 145.32(2) . . ? O2A K1 O3A 58.63(2) . . ? O4A K1 O3A 57.76(2) . . ? O1A K1 O3A 111.00(2) . . ? O1 K1 O5A 123.79(3) . . ? O2 K1 O5A 101.68(3) . . ? O6A K1 O5A 56.89(2) . . ? O2A K1 O5A 144.26(2) . . ? O4A K1 O5A 57.41(2) . . ? O1A K1 O5A 108.62(2) . . ? O3A K1 O5A 106.13(2) . . ? O1 K1 C7 23.69(2) . . ? O2 K1 C7 23.74(2) . . ? O6A K1 C7 94.45(2) . . ? O2A K1 C7 101.84(3) . . ? O4A K1 C7 111.44(3) . . ? O1A K1 C7 97.18(2) . . ? O3A K1 C7 120.15(2) . . ? O5A K1 C7 113.20(2) . . ? C4 C5 C6 123.26(9) . . ? C4 C5 N2 117.60(9) . . ? C6 C5 N2 119.12(9) . . ? C3 C2 C1 118.96(8) . . ? C3 C2 H2 121.8(8) . . ? C1 C2 H2 119.2(8) . . ? C4 C3 C2 123.32(9) . . ? C4 C3 N1 117.39(8) . . ? C2 C3 N1 119.28(8) . . ? O1 C7 O2 127.40(9) . . ? O1 C7 C1 116.14(8) . . ? O2 C7 C1 116.46(9) . . ? O1 C7 K1 63.09(5) . . ? O2 C7 K1 64.70(5) . . ? C1 C7 K1 173.78(6) . . ? C5 C6 C1 119.16(9) . . ? C5 C6 H6 121.2(9) . . ? C1 C6 H6 119.6(9) . . ? C5 C4 C3 115.90(9) . . ? C5 C4 H4 121.4(8) . . ? C3 C4 H4 122.6(8) . . ? C6 C1 C2 119.36(8) . . ? C6 C1 C7 120.22(8) . . ? C2 C1 C7 120.34(8) . . ? C7 O1 K1 93.22(6) . . ? C7 O2 K1 91.56(6) . . ? O3 N1 O4 124.49(9) . . ? O3 N1 C3 117.64(9) . . ? O4 N1 C3 117.87(9) . . ? O6 N2 O5 124.40(9) . . ? O6 N2 C5 118.07(9) . . ? O5 N2 C5 117.53(9) . . ? C7A O4A C6A 111.60(9) . . ? C7A O4A K1 120.71(6) . . ? C6A O4A K1 120.40(6) . . ? C8A O5A C9A 111.15(9) . . ? C8A O5A K1 107.08(7) . . ? C9A O5A K1 112.70(6) . . ? C1A O1A C12A 111.79(9) . . ? C1A O1A K1 108.22(7) . . ? C12A O1A K1 103.69(6) . . ? C10A O6A C11A 111.78(8) . . ? C10A O6A K1 122.57(6) . . ? C11A O6A K1 119.54(6) . . ? C4A O3A C5A 111.16(9) . . ? C4A O3A K1 108.53(7) . . ? C5A O3A K1 107.10(7) . . ? C2A O2A C3A 111.91(9) . . ? C2A O2A K1 119.58(7) . . ? C3A O2A K1 119.33(7) . . ? O3A C5A C6A 109.19(9) . . ? O3A C5A H5AA 108.9(9) . . ? C6A C5A H5AA 113.0(9) . . ? O3A C5A H5AB 110.1(10) . . ? C6A C5A H5AB 108.5(10) . . ? H5AA C5A H5AB 107.1(13) . . ? O4A C7A C8A 109.52(9) . . ? O4A C7A H7AA 108.7(9) . . ? C8A C7A H7AA 112.0(9) . . ? O4A C7A H7AB 108.9(10) . . ? C8A C7A H7AB 110.8(10) . . ? H7AA C7A H7AB 106.8(13) . . ? O6A C11A C12A 109.50(8) . . ? O6A C11A H11A 108.7(9) . . ? C12A C11A H11A 110.5(9) . . ? O6A C11A H11B 111.3(10) . . ? C12A C11A H11B 109.3(10) . . ? H11A C11A H11B 107.6(13) . . ? O6A C10A C9A 108.50(9) . . ? O6A C10A H10A 109.9(8) . . ? C9A C10A H10A 110.7(8) . . ? O6A C10A H10B 112.3(10) . . ? C9A C10A H10B 107.2(10) . . ? H10A C10A H10B 108.2(13) . . ? O1A C12A C11A 107.51(9) . . ? O1A C12A H12A 109.1(8) . . ? C11A C12A H12A 110.3(8) . . ? O1A C12A H12B 110.7(9) . . ? C11A C12A H12B 108.9(9) . . ? H12A C12A H12B 110.3(12) . . ? O5A C9A C10A 108.88(9) . . ? O5A C9A H9AA 108.3(9) . . ? C10A C9A H9AA 112.4(9) . . ? O5A C9A H9AB 109.4(9) . . ? C10A C9A H9AB 109.7(9) . . ? H9AA C9A H9AB 108.1(13) . . ? O4A C6A C5A 108.37(9) . . ? O4A C6A H6AA 110.2(9) . . ? C5A C6A H6AA 110.8(9) . . ? O4A C6A H6AB 109.8(10) . . ? C5A C6A H6AB 110.0(10) . . ? H6AA C6A H6AB 107.7(13) . . ? O1A C1A C2A 108.13(10) . . ? O1A C1A H1AA 109.0(9) . . ? C2A C1A H1AA 110.3(9) . . ? O1A C1A H1AB 110.1(11) . . ? C2A C1A H1AB 109.2(11) . . ? H1AA C1A H1AB 110.1(14) . . ? O5A C8A C7A 108.89(9) . . ? O5A C8A H8AA 109.0(9) . . ? C7A C8A H8AA 110.1(10) . . ? O5A C8A H8AB 110.9(10) . . ? C7A C8A H8AB 109.8(10) . . ? H8AA C8A H8AB 108.1(14) . . ? O3A C4A C3A 109.08(10) . . ? O3A C4A H4AA 111.1(10) . . ? C3A C4A H4AA 109.3(9) . . ? O3A C4A H4AB 109.1(10) . . ? C3A C4A H4AB 108.8(10) . . ? H4AA C4A H4AB 109.5(14) . . ? O2A C2A C1A 108.75(10) . . ? O2A C2A H2AA 108.7(9) . . ? C1A C2A H2AA 111.5(10) . . ? O2A C2A H2AB 109.4(10) . . ? C1A C2A H2AB 108.9(11) . . ? H2AA C2A H2AB 109.5(14) . . ? O2A C3A C4A 109.08(10) . . ? O2A C3A H3AA 110.7(10) . . ? C4A C3A H3AA 109.2(10) . . ? O2A C3A H3AB 107.6(10) . . ? C4A C3A H3AB 113.5(10) . . ? H3AA C3A H3AB 106.8(14) . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 28.90 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.567 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.060 data_2_1_K_crown_V _database_code_depnum_ccdc_archive 'CCDC 868626' #TrackingRef '13948_web_deposit_cif_file_0_ColinSeaton_1347541186.Complied_cifs.cif' _chemical_name_systematic ; (1,4,7,10,13,16-hexaoxacyclooctadecane)potassium 3,5-dinitrobenzoate 3,5-dinitrobenzoic acid ; _chemical_name_common ; (1,4,7,10,13,16-hexaoxacyclooctadecane)potassium 3,5- dinitrobenzoate 3,5-dinitrobenzoic acid ; _chemical_melting_point ? _chemical_formula_moiety 'C12 H24 K O6, C7 H3 N2 O6, C7 H4 N2 O6)' _chemical_formula_sum 'C26 H31 K N4 O18' _chemical_formula_weight 726.65 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' K K 0.2009 0.2494 '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 9.2865(3) _cell_length_b 13.1382(4) _cell_length_c 14.0544(4) _cell_angle_alpha 71.4950(10) _cell_angle_beta 79.2300(10) _cell_angle_gamma 86.2320(10) _cell_volume 1597.41(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9924 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 30.98 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.82 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.254 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8182 _exptl_absorpt_correction_T_max 0.9382 _exptl_absorpt_process_details 'Bruker SAINT' _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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24828 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 31.04 _reflns_number_total 8680 _reflns_number_gt 7504 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0807P)^2^+0.7197P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8680 _refine_ls_number_parameters 566 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.1079 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 0.829 _refine_ls_restrained_S_all 0.829 _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 K1 K -0.32236(3) 0.528867(18) 0.215225(18) 0.02173(7) Uani 1 1 d . . . O O -0.43525(9) 0.73272(7) 0.19301(6) 0.02435(17) Uani 1 1 d . . . O0AA O -0.05657(10) 0.62448(7) 0.19418(8) 0.0319(2) Uani 1 1 d . . . O1AA O -0.59572(10) 0.45949(7) 0.25172(7) 0.03018(19) Uani 1 1 d . . . O2AA O -0.83035(9) 0.44320(6) 0.33053(7) 0.02692(18) Uani 1 1 d . . . O3AA O 0.12189(10) 0.63677(7) 0.27756(8) 0.0314(2) Uani 1 1 d . . . O4AA O -0.40744(10) 0.64265(7) 0.03075(7) 0.02831(18) Uani 1 1 d . . . O5AA O -0.19646(10) 0.32733(8) 0.24362(8) 0.0330(2) Uani 1 1 d . . . O6AA O -0.21291(11) 1.11696(7) 0.02397(7) 0.0330(2) Uani 1 1 d . . . O7AA O -0.30778(10) 0.38716(8) 0.42868(8) 0.0328(2) Uani 1 1 d . . . O8AA O -0.20757(11) 0.47379(8) 0.04429(7) 0.0329(2) Uani 1 1 d . . . C C -0.70175(12) 0.40741(9) 0.30602(8) 0.0207(2) Uani 1 1 d . . . O9AA O -0.35945(12) 0.60215(8) 0.37464(7) 0.0342(2) Uani 1 1 d . . . C0AA C 0.10435(12) 0.85410(9) 0.22217(9) 0.0209(2) Uani 1 1 d . . . C1AA C 0.02042(12) 0.67523(9) 0.22403(9) 0.0219(2) Uani 1 1 d . . . N N -0.22494(12) 1.01982(9) 0.06031(9) 0.0294(2) Uani 1 1 d . . . C2AA C 0.00462(11) 0.79603(8) 0.19751(8) 0.0200(2) Uani 1 1 d . . . C3AA C -0.68637(12) 0.28668(8) 0.35053(8) 0.0202(2) Uani 1 1 d . . . C4AA C -0.77762(14) 0.11828(9) 0.46680(9) 0.0252(2) Uani 1 1 d . . . N0AA N -0.43461(13) 0.06476(9) 0.30848(9) 0.0329(2) Uani 1 1 d . . . C5AA C 0.09107(12) 0.96485(9) 0.19427(9) 0.0219(2) Uani 1 1 d . . . C6AA C -0.79429(13) 0.22841(9) 0.42773(9) 0.0224(2) Uani 1 1 d . . . O0BA O 0.17291(12) 1.12153(7) 0.20743(9) 0.0414(3) Uani 1 1 d . . . O1BA O -0.41913(13) -0.03094(8) 0.35298(9) 0.0441(3) Uani 1 1 d . . . C7AA C -0.66063(15) 0.06248(9) 0.43062(10) 0.0278(2) Uani 1 1 d . . . C8AA C -0.11307(12) 0.96039(9) 0.11933(9) 0.0225(2) Uani 1 1 d . . . C9AA C -0.01629(12) 1.02078(9) 0.14256(9) 0.0230(2) Uani 1 1 d . . . N1AA N -0.89065(14) 0.05767(9) 0.54949(9) 0.0331(2) Uani 1 1 d . . . C0BA C -0.55705(13) 0.12261(9) 0.35272(9) 0.0254(2) Uani 1 1 d . . . C1BA C -0.10654(12) 0.84944(9) 0.14608(9) 0.0226(2) Uani 1 1 d . . . C2BA C -0.56525(13) 0.23341(9) 0.31291(9) 0.0229(2) Uani 1 1 d . . . N2AA N 0.19657(11) 1.02615(8) 0.22010(9) 0.0273(2) Uani 1 1 d . . . O2BA O 0.30232(12) 0.97829(8) 0.25326(11) 0.0465(3) Uani 1 1 d . . . C3BA C -0.21482(16) 0.45436(11) 0.45254(11) 0.0333(3) Uani 1 1 d . . . C4BA C -0.52867(14) 0.76100(11) 0.11843(10) 0.0293(2) Uani 1 1 d . . . O3BA O -0.32043(15) 0.96879(10) 0.04838(13) 0.0646(4) Uani 1 1 d . . . C5BA C -0.40847(15) 0.70858(11) 0.36479(10) 0.0300(3) Uani 1 1 d . . . O4BA O -0.86640(17) -0.03583(9) 0.59296(11) 0.0622(4) Uani 1 1 d . . . O5BA O -1.00393(14) 0.10384(10) 0.57113(9) 0.0521(3) Uani 1 1 d . . . O6BA O -0.35728(14) 0.11520(10) 0.22982(10) 0.0502(3) Uani 1 1 d . . . C6BA C -0.51111(14) 0.73891(11) 0.28902(10) 0.0306(3) Uani 1 1 d . . . C7BA C -0.44270(15) 0.75249(11) 0.01983(10) 0.0304(3) Uani 1 1 d . . . C8BA C -0.30070(17) 0.55186(12) 0.46467(10) 0.0338(3) Uani 1 1 d . . . C9BA C -0.12717(15) 0.29575(11) 0.33138(13) 0.0359(3) Uani 1 1 d . . . C0CA C -0.24036(17) 0.28782(11) 0.42486(12) 0.0378(3) Uani 1 1 d . . . C1CA C -0.3126(2) 0.63032(13) -0.05617(11) 0.0414(3) Uani 1 1 d . . . C2CA C -0.1661(2) 0.36437(13) 0.06318(13) 0.0456(4) Uani 1 1 d . . . C3CA C -0.28035(18) 0.51310(13) -0.04026(11) 0.0382(3) Uani 1 1 d . . . C4CA C -0.09183(19) 0.33151(15) 0.15418(14) 0.0471(4) Uani 1 1 d . . . H7BA H -0.355(2) 0.7943(14) 0.0006(13) 0.037(4) Uiso 1 1 d . . . H4BA H -0.6117(19) 0.7150(14) 0.1400(13) 0.032(4) Uiso 1 1 d . . . H0AA H 0.1789(18) 0.8206(13) 0.2556(12) 0.028(4) Uiso 1 1 d . . . H5BA H -0.3268(19) 0.7568(14) 0.3420(13) 0.031(4) Uiso 1 1 d . . . H9AA H -0.0242(18) 1.0944(14) 0.1236(13) 0.033(4) Uiso 1 1 d . . . H6AA H -0.8768(18) 0.2619(13) 0.4550(12) 0.029(4) Uiso 1 1 d . . . H1BA H -0.1727(19) 0.8130(14) 0.1291(13) 0.035(4) Uiso 1 1 d . . . H4BB H -0.5644(19) 0.8332(14) 0.1087(13) 0.033(4) Uiso 1 1 d . . . H9BA H -0.0524(19) 0.3479(14) 0.3240(13) 0.036(4) Uiso 1 1 d . . . H5BB H -0.457(2) 0.7139(14) 0.4287(14) 0.038(4) Uiso 1 1 d . . . H7AA H -0.6514(19) -0.0106(15) 0.4563(13) 0.038(4) Uiso 1 1 d . . . H8BA H -0.383(2) 0.5326(15) 0.5236(14) 0.040(5) Uiso 1 1 d . . . H0CA H -0.196(2) 0.2564(15) 0.4845(15) 0.043(5) Uiso 1 1 d . . . H8BB H -0.232(2) 0.5978(15) 0.4781(14) 0.044(5) Uiso 1 1 d . . . H2BA H -0.4924(18) 0.2711(13) 0.2630(13) 0.030(4) Uiso 1 1 d . . . H6BA H -0.5497(19) 0.8114(14) 0.2823(13) 0.034(4) Uiso 1 1 d . . . H6BB H -0.601(2) 0.6906(15) 0.3138(14) 0.042(5) Uiso 1 1 d . . . H3BA H -0.130(2) 0.4761(14) 0.3976(14) 0.039(5) Uiso 1 1 d . . . H3CA H -0.368(2) 0.4739(16) -0.0301(15) 0.046(5) Uiso 1 1 d . . . H0CB H -0.323(2) 0.2444(16) 0.4249(15) 0.050(5) Uiso 1 1 d . . . H3BB H -0.183(2) 0.4157(16) 0.5177(15) 0.047(5) Uiso 1 1 d . . . H9BB H -0.080(2) 0.2280(16) 0.3355(15) 0.045(5) Uiso 1 1 d . . . H7BB H -0.496(2) 0.7805(16) -0.0323(15) 0.047(5) Uiso 1 1 d . . . H3CB H -0.214(2) 0.5056(16) -0.1008(16) 0.051(5) Uiso 1 1 d . . . H2CA H -0.252(2) 0.3221(17) 0.0729(16) 0.055(6) Uiso 1 1 d . . . H1CA H -0.215(3) 0.6643(18) -0.0643(17) 0.060(6) Uiso 1 1 d . . . H2CB H -0.095(2) 0.3580(17) 0.0068(17) 0.058(6) Uiso 1 1 d . . . H1 H -0.015(2) 0.3880(18) 0.1462(17) 0.057(6) Uiso 1 1 d . . . H4CA H -0.050(3) 0.2588(19) 0.1602(17) 0.062(6) Uiso 1 1 d . . . H1CB H -0.359(3) 0.6586(19) -0.1172(19) 0.068(7) Uiso 1 1 d . . . H3AA H 0.143(3) 0.552(2) 0.292(2) 0.089(8) 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 K1 0.02259(12) 0.02085(12) 0.02426(12) -0.00983(9) -0.00568(9) 0.00077(8) O 0.0216(4) 0.0266(4) 0.0256(4) -0.0087(3) -0.0063(3) 0.0042(3) O0AA 0.0295(4) 0.0239(4) 0.0472(5) -0.0133(4) -0.0143(4) -0.0024(3) O1AA 0.0251(4) 0.0239(4) 0.0368(5) -0.0035(4) -0.0028(4) -0.0044(3) O2AA 0.0237(4) 0.0179(4) 0.0362(5) -0.0049(3) -0.0043(3) 0.0007(3) O3AA 0.0336(5) 0.0178(4) 0.0468(5) -0.0079(4) -0.0214(4) 0.0024(3) O4AA 0.0301(4) 0.0304(4) 0.0248(4) -0.0097(3) -0.0031(3) -0.0021(3) O5AA 0.0292(4) 0.0287(4) 0.0458(5) -0.0162(4) -0.0120(4) 0.0052(3) O6AA 0.0357(5) 0.0258(4) 0.0351(5) -0.0039(4) -0.0133(4) 0.0077(4) O7AA 0.0313(5) 0.0296(5) 0.0372(5) -0.0070(4) -0.0118(4) -0.0004(4) O8AA 0.0358(5) 0.0332(5) 0.0358(5) -0.0199(4) -0.0054(4) 0.0013(4) C 0.0234(5) 0.0180(5) 0.0221(5) -0.0056(4) -0.0081(4) -0.0013(4) O9AA 0.0517(6) 0.0309(5) 0.0259(4) -0.0142(4) -0.0159(4) 0.0122(4) C0AA 0.0192(5) 0.0192(5) 0.0261(5) -0.0083(4) -0.0073(4) 0.0022(4) C1AA 0.0199(5) 0.0187(5) 0.0263(5) -0.0065(4) -0.0032(4) -0.0011(4) N 0.0271(5) 0.0267(5) 0.0353(6) -0.0072(4) -0.0139(4) 0.0049(4) C2AA 0.0181(4) 0.0183(5) 0.0238(5) -0.0072(4) -0.0035(4) -0.0001(4) C3AA 0.0236(5) 0.0178(5) 0.0212(5) -0.0060(4) -0.0083(4) -0.0003(4) C4AA 0.0332(6) 0.0207(5) 0.0216(5) -0.0032(4) -0.0084(4) -0.0059(4) N0AA 0.0377(6) 0.0295(5) 0.0383(6) -0.0175(5) -0.0149(5) 0.0108(4) C5AA 0.0209(5) 0.0200(5) 0.0277(5) -0.0104(4) -0.0063(4) -0.0005(4) C6AA 0.0258(5) 0.0207(5) 0.0223(5) -0.0066(4) -0.0077(4) -0.0012(4) O0BA 0.0447(6) 0.0193(4) 0.0676(7) -0.0149(4) -0.0259(5) 0.0013(4) O1BA 0.0535(6) 0.0289(5) 0.0553(7) -0.0173(5) -0.0219(5) 0.0178(4) C7AA 0.0398(7) 0.0185(5) 0.0278(6) -0.0068(4) -0.0136(5) 0.0006(4) C8AA 0.0196(5) 0.0226(5) 0.0252(5) -0.0058(4) -0.0076(4) 0.0032(4) C9AA 0.0239(5) 0.0187(5) 0.0265(5) -0.0068(4) -0.0056(4) 0.0019(4) N1AA 0.0425(6) 0.0280(5) 0.0263(5) -0.0028(4) -0.0062(5) -0.0115(5) C0BA 0.0297(6) 0.0238(5) 0.0277(6) -0.0121(4) -0.0121(4) 0.0056(4) C1BA 0.0193(5) 0.0227(5) 0.0267(5) -0.0075(4) -0.0062(4) -0.0013(4) C2BA 0.0248(5) 0.0224(5) 0.0232(5) -0.0078(4) -0.0077(4) 0.0009(4) N2AA 0.0268(5) 0.0214(5) 0.0393(6) -0.0134(4) -0.0127(4) 0.0009(4) O2BA 0.0385(5) 0.0333(5) 0.0860(9) -0.0307(5) -0.0384(6) 0.0113(4) C3BA 0.0355(7) 0.0331(6) 0.0335(7) -0.0084(5) -0.0156(6) 0.0013(5) C4BA 0.0239(5) 0.0312(6) 0.0337(6) -0.0090(5) -0.0115(5) 0.0062(5) O3BA 0.0543(7) 0.0365(6) 0.1090(12) -0.0051(7) -0.0592(8) -0.0022(5) C5BA 0.0365(6) 0.0289(6) 0.0289(6) -0.0158(5) -0.0059(5) 0.0049(5) O4BA 0.0769(9) 0.0230(5) 0.0657(8) 0.0061(5) 0.0086(7) -0.0126(5) O5BA 0.0456(6) 0.0540(7) 0.0375(6) 0.0048(5) 0.0072(5) -0.0035(5) O6BA 0.0515(7) 0.0447(6) 0.0492(7) -0.0183(5) 0.0072(5) 0.0108(5) C6BA 0.0282(6) 0.0326(6) 0.0324(6) -0.0144(5) -0.0044(5) 0.0085(5) C7BA 0.0316(6) 0.0311(6) 0.0279(6) -0.0052(5) -0.0113(5) 0.0024(5) C8BA 0.0415(7) 0.0384(7) 0.0260(6) -0.0124(5) -0.0141(5) 0.0033(6) C9BA 0.0317(6) 0.0228(6) 0.0564(9) -0.0112(6) -0.0200(6) 0.0061(5) C0CA 0.0410(7) 0.0241(6) 0.0463(8) -0.0027(5) -0.0178(6) -0.0004(5) C1CA 0.0538(9) 0.0442(8) 0.0226(6) -0.0099(6) 0.0002(6) 0.0036(7) C2CA 0.0579(10) 0.0382(8) 0.0472(9) -0.0273(7) -0.0038(7) 0.0098(7) C3CA 0.0434(8) 0.0469(8) 0.0303(7) -0.0219(6) -0.0033(6) -0.0015(6) C4CA 0.0429(8) 0.0448(9) 0.0579(10) -0.0266(8) -0.0080(7) 0.0206(7) _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 K1 O1AA 2.6569(9) . ? K1 O9AA 2.6652(9) . ? K1 O8AA 2.7343(9) . ? K1 O 2.7554(9) . ? K1 O5AA 2.7629(9) . ? K1 O0AA 2.7671(9) . ? K1 O4AA 2.7805(9) . ? K1 O7AA 3.0096(10) . ? K1 C4CA 3.4697(15) . ? K1 C3BA 3.4819(14) . ? K1 C6BA 3.5022(13) . ? K1 C4BA 3.5206(12) . ? O C6BA 1.4249(15) . ? O C4BA 1.4282(14) . ? O0AA C1AA 1.2182(14) . ? O1AA C 1.2232(14) . ? O2AA C 1.2811(14) . ? O3AA C1AA 1.2924(14) . ? O3AA H3AA 1.08(3) . ? O4AA C1CA 1.4140(17) . ? O4AA C7BA 1.4246(16) . ? O5AA C4CA 1.426(2) . ? O5AA C9BA 1.4298(17) . ? O6AA N 1.2189(14) . ? O7AA C0CA 1.4223(17) . ? O7AA C3BA 1.4259(16) . ? O8AA C3CA 1.4143(18) . ? O8AA C2CA 1.4172(18) . ? C C3AA 1.5171(14) . ? O9AA C5BA 1.4136(15) . ? O9AA C8BA 1.4195(15) . ? C0AA C5AA 1.3850(15) . ? C0AA C2AA 1.3930(15) . ? C0AA H0AA 0.919(16) . ? C1AA C2AA 1.5146(15) . ? N O3BA 1.2121(15) . ? N C8AA 1.4769(14) . ? C2AA C1BA 1.3936(15) . ? C3AA C6AA 1.3910(16) . ? C3AA C2BA 1.3941(16) . ? C4AA C7AA 1.3790(18) . ? C4AA C6AA 1.3846(16) . ? C4AA N1AA 1.4673(16) . ? N0AA O6BA 1.2156(17) . ? N0AA O1BA 1.2262(15) . ? N0AA C0BA 1.4762(16) . ? C5AA C9AA 1.3775(15) . ? C5AA N2AA 1.4706(14) . ? C6AA H6AA 0.938(17) . ? O0BA N2AA 1.2196(13) . ? C7AA C0BA 1.3803(18) . ? C7AA H7AA 0.917(18) . ? C8AA C9AA 1.3826(16) . ? C8AA C1BA 1.3852(16) . ? C9AA H9AA 0.920(17) . ? N1AA O4BA 1.2130(16) . ? N1AA O5BA 1.2168(18) . ? C0BA C2BA 1.3866(16) . ? C1BA H1BA 0.911(18) . ? C2BA H2BA 0.917(17) . ? N2AA O2BA 1.2169(14) . ? C3BA C8BA 1.503(2) . ? C3BA H3BA 0.980(19) . ? C3BA H3BB 0.98(2) . ? C4BA C7BA 1.4977(19) . ? C4BA H4BA 0.954(17) . ? C4BA H4BB 0.961(18) . ? C5BA C6BA 1.5038(18) . ? C5BA H5BA 0.961(17) . ? C5BA H5BB 0.947(19) . ? C6BA H6BA 0.977(18) . ? C6BA H6BB 1.022(19) . ? C7BA H7BA 0.961(18) . ? C7BA H7BB 0.93(2) . ? C8BA H8BA 0.992(19) . ? C8BA H8BB 0.986(19) . ? C9BA C0CA 1.501(2) . ? C9BA H9BA 0.976(18) . ? C9BA H9BB 0.96(2) . ? C0CA H0CA 0.964(19) . ? C0CA H0CB 0.98(2) . ? C1CA C3CA 1.502(2) . ? C1CA H1CA 1.00(2) . ? C1CA H1CB 0.99(2) . ? C2CA C4CA 1.496(3) . ? C2CA H2CA 0.96(2) . ? C2CA H2CB 0.96(2) . ? C3CA H3CA 0.96(2) . ? C3CA H3CB 0.98(2) . ? C4CA H1 1.03(2) . ? C4CA H4CA 0.99(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1AA K1 O9AA 94.71(3) . . ? O1AA K1 O8AA 101.13(3) . . ? O9AA K1 O8AA 164.16(3) . . ? O1AA K1 O 88.04(3) . . ? O9AA K1 O 61.50(3) . . ? O8AA K1 O 118.81(3) . . ? O1AA K1 O5AA 94.70(3) . . ? O9AA K1 O5AA 115.94(3) . . ? O8AA K1 O5AA 62.87(3) . . ? O K1 O5AA 176.46(3) . . ? O1AA K1 O0AA 170.60(3) . . ? O9AA K1 O0AA 76.84(3) . . ? O8AA K1 O0AA 87.38(3) . . ? O K1 O0AA 84.32(3) . . ? O5AA K1 O0AA 92.73(3) . . ? O1AA K1 O4AA 80.19(3) . . ? O9AA K1 O4AA 123.35(3) . . ? O8AA K1 O4AA 60.53(3) . . ? O K1 O4AA 61.96(3) . . ? O5AA K1 O4AA 120.69(3) . . ? O0AA K1 O4AA 100.90(3) . . ? O1AA K1 O7AA 85.60(3) . . ? O9AA K1 O7AA 56.82(3) . . ? O8AA K1 O7AA 123.86(3) . . ? O K1 O7AA 117.07(3) . . ? O5AA K1 O7AA 61.04(3) . . ? O0AA K1 O7AA 93.00(3) . . ? O4AA K1 O7AA 165.77(3) . . ? O1AA K1 C4CA 107.48(4) . . ? O9AA K1 C4CA 131.41(4) . . ? O8AA K1 C4CA 42.65(4) . . ? O K1 C4CA 156.92(4) . . ? O5AA K1 C4CA 23.08(4) . . ? O0AA K1 C4CA 81.47(4) . . ? O4AA K1 C4CA 103.07(4) . . ? O7AA K1 C4CA 81.88(4) . . ? O1AA K1 C3BA 105.29(3) . . ? O9AA K1 C3BA 42.90(3) . . ? O8AA K1 C3BA 130.31(3) . . ? O K1 C3BA 103.54(3) . . ? O5AA K1 C3BA 73.59(3) . . ? O0AA K1 C3BA 71.38(3) . . ? O4AA K1 C3BA 164.72(3) . . ? O7AA K1 C3BA 23.99(3) . . ? C4CA K1 C3BA 89.04(4) . . ? O1AA K1 C6BA 80.10(3) . . ? O9AA K1 C6BA 42.42(3) . . ? O8AA K1 C6BA 140.88(3) . . ? O K1 C6BA 22.53(3) . . ? O5AA K1 C6BA 156.17(3) . . ? O0AA K1 C6BA 90.79(3) . . ? O4AA K1 C6BA 81.60(3) . . ? O7AA K1 C6BA 95.26(3) . . ? C4CA K1 C6BA 171.57(4) . . ? C3BA K1 C6BA 85.29(3) . . ? O1AA K1 C4BA 75.49(3) . . ? O9AA K1 C4BA 81.44(3) . . ? O8AA K1 C4BA 102.60(3) . . ? O K1 C4BA 22.32(3) . . ? O5AA K1 C4BA 161.06(3) . . ? O0AA K1 C4BA 98.91(3) . . ? O4AA K1 C4BA 42.41(3) . . ? O7AA K1 C4BA 132.49(3) . . ? C4CA K1 C4BA 145.23(4) . . ? C3BA K1 C4BA 124.31(3) . . ? C6BA K1 C4BA 39.23(3) . . ? C6BA O C4BA 111.43(9) . . ? C6BA O K1 109.66(7) . . ? C4BA O K1 110.55(7) . . ? C1AA O0AA K1 149.48(9) . . ? C O1AA K1 153.13(8) . . ? C1AA O3AA H3AA 115.1(15) . . ? C1CA O4AA C7BA 111.86(10) . . ? C1CA O4AA K1 114.51(8) . . ? C7BA O4AA K1 114.26(7) . . ? C4CA O5AA C9BA 110.45(11) . . ? C4CA O5AA K1 107.51(9) . . ? C9BA O5AA K1 111.18(7) . . ? C0CA O7AA C3BA 112.95(10) . . ? C0CA O7AA K1 109.15(8) . . ? C3BA O7AA K1 96.91(7) . . ? C3CA O8AA C2CA 112.73(11) . . ? C3CA O8AA K1 117.32(8) . . ? C2CA O8AA K1 114.54(9) . . ? O1AA C O2AA 127.12(10) . . ? O1AA C C3AA 119.13(10) . . ? O2AA C C3AA 113.74(9) . . ? C5BA O9AA C8BA 113.76(10) . . ? C5BA O9AA K1 120.33(7) . . ? C8BA O9AA K1 124.15(8) . . ? C5AA C0AA C2AA 118.87(10) . . ? C5AA C0AA H0AA 119.7(10) . . ? C2AA C0AA H0AA 121.5(10) . . ? O0AA C1AA O3AA 126.50(11) . . ? O0AA C1AA C2AA 120.50(10) . . ? O3AA C1AA C2AA 113.00(9) . . ? O3BA N O6AA 124.01(11) . . ? O3BA N C8AA 118.06(11) . . ? O6AA N C8AA 117.89(10) . . ? C0AA C2AA C1BA 119.97(10) . . ? C0AA C2AA C1AA 119.71(9) . . ? C1BA C2AA C1AA 120.29(9) . . ? C6AA C3AA C2BA 119.71(10) . . ? C6AA C3AA C 120.18(10) . . ? C2BA C3AA C 120.10(10) . . ? C7AA C4AA C6AA 123.05(11) . . ? C7AA C4AA N1AA 118.33(11) . . ? C6AA C4AA N1AA 118.61(11) . . ? O6BA N0AA O1BA 124.65(12) . . ? O6BA N0AA C0BA 117.60(11) . . ? O1BA N0AA C0BA 117.74(12) . . ? C9AA C5AA C0AA 122.98(10) . . ? C9AA C5AA N2AA 118.16(10) . . ? C0AA C5AA N2AA 118.86(10) . . ? C4AA C6AA C3AA 118.96(11) . . ? C4AA C6AA H6AA 119.2(10) . . ? C3AA C6AA H6AA 121.8(10) . . ? C0BA C7AA C4AA 116.40(11) . . ? C0BA C7AA H7AA 121.3(11) . . ? C4AA C7AA H7AA 122.3(11) . . ? C9AA C8AA C1BA 123.30(10) . . ? C9AA C8AA N 116.90(10) . . ? C1BA C8AA N 119.77(10) . . ? C5AA C9AA C8AA 116.46(10) . . ? C5AA C9AA H9AA 122.7(11) . . ? C8AA C9AA H9AA 120.8(11) . . ? O4BA N1AA O5BA 123.31(13) . . ? O4BA N1AA C4AA 118.38(13) . . ? O5BA N1AA C4AA 118.31(11) . . ? C7AA C0BA C2BA 123.13(11) . . ? C7AA C0BA N0AA 117.76(11) . . ? C2BA C0BA N0AA 119.08(11) . . ? C8AA C1BA C2AA 118.40(10) . . ? C8AA C1BA H1BA 120.2(11) . . ? C2AA C1BA H1BA 121.3(11) . . ? C0BA C2BA C3AA 118.68(11) . . ? C0BA C2BA H2BA 120.8(10) . . ? C3AA C2BA H2BA 120.5(10) . . ? O0BA N2AA O2BA 123.89(10) . . ? O0BA N2AA C5AA 118.29(10) . . ? O2BA N2AA C5AA 117.82(10) . . ? O7AA C3BA C8BA 108.71(11) . . ? O7AA C3BA K1 59.10(6) . . ? C8BA C3BA K1 84.43(7) . . ? O7AA C3BA H3BA 109.8(11) . . ? C8BA C3BA H3BA 109.9(11) . . ? K1 C3BA H3BA 69.1(10) . . ? O7AA C3BA H3BB 109.5(12) . . ? C8BA C3BA H3BB 108.1(12) . . ? K1 C3BA H3BB 166.0(12) . . ? H3BA C3BA H3BB 110.9(15) . . ? O C4BA C7BA 108.72(10) . . ? O C4BA K1 47.12(5) . . ? C7BA C4BA K1 81.15(7) . . ? O C4BA H4BA 110.7(10) . . ? C7BA C4BA H4BA 110.3(10) . . ? K1 C4BA H4BA 86.4(10) . . ? O C4BA H4BB 110.3(10) . . ? C7BA C4BA H4BB 109.3(10) . . ? K1 C4BA H4BB 157.4(10) . . ? H4BA C4BA H4BB 107.5(14) . . ? O9AA C5BA C6BA 108.21(10) . . ? O9AA C5BA H5BA 110.4(10) . . ? C6BA C5BA H5BA 110.2(10) . . ? O9AA C5BA H5BB 110.3(11) . . ? C6BA C5BA H5BB 110.6(11) . . ? H5BA C5BA H5BB 107.2(15) . . ? O C6BA C5BA 109.45(10) . . ? O C6BA K1 47.81(5) . . ? C5BA C6BA K1 81.16(7) . . ? O C6BA H6BA 110.4(10) . . ? C5BA C6BA H6BA 110.2(10) . . ? K1 C6BA H6BA 158.1(10) . . ? O C6BA H6BB 110.6(11) . . ? C5BA C6BA H6BB 111.2(10) . . ? K1 C6BA H6BB 87.1(11) . . ? H6BA C6BA H6BB 105.0(15) . . ? O4AA C7BA C4BA 109.13(10) . . ? O4AA C7BA H7BA 110.3(11) . . ? C4BA C7BA H7BA 110.5(11) . . ? O4AA C7BA H7BB 110.2(12) . . ? C4BA C7BA H7BB 110.4(12) . . ? H7BA C7BA H7BB 106.3(16) . . ? O9AA C8BA C3BA 108.52(11) . . ? O9AA C8BA H8BA 108.8(11) . . ? C3BA C8BA H8BA 111.5(11) . . ? O9AA C8BA H8BB 113.3(11) . . ? C3BA C8BA H8BB 106.5(11) . . ? H8BA C8BA H8BB 108.2(15) . . ? O5AA C9BA C0CA 109.42(11) . . ? O5AA C9BA H9BA 109.9(10) . . ? C0CA C9BA H9BA 110.3(10) . . ? O5AA C9BA H9BB 108.2(12) . . ? C0CA C9BA H9BB 110.9(12) . . ? H9BA C9BA H9BB 108.1(15) . . ? O7AA C0CA C9BA 114.49(11) . . ? O7AA C0CA H0CA 109.3(12) . . ? C9BA C0CA H0CA 109.1(11) . . ? O7AA C0CA H0CB 103.5(12) . . ? C9BA C0CA H0CB 109.1(12) . . ? H0CA C0CA H0CB 111.4(16) . . ? O4AA C1CA C3CA 109.29(12) . . ? O4AA C1CA H1CA 110.1(13) . . ? C3CA C1CA H1CA 105.6(13) . . ? O4AA C1CA H1CB 110.5(14) . . ? C3CA C1CA H1CB 108.2(14) . . ? H1CA C1CA H1CB 113.0(19) . . ? O8AA C2CA C4CA 108.02(12) . . ? O8AA C2CA H2CA 109.3(13) . . ? C4CA C2CA H2CA 112.5(13) . . ? O8AA C2CA H2CB 108.6(13) . . ? C4CA C2CA H2CB 106.8(13) . . ? H2CA C2CA H2CB 111.5(18) . . ? O8AA C3CA C1CA 108.15(12) . . ? O8AA C3CA H3CA 111.2(12) . . ? C1CA C3CA H3CA 111.3(12) . . ? O8AA C3CA H3CB 108.2(12) . . ? C1CA C3CA H3CB 108.6(12) . . ? H3CA C3CA H3CB 109.4(17) . . ? O5AA C4CA C2CA 109.76(13) . . ? O5AA C4CA K1 49.41(6) . . ? C2CA C4CA K1 81.28(8) . . ? O5AA C4CA H1 107.4(13) . . ? C2CA C4CA H1 109.4(12) . . ? K1 C4CA H1 80.5(12) . . ? O5AA C4CA H4CA 109.4(13) . . ? C2CA C4CA H4CA 107.3(13) . . ? K1 C4CA H4CA 158.5(13) . . ? H1 C4CA H4CA 113.6(18) . . ? _diffrn_measured_fraction_theta_max 0.849 _diffrn_reflns_theta_full 26.78 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.380 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.059 data_K_complex_I _database_code_depnum_ccdc_archive 'CCDC 901373' #TrackingRef '13948_web_deposit_cif_file_0_ColinSeaton_1347541186.Complied_cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Potassium 3,5-dinitrobenzoate 4-(N,N'-dimethylamino)benzoic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H3 K N2 O6, C9 H11 N O2' _chemical_formula_sum 'C16 H14 K N3 O8' _chemical_formula_weight 415.40 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 19.7525(3) _cell_length_b 10.7903(2) _cell_length_c 8.27930(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.5560(10) _cell_angle_gamma 90.00 _cell_volume 1740.13(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9984 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 29.83 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.359 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8810 _exptl_absorpt_correction_T_max 0.9770 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 76419 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 32.08 _reflns_number_total 6089 _reflns_number_gt 4388 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0608P)^2^+0.3177P] 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 6089 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1195 _refine_ls_wR_factor_gt 0.1072 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.305 _refine_ls_shift/su_mean 0.005 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 K1 K 0.198165(16) 0.73112(3) 0.34847(4) 0.03895(9) Uani 1 1 d . . . C1A C 0.13913(6) 1.11207(11) 0.10070(15) 0.0291(2) Uani 1 1 d . . . C2A C 0.16316(6) 1.22835(12) 0.15363(16) 0.0318(2) Uani 1 1 d . . . H2A H 0.2015 1.2361 0.2350 0.038 Uiso 1 1 calc R . . C3A C 0.12953(6) 1.33275(11) 0.08412(15) 0.0310(2) Uani 1 1 d . . . C4A C 0.07169(6) 1.32744(12) -0.03493(15) 0.0316(2) Uani 1 1 d . . . H4A H 0.0491 1.3985 -0.0789 0.038 Uiso 1 1 calc R . . C5A C 0.04937(6) 1.20977(11) -0.08470(15) 0.0289(2) Uani 1 1 d . . . C6A C 0.08179(6) 1.10247(11) -0.02183(15) 0.0294(2) Uani 1 1 d . . . H6A H 0.0656 1.0253 -0.0606 0.035 Uiso 1 1 calc R . . C7A C 0.17393(6) 0.99605(12) 0.17803(16) 0.0338(3) Uani 1 1 d . . . O1A O 0.20659(5) 1.00841(11) 0.32014(13) 0.0472(3) Uani 1 1 d . . . O2A O 0.16578(7) 0.89912(10) 0.09671(13) 0.0503(3) Uani 1 1 d . . . N3A N 0.15484(7) 1.45555(11) 0.14465(15) 0.0397(3) Uani 1 1 d . . . O3A O 0.20829(7) 1.46007(11) 0.24103(16) 0.0614(3) Uani 1 1 d . . . O4A O 0.12079(7) 1.54605(10) 0.09876(18) 0.0641(4) Uani 1 1 d . . . N5A N -0.01178(6) 1.19804(12) -0.21284(14) 0.0372(2) Uani 1 1 d . . . O5A O -0.03912(6) 1.29220(12) -0.27242(17) 0.0600(3) Uani 1 1 d . . . O6A O -0.03114(6) 1.09422(12) -0.25532(17) 0.0626(3) Uani 1 1 d . . . C1B C 0.40588(6) 0.61132(11) 0.20333(15) 0.0297(2) Uani 1 1 d . . . C2B C 0.45569(7) 0.52684(13) 0.17282(16) 0.0351(3) Uani 1 1 d . . . H2B H 0.4445 0.4683 0.0903 0.042 Uiso 1 1 calc R . . C3B C 0.52087(7) 0.52805(13) 0.26151(17) 0.0367(3) Uani 1 1 d . . . H3B H 0.5530 0.4710 0.2373 0.044 Uiso 1 1 calc R . . C4B C 0.53993(6) 0.61425(12) 0.38859(15) 0.0320(2) Uani 1 1 d . . . C5B C 0.48918(7) 0.69901(12) 0.42039(17) 0.0354(3) Uani 1 1 d . . . H5B H 0.4998 0.7568 0.5041 0.042 Uiso 1 1 calc R . . C6B C 0.42425(7) 0.69696(12) 0.32881(17) 0.0339(3) Uani 1 1 d . . . H6B H 0.3919 0.7542 0.3513 0.041 Uiso 1 1 calc R . . C7B C 0.33663(6) 0.61189(12) 0.10601(16) 0.0324(3) Uani 1 1 d . . . O1B O 0.29122(5) 0.68451(10) 0.12519(13) 0.0427(2) Uani 1 1 d . . . O2B O 0.32752(6) 0.52557(12) -0.00914(15) 0.0538(3) Uani 1 1 d . . . H2BO H 0.2869(12) 0.523(2) -0.060(3) 0.074(7) Uiso 1 1 d . . . N1B N 0.60495(6) 0.61558(12) 0.47620(15) 0.0429(3) Uani 1 1 d . . . C8B C 0.62517(9) 0.70314(18) 0.6075(2) 0.0560(4) Uani 1 1 d . . . H8B1 H 0.6356 0.7815 0.5625 0.084 Uiso 1 1 calc R . . H8B2 H 0.6650 0.6726 0.6787 0.084 Uiso 1 1 calc R . . H8B3 H 0.5883 0.7135 0.6687 0.084 Uiso 1 1 calc R . . C9B C 0.65724(8) 0.5333(2) 0.4342(2) 0.0565(4) Uani 1 1 d . . . H9B1 H 0.6433 0.4489 0.4448 0.085 Uiso 1 1 calc R . . H9B2 H 0.6997 0.5480 0.5066 0.085 Uiso 1 1 calc R . . H9B3 H 0.6633 0.5485 0.3232 0.085 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 K1 0.04857(17) 0.03293(15) 0.03337(16) 0.00299(11) 0.00099(12) -0.00697(12) C1A 0.0302(5) 0.0283(6) 0.0292(6) 0.0011(4) 0.0058(4) 0.0037(4) C2A 0.0309(5) 0.0329(6) 0.0308(6) -0.0013(5) 0.0030(4) 0.0003(5) C3A 0.0364(6) 0.0267(5) 0.0307(6) -0.0029(4) 0.0081(5) -0.0020(5) C4A 0.0359(6) 0.0275(6) 0.0318(6) 0.0025(5) 0.0067(5) 0.0038(4) C5A 0.0264(5) 0.0319(6) 0.0280(6) 0.0010(4) 0.0034(4) 0.0019(4) C6A 0.0312(5) 0.0264(5) 0.0305(6) -0.0014(4) 0.0056(4) -0.0004(4) C7A 0.0336(6) 0.0336(6) 0.0346(7) 0.0050(5) 0.0071(5) 0.0087(5) O1A 0.0456(6) 0.0487(6) 0.0420(6) 0.0052(5) -0.0080(4) 0.0105(5) O2A 0.0752(8) 0.0330(5) 0.0421(6) -0.0001(4) 0.0075(5) 0.0190(5) N3A 0.0510(7) 0.0310(6) 0.0379(6) -0.0040(5) 0.0094(5) -0.0059(5) O3A 0.0690(8) 0.0449(7) 0.0620(8) -0.0036(6) -0.0137(6) -0.0186(6) O4A 0.0778(9) 0.0299(6) 0.0799(9) -0.0119(6) -0.0008(7) 0.0066(5) N5A 0.0303(5) 0.0445(6) 0.0350(6) 0.0003(5) 0.0002(4) 0.0015(4) O5A 0.0507(6) 0.0564(7) 0.0643(8) 0.0068(6) -0.0160(6) 0.0157(5) O6A 0.0563(7) 0.0531(7) 0.0686(8) -0.0074(6) -0.0181(6) -0.0109(6) C1B 0.0292(5) 0.0308(6) 0.0292(6) 0.0010(4) 0.0051(4) 0.0008(4) C2B 0.0359(6) 0.0361(6) 0.0324(6) -0.0072(5) 0.0030(5) 0.0033(5) C3B 0.0340(6) 0.0392(7) 0.0364(7) -0.0055(5) 0.0044(5) 0.0085(5) C4B 0.0307(5) 0.0357(6) 0.0294(6) 0.0030(5) 0.0041(5) 0.0010(5) C5B 0.0370(6) 0.0325(6) 0.0356(7) -0.0072(5) 0.0030(5) 0.0003(5) C6B 0.0331(6) 0.0311(6) 0.0380(7) -0.0038(5) 0.0070(5) 0.0033(5) C7B 0.0320(6) 0.0341(6) 0.0310(6) 0.0013(5) 0.0049(5) -0.0002(5) O1B 0.0334(5) 0.0441(6) 0.0489(6) -0.0042(5) 0.0017(4) 0.0084(4) O2B 0.0368(5) 0.0645(7) 0.0545(7) -0.0257(6) -0.0085(5) 0.0091(5) N1B 0.0333(5) 0.0530(7) 0.0396(6) -0.0058(5) -0.0016(5) 0.0048(5) C8B 0.0473(8) 0.0561(10) 0.0577(10) -0.0103(8) -0.0109(7) -0.0025(7) C9B 0.0350(7) 0.0823(13) 0.0502(9) -0.0040(9) 0.0010(6) 0.0160(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 K1 O2A 2.6542(11) 4_576 ? K1 O2A 2.7563(11) . ? K1 O1B 2.8386(11) 4_576 ? K1 O1B 2.8595(11) . ? K1 O1A 3.0079(12) . ? K1 O3A 3.0731(13) 1_545 ? K1 O4A 3.0902(13) 1_545 ? K1 O5A 3.1099(13) 3_575 ? K1 C7A 3.1887(13) . ? K1 N3A 3.4558(12) 1_545 ? K1 K1 4.1596 4_576 ? K1 K1 4.1597 4_575 ? C1A C2A 1.3865(17) . ? C1A C6A 1.3934(17) . ? C1A C7A 1.5177(17) . ? C2A C3A 1.3836(18) . ? C2A H2A 0.9300 . ? C3A C4A 1.3807(18) . ? C3A N3A 1.4743(16) . ? C4A C5A 1.3842(17) . ? C4A H4A 0.9300 . ? C5A C6A 1.3823(17) . ? C5A N5A 1.4749(16) . ? C6A H6A 0.9300 . ? C7A O2A 1.2398(17) . ? C7A O1A 1.2515(17) . ? O2A K1 2.6542(11) 4_575 ? N3A O4A 1.2105(17) . ? N3A O3A 1.2142(17) . ? N3A K1 3.4558(12) 1_565 ? O3A K1 3.0732(13) 1_565 ? O4A K1 3.0901(13) 1_565 ? N5A O6A 1.2166(17) . ? N5A O5A 1.2161(16) . ? O5A K1 3.1100(13) 3_575 ? C1B C6B 1.3928(18) . ? C1B C2B 1.3948(17) . ? C1B C7B 1.4678(17) . ? C2B C3B 1.3722(18) . ? C2B H2B 0.9300 . ? C3B C4B 1.4080(18) . ? C3B H3B 0.9300 . ? C4B N1B 1.3663(17) . ? C4B C5B 1.4135(18) . ? C5B C6B 1.3774(19) . ? C5B H5B 0.9300 . ? C6B H6B 0.9300 . ? C7B O1B 1.2211(16) . ? C7B O2B 1.3236(17) . ? O1B K1 2.8387(11) 4_575 ? O2B H2BO 0.84(2) . ? N1B C9B 1.447(2) . ? N1B C8B 1.446(2) . ? C8B H8B1 0.9600 . ? C8B H8B2 0.9600 . ? C8B H8B3 0.9600 . ? C9B H9B1 0.9600 . ? C9B H9B2 0.9600 . ? C9B H9B3 0.9600 . ? 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 O2A K1 O2A 151.44(5) 4_576 . ? O2A K1 O1B 75.63(3) 4_576 4_576 ? O2A K1 O1B 115.93(3) . 4_576 ? O2A K1 O1B 132.13(4) 4_576 . ? O2A K1 O1B 73.75(3) . . ? O1B K1 O1B 100.29(3) 4_576 . ? O2A K1 O1A 127.64(4) 4_576 . ? O2A K1 O1A 45.23(3) . . ? O1B K1 O1A 72.97(3) 4_576 . ? O1B K1 O1A 94.29(3) . . ? O2A K1 O3A 75.87(4) 4_576 1_545 ? O2A K1 O3A 115.16(3) . 1_545 ? O1B K1 O3A 118.31(3) 4_576 1_545 ? O1B K1 O3A 64.26(4) . 1_545 ? O1A K1 O3A 156.49(4) . 1_545 ? O2A K1 O4A 91.14(4) 4_576 1_545 ? O2A K1 O4A 83.81(4) . 1_545 ? O1B K1 O4A 158.32(4) 4_576 1_545 ? O1B K1 O4A 75.72(4) . 1_545 ? O1A K1 O4A 128.19(3) . 1_545 ? O3A K1 O4A 40.54(3) 1_545 1_545 ? O2A K1 O5A 75.45(4) 4_576 3_575 ? O2A K1 O5A 78.48(4) . 3_575 ? O1B K1 O5A 133.34(4) 4_576 3_575 ? O1B K1 O5A 126.22(3) . 3_575 ? O1A K1 O5A 97.58(3) . 3_575 ? O3A K1 O5A 88.65(4) 1_545 3_575 ? O4A K1 O5A 56.05(4) 1_545 3_575 ? O2A K1 C7A 141.22(4) 4_576 . ? O2A K1 C7A 22.60(3) . . ? O1B K1 C7A 95.69(3) 4_576 . ? O1B K1 C7A 86.39(3) . . ? O1A K1 C7A 23.07(3) . . ? O3A K1 C7A 137.50(4) 1_545 . ? O4A K1 C7A 105.19(4) 1_545 . ? O5A K1 C7A 84.87(3) 3_575 . ? O2A K1 N3A 81.40(3) 4_576 1_545 ? O2A K1 N3A 100.90(3) . 1_545 ? O1B K1 N3A 138.14(3) 4_576 1_545 ? O1B K1 N3A 70.53(3) . 1_545 ? O1A K1 N3A 146.12(3) . 1_545 ? O3A K1 N3A 20.37(3) 1_545 1_545 ? O4A K1 N3A 20.34(3) 1_545 1_545 ? O5A K1 N3A 70.82(3) 3_575 1_545 ? C7A K1 N3A 123.26(3) . 1_545 ? O2A K1 K1 40.66(2) 4_576 4_576 ? O2A K1 K1 130.53(3) . 4_576 ? O1B K1 K1 43.31(2) 4_576 4_576 ? O1B K1 K1 140.07(2) . 4_576 ? O1A K1 K1 89.39(2) . 4_576 ? O3A K1 K1 113.08(3) 1_545 4_576 ? O4A K1 K1 130.35(3) 1_545 4_576 ? O5A K1 K1 92.44(3) 3_575 4_576 ? C7A K1 K1 109.14(3) . 4_576 ? N3A K1 K1 121.96(2) 1_545 4_576 ? O2A K1 K1 149.57(3) 4_576 4_575 ? O2A K1 K1 38.86(2) . 4_575 ? O1B K1 K1 131.67(2) 4_576 4_575 ? O1B K1 K1 42.92(2) . 4_575 ? O1A K1 K1 79.39(2) . 4_575 ? O3A K1 K1 78.13(3) 1_545 4_575 ? O4A K1 K1 58.61(3) 1_545 4_575 ? O5A K1 K1 88.47(3) 3_575 4_575 ? C7A K1 K1 59.77(2) . 4_575 ? N3A K1 K1 68.85(2) 1_545 4_575 ? K1 K1 K1 168.760(17) 4_576 4_575 ? C2A C1A C6A 119.44(11) . . ? C2A C1A C7A 120.39(11) . . ? C6A C1A C7A 120.15(11) . . ? C3A C2A C1A 119.33(12) . . ? C3A C2A H2A 120.3 . . ? C1A C2A H2A 120.3 . . ? C4A C3A C2A 123.12(12) . . ? C4A C3A N3A 118.27(11) . . ? C2A C3A N3A 118.56(12) . . ? C3A C4A C5A 115.81(11) . . ? C3A C4A H4A 122.1 . . ? C5A C4A H4A 122.1 . . ? C6A C5A C4A 123.47(11) . . ? C6A C5A N5A 118.15(11) . . ? C4A C5A N5A 118.37(11) . . ? C5A C6A C1A 118.80(11) . . ? C5A C6A H6A 120.6 . . ? C1A C6A H6A 120.6 . . ? O2A C7A O1A 126.91(13) . . ? O2A C7A C1A 117.25(12) . . ? O1A C7A C1A 115.81(12) . . ? O2A C7A K1 58.70(7) . . ? O1A C7A K1 70.33(8) . . ? C1A C7A K1 161.87(8) . . ? C7A O1A K1 86.60(8) . . ? C7A O2A K1 147.24(10) . 4_575 ? C7A O2A K1 98.70(8) . . ? K1 O2A K1 100.48(3) 4_575 . ? O4A N3A O3A 123.43(13) . . ? O4A N3A C3A 118.62(12) . . ? O3A N3A C3A 117.93(12) . . ? O4A N3A K1 62.53(8) . 1_565 ? O3A N3A K1 61.75(8) . 1_565 ? C3A N3A K1 169.06(8) . 1_565 ? N3A O3A K1 97.89(9) . 1_565 ? N3A O4A K1 97.13(9) . 1_565 ? O6A N5A O5A 123.71(13) . . ? O6A N5A C5A 117.87(11) . . ? O5A N5A C5A 118.40(12) . . ? N5A O5A K1 112.34(10) . 3_575 ? C6B C1B C2B 117.67(12) . . ? C6B C1B C7B 120.69(11) . . ? C2B C1B C7B 121.63(11) . . ? C3B C2B C1B 121.62(12) . . ? C3B C2B H2B 119.2 . . ? C1B C2B H2B 119.2 . . ? C2B C3B C4B 121.12(12) . . ? C2B C3B H3B 119.4 . . ? C4B C3B H3B 119.4 . . ? N1B C4B C3B 120.98(12) . . ? N1B C4B C5B 121.84(12) . . ? C3B C4B C5B 117.18(11) . . ? C6B C5B C4B 120.75(12) . . ? C6B C5B H5B 119.6 . . ? C4B C5B H5B 119.6 . . ? C5B C6B C1B 121.65(12) . . ? C5B C6B H6B 119.2 . . ? C1B C6B H6B 119.2 . . ? O1B C7B O2B 122.03(12) . . ? O1B C7B C1B 124.68(12) . . ? O2B C7B C1B 113.28(11) . . ? C7B O1B K1 119.47(9) . 4_575 ? C7B O1B K1 139.62(9) . . ? K1 O1B K1 93.77(3) 4_575 . ? C7B O2B H2BO 112.7(16) . . ? C4B N1B C9B 120.75(13) . . ? C4B N1B C8B 121.61(13) . . ? C9B N1B C8B 117.55(13) . . ? N1B C8B H8B1 109.5 . . ? N1B C8B H8B2 109.5 . . ? H8B1 C8B H8B2 109.5 . . ? N1B C8B H8B3 109.5 . . ? H8B1 C8B H8B3 109.5 . . ? H8B2 C8B H8B3 109.5 . . ? N1B C9B H9B1 109.5 . . ? N1B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? N1B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 32.08 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.347 _refine_diff_density_min -0.457 _refine_diff_density_rms 0.055 data_Na_complex_II _database_code_depnum_ccdc_archive 'CCDC 901374' #TrackingRef '13948_web_deposit_cif_file_0_ColinSeaton_1347541186.Complied_cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Sodium 3,5-dinitrobenzoate 4-(N, N'-dimethylamino)benzoic acid dihydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 N3 Na O10' _chemical_formula_sum 'C16 H18 N3 Na O10' _chemical_formula_weight 435.32 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7840(7) _cell_length_b 7.6611(8) _cell_length_c 18.6422(18) _cell_angle_alpha 81.212(5) _cell_angle_beta 87.658(4) _cell_angle_gamma 86.753(5) _cell_volume 955.47(17) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9957 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 28.80 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9364 _exptl_absorpt_correction_T_max 0.9777 _exptl_absorpt_process_details 'Bruker SAINT' _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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25181 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4221 _reflns_number_gt 3425 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.3616P] 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 refU _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4221 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.2005 _refine_ls_wR_factor_gt 0.1938 _refine_ls_goodness_of_fit_ref 1.295 _refine_ls_restrained_S_all 1.295 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.002 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 Na1 Na 0.36091(12) 0.74837(12) 0.04868(5) 0.0249(3) Uani 1 1 d . . . O1 O 0.3542(2) 0.9992(2) 0.09968(11) 0.0328(5) Uani 1 1 d . . . O2 O 0.3380(3) 0.4566(2) 0.09316(11) 0.0348(5) Uani 1 1 d . . . C1A C 0.1749(3) 0.7664(3) -0.19079(13) 0.0198(5) Uani 1 1 d . . . C2A C 0.3372(3) 0.8304(3) -0.23308(13) 0.0213(5) Uani 1 1 d . . . H2A H 0.4436 0.8764 -0.2115 0.026 Uiso 1 1 calc R . . C3A C 0.3401(3) 0.8255(3) -0.30690(13) 0.0233(5) Uani 1 1 d . . . C4A C 0.1914(4) 0.7552(3) -0.34036(13) 0.0266(5) Uani 1 1 d . . . H4A H 0.1974 0.7505 -0.3910 0.032 Uiso 1 1 calc R . . C5A C 0.0349(3) 0.6926(3) -0.29693(14) 0.0246(5) Uani 1 1 d . . . C6A C 0.0203(3) 0.6979(3) -0.22333(13) 0.0229(5) Uani 1 1 d . . . H6A H -0.0923 0.6560 -0.1953 0.027 Uiso 1 1 calc R . . C7A C 0.1639(3) 0.7712(3) -0.11024(13) 0.0200(5) Uani 1 1 d . . . O1A O 0.3204(2) 0.7854(2) -0.07840(9) 0.0237(4) Uani 1 1 d . . . O2A O -0.0050(2) 0.7608(3) -0.07947(9) 0.0299(4) Uani 1 1 d . . . N1A N -0.1252(3) 0.6155(3) -0.33102(13) 0.0323(5) Uani 1 1 d . . . O3A O -0.2698(3) 0.5694(3) -0.29307(12) 0.0401(5) Uani 1 1 d . . . O4A O -0.1041(3) 0.6019(3) -0.39537(11) 0.0489(6) Uani 1 1 d . . . N2A N 0.5082(3) 0.8975(3) -0.35229(12) 0.0302(5) Uani 1 1 d . . . O5A O 0.5129(3) 0.8835(3) -0.41670(11) 0.0464(6) Uani 1 1 d . . . O6A O 0.6352(3) 0.9661(3) -0.32270(11) 0.0387(5) Uani 1 1 d . . . C1B C -0.1716(3) 0.7377(3) 0.16991(13) 0.0199(5) Uani 1 1 d . . . C2B C -0.0135(3) 0.7897(3) 0.20651(13) 0.0225(5) Uani 1 1 d . . . H2B H 0.1047 0.8221 0.1799 0.027 Uiso 1 1 calc R . . C3B C -0.0253(3) 0.7949(3) 0.28009(13) 0.0246(5) Uani 1 1 d . . . H3B H 0.0842 0.8311 0.3033 0.029 Uiso 1 1 calc R . . C4B C -0.1982(4) 0.7470(3) 0.32131(13) 0.0243(5) Uani 1 1 d . . . C5B C -0.3555(3) 0.6889(3) 0.28468(13) 0.0259(5) Uani 1 1 d . . . H5B H -0.4718 0.6512 0.3113 0.031 Uiso 1 1 calc R . . C6B C -0.3417(3) 0.6864(3) 0.21144(13) 0.0240(5) Uani 1 1 d . . . H6B H -0.4502 0.6490 0.1880 0.029 Uiso 1 1 calc R . . C7B C -0.1650(3) 0.7351(3) 0.09155(13) 0.0214(5) Uani 1 1 d . . . O1B O 0.0048(2) 0.7756(3) 0.05751(9) 0.0290(4) Uani 1 1 d . . . O2B O -0.3053(2) 0.6986(3) 0.05810(10) 0.0313(4) Uani 1 1 d . . . N1B N -0.2160(3) 0.7577(3) 0.39409(12) 0.0333(5) Uani 1 1 d . . . C8B C -0.0520(5) 0.8110(4) 0.43259(15) 0.0409(7) Uani 1 1 d . . . H8B1 H 0.0450 0.7113 0.4426 0.061 Uiso 1 1 calc R . . H8B2 H -0.1015 0.8472 0.4785 0.061 Uiso 1 1 calc R . . H8B3 H 0.0108 0.9104 0.4026 0.061 Uiso 1 1 calc R . . C9B C -0.3745(5) 0.6714(4) 0.43847(15) 0.0427(7) Uani 1 1 d . . . H9B1 H -0.5011 0.7336 0.4253 0.064 Uiso 1 1 calc R . . H9B2 H -0.3518 0.6741 0.4899 0.064 Uiso 1 1 calc R . . H9B3 H -0.3772 0.5484 0.4301 0.064 Uiso 1 1 calc R . . H1BO H 0.0012 0.7804 0.0080 0.091(16) Uiso 1 1 d . . . H21 H 0.4489 0.3960 0.0918 0.061(11) Uiso 1 1 d . . . H22 H 0.2594 0.3873 0.0805 0.073(13) Uiso 1 1 d . . . H11 H 0.2713 1.0765 0.0967 0.042(9) Uiso 1 1 d . . . H12 H 0.4471 1.0645 0.0944 0.056(11) 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 Na1 0.0143(5) 0.0291(5) 0.0321(5) -0.0061(4) -0.0062(4) -0.0021(4) O1 0.0179(9) 0.0227(9) 0.0586(13) -0.0063(8) -0.0053(8) -0.0029(7) O2 0.0175(9) 0.0276(10) 0.0601(13) -0.0076(9) -0.0035(8) -0.0042(7) C1A 0.0118(10) 0.0178(11) 0.0303(12) -0.0045(9) -0.0036(9) 0.0004(8) C2A 0.0155(11) 0.0184(11) 0.0308(12) -0.0061(9) -0.0027(9) 0.0004(8) C3A 0.0176(11) 0.0209(12) 0.0307(12) -0.0029(9) 0.0015(9) 0.0001(9) C4A 0.0291(13) 0.0266(13) 0.0245(12) -0.0058(9) -0.0052(10) 0.0031(10) C5A 0.0188(11) 0.0214(12) 0.0352(13) -0.0079(10) -0.0103(10) 0.0019(9) C6A 0.0157(11) 0.0211(12) 0.0319(13) -0.0030(9) -0.0051(9) -0.0003(9) C7A 0.0118(10) 0.0185(11) 0.0294(12) -0.0023(9) -0.0033(9) 0.0002(8) O1A 0.0140(8) 0.0291(9) 0.0290(9) -0.0059(7) -0.0044(6) -0.0037(6) O2A 0.0125(8) 0.0496(12) 0.0274(9) -0.0055(8) 0.0002(7) -0.0019(7) N1A 0.0269(12) 0.0262(11) 0.0457(14) -0.0085(9) -0.0167(10) 0.0013(9) O3A 0.0239(10) 0.0388(11) 0.0608(13) -0.0120(9) -0.0130(9) -0.0078(8) O4A 0.0518(13) 0.0607(15) 0.0390(12) -0.0160(10) -0.0201(10) -0.0074(11) N2A 0.0248(11) 0.0299(12) 0.0342(12) -0.0036(9) 0.0071(9) 0.0027(9) O5A 0.0429(12) 0.0647(15) 0.0309(11) -0.0082(10) 0.0115(9) -0.0032(10) O6A 0.0240(10) 0.0438(12) 0.0488(12) -0.0072(9) 0.0060(8) -0.0115(8) C1B 0.0138(10) 0.0170(11) 0.0288(12) -0.0031(9) -0.0027(9) 0.0002(8) C2B 0.0127(10) 0.0244(12) 0.0299(12) -0.0022(9) -0.0013(9) -0.0021(8) C3B 0.0192(11) 0.0268(12) 0.0282(12) -0.0040(9) -0.0052(9) -0.0031(9) C4B 0.0233(12) 0.0212(12) 0.0285(13) -0.0045(9) -0.0018(10) 0.0003(9) C5B 0.0184(11) 0.0296(13) 0.0293(13) -0.0027(10) 0.0031(9) -0.0055(9) C6B 0.0145(11) 0.0255(12) 0.0326(13) -0.0049(10) -0.0032(9) -0.0028(9) C7B 0.0110(10) 0.0232(12) 0.0304(12) -0.0057(9) -0.0027(9) 0.0010(8) O1B 0.0110(8) 0.0513(12) 0.0256(9) -0.0070(8) -0.0006(6) -0.0055(7) O2B 0.0134(8) 0.0505(12) 0.0324(10) -0.0116(8) -0.0041(7) -0.0061(7) N1B 0.0337(12) 0.0427(14) 0.0246(11) -0.0076(9) 0.0011(9) -0.0070(10) C8B 0.0496(18) 0.0470(18) 0.0288(14) -0.0110(12) -0.0051(13) -0.0091(14) C9B 0.0469(18) 0.0516(19) 0.0308(14) -0.0091(13) 0.0116(13) -0.0139(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 Na1 O1 2.268(2) . ? Na1 O2 2.274(2) . ? Na1 O2B 2.2841(18) 1_655 ? Na1 O1A 2.3679(19) . ? Na1 O1B 2.4138(18) . ? Na1 H1BO 2.5723(9) . ? O1 H11 0.7903(18) . ? O1 H12 0.8200(16) . ? O2 H21 0.8625(18) . ? O2 H22 0.8382(18) . ? C1A C2A 1.395(3) . ? C1A C6A 1.398(3) . ? C1A C7A 1.506(3) . ? C2A C3A 1.382(3) . ? C2A H2A 0.9500 . ? C3A C4A 1.383(3) . ? C3A N2A 1.473(3) . ? C4A C5A 1.372(4) . ? C4A H4A 0.9500 . ? C5A C6A 1.378(4) . ? C5A N1A 1.475(3) . ? C6A H6A 0.9500 . ? C7A O1A 1.256(3) . ? C7A O2A 1.261(3) . ? N1A O4A 1.222(3) . ? N1A O3A 1.222(3) . ? N2A O5A 1.221(3) . ? N2A O6A 1.226(3) . ? C1B C2B 1.402(3) . ? C1B C6B 1.404(3) . ? C1B C7B 1.463(3) . ? C2B C3B 1.377(3) . ? C2B H2B 0.9500 . ? C3B C4B 1.411(3) . ? C3B H3B 0.9500 . ? C4B N1B 1.372(3) . ? C4B C5B 1.417(3) . ? C5B C6B 1.368(4) . ? C5B H5B 0.9500 . ? C6B H6B 0.9500 . ? C7B O2B 1.227(3) . ? C7B O1B 1.322(3) . ? O1B H1BO 0.9194(17) . ? O2B Na1 2.2840(18) 1_455 ? N1B C9B 1.455(4) . ? N1B C8B 1.458(4) . ? C8B H8B1 0.9800 . ? C8B H8B2 0.9800 . ? C8B H8B3 0.9800 . ? C9B H9B1 0.9800 . ? C9B H9B2 0.9800 . ? C9B H9B3 0.9800 . ? 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 O1 Na1 O2 134.28(9) . . ? O1 Na1 O2B 93.73(7) . 1_655 ? O2 Na1 O2B 86.36(7) . 1_655 ? O1 Na1 O1A 116.38(8) . . ? O2 Na1 O1A 108.09(7) . . ? O2B Na1 O1A 102.59(7) 1_655 . ? O1 Na1 O1B 85.94(7) . . ? O2 Na1 O1B 87.54(7) . . ? O2B Na1 O1B 171.12(8) 1_655 . ? O1A Na1 O1B 85.44(6) . . ? O1 Na1 H1BO 96.75(5) . . ? O2 Na1 H1BO 92.74(5) . . ? O2B Na1 H1BO 166.16(6) 1_655 . ? O1A Na1 H1BO 64.56(4) . . ? O1B Na1 H1BO 20.94(4) . . ? Na1 O1 H11 127.67(16) . . ? Na1 O1 H12 121.59(17) . . ? H11 O1 H12 95.32(18) . . ? Na1 O2 H21 113.56(14) . . ? Na1 O2 H22 126.82(17) . . ? H21 O2 H22 101.6(2) . . ? C2A C1A C6A 119.9(2) . . ? C2A C1A C7A 120.60(19) . . ? C6A C1A C7A 119.5(2) . . ? C3A C2A C1A 118.7(2) . . ? C3A C2A H2A 120.6 . . ? C1A C2A H2A 120.6 . . ? C2A C3A C4A 122.7(2) . . ? C2A C3A N2A 119.1(2) . . ? C4A C3A N2A 118.2(2) . . ? C5A C4A C3A 116.9(2) . . ? C5A C4A H4A 121.6 . . ? C3A C4A H4A 121.6 . . ? C4A C5A C6A 123.3(2) . . ? C4A C5A N1A 118.1(2) . . ? C6A C5A N1A 118.6(2) . . ? C5A C6A C1A 118.5(2) . . ? C5A C6A H6A 120.8 . . ? C1A C6A H6A 120.8 . . ? O1A C7A O2A 124.5(2) . . ? O1A C7A C1A 118.74(19) . . ? O2A C7A C1A 116.76(18) . . ? C7A O1A Na1 126.66(15) . . ? O4A N1A O3A 124.4(2) . . ? O4A N1A C5A 117.7(2) . . ? O3A N1A C5A 117.9(2) . . ? O5A N2A O6A 124.3(2) . . ? O5A N2A C3A 117.9(2) . . ? O6A N2A C3A 117.8(2) . . ? C2B C1B C6B 117.5(2) . . ? C2B C1B C7B 122.8(2) . . ? C6B C1B C7B 119.73(19) . . ? C3B C2B C1B 121.6(2) . . ? C3B C2B H2B 119.2 . . ? C1B C2B H2B 119.2 . . ? C2B C3B C4B 120.7(2) . . ? C2B C3B H3B 119.7 . . ? C4B C3B H3B 119.7 . . ? N1B C4B C3B 121.7(2) . . ? N1B C4B C5B 120.7(2) . . ? C3B C4B C5B 117.6(2) . . ? C6B C5B C4B 120.8(2) . . ? C6B C5B H5B 119.6 . . ? C4B C5B H5B 119.6 . . ? C5B C6B C1B 121.8(2) . . ? C5B C6B H6B 119.1 . . ? C1B C6B H6B 119.1 . . ? O2B C7B O1B 120.8(2) . . ? O2B C7B C1B 123.7(2) . . ? O1B C7B C1B 115.55(18) . . ? C7B O1B Na1 151.12(15) . . ? C7B O1B H1BO 113.28(17) . . ? Na1 O1B H1BO 89.29(11) . . ? C7B O2B Na1 142.05(17) . 1_455 ? C4B N1B C9B 120.3(2) . . ? C4B N1B C8B 120.9(2) . . ? C9B N1B C8B 116.7(2) . . ? N1B C8B H8B1 109.5 . . ? N1B C8B H8B2 109.5 . . ? H8B1 C8B H8B2 109.5 . . ? N1B C8B H8B3 109.5 . . ? H8B1 C8B H8B3 109.5 . . ? H8B2 C8B H8B3 109.5 . . ? N1B C9B H9B1 109.5 . . ? N1B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? N1B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.430 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.075 data_III _database_code_depnum_ccdc_archive 'CCDC 901375' #TrackingRef '15348_web_deposit_cif_file_0_ColinSeaton_1352638926.NH4_complex_III_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Ammonium 3,5-dinitrobenzoate 4-(N,N'-dimethylamino)benzoate ; _chemical_name_common "Ammonium 3,5-dinitrobenzoate 4-(N,N'-dimethylamino)benzoate" _chemical_melting_point ? _chemical_formula_moiety 'C7 H3 N2 O6, C9 H10 N O2, 2(H4 N)' _chemical_formula_sum 'C16 H21 N5 O8' _chemical_formula_weight 411.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1722(4) _cell_length_b 8.4443(6) _cell_length_c 18.7848(12) _cell_angle_alpha 83.049(4) _cell_angle_beta 82.207(4) _cell_angle_gamma 86.054(4) _cell_volume 961.52(11) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3866 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 22.17 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9618 _exptl_absorpt_correction_T_max 0.9933 _exptl_absorpt_process_details 'Bruker ApexII v2011-4.1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17084 _diffrn_reflns_av_R_equivalents 0.1009 _diffrn_reflns_av_sigmaI/netI 0.1038 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3323 _reflns_number_gt 1474 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics CrystalMaker _computing_publication_material CrystalMaker _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^)+(0.0949P)^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 3323 _refine_ls_number_parameters 296 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1685 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1721 _refine_ls_wR_factor_gt 0.1431 _refine_ls_goodness_of_fit_ref 0.863 _refine_ls_restrained_S_all 0.863 _refine_ls_shift/su_max 0.037 _refine_ls_shift/su_mean 0.002 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 O1A O 0.0030(4) 0.5538(3) 0.08695(13) 0.0560(7) Uani 1 1 d . . . O2A O 0.3386(4) 0.6365(3) 0.07353(14) 0.0674(8) Uani 1 1 d . . . C1A C 0.2139(5) 0.4799(4) 0.18304(17) 0.0365(8) Uani 1 1 d . . . C2A C 0.4045(5) 0.4931(4) 0.21354(18) 0.0404(9) Uani 1 1 d . . . H2A H 0.5184 0.5488 0.1864 0.049 Uiso 1 1 calc R . . C3A C 0.4289(5) 0.4259(4) 0.28271(18) 0.0393(9) Uani 1 1 d . . . H3A H 0.5577 0.4383 0.3015 0.047 Uiso 1 1 calc R . . C4A C 0.2627(5) 0.3390(4) 0.32526(18) 0.0384(8) Uani 1 1 d . . . C5A C 0.0740(5) 0.3233(4) 0.29332(18) 0.0434(9) Uani 1 1 d . . . H5A H -0.0390 0.2647 0.3193 0.052 Uiso 1 1 calc R . . C6A C 0.0527(5) 0.3929(4) 0.22423(18) 0.0420(9) Uani 1 1 d . . . H6A H -0.0752 0.3805 0.2049 0.050 Uiso 1 1 calc R . . C7A C 0.1845(6) 0.5620(4) 0.10967(19) 0.0455(9) Uani 1 1 d . . . N1A N 0.2851(4) 0.2701(3) 0.39417(15) 0.0454(8) Uani 1 1 d . . . C8A C 0.4488(6) 0.3241(5) 0.4337(2) 0.0687(13) Uani 1 1 d . . . H8A1 H 0.5926 0.2999 0.4096 0.103 Uiso 1 1 calc R . . H8A2 H 0.4342 0.2705 0.4820 0.103 Uiso 1 1 calc R . . H8A3 H 0.4274 0.4373 0.4354 0.103 Uiso 1 1 calc R . . C9A C 0.1044(6) 0.1913(5) 0.43901(19) 0.0585(11) Uani 1 1 d . . . H9A1 H -0.0095 0.2696 0.4523 0.088 Uiso 1 1 calc R . . H9A2 H 0.1549 0.1359 0.4819 0.088 Uiso 1 1 calc R . . H9A3 H 0.0481 0.1164 0.4125 0.088 Uiso 1 1 calc R . . O1B O 1.0086(4) 0.9742(3) -0.10896(14) 0.0634(8) Uani 1 1 d . . . O2B O 0.6628(5) 0.9044(3) -0.09176(14) 0.0685(8) Uani 1 1 d . . . C1B C 0.7955(5) 1.0432(4) -0.20441(17) 0.0396(9) Uani 1 1 d . . . C2B C 0.6250(5) 1.0019(4) -0.23811(18) 0.0419(9) Uani 1 1 d . . . H2B H 0.5228 0.9324 -0.2133 0.050 Uiso 1 1 calc R . . C3B C 0.6069(5) 1.0639(4) -0.30837(18) 0.0394(9) Uani 1 1 d . . . C4B C 0.7487(5) 1.1723(4) -0.34670(18) 0.0426(9) Uani 1 1 d . . . H4B H 0.7321 1.2160 -0.3937 0.051 Uiso 1 1 calc R . . C5B C 0.9153(5) 1.2124(4) -0.31212(19) 0.0414(9) Uani 1 1 d . . . C6B C 0.9407(5) 1.1502(4) -0.24218(19) 0.0399(9) Uani 1 1 d . . . H6B H 1.0558 1.1804 -0.2204 0.048 Uiso 1 1 calc R . . C7B C 0.8250(7) 0.9680(4) -0.1287(2) 0.0490(10) Uani 1 1 d . . . N1B N 0.4297(5) 1.0140(4) -0.34360(19) 0.0494(8) Uani 1 1 d . . . O3B O 0.2967(4) 0.9271(3) -0.30783(15) 0.0660(8) Uani 1 1 d . . . O4B O 0.4220(4) 1.0646(3) -0.40752(16) 0.0723(9) Uani 1 1 d . . . N2B N 1.0729(5) 1.3246(4) -0.3525(2) 0.0560(9) Uani 1 1 d . . . O5B O 1.0319(5) 1.3935(3) -0.41049(16) 0.0769(9) Uani 1 1 d . . . O6B O 1.2365(4) 1.3418(3) -0.32458(16) 0.0721(9) Uani 1 1 d . . . N1C N 0.2646(8) 0.6932(6) -0.0671(2) 0.0561(10) Uani 1 1 d . . . H1C H 0.277(6) 0.680(5) -0.005(3) 0.097(14) Uiso 1 1 d . . . H2C H 0.176(7) 0.787(6) -0.077(2) 0.094(17) Uiso 1 1 d . . . H3C H 0.185(6) 0.619(5) -0.078(2) 0.075(15) Uiso 1 1 d . . . H4C H 0.386(6) 0.690(5) -0.090(2) 0.065(16) Uiso 1 1 d . . . N1D N 0.7225(7) 0.8122(5) 0.0519(2) 0.0567(10) Uani 1 1 d . . . H1D H 0.824(7) 0.709(6) 0.059(2) 0.097(16) Uiso 1 1 d . . . H2D H 0.583(8) 0.765(6) 0.073(2) 0.107(17) Uiso 1 1 d . . . H3D H 0.726(5) 0.838(4) 0.002(2) 0.053(11) Uiso 1 1 d . . . H4D H 0.758(7) 0.890(6) 0.070(2) 0.080(17) 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 O1A 0.0572(16) 0.0482(18) 0.0650(17) 0.0060(13) -0.0262(13) -0.0062(13) O2A 0.0677(18) 0.078(2) 0.0555(17) 0.0174(15) -0.0166(14) -0.0263(16) C1A 0.038(2) 0.029(2) 0.043(2) -0.0047(17) -0.0092(16) -0.0008(16) C2A 0.0371(19) 0.030(2) 0.054(2) -0.0038(18) -0.0015(16) -0.0062(16) C3A 0.0370(19) 0.033(2) 0.049(2) -0.0014(18) -0.0118(16) -0.0061(16) C4A 0.040(2) 0.028(2) 0.048(2) -0.0083(18) -0.0067(16) 0.0001(16) C5A 0.041(2) 0.039(2) 0.052(2) -0.0058(19) -0.0047(17) -0.0118(17) C6A 0.0348(19) 0.043(2) 0.052(2) -0.0085(19) -0.0137(17) -0.0033(17) C7A 0.051(2) 0.033(2) 0.054(2) -0.0056(19) -0.0124(19) -0.0030(19) N1A 0.0481(18) 0.0412(19) 0.0456(18) 0.0080(15) -0.0087(14) -0.0113(15) C8A 0.071(3) 0.078(3) 0.060(3) 0.005(2) -0.024(2) -0.021(2) C9A 0.065(2) 0.058(3) 0.052(2) 0.006(2) -0.0107(19) -0.013(2) O1B 0.0759(18) 0.0456(18) 0.0746(19) -0.0009(14) -0.0373(15) -0.0010(14) O2B 0.0772(19) 0.070(2) 0.0570(17) 0.0103(15) -0.0143(14) -0.0126(16) C1B 0.044(2) 0.032(2) 0.043(2) -0.0053(17) -0.0100(16) 0.0030(17) C2B 0.048(2) 0.025(2) 0.053(2) -0.0032(18) -0.0082(17) -0.0003(16) C3B 0.041(2) 0.028(2) 0.052(2) -0.0087(18) -0.0147(17) 0.0042(16) C4B 0.053(2) 0.023(2) 0.052(2) -0.0026(18) -0.0098(18) 0.0028(17) C5B 0.047(2) 0.023(2) 0.054(2) -0.0065(18) -0.0021(17) -0.0032(17) C6B 0.038(2) 0.026(2) 0.058(2) -0.0158(18) -0.0107(17) 0.0046(16) C7B 0.057(3) 0.035(2) 0.057(3) -0.007(2) -0.018(2) 0.003(2) N1B 0.052(2) 0.0315(19) 0.068(2) -0.0095(17) -0.0203(18) 0.0030(16) O3B 0.0526(17) 0.0543(19) 0.096(2) -0.0159(16) -0.0153(15) -0.0138(15) O4B 0.095(2) 0.056(2) 0.074(2) -0.0036(16) -0.0445(16) -0.0006(15) N2B 0.057(2) 0.032(2) 0.080(3) -0.0160(19) 0.0012(19) -0.0091(17) O5B 0.108(2) 0.051(2) 0.068(2) 0.0100(16) -0.0029(17) -0.0218(17) O6B 0.0614(18) 0.0439(18) 0.112(2) -0.0108(16) -0.0048(16) -0.0204(14) N1C 0.052(3) 0.056(3) 0.061(3) 0.002(2) -0.010(2) -0.010(2) N1D 0.070(3) 0.048(3) 0.054(3) 0.004(2) -0.017(2) -0.014(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 O1A C7A 1.261(4) . ? O2A C7A 1.251(4) . ? C1A C6A 1.372(4) . ? C1A C2A 1.393(4) . ? C1A C7A 1.494(4) . ? C2A C3A 1.377(4) . ? C2A H2A 0.9300 . ? C3A C4A 1.403(4) . ? C3A H3A 0.9300 . ? C4A N1A 1.374(4) . ? C4A C5A 1.402(4) . ? C5A C6A 1.378(4) . ? C5A H5A 0.9300 . ? C6A H6A 0.9300 . ? N1A C9A 1.452(4) . ? N1A C8A 1.459(4) . ? C8A H8A1 0.9600 . ? C8A H8A2 0.9600 . ? C8A H8A3 0.9600 . ? C9A H9A1 0.9600 . ? C9A H9A2 0.9600 . ? C9A H9A3 0.9600 . ? O1B C7B 1.245(4) . ? O2B C7B 1.252(4) . ? C1B C6B 1.381(4) . ? C1B C2B 1.384(4) . ? C1B C7B 1.515(5) . ? C2B C3B 1.376(4) . ? C2B H2B 0.9300 . ? C3B C4B 1.380(4) . ? C3B N1B 1.462(4) . ? C4B C5B 1.370(4) . ? C4B H4B 0.9300 . ? C5B C6B 1.380(4) . ? C5B N2B 1.473(4) . ? C6B H6B 0.9300 . ? N1B O3B 1.216(3) . ? N1B O4B 1.231(4) . ? N2B O5B 1.221(4) . ? N2B O6B 1.224(4) . ? N1C H1C 1.18(5) . ? N1C H2C 0.95(5) . ? N1C H3C 0.88(4) . ? N1C H4C 0.81(4) . ? N1D H1D 1.04(5) . ? N1D H2D 0.98(5) . ? N1D H3D 0.93(4) . ? N1D H4D 0.83(5) . ? 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 C6A C1A C2A 117.1(3) . . ? C6A C1A C7A 121.8(3) . . ? C2A C1A C7A 121.1(3) . . ? C3A C2A C1A 121.8(3) . . ? C3A C2A H2A 119.1 . . ? C1A C2A H2A 119.1 . . ? C2A C3A C4A 121.1(3) . . ? C2A C3A H3A 119.4 . . ? C4A C3A H3A 119.4 . . ? N1A C4A C3A 121.9(3) . . ? N1A C4A C5A 121.6(3) . . ? C3A C4A C5A 116.5(3) . . ? C6A C5A C4A 121.2(3) . . ? C6A C5A H5A 119.4 . . ? C4A C5A H5A 119.4 . . ? C5A C6A C1A 122.2(3) . . ? C5A C6A H6A 118.9 . . ? C1A C6A H6A 118.9 . . ? O1A C7A O2A 122.7(3) . . ? O1A C7A C1A 118.1(3) . . ? O2A C7A C1A 119.3(3) . . ? C4A N1A C9A 120.7(3) . . ? C4A N1A C8A 120.2(3) . . ? C9A N1A C8A 115.1(3) . . ? N1A C8A H8A1 109.5 . . ? N1A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? N1A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? N1A C9A H9A1 109.5 . . ? N1A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? N1A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? C6B C1B C2B 118.5(3) . . ? C6B C1B C7B 121.1(3) . . ? C2B C1B C7B 120.3(3) . . ? C3B C2B C1B 119.9(3) . . ? C3B C2B H2B 120.1 . . ? C1B C2B H2B 120.1 . . ? C2B C3B C4B 122.5(3) . . ? C2B C3B N1B 118.8(3) . . ? C4B C3B N1B 118.7(3) . . ? C5B C4B C3B 116.6(3) . . ? C5B C4B H4B 121.7 . . ? C3B C4B H4B 121.7 . . ? C4B C5B C6B 122.4(3) . . ? C4B C5B N2B 117.8(3) . . ? C6B C5B N2B 119.8(3) . . ? C5B C6B C1B 120.1(3) . . ? C5B C6B H6B 119.9 . . ? C1B C6B H6B 119.9 . . ? O1B C7B O2B 125.9(4) . . ? O1B C7B C1B 117.1(3) . . ? O2B C7B C1B 117.0(3) . . ? O3B N1B O4B 123.8(3) . . ? O3B N1B C3B 118.2(3) . . ? O4B N1B C3B 118.0(3) . . ? O5B N2B O6B 124.8(3) . . ? O5B N2B C5B 118.5(3) . . ? O6B N2B C5B 116.7(4) . . ? H1C N1C H2C 107(3) . . ? H1C N1C H3C 111(3) . . ? H2C N1C H3C 102(3) . . ? H1C N1C H4C 110(3) . . ? H2C N1C H4C 116(4) . . ? H3C N1C H4C 110(4) . . ? H1D N1D H2D 98(3) . . ? H1D N1D H3D 105(3) . . ? H2D N1D H3D 111(3) . . ? H1D N1D H4D 115(4) . . ? H2D N1D H4D 117(4) . . ? H3D N1D H4D 110(4) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.220 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.059 data_VI _database_code_depnum_ccdc_archive 'CCDC 901376' #TrackingRef '15349_web_deposit_cif_file_1_ColinSeaton_1352638926.NH4_crown_VI_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (1,4,7,10,13,16-hexaoxacyclooctadecane)ammonium 3,5-dinitrobenzoate ; _chemical_name_common ;(1,4,7,10,13,16-hexaoxacyclooctadecane)ammonium 3,5- dinitrobenzoate ; _chemical_melting_point ? _chemical_formula_moiety 'C12 H24 O6, C7 H3 N2 O6, H4 N' _chemical_formula_sum 'C19 H31 N3 O12' _chemical_formula_weight 493.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.4622(3) _cell_length_b 8.2534(2) _cell_length_c 25.9532(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.485(2) _cell_angle_gamma 90.00 _cell_volume 2455.14(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5373 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 20.40 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9741 _exptl_absorpt_correction_T_max 0.9913 _exptl_absorpt_process_details 'Bruker APEX 2011.v4-1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 48026 _diffrn_reflns_av_R_equivalents 0.0679 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 25.25 _reflns_number_total 4429 _reflns_number_gt 2383 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^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 4429 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1171 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1799 _refine_ls_wR_factor_gt 0.1509 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 O1A O 0.47007(17) 0.4890(2) 0.18470(8) 0.0631(6) Uani 1 1 d . . . O2A O 0.50610(17) 0.7401(3) 0.11234(8) 0.0663(6) Uani 1 1 d . . . O3A O 0.3463(2) 1.0004(2) 0.11278(8) 0.0702(6) Uani 1 1 d . . . O4A O 0.21377(18) 1.0578(3) 0.20441(8) 0.0688(6) Uani 1 1 d . . . O5A O 0.15881(17) 0.7883(3) 0.26719(8) 0.0669(6) Uani 1 1 d . . . O6A O 0.34065(18) 0.5552(2) 0.27372(8) 0.0637(6) Uani 1 1 d . . . C1A C 0.5641(3) 0.4952(4) 0.14811(14) 0.0706(10) Uani 1 1 d . . . H1A1 H 0.5891 0.3860 0.1400 0.085 Uiso 1 1 calc R . . H1A2 H 0.6299 0.5526 0.1632 0.085 Uiso 1 1 calc R . . C2A C 0.5264(3) 0.5775(4) 0.10081(13) 0.0717(10) Uani 1 1 d . . . H2A1 H 0.5863 0.5686 0.0748 0.086 Uiso 1 1 calc R . . H2A2 H 0.4556 0.5279 0.0875 0.086 Uiso 1 1 calc R . . C3A C 0.4786(3) 0.8358(5) 0.06813(12) 0.0856(11) Uani 1 1 d . . . H3A1 H 0.4128 0.7890 0.0497 0.103 Uiso 1 1 calc R . . H3A2 H 0.5448 0.8387 0.0451 0.103 Uiso 1 1 calc R . . C4A C 0.4498(4) 1.0011(5) 0.08514(14) 0.0870(11) Uani 1 1 d . . . H4A1 H 0.5125 1.0430 0.1066 0.104 Uiso 1 1 calc R . . H4A2 H 0.4416 1.0714 0.0554 0.104 Uiso 1 1 calc R . . C5A C 0.3153(4) 1.1568(4) 0.13237(15) 0.0822(11) Uani 1 1 d . . . H5A1 H 0.3099 1.2337 0.1042 0.099 Uiso 1 1 calc R . . H5A2 H 0.3751 1.1942 0.1562 0.099 Uiso 1 1 calc R . . C6A C 0.2014(4) 1.1475(4) 0.15923(16) 0.0891(12) Uani 1 1 d . . . H6A1 H 0.1744 1.2559 0.1674 0.107 Uiso 1 1 calc R . . H6A2 H 0.1438 1.0967 0.1369 0.107 Uiso 1 1 calc R . . C7A C 0.1049(3) 1.0387(5) 0.23097(16) 0.0849(11) Uani 1 1 d . . . H7A1 H 0.0495 0.9827 0.2089 0.102 Uiso 1 1 calc R . . H7A2 H 0.0730 1.1444 0.2391 0.102 Uiso 1 1 calc R . . C8A C 0.1228(3) 0.9454(5) 0.27889(14) 0.0803(11) Uani 1 1 d . . . H8A1 H 0.1814 0.9982 0.3002 0.096 Uiso 1 1 calc R . . H8A2 H 0.0505 0.9415 0.2981 0.096 Uiso 1 1 calc R . . C9A C 0.1834(3) 0.6925(5) 0.31155(12) 0.0728(10) Uani 1 1 d . . . H9A1 H 0.1123 0.6766 0.3309 0.087 Uiso 1 1 calc R . . H9A2 H 0.2388 0.7492 0.3335 0.087 Uiso 1 1 calc R . . C10A C 0.2321(3) 0.5333(5) 0.29696(13) 0.0777(10) Uani 1 1 d . . . H10A H 0.2409 0.4659 0.3274 0.093 Uiso 1 1 calc R . . H10B H 0.1793 0.4790 0.2732 0.093 Uiso 1 1 calc R . . C11A C 0.4004(3) 0.4047(4) 0.26492(12) 0.0722(10) Uani 1 1 d . . . H11A H 0.3484 0.3294 0.2476 0.087 Uiso 1 1 calc R . . H11B H 0.4235 0.3573 0.2977 0.087 Uiso 1 1 calc R . . C12A C 0.5046(3) 0.4316(4) 0.23316(13) 0.0730(10) Uani 1 1 d . . . H12A H 0.5556 0.5099 0.2498 0.088 Uiso 1 1 calc R . . H12B H 0.5473 0.3309 0.2294 0.088 Uiso 1 1 calc R . . O2B O 0.0977(2) 0.5285(3) 0.12094(8) 0.0696(6) Uani 1 1 d . . . O1B O 0.2412(2) 0.5362(3) 0.06410(9) 0.0770(7) Uani 1 1 d . . . N1B N -0.2152(2) 0.1764(3) 0.03697(10) 0.0586(7) Uani 1 1 d . . . O3B O -0.2680(2) 0.2573(4) 0.06849(10) 0.0989(9) Uani 1 1 d . . . O4B O -0.2544(2) 0.0570(3) 0.01542(10) 0.0821(7) Uani 1 1 d . . . N2B N 0.1007(2) 0.1997(4) -0.08728(11) 0.0684(8) Uani 1 1 d . . . O5B O 0.0517(2) 0.0940(3) -0.11165(10) 0.0992(9) Uani 1 1 d . . . O6B O 0.1854(2) 0.2745(3) -0.10254(10) 0.1007(9) Uani 1 1 d . . . C1B C 0.0757(2) 0.3783(3) 0.04410(10) 0.0422(7) Uani 1 1 d . . . C2B C -0.0350(2) 0.3273(3) 0.05705(9) 0.0439(7) Uani 1 1 d . . . H2B H -0.0674 0.3577 0.0883 0.053 Uiso 1 1 calc R . . C3B C -0.0971(2) 0.2310(3) 0.02329(10) 0.0412(6) Uani 1 1 d . . . C4B C -0.0540(2) 0.1828(3) -0.02358(10) 0.0435(7) Uani 1 1 d . . . H4B H -0.0964 0.1158 -0.0457 0.052 Uiso 1 1 calc R . . C5B C 0.0551(2) 0.2390(3) -0.03600(10) 0.0455(7) Uani 1 1 d . . . C6B C 0.1205(2) 0.3342(3) -0.00312(11) 0.0456(7) Uani 1 1 d . . . H6B H 0.1944 0.3686 -0.0127 0.055 Uiso 1 1 calc R . . C7B C 0.1453(3) 0.4911(3) 0.07961(12) 0.0526(7) Uani 1 1 d . . . N1C N 0.2733(3) 0.7116(4) 0.16951(11) 0.0446(6) Uani 1 1 d . . . H1C H 0.222(3) 0.658(4) 0.1518(13) 0.075(11) Uiso 1 1 d . . . H2C H 0.328(3) 0.646(5) 0.1742(15) 0.098(14) Uiso 1 1 d . . . H3C H 0.302(3) 0.784(5) 0.1515(14) 0.090(14) Uiso 1 1 d . . . H4C H 0.235(4) 0.750(5) 0.199(2) 0.136(18) 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 O1A 0.0571(13) 0.0570(13) 0.0750(14) 0.0028(10) -0.0126(12) 0.0135(10) O2A 0.0611(13) 0.0740(15) 0.0640(14) -0.0125(11) 0.0066(11) -0.0030(11) O3A 0.0898(17) 0.0558(14) 0.0651(14) 0.0120(10) 0.0015(13) -0.0141(11) O4A 0.0634(14) 0.0620(14) 0.0809(15) -0.0008(12) -0.0142(12) 0.0149(11) O5A 0.0578(13) 0.0846(16) 0.0584(13) -0.0178(12) 0.0089(10) -0.0034(11) O6A 0.0685(14) 0.0608(14) 0.0617(13) 0.0137(10) -0.0003(11) -0.0166(11) C1A 0.0433(18) 0.067(2) 0.102(3) -0.0174(19) 0.0128(19) 0.0168(15) C2A 0.0514(19) 0.087(3) 0.077(2) -0.018(2) 0.0129(17) 0.0042(18) C3A 0.091(3) 0.119(3) 0.0467(19) 0.021(2) 0.0183(18) -0.007(2) C4A 0.104(3) 0.085(3) 0.072(2) 0.021(2) 0.004(2) -0.018(2) C5A 0.121(3) 0.0378(19) 0.087(2) 0.0192(17) -0.017(2) -0.0078(19) C6A 0.105(3) 0.058(2) 0.104(3) 0.007(2) -0.016(3) 0.020(2) C7A 0.055(2) 0.089(3) 0.111(3) -0.019(2) -0.005(2) 0.0307(19) C8A 0.050(2) 0.107(3) 0.085(3) -0.030(2) 0.0030(18) 0.008(2) C9A 0.059(2) 0.114(3) 0.0452(18) 0.0043(19) 0.0141(15) -0.027(2) C10A 0.086(3) 0.086(3) 0.062(2) 0.0093(19) 0.0108(19) -0.026(2) C11A 0.113(3) 0.0409(18) 0.063(2) 0.0167(15) -0.019(2) 0.0046(18) C12A 0.082(2) 0.053(2) 0.083(2) 0.0024(18) -0.021(2) 0.0154(17) O2B 0.0857(16) 0.0697(14) 0.0530(13) -0.0121(11) -0.0136(12) -0.0074(11) O1B 0.0575(14) 0.0832(17) 0.0901(17) -0.0122(13) -0.0132(13) -0.0194(12) N1B 0.0491(16) 0.0766(19) 0.0500(15) 0.0034(14) 0.0004(13) -0.0062(14) O3B 0.0680(16) 0.149(3) 0.0800(17) -0.0364(17) 0.0282(14) -0.0157(16) O4B 0.0658(14) 0.0815(17) 0.0989(18) -0.0093(15) 0.0007(13) -0.0265(13) N2B 0.0621(18) 0.0752(19) 0.0683(18) -0.0259(15) 0.0206(15) -0.0043(15) O5B 0.1010(19) 0.109(2) 0.0882(18) -0.0601(16) 0.0312(15) -0.0216(16) O6B 0.0868(18) 0.127(2) 0.0890(18) -0.0340(16) 0.0448(15) -0.0282(17) C1B 0.0481(17) 0.0353(14) 0.0429(15) 0.0039(12) -0.0099(13) 0.0053(12) C2B 0.0544(18) 0.0453(15) 0.0319(13) 0.0015(12) -0.0038(12) 0.0033(13) C3B 0.0388(15) 0.0423(15) 0.0426(15) 0.0055(12) -0.0018(12) 0.0014(12) C4B 0.0463(16) 0.0371(15) 0.0469(16) -0.0039(12) -0.0042(13) 0.0006(12) C5B 0.0489(17) 0.0407(15) 0.0470(16) -0.0081(12) 0.0035(13) 0.0066(13) C6B 0.0404(15) 0.0375(15) 0.0589(18) -0.0003(13) -0.0017(13) 0.0044(12) C7B 0.062(2) 0.0412(16) 0.0545(19) 0.0040(14) -0.0175(16) 0.0012(15) N1C 0.0451(16) 0.0449(15) 0.0439(15) 0.0008(13) -0.0035(13) -0.0021(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 O1A C12A 1.398(4) . ? O1A C1A 1.443(4) . ? O2A C2A 1.395(4) . ? O2A C3A 1.426(4) . ? O3A C4A 1.392(4) . ? O3A C5A 1.433(4) . ? O4A C6A 1.393(4) . ? O4A C7A 1.439(4) . ? O5A C8A 1.394(4) . ? O5A C9A 1.423(4) . ? O6A C10A 1.399(4) . ? O6A C11A 1.438(4) . ? C1A C2A 1.465(5) . ? C1A H1A1 0.9700 . ? C1A H1A2 0.9700 . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? C3A C4A 1.472(5) . ? C3A H3A1 0.9700 . ? C3A H3A2 0.9700 . ? C4A H4A1 0.9700 . ? C4A H4A2 0.9700 . ? C5A C6A 1.487(5) . ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C7A C8A 1.476(5) . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C9A C10A 1.479(5) . ? C9A H9A1 0.9700 . ? C9A H9A2 0.9700 . ? C10A H10A 0.9700 . ? C10A H10B 0.9700 . ? C11A C12A 1.473(4) . ? C11A H11A 0.9700 . ? C11A H11B 0.9700 . ? C12A H12A 0.9700 . ? C12A H12B 0.9700 . ? O2B C7B 1.246(4) . ? O1B C7B 1.231(4) . ? N1B O4B 1.217(3) . ? N1B O3B 1.221(3) . ? N1B C3B 1.473(3) . ? N2B O5B 1.213(3) . ? N2B O6B 1.219(3) . ? N2B C5B 1.470(4) . ? C1B C6B 1.381(4) . ? C1B C2B 1.382(4) . ? C1B C7B 1.530(4) . ? C2B C3B 1.376(4) . ? C2B H2B 0.9300 . ? C3B C4B 1.376(4) . ? C4B C5B 1.375(4) . ? C4B H4B 0.9300 . ? C5B C6B 1.377(4) . ? C6B H6B 0.9300 . ? N1C H1C 0.87(4) . ? N1C H2C 0.84(4) . ? N1C H3C 0.83(4) . ? N1C H4C 0.93(5) . ? 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 C12A O1A C1A 113.4(2) . . ? C2A O2A C3A 113.4(3) . . ? C4A O3A C5A 113.2(3) . . ? C6A O4A C7A 112.3(3) . . ? C8A O5A C9A 113.4(3) . . ? C10A O6A C11A 112.6(2) . . ? O1A C1A C2A 110.6(2) . . ? O1A C1A H1A1 109.5 . . ? C2A C1A H1A1 109.5 . . ? O1A C1A H1A2 109.5 . . ? C2A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 108.1 . . ? O2A C2A C1A 108.3(3) . . ? O2A C2A H2A1 110.0 . . ? C1A C2A H2A1 110.0 . . ? O2A C2A H2A2 110.0 . . ? C1A C2A H2A2 110.0 . . ? H2A1 C2A H2A2 108.4 . . ? O2A C3A C4A 108.7(3) . . ? O2A C3A H3A1 110.0 . . ? C4A C3A H3A1 110.0 . . ? O2A C3A H3A2 109.9 . . ? C4A C3A H3A2 110.0 . . ? H3A1 C3A H3A2 108.3 . . ? O3A C4A C3A 110.2(3) . . ? O3A C4A H4A1 109.6 . . ? C3A C4A H4A1 109.6 . . ? O3A C4A H4A2 109.6 . . ? C3A C4A H4A2 109.6 . . ? H4A1 C4A H4A2 108.1 . . ? O3A C5A C6A 110.0(3) . . ? O3A C5A H5A1 109.7 . . ? C6A C5A H5A1 109.7 . . ? O3A C5A H5A2 109.7 . . ? C6A C5A H5A2 109.7 . . ? H5A1 C5A H5A2 108.2 . . ? O4A C6A C5A 109.8(3) . . ? O4A C6A H6A1 109.7 . . ? C5A C6A H6A1 109.7 . . ? O4A C6A H6A2 109.7 . . ? C5A C6A H6A2 109.7 . . ? H6A1 C6A H6A2 108.2 . . ? O4A C7A C8A 110.3(3) . . ? O4A C7A H7A1 109.6 . . ? C8A C7A H7A1 109.6 . . ? O4A C7A H7A2 109.6 . . ? C8A C7A H7A2 109.6 . . ? H7A1 C7A H7A2 108.1 . . ? O5A C8A C7A 109.9(3) . . ? O5A C8A H8A1 109.7 . . ? C7A C8A H8A1 109.7 . . ? O5A C8A H8A2 109.7 . . ? C7A C8A H8A2 109.7 . . ? H8A1 C8A H8A2 108.2 . . ? O5A C9A C10A 111.1(3) . . ? O5A C9A H9A1 109.4 . . ? C10A C9A H9A1 109.4 . . ? O5A C9A H9A2 109.4 . . ? C10A C9A H9A2 109.4 . . ? H9A1 C9A H9A2 108.0 . . ? O6A C10A C9A 109.5(3) . . ? O6A C10A H10A 109.8 . . ? C9A C10A H10A 109.8 . . ? O6A C10A H10B 109.8 . . ? C9A C10A H10B 109.8 . . ? H10A C10A H10B 108.2 . . ? O6A C11A C12A 110.4(2) . . ? O6A C11A H11A 109.6 . . ? C12A C11A H11A 109.6 . . ? O6A C11A H11B 109.6 . . ? C12A C11A H11B 109.6 . . ? H11A C11A H11B 108.1 . . ? O1A C12A C11A 109.2(3) . . ? O1A C12A H12A 109.8 . . ? C11A C12A H12A 109.8 . . ? O1A C12A H12B 109.8 . . ? C11A C12A H12B 109.8 . . ? H12A C12A H12B 108.3 . . ? O4B N1B O3B 124.6(3) . . ? O4B N1B C3B 118.3(3) . . ? O3B N1B C3B 117.1(3) . . ? O5B N2B O6B 124.2(3) . . ? O5B N2B C5B 117.6(3) . . ? O6B N2B C5B 118.2(3) . . ? C6B C1B C2B 119.0(2) . . ? C6B C1B C7B 120.0(3) . . ? C2B C1B C7B 120.9(2) . . ? C3B C2B C1B 119.5(2) . . ? C3B C2B H2B 120.3 . . ? C1B C2B H2B 120.3 . . ? C2B C3B C4B 122.9(2) . . ? C2B C3B N1B 119.6(2) . . ? C4B C3B N1B 117.5(2) . . ? C5B C4B C3B 116.3(2) . . ? C5B C4B H4B 121.8 . . ? C3B C4B H4B 121.8 . . ? C4B C5B C6B 122.6(2) . . ? C4B C5B N2B 118.0(2) . . ? C6B C5B N2B 119.4(3) . . ? C1B C6B C5B 119.7(3) . . ? C1B C6B H6B 120.1 . . ? C5B C6B H6B 120.1 . . ? O1B C7B O2B 127.2(3) . . ? O1B C7B C1B 116.7(3) . . ? O2B C7B C1B 116.1(3) . . ? H1C N1C H2C 105(3) . . ? H1C N1C H3C 110(3) . . ? H2C N1C H3C 104(4) . . ? H1C N1C H4C 106(3) . . ? H2C N1C H4C 117(4) . . ? H3C N1C H4C 114(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.355 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.044