# Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Kwang Lee' _publ_contact_author_email KMLEE@NKNU.EDU.TW _publ_section_title ; Anion-Controlled Assemble of C-H---X Hydrogen Bonded Helical Tubes or Catemers by Crescent Imidazolium Salts ; loop_ _publ_author_name 'Kwang Lee' 'Jack C C Chen' 'Chao-June Huang' 'Ivan J. B. Lin' data_1 _database_code_depnum_ccdc_archive 'CCDC 153355' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Br N5 O' _chemical_formula_weight 284.13 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' 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 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 26.020(6) _cell_length_b 7.128(2) _cell_length_c 11.941(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.79(2) _cell_angle_gamma 90.00 _cell_volume 2175.5(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.63 _cell_measurement_theta_max 12.86 _exptl_crystal_description column _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.6 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.735 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 3.766 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6560 _exptl_absorpt_correction_T_max 0.9360 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 297 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.94 _diffrn_reflns_number 7247 _diffrn_reflns_av_R_equivalents 0.0624 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1908 _reflns_number_gt 1645 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'Bruker SHELXS' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0663P)^2^+2.7284P] 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 0.0036(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1908 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.1044 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.003 _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 0.071133(14) 0.18588(6) 0.57926(3) 0.0397(2) Uani 1 1 d . . . O1 O 0.13521(10) 0.7624(5) 0.7768(3) 0.0472(7) Uani 1 1 d . . . N1 N 0.15296(11) 0.6266(4) 0.4531(2) 0.0281(6) Uani 1 1 d . . . N2 N 0.09189(11) 0.6812(4) 0.5469(3) 0.0302(7) Uani 1 1 d . . . N3 N 0.23555(11) 0.5021(4) 0.5127(2) 0.0332(7) Uani 1 1 d . . . N4 N 0.20815(12) 0.6100(5) 0.3224(3) 0.0385(7) Uani 1 1 d . . . N5 N 0.05609(12) 0.7521(7) 0.8191(3) 0.0576(11) Uani 1 1 d . . . H9 H 0.0669 0.7801 0.8896 0.069 Uiso 1 1 calc R . . H10 H 0.0233 0.7330 0.7940 0.069 Uiso 1 1 calc R . . C1 C 0.13849(12) 0.6032(5) 0.5533(3) 0.0293(7) Uani 1 1 d . . . H1 H 0.1577 0.5429 0.6166 0.035 Uiso 1 1 calc R . . C2 C 0.11398(15) 0.7190(6) 0.3795(3) 0.0367(9) Uani 1 1 d . . . H2 H 0.1142 0.7518 0.3042 0.044 Uiso 1 1 calc R . . C3 C 0.07548(15) 0.7522(6) 0.4385(3) 0.0369(8) Uani 1 1 d . . . H3 H 0.0438 0.8117 0.4112 0.044 Uiso 1 1 calc R . . C4 C 0.20239(13) 0.5744(5) 0.4275(3) 0.0284(7) Uani 1 1 d . . . C5 C 0.25520(15) 0.5661(7) 0.3009(4) 0.0470(10) Uani 1 1 d . . . H4 H 0.2621 0.5884 0.2284 0.056 Uiso 1 1 calc R . . C6 C 0.29360(14) 0.4894(6) 0.3817(3) 0.0411(9) Uani 1 1 d . . . H5 H 0.3262 0.4595 0.3656 0.049 Uiso 1 1 calc R . . C7 C 0.28214(14) 0.4584(5) 0.4874(3) 0.0382(9) Uani 1 1 d . . . H6 H 0.3075 0.4052 0.5436 0.046 Uiso 1 1 calc R . . C8 C 0.06004(14) 0.6811(6) 0.6348(3) 0.0354(9) Uani 1 1 d . . . H7 H 0.0459 0.5562 0.6402 0.042 Uiso 1 1 calc R . . H8 H 0.0308 0.7659 0.6122 0.042 Uiso 1 1 calc R . . C9 C 0.08929(15) 0.7387(6) 0.7504(3) 0.0384(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 Br1 0.0394(3) 0.0467(3) 0.0316(3) -0.00371(15) 0.00343(17) 0.00364(16) O1 0.0263(14) 0.0747(19) 0.0407(17) -0.0085(14) 0.0063(12) -0.0054(13) N1 0.0228(14) 0.0354(15) 0.0261(15) -0.0022(12) 0.0048(12) 0.0026(12) N2 0.0238(14) 0.0378(16) 0.0301(16) -0.0038(12) 0.0076(13) 0.0024(12) N3 0.0275(14) 0.0403(17) 0.0321(17) 0.0048(13) 0.0058(12) 0.0020(13) N4 0.0317(16) 0.059(2) 0.0252(16) 0.0010(15) 0.0066(13) 0.0020(15) N5 0.0181(15) 0.133(3) 0.0246(18) -0.023(2) 0.0100(13) -0.0080(19) C1 0.0237(16) 0.0358(19) 0.0287(18) -0.0004(14) 0.0059(14) 0.0018(14) C2 0.0335(19) 0.047(2) 0.028(2) 0.0030(16) 0.0023(15) 0.0083(16) C3 0.0313(19) 0.047(2) 0.031(2) -0.0002(17) 0.0016(15) 0.0093(17) C4 0.0259(16) 0.0287(17) 0.0314(18) -0.0068(14) 0.0072(14) -0.0018(13) C5 0.041(2) 0.069(3) 0.034(2) -0.005(2) 0.0156(17) 0.001(2) C6 0.0287(18) 0.049(2) 0.048(2) -0.0072(18) 0.0129(17) 0.0004(16) C7 0.0284(18) 0.039(2) 0.046(2) 0.0029(17) 0.0049(16) 0.0030(16) C8 0.0248(17) 0.049(2) 0.035(2) -0.0021(16) 0.0116(16) 0.0001(15) C9 0.032(2) 0.047(2) 0.037(2) -0.0013(17) 0.0093(16) 0.0012(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 C9 1.189(5) . ? N1 C1 1.330(5) . ? N1 C2 1.379(5) . ? N1 C4 1.426(4) . ? N2 C1 1.323(5) . ? N2 C3 1.381(5) . ? N2 C8 1.454(5) . ? N3 C4 1.310(4) . ? N3 C7 1.340(5) . ? N4 C4 1.317(5) . ? N4 C5 1.334(5) . ? N5 C9 1.301(5) . ? C2 C3 1.349(6) . ? C5 C6 1.367(6) . ? C6 C7 1.368(6) . ? C8 C9 1.503(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 C1 N1 C2 109.5(3) . . ? C1 N1 C4 125.3(3) . . ? C2 N1 C4 125.0(3) . . ? C1 N2 C3 109.1(3) . . ? C1 N2 C8 126.8(3) . . ? C3 N2 C8 124.0(3) . . ? C4 N3 C7 114.1(3) . . ? C4 N4 C5 114.3(3) . . ? N2 C1 N1 107.8(3) . . ? C3 C2 N1 106.3(3) . . ? C2 C3 N2 107.2(3) . . ? N3 C4 N4 129.8(3) . . ? N3 C4 N1 115.2(3) . . ? N4 C4 N1 115.0(3) . . ? N4 C5 C6 122.2(4) . . ? C5 C6 C7 117.4(3) . . ? N3 C7 C6 122.2(4) . . ? N2 C8 C9 113.8(3) . . ? O1 C9 N5 125.1(4) . . ? O1 C9 C8 126.3(4) . . ? N5 C9 C8 108.5(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.606 _refine_diff_density_min -0.656 _refine_diff_density_rms 0.102 #=END data_2 _database_code_depnum_ccdc_archive 'CCDC 153356' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 F6 N5 O P' _chemical_formula_weight 349.19 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 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 12.9852(16) _cell_length_b 24.937(2) _cell_length_c 8.9006(12) _cell_angle_alpha 90.00 _cell_angle_beta 104.745(16) _cell_angle_gamma 90.00 _cell_volume 2787.2(6) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 21 _cell_measurement_theta_min 10.01 _cell_measurement_theta_max 12.92 _exptl_crystal_description column _exptl_crystal_colour white _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.664 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.275 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7837 _exptl_absorpt_correction_T_max 0.8638 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 397 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.94 _diffrn_reflns_number 11693 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4925 _reflns_number_gt 3701 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'Bruker SHELXS' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0583P)^2^+0.9559P] 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 0.0035(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4925 _refine_ls_number_parameters 508 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1181 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.106 _refine_ls_shift/su_mean 0.005 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.36291(5) 0.34843(3) 0.49575(8) 0.0564(2) Uani 1 1 d . . . P2 P 0.86570(5) 0.37355(3) 0.51170(7) 0.0536(2) Uani 1 1 d . . . F1' F 0.3423(13) 0.2861(4) 0.5001(19) 0.147(5) Uani 0.448(17) 1 d P A 1 F2' F 0.2448(9) 0.3568(9) 0.496(2) 0.164(6) Uani 0.448(17) 1 d P A 1 F3' F 0.3825(11) 0.4014(5) 0.5305(17) 0.206(7) Uani 0.448(17) 1 d P A 1 F4' F 0.3930(13) 0.3304(8) 0.6690(15) 0.145(6) Uani 0.448(17) 1 d P A 1 F5' F 0.4780(7) 0.3394(7) 0.4949(17) 0.130(5) Uani 0.448(17) 1 d P A 1 F6' F 0.3285(10) 0.3661(5) 0.3242(13) 0.118(4) Uani 0.448(17) 1 d P A 1 F7' F 0.8479(9) 0.3161(4) 0.4331(15) 0.121(2) Uani 0.61(2) 1 d P B 2 F8' F 0.8916(8) 0.4305(3) 0.5524(17) 0.160(4) Uani 0.61(2) 1 d P B 2 F9' F 0.7482(6) 0.3729(5) 0.5234(11) 0.098(3) Uani 0.61(2) 1 d P B 2 F10' F 0.8960(12) 0.3588(6) 0.6885(10) 0.117(4) Uani 0.61(2) 1 d P B 2 F11' F 0.8305(6) 0.3900(4) 0.3337(9) 0.089(2) Uani 0.61(2) 1 d P B 2 F12' F 0.9836(4) 0.3673(4) 0.5023(10) 0.082(2) Uani 0.61(2) 1 d P B 2 F1 F 0.3801(8) 0.2907(3) 0.4430(11) 0.120(3) Uani 0.552(17) 1 d P A 3 F2 F 0.2476(7) 0.3382(5) 0.5030(14) 0.115(3) Uani 0.552(17) 1 d P A 3 F3 F 0.3528(9) 0.4128(3) 0.5285(8) 0.118(3) Uani 0.552(17) 1 d P A 3 F4 F 0.4061(10) 0.3454(5) 0.6771(12) 0.106(3) Uani 0.552(17) 1 d P A 3 F5 F 0.4794(6) 0.3590(6) 0.4867(15) 0.135(4) Uani 0.552(17) 1 d P A 3 F6 F 0.3210(7) 0.3531(5) 0.3147(10) 0.122(4) Uani 0.552(17) 1 d P A 3 F7 F 0.8124(17) 0.3188(8) 0.474(2) 0.134(5) Uani 0.39(2) 1 d P B 4 F8 F 0.9041(7) 0.4283(5) 0.6058(19) 0.109(4) Uani 0.39(2) 1 d P B 4 F9 F 0.7497(12) 0.3992(11) 0.5135(18) 0.120(6) Uani 0.39(2) 1 d P B 4 F10 F 0.8922(19) 0.3422(10) 0.671(2) 0.125(6) Uani 0.39(2) 1 d P B 4 F11 F 0.8422(12) 0.4020(6) 0.3531(18) 0.105(5) Uani 0.39(2) 1 d P B 4 F12 F 0.9755(10) 0.3554(7) 0.5032(17) 0.105(4) Uani 0.39(2) 1 d P B 4 O1 O 0.66454(15) 0.28261(7) 0.04826(19) 0.0639(5) Uani 1 1 d . . . O2 O 1.10218(19) 0.21839(8) 0.5180(2) 0.0815(6) Uani 1 1 d . . . N1 N 0.41906(13) 0.39333(7) 0.0207(2) 0.0429(4) Uani 1 1 d . . . N2 N 0.52007(14) 0.33482(7) 0.1623(2) 0.0450(4) Uani 1 1 d . . . N3 N 0.24232(15) 0.38770(8) -0.1121(3) 0.0617(6) Uani 1 1 d . . . N4 N 0.34423(16) 0.46500(8) -0.1331(3) 0.0630(6) Uani 1 1 d . . . N5 N 0.68832(18) 0.21711(8) 0.2259(2) 0.0642(6) Uani 1 1 d . . . H10 H 0.7354 0.2010 0.1895 0.077 Uiso 1 1 calc R . . H9 H 0.6704 0.2041 0.3051 0.077 Uiso 1 1 calc R . . N6 N 0.88939(14) 0.09618(7) 0.5193(2) 0.0502(5) Uani 1 1 d . . . N7 N 0.98111(16) 0.15924(8) 0.6541(2) 0.0562(5) Uani 1 1 d . . . N8 N 0.71599(17) 0.09700(8) 0.3697(2) 0.0627(6) Uani 1 1 d . . . N9 N 0.82320(17) 0.01906(8) 0.3845(3) 0.0658(6) Uani 1 1 d . . . N10 N 1.15537(17) 0.27279(8) 0.7245(2) 0.0619(5) Uani 1 1 d . . . H20 H 1.2028 0.2885 0.6881 0.074 Uiso 1 1 calc R . . H19 H 1.1466 0.2821 0.8135 0.074 Uiso 1 1 calc R . . C1 C 0.42696(17) 0.34213(8) 0.0660(3) 0.0455(5) Uani 1 1 d . . . H1 H 0.3748 0.3160 0.0342 0.055 Uiso 1 1 calc R . . C2 C 0.51207(17) 0.41901(9) 0.0931(3) 0.0559(6) Uani 1 1 d . . . H2 H 0.5284 0.4549 0.0826 0.067 Uiso 1 1 calc R . . C3 C 0.57443(19) 0.38243(9) 0.1815(3) 0.0609(7) Uani 1 1 d . . . H3 H 0.6425 0.3882 0.2447 0.073 Uiso 1 1 calc R . . C4 C 0.32842(17) 0.41710(9) -0.0827(3) 0.0464(5) Uani 1 1 d . . . C5 C 0.1584(2) 0.41050(12) -0.2095(4) 0.0772(8) Uani 1 1 d . . . H6 H 0.0941 0.3920 -0.2347 0.093 Uiso 1 1 calc R . . C6 C 0.1631(2) 0.45961(12) -0.2733(4) 0.0823(9) Uani 1 1 d . . . H5 H 0.1041 0.4747 -0.3422 0.099 Uiso 1 1 calc R . . C7 C 0.2579(2) 0.48569(11) -0.2318(4) 0.0813(9) Uani 1 1 d . . . H4 H 0.2632 0.5194 -0.2738 0.098 Uiso 1 1 calc R . . C8 C 0.56198(19) 0.28435(9) 0.2354(3) 0.0513(6) Uani 1 1 d . . . H8 H 0.5041 0.2589 0.2261 0.062 Uiso 1 1 calc R . . H7 H 0.5939 0.2903 0.3451 0.062 Uiso 1 1 calc R . . C9 C 0.64400(17) 0.26134(8) 0.1608(2) 0.0443(5) Uani 1 1 d . . . C10 C 0.8887(2) 0.14772(9) 0.5606(3) 0.0519(6) Uani 1 1 d . . . H11 H 0.8320 0.1714 0.5282 0.062 Uiso 1 1 calc R . . C11 C 0.9869(2) 0.07515(11) 0.5926(3) 0.0712(8) Uani 1 1 d . . . H12 H 1.0095 0.0401 0.5852 0.085 Uiso 1 1 calc R . . C12 C 1.0432(2) 0.11453(11) 0.6763(4) 0.0767(8) Uani 1 1 d . . . H13 H 1.1123 0.1119 0.7386 0.092 Uiso 1 1 calc R . . C13 C 0.80322(19) 0.06886(9) 0.4173(3) 0.0505(5) Uani 1 1 d . . . C14 C 0.6363(2) 0.07094(13) 0.2722(4) 0.0773(8) Uani 1 1 d . . . H16 H 0.5719 0.0886 0.2336 0.093 Uiso 1 1 calc R . . C15 C 0.6463(2) 0.01918(13) 0.2273(4) 0.0806(9) Uani 1 1 d . . . H15 H 0.5905 0.0014 0.1592 0.097 Uiso 1 1 calc R . . C16 C 0.7409(3) -0.00500(12) 0.2863(4) 0.0810(9) Uani 1 1 d . . . H14 H 0.7494 -0.0402 0.2573 0.097 Uiso 1 1 calc R . . C17 C 1.0158(2) 0.21153(10) 0.7208(3) 0.0635(7) Uani 1 1 d . . . H17 H 1.0469 0.2079 0.8316 0.076 Uiso 1 1 calc R . . H18 H 0.9551 0.2354 0.7056 0.076 Uiso 1 1 calc R . . C18 C 1.0967(2) 0.23479(9) 0.6447(3) 0.0527(6) 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 P1 0.0498(4) 0.0650(4) 0.0551(4) 0.0019(3) 0.0146(3) 0.0016(3) P2 0.0407(3) 0.0718(4) 0.0462(4) 0.0027(3) 0.0070(3) -0.0008(3) F1' 0.163(9) 0.073(4) 0.170(11) 0.009(5) -0.023(7) -0.040(5) F2' 0.060(6) 0.281(17) 0.154(8) 0.053(10) 0.033(6) 0.070(8) F3' 0.149(8) 0.056(5) 0.361(18) -0.041(6) -0.029(8) 0.022(5) F4' 0.139(10) 0.215(12) 0.083(8) 0.078(8) 0.033(6) 0.079(9) F5' 0.068(6) 0.220(11) 0.105(6) 0.000(7) 0.030(5) 0.075(8) F6' 0.152(9) 0.130(6) 0.085(7) 0.058(5) 0.054(6) 0.079(6) F7' 0.127(5) 0.087(3) 0.163(6) -0.044(4) 0.063(4) -0.042(3) F8' 0.248(10) 0.074(4) 0.133(7) -0.026(4) 0.003(5) -0.017(4) F9' 0.041(2) 0.171(7) 0.084(3) 0.042(4) 0.0189(19) 0.012(4) F10' 0.089(4) 0.215(11) 0.040(3) 0.013(5) 0.007(3) 0.019(6) F11' 0.050(2) 0.172(7) 0.045(2) 0.007(3) 0.0110(16) 0.019(3) F12' 0.035(2) 0.143(5) 0.063(3) 0.000(3) 0.002(2) -0.012(3) F1 0.156(6) 0.061(3) 0.158(5) -0.016(3) 0.066(4) 0.014(3) F2 0.072(5) 0.172(7) 0.111(5) 0.021(4) 0.041(4) -0.046(6) F3 0.197(7) 0.054(3) 0.114(4) -0.002(2) 0.060(4) 0.047(3) F4 0.114(5) 0.144(5) 0.057(4) -0.022(4) 0.015(3) -0.018(4) F5 0.074(5) 0.228(9) 0.111(6) -0.066(6) 0.037(4) -0.069(6) F6 0.076(4) 0.232(9) 0.050(4) -0.018(4) 0.003(3) -0.009(5) F7 0.140(12) 0.124(9) 0.143(10) -0.017(6) 0.043(6) -0.080(9) F8 0.074(5) 0.133(8) 0.119(7) -0.083(6) 0.023(4) -0.002(4) F9 0.070(5) 0.222(15) 0.068(5) 0.008(8) 0.016(4) 0.070(8) F10 0.089(6) 0.169(11) 0.117(12) 0.093(9) 0.029(9) 0.015(7) F11 0.116(8) 0.097(6) 0.106(9) 0.069(6) 0.033(6) 0.047(5) F12 0.107(8) 0.133(7) 0.076(6) 0.004(5) 0.025(6) 0.086(7) O1 0.0945(13) 0.0550(10) 0.0496(10) 0.0066(8) 0.0320(9) 0.0083(9) O2 0.1345(18) 0.0700(12) 0.0503(11) -0.0075(9) 0.0423(11) -0.0108(12) N1 0.0394(9) 0.0381(9) 0.0471(10) -0.0003(8) 0.0032(8) -0.0011(7) N2 0.0463(10) 0.0411(10) 0.0458(10) 0.0057(8) 0.0082(8) 0.0036(8) N3 0.0465(11) 0.0570(12) 0.0710(14) -0.0041(10) -0.0045(10) -0.0051(9) N4 0.0590(12) 0.0425(11) 0.0734(14) 0.0061(10) -0.0089(11) 0.0002(9) N5 0.0813(15) 0.0596(13) 0.0579(13) 0.0153(10) 0.0290(11) 0.0250(11) N6 0.0542(11) 0.0451(10) 0.0494(11) -0.0046(8) 0.0097(9) 0.0028(8) N7 0.0611(12) 0.0493(11) 0.0602(12) -0.0116(10) 0.0193(10) -0.0040(9) N8 0.0606(13) 0.0597(13) 0.0620(13) 0.0027(10) 0.0049(10) 0.0082(10) N9 0.0684(13) 0.0485(12) 0.0724(14) -0.0089(10) 0.0031(11) 0.0016(10) N10 0.0779(14) 0.0620(13) 0.0509(12) -0.0036(10) 0.0258(11) -0.0154(11) C1 0.0484(12) 0.0387(11) 0.0475(12) -0.0011(9) 0.0085(10) -0.0026(9) C2 0.0473(13) 0.0396(12) 0.0699(16) 0.0032(11) -0.0049(11) -0.0051(10) C3 0.0460(13) 0.0498(13) 0.0746(17) 0.0023(12) -0.0074(12) -0.0031(11) C4 0.0448(12) 0.0424(12) 0.0463(12) -0.0063(10) 0.0010(10) 0.0040(9) C5 0.0496(15) 0.0768(19) 0.089(2) -0.0129(16) -0.0121(14) -0.0006(13) C6 0.0681(18) 0.0702(19) 0.085(2) -0.0085(16) -0.0241(15) 0.0202(15) C7 0.083(2) 0.0499(15) 0.087(2) 0.0087(14) -0.0218(17) 0.0099(14) C8 0.0599(14) 0.0467(12) 0.0480(13) 0.0120(10) 0.0153(11) 0.0099(10) C9 0.0560(13) 0.0401(11) 0.0354(11) -0.0037(9) 0.0091(10) -0.0014(10) C10 0.0620(15) 0.0442(12) 0.0509(13) -0.0010(10) 0.0171(12) 0.0030(11) C11 0.0615(16) 0.0540(15) 0.088(2) -0.0162(14) 0.0010(14) 0.0157(12) C12 0.0594(16) 0.0667(17) 0.094(2) -0.0220(16) 0.0010(15) 0.0070(13) C13 0.0586(14) 0.0488(13) 0.0434(12) 0.0013(10) 0.0115(11) 0.0016(11) C14 0.0621(17) 0.086(2) 0.0733(19) 0.0109(16) -0.0023(14) 0.0065(15) C15 0.078(2) 0.078(2) 0.0724(19) -0.0028(16) -0.0048(16) -0.0171(16) C16 0.090(2) 0.0552(16) 0.085(2) -0.0124(15) 0.0001(17) -0.0053(15) C17 0.0792(17) 0.0541(14) 0.0628(16) -0.0179(12) 0.0282(14) -0.0126(13) C18 0.0722(16) 0.0457(13) 0.0419(13) 0.0055(10) 0.0177(11) 0.0057(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 P1 F3' 1.365(11) . ? P1 F5' 1.514(9) . ? P1 F2 1.537(8) . ? P1 F6' 1.542(10) . ? P1 F1 1.548(7) . ? P1 F2' 1.549(12) . ? P1 F5 1.557(9) . ? P1 F4' 1.558(13) . ? P1 F6 1.569(8) . ? P1 F4 1.570(10) . ? P1 F1' 1.578(9) . ? P1 F3 1.642(7) . ? P2 F8' 1.482(8) . ? P2 F12 1.516(10) . ? P2 F7 1.528(14) . ? P2 F11 1.540(11) . ? P2 F9' 1.556(8) . ? P2 F12' 1.562(6) . ? P2 F10' 1.565(9) . ? P2 F10 1.577(16) . ? P2 F11' 1.587(7) . ? P2 F7' 1.586(9) . ? P2 F8 1.613(11) . ? P2 F9 1.641(13) . ? O1 C9 1.221(3) . ? O2 C18 1.219(3) . ? N1 C1 1.335(3) . ? N1 C2 1.374(3) . ? N1 C4 1.426(3) . ? N2 C1 1.305(3) . ? N2 C3 1.370(3) . ? N2 C8 1.457(3) . ? N3 C4 1.307(3) . ? N3 C5 1.335(3) . ? N4 C4 1.310(3) . ? N4 C7 1.339(3) . ? N5 C9 1.309(3) . ? N6 C10 1.337(3) . ? N6 C11 1.373(3) . ? N6 C13 1.423(3) . ? N7 C10 1.307(3) . ? N7 C12 1.360(3) . ? N7 C17 1.456(3) . ? N8 C13 1.308(3) . ? N8 C14 1.338(3) . ? N9 C13 1.316(3) . ? N9 C16 1.338(3) . ? N10 C18 1.307(3) . ? C2 C3 1.335(3) . ? C5 C6 1.358(4) . ? C6 C7 1.358(4) . ? C8 C9 1.505(3) . ? C11 C12 1.332(4) . ? C14 C15 1.367(4) . ? C15 C16 1.349(4) . ? C17 C18 1.504(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 F3' P1 F5' 91.0(7) . . ? F3' P1 F2 106.2(7) . . ? F5' P1 F2 161.7(7) . . ? F3' P1 F6' 86.5(8) . . ? F5' P1 F6' 94.3(8) . . ? F2 P1 F6' 92.8(7) . . ? F3' P1 F1 159.3(6) . . ? F5' P1 F1 69.0(6) . . ? F2 P1 F1 94.3(5) . . ? F6' P1 F1 89.6(6) . . ? F3' P1 F2' 89.8(8) . . ? F5' P1 F2' 179.1(8) . . ? F2 P1 F2' 17.4(10) . . ? F6' P1 F2' 85.8(8) . . ? F1 P1 F2' 110.2(8) . . ? F3' P1 F5 73.8(7) . . ? F5' P1 F5 18.5(8) . . ? F2 P1 F5 179.5(7) . . ? F6' P1 F5 86.6(7) . . ? F1 P1 F5 85.7(5) . . ? F2' P1 F5 162.4(8) . . ? F3' P1 F4' 94.0(10) . . ? F5' P1 F4' 87.9(8) . . ? F2 P1 F4' 84.9(8) . . ? F6' P1 F4' 177.8(8) . . ? F1 P1 F4' 90.7(9) . . ? F2' P1 F4' 92.0(9) . . ? F5 P1 F4' 95.6(8) . . ? F3' P1 F6 99.0(7) . . ? F5' P1 F6 95.2(7) . . ? F2 P1 F6 88.2(6) . . ? F6' P1 F6 12.6(8) . . ? F1 P1 F6 78.3(6) . . ? F2' P1 F6 84.8(8) . . ? F5 P1 F6 91.3(6) . . ? F4' P1 F6 166.6(8) . . ? F3' P1 F4 79.4(7) . . ? F5' P1 F4 84.4(8) . . ? F2 P1 F4 92.6(7) . . ? F6' P1 F4 165.8(6) . . ? F1 P1 F4 103.0(6) . . ? F2' P1 F4 95.6(8) . . ? F5 P1 F4 87.9(7) . . ? F4' P1 F4 15.0(10) . . ? F6 P1 F4 178.4(6) . . ? F3' P1 F1' 165.7(8) . . ? F5' P1 F1' 91.6(7) . . ? F2 P1 F1' 70.3(7) . . ? F6' P1 F1' 107.3(9) . . ? F1 P1 F1' 29.6(6) . . ? F2' P1 F1' 87.6(7) . . ? F5 P1 F1' 109.9(6) . . ? F4' P1 F1' 72.1(12) . . ? F6 P1 F1' 94.7(8) . . ? F4 P1 F1' 86.9(7) . . ? F3' P1 F3 14.8(8) . . ? F5' P1 F3 105.7(6) . . ? F2 P1 F3 91.9(5) . . ? F6' P1 F3 83.1(5) . . ? F1 P1 F3 170.7(4) . . ? F2' P1 F3 75.2(8) . . ? F5 P1 F3 88.1(5) . . ? F4' P1 F3 96.8(7) . . ? F6 P1 F3 95.0(5) . . ? F4 P1 F3 83.6(5) . . ? F1' P1 F3 159.4(8) . . ? F8' P2 F12 98.1(7) . . ? F8' P2 F7 166.0(10) . . ? F12 P2 F7 95.8(8) . . ? F8' P2 F11 76.2(7) . . ? F12 P2 F11 93.5(8) . . ? F7 P2 F11 103.8(11) . . ? F8' P2 F9' 99.1(6) . . ? F12 P2 F9' 162.0(6) . . ? F7 P2 F9' 66.9(8) . . ? F11 P2 F9' 95.5(6) . . ? F8' P2 F12' 86.9(5) . . ? F12 P2 F12' 11.7(8) . . ? F7 P2 F12' 107.1(9) . . ? F11 P2 F12' 88.0(6) . . ? F9' P2 F12' 173.6(4) . . ? F8' P2 F10' 89.8(6) . . ? F12 P2 F10' 88.9(8) . . ? F7 P2 F10' 89.6(10) . . ? F11 P2 F10' 166.0(8) . . ? F9' P2 F10' 86.0(7) . . ? F12' P2 F10' 91.8(7) . . ? F8' P2 F10 105.7(8) . . ? F12 P2 F10 84.5(11) . . ? F7 P2 F10 74.7(12) . . ? F11 P2 F10 177.4(10) . . ? F9' P2 F10 85.9(9) . . ? F12' P2 F10 90.3(10) . . ? F10' P2 F10 16.1(12) . . ? F8' P2 F11' 89.2(5) . . ? F12 P2 F11' 93.6(6) . . ? F7 P2 F11' 90.8(8) . . ? F11 P2 F11' 13.1(9) . . ? F9' P2 F11' 91.8(4) . . ? F12' P2 F11' 90.6(4) . . ? F10' P2 F11' 177.4(6) . . ? F10 P2 F11' 165.1(9) . . ? F8' P2 F7' 166.4(8) . . ? F12 P2 F7' 75.0(6) . . ? F7 P2 F7' 24.4(6) . . ? F11 P2 F7' 92.3(10) . . ? F9' P2 F7' 89.1(4) . . ? F12' P2 F7' 85.5(4) . . ? F10' P2 F7' 101.7(8) . . ? F10 P2 F7' 85.6(12) . . ? F11' P2 F7' 79.7(7) . . ? F8' P2 F8 16.6(8) . . ? F12 P2 F8 96.3(7) . . ? F7 P2 F8 158.8(12) . . ? F11 P2 F8 92.8(8) . . ? F9' P2 F8 98.8(6) . . ? F12' P2 F8 86.3(4) . . ? F10' P2 F8 73.2(7) . . ? F10 P2 F8 89.1(9) . . ? F11' P2 F8 105.8(6) . . ? F7' P2 F8 170.1(6) . . ? F8' P2 F9 77.0(10) . . ? F12 P2 F9 174.1(9) . . ? F7 P2 F9 89.1(8) . . ? F11 P2 F9 82.0(9) . . ? F9' P2 F9 23.7(8) . . ? F12' P2 F9 162.7(9) . . ? F10' P2 F9 94.5(9) . . ? F10 P2 F9 100.1(13) . . ? F11' P2 F9 83.0(7) . . ? F7' P2 F9 109.0(8) . . ? F8 P2 F9 80.1(8) . . ? C1 N1 C2 108.26(17) . . ? C1 N1 C4 125.45(18) . . ? C2 N1 C4 126.28(18) . . ? C1 N2 C3 108.83(18) . . ? C1 N2 C8 126.34(19) . . ? C3 N2 C8 124.82(19) . . ? C4 N3 C5 114.0(2) . . ? C4 N4 C7 113.4(2) . . ? C10 N6 C11 107.9(2) . . ? C10 N6 C13 125.2(2) . . ? C11 N6 C13 126.95(19) . . ? C10 N7 C12 109.1(2) . . ? C10 N7 C17 126.5(2) . . ? C12 N7 C17 124.4(2) . . ? C13 N8 C14 114.4(2) . . ? C13 N9 C16 113.5(2) . . ? N2 C1 N1 108.62(18) . . ? C3 C2 N1 106.7(2) . . ? C2 C3 N2 107.6(2) . . ? N3 C4 N4 130.1(2) . . ? N3 C4 N1 114.8(2) . . ? N4 C4 N1 115.11(19) . . ? N3 C5 C6 122.7(3) . . ? C5 C6 C7 116.9(2) . . ? N4 C7 C6 122.9(3) . . ? N2 C8 C9 110.96(18) . . ? O1 C9 N5 124.5(2) . . ? O1 C9 C8 121.55(19) . . ? N5 C9 C8 113.98(19) . . ? N7 C10 N6 108.5(2) . . ? C12 C11 N6 107.0(2) . . ? C11 C12 N7 107.6(2) . . ? N8 C13 N9 129.6(2) . . ? N8 C13 N6 115.2(2) . . ? N9 C13 N6 115.2(2) . . ? N8 C14 C15 122.2(3) . . ? C16 C15 C14 117.0(3) . . ? N9 C16 C15 123.4(3) . . ? N7 C17 C18 109.9(2) . . ? O2 C18 N10 125.7(2) . . ? O2 C18 C17 120.0(2) . . ? N10 C18 C17 114.3(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.291 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.041 # END data_2 _database_code_depnum_ccdc_archive 'CCDC 713462' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 N6 O4' _chemical_formula_weight 266.23 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 13.8870(4) _cell_length_b 7.1595(2) _cell_length_c 11.3891(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.5050(10) _cell_angle_gamma 90.00 _cell_volume 1116.80(6) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14511 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2764 _reflns_number_gt 2339 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0595P)^2^+0.2009P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2764 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1114 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.005 _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 0.32278(7) 0.14020(13) -0.04014(8) 0.0281(2) Uani 1 1 d . . . N2 N 0.20594(7) 0.11956(13) 0.06221(8) 0.0302(2) Uani 1 1 d . . . N4 N 0.42971(7) 0.11449(15) -0.17605(8) 0.0353(2) Uani 1 1 d . . . N3 N 0.47769(7) 0.26620(15) 0.01100(9) 0.0345(2) Uani 1 1 d . . . C9 C 0.20208(8) 0.03659(16) 0.27204(10) 0.0299(2) Uani 1 1 d . . . C6 C 0.59150(9) 0.23300(18) -0.12262(11) 0.0373(3) Uani 1 1 d . . . C1 C 0.29372(8) 0.19086(16) 0.06177(10) 0.0301(2) Uani 1 1 d . . . C5 C 0.52004(9) 0.1424(2) -0.20014(11) 0.0383(3) Uani 1 1 d . . . C7 C 0.56678(9) 0.29457(18) -0.01692(12) 0.0372(3) Uani 1 1 d . . . C3 C 0.17762(9) 0.02081(18) -0.04182(10) 0.0347(3) Uani 1 1 d . . . C2 C 0.25001(9) 0.03291(17) -0.10612(10) 0.0332(3) Uani 1 1 d . . . C8 C 0.15040(8) 0.13417(19) 0.15987(10) 0.0343(3) Uani 1 1 d . . . N6 N 0.90877(7) 0.13767(15) 0.37827(9) 0.0360(2) Uani 1 1 d . . . O4 O 0.82199(7) 0.11557(18) 0.39251(9) 0.0555(3) Uani 1 1 d . . . O3 O 0.93648(7) 0.06481(18) 0.29050(9) 0.0555(3) Uani 1 1 d . . . O2 O 0.96687(8) 0.22535(18) 0.45234(11) 0.0636(3) Uani 1 1 d . . . O1 O 0.29028(6) 0.00897(14) 0.28775(8) 0.0419(2) Uani 1 1 d . . . N5 N 0.14433(9) -0.00367(19) 0.34928(11) 0.0472(3) Uani 1 1 d . . . H8 H 0.0875(13) 0.081(2) 0.1314(15) 0.050(4) Uiso 1 1 d . . . H9 H 0.1667(13) -0.051(3) 0.4192(18) 0.061(5) Uiso 1 1 d . . . C4 C 0.41640(8) 0.17828(15) -0.07087(9) 0.0276(2) Uani 1 1 d . . . H1 H 0.3276(11) 0.264(2) 0.1191(13) 0.040(4) Uiso 1 1 d . . . H7 H 0.1444(11) 0.262(2) 0.1763(13) 0.045(4) Uiso 1 1 d . . . H5 H 0.6536(12) 0.246(2) -0.1409(13) 0.046(4) Uiso 1 1 d . . . H2 H 0.2565(11) -0.019(2) -0.1815(15) 0.045(4) Uiso 1 1 d . . . H3 H 0.1166(12) -0.044(2) -0.0576(14) 0.049(4) Uiso 1 1 d . . . H4 H 0.5302(12) 0.094(2) -0.2740(15) 0.054(5) Uiso 1 1 d . . . H6 H 0.6133(12) 0.354(2) 0.0397(15) 0.050(4) Uiso 1 1 d . . . H10 H 0.0806(15) 0.016(2) 0.3302(16) 0.057(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0259(4) 0.0327(5) 0.0255(4) 0.0021(3) 0.0039(3) -0.0012(4) N2 0.0253(4) 0.0385(5) 0.0270(4) 0.0021(4) 0.0046(3) -0.0004(4) N4 0.0314(5) 0.0465(6) 0.0283(5) -0.0013(4) 0.0058(4) 0.0000(4) N3 0.0296(5) 0.0398(5) 0.0342(5) -0.0046(4) 0.0058(4) -0.0024(4) C9 0.0276(5) 0.0340(5) 0.0289(5) -0.0032(4) 0.0072(4) 0.0005(4) C6 0.0275(6) 0.0418(6) 0.0441(6) 0.0065(5) 0.0105(5) 0.0019(5) C1 0.0272(5) 0.0357(6) 0.0274(5) -0.0005(4) 0.0042(4) -0.0012(4) C5 0.0343(6) 0.0507(7) 0.0315(6) 0.0025(5) 0.0105(5) 0.0044(5) C7 0.0285(6) 0.0380(6) 0.0442(6) -0.0030(5) 0.0036(5) -0.0028(5) C3 0.0297(6) 0.0437(6) 0.0296(5) 0.0003(4) 0.0024(4) -0.0055(5) C2 0.0312(6) 0.0406(6) 0.0269(5) -0.0016(4) 0.0020(4) -0.0044(5) C8 0.0248(5) 0.0475(7) 0.0318(6) 0.0015(5) 0.0083(4) 0.0048(5) N6 0.0330(5) 0.0404(5) 0.0344(5) 0.0002(4) 0.0049(4) 0.0049(4) O4 0.0310(5) 0.0865(8) 0.0501(6) -0.0033(5) 0.0100(4) 0.0056(5) O3 0.0427(6) 0.0859(8) 0.0395(5) -0.0153(5) 0.0115(4) -0.0030(5) O2 0.0466(6) 0.0716(7) 0.0701(7) -0.0343(6) 0.0027(5) -0.0042(5) O1 0.0276(4) 0.0622(6) 0.0365(5) 0.0059(4) 0.0068(3) 0.0080(4) N5 0.0340(6) 0.0724(8) 0.0383(6) 0.0132(5) 0.0146(5) 0.0043(5) C4 0.0265(5) 0.0294(5) 0.0268(5) 0.0038(4) 0.0046(4) 0.0020(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 1.3401(14) . ? N1 C2 1.3875(14) . ? N1 C4 1.4275(13) . ? N2 C1 1.3224(14) . ? N2 C3 1.3800(15) . ? N2 C8 1.4582(14) . ? N4 C4 1.3231(14) . ? N4 C5 1.3426(15) . ? N3 C4 1.3145(15) . ? N3 C7 1.3428(15) . ? C9 O1 1.2244(14) . ? C9 N5 1.3164(15) . ? C9 C8 1.5272(16) . ? C6 C5 1.3768(19) . ? C6 C7 1.3775(18) . ? C3 C2 1.3407(17) . ? N6 O2 1.2377(14) . ? N6 O3 1.2436(14) . ? N6 O4 1.2522(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 N1 C2 108.81(9) . . ? C1 N1 C4 125.26(9) . . ? C2 N1 C4 125.75(9) . . ? C1 N2 C3 109.06(9) . . ? C1 N2 C8 125.40(10) . . ? C3 N2 C8 125.45(10) . . ? C4 N4 C5 114.11(10) . . ? C4 N3 C7 114.73(10) . . ? O1 C9 N5 124.90(12) . . ? O1 C9 C8 121.11(10) . . ? N5 C9 C8 113.90(10) . . ? C5 C6 C7 117.00(11) . . ? N2 C1 N1 107.96(10) . . ? N4 C5 C6 122.54(11) . . ? N3 C7 C6 122.06(11) . . ? C2 C3 N2 107.63(10) . . ? C3 C2 N1 106.54(10) . . ? N2 C8 C9 111.75(9) . . ? O2 N6 O3 120.47(11) . . ? O2 N6 O4 120.58(11) . . ? O3 N6 O4 118.90(11) . . ? N3 C4 N4 129.54(10) . . ? N3 C4 N1 115.26(9) . . ? N4 C4 N1 115.16(10) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.191 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.055 # END data_4 _database_code_depnum_ccdc_archive 'CCDC 713463' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 B F4 N5 O' _chemical_formula_weight 291.03 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' 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 15.0019(17) _cell_length_b 5.3086(6) _cell_length_c 15.7979(17) _cell_angle_alpha 90.00 _cell_angle_beta 112.159(2) _cell_angle_gamma 90.00 _cell_volume 1165.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2192 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 27.87 _exptl_crystal_description Columnar _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.80859 _exptl_absorpt_correction_T_max 0.96853 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8149 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2870 _reflns_number_gt 2235 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0509P)^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 2870 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1008 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.976 _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 0.28961(7) 0.06646(17) 0.41459(7) 0.0290(3) Uani 1 1 d . . . F2 F 0.37376(6) 0.42615(18) 0.41916(7) 0.0272(3) Uani 1 1 d . . . F3 F 0.24997(7) 0.42358(18) 0.47015(6) 0.0275(3) Uani 1 1 d . . . F4 F 0.21915(7) 0.3874(2) 0.31844(6) 0.0324(3) Uani 1 1 d . . . O1 O -0.43784(8) -0.2112(2) 0.31990(8) 0.0241(3) Uani 1 1 d . . . N3 N -0.06603(9) -0.1967(2) 0.41519(8) 0.0165(3) Uani 1 1 d . . . N4 N -0.04049(9) 0.1515(2) 0.33072(9) 0.0176(3) Uani 1 1 d . . . N1 N -0.18078(8) 0.1236(2) 0.35773(8) 0.0138(3) Uani 1 1 d . . . N2 N -0.31682(9) 0.1986(2) 0.36913(8) 0.0149(3) Uani 1 1 d . . . N5 N -0.53185(9) -0.0674(3) 0.39216(9) 0.0199(3) Uani 1 1 d . . . H9 H -0.5694 -0.2010 0.3778 0.024 Uiso 1 1 calc R . . H10 H -0.5430 0.0547 0.4245 0.024 Uiso 1 1 calc R . . B1 B 0.28289(12) 0.3273(3) 0.40527(12) 0.0177(4) Uani 1 1 d . . . C7 C 0.02047(11) -0.2874(3) 0.42274(10) 0.0184(3) Uani 1 1 d . . . H6 H 0.0424 -0.4402 0.4552 0.022 Uiso 1 1 calc R . . C6 C 0.07870(11) -0.1679(3) 0.38535(10) 0.0193(3) Uani 1 1 d . . . H5 H 0.1392 -0.2359 0.3907 0.023 Uiso 1 1 calc R . . C5 C 0.04481(11) 0.0549(3) 0.33987(10) 0.0192(3) Uani 1 1 d . . . H4 H 0.0836 0.1430 0.3141 0.023 Uiso 1 1 calc R . . C4 C -0.08972(10) 0.0157(3) 0.36865(10) 0.0143(3) Uani 1 1 d . . . C2 C -0.21871(11) 0.3357(3) 0.30576(10) 0.0171(3) Uani 1 1 d . . . H2 H -0.1903 0.4303 0.2714 0.021 Uiso 1 1 calc R . . C3 C -0.30307(11) 0.3818(3) 0.31328(10) 0.0171(3) Uani 1 1 d . . . H3 H -0.3458 0.5163 0.2852 0.020 Uiso 1 1 calc R . . C1 C -0.24230(10) 0.0421(3) 0.39540(10) 0.0150(3) Uani 1 1 d . . . H1 H -0.2340 -0.1010 0.4337 0.018 Uiso 1 1 calc R . . C8 C -0.39984(11) 0.1897(3) 0.39637(11) 0.0174(3) Uani 1 1 d . . . H7 H -0.4418 0.3367 0.3701 0.021 Uiso 1 1 calc R . . H8 H -0.3771 0.2015 0.4638 0.021 Uiso 1 1 calc R . . C9 C -0.45798(10) -0.0501(3) 0.36487(10) 0.0156(3) 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 0.0265(5) 0.0183(5) 0.0483(7) 0.0020(4) 0.0212(5) 0.0017(4) F2 0.0172(5) 0.0255(6) 0.0400(6) -0.0024(4) 0.0121(4) -0.0049(4) F3 0.0285(6) 0.0297(6) 0.0289(5) -0.0040(4) 0.0162(4) 0.0019(4) F4 0.0259(6) 0.0450(7) 0.0223(5) 0.0105(5) 0.0047(4) -0.0040(5) O1 0.0222(6) 0.0189(6) 0.0361(7) -0.0073(5) 0.0165(5) -0.0007(5) N3 0.0151(6) 0.0159(7) 0.0179(6) -0.0013(5) 0.0057(5) -0.0002(5) N4 0.0153(7) 0.0188(7) 0.0197(7) 0.0001(5) 0.0075(5) -0.0012(5) N1 0.0122(6) 0.0157(7) 0.0133(6) -0.0001(5) 0.0048(5) 0.0003(5) N2 0.0137(6) 0.0162(7) 0.0162(6) -0.0019(5) 0.0070(5) 0.0003(5) N5 0.0161(7) 0.0227(8) 0.0234(7) -0.0047(6) 0.0102(6) -0.0033(5) B1 0.0143(8) 0.0173(9) 0.0220(9) 0.0013(7) 0.0073(7) 0.0004(7) C7 0.0170(8) 0.0175(8) 0.0191(8) -0.0029(6) 0.0047(6) 0.0011(6) C6 0.0131(8) 0.0231(9) 0.0218(8) -0.0053(7) 0.0067(6) 0.0015(6) C5 0.0137(8) 0.0246(9) 0.0210(8) -0.0013(7) 0.0085(6) -0.0022(6) C4 0.0112(7) 0.0157(8) 0.0154(7) -0.0042(6) 0.0043(6) -0.0011(6) C2 0.0184(8) 0.0166(8) 0.0171(8) 0.0037(6) 0.0075(6) 0.0020(6) C3 0.0178(8) 0.0162(8) 0.0164(7) 0.0023(6) 0.0055(6) 0.0026(6) C1 0.0143(7) 0.0151(8) 0.0164(7) -0.0021(6) 0.0068(6) -0.0015(6) C8 0.0147(8) 0.0189(8) 0.0227(8) -0.0017(6) 0.0115(6) 0.0004(6) C9 0.0120(7) 0.0171(8) 0.0162(7) 0.0022(6) 0.0036(6) 0.0037(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 F1 B1 1.392(2) . ? F2 B1 1.399(2) . ? F3 B1 1.392(2) . ? F4 B1 1.381(2) . ? O1 C9 1.2203(18) . ? N3 C4 1.320(2) . ? N3 C7 1.3466(19) . ? N4 C4 1.3259(19) . ? N4 C5 1.3350(19) . ? N1 C1 1.3444(18) . ? N1 C2 1.3831(19) . ? N1 C4 1.4304(18) . ? N2 C1 1.3275(19) . ? N2 C3 1.3798(19) . ? N2 C8 1.4638(18) . ? N5 C9 1.3352(19) . ? N5 H9 0.8800 . ? N5 H10 0.8800 . ? C7 C6 1.380(2) . ? C7 H6 0.9500 . ? C6 C5 1.378(2) . ? C6 H5 0.9500 . ? C5 H4 0.9500 . ? C2 C3 1.338(2) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C1 H1 0.9500 . ? C8 C9 1.517(2) . ? C8 H7 0.9900 . ? C8 H8 0.9900 . ? 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 C4 N3 C7 113.77(13) . . ? C4 N4 C5 114.62(14) . . ? C1 N1 C2 109.10(13) . . ? C1 N1 C4 126.98(13) . . ? C2 N1 C4 123.91(13) . . ? C1 N2 C3 109.23(12) . . ? C1 N2 C8 126.69(13) . . ? C3 N2 C8 124.04(12) . . ? C9 N5 H9 120.0 . . ? C9 N5 H10 120.0 . . ? H9 N5 H10 120.0 . . ? F4 B1 F3 109.97(13) . . ? F4 B1 F1 109.26(14) . . ? F3 B1 F1 108.60(14) . . ? F4 B1 F2 109.75(14) . . ? F3 B1 F2 110.02(13) . . ? F1 B1 F2 109.21(13) . . ? N3 C7 C6 122.84(15) . . ? N3 C7 H6 118.6 . . ? C6 C7 H6 118.6 . . ? C5 C6 C7 116.69(14) . . ? C5 C6 H5 121.7 . . ? C7 C6 H5 121.7 . . ? N4 C5 C6 122.45(14) . . ? N4 C5 H4 118.8 . . ? C6 C5 H4 118.8 . . ? N3 C4 N4 129.61(14) . . ? N3 C4 N1 116.98(13) . . ? N4 C4 N1 113.40(13) . . ? C3 C2 N1 106.70(13) . . ? C3 C2 H2 126.6 . . ? N1 C2 H2 126.6 . . ? C2 C3 N2 107.62(13) . . ? C2 C3 H3 126.2 . . ? N2 C3 H3 126.2 . . ? N2 C1 N1 107.35(13) . . ? N2 C1 H1 126.3 . . ? N1 C1 H1 126.3 . . ? N2 C8 C9 112.23(12) . . ? N2 C8 H7 109.2 . . ? C9 C8 H7 109.2 . . ? N2 C8 H8 109.2 . . ? C9 C8 H8 109.2 . . ? H7 C8 H8 107.9 . . ? O1 C9 N5 123.90(14) . . ? O1 C9 C8 122.75(14) . . ? N5 C9 C8 113.35(13) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.306 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.056