# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author 'Kwang-Ming Lee' _publ_contact_author_address ; Department of Chemistry National Kaohsiung Normal University, 62, Shen-Shung Road, Kaohsiung 824, Taiwan ; _publ_contact_author_email kmlee@nknucc.nknu.edu.tw _publ_contact_author_fax 886-7-6051083 _publ_contact_author_phone '886-7-7172930 ext 7119' _publ_section_title ; Self-assembly of Seven Diamide-containing Pyridinium Salts via Nonconventional C-H\^a\^a\^aO Hydrogen Bonding Catemers ; _publ_contact_author_name 'Kwang-Ming Lee' _publ_author_name 'Kwang-Ming Lee' data_838304 _database_code_depnum_ccdc_archive 'CCDC 838304' #TrackingRef '838304-10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 Cl N3 O2' _chemical_formula_weight 215.64 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' 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' _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.3951(4) _cell_length_b 8.1557(7) _cell_length_c 11.4412(9) _cell_angle_alpha 80.447(2) _cell_angle_beta 84.791(2) _cell_angle_gamma 72.016(2) _cell_volume 471.77(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5634 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Lump _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.382 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8501 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 7449 _diffrn_reflns_av_R_equivalents 0.0140 _diffrn_reflns_av_sigmaI/netI 0.0122 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 26.53 _reflns_number_total 1933 _reflns_number_gt 1850 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.34A (Bruker AXS, 2006)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0301P)^2^+0.2938P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1933 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_ref 0.0687 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.17987(6) 0.20252(4) 0.63083(3) 0.01727(11) Uani 1 1 d . . . O1 O 0.80272(18) 0.36874(12) 0.93731(8) 0.0183(2) Uani 1 1 d . . . O2 O -0.20506(17) 0.89364(11) 0.82257(8) 0.0151(2) Uani 1 1 d . . . N1 N 0.7008(2) 0.15033(14) 1.06252(10) 0.0164(2) Uani 1 1 d . . . H1A H 0.8337 0.1318 1.1074 0.020 Uiso 1 1 calc R . . H1B H 0.5931 0.0870 1.0799 0.020 Uiso 1 1 calc R . . N2 N 0.38692(19) 0.43433(13) 0.79969(9) 0.0112(2) Uani 1 1 d . . . N3 N -0.2629(2) 0.92321(14) 0.62499(9) 0.0147(2) Uani 1 1 d . . . H3A H -0.4097 1.0085 0.6280 0.018 Uiso 1 1 calc R . . H3B H -0.2018 0.8863 0.5570 0.018 Uiso 1 1 calc R . . C1 C 0.6627(2) 0.27455(15) 0.96804(11) 0.0129(2) Uani 1 1 d . . . C2 C 0.4344(2) 0.28398(15) 0.89472(11) 0.0130(2) Uani 1 1 d . . . H2B H 0.4729 0.1754 0.8594 0.016 Uiso 1 1 calc R . . H2A H 0.2754 0.2940 0.9471 0.016 Uiso 1 1 calc R . . C3 C 0.1641(2) 0.56615(15) 0.80171(10) 0.0117(2) Uani 1 1 d . . . H3 H 0.0403 0.5641 0.8661 0.014 Uiso 1 1 calc R . . C4 C 0.1144(2) 0.70489(15) 0.71034(11) 0.0120(2) Uani 1 1 d . . . C5 C -0.1345(2) 0.85067(15) 0.72250(11) 0.0125(2) Uani 1 1 d . . . C6 C 0.2981(2) 0.70721(16) 0.61705(11) 0.0145(3) Uani 1 1 d . . . H6 H 0.2652 0.7998 0.5526 0.017 Uiso 1 1 calc R . . C7 C 0.5308(2) 0.57184(17) 0.61963(11) 0.0152(3) Uani 1 1 d . . . H7 H 0.6617 0.5739 0.5585 0.018 Uiso 1 1 calc R . . C8 C 0.5705(2) 0.43491(16) 0.71109(11) 0.0138(2) Uani 1 1 d . . . H8 H 0.7271 0.3407 0.7120 0.017 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 0.01157(16) 0.02117(17) 0.01777(17) -0.00711(12) -0.00031(11) -0.00088(12) O1 0.0153(4) 0.0236(5) 0.0179(5) 0.0011(4) -0.0029(3) -0.0101(4) O2 0.0134(4) 0.0163(4) 0.0136(4) -0.0030(3) -0.0007(3) -0.0011(3) N1 0.0168(5) 0.0162(5) 0.0166(5) 0.0006(4) -0.0053(4) -0.0057(4) N2 0.0106(5) 0.0110(5) 0.0126(5) -0.0023(4) -0.0019(4) -0.0032(4) N3 0.0128(5) 0.0142(5) 0.0145(5) -0.0026(4) -0.0026(4) 0.0006(4) C1 0.0102(6) 0.0131(5) 0.0143(6) -0.0043(4) 0.0005(4) -0.0009(4) C2 0.0117(6) 0.0107(5) 0.0158(6) -0.0002(4) -0.0027(4) -0.0028(4) C3 0.0092(5) 0.0131(5) 0.0136(6) -0.0043(4) -0.0007(4) -0.0034(4) C4 0.0108(6) 0.0121(5) 0.0137(6) -0.0033(4) -0.0023(4) -0.0032(4) C5 0.0115(6) 0.0113(5) 0.0154(6) -0.0015(4) -0.0006(4) -0.0044(4) C6 0.0158(6) 0.0157(6) 0.0128(6) -0.0013(4) -0.0019(5) -0.0057(5) C7 0.0133(6) 0.0201(6) 0.0136(6) -0.0050(5) 0.0020(4) -0.0062(5) C8 0.0099(5) 0.0159(6) 0.0159(6) -0.0066(5) -0.0006(4) -0.0021(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 C1 1.2266(15) . ? O2 C5 1.2451(15) . ? N1 C1 1.3362(16) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 C3 1.3441(15) . ? N2 C8 1.3520(16) . ? N2 C2 1.4715(15) . ? N3 C5 1.3201(16) . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? C1 C2 1.5282(16) . ? C2 H2B 0.9900 . ? C2 H2A 0.9900 . ? C3 C4 1.3841(17) . ? C3 H3 0.9500 . ? C4 C6 1.3912(17) . ? C4 C5 1.5071(16) . ? C6 C7 1.3912(18) . ? C6 H6 0.9500 . ? C7 C8 1.3759(18) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? 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 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C3 N2 C8 121.52(10) . . ? C3 N2 C2 120.03(10) . . ? C8 N2 C2 118.45(10) . . ? C5 N3 H3A 120.0 . . ? C5 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? O1 C1 N1 124.40(11) . . ? O1 C1 C2 121.54(11) . . ? N1 C1 C2 113.97(10) . . ? N2 C2 C1 111.00(9) . . ? N2 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? N2 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? H2B C2 H2A 108.0 . . ? N2 C3 C4 120.25(11) . . ? N2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C6 119.37(11) . . ? C3 C4 C5 116.67(10) . . ? C6 C4 C5 123.88(11) . . ? O2 C5 N3 124.75(11) . . ? O2 C5 C4 118.37(11) . . ? N3 C5 C4 116.88(11) . . ? C4 C6 C7 118.99(11) . . ? C4 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C8 C7 C6 119.74(11) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? N2 C8 C7 120.07(11) . . ? N2 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.53 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.399 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.045 # END data_838305 _database_code_depnum_ccdc_archive 'CCDC 838305' #TrackingRef '838304-10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 Br N3 O2' _chemical_formula_weight 260.10 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' 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 'P 1 21/n 1' _symmetry_space_group_name_hall '-P 2yn' 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 10.3283(8) _cell_length_b 8.1976(7) _cell_length_c 12.3290(9) _cell_angle_alpha 90.00 _cell_angle_beta 114.243(3) _cell_angle_gamma 90.00 _cell_volume 951.81(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5398 _cell_measurement_theta_min 3.0755 _cell_measurement_theta_max 26.3569 _exptl_crystal_description Columnar _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.815 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 4.296 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7754 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 7935 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 26.36 _reflns_number_total 1937 _reflns_number_gt 1832 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.34A (Bruker AXS, 2006)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0172P)^2^+0.8088P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1937 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0182 _refine_ls_R_factor_gt 0.0168 _refine_ls_wR_factor_ref 0.0420 _refine_ls_wR_factor_gt 0.0416 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 Br1 Br 0.756031(16) 0.892408(19) 0.905524(13) 0.01267(6) Uani 1 1 d . . . O1 O 0.10833(12) 0.64526(14) 0.68310(10) 0.0149(2) Uani 1 1 d . . . O2 O 0.57406(12) 0.43667(14) 1.15911(10) 0.0127(2) Uani 1 1 d . . . N1 N 0.13794(15) 0.40814(17) 0.60015(12) 0.0153(3) Uani 1 1 d . . . H1A H 0.1354 0.4561 0.5354 0.018 Uiso 1 1 calc R . . H1B H 0.1493 0.3018 0.6084 0.018 Uiso 1 1 calc R . . N2 N 0.16935(13) 0.48606(16) 0.89904(11) 0.0098(3) Uani 1 1 d . . . N3 N 0.49898(14) 0.50962(17) 1.30113(11) 0.0137(3) Uani 1 1 d . . . H3A H 0.5794 0.4809 1.3598 0.016 Uiso 1 1 calc R . . H3B H 0.4295 0.5500 1.3167 0.016 Uiso 1 1 calc R . . C1 C 0.12461(16) 0.4965(2) 0.68564(13) 0.0117(3) Uani 1 1 d . . . C2 C 0.12527(17) 0.39147(19) 0.78845(13) 0.0116(3) Uani 1 1 d . . . H2B H 0.0289 0.3469 0.7676 0.014 Uiso 1 1 calc R . . H2A H 0.1910 0.2985 0.8009 0.014 Uiso 1 1 calc R . . C3 C 0.29648(16) 0.45556(19) 0.98757(13) 0.0097(3) Uani 1 1 d . . . H3 H 0.3571 0.3759 0.9771 0.012 Uiso 1 1 calc R . . C4 C 0.33980(16) 0.53962(19) 1.09421(13) 0.0099(3) Uani 1 1 d . . . C5 C 0.48243(16) 0.49199(19) 1.18869(13) 0.0108(3) Uani 1 1 d . . . C6 C 0.25125(17) 0.6577(2) 1.10741(14) 0.0131(3) Uani 1 1 d . . . H6 H 0.2797 0.7173 1.1796 0.016 Uiso 1 1 calc R . . C7 C 0.11992(17) 0.6884(2) 1.01368(14) 0.0133(3) Uani 1 1 d . . . H7 H 0.0585 0.7694 1.0214 0.016 Uiso 1 1 calc R . . C8 C 0.08044(17) 0.60013(19) 0.91012(14) 0.0123(3) Uani 1 1 d . . . H8 H -0.0092 0.6191 0.8463 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 0.01182(9) 0.01403(10) 0.01304(9) -0.00073(6) 0.00601(6) -0.00147(6) O1 0.0159(6) 0.0117(6) 0.0155(6) 0.0026(4) 0.0048(5) 0.0009(4) O2 0.0118(5) 0.0133(5) 0.0134(5) 0.0013(4) 0.0056(4) 0.0014(4) N1 0.0200(7) 0.0143(7) 0.0125(6) 0.0016(5) 0.0077(6) 0.0011(6) N2 0.0112(6) 0.0091(6) 0.0093(6) 0.0010(5) 0.0043(5) -0.0009(5) N3 0.0104(6) 0.0189(7) 0.0101(6) 0.0007(5) 0.0026(5) 0.0034(5) C1 0.0069(7) 0.0159(8) 0.0098(7) 0.0013(6) 0.0010(6) -0.0011(6) C2 0.0133(7) 0.0114(8) 0.0095(7) -0.0014(6) 0.0040(6) -0.0017(6) C3 0.0103(7) 0.0079(7) 0.0125(7) 0.0032(6) 0.0063(6) 0.0002(6) C4 0.0102(7) 0.0094(7) 0.0108(7) 0.0026(6) 0.0048(6) -0.0014(6) C5 0.0122(7) 0.0078(7) 0.0117(7) 0.0007(6) 0.0043(6) -0.0022(6) C6 0.0173(8) 0.0105(8) 0.0127(7) 0.0006(6) 0.0074(6) -0.0010(6) C7 0.0142(8) 0.0115(8) 0.0158(8) 0.0020(6) 0.0076(6) 0.0036(6) C8 0.0104(7) 0.0129(8) 0.0134(7) 0.0037(6) 0.0048(6) 0.0014(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 O1 C1 1.229(2) . ? O2 C5 1.2320(19) . ? N1 C1 1.332(2) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 C3 1.342(2) . ? N2 C8 1.356(2) . ? N2 C2 1.4690(19) . ? N3 C5 1.333(2) . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? C1 C2 1.530(2) . ? C2 H2B 0.9900 . ? C2 H2A 0.9900 . ? C3 C4 1.386(2) . ? C3 H3 0.9500 . ? C4 C6 1.387(2) . ? C4 C5 1.507(2) . ? C6 C7 1.397(2) . ? C6 H6 0.9500 . ? C7 C8 1.376(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? 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 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C3 N2 C8 121.56(13) . . ? C3 N2 C2 118.91(13) . . ? C8 N2 C2 119.53(13) . . ? C5 N3 H3A 120.0 . . ? C5 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? O1 C1 N1 125.24(14) . . ? O1 C1 C2 122.23(14) . . ? N1 C1 C2 112.49(14) . . ? N2 C2 C1 111.47(13) . . ? N2 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? N2 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? H2B C2 H2A 108.0 . . ? N2 C3 C4 120.39(14) . . ? N2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C3 C4 C6 119.14(14) . . ? C3 C4 C5 115.91(13) . . ? C6 C4 C5 124.95(14) . . ? O2 C5 N3 124.17(14) . . ? O2 C5 C4 119.51(13) . . ? N3 C5 C4 116.30(13) . . ? C4 C6 C7 119.46(15) . . ? C4 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C8 C7 C6 119.35(15) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? N2 C8 C7 120.09(14) . . ? N2 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.410 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.054 # END data_838306 _database_code_depnum_ccdc_archive 'CCDC 838306' #TrackingRef '838304-10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 B F4 N3 O2' _chemical_formula_weight 267.00 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' B B 0.0013 0.0007 '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 'P 1 21/c 1' _symmetry_space_group_name_hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.5624(4) _cell_length_b 8.3426(4) _cell_length_c 12.2163(5) _cell_angle_alpha 90.00 _cell_angle_beta 116.412(2) _cell_angle_gamma 90.00 _cell_volume 1055.39(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5246 _cell_measurement_theta_min 3.0706 _cell_measurement_theta_max 26.3691 _exptl_crystal_description Lump _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.680 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.165 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8723 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 8738 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 26.38 _reflns_number_total 2137 _reflns_number_gt 2000 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.34A (Bruker AXS, 2006)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0335P)^2^+0.6090P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2137 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0805 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 B1 B 0.36922(14) 0.87439(18) 0.11630(13) 0.0162(3) Uani 1 1 d . . . F1 F 0.24697(7) 0.90456(11) 0.02148(7) 0.0259(2) Uani 1 1 d . . . F2 F 0.42881(8) 0.75123(11) 0.08392(8) 0.0303(2) Uani 1 1 d . . . F3 F 0.35751(8) 0.83108(13) 0.21982(7) 0.0338(2) Uani 1 1 d . . . F4 F 0.44564(8) 1.01056(10) 0.13855(10) 0.0372(3) Uani 1 1 d . . . O1 O 0.91193(9) -0.08080(11) 0.82727(8) 0.0190(2) Uani 1 1 d . . . O2 O 0.91719(8) 0.00953(11) 0.32361(8) 0.0164(2) Uani 1 1 d . . . N1 N 1.01055(11) 0.15758(14) 0.90381(10) 0.0191(2) Uani 1 1 d . . . H1A H 1.0560 0.1194 0.9779 0.023 Uiso 1 1 calc R . . H1B H 1.0183 0.2589 0.8881 0.023 Uiso 1 1 calc R . . N2 N 0.79024(10) 0.04353(12) 0.58968(9) 0.0127(2) Uani 1 1 d . . . N3 N 0.71389(10) -0.04490(13) 0.18135(9) 0.0178(2) Uani 1 1 d . . . H3A H 0.7339 -0.0332 0.1202 0.021 Uiso 1 1 calc R . . H3B H 0.6344 -0.0697 0.1668 0.021 Uiso 1 1 calc R . . C1 C 0.92973(12) 0.06170(15) 0.81504(11) 0.0147(3) Uani 1 1 d . . . C2 C 0.85526(12) 0.15193(15) 0.69472(11) 0.0142(3) Uani 1 1 d . . . H2B H 0.7899 0.2216 0.7022 0.017 Uiso 1 1 calc R . . H2A H 0.9159 0.2216 0.6795 0.017 Uiso 1 1 calc R . . C3 C 0.82387(11) 0.04940(14) 0.49765(11) 0.0128(2) Uani 1 1 d . . . H3 H 0.8919 0.1183 0.5036 0.015 Uiso 1 1 calc R . . C4 C 0.76055(12) -0.04381(14) 0.39438(11) 0.0133(2) Uani 1 1 d . . . C5 C 0.80392(12) -0.02514(14) 0.29589(11) 0.0136(2) Uani 1 1 d . . . C6 C 0.66207(12) -0.14530(15) 0.38728(11) 0.0151(3) Uani 1 1 d . . . H6 H 0.6181 -0.2113 0.3176 0.018 Uiso 1 1 calc R . . C7 C 0.62882(12) -0.14892(15) 0.48357(11) 0.0165(3) Uani 1 1 d . . . H7 H 0.5617 -0.2176 0.4800 0.020 Uiso 1 1 calc R . . C8 C 0.69359(12) -0.05266(15) 0.58397(11) 0.0156(3) Uani 1 1 d . . . H8 H 0.6704 -0.0538 0.6494 0.019 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 B1 0.0159(7) 0.0190(7) 0.0141(7) -0.0010(5) 0.0070(6) -0.0010(5) F1 0.0178(4) 0.0392(5) 0.0167(4) 0.0047(3) 0.0041(3) -0.0008(3) F2 0.0284(5) 0.0312(5) 0.0375(5) -0.0125(4) 0.0201(4) -0.0007(4) F3 0.0287(5) 0.0595(6) 0.0176(4) 0.0096(4) 0.0143(4) 0.0114(4) F4 0.0223(5) 0.0183(4) 0.0594(7) 0.0011(4) 0.0078(4) -0.0030(3) O1 0.0225(5) 0.0175(5) 0.0148(5) 0.0023(4) 0.0064(4) -0.0007(4) O2 0.0154(5) 0.0199(5) 0.0147(4) -0.0008(3) 0.0076(4) -0.0001(3) N1 0.0222(6) 0.0181(5) 0.0119(5) 0.0021(4) 0.0030(4) -0.0016(4) N2 0.0138(5) 0.0142(5) 0.0093(5) 0.0006(4) 0.0043(4) 0.0014(4) N3 0.0170(5) 0.0255(6) 0.0111(5) -0.0012(4) 0.0065(4) -0.0031(4) C1 0.0147(6) 0.0186(6) 0.0119(6) 0.0010(5) 0.0069(5) 0.0018(5) C2 0.0170(6) 0.0146(6) 0.0103(6) -0.0013(5) 0.0055(5) 0.0003(5) C3 0.0126(6) 0.0138(6) 0.0116(6) 0.0030(4) 0.0051(5) 0.0026(4) C4 0.0142(6) 0.0138(6) 0.0109(6) 0.0025(4) 0.0048(5) 0.0034(5) C5 0.0165(6) 0.0113(5) 0.0134(6) 0.0004(4) 0.0071(5) 0.0018(4) C6 0.0157(6) 0.0148(6) 0.0124(6) 0.0007(5) 0.0040(5) 0.0011(5) C7 0.0160(6) 0.0170(6) 0.0156(6) 0.0028(5) 0.0063(5) -0.0009(5) C8 0.0159(6) 0.0182(6) 0.0142(6) 0.0038(5) 0.0080(5) 0.0018(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 B1 F3 1.3786(16) . ? B1 F2 1.3889(16) . ? B1 F4 1.3898(17) . ? B1 F1 1.3952(16) . ? O1 C1 1.2269(16) . ? O2 C5 1.2325(15) . ? N1 C1 1.3370(17) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 C3 1.3441(15) . ? N2 C8 1.3522(16) . ? N2 C2 1.4736(15) . ? N3 C5 1.3315(16) . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? C1 C2 1.5305(16) . ? C2 H2B 0.9900 . ? C2 H2A 0.9900 . ? C3 C4 1.3822(17) . ? C3 H3 0.9500 . ? C4 C6 1.3904(18) . ? C4 C5 1.5034(16) . ? C6 C7 1.3909(17) . ? C6 H6 0.9500 . ? C7 C8 1.3759(18) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? 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 B1 F2 109.33(11) . . ? F3 B1 F4 110.38(12) . . ? F2 B1 F4 107.91(11) . . ? F3 B1 F1 109.41(11) . . ? F2 B1 F1 110.16(11) . . ? F4 B1 F1 109.64(11) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C3 N2 C8 121.23(11) . . ? C3 N2 C2 118.73(10) . . ? C8 N2 C2 119.93(10) . . ? C5 N3 H3A 120.0 . . ? C5 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? O1 C1 N1 125.13(12) . . ? O1 C1 C2 122.71(11) . . ? N1 C1 C2 112.11(11) . . ? N2 C2 C1 112.68(10) . . ? N2 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? N2 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? H2B C2 H2A 107.8 . . ? N2 C3 C4 120.67(11) . . ? N2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C6 119.09(11) . . ? C3 C4 C5 116.25(11) . . ? C6 C4 C5 124.66(11) . . ? O2 C5 N3 123.80(11) . . ? O2 C5 C4 119.76(11) . . ? N3 C5 C4 116.43(11) . . ? C4 C6 C7 119.16(11) . . ? C4 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C8 C7 C6 119.71(12) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? N2 C8 C7 120.13(11) . . ? N2 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.316 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.042 # END data_838307 _database_code_depnum_ccdc_archive 'CCDC 838307' #TrackingRef '838304-10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 N4 O5' _chemical_formula_weight 242.20 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4520(3) _cell_length_b 6.1264(3) _cell_length_c 15.5624(8) _cell_angle_alpha 99.478(3) _cell_angle_beta 92.657(3) _cell_angle_gamma 99.407(3) _cell_volume 504.38(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4263 _cell_measurement_theta_min 2.6614 _cell_measurement_theta_max 26.3862 _exptl_crystal_description Columnar _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 252 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9122 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 8320 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 26.45 _reflns_number_total 2060 _reflns_number_gt 1878 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.34A (Bruker AXS, 2006)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2060 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.1196 _refine_ls_wR_factor_gt 0.1044 _refine_ls_goodness_of_fit_ref 1.930 _refine_ls_restrained_S_all 1.930 _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 1.24498(16) 0.21126(15) 0.84626(6) 0.0151(3) Uani 1 1 d . . . O2 O 0.80963(18) -0.27850(16) 0.50168(6) 0.0213(3) Uani 1 1 d . . . O3 O 0.03888(15) 0.67602(15) 0.83644(6) 0.0159(3) Uani 1 1 d . . . O4 O 0.39283(17) 0.73294(15) 0.77801(7) 0.0181(3) Uani 1 1 d . . . O5 O 0.38368(17) 0.75049(17) 0.91876(7) 0.0216(3) Uani 1 1 d . . . N1 N 1.1331(2) 0.26090(18) 0.98537(8) 0.0158(3) Uani 1 1 d . . . H1A H 1.2842 0.2815 1.0077 0.019 Uiso 1 1 calc R . . H1B H 1.0123 0.2658 1.0189 0.019 Uiso 1 1 calc R . . N2 N 0.77104(18) 0.16475(17) 0.77543(7) 0.0116(3) Uani 1 1 d . . . N3 N 1.0893(2) -0.3110(2) 0.60875(8) 0.0181(3) Uani 1 1 d . . . H3A H 1.1416 -0.4199 0.5768 0.022 Uiso 1 1 calc R . . H3B H 1.1532 -0.2626 0.6614 0.022 Uiso 1 1 calc R . . N4 N 0.27340(19) 0.71964(18) 0.84432(8) 0.0134(3) Uani 1 1 d . . . C1 C 1.0864(2) 0.2215(2) 0.89940(9) 0.0117(3) Uani 1 1 d . . . C2 C 0.8086(2) 0.1836(2) 0.87072(9) 0.0122(3) Uani 1 1 d . . . H2A H 0.7252 0.0472 0.8882 0.015 Uiso 1 1 calc R . . H2B H 0.7357 0.3081 0.8993 0.015 Uiso 1 1 calc R . . C3 C 0.8527(2) -0.0039(2) 0.72467(9) 0.0121(3) Uani 1 1 d . . . H3 H 0.9277 -0.1057 0.7502 0.014 Uiso 1 1 calc R . . C4 C 0.8262(2) -0.0270(2) 0.63503(9) 0.0133(3) Uani 1 1 d . . . C5 C 0.9089(2) -0.2169(2) 0.57660(9) 0.0156(3) Uani 1 1 d . . . C6 C 0.7077(2) 0.1251(2) 0.59830(9) 0.0159(3) Uani 1 1 d . . . H6 H 0.6855 0.1121 0.5379 0.019 Uiso 1 1 calc R . . C7 C 0.6242(2) 0.2946(2) 0.65229(10) 0.0155(3) Uani 1 1 d . . . H7 H 0.5439 0.3961 0.6285 0.019 Uiso 1 1 calc R . . C8 C 0.6591(2) 0.3137(2) 0.74073(10) 0.0135(3) Uani 1 1 d . . . H8 H 0.6055 0.4299 0.7772 0.016 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 O1 0.0113(5) 0.0176(5) 0.0166(6) 0.0022(4) 0.0036(4) 0.0028(4) O2 0.0247(5) 0.0251(6) 0.0129(6) -0.0027(4) -0.0042(4) 0.0085(4) O3 0.0082(5) 0.0175(5) 0.0220(6) 0.0054(4) -0.0001(4) 0.0011(4) O4 0.0185(5) 0.0177(5) 0.0194(6) 0.0035(4) 0.0090(4) 0.0047(4) O5 0.0199(5) 0.0260(6) 0.0174(6) 0.0060(5) -0.0080(4) 0.0003(4) N1 0.0118(6) 0.0210(7) 0.0143(7) 0.0024(5) -0.0004(5) 0.0025(5) N2 0.0083(5) 0.0127(6) 0.0131(6) 0.0019(5) -0.0001(4) 0.0000(4) N3 0.0194(6) 0.0204(6) 0.0138(7) -0.0028(5) -0.0006(5) 0.0084(5) N4 0.0125(6) 0.0110(6) 0.0169(7) 0.0034(5) 0.0002(5) 0.0021(4) C1 0.0122(6) 0.0073(6) 0.0156(7) 0.0024(5) 0.0003(5) 0.0017(5) C2 0.0115(6) 0.0144(7) 0.0106(7) 0.0018(5) 0.0022(5) 0.0022(5) C3 0.0098(6) 0.0112(7) 0.0151(8) 0.0020(6) 0.0000(5) 0.0022(5) C4 0.0103(6) 0.0142(7) 0.0148(8) 0.0025(6) 0.0002(5) 0.0005(5) C5 0.0150(6) 0.0173(7) 0.0141(8) 0.0027(6) 0.0017(6) 0.0011(5) C6 0.0140(6) 0.0202(7) 0.0126(7) 0.0045(6) -0.0013(5) -0.0003(5) C7 0.0126(6) 0.0156(7) 0.0199(8) 0.0064(6) -0.0005(6) 0.0037(5) C8 0.0078(6) 0.0119(6) 0.0212(8) 0.0033(6) 0.0016(5) 0.0019(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 O1 C1 1.2256(16) . ? O2 C5 1.2346(16) . ? O3 N4 1.2587(13) . ? O4 N4 1.2522(15) . ? O5 N4 1.2513(15) . ? N1 C1 1.3248(18) . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N2 C3 1.3430(17) . ? N2 C8 1.3454(17) . ? N2 C2 1.4703(17) . ? N3 C5 1.3360(17) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? C1 C2 1.5282(17) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.3772(19) . ? C3 H3 0.9300 . ? C4 C6 1.3968(19) . ? C4 C5 1.4982(19) . ? C6 C7 1.377(2) . ? C6 H6 0.9300 . ? C7 C8 1.364(2) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C3 N2 C8 121.40(12) . . ? C3 N2 C2 118.08(11) . . ? C8 N2 C2 120.52(11) . . ? C5 N3 H3A 120.0 . . ? C5 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? O5 N4 O4 120.97(11) . . ? O5 N4 O3 119.21(12) . . ? O4 N4 O3 119.81(11) . . ? O1 C1 N1 124.95(12) . . ? O1 C1 C2 121.72(12) . . ? N1 C1 C2 113.32(12) . . ? N2 C2 C1 110.56(11) . . ? N2 C2 H2A 109.5 . . ? C1 C2 H2A 109.5 . . ? N2 C2 H2B 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? N2 C3 C4 120.47(12) . . ? N2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C3 C4 C6 118.60(13) . . ? C3 C4 C5 121.76(12) . . ? C6 C4 C5 119.57(12) . . ? O2 C5 N3 123.17(13) . . ? O2 C5 C4 119.18(12) . . ? N3 C5 C4 117.65(12) . . ? C7 C6 C4 119.37(13) . . ? C7 C6 H6 120.3 . . ? C4 C6 H6 120.3 . . ? C8 C7 C6 119.95(13) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? N2 C8 C7 120.19(13) . . ? N2 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.358 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.057 # END data_838308 _database_code_depnum_ccdc_archive 'CCDC 838308' #TrackingRef '838304-10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 F3 N3 O5 S' _chemical_formula_weight 329.26 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' 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' _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4003(2) _cell_length_b 8.9153(2) _cell_length_c 10.3151(3) _cell_angle_alpha 101.5700(10) _cell_angle_beta 103.4520(10) _cell_angle_gamma 111.6400(10) _cell_volume 662.40(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7375 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Lump _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.307 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8845 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 10291 _diffrn_reflns_av_R_equivalents 0.0150 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 26.51 _reflns_number_total 2702 _reflns_number_gt 2530 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.34A (Bruker AXS, 2006)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0337P)^2^+0.4295P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2702 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0358 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0847 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_restrained_S_all 1.171 _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 0.48077(15) 0.67299(13) 0.43378(11) 0.0190(2) Uani 1 1 d . . . O2 O 0.75696(15) 0.85638(14) -0.04335(11) 0.0216(2) Uani 1 1 d . . . N1 N 0.35768(18) 0.39214(16) 0.31293(13) 0.0187(3) Uani 1 1 d . . . H1A H 0.3890 0.3640 0.3887 0.022 Uiso 1 1 calc R . . H1B H 0.2989 0.3130 0.2303 0.022 Uiso 1 1 calc R . . N2 N 0.43252(16) 0.76097(15) 0.19395(12) 0.0130(2) Uani 1 1 d . . . N3 N 0.86449(18) 1.14152(17) 0.04044(15) 0.0219(3) Uani 1 1 d . . . H3A H 0.9318 1.1590 -0.0138 0.026 Uiso 1 1 calc R . . H3B H 0.8641 1.2284 0.0984 0.026 Uiso 1 1 calc R . . C1 C 0.39904(19) 0.55323(19) 0.32330(15) 0.0148(3) Uani 1 1 d . . . C2 C 0.32836(19) 0.58299(18) 0.18482(15) 0.0149(3) Uani 1 1 d . . . H2A H 0.3397 0.5059 0.1075 0.018 Uiso 1 1 calc R . . H2B H 0.1981 0.5569 0.1637 0.018 Uiso 1 1 calc R . . C3 C 0.54245(19) 0.79625(18) 0.11708(14) 0.0138(3) Uani 1 1 d . . . H3 H 0.5477 0.7058 0.0542 0.017 Uiso 1 1 calc R . . C4 C 0.64789(19) 0.96234(18) 0.12832(14) 0.0141(3) Uani 1 1 d . . . C5 C 0.76351(19) 0.98408(19) 0.03486(15) 0.0159(3) Uani 1 1 d . . . C6 C 0.6399(2) 1.09345(19) 0.22235(15) 0.0169(3) Uani 1 1 d . . . H6 H 0.7131 1.2088 0.2335 0.020 Uiso 1 1 calc R . . C7 C 0.5238(2) 1.05358(19) 0.29958(15) 0.0176(3) Uani 1 1 d . . . H7 H 0.5162 1.1418 0.3632 0.021 Uiso 1 1 calc R . . C8 C 0.4202(2) 0.88658(19) 0.28368(15) 0.0159(3) Uani 1 1 d . . . H8 H 0.3397 0.8590 0.3356 0.019 Uiso 1 1 calc R . . S1 S 0.12703(5) 0.40586(4) 0.78232(4) 0.01463(12) Uani 1 1 d . . . F1 F -0.1019(2) 0.2030(3) 0.53320(17) 0.0484(6) Uani 0.730(2) 1 d P A 1 F2 F 0.1374(2) 0.1616(2) 0.6038(2) 0.0469(5) Uani 0.730(2) 1 d P A 1 F3 F 0.1578(3) 0.3780(3) 0.53281(19) 0.0513(6) Uani 0.730(2) 1 d P A 1 O3 O 0.0160(6) 0.2862(5) 0.8376(3) 0.0284(7) Uani 0.730(2) 1 d P A 1 O4 O 0.0623(3) 0.5350(3) 0.7607(2) 0.0242(4) Uani 0.730(2) 1 d P A 1 O5 O 0.3218(11) 0.4735(8) 0.8472(7) 0.0206(8) Uani 0.730(2) 1 d P A 1 C9 C 0.0770(5) 0.2810(5) 0.6025(4) 0.0267(7) Uani 0.730(2) 1 d P A 1 F11 F -0.1003(6) 0.3045(8) 0.5348(5) 0.0484(6) Uani 0.270(2) 1 d P A 2 F21 F 0.1087(7) 0.2153(7) 0.5461(7) 0.0469(5) Uani 0.270(2) 1 d P A 2 F31 F 0.1698(8) 0.4775(10) 0.5615(5) 0.0513(6) Uani 0.270(2) 1 d P A 2 O41 O 0.0883(10) 0.5413(9) 0.8177(6) 0.0242(4) Uani 0.270(2) 1 d P A 2 C91 C 0.0774(13) 0.3493(12) 0.5958(10) 0.0239(18) Uani 0.270(2) 1 d P A 2 O31 O 0.0155(19) 0.2552(17) 0.8024(11) 0.0284(7) Uani 0.270(2) 1 d P A 2 O51 O 0.317(3) 0.445(3) 0.829(2) 0.0206(8) Uani 0.270(2) 1 d P 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 O1 0.0264(6) 0.0163(5) 0.0133(5) 0.0034(4) 0.0055(4) 0.0097(5) O2 0.0243(6) 0.0192(6) 0.0186(5) 0.0024(4) 0.0112(4) 0.0062(5) N1 0.0276(7) 0.0157(6) 0.0130(6) 0.0049(5) 0.0064(5) 0.0097(5) N2 0.0135(6) 0.0140(6) 0.0117(5) 0.0047(5) 0.0037(4) 0.0060(5) N3 0.0224(7) 0.0194(7) 0.0278(7) 0.0100(6) 0.0155(6) 0.0077(6) C1 0.0155(7) 0.0173(7) 0.0145(7) 0.0056(5) 0.0079(5) 0.0082(6) C2 0.0146(6) 0.0138(7) 0.0144(7) 0.0045(5) 0.0051(5) 0.0042(6) C3 0.0148(6) 0.0165(7) 0.0108(6) 0.0043(5) 0.0036(5) 0.0081(6) C4 0.0141(6) 0.0161(7) 0.0120(6) 0.0056(5) 0.0032(5) 0.0067(6) C5 0.0146(7) 0.0190(7) 0.0142(7) 0.0067(6) 0.0044(5) 0.0070(6) C6 0.0187(7) 0.0144(7) 0.0155(7) 0.0045(5) 0.0031(6) 0.0068(6) C7 0.0218(7) 0.0182(7) 0.0145(7) 0.0032(6) 0.0055(6) 0.0120(6) C8 0.0175(7) 0.0208(7) 0.0132(6) 0.0060(6) 0.0062(5) 0.0113(6) S1 0.01473(19) 0.01404(19) 0.01306(18) 0.00325(13) 0.00543(13) 0.00420(14) F1 0.0225(6) 0.0708(14) 0.0247(7) -0.0180(9) -0.0065(5) 0.0175(9) F2 0.0366(8) 0.0357(10) 0.0539(12) -0.0163(8) 0.0053(8) 0.0222(7) F3 0.0466(9) 0.108(2) 0.0231(8) 0.0288(11) 0.0253(8) 0.0460(14) O3 0.0249(7) 0.0354(18) 0.0273(19) 0.0212(15) 0.0125(14) 0.0076(11) O4 0.0232(9) 0.0198(7) 0.0348(13) 0.0110(11) 0.0113(11) 0.0127(7) O5 0.0162(7) 0.020(2) 0.015(2) -0.0016(15) 0.0010(13) 0.0031(17) C9 0.0186(12) 0.034(2) 0.0232(14) -0.0032(16) 0.0036(10) 0.0150(16) F11 0.0225(6) 0.0708(14) 0.0247(7) -0.0180(9) -0.0065(5) 0.0175(9) F21 0.0366(8) 0.0357(10) 0.0539(12) -0.0163(8) 0.0053(8) 0.0222(7) F31 0.0466(9) 0.108(2) 0.0231(8) 0.0288(11) 0.0253(8) 0.0460(14) O41 0.0232(9) 0.0198(7) 0.0348(13) 0.0110(11) 0.0113(11) 0.0127(7) C91 0.020(3) 0.025(5) 0.017(3) 0.001(4) 0.002(3) 0.006(4) O31 0.0249(7) 0.0354(18) 0.0273(19) 0.0212(15) 0.0125(14) 0.0076(11) O51 0.0162(7) 0.020(2) 0.015(2) -0.0016(15) 0.0010(13) 0.0031(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 O1 C1 1.2318(18) . ? O2 C5 1.2307(18) . ? N1 C1 1.3221(19) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 C3 1.3442(18) . ? N2 C8 1.3551(18) . ? N2 C2 1.4731(18) . ? N3 C5 1.326(2) . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? C1 C2 1.529(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.381(2) . ? C3 H3 0.9500 . ? C4 C6 1.394(2) . ? C4 C5 1.511(2) . ? C6 C7 1.390(2) . ? C6 H6 0.9500 . ? C7 C8 1.372(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? S1 O5 1.446(8) . ? S1 O41 1.366(7) . ? S1 O3 1.446(4) . ? S1 O31 1.414(14) . ? S1 O4 1.476(2) . ? S1 O51 1.44(3) . ? S1 C9 1.822(3) . ? S1 C91 1.792(9) . ? F1 C9 1.335(4) . ? F2 C9 1.339(4) . ? F3 C9 1.330(5) . ? F11 C91 1.344(11) . ? F21 C91 1.345(10) . ? F31 C91 1.292(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 C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C3 N2 C8 121.26(13) . . ? C3 N2 C2 119.60(12) . . ? C8 N2 C2 119.10(12) . . ? C5 N3 H3A 120.0 . . ? C5 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? O1 C1 N1 124.95(14) . . ? O1 C1 C2 120.47(13) . . ? N1 C1 C2 114.51(12) . . ? N2 C2 C1 110.33(11) . . ? N2 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? N2 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? N2 C3 C4 120.83(13) . . ? N2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C6 118.73(13) . . ? C3 C4 C5 115.44(13) . . ? C6 C4 C5 125.83(13) . . ? O2 C5 N3 123.73(14) . . ? O2 C5 C4 118.83(13) . . ? N3 C5 C4 117.44(13) . . ? C7 C6 C4 119.32(14) . . ? C7 C6 H6 120.3 . . ? C4 C6 H6 120.3 . . ? C8 C7 C6 119.84(14) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? N2 C8 C7 120.00(13) . . ? N2 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? O5 S1 O41 105.0(4) . . ? O5 S1 O3 116.6(4) . . ? O41 S1 O3 102.5(3) . . ? O5 S1 O31 118.1(7) . . ? O41 S1 O31 115.9(6) . . ? O3 S1 O31 16.3(4) . . ? O5 S1 O4 114.3(3) . . ? O41 S1 O4 22.3(2) . . ? O3 S1 O4 112.65(19) . . ? O31 S1 O4 121.3(6) . . ? O5 S1 O51 10.7(8) . . ? O41 S1 O51 115.2(8) . . ? O3 S1 O51 115.0(11) . . ? O31 S1 O51 113.3(12) . . ? O4 S1 O51 122.5(9) . . ? O5 S1 C9 105.2(2) . . ? O41 S1 C9 124.4(3) . . ? O3 S1 C9 104.10(17) . . ? O31 S1 C9 88.3(4) . . ? O4 S1 C9 102.06(14) . . ? O51 S1 C9 95.9(7) . . ? O5 S1 C91 107.5(4) . . ? O41 S1 C91 105.6(4) . . ? O3 S1 C91 118.2(3) . . ? O31 S1 C91 103.9(5) . . ? O4 S1 C91 83.3(3) . . ? O51 S1 C91 100.6(9) . . ? C9 S1 C91 19.9(2) . . ? F2 C9 F3 108.1(3) . . ? F2 C9 F1 108.0(3) . . ? F3 C9 F1 108.7(3) . . ? F2 C9 S1 109.6(2) . . ? F3 C9 S1 111.3(3) . . ? F1 C9 S1 111.0(2) . . ? F21 C91 F31 110.2(8) . . ? F21 C91 F11 107.5(7) . . ? F31 C91 F11 108.2(8) . . ? F21 C91 S1 111.9(7) . . ? F31 C91 S1 110.7(6) . . ? F11 C91 S1 108.1(6) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.51 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.477 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.049 # END data_838309 _database_code_depnum_ccdc_archive 'CCDC 838309' #TrackingRef '838304-10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 F6 N3 O2 P' _chemical_formula_weight 325.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 13.2470(10) _cell_length_b 11.2054(10) _cell_length_c 15.5055(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2301.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4139 _cell_measurement_theta_min 2.6272 _cell_measurement_theta_max 26.3967 _exptl_crystal_description Lump _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.877 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.327 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8970 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 17454 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 26.40 _reflns_number_total 2356 _reflns_number_gt 1944 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.34A (Bruker AXS, 2006)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0345P)^2^+1.3165P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2356 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0775 _refine_ls_wR_factor_gt 0.0714 _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 P1 P 0.31229(3) 0.88143(4) 0.14978(3) 0.01462(12) Uani 1 1 d . . . F1 F 0.40171(8) 0.87232(11) 0.08077(7) 0.0325(3) Uani 1 1 d . . . F2 F 0.31771(8) 1.02426(9) 0.14447(6) 0.0254(3) Uani 1 1 d . . . F3 F 0.23122(7) 0.88174(9) 0.07278(6) 0.0228(2) Uani 1 1 d . . . F4 F 0.30633(9) 0.74050(10) 0.15554(8) 0.0366(3) Uani 1 1 d . . . F5 F 0.22276(7) 0.89339(10) 0.21848(7) 0.0276(3) Uani 1 1 d . . . F6 F 0.39318(7) 0.88316(9) 0.22667(6) 0.0250(2) Uani 1 1 d . . . O1 O 0.04332(8) 0.61779(10) 0.46532(7) 0.0179(3) Uani 1 1 d . . . O2 O 0.43309(8) 0.56605(11) 0.32433(7) 0.0184(3) Uani 1 1 d . . . N1 N -0.04494(10) 0.52156(13) 0.36123(9) 0.0182(3) Uani 1 1 d . . . H1A H -0.0780 0.4769 0.3984 0.022 Uiso 1 1 calc R . . H1B H -0.0564 0.5139 0.3056 0.022 Uiso 1 1 calc R . . N2 N 0.16386(10) 0.72999(12) 0.35505(8) 0.0134(3) Uani 1 1 d . . . N3 N 0.51956(10) 0.69691(13) 0.40613(9) 0.0188(3) Uani 1 1 d . . . H3A H 0.5772 0.6599 0.3973 0.023 Uiso 1 1 calc R . . H3B H 0.5177 0.7612 0.4386 0.023 Uiso 1 1 calc R . . C1 C 0.02176(11) 0.60008(14) 0.38891(10) 0.0137(3) Uani 1 1 d . . . C2 C 0.07383(11) 0.67280(15) 0.31820(10) 0.0147(3) Uani 1 1 d . . . H2A H 0.0935 0.6199 0.2699 0.018 Uiso 1 1 calc R . . H2B H 0.0271 0.7343 0.2957 0.018 Uiso 1 1 calc R . . C3 C 0.25390(12) 0.67608(14) 0.34684(9) 0.0135(3) Uani 1 1 d . . . H3 H 0.2593 0.6049 0.3139 0.016 Uiso 1 1 calc R . . C4 C 0.33883(11) 0.72330(14) 0.38589(10) 0.0135(3) Uani 1 1 d . . . C5 C 0.43536(12) 0.65566(15) 0.37045(10) 0.0149(3) Uani 1 1 d . . . C6 C 0.32907(12) 0.82737(15) 0.43378(10) 0.0154(3) Uani 1 1 d . . . H6 H 0.3862 0.8611 0.4616 0.019 Uiso 1 1 calc R . . C7 C 0.23557(12) 0.88171(14) 0.44076(10) 0.0168(3) Uani 1 1 d . . . H7 H 0.2283 0.9534 0.4729 0.020 Uiso 1 1 calc R . . C8 C 0.15323(12) 0.83122(14) 0.40092(10) 0.0157(3) Uani 1 1 d . . . H8 H 0.0888 0.8678 0.4058 0.019 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 0.0143(2) 0.0142(2) 0.0154(2) 0.00036(16) 0.00026(16) 0.00122(15) F1 0.0178(5) 0.0570(8) 0.0228(5) -0.0072(5) 0.0050(4) 0.0065(5) F2 0.0306(6) 0.0159(5) 0.0297(6) 0.0035(4) -0.0044(4) -0.0035(4) F3 0.0195(5) 0.0282(6) 0.0206(5) -0.0017(4) -0.0042(4) -0.0004(4) F4 0.0454(7) 0.0137(5) 0.0506(8) 0.0009(5) -0.0126(6) 0.0027(5) F5 0.0214(5) 0.0394(7) 0.0221(5) 0.0077(5) 0.0074(4) 0.0030(4) F6 0.0236(5) 0.0312(6) 0.0202(5) 0.0024(4) -0.0067(4) 0.0020(4) O1 0.0208(6) 0.0192(6) 0.0137(6) -0.0004(5) 0.0011(5) -0.0032(5) O2 0.0176(6) 0.0178(6) 0.0197(6) -0.0028(5) 0.0015(5) 0.0012(5) N1 0.0185(7) 0.0196(7) 0.0164(7) 0.0021(6) -0.0010(6) -0.0049(6) N2 0.0140(6) 0.0139(7) 0.0122(6) 0.0026(5) 0.0009(5) -0.0014(5) N3 0.0136(6) 0.0228(8) 0.0201(7) -0.0054(6) 0.0001(6) 0.0030(6) C1 0.0124(7) 0.0129(8) 0.0160(8) 0.0000(6) 0.0014(6) 0.0034(6) C2 0.0130(7) 0.0162(8) 0.0148(8) 0.0006(6) -0.0006(6) -0.0020(6) C3 0.0166(7) 0.0126(8) 0.0113(7) 0.0016(6) 0.0027(6) 0.0008(6) C4 0.0146(7) 0.0146(8) 0.0113(7) 0.0029(6) 0.0022(6) -0.0006(6) C5 0.0173(8) 0.0158(8) 0.0118(7) 0.0033(6) 0.0017(6) 0.0011(6) C6 0.0164(8) 0.0167(8) 0.0132(8) 0.0019(6) -0.0004(6) -0.0025(6) C7 0.0219(8) 0.0142(8) 0.0142(8) -0.0005(6) 0.0023(7) 0.0000(7) C8 0.0165(8) 0.0158(8) 0.0146(8) 0.0026(6) 0.0035(6) 0.0018(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 F4 1.5837(11) . ? P1 F1 1.5997(11) . ? P1 F5 1.5997(10) . ? P1 F6 1.6031(10) . ? P1 F2 1.6042(11) . ? P1 F3 1.6060(10) . ? O1 C1 1.2348(19) . ? O2 C5 1.233(2) . ? N1 C1 1.319(2) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 C3 1.343(2) . ? N2 C8 1.346(2) . ? N2 C2 1.4695(19) . ? N3 C5 1.328(2) . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? C1 C2 1.530(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.383(2) . ? C3 H3 0.9500 . ? C4 C6 1.389(2) . ? C4 C5 1.506(2) . ? C6 C7 1.384(2) . ? C6 H6 0.9500 . ? C7 C8 1.375(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? 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 F4 P1 F1 90.63(7) . . ? F4 P1 F5 90.52(6) . . ? F1 P1 F5 178.84(7) . . ? F4 P1 F6 90.20(6) . . ? F1 P1 F6 90.19(6) . . ? F5 P1 F6 89.96(6) . . ? F4 P1 F2 179.59(7) . . ? F1 P1 F2 89.78(6) . . ? F5 P1 F2 89.07(6) . . ? F6 P1 F2 89.78(5) . . ? F4 P1 F3 90.61(6) . . ? F1 P1 F3 89.88(6) . . ? F5 P1 F3 89.95(6) . . ? F6 P1 F3 179.19(6) . . ? F2 P1 F3 89.41(5) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C3 N2 C8 121.46(14) . . ? C3 N2 C2 119.19(13) . . ? C8 N2 C2 119.21(13) . . ? C5 N3 H3A 120.0 . . ? C5 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? O1 C1 N1 125.06(15) . . ? O1 C1 C2 119.84(14) . . ? N1 C1 C2 115.09(14) . . ? N2 C2 C1 108.63(12) . . ? N2 C2 H2A 110.0 . . ? C1 C2 H2A 110.0 . . ? N2 C2 H2B 110.0 . . ? C1 C2 H2B 110.0 . . ? H2A C2 H2B 108.3 . . ? N2 C3 C4 120.59(15) . . ? N2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C6 118.67(15) . . ? C3 C4 C5 115.39(14) . . ? C6 C4 C5 125.94(14) . . ? O2 C5 N3 123.05(15) . . ? O2 C5 C4 118.78(14) . . ? N3 C5 C4 118.16(14) . . ? C7 C6 C4 119.64(15) . . ? C7 C6 H6 120.2 . . ? C4 C6 H6 120.2 . . ? C8 C7 C6 119.57(15) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? N2 C8 C7 120.07(15) . . ? N2 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.323 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.051 # END data_838310 _database_code_depnum_ccdc_archive 'CCDC 838310' #TrackingRef '838304-10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H30 B N3 O2' _chemical_formula_weight 499.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_hall 'P 2c -2ac' 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 9.7596(3) _cell_length_b 15.6860(5) _cell_length_c 16.8530(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2580.01(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5354 _cell_measurement_theta_min 2.4581 _cell_measurement_theta_max 26.3225 _exptl_crystal_description Lump _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8916 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 20147 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 26.40 _reflns_number_total 5121 _reflns_number_gt 4724 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.34A (Bruker AXS, 2006)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0666P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(12) _refine_ls_number_reflns 5121 _refine_ls_number_parameters 343 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.1102 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _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 B1 B 0.8643(2) 0.74555(12) 0.25906(13) 0.0156(4) Uani 1 1 d . . . O1 O 0.07891(14) 0.55826(9) 0.92349(9) 0.0265(3) Uani 1 1 d . . . O2 O 0.26206(15) 0.97272(9) 0.90283(11) 0.0338(4) Uani 1 1 d . . . N1 N -0.14533(17) 0.52243(10) 0.91397(11) 0.0235(4) Uani 1 1 d . . . H1A H -0.1275 0.4702 0.8980 0.028 Uiso 1 1 calc R . . H1B H -0.2308 0.5393 0.9196 0.028 Uiso 1 1 calc R . . N2 N 0.02452(15) 0.72207(10) 0.97312(10) 0.0157(3) Uani 1 1 d . . . N3 N 0.03516(18) 0.97105(11) 0.87860(11) 0.0243(4) Uani 1 1 d . . . H3A H 0.0364 1.0213 0.8554 0.029 Uiso 1 1 calc R . . H3B H -0.0424 0.9429 0.8831 0.029 Uiso 1 1 calc R . . C1 C -0.04251(19) 0.57628(12) 0.92969(12) 0.0190(4) Uani 1 1 d . . . C2 C -0.09105(19) 0.66387(11) 0.95802(12) 0.0171(4) Uani 1 1 d . . . H2B H -0.1518 0.6892 0.9173 0.020 Uiso 1 1 calc R . . H2A H -0.1450 0.6570 1.0074 0.020 Uiso 1 1 calc R . . C3 C 0.03415(18) 0.79553(12) 0.93162(11) 0.0162(4) Uani 1 1 d . . . H3 H -0.0316 0.8084 0.8918 0.019 Uiso 1 1 calc R . . C4 C 0.13952(18) 0.85192(12) 0.94698(12) 0.0175(4) Uani 1 1 d . . . C5 C 0.15011(19) 0.93779(12) 0.90675(13) 0.0199(4) Uani 1 1 d . . . C6 C 0.2386(2) 0.82971(12) 1.00268(13) 0.0224(4) Uani 1 1 d . . . H6 H 0.3146 0.8662 1.0119 0.027 Uiso 1 1 calc R . . C7 C 0.2259(2) 0.75453(12) 1.04439(13) 0.0235(4) Uani 1 1 d . . . H7 H 0.2924 0.7394 1.0831 0.028 Uiso 1 1 calc R . . C8 C 0.1168(2) 0.70157(13) 1.02987(12) 0.0205(4) Uani 1 1 d . . . H8 H 0.1061 0.6506 1.0596 0.025 Uiso 1 1 calc R . . C9 C 0.69662(19) 0.75159(11) 0.24759(11) 0.0147(4) Uani 1 1 d . . . C10 C 0.6116(2) 0.67973(12) 0.25751(11) 0.0173(4) Uani 1 1 d . . . H10 H 0.6530 0.6262 0.2684 0.021 Uiso 1 1 calc R . . C11 C 0.4697(2) 0.68391(12) 0.25204(12) 0.0206(4) Uani 1 1 d . . . H11 H 0.4165 0.6338 0.2592 0.025 Uiso 1 1 calc R . . C12 C 0.4052(2) 0.76103(13) 0.23608(12) 0.0216(4) Uani 1 1 d . . . H12 H 0.3083 0.7639 0.2314 0.026 Uiso 1 1 calc R . . C13 C 0.4846(2) 0.83372(13) 0.22712(11) 0.0206(4) Uani 1 1 d . . . H13 H 0.4421 0.8870 0.2164 0.025 Uiso 1 1 calc R . . C14 C 0.6272(2) 0.82879(12) 0.23383(11) 0.0181(4) Uani 1 1 d . . . H14 H 0.6793 0.8797 0.2289 0.022 Uiso 1 1 calc R . . C15 C 0.94276(18) 0.82705(11) 0.21807(12) 0.0161(4) Uani 1 1 d . . . C16 C 0.9030(2) 0.85718(12) 0.14312(12) 0.0195(4) Uani 1 1 d . . . H16 H 0.8279 0.8306 0.1173 0.023 Uiso 1 1 calc R . . C17 C 0.9688(2) 0.92421(13) 0.10510(12) 0.0236(5) Uani 1 1 d . . . H17 H 0.9364 0.9439 0.0552 0.028 Uiso 1 1 calc R . . C18 C 1.0817(2) 0.96240(13) 0.13999(13) 0.0245(5) Uani 1 1 d . . . H18 H 1.1276 1.0080 0.1141 0.029 Uiso 1 1 calc R . . C19 C 1.1267(2) 0.93347(12) 0.21298(13) 0.0224(4) Uani 1 1 d . . . H19 H 1.2049 0.9587 0.2370 0.027 Uiso 1 1 calc R . . C20 C 1.0575(2) 0.86722(11) 0.25153(12) 0.0182(4) Uani 1 1 d . . . H20 H 1.0892 0.8488 0.3020 0.022 Uiso 1 1 calc R . . C21 C 0.93072(19) 0.66062(11) 0.21645(11) 0.0148(4) Uani 1 1 d . . . C22 C 1.06588(19) 0.63543(12) 0.23453(11) 0.0176(4) Uani 1 1 d . . . H22 H 1.1177 0.6688 0.2708 0.021 Uiso 1 1 calc R . . C23 C 1.1260(2) 0.56347(12) 0.20109(12) 0.0195(4) Uani 1 1 d . . . H23 H 1.2169 0.5481 0.2153 0.023 Uiso 1 1 calc R . . C24 C 1.0538(2) 0.51412(12) 0.14707(12) 0.0194(4) Uani 1 1 d . . . H24 H 1.0939 0.4644 0.1249 0.023 Uiso 1 1 calc R . . C25 C 0.9224(2) 0.53838(12) 0.12588(12) 0.0186(4) Uani 1 1 d . . . H25 H 0.8723 0.5059 0.0881 0.022 Uiso 1 1 calc R . . C26 C 0.86367(19) 0.61072(12) 0.16016(11) 0.0157(4) Uani 1 1 d . . . H26 H 0.7738 0.6267 0.1444 0.019 Uiso 1 1 calc R . . C27 C 0.88753(18) 0.74235(11) 0.35609(12) 0.0149(4) Uani 1 1 d . . . C28 C 0.92697(19) 0.66961(12) 0.39864(12) 0.0191(4) Uani 1 1 d . . . H28 H 0.9456 0.6186 0.3703 0.023 Uiso 1 1 calc R . . C29 C 0.93997(19) 0.66928(13) 0.48132(12) 0.0230(5) Uani 1 1 d . . . H29 H 0.9684 0.6189 0.5079 0.028 Uiso 1 1 calc R . . C30 C 0.9116(2) 0.74199(14) 0.52442(13) 0.0252(5) Uani 1 1 d . . . H30 H 0.9210 0.7421 0.5805 0.030 Uiso 1 1 calc R . . C31 C 0.8695(2) 0.81471(13) 0.48504(12) 0.0237(5) Uani 1 1 d . . . H31 H 0.8491 0.8650 0.5142 0.028 Uiso 1 1 calc R . . C32 C 0.85671(19) 0.81446(12) 0.40244(12) 0.0190(4) Uani 1 1 d . . . H32 H 0.8261 0.8648 0.3766 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 B1 0.0145(10) 0.0142(9) 0.0180(11) -0.0007(8) -0.0010(8) 0.0006(8) O1 0.0193(7) 0.0239(7) 0.0364(9) -0.0029(6) -0.0002(6) 0.0038(6) O2 0.0187(8) 0.0241(7) 0.0588(11) 0.0111(7) 0.0022(7) -0.0043(6) N1 0.0210(9) 0.0194(8) 0.0301(10) -0.0015(7) -0.0022(7) 0.0007(7) N2 0.0146(8) 0.0173(7) 0.0154(8) 0.0005(6) 0.0004(6) 0.0006(6) N3 0.0212(9) 0.0166(8) 0.0352(11) 0.0048(7) -0.0032(7) -0.0005(7) C1 0.0192(10) 0.0198(9) 0.0180(10) 0.0030(8) -0.0014(8) 0.0005(8) C2 0.0130(9) 0.0194(9) 0.0187(10) 0.0021(8) -0.0008(7) -0.0008(7) C3 0.0150(9) 0.0194(9) 0.0142(9) 0.0002(7) 0.0006(7) 0.0046(7) C4 0.0152(9) 0.0186(9) 0.0189(10) -0.0019(8) 0.0043(7) 0.0019(7) C5 0.0180(10) 0.0176(9) 0.0240(10) -0.0015(8) 0.0035(8) -0.0002(8) C6 0.0184(10) 0.0229(10) 0.0259(11) -0.0024(8) -0.0018(8) -0.0013(8) C7 0.0188(10) 0.0291(10) 0.0226(10) 0.0011(8) -0.0070(8) 0.0002(9) C8 0.0201(10) 0.0246(11) 0.0168(10) 0.0044(8) -0.0017(8) 0.0029(8) C9 0.0155(9) 0.0181(8) 0.0104(8) -0.0018(6) 0.0005(7) 0.0009(7) C10 0.0180(10) 0.0186(9) 0.0153(9) -0.0020(7) 0.0004(7) 0.0011(7) C11 0.0199(10) 0.0238(10) 0.0180(10) -0.0024(8) 0.0019(8) -0.0048(8) C12 0.0113(9) 0.0346(11) 0.0189(10) -0.0020(9) 0.0000(8) 0.0012(8) C13 0.0201(10) 0.0246(10) 0.0171(10) -0.0003(8) -0.0005(8) 0.0065(8) C14 0.0175(10) 0.0184(9) 0.0186(10) -0.0004(8) 0.0016(8) -0.0009(7) C15 0.0151(9) 0.0135(8) 0.0197(10) -0.0024(7) 0.0035(7) 0.0033(7) C16 0.0201(10) 0.0213(10) 0.0171(10) -0.0002(8) 0.0019(8) 0.0014(8) C17 0.0320(12) 0.0221(10) 0.0168(10) 0.0036(8) 0.0062(8) 0.0045(9) C18 0.0304(11) 0.0157(9) 0.0274(12) 0.0022(8) 0.0142(9) -0.0020(8) C19 0.0200(10) 0.0171(9) 0.0300(12) -0.0040(8) 0.0059(8) -0.0021(8) C20 0.0179(10) 0.0173(9) 0.0194(10) -0.0013(8) 0.0022(8) 0.0008(7) C21 0.0147(9) 0.0146(8) 0.0150(9) 0.0024(7) 0.0024(7) -0.0013(7) C22 0.0185(10) 0.0176(9) 0.0167(10) 0.0001(7) -0.0002(8) -0.0026(7) C23 0.0177(10) 0.0221(10) 0.0188(10) 0.0022(8) 0.0014(8) 0.0037(8) C24 0.0248(10) 0.0140(9) 0.0195(10) 0.0008(7) 0.0050(8) 0.0033(8) C25 0.0233(10) 0.0177(9) 0.0150(9) -0.0004(8) 0.0000(8) -0.0042(8) C26 0.0147(9) 0.0160(9) 0.0165(9) 0.0016(7) 0.0017(7) -0.0008(7) C27 0.0086(8) 0.0188(9) 0.0175(9) -0.0003(7) 0.0014(7) -0.0025(7) C28 0.0145(9) 0.0232(10) 0.0197(11) -0.0001(8) 0.0024(7) 0.0001(7) C29 0.0153(10) 0.0326(11) 0.0211(11) 0.0071(9) 0.0009(8) 0.0016(8) C30 0.0176(10) 0.0421(13) 0.0158(10) -0.0015(9) 0.0011(8) -0.0070(9) C31 0.0221(11) 0.0265(11) 0.0223(11) -0.0076(9) 0.0061(8) -0.0090(8) C32 0.0167(9) 0.0187(9) 0.0217(11) -0.0017(8) 0.0034(8) -0.0035(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 B1 C15 1.642(3) . ? B1 C21 1.646(3) . ? B1 C9 1.651(3) . ? B1 C27 1.652(3) . ? O1 C1 1.223(2) . ? O2 C5 1.224(2) . ? N1 C1 1.338(3) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 C3 1.351(2) . ? N2 C8 1.352(2) . ? N2 C2 1.473(2) . ? N3 C5 1.325(3) . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? C1 C2 1.530(3) . ? C2 H2B 0.9900 . ? C2 H2A 0.9900 . ? C3 C4 1.381(3) . ? C3 H3 0.9500 . ? C4 C6 1.392(3) . ? C4 C5 1.512(3) . ? C6 C7 1.379(3) . ? C6 H6 0.9500 . ? C7 C8 1.372(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C14 1.407(3) . ? C9 C10 1.410(3) . ? C10 C11 1.389(3) . ? C10 H10 0.9500 . ? C11 C12 1.390(3) . ? C11 H11 0.9500 . ? C12 C13 1.387(3) . ? C12 H12 0.9500 . ? C13 C14 1.398(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C20 1.403(3) . ? C15 C16 1.403(3) . ? C16 C17 1.388(3) . ? C16 H16 0.9500 . ? C17 C18 1.385(3) . ? C17 H17 0.9500 . ? C18 C19 1.383(3) . ? C18 H18 0.9500 . ? C19 C20 1.399(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C26 1.393(3) . ? C21 C22 1.410(3) . ? C22 C23 1.391(3) . ? C22 H22 0.9500 . ? C23 C24 1.387(3) . ? C23 H23 0.9500 . ? C24 C25 1.385(3) . ? C24 H24 0.9500 . ? C25 C26 1.396(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.402(3) . ? C27 C32 1.407(3) . ? C28 C29 1.399(3) . ? C28 H28 0.9500 . ? C29 C30 1.380(3) . ? C29 H29 0.9500 . ? C30 C31 1.383(3) . ? C30 H30 0.9500 . ? C31 C32 1.398(3) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? 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 C15 B1 C21 105.25(15) . . ? C15 B1 C9 111.60(15) . . ? C21 B1 C9 112.68(15) . . ? C15 B1 C27 112.10(15) . . ? C21 B1 C27 110.69(15) . . ? C9 B1 C27 104.69(15) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C3 N2 C8 121.50(16) . . ? C3 N2 C2 119.50(15) . . ? C8 N2 C2 118.98(16) . . ? C5 N3 H3A 120.0 . . ? C5 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? O1 C1 N1 124.33(18) . . ? O1 C1 C2 122.30(17) . . ? N1 C1 C2 113.36(16) . . ? N2 C2 C1 111.92(15) . . ? N2 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? N2 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? H2B C2 H2A 107.9 . . ? N2 C3 C4 120.07(17) . . ? N2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C6 118.91(17) . . ? C3 C4 C5 122.52(17) . . ? C6 C4 C5 118.56(17) . . ? O2 C5 N3 124.07(18) . . ? O2 C5 C4 118.95(17) . . ? N3 C5 C4 116.98(16) . . ? C7 C6 C4 119.70(18) . . ? C7 C6 H6 120.1 . . ? C4 C6 H6 120.2 . . ? C8 C7 C6 119.79(19) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? N2 C8 C7 119.91(19) . . ? N2 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C14 C9 C10 115.09(17) . . ? C14 C9 B1 123.11(16) . . ? C10 C9 B1 121.60(16) . . ? C11 C10 C9 122.77(18) . . ? C11 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? C10 C11 C12 120.37(18) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 118.89(18) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C12 C13 C14 120.14(18) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C9 122.71(18) . . ? C13 C14 H14 118.6 . . ? C9 C14 H14 118.6 . . ? C20 C15 C16 115.53(18) . . ? C20 C15 B1 123.54(18) . . ? C16 C15 B1 120.80(17) . . ? C17 C16 C15 122.87(19) . . ? C17 C16 H16 118.6 . . ? C15 C16 H16 118.6 . . ? C18 C17 C16 119.96(19) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C19 C18 C17 119.24(19) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 120.22(19) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C15 122.15(19) . . ? C19 C20 H20 118.9 . . ? C15 C20 H20 118.9 . . ? C26 C21 C22 115.41(17) . . ? C26 C21 B1 124.53(16) . . ? C22 C21 B1 120.04(16) . . ? C23 C22 C21 122.29(18) . . ? C23 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? C24 C23 C22 120.27(18) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C25 C24 C23 119.12(18) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C24 C25 C26 119.77(18) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C21 C26 C25 123.07(18) . . ? C21 C26 H26 118.5 . . ? C25 C26 H26 118.5 . . ? C28 C27 C32 115.40(18) . . ? C28 C27 B1 124.69(16) . . ? C32 C27 B1 119.73(16) . . ? C29 C28 C27 122.52(19) . . ? C29 C28 H28 118.7 . . ? C27 C28 H28 118.7 . . ? C30 C29 C28 120.19(19) . . ? C30 C29 H29 119.9 . . ? C28 C29 H29 119.9 . . ? C29 C30 C31 119.3(2) . . ? C29 C30 H30 120.4 . . ? C31 C30 H30 120.4 . . ? C30 C31 C32 120.15(19) . . ? C30 C31 H31 119.9 . . ? C32 C31 H31 119.9 . . ? C31 C32 C27 122.43(18) . . ? C31 C32 H32 118.8 . . ? C27 C32 H32 118.8 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.248 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.088