# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jonathan Steed' _publ_contact_author_address ; Department of Chemistry University of Durham South Road Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email JON.STEED@DURHAM.AC.UK _publ_section_title ; Unusual variations in the incidence of Z'>1 in oxo-anion structures ; loop_ _publ_author_name 'Jonathan Steed' 'Kirsty Anderson' 'Andres E. Goeta' 'Kirsty S. B. Hancock' data_2c _database_code_depnum_ccdc_archive 'CCDC 299177' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C6 H10 N2), 2(H2 O4 P), H O4 P' _chemical_formula_sum 'C12 H25 N4 O12 P3' _chemical_formula_weight 510.27 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' P P 0.1023 0.0942 '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 10.9056(6) _cell_length_b 13.2510(4) _cell_length_c 15.7992(8) _cell_angle_alpha 113.296(3) _cell_angle_beta 99.154(3) _cell_angle_gamma 95.774(3) _cell_volume 2036.36(16) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.664 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.364 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8390 _exptl_absorpt_correction_T_max 0.9645 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16581 _diffrn_reflns_av_R_equivalents 0.0865 _diffrn_reflns_av_sigmaI/netI 0.1373 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.50 _reflns_number_total 9285 _reflns_number_gt 5912 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _refine_special_details ; N and C hydrogens in calculated positions. HPO4/H2PO4 hydrogens located in difference map and then fixed in position 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^)+(0.0470P)^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 'see above' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0029(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9285 _refine_ls_number_parameters 568 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1150 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_ref 0.1256 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.035 _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 P1 P 0.76953(8) 0.35006(6) 0.00241(6) 0.0114(2) Uani 1 1 d . . . P2 P 0.81525(8) 0.29930(6) 0.28622(6) 0.01078(19) Uani 1 1 d . . . P3 P 0.67488(8) 0.66312(6) 0.19987(6) 0.01016(19) Uani 1 1 d . . . P4 P 0.70634(8) 0.63314(6) 0.45013(6) 0.01038(19) Uani 1 1 d . . . P5 P 1.01544(8) 0.89741(6) 0.15880(6) 0.01092(19) Uani 1 1 d . . . P6 P 0.54665(8) 0.88978(6) 0.65615(6) 0.01100(19) Uani 1 1 d . . . O1 O 0.7433(2) 0.23040(17) -0.06913(16) 0.0164(5) Uani 1 1 d . . . O2 O 0.8154(2) 0.43645(17) -0.03101(15) 0.0142(5) Uani 1 1 d . . . O3 O 0.8756(2) 0.37100(17) 0.09111(15) 0.0161(5) Uani 1 1 d . . . O4 O 0.6429(2) 0.36925(16) 0.03454(16) 0.0159(5) Uani 1 1 d . . . O5 O 0.8627(2) 0.26803(17) 0.19626(15) 0.0150(5) Uani 1 1 d . . . O6 O 0.9210(2) 0.34641(17) 0.37484(15) 0.0137(5) Uani 1 1 d . . . O7 O 0.7224(2) 0.38332(17) 0.29342(16) 0.0173(5) Uani 1 1 d . . . O8 O 0.7341(2) 0.19176(16) 0.28012(15) 0.0149(5) Uani 1 1 d . . . O9 O 0.5931(2) 0.55014(16) 0.13320(15) 0.0135(5) Uani 1 1 d . . . O10 O 0.7023(2) 0.73345(16) 0.14564(15) 0.0140(5) Uani 1 1 d . . . O11 O 0.8094(2) 0.64235(17) 0.23981(15) 0.0136(5) Uani 1 1 d . . . O12 O 0.6152(2) 0.72294(16) 0.28254(15) 0.0137(5) Uani 1 1 d . . . O13 O 0.8060(2) 0.59506(16) 0.39247(15) 0.0127(5) Uani 1 1 d . . . O14 O 0.5740(2) 0.61107(16) 0.38077(15) 0.0128(5) Uani 1 1 d . . . O15 O 0.7398(2) 0.75919(16) 0.51205(15) 0.0131(5) Uani 1 1 d . . . O16 O 0.6835(2) 0.56506(17) 0.50596(15) 0.0141(5) Uani 1 1 d . . . O17 O 1.0067(2) 0.90459(17) 0.06579(15) 0.0147(5) Uani 1 1 d . . . O18 O 0.9708(2) 0.98879(17) 0.23119(15) 0.0175(5) Uani 1 1 d . . . O19 O 1.1573(2) 0.89244(17) 0.19857(15) 0.0146(5) Uani 1 1 d . . . O20 O 0.9427(2) 0.77910(16) 0.14386(16) 0.0144(5) Uani 1 1 d . . . O21 O 0.5700(2) 0.86602(17) 0.55555(15) 0.0130(5) Uani 1 1 d . . . O22 O 0.4933(2) 0.99560(17) 0.69374(15) 0.0139(5) Uani 1 1 d . . . O23 O 0.6809(2) 0.90409(17) 0.71970(15) 0.0153(5) Uani 1 1 d . . . O24 O 0.4674(2) 0.78886(17) 0.65511(15) 0.0141(5) Uani 1 1 d . . . N1 N 0.1354(2) -0.0605(2) -0.05937(18) 0.0128(6) Uani 1 1 d . . . H1A H 0.0771 -0.0244 -0.0776 0.019 Uiso 1 1 calc R . . H1B H 0.1151 -0.0756 -0.0114 0.019 Uiso 1 1 calc R . . H1C H 0.1362 -0.1256 -0.1091 0.019 Uiso 1 1 calc R . . N2 N 0.4807(3) 0.1412(2) -0.12557(17) 0.0127(6) Uani 1 1 d . . . H2A H 0.4860 0.0792 -0.1765 0.019 Uiso 1 1 calc R . . H2B H 0.5591 0.1832 -0.0968 0.019 Uiso 1 1 calc R . . H2C H 0.4297 0.1819 -0.1447 0.019 Uiso 1 1 calc R . . H23O H 0.7324 0.9785 0.7489 0.015 Uiso 1 1 d R . . H20O H 0.8569 0.7773 0.1515 0.015 Uiso 1 1 d R . . H8O H 0.6563 0.1882 0.3025 0.015 Uiso 1 1 d R . . H14O H 0.5780 0.6467 0.3352 0.015 Uiso 1 1 d R . . H11O H 0.7988 0.6226 0.2876 0.015 Uiso 1 1 d R . . H7O H 0.7589 0.4474 0.3223 0.015 Uiso 1 1 d R . . H21O H 0.6449 0.8039 0.5342 0.015 Uiso 1 1 d R . . H4O H 0.6399 0.4423 0.0671 0.015 Uiso 1 1 d R . . H3O H 0.8299 0.3093 0.1011 0.015 Uiso 1 1 d R . . H19O H 1.1916 0.8320 0.1618 0.015 Uiso 1 1 d R . . N3 N 0.8751(3) 0.4718(2) -0.44757(18) 0.0124(6) Uani 1 1 d . . . H3A H 0.9462 0.5241 -0.4154 0.019 Uiso 1 1 calc R . . H3B H 0.8113 0.5054 -0.4622 0.019 Uiso 1 1 calc R . . H3C H 0.8900 0.4202 -0.5016 0.019 Uiso 1 1 calc R . . N4 N 0.9616(2) 0.4144(2) -0.15662(18) 0.0126(6) Uani 1 1 d . . . H4A H 0.9143 0.4249 -0.1122 0.019 Uiso 1 1 calc R . . H4B H 1.0200 0.4772 -0.1389 0.019 Uiso 1 1 calc R . . H4C H 1.0014 0.3557 -0.1622 0.019 Uiso 1 1 calc R . . N5 N 0.6505(3) 0.5710(2) -0.05066(18) 0.0129(6) Uani 1 1 d . . . H5A H 0.5725 0.5274 -0.0768 0.019 Uiso 1 1 calc R . . H5B H 0.6481 0.6288 0.0044 0.019 Uiso 1 1 calc R . . H5C H 0.7070 0.5296 -0.0390 0.019 Uiso 1 1 calc R . . N6 N 0.5588(2) 0.6053(2) -0.35148(18) 0.0122(6) Uani 1 1 d . . . H6A H 0.5003 0.5432 -0.3671 0.018 Uiso 1 1 calc R . . H6B H 0.6029 0.5934 -0.3978 0.018 Uiso 1 1 calc R . . H6C H 0.5192 0.6644 -0.3450 0.018 Uiso 1 1 calc R . . N7 N 0.6439(2) 0.93216(19) 0.41779(18) 0.0112(6) Uani 1 1 d . . . H7A H 0.5916 0.9610 0.3860 0.017 Uiso 1 1 calc R . . H7B H 0.6078 0.9220 0.4626 0.017 Uiso 1 1 calc R . . H7C H 0.6574 0.8654 0.3766 0.017 Uiso 1 1 calc R . . N8 N 1.0089(2) 1.1607(2) 0.39508(18) 0.0116(6) Uani 1 1 d . . . H8A H 0.9756 1.2177 0.3876 0.017 Uiso 1 1 calc R . . H8B H 1.0019 1.1036 0.3375 0.017 Uiso 1 1 calc R . . H8C H 1.0917 1.1852 0.4248 0.017 Uiso 1 1 calc R . . C1 C 0.2601(3) 0.0101(2) -0.0273(2) 0.0116(7) Uani 1 1 d . . . C2 C 0.3116(3) 0.0386(2) -0.0910(2) 0.0116(7) Uani 1 1 d . . . H2 H 0.2680 0.0113 -0.1550 0.014 Uiso 1 1 calc R . . C3 C 0.4281(3) 0.1079(2) -0.0594(2) 0.0106(7) Uani 1 1 d . . . C4 C 0.4927(3) 0.1490(2) 0.0343(2) 0.0141(7) Uani 1 1 d . . . H4 H 0.5733 0.1958 0.0550 0.017 Uiso 1 1 calc R . . C5 C 0.4377(3) 0.1205(2) 0.0966(2) 0.0151(7) Uani 1 1 d . . . H5 H 0.4805 0.1493 0.1609 0.018 Uiso 1 1 calc R . . C6 C 0.3211(3) 0.0507(2) 0.0669(2) 0.0149(7) Uani 1 1 d . . . H6 H 0.2839 0.0311 0.1099 0.018 Uiso 1 1 calc R . . C7 C 0.8394(3) 0.4169(2) -0.3891(2) 0.0133(7) Uani 1 1 d . . . C8 C 0.9175(3) 0.4420(2) -0.3026(2) 0.0120(7) Uani 1 1 d . . . H8 H 0.9952 0.4930 -0.2817 0.014 Uiso 1 1 calc R . . C9 C 0.8796(3) 0.3911(2) -0.2472(2) 0.0115(7) Uani 1 1 d . . . C10 C 0.7662(3) 0.3181(3) -0.2760(2) 0.0156(7) Uani 1 1 d . . . H10 H 0.7412 0.2846 -0.2367 0.019 Uiso 1 1 calc R . . C11 C 0.6885(3) 0.2939(3) -0.3632(2) 0.0174(8) Uani 1 1 d . . . H11 H 0.6102 0.2439 -0.3835 0.021 Uiso 1 1 calc R . . C12 C 0.7253(3) 0.3426(3) -0.4203(2) 0.0159(7) Uani 1 1 d . . . H12 H 0.6732 0.3254 -0.4802 0.019 Uiso 1 1 calc R . . C13 C 0.6887(3) 0.6150(2) -0.1160(2) 0.0113(7) Uani 1 1 d . . . C14 C 0.6053(3) 0.5917(2) -0.2000(2) 0.0123(7) Uani 1 1 d . . . H14 H 0.5224 0.5508 -0.2141 0.015 Uiso 1 1 calc R . . C15 C 0.6451(3) 0.6291(2) -0.2628(2) 0.0104(7) Uani 1 1 d . . . C16 C 0.7646(3) 0.6915(2) -0.2425(2) 0.0143(7) Uani 1 1 d . . . H16 H 0.7905 0.7172 -0.2863 0.017 Uiso 1 1 calc R . . C17 C 0.8454(3) 0.7156(3) -0.1572(2) 0.0172(8) Uani 1 1 d . . . H17 H 0.9271 0.7590 -0.1423 0.021 Uiso 1 1 calc R . . C18 C 0.8087(3) 0.6773(2) -0.0929(2) 0.0150(7) Uani 1 1 d . . . H18 H 0.8646 0.6935 -0.0348 0.018 Uiso 1 1 calc R . . C19 C 0.7643(3) 1.0093(2) 0.4630(2) 0.0128(7) Uani 1 1 d . . . C20 C 0.8268(3) 1.0475(2) 0.4082(2) 0.0116(7) Uani 1 1 d . . . H20 H 0.7926 1.0233 0.3428 0.014 Uiso 1 1 calc R . . C21 C 0.9406(3) 1.1218(2) 0.4516(2) 0.0113(7) Uani 1 1 d . . . C22 C 0.9917(3) 1.1581(3) 0.5475(2) 0.0152(7) Uani 1 1 d . . . H22 H 1.0700 1.2085 0.5762 0.018 Uiso 1 1 calc R . . C23 C 0.9261(3) 1.1195(2) 0.6002(2) 0.0156(7) Uani 1 1 d . . . H23 H 0.9595 1.1446 0.6659 0.019 Uiso 1 1 calc R . . C24 C 0.8130(3) 1.0451(2) 0.5588(2) 0.0148(7) Uani 1 1 d . . . H24 H 0.7691 1.0187 0.5956 0.018 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 P1 0.0099(4) 0.0125(4) 0.0113(4) 0.0045(3) 0.0026(3) 0.0016(3) P2 0.0110(4) 0.0107(4) 0.0105(4) 0.0040(3) 0.0027(3) 0.0022(3) P3 0.0107(4) 0.0101(4) 0.0096(4) 0.0040(3) 0.0028(3) 0.0015(3) P4 0.0105(5) 0.0107(4) 0.0100(4) 0.0044(3) 0.0025(3) 0.0017(3) P5 0.0109(4) 0.0116(4) 0.0107(4) 0.0047(3) 0.0033(3) 0.0021(3) P6 0.0118(5) 0.0120(4) 0.0104(4) 0.0054(3) 0.0031(3) 0.0032(3) O1 0.0138(13) 0.0138(11) 0.0167(12) 0.0006(10) 0.0051(10) 0.0036(9) O2 0.0131(13) 0.0191(11) 0.0136(12) 0.0097(10) 0.0037(10) 0.0036(9) O3 0.0133(13) 0.0169(11) 0.0177(12) 0.0096(10) -0.0009(10) -0.0032(9) O4 0.0136(13) 0.0109(11) 0.0201(13) 0.0015(10) 0.0081(10) 0.0028(9) O5 0.0192(13) 0.0154(11) 0.0130(12) 0.0067(10) 0.0070(10) 0.0052(9) O6 0.0152(13) 0.0152(11) 0.0101(11) 0.0057(9) 0.0010(10) 0.0016(9) O7 0.0157(13) 0.0108(11) 0.0219(13) 0.0046(10) 0.0001(10) 0.0034(9) O8 0.0147(13) 0.0126(11) 0.0207(13) 0.0086(10) 0.0091(10) 0.0012(9) O9 0.0114(12) 0.0123(10) 0.0159(12) 0.0041(9) 0.0049(10) 0.0026(9) O10 0.0133(13) 0.0152(11) 0.0169(12) 0.0097(10) 0.0052(10) 0.0011(9) O11 0.0124(13) 0.0189(11) 0.0141(12) 0.0106(10) 0.0041(10) 0.0047(9) O12 0.0192(13) 0.0129(11) 0.0107(11) 0.0055(9) 0.0060(10) 0.0039(9) O13 0.0144(13) 0.0118(10) 0.0132(12) 0.0054(9) 0.0052(10) 0.0043(9) O14 0.0108(12) 0.0149(11) 0.0133(12) 0.0079(9) 0.0007(10) -0.0001(9) O15 0.0098(12) 0.0109(10) 0.0166(12) 0.0032(9) 0.0037(10) 0.0030(9) O16 0.0177(13) 0.0164(11) 0.0140(12) 0.0099(9) 0.0082(10) 0.0054(9) O17 0.0148(13) 0.0178(11) 0.0144(12) 0.0089(10) 0.0050(10) 0.0042(9) O18 0.0144(13) 0.0180(11) 0.0147(12) 0.0015(10) 0.0020(10) 0.0028(9) O19 0.0108(12) 0.0154(11) 0.0152(12) 0.0037(10) 0.0026(10) 0.0036(9) O20 0.0095(12) 0.0148(11) 0.0232(13) 0.0108(10) 0.0076(10) 0.0026(9) O21 0.0132(13) 0.0149(11) 0.0123(11) 0.0060(9) 0.0052(10) 0.0033(9) O22 0.0174(13) 0.0121(10) 0.0123(12) 0.0039(9) 0.0055(10) 0.0050(9) O23 0.0127(13) 0.0162(11) 0.0145(12) 0.0058(9) -0.0012(10) 0.0015(9) O24 0.0116(12) 0.0151(11) 0.0181(12) 0.0083(10) 0.0066(10) 0.0030(9) N1 0.0137(15) 0.0152(13) 0.0123(14) 0.0078(11) 0.0055(12) 0.0026(11) N2 0.0111(15) 0.0135(13) 0.0121(14) 0.0041(11) 0.0020(12) 0.0016(11) N3 0.0122(15) 0.0152(13) 0.0102(14) 0.0054(11) 0.0025(12) 0.0033(11) N4 0.0113(15) 0.0153(13) 0.0123(14) 0.0064(11) 0.0042(12) 0.0024(11) N5 0.0132(15) 0.0147(13) 0.0122(14) 0.0073(11) 0.0018(12) 0.0039(11) N6 0.0125(15) 0.0126(13) 0.0121(14) 0.0056(11) 0.0034(12) 0.0024(11) N7 0.0115(15) 0.0123(13) 0.0092(13) 0.0046(11) 0.0006(11) 0.0020(10) N8 0.0109(15) 0.0111(12) 0.0128(14) 0.0048(11) 0.0028(11) 0.0018(10) C1 0.0120(18) 0.0100(15) 0.0131(17) 0.0043(13) 0.0039(14) 0.0040(12) C2 0.0150(18) 0.0126(15) 0.0074(15) 0.0034(13) 0.0030(13) 0.0060(13) C3 0.0110(17) 0.0122(15) 0.0112(16) 0.0056(13) 0.0048(13) 0.0062(12) C4 0.0114(18) 0.0131(15) 0.0168(17) 0.0059(14) 0.0021(14) 0.0018(13) C5 0.0191(19) 0.0166(16) 0.0093(16) 0.0057(14) 0.0016(14) 0.0042(14) C6 0.022(2) 0.0144(16) 0.0124(17) 0.0080(14) 0.0062(15) 0.0062(14) C7 0.0173(19) 0.0112(15) 0.0115(16) 0.0032(13) 0.0059(14) 0.0054(13) C8 0.0109(17) 0.0111(15) 0.0137(17) 0.0042(13) 0.0037(14) 0.0030(12) C9 0.0097(17) 0.0118(15) 0.0113(16) 0.0031(13) 0.0008(13) 0.0048(12) C10 0.0157(19) 0.0183(16) 0.0177(18) 0.0114(14) 0.0057(15) 0.0052(14) C11 0.0157(19) 0.0136(16) 0.0185(18) 0.0045(14) 0.0007(15) -0.0021(13) C12 0.0137(18) 0.0166(16) 0.0137(17) 0.0038(14) 0.0001(14) 0.0020(13) C13 0.0116(18) 0.0105(15) 0.0108(16) 0.0026(13) 0.0034(14) 0.0040(12) C14 0.0099(17) 0.0115(15) 0.0131(16) 0.0034(13) 0.0023(14) -0.0008(12) C15 0.0098(17) 0.0103(14) 0.0102(16) 0.0034(13) 0.0004(13) 0.0043(12) C16 0.0175(19) 0.0127(15) 0.0148(17) 0.0069(13) 0.0052(15) 0.0039(13) C17 0.0119(18) 0.0171(16) 0.0195(18) 0.0068(14) 0.0009(15) -0.0024(13) C18 0.0139(18) 0.0164(16) 0.0121(17) 0.0045(14) 0.0009(14) 0.0003(13) C19 0.0136(18) 0.0098(15) 0.0160(17) 0.0050(13) 0.0057(14) 0.0040(12) C20 0.0090(17) 0.0147(15) 0.0116(16) 0.0065(13) 0.0011(13) 0.0021(12) C21 0.0112(17) 0.0119(15) 0.0146(17) 0.0070(13) 0.0068(14) 0.0051(12) C22 0.0175(19) 0.0133(15) 0.0124(17) 0.0033(13) 0.0024(14) 0.0023(13) C23 0.0203(19) 0.0144(16) 0.0109(17) 0.0049(14) 0.0022(14) 0.0014(14) C24 0.0176(19) 0.0151(16) 0.0140(17) 0.0066(14) 0.0064(14) 0.0062(13) _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 P1 O1 1.504(2) . ? P1 O2 1.512(2) . ? P1 O4 1.556(2) . ? P1 O3 1.578(2) . ? P2 O5 1.507(2) . ? P2 O6 1.526(2) . ? P2 O8 1.560(2) . ? P2 O7 1.562(2) . ? P3 O12 1.521(2) . ? P3 O9 1.527(2) . ? P3 O10 1.533(2) . ? P3 O11 1.597(2) . ? P4 O16 1.519(2) . ? P4 O13 1.526(2) . ? P4 O15 1.533(2) . ? P4 O14 1.590(2) . ? P5 O18 1.487(2) . ? P5 O17 1.499(2) . ? P5 O19 1.592(2) . ? P5 O20 1.594(2) . ? P6 O22 1.507(2) . ? P6 O24 1.510(2) . ? P6 O21 1.562(2) . ? P6 O23 1.586(2) . ? N1 C1 1.460(4) . ? N2 C3 1.457(4) . ? N3 C7 1.458(4) . ? N4 C9 1.459(4) . ? N5 C13 1.464(4) . ? N6 C15 1.456(4) . ? N7 C19 1.460(4) . ? N8 C21 1.454(4) . ? C1 C2 1.381(4) . ? C1 C6 1.388(4) . ? C2 C3 1.380(4) . ? C3 C4 1.391(4) . ? C4 C5 1.381(4) . ? C5 C6 1.386(5) . ? C7 C8 1.384(5) . ? C7 C12 1.391(4) . ? C8 C9 1.385(4) . ? C9 C10 1.380(4) . ? C10 C11 1.394(5) . ? C11 C12 1.384(5) . ? C13 C14 1.386(5) . ? C13 C18 1.386(4) . ? C14 C15 1.379(4) . ? C15 C16 1.387(4) . ? C16 C17 1.386(5) . ? C17 C18 1.395(5) . ? C19 C24 1.388(5) . ? C19 C20 1.390(4) . ? C20 C21 1.388(4) . ? C21 C22 1.392(5) . ? C22 C23 1.385(5) . ? C23 C24 1.383(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 O1 P1 O2 116.15(13) . . ? O1 P1 O4 104.56(12) . . ? O2 P1 O4 111.30(13) . . ? O1 P1 O3 111.96(13) . . ? O2 P1 O3 104.10(12) . . ? O4 P1 O3 108.74(13) . . ? O5 P2 O6 113.32(13) . . ? O5 P2 O8 107.38(12) . . ? O6 P2 O8 109.55(13) . . ? O5 P2 O7 110.93(14) . . ? O6 P2 O7 110.08(12) . . ? O8 P2 O7 105.22(13) . . ? O12 P3 O9 110.92(12) . . ? O12 P3 O10 112.76(12) . . ? O9 P3 O10 110.54(13) . . ? O12 P3 O11 108.73(13) . . ? O9 P3 O11 108.41(12) . . ? O10 P3 O11 105.23(12) . . ? O16 P4 O13 112.07(12) . . ? O16 P4 O15 112.89(12) . . ? O13 P4 O15 110.53(12) . . ? O16 P4 O14 104.66(13) . . ? O13 P4 O14 109.45(12) . . ? O15 P4 O14 106.91(12) . . ? O18 P5 O17 114.91(14) . . ? O18 P5 O19 110.00(13) . . ? O17 P5 O19 109.15(13) . . ? O18 P5 O20 110.06(12) . . ? O17 P5 O20 110.22(13) . . ? O19 P5 O20 101.67(12) . . ? O22 P6 O24 114.24(13) . . ? O22 P6 O21 109.96(13) . . ? O24 P6 O21 110.52(12) . . ? O22 P6 O23 110.36(12) . . ? O24 P6 O23 105.72(13) . . ? O21 P6 O23 105.62(12) . . ? C2 C1 C6 121.8(3) . . ? C2 C1 N1 118.9(3) . . ? C6 C1 N1 119.3(3) . . ? C3 C2 C1 118.4(3) . . ? C2 C3 C4 121.4(3) . . ? C2 C3 N2 118.5(3) . . ? C4 C3 N2 120.1(3) . . ? C5 C4 C3 118.9(3) . . ? C4 C5 C6 121.1(3) . . ? C5 C6 C1 118.5(3) . . ? C8 C7 C12 121.4(3) . . ? C8 C7 N3 119.6(3) . . ? C12 C7 N3 119.1(3) . . ? C9 C8 C7 118.4(3) . . ? C10 C9 C8 121.4(3) . . ? C10 C9 N4 119.2(3) . . ? C8 C9 N4 119.4(3) . . ? C9 C10 C11 119.4(3) . . ? C12 C11 C10 120.2(3) . . ? C11 C12 C7 119.2(3) . . ? C14 C13 C18 121.6(3) . . ? C14 C13 N5 119.4(3) . . ? C18 C13 N5 119.0(3) . . ? C15 C14 C13 118.6(3) . . ? C14 C15 C16 121.6(3) . . ? C14 C15 N6 119.3(3) . . ? C16 C15 N6 119.0(3) . . ? C17 C16 C15 118.7(3) . . ? C16 C17 C18 121.1(3) . . ? C13 C18 C17 118.4(3) . . ? C24 C19 C20 121.2(3) . . ? C24 C19 N7 120.3(3) . . ? C20 C19 N7 118.5(3) . . ? C21 C20 C19 118.4(3) . . ? C20 C21 C22 121.4(3) . . ? C20 C21 N8 119.2(3) . . ? C22 C21 N8 119.4(3) . . ? C23 C22 C21 118.7(3) . . ? C22 C23 C24 121.1(3) . . ? C23 C24 C19 119.2(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 C6 C1 C2 C3 1.2(5) . . . . ? N1 C1 C2 C3 178.3(3) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C1 C2 C3 N2 -177.9(3) . . . . ? C2 C3 C4 C5 -0.8(5) . . . . ? N2 C3 C4 C5 176.7(3) . . . . ? C3 C4 C5 C6 1.1(5) . . . . ? C4 C5 C6 C1 -0.3(5) . . . . ? C2 C1 C6 C5 -0.8(5) . . . . ? N1 C1 C6 C5 -178.0(3) . . . . ? C12 C7 C8 C9 0.1(5) . . . . ? N3 C7 C8 C9 178.2(3) . . . . ? C7 C8 C9 C10 -0.9(5) . . . . ? C7 C8 C9 N4 178.7(3) . . . . ? C8 C9 C10 C11 0.8(5) . . . . ? N4 C9 C10 C11 -178.9(3) . . . . ? C9 C10 C11 C12 0.2(5) . . . . ? C10 C11 C12 C7 -1.0(5) . . . . ? C8 C7 C12 C11 0.8(5) . . . . ? N3 C7 C12 C11 -177.2(3) . . . . ? C18 C13 C14 C15 1.9(5) . . . . ? N5 C13 C14 C15 -176.8(3) . . . . ? C13 C14 C15 C16 -1.7(5) . . . . ? C13 C14 C15 N6 179.9(3) . . . . ? C14 C15 C16 C17 0.4(5) . . . . ? N6 C15 C16 C17 178.8(3) . . . . ? C15 C16 C17 C18 0.7(5) . . . . ? C14 C13 C18 C17 -0.8(5) . . . . ? N5 C13 C18 C17 177.9(3) . . . . ? C16 C17 C18 C13 -0.5(5) . . . . ? C24 C19 C20 C21 0.6(5) . . . . ? N7 C19 C20 C21 179.3(3) . . . . ? C19 C20 C21 C22 -0.2(5) . . . . ? C19 C20 C21 N8 178.6(3) . . . . ? C20 C21 C22 C23 -0.6(5) . . . . ? N8 C21 C22 C23 -179.4(3) . . . . ? C21 C22 C23 C24 0.9(5) . . . . ? C22 C23 C24 C19 -0.5(5) . . . . ? C20 C19 C24 C23 -0.3(5) . . . . ? N7 C19 C24 C23 -179.0(3) . . . . ? 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 O17 0.91 1.87 2.728(4) 155.9 2_665 N1 H1A O18 0.91 2.63 3.298(4) 130.5 2_665 N1 H1B O17 0.91 1.90 2.751(3) 155.3 1_445 N1 H1C O5 0.91 1.85 2.749(3) 170.7 2_655 N3 H3A O6 0.91 1.95 2.826(3) 162.3 2_765 N3 H3B O16 0.91 1.77 2.679(4) 177.5 1_554 N3 H3C O6 0.91 1.91 2.795(3) 163.7 1_554 N5 H5A O9 0.91 1.87 2.779(3) 174.1 2_665 N5 H5B O10 0.91 2.05 2.913(3) 157.0 . N5 H5C O2 0.91 1.82 2.724(4) 173.1 . N6 H6A O16 0.91 2.53 3.229(3) 133.5 2_665 N6 H6B O16 0.91 1.81 2.716(3) 177.1 1_554 N6 H6C O24 0.91 1.80 2.691(3) 167.1 1_554 N4 H4A O2 0.91 1.78 2.684(3) 176.0 . N4 H4B O3 0.91 1.99 2.895(3) 169.9 2_765 N4 H4C O20 0.91 2.05 2.931(3) 161.3 2_765 N4 H4C O11 0.91 2.56 3.028(3) 112.2 2_765 N8 H8A O6 0.91 1.93 2.842(3) 174.6 1_565 N8 H8B O18 0.91 1.72 2.621(3) 172.5 . N8 H8C O15 0.91 1.86 2.774(3) 177.8 2_776 N7 H7A O22 0.91 1.76 2.654(4) 168.4 2_676 N7 H7B O21 0.91 1.97 2.842(3) 160.9 . N7 H7C O12 0.91 1.84 2.698(3) 156.9 . N2 H2A O22 0.91 1.93 2.777(3) 155.1 1_544 N2 H2B O1 0.91 1.97 2.841(3) 160.2 . N2 H2B O4 0.91 2.47 3.181(3) 134.8 . N2 H2C O10 0.91 1.91 2.779(4) 158.2 2_665 O23 H23O O19 0.97 1.79 2.759(3) 173.4 2_776 O20 H20O O10 0.96 1.70 2.637(3) 163.1 . O8 H8O O24 0.97 1.60 2.561(3) 167.4 2_666 O14 H14O O12 1.01 1.60 2.591(3) 165.6 . O11 H11O O13 0.91 1.82 2.726(3) 170.0 . O7 H7O O13 0.81 1.79 2.591(3) 167.1 . O21 H21O O15 1.21 1.27 2.463(3) 166.1 . O4 H4O O9 0.91 1.59 2.459(3) 159.4 . O3 H3O O5 0.99 1.79 2.544(3) 129.8 . O19 H19O O1 0.94 1.68 2.537(3) 150.0 2_765 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.437 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.102 data_1h _database_code_depnum_ccdc_archive 'CCDC 299178' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C6 H10 N2)4, (SO4)3, (HSO4)2, (H2O)4' _chemical_formula_sum 'C24 H25 N8 O24 S5' _chemical_formula_weight 969.82 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' S S 0.1246 0.1234 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.5897(15) _cell_length_b 27.591(6) _cell_length_c 19.190(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.58(3) _cell_angle_gamma 90.00 _cell_volume 4016.9(14) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1988 _exptl_absorpt_coefficient_mu 0.387 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8300 _exptl_absorpt_correction_T_max 0.9623 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23828 _diffrn_reflns_av_R_equivalents 0.0867 _diffrn_reflns_av_sigmaI/netI 0.1700 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.06 _diffrn_reflns_theta_max 26.00 _reflns_number_total 14446 _reflns_number_gt 8507 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; unable to locate hydrogen atoms on SO4, HSO4 and H2O groups so formula deduced on a charge balance basis 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^)+(0.0310P)^2^+0.4105P] 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 calc _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00114(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.29(8) _refine_ls_number_reflns 14446 _refine_ls_number_parameters 1101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1435 _refine_ls_R_factor_gt 0.0729 _refine_ls_wR_factor_ref 0.1630 _refine_ls_wR_factor_gt 0.1363 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.002 _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 S1 S 0.7943(2) 0.28455(8) 0.66998(10) 0.0234(5) Uani 1 1 d . . . S2 S 0.7772(2) 0.28294(8) 0.16042(10) 0.0252(5) Uani 1 1 d . . . S3 S 0.8948(2) 0.11496(7) 0.69063(9) 0.0171(4) Uani 1 1 d . . . S4 S 0.4318(2) 0.11204(7) 0.52464(9) 0.0163(4) Uani 1 1 d . . . S5 S 0.9150(2) 0.11351(7) 0.19358(9) 0.0157(4) Uani 1 1 d . . . S6 S 0.4012(2) 0.11448(7) 0.02349(8) 0.0153(4) Uani 1 1 d . . . S7 S 0.7889(2) 0.01636(7) 0.94101(9) 0.0163(4) Uani 1 1 d . . . S8 S 0.3233(2) 0.01359(7) 0.77481(9) 0.0170(5) Uani 1 1 d . . . S9 S 0.8164(2) 0.01449(7) 0.44197(9) 0.0153(4) Uani 1 1 d . . . S10 S 0.3234(2) 0.01866(7) 0.27296(9) 0.0166(5) Uani 1 1 d . . . O1 O 0.7627(7) 0.3212(2) 0.7211(3) 0.0411(16) Uani 1 1 d . . . O2 O 0.6910(6) 0.2908(2) 0.6064(2) 0.0270(13) Uani 1 1 d . . . O3 O 0.9810(6) 0.2787(2) 0.6562(3) 0.0390(15) Uani 1 1 d . . . O4 O 0.7363(6) 0.2363(2) 0.7052(2) 0.0279(13) Uani 1 1 d . . . O5 O 0.7374(6) 0.3083(2) 0.2236(2) 0.0368(15) Uani 1 1 d . . . O6 O 0.8474(7) 0.3164(3) 0.1089(3) 0.061(2) Uani 1 1 d . . . O7 O 0.6304(6) 0.2558(3) 0.1292(3) 0.0517(19) Uani 1 1 d . . . O8 O 0.9305(6) 0.2459(2) 0.1755(3) 0.0401(16) Uani 1 1 d . . . O9 O 0.8361(7) 0.15716(19) 0.6478(2) 0.0279(14) Uani 1 1 d . . . O10 O 0.9312(6) 0.07439(19) 0.6427(2) 0.0196(12) Uani 1 1 d . . . O11 O 0.7532(5) 0.1020(2) 0.7382(2) 0.0231(13) Uani 1 1 d . . . O12 O 1.0536(5) 0.12680(19) 0.7312(2) 0.0220(12) Uani 1 1 d . . . O13 O 0.3387(6) 0.15328(19) 0.5581(2) 0.0222(12) Uani 1 1 d . . . O14 O 0.5913(5) 0.12854(19) 0.4912(2) 0.0200(12) Uani 1 1 d . . . O15 O 0.3056(6) 0.08983(19) 0.4732(2) 0.0215(13) Uani 1 1 d . . . O16 O 0.4727(6) 0.07578(19) 0.5790(2) 0.0184(12) Uani 1 1 d . . . O17 O 0.8147(6) 0.15482(18) 0.1605(2) 0.0220(12) Uani 1 1 d . . . O18 O 0.9449(6) 0.07688(18) 0.1392(2) 0.0188(12) Uani 1 1 d . . . O19 O 0.8026(6) 0.09207(19) 0.2475(2) 0.0201(12) Uani 1 1 d . . . O20 O 1.0813(5) 0.13100(18) 0.2242(2) 0.0191(12) Uani 1 1 d . . . O21 O 0.2966(5) 0.15330(18) 0.0565(2) 0.0207(12) Uani 1 1 d . . . O22 O 0.5583(5) 0.13555(19) -0.0070(2) 0.0203(12) Uani 1 1 d . . . O23 O 0.2889(5) 0.09077(17) -0.0304(2) 0.0166(12) Uani 1 1 d . . . O24 O 0.4487(6) 0.07894(18) 0.0776(2) 0.0198(12) Uani 1 1 d . . . O25 O 0.9175(5) 0.03565(17) 0.9942(2) 0.0171(12) Uani 1 1 d . . . O26 O 0.7552(6) 0.05383(18) 0.8877(2) 0.0205(12) Uani 1 1 d . . . O27 O 0.8731(6) -0.02605(19) 0.9060(2) 0.0195(12) Uani 1 1 d . . . O28 O 0.6281(5) 0.00104(19) 0.9746(2) 0.0207(12) Uani 1 1 d . . . O29 O 0.2915(6) 0.05437(19) 0.8215(2) 0.0220(12) Uani 1 1 d . . . O30 O 0.4720(5) 0.0243(2) 0.7292(2) 0.0239(13) Uani 1 1 d . . . O31 O 0.1639(6) 0.00486(19) 0.7309(2) 0.0231(13) Uani 1 1 d . . . O32 O 0.3650(7) -0.0298(2) 0.8172(2) 0.0309(14) Uani 1 1 d . . . O33 O 0.9362(5) 0.03558(18) 0.4965(2) 0.0194(12) Uani 1 1 d . . . O34 O 0.7773(6) 0.05147(18) 0.3893(2) 0.0183(12) Uani 1 1 d . . . O35 O 0.9159(6) -0.02602(19) 0.4078(2) 0.0200(12) Uani 1 1 d . . . O36 O 0.6582(5) -0.00389(18) 0.4727(2) 0.0186(12) Uani 1 1 d . . . O37 O 0.2859(6) 0.05511(18) 0.3267(2) 0.0181(12) Uani 1 1 d . . . O38 O 0.4355(6) 0.04158(19) 0.2191(2) 0.0207(12) Uani 1 1 d . . . O39 O 0.1611(5) -0.00027(18) 0.2412(2) 0.0214(12) Uani 1 1 d . . . O40 O 0.4284(6) -0.02078(18) 0.3076(2) 0.0194(12) Uani 1 1 d . . . N1 N 0.7247(7) 0.4886(2) 0.5565(3) 0.0174(14) Uani 1 1 d . . . H1C H 0.6972 0.5183 0.5389 0.021 Uiso 1 1 calc R . . H1B H 0.8400 0.4881 0.5708 0.021 Uiso 1 1 calc R . . H1A H 0.6555 0.4821 0.5933 0.021 Uiso 1 1 calc R . . N2 N 0.7912(7) 0.5089(2) 0.4102(3) 0.0184(14) Uani 1 1 d . . . H2C H 0.8840 0.5179 0.4384 0.022 Uiso 1 1 calc R . . H2B H 0.7036 0.5313 0.4133 0.022 Uiso 1 1 calc R . . H2A H 0.8266 0.5071 0.3654 0.022 Uiso 1 1 calc R . . N3 N 0.5272(7) 0.1268(2) 0.8468(3) 0.0208(15) Uani 1 1 d . . . H3C H 0.6349 0.1217 0.8285 0.025 Uiso 1 1 calc R . . H3B H 0.4545 0.1016 0.8356 0.025 Uiso 1 1 calc R . . H3A H 0.5387 0.1292 0.8940 0.025 Uiso 1 1 calc R . . N4 N 0.4036(7) 0.1351(2) 0.7042(3) 0.0174(14) Uani 1 1 d . . . H4C H 0.3080 0.1159 0.7107 0.021 Uiso 1 1 calc R . . H4B H 0.5037 0.1178 0.7135 0.021 Uiso 1 1 calc R . . H4A H 0.4031 0.1456 0.6593 0.021 Uiso 1 1 calc R . . N5 N -0.0326(7) 0.1367(2) 0.5189(3) 0.0170(14) Uani 1 1 d . . . H5A H -0.0545 0.1071 0.5000 0.020 Uiso 1 1 calc R . . H5B H -0.1071 0.1420 0.5545 0.020 Uiso 1 1 calc R . . H5C H 0.0808 0.1379 0.5356 0.020 Uiso 1 1 calc R . . N6 N 0.0427(6) 0.1193(2) 0.3733(3) 0.0185(15) Uani 1 1 d . . . H6A H 0.1429 0.1121 0.3983 0.022 Uiso 1 1 calc R . . H6B H 0.0668 0.1208 0.3272 0.022 Uiso 1 1 calc R . . H6C H -0.0396 0.0959 0.3803 0.022 Uiso 1 1 calc R . . N7 N 0.5442(6) 0.1235(2) 0.3428(3) 0.0127(13) Uani 1 1 d . . . H7A H 0.4565 0.1011 0.3448 0.015 Uiso 1 1 calc R . . H7B H 0.5964 0.1270 0.3858 0.015 Uiso 1 1 calc R . . H7C H 0.6257 0.1136 0.3120 0.015 Uiso 1 1 calc R . . N8 N 0.4524(7) 0.1430(2) 0.1975(3) 0.0177(14) Uani 1 1 d . . . H8A H 0.3579 0.1422 0.1673 0.021 Uiso 1 1 calc R . . H8B H 0.4672 0.1133 0.2175 0.021 Uiso 1 1 calc R . . H8C H 0.5508 0.1510 0.1740 0.021 Uiso 1 1 calc R . . N9 N 0.9403(7) 0.1366(2) 0.0195(3) 0.0149(14) Uani 1 1 d . . . H9C H 1.0567 0.1338 0.0316 0.018 Uiso 1 1 calc R . . H9B H 0.9001 0.1078 0.0022 0.018 Uiso 1 1 calc R . . H9A H 0.8785 0.1447 0.0578 0.018 Uiso 1 1 calc R . . N10 N 1.0219(7) 0.1186(2) -0.1248(3) 0.0182(14) Uani 1 1 d . . . H10C H 0.9282 0.0984 -0.1316 0.022 Uiso 1 1 calc R . . H10B H 1.0955 0.1061 -0.0911 0.022 Uiso 1 1 calc R . . H10A H 1.0809 0.1216 -0.1652 0.022 Uiso 1 1 calc R . . N11 N 0.8188(7) -0.0061(2) 0.7611(3) 0.0214(15) Uani 1 1 d . . . H11A H 0.8125 -0.0171 0.8057 0.026 Uiso 1 1 calc R . . H11B H 0.7204 0.0114 0.7500 0.026 Uiso 1 1 calc R . . H11C H 0.9157 0.0130 0.7572 0.026 Uiso 1 1 calc R . . N12 N 0.6961(7) 0.0025(2) 0.6192(3) 0.0169(14) Uani 1 1 d . . . H12C H 0.5903 0.0066 0.6396 0.020 Uiso 1 1 calc R . . H12B H 0.6796 0.0014 0.5721 0.020 Uiso 1 1 calc R . . H12A H 0.7684 0.0277 0.6307 0.020 Uiso 1 1 calc R . . N13 N 0.7872(7) -0.0088(2) 0.2675(3) 0.0138(13) Uani 1 1 d . . . H13C H 0.8429 -0.0180 0.3080 0.017 Uiso 1 1 calc R . . H13B H 0.6693 -0.0064 0.2743 0.017 Uiso 1 1 calc R . . H13A H 0.8296 0.0204 0.2538 0.017 Uiso 1 1 calc R . . N14 N 0.6871(7) 0.0097(2) 0.1223(3) 0.0210(15) Uani 1 1 d . . . H14C H 0.6441 0.0078 0.0777 0.025 Uiso 1 1 calc R . . H14B H 0.7712 0.0332 0.1253 0.025 Uiso 1 1 calc R . . H14A H 0.5980 0.0171 0.1512 0.025 Uiso 1 1 calc R . . N15 N 0.1935(7) 0.0094(2) 0.0937(3) 0.0170(14) Uani 1 1 d . . . H15A H 0.2749 0.0325 0.0844 0.020 Uiso 1 1 calc R . . H15B H 0.1730 0.0091 0.1402 0.020 Uiso 1 1 calc R . . H15C H 0.0914 0.0159 0.0696 0.020 Uiso 1 1 calc R . . N16 N 0.2506(6) -0.0107(2) -0.0515(3) 0.0151(14) Uani 1 1 d . . . H16C H 0.3259 0.0146 -0.0451 0.018 Uiso 1 1 calc R . . H16B H 0.1375 -0.0001 -0.0486 0.018 Uiso 1 1 calc R . . H16A H 0.2665 -0.0241 -0.0942 0.018 Uiso 1 1 calc R . . C1 C 0.6943(8) 0.4514(3) 0.5018(3) 0.0147(17) Uani 1 1 d . . . C2 C 0.7259(9) 0.4614(3) 0.4322(4) 0.0181(17) Uani 1 1 d . . . C3 C 0.6964(9) 0.4256(3) 0.3833(4) 0.0220(19) Uani 1 1 d . . . H3 H 0.7151 0.4323 0.3355 0.026 Uiso 1 1 calc R . . C4 C 0.6404(9) 0.3803(3) 0.4026(4) 0.0241(19) Uani 1 1 d . . . H4 H 0.6221 0.3559 0.3682 0.029 Uiso 1 1 calc R . . C5 C 0.6106(9) 0.3701(3) 0.4718(4) 0.0218(19) Uani 1 1 d . . . H5 H 0.5703 0.3390 0.4852 0.026 Uiso 1 1 calc R . . C6 C 0.6410(8) 0.4065(3) 0.5219(4) 0.0165(17) Uani 1 1 d . . . H6 H 0.6243 0.3999 0.5698 0.020 Uiso 1 1 calc R . . C7 C 0.4521(8) 0.1720(3) 0.8184(4) 0.0204(18) Uani 1 1 d . . . C8 C 0.3971(8) 0.1769(3) 0.7513(4) 0.0164(17) Uani 1 1 d . . . C9 C 0.3290(9) 0.2204(3) 0.7262(4) 0.0200(18) Uani 1 1 d . . . H9 H 0.2893 0.2230 0.6790 0.024 Uiso 1 1 calc R . . C10 C 0.3191(9) 0.2599(3) 0.7704(4) 0.027(2) Uani 1 1 d . . . H10 H 0.2742 0.2899 0.7534 0.032 Uiso 1 1 calc R . . C11 C 0.3753(9) 0.2555(3) 0.8401(4) 0.0262(19) Uani 1 1 d . . . H11 H 0.3670 0.2824 0.8708 0.031 Uiso 1 1 calc R . . C12 C 0.4435(9) 0.2115(3) 0.8643(4) 0.0237(19) Uani 1 1 d . . . H12 H 0.4837 0.2083 0.9114 0.028 Uiso 1 1 calc R . . C13 C -0.0597(8) 0.1742(3) 0.4655(4) 0.0156(17) Uani 1 1 d . . . C14 C -0.0244(8) 0.1656(3) 0.3959(4) 0.0170(18) Uani 1 1 d . . . C15 C -0.0567(9) 0.2031(3) 0.3469(4) 0.025(2) Uani 1 1 d . . . H15 H -0.0345 0.1977 0.2991 0.030 Uiso 1 1 calc R . . C16 C -0.1198(9) 0.2472(3) 0.3680(4) 0.0172(17) Uani 1 1 d . . . H16 H -0.1431 0.2720 0.3346 0.021 Uiso 1 1 calc R . . C17 C -0.1500(9) 0.2557(3) 0.4388(4) 0.0219(18) Uani 1 1 d . . . H17 H -0.1905 0.2866 0.4535 0.026 Uiso 1 1 calc R . . C18 C -0.1210(8) 0.2194(3) 0.4870(4) 0.0220(19) Uani 1 1 d . . . H18 H -0.1427 0.2251 0.5349 0.026 Uiso 1 1 calc R . . C19 C 0.4707(8) 0.1697(3) 0.3203(4) 0.0190(18) Uani 1 1 d . . . C20 C 0.4222(8) 0.1793(3) 0.2522(4) 0.0195(18) Uani 1 1 d . . . C21 C 0.3474(9) 0.2228(3) 0.2349(4) 0.0238(19) Uani 1 1 d . . . H21 H 0.3073 0.2282 0.1882 0.029 Uiso 1 1 calc R . . C22 C 0.3285(9) 0.2591(3) 0.2836(4) 0.027(2) Uani 1 1 d . . . H22 H 0.2840 0.2900 0.2699 0.033 Uiso 1 1 calc R . . C23 C 0.3756(9) 0.2500(3) 0.3532(4) 0.0228(18) Uani 1 1 d . . . H23 H 0.3581 0.2741 0.3877 0.027 Uiso 1 1 calc R . . C24 C 0.4482(8) 0.2055(3) 0.3717(4) 0.0198(18) Uani 1 1 d . . . H24 H 0.4825 0.1992 0.4188 0.024 Uiso 1 1 calc R . . C25 C 0.9170(8) 0.1747(3) -0.0342(4) 0.0149(17) Uani 1 1 d . . . C26 C 0.9604(9) 0.1657(3) -0.1031(4) 0.0170(18) Uani 1 1 d . . . C27 C 0.9422(8) 0.2033(3) -0.1511(4) 0.0175(18) Uani 1 1 d . . . H27 H 0.9694 0.1979 -0.1985 0.021 Uiso 1 1 calc R . . C28 C 0.8852(9) 0.2480(3) -0.1304(4) 0.0206(18) Uani 1 1 d . . . H28 H 0.8719 0.2734 -0.1635 0.025 Uiso 1 1 calc R . . C29 C 0.8473(9) 0.2560(3) -0.0621(4) 0.0235(19) Uani 1 1 d . . . H29 H 0.8091 0.2873 -0.0482 0.028 Uiso 1 1 calc R . . C30 C 0.8636(9) 0.2200(3) -0.0138(4) 0.0239(19) Uani 1 1 d . . . H30 H 0.8381 0.2262 0.0336 0.029 Uiso 1 1 calc R . . C31 C 0.8312(8) -0.0470(3) 0.7140(4) 0.0172(17) Uani 1 1 d . . . C32 C 0.7773(8) -0.0434(3) 0.6438(4) 0.0166(17) Uani 1 1 d . . . C33 C 0.7971(8) -0.0816(3) 0.5989(4) 0.0186(18) Uani 1 1 d . . . H33 H 0.7563 -0.0790 0.5518 0.022 Uiso 1 1 calc R . . C34 C 0.8771(9) -0.1243(3) 0.6225(4) 0.0218(19) Uani 1 1 d . . . H34 H 0.8912 -0.1506 0.5912 0.026 Uiso 1 1 calc R . . C35 C 0.9351(9) -0.1286(3) 0.6899(4) 0.0190(18) Uani 1 1 d . . . H35 H 0.9905 -0.1576 0.7057 0.023 Uiso 1 1 calc R . . C36 C 0.9118(8) -0.0893(3) 0.7360(4) 0.0216(18) Uani 1 1 d . . . H36 H 0.9525 -0.0921 0.7831 0.026 Uiso 1 1 calc R . . C37 C 0.8192(8) -0.0452(3) 0.2133(3) 0.0174(18) Uani 1 1 d . . . C38 C 0.7655(9) -0.0375(3) 0.1431(4) 0.0159(17) Uani 1 1 d . . . C39 C 0.7903(9) -0.0732(3) 0.0944(4) 0.0205(18) Uani 1 1 d . . . H39 H 0.7554 -0.0679 0.0471 0.025 Uiso 1 1 calc R . . C40 C 0.8654(9) -0.1163(3) 0.1141(4) 0.025(2) Uani 1 1 d . . . H40 H 0.8812 -0.1411 0.0804 0.030 Uiso 1 1 calc R . . C41 C 0.9191(9) -0.1243(3) 0.1836(4) 0.0213(18) Uani 1 1 d . . . H41 H 0.9725 -0.1542 0.1968 0.026 Uiso 1 1 calc R . . C42 C 0.8945(8) -0.0884(3) 0.2335(4) 0.0155(17) Uani 1 1 d . . . H42 H 0.9294 -0.0937 0.2808 0.019 Uiso 1 1 calc R . . C43 C 0.2596(8) -0.0377(3) 0.0729(4) 0.0176(18) Uani 1 1 d . . . C44 C 0.2857(9) -0.0472(3) 0.0024(3) 0.0175(17) Uani 1 1 d . . . C45 C 0.3475(8) -0.0920(3) -0.0175(4) 0.0216(19) Uani 1 1 d . . . H45 H 0.3624 -0.0989 -0.0654 0.026 Uiso 1 1 calc R . . C46 C 0.3884(9) -0.1274(3) 0.0330(4) 0.0219(19) Uani 1 1 d . . . H46 H 0.4332 -0.1580 0.0193 0.026 Uiso 1 1 calc R . . C47 C 0.3635(9) -0.1177(3) 0.1015(4) 0.026(2) Uani 1 1 d . . . H47 H 0.3880 -0.1420 0.1356 0.031 Uiso 1 1 calc R . . C48 C 0.3025(9) -0.0726(3) 0.1221(4) 0.0167(17) Uani 1 1 d . . . H48 H 0.2903 -0.0657 0.1703 0.020 Uiso 1 1 calc R . . O1S O 1.1481(6) 0.3078(2) 0.5506(2) 0.0317(14) Uani 1 1 d . . . O2S O 0.4086(6) 0.25089(19) 0.5371(2) 0.0264(12) Uani 1 1 d . . . O3S O 0.3688(6) 0.2501(2) 0.0336(2) 0.0294(13) Uani 1 1 d . . . O4S O 1.1409(6) 0.3183(2) 0.0459(2) 0.0307(13) Uani 1 1 d . . . O5S O 0.5149(6) -0.1166(2) 0.2991(3) 0.0331(14) Uani 1 1 d . . . O6S O 0.5068(6) -0.1183(2) 0.7874(3) 0.0313(14) Uani 1 1 d . . . O7S O 0.7079(6) -0.11309(19) 0.9005(3) 0.0304(13) Uani 1 1 d . . . O8S O 0.7429(6) -0.1133(2) 0.4089(3) 0.0319(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0203(10) 0.0209(12) 0.0287(11) 0.0012(10) -0.0023(8) 0.0000(9) S2 0.0226(10) 0.0270(13) 0.0261(11) 0.0031(10) 0.0024(8) 0.0017(9) S3 0.0172(9) 0.0171(11) 0.0172(10) 0.0002(9) 0.0033(7) 0.0003(9) S4 0.0142(9) 0.0204(12) 0.0144(10) -0.0004(9) 0.0012(7) 0.0007(9) S5 0.0159(9) 0.0157(11) 0.0156(10) 0.0011(9) 0.0017(7) 0.0021(9) S6 0.0137(9) 0.0174(11) 0.0148(10) -0.0003(8) 0.0003(7) 0.0001(9) S7 0.0152(9) 0.0194(12) 0.0143(10) 0.0001(8) 0.0006(7) -0.0027(9) S8 0.0178(9) 0.0193(13) 0.0138(10) -0.0008(9) 0.0008(7) -0.0013(9) S9 0.0174(9) 0.0160(11) 0.0125(10) 0.0007(8) 0.0013(7) 0.0001(9) S10 0.0141(9) 0.0201(13) 0.0157(10) -0.0011(9) 0.0030(7) -0.0013(8) O1 0.053(4) 0.026(4) 0.043(3) -0.015(3) -0.013(3) 0.015(3) O2 0.029(3) 0.029(4) 0.023(3) 0.004(3) -0.004(2) 0.006(2) O3 0.019(3) 0.043(4) 0.055(4) 0.020(3) 0.006(2) 0.000(3) O4 0.023(3) 0.029(4) 0.032(3) 0.003(3) 0.010(2) 0.002(2) O5 0.040(3) 0.046(4) 0.025(3) -0.008(3) -0.004(2) 0.009(3) O6 0.047(4) 0.063(5) 0.073(5) 0.030(4) 0.011(3) 0.009(4) O7 0.026(3) 0.078(5) 0.051(4) -0.018(4) -0.016(3) 0.009(3) O8 0.016(3) 0.059(5) 0.045(3) 0.000(3) -0.009(2) 0.006(3) O9 0.048(3) 0.013(3) 0.022(3) 0.003(2) -0.001(3) 0.003(3) O10 0.021(3) 0.024(3) 0.015(3) -0.003(2) 0.003(2) 0.003(2) O11 0.017(2) 0.036(4) 0.017(3) -0.001(2) 0.007(2) -0.002(2) O12 0.015(2) 0.029(4) 0.022(3) -0.008(2) 0.003(2) -0.002(2) O13 0.023(3) 0.023(3) 0.020(3) 0.001(2) 0.004(2) 0.002(2) O14 0.014(2) 0.027(3) 0.019(3) 0.004(2) 0.005(2) -0.001(2) O15 0.017(3) 0.028(3) 0.019(3) 0.000(2) -0.007(2) 0.002(2) O16 0.018(3) 0.030(3) 0.007(3) 0.001(2) -0.004(2) 0.002(2) O17 0.027(3) 0.016(3) 0.023(3) -0.002(2) 0.000(2) 0.005(2) O18 0.023(3) 0.013(3) 0.020(3) -0.001(2) 0.000(2) 0.000(2) O19 0.018(3) 0.025(3) 0.018(3) -0.001(2) 0.007(2) -0.007(2) O20 0.015(2) 0.028(3) 0.015(3) -0.005(2) -0.0004(19) -0.003(2) O21 0.016(3) 0.027(3) 0.019(3) -0.001(2) -0.001(2) 0.006(2) O22 0.018(3) 0.024(3) 0.019(3) 0.002(2) 0.005(2) 0.001(2) O23 0.015(2) 0.018(3) 0.017(3) -0.005(2) -0.001(2) -0.002(2) O24 0.019(3) 0.020(3) 0.020(3) 0.004(2) 0.002(2) 0.001(2) O25 0.015(2) 0.019(3) 0.017(3) -0.001(2) -0.001(2) -0.005(2) O26 0.018(3) 0.021(3) 0.022(3) 0.003(2) -0.002(2) 0.001(2) O27 0.022(3) 0.017(3) 0.019(3) -0.003(2) 0.001(2) -0.002(2) O28 0.011(2) 0.034(4) 0.018(3) -0.003(2) 0.0031(19) -0.002(2) O29 0.020(3) 0.023(3) 0.023(3) -0.003(2) 0.001(2) -0.001(2) O30 0.017(3) 0.036(4) 0.019(3) -0.001(3) 0.010(2) -0.005(3) O31 0.019(3) 0.036(4) 0.014(3) -0.005(2) 0.000(2) -0.006(2) O32 0.052(3) 0.028(4) 0.013(3) 0.004(3) 0.001(2) 0.007(3) O33 0.020(3) 0.027(3) 0.012(3) -0.003(2) -0.005(2) -0.002(2) O34 0.022(3) 0.018(3) 0.016(3) 0.004(2) 0.003(2) 0.000(2) O35 0.024(3) 0.022(3) 0.014(3) -0.007(2) 0.000(2) 0.001(2) O36 0.019(3) 0.021(3) 0.016(3) 0.003(2) 0.005(2) -0.006(2) O37 0.022(3) 0.017(3) 0.016(3) -0.006(2) 0.002(2) 0.000(2) O38 0.020(3) 0.024(3) 0.018(3) -0.001(2) 0.005(2) -0.007(2) O39 0.015(2) 0.023(3) 0.025(3) -0.003(2) -0.001(2) -0.002(2) O40 0.021(3) 0.023(3) 0.014(3) -0.001(2) 0.000(2) 0.006(2) N1 0.017(3) 0.018(4) 0.017(3) 0.001(3) -0.001(3) 0.003(3) N2 0.018(3) 0.020(4) 0.018(3) 0.000(3) 0.005(2) 0.003(3) N3 0.019(3) 0.032(5) 0.012(3) -0.001(3) 0.002(2) -0.001(3) N4 0.025(3) 0.022(4) 0.006(3) 0.004(3) -0.002(2) 0.004(3) N5 0.014(3) 0.023(4) 0.013(3) 0.002(3) 0.000(2) 0.002(3) N6 0.009(3) 0.032(4) 0.014(3) -0.007(3) 0.001(2) 0.005(3) N7 0.016(3) 0.010(4) 0.012(3) 0.002(3) 0.007(2) 0.000(3) N8 0.018(3) 0.014(4) 0.022(3) 0.002(3) 0.002(2) 0.007(3) N9 0.012(3) 0.020(4) 0.013(3) 0.002(3) 0.001(2) -0.002(3) N10 0.028(3) 0.020(4) 0.007(3) 0.004(3) 0.008(2) -0.007(3) N11 0.010(3) 0.029(4) 0.025(4) 0.002(3) 0.002(3) 0.003(3) N12 0.018(3) 0.023(4) 0.010(3) 0.002(3) 0.001(2) 0.000(3) N13 0.018(3) 0.012(4) 0.012(3) 0.001(3) 0.001(2) -0.004(3) N14 0.013(3) 0.027(4) 0.024(3) -0.001(3) 0.001(2) 0.000(3) N15 0.023(3) 0.016(4) 0.012(3) 0.006(3) 0.002(2) -0.001(3) N16 0.012(3) 0.018(4) 0.016(3) -0.007(3) 0.001(2) 0.003(3) C1 0.011(4) 0.022(5) 0.012(4) -0.004(3) 0.001(3) 0.001(3) C2 0.014(4) 0.020(5) 0.021(4) 0.008(4) 0.007(3) 0.005(3) C3 0.024(4) 0.028(5) 0.014(4) 0.000(4) -0.004(3) 0.000(4) C4 0.024(4) 0.020(5) 0.028(5) -0.004(4) 0.001(3) -0.002(4) C5 0.026(4) 0.018(5) 0.022(5) 0.008(4) 0.002(3) 0.000(3) C6 0.017(4) 0.020(5) 0.013(4) 0.002(3) 0.003(3) 0.000(3) C7 0.013(4) 0.014(5) 0.035(5) 0.004(4) 0.008(3) -0.004(3) C8 0.010(4) 0.023(5) 0.016(4) 0.001(4) -0.003(3) -0.004(3) C9 0.021(4) 0.022(5) 0.016(4) 0.003(4) 0.002(3) -0.002(4) C10 0.027(4) 0.030(6) 0.022(5) -0.002(4) 0.000(3) 0.006(4) C11 0.028(4) 0.020(5) 0.031(5) -0.007(4) 0.003(4) 0.004(4) C12 0.021(4) 0.032(6) 0.017(4) -0.003(4) -0.004(3) -0.006(4) C13 0.005(3) 0.023(5) 0.019(4) 0.001(4) 0.001(3) -0.003(3) C14 0.010(4) 0.019(5) 0.023(5) 0.000(4) 0.007(3) 0.003(3) C15 0.021(4) 0.037(6) 0.016(4) 0.004(4) -0.002(3) -0.007(4) C16 0.022(4) 0.004(4) 0.026(5) 0.006(3) 0.006(3) 0.000(3) C17 0.028(4) 0.011(5) 0.027(5) 0.004(4) 0.004(3) 0.005(4) C18 0.009(4) 0.032(5) 0.025(5) 0.007(4) 0.008(3) 0.003(4) C19 0.009(4) 0.018(5) 0.030(5) -0.004(4) -0.005(3) 0.001(3) C20 0.016(4) 0.023(5) 0.019(4) -0.006(4) 0.007(3) -0.003(4) C21 0.023(4) 0.022(5) 0.026(5) 0.000(4) -0.001(3) 0.008(4) C22 0.019(4) 0.035(6) 0.029(5) -0.001(4) 0.002(3) 0.009(4) C23 0.022(4) 0.020(5) 0.027(5) -0.009(4) -0.003(3) 0.003(4) C24 0.016(4) 0.026(5) 0.017(4) -0.007(4) 0.004(3) -0.005(3) C25 0.013(4) 0.011(4) 0.020(4) 0.004(3) 0.005(3) -0.004(3) C26 0.017(4) 0.025(5) 0.009(4) -0.001(3) -0.003(3) -0.005(3) C27 0.007(3) 0.026(5) 0.019(4) 0.002(4) 0.000(3) -0.004(3) C28 0.023(4) 0.021(5) 0.018(4) 0.003(4) 0.001(3) -0.003(4) C29 0.029(4) 0.016(5) 0.025(5) -0.002(4) -0.002(3) -0.004(4) C30 0.022(4) 0.032(6) 0.018(4) -0.006(4) 0.000(3) -0.006(4) C31 0.010(4) 0.007(4) 0.034(5) -0.003(4) 0.003(3) 0.001(3) C32 0.013(4) 0.019(5) 0.017(4) 0.000(4) 0.000(3) -0.002(3) C33 0.014(4) 0.022(5) 0.020(4) -0.001(4) 0.007(3) 0.004(3) C34 0.018(4) 0.012(5) 0.036(5) -0.005(4) 0.000(4) 0.001(3) C35 0.018(4) 0.011(5) 0.029(5) 0.009(4) 0.009(3) 0.001(3) C36 0.015(4) 0.027(5) 0.023(5) 0.004(4) 0.005(3) 0.001(4) C37 0.012(4) 0.028(5) 0.012(4) 0.000(3) 0.001(3) -0.011(3) C38 0.016(4) 0.015(5) 0.017(4) 0.002(3) 0.001(3) -0.010(3) C39 0.018(4) 0.027(5) 0.017(4) 0.007(4) 0.000(3) 0.001(4) C40 0.028(4) 0.033(6) 0.014(4) -0.006(4) 0.002(3) 0.005(4) C41 0.023(4) 0.011(5) 0.030(5) 0.005(4) 0.000(3) 0.006(3) C42 0.016(4) 0.015(5) 0.015(4) 0.007(3) 0.006(3) -0.008(3) C43 0.011(4) 0.020(5) 0.022(5) -0.006(4) -0.001(3) -0.003(3) C44 0.016(4) 0.024(5) 0.012(4) 0.011(3) 0.001(3) 0.002(3) C45 0.016(4) 0.031(6) 0.018(4) -0.004(4) 0.006(3) -0.002(4) C46 0.023(4) 0.023(5) 0.020(5) 0.001(4) 0.003(3) 0.002(3) C47 0.016(4) 0.035(6) 0.027(5) 0.009(4) 0.001(3) 0.004(4) C48 0.024(4) 0.017(5) 0.010(4) -0.003(3) 0.005(3) -0.004(3) O1S 0.032(3) 0.028(4) 0.034(3) 0.003(3) -0.005(2) -0.002(3) O2S 0.024(3) 0.024(3) 0.031(3) 0.003(3) 0.003(2) 0.003(2) O3S 0.036(3) 0.023(3) 0.029(3) -0.004(3) 0.000(2) 0.004(3) O4S 0.038(3) 0.032(4) 0.022(3) 0.001(3) 0.002(2) 0.001(3) O5S 0.026(3) 0.031(4) 0.042(3) -0.003(3) 0.000(2) 0.000(3) O6S 0.029(3) 0.024(4) 0.041(3) 0.007(3) 0.009(2) -0.003(3) O7S 0.032(3) 0.019(3) 0.040(3) 0.005(3) 0.007(2) -0.001(3) O8S 0.030(3) 0.028(4) 0.038(3) 0.005(3) 0.006(2) 0.000(3) _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 S1 O1 1.434(6) . ? S1 O2 1.442(4) . ? S1 O3 1.458(5) . ? S1 O4 1.562(6) . ? S2 O5 1.438(5) . ? S2 O7 1.458(6) . ? S2 O6 1.463(6) . ? S2 O8 1.570(6) . ? S3 O12 1.454(4) . ? S3 O11 1.474(5) . ? S3 O10 1.479(5) . ? S3 O9 1.487(5) . ? S4 O14 1.458(5) . ? S4 O16 1.473(5) . ? S4 O15 1.488(5) . ? S4 O13 1.494(5) . ? S5 O20 1.460(4) . ? S5 O18 1.475(5) . ? S5 O19 1.482(5) . ? S5 O17 1.502(5) . ? S6 O22 1.463(5) . ? S6 O24 1.466(5) . ? S6 O23 1.474(4) . ? S6 O21 1.486(5) . ? S7 O28 1.458(5) . ? S7 O26 1.472(5) . ? S7 O25 1.492(4) . ? S7 O27 1.501(5) . ? S8 O29 1.462(5) . ? S8 O31 1.474(4) . ? S8 O30 1.477(5) . ? S8 O32 1.477(5) . ? S9 O36 1.444(5) . ? S9 O34 1.461(5) . ? S9 O33 1.485(4) . ? S9 O35 1.508(5) . ? S10 O39 1.456(4) . ? S10 O37 1.474(5) . ? S10 O40 1.494(5) . ? S10 O38 1.498(5) . ? N1 C1 1.481(8) . ? N2 C2 1.467(9) . ? N3 C7 1.470(9) . ? N4 C8 1.466(9) . ? N5 C13 1.466(9) . ? N6 C14 1.445(9) . ? N7 C19 1.451(9) . ? N8 C20 1.473(9) . ? N9 C25 1.480(8) . ? N10 C26 1.446(10) . ? N11 C31 1.450(9) . ? N12 C32 1.479(9) . ? N13 C37 1.471(9) . ? N14 C38 1.483(9) . ? N15 C43 1.453(9) . ? N16 C44 1.462(8) . ? C1 C6 1.360(10) . ? C1 C2 1.391(9) . ? C2 C3 1.377(10) . ? C3 C4 1.374(11) . ? C4 C5 1.382(10) . ? C5 C6 1.406(10) . ? C7 C8 1.349(9) . ? C7 C12 1.405(11) . ? C8 C9 1.388(10) . ? C9 C10 1.384(10) . ? C10 C11 1.398(10) . ? C11 C12 1.395(11) . ? C13 C14 1.391(9) . ? C13 C18 1.398(10) . ? C14 C15 1.414(11) . ? C15 C16 1.372(11) . ? C16 C17 1.404(10) . ? C17 C18 1.378(10) . ? C19 C20 1.374(9) . ? C19 C24 1.411(10) . ? C20 C21 1.364(10) . ? C21 C22 1.381(10) . ? C22 C23 1.396(9) . ? C23 C24 1.388(10) . ? C25 C30 1.374(10) . ? C25 C26 1.394(9) . ? C26 C27 1.391(10) . ? C27 C28 1.369(10) . ? C28 C29 1.367(10) . ? C29 C30 1.364(10) . ? C31 C36 1.378(10) . ? C31 C32 1.401(9) . ? C32 C33 1.375(10) . ? C33 C34 1.394(10) . ? C34 C35 1.360(10) . ? C35 C36 1.415(10) . ? C37 C42 1.373(10) . ? C37 C38 1.412(9) . ? C38 C39 1.374(10) . ? C39 C40 1.369(11) . ? C40 C41 1.401(9) . ? C41 C42 1.393(10) . ? C43 C48 1.382(10) . ? C43 C44 1.397(9) . ? C44 C45 1.379(10) . ? C45 C46 1.403(10) . ? C46 C47 1.361(10) . ? C47 C48 1.389(11) . ? 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 S1 O2 113.4(3) . . ? O1 S1 O3 112.5(3) . . ? O2 S1 O3 111.6(3) . . ? O1 S1 O4 104.5(3) . . ? O2 S1 O4 108.3(3) . . ? O3 S1 O4 105.7(3) . . ? O5 S2 O7 114.8(3) . . ? O5 S2 O6 110.6(4) . . ? O7 S2 O6 109.6(4) . . ? O5 S2 O8 109.5(3) . . ? O7 S2 O8 107.1(4) . . ? O6 S2 O8 104.7(3) . . ? O12 S3 O11 109.3(3) . . ? O12 S3 O10 109.7(3) . . ? O11 S3 O10 110.7(3) . . ? O12 S3 O9 110.6(3) . . ? O11 S3 O9 108.6(3) . . ? O10 S3 O9 107.9(3) . . ? O14 S4 O16 111.2(3) . . ? O14 S4 O15 111.3(3) . . ? O16 S4 O15 108.0(3) . . ? O14 S4 O13 111.1(3) . . ? O16 S4 O13 107.8(3) . . ? O15 S4 O13 107.2(3) . . ? O20 S5 O18 111.3(3) . . ? O20 S5 O19 111.0(3) . . ? O18 S5 O19 108.9(3) . . ? O20 S5 O17 110.0(3) . . ? O18 S5 O17 107.9(3) . . ? O19 S5 O17 107.6(3) . . ? O22 S6 O24 111.2(3) . . ? O22 S6 O23 111.0(3) . . ? O24 S6 O23 109.0(3) . . ? O22 S6 O21 109.6(3) . . ? O24 S6 O21 107.7(3) . . ? O23 S6 O21 108.3(3) . . ? O28 S7 O26 112.3(3) . . ? O28 S7 O25 109.9(3) . . ? O26 S7 O25 108.9(3) . . ? O28 S7 O27 110.1(3) . . ? O26 S7 O27 107.7(3) . . ? O25 S7 O27 107.8(3) . . ? O29 S8 O31 109.2(3) . . ? O29 S8 O30 110.5(3) . . ? O31 S8 O30 108.8(3) . . ? O29 S8 O32 108.9(3) . . ? O31 S8 O32 110.0(3) . . ? O30 S8 O32 109.5(3) . . ? O36 S9 O34 111.8(3) . . ? O36 S9 O33 110.5(3) . . ? O34 S9 O33 108.8(3) . . ? O36 S9 O35 110.4(3) . . ? O34 S9 O35 108.2(3) . . ? O33 S9 O35 107.0(3) . . ? O39 S10 O37 111.1(3) . . ? O39 S10 O40 111.1(3) . . ? O37 S10 O40 107.3(3) . . ? O39 S10 O38 110.7(3) . . ? O37 S10 O38 108.7(3) . . ? O40 S10 O38 108.0(3) . . ? C6 C1 C2 121.0(7) . . ? C6 C1 N1 118.0(6) . . ? C2 C1 N1 120.9(7) . . ? C3 C2 C1 118.8(7) . . ? C3 C2 N2 119.7(6) . . ? C1 C2 N2 121.5(7) . . ? C4 C3 C2 121.0(7) . . ? C3 C4 C5 120.2(7) . . ? C4 C5 C6 118.9(7) . . ? C1 C6 C5 120.0(7) . . ? C8 C7 C12 120.3(7) . . ? C8 C7 N3 123.1(7) . . ? C12 C7 N3 116.7(7) . . ? C7 C8 C9 121.2(7) . . ? C7 C8 N4 119.7(7) . . ? C9 C8 N4 119.1(6) . . ? C10 C9 C8 119.6(7) . . ? C9 C10 C11 119.9(7) . . ? C12 C11 C10 119.6(7) . . ? C11 C12 C7 119.3(7) . . ? C14 C13 C18 120.7(7) . . ? C14 C13 N5 121.7(7) . . ? C18 C13 N5 117.6(6) . . ? C13 C14 C15 118.6(7) . . ? C13 C14 N6 121.1(7) . . ? C15 C14 N6 120.3(7) . . ? C16 C15 C14 120.6(7) . . ? C15 C16 C17 120.1(7) . . ? C18 C17 C16 120.1(7) . . ? C17 C18 C13 119.9(7) . . ? C20 C19 C24 119.7(7) . . ? C20 C19 N7 123.0(7) . . ? C24 C19 N7 117.3(6) . . ? C21 C20 C19 120.0(7) . . ? C21 C20 N8 119.8(6) . . ? C19 C20 N8 120.1(7) . . ? C20 C21 C22 121.6(7) . . ? C21 C22 C23 119.3(8) . . ? C24 C23 C22 119.5(7) . . ? C23 C24 C19 119.7(7) . . ? C30 C25 C26 120.8(7) . . ? C30 C25 N9 118.6(6) . . ? C26 C25 N9 120.5(7) . . ? C27 C26 C25 118.2(7) . . ? C27 C26 N10 120.4(6) . . ? C25 C26 N10 121.3(7) . . ? C28 C27 C26 120.4(7) . . ? C29 C28 C27 120.1(7) . . ? C30 C29 C28 121.1(8) . . ? C29 C30 C25 119.4(7) . . ? C36 C31 C32 118.0(7) . . ? C36 C31 N11 120.3(7) . . ? C32 C31 N11 121.5(6) . . ? C33 C32 C31 121.0(7) . . ? C33 C32 N12 120.5(6) . . ? C31 C32 N12 118.5(6) . . ? C32 C33 C34 119.9(7) . . ? C35 C34 C33 120.7(7) . . ? C34 C35 C36 119.0(7) . . ? C31 C36 C35 121.4(7) . . ? C42 C37 C38 120.4(7) . . ? C42 C37 N13 117.9(6) . . ? C38 C37 N13 121.6(7) . . ? C39 C38 C37 120.0(7) . . ? C39 C38 N14 120.5(6) . . ? C37 C38 N14 119.5(6) . . ? C40 C39 C38 119.9(7) . . ? C39 C40 C41 120.5(7) . . ? C42 C41 C40 120.1(7) . . ? C37 C42 C41 119.0(7) . . ? C48 C43 C44 119.6(7) . . ? C48 C43 N15 120.7(6) . . ? C44 C43 N15 119.6(7) . . ? C45 C44 C43 119.6(7) . . ? C45 C44 N16 118.6(6) . . ? C43 C44 N16 121.8(7) . . ? C44 C45 C46 120.2(7) . . ? C47 C46 C45 119.8(8) . . ? C46 C47 C48 120.4(7) . . ? C43 C48 C47 120.3(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 C6 C1 C2 C3 2.2(10) . . . . ? N1 C1 C2 C3 179.7(6) . . . . ? C6 C1 C2 N2 -177.2(6) . . . . ? N1 C1 C2 N2 0.4(9) . . . . ? C1 C2 C3 C4 -1.3(10) . . . . ? N2 C2 C3 C4 178.0(6) . . . . ? C2 C3 C4 C5 0.7(11) . . . . ? C3 C4 C5 C6 -0.9(11) . . . . ? C2 C1 C6 C5 -2.4(10) . . . . ? N1 C1 C6 C5 -180.0(6) . . . . ? C4 C5 C6 C1 1.7(10) . . . . ? C12 C7 C8 C9 -0.9(10) . . . . ? N3 C7 C8 C9 -179.1(6) . . . . ? C12 C7 C8 N4 -178.8(6) . . . . ? N3 C7 C8 N4 2.9(10) . . . . ? C7 C8 C9 C10 0.9(11) . . . . ? N4 C8 C9 C10 178.8(6) . . . . ? C8 C9 C10 C11 -0.9(10) . . . . ? C9 C10 C11 C12 1.0(11) . . . . ? C10 C11 C12 C7 -1.0(11) . . . . ? C8 C7 C12 C11 0.9(10) . . . . ? N3 C7 C12 C11 179.3(6) . . . . ? C18 C13 C14 C15 -1.8(10) . . . . ? N5 C13 C14 C15 178.9(6) . . . . ? C18 C13 C14 N6 178.6(6) . . . . ? N5 C13 C14 N6 -0.7(9) . . . . ? C13 C14 C15 C16 0.7(10) . . . . ? N6 C14 C15 C16 -179.8(6) . . . . ? C14 C15 C16 C17 1.1(10) . . . . ? C15 C16 C17 C18 -1.8(10) . . . . ? C16 C17 C18 C13 0.7(10) . . . . ? C14 C13 C18 C17 1.1(10) . . . . ? N5 C13 C18 C17 -179.5(6) . . . . ? C24 C19 C20 C21 -2.1(10) . . . . ? N7 C19 C20 C21 177.4(6) . . . . ? C24 C19 C20 N8 177.3(6) . . . . ? N7 C19 C20 N8 -3.2(10) . . . . ? C19 C20 C21 C22 4.2(11) . . . . ? N8 C20 C21 C22 -175.3(6) . . . . ? C20 C21 C22 C23 -4.6(11) . . . . ? C21 C22 C23 C24 3.0(10) . . . . ? C22 C23 C24 C19 -1.1(10) . . . . ? C20 C19 C24 C23 0.6(10) . . . . ? N7 C19 C24 C23 -178.9(6) . . . . ? C30 C25 C26 C27 -2.2(10) . . . . ? N9 C25 C26 C27 -177.7(6) . . . . ? C30 C25 C26 N10 178.1(6) . . . . ? N9 C25 C26 N10 2.6(9) . . . . ? C25 C26 C27 C28 0.8(10) . . . . ? N10 C26 C27 C28 -179.5(6) . . . . ? C26 C27 C28 C29 0.6(10) . . . . ? C27 C28 C29 C30 -0.7(11) . . . . ? C28 C29 C30 C25 -0.7(11) . . . . ? C26 C25 C30 C29 2.2(10) . . . . ? N9 C25 C30 C29 177.7(6) . . . . ? C36 C31 C32 C33 2.8(10) . . . . ? N11 C31 C32 C33 177.0(6) . . . . ? C36 C31 C32 N12 -178.0(6) . . . . ? N11 C31 C32 N12 -3.8(10) . . . . ? C31 C32 C33 C34 -2.1(10) . . . . ? N12 C32 C33 C34 178.7(6) . . . . ? C32 C33 C34 C35 0.4(11) . . . . ? C33 C34 C35 C36 0.5(10) . . . . ? C32 C31 C36 C35 -1.8(10) . . . . ? N11 C31 C36 C35 -176.1(6) . . . . ? C34 C35 C36 C31 0.2(11) . . . . ? C42 C37 C38 C39 -0.7(10) . . . . ? N13 C37 C38 C39 -177.1(6) . . . . ? C42 C37 C38 N14 -179.0(6) . . . . ? N13 C37 C38 N14 4.7(9) . . . . ? C37 C38 C39 C40 0.7(10) . . . . ? N14 C38 C39 C40 179.0(6) . . . . ? C38 C39 C40 C41 -0.7(11) . . . . ? C39 C40 C41 C42 0.8(11) . . . . ? C38 C37 C42 C41 0.7(10) . . . . ? N13 C37 C42 C41 177.2(6) . . . . ? C40 C41 C42 C37 -0.8(10) . . . . ? C48 C43 C44 C45 2.6(10) . . . . ? N15 C43 C44 C45 -179.7(6) . . . . ? C48 C43 C44 N16 -176.9(6) . . . . ? N15 C43 C44 N16 0.8(9) . . . . ? C43 C44 C45 C46 -1.7(10) . . . . ? N16 C44 C45 C46 177.8(6) . . . . ? C44 C45 C46 C47 1.3(10) . . . . ? C45 C46 C47 C48 -1.8(11) . . . . ? C44 C43 C48 C47 -3.0(10) . . . . ? N15 C43 C48 C47 179.2(6) . . . . ? C46 C47 C48 C43 2.7(11) . . . . ? 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 H1C O15 0.91 1.99 2.860(8) 160.3 2_656 N1 H1B O35 0.91 1.93 2.823(7) 168.1 2_756 N1 H1B O33 0.91 2.53 3.079(7) 119.5 2_756 N1 H1A O40 0.91 2.02 2.897(7) 160.3 2_656 N2 H2C O33 0.91 1.89 2.796(7) 175.0 2_756 N2 H2B O16 0.91 1.82 2.735(7) 179.0 2_656 N2 H2A O31 0.91 1.85 2.741(7) 165.0 2_656 N3 H3C O11 0.91 2.05 2.820(7) 142.0 . N3 H3B O29 0.91 1.81 2.718(8) 172.7 . N3 H3A O22 0.91 1.91 2.819(7) 178.6 1_556 N3 H3A O23 0.91 2.64 3.170(7) 117.8 1_556 N4 H4C O12 0.91 2.00 2.730(7) 135.7 1_455 N4 H4B O11 0.91 1.99 2.864(7) 161.1 . N4 H4B O30 0.91 2.61 3.135(8) 117.4 . N4 H4A O13 0.91 2.00 2.878(7) 161.5 . N5 H5A O33 0.91 1.97 2.833(8) 156.7 1_455 N5 H5B O9 0.91 1.90 2.750(7) 154.7 1_455 N5 H5C O13 0.91 2.04 2.932(7) 167.3 . N5 H5C O15 0.91 2.49 3.026(7) 117.8 . N6 H6A O15 0.91 1.97 2.848(7) 162.1 . N6 H6B O20 0.91 2.00 2.903(7) 169.9 1_455 N6 H6B O19 0.91 2.61 3.078(7) 112.6 1_455 N6 H6C O34 0.91 1.87 2.773(8) 174.5 1_455 N7 H7A O37 0.91 1.84 2.733(7) 166.6 . N7 H7B O14 0.91 2.02 2.863(7) 152.6 . N7 H7C O19 0.91 1.94 2.854(7) 179.1 . N8 H8A O21 0.91 2.19 2.936(7) 139.4 . N8 H8A O20 0.91 2.41 2.895(7) 113.3 1_455 N8 H8B O38 0.91 1.99 2.831(8) 152.4 . N8 H8B O19 0.91 2.66 3.133(7) 113.3 . N8 H8C O17 0.91 2.03 2.878(7) 154.5 . N9 H9C O21 0.91 1.95 2.815(6) 159.1 1_655 N9 H9C O23 0.91 2.46 3.107(7) 128.4 1_655 N9 H9B O25 0.91 2.00 2.831(8) 150.8 1_554 N9 H9A O17 0.91 2.06 2.937(7) 160.9 . N10 H10C O26 0.91 1.84 2.715(7) 159.5 1_554 N10 H10B O23 0.91 1.90 2.788(7) 165.9 1_655 N10 H10A O12 0.91 2.00 2.790(7) 144.5 1_554 N11 H11A O27 0.91 1.98 2.854(7) 159.7 . N11 H11B O30 0.91 1.95 2.814(7) 158.1 . N11 H11B O11 0.91 2.52 3.054(9) 117.7 . N11 H11C O31 0.91 1.98 2.715(7) 137.1 1_655 N12 H12C O30 0.91 2.02 2.812(7) 144.5 . N12 H12B O36 0.91 1.92 2.824(7) 176.1 . N12 H12B O33 0.91 2.64 3.153(7) 116.8 . N12 H12A O10 0.91 1.80 2.698(8) 171.2 . N13 H13C O35 0.91 1.99 2.878(7) 164.3 . N13 H13B O40 0.91 1.99 2.868(7) 161.0 . N13 H13B O38 0.91 2.43 3.128(7) 133.3 . N13 H13A O19 0.91 1.99 2.814(8) 149.4 . N14 H14C O28 0.91 1.99 2.867(7) 162.4 1_554 N14 H14B O18 0.91 1.80 2.708(7) 174.3 . N14 H14A O38 0.91 1.94 2.840(7) 170.1 . N15 H15A O24 0.91 1.85 2.750(7) 172.6 . N15 H15B O39 0.91 1.96 2.861(7) 169.8 . N15 H15B O38 0.91 2.63 3.115(7) 114.5 . N15 H15C O25 0.91 2.01 2.888(7) 162.7 1_454 N16 H16C O23 0.91 2.14 2.844(8) 133.6 . N16 H16C O28 0.91 2.34 2.913(6) 120.4 1_554 N16 H16B O25 0.91 2.12 2.987(7) 157.8 1_454 N16 H16B O27 0.91 2.28 2.987(7) 134.2 1_454 N16 H16A O32 0.91 1.88 2.739(7) 156.1 1_554 _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.480 _refine_diff_density_min -0.512 _refine_diff_density_rms 0.099 # Attachment 'all.cif' data_1a _database_code_depnum_ccdc_archive 'CCDC 299854' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, 2(B F4)' _chemical_formula_sum 'C6 H10 B2 F8 N2' _chemical_formula_weight 283.78 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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 11.180(2) _cell_length_b 7.1600(14) _cell_length_c 13.983(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.27(3) _cell_angle_gamma 90.00 _cell_volume 1119.1(4) _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 colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.684 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.193 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9097 _exptl_absorpt_correction_T_max 0.9810 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type kappaccd _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 7843 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2567 _reflns_number_gt 2250 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _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^)+(0.0403P)^2^+0.3315P] 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 calc _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.016(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2567 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0369 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0775 _refine_ls_wR_factor_gt 0.0739 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.023 _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 N1 N 0.66028(8) 0.34442(12) 0.79667(6) 0.0139(2) Uani 1 1 d . . . H1A H 0.6298 0.4094 0.7458 0.021 Uiso 1 1 calc R . . H1B H 0.6051 0.3398 0.8435 0.021 Uiso 1 1 calc R . . H1C H 0.6786 0.2263 0.7779 0.021 Uiso 1 1 calc R . . N2 N 0.65055(8) 0.66050(12) 0.93095(6) 0.01327(19) Uani 1 1 d . . . H2A H 0.6212 0.5795 0.9748 0.020 Uiso 1 1 calc R . . H2B H 0.5972 0.6723 0.8812 0.020 Uiso 1 1 calc R . . H2C H 0.6627 0.7740 0.9588 0.020 Uiso 1 1 calc R . . C1 C 0.76891(9) 0.43762(15) 0.83341(7) 0.0135(2) Uani 1 1 d . . . C2 C 0.76441(9) 0.58906(15) 0.89550(7) 0.0129(2) Uani 1 1 d . . . C3 C 0.86910(10) 0.67547(16) 0.92633(8) 0.0173(2) Uani 1 1 d . . . H3 H 0.8661 0.7794 0.9685 0.021 Uiso 1 1 calc R . . C4 C 0.97861(10) 0.60979(18) 0.89550(8) 0.0217(3) Uani 1 1 d . . . H4 H 1.0505 0.6691 0.9166 0.026 Uiso 1 1 calc R . . C5 C 0.98343(10) 0.45831(18) 0.83417(8) 0.0229(3) Uani 1 1 d . . . H5 H 1.0585 0.4134 0.8135 0.028 Uiso 1 1 calc R . . C6 C 0.87822(10) 0.37193(17) 0.80288(8) 0.0192(2) Uani 1 1 d . . . H6 H 0.8813 0.2681 0.7607 0.023 Uiso 1 1 calc R . . B1 B 0.64896(11) 1.16304(17) 1.04238(8) 0.0142(2) Uani 1 1 d . . . F1 F 0.58861(6) -0.28231(9) 0.74008(4) 0.01808(17) Uani 1 1 d . . . F2 F 0.56877(6) -0.02764(10) 0.64548(5) 0.02477(18) Uani 1 1 d . . . F3 F 0.73082(7) -0.21613(11) 0.63026(5) 0.02719(19) Uani 1 1 d . . . F4 F 0.71410(6) -0.03406(9) 0.76269(5) 0.02082(17) Uani 1 1 d . . . B2 B 0.65252(11) -0.14001(17) 0.69383(8) 0.0142(2) Uani 1 1 d . . . F5 F 0.74183(6) 1.24460(11) 1.09397(5) 0.02411(18) Uani 1 1 d . . . F6 F 0.58845(6) 1.29812(9) 0.98580(4) 0.01898(17) Uani 1 1 d . . . F7 F 0.56681(6) 1.08630(10) 1.10491(5) 0.02007(17) Uani 1 1 d . . . F8 F 0.69325(7) 1.02726(9) 0.98094(5) 0.02235(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0148(4) 0.0139(4) 0.0129(4) -0.0031(3) 0.0009(3) 0.0006(3) N2 0.0141(4) 0.0117(4) 0.0140(4) -0.0025(3) 0.0012(3) 0.0000(3) C1 0.0141(5) 0.0149(5) 0.0114(4) 0.0019(4) -0.0005(4) -0.0009(4) C2 0.0134(5) 0.0130(5) 0.0125(5) 0.0022(4) 0.0018(4) 0.0002(4) C3 0.0176(5) 0.0172(5) 0.0170(5) 0.0011(4) -0.0006(4) -0.0035(4) C4 0.0143(5) 0.0277(6) 0.0229(6) 0.0056(5) -0.0012(4) -0.0048(5) C5 0.0142(5) 0.0316(7) 0.0232(6) 0.0037(5) 0.0044(4) 0.0036(5) C6 0.0188(5) 0.0213(6) 0.0177(5) -0.0003(4) 0.0041(4) 0.0039(5) B1 0.0171(6) 0.0123(5) 0.0133(5) -0.0007(4) 0.0014(4) -0.0005(4) F1 0.0244(4) 0.0138(3) 0.0161(3) 0.0029(2) 0.0009(3) -0.0005(3) F2 0.0169(3) 0.0247(4) 0.0325(4) 0.0163(3) -0.0050(3) -0.0025(3) F3 0.0222(4) 0.0351(4) 0.0245(4) -0.0129(3) 0.0080(3) -0.0024(3) F4 0.0261(4) 0.0168(3) 0.0194(3) -0.0045(3) -0.0043(3) -0.0004(3) B2 0.0160(6) 0.0146(6) 0.0120(5) 0.0005(4) 0.0001(4) 0.0006(4) F5 0.0181(3) 0.0268(4) 0.0274(4) -0.0090(3) -0.0014(3) -0.0029(3) F6 0.0271(4) 0.0152(3) 0.0148(3) 0.0035(2) 0.0026(3) 0.0025(3) F7 0.0223(4) 0.0210(3) 0.0171(3) 0.0053(3) 0.0035(3) -0.0026(3) F8 0.0287(4) 0.0150(3) 0.0236(3) -0.0057(3) 0.0056(3) 0.0018(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.4685(14) . ? N2 C2 1.4683(14) . ? C6 C1 1.3857(15) . ? C6 C5 1.3910(17) . ? C3 C2 1.3842(15) . ? C3 C4 1.3891(17) . ? C2 C1 1.3906(15) . ? C4 C5 1.3844(18) . ? F1 B2 1.4097(14) . ? F2 B2 1.3976(14) . ? F8 B1 1.3954(14) . ? F4 B2 1.3954(14) . ? F5 B1 1.3807(14) . ? F6 B1 1.4125(14) . ? F7 B1 1.3949(14) . ? F3 B2 1.3741(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C6 C5 119.85(11) . . ? C2 C3 C4 119.81(11) . . ? C3 C2 C1 120.06(10) . . ? C3 C2 N2 118.20(10) . . ? C1 C2 N2 121.73(9) . . ? C5 C4 C3 120.27(11) . . ? C6 C1 C2 120.08(10) . . ? C6 C1 N1 117.79(10) . . ? C2 C1 N1 122.12(9) . . ? C4 C5 C6 119.93(11) . . ? F5 B1 F7 109.69(9) . . ? F5 B1 F8 110.08(9) . . ? F7 B1 F8 111.04(9) . . ? F5 B1 F6 110.39(9) . . ? F7 B1 F6 107.88(9) . . ? F8 B1 F6 107.72(9) . . ? F3 B2 F4 110.51(10) . . ? F3 B2 F2 110.18(9) . . ? F4 B2 F2 109.62(9) . . ? F3 B2 F1 110.29(10) . . ? F4 B2 F1 108.89(9) . . ? F2 B2 F1 107.28(9) . . ? 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 C4 C3 C2 C1 -0.36(16) . . . . ? C4 C3 C2 N2 178.97(10) . . . . ? C2 C3 C4 C5 -0.04(17) . . . . ? C5 C6 C1 C2 -0.26(16) . . . . ? C5 C6 C1 N1 178.64(10) . . . . ? C3 C2 C1 C6 0.52(16) . . . . ? N2 C2 C1 C6 -178.79(10) . . . . ? C3 C2 C1 N1 -178.34(10) . . . . ? N2 C2 C1 N1 2.35(15) . . . . ? C3 C4 C5 C6 0.30(18) . . . . ? C1 C6 C5 C4 -0.14(18) . . . . ? 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 F7 0.91 2.08 2.8988(13) 149.5 4_575 N1 H1A F1 0.91 2.26 2.8954(12) 126.9 1_565 N1 H1B F6 0.91 2.02 2.8005(13) 142.3 1_545 N1 H1B F2 0.91 2.17 2.8536(13) 131.1 2_656 N1 H1C F4 0.91 1.92 2.8185(12) 169.5 . N2 H2A F6 0.91 2.05 2.7975(12) 138.0 1_545 N2 H2A F2 0.91 2.50 3.2956(14) 146.5 4_566 N2 H2B F1 0.91 2.00 2.7727(12) 141.7 1_565 N2 H2B F2 0.91 2.37 2.9754(13) 124.3 2_656 N2 H2B F7 0.91 2.53 3.0643(12) 118.0 3_677 N2 H2C F8 0.91 1.87 2.7564(12) 164.1 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.269 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.074 data_1b _database_code_depnum_ccdc_archive 'CCDC 299855' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C6 H10 N2, 2(Br)' _chemical_formula_sum 'C6 H10 Br2 N2' _chemical_formula_weight 269.98 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' Br Br -0.2901 2.4595 '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 13.5054(10) _cell_length_b 7.4498(10) _cell_length_c 9.418(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.351(6) _cell_angle_gamma 90.00 _cell_volume 888.5(8) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.018 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 9.056 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0929 _exptl_absorpt_correction_T_max 0.4645 _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 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1983 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0686 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 25.98 _reflns_number_total 1064 _reflns_number_gt 1007 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _refine_special_details ; Platon suggests missed symmetry however no suitable higher symmetry structure could be found. The large residual electron density peak may be unrefined solvent/water but attempts to model this failed. Some atoms have been refined isotropically as refining them anisotropically leads to non-positive-definites. Although the maximum shift/error and R1 and wR2 are large for this compound (due to reasons above), the relative structure of the compound is not in doubt. 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^)+(0.0000P)^2^+85.9886P] 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 calc _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1064 _refine_ls_number_parameters 68 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1045 _refine_ls_R_factor_gt 0.1014 _refine_ls_wR_factor_ref 0.2542 _refine_ls_wR_factor_gt 0.2528 _refine_ls_goodness_of_fit_ref 1.222 _refine_ls_restrained_S_all 1.222 _refine_ls_shift/su_max 4.663 _refine_ls_shift/su_mean 0.069 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 Br1 Br 0.52910(12) 0.2304(3) -0.6107(2) 0.0095(6) Uani 1 1 d . . . Br2 Br 0.73623(12) -0.2331(3) -0.5082(2) 0.0099(6) Uani 1 1 d . . . C1 C 0.7702(11) 0.182(2) -0.237(2) 0.000(3) Uiso 1 1 d . . . C2 C 0.7650(13) 0.369(3) -0.247(3) 0.008(4) Uiso 1 1 d . . . C4 C 0.9566(14) 0.350(3) -0.156(3) 0.015(5) Uani 1 1 d . . . H4 H 1.0208 0.4150 -0.1340 0.017 Uiso 1 1 calc R . . C5 C 0.9585(14) 0.166(3) -0.139(3) 0.012(4) Uiso 1 1 d . . . H5 H 1.0242 0.1064 -0.0963 0.014 Uiso 1 1 calc R . . N2 N 0.6682(12) 0.451(3) -0.312(3) 0.018(5) Uani 1 1 d . . . H2A H 0.6199 0.3695 -0.3665 0.027 Uiso 1 1 calc R . . H2B H 0.6739 0.5410 -0.3745 0.027 Uiso 1 1 calc R . . H2C H 0.6470 0.4983 -0.2382 0.027 Uiso 1 1 calc R . . N1 N 0.6696(11) 0.057(2) -0.273(2) 0.010(3) Uiso 1 1 d . . . H1A H 0.6137 0.1226 -0.2705 0.015 Uiso 1 1 calc R . . H1B H 0.6833 -0.0324 -0.2028 0.015 Uiso 1 1 calc R . . H1C H 0.6542 0.0073 -0.3669 0.015 Uiso 1 1 calc R . . C6 C 0.8627(13) 0.065(3) -0.184(3) 0.013(5) Uani 1 1 d . . . H6 H 0.8596 -0.0620 -0.1798 0.016 Uiso 1 1 calc R . . C3 C 0.8616(14) 0.439(3) -0.205(3) 0.012(4) Uiso 1 1 d . . . H3 H 0.8652 0.5657 -0.2095 0.015 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 Br1 0.0039(9) 0.0152(11) 0.0088(13) 0.0035(8) 0.0012(6) 0.0057(6) Br2 0.0075(9) 0.0139(11) 0.0077(13) -0.0028(8) 0.0018(6) -0.0066(6) C4 0.005(8) 0.018(12) 0.024(15) -0.008(10) 0.010(7) -0.004(7) N2 0.007(7) 0.028(11) 0.020(14) 0.009(8) 0.006(7) -0.002(6) C6 0.012(9) 0.006(11) 0.018(16) 0.002(8) 0.001(7) 0.002(6) _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 C1 C2 1.39(3) . ? C1 C6 1.46(2) . ? C1 N1 1.59(2) . ? C2 C3 1.33(3) . ? C2 N2 1.38(2) . ? C4 C3 1.37(3) . ? C4 C5 1.38(3) . ? C5 C6 1.43(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 C2 C1 C6 129.4(15) . . ? C2 C1 N1 123.7(13) . . ? C6 C1 N1 106.8(14) . . ? C3 C2 N2 130(2) . . ? C3 C2 C1 110.4(16) . . ? N2 C2 C1 119.5(16) . . ? C3 C4 C5 119.6(18) . . ? C4 C5 C6 120.8(18) . . ? C5 C6 C1 111.4(17) . . ? C2 C3 C4 128(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 3(4) . . . . ? N1 C1 C2 C3 178(2) . . . . ? C6 C1 C2 N2 175(2) . . . . ? N1 C1 C2 N2 -10(3) . . . . ? C3 C4 C5 C6 6(4) . . . . ? C4 C5 C6 C1 -4(3) . . . . ? C2 C1 C6 C5 -1(4) . . . . ? N1 C1 C6 C5 -176(2) . . . . ? N2 C2 C3 C4 -172(3) . . . . ? C1 C2 C3 C4 -1(4) . . . . ? C5 C4 C3 C2 -3(4) . . . . ? 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 N2 H2A Br1 0.91 2.43 3.24(2) 147.7 . N2 H2A N1 0.91 2.50 2.96(3) 112.0 . N2 H2B Br2 0.91 2.42 3.310(19) 165.6 1_565 N2 H2C Br2 0.91 2.72 3.41(2) 133.4 4_566 N2 H2C Br1 0.91 2.87 3.382(19) 117.5 4_566 N1 H1A Br1 0.91 2.44 3.238(17) 146.2 4_566 N1 H1B Br2 0.91 2.45 3.359(19) 175.1 4_556 N1 H1C Br2 0.91 2.69 3.428(19) 138.9 . N1 H1C Br1 0.91 2.86 3.35(2) 114.6 . _diffrn_measured_fraction_theta_max 0.611 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.611 _refine_diff_density_max 3.948 _refine_diff_density_min -3.706 _refine_diff_density_rms 0.309 data_1c _database_code_depnum_ccdc_archive 'CCDC 299856' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, Cl2' _chemical_formula_sum 'C6 H10 Cl2 N2' _chemical_formula_weight 181.06 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 7.3184(6) _cell_length_b 14.5495(9) _cell_length_c 7.8594(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.794(5) _cell_angle_gamma 90.00 _cell_volume 833.93(11) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.705 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5390 _exptl_absorpt_correction_T_max 0.8718 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2797 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 25.96 _reflns_number_total 814 _reflns_number_gt 746 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _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^)+(0.0000P)^2^+1.5911P] 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 calc _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 814 _refine_ls_number_parameters 46 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0749 _refine_ls_wR_factor_gt 0.0565 _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_restrained_S_all 1.192 _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 Cl1 Cl 0.02436(6) 0.17565(3) 0.48744(6) 0.01548(17) Uani 1 1 d . . . N1 N -0.3118(2) 0.16451(10) 0.7038(2) 0.0135(4) Uani 1 1 d . . . H1A H -0.2579 0.1828 0.8067 0.016 Uiso 1 1 calc R . . H1B H -0.3919 0.2085 0.6619 0.016 Uiso 1 1 calc R . . H1C H -0.2242 0.1558 0.6297 0.016 Uiso 1 1 calc R . . C1 C -0.4109(3) 0.07805(12) 0.7246(2) 0.0126(4) Uani 1 1 d . . . C2 C -0.3215(3) -0.00429(13) 0.6986(3) 0.0162(4) Uani 1 1 d . . . H2 H -0.2002 -0.0043 0.6639 0.019 Uiso 1 1 calc R . . C3 C -0.4115(3) -0.08694(13) 0.7238(3) 0.0194(4) Uani 1 1 d . . . H3 H -0.3517 -0.1436 0.7052 0.023 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 Cl1 0.0128(3) 0.0188(3) 0.0151(3) 0.00212(17) 0.00270(18) 0.00184(17) N1 0.0119(8) 0.0146(8) 0.0143(8) 0.0010(6) 0.0023(6) -0.0003(6) C1 0.0136(9) 0.0134(9) 0.0106(9) 0.0002(7) 0.0004(7) -0.0012(7) C2 0.0139(9) 0.0187(10) 0.0162(10) 0.0002(7) 0.0029(8) 0.0022(7) C3 0.0220(11) 0.0134(10) 0.0229(10) -0.0005(8) 0.0016(8) 0.0052(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.468(2) . ? C1 C2 1.388(3) . ? C1 C1 1.395(4) 2_456 ? C2 C3 1.393(3) . ? C3 C3 1.392(4) 2_456 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C1 120.35(11) . 2_456 ? C2 C1 N1 118.67(17) . . ? C1 C1 N1 120.94(10) 2_456 . ? C1 C2 C3 119.33(18) . . ? C3 C3 C2 120.31(11) 2_456 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 -0.1(3) 2_456 . . . ? N1 C1 C2 C3 177.74(18) . . . . ? C1 C2 C3 C3 -0.6(4) . . . 2_456 ? 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 Cl1 0.91 2.26 3.0804(17) 150.5 2_556 N1 H1B Cl1 0.91 2.23 3.1137(16) 163.8 7_456 N1 H1C Cl1 0.91 2.23 3.1095(17) 161.7 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.96 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.360 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.082 data_1d _database_code_depnum_ccdc_archive 'CCDC 299857' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, 2(C2 F3 O2)' _chemical_formula_sum 'C10 H10 F6 N2 O4' _chemical_formula_weight 336.20 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.649(3) _cell_length_b 8.6558(9) _cell_length_c 11.7964(13) _cell_angle_alpha 90.00 _cell_angle_beta 102.093(6) _cell_angle_gamma 90.00 _cell_volume 2560.9(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.744 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9460 _exptl_absorpt_correction_T_max 0.9815 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KAppa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6459 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_sigmaI/netI 0.0746 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2815 _reflns_number_gt 2213 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _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^)+(0.0120P)^2^+1.9336P] 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 fixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0051(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2815 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0891 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 F1 F 0.30063(5) -0.24301(14) 0.85220(11) 0.0314(3) Uani 1 1 d . . . F2 F 0.23403(5) -0.39235(12) 0.78938(11) 0.0267(3) Uani 1 1 d . . . F3 F 0.25786(4) -0.22474(12) 0.67539(10) 0.0220(3) Uani 1 1 d . . . F4 F -0.05927(4) -0.20449(12) 0.90122(10) 0.0221(3) Uani 1 1 d . . . F5 F -0.00815(5) -0.31017(13) 1.04910(11) 0.0276(3) Uani 1 1 d . . . F6 F 0.00061(5) -0.36808(13) 0.87688(12) 0.0328(3) Uani 1 1 d . . . O1 O 0.22487(5) -0.07577(14) 0.91798(11) 0.0187(3) Uani 1 1 d . . . O2 O 0.17100(5) -0.11103(14) 0.74265(11) 0.0158(3) Uani 1 1 d . . . O3 O 0.07595(5) -0.13916(14) 1.01285(11) 0.0160(3) Uani 1 1 d . . . O4 O 0.01750(5) -0.01557(15) 0.87426(11) 0.0190(3) Uani 1 1 d . . . N1 N 0.09193(6) 0.09703(18) 0.75798(14) 0.0138(3) Uani 1 1 d . . . N2 N 0.15067(6) 0.09400(18) 0.99678(14) 0.0133(3) Uani 1 1 d . . . C1 C 0.11001(7) 0.24151(19) 0.81890(16) 0.0126(4) Uani 1 1 d . . . C2 C 0.13707(7) 0.23978(19) 0.93404(16) 0.0128(4) Uani 1 1 d . . . C3 C 0.15280(7) 0.3780(2) 0.99028(17) 0.0169(4) Uani 1 1 d . . . H3 H 0.1716 0.3778 1.0688 0.020 Uiso 1 1 calc R . . C4 C 0.14106(8) 0.5166(2) 0.93146(18) 0.0211(4) Uani 1 1 d . . . H4 H 0.1516 0.6114 0.9701 0.025 Uiso 1 1 calc R . . C5 C 0.11418(8) 0.5175(2) 0.81715(17) 0.0192(4) Uani 1 1 d . . . H5 H 0.1063 0.6128 0.7773 0.023 Uiso 1 1 calc R . . C6 C 0.09861(7) 0.3801(2) 0.76048(16) 0.0165(4) Uani 1 1 d . . . H6 H 0.0802 0.3807 0.6817 0.020 Uiso 1 1 calc R . . C7 C 0.21250(7) -0.13172(19) 0.81978(16) 0.0128(4) Uani 1 1 d . . . C8 C 0.25223(7) -0.2478(2) 0.78462(16) 0.0161(4) Uani 1 1 d . . . C9 C 0.03204(7) -0.1214(2) 0.94474(16) 0.0130(4) Uani 1 1 d . . . C10 C -0.00909(7) -0.2519(2) 0.94415(17) 0.0171(4) Uani 1 1 d . . . H11 H 0.0781(9) 0.118(2) 0.678(2) 0.028(6) Uiso 1 1 d . . . H12 H 0.0652(11) 0.052(3) 0.789(2) 0.037(7) Uiso 1 1 d . . . H13 H 0.1189(10) 0.027(2) 0.764(2) 0.024(6) Uiso 1 1 d . . . H21 H 0.1759(10) 0.039(2) 0.968(2) 0.031(6) Uiso 1 1 d . . . H22 H 0.1641(9) 0.112(2) 1.076(2) 0.027(6) Uiso 1 1 d . . . H23 H 0.1210(10) 0.028(3) 0.990(2) 0.032(6) 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 F1 0.0141(6) 0.0509(8) 0.0261(7) -0.0134(6) -0.0030(5) 0.0087(6) F2 0.0310(7) 0.0151(5) 0.0383(8) 0.0010(5) 0.0170(6) 0.0032(5) F3 0.0226(6) 0.0279(6) 0.0179(6) -0.0018(5) 0.0097(5) 0.0013(5) F4 0.0106(5) 0.0258(6) 0.0282(7) 0.0000(5) 0.0004(5) -0.0011(4) F5 0.0225(6) 0.0287(6) 0.0308(7) 0.0137(5) 0.0037(6) -0.0048(5) F6 0.0250(7) 0.0227(6) 0.0509(9) -0.0197(6) 0.0083(6) -0.0032(5) O1 0.0192(7) 0.0225(7) 0.0141(7) -0.0035(6) 0.0025(6) 0.0029(6) O2 0.0135(6) 0.0185(6) 0.0146(7) -0.0001(5) 0.0009(6) 0.0016(5) O3 0.0129(6) 0.0189(6) 0.0156(7) -0.0003(5) 0.0014(6) 0.0008(5) O4 0.0163(7) 0.0234(7) 0.0175(7) 0.0066(6) 0.0037(6) 0.0009(5) N1 0.0130(8) 0.0154(8) 0.0124(8) -0.0005(6) 0.0012(7) -0.0004(6) N2 0.0131(7) 0.0157(8) 0.0105(8) 0.0000(6) 0.0013(7) -0.0003(6) C1 0.0106(8) 0.0135(8) 0.0139(9) -0.0024(7) 0.0034(7) -0.0006(7) C2 0.0107(8) 0.0142(8) 0.0140(9) 0.0029(7) 0.0036(7) 0.0011(7) C3 0.0162(9) 0.0201(9) 0.0126(9) -0.0018(8) -0.0007(8) -0.0001(7) C4 0.0222(10) 0.0145(9) 0.0250(11) -0.0026(8) 0.0014(9) -0.0003(8) C5 0.0192(10) 0.0152(9) 0.0217(10) 0.0048(8) 0.0008(8) 0.0000(7) C6 0.0143(9) 0.0211(9) 0.0128(9) 0.0027(8) 0.0000(8) 0.0003(7) C7 0.0131(9) 0.0116(8) 0.0146(9) 0.0011(7) 0.0053(8) -0.0019(7) C8 0.0135(9) 0.0193(9) 0.0148(9) -0.0011(8) 0.0016(8) 0.0002(7) C9 0.0126(8) 0.0155(9) 0.0116(9) -0.0044(7) 0.0039(7) 0.0007(7) C10 0.0142(9) 0.0174(9) 0.0187(10) -0.0017(8) 0.0014(8) 0.0002(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 F1 C8 1.328(2) . ? F2 C8 1.341(2) . ? F3 C8 1.341(2) . ? F4 C10 1.345(2) . ? F5 C10 1.332(2) . ? F6 C10 1.336(2) . ? O1 C7 1.234(2) . ? O2 C7 1.260(2) . ? O3 C9 1.248(2) . ? O4 C9 1.241(2) . ? N1 C1 1.468(2) . ? N2 C2 1.467(2) . ? C1 C6 1.384(2) . ? C1 C2 1.390(3) . ? C2 C3 1.387(2) . ? C3 C4 1.387(3) . ? C4 C5 1.380(3) . ? C5 C6 1.382(3) . ? C7 C8 1.548(2) . ? C9 C10 1.545(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 C6 C1 C2 120.41(17) . . ? C6 C1 N1 118.84(17) . . ? C2 C1 N1 120.73(16) . . ? C3 C2 C1 119.60(16) . . ? C3 C2 N2 119.09(17) . . ? C1 C2 N2 121.29(16) . . ? C4 C3 C2 119.73(18) . . ? C5 C4 C3 120.38(18) . . ? C4 C5 C6 120.15(17) . . ? C5 C6 C1 119.72(18) . . ? O1 C7 O2 129.35(16) . . ? O1 C7 C8 116.87(16) . . ? O2 C7 C8 113.75(15) . . ? F1 C8 F2 107.08(15) . . ? F1 C8 F3 107.27(14) . . ? F2 C8 F3 106.70(14) . . ? F1 C8 C7 113.83(15) . . ? F2 C8 C7 109.87(14) . . ? F3 C8 C7 111.73(15) . . ? O4 C9 O3 128.78(16) . . ? O4 C9 C10 115.33(16) . . ? O3 C9 C10 115.83(15) . . ? F5 C10 F6 107.32(15) . . ? F5 C10 F4 107.15(14) . . ? F6 C10 F4 106.78(16) . . ? F5 C10 C9 113.16(16) . . ? F6 C10 C9 109.95(14) . . ? F4 C10 C9 112.16(14) . . ? 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 C6 C1 C2 C3 -0.2(3) . . . . ? N1 C1 C2 C3 -178.74(15) . . . . ? C6 C1 C2 N2 -178.54(15) . . . . ? N1 C1 C2 N2 2.9(2) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? N2 C2 C3 C4 178.87(16) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C4 C5 C6 C1 0.1(3) . . . . ? C2 C1 C6 C5 -0.1(2) . . . . ? N1 C1 C6 C5 178.47(16) . . . . ? O1 C7 C8 F1 -16.5(2) . . . . ? O2 C7 C8 F1 164.94(15) . . . . ? O1 C7 C8 F2 103.54(18) . . . . ? O2 C7 C8 F2 -74.99(19) . . . . ? O1 C7 C8 F3 -138.22(16) . . . . ? O2 C7 C8 F3 43.2(2) . . . . ? O4 C9 C10 F5 -144.70(15) . . . . ? O3 C9 C10 F5 37.8(2) . . . . ? O4 C9 C10 F6 95.32(18) . . . . ? O3 C9 C10 F6 -82.23(19) . . . . ? O4 C9 C10 F4 -23.3(2) . . . . ? O3 C9 C10 F4 159.12(15) . . . . ? 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 H13 O2 0.91(2) 1.85(2) 2.746(2) 168(2) . N1 H12 O4 0.93(3) 1.84(3) 2.752(2) 169(2) . N1 H11 O3 0.95(3) 1.95(2) 2.858(2) 159(2) 6 N2 H23 O3 0.94(3) 1.91(2) 2.817(2) 162(2) . N2 H22 O2 0.94(2) 1.94(2) 2.841(2) 161(2) 6_556 N2 H22 F3 0.94(2) 2.63(2) 3.294(2) 128.0(17) 6_556 N2 H21 O1 0.92(2) 1.80(2) 2.718(2) 177(2) . _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.295 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.058 data_1e _database_code_depnum_ccdc_archive 'CCDC 299858' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, (H2 P O4)2' _chemical_formula_sum 'C6 H14 N2 O8 P2' _chemical_formula_weight 304.13 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' P P 0.1023 0.0942 '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 6.6630(2) _cell_length_b 9.8070(6) _cell_length_c 10.1060(6) _cell_angle_alpha 66.947(3) _cell_angle_beta 73.474(4) _cell_angle_gamma 73.262(4) _cell_volume 570.74(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.770 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.419 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8502 _exptl_absorpt_correction_T_max 0.9024 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4490 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0520 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2620 _reflns_number_gt 2324 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _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^)+(0.0104P)^2^+0.4651P] 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 fixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.031(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2620 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 P1 P 0.72351(6) 0.74759(5) 0.99978(5) 0.00950(13) Uani 1 1 d . . . P2 P 0.83287(6) 0.40615(5) 0.72273(5) 0.01068(14) Uani 1 1 d . . . O1 O 0.87826(18) 0.66158(14) 0.89389(14) 0.0135(3) Uani 1 1 d . . . O2 O 0.69312(19) 0.62571(14) 1.15761(13) 0.0142(3) Uani 1 1 d . . . O3 O 0.50376(18) 0.80216(14) 0.96075(13) 0.0127(3) Uani 1 1 d . . . O4 O 0.83458(18) 0.86326(14) 0.99345(13) 0.0139(3) Uani 1 1 d . . . O5 O 0.72216(19) 0.49539(14) 0.82450(14) 0.0162(3) Uani 1 1 d . . . O6 O 0.80294(19) 0.23765(14) 0.80394(14) 0.0142(3) Uani 1 1 d . . . O7 O 1.07095(18) 0.39978(15) 0.66866(13) 0.0164(3) Uani 1 1 d . . . O8 O 0.72074(19) 0.46591(16) 0.58841(15) 0.0173(3) Uani 1 1 d . . . N1 N 0.1635(2) 0.98689(18) 0.82072(17) 0.0120(3) Uani 1 1 d . . . N2 N 0.3148(2) 0.68048(17) 0.82906(17) 0.0124(3) Uani 1 1 d . . . C1 C 0.2221(2) 0.95205(19) 0.68540(18) 0.0109(3) Uani 1 1 d . . . C2 C 0.2931(2) 0.80309(19) 0.68945(19) 0.0108(3) Uani 1 1 d . . . C3 C 0.3413(3) 0.7681(2) 0.5622(2) 0.0148(4) Uani 1 1 d . . . H3 H 0.3870 0.6659 0.5656 0.018 Uiso 1 1 calc R . . C4 C 0.3219(3) 0.8843(2) 0.4299(2) 0.0170(4) Uani 1 1 d . . . H4 H 0.3542 0.8614 0.3422 0.020 Uiso 1 1 calc R . . C5 C 0.2557(3) 1.0338(2) 0.4246(2) 0.0168(4) Uani 1 1 d . . . H5 H 0.2453 1.1127 0.3333 0.020 Uiso 1 1 calc R . . C6 C 0.2045(3) 1.0682(2) 0.5527(2) 0.0140(4) Uani 1 1 d . . . H6A H 0.1578 1.1704 0.5494 0.017 Uiso 1 1 calc R . . H1 H 0.823(5) 0.600(3) 0.876(3) 0.055(9) Uiso 1 1 d . . . H2 H 0.782(5) 0.619(3) 1.212(3) 0.049(8) Uiso 1 1 d . . . H6 H 0.696(4) 0.227(3) 0.875(3) 0.038(7) Uiso 1 1 d . . . H8 H 0.791(4) 0.510(3) 0.508(3) 0.039(8) Uiso 1 1 d . . . H11 H 0.271(4) 0.959(2) 0.868(2) 0.017(5) Uiso 1 1 d . . . H12 H 0.118(4) 1.086(3) 0.804(2) 0.022(6) Uiso 1 1 d . . . H13 H 0.050(4) 0.936(3) 0.887(3) 0.032(6) Uiso 1 1 d . . . H21 H 0.361(4) 0.709(3) 0.884(3) 0.028(6) Uiso 1 1 d . . . H22 H 0.190(4) 0.651(3) 0.870(3) 0.026(6) Uiso 1 1 d . . . H23 H 0.411(4) 0.599(3) 0.816(3) 0.039(7) 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 P1 0.0097(2) 0.0101(2) 0.0098(2) -0.00353(17) -0.00307(15) -0.00217(15) P2 0.0087(2) 0.0130(2) 0.0109(2) -0.00531(17) -0.00241(15) -0.00063(15) O1 0.0113(6) 0.0157(6) 0.0170(6) -0.0098(5) -0.0021(5) -0.0025(5) O2 0.0160(6) 0.0166(6) 0.0107(6) -0.0003(5) -0.0062(5) -0.0068(5) O3 0.0110(5) 0.0144(6) 0.0130(6) -0.0044(5) -0.0046(4) -0.0011(4) O4 0.0155(6) 0.0152(6) 0.0144(6) -0.0067(5) -0.0020(5) -0.0067(5) O5 0.0149(6) 0.0183(7) 0.0205(7) -0.0133(6) 0.0000(5) -0.0042(5) O6 0.0137(6) 0.0118(6) 0.0145(6) -0.0049(5) -0.0016(5) 0.0007(5) O7 0.0102(6) 0.0271(7) 0.0112(6) -0.0060(5) -0.0020(4) -0.0032(5) O8 0.0128(6) 0.0234(7) 0.0123(7) 0.0004(5) -0.0049(5) -0.0055(5) N1 0.0130(7) 0.0114(8) 0.0127(7) -0.0061(6) -0.0038(6) 0.0002(6) N2 0.0117(7) 0.0104(7) 0.0154(8) -0.0046(6) -0.0040(6) -0.0010(6) C1 0.0082(7) 0.0138(8) 0.0121(8) -0.0052(7) -0.0023(6) -0.0025(6) C2 0.0089(7) 0.0115(8) 0.0125(8) -0.0039(7) -0.0030(6) -0.0019(6) C3 0.0125(8) 0.0181(9) 0.0187(9) -0.0109(7) -0.0023(6) -0.0042(6) C4 0.0131(8) 0.0286(10) 0.0142(9) -0.0109(8) -0.0026(6) -0.0062(7) C5 0.0123(8) 0.0246(10) 0.0112(8) -0.0009(7) -0.0035(6) -0.0064(7) C6 0.0102(7) 0.0130(8) 0.0165(9) -0.0026(7) -0.0036(6) -0.0013(6) _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 P1 O4 1.4961(12) . ? P1 O3 1.5159(12) . ? P1 O2 1.5736(13) . ? P1 O1 1.5806(13) . ? P2 O5 1.5064(13) . ? P2 O7 1.5151(12) . ? P2 O8 1.5640(13) . ? P2 O6 1.5743(13) . ? N1 C1 1.458(2) . ? N2 C2 1.464(2) . ? C1 C6 1.388(2) . ? C1 C2 1.388(2) . ? C2 C3 1.386(2) . ? C3 C4 1.387(3) . ? C4 C5 1.387(3) . ? C5 C6 1.389(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 O4 P1 O3 117.88(7) . . ? O4 P1 O2 111.19(7) . . ? O3 P1 O2 105.12(7) . . ? O4 P1 O1 106.37(7) . . ? O3 P1 O1 109.21(7) . . ? O2 P1 O1 106.58(7) . . ? O5 P2 O7 116.19(7) . . ? O5 P2 O8 110.05(7) . . ? O7 P2 O8 109.41(7) . . ? O5 P2 O6 108.92(7) . . ? O7 P2 O6 106.52(7) . . ? O8 P2 O6 105.12(7) . . ? C6 C1 C2 120.11(16) . . ? C6 C1 N1 119.79(15) . . ? C2 C1 N1 120.10(15) . . ? C3 C2 C1 120.62(16) . . ? C3 C2 N2 119.15(15) . . ? C1 C2 N2 120.23(15) . . ? C2 C3 C4 119.12(16) . . ? C3 C4 C5 120.56(17) . . ? C4 C5 C6 120.13(17) . . ? C1 C6 C5 119.44(17) . . ? 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 C6 C1 C2 C3 -1.8(2) . . . . ? N1 C1 C2 C3 177.48(14) . . . . ? C6 C1 C2 N2 179.09(15) . . . . ? N1 C1 C2 N2 -1.6(2) . . . . ? C1 C2 C3 C4 1.3(2) . . . . ? N2 C2 C3 C4 -179.61(15) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? C3 C4 C5 C6 -1.1(3) . . . . ? C2 C1 C6 C5 0.9(2) . . . . ? N1 C1 C6 C5 -178.44(14) . . . . ? C4 C5 C6 C1 0.6(2) . . . . ? 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 O1 H1 O5 0.88(3) 1.67(3) 2.5527(18) 174(3) . O2 H2 O7 0.88(3) 1.69(3) 2.5723(17) 174(3) 2_767 O6 H6 O3 0.85(3) 1.79(3) 2.6365(18) 173(3) 2_667 O6 H6 O2 0.85(3) 2.62(3) 3.1619(17) 122(2) 2_667 O8 H8 O7 0.83(3) 1.77(3) 2.5947(18) 176(3) 2_766 N1 H13 O4 0.97(3) 1.68(3) 2.6491(19) 174(2) 1_455 N1 H12 O6 0.89(2) 2.20(2) 2.8897(19) 134.1(19) 1_465 N1 H11 O3 0.89(2) 1.99(2) 2.8063(19) 151(2) . N2 H23 O5 0.90(3) 2.04(3) 2.7963(19) 142(2) . N2 H23 O2 0.90(3) 2.40(3) 2.968(2) 122(2) 2_667 N2 H22 O1 0.89(3) 2.00(3) 2.8385(19) 156(2) 1_455 N2 H21 O3 0.87(3) 1.95(3) 2.800(2) 166(2) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.276 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.068 data_1f _database_code_depnum_ccdc_archive 'CCDC 299859' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, 2(N O3)' _chemical_formula_sum 'C6 H10 N4 O6' _chemical_formula_weight 234.18 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 12.6849(14) _cell_length_b 7.9519(6) _cell_length_c 10.3950(10) _cell_angle_alpha 90.00 _cell_angle_beta 105.817(5) _cell_angle_gamma 90.00 _cell_volume 1008.83(17) _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 block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.138 _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 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5968 _diffrn_reflns_av_R_equivalents 0.0835 _diffrn_reflns_av_sigmaI/netI 0.0715 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1768 _reflns_number_gt 1405 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _refine_special_details ; The large R1 and wR2 values may be due to unresolved twinning in the data. The connectivity of the structure is unaffected by this. 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^)+(0.2000P)^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 calc _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.21(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1768 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1657 _refine_ls_R_factor_gt 0.1472 _refine_ls_wR_factor_ref 0.4357 _refine_ls_wR_factor_gt 0.4231 _refine_ls_goodness_of_fit_ref 1.866 _refine_ls_restrained_S_all 1.866 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2301(4) -0.2401(5) 0.6512(5) 0.0208(14) Uani 1 1 d . . . O2 O 0.2519(4) -0.3705(5) 0.8405(5) 0.0226(14) Uani 1 1 d . . . O3 O 0.2083(5) -0.1064(6) 0.8250(5) 0.0340(16) Uani 1 1 d . . . O4 O -0.0049(4) 0.1297(6) 0.6327(4) 0.0229(14) Uani 1 1 d . . . O5 O 0.1222(4) 0.2577(5) 0.7850(5) 0.0192(14) Uani 1 1 d . . . O6 O -0.0026(4) 0.1127(6) 0.8418(5) 0.0242(14) Uani 1 1 d . . . N1 N 0.1773(4) 0.4316(6) 0.5735(5) 0.0152(14) Uani 1 1 d . . . H1A H 0.1933 0.5378 0.6054 0.018 Uiso 1 1 calc R . . H1B H 0.1387 0.3774 0.6230 0.018 Uiso 1 1 calc R . . H1C H 0.1366 0.4363 0.4867 0.018 Uiso 1 1 calc R . . N2 N 0.1795(4) 0.0674(6) 0.5370(5) 0.0151(14) Uani 1 1 d . . . H2A H 0.1569 0.0501 0.4471 0.018 Uiso 1 1 calc R . . H2B H 0.1267 0.1240 0.5634 0.018 Uiso 1 1 calc R . . H2C H 0.1921 -0.0335 0.5798 0.018 Uiso 1 1 calc R . . N3 N 0.2296(5) -0.2400(6) 0.7767(6) 0.0187(15) Uani 1 1 d . . . N4 N 0.0368(4) 0.1659(7) 0.7529(6) 0.0182(15) Uani 1 1 d . . . C1 C 0.2797(5) 0.3398(8) 0.5820(7) 0.0167(16) Uani 1 1 d . . . C2 C 0.3756(6) 0.4328(9) 0.6061(7) 0.0220(17) Uani 1 1 d . . . H2 H 0.3743 0.5518 0.6137 0.026 Uiso 1 1 calc R . . C3 C 0.4747(6) 0.3473(9) 0.6190(7) 0.0234(18) Uani 1 1 d . . . H3 H 0.5412 0.4089 0.6345 0.028 Uiso 1 1 calc R . . C4 C 0.4762(6) 0.1737(9) 0.6092(7) 0.0219(17) Uani 1 1 d . . . H4 H 0.5438 0.1169 0.6188 0.026 Uiso 1 1 calc R . . C5 C 0.3796(5) 0.0821(8) 0.5857(6) 0.0194(17) Uani 1 1 d . . . H5 H 0.3810 -0.0371 0.5802 0.023 Uiso 1 1 calc R . . C6 C 0.2807(5) 0.1664(8) 0.5701(6) 0.0163(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.027(3) 0.016(2) 0.021(3) 0.0007(16) 0.009(2) -0.0006(17) O2 0.019(3) 0.022(3) 0.023(3) 0.008(2) 0.000(2) 0.0001(18) O3 0.046(4) 0.030(3) 0.028(3) -0.008(2) 0.013(3) 0.006(2) O4 0.019(3) 0.035(3) 0.015(3) -0.0071(19) 0.005(2) -0.0041(19) O5 0.018(3) 0.020(3) 0.019(3) -0.0033(16) 0.003(2) -0.0025(17) O6 0.018(3) 0.035(3) 0.020(3) 0.006(2) 0.006(2) 0.0007(19) N1 0.015(3) 0.014(3) 0.017(3) 0.003(2) 0.005(2) -0.001(2) N2 0.014(3) 0.013(3) 0.018(3) -0.002(2) 0.002(2) -0.001(2) N3 0.014(3) 0.018(3) 0.023(4) -0.002(2) 0.003(2) 0.000(2) N4 0.013(3) 0.021(3) 0.023(3) -0.002(2) 0.007(2) 0.002(2) C1 0.018(3) 0.016(3) 0.018(3) -0.004(2) 0.009(3) 0.001(2) C2 0.023(4) 0.020(3) 0.023(4) -0.002(3) 0.007(3) -0.002(3) C3 0.018(4) 0.031(4) 0.022(4) -0.002(3) 0.005(3) -0.003(3) C4 0.019(4) 0.025(4) 0.022(4) 0.000(3) 0.006(3) 0.004(3) C5 0.017(4) 0.022(3) 0.020(4) -0.003(3) 0.006(3) 0.005(3) C6 0.014(3) 0.022(3) 0.013(3) 0.000(2) 0.003(2) 0.000(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 O1 N3 1.307(9) . ? O2 N3 1.222(7) . ? O3 N3 1.237(7) . ? O4 N4 1.250(7) . ? O5 N4 1.274(7) . ? O6 N4 1.239(7) . ? N1 C1 1.472(8) . ? N2 C6 1.464(8) . ? C1 C6 1.385(10) . ? C1 C2 1.388(9) . ? C2 C3 1.403(9) . ? C3 C4 1.385(11) . ? C4 C5 1.388(9) . ? C5 C6 1.392(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 N3 O3 123.6(6) . . ? O2 N3 O1 118.5(5) . . ? O3 N3 O1 117.9(5) . . ? O6 N4 O4 121.4(5) . . ? O6 N4 O5 119.2(5) . . ? O4 N4 O5 119.4(5) . . ? C6 C1 C2 121.2(5) . . ? C6 C1 N1 121.2(5) . . ? C2 C1 N1 117.6(5) . . ? C1 C2 C3 118.5(6) . . ? C4 C3 C2 120.4(6) . . ? C3 C4 C5 120.5(6) . . ? C4 C5 C6 119.5(6) . . ? C1 C6 C5 119.9(6) . . ? C1 C6 N2 121.8(5) . . ? C5 C6 N2 118.2(6) . . ? 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 C6 C1 C2 C3 -0.3(10) . . . . ? N1 C1 C2 C3 178.0(6) . . . . ? C1 C2 C3 C4 -0.7(10) . . . . ? C2 C3 C4 C5 0.5(10) . . . . ? C3 C4 C5 C6 0.8(10) . . . . ? C2 C1 C6 C5 1.6(9) . . . . ? N1 C1 C6 C5 -176.6(6) . . . . ? C2 C1 C6 N2 -176.4(6) . . . . ? N1 C1 C6 N2 5.4(9) . . . . ? C4 C5 C6 C1 -1.8(9) . . . . ? C4 C5 C6 N2 176.2(6) . . . . ? 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 O1 0.91 1.86 2.761(6) 173.0 1_565 N1 H1A N3 0.91 2.46 3.310(7) 155.4 1_565 N1 H1A O2 0.91 2.46 3.106(7) 127.9 1_565 N1 H1B O5 0.91 1.99 2.842(7) 154.2 . N1 H1B N4 0.91 2.70 3.596(8) 169.6 . N1 H1C O6 0.91 2.02 2.852(7) 151.0 4_565 N1 H1C O3 0.91 2.51 3.051(7) 118.3 4_565 N1 H1C N4 0.91 2.55 3.413(8) 158.9 4_565 N1 H1C O5 0.91 2.57 3.256(7) 132.8 4_565 N2 H2A O5 0.91 2.23 2.878(7) 127.9 4_565 N2 H2A O2 0.91 2.33 2.914(7) 121.4 4 N2 H2A O4 0.91 2.36 2.889(6) 116.8 3_556 N2 H2B O4 0.91 1.99 2.824(7) 151.6 . N2 H2B O5 0.91 2.55 3.239(7) 132.7 . N2 H2B N4 0.91 2.55 3.339(8) 144.9 . N2 H2C O1 0.91 1.81 2.717(6) 172.0 . N2 H2C O3 0.91 2.57 3.227(8) 129.9 . N2 H2C N3 0.91 2.57 3.424(7) 157.6 . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.544 _refine_diff_density_min -0.909 _refine_diff_density_rms 0.311 data_1g _database_code_depnum_ccdc_archive 'CCDC 299860' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, SiF6' _chemical_formula_sum 'C6 H10 F6 N2 Si' _chemical_formula_weight 252.25 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' 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 P2/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 5.5242(2) _cell_length_b 11.1775(8) _cell_length_c 7.6086(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.75(3) _cell_angle_gamma 90.00 _cell_volume 469.77(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.783 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.312 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7883 _exptl_absorpt_correction_T_max 0.9402 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1922 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1001 _reflns_number_gt 924 _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 ? _computing_publication_material ? _refine_special_details ; The structure can be refined in Pmmn (as suggested by Platon) but R1 = 0.0759. In the monoclinic solution the anion is slightly offset compared to the cation, giving beta = 90.8 (>>90 for an otherwise precise structure). In Pmmn (with beta forced to be 90) the molecule is on a mirror and the offset manifests itself in elongated ellipsoids and the large R1 value. Therefore while the anion fits the Pmmn space group the cation does not therefore we believe the lower symmetry solution is the correct one. ; _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^)+(0.0377P)^2^+0.5465P] 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 calc _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.050(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1001 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 0.2500 0.13704(5) 0.2500 0.0106(2) Uani 1 2 d S . . F1 F 0.0310(2) 0.24076(9) 0.26070(14) 0.0160(3) Uani 1 1 d . . . F2 F 0.2241(2) 0.13529(10) 0.02898(14) 0.0187(3) Uani 1 1 d . . . F3 F 0.0347(2) 0.02876(9) 0.26063(15) 0.0175(3) Uani 1 1 d . . . N1 N 0.2578(3) -0.16139(13) 0.0566(2) 0.0124(3) Uani 1 1 d . . . H13 H 0.101(6) -0.136(2) 0.049(4) 0.029(7) Uiso 1 1 d . . . H12 H 0.318(5) -0.177(2) -0.045(4) 0.030(7) Uiso 1 1 d . . . H11 H 0.349(5) -0.104(2) 0.109(3) 0.027(7) Uiso 1 1 d . . . C1 C 0.2547(3) -0.27257(14) 0.1590(2) 0.0116(4) Uani 1 1 d . . . C2 C 0.2557(4) -0.38016(15) 0.0674(2) 0.0148(4) Uani 1 1 d . . . H2 H 0.2586 -0.3801 -0.0574 0.018 Uiso 1 1 calc R . . C3 C 0.2523(3) -0.48790(15) 0.1586(2) 0.0164(4) Uani 1 1 d . . . H3 H 0.2532 -0.5615 0.0961 0.020 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 0.0132(4) 0.0094(3) 0.0093(3) 0.000 0.0006(2) 0.000 F1 0.0174(6) 0.0119(5) 0.0188(6) 0.0008(4) 0.0032(4) 0.0036(4) F2 0.0173(6) 0.0292(6) 0.0096(5) -0.0027(4) -0.0001(4) 0.0023(4) F3 0.0142(6) 0.0115(5) 0.0267(6) 0.0001(4) -0.0001(4) -0.0015(4) N1 0.0160(8) 0.0116(7) 0.0097(7) 0.0004(5) 0.0010(5) -0.0003(6) C1 0.0127(9) 0.0108(8) 0.0114(9) 0.0013(6) 0.0009(6) -0.0002(6) C2 0.0186(10) 0.0135(8) 0.0122(8) -0.0017(6) 0.0008(6) -0.0001(6) C3 0.0191(10) 0.0108(8) 0.0193(10) -0.0029(6) 0.0018(7) -0.0001(6) _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 1.6786(11) 2 ? Si1 F1 1.6786(11) . ? Si1 F2 1.6860(11) 2 ? Si1 F2 1.6860(11) . ? Si1 F3 1.6993(11) . ? Si1 F3 1.6993(11) 2 ? N1 C1 1.467(2) . ? C1 C1 1.387(3) 2 ? C1 C2 1.390(2) . ? C2 C3 1.390(2) . ? C3 C3 1.392(4) 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 F1 Si1 F1 92.63(8) 2 . ? F1 Si1 F2 90.26(5) 2 2 ? F1 Si1 F2 90.65(5) . 2 ? F1 Si1 F2 90.65(5) 2 . ? F1 Si1 F2 90.26(5) . . ? F2 Si1 F2 178.68(8) 2 . ? F1 Si1 F3 178.27(6) 2 . ? F1 Si1 F3 89.10(5) . . ? F2 Si1 F3 89.69(6) 2 . ? F2 Si1 F3 89.37(6) . . ? F1 Si1 F3 89.10(5) 2 2 ? F1 Si1 F3 178.27(6) . 2 ? F2 Si1 F3 89.37(6) 2 2 ? F2 Si1 F3 89.69(6) . 2 ? F3 Si1 F3 89.17(8) . 2 ? C1 C1 C2 120.07(10) 2 . ? C1 C1 N1 122.09(9) 2 . ? C2 C1 N1 117.83(15) . . ? C3 C2 C1 119.97(16) . . ? C2 C3 C3 119.96(10) . 2 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 -1.4(3) 2 . . . ? N1 C1 C2 C3 -179.85(16) . . . . ? C1 C2 C3 C3 0.1(3) . . . 2 ? 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 H13 F2 0.91(3) 1.88(3) 2.748(2) 157(2) 3 N1 H12 F1 0.87(3) 2.03(3) 2.8674(19) 163(3) 4_655 N1 H12 F3 0.87(3) 2.53(3) 3.1145(19) 126(2) 4_655 N1 H11 F3 0.90(3) 1.89(3) 2.7791(19) 166(3) 2 _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.522 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.067 data_2a _database_code_depnum_ccdc_archive 'CCDC 299861' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, 2(BF4)' _chemical_formula_sum 'C6 H10 B2 F8 N2' _chemical_formula_weight 283.78 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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 7.2396(13) _cell_length_b 8.8215(16) _cell_length_c 9.4429(16) _cell_angle_alpha 73.712(11) _cell_angle_beta 74.877(9) _cell_angle_gamma 76.677(9) _cell_volume 550.70(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.711 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 0.196 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9435 _exptl_absorpt_correction_T_max 0.9807 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4105 _diffrn_reflns_av_R_equivalents 0.0730 _diffrn_reflns_av_sigmaI/netI 0.1446 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2518 _reflns_number_gt 1352 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _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^)+(0.0304P)^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 calc _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.030(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2518 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1463 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1349 _refine_ls_wR_factor_gt 0.1097 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 F1 F 0.4211(3) 1.2258(2) 0.3101(2) 0.0408(6) Uani 1 1 d . . . F2 F 0.4407(3) 0.9694(2) 0.3049(2) 0.0503(7) Uani 1 1 d . . . F3 F 0.1704(3) 1.09187(19) 0.43977(18) 0.0294(5) Uani 1 1 d . . . F4 F 0.2315(3) 1.1673(2) 0.18478(19) 0.0405(6) Uani 1 1 d . . . F5 F -0.0455(3) 0.1202(2) 0.8026(2) 0.0372(6) Uani 1 1 d . . . F6 F -0.2742(3) 0.0805(2) 1.0235(2) 0.0357(5) Uani 1 1 d . . . F7 F -0.2981(3) 0.3199(2) 0.8558(2) 0.0391(5) Uani 1 1 d . . . F8 F -0.0562(3) 0.2440(2) 0.98686(19) 0.0286(5) Uani 1 1 d . . . N1 N 0.1827(4) 0.8298(3) 0.6949(3) 0.0230(6) Uani 1 1 d . . . H1A H 0.0787 0.8391 0.7725 0.035 Uiso 1 1 calc R . . H1B H 0.1588 0.9053 0.6106 0.035 Uiso 1 1 calc R . . H1C H 0.2898 0.8443 0.7194 0.035 Uiso 1 1 calc R . . N2 N 0.3405(4) 0.2452(3) 0.8658(3) 0.0248(6) Uani 1 1 d . . . H2A H 0.4307 0.2619 0.9086 0.037 Uiso 1 1 calc R . . H2B H 0.3891 0.1590 0.8242 0.037 Uiso 1 1 calc R . . H2C H 0.2314 0.2264 0.9375 0.037 Uiso 1 1 calc R . . C1 C 0.2161(4) 0.6689(3) 0.6658(3) 0.0216(7) Uani 1 1 d . . . C2 C 0.2616(4) 0.5368(3) 0.7785(3) 0.0226(7) Uani 1 1 d . . . H2 H 0.2712 0.5478 0.8734 0.027 Uiso 1 1 calc R . . C3 C 0.2923(4) 0.3881(3) 0.7473(3) 0.0219(7) Uani 1 1 d . . . C4 C 0.2793(4) 0.3683(3) 0.6102(3) 0.0228(7) Uani 1 1 d . . . H4 H 0.2988 0.2642 0.5929 0.027 Uiso 1 1 calc R . . C5 C 0.2372(5) 0.5031(4) 0.4990(3) 0.0259(8) Uani 1 1 d . . . H5 H 0.2305 0.4918 0.4034 0.031 Uiso 1 1 calc R . . C6 C 0.2047(5) 0.6548(4) 0.5259(3) 0.0242(7) Uani 1 1 d . . . H6 H 0.1751 0.7476 0.4497 0.029 Uiso 1 1 calc R . . B1 B 0.3171(6) 1.1150(4) 0.3086(4) 0.0247(9) Uani 1 1 d . . . B2 B -0.1685(6) 0.1902(4) 0.9155(4) 0.0258(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0338(12) 0.0485(12) 0.0483(13) -0.0222(11) -0.0046(10) -0.0143(10) F2 0.0525(15) 0.0253(10) 0.0495(13) -0.0050(10) 0.0117(11) 0.0095(10) F3 0.0304(11) 0.0297(10) 0.0206(9) -0.0006(8) -0.0019(8) -0.0012(8) F4 0.0355(13) 0.0626(14) 0.0227(10) -0.0011(10) -0.0101(9) -0.0131(10) F5 0.0482(14) 0.0375(11) 0.0269(10) -0.0122(9) -0.0019(9) -0.0106(10) F6 0.0410(13) 0.0287(10) 0.0328(11) -0.0010(8) 0.0000(9) -0.0136(9) F7 0.0350(12) 0.0331(11) 0.0460(12) 0.0039(9) -0.0194(10) -0.0034(9) F8 0.0315(11) 0.0315(10) 0.0254(10) -0.0077(8) -0.0072(8) -0.0075(8) N1 0.0285(16) 0.0179(13) 0.0208(13) -0.0025(11) -0.0082(11) 0.0006(11) N2 0.0326(17) 0.0176(13) 0.0218(14) -0.0023(11) -0.0049(12) -0.0033(12) C1 0.0220(17) 0.0162(14) 0.0265(17) -0.0047(13) -0.0068(14) -0.0014(13) C2 0.0244(18) 0.0247(16) 0.0184(15) -0.0061(13) -0.0038(13) -0.0034(14) C3 0.0255(18) 0.0174(15) 0.0202(16) -0.0030(13) -0.0044(13) -0.0006(13) C4 0.0221(18) 0.0175(15) 0.0268(16) -0.0042(13) -0.0034(14) -0.0029(13) C5 0.0274(19) 0.0276(17) 0.0214(16) -0.0072(14) -0.0037(14) -0.0018(14) C6 0.0283(19) 0.0219(16) 0.0187(16) 0.0000(13) -0.0066(14) -0.0009(14) B1 0.031(2) 0.0214(18) 0.0192(18) -0.0045(15) -0.0024(16) -0.0033(16) B2 0.029(2) 0.0228(18) 0.0236(18) -0.0027(16) -0.0071(17) -0.0025(17) _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 F1 B1 1.370(4) . ? F2 B1 1.389(4) . ? F3 B1 1.405(4) . ? F4 B1 1.381(4) . ? F5 B2 1.390(4) . ? F6 B2 1.394(4) . ? F7 B2 1.388(4) . ? F8 B2 1.409(4) . ? N1 C1 1.475(3) . ? N2 C3 1.474(4) . ? C1 C2 1.382(4) . ? C1 C6 1.386(4) . ? C2 C3 1.380(4) . ? C3 C4 1.383(4) . ? C4 C5 1.382(4) . ? C5 C6 1.388(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 122.1(3) . . ? C2 C1 N1 118.7(3) . . ? C6 C1 N1 119.2(3) . . ? C3 C2 C1 117.1(3) . . ? C2 C3 C4 122.7(3) . . ? C2 C3 N2 118.3(3) . . ? C4 C3 N2 119.0(2) . . ? C5 C4 C3 118.6(3) . . ? C4 C5 C6 120.5(3) . . ? C1 C6 C5 118.9(3) . . ? F1 B1 F4 109.9(3) . . ? F1 B1 F2 109.0(3) . . ? F4 B1 F2 110.7(3) . . ? F1 B1 F3 110.6(2) . . ? F4 B1 F3 108.6(3) . . ? F2 B1 F3 108.1(3) . . ? F7 B2 F5 110.9(3) . . ? F7 B2 F6 108.5(3) . . ? F5 B2 F6 111.1(3) . . ? F7 B2 F8 108.8(3) . . ? F5 B2 F8 108.9(3) . . ? F6 B2 F8 108.6(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 C6 C1 C2 C3 -1.1(5) . . . . ? N1 C1 C2 C3 -179.9(3) . . . . ? C1 C2 C3 C4 0.0(5) . . . . ? C1 C2 C3 N2 -179.8(3) . . . . ? C2 C3 C4 C5 1.2(5) . . . . ? N2 C3 C4 C5 -178.9(3) . . . . ? C3 C4 C5 C6 -1.4(5) . . . . ? C2 C1 C6 C5 0.9(5) . . . . ? N1 C1 C6 C5 179.7(3) . . . . ? C4 C5 C6 C1 0.3(5) . . . . ? 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 F8 0.91 2.16 2.835(3) 130.6 2_567 N1 H1A F4 0.91 2.19 2.913(3) 136.2 2_576 N1 H1B F3 0.91 1.96 2.837(3) 162.8 . N1 H1B F3 0.91 2.54 3.003(3) 111.9 2_576 N1 H1C F1 0.91 2.01 2.787(4) 142.5 2_676 N2 H2A F7 0.91 2.04 2.814(3) 141.7 1_655 N2 H2A F6 0.91 2.64 3.346(4) 135.2 1_655 N2 H2B F2 0.91 1.91 2.772(3) 158.3 2_666 N2 H2B F6 0.91 2.39 2.875(3) 113.5 2_557 N2 H2C F8 0.91 1.99 2.801(3) 147.6 . N2 H2C F4 0.91 2.25 2.832(3) 121.7 1_546 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.269 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.069 data_2b _database_code_depnum_ccdc_archive 'CCDC 299862' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, 2(Br)' _chemical_formula_sum 'C6 H10 Br2 N2' _chemical_formula_weight 269.98 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 8.3858(17) _cell_length_b 8.1422(16) _cell_length_c 13.592(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.82(3) _cell_angle_gamma 90.00 _cell_volume 926.9(3) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.935 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 8.680 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0979 _exptl_absorpt_correction_T_max 0.4773 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3417 _diffrn_reflns_av_R_equivalents 0.1037 _diffrn_reflns_av_sigmaI/netI 0.0998 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1784 _reflns_number_gt 1534 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Largest residual electron density peaks are close to the bromines. 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^)+(0.0566P)^2^+22.2283P] 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 calc _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1784 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0913 _refine_ls_R_factor_gt 0.0822 _refine_ls_wR_factor_ref 0.2095 _refine_ls_wR_factor_gt 0.2037 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.162 _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 Br1 Br 0.01953(13) 0.02920(13) 0.32127(8) 0.0181(4) Uani 1 1 d . . . Br2 Br 0.51188(12) 0.00232(12) 0.65410(8) 0.0159(4) Uani 1 1 d . . . N1 N 0.2205(11) 0.8548(12) 0.5108(7) 0.019(2) Uani 1 1 d . . . H1A H 0.1923 0.8964 0.4503 0.028 Uiso 1 1 calc R . . H1B H 0.3137 0.9017 0.5337 0.028 Uiso 1 1 calc R . . H1C H 0.1424 0.8771 0.5531 0.028 Uiso 1 1 calc R . . N2 N 0.2700(12) 0.3531(11) 0.3136(7) 0.020(2) Uani 1 1 d . . . H2A H 0.2957 0.2453 0.3224 0.031 Uiso 1 1 calc R . . H2B H 0.3423 0.4015 0.2751 0.031 Uiso 1 1 calc R . . H2C H 0.1708 0.3612 0.2838 0.031 Uiso 1 1 calc R . . C1 C 0.2415(12) 0.6774(14) 0.5035(8) 0.016(2) Uani 1 1 d . . . C2 C 0.2387(13) 0.6038(13) 0.4131(8) 0.016(2) Uani 1 1 d . . . H2 H 0.2148 0.6652 0.3548 0.020 Uiso 1 1 calc R . . C3 C 0.2722(13) 0.4349(13) 0.4087(8) 0.016(2) Uani 1 1 d . . . C4 C 0.3027(15) 0.3451(14) 0.4936(8) 0.020(2) Uani 1 1 d . . . H4 H 0.3193 0.2299 0.4899 0.024 Uiso 1 1 calc R . . C5 C 0.3093(18) 0.4243(15) 0.5854(9) 0.031(3) Uani 1 1 d . . . H5 H 0.3373 0.3641 0.6436 0.037 Uiso 1 1 calc R . . C6 C 0.2746(15) 0.5914(14) 0.5911(8) 0.021(2) Uani 1 1 d . . . H6 H 0.2734 0.6454 0.6530 0.026 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 Br1 0.0204(6) 0.0127(5) 0.0212(6) 0.0004(4) 0.0007(4) 0.0005(4) Br2 0.0202(6) 0.0097(5) 0.0179(6) -0.0006(4) 0.0022(4) 0.0027(4) N1 0.015(5) 0.020(5) 0.021(5) 0.000(4) 0.003(4) 0.003(4) N2 0.026(5) 0.014(4) 0.022(5) -0.003(4) 0.010(4) 0.000(4) C1 0.011(5) 0.012(5) 0.024(6) 0.003(4) 0.002(4) 0.002(4) C2 0.017(5) 0.015(5) 0.017(5) 0.003(4) 0.001(4) -0.002(4) C3 0.012(5) 0.014(5) 0.024(6) -0.004(4) 0.006(4) 0.002(4) C4 0.028(6) 0.014(5) 0.017(5) -0.001(4) 0.001(5) 0.001(5) C5 0.053(9) 0.015(6) 0.024(6) 0.003(5) 0.006(6) 0.010(6) C6 0.034(7) 0.016(6) 0.014(5) 0.001(4) -0.001(5) 0.005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.460(14) . ? N2 C3 1.454(13) . ? C1 C2 1.366(15) . ? C1 C6 1.398(15) . ? C2 C3 1.405(15) . ? C3 C4 1.380(15) . ? C4 C5 1.403(16) . ? C5 C6 1.394(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 C2 C1 C6 122.7(11) . . ? C2 C1 N1 119.9(9) . . ? C6 C1 N1 117.2(10) . . ? C1 C2 C3 118.2(10) . . ? C4 C3 C2 120.8(10) . . ? C4 C3 N2 119.6(10) . . ? C2 C3 N2 119.5(10) . . ? C3 C4 C5 119.8(11) . . ? C6 C5 C4 119.9(11) . . ? C5 C6 C1 118.3(10) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 2.992 _refine_diff_density_min -1.985 _refine_diff_density_rms 0.336 data_2d _database_code_depnum_ccdc_archive 'CCDC 299863' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, 2(H O4 S)' _chemical_formula_sum 'C6 H12 N2 O8 S2' _chemical_formula_weight 304.30 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' S S 0.1246 0.1234 '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 7.1298(9) _cell_length_b 8.8359(8) _cell_length_c 10.3489(14) _cell_angle_alpha 65.177(8) _cell_angle_beta 87.006(8) _cell_angle_gamma 77.515(8) _cell_volume 577.19(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.751 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.499 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7885 _exptl_absorpt_correction_T_max 0.9518 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4537 _diffrn_reflns_av_R_equivalents 0.0667 _diffrn_reflns_av_sigmaI/netI 0.1277 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2640 _reflns_number_gt 2264 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _refine_special_details ; N and C hydrogens calculated, O hydrogens located in difference map and then fixed 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^)+(0.0481P)^2^+0.0607P] 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 'see above' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.030(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2640 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1540 _refine_ls_wR_factor_gt 0.1474 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 S1 S 0.30796(7) 0.14595(6) 0.27187(5) 0.0133(2) Uani 1 1 d . . . S2 S 0.21152(7) 0.76357(6) 0.00545(5) 0.0131(2) Uani 1 1 d . . . O1 O 0.1510(2) 0.1152(2) 0.36948(17) 0.0181(4) Uani 1 1 d . . . O2 O 0.2342(2) 0.1576(2) 0.12881(16) 0.0214(4) Uani 1 1 d . . . O3 O 0.4754(2) 0.0063(2) 0.32212(17) 0.0197(4) Uani 1 1 d . . . O4 O 0.3613(2) 0.3081(2) 0.23985(17) 0.0193(4) Uani 1 1 d . . . O5 O 0.3815(2) 0.8170(2) 0.02182(19) 0.0262(4) Uani 1 1 d . . . O6 O 0.0806(2) 0.7452(2) 0.11910(17) 0.0231(4) Uani 1 1 d . . . O7 O 0.1161(2) 0.8727(2) -0.13603(16) 0.0171(4) Uani 1 1 d . . . O8 O 0.2746(3) 0.5871(2) -0.00176(18) 0.0272(5) Uani 1 1 d . . . H8 H 0.2872 0.5089 0.0812 0.033 Uiso 1 1 calc R . . N1 N 0.6922(3) 0.8167(2) 0.18000(18) 0.0145(4) Uani 1 1 d . . . H1A H 0.8086 0.8321 0.1426 0.022 Uiso 1 1 calc R . . H1B H 0.6399 0.9023 0.2065 0.022 Uiso 1 1 calc R . . H1C H 0.6128 0.8178 0.1134 0.022 Uiso 1 1 calc R . . N2 N 0.7419(3) 0.2002(2) 0.3806(2) 0.0154(4) Uani 1 1 d . . . H2A H 0.6284 0.2147 0.3361 0.023 Uiso 1 1 calc R . . H2B H 0.7545 0.1082 0.4665 0.023 Uiso 1 1 calc R . . H2C H 0.8408 0.1826 0.3258 0.023 Uiso 1 1 calc R . . C1 C 0.7168(3) 0.6528(3) 0.3044(2) 0.0131(5) Uani 1 1 d . . . C2 C 0.7191(3) 0.5076(3) 0.2828(2) 0.0138(5) Uani 1 1 d . . . H2 H 0.7035 0.5139 0.1900 0.017 Uiso 1 1 calc R . . C3 C 0.7452(3) 0.3526(3) 0.4023(2) 0.0138(5) Uani 1 1 d . . . C4 C 0.7702(3) 0.3413(3) 0.5383(2) 0.0157(5) Uani 1 1 d . . . H4 H 0.7886 0.2338 0.6184 0.019 Uiso 1 1 calc R . . C5 C 0.7680(3) 0.4882(3) 0.5557(2) 0.0163(5) Uani 1 1 d . . . H5 H 0.7848 0.4814 0.6486 0.020 Uiso 1 1 calc R . . H1 H 0.0964 0.1392 0.1384 0.074(14) Uiso 1 1 d R . . C6 C 0.7415(3) 0.6461(3) 0.4390(2) 0.0148(5) Uani 1 1 d . . . H6 H 0.7404 0.7470 0.4512 0.018 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 S1 0.0131(4) 0.0137(3) 0.0138(3) -0.0068(2) 0.0013(2) -0.0020(2) S2 0.0136(4) 0.0136(3) 0.0115(3) -0.0049(2) 0.0011(2) -0.0024(2) O1 0.0156(8) 0.0227(9) 0.0161(8) -0.0087(7) 0.0032(6) -0.0036(7) O2 0.0171(9) 0.0363(10) 0.0161(8) -0.0149(7) 0.0025(6) -0.0088(7) O3 0.0178(9) 0.0166(8) 0.0224(9) -0.0083(7) -0.0004(6) 0.0017(6) O4 0.0237(9) 0.0142(8) 0.0207(8) -0.0071(7) 0.0000(7) -0.0055(7) O5 0.0202(9) 0.0321(10) 0.0232(9) -0.0052(8) -0.0042(7) -0.0117(8) O6 0.0194(9) 0.0285(10) 0.0143(8) -0.0053(7) 0.0054(6) -0.0001(7) O7 0.0150(8) 0.0185(8) 0.0139(8) -0.0022(6) -0.0011(6) -0.0048(6) O8 0.0488(12) 0.0140(8) 0.0164(8) -0.0067(7) 0.0009(8) -0.0010(8) N1 0.0164(10) 0.0127(9) 0.0130(9) -0.0053(7) 0.0019(7) -0.0011(7) N2 0.0152(10) 0.0140(9) 0.0177(9) -0.0074(7) 0.0021(7) -0.0035(7) C1 0.0109(11) 0.0148(10) 0.0126(10) -0.0053(8) 0.0019(8) -0.0017(8) C2 0.0144(11) 0.0162(11) 0.0129(10) -0.0086(9) 0.0016(8) -0.0025(8) C3 0.0109(11) 0.0143(10) 0.0177(10) -0.0086(9) 0.0019(8) -0.0022(8) C4 0.0173(12) 0.0151(11) 0.0130(10) -0.0042(9) 0.0018(8) -0.0034(8) C5 0.0151(11) 0.0199(11) 0.0126(10) -0.0072(9) -0.0001(8) -0.0004(9) C6 0.0164(12) 0.0149(11) 0.0152(10) -0.0088(9) 0.0013(8) -0.0027(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 S1 O3 1.4517(17) . ? S1 O1 1.4593(16) . ? S1 O4 1.4600(17) . ? S1 O2 1.5523(16) . ? S2 O5 1.4338(17) . ? S2 O6 1.4395(16) . ? S2 O7 1.4735(16) . ? S2 O8 1.5586(18) . ? N1 C1 1.461(3) . ? N2 C3 1.460(3) . ? C1 C2 1.388(3) . ? C1 C6 1.388(3) . ? C2 C3 1.389(3) . ? C3 C4 1.387(3) . ? C4 C5 1.381(3) . ? C5 C6 1.391(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 O3 S1 O1 112.12(10) . . ? O3 S1 O4 110.54(10) . . ? O1 S1 O4 113.02(10) . . ? O3 S1 O2 107.44(10) . . ? O1 S1 O2 106.87(9) . . ? O4 S1 O2 106.46(9) . . ? O5 S2 O6 114.59(11) . . ? O5 S2 O7 110.92(10) . . ? O6 S2 O7 112.41(10) . . ? O5 S2 O8 108.05(12) . . ? O6 S2 O8 107.90(10) . . ? O7 S2 O8 102.07(10) . . ? C2 C1 C6 122.2(2) . . ? C2 C1 N1 118.30(19) . . ? C6 C1 N1 119.5(2) . . ? C1 C2 C3 117.5(2) . . ? C4 C3 C2 121.9(2) . . ? C4 C3 N2 120.46(19) . . ? C2 C3 N2 117.68(19) . . ? C5 C4 C3 119.1(2) . . ? C4 C5 C6 120.8(2) . . ? C1 C6 C5 118.5(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.7(3) . . . . ? N1 C1 C2 C3 179.17(19) . . . . ? C1 C2 C3 C4 -0.7(3) . . . . ? C1 C2 C3 N2 178.17(19) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? N2 C3 C4 C5 -178.44(19) . . . . ? C3 C4 C5 C6 -0.1(3) . . . . ? C2 C1 C6 C5 -0.5(3) . . . . ? N1 C1 C6 C5 -178.92(19) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? 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 O6 0.91 1.97 2.803(2) 151.9 1_655 N1 H1B O3 0.91 1.99 2.841(2) 154.9 1_565 N1 H1C O5 0.91 1.95 2.821(3) 160.4 . N1 H1C O2 0.91 2.62 3.132(2) 116.1 2_665 N2 H2A O4 0.91 2.03 2.919(3) 164.7 . N2 H2A O3 0.91 2.39 3.051(3) 129.6 . N2 H2B O1 0.91 1.99 2.876(2) 163.8 2_656 N2 H2B O3 0.91 2.64 3.348(2) 134.9 2_656 N2 H2C O1 0.91 2.18 2.859(2) 130.7 1_655 N2 H2C O7 0.91 2.21 2.943(3) 137.7 2_665 O8 H8 O4 0.84 1.83 2.653(2) 164.7 . O2 H1 O7 1.02 1.54 2.562(2) 173.7 2_565 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.964 _refine_diff_density_min -0.796 _refine_diff_density_rms 0.147 data_2e _database_code_depnum_ccdc_archive 'CCDC 299864' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'C6 H10 N2, 2(N O3), H2 O' _chemical_formula_moiety ? _chemical_formula_sum 'C6 H12 N4 O7' _chemical_formula_weight 252.20 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 10.677(2) _cell_length_b 6.8471(18) _cell_length_c 15.621(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.610(10) _cell_angle_gamma 90.00 _cell_volume 1082.2(4) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9327 _exptl_absorpt_correction_T_max 0.9860 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5985 _diffrn_reflns_av_R_equivalents 0.1332 _diffrn_reflns_av_sigmaI/netI 0.1427 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2124 _reflns_number_gt 1211 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _refine_special_details ; N and C hydrogens in calculated positions, water hydrogens located in the difference map and then fixed 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^)+(0.0063P)^2^+0.4640P] 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 'see above' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0098(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2124 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1347 _refine_ls_R_factor_gt 0.0660 _refine_ls_wR_factor_ref 0.1251 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.2580(2) 0.8222(4) 0.45346(19) 0.0437(8) Uani 1 1 d . . . O2 O -0.0650(2) 0.6965(4) 0.47567(15) 0.0304(7) Uani 1 1 d . . . O3 O -0.1425(2) 0.9116(4) 0.36932(17) 0.0430(8) Uani 1 1 d . . . O4 O 0.1989(2) 0.5847(4) 0.69761(15) 0.0297(7) Uani 1 1 d . . . O5 O 0.4126(2) 0.5515(4) 0.73489(15) 0.0254(6) Uani 1 1 d . . . O6 O 0.3070(2) 0.4184(3) 0.81790(15) 0.0246(6) Uani 1 1 d . . . O7 O -0.0498(3) 0.6287(4) 0.17756(18) 0.0276(7) Uani 1 1 d . . . N1 N 0.0706(2) 0.5316(4) 0.36214(17) 0.0228(7) Uani 1 1 d . . . H1A H 0.0205 0.5803 0.3946 0.034 Uiso 1 1 calc R . . H1B H 0.0688 0.3988 0.3634 0.034 Uiso 1 1 calc R . . H1C H 0.0378 0.5736 0.3040 0.034 Uiso 1 1 calc R . . N2 N 0.4113(2) 0.8435(4) 0.61029(17) 0.0226(7) Uani 1 1 d . . . H2A H 0.4978 0.8793 0.6264 0.034 Uiso 1 1 calc R . . H2B H 0.3998 0.7570 0.6514 0.034 Uiso 1 1 calc R . . H2C H 0.3604 0.9510 0.6086 0.034 Uiso 1 1 calc R . . N3 N -0.1551(3) 0.8110(5) 0.43264(19) 0.0267(7) Uani 1 1 d . . . N4 N 0.3045(3) 0.5184(4) 0.74952(19) 0.0251(7) Uani 1 1 d . . . C1 C 0.2078(3) 0.5997(5) 0.4016(2) 0.0208(8) Uani 1 1 d . . . C2 C 0.2438(3) 0.6868(5) 0.4857(2) 0.0211(8) Uani 1 1 d . . . H2 H 0.1824 0.7011 0.5179 0.025 Uiso 1 1 calc R . . C3 C 0.3723(3) 0.7523(5) 0.5212(2) 0.0216(8) Uani 1 1 d . . . C4 C 0.4626(3) 0.7334(5) 0.4757(2) 0.0205(8) Uani 1 1 d . . . H4 H 0.5507 0.7790 0.5017 0.025 Uiso 1 1 calc R . . C5 C 0.4227(3) 0.6466(5) 0.3912(2) 0.0228(8) Uani 1 1 d . . . H5 H 0.4839 0.6335 0.3588 0.027 Uiso 1 1 calc R . . C6 C 0.2950(3) 0.5786(5) 0.3535(2) 0.0232(8) Uani 1 1 d . . . H6 H 0.2678 0.5187 0.2956 0.028 Uiso 1 1 calc R . . H71 H -0.131(4) 0.592(5) 0.174(2) 0.041(12) Uiso 1 1 d . . . H72 H -0.019(4) 0.571(6) 0.151(3) 0.043(16) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0289(14) 0.0393(19) 0.071(2) 0.0094(16) 0.0278(14) 0.0105(13) O2 0.0248(13) 0.0363(18) 0.0275(14) 0.0050(13) 0.0046(11) 0.0108(12) O3 0.0397(15) 0.053(2) 0.0327(15) 0.0229(14) 0.0067(13) -0.0061(14) O4 0.0204(12) 0.0350(18) 0.0257(14) 0.0065(12) -0.0037(11) 0.0048(12) O5 0.0208(12) 0.0305(16) 0.0264(13) 0.0016(11) 0.0096(10) -0.0009(11) O6 0.0234(12) 0.0258(16) 0.0230(13) 0.0065(11) 0.0050(10) 0.0005(11) O7 0.0248(15) 0.0320(18) 0.0258(15) -0.0012(13) 0.0078(12) -0.0031(13) N1 0.0219(14) 0.0247(19) 0.0203(15) -0.0003(13) 0.0046(12) -0.0001(13) N2 0.0195(14) 0.0248(19) 0.0213(15) -0.0015(14) 0.0035(12) 0.0013(13) N3 0.0251(17) 0.023(2) 0.0298(17) -0.0013(15) 0.0061(14) -0.0007(15) N4 0.0250(16) 0.024(2) 0.0243(17) -0.0058(15) 0.0048(14) -0.0030(14) C1 0.0168(16) 0.022(2) 0.0209(18) 0.0035(16) 0.0018(14) 0.0009(15) C2 0.0222(17) 0.017(2) 0.0228(19) 0.0013(16) 0.0059(15) 0.0038(16) C3 0.0235(18) 0.019(2) 0.0177(18) -0.0007(16) 0.0001(15) 0.0008(15) C4 0.0142(16) 0.019(2) 0.026(2) 0.0068(16) 0.0039(15) 0.0002(15) C5 0.0235(18) 0.023(2) 0.0226(19) 0.0033(17) 0.0081(15) 0.0012(16) C6 0.0264(18) 0.025(2) 0.0187(18) 0.0022(16) 0.0075(15) 0.0024(16) _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 O1 N3 1.243(3) . ? O2 N3 1.256(3) . ? O3 N3 1.247(3) . ? O4 N4 1.245(3) . ? O5 N4 1.266(3) . ? O6 N4 1.262(3) . ? N1 C1 1.471(4) . ? N2 C3 1.460(4) . ? C1 C6 1.378(4) . ? C1 C2 1.380(4) . ? C2 C3 1.381(4) . ? C3 C4 1.374(4) . ? C4 C5 1.385(4) . ? C5 C6 1.383(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 N3 O3 120.1(3) . . ? O1 N3 O2 119.2(3) . . ? O3 N3 O2 120.7(3) . . ? O4 N4 O6 121.2(3) . . ? O4 N4 O5 120.4(3) . . ? O6 N4 O5 118.4(3) . . ? C6 C1 C2 122.2(3) . . ? C6 C1 N1 119.6(3) . . ? C2 C1 N1 118.3(3) . . ? C1 C2 C3 117.5(3) . . ? C4 C3 C2 122.2(3) . . ? C4 C3 N2 120.0(3) . . ? C2 C3 N2 117.8(3) . . ? C3 C4 C5 118.7(3) . . ? C6 C5 C4 120.8(3) . . ? C1 C6 C5 118.6(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 C6 C1 C2 C3 -0.4(5) . . . . ? N1 C1 C2 C3 -179.1(3) . . . . ? C1 C2 C3 C4 0.1(5) . . . . ? C1 C2 C3 N2 -179.6(3) . . . . ? C2 C3 C4 C5 0.4(5) . . . . ? N2 C3 C4 C5 -179.9(3) . . . . ? C3 C4 C5 C6 -0.5(5) . . . . ? C2 C1 C6 C5 0.3(5) . . . . ? N1 C1 C6 C5 178.9(3) . . . . ? C4 C5 C6 C1 0.2(5) . . . . ? 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 O7 H72 O3 0.72(4) 2.15(4) 2.815(4) 153(4) 2_545 O7 H71 O6 0.89(4) 1.93(4) 2.789(3) 164(3) 3_566 O7 H71 N4 0.89(4) 2.62(4) 3.419(4) 151(3) 3_566 O7 H71 O4 0.89(4) 2.64(4) 3.233(4) 126(3) 3_566 N1 H1A O2 0.91 1.95 2.856(3) 172.5 . N1 H1A N3 0.91 2.66 3.518(4) 157.5 . N1 H1B O7 0.91 1.95 2.821(4) 160.6 2_545 N1 H1C O7 0.91 1.93 2.836(4) 171.2 . N2 H2A O6 0.91 2.00 2.901(3) 168.3 2_656 N2 H2A O5 0.91 2.38 2.917(3) 117.5 2_656 N2 H2A N4 0.91 2.55 3.346(4) 146.2 2_656 N2 H2B O5 0.91 1.89 2.787(4) 166.7 . N2 H2B N4 0.91 2.65 3.545(4) 166.0 . N2 H2C O1 0.91 1.97 2.805(4) 152.2 3_576 N2 H2C O3 0.91 2.63 3.425(4) 146.0 3_576 N2 H2C N3 0.91 2.64 3.515(4) 161.3 3_576 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.267 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.064 data_2f _database_code_depnum_ccdc_archive 'CCDC 299865' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, F6 Si, H2 O' _chemical_formula_sum 'C6 H12 F6 N2 O Si' _chemical_formula_weight 270.27 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' 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' 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 P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.9269(11) _cell_length_b 6.0679(10) _cell_length_c 10.4425(15) _cell_angle_alpha 90.00 _cell_angle_beta 113.210(9) _cell_angle_gamma 90.00 _cell_volume 519.86(13) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.727 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.295 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8665 _exptl_absorpt_correction_T_max 0.9711 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Kappa _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3030 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.1159 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1798 _reflns_number_gt 1736 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _refine_special_details ; C and N hydrogens in calculated positions, water hydrogens located in the difference map and refined. O-H distances DFIX'ed at 0.9 Ang 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^)+(0.0000P)^2^+0.2185P] 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 'see above' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.072(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(19) _refine_ls_number_reflns 1798 _refine_ls_number_parameters 156 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1222 _refine_ls_wR_factor_gt 0.1201 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.032 _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 0.41717(9) 0.98129(14) 0.73646(8) 0.0175(3) Uani 1 1 d . . . F1 F 0.4761(2) 1.0328(3) 0.60394(17) 0.0246(5) Uani 1 1 d . . . F2 F 0.3646(2) 0.9269(3) 0.87276(17) 0.0227(5) Uani 1 1 d . . . F3 F 0.5978(2) 0.8530(4) 0.82164(18) 0.0289(5) Uani 1 1 d . . . F4 F 0.2433(2) 1.1207(5) 0.6560(2) 0.0443(7) Uani 1 1 d . . . F5 F 0.5057(3) 1.2161(3) 0.8195(2) 0.0359(6) Uani 1 1 d . . . F6 F 0.3331(3) 0.7454(4) 0.6642(2) 0.0379(6) Uani 1 1 d . . . O1 O -0.0853(3) 1.0482(5) 0.5435(3) 0.0360(7) Uani 1 1 d D . . N1 N -0.2533(3) 0.7491(5) 0.6274(3) 0.0202(6) Uani 1 1 d . . . H1A H -0.3247 0.6807 0.5498 0.030 Uiso 1 1 calc R . . H1B H -0.1949 0.8509 0.6023 0.030 Uiso 1 1 calc R . . H1C H -0.3092 0.8173 0.6725 0.030 Uiso 1 1 calc R . . N2 N 0.3031(3) 0.4813(5) 0.8948(2) 0.0166(5) Uani 1 1 d . . . H2A H 0.3532 0.4328 0.9841 0.025 Uiso 1 1 calc R . . H2B H 0.3272 0.6261 0.8904 0.025 Uiso 1 1 calc R . . H2C H 0.3387 0.4013 0.8385 0.025 Uiso 1 1 calc R . . C1 C -0.1419(4) 0.5855(5) 0.7201(3) 0.0168(6) Uani 1 1 d . . . C2 C 0.0251(4) 0.6145(5) 0.7619(3) 0.0161(6) Uani 1 1 d . . . H2 H 0.0682 0.7385 0.7324 0.019 Uiso 1 1 calc R . . C3 C 0.1264(3) 0.4550(5) 0.8485(3) 0.0161(6) Uani 1 1 d . . . C4 C 0.0668(4) 0.2740(6) 0.8925(3) 0.0214(7) Uani 1 1 d . . . H4 H 0.1389 0.1673 0.9518 0.026 Uiso 1 1 calc R . . C5 C -0.1012(4) 0.2504(6) 0.8485(3) 0.0243(7) Uani 1 1 d . . . H5 H -0.1440 0.1261 0.8778 0.029 Uiso 1 1 calc R . . C6 C -0.2071(4) 0.4067(6) 0.7619(3) 0.0246(8) Uani 1 1 d . . . H6 H -0.3218 0.3907 0.7322 0.029 Uiso 1 1 calc R . . H1W H -0.157(4) 1.133(6) 0.480(3) 0.024(9) Uiso 1 1 d D . . H2W H 0.016(4) 1.098(11) 0.574(6) 0.068(16) Uiso 1 1 d 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 Si1 0.0125(4) 0.0178(5) 0.0229(4) 0.0029(3) 0.0079(3) -0.0008(3) F1 0.0206(8) 0.0302(12) 0.0259(9) 0.0110(8) 0.0122(7) 0.0059(9) F2 0.0216(9) 0.0235(11) 0.0255(9) -0.0032(7) 0.0120(7) -0.0045(8) F3 0.0208(9) 0.0471(14) 0.0171(9) -0.0013(8) 0.0056(7) 0.0126(9) F4 0.0245(10) 0.0618(17) 0.0523(13) 0.0316(12) 0.0214(10) 0.0197(11) F5 0.0425(12) 0.0218(11) 0.0598(13) -0.0128(10) 0.0377(11) -0.0130(10) F6 0.0491(13) 0.0398(14) 0.0273(9) -0.0151(10) 0.0177(9) -0.0284(12) O1 0.0249(12) 0.0387(16) 0.0337(13) 0.0155(13) 0.0000(10) -0.0059(12) N1 0.0133(12) 0.0237(16) 0.0222(12) -0.0077(12) 0.0056(10) 0.0010(11) N2 0.0161(11) 0.0147(12) 0.0181(11) 0.0015(11) 0.0058(9) 0.0012(11) C1 0.0177(14) 0.0204(16) 0.0139(12) -0.0052(12) 0.0079(11) -0.0020(13) C2 0.0192(14) 0.0176(16) 0.0147(12) 0.0008(11) 0.0100(11) -0.0026(13) C3 0.0163(14) 0.0194(16) 0.0141(12) -0.0031(12) 0.0076(10) -0.0024(13) C4 0.0248(16) 0.0210(17) 0.0163(13) 0.0012(13) 0.0058(12) -0.0073(14) C5 0.0316(16) 0.0209(19) 0.0241(15) -0.0013(14) 0.0149(13) -0.0141(15) C6 0.0183(15) 0.036(2) 0.0222(14) -0.0042(14) 0.0105(13) -0.0095(15) _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 F6 1.654(2) . ? Si1 F4 1.674(2) . ? Si1 F1 1.6922(17) . ? Si1 F5 1.693(2) . ? Si1 F3 1.6930(19) . ? Si1 F2 1.6973(17) . ? N1 C1 1.467(4) . ? N2 C3 1.465(3) . ? C1 C6 1.381(5) . ? C1 C2 1.390(4) . ? C2 C3 1.388(4) . ? C3 C4 1.376(5) . ? C4 C5 1.392(4) . ? C5 C6 1.392(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 F6 Si1 F4 92.54(14) . . ? F6 Si1 F1 91.05(10) . . ? F4 Si1 F1 91.25(10) . . ? F6 Si1 F5 176.68(12) . . ? F4 Si1 F5 89.14(14) . . ? F1 Si1 F5 91.77(10) . . ? F6 Si1 F3 90.49(13) . . ? F4 Si1 F3 176.97(15) . . ? F1 Si1 F3 88.63(9) . . ? F5 Si1 F3 87.84(12) . . ? F6 Si1 F2 89.34(10) . . ? F4 Si1 F2 90.64(10) . . ? F1 Si1 F2 178.05(10) . . ? F5 Si1 F2 87.78(10) . . ? F3 Si1 F2 89.46(9) . . ? C6 C1 C2 122.3(3) . . ? C6 C1 N1 118.7(3) . . ? C2 C1 N1 119.0(3) . . ? C3 C2 C1 117.3(3) . . ? C4 C3 C2 122.4(3) . . ? C4 C3 N2 119.0(3) . . ? C2 C3 N2 118.6(3) . . ? C3 C4 C5 118.7(3) . . ? C4 C5 C6 120.9(3) . . ? C1 C6 C5 118.5(3) . . ? 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 N2 H2A F3 0.91 1.96 2.845(3) 163.7 2_647 N2 H2B F2 0.91 1.88 2.787(3) 176.6 . N2 H2C F5 0.91 1.94 2.756(3) 148.6 1_545 N1 H1A F1 0.91 1.87 2.780(3) 177.1 2_546 N1 H1B O1 0.91 1.80 2.710(4) 177.0 . N1 H1C F3 0.91 2.04 2.900(3) 155.9 1_455 O1 H1W F6 0.885(19) 1.82(2) 2.692(3) 166(4) 2_556 O1 H2W F4 0.89(5) 1.87(3) 2.732(3) 164(6) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.702 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.134 data_2g _database_code_depnum_ccdc_archive 'CCDC 299866' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, F6 Si, H2 O' _chemical_formula_sum 'C6 H12 F6 N2 O Si' _chemical_formula_weight 270.27 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' 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' 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.9265(18) _cell_length_b 6.0639(12) _cell_length_c 10.440(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.15(3) _cell_angle_gamma 90.00 _cell_volume 519.59(18) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.727 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.295 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9433 _exptl_absorpt_correction_T_max 0.9711 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3125 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0725 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1960 _reflns_number_gt 1756 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _refine_special_details ; N and C hydrogens in calculated positions. Water hydrogens located in difference map and then fixed 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^)+(0.0178P)^2^+0.6559P] 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 'see above' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.046(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(2) _refine_ls_number_reflns 1960 _refine_ls_number_parameters 154 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.0999 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 -0.41700(11) 0.86947(17) 0.76354(10) 0.0176(3) Uani 1 1 d . . . F1 F -0.3643(2) 0.8154(3) 0.6273(2) 0.0226(5) Uani 1 1 d . . . F2 F -0.2429(3) 1.0088(5) 0.8443(3) 0.0445(8) Uani 1 1 d . . . F3 F -0.3333(3) 0.6332(4) 0.8358(2) 0.0382(7) Uani 1 1 d . . . F4 F -0.4760(2) 0.9217(4) 0.8960(2) 0.0250(5) Uani 1 1 d . . . F5 F -0.5976(2) 0.7405(4) 0.6786(2) 0.0266(6) Uani 1 1 d . . . F6 F -0.5042(3) 1.1044(4) 0.6813(3) 0.0366(7) Uani 1 1 d . . . O1 O 0.0841(4) 0.9362(6) 0.9560(3) 0.0370(8) Uani 1 1 d . . . N1 N 0.2530(3) 0.6381(6) 0.8731(3) 0.0197(7) Uani 1 1 d . . . H1C H 0.2025 0.7079 0.9223 0.024 Uiso 1 1 calc R . . H1B H 0.2806 0.7385 0.8213 0.024 Uiso 1 1 calc R . . H1A H 0.3445 0.5698 0.9331 0.024 Uiso 1 1 calc R . . N2 N -0.3028(3) 0.3701(5) 0.6048(3) 0.0171(6) Uani 1 1 d . . . H2C H -0.3411 0.2755 0.6526 0.021 Uiso 1 1 calc R . . H2B H -0.3511 0.3399 0.5121 0.021 Uiso 1 1 calc R . . H2A H -0.3261 0.5111 0.6204 0.021 Uiso 1 1 calc R . . C1 C 0.1419(4) 0.4727(6) 0.7802(3) 0.0165(7) Uani 1 1 d . . . C2 C -0.0244(4) 0.5031(6) 0.7378(3) 0.0151(7) Uani 1 1 d . . . H2 H -0.0672 0.6284 0.7664 0.018 Uiso 1 1 calc R . . C3 C -0.1260(4) 0.3438(6) 0.6521(3) 0.0147(7) Uani 1 1 d . . . C4 C -0.0667(4) 0.1622(6) 0.6076(3) 0.0206(8) Uani 1 1 d . . . H4 H -0.1391 0.0557 0.5485 0.025 Uiso 1 1 calc R . . C5 C 0.1014(5) 0.1378(7) 0.6510(4) 0.0241(8) Uani 1 1 d . . . H5 H 0.1443 0.0141 0.6209 0.029 Uiso 1 1 calc R . . C6 C 0.2065(4) 0.2943(7) 0.7384(3) 0.0229(9) Uani 1 1 d . . . H6 H 0.3212 0.2781 0.7686 0.027 Uiso 1 1 calc R . . H11 H 0.135(7) 1.023(10) 0.996(6) 0.048(18) Uiso 1 1 d . . . H12 H -0.013(7) 0.995(10) 0.921(5) 0.053(16) 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 Si1 0.0123(4) 0.0196(5) 0.0201(4) -0.0028(4) 0.0054(3) 0.0010(4) F1 0.0213(10) 0.0242(13) 0.0240(10) 0.0021(9) 0.0107(8) 0.0038(9) F2 0.0245(13) 0.066(2) 0.0482(15) -0.0308(14) 0.0204(11) -0.0205(13) F3 0.0497(15) 0.0405(16) 0.0257(11) 0.0139(11) 0.0162(11) 0.0276(14) F4 0.0196(10) 0.0320(14) 0.0256(10) -0.0117(9) 0.0113(8) -0.0074(9) F5 0.0196(11) 0.0433(15) 0.0135(10) -0.0003(9) 0.0029(8) -0.0123(10) F6 0.0438(15) 0.0223(13) 0.0598(16) 0.0131(12) 0.0376(13) 0.0117(12) O1 0.0243(16) 0.041(2) 0.0338(16) -0.0156(15) -0.0013(12) 0.0030(15) N1 0.0136(14) 0.0242(17) 0.0193(14) 0.0057(13) 0.0045(11) -0.0010(14) N2 0.0149(13) 0.0172(15) 0.0178(13) -0.0032(13) 0.0047(10) -0.0029(14) C1 0.0175(17) 0.0210(19) 0.0115(14) 0.0044(13) 0.0064(13) 0.0004(16) C2 0.0161(16) 0.0158(17) 0.0143(15) 0.0026(13) 0.0070(13) 0.0042(15) C3 0.0150(14) 0.0178(18) 0.0118(14) 0.0028(13) 0.0059(12) 0.0012(15) C4 0.0262(19) 0.0180(18) 0.0151(16) -0.0009(14) 0.0054(14) 0.0044(17) C5 0.030(2) 0.023(2) 0.0210(17) -0.0001(16) 0.0124(15) 0.0094(18) C6 0.0159(17) 0.036(2) 0.0174(17) 0.0027(16) 0.0067(13) 0.0077(16) _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 F3 1.654(3) . ? Si1 F2 1.676(3) . ? Si1 F6 1.687(2) . ? Si1 F4 1.692(2) . ? Si1 F5 1.695(2) . ? Si1 F1 1.697(2) . ? N1 C1 1.474(5) . ? N2 C3 1.466(4) . ? C1 C6 1.376(5) . ? C1 C2 1.384(5) . ? C2 C3 1.385(5) . ? C3 C4 1.378(5) . ? C4 C5 1.394(5) . ? C5 C6 1.393(6) . ? 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 F3 Si1 F2 92.53(16) . . ? F3 Si1 F6 176.88(14) . . ? F2 Si1 F6 88.94(16) . . ? F3 Si1 F4 91.12(12) . . ? F2 Si1 F4 91.14(11) . . ? F6 Si1 F4 91.60(12) . . ? F3 Si1 F5 90.26(14) . . ? F2 Si1 F5 177.20(17) . . ? F6 Si1 F5 88.27(13) . . ? F4 Si1 F5 88.62(11) . . ? F3 Si1 F1 89.44(11) . . ? F2 Si1 F1 90.63(12) . . ? F6 Si1 F1 87.79(11) . . ? F4 Si1 F1 178.12(12) . . ? F5 Si1 F1 89.58(11) . . ? C6 C1 C2 122.3(3) . . ? C6 C1 N1 119.1(3) . . ? C2 C1 N1 118.6(3) . . ? C1 C2 C3 117.4(3) . . ? C4 C3 C2 122.3(3) . . ? C4 C3 N2 118.6(3) . . ? C2 C3 N2 119.1(3) . . ? C3 C4 C5 118.8(3) . . ? C6 C5 C4 120.2(3) . . ? C1 C6 C5 119.0(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 C6 C1 C2 C3 1.0(5) . . . . ? N1 C1 C2 C3 -179.1(3) . . . . ? C1 C2 C3 C4 -1.0(5) . . . . ? C1 C2 C3 N2 -179.9(3) . . . . ? C2 C3 C4 C5 0.3(5) . . . . ? N2 C3 C4 C5 179.3(3) . . . . ? C3 C4 C5 C6 0.3(5) . . . . ? C2 C1 C6 C5 -0.4(5) . . . . ? N1 C1 C6 C5 179.7(3) . . . . ? C4 C5 C6 C1 -0.3(5) . . . . ? 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 O1 H12 F2 0.87(6) 1.89(6) 2.719(4) 158(6) . O1 H11 F3 0.72(6) 2.05(6) 2.702(4) 151(6) 2_557 N1 H1C O1 0.91 1.86 2.705(5) 154.0 . N1 H1C F2 0.91 2.62 3.089(4) 113.2 2_547 N1 H1B F5 0.91 2.16 2.901(4) 137.7 1_655 N1 H1B F4 0.91 2.29 2.900(4) 124.4 1_655 N1 H1A F4 0.91 1.93 2.779(4) 154.6 2_547 N2 H2C F6 0.91 1.91 2.756(4) 154.7 1_545 N2 H2C F2 0.91 2.45 3.207(5) 140.6 1_545 N2 H2B F5 0.91 1.95 2.845(3) 165.7 2_446 N2 H2B F1 0.91 2.38 3.025(3) 127.4 2_446 N2 H2B F6 0.91 2.50 3.141(4) 127.4 2_446 N2 H2A F1 0.91 1.88 2.784(4) 170.3 . N2 H2A F3 0.91 2.39 2.992(4) 123.5 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.659 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.073 data_2h _database_code_depnum_ccdc_archive 'CCDC 299867' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H9 N2, Cl' _chemical_formula_sum 'C6 H9 Cl N2' _chemical_formula_weight 144.60 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.7025(11) _cell_length_b 8.5328(17) _cell_length_c 14.781(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 719.2(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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.440 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8792 _exptl_absorpt_correction_T_max 0.9573 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4119 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0678 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1408 _reflns_number_gt 1229 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _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^)+(0.0070P)^2^+0.1305P] 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 calc _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(9) _refine_ls_number_reflns 1408 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0705 _refine_ls_wR_factor_gt 0.0675 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 Cl1 Cl 0.09835(10) 0.18764(7) 0.61393(4) 0.02326(17) Uani 1 1 d . . . N1 N 0.2804(4) 0.1606(3) 0.21805(14) 0.0237(5) Uani 1 1 d . . . N2 N -0.0795(4) 0.6374(2) 0.09804(16) 0.0231(5) Uani 1 1 d . . . C1 C 0.1047(5) 0.2339(3) 0.16773(14) 0.0187(5) Uani 1 1 d . . . C2 C 0.1045(5) 0.3972(3) 0.15617(15) 0.0188(5) Uani 1 1 d . . . C3 C -0.0780(4) 0.4660(2) 0.10994(16) 0.0172(5) Uani 1 1 d . . . C4 C -0.2626(4) 0.3820(3) 0.07412(17) 0.0210(5) Uani 1 1 d . . . C5 C -0.2608(4) 0.2197(3) 0.08487(16) 0.0215(6) Uani 1 1 d . . . C6 C -0.0808(4) 0.1475(3) 0.13170(15) 0.0213(5) Uani 1 1 d . . . H1 H 0.318(5) 0.065(4) 0.199(2) 0.058(11) Uiso 1 1 d . . . H2 H 0.408(4) 0.216(3) 0.2244(16) 0.029(7) Uiso 1 1 d . . . H3 H 0.225(4) 0.454(3) 0.1781(18) 0.021(7) Uiso 1 1 d . . . H4 H 0.059(5) 0.682(3) 0.1106(16) 0.028(6) Uiso 1 1 d . . . H5 H -0.121(6) 0.663(4) 0.038(3) 0.080(11) Uiso 1 1 d . . . H6 H -0.206(6) 0.683(4) 0.135(2) 0.065(10) Uiso 1 1 d . . . H7 H -0.377(4) 0.432(2) 0.0435(15) 0.013(6) Uiso 1 1 d . . . H8 H -0.402(5) 0.158(3) 0.0616(15) 0.028(6) Uiso 1 1 d . . . H9 H -0.084(5) 0.032(3) 0.1392(17) 0.045(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 Cl1 0.0201(3) 0.0236(3) 0.0261(3) -0.0029(3) 0.0014(3) 0.0000(3) N1 0.0217(11) 0.0271(13) 0.0224(12) 0.0001(10) -0.0010(9) -0.0018(11) N2 0.0183(10) 0.0197(9) 0.0312(13) -0.0035(9) 0.0054(11) -0.0012(10) C1 0.0207(11) 0.0260(12) 0.0093(11) 0.0006(9) 0.0037(12) -0.0016(12) C2 0.0167(11) 0.0257(12) 0.0141(12) -0.0054(9) 0.0030(12) -0.0057(12) C3 0.0190(11) 0.0193(11) 0.0131(11) -0.0011(10) 0.0066(13) -0.0010(10) C4 0.0187(12) 0.0282(12) 0.0161(13) 0.0000(11) 0.0009(10) -0.0019(12) C5 0.0202(12) 0.0270(14) 0.0173(13) -0.0062(10) 0.0039(10) -0.0075(11) C6 0.0241(12) 0.0226(13) 0.0172(12) -0.0005(9) 0.0039(11) -0.0059(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.396(3) . ? N2 C3 1.473(3) . ? C1 C6 1.395(3) . ? C1 C2 1.404(3) . ? C2 C3 1.377(4) . ? C3 C4 1.379(3) . ? C4 C5 1.394(3) . ? C5 C6 1.383(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 C6 C1 N1 120.7(2) . . ? C6 C1 C2 118.5(3) . . ? N1 C1 C2 120.7(3) . . ? C3 C2 C1 119.0(3) . . ? C2 C3 C4 123.1(2) . . ? C2 C3 N2 119.1(2) . . ? C4 C3 N2 117.8(2) . . ? C3 C4 C5 117.8(2) . . ? C6 C5 C4 120.4(2) . . ? C5 C6 C1 121.2(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.0(4) . . . . ? N1 C1 C2 C3 -176.8(2) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C1 C2 C3 N2 179.7(2) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? N2 C3 C4 C5 179.6(2) . . . . ? C3 C4 C5 C6 1.3(4) . . . . ? C4 C5 C6 C1 -1.2(4) . . . . ? N1 C1 C6 C5 177.4(2) . . . . ? C2 C1 C6 C5 0.5(3) . . . . ? 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 H2 Cl1 0.87(3) 2.75(2) 3.336(2) 125.7(19) 3_556 N1 H1 Cl1 0.88(3) 2.55(3) 3.417(2) 168(3) 2_554 N2 H6 N1 0.99(3) 2.22(3) 2.957(3) 130(3) 4 N2 H6 Cl1 0.99(3) 2.51(3) 3.322(2) 139(2) 2_464 N2 H5 Cl1 0.94(4) 2.26(4) 3.164(3) 160(3) 4 N2 H4 Cl1 0.90(3) 2.25(3) 3.132(2) 169(2) 2_564 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.214 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.066 data_3a _database_code_depnum_ccdc_archive 'CCDC 299868' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, 2(Br)' _chemical_formula_sum 'C6 H10 Br2 N2' _chemical_formula_weight 269.98 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' Br Br -0.2901 2.4595 '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 4.4488(5) _cell_length_b 6.089(5) _cell_length_c 8.701(6) _cell_angle_alpha 103.616(4) _cell_angle_beta 104.616(5) _cell_angle_gamma 101.392(5) _cell_volume 213.2(2) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.102 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 130 _exptl_absorpt_coefficient_mu 9.433 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0883 _exptl_absorpt_correction_T_max 0.4522 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1357 _diffrn_reflns_av_R_equivalents 0.0943 _diffrn_reflns_av_sigmaI/netI 0.0999 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.78 _diffrn_reflns_theta_max 25.99 _reflns_number_total 824 _reflns_number_gt 806 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _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^)+(0.0084P)^2^+0.2600P] 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 calc _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.12(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 824 _refine_ls_number_parameters 47 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0921 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _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 Br1 Br 0.30787(7) 0.69444(5) 0.36215(3) 0.0102(3) Uani 1 1 d . . . N1 N 0.0346(7) 0.8626(5) 0.6800(3) 0.0095(7) Uani 1 1 d . . . H1A H -0.0469 0.9843 0.6642 0.011 Uiso 1 1 calc R . . H1B H -0.1282 0.7389 0.6713 0.011 Uiso 1 1 calc R . . H1C H 0.1308 0.8192 0.6014 0.011 Uiso 1 1 calc R . . C1 C 0.3219(9) 1.1536(6) 0.9570(4) 0.0107(8) Uani 1 1 d . . . H1 H 0.1995 1.2569 0.9266 0.013 Uiso 1 1 calc R . . C2 C 0.2741(9) 0.9362(6) 0.8465(4) 0.0089(7) Uani 1 1 d . . . C3 C 0.4493(9) 0.7808(6) 0.8873(4) 0.0101(7) Uani 1 1 d . . . H3 H 0.4125 0.6320 0.8096 0.012 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 Br1 0.0114(4) 0.0053(3) 0.0124(4) 0.0012(2) 0.0034(2) 0.0014(2) N1 0.0117(17) 0.0062(15) 0.0082(15) -0.0002(12) 0.0023(13) 0.0009(13) C1 0.0131(19) 0.0093(18) 0.0113(17) 0.0036(14) 0.0051(15) 0.0042(15) C2 0.0084(17) 0.0078(17) 0.0098(16) 0.0036(14) 0.0038(14) -0.0016(14) C3 0.0101(18) 0.0051(16) 0.0145(17) 0.0002(13) 0.0059(15) 0.0014(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 N1 C2 1.470(5) . ? C1 C2 1.382(5) . ? C1 C3 1.385(5) 2_677 ? C2 C3 1.393(5) . ? C3 C1 1.385(5) 2_677 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C3 119.2(4) . 2_677 ? C1 C2 C3 121.8(3) . . ? C1 C2 N1 120.4(3) . . ? C3 C2 N1 117.8(3) . . ? C1 C3 C2 119.0(3) 2_677 . ? 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 C3 C1 C2 C3 0.1(6) 2_677 . . . ? C3 C1 C2 N1 -179.5(3) 2_677 . . . ? C1 C2 C3 C1 -0.1(6) . . . 2_677 ? N1 C2 C3 C1 179.6(3) . . . 2_677 ? 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 Br1 0.91 2.49 3.397(4) 174.0 2_576 N1 H1B Br1 0.91 2.52 3.324(4) 146.9 2_566 N1 H1C Br1 0.91 2.42 3.321(3) 171.3 . _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 1.700 _refine_diff_density_min -1.840 _refine_diff_density_rms 0.474 data_3b _database_code_depnum_ccdc_archive 'CCDC 299869' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, 2(Cl)' _chemical_formula_sum 'C6 H10 Cl2 N2' _chemical_formula_weight 181.06 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' Cl Cl 0.1484 0.1585 '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 4.2850(2) _cell_length_b 5.8053(15) _cell_length_c 8.6259(6) _cell_angle_alpha 71.035(4) _cell_angle_beta 76.868(5) _cell_angle_gamma 79.631(5) _cell_volume 196.30(5) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 94 _exptl_absorpt_coefficient_mu 0.749 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7058 _exptl_absorpt_correction_T_max 0.9289 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1501 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0702 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 27.49 _reflns_number_total 875 _reflns_number_gt 843 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-seed _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^)+(0.0000P)^2^+0.0334P] 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 calc _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 875 _refine_ls_number_parameters 47 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0209 _refine_ls_wR_factor_ref 0.0667 _refine_ls_wR_factor_gt 0.0658 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 Cl1 Cl 0.43566(5) 0.80105(4) 0.87150(3) 0.00941(15) Uani 1 1 d . . . N1 N 0.1393(2) 0.35621(18) 0.82629(12) 0.0084(2) Uani 1 1 d . . . C1 C 0.0665(2) 0.4327(2) 0.65763(14) 0.0074(3) Uani 1 1 d . . . H1A H 0.2443 0.4713 0.8376 0.013 Uiso 1 1 calc R . . H1B H 0.2667 0.2100 0.8439 0.013 Uiso 1 1 calc R . . H1C H -0.0477 0.3399 0.9021 0.013 Uiso 1 1 calc R . . C2 C -0.0729(3) 0.2724(2) 0.61129(15) 0.0087(3) Uani 1 1 d . . . H2 H -0.1211 0.1180 0.6879 0.010 Uiso 1 1 calc R . . C3 C -0.1409(3) 0.3413(2) 0.45140(15) 0.0090(2) Uani 1 1 d . . . H3 H -0.2370 0.2349 0.4173 0.011 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 Cl1 0.0116(2) 0.0072(2) 0.0096(2) -0.00127(13) -0.00273(13) -0.00264(12) N1 0.0100(5) 0.0080(5) 0.0075(5) -0.0021(4) -0.0016(4) -0.0019(3) C1 0.0067(5) 0.0085(5) 0.0064(6) -0.0028(4) -0.0007(4) 0.0009(4) C2 0.0096(5) 0.0059(5) 0.0090(6) -0.0006(4) -0.0001(4) -0.0021(4) C3 0.0091(5) 0.0084(5) 0.0111(6) -0.0047(4) -0.0019(4) -0.0015(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.4655(15) . ? C2 C3 1.3889(17) . ? C2 C1 1.3899(16) . ? C3 C1 1.3859(16) 2_566 ? C1 C3 1.3859(16) 2_566 ? 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 C3 C2 C1 119.07(10) . . ? C1 C3 C2 119.05(11) 2_566 . ? C3 C1 C2 121.88(11) 2_566 . ? C3 C1 N1 119.76(10) 2_566 . ? C2 C1 N1 118.36(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 C1 0.27(17) . . . 2_566 ? C3 C2 C1 C3 -0.27(18) . . . 2_566 ? C3 C2 C1 N1 -179.45(9) . . . . ? 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 Cl1 0.91 2.34 3.2394(12) 171.2 . N1 H1B Cl1 0.91 2.30 3.1759(12) 160.3 1_545 N1 H1C Cl1 0.91 2.29 3.1691(10) 163.8 2_567 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.394 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.144 data_3c _database_code_depnum_ccdc_archive 'CCDC 299870' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, 2(C2 F3 O2)' _chemical_formula_sum 'C10 H10 F6 N2 O4' _chemical_formula_weight 336.20 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' _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 5.9661(5) _cell_length_b 16.0900(14) _cell_length_c 7.2186(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.075(5) _cell_angle_gamma 90.00 _cell_volume 680.04(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9328 _exptl_absorpt_correction_T_max 0.9826 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5611 _diffrn_reflns_av_R_equivalents 0.0714 _diffrn_reflns_av_sigmaI/netI 0.0589 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1544 _reflns_number_gt 1293 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-seed _refine_special_details ; R1 possibly high due to twinning, Platon alert: 930_ALERT_2_B Check Twin Law ( 4 0 -1)[ 1 0 0] Estimated BASF 0.26 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^)+(0.1125P)^2^+1.0543P] 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 calc _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.079(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1544 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0929 _refine_ls_R_factor_gt 0.0825 _refine_ls_wR_factor_ref 0.2162 _refine_ls_wR_factor_gt 0.2111 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _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 F1 F -0.2821(3) 0.85159(13) 0.4718(3) 0.0314(6) Uani 1 1 d . . . F2 F 0.0358(4) 0.91334(11) 0.5840(3) 0.0279(6) Uani 1 1 d . . . F3 F -0.0764(4) 0.90214(13) 0.2831(3) 0.0312(6) Uani 1 1 d . . . O1 O -0.0524(4) 0.71914(14) 0.3674(4) 0.0267(6) Uani 1 1 d . . . O2 O 0.2714(4) 0.78178(14) 0.5076(3) 0.0225(6) Uani 1 1 d . . . N1 N 0.5048(5) 0.66242(16) 0.3489(4) 0.0173(6) Uani 1 1 d . . . C1 C 0.5021(5) 0.57806(18) 0.4274(4) 0.0174(7) Uani 1 1 d . . . C2 C 0.3405(5) 0.5583(2) 0.5328(4) 0.0219(7) Uani 1 1 d . . . H2 H 0.2318 0.5986 0.5539 0.026 Uiso 1 1 calc R . . C3 C 0.6625(5) 0.52087(19) 0.3920(4) 0.0214(7) Uani 1 1 d . . . H3 H 0.7720 0.5356 0.3179 0.026 Uiso 1 1 calc R . . C4 C 0.0619(5) 0.77880(18) 0.4433(4) 0.0180(7) Uani 1 1 d . . . C5 C -0.0672(6) 0.86231(19) 0.4485(4) 0.0210(7) Uani 1 1 d . . . H11 H 0.648(7) 0.679(2) 0.351(5) 0.017(9) Uiso 1 1 d . . . H12 H 0.425(7) 0.698(3) 0.403(6) 0.022(9) Uiso 1 1 d . . . H13 H 0.418(8) 0.663(3) 0.224(7) 0.036(12) 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 F1 0.0219(10) 0.0325(11) 0.0416(12) 0.0010(9) 0.0108(9) 0.0059(8) F2 0.0379(12) 0.0167(9) 0.0286(10) -0.0038(7) 0.0048(9) 0.0028(8) F3 0.0397(13) 0.0314(11) 0.0231(10) 0.0107(8) 0.0074(8) 0.0074(9) O1 0.0232(12) 0.0228(11) 0.0338(13) -0.0095(10) 0.0050(9) -0.0039(9) O2 0.0189(11) 0.0229(11) 0.0250(11) -0.0057(9) 0.0028(8) 0.0014(8) N1 0.0182(13) 0.0139(11) 0.0199(13) 0.0012(9) 0.0037(10) 0.0006(10) C1 0.0178(14) 0.0173(13) 0.0166(13) 0.0009(10) 0.0017(11) 0.0010(11) C2 0.0223(15) 0.0184(14) 0.0263(15) 0.0014(11) 0.0082(12) 0.0046(12) C3 0.0227(15) 0.0193(14) 0.0246(15) 0.0024(11) 0.0102(12) 0.0020(11) C4 0.0202(14) 0.0171(13) 0.0175(13) 0.0005(11) 0.0056(10) -0.0003(11) C5 0.0228(15) 0.0201(14) 0.0204(15) 0.0021(11) 0.0054(11) 0.0022(12) _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 F1 C5 1.336(4) . ? F2 C5 1.333(4) . ? F3 C5 1.347(4) . ? O1 C4 1.242(4) . ? O2 C4 1.248(4) . ? N1 C1 1.472(4) . ? C1 C2 1.376(4) . ? C1 C3 1.386(4) . ? C2 C3 1.386(4) 3_666 ? C3 C2 1.386(4) 3_666 ? C4 C5 1.553(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C3 122.1(3) . . ? C2 C1 N1 119.1(3) . . ? C3 C1 N1 118.8(3) . . ? C1 C2 C3 119.5(3) . 3_666 ? C1 C3 C2 118.5(3) . 3_666 ? O1 C4 O2 128.3(3) . . ? O1 C4 C5 116.5(3) . . ? O2 C4 C5 115.1(3) . . ? F2 C5 F1 107.8(3) . . ? F2 C5 F3 107.0(2) . . ? F1 C5 F3 107.2(2) . . ? F2 C5 C4 112.9(3) . . ? F1 C5 C4 112.6(3) . . ? F3 C5 C4 109.0(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C1 C2 C3 0.5(5) . . . 3_666 ? N1 C1 C2 C3 -179.7(3) . . . 3_666 ? C2 C1 C3 C2 -0.5(5) . . . 3_666 ? N1 C1 C3 C2 179.7(3) . . . 3_666 ? O1 C4 C5 F2 157.6(3) . . . . ? O2 C4 C5 F2 -26.0(4) . . . . ? O1 C4 C5 F1 35.2(4) . . . . ? O2 C4 C5 F1 -148.4(3) . . . . ? O1 C4 C5 F3 -83.6(3) . . . . ? O2 C4 C5 F3 92.7(3) . . . . ? 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 H13 O2 0.95(5) 1.86(5) 2.738(3) 153(4) 4_575 N1 H13 F2 0.95(5) 2.62(5) 3.304(3) 130(4) 4_575 N1 H12 O2 0.88(4) 1.87(4) 2.748(3) 174(4) . N1 H11 O1 0.89(4) 1.89(4) 2.774(4) 176(4) 1_655 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.928 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.131 data_3d _database_code_depnum_ccdc_archive 'CCDC 299871' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, F6 Si' _chemical_formula_sum 'C6 H10 F6 N2 Si' _chemical_formula_weight 252.25 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.5834(11) _cell_length_b 9.4219(19) _cell_length_c 9.6386(19) _cell_angle_alpha 80.826(7) _cell_angle_beta 89.959(6) _cell_angle_gamma 73.219(6) _cell_volume 478.70(16) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.750 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.306 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7492 _exptl_absorpt_correction_T_max 0.9413 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3157 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0921 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1681 _reflns_number_gt 1259 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _refine_special_details ; Platon suggests C2/c as an alternative space group however it was not possible to refine the structure in this space group 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^)+(0.0000P)^2^+2.5965P] 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 calc _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.033(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1681 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0884 _refine_ls_R_factor_gt 0.0676 _refine_ls_wR_factor_ref 0.1779 _refine_ls_wR_factor_gt 0.1670 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.1575(7) 0.8179(4) 0.4428(4) 0.0120(8) Uani 1 1 d . . . H1A H -0.3263 0.8521 0.4495 0.018 Uiso 1 1 calc R . . H1B H -0.1161 0.8504 0.3546 0.018 Uiso 1 1 calc R . . H1C H -0.0800 0.8534 0.5067 0.018 Uiso 1 1 calc R . . N2 N 0.6645(7) 0.1816(4) 1.0563(4) 0.0124(8) Uani 1 1 d . . . H2A H 0.6298 0.1496 1.1461 0.019 Uiso 1 1 calc R . . H2B H 0.8326 0.1488 1.0461 0.019 Uiso 1 1 calc R . . H2C H 0.5840 0.1442 0.9955 0.019 Uiso 1 1 calc R . . C1 C -0.0775(8) 0.6543(5) 0.4710(5) 0.0129(10) Uani 1 1 d . . . C2 C -0.2110(9) 0.5803(5) 0.5607(5) 0.0207(11) Uani 1 1 d . . . H2 H -0.3552 0.6357 0.6019 0.025 Uiso 1 1 calc R . . C3 C -0.1335(9) 0.4238(5) 0.5907(6) 0.0208(11) Uani 1 1 d . . . H3 H -0.2239 0.3715 0.6525 0.025 Uiso 1 1 calc R . . C4 C 0.5796(8) 0.3458(5) 1.0263(4) 0.0120(10) Uani 1 1 d . . . C5 C 0.3721(9) 0.4179(5) 0.9379(6) 0.0215(11) Uani 1 1 d . . . H5 H 0.2847 0.3615 0.8960 0.026 Uiso 1 1 calc R . . C6 C 0.2915(9) 0.5741(5) 0.9107(5) 0.0196(11) Uani 1 1 d . . . H6 H 0.1493 0.6255 0.8493 0.023 Uiso 1 1 calc R . . Si1 Si -0.2535(2) 0.99682(14) 0.75064(13) 0.0109(4) Uani 1 1 d . . . F1 F -0.0860(5) 1.1041(3) 0.8028(3) 0.0175(7) Uani 1 1 d . . . F2 F -0.4202(5) 0.8886(3) 0.6994(3) 0.0174(7) Uani 1 1 d . . . F3 F -0.5151(5) 1.1035(3) 0.8128(3) 0.0180(7) Uani 1 1 d . . . F4 F 0.0080(5) 0.8897(3) 0.6888(3) 0.0165(7) Uani 1 1 d . . . F5 F -0.3191(5) 1.1088(3) 0.5921(3) 0.0174(7) Uani 1 1 d . . . F6 F -0.1879(5) 0.8854(3) 0.9093(3) 0.0168(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0127(19) 0.0135(19) 0.0106(19) -0.0032(15) 0.0034(15) -0.0045(15) N2 0.0130(19) 0.0126(19) 0.0102(19) 0.0012(15) 0.0002(15) -0.0032(15) C1 0.015(2) 0.013(2) 0.009(2) -0.0003(18) -0.0020(18) -0.0033(18) C2 0.022(3) 0.016(2) 0.021(3) 0.001(2) 0.010(2) -0.0016(19) C3 0.019(2) 0.014(2) 0.029(3) -0.001(2) 0.012(2) -0.0037(19) C4 0.015(2) 0.012(2) 0.009(2) 0.0009(18) 0.0045(18) -0.0044(18) C5 0.022(3) 0.016(2) 0.028(3) -0.005(2) -0.007(2) -0.006(2) C6 0.020(2) 0.017(2) 0.020(3) -0.002(2) -0.005(2) -0.003(2) Si1 0.0123(6) 0.0135(7) 0.0073(6) -0.0012(5) 0.0007(4) -0.0044(5) F1 0.0183(14) 0.0206(14) 0.0160(14) -0.0010(11) -0.0007(11) -0.0107(11) F2 0.0190(14) 0.0209(14) 0.0161(14) -0.0070(11) 0.0017(11) -0.0098(11) F3 0.0173(14) 0.0205(14) 0.0177(15) -0.0071(11) 0.0054(11) -0.0059(11) F4 0.0132(13) 0.0180(14) 0.0149(14) -0.0023(11) 0.0027(11) 0.0007(11) F5 0.0193(14) 0.0197(14) 0.0111(14) 0.0024(11) -0.0012(11) -0.0052(11) F6 0.0192(14) 0.0204(14) 0.0095(13) 0.0017(11) 0.0010(11) -0.0061(11) _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 F3 1.687(3) . ? Si1 F6 1.686(3) . ? Si1 F4 1.687(3) . ? Si1 F5 1.687(3) . ? Si1 F1 1.691(3) . ? Si1 F2 1.691(3) . ? N2 C4 1.462(6) . ? N1 C1 1.456(6) . ? C5 C4 1.375(7) . ? C5 C6 1.390(7) . ? C2 C1 1.377(6) . ? C2 C3 1.393(7) . ? C6 C4 1.384(7) 2_667 ? C3 C1 1.386(7) 2_566 ? C1 C3 1.386(7) 2_566 ? C4 C6 1.384(7) 2_667 ? 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 F3 Si1 F6 89.63(14) . . ? F3 Si1 F4 179.82(16) . . ? F6 Si1 F4 90.22(14) . . ? F3 Si1 F5 90.28(14) . . ? F6 Si1 F5 179.83(16) . . ? F4 Si1 F5 89.87(14) . . ? F3 Si1 F1 90.54(15) . . ? F6 Si1 F1 89.26(14) . . ? F4 Si1 F1 89.56(15) . . ? F5 Si1 F1 90.59(14) . . ? F3 Si1 F2 89.55(14) . . ? F6 Si1 F2 90.37(14) . . ? F4 Si1 F2 90.35(15) . . ? F5 Si1 F2 89.79(14) . . ? F1 Si1 F2 179.61(16) . . ? C4 C5 C6 119.3(5) . . ? C1 C2 C3 119.7(5) . . ? C4 C6 C5 119.4(5) 2_667 . ? C1 C3 C2 119.0(4) 2_566 . ? C2 C1 C3 121.3(4) . 2_566 ? C2 C1 N1 119.1(4) . . ? C3 C1 N1 119.5(4) 2_566 . ? C5 C4 C6 121.2(4) . 2_667 ? C5 C4 N2 119.7(4) . . ? C6 C4 N2 119.1(4) 2_667 . ? 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 C4 C5 C6 C4 -0.5(8) . . . 2_667 ? C1 C2 C3 C1 -0.1(9) . . . 2_566 ? C3 C2 C1 C3 0.1(9) . . . 2_566 ? C3 C2 C1 N1 -178.7(4) . . . . ? C6 C5 C4 C6 0.5(8) . . . 2_667 ? C6 C5 C4 N2 179.6(4) . . . . ? 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 N2 H2A F2 0.91 1.95 2.804(4) 156.5 2_567 N2 H2A F4 0.91 2.48 2.932(4) 111.2 2_667 N2 H2A F3 0.91 2.61 3.117(4) 115.6 2_567 N2 H2B F6 0.91 1.95 2.814(4) 157.2 2_667 N2 H2B F1 0.91 2.60 3.132(4) 118.1 2_667 N2 H2C F3 0.91 1.97 2.835(5) 157.5 1_645 N2 H2C F6 0.91 2.47 2.914(4) 110.6 2_567 N1 H1A F5 0.91 1.94 2.809(4) 160.2 2_476 N1 H1A F2 0.91 2.63 3.181(4) 119.7 2_476 N1 H1B F1 0.91 1.96 2.830(4) 160.4 2_576 N1 H1C F4 0.91 1.93 2.795(5) 157.7 . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.565 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.104 data_3e _database_code_depnum_ccdc_archive 'CCDC 299872' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2, O4 S' _chemical_formula_sum 'C6 H10 N2 O4 S' _chemical_formula_weight 206.22 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.6270(13) _cell_length_b 7.3642(15) _cell_length_c 18.130(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 884.8(3) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.351 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8440 _exptl_absorpt_correction_T_max 0.9657 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5658 _diffrn_reflns_av_R_equivalents 0.0614 _diffrn_reflns_av_sigmaI/netI 0.0671 _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 -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1727 _reflns_number_gt 1508 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _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^)+(0.0156P)^2^+0.4078P] 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 calc _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.016(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.19(13) _refine_ls_number_reflns 1727 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0856 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.015 _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 S1 S 0.26229(10) 0.52234(7) 0.02194(3) 0.01134(19) Uani 1 1 d . . . O1 O 0.2715(3) 0.5337(2) -0.05938(8) 0.0171(4) Uani 1 1 d . . . O2 O 0.0660(3) 0.4244(3) 0.04388(12) 0.0156(5) Uani 1 1 d . . . O3 O 0.2627(4) 0.7046(2) 0.05501(9) 0.0203(4) Uani 1 1 d . . . O4 O 0.4505(3) 0.4183(3) 0.04829(12) 0.0154(5) Uani 1 1 d . . . N1 N 0.7637(4) 0.6226(3) 0.11265(12) 0.0133(4) Uani 1 1 d . . . N2 N 0.7491(5) 0.5733(3) 0.42412(11) 0.0130(4) Uani 1 1 d . . . C1 C 0.7598(5) 0.6128(3) 0.19298(13) 0.0122(5) Uani 1 1 d . . . C2 C 0.5783(4) 0.5510(4) 0.22814(15) 0.0162(6) Uani 1 1 d . . . C3 C 0.5745(4) 0.5412(4) 0.30448(15) 0.0162(6) Uani 1 1 d . . . C4 C 0.7523(5) 0.5919(3) 0.34392(12) 0.0125(5) Uani 1 1 d . . . C5 C 0.9344(4) 0.6559(4) 0.30923(15) 0.0147(6) Uani 1 1 d . . . C6 C 0.9379(4) 0.6671(4) 0.23237(15) 0.0143(6) Uani 1 1 d . . . H2 H 0.460(4) 0.526(4) 0.1981(14) 0.010(6) Uiso 1 1 d . . . H3 H 0.450(4) 0.501(4) 0.3284(15) 0.016(7) Uiso 1 1 d . . . H5 H 1.051(5) 0.694(5) 0.341(2) 0.032(9) Uiso 1 1 d . . . H6 H 1.066(5) 0.708(4) 0.2077(15) 0.010(7) Uiso 1 1 d . . . H11 H 0.659(6) 0.581(5) 0.095(2) 0.029(11) Uiso 1 1 d . . . H12 H 0.889(5) 0.556(4) 0.0929(16) 0.016(8) Uiso 1 1 d . . . H13 H 0.761(5) 0.748(4) 0.0956(14) 0.021(7) Uiso 1 1 d . . . H21 H 0.645(5) 0.604(5) 0.4437(19) 0.015(9) Uiso 1 1 d . . . H22 H 0.745(6) 0.452(5) 0.4387(16) 0.030(8) Uiso 1 1 d . . . H23 H 0.861(6) 0.627(6) 0.442(2) 0.033(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 S1 0.0150(3) 0.0083(3) 0.0107(3) 0.0000(2) -0.0004(3) -0.0009(3) O1 0.0269(10) 0.0162(8) 0.0083(8) 0.0001(7) 0.0006(8) 0.0026(11) O2 0.0170(10) 0.0123(12) 0.0174(12) 0.0023(9) 0.0012(8) -0.0008(8) O3 0.0309(11) 0.0088(8) 0.0213(10) -0.0059(7) 0.0008(11) 0.0000(10) O4 0.0161(10) 0.0122(12) 0.0179(11) 0.0010(9) -0.0036(8) -0.0008(8) N1 0.0129(12) 0.0153(10) 0.0117(11) 0.0004(8) -0.0004(12) -0.0015(13) N2 0.0180(12) 0.0112(10) 0.0097(10) -0.0001(8) 0.0012(13) 0.0007(13) C1 0.0192(13) 0.0095(10) 0.0078(11) 0.0004(8) 0.0007(14) 0.0016(14) C2 0.0160(13) 0.0202(14) 0.0126(14) 0.0008(12) -0.0033(11) -0.0016(12) C3 0.0163(13) 0.0183(14) 0.0140(14) 0.0020(12) 0.0043(11) -0.0011(12) C4 0.0196(13) 0.0094(10) 0.0085(12) 0.0006(8) 0.0023(14) 0.0037(14) C5 0.0176(14) 0.0130(13) 0.0134(15) 0.0006(12) -0.0036(12) -0.0008(11) C6 0.0153(14) 0.0147(14) 0.0129(14) 0.0021(12) 0.0042(12) -0.0020(11) _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 S1 O3 1.4700(16) . ? S1 O1 1.4780(16) . ? S1 O4 1.540(2) . ? S1 O2 1.540(2) . ? N1 C1 1.458(3) . ? N2 C4 1.461(3) . ? C1 C2 1.435(4) . ? C1 C6 1.436(4) . ? C2 C3 1.386(4) . ? C3 C4 1.428(4) . ? C4 C5 1.440(4) . ? C5 C6 1.396(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O1 110.81(10) . . ? O3 S1 O4 109.04(12) . . ? O1 S1 O4 107.70(12) . . ? O3 S1 O2 108.91(13) . . ? O1 S1 O2 108.61(12) . . ? O4 S1 O2 111.78(9) . . ? C2 C1 C6 123.8(2) . . ? C2 C1 N1 118.3(3) . . ? C6 C1 N1 117.9(3) . . ? C3 C2 C1 118.4(2) . . ? C2 C3 C4 118.1(2) . . ? C3 C4 C5 123.9(2) . . ? C3 C4 N2 117.5(3) . . ? C5 C4 N2 118.5(3) . . ? C6 C5 C4 118.0(2) . . ? C5 C6 C1 117.8(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.7(4) . . . . ? N1 C1 C2 C3 179.9(2) . . . . ? C1 C2 C3 C4 -0.5(4) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? C2 C3 C4 N2 -177.4(2) . . . . ? C3 C4 C5 C6 -0.7(4) . . . . ? N2 C4 C5 C6 177.8(2) . . . . ? C4 C5 C6 C1 -0.4(4) . . . . ? C2 C1 C6 C5 1.1(4) . . . . ? N1 C1 C6 C5 -179.4(2) . . . . ? 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 H13 O1 0.97(3) 1.74(3) 2.710(3) 175(3) 3_565 N1 H12 O2 1.03(3) 1.76(3) 2.775(3) 167(3) 1_655 N1 H11 O4 0.82(4) 2.02(4) 2.817(3) 164(4) . N2 H23 O2 0.90(4) 2.26(4) 2.919(3) 130(3) 4_655 N2 H23 O4 0.90(4) 2.31(4) 3.006(3) 133(3) 2_665 N2 H22 O3 0.93(3) 1.83(3) 2.743(3) 167(3) 4_645 N2 H21 O2 0.81(3) 2.30(3) 3.012(3) 147(3) 2_565 N2 H21 O4 0.81(3) 2.41(4) 2.908(3) 121(3) 4_655 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.322 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.068 data_4a _database_code_depnum_ccdc_archive 'CCDC 299873' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 N, B F4' _chemical_formula_sum 'C6 H8 B F4 N' _chemical_formula_weight 180.94 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.3752(16) _cell_length_b 5.7860(9) _cell_length_c 9.3866(19) _cell_angle_alpha 90.00 _cell_angle_beta 97.620(11) _cell_angle_gamma 90.00 _cell_volume 397.02(13) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 184 _exptl_absorpt_coefficient_mu 0.154 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9269 _exptl_absorpt_correction_T_max 0.9847 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2751 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.1385 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.15 _diffrn_reflns_theta_max 26.36 _reflns_number_total 1543 _reflns_number_gt 1303 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _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^)+(0.0634P)^2^+0.1937P] 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 calc _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.09(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(17) _refine_ls_number_reflns 1543 _refine_ls_number_parameters 111 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.1859 _refine_ls_wR_factor_gt 0.1786 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.003 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 F1 F 0.1413(3) 0.7027(4) 0.9016(2) 0.0331(7) Uani 1 1 d . . . F2 F 0.1522(3) 1.0985(4) 0.9078(2) 0.0329(7) Uani 1 1 d . . . F3 F 0.3161(4) 0.8878(5) 1.0860(2) 0.0425(7) Uani 1 1 d . . . F4 F 0.4012(3) 0.8895(5) 0.8593(2) 0.0412(7) Uani 1 1 d . . . N1 N 0.7750(4) 0.9005(7) 0.8430(3) 0.0250(7) Uani 1 1 d . . . H11 H 0.6678 0.8460 0.8680 0.038 Uiso 1 1 calc R . . H12 H 0.7940 1.0472 0.8765 0.038 Uiso 1 1 calc R . . H13 H 0.8687 0.8084 0.8820 0.038 Uiso 1 1 calc R . . C1 C 0.7659(4) 0.9000(8) 0.6838(3) 0.0218(7) Uani 1 1 d . . . C2 C 0.8363(5) 1.0884(7) 0.6177(4) 0.0248(8) Uani 1 1 d . . . H2 H 0.8909 1.2140 0.6728 0.030 Uiso 1 1 calc R . . C3 C 0.8247(5) 1.0882(7) 0.4677(4) 0.0271(9) Uani 1 1 d . . . H3 H 0.8723 1.2146 0.4198 0.033 Uiso 1 1 calc R . . C4 C 0.7436(5) 0.9033(9) 0.3883(3) 0.0280(8) Uani 1 1 d . . . H4 H 0.7354 0.9048 0.2865 0.034 Uiso 1 1 calc R . . C5 C 0.6738(5) 0.7145(7) 0.4581(4) 0.0268(8) Uani 1 1 d . . . H5 H 0.6191 0.5885 0.4034 0.032 Uiso 1 1 calc R . . C6 C 0.6849(5) 0.7123(7) 0.6079(4) 0.0241(8) Uani 1 1 d . . . H6 H 0.6384 0.5859 0.6565 0.029 Uiso 1 1 calc R . . B1 B 0.2554(5) 0.8922(10) 0.9378(4) 0.0254(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0305(15) 0.0329(13) 0.0362(14) -0.0032(11) 0.0054(11) -0.0014(11) F2 0.0319(15) 0.0297(12) 0.0372(15) -0.0015(11) 0.0054(11) 0.0051(11) F3 0.0588(15) 0.0431(14) 0.0234(10) -0.0001(13) -0.0027(10) -0.0018(17) F4 0.0277(12) 0.0545(15) 0.0442(12) -0.0015(16) 0.0156(10) 0.0010(15) N1 0.0235(15) 0.0287(14) 0.0235(13) -0.0049(17) 0.0055(11) 0.0023(18) C1 0.0162(14) 0.0265(15) 0.0228(14) -0.0004(19) 0.0029(12) 0.001(2) C2 0.0190(18) 0.0259(17) 0.0296(19) -0.0033(15) 0.0034(14) 0.0018(16) C3 0.023(2) 0.030(2) 0.029(2) 0.0037(16) 0.0078(15) 0.0065(18) C4 0.0286(18) 0.0356(19) 0.0210(14) 0.0028(19) 0.0079(13) 0.012(2) C5 0.0228(19) 0.0266(18) 0.0306(19) -0.0068(16) 0.0021(15) 0.0052(17) C6 0.0230(19) 0.0229(17) 0.0271(18) 0.0013(15) 0.0066(15) 0.0004(17) B1 0.0218(18) 0.032(2) 0.0232(17) 0.001(2) 0.0066(14) 0.003(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 F1 B1 1.397(6) . ? F2 B1 1.424(6) . ? F3 B1 1.404(4) . ? F4 B1 1.382(4) . ? N1 C1 1.487(4) . ? C1 C2 1.389(6) . ? C1 C6 1.389(5) . ? C2 C3 1.400(5) . ? C3 C4 1.392(6) . ? C4 C5 1.406(6) . ? C5 C6 1.398(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 C2 C1 C6 123.0(3) . . ? C2 C1 N1 118.6(3) . . ? C6 C1 N1 118.4(3) . . ? C1 C2 C3 118.2(4) . . ? C4 C3 C2 120.2(4) . . ? C3 C4 C5 120.4(3) . . ? C6 C5 C4 120.0(3) . . ? C1 C6 C5 118.2(3) . . ? F4 B1 F1 110.3(4) . . ? F4 B1 F3 111.1(3) . . ? F1 B1 F3 109.3(3) . . ? F4 B1 F2 109.7(4) . . ? F1 B1 F2 108.7(3) . . ? F3 B1 F2 107.7(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 C6 C1 C2 C3 0.0(5) . . . . ? N1 C1 C2 C3 -179.1(3) . . . . ? C1 C2 C3 C4 0.3(5) . . . . ? C2 C3 C4 C5 -0.5(5) . . . . ? C3 C4 C5 C6 0.3(5) . . . . ? C2 C1 C6 C5 -0.2(5) . . . . ? N1 C1 C6 C5 178.9(3) . . . . ? C4 C5 C6 C1 0.0(5) . . . . ? 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 H11 F4 0.91 1.97 2.782(3) 147.1 . N1 H12 F3 0.91 2.18 2.994(5) 149.0 2_657 N1 H12 F1 0.91 2.26 2.966(4) 133.9 2_657 N1 H13 F1 0.91 2.09 2.918(4) 151.5 1_655 N1 H13 F2 0.91 2.34 2.912(4) 120.7 2_647 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.546 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.093 data_4b _database_code_depnum_ccdc_archive 'CCDC 299874' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 N, Br' _chemical_formula_sum 'C6 H8 Br N' _chemical_formula_weight 174.04 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' Br Br -0.2901 2.4595 '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)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 6.8425(14) _cell_length_b 5.9749(12) _cell_length_c 8.4158(17) _cell_angle_alpha 90.00 _cell_angle_beta 91.35(3) _cell_angle_gamma 90.00 _cell_volume 343.97(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description colourless _exptl_crystal_colour block _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.680 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 172 _exptl_absorpt_coefficient_mu 5.869 _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 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 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2241 _diffrn_reflns_av_R_equivalents 0.0958 _diffrn_reflns_av_sigmaI/netI 0.0835 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 4.18 _diffrn_reflns_theta_max 28.32 _reflns_number_total 894 _reflns_number_gt 823 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _refine_special_details ; no hydrogen was fixed/located on C2 large residual electron density peak is near Br suggesting that it may be disordered over two sites however refinement of a split Br atom did not improve the refinement 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^)+(0.1312P)^2^+1.5712P] 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 calc _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.09(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 894 _refine_ls_number_parameters 64 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0763 _refine_ls_wR_factor_ref 0.2005 _refine_ls_wR_factor_gt 0.1983 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.090 _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 Br1 Br 0.72368(11) 0.2500 0.05366(9) 0.0197(5) Uani 1 2 d S . . C1 C 0.2316(12) 0.2500 0.2859(11) 0.0191(18) Uani 1 2 d S . . N2 N 0.2079(11) 0.2500 0.1114(9) 0.0175(14) Uani 1 2 d S A . H2A H 0.2708 0.1295 0.0707 0.026 Uiso 0.50 1 calc PR . . H2B H 0.2597 0.3779 0.0715 0.026 Uiso 0.50 1 calc PR . . H2C H 0.0785 0.2426 0.0843 0.026 Uiso 1 2 calc SR . . C2 C 0.2649(13) 0.2500 0.6117(11) 0.026(2) Uani 1 2 d S . . C3 C 0.3089(18) 0.431(2) 0.3625(15) 0.018(2) Uani 0.50 1 d P A 1 H3 H 0.3514 0.5575 0.3046 0.022 Uiso 0.50 1 calc PR A 1 C4 C 0.3246(19) 0.426(3) 0.5301(16) 0.023(3) Uani 0.50 1 d P A 1 H4 H 0.3787 0.5514 0.5853 0.028 Uiso 0.50 1 calc PR A 1 C5 C 0.1692(18) 0.056(3) 0.3666(17) 0.022(3) Uani 0.50 1 d P A 2 H5 H 0.1164 -0.0682 0.3101 0.027 Uiso 0.50 1 calc PR A 2 C6 C 0.1878(19) 0.054(3) 0.5316(17) 0.024(3) Uani 0.50 1 d P A 2 H6 H 0.1505 -0.0740 0.5905 0.029 Uiso 0.50 1 calc PR A 2 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 Br1 0.0225(6) 0.0165(7) 0.0200(6) 0.000 0.0018(3) 0.000 C1 0.017(3) 0.023(5) 0.017(4) 0.000 0.000(3) 0.000 N2 0.023(3) 0.013(4) 0.016(3) 0.000 0.001(2) 0.000 C2 0.022(4) 0.042(7) 0.015(4) 0.000 0.004(3) 0.000 C3 0.024(6) 0.008(6) 0.022(6) 0.000(4) -0.002(4) -0.001(4) C4 0.021(6) 0.023(7) 0.025(6) -0.002(5) -0.004(4) 0.003(5) C5 0.019(6) 0.019(7) 0.030(6) -0.003(5) 0.005(4) -0.002(5) C6 0.021(6) 0.026(8) 0.025(6) 0.010(5) 0.006(4) 0.002(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 C1 C3 1.359(14) . ? C1 C3 1.359(14) 4_565 ? C1 C5 1.413(16) 4_565 ? C1 C5 1.413(16) . ? C1 N2 1.474(11) . ? C2 C4 1.327(18) 4_565 ? C2 C4 1.327(18) . ? C2 C6 1.445(18) . ? C2 C6 1.445(18) 4_565 ? C3 C4 1.412(18) . ? C5 C6 1.39(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 C3 C1 C3 105.3(12) . 4_565 ? C3 C1 C5 40.5(8) . 4_565 ? C3 C1 C5 122.8(10) 4_565 4_565 ? C3 C1 C5 122.8(10) . . ? C3 C1 C5 40.5(8) 4_565 . ? C5 C1 C5 110.0(13) 4_565 . ? C3 C1 N2 120.4(7) . . ? C3 C1 N2 120.4(7) 4_565 . ? C5 C1 N2 116.9(7) 4_565 . ? C5 C1 N2 116.9(7) . . ? C4 C2 C4 105.1(14) 4_565 . ? C4 C2 C6 39.5(8) 4_565 . ? C4 C2 C6 121.0(11) . . ? C4 C2 C6 121.0(11) 4_565 4_565 ? C4 C2 C6 39.5(8) . 4_565 ? C6 C2 C6 108.3(13) . 4_565 ? C1 C3 C4 118.6(12) . . ? C2 C4 C3 121.0(13) . . ? C6 C5 C1 117.8(12) . . ? C5 C6 C2 118.8(12) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 6.249 _refine_diff_density_min -1.376 _refine_diff_density_rms 0.311 data_4c _database_code_depnum_ccdc_archive 'CCDC 299875' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 N, Cl' _chemical_formula_sum 'C6 H8 Cl N' _chemical_formula_weight 129.58 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 15.760(3) _cell_length_b 5.3285(10) _cell_length_c 8.3932(11) _cell_angle_alpha 90.00 _cell_angle_beta 101.102(11) _cell_angle_gamma 90.00 _cell_volume 691.6(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 colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.446 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8077 _exptl_absorpt_correction_T_max 0.9567 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2122 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0598 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.04 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1486 _reflns_number_gt 1375 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _refine_special_details ; checks showed an 87% fit in C2/c. The aryl groups obey this symmetry but the ammonium groups (which form ordered polar stacks in Cc) do not, therefore we believe that Cc is the correct space group. 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^)+(0.0000P)^2^+0.4193P] 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 calc _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(9) _refine_ls_number_reflns 1486 _refine_ls_number_parameters 74 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0798 _refine_ls_wR_factor_gt 0.0774 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.055 _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 Cl1 Cl 0.83856(6) -0.26882(7) 0.71593(9) 0.02251(14) Uani 1 1 d . . . C1 C 0.6777(2) 0.2470(6) 0.5009(5) 0.0198(7) Uani 1 1 d . . . C5 C 0.5477(2) 0.4520(6) 0.3688(5) 0.0280(9) Uani 1 1 d . . . H5 H 0.5195 0.5839 0.3029 0.034 Uiso 1 1 calc R . . C3 C 0.5395(2) 0.0810(6) 0.5274(5) 0.0283(8) Uani 1 1 d . . . H3 H 0.5054 -0.0414 0.5683 0.034 Uiso 1 1 calc R . . C6 C 0.6376(2) 0.4384(6) 0.4035(5) 0.0272(8) Uani 1 1 d . . . H6 H 0.6712 0.5599 0.3605 0.033 Uiso 1 1 calc R . . C2 C 0.6292(2) 0.0670(6) 0.5651(5) 0.0267(8) Uani 1 1 d . . . H2 H 0.6571 -0.0629 0.6332 0.032 Uiso 1 1 calc R . . C4 C 0.5001(3) 0.2740(7) 0.4301(5) 0.0288(9) Uani 1 1 d . . . H4 H 0.4388 0.2833 0.4054 0.035 Uiso 1 1 calc R . . N1 N 0.77208(15) 0.2349(3) 0.5392(3) 0.0221(4) Uani 1 1 d . . . H1A H 0.7931 0.2389 0.4456 0.033 Uiso 1 1 calc R . . H1B H 0.7889 0.0900 0.5936 0.033 Uiso 1 1 calc R . . H1C H 0.7930 0.3683 0.6024 0.033 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 Cl1 0.0189(2) 0.0220(2) 0.0270(2) 0.0005(6) 0.00524(16) -0.0007(6) C1 0.0176(17) 0.0209(15) 0.0220(17) -0.0051(12) 0.0066(14) -0.0020(11) C5 0.026(2) 0.027(2) 0.031(2) -0.0020(16) 0.0047(16) 0.0023(15) C3 0.0249(19) 0.0284(17) 0.033(2) 0.0018(15) 0.0091(16) -0.0052(13) C6 0.029(2) 0.0231(15) 0.030(2) 0.0029(14) 0.0080(16) 0.0032(13) C2 0.030(2) 0.0228(18) 0.027(2) 0.0060(15) 0.0053(15) 0.0041(14) C4 0.026(2) 0.0302(18) 0.029(2) -0.0039(16) 0.0015(16) 0.0060(15) N1 0.0222(9) 0.0196(9) 0.0249(10) 0.0021(9) 0.0058(8) -0.0009(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 C1 C6 1.382(6) . ? C1 C2 1.397(6) . ? C1 N1 1.462(5) . ? C5 C4 1.369(6) . ? C5 C6 1.393(5) . ? C3 C4 1.384(6) . ? C3 C2 1.389(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 C6 C1 C2 120.9(4) . . ? C6 C1 N1 119.5(3) . . ? C2 C1 N1 119.6(4) . . ? C4 C5 C6 119.6(4) . . ? C4 C3 C2 119.7(4) . . ? C1 C6 C5 119.5(4) . . ? C3 C2 C1 118.9(4) . . ? C5 C4 C3 121.4(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C6 C5 0.0(6) . . . . ? N1 C1 C6 C5 -179.1(3) . . . . ? C4 C5 C6 C1 -0.7(6) . . . . ? C4 C3 C2 C1 -1.1(5) . . . . ? C6 C1 C2 C3 0.9(6) . . . . ? N1 C1 C2 C3 -180.0(3) . . . . ? C6 C5 C4 C3 0.5(6) . . . . ? C2 C3 C4 C5 0.4(6) . . . . ? 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 H1C Cl1 0.91 2.21 3.1131(19) 169.9 1_565 N1 H1B Cl1 0.91 2.24 3.1469(18) 175.5 . N1 H1A Cl1 0.91 2.19 3.096(2) 176.5 2_554 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.180 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.047 data_4d _database_code_depnum_ccdc_archive 'CCDC 299876' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 N, C2 F3 O2' _chemical_formula_sum 'C8 H8 F3 N O2' _chemical_formula_weight 207.15 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.334(2) _cell_length_b 8.8820(18) _cell_length_c 19.973(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.07(3) _cell_angle_gamma 90.00 _cell_volume 1815.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.148 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8660 _exptl_absorpt_correction_T_max 0.9853 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10454 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0570 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3551 _reflns_number_gt 2876 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _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^)+(0.0245P)^2^+0.9729P] 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 calc _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0131(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3551 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 F1 F -0.00161(11) 1.45857(14) -0.10104(8) 0.0523(4) Uani 1 1 d . . . F2 F 0.07870(12) 1.64242(15) -0.14785(6) 0.0444(3) Uani 1 1 d . . . F3 F 0.02993(12) 1.66754(17) -0.04843(7) 0.0526(4) Uani 1 1 d . . . F4 F 0.33328(12) 0.83170(13) 0.15573(5) 0.0360(3) Uani 1 1 d . . . F5 F 0.24505(11) 0.66036(12) 0.08911(6) 0.0347(3) Uani 1 1 d . . . F6 F 0.44657(11) 0.71841(15) 0.08861(6) 0.0407(3) Uani 1 1 d . . . O1 O 0.23122(12) 1.39229(14) -0.03660(6) 0.0248(3) Uani 1 1 d . . . O2 O 0.30403(13) 1.62206(15) -0.05952(7) 0.0341(4) Uani 1 1 d . . . O3 O 0.16723(11) 0.93432(14) 0.03560(6) 0.0241(3) Uani 1 1 d . . . O4 O 0.37046(11) 0.95151(13) 0.00869(6) 0.0226(3) Uani 1 1 d . . . N1 N 0.08011(14) 1.13320(16) -0.06607(7) 0.0199(3) Uani 1 1 d . . . H1A H -0.0067 1.1381 -0.0628 0.024 Uiso 1 1 calc R . . H1B H 0.1174 1.2248 -0.0562 0.024 Uiso 1 1 calc R . . H1C H 0.1188 1.0635 -0.0364 0.024 Uiso 1 1 calc R . . N2 N 0.55076(13) 1.74154(16) -0.04091(7) 0.0186(3) Uani 1 1 d . . . H2A H 0.5361 1.8316 -0.0216 0.022 Uiso 1 1 calc R . . H2B H 0.6188 1.6941 -0.0156 0.022 Uiso 1 1 calc R . . H2C H 0.4778 1.6833 -0.0430 0.022 Uiso 1 1 calc R . . C1 C 0.09769(17) 1.08993(19) -0.13507(9) 0.0207(4) Uani 1 1 d . . . C2 C 0.20654(18) 1.1408(2) -0.16165(10) 0.0273(4) Uani 1 1 d . . . H2 H 0.2702 1.2015 -0.1353 0.033 Uiso 1 1 calc R . . C3 C 0.2210(2) 1.1014(2) -0.22745(11) 0.0342(5) Uani 1 1 d . . . H3 H 0.2945 1.1365 -0.2466 0.041 Uiso 1 1 calc R . . C4 C 0.1291(2) 1.0117(2) -0.26517(10) 0.0356(5) Uani 1 1 d . . . H4 H 0.1398 0.9849 -0.3101 0.043 Uiso 1 1 calc R . . C5 C 0.0214(2) 0.9606(2) -0.23772(10) 0.0337(5) Uani 1 1 d . . . H5 H -0.0413 0.8984 -0.2638 0.040 Uiso 1 1 calc R . . C6 C 0.00468(19) 1.0000(2) -0.17210(10) 0.0269(4) Uani 1 1 d . . . H6 H -0.0693 0.9658 -0.1531 0.032 Uiso 1 1 calc R . . C7 C 0.58227(16) 1.76676(19) -0.10959(8) 0.0179(4) Uani 1 1 d . . . C8 C 0.49465(17) 1.8471(2) -0.15453(9) 0.0242(4) Uani 1 1 d . . . H8 H 0.4159 1.8845 -0.1414 0.029 Uiso 1 1 calc R . . C9 C 0.52410(19) 1.8719(2) -0.21926(10) 0.0288(4) Uani 1 1 d . . . H9 H 0.4652 1.9275 -0.2508 0.035 Uiso 1 1 calc R . . C10 C 0.63878(19) 1.8161(2) -0.23835(9) 0.0274(4) Uani 1 1 d . . . H10 H 0.6584 1.8338 -0.2828 0.033 Uiso 1 1 calc R . . C11 C 0.72464(18) 1.7347(2) -0.19278(9) 0.0268(4) Uani 1 1 d . . . H11 H 0.8028 1.6957 -0.2061 0.032 Uiso 1 1 calc R . . C12 C 0.69687(17) 1.7098(2) -0.12746(9) 0.0224(4) Uani 1 1 d . . . H12 H 0.7557 1.6545 -0.0958 0.027 Uiso 1 1 calc R . . C13 C 0.08113(17) 1.57342(19) -0.08875(9) 0.0211(4) Uani 1 1 d . . . C14 C 0.22045(16) 1.52424(19) -0.05844(8) 0.0192(4) Uani 1 1 d . . . C15 C 0.32829(16) 0.7761(2) 0.09292(9) 0.0222(4) Uani 1 1 d . . . C16 C 0.28594(16) 0.89897(18) 0.03975(9) 0.0186(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0256(6) 0.0337(7) 0.0889(11) 0.0153(7) -0.0224(6) -0.0101(5) F2 0.0396(7) 0.0587(9) 0.0344(7) 0.0219(6) 0.0033(5) 0.0097(6) F3 0.0328(7) 0.0815(11) 0.0418(8) -0.0260(7) -0.0002(6) 0.0238(7) F4 0.0484(7) 0.0403(7) 0.0193(6) 0.0012(5) 0.0047(5) -0.0052(5) F5 0.0415(7) 0.0233(6) 0.0385(7) 0.0077(5) 0.0034(5) -0.0089(5) F6 0.0277(6) 0.0555(8) 0.0404(7) 0.0211(6) 0.0100(5) 0.0173(5) O1 0.0217(7) 0.0224(7) 0.0287(7) 0.0022(5) -0.0019(5) 0.0002(5) O2 0.0222(7) 0.0331(8) 0.0462(9) 0.0035(7) 0.0023(6) -0.0108(6) O3 0.0175(6) 0.0272(7) 0.0284(7) 0.0054(5) 0.0059(5) 0.0018(5) O4 0.0222(6) 0.0192(6) 0.0282(7) 0.0000(5) 0.0101(5) -0.0046(5) N1 0.0175(7) 0.0194(7) 0.0231(8) 0.0020(6) 0.0040(6) -0.0010(6) N2 0.0153(7) 0.0190(7) 0.0215(7) 0.0004(6) 0.0026(6) -0.0007(5) C1 0.0228(9) 0.0191(8) 0.0208(9) 0.0043(7) 0.0052(7) 0.0043(7) C2 0.0238(10) 0.0264(10) 0.0336(11) 0.0032(8) 0.0099(8) 0.0016(7) C3 0.0380(12) 0.0336(11) 0.0351(11) 0.0044(9) 0.0192(9) 0.0077(9) C4 0.0533(13) 0.0308(11) 0.0247(10) 0.0017(9) 0.0125(9) 0.0129(10) C5 0.0448(12) 0.0279(10) 0.0277(10) -0.0044(9) 0.0022(9) -0.0003(9) C6 0.0288(10) 0.0236(9) 0.0290(10) 0.0010(8) 0.0062(8) -0.0022(8) C7 0.0188(8) 0.0170(8) 0.0181(8) -0.0020(7) 0.0026(6) -0.0034(6) C8 0.0211(9) 0.0248(9) 0.0267(10) 0.0010(8) 0.0038(7) 0.0029(7) C9 0.0326(11) 0.0281(10) 0.0243(10) 0.0034(8) -0.0002(8) 0.0025(8) C10 0.0350(11) 0.0286(10) 0.0193(9) -0.0018(8) 0.0064(8) -0.0051(8) C11 0.0225(9) 0.0302(10) 0.0288(10) -0.0040(8) 0.0076(8) -0.0001(7) C12 0.0191(9) 0.0239(9) 0.0238(9) -0.0005(7) 0.0017(7) 0.0013(7) C13 0.0232(9) 0.0183(9) 0.0220(9) 0.0018(7) 0.0039(7) -0.0027(7) C14 0.0192(9) 0.0214(9) 0.0172(8) -0.0027(7) 0.0033(6) -0.0020(7) C15 0.0180(9) 0.0258(9) 0.0233(9) 0.0019(8) 0.0047(7) -0.0013(7) C16 0.0193(9) 0.0165(8) 0.0202(9) -0.0042(7) 0.0037(7) -0.0034(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 F1 C13 1.332(2) . ? F2 C13 1.327(2) . ? F3 C13 1.322(2) . ? F4 C15 1.342(2) . ? F5 C15 1.336(2) . ? F6 C15 1.339(2) . ? O1 C14 1.250(2) . ? O2 C14 1.227(2) . ? O3 C16 1.258(2) . ? O4 C16 1.232(2) . ? N1 C1 1.466(2) . ? N2 C7 1.471(2) . ? C1 C6 1.382(3) . ? C1 C2 1.385(3) . ? C2 C3 1.388(3) . ? C3 C4 1.379(3) . ? C4 C5 1.385(3) . ? C5 C6 1.391(3) . ? C7 C12 1.380(2) . ? C7 C8 1.381(2) . ? C8 C9 1.387(3) . ? C9 C10 1.386(3) . ? C10 C11 1.383(3) . ? C11 C12 1.392(3) . ? C13 C14 1.544(2) . ? C15 C16 1.542(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 C6 C1 C2 121.64(17) . . ? C6 C1 N1 119.08(16) . . ? C2 C1 N1 119.29(16) . . ? C1 C2 C3 118.81(19) . . ? C4 C3 C2 120.35(19) . . ? C3 C4 C5 120.20(18) . . ? C4 C5 C6 120.25(19) . . ? C1 C6 C5 118.75(18) . . ? C12 C7 C8 121.99(16) . . ? C12 C7 N2 119.71(15) . . ? C8 C7 N2 118.30(15) . . ? C7 C8 C9 118.58(17) . . ? C10 C9 C8 120.51(17) . . ? C11 C10 C9 120.00(17) . . ? C10 C11 C12 120.16(17) . . ? C7 C12 C11 118.75(16) . . ? F3 C13 F2 106.90(15) . . ? F3 C13 F1 107.18(16) . . ? F2 C13 F1 104.97(15) . . ? F3 C13 C14 111.78(14) . . ? F2 C13 C14 112.29(14) . . ? F1 C13 C14 113.25(14) . . ? O2 C14 O1 129.90(17) . . ? O2 C14 C13 114.36(15) . . ? O1 C14 C13 115.74(14) . . ? F5 C15 F6 106.73(15) . . ? F5 C15 F4 106.03(14) . . ? F6 C15 F4 106.56(14) . . ? F5 C15 C16 112.77(14) . . ? F6 C15 C16 113.57(14) . . ? F4 C15 C16 110.69(14) . . ? O4 C16 O3 128.77(16) . . ? O4 C16 C15 117.51(15) . . ? O3 C16 C15 113.69(14) . . ? 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 C6 C1 C2 C3 0.8(3) . . . . ? N1 C1 C2 C3 -178.82(16) . . . . ? C1 C2 C3 C4 -0.8(3) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C2 C1 C6 C5 -0.2(3) . . . . ? N1 C1 C6 C5 179.41(17) . . . . ? C4 C5 C6 C1 -0.4(3) . . . . ? C12 C7 C8 C9 -0.6(3) . . . . ? N2 C7 C8 C9 179.68(16) . . . . ? C7 C8 C9 C10 0.4(3) . . . . ? C8 C9 C10 C11 0.2(3) . . . . ? C9 C10 C11 C12 -0.6(3) . . . . ? C8 C7 C12 C11 0.2(3) . . . . ? N2 C7 C12 C11 179.89(16) . . . . ? C10 C11 C12 C7 0.4(3) . . . . ? F3 C13 C14 O2 -73.0(2) . . . . ? F2 C13 C14 O2 47.1(2) . . . . ? F1 C13 C14 O2 165.81(16) . . . . ? F3 C13 C14 O1 106.88(18) . . . . ? F2 C13 C14 O1 -132.99(16) . . . . ? F1 C13 C14 O1 -14.3(2) . . . . ? F5 C15 C16 O4 -135.22(16) . . . . ? F6 C15 C16 O4 -13.6(2) . . . . ? F4 C15 C16 O4 106.18(17) . . . . ? F5 C15 C16 O3 46.5(2) . . . . ? F6 C15 C16 O3 168.06(15) . . . . ? F4 C15 C16 O3 -72.12(18) . . . . ? 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 O3 0.91 1.93 2.7748(19) 154.3 3_575 N1 H1B O1 0.91 1.90 2.7969(19) 167.0 . N1 H1B F1 0.91 2.51 3.0639(19) 119.4 . N1 H1C O3 0.91 1.85 2.7461(19) 166.7 . N2 H2A O4 0.91 2.15 2.8918(19) 137.6 3_685 N2 H2A O4 0.91 2.17 2.9068(19) 137.2 1_565 N2 H2B O1 0.91 1.90 2.812(2) 175.8 3_685 N2 H2C O2 0.91 1.86 2.7384(19) 161.2 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.297 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.049 data_4e _database_code_depnum_ccdc_archive 'CCDC 299877' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 N, H2 P O4, H2 O' _chemical_formula_sum 'C6 H12 N O5 P' _chemical_formula_weight 209.14 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.6419(19) _cell_length_b 21.039(4) _cell_length_c 10.100(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.639(3) _cell_angle_gamma 90.00 _cell_volume 1917.3(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.279 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8966 _exptl_absorpt_correction_T_max 0.9463 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10584 _diffrn_reflns_av_R_equivalents 0.0876 _diffrn_reflns_av_sigmaI/netI 0.0819 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3314 _reflns_number_gt 2199 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Due to poor data quality and disorder, the carbon atoms were refined isotropically. The maxiumum shift/error is also slightly large but could not be reduced by further refinement and is probably an artifact of the disorder/poor data quality. Although the residuals are high the connectivity of the structure is not in doubt. 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^)+(0.0905P)^2^+33.1815P] 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 calc _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.026(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3314 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1660 _refine_ls_R_factor_gt 0.1229 _refine_ls_wR_factor_ref 0.3168 _refine_ls_wR_factor_gt 0.2944 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.958 _refine_ls_shift/su_mean 0.028 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 P1 P -0.2494(3) -0.04183(10) 0.2822(2) 0.0174(7) Uani 1 1 d . . . P2 P -0.7501(2) -0.04221(11) 0.2821(2) 0.0154(6) Uani 1 1 d . . . O1 O -0.2941(7) -0.0777(3) 0.1353(7) 0.0274(16) Uani 1 1 d . . . H1 H -0.4091 -0.0812 0.0784 0.033 Uiso 1 1 d R . . O2 O -0.3296(7) -0.0767(3) 0.3702(7) 0.0276(16) Uani 1 1 d . . . H21 H -0.4373 -0.0649 0.3451 0.033 Uiso 1 1 d R . . O3 O -0.0879(7) -0.0499(3) 0.3531(6) 0.0201(14) Uani 1 1 d . . . O4 O -0.2991(7) 0.0273(3) 0.2582(6) 0.0229(14) Uani 1 1 d . . . O5 O -0.7945(6) -0.0775(3) 0.1356(6) 0.0202(14) Uani 1 1 d . . . H51 H -0.8820 -0.0680 0.0858 0.030 Uiso 1 1 calc R . . O6 O -0.8242(7) -0.0775(3) 0.3764(6) 0.0198(14) Uani 1 1 d . . . H61 H -0.9359 -0.0667 0.3688 0.024 Uiso 1 1 d R . . O7 O -0.5840(6) -0.0525(3) 0.3584(6) 0.0233(15) Uani 1 1 d . . . O8 O -0.7967(6) 0.0263(3) 0.2593(6) 0.0170(13) Uiso 1 1 d . . . N1 N -0.5029(8) 0.0859(3) 0.3596(9) 0.0206(17) Uani 1 1 d . C . H12N H -0.5965 0.0706 0.3182 0.031 Uiso 1 1 calc R . . H11N H -0.4724 0.0797 0.4548 0.031 Uiso 1 1 calc R . . H13N H -0.4407 0.0652 0.3243 0.031 Uiso 1 1 calc R . . N2 N 0.0000(8) 0.0855(3) 0.3606(7) 0.0192(16) Uani 1 1 d . D . H21N H 0.0643 0.0658 0.3262 0.029 Uiso 1 1 calc R . . H23N H -0.0938 0.0718 0.3122 0.029 Uiso 1 1 calc R . . H22N H 0.0244 0.0760 0.4540 0.029 Uiso 1 1 calc R . . C1 C -0.5013(9) 0.1541(4) 0.3301(8) 0.0148(17) Uiso 1 1 d . . . C4 C -0.4904(10) 0.2835(5) 0.2875(10) 0.025(2) Uiso 1 1 d . . . H4 H -0.4678 0.3254 0.2662 0.030 Uiso 1 1 calc R A 1 C7 C 0.0081(10) 0.1550(4) 0.3433(9) 0.0203(19) Uiso 1 1 d . . . C10 C 0.0161(12) 0.2838(5) 0.2978(11) 0.033(2) Uiso 1 1 d . . . H10 H 0.0261 0.3251 0.2643 0.040 Uiso 1 1 calc R B 1 O1S O -0.5795(7) -0.0803(3) 0.0032(6) 0.0251(15) Uani 1 1 d . . . H11S H -0.6216 -0.0542 -0.0777 0.030 Uiso 1 1 d R . . H12S H -0.6396 -0.0918 0.0512 0.030 Uiso 1 1 d R . . O2S O -1.0755(7) -0.0793(4) 0.0013(7) 0.0362(19) Uani 1 1 d . . . H22S H -1.1631 -0.0681 0.0439 0.043 Uiso 1 1 d R . . H21S H -1.1272 -0.0544 -0.0782 0.043 Uiso 1 1 d R . . C2 C -0.5678(14) 0.1783(6) 0.2077(14) 0.000(3) Uiso 0.50 1 d P C 1 H2 H -0.6247 0.1522 0.1310 0.000 Uiso 0.50 1 calc PR C 1 C3 C -0.5557(15) 0.2441(6) 0.1879(15) 0.004(3) Uiso 0.50 1 d P C 1 H3 H -0.5987 0.2604 0.0945 0.005 Uiso 0.50 1 calc PR C 1 C5 C -0.4495(17) 0.2617(7) 0.4416(16) 0.011(3) Uiso 0.50 1 d P C 1 H5 H -0.4203 0.2907 0.5186 0.013 Uiso 0.50 1 calc PR C 1 C6 C -0.4584(18) 0.1950(7) 0.4611(17) 0.014(3) Uiso 0.50 1 d P C 1 H6 H -0.4383 0.1771 0.5524 0.016 Uiso 0.50 1 calc PR C 1 C8 C 0.1216(15) 0.1873(6) 0.3960(14) 0.000(3) Uiso 0.50 1 d P D 1 H8 H 0.2088 0.1669 0.4564 0.000 Uiso 0.50 1 calc PR D 1 C9 C 0.1278(16) 0.2528(6) 0.3711(14) 0.003(3) Uiso 0.50 1 d P D 1 H9 H 0.2198 0.2743 0.4112 0.004 Uiso 0.50 1 calc PR D 1 C11 C -0.1331(17) 0.2541(7) 0.2643(16) 0.010(3) Uiso 0.50 1 d P D 1 H11 H -0.2204 0.2793 0.2306 0.013 Uiso 0.50 1 calc PR D 1 C12 C -0.1417(17) 0.1919(7) 0.2826(15) 0.010(3) Uiso 0.50 1 d P D 1 H12 H -0.2344 0.1709 0.2599 0.012 Uiso 0.50 1 calc PR D 1 C2A C -0.6130(15) 0.1835(6) 0.2569(14) 0.001(3) Uiso 0.50 1 d P C 2 H2A H -0.7042 0.1614 0.2167 0.001 Uiso 0.50 1 calc PR C 2 C3A C -0.6073(16) 0.2511(6) 0.2313(15) 0.005(3) Uiso 0.50 1 d P C 2 H3A H -0.6939 0.2718 0.1705 0.006 Uiso 0.50 1 calc PR C 2 C5A C -0.3396(19) 0.2486(8) 0.3486(17) 0.018(3) Uiso 0.50 1 d P C 2 H5A H -0.2484 0.2706 0.3691 0.021 Uiso 0.50 1 calc PR C 2 C6A C -0.3438(17) 0.1835(7) 0.3722(16) 0.011(3) Uiso 0.50 1 d P C 2 H6A H -0.2563 0.1588 0.4113 0.013 Uiso 0.50 1 calc PR C 2 C8A C 0.0791(14) 0.1938(6) 0.4441(14) 0.000(3) Uiso 0.50 1 d P D 2 H8A H 0.1292 0.1793 0.5379 0.000 Uiso 0.50 1 calc PR D 2 C9A C 0.0788(16) 0.2573(6) 0.4090(15) 0.003(3) Uiso 0.50 1 d P D 2 H9A H 0.1366 0.2842 0.4836 0.003 Uiso 0.50 1 calc PR D 2 C11A C -0.033(2) 0.2410(8) 0.1599(19) 0.021(4) Uiso 0.50 1 d P D 2 H11A H -0.0586 0.2580 0.0672 0.026 Uiso 0.50 1 calc PR D 2 C12A C -0.0353(18) 0.1754(8) 0.1870(17) 0.015(3) Uiso 0.50 1 d P D 2 H12A H -0.0622 0.1451 0.1125 0.018 Uiso 0.50 1 calc PR D 2 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 P1 0.0192(12) 0.0166(12) 0.0191(13) -0.0012(9) 0.0101(10) 0.0031(9) P2 0.0061(11) 0.0240(12) 0.0153(12) 0.0034(9) 0.0027(8) -0.0015(8) O1 0.023(4) 0.032(4) 0.026(4) -0.012(3) 0.007(3) 0.012(3) O2 0.011(3) 0.028(4) 0.041(4) 0.004(3) 0.006(3) 0.002(3) O3 0.021(3) 0.019(3) 0.027(3) 0.006(2) 0.016(3) -0.004(2) O4 0.028(3) 0.024(3) 0.021(3) -0.002(3) 0.014(3) 0.005(3) O5 0.014(3) 0.029(4) 0.015(3) 0.002(3) 0.003(3) -0.008(3) O6 0.023(3) 0.024(3) 0.014(3) 0.010(2) 0.010(3) 0.005(2) O7 0.010(3) 0.039(4) 0.015(3) -0.001(3) -0.002(2) 0.008(3) N1 0.018(4) 0.016(4) 0.038(5) -0.004(3) 0.022(4) 0.002(3) N2 0.019(4) 0.022(4) 0.009(3) 0.004(3) -0.004(3) -0.002(3) O1S 0.028(4) 0.031(4) 0.019(3) 0.002(3) 0.012(3) 0.022(3) O2S 0.016(3) 0.059(5) 0.023(4) 0.022(3) -0.006(3) -0.025(3) _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 P1 O3 1.477(7) . ? P1 O4 1.524(7) . ? P1 O2 1.552(7) . ? P1 O1 1.583(6) . ? P2 O8 1.503(6) . ? P2 O7 1.528(6) . ? P2 O6 1.565(6) . ? P2 O5 1.574(6) . ? N1 C1 1.466(11) . ? N2 C7 1.478(11) . ? C1 C2A 1.237(16) . ? C1 C2 1.281(15) . ? C1 C6 1.509(17) . ? C1 C6A 1.554(17) . ? C4 C3A 1.267(17) . ? C4 C3 1.284(17) . ? C4 C5 1.535(17) . ? C4 C5A 1.549(19) . ? C7 C8 1.238(16) . ? C7 C8A 1.296(16) . ? C7 C12A 1.545(18) . ? C7 C12 1.562(17) . ? C10 C9A 1.208(17) . ? C10 C9 1.254(17) . ? C10 C11 1.494(18) . ? C10 C11A 1.58(2) . ? C2 C3 1.409(18) . ? C5 C6 1.42(2) . ? C8 C9 1.405(19) . ? C11 C12 1.33(2) . ? C2A C3A 1.450(19) . ? C5A C6A 1.39(2) . ? C8A C9A 1.381(19) . ? C11A C12A 1.41(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 O3 P1 O4 113.9(4) . . ? O3 P1 O2 108.7(3) . . ? O4 P1 O2 110.5(3) . . ? O3 P1 O1 106.9(3) . . ? O4 P1 O1 109.9(4) . . ? O2 P1 O1 106.6(4) . . ? O8 P2 O7 114.7(4) . . ? O8 P2 O6 111.8(3) . . ? O7 P2 O6 104.4(3) . . ? O8 P2 O5 109.9(3) . . ? O7 P2 O5 107.3(3) . . ? O6 P2 O5 108.5(3) . . ? C2A C1 C2 35.8(7) . . ? C2A C1 N1 122.8(9) . . ? C2 C1 N1 123.3(9) . . ? C2A C1 C6 98.6(10) . . ? C2 C1 C6 120.5(10) . . ? N1 C1 C6 113.5(9) . . ? C2A C1 C6A 121.7(10) . . ? C2 C1 C6A 102.3(10) . . ? N1 C1 C6A 114.4(8) . . ? C6 C1 C6A 66.0(9) . . ? C3A C4 C3 35.8(8) . . ? C3A C4 C5 99.4(11) . . ? C3 C4 C5 118.8(11) . . ? C3A C4 C5A 119.0(11) . . ? C3 C4 C5A 98.0(11) . . ? C5 C4 C5A 65.5(9) . . ? C8 C7 C8A 34.3(7) . . ? C8 C7 N2 124.7(10) . . ? C8A C7 N2 124.5(9) . . ? C8 C7 C12A 99.6(10) . . ? C8A C7 C12A 120.3(11) . . ? N2 C7 C12A 112.9(9) . . ? C8 C7 C12 116.7(10) . . ? C8A C7 C12 98.9(10) . . ? N2 C7 C12 117.3(8) . . ? C12A C7 C12 65.2(9) . . ? C9A C10 C9 33.5(8) . . ? C9A C10 C11 98.3(11) . . ? C9 C10 C11 118.3(12) . . ? C9A C10 C11A 116.8(12) . . ? C9 C10 C11A 98.8(11) . . ? C11 C10 C11A 66.3(10) . . ? C1 C2 C3 119.3(12) . . ? C4 C3 C2 124.4(13) . . ? C6 C5 C4 115.3(12) . . ? C5 C6 C1 116.9(13) . . ? C7 C8 C9 123.3(12) . . ? C10 C9 C8 122.3(13) . . ? C12 C11 C10 118.8(14) . . ? C11 C12 C7 116.8(13) . . ? C1 C2A C3A 121.2(12) . . ? C4 C3A C2A 122.1(13) . . ? C6A C5A C4 117.0(14) . . ? C5A C6A C1 115.5(13) . . ? C7 C8A C9A 117.1(12) . . ? C10 C9A C8A 129.8(13) . . ? C12A C11A C10 114.0(14) . . ? C11A C12A C7 117.0(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 O1 H1 O1S 1.06 1.55 2.602(9) 174.3 . O2 H21 O7 1.01 1.49 2.466(8) 161.0 . O5 H51 O2S 0.84 1.77 2.567(8) 157.0 . O6 H61 O3 1.08 1.46 2.536(8) 177.3 1_455 N1 H12N O8 0.91 2.03 2.933(9) 169.2 . N1 H11N O7 0.91 1.86 2.760(10) 170.4 3_456 N1 H13N O4 0.91 1.89 2.801(9) 175.2 . N2 H21N O8 0.91 1.89 2.803(10) 178.1 1_655 N2 H23N O4 0.91 2.08 2.964(10) 163.0 . N2 H22N O3 0.91 1.91 2.814(9) 174.4 3_556 O1S H11S O4 0.95 1.80 2.721(9) 162.4 3_455 O1S H12S O5 0.91 1.99 2.836(8) 154.8 . O2S H22S O1 1.10 1.82 2.879(9) 160.2 1_455 O2S H21S O8 0.94 1.81 2.720(8) 161.3 3_355 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.684 _refine_diff_density_min -1.904 _refine_diff_density_rms 0.142 data_4f _database_code_depnum_ccdc_archive 'CCDC 299878' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 N, H O4 S' _chemical_formula_sum 'C6 H9 N O4 S' _chemical_formula_weight 191.20 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 14.2459(7) _cell_length_b 9.1043(6) _cell_length_c 12.6132(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1635.92(18) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.370 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7087 _exptl_absorpt_correction_T_max 0.9297 _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 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7565 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3063 _reflns_number_gt 2846 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _refine_special_details ; N and C hydrogens in calculated positions, O hydrogen atoms located then fixed. Platon checks show that there may be some additional symmetry but this is pseudosymmetry 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^)+(0.0321P)^2^+0.6268P] 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 'see above' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0074(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(9) _refine_ls_number_reflns 3063 _refine_ls_number_parameters 241 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0797 _refine_ls_wR_factor_gt 0.0774 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.77689(5) 0.01404(6) 0.29921(5) 0.01245(17) Uani 1 1 d . . . S2 S 1.02496(4) -0.00502(5) 0.07922(6) 0.01323(18) Uani 1 1 d . . . O1 O 0.85649(13) 0.13148(18) 0.29319(18) 0.0180(4) Uani 1 1 d . . . O2 O 0.7388(2) -0.00122(17) 0.1917(2) 0.0197(6) Uani 1 1 d . . . O3 O 0.81832(11) -0.12295(17) 0.33578(17) 0.0168(4) Uani 1 1 d . . . O4 O 0.70944(10) 0.07617(19) 0.37289(18) 0.0191(4) Uani 1 1 d . . . O5 O 1.06312(12) 0.13868(17) 0.05560(16) 0.0179(4) Uani 1 1 d . . . O6 O 1.10767(12) -0.11843(18) 0.07844(18) 0.0177(4) Uani 1 1 d . . . O7 O 0.9860(2) -0.0128(2) 0.1872(2) 0.0233(6) Uani 1 1 d . . . O8 O 0.96144(11) -0.0591(2) -0.00058(19) 0.0206(4) Uani 1 1 d . . . N1 N 0.52998(13) 0.2059(2) 0.3573(2) 0.0151(4) Uani 1 1 d . . . N2 N 0.78409(13) -0.1899(2) 0.0242(2) 0.0155(4) Uani 1 1 d . . . C1 C 0.53488(16) 0.3656(3) 0.3397(2) 0.0141(6) Uani 1 1 d . . . C2 C 0.49749(18) 0.4581(3) 0.4158(2) 0.0170(5) Uani 1 1 d . . . H2 H 0.4675 0.4195 0.4770 0.020 Uiso 1 1 calc R . . C3 C 0.5049(2) 0.6095(3) 0.4005(3) 0.0205(6) Uani 1 1 d . . . H3 H 0.4797 0.6753 0.4516 0.025 Uiso 1 1 calc R . . C4 C 0.54921(17) 0.6640(3) 0.3104(3) 0.0213(6) Uani 1 1 d . . . H4 H 0.5544 0.7672 0.3004 0.026 Uiso 1 1 calc R . . C5 C 0.58583(19) 0.5692(3) 0.2352(3) 0.0210(6) Uani 1 1 d . . . H5 H 0.6157 0.6076 0.1738 0.025 Uiso 1 1 calc R . . C6 C 0.57913(18) 0.4182(3) 0.2492(3) 0.0188(6) Uani 1 1 d . . . H6 H 0.6042 0.3524 0.1980 0.023 Uiso 1 1 calc R . . C7 C 0.78847(17) -0.3488(3) 0.0427(2) 0.0134(6) Uani 1 1 d . . . C8 C 0.82992(18) -0.3996(3) 0.1355(3) 0.0179(6) Uani 1 1 d . . . H8 H 0.8543 -0.3329 0.1865 0.021 Uiso 1 1 calc R . . C9 C 0.8348(2) -0.5509(3) 0.1518(3) 0.0223(6) Uani 1 1 d . . . H9 H 0.8633 -0.5885 0.2142 0.027 Uiso 1 1 calc R . . C10 C 0.79792(18) -0.6467(3) 0.0768(3) 0.0237(7) Uani 1 1 d . . . H10 H 0.8021 -0.7497 0.0879 0.028 Uiso 1 1 calc R . . H1B H 0.4954 0.1843 0.4176 0.036(9) Uiso 1 1 d R . . H2A H 0.7418 -0.1714 -0.0282 0.023(8) Uiso 1 1 d R . . H1A H 0.5861 0.1665 0.3724 0.033(9) Uiso 1 1 d R . . C11 C 0.7553(2) -0.5934(3) -0.0138(3) 0.0210(6) Uani 1 1 d . . . H11 H 0.7291 -0.6595 -0.0640 0.025 Uiso 1 1 calc R . . C12 C 0.75089(19) -0.4435(3) -0.0313(2) 0.0169(5) Uani 1 1 d . . . H12 H 0.7222 -0.4061 -0.0937 0.020 Uiso 1 1 calc R . . H2B H 0.843(2) -0.155(3) 0.014(3) 0.028(8) Uiso 1 1 d . . . H1C H 0.5084(19) 0.163(3) 0.305(3) 0.022(8) Uiso 1 1 d . . . H2C H 0.752(3) -0.131(4) 0.096(4) 0.066(11) Uiso 1 1 d . . . H1O H 0.900(2) 0.098(4) 0.260(3) 0.028(9) Uiso 1 1 d . . . H6O H 1.148(2) -0.090(3) 0.111(3) 0.028(9) 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 S1 0.0115(4) 0.0125(3) 0.0134(4) 0.0013(3) 0.0004(3) 0.00056(18) S2 0.0119(4) 0.0132(3) 0.0146(4) 0.0009(2) 0.0005(3) 0.00005(18) O1 0.0169(8) 0.0149(8) 0.0223(10) -0.0014(8) 0.0038(8) -0.0014(6) O2 0.0168(12) 0.0232(11) 0.0193(16) -0.0042(7) -0.0054(11) 0.0037(6) O3 0.0171(8) 0.0146(8) 0.0187(10) 0.0038(7) 0.0018(7) 0.0039(6) O4 0.0154(7) 0.0203(9) 0.0215(10) -0.0006(8) 0.0048(7) 0.0039(7) O5 0.0220(8) 0.0127(8) 0.0190(10) 0.0022(7) -0.0014(8) -0.0039(7) O6 0.0134(8) 0.0161(8) 0.0236(10) -0.0024(8) -0.0033(8) 0.0017(6) O7 0.0281(16) 0.0247(11) 0.0170(16) 0.0056(8) 0.0076(12) 0.0071(8) O8 0.0167(8) 0.0192(9) 0.0259(11) 0.0005(8) -0.0076(7) -0.0030(7) N1 0.0150(9) 0.0143(10) 0.0160(11) 0.0001(9) -0.0014(9) 0.0006(7) N2 0.0148(9) 0.0140(10) 0.0176(11) 0.0007(9) -0.0024(8) -0.0014(7) C1 0.0109(11) 0.0122(11) 0.0193(15) 0.0015(10) -0.0056(10) 0.0000(8) C2 0.0152(11) 0.0195(13) 0.0164(15) -0.0012(12) 0.0007(10) -0.0005(11) C3 0.0174(11) 0.0152(12) 0.0288(17) -0.0063(12) -0.0025(12) 0.0045(10) C4 0.0165(11) 0.0147(12) 0.0327(17) 0.0051(13) -0.0066(12) 0.0005(9) C5 0.0174(12) 0.0226(14) 0.0231(16) 0.0080(13) 0.0003(12) -0.0032(11) C6 0.0160(11) 0.0218(13) 0.0185(14) -0.0033(12) 0.0014(11) 0.0014(10) C7 0.0125(10) 0.0114(11) 0.0163(14) 0.0018(10) 0.0009(10) -0.0017(8) C8 0.0179(11) 0.0197(13) 0.0160(14) 0.0022(12) -0.0004(11) -0.0002(10) C9 0.0236(13) 0.0208(14) 0.0223(16) 0.0088(13) 0.0003(12) 0.0028(10) C10 0.0201(12) 0.0151(12) 0.0358(18) 0.0074(13) 0.0035(13) 0.0016(9) C11 0.0191(11) 0.0186(12) 0.0255(17) -0.0050(12) 0.0014(12) -0.0030(10) C12 0.0158(10) 0.0190(12) 0.0159(15) 0.0003(12) -0.0022(10) 0.0004(11) _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 S1 O4 1.452(2) . ? S1 O3 1.4549(17) . ? S1 O2 1.467(3) . ? S1 O1 1.5605(17) . ? S2 O8 1.440(2) . ? S2 O5 1.4477(17) . ? S2 O7 1.472(3) . ? S2 O6 1.5666(17) . ? N1 C1 1.472(3) . ? N2 C7 1.467(3) . ? C1 C2 1.383(4) . ? C1 C6 1.390(4) . ? C2 C3 1.396(3) . ? C3 C4 1.392(4) . ? C4 C5 1.385(4) . ? C5 C6 1.390(4) . ? C7 C12 1.378(4) . ? C7 C8 1.391(4) . ? C8 C9 1.395(4) . ? C9 C10 1.390(4) . ? C10 C11 1.382(4) . ? C11 C12 1.384(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 S1 O3 113.56(14) . . ? O4 S1 O2 112.59(14) . . ? O3 S1 O2 111.21(11) . . ? O4 S1 O1 104.20(11) . . ? O3 S1 O1 107.94(10) . . ? O2 S1 O1 106.76(13) . . ? O8 S2 O5 113.63(14) . . ? O8 S2 O7 113.16(15) . . ? O5 S2 O7 112.06(12) . . ? O8 S2 O6 104.06(12) . . ? O5 S2 O6 108.17(10) . . ? O7 S2 O6 104.91(14) . . ? C2 C1 C6 122.4(2) . . ? C2 C1 N1 118.6(2) . . ? C6 C1 N1 119.0(2) . . ? C1 C2 C3 118.4(3) . . ? C4 C3 C2 120.0(3) . . ? C5 C4 C3 120.5(3) . . ? C4 C5 C6 120.3(2) . . ? C1 C6 C5 118.4(2) . . ? C12 C7 C8 121.8(2) . . ? C12 C7 N2 119.5(2) . . ? C8 C7 N2 118.6(2) . . ? C7 C8 C9 118.2(3) . . ? C10 C9 C8 120.1(3) . . ? C11 C10 C9 120.5(2) . . ? C10 C11 C12 119.9(2) . . ? C7 C12 C11 119.4(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.1(4) . . . . ? N1 C1 C2 C3 178.0(2) . . . . ? C1 C2 C3 C4 -0.1(4) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C3 C4 C5 C6 -0.3(4) . . . . ? C2 C1 C6 C5 0.1(4) . . . . ? N1 C1 C6 C5 -178.1(2) . . . . ? C4 C5 C6 C1 0.1(3) . . . . ? C12 C7 C8 C9 1.4(4) . . . . ? N2 C7 C8 C9 -179.3(2) . . . . ? C7 C8 C9 C10 -0.6(4) . . . . ? C8 C9 C10 C11 -0.7(4) . . . . ? C9 C10 C11 C12 1.3(4) . . . . ? C8 C7 C12 C11 -0.8(4) . . . . ? N2 C7 C12 C11 179.8(2) . . . . ? C10 C11 C12 C7 -0.6(3) . . . . ? 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 H1B O5 0.93 1.97 2.897(3) 172.9 3_655 N1 H1B O8 0.93 2.52 3.008(3) 113.2 3_655 N2 H2A O3 0.91 1.97 2.855(3) 164.3 3_654 N1 H1A O4 0.90 1.94 2.823(2) 167.8 . N2 H2B O8 0.90(3) 1.91(3) 2.811(2) 173(3) . N1 H1C O7 0.82(3) 2.05(3) 2.843(4) 163(3) 4_455 O6 H6O O2 0.75(3) 1.85(3) 2.592(3) 173(3) 4 O1 H1O O7 0.81(3) 1.83(3) 2.630(3) 169(3) . N2 H2C O2 1.14(5) 1.70(4) 2.798(4) 159(3) . N2 H2A O5 0.91 2.77 3.207(2) 110.6 4_455 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.259 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.054 data_4g _database_code_depnum_ccdc_archive 'CCDC 299879' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 N, N O3' _chemical_formula_sum 'C6 H8 N2 O3' _chemical_formula_weight 156.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pcab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x+1/2, -y, -z+1/2' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x-1/2, y, z-1/2' 'x-1/2, -y-1/2, z' _cell_length_a 9.1787(3) _cell_length_b 9.9711(4) _cell_length_c 16.0278(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1466.89(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 'not known' _exptl_crystal_size_mid 'not known' _exptl_crystal_size_min 'not known' _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.115 _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 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2621 _diffrn_reflns_av_R_equivalents 0.0148 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.95 _diffrn_reflns_theta_max 25.98 _reflns_number_total 1415 _reflns_number_gt 1315 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _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^)+(0.0499P)^2^+0.3082P] 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 calc _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.041(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1415 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0915 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _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 O1 O 0.88393(8) 0.27709(8) 0.70234(4) 0.0251(2) Uani 1 1 d . . . O2 O 0.70146(9) 0.36234(8) 0.77025(5) 0.0275(2) Uani 1 1 d . . . O3 O 0.92002(9) 0.44113(8) 0.78913(5) 0.0262(2) Uani 1 1 d . . . N1 N 0.83518(10) 0.36177(8) 0.75511(5) 0.0211(2) Uani 1 1 d . . . N2 N 0.65364(10) 0.11372(10) 0.65044(6) 0.0209(3) Uani 1 1 d . . . C1 C 0.65977(12) 0.10958(10) 0.55908(7) 0.0208(3) Uani 1 1 d . . . C2 C 0.77113(12) 0.03802(12) 0.52119(7) 0.0261(3) Uani 1 1 d . . . H2 H 0.8412 -0.0087 0.5537 0.031 Uiso 1 1 calc R . . C3 C 0.77807(14) 0.03611(12) 0.43443(7) 0.0308(3) Uani 1 1 d . . . H3 H 0.8538 -0.0119 0.4072 0.037 Uiso 1 1 calc R . . C4 C 0.67451(15) 0.10423(11) 0.38763(7) 0.0310(3) Uani 1 1 d . . . H4 H 0.6799 0.1028 0.3284 0.037 Uiso 1 1 calc R . . C5 C 0.56359(14) 0.17412(11) 0.42658(7) 0.0296(3) Uani 1 1 d . . . H5 H 0.4927 0.2199 0.3941 0.036 Uiso 1 1 calc R . . C6 C 0.55566(12) 0.17750(11) 0.51338(7) 0.0248(3) Uani 1 1 d . . . H6 H 0.4801 0.2256 0.5406 0.030 Uiso 1 1 calc R . . H21 H 0.5708(17) 0.1535(15) 0.6664(10) 0.033(4) Uiso 1 1 d . . . H22 H 0.6605(16) 0.0326(16) 0.6727(9) 0.033(4) Uiso 1 1 d . . . H23 H 0.7287(17) 0.1662(15) 0.6683(9) 0.033(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0242(4) 0.0262(4) 0.0250(4) -0.0058(3) 0.0046(3) -0.0005(3) O2 0.0203(4) 0.0301(4) 0.0319(5) -0.0043(3) 0.0042(3) -0.0001(3) O3 0.0263(4) 0.0273(4) 0.0251(4) -0.0036(3) -0.0018(3) -0.0049(3) N1 0.0223(5) 0.0219(5) 0.0190(4) 0.0010(3) 0.0008(4) 0.0002(3) N2 0.0207(5) 0.0229(5) 0.0191(5) 0.0008(3) 0.0007(4) -0.0001(4) C1 0.0219(5) 0.0206(5) 0.0198(5) 0.0007(4) 0.0003(4) -0.0048(4) C2 0.0254(6) 0.0286(6) 0.0243(6) -0.0001(4) 0.0009(4) -0.0004(4) C3 0.0359(7) 0.0302(6) 0.0262(6) -0.0044(5) 0.0072(5) -0.0029(5) C4 0.0466(7) 0.0266(6) 0.0197(6) 0.0006(4) -0.0001(5) -0.0101(5) C5 0.0379(7) 0.0252(6) 0.0258(6) 0.0048(4) -0.0078(5) -0.0051(5) C6 0.0259(6) 0.0229(6) 0.0256(6) 0.0014(4) -0.0014(4) -0.0014(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.2762(11) . ? O2 N1 1.2511(12) . ? O3 N1 1.2368(12) . ? N2 C1 1.4660(13) . ? C1 C6 1.3814(15) . ? C1 C2 1.3866(16) . ? C2 C3 1.3922(16) . ? C3 C4 1.3883(18) . ? C4 C5 1.3828(18) . ? C5 C6 1.3935(16) . ? 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 O3 N1 O2 121.96(9) . . ? O3 N1 O1 119.65(9) . . ? O2 N1 O1 118.39(9) . . ? C6 C1 C2 122.00(10) . . ? C6 C1 N2 119.29(10) . . ? C2 C1 N2 118.70(9) . . ? C1 C2 C3 118.57(10) . . ? C4 C3 C2 120.11(11) . . ? C5 C4 C3 120.45(10) . . ? C4 C5 C6 120.09(10) . . ? C1 C6 C5 118.78(10) . . ? 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 C6 C1 C2 C3 0.56(16) . . . . ? N2 C1 C2 C3 -178.95(10) . . . . ? C1 C2 C3 C4 -0.35(17) . . . . ? C2 C3 C4 C5 -0.17(17) . . . . ? C3 C4 C5 C6 0.50(17) . . . . ? C2 C1 C6 C5 -0.25(16) . . . . ? N2 C1 C6 C5 179.26(9) . . . . ? C4 C5 C6 C1 -0.29(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 N2 H23 O1 0.912(16) 1.884(16) 2.7952(12) 178.5(14) . N2 H23 O2 0.912(16) 2.561(15) 3.1662(12) 124.4(11) . N2 H23 N1 0.912(16) 2.587(16) 3.4217(13) 152.5(12) . N2 H22 O2 0.886(16) 1.965(16) 2.8445(13) 171.7(14) 6_557 N2 H22 N1 0.886(16) 2.610(16) 3.3733(13) 144.8(12) 6_557 N2 H22 O3 0.886(16) 2.623(15) 3.1428(13) 118.4(11) 6_557 N2 H21 O1 0.895(16) 1.937(17) 2.8295(12) 174.6(13) 8_565 N2 H21 O3 0.895(16) 2.583(16) 3.1367(12) 120.7(12) 8_565 N2 H21 N1 0.895(16) 2.592(16) 3.3791(13) 147.1(12) 8_565 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.170 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.038 data_4h _database_code_depnum_ccdc_archive 'CCDC 299880' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 F6 N2 O2 Si' _chemical_formula_weight 366.39 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' 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' 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 9.2142(6) _cell_length_b 5.8046(3) _cell_length_c 14.4759(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.110(3) _cell_angle_gamma 90.00 _cell_volume 773.71(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.226 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min 0.8955 _exptl_absorpt_correction_T_max 0.9778 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type kappaccd _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5710 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1768 _reflns_number_gt 1526 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement denzosmn _computing_data_reduction denzosmn _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^)+(0.0199P)^2^+0.3814P] 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 SHELXL _refine_ls_extinction_coef 0.010(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1768 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0725 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 1.0000 1.0000 0.5000 0.01315(15) Uani 1 2 d S . . F1 F 1.10010(9) 0.80703(15) 0.44120(6) 0.0262(2) Uani 1 1 d . . . F2 F 1.14440(8) 1.04884(14) 0.57260(6) 0.0244(2) Uani 1 1 d . . . F3 F 0.94630(9) 0.78863(15) 0.56867(6) 0.0262(2) Uani 1 1 d . . . N1 N 0.78857(12) 0.48475(19) 0.41401(8) 0.0165(3) Uani 1 1 d . . . H1A H 0.8369 0.4348 0.3641 0.025 Uiso 1 1 calc R . . H1B H 0.8121 0.3941 0.4636 0.025 Uiso 1 1 calc R . . H1C H 0.8141 0.6331 0.4269 0.025 Uiso 1 1 calc R . . C6 C 0.56442(14) 0.6556(2) 0.34883(9) 0.0168(3) Uani 1 1 d . . . H6 H 0.6190 0.7868 0.3318 0.020 Uiso 1 1 calc R . . C2 C 0.55514(14) 0.2779(2) 0.41933(9) 0.0159(3) Uani 1 1 d . . . H2 H 0.6035 0.1530 0.4497 0.019 Uiso 1 1 calc R . . C1 C 0.63112(14) 0.4722(2) 0.39373(9) 0.0139(3) Uani 1 1 d . . . C3 C 0.40610(14) 0.2700(2) 0.39949(10) 0.0179(3) Uani 1 1 d . . . H3 H 0.3517 0.1389 0.4169 0.021 Uiso 1 1 calc R . . C4 C 0.33656(15) 0.4525(2) 0.35446(10) 0.0183(3) Uani 1 1 d . . . H4 H 0.2349 0.4459 0.3411 0.022 Uiso 1 1 calc R . . C5 C 0.41537(15) 0.6446(2) 0.32890(9) 0.0186(3) Uani 1 1 d . . . H5 H 0.3676 0.7689 0.2978 0.022 Uiso 1 1 calc R . . O1 O 0.93328(12) 0.3657(2) 0.25142(8) 0.0270(3) Uani 1 1 d . . . H1S H 0.978(3) 0.248(4) 0.2660(17) 0.061(8) Uiso 1 1 d . . . H2S H 0.913(2) 0.358(4) 0.1938(18) 0.052(7) 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 Si1 0.0111(3) 0.0118(3) 0.0167(3) -0.00090(19) 0.00065(19) 0.00007(18) F1 0.0310(5) 0.0270(5) 0.0205(5) -0.0037(4) -0.0001(4) 0.0162(4) F2 0.0202(4) 0.0188(4) 0.0331(5) -0.0018(4) -0.0112(4) -0.0006(3) F3 0.0176(4) 0.0253(5) 0.0359(5) 0.0144(4) 0.0031(4) -0.0002(3) N1 0.0143(5) 0.0171(6) 0.0182(6) -0.0013(5) 0.0003(4) -0.0006(4) C6 0.0205(7) 0.0159(6) 0.0142(6) 0.0006(5) 0.0015(5) -0.0009(5) C2 0.0189(6) 0.0148(6) 0.0140(6) 0.0001(5) 0.0017(5) 0.0020(5) C1 0.0130(6) 0.0163(7) 0.0125(6) -0.0026(5) 0.0005(5) -0.0001(5) C3 0.0191(7) 0.0170(7) 0.0178(7) -0.0015(5) 0.0038(5) -0.0026(5) C4 0.0152(6) 0.0235(7) 0.0163(7) -0.0038(6) -0.0001(5) 0.0010(5) C5 0.0209(7) 0.0187(7) 0.0160(7) 0.0010(6) -0.0014(5) 0.0040(5) O1 0.0242(6) 0.0379(7) 0.0189(6) -0.0002(5) 0.0006(4) 0.0053(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 F3 1.6657(8) 3_776 ? Si1 F3 1.6657(8) . ? Si1 F2 1.6888(8) 3_776 ? Si1 F2 1.6888(8) . ? Si1 F1 1.6993(8) 3_776 ? Si1 F1 1.6993(8) . ? N1 C1 1.4713(16) . ? C6 C1 1.3795(19) . ? C6 C5 1.3944(19) . ? C2 C1 1.3853(18) . ? C2 C3 1.3934(19) . ? C3 C4 1.388(2) . ? C4 C5 1.3885(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F3 Si1 F3 180.00(4) 3_776 . ? F3 Si1 F2 89.82(4) 3_776 3_776 ? F3 Si1 F2 90.18(4) . 3_776 ? F3 Si1 F2 90.18(4) 3_776 . ? F3 Si1 F2 89.82(4) . . ? F2 Si1 F2 180.0 3_776 . ? F3 Si1 F1 89.55(4) 3_776 3_776 ? F3 Si1 F1 90.45(4) . 3_776 ? F2 Si1 F1 89.58(4) 3_776 3_776 ? F2 Si1 F1 90.42(4) . 3_776 ? F3 Si1 F1 90.45(4) 3_776 . ? F3 Si1 F1 89.55(4) . . ? F2 Si1 F1 90.42(4) 3_776 . ? F2 Si1 F1 89.58(4) . . ? F1 Si1 F1 180.00(5) 3_776 . ? C1 C6 C5 118.73(12) . . ? C1 C2 C3 118.41(12) . . ? C6 C1 C2 122.24(12) . . ? C6 C1 N1 118.34(12) . . ? C2 C1 N1 119.41(12) . . ? C4 C3 C2 120.39(13) . . ? C3 C4 C5 120.08(13) . . ? C4 C5 C6 120.15(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C6 C1 C2 0.2(2) . . . . ? C5 C6 C1 N1 179.66(12) . . . . ? C3 C2 C1 C6 -0.6(2) . . . . ? C3 C2 C1 N1 179.95(12) . . . . ? C1 C2 C3 C4 0.5(2) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? C3 C4 C5 C6 -0.4(2) . . . . ? C1 C6 C5 C4 0.3(2) . . . . ? 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 O1 0.91 1.93 2.8330(16) 172.8 . N1 H1B F1 0.91 1.96 2.8558(14) 168.6 3_766 N1 H1C F2 0.91 1.89 2.7821(14) 168.0 3_776 N1 H1C F3 0.91 2.52 3.1618(15) 128.3 . O1 H1S O1 0.82(3) 2.38(3) 3.1529(9) 157(2) 2_745 O1 H1S F3 0.82(3) 2.48(3) 2.9332(16) 116(2) 3_766 O1 H2S F1 0.85(3) 1.98(3) 2.8147(15) 170(2) 2_745 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.276 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.113