data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Marina Fonari' _publ_contact_author_address ; Institute of Applied Physics Academy of Sciences of Moldova Academy str 5 Chisinau MD2028 MOLDOVA ; _publ_contact_author_email FONARI.XRAY@PHYS.ASM.MD _publ_section_title ; Two new onium fluorosilicates, the products of interaction of fluorosilicic acid with 12-membered macrocycles: structures and spectroscopic properties ; loop_ _publ_author_name 'Marina Fonari' 'Vladimir B. Arion' 'Stepan S. Basok' 'Alim A. Ennan' 'Eduard V. Ganin' ; V.O.Gelmboldt ; 'Hanspeter Kahlig' 'B. Keppler' 'Larisa V. Koroeva' 'Sergiu Shova' 'Yurii A. Simonov' data_sesh029 _database_code_depnum_ccdc_archive 'CCDC 635343' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(2,3,5,6,8,9-hexahydro-1,4,7,10-benzotetraoxacyclododecin- 12-aminium) hexafluorosilicate dihydrate ; _chemical_name_common ; bis(2,3,5,6,8,9-hexahydro-1,4,7,10-benzotetraoxacyclododecin- 12-aminium) hexafluorosilicate dihydrate ; _chemical_melting_point '180/o C' _chemical_formula_moiety '2(C12 H18 N O4),F6 Si, 2(H2 O)' _chemical_formula_sum 'C24 H40 F6 N2 O10 Si' _chemical_formula_weight 658.67 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 21.8548(6) _cell_length_b 8.0635(2) _cell_length_c 8.5300(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.599(2) _cell_angle_gamma 90.00 _cell_volume 1486.31(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1883 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.91 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 0.173 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'X8APEX II CCD diffractometer' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33020 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 30.82 _reflns_number_total 4660 _reflns_number_gt 3275 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0686P)^2^+0.3154P] 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 4660 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1515 _refine_ls_wR_factor_gt 0.1370 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Si1 Si 0.0000 0.5000 0.5000 0.0557(2) Uani 1 2 d S . . F1 F 0.06654(7) 0.5808(2) 0.46575(18) 0.0962(5) Uani 1 1 d . . . F2 F 0.00811(6) 0.59553(17) 0.67585(14) 0.0762(4) Uani 1 1 d . . . F3 F 0.03828(7) 0.33827(18) 0.58656(15) 0.0871(5) Uani 1 1 d . . . O1 O 0.26646(5) 0.59412(13) 0.69509(15) 0.0475(3) Uani 1 1 d . . . O2 O 0.32565(5) 0.31969(15) 0.77679(12) 0.0439(3) Uani 1 1 d . . . O3 O 0.42593(6) 0.54301(16) 0.87868(14) 0.0533(3) Uani 1 1 d . . . O4 O 0.35193(6) 0.85144(16) 0.79608(14) 0.0516(3) Uani 1 1 d . . . N1 N 0.08590(6) 0.4024(2) 0.91466(19) 0.0515(4) Uani 1 1 d . . . H1A H 0.0709(14) 0.298(4) 0.944(4) 0.105(10) Uiso 1 1 d . . . H1B H 0.0626(11) 0.432(3) 0.830(3) 0.077(7) Uiso 1 1 d . . . H1C H 0.0848(9) 0.482(3) 0.999(3) 0.056(6) Uiso 1 1 d . . . O1W O 0.09171(9) 0.6204(3) 1.1568(3) 0.0819(5) Uani 1 1 d . . . H1W1 H 0.0794(16) 0.594(4) 1.249(5) 0.119(12) Uiso 1 1 d . . . H2W1 H 0.0699(17) 0.694(5) 1.120(4) 0.114(13) Uiso 1 1 d . . . C1 C 0.23563(6) 0.48134(17) 0.77157(16) 0.0349(3) Uani 1 1 d . . . C2 C 0.26742(6) 0.33474(18) 0.81641(16) 0.0365(3) Uani 1 1 d . . . C3 C 0.37396(7) 0.2825(2) 0.9036(2) 0.0461(3) Uani 1 1 d . . . H3A H 0.3808 0.1637 0.9107 0.055 Uiso 1 1 calc R . . H3B H 0.3628 0.3208 1.0034 0.055 Uiso 1 1 calc R . . C4 C 0.43150(7) 0.3686(2) 0.8707(2) 0.0511(4) Uani 1 1 d . . . H4A H 0.4663 0.3326 0.9474 0.061 Uiso 1 1 calc R . . H4B H 0.4398 0.3376 0.7660 0.061 Uiso 1 1 calc R . . C5 C 0.41793(8) 0.6246(2) 0.7297(2) 0.0534(4) Uani 1 1 d . . . H5A H 0.3817 0.5811 0.6628 0.064 Uiso 1 1 calc R . . H5B H 0.4537 0.6052 0.6771 0.064 Uiso 1 1 calc R . . C6 C 0.41026(8) 0.8070(2) 0.7550(2) 0.0569(4) Uani 1 1 d . . . H6A H 0.4424 0.8437 0.8386 0.068 Uiso 1 1 calc R . . H6B H 0.4160 0.8652 0.6588 0.068 Uiso 1 1 calc R . . C7 C 0.30366(8) 0.8636(2) 0.6661(2) 0.0470(4) Uani 1 1 d . . . H7A H 0.3178 0.8223 0.5709 0.056 Uiso 1 1 calc R . . H7B H 0.2918 0.9788 0.6487 0.056 Uiso 1 1 calc R . . C8 C 0.24903(7) 0.7644(2) 0.6992(2) 0.0466(4) Uani 1 1 d . . . H8A H 0.2386 0.7926 0.8025 0.056 Uiso 1 1 calc R . . H8B H 0.2134 0.7864 0.6196 0.056 Uiso 1 1 calc R . . C9 C 0.23974(8) 0.2128(2) 0.8938(2) 0.0478(4) Uani 1 1 d . . . H9A H 0.2613 0.1160 0.9248 0.057 Uiso 1 1 calc R . . C10 C 0.17959(8) 0.2334(2) 0.9260(2) 0.0499(4) Uani 1 1 d . . . H10A H 0.1606 0.1508 0.9776 0.060 Uiso 1 1 calc R . . C11 C 0.14916(6) 0.3767(2) 0.88059(17) 0.0409(3) Uani 1 1 d . . . C12 C 0.17586(6) 0.50297(19) 0.80449(17) 0.0392(3) Uani 1 1 d . . . H12A H 0.1542 0.6003 0.7760 0.047 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 Si1 0.0512(4) 0.0713(5) 0.0437(3) -0.0089(3) 0.0038(3) 0.0260(3) F1 0.0692(8) 0.1438(15) 0.0777(9) -0.0103(9) 0.0176(7) -0.0088(9) F2 0.0937(9) 0.0854(9) 0.0480(6) -0.0169(6) 0.0056(6) 0.0229(7) F3 0.1141(11) 0.0857(9) 0.0582(7) -0.0027(6) 0.0024(7) 0.0516(8) O1 0.0454(6) 0.0372(6) 0.0653(7) 0.0049(5) 0.0260(5) -0.0033(4) O2 0.0359(5) 0.0581(7) 0.0377(5) -0.0013(5) 0.0055(4) 0.0039(4) O3 0.0591(7) 0.0540(7) 0.0444(6) -0.0017(5) -0.0001(5) -0.0070(5) O4 0.0530(7) 0.0534(7) 0.0488(6) -0.0010(5) 0.0095(5) -0.0085(5) N1 0.0336(6) 0.0747(11) 0.0467(8) 0.0078(8) 0.0074(6) -0.0115(6) O1W 0.0793(12) 0.0813(12) 0.0903(13) -0.0051(10) 0.0295(10) 0.0052(10) C1 0.0340(6) 0.0366(7) 0.0345(6) -0.0001(5) 0.0064(5) -0.0070(5) C2 0.0340(6) 0.0423(7) 0.0328(6) -0.0035(5) 0.0032(5) -0.0028(5) C3 0.0424(8) 0.0444(8) 0.0499(8) 0.0035(7) 0.0018(6) 0.0081(6) C4 0.0372(7) 0.0574(10) 0.0575(10) -0.0026(8) 0.0035(7) 0.0071(7) C5 0.0444(8) 0.0689(11) 0.0491(9) 0.0040(8) 0.0146(7) -0.0029(8) C6 0.0452(9) 0.0619(11) 0.0644(11) 0.0109(9) 0.0102(8) -0.0162(8) C7 0.0508(9) 0.0405(8) 0.0512(8) 0.0109(7) 0.0121(7) -0.0038(6) C8 0.0422(8) 0.0401(8) 0.0594(9) 0.0113(7) 0.0136(7) 0.0026(6) C9 0.0518(9) 0.0437(8) 0.0474(8) 0.0106(7) 0.0060(7) -0.0002(7) C10 0.0503(9) 0.0537(9) 0.0459(8) 0.0124(7) 0.0079(7) -0.0150(7) C11 0.0322(6) 0.0562(9) 0.0340(6) 0.0004(6) 0.0042(5) -0.0120(6) C12 0.0337(6) 0.0429(8) 0.0409(7) 0.0032(6) 0.0057(5) -0.0039(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 Si1 F1 1.6588(15) 3_566 ? Si1 F1 1.6588(15) . ? Si1 F3 1.6617(12) . ? Si1 F3 1.6617(12) 3_566 ? Si1 F2 1.6719(11) . ? Si1 F2 1.6719(11) 3_566 ? O1 C1 1.3557(16) . ? O1 C8 1.4266(19) . ? O2 C2 1.3702(17) . ? O2 C3 1.4260(19) . ? O3 C4 1.414(2) . ? O3 C5 1.419(2) . ? O4 C7 1.415(2) . ? O4 C6 1.418(2) . ? N1 C11 1.4692(19) . ? N1 H1A 0.95(3) . ? N1 H1B 0.86(3) . ? N1 H1C 0.97(2) . ? O1W H1W1 0.90(4) . ? O1W H2W1 0.80(4) . ? C1 C12 1.3877(19) . ? C1 C2 1.395(2) . ? C2 C9 1.374(2) . ? C3 C4 1.499(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.500(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.499(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.393(2) . ? C9 H9A 0.9300 . ? C10 C11 1.360(2) . ? C10 H10A 0.9300 . ? C11 C12 1.382(2) . ? C12 H12A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 Si1 F1 180.00(4) 3_566 . ? F1 Si1 F3 90.57(9) 3_566 . ? F1 Si1 F3 89.43(9) . . ? F1 Si1 F3 89.43(9) 3_566 3_566 ? F1 Si1 F3 90.57(9) . 3_566 ? F3 Si1 F3 180.00(8) . 3_566 ? F1 Si1 F2 90.06(8) 3_566 . ? F1 Si1 F2 89.94(8) . . ? F3 Si1 F2 89.09(6) . . ? F3 Si1 F2 90.91(6) 3_566 . ? F1 Si1 F2 89.94(8) 3_566 3_566 ? F1 Si1 F2 90.06(7) . 3_566 ? F3 Si1 F2 90.91(6) . 3_566 ? F3 Si1 F2 89.09(6) 3_566 3_566 ? F2 Si1 F2 180.0 . 3_566 ? C1 O1 C8 118.68(11) . . ? C2 O2 C3 116.18(11) . . ? C4 O3 C5 114.71(14) . . ? C7 O4 C6 114.63(13) . . ? C11 N1 H1A 107.2(17) . . ? C11 N1 H1B 109.3(16) . . ? H1A N1 H1B 106(2) . . ? C11 N1 H1C 111.7(12) . . ? H1A N1 H1C 110(2) . . ? H1B N1 H1C 112(2) . . ? H1W1 O1W H2W1 106(3) . . ? O1 C1 C12 124.31(13) . . ? O1 C1 C2 115.94(12) . . ? C12 C1 C2 119.74(13) . . ? O2 C2 C9 123.17(14) . . ? O2 C2 C1 116.75(13) . . ? C9 C2 C1 120.07(13) . . ? O2 C3 C4 107.89(13) . . ? O2 C3 H3A 110.1 . . ? C4 C3 H3A 110.1 . . ? O2 C3 H3B 110.1 . . ? C4 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? O3 C4 C3 111.78(13) . . ? O3 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? O3 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? O3 C5 C6 109.08(15) . . ? O3 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? O3 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? O4 C6 C5 114.06(14) . . ? O4 C6 H6A 108.7 . . ? C5 C6 H6A 108.7 . . ? O4 C6 H6B 108.7 . . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? O4 C7 C8 109.68(13) . . ? O4 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? O4 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? O1 C8 C7 106.62(12) . . ? O1 C8 H8A 110.4 . . ? C7 C8 H8A 110.4 . . ? O1 C8 H8B 110.4 . . ? C7 C8 H8B 110.4 . . ? H8A C8 H8B 108.6 . . ? C2 C9 C10 120.40(15) . . ? C2 C9 H9A 119.8 . . ? C10 C9 H9A 119.8 . . ? C11 C10 C9 118.73(14) . . ? C11 C10 H10A 120.6 . . ? C9 C10 H10A 120.6 . . ? C10 C11 C12 122.44(14) . . ? C10 C11 N1 119.86(14) . . ? C12 C11 N1 117.69(15) . . ? C11 C12 C1 118.60(14) . . ? C11 C12 H12A 120.7 . . ? C1 C12 H12A 120.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 -0.82(18) . . . . ? C1 C2 O2 C3 125.85(14) . . . . ? C2 O2 C3 C4 -145.71(14) . . . . ? O2 C3 C4 O3 66.95(17) . . . . ? C3 C4 O3 C5 -106.03(16) . . . . ? C4 O3 C5 C6 177.86(14) . . . . ? O3 C5 C6 O4 -73.69(19) . . . . ? C5 C6 O4 C7 -81.09(18) . . . . ? C6 O4 C7 C8 129.30(15) . . . . ? O4 C7 C8 O1 -69.60(17) . . . . ? C7 C8 O1 C1 157.87(13) . . . . ? C8 O1 C1 C2 -156.32(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A F3 0.95(3) 1.86(3) 2.731(2) 151(3) 4_566 N1 H1A F2 0.95(3) 2.48(3) 3.235(2) 136(2) 2_546 N1 H1B F2 0.86(3) 2.10(3) 2.903(2) 156(2) . N1 H1B F3 0.86(3) 2.20(3) 2.883(2) 137(2) . N1 H1C O1W 0.97(2) 1.74(2) 2.701(3) 173.6(19) . O1W H1W1 F1 0.90(4) 1.91(4) 2.790(3) 166(3) 1_556 O1W H1W1 F2 0.90(4) 2.60(4) 3.280(3) 133(3) 3_567 O1W H2W1 F1 0.80(4) 2.24(4) 2.915(3) 143(3) 4_576 O1W H2W1 F2 0.80(4) 2.26(4) 2.949(3) 145(3) 4_576 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.82 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.380 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.055 data_sesh037 _database_code_depnum_ccdc_archive 'CCDC 635344' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(1,4,7-trioxa-10-azoniacyclododecane) bis(aquapentafluorosilicate) trihydrate ; _chemical_name_common ;bis(1,4,7-trioxa-10-azoniacyclododecane) bis(aquapentafluorosilicate) trihydrate ; _chemical_melting_point 110/oC _chemical_formula_moiety '2(C8 H18 N O3), 2(F5 H2 O1 Si1), 2(H2 O1), O1' _chemical_formula_sum 'C16 H46 F10 N2 O11 Si2' _chemical_formula_weight 688.73 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.8889(7) _cell_length_b 9.3635(5) _cell_length_c 20.3291(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.900(3) _cell_angle_gamma 90.00 _cell_volume 2827.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'X8APEX II CCD diffractometer' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 88034 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6465 _reflns_number_gt 5432 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP for windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0554P)^2^+3.3768P] 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 6465 _refine_ls_number_parameters 413 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1199 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 Si1 Si 0.15457(3) 0.25527(5) 0.47664(2) 0.01152(12) Uani 1 1 d . . . F1 F 0.05446(8) 0.32955(13) 0.45929(6) 0.0246(3) Uani 1 1 d . . . F2 F 0.15024(9) 0.28576(13) 0.55592(6) 0.0250(3) Uani 1 1 d . . . F3 F 0.20939(7) 0.41240(11) 0.46784(5) 0.0159(2) Uani 1 1 d . . . F4 F 0.16527(8) 0.22738(12) 0.39564(5) 0.0218(3) Uani 1 1 d . . . F5 F 0.11096(7) 0.09305(12) 0.48416(6) 0.0195(2) Uani 1 1 d . . . O1W O 0.26696(9) 0.17646(16) 0.49416(8) 0.0231(3) Uani 1 1 d D . . H1W1 H 0.272(2) 0.087(4) 0.4979(16) 0.051(9) Uiso 1 1 d . . . H2W1 H 0.3115(17) 0.222(3) 0.4770(15) 0.049(9) Uiso 1 1 d D . . Si2 Si 0.34062(3) -0.24377(5) 0.01565(2) 0.01303(12) Uani 1 1 d . . . F6 F 0.32048(8) -0.22241(13) -0.06437(6) 0.0228(3) Uani 1 1 d . . . F7 F 0.38433(7) -0.07782(12) 0.02209(6) 0.0206(2) Uani 1 1 d . . . F8 F 0.35455(8) -0.25721(12) 0.09830(6) 0.0209(2) Uani 1 1 d . . . F9 F 0.44049(7) -0.31681(13) 0.00687(7) 0.0240(3) Uani 1 1 d . . . F10 F 0.28659(7) -0.40019(12) 0.01320(6) 0.0204(2) Uani 1 1 d . . . O2W O 0.22970(9) -0.15894(15) 0.02861(6) 0.0150(3) Uani 1 1 d D . . H1W2 H 0.1834(16) -0.214(3) 0.0192(15) 0.043(8) Uiso 1 1 d D . . H2W2 H 0.221(2) -0.075(4) 0.0122(15) 0.042(8) Uiso 1 1 d . . . N1 N 0.15885(11) 0.49178(17) 0.32817(8) 0.0144(3) Uani 1 1 d . . . H1N1 H 0.1519(15) 0.420(3) 0.3514(12) 0.014(6) Uiso 1 1 d . . . H2N1 H 0.1362(17) 0.480(3) 0.2904(14) 0.023(6) Uiso 1 1 d . . . N2 N 0.34195(11) 0.00293(17) 0.16352(8) 0.0151(3) Uani 1 1 d . . . H1N2 H 0.3698(17) -0.010(3) 0.2014(14) 0.025(6) Uiso 1 1 d . . . H2N2 H 0.3494(16) -0.071(3) 0.1393(12) 0.020(6) Uiso 1 1 d . . . O1 O 0.23690(10) 0.35818(15) 0.22375(7) 0.0200(3) Uani 1 1 d . . . O2 O 0.10771(9) 0.57099(15) 0.19760(6) 0.0174(3) Uani 1 1 d . . . O3 O -0.02121(9) 0.55570(16) 0.28910(7) 0.0220(3) Uani 1 1 d . . . O4 O 0.26819(9) -0.14569(14) 0.26598(7) 0.0178(3) Uani 1 1 d . . . O5 O 0.39359(9) 0.07091(15) 0.29406(7) 0.0174(3) Uani 1 1 d . . . O6 O 0.52085(10) 0.07204(16) 0.20156(8) 0.0240(3) Uani 1 1 d . . . C1 C 0.25699(12) 0.5108(2) 0.32050(9) 0.0166(4) Uani 1 1 d . . . H1A H 0.2891 0.5168 0.3636 0.020 Uiso 1 1 calc R . . H1B H 0.2671 0.5988 0.2969 0.020 Uiso 1 1 calc R . . C2 C 0.29149(13) 0.3854(2) 0.28278(9) 0.0182(4) Uani 1 1 d . . . H2A H 0.3527 0.4047 0.2718 0.022 Uiso 1 1 calc R . . H2B H 0.2925 0.3011 0.3105 0.022 Uiso 1 1 calc R . . C3 C 0.24443(15) 0.4610(2) 0.17242(10) 0.0233(4) Uani 1 1 d . . . H3A H 0.2777 0.4205 0.1375 0.028 Uiso 1 1 calc R . . H3B H 0.2768 0.5443 0.1897 0.028 Uiso 1 1 calc R . . C4 C 0.15181(15) 0.5038(2) 0.14549(9) 0.0225(4) Uani 1 1 d . . . H4A H 0.1558 0.5694 0.1089 0.027 Uiso 1 1 calc R . . H4B H 0.1182 0.4203 0.1298 0.027 Uiso 1 1 calc R . . C5 C 0.01648(14) 0.6076(2) 0.17938(10) 0.0234(4) Uani 1 1 d . . . H5A H -0.0165 0.5239 0.1632 0.028 Uiso 1 1 calc R . . H5B H 0.0138 0.6792 0.1448 0.028 Uiso 1 1 calc R . . C6 C -0.02374(13) 0.6652(2) 0.24000(10) 0.0217(4) Uani 1 1 d . . . H6A H 0.0102 0.7477 0.2565 0.026 Uiso 1 1 calc R . . H6B H -0.0854 0.6947 0.2293 0.026 Uiso 1 1 calc R . . C7 C 0.01407(14) 0.5985(2) 0.35295(10) 0.0245(4) Uani 1 1 d . . . H7A H 0.0004 0.5260 0.3848 0.029 Uiso 1 1 calc R . . H7B H -0.0146 0.6867 0.3652 0.029 Uiso 1 1 calc R . . C8 C 0.11501(14) 0.6206(2) 0.35487(10) 0.0207(4) Uani 1 1 d . . . H8A H 0.1285 0.7036 0.3288 0.025 Uiso 1 1 calc R . . H8B H 0.1383 0.6373 0.3999 0.025 Uiso 1 1 calc R . . C9 C 0.24372(12) 0.0169(2) 0.17298(9) 0.0166(4) Uani 1 1 d . . . H9A H 0.2104 0.0267 0.1306 0.020 Uiso 1 1 calc R . . H9B H 0.2330 0.1012 0.1990 0.020 Uiso 1 1 calc R . . C10 C 0.21257(13) -0.1149(2) 0.20793(10) 0.0180(4) Uani 1 1 d . . . H10A H 0.1511 -0.1008 0.2196 0.022 Uiso 1 1 calc R . . H10B H 0.2131 -0.1959 0.1782 0.022 Uiso 1 1 calc R . . C11 C 0.26008(13) -0.0479(2) 0.31952(10) 0.0194(4) Uani 1 1 d . . . H11A H 0.2289 -0.0935 0.3542 0.023 Uiso 1 1 calc R . . H11B H 0.2255 0.0350 0.3043 0.023 Uiso 1 1 calc R . . C12 C 0.35268(14) -0.0025(2) 0.34569(9) 0.0205(4) Uani 1 1 d . . . H12A H 0.3486 0.0599 0.3835 0.025 Uiso 1 1 calc R . . H12B H 0.3883 -0.0854 0.3594 0.025 Uiso 1 1 calc R . . C13 C 0.48358(14) 0.1148(2) 0.31229(10) 0.0241(4) Uani 1 1 d . . . H13A H 0.5196 0.0335 0.3276 0.029 Uiso 1 1 calc R . . H13B H 0.4840 0.1847 0.3475 0.029 Uiso 1 1 calc R . . C14 C 0.52129(14) 0.1792(2) 0.25207(11) 0.0245(4) Uani 1 1 d . . . H14A H 0.4849 0.2601 0.2368 0.029 Uiso 1 1 calc R . . H14B H 0.5823 0.2123 0.2627 0.029 Uiso 1 1 calc R . . C15 C 0.48429(15) 0.1156(2) 0.13812(11) 0.0260(4) Uani 1 1 d . . . H15A H 0.4986 0.0446 0.1057 0.031 Uiso 1 1 calc R . . H15B H 0.5117 0.2052 0.1263 0.031 Uiso 1 1 calc R . . C16 C 0.38296(14) 0.1341(2) 0.13689(10) 0.0205(4) Uani 1 1 d . . . H16A H 0.3685 0.2161 0.1634 0.025 Uiso 1 1 calc R . . H16B H 0.3588 0.1507 0.0920 0.025 Uiso 1 1 calc R . . O3W O 0.40219(10) 0.31975(17) 0.45522(8) 0.0220(3) Uani 1 1 d . . . H1W3 H 0.3957(19) 0.400(3) 0.4716(14) 0.033(7) Uiso 1 1 d . . . H2W3 H 0.450(2) 0.292(4) 0.4668(16) 0.047(9) Uiso 1 1 d . . . O4W O 0.08957(10) -0.30218(16) -0.01211(8) 0.0204(3) Uani 1 1 d . . . H1W4 H 0.091(2) -0.392(4) -0.0138(15) 0.047(9) Uiso 1 1 d . . . H2W4 H 0.044(2) -0.277(4) 0.0022(16) 0.047(9) Uiso 1 1 d . . . O5W O 0.5627(5) -0.4131(8) -0.0720(4) 0.0407(17) Uiso 0.25 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Si1 0.0128(2) 0.0097(2) 0.0121(2) 0.00102(17) 0.00135(17) -0.00074(17) F1 0.0155(5) 0.0197(6) 0.0385(7) 0.0072(5) 0.0014(5) 0.0028(4) F2 0.0372(7) 0.0240(6) 0.0143(5) -0.0011(5) 0.0063(5) -0.0020(5) F3 0.0179(5) 0.0110(5) 0.0188(5) 0.0004(4) 0.0013(4) -0.0021(4) F4 0.0342(7) 0.0187(6) 0.0125(5) -0.0024(4) 0.0027(5) -0.0074(5) F5 0.0176(5) 0.0140(5) 0.0269(6) 0.0040(4) 0.0019(4) -0.0037(4) O1W 0.0142(7) 0.0135(7) 0.0421(9) 0.0050(6) 0.0040(6) 0.0005(5) Si2 0.0128(2) 0.0098(2) 0.0164(2) -0.00186(18) 0.00026(18) -0.00018(17) F6 0.0268(6) 0.0256(6) 0.0165(5) -0.0022(5) 0.0048(5) 0.0025(5) F7 0.0178(5) 0.0126(5) 0.0313(6) -0.0003(5) 0.0002(5) -0.0027(4) F8 0.0260(6) 0.0184(6) 0.0172(5) 0.0000(4) -0.0053(5) 0.0058(5) F9 0.0138(5) 0.0186(6) 0.0398(7) -0.0042(5) 0.0034(5) 0.0026(4) F10 0.0171(5) 0.0111(5) 0.0330(6) -0.0038(5) 0.0019(5) -0.0012(4) O2W 0.0151(6) 0.0128(6) 0.0170(6) 0.0017(5) 0.0010(5) 0.0014(5) N1 0.0189(8) 0.0139(7) 0.0103(7) 0.0008(6) 0.0001(6) 0.0018(6) N2 0.0182(8) 0.0117(7) 0.0152(7) -0.0013(6) 0.0011(6) 0.0003(6) O1 0.0302(8) 0.0143(6) 0.0156(6) -0.0001(5) 0.0027(5) 0.0019(5) O2 0.0211(7) 0.0189(7) 0.0118(6) -0.0004(5) -0.0010(5) 0.0017(5) O3 0.0193(7) 0.0217(7) 0.0250(7) 0.0074(6) 0.0009(6) -0.0027(6) O4 0.0205(7) 0.0139(6) 0.0190(7) 0.0008(5) 0.0013(5) 0.0012(5) O5 0.0153(6) 0.0198(7) 0.0172(6) -0.0019(5) 0.0013(5) -0.0027(5) O6 0.0210(7) 0.0234(7) 0.0283(8) -0.0093(6) 0.0060(6) -0.0006(6) C1 0.0176(9) 0.0146(8) 0.0177(9) 0.0004(7) 0.0016(7) -0.0001(7) C2 0.0196(9) 0.0159(9) 0.0193(9) 0.0010(7) 0.0025(7) 0.0028(7) C3 0.0327(11) 0.0194(10) 0.0191(9) 0.0034(8) 0.0107(8) 0.0059(8) C4 0.0358(11) 0.0213(10) 0.0106(8) -0.0005(7) 0.0021(8) 0.0032(8) C5 0.0234(10) 0.0274(11) 0.0184(9) 0.0032(8) -0.0072(8) 0.0006(8) C6 0.0173(9) 0.0233(10) 0.0243(10) 0.0071(8) -0.0017(7) 0.0015(8) C7 0.0257(10) 0.0288(11) 0.0196(9) 0.0051(8) 0.0067(8) 0.0080(8) C8 0.0247(10) 0.0201(9) 0.0169(9) -0.0041(7) -0.0016(7) 0.0087(8) C9 0.0166(9) 0.0153(9) 0.0178(9) -0.0014(7) 0.0002(7) 0.0020(7) C10 0.0161(9) 0.0152(9) 0.0224(9) -0.0018(7) -0.0013(7) -0.0003(7) C11 0.0221(9) 0.0170(9) 0.0197(9) -0.0021(7) 0.0057(7) -0.0008(7) C12 0.0245(10) 0.0211(9) 0.0160(9) -0.0002(7) 0.0015(7) -0.0008(8) C13 0.0190(10) 0.0281(11) 0.0248(10) -0.0085(8) -0.0010(8) -0.0040(8) C14 0.0186(9) 0.0241(10) 0.0314(11) -0.0112(9) 0.0064(8) -0.0065(8) C15 0.0276(11) 0.0245(10) 0.0273(11) -0.0049(8) 0.0127(9) -0.0060(8) C16 0.0268(10) 0.0144(9) 0.0207(9) 0.0015(7) 0.0054(8) -0.0027(7) O3W 0.0146(7) 0.0229(8) 0.0289(8) -0.0046(6) 0.0037(6) -0.0005(6) O4W 0.0137(7) 0.0155(7) 0.0326(8) 0.0033(6) 0.0053(6) 0.0009(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 Si1 F2 1.6424(12) . ? Si1 F1 1.6608(12) . ? Si1 F5 1.6631(12) . ? Si1 F4 1.6854(12) . ? Si1 F3 1.6979(11) . ? Si1 O1W 1.8414(15) . ? O1W H1W1 0.85(4) . ? O1W H2W1 0.878(18) . ? Si2 F6 1.6463(12) . ? Si2 F9 1.6574(12) . ? Si2 F10 1.6701(12) . ? Si2 F8 1.6836(12) . ? Si2 F7 1.6863(12) . ? Si2 O2W 1.8673(14) . ? O2W H1W2 0.870(18) . ? O2W H2W2 0.86(3) . ? N1 C1 1.491(2) . ? N1 C8 1.491(2) . ? N1 H1N1 0.83(3) . ? N1 H2N1 0.83(3) . ? N2 C16 1.490(2) . ? N2 C9 1.494(2) . ? N2 H1N2 0.86(3) . ? N2 H2N2 0.86(3) . ? O1 C2 1.426(2) . ? O1 C3 1.430(2) . ? O2 C5 1.425(2) . ? O2 C4 1.430(2) . ? O3 C7 1.424(3) . ? O3 C6 1.430(2) . ? O4 C10 1.424(2) . ? O4 C11 1.434(2) . ? O5 C12 1.426(2) . ? O5 C13 1.426(2) . ? O6 C15 1.425(3) . ? O6 C14 1.435(2) . ? C1 C2 1.512(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.503(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.506(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.515(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.512(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.505(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.507(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.517(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? O3W H1W3 0.83(3) . ? O3W H2W3 0.79(3) . ? O4W H1W4 0.84(4) . ? O4W H2W4 0.79(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F2 Si1 F1 92.35(7) . . ? F2 Si1 F5 91.54(6) . . ? F1 Si1 F5 92.96(6) . . ? F2 Si1 F4 176.66(7) . . ? F1 Si1 F4 90.03(7) . . ? F5 Si1 F4 90.67(6) . . ? F2 Si1 F3 90.23(6) . . ? F1 Si1 F3 92.62(6) . . ? F5 Si1 F3 174.07(6) . . ? F4 Si1 F3 87.32(6) . . ? F2 Si1 O1W 88.60(7) . . ? F1 Si1 O1W 178.34(7) . . ? F5 Si1 O1W 88.37(6) . . ? F4 Si1 O1W 88.96(7) . . ? F3 Si1 O1W 86.02(6) . . ? Si1 O1W H1W1 120(2) . . ? Si1 O1W H2W1 116(2) . . ? H1W1 O1W H2W1 116(3) . . ? F6 Si2 F9 92.75(7) . . ? F6 Si2 F10 91.26(6) . . ? F9 Si2 F10 93.94(6) . . ? F6 Si2 F8 175.63(6) . . ? F9 Si2 F8 91.50(6) . . ? F10 Si2 F8 89.47(6) . . ? F6 Si2 F7 90.47(6) . . ? F9 Si2 F7 92.54(6) . . ? F10 Si2 F7 173.21(6) . . ? F8 Si2 F7 88.32(6) . . ? F6 Si2 O2W 89.10(6) . . ? F9 Si2 O2W 177.88(7) . . ? F10 Si2 O2W 87.04(6) . . ? F8 Si2 O2W 86.63(6) . . ? F7 Si2 O2W 86.42(6) . . ? Si2 O2W H1W2 114(2) . . ? Si2 O2W H2W2 116(2) . . ? H1W2 O2W H2W2 111(3) . . ? C1 N1 C8 113.45(15) . . ? C1 N1 H1N1 108.4(16) . . ? C8 N1 H1N1 111.9(16) . . ? C1 N1 H2N1 105.1(17) . . ? C8 N1 H2N1 106.7(18) . . ? H1N1 N1 H2N1 111(2) . . ? C16 N2 C9 113.82(15) . . ? C16 N2 H1N2 104.7(18) . . ? C9 N2 H1N2 108.3(17) . . ? C16 N2 H2N2 112.4(16) . . ? C9 N2 H2N2 108.0(16) . . ? H1N2 N2 H2N2 109(2) . . ? C2 O1 C3 115.17(16) . . ? C5 O2 C4 113.00(15) . . ? C7 O3 C6 115.15(16) . . ? C10 O4 C11 115.19(15) . . ? C12 O5 C13 112.86(15) . . ? C15 O6 C14 115.50(17) . . ? N1 C1 C2 109.24(15) . . ? N1 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 . . ? N1 C1 H1B 109.8 . . ? C2 C1 H1B 109.8 . . ? H1A C1 H1B 108.3 . . ? O1 C2 C1 111.83(15) . . ? O1 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? O1 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? O1 C3 C4 109.25(17) . . ? O1 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? O1 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.3 . . ? O2 C4 C3 107.67(16) . . ? O2 C4 H4A 110.2 . . ? C3 C4 H4A 110.2 . . ? O2 C4 H4B 110.2 . . ? C3 C4 H4B 110.2 . . ? H4A C4 H4B 108.5 . . ? O2 C5 C6 107.36(15) . . ? O2 C5 H5A 110.2 . . ? C6 C5 H5A 110.2 . . ? O2 C5 H5B 110.2 . . ? C6 C5 H5B 110.2 . . ? H5A C5 H5B 108.5 . . ? O3 C6 C5 108.73(17) . . ? O3 C6 H6A 109.9 . . ? C5 C6 H6A 109.9 . . ? O3 C6 H6B 109.9 . . ? C5 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? O3 C7 C8 111.45(16) . . ? O3 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? O3 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? N1 C8 C7 109.78(17) . . ? N1 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? N1 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? N2 C9 C10 108.88(15) . . ? N2 C9 H9A 109.9 . . ? C10 C9 H9A 109.9 . . ? N2 C9 H9B 109.9 . . ? C10 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? O4 C10 C9 112.00(15) . . ? O4 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? O4 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? O4 C11 C12 109.05(15) . . ? O4 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? O4 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? O5 C12 C11 107.63(16) . . ? O5 C12 H12A 110.2 . . ? C11 C12 H12A 110.2 . . ? O5 C12 H12B 110.2 . . ? C11 C12 H12B 110.2 . . ? H12A C12 H12B 108.5 . . ? O5 C13 C14 107.42(17) . . ? O5 C13 H13A 110.2 . . ? C14 C13 H13A 110.2 . . ? O5 C13 H13B 110.2 . . ? C14 C13 H13B 110.2 . . ? H13A C13 H13B 108.5 . . ? O6 C14 C13 108.55(17) . . ? O6 C14 H14A 110.0 . . ? C13 C14 H14A 110.0 . . ? O6 C14 H14B 110.0 . . ? C13 C14 H14B 110.0 . . ? H14A C14 H14B 108.4 . . ? O6 C15 C16 111.47(16) . . ? O6 C15 H15A 109.3 . . ? C16 C15 H15A 109.3 . . ? O6 C15 H15B 109.3 . . ? C16 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? N2 C16 C15 109.35(16) . . ? N2 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? N2 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.3 . . ? H1W3 O3W H2W3 108(3) . . ? H1W4 O4W H2W4 110(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 O1 50.1(2) . . . . ? C1 C2 O1 C3 71.6(2) . . . . ? C2 O1 C3 C4 -132.32(17) . . . . ? O1 C3 C4 O2 63.1(2) . . . . ? C3 C4 O2 C5 -175.83(16) . . . . ? C4 O2 C5 C6 175.22(16) . . . . ? O2 C5 C6 O3 -61.7(2) . . . . ? C5 C6 O3 C7 131.44(17) . . . . ? C6 O3 C7 C8 -72.3(2) . . . . ? O3 C7 C8 N1 -52.0(2) . . . . ? C7 C8 N1 C1 172.93(15) . . . . ? C8 N1 C1 C2 -170.49(15) . . . . ? N2 C9 C10 O4 51.1(2) . . . . ? C9 C10 O4 C11 70.5(2) . . . . ? C10 O4 C11 C12 -131.24(17) . . . . ? O4 C11 C12 O5 62.8(2) . . . . ? C11 C12 O5 C13 -177.78(16) . . . . ? C12 O5 C13 C14 175.27(16) . . . . ? O5 C13 C14 O6 -60.8(2) . . . . ? C13 C14 O6 C15 131.97(18) . . . . ? C14 O6 C15 C16 -71.3(2) . . . . ? O6 C15 C16 N2 -51.6(2) . . . . ? C15 C16 N2 C9 172.26(16) . . . . ? C16 N2 C9 C10 -172.94(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1W1 F10 0.85(4) 1.78(4) 2.6290(18) 175(3) 4_556 O1W H2W1 O3W 0.878(18) 1.716(19) 2.588(2) 171(3) . O2W H1W2 O4W 0.870(18) 1.710(18) 2.569(2) 169(3) . O2W H2W2 F3 0.86(3) 1.77(3) 2.6261(17) 172(3) 4_565 N1 H1N1 F4 0.83(3) 2.02(3) 2.829(2) 164(2) . N1 H1N1 F3 0.83(3) 2.46(2) 2.9816(19) 121.3(19) . N1 H2N1 O2 0.83(3) 2.09(3) 2.811(2) 146(2) . N1 H2N1 O1 0.83(3) 2.38(3) 2.785(2) 111(2) . N2 H1N2 O5 0.86(3) 2.04(3) 2.786(2) 145(2) . N2 H1N2 O6 0.86(3) 2.38(3) 2.799(2) 111(2) . N2 H2N2 F8 0.86(3) 1.94(3) 2.786(2) 169(2) . N2 H2N2 F7 0.86(3) 2.47(3) 3.079(2) 128(2) . O3W H1W3 F7 0.83(3) 1.97(3) 2.794(2) 172(3) 4_566 O3W H2W3 F9 0.79(3) 1.96(4) 2.733(2) 168(3) 2_655 O4W H1W4 F5 0.84(4) 1.90(4) 2.7437(19) 173(3) 4 O4W H2W4 F1 0.79(3) 1.98(3) 2.7543(19) 167(3) 2_545 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.594 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.071