# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_d:\determination\solution\hrk909\hrk909h _database_code_depnum_ccdc_archive 'CCDC 877910' #TrackingRef '877910-corrected.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 Br N3 O1' _chemical_formula_sum 'C11 H8 Br N3 O1' _chemical_formula_weight 278.10 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 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 7.28110(10) _cell_length_b 7.40480(10) _cell_length_c 9.79160(10) _cell_angle_alpha 92.7400(10) _cell_angle_beta 95.6200(10) _cell_angle_gamma 91.1540(10) _cell_volume 524.613(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 13651 _cell_measurement_theta_min 2.09 _cell_measurement_theta_max 28.00 _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.322 _exptl_crystal_size_mid 0.275 _exptl_crystal_size_min 0.032 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 3.897 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.300 _exptl_absorpt_correction_T_max 0.890 _exptl_absorpt_process_details 'SADABS (Sheldric, 1998a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'APEX2 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13651 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2529 _reflns_number_gt 2358 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; 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^)+(0.0354P)^2^+0.1118P] 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 2529 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0263 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0621 _refine_ls_wR_factor_gt 0.0608 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.014 _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 C1 C 0.4045(2) 0.9498(2) 1.17113(18) 0.0254(3) Uani 1 1 d . . . H1 H 0.4476 1.0481 1.1230 0.031 Uiso 1 1 calc R . . C2 C 0.3969(2) 0.9707(2) 1.31277(18) 0.0284(3) Uani 1 1 d . . . H2 H 0.4350 1.0834 1.3582 0.034 Uiso 1 1 calc R . . C3 C 0.2858(2) 0.6833(2) 1.31695(17) 0.0261(3) Uani 1 1 d . . . H3 H 0.2430 0.5849 1.3650 0.031 Uiso 1 1 calc R . . C4 C 0.2928(2) 0.6628(2) 1.17560(16) 0.0210(3) Uani 1 1 d . . . C5 C 0.2326(2) 0.4834(2) 1.10381(16) 0.0224(3) Uani 1 1 d . . . C6 C 0.1974(2) 0.3397(2) 0.86748(16) 0.0205(3) Uani 1 1 d . . . C7 C 0.2172(2) 0.3679(2) 0.72920(17) 0.0224(3) Uani 1 1 d . . . C8 C 0.1836(2) 0.2299(2) 0.62804(17) 0.0258(3) Uani 1 1 d . . . H8 H 0.1983 0.2520 0.5349 0.031 Uiso 1 1 calc R . . C9 C 0.1284(2) 0.0598(2) 0.66396(18) 0.0270(3) Uani 1 1 d . . . H9 H 0.1066 -0.0358 0.5957 0.032 Uiso 1 1 calc R . . C10 C 0.1051(2) 0.0299(2) 0.80007(18) 0.0253(3) Uani 1 1 d . . . H10 H 0.0659 -0.0864 0.8244 0.030 Uiso 1 1 calc R . . C11 C 0.1386(2) 0.1683(2) 0.90131(17) 0.0235(3) Uani 1 1 d . . . H11 H 0.1214 0.1460 0.9940 0.028 Uiso 1 1 calc R . . N1 N 0.35259(18) 0.79462(19) 1.10161(14) 0.0230(3) Uani 1 1 d . . . N2 N 0.3383(2) 0.8390(2) 1.38682(15) 0.0300(3) Uani 1 1 d . . . N3 N 0.23971(19) 0.48338(19) 0.96534(14) 0.0229(3) Uani 1 1 d . . . H3B H 0.2752 0.5860 0.9331 0.027 Uiso 1 1 calc R . . O1 O 0.1835(2) 0.35733(18) 1.16795(13) 0.0348(3) Uani 1 1 d . . . Br1 Br 0.29259(3) 0.59835(2) 0.674996(16) 0.03164(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0268(7) 0.0214(8) 0.0275(8) 0.0001(6) 0.0013(6) -0.0026(6) C2 0.0297(8) 0.0258(8) 0.0289(8) -0.0057(6) 0.0025(6) -0.0039(6) C3 0.0311(8) 0.0269(8) 0.0204(8) 0.0012(6) 0.0041(6) -0.0036(6) C4 0.0218(6) 0.0208(7) 0.0202(7) -0.0001(5) 0.0009(5) 0.0007(5) C5 0.0247(7) 0.0218(7) 0.0204(7) -0.0002(6) 0.0023(6) -0.0007(6) C6 0.0206(6) 0.0199(7) 0.0208(7) -0.0010(6) 0.0023(5) 0.0000(5) C7 0.0275(7) 0.0171(7) 0.0231(7) 0.0019(6) 0.0040(6) 0.0003(6) C8 0.0332(8) 0.0249(8) 0.0194(7) 0.0003(6) 0.0026(6) 0.0030(6) C9 0.0310(8) 0.0221(8) 0.0267(8) -0.0049(6) 0.0008(6) 0.0003(6) C10 0.0254(7) 0.0195(7) 0.0310(8) -0.0002(6) 0.0040(6) -0.0018(6) C11 0.0258(7) 0.0221(8) 0.0230(7) 0.0018(6) 0.0046(6) -0.0010(6) N1 0.0249(6) 0.0223(7) 0.0217(6) 0.0015(5) 0.0016(5) -0.0008(5) N2 0.0367(8) 0.0311(8) 0.0219(7) -0.0045(6) 0.0047(6) -0.0051(6) N3 0.0312(7) 0.0181(6) 0.0193(6) 0.0007(5) 0.0035(5) -0.0040(5) O1 0.0564(8) 0.0255(6) 0.0223(6) 0.0011(5) 0.0060(5) -0.0106(6) Br1 0.05141(13) 0.02108(10) 0.02356(10) 0.00404(6) 0.00885(7) -0.00300(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 C1 N1 1.336(2) . ? C1 C2 1.395(2) . ? C1 H1 0.9500 . ? C2 N2 1.331(3) . ? C2 H2 0.9500 . ? C3 N2 1.341(2) . ? C3 C4 1.391(2) . ? C3 H3 0.9500 . ? C4 N1 1.334(2) . ? C4 C5 1.509(2) . ? C5 O1 1.216(2) . ? C5 N3 1.362(2) . ? C6 C11 1.396(2) . ? C6 C7 1.401(2) . ? C6 N3 1.406(2) . ? C7 C8 1.389(2) . ? C7 Br1 1.8977(16) . ? C8 C9 1.386(3) . ? C8 H8 0.9500 . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 C11 1.392(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? N3 H3B 0.8800 . ? 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 N1 C1 C2 121.47(16) . . ? N1 C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? N2 C2 C1 122.59(16) . . ? N2 C2 H2 118.7 . . ? C1 C2 H2 118.7 . . ? N2 C3 C4 121.44(16) . . ? N2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? N1 C4 C3 122.56(15) . . ? N1 C4 C5 118.88(14) . . ? C3 C4 C5 118.56(15) . . ? O1 C5 N3 126.27(15) . . ? O1 C5 C4 121.09(14) . . ? N3 C5 C4 112.64(14) . . ? C11 C6 C7 117.95(14) . . ? C11 C6 N3 123.25(14) . . ? C7 C6 N3 118.79(14) . . ? C8 C7 C6 121.67(15) . . ? C8 C7 Br1 117.98(12) . . ? C6 C7 Br1 120.35(12) . . ? C9 C8 C7 119.53(15) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 119.68(16) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C9 C10 C11 120.73(16) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C6 120.41(15) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? C4 N1 C1 116.01(14) . . ? C2 N2 C3 115.94(15) . . ? C5 N3 C6 128.02(14) . . ? C5 N3 H3B 116.0 . . ? C6 N3 H3B 116.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 0.1(3) . . . . ? N2 C3 C4 N1 0.5(3) . . . . ? N2 C3 C4 C5 179.66(15) . . . . ? N1 C4 C5 O1 177.28(15) . . . . ? C3 C4 C5 O1 -1.9(2) . . . . ? N1 C4 C5 N3 -3.0(2) . . . . ? C3 C4 C5 N3 177.75(14) . . . . ? C11 C6 C7 C8 -1.3(2) . . . . ? N3 C6 C7 C8 177.82(15) . . . . ? C11 C6 C7 Br1 178.98(11) . . . . ? N3 C6 C7 Br1 -1.9(2) . . . . ? C6 C7 C8 C9 0.2(2) . . . . ? Br1 C7 C8 C9 179.95(12) . . . . ? C7 C8 C9 C10 0.8(3) . . . . ? C8 C9 C10 C11 -0.7(3) . . . . ? C9 C10 C11 C6 -0.4(2) . . . . ? C7 C6 C11 C10 1.4(2) . . . . ? N3 C6 C11 C10 -177.71(15) . . . . ? C3 C4 N1 C1 -0.6(2) . . . . ? C5 C4 N1 C1 -179.77(14) . . . . ? C2 C1 N1 C4 0.3(2) . . . . ? C1 C2 N2 C3 -0.2(3) . . . . ? C4 C3 N2 C2 0.0(2) . . . . ? O1 C5 N3 C6 -1.7(3) . . . . ? C4 C5 N3 C6 178.65(14) . . . . ? C11 C6 N3 C5 0.1(3) . . . . ? C7 C6 N3 C5 -178.91(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.400 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.065 data_d:\determination\solution\hrk809\hrk809h _database_code_depnum_ccdc_archive 'CCDC 877911' #TrackingRef '877911-corrected.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 Cl N3 O' _chemical_formula_sum 'C11 H8 Cl N3 O' _chemical_formula_weight 233.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 7.26070(10) _cell_length_b 7.30810(10) _cell_length_c 9.69630(10) _cell_angle_alpha 95.1400(10) _cell_angle_beta 91.7500(10) _cell_angle_gamma 90.4940(10) _cell_volume 512.163(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 13508 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 28.00 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.192 _exptl_crystal_size_mid 0.137 _exptl_crystal_size_min 0.111 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.352 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.945 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details 'SADABS (Sheldric, 1998a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'APEX2 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13508 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2484 _reflns_number_gt 2229 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; 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^)+(0.0535P)^2^+0.1066P] 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 2484 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0903 _refine_ls_wR_factor_gt 0.0867 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.010 _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 C1 C 0.45536(16) 0.40876(16) 0.67164(13) 0.0260(2) Uani 1 1 d . . . H1 H 0.5552 0.4526 0.6222 0.031 Uiso 1 1 calc R . . C2 C 0.47539(17) 0.40124(17) 0.81448(13) 0.0290(3) Uani 1 1 d . . . H2 H 0.5890 0.4400 0.8594 0.035 Uiso 1 1 calc R . . C3 C 0.18511(17) 0.28820(16) 0.82106(12) 0.0272(2) Uani 1 1 d . . . H3 H 0.0854 0.2443 0.8706 0.033 Uiso 1 1 calc R . . C4 C 0.16468(15) 0.29495(14) 0.67857(11) 0.0218(2) Uani 1 1 d . . . C5 C -0.01489(15) 0.23327(15) 0.60678(12) 0.0233(2) Uani 1 1 d . . . C6 C -0.15475(15) 0.19784(14) 0.36821(11) 0.0215(2) Uani 1 1 d . . . C7 C -0.12190(16) 0.21907(16) 0.22863(12) 0.0243(2) Uani 1 1 d . . . C8 C -0.25883(17) 0.18652(17) 0.12633(13) 0.0287(3) Uani 1 1 d . . . H8 H -0.2335 0.2021 0.0325 0.034 Uiso 1 1 calc R . . C9 C -0.43323(17) 0.13098(17) 0.16176(13) 0.0291(3) Uani 1 1 d . . . H9 H -0.5286 0.1105 0.0927 0.035 Uiso 1 1 calc R . . C10 C -0.46702(16) 0.10576(16) 0.29858(13) 0.0268(2) Uani 1 1 d . . . H10 H -0.5858 0.0660 0.3226 0.032 Uiso 1 1 calc R . . C11 C -0.33000(16) 0.13774(15) 0.40118(12) 0.0245(2) Uani 1 1 d . . . H11 H -0.3555 0.1187 0.4944 0.029 Uiso 1 1 calc R . . N1 N 0.29966(13) 0.35603(13) 0.60280(10) 0.0240(2) Uani 1 1 d . . . N2 N 0.34127(16) 0.34181(15) 0.89020(11) 0.0314(2) Uani 1 1 d . . . N3 N -0.01184(13) 0.23931(13) 0.46680(10) 0.0240(2) Uani 1 1 d . . . H3B H 0.0935 0.2737 0.4341 0.029 Uiso 1 1 calc R . . O1 O -0.14466(12) 0.18426(14) 0.67139(9) 0.0346(2) Uani 1 1 d . . . Cl1 Cl 0.09484(4) 0.29093(5) 0.18169(3) 0.03548(12) 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 C1 0.0230(5) 0.0281(5) 0.0267(6) 0.0015(4) 0.0006(4) -0.0036(4) C2 0.0273(6) 0.0318(6) 0.0273(6) 0.0015(5) -0.0056(5) -0.0057(4) C3 0.0277(6) 0.0330(6) 0.0210(6) 0.0032(4) 0.0000(4) -0.0042(5) C4 0.0225(5) 0.0222(5) 0.0203(5) 0.0007(4) 0.0002(4) -0.0004(4) C5 0.0224(5) 0.0258(5) 0.0215(5) 0.0019(4) -0.0001(4) -0.0011(4) C6 0.0217(5) 0.0219(5) 0.0208(5) 0.0017(4) -0.0022(4) -0.0006(4) C7 0.0222(5) 0.0286(5) 0.0223(5) 0.0037(4) 0.0014(4) 0.0000(4) C8 0.0292(6) 0.0360(6) 0.0209(5) 0.0026(5) -0.0021(4) 0.0016(5) C9 0.0264(6) 0.0328(6) 0.0272(6) 0.0002(5) -0.0064(4) -0.0006(4) C10 0.0221(5) 0.0276(5) 0.0305(6) 0.0037(4) -0.0023(4) -0.0034(4) C11 0.0238(5) 0.0268(5) 0.0232(5) 0.0041(4) -0.0001(4) -0.0032(4) N1 0.0234(5) 0.0265(4) 0.0220(5) 0.0012(4) 0.0004(4) -0.0018(4) N2 0.0341(6) 0.0375(5) 0.0223(5) 0.0034(4) -0.0046(4) -0.0062(4) N3 0.0202(4) 0.0329(5) 0.0188(5) 0.0033(4) 0.0000(3) -0.0053(4) O1 0.0255(4) 0.0548(6) 0.0238(5) 0.0053(4) 0.0017(3) -0.0095(4) Cl1 0.02445(16) 0.0576(2) 0.02562(17) 0.01006(13) 0.00394(11) -0.00520(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.3313(15) . ? C1 C2 1.3943(17) . ? C1 H1 0.9500 . ? C2 N2 1.3302(17) . ? C2 H2 0.9500 . ? C3 N2 1.3370(16) . ? C3 C4 1.3903(16) . ? C3 H3 0.9500 . ? C4 N1 1.3397(15) . ? C4 C5 1.5053(15) . ? C5 O1 1.2162(14) . ? C5 N3 1.3628(14) . ? C6 C11 1.3981(16) . ? C6 N3 1.4016(14) . ? C6 C7 1.4034(16) . ? C7 C8 1.3865(16) . ? C7 Cl1 1.7411(12) . ? C8 C9 1.3888(18) . ? C8 H8 0.9500 . ? C9 C10 1.3845(18) . ? C9 H9 0.9500 . ? C10 C11 1.3885(16) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? N3 H3B 0.8800 . ? 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 N1 C1 C2 121.59(11) . . ? N1 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? N2 C2 C1 122.44(11) . . ? N2 C2 H2 118.8 . . ? C1 C2 H2 118.8 . . ? N2 C3 C4 121.78(11) . . ? N2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? N1 C4 C3 122.05(10) . . ? N1 C4 C5 118.72(10) . . ? C3 C4 C5 119.23(10) . . ? O1 C5 N3 125.91(11) . . ? O1 C5 C4 121.41(10) . . ? N3 C5 C4 112.68(10) . . ? C11 C6 N3 123.61(10) . . ? C11 C6 C7 117.78(10) . . ? N3 C6 C7 118.61(10) . . ? C8 C7 C6 121.66(11) . . ? C8 C7 Cl1 118.71(9) . . ? C6 C7 Cl1 119.63(9) . . ? C7 C8 C9 119.63(11) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 119.48(11) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 121.01(11) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C10 C11 C6 120.41(11) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? C1 N1 C4 116.15(10) . . ? C2 N2 C3 116.00(10) . . ? C5 N3 C6 128.39(10) . . ? C5 N3 H3B 115.8 . . ? C6 N3 H3B 115.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -0.14(19) . . . . ? N2 C3 C4 N1 -0.26(18) . . . . ? N2 C3 C4 C5 -179.77(10) . . . . ? N1 C4 C5 O1 -176.73(10) . . . . ? C3 C4 C5 O1 2.80(17) . . . . ? N1 C4 C5 N3 3.39(14) . . . . ? C3 C4 C5 N3 -177.08(10) . . . . ? C11 C6 C7 C8 1.62(17) . . . . ? N3 C6 C7 C8 -177.79(10) . . . . ? C11 C6 C7 Cl1 -179.24(8) . . . . ? N3 C6 C7 Cl1 1.35(14) . . . . ? C6 C7 C8 C9 -0.18(18) . . . . ? Cl1 C7 C8 C9 -179.32(9) . . . . ? C7 C8 C9 C10 -1.13(18) . . . . ? C8 C9 C10 C11 0.96(18) . . . . ? C9 C10 C11 C6 0.54(18) . . . . ? N3 C6 C11 C10 177.59(10) . . . . ? C7 C6 C11 C10 -1.79(16) . . . . ? C2 C1 N1 C4 -0.30(16) . . . . ? C3 C4 N1 C1 0.49(16) . . . . ? C5 C4 N1 C1 180.00(9) . . . . ? C1 C2 N2 C3 0.37(18) . . . . ? C4 C3 N2 C2 -0.18(18) . . . . ? O1 C5 N3 C6 2.32(19) . . . . ? C4 C5 N3 C6 -177.80(10) . . . . ? C11 C6 N3 C5 -1.25(18) . . . . ? C7 C6 N3 C5 178.12(11) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.329 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.047 data_hrk709h _database_code_depnum_ccdc_archive 'CCDC 877914' #TrackingRef '3Br.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 Br N3 O' _chemical_formula_sum 'C11 H8 Br N3 O' _chemical_formula_weight 278.11 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 P21/n _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 10.15680(10) _cell_length_b 11.0027(2) _cell_length_c 18.8432(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.4000(10) _cell_angle_gamma 90.00 _cell_volume 2105.14(5) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Chunk _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.352 _exptl_crystal_size_mid 0.179 _exptl_crystal_size_min 0.164 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.755 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 3.885 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.440 _exptl_absorpt_correction_T_max 0.530 _exptl_absorpt_process_details 'SADABS (Sheldric, 1998a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'APEX2 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 51211 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 36.39 _reflns_number_total 10232 _reflns_number_gt 6724 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+1.0356P] 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 10232 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1114 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 C1 C 0.9497(2) 0.04128(18) -0.08761(10) 0.0263(4) Uani 1 1 d . . . H1 H 1.0008 -0.0295 -0.0955 0.032 Uiso 1 1 calc R . . C2 C 0.9799(2) 0.14718(19) -0.12361(11) 0.0291(4) Uani 1 1 d . . . H2 H 1.0526 0.1474 -0.1544 0.035 Uiso 1 1 calc R . . C3 C 0.8080(2) 0.24208(18) -0.07261(12) 0.0306(4) Uani 1 1 d . . . H3 H 0.7529 0.3111 -0.0673 0.037 Uiso 1 1 calc R . . C4 C 0.78059(19) 0.13733(16) -0.03487(10) 0.0230(3) Uani 1 1 d . . . C5 C 0.67020(19) 0.13959(17) 0.01709(10) 0.0240(3) Uani 1 1 d . . . C6 C 0.55385(18) 0.00787(16) 0.10207(10) 0.0226(3) Uani 1 1 d . . . C7 C 0.45405(18) 0.08948(16) 0.11887(10) 0.0228(3) Uani 1 1 d . . . H7 H 0.4464 0.1658 0.0956 0.027 Uiso 1 1 calc R . . C8 C 0.36630(18) 0.05555(17) 0.17065(10) 0.0230(3) Uani 1 1 d . . . C9 C 0.3715(2) -0.05505(19) 0.20528(12) 0.0316(4) Uani 1 1 d . . . H9 H 0.3086 -0.0761 0.2397 0.038 Uiso 1 1 calc R . . C10 C 0.4723(2) -0.1345(2) 0.18777(13) 0.0368(5) Uani 1 1 d . . . H10 H 0.4788 -0.2111 0.2109 0.044 Uiso 1 1 calc R . . C11 C 0.5633(2) -0.10355(18) 0.13708(12) 0.0297(4) Uani 1 1 d . . . H11 H 0.6322 -0.1584 0.1262 0.036 Uiso 1 1 calc R . . C12 C 1.2941(2) 0.45476(19) 0.01148(12) 0.0312(4) Uani 1 1 d . . . H12 H 1.3512 0.5225 0.0067 0.037 Uiso 1 1 calc R . . C13 C 1.3267(2) 0.34555(19) -0.02080(12) 0.0308(4) Uani 1 1 d . . . H13 H 1.4060 0.3406 -0.0463 0.037 Uiso 1 1 calc R . . C14 C 1.1406(2) 0.26022(17) 0.02047(11) 0.0275(4) Uani 1 1 d . . . H14 H 1.0825 0.1930 0.0244 0.033 Uiso 1 1 calc R . . C15 C 1.10934(18) 0.36863(16) 0.05385(10) 0.0221(3) Uani 1 1 d . . . C16 C 0.98684(19) 0.37470(16) 0.09679(10) 0.0235(3) Uani 1 1 d . . . C17 C 0.85373(18) 0.51578(15) 0.16703(9) 0.0214(3) Uani 1 1 d . . . C18 C 0.73301(19) 0.45601(17) 0.15863(10) 0.0234(3) Uani 1 1 d . . . H18 H 0.7219 0.3919 0.1252 0.028 Uiso 1 1 calc R . . C19 C 0.62971(19) 0.49302(17) 0.20052(10) 0.0250(3) Uani 1 1 d . . . C20 C 0.6420(2) 0.58523(18) 0.25068(11) 0.0275(4) Uani 1 1 d . . . H20 H 0.5701 0.6075 0.2793 0.033 Uiso 1 1 calc R . . C21 C 0.7630(2) 0.64377(17) 0.25766(11) 0.0282(4) Uani 1 1 d . . . H21 H 0.7737 0.7076 0.2912 0.034 Uiso 1 1 calc R . . C22 C 0.8683(2) 0.61029(17) 0.21628(10) 0.0247(3) Uani 1 1 d . . . H22 H 0.9501 0.6515 0.2214 0.030 Uiso 1 1 calc R . . N1 N 0.85081(16) 0.03558(14) -0.04208(9) 0.0239(3) Uani 1 1 d . . . N2 N 0.90958(19) 0.24909(16) -0.11628(10) 0.0323(4) Uani 1 1 d . . . N3 N 0.64869(16) 0.03232(14) 0.05020(9) 0.0244(3) Uani 1 1 d . . . H3A H 0.6993 -0.0288 0.0381 0.029 Uiso 1 1 calc R . . N4 N 1.18526(17) 0.46747(15) 0.04897(9) 0.0272(3) Uani 1 1 d . . . N5 N 1.25000(18) 0.24750(16) -0.01701(10) 0.0306(4) Uani 1 1 d . . . N6 N 0.96242(16) 0.48557(14) 0.12523(9) 0.0234(3) Uani 1 1 d . . . H6A H 1.0194 0.5438 0.1169 0.028 Uiso 1 1 calc R . . O1 O 0.60874(16) 0.23396(13) 0.02654(9) 0.0345(3) Uani 1 1 d . . . O2 O 0.91847(16) 0.28379(13) 0.10426(9) 0.0354(3) Uani 1 1 d . . . Br1 Br 0.23378(2) 0.168200(18) 0.196523(12) 0.03065(6) Uani 1 1 d . . . Br2 Br 0.46555(2) 0.41278(2) 0.187127(13) 0.03901(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0270(9) 0.0252(8) 0.0270(9) -0.0029(7) 0.0077(7) 0.0004(7) C2 0.0293(10) 0.0309(9) 0.0276(9) -0.0014(7) 0.0106(7) -0.0043(7) C3 0.0334(10) 0.0209(8) 0.0381(11) 0.0008(7) 0.0136(8) -0.0005(7) C4 0.0243(8) 0.0206(7) 0.0245(8) -0.0024(6) 0.0065(6) -0.0035(6) C5 0.0241(8) 0.0226(8) 0.0256(8) -0.0019(6) 0.0059(6) -0.0027(6) C6 0.0232(8) 0.0220(7) 0.0227(8) -0.0024(6) 0.0065(6) -0.0015(6) C7 0.0225(8) 0.0227(8) 0.0233(8) -0.0015(6) 0.0050(6) -0.0004(6) C8 0.0201(8) 0.0247(8) 0.0245(8) -0.0037(6) 0.0057(6) -0.0009(6) C9 0.0314(10) 0.0280(9) 0.0359(11) 0.0024(8) 0.0137(8) -0.0013(7) C10 0.0396(12) 0.0275(9) 0.0443(12) 0.0089(8) 0.0196(10) 0.0044(8) C11 0.0325(10) 0.0231(8) 0.0342(10) 0.0016(7) 0.0136(8) 0.0035(7) C12 0.0277(10) 0.0292(9) 0.0370(11) -0.0029(8) 0.0096(8) -0.0040(7) C13 0.0263(9) 0.0320(10) 0.0347(10) 0.0000(8) 0.0097(8) 0.0050(7) C14 0.0311(10) 0.0206(8) 0.0313(9) -0.0017(7) 0.0079(7) 0.0020(7) C15 0.0233(8) 0.0203(7) 0.0229(8) 0.0009(6) 0.0043(6) 0.0023(6) C16 0.0239(8) 0.0205(7) 0.0264(8) -0.0003(6) 0.0062(6) 0.0015(6) C17 0.0233(8) 0.0193(7) 0.0217(8) 0.0010(6) 0.0061(6) 0.0017(6) C18 0.0241(8) 0.0225(7) 0.0239(8) 0.0001(6) 0.0046(6) 0.0004(6) C19 0.0224(8) 0.0265(8) 0.0263(9) 0.0018(6) 0.0054(6) 0.0009(6) C20 0.0289(9) 0.0262(8) 0.0279(9) 0.0000(7) 0.0095(7) 0.0044(7) C21 0.0344(10) 0.0225(8) 0.0281(9) -0.0044(7) 0.0081(8) 0.0012(7) C22 0.0275(9) 0.0218(8) 0.0250(8) -0.0008(6) 0.0051(7) -0.0001(6) N1 0.0241(7) 0.0224(7) 0.0254(7) -0.0010(5) 0.0063(6) -0.0005(5) N2 0.0326(9) 0.0267(8) 0.0384(10) 0.0045(7) 0.0134(7) -0.0026(6) N3 0.0263(8) 0.0216(7) 0.0257(7) -0.0005(5) 0.0105(6) 0.0008(6) N4 0.0260(8) 0.0240(7) 0.0319(8) -0.0032(6) 0.0076(6) -0.0016(6) N5 0.0322(9) 0.0256(8) 0.0346(9) -0.0009(6) 0.0108(7) 0.0057(6) N6 0.0235(7) 0.0193(6) 0.0276(7) -0.0020(5) 0.0084(6) -0.0012(5) O1 0.0352(8) 0.0232(6) 0.0459(9) 0.0013(6) 0.0177(7) 0.0038(6) O2 0.0347(8) 0.0220(6) 0.0505(9) -0.0031(6) 0.0183(7) -0.0037(6) Br1 0.02340(10) 0.02878(10) 0.04032(12) -0.00361(8) 0.01179(7) 0.00152(7) Br2 0.02347(10) 0.05018(14) 0.04379(13) -0.01089(10) 0.00896(8) -0.00615(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.338(2) . ? C1 C2 1.386(3) . ? C1 H1 0.9500 . ? C2 N2 1.338(3) . ? C2 H2 0.9500 . ? C3 N2 1.337(3) . ? C3 C4 1.386(3) . ? C3 H3 0.9500 . ? C4 N1 1.336(2) . ? C4 C5 1.507(2) . ? C5 O1 1.227(2) . ? C5 N3 1.355(2) . ? C6 C11 1.394(3) . ? C6 C7 1.396(3) . ? C6 N3 1.415(2) . ? C7 C8 1.389(2) . ? C7 H7 0.9500 . ? C8 C9 1.381(3) . ? C8 Br1 1.9020(18) . ? C9 C10 1.392(3) . ? C9 H9 0.9500 . ? C10 C11 1.388(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 N4 1.334(3) . ? C12 C13 1.390(3) . ? C12 H12 0.9500 . ? C13 N5 1.333(3) . ? C13 H13 0.9500 . ? C14 N5 1.339(3) . ? C14 C15 1.389(3) . ? C14 H14 0.9500 . ? C15 N4 1.338(2) . ? C15 C16 1.502(2) . ? C16 O2 1.228(2) . ? C16 N6 1.358(2) . ? C17 C18 1.397(3) . ? C17 C22 1.399(3) . ? C17 N6 1.411(2) . ? C18 C19 1.389(3) . ? C18 H18 0.9500 . ? C19 C20 1.390(3) . ? C19 Br2 1.898(2) . ? C20 C21 1.391(3) . ? C20 H20 0.9500 . ? C21 C22 1.389(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? N3 H3A 0.8800 . ? N6 H6A 0.8800 . ? 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 N1 C1 C2 122.11(18) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? N2 C2 C1 121.92(18) . . ? N2 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? N2 C3 C4 122.09(19) . . ? N2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? N1 C4 C3 122.01(17) . . ? N1 C4 C5 119.18(16) . . ? C3 C4 C5 118.80(17) . . ? O1 C5 N3 125.59(17) . . ? O1 C5 C4 119.85(17) . . ? N3 C5 C4 114.56(16) . . ? C11 C6 C7 120.00(17) . . ? C11 C6 N3 117.00(16) . . ? C7 C6 N3 123.00(16) . . ? C8 C7 C6 117.93(17) . . ? C8 C7 H7 121.0 . . ? C6 C7 H7 121.0 . . ? C9 C8 C7 123.45(17) . . ? C9 C8 Br1 118.16(14) . . ? C7 C8 Br1 118.38(14) . . ? C8 C9 C10 117.46(18) . . ? C8 C9 H9 121.3 . . ? C10 C9 H9 121.3 . . ? C11 C10 C9 121.0(2) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C6 120.15(19) . . ? C10 C11 H11 119.9 . . ? C6 C11 H11 119.9 . . ? N4 C12 C13 122.11(19) . . ? N4 C12 H12 118.9 . . ? C13 C12 H12 118.9 . . ? N5 C13 C12 122.02(18) . . ? N5 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? N5 C14 C15 122.03(18) . . ? N5 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? N4 C15 C14 121.93(17) . . ? N4 C15 C16 119.17(16) . . ? C14 C15 C16 118.91(17) . . ? O2 C16 N6 125.27(17) . . ? O2 C16 C15 120.25(16) . . ? N6 C16 C15 114.47(16) . . ? C18 C17 C22 120.21(16) . . ? C18 C17 N6 121.48(16) . . ? C22 C17 N6 118.28(17) . . ? C19 C18 C17 118.07(17) . . ? C19 C18 H18 121.0 . . ? C17 C18 H18 121.0 . . ? C18 C19 C20 122.93(18) . . ? C18 C19 Br2 117.46(14) . . ? C20 C19 Br2 119.61(14) . . ? C19 C20 C21 117.84(17) . . ? C19 C20 H20 121.1 . . ? C21 C20 H20 121.1 . . ? C22 C21 C20 120.98(18) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C22 C17 119.96(18) . . ? C21 C22 H22 120.0 . . ? C17 C22 H22 120.0 . . ? C4 N1 C1 115.90(16) . . ? C3 N2 C2 115.89(17) . . ? C5 N3 C6 127.14(16) . . ? C5 N3 H3A 116.4 . . ? C6 N3 H3A 116.4 . . ? C12 N4 C15 115.96(17) . . ? C13 N5 C14 115.92(17) . . ? C16 N6 C17 125.79(16) . . ? C16 N6 H6A 117.1 . . ? C17 N6 H6A 117.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -1.8(3) . . . . ? N2 C3 C4 N1 -2.8(3) . . . . ? N2 C3 C4 C5 175.8(2) . . . . ? N1 C4 C5 O1 176.78(19) . . . . ? C3 C4 C5 O1 -1.8(3) . . . . ? N1 C4 C5 N3 -2.9(3) . . . . ? C3 C4 C5 N3 178.50(19) . . . . ? C11 C6 C7 C8 -0.2(3) . . . . ? N3 C6 C7 C8 179.88(18) . . . . ? C6 C7 C8 C9 -1.1(3) . . . . ? C6 C7 C8 Br1 177.75(14) . . . . ? C7 C8 C9 C10 1.4(3) . . . . ? Br1 C8 C9 C10 -177.47(18) . . . . ? C8 C9 C10 C11 -0.4(4) . . . . ? C9 C10 C11 C6 -0.8(4) . . . . ? C7 C6 C11 C10 1.1(3) . . . . ? N3 C6 C11 C10 -178.9(2) . . . . ? N4 C12 C13 N5 1.0(4) . . . . ? N5 C14 C15 N4 1.7(3) . . . . ? N5 C14 C15 C16 -178.16(19) . . . . ? N4 C15 C16 O2 -177.2(2) . . . . ? C14 C15 C16 O2 2.7(3) . . . . ? N4 C15 C16 N6 2.3(3) . . . . ? C14 C15 C16 N6 -177.80(18) . . . . ? C22 C17 C18 C19 -0.2(3) . . . . ? N6 C17 C18 C19 -178.39(17) . . . . ? C17 C18 C19 C20 -0.9(3) . . . . ? C17 C18 C19 Br2 178.87(14) . . . . ? C18 C19 C20 C21 1.3(3) . . . . ? Br2 C19 C20 C21 -178.45(15) . . . . ? C19 C20 C21 C22 -0.6(3) . . . . ? C20 C21 C22 C17 -0.5(3) . . . . ? C18 C17 C22 C21 0.9(3) . . . . ? N6 C17 C22 C21 179.10(18) . . . . ? C3 C4 N1 C1 0.4(3) . . . . ? C5 C4 N1 C1 -178.11(17) . . . . ? C2 C1 N1 C4 1.8(3) . . . . ? C4 C3 N2 C2 2.7(3) . . . . ? C1 C2 N2 C3 -0.5(3) . . . . ? O1 C5 N3 C6 -0.8(3) . . . . ? C4 C5 N3 C6 178.90(18) . . . . ? C11 C6 N3 C5 -170.0(2) . . . . ? C7 C6 N3 C5 10.0(3) . . . . ? C13 C12 N4 C15 0.2(3) . . . . ? C14 C15 N4 C12 -1.4(3) . . . . ? C16 C15 N4 C12 178.42(19) . . . . ? C12 C13 N5 C14 -0.8(3) . . . . ? C15 C14 N5 C13 -0.5(3) . . . . ? O2 C16 N6 C17 -1.1(3) . . . . ? C15 C16 N6 C17 179.39(17) . . . . ? C18 C17 N6 C16 -29.0(3) . . . . ? C22 C17 N6 C16 152.77(19) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 36.39 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.078 _refine_diff_density_min -1.411 _refine_diff_density_rms 0.100 data_d:\determination\solution\c266\khc266 _database_code_depnum_ccdc_archive 'CCDC 907173' #TrackingRef '877913-corrected.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H8 I1 N3 O1' _chemical_formula_weight 325.10 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.8485(5) _cell_length_b 13.4762(12) _cell_length_c 16.8631(18) _cell_angle_alpha 90.00 _cell_angle_beta 95.849(9) _cell_angle_gamma 90.00 _cell_volume 1096.09(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7093 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 28 _exptl_crystal_description Needle _exptl_crystal_colour 'Light yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.970 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 2.902 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8010 _exptl_absorpt_correction_T_max 0.8581 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7093 _diffrn_reflns_av_R_equivalents 0.0995 _diffrn_reflns_av_sigmaI/netI 0.1148 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2640 _reflns_number_gt 1923 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0717P)^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 SHELXL _refine_ls_extinction_coef 0.0049(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2640 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0835 _refine_ls_R_factor_gt 0.0602 _refine_ls_wR_factor_ref 0.1576 _refine_ls_wR_factor_gt 0.1477 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _refine_ls_shift/su_max 0.005 _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 C1 C 1.0749(16) 0.4269(5) 0.3585(5) 0.0299(16) Uani 1 1 d . . . H1 H 1.0865 0.4615 0.3113 0.036 Uiso 1 1 calc R . . C2 C 1.2541(16) 0.4515(5) 0.4247(5) 0.0305(16) Uani 1 1 d . . . H2 H 1.3762 0.5042 0.4212 0.037 Uiso 1 1 calc R . . C3 C 1.0739(16) 0.3279(5) 0.4954(5) 0.0293(15) Uani 1 1 d . . . H3 H 1.0731 0.2900 0.5415 0.035 Uiso 1 1 calc R . . C4 C 0.8843(15) 0.3061(5) 0.4304(4) 0.0230(13) Uani 1 1 d . . . C5 C 0.6766(15) 0.2244(5) 0.4359(4) 0.0260(13) Uani 1 1 d . . . C6 C 0.3047(14) 0.1373(4) 0.3507(4) 0.0192(12) Uani 1 1 d . . . C7 C 0.1475(14) 0.1363(5) 0.2766(4) 0.0210(13) Uani 1 1 d . . . C8 C -0.0534(15) 0.0643(5) 0.2581(4) 0.0263(14) Uani 1 1 d . . . H8 H -0.1523 0.0637 0.2079 0.032 Uiso 1 1 calc R . . C9 C -0.1076(18) -0.0060(5) 0.3134(5) 0.0314(16) Uani 1 1 d . . . H9 H -0.2449 -0.0533 0.3011 0.038 Uiso 1 1 calc R . . C10 C 0.0450(16) -0.0059(5) 0.3879(4) 0.0287(15) Uani 1 1 d . . . H10 H 0.0088 -0.0534 0.4255 0.034 Uiso 1 1 calc R . . C11 C 0.2506(17) 0.0643(5) 0.4066(4) 0.0285(16) Uani 1 1 d . . . H11 H 0.3530 0.0631 0.4564 0.034 Uiso 1 1 calc R . . N1 N 0.8835(13) 0.3543(4) 0.3602(4) 0.0275(12) Uani 1 1 d . . . N2 N 1.2577(14) 0.4018(5) 0.4938(4) 0.0350(15) Uani 1 1 d . . . N3 N 0.5132(13) 0.2081(4) 0.3683(3) 0.0245(12) Uani 1 1 d . . . H3B H 0.5406 0.2472 0.3296 0.029 Uiso 1 1 calc R . . O1 O 0.6672(12) 0.1799(4) 0.4985(3) 0.0310(11) Uani 1 1 d . . . I1 I 0.21021(11) 0.24017(3) 0.18659(3) 0.0297(2) 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 C1 0.028(4) 0.027(3) 0.036(4) 0.004(3) 0.007(3) 0.000(3) C2 0.030(4) 0.025(3) 0.036(4) -0.003(3) 0.001(3) -0.003(3) C3 0.027(4) 0.025(3) 0.036(4) 0.004(3) 0.005(3) 0.000(3) C4 0.024(3) 0.022(3) 0.023(3) -0.002(2) 0.005(3) 0.001(3) C5 0.027(4) 0.026(3) 0.036(4) 0.004(3) 0.007(3) 0.000(3) C6 0.019(3) 0.020(3) 0.019(3) -0.002(2) 0.004(2) 0.001(2) C7 0.021(3) 0.021(3) 0.021(3) 0.004(2) 0.007(3) 0.002(2) C8 0.026(3) 0.024(3) 0.029(4) -0.004(3) 0.003(3) -0.002(3) C9 0.034(4) 0.025(3) 0.036(4) -0.002(3) 0.007(3) -0.005(3) C10 0.032(4) 0.025(3) 0.030(4) 0.002(3) 0.009(3) -0.003(3) C11 0.036(4) 0.028(3) 0.024(4) 0.000(3) 0.011(3) -0.003(3) N1 0.028(4) 0.027(3) 0.036(4) 0.004(3) 0.007(3) 0.000(3) N2 0.030(3) 0.044(4) 0.031(4) -0.005(3) 0.005(3) -0.007(3) N3 0.025(3) 0.026(3) 0.023(3) 0.003(2) 0.005(2) -0.005(2) O1 0.034(3) 0.039(3) 0.019(2) 0.002(2) -0.001(2) -0.006(2) I1 0.0336(3) 0.0349(3) 0.0209(3) 0.00581(19) 0.00421(18) -0.00382(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.350(9) . ? C1 C2 1.383(12) . ? C1 H1 0.9300 . ? C2 N2 1.343(10) . ? C2 H2 0.9300 . ? C3 N2 1.339(10) . ? C3 C4 1.389(11) . ? C3 H3 0.9300 . ? C4 N1 1.349(9) . ? C4 C5 1.501(9) . ? C5 O1 1.219(8) . ? C5 N3 1.339(10) . ? C6 C7 1.396(10) . ? C6 N3 1.399(8) . ? C6 C11 1.406(9) . ? C7 C8 1.387(9) . ? C7 I1 2.109(6) . ? C8 C9 1.373(10) . ? C8 H8 0.9300 . ? C9 C10 1.393(11) . ? C9 H9 0.9300 . ? C10 C11 1.387(10) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? N3 H3B 0.8600 . ? 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 N1 C1 C2 122.2(7) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? N2 C2 C1 122.2(7) . . ? N2 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? N2 C3 C4 122.0(7) . . ? N2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? N1 C4 C3 122.2(6) . . ? N1 C4 C5 117.7(6) . . ? C3 C4 C5 120.0(6) . . ? O1 C5 N3 125.8(7) . . ? O1 C5 C4 119.9(7) . . ? N3 C5 C4 114.2(6) . . ? C7 C6 N3 120.8(6) . . ? C7 C6 C11 118.2(6) . . ? N3 C6 C11 121.0(7) . . ? C8 C7 C6 121.0(6) . . ? C8 C7 I1 116.9(5) . . ? C6 C7 I1 122.2(5) . . ? C9 C8 C7 120.6(7) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 119.4(7) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C11 C10 C9 120.6(7) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C6 120.2(7) . . ? C10 C11 H11 119.9 . . ? C6 C11 H11 119.9 . . ? C4 N1 C1 115.3(7) . . ? C3 N2 C2 116.0(7) . . ? C5 N3 C6 130.1(6) . . ? C5 N3 H3B 114.9 . . ? C6 N3 H3B 114.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 3.1(11) . . . . ? N2 C3 C4 N1 3.7(11) . . . . ? N2 C3 C4 C5 -178.1(6) . . . . ? N1 C4 C5 O1 -178.9(6) . . . . ? C3 C4 C5 O1 2.9(10) . . . . ? N1 C4 C5 N3 0.8(9) . . . . ? C3 C4 C5 N3 -177.4(6) . . . . ? N3 C6 C7 C8 178.0(6) . . . . ? C11 C6 C7 C8 -1.1(9) . . . . ? N3 C6 C7 I1 -0.1(8) . . . . ? C11 C6 C7 I1 -179.2(5) . . . . ? C6 C7 C8 C9 1.9(10) . . . . ? I1 C7 C8 C9 -179.9(5) . . . . ? C7 C8 C9 C10 -1.3(11) . . . . ? C8 C9 C10 C11 -0.1(11) . . . . ? C9 C10 C11 C6 0.9(11) . . . . ? C7 C6 C11 C10 -0.3(10) . . . . ? N3 C6 C11 C10 -179.3(6) . . . . ? C3 C4 N1 C1 -1.7(9) . . . . ? C5 C4 N1 C1 -179.9(6) . . . . ? C2 C1 N1 C4 -1.5(10) . . . . ? C4 C3 N2 C2 -2.2(10) . . . . ? C1 C2 N2 C3 -1.1(11) . . . . ? O1 C5 N3 C6 -2.3(12) . . . . ? C4 C5 N3 C6 178.0(6) . . . . ? C7 C6 N3 C5 176.6(7) . . . . ? C11 C6 N3 C5 -4.4(10) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.451 _refine_diff_density_min -0.551 _refine_diff_density_rms 0.259 data_d:\determination\solution\c41\khc41 _database_code_depnum_ccdc_archive 'CCDC 907174' #TrackingRef '877917-corrected.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H8 I1 N3 O' _chemical_formula_weight 325.10 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.3086(3) _cell_length_b 12.7522(6) _cell_length_c 19.6521(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.258(5) _cell_angle_gamma 90.00 _cell_volume 1078.93(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6556 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 28.00 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.001 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 2.948 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7226 _exptl_absorpt_correction_T_max 0.8111 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6556 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2596 _reflns_number_gt 2109 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0743P)^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 2596 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.010 _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 C1 C 1.7793(13) 0.4988(5) -0.2411(3) 0.0274(11) Uani 1 1 d . . . H1 H 1.8436 0.5629 -0.2229 0.033 Uiso 1 1 calc R . . C2 C 1.8749(12) 0.4693(5) -0.3046(3) 0.0263(11) Uani 1 1 d . . . H2 H 2.0039 0.5145 -0.3276 0.032 Uiso 1 1 calc R . . C3 C 1.6098(12) 0.3186(5) -0.2981(3) 0.0264(11) Uani 1 1 d . . . H3 H 1.5449 0.2547 -0.3166 0.032 Uiso 1 1 calc R . . C4 C 1.5139(10) 0.3460(4) -0.2343(3) 0.0181(10) Uani 1 1 d . . . C5 C 1.3125(10) 0.2721(4) -0.1956(3) 0.0201(10) Uani 1 1 d . . . C6 C 1.0297(10) 0.2666(4) -0.0874(3) 0.0195(10) Uani 1 1 d . . . C7 C 0.9210(11) 0.3337(4) -0.0372(3) 0.0183(9) Uani 1 1 d . . . H7 H 0.9682 0.4048 -0.0381 0.022 Uiso 1 1 calc R . . C8 C 0.7419(11) 0.2931(4) 0.0138(3) 0.0207(10) Uani 1 1 d . . . C9 C 0.6658(12) 0.1871(5) 0.0151(3) 0.0252(11) Uani 1 1 d . . . H9 H 0.5462 0.1600 0.0494 0.030 Uiso 1 1 calc R . . C10 C 0.7715(14) 0.1233(4) -0.0354(3) 0.0264(12) Uani 1 1 d . . . H10 H 0.7216 0.0524 -0.0349 0.032 Uiso 1 1 calc R . . C11 C 0.9510(12) 0.1617(5) -0.0873(3) 0.0258(11) Uani 1 1 d . . . H11 H 1.0168 0.1173 -0.1214 0.031 Uiso 1 1 calc R . . N1 N 1.5973(10) 0.4373(4) -0.2055(2) 0.0236(9) Uani 1 1 d . . . N2 N 1.7919(12) 0.3800(4) -0.3343(3) 0.0318(11) Uani 1 1 d . . . N3 N 1.2178(9) 0.3126(4) -0.1363(2) 0.0201(8) Uani 1 1 d . . . H3B H 1.2811 0.3752 -0.1271 0.024 Uiso 1 1 calc R . . O1 O 1.2437(10) 0.1857(4) -0.2179(2) 0.0328(9) Uani 1 1 d . . . I1 I 0.58677(7) 0.39413(3) 0.089043(17) 0.02308(14) 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 C1 0.032(2) 0.026(3) 0.025(3) -0.003(2) 0.010(2) -0.004(2) C2 0.026(2) 0.030(3) 0.024(3) 0.005(2) 0.008(2) 0.003(2) C3 0.030(2) 0.030(3) 0.020(3) -0.001(2) 0.009(2) 0.000(2) C4 0.0149(19) 0.022(3) 0.017(2) 0.000(2) 0.0040(17) 0.0046(17) C5 0.016(2) 0.027(3) 0.017(3) -0.001(2) 0.0044(17) 0.0016(18) C6 0.0147(18) 0.029(3) 0.016(2) 0.003(2) 0.0030(16) -0.0020(18) C7 0.021(2) 0.017(2) 0.017(2) 0.0004(19) 0.0036(17) -0.0006(17) C8 0.020(2) 0.027(3) 0.016(2) -0.003(2) 0.0052(17) 0.0039(19) C9 0.027(2) 0.026(3) 0.023(3) 0.003(2) 0.007(2) -0.005(2) C10 0.033(3) 0.021(3) 0.026(3) -0.002(2) 0.009(2) -0.007(2) C11 0.027(2) 0.027(3) 0.023(3) -0.006(2) 0.010(2) -0.003(2) N1 0.023(2) 0.025(2) 0.023(2) 0.0000(19) 0.0049(17) -0.0005(17) N2 0.035(2) 0.038(3) 0.024(3) -0.003(2) 0.012(2) 0.001(2) N3 0.0229(18) 0.020(2) 0.018(2) -0.0021(18) 0.0094(15) -0.0032(16) O1 0.042(2) 0.030(2) 0.028(2) -0.0065(19) 0.0144(18) -0.0084(18) I1 0.02269(18) 0.0286(2) 0.0185(2) -0.00310(15) 0.00891(12) -0.00016(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.328(7) . ? C1 C2 1.382(8) . ? C1 H1 0.9300 . ? C2 N2 1.322(8) . ? C2 H2 0.9300 . ? C3 N2 1.334(8) . ? C3 C4 1.381(7) . ? C3 H3 0.9300 . ? C4 N1 1.337(7) . ? C4 C5 1.507(7) . ? C5 O1 1.218(7) . ? C5 N3 1.354(7) . ? C6 C11 1.380(8) . ? C6 C7 1.400(7) . ? C6 N3 1.409(6) . ? C7 C8 1.390(7) . ? C7 H7 0.9300 . ? C8 C9 1.392(8) . ? C8 I1 2.090(5) . ? C9 C10 1.374(8) . ? C9 H9 0.9300 . ? C10 C11 1.393(8) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? N3 H3B 0.8600 . ? 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 N1 C1 C2 121.2(5) . . ? N1 C1 H1 119.4 . . ? C2 C1 H1 119.4 . . ? N2 C2 C1 123.2(5) . . ? N2 C2 H2 118.4 . . ? C1 C2 H2 118.4 . . ? N2 C3 C4 122.6(6) . . ? N2 C3 H3 118.7 . . ? C4 C3 H3 118.7 . . ? N1 C4 C3 121.4(5) . . ? N1 C4 C5 118.8(5) . . ? C3 C4 C5 119.9(5) . . ? O1 C5 N3 125.3(5) . . ? O1 C5 C4 121.4(5) . . ? N3 C5 C4 113.2(5) . . ? C11 C6 C7 120.2(5) . . ? C11 C6 N3 123.5(5) . . ? C7 C6 N3 116.3(5) . . ? C8 C7 C6 119.4(5) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 120.9(5) . . ? C7 C8 I1 118.9(4) . . ? C9 C8 I1 120.3(4) . . ? C10 C9 C8 118.4(5) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? C9 C10 C11 122.1(5) . . ? C9 C10 H10 119.0 . . ? C11 C10 H10 119.0 . . ? C6 C11 C10 119.0(5) . . ? C6 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C1 N1 C4 116.4(5) . . ? C2 N2 C3 115.2(5) . . ? C5 N3 C6 129.0(5) . . ? C5 N3 H3B 115.5 . . ? C6 N3 H3B 115.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 0.6(9) . . . . ? N2 C3 C4 N1 0.7(8) . . . . ? N2 C3 C4 C5 -179.0(5) . . . . ? N1 C4 C5 O1 -176.0(5) . . . . ? C3 C4 C5 O1 3.6(7) . . . . ? N1 C4 C5 N3 5.0(6) . . . . ? C3 C4 C5 N3 -175.3(5) . . . . ? C11 C6 C7 C8 2.1(7) . . . . ? N3 C6 C7 C8 -178.1(4) . . . . ? C6 C7 C8 C9 -1.0(7) . . . . ? C6 C7 C8 I1 179.2(3) . . . . ? C7 C8 C9 C10 -0.1(8) . . . . ? I1 C8 C9 C10 179.8(4) . . . . ? C8 C9 C10 C11 0.0(9) . . . . ? C7 C6 C11 C10 -2.2(8) . . . . ? N3 C6 C11 C10 178.0(5) . . . . ? C9 C10 C11 C6 1.1(9) . . . . ? C2 C1 N1 C4 0.2(8) . . . . ? C3 C4 N1 C1 -0.8(7) . . . . ? C5 C4 N1 C1 178.8(5) . . . . ? C1 C2 N2 C3 -0.7(9) . . . . ? C4 C3 N2 C2 0.1(8) . . . . ? O1 C5 N3 C6 1.2(9) . . . . ? C4 C5 N3 C6 -179.9(5) . . . . ? C11 C6 N3 C5 11.5(8) . . . . ? C7 C6 N3 C5 -168.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.012 _refine_diff_density_min -1.135 _refine_diff_density_rms 0.233 data_d:\determination\solution\c267\khc267 _database_code_depnum_ccdc_archive 'CCDC 907175' #TrackingRef '877918-corrected.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 I1 N3 O1' _chemical_formula_sum 'C11 H8 I1 N3 O1' _chemical_formula_weight 325.10 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' I I -0.4742 1.8119 '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 5.9493(5) _cell_length_b 7.6138(8) _cell_length_c 12.9655(12) _cell_angle_alpha 79.339(8) _cell_angle_beta 85.153(8) _cell_angle_gamma 69.377(7) _cell_volume 540.05(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5480 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 28.00 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.999 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 2.945 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6011 _exptl_absorpt_correction_T_max 0.7119 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5480 _diffrn_reflns_av_R_equivalents 0.1142 _diffrn_reflns_av_sigmaI/netI 0.1388 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2601 _reflns_number_gt 1686 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0707P)^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 2601 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1108 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.1512 _refine_ls_wR_factor_gt 0.1346 _refine_ls_goodness_of_fit_ref 0.926 _refine_ls_restrained_S_all 0.926 _refine_ls_shift/su_max 0.005 _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 C1 C 0.4593(16) -0.5155(14) 0.7818(7) 0.032(2) Uani 1 1 d . . . H1 H 0.3163 -0.5247 0.8129 0.039 Uiso 1 1 calc R . . C2 C 0.6661(16) -0.5994(13) 0.8385(7) 0.034(2) Uani 1 1 d . . . H2 H 0.6596 -0.6692 0.9050 0.041 Uiso 1 1 calc R . . C3 C 0.8724(17) -0.4863(13) 0.7016(7) 0.0312(19) Uani 1 1 d . . . H3 H 1.0131 -0.4723 0.6704 0.037 Uiso 1 1 calc R . . C4 C 0.6666(15) -0.4086(13) 0.6467(7) 0.0295(19) Uani 1 1 d . . . C5 C 0.6738(17) -0.2990(14) 0.5374(7) 0.0320(18) Uani 1 1 d . . . C6 C 0.4051(15) -0.1233(12) 0.3842(6) 0.0260(18) Uani 1 1 d . . . C7 C 0.5785(16) -0.0970(14) 0.3092(7) 0.033(2) Uani 1 1 d . . . H7 H 0.7402 -0.1468 0.3259 0.040 Uiso 1 1 calc R . . C8 C 0.5088(15) 0.0029(13) 0.2103(7) 0.0283(18) Uani 1 1 d . . . H8 H 0.6243 0.0202 0.1604 0.034 Uiso 1 1 calc R . . C9 C 0.2723(16) 0.0766(12) 0.1851(7) 0.031(2) Uani 1 1 d . . . C10 C 0.0970(17) 0.0521(14) 0.2599(7) 0.034(2) Uani 1 1 d . . . H10 H -0.0645 0.1038 0.2427 0.041 Uiso 1 1 calc R . . C11 C 0.1634(15) -0.0490(13) 0.3594(6) 0.0307(19) Uani 1 1 d . . . H11 H 0.0477 -0.0669 0.4091 0.037 Uiso 1 1 calc R . . N1 N 0.4554(13) -0.4207(11) 0.6836(6) 0.0326(17) Uani 1 1 d . . . N2 N 0.8789(13) -0.5842(12) 0.8011(6) 0.0369(18) Uani 1 1 d . . . N3 N 0.4565(13) -0.2299(11) 0.4863(6) 0.0332(17) Uani 1 1 d . . . H3B H 0.3386 -0.2549 0.5209 0.040 Uiso 1 1 calc R . . O1 O 0.8601(12) -0.2768(10) 0.4970(5) 0.0402(16) Uani 1 1 d . . . I1 I 0.16424(12) 0.21616(10) 0.03258(5) 0.0348(2) 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 C1 0.030(4) 0.046(6) 0.023(4) 0.006(4) -0.001(3) -0.021(4) C2 0.036(5) 0.034(5) 0.029(5) 0.006(4) -0.003(4) -0.014(4) C3 0.034(5) 0.032(5) 0.029(4) 0.001(4) 0.004(4) -0.017(4) C4 0.030(4) 0.032(5) 0.026(4) -0.002(4) 0.005(3) -0.014(4) C5 0.033(4) 0.036(5) 0.025(4) 0.007(4) -0.006(3) -0.013(4) C6 0.033(4) 0.026(4) 0.021(4) 0.001(3) -0.001(3) -0.015(4) C7 0.032(4) 0.038(5) 0.030(5) -0.007(4) 0.002(4) -0.013(4) C8 0.029(4) 0.033(5) 0.025(4) -0.008(4) 0.001(3) -0.011(4) C9 0.036(5) 0.025(5) 0.028(4) 0.001(4) -0.002(4) -0.008(4) C10 0.035(5) 0.039(5) 0.030(5) -0.003(4) -0.003(4) -0.015(4) C11 0.030(4) 0.040(5) 0.021(4) 0.005(4) 0.009(3) -0.018(4) N1 0.030(4) 0.034(4) 0.027(4) 0.009(3) -0.005(3) -0.009(3) N2 0.032(4) 0.042(5) 0.036(4) 0.004(4) -0.008(3) -0.014(4) N3 0.026(4) 0.043(5) 0.033(4) 0.005(3) 0.003(3) -0.020(3) O1 0.039(4) 0.047(4) 0.033(3) 0.006(3) 0.003(3) -0.022(3) I1 0.0364(3) 0.0384(4) 0.0263(3) 0.0045(2) -0.0053(2) -0.0126(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.340(11) . ? C1 C2 1.374(13) . ? C1 H1 0.9300 . ? C2 N2 1.353(11) . ? C2 H2 0.9300 . ? C3 C4 1.355(13) . ? C3 N2 1.362(12) . ? C3 H3 0.9300 . ? C4 N1 1.334(11) . ? C4 C5 1.511(12) . ? C5 O1 1.238(10) . ? C5 N3 1.387(12) . ? C6 C11 1.389(12) . ? C6 C7 1.398(11) . ? C6 N3 1.415(11) . ? C7 C8 1.379(13) . ? C7 H7 0.9300 . ? C8 C9 1.362(13) . ? C8 H8 0.9300 . ? C9 C10 1.401(12) . ? C9 I1 2.100(9) . ? C10 C11 1.385(12) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? N3 H3B 0.8600 . ? 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 N1 C1 C2 122.6(8) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? N2 C2 C1 122.3(8) . . ? N2 C2 H2 118.8 . . ? C1 C2 H2 118.8 . . ? C4 C3 N2 121.8(8) . . ? C4 C3 H3 119.1 . . ? N2 C3 H3 119.1 . . ? N1 C4 C3 124.0(8) . . ? N1 C4 C5 117.5(8) . . ? C3 C4 C5 118.5(8) . . ? O1 C5 N3 123.4(8) . . ? O1 C5 C4 122.3(8) . . ? N3 C5 C4 114.3(8) . . ? C11 C6 C7 120.3(8) . . ? C11 C6 N3 115.1(7) . . ? C7 C6 N3 124.6(8) . . ? C8 C7 C6 119.8(8) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C7 120.5(8) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 120.2(8) . . ? C8 C9 I1 121.1(6) . . ? C10 C9 I1 118.7(7) . . ? C11 C10 C9 120.2(8) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C6 119.1(7) . . ? C10 C11 H11 120.4 . . ? C6 C11 H11 120.4 . . ? C4 N1 C1 114.7(7) . . ? C2 N2 C3 114.4(8) . . ? C5 N3 C6 128.0(7) . . ? C5 N3 H3B 116.0 . . ? C6 N3 H3B 116.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 3.4(16) . . . . ? N2 C3 C4 N1 -0.3(15) . . . . ? N2 C3 C4 C5 178.9(9) . . . . ? N1 C4 C5 O1 178.6(9) . . . . ? C3 C4 C5 O1 -0.6(15) . . . . ? N1 C4 C5 N3 -2.6(13) . . . . ? C3 C4 C5 N3 178.2(9) . . . . ? C11 C6 C7 C8 0.0(14) . . . . ? N3 C6 C7 C8 177.2(9) . . . . ? C6 C7 C8 C9 0.1(14) . . . . ? C7 C8 C9 C10 0.3(14) . . . . ? C7 C8 C9 I1 -176.6(7) . . . . ? C8 C9 C10 C11 -0.7(14) . . . . ? I1 C9 C10 C11 176.2(7) . . . . ? C9 C10 C11 C6 0.8(14) . . . . ? C7 C6 C11 C10 -0.4(14) . . . . ? N3 C6 C11 C10 -177.9(8) . . . . ? C3 C4 N1 C1 0.8(14) . . . . ? C5 C4 N1 C1 -178.4(9) . . . . ? C2 C1 N1 C4 -2.3(14) . . . . ? C1 C2 N2 C3 -2.7(14) . . . . ? C4 C3 N2 C2 1.2(14) . . . . ? O1 C5 N3 C6 -1.1(16) . . . . ? C4 C5 N3 C6 -179.8(9) . . . . ? C11 C6 N3 C5 -170.8(9) . . . . ? C7 C6 N3 C5 11.9(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.479 _refine_diff_density_min -1.317 _refine_diff_density_rms 0.221 data_d:\determination\solution\2-f\2-f _database_code_depnum_ccdc_archive 'CCDC 919731' #TrackingRef '2-F-Mojaddad.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 F N3 O' _chemical_formula_sum 'C11 H8 F N3 O' _chemical_formula_weight 217.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9967(5) _cell_length_b 7.5829(6) _cell_length_c 19.4101(12) _cell_angle_alpha 98.546(6) _cell_angle_beta 99.133(6) _cell_angle_gamma 96.346(6) _cell_volume 995.93(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9275 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 28.00 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.620 _exptl_absorpt_correction_T_max 0.954 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9275 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4751 _reflns_number_gt 3231 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0708P)^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 4751 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0863 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1339 _refine_ls_wR_factor_gt 0.1146 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.002 _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 C1 C 0.4025(3) 0.4725(3) -0.11716(12) 0.0441(5) Uani 1 1 d . . . H1 H 0.4194 0.5902 -0.0930 0.053 Uiso 1 1 calc R . . C2 C 0.4171(3) 0.4423(3) -0.18786(12) 0.0464(5) Uani 1 1 d . . . H2 H 0.4403 0.5412 -0.2100 0.056 Uiso 1 1 calc R . . C3 C 0.3649(3) 0.1419(3) -0.19089(10) 0.0391(4) Uani 1 1 d . . . H3 H 0.3531 0.0241 -0.2145 0.047 Uiso 1 1 calc R . . C4 C 0.3462(2) 0.1722(2) -0.12023(9) 0.0316(4) Uani 1 1 d . . . C5 C 0.3001(2) 0.0164(2) -0.08340(9) 0.0305(4) Uani 1 1 d . . . C6 C 0.2224(2) -0.0378(2) 0.03284(9) 0.0306(4) Uani 1 1 d . . . C7 C 0.2043(2) 0.0507(2) 0.09929(10) 0.0336(4) Uani 1 1 d . . . C8 C 0.1575(2) -0.0366(3) 0.15245(10) 0.0384(4) Uani 1 1 d . . . H8 H 0.1466 0.0276 0.1961 0.046 Uiso 1 1 calc R . . C9 C 0.1268(2) -0.2231(3) 0.13961(10) 0.0384(4) Uani 1 1 d . . . H9 H 0.0967 -0.2858 0.1750 0.046 Uiso 1 1 calc R . . C10 C 0.1409(2) -0.3157(3) 0.07430(10) 0.0382(4) Uani 1 1 d . . . H10 H 0.1186 -0.4409 0.0660 0.046 Uiso 1 1 calc R . . C11 C 0.1879(2) -0.2254(2) 0.02064(10) 0.0349(4) Uani 1 1 d . . . H11 H 0.1964 -0.2898 -0.0232 0.042 Uiso 1 1 calc R . . C12 C 0.6405(3) 0.0735(3) 0.58730(12) 0.0557(6) Uani 1 1 d . . . H12 H 0.5087 0.0342 0.5696 0.067 Uiso 1 1 calc R . . C13 C 0.7140(3) 0.0654(3) 0.65715(11) 0.0531(5) Uani 1 1 d . . . H13 H 0.6291 0.0218 0.6850 0.064 Uiso 1 1 calc R . . C14 C 1.0138(3) 0.1815(3) 0.64350(11) 0.0467(5) Uani 1 1 d . . . H14 H 1.1456 0.2204 0.6612 0.056 Uiso 1 1 calc R . . C15 C 0.9409(3) 0.1917(3) 0.57394(10) 0.0393(4) Uani 1 1 d . . . C16 C 1.0730(3) 0.2678(3) 0.52855(10) 0.0418(4) Uani 1 1 d . . . C17 C 1.0575(3) 0.3238(3) 0.40488(10) 0.0387(4) Uani 1 1 d . . . C18 C 0.9349(3) 0.2952(3) 0.33945(10) 0.0406(4) Uani 1 1 d . . . C19 C 0.9926(3) 0.3391(3) 0.27927(11) 0.0456(5) Uani 1 1 d . . . H19 H 0.9062 0.3164 0.2363 0.055 Uiso 1 1 calc R . . C20 C 1.1831(3) 0.4182(3) 0.28419(12) 0.0495(5) Uani 1 1 d . . . H20 H 1.2262 0.4501 0.2442 0.059 Uiso 1 1 calc R . . C21 C 1.3095(3) 0.4498(3) 0.34835(12) 0.0501(5) Uani 1 1 d . . . H21 H 1.4373 0.5030 0.3511 0.060 Uiso 1 1 calc R . . C22 C 1.2492(3) 0.4036(3) 0.40865(11) 0.0462(5) Uani 1 1 d . . . H22 H 1.3361 0.4258 0.4515 0.055 Uiso 1 1 calc R . . N1 N 0.3649(2) 0.3377(2) -0.08275(8) 0.0371(4) Uani 1 1 d . . . N2 N 0.3996(2) 0.2781(3) -0.22603(9) 0.0471(4) Uani 1 1 d . . . N3 N 0.27289(19) 0.06875(19) -0.01642(8) 0.0318(3) Uani 1 1 d . . . H3A H 0.2888 0.1831 -0.0020 0.038 Uiso 1 1 calc R . . N4 N 0.7534(2) 0.1360(2) 0.54492(9) 0.0473(4) Uani 1 1 d . . . N5 N 0.9009(3) 0.1173(3) 0.68610(9) 0.0513(4) Uani 1 1 d . . . N6 N 0.9796(2) 0.2692(2) 0.46182(8) 0.0425(4) Uani 1 1 d . . . H6A H 0.8562 0.2317 0.4533 0.051 Uiso 1 1 calc R . . O1 O 0.28891(19) -0.13943(17) -0.11295(7) 0.0397(3) Uani 1 1 d . . . O2 O 1.2451(2) 0.3208(2) 0.55111(8) 0.0604(4) Uani 1 1 d . . . F1 F 0.23366(16) 0.23449(14) 0.11039(6) 0.0442(3) Uani 1 1 d . . . F2 F 0.74763(16) 0.21601(18) 0.33597(6) 0.0527(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 C1 0.0387(10) 0.0340(10) 0.0655(14) 0.0146(9) 0.0197(9) 0.0078(8) C2 0.0338(9) 0.0469(12) 0.0650(14) 0.0290(11) 0.0097(9) 0.0066(8) C3 0.0356(9) 0.0426(11) 0.0376(10) 0.0090(8) 0.0035(7) 0.0003(8) C4 0.0230(7) 0.0332(9) 0.0381(9) 0.0074(7) 0.0022(6) 0.0042(6) C5 0.0261(8) 0.0311(9) 0.0331(9) 0.0049(7) 0.0015(6) 0.0040(6) C6 0.0230(7) 0.0330(9) 0.0356(9) 0.0077(7) 0.0033(6) 0.0037(6) C7 0.0300(8) 0.0303(9) 0.0386(10) 0.0040(7) 0.0030(7) 0.0031(7) C8 0.0339(9) 0.0482(11) 0.0329(9) 0.0084(8) 0.0040(7) 0.0056(8) C9 0.0319(9) 0.0461(11) 0.0402(10) 0.0174(9) 0.0061(7) 0.0054(7) C10 0.0323(9) 0.0345(10) 0.0488(11) 0.0129(8) 0.0060(8) 0.0026(7) C11 0.0305(8) 0.0337(10) 0.0404(10) 0.0053(8) 0.0081(7) 0.0032(7) C12 0.0506(12) 0.0649(15) 0.0464(12) 0.0108(11) 0.0033(10) -0.0080(10) C13 0.0613(13) 0.0551(14) 0.0408(12) 0.0096(10) 0.0085(10) -0.0020(10) C14 0.0494(11) 0.0515(12) 0.0367(11) 0.0055(9) 0.0015(9) 0.0082(9) C15 0.0438(10) 0.0352(10) 0.0352(10) 0.0013(8) 0.0003(8) 0.0056(7) C16 0.0401(10) 0.0458(11) 0.0355(10) 0.0015(8) 0.0006(8) 0.0050(8) C17 0.0407(10) 0.0378(10) 0.0352(10) 0.0016(8) 0.0056(8) 0.0037(7) C18 0.0367(9) 0.0415(11) 0.0408(11) 0.0033(8) 0.0039(8) 0.0016(8) C19 0.0497(11) 0.0512(12) 0.0361(10) 0.0072(9) 0.0051(8) 0.0114(9) C20 0.0540(12) 0.0522(13) 0.0458(12) 0.0099(10) 0.0161(10) 0.0098(9) C21 0.0430(11) 0.0538(13) 0.0525(13) 0.0043(10) 0.0129(9) 0.0026(9) C22 0.0406(10) 0.0507(12) 0.0425(11) -0.0006(9) 0.0040(8) 0.0019(8) N1 0.0334(7) 0.0299(8) 0.0499(9) 0.0074(7) 0.0128(7) 0.0043(6) N2 0.0401(9) 0.0581(12) 0.0442(10) 0.0221(9) 0.0033(7) 0.0001(7) N3 0.0328(7) 0.0276(8) 0.0350(8) 0.0053(6) 0.0072(6) 0.0026(5) N4 0.0476(9) 0.0521(11) 0.0374(9) 0.0065(8) 0.0009(7) -0.0033(8) N5 0.0587(11) 0.0554(11) 0.0383(9) 0.0090(8) 0.0049(8) 0.0061(8) N6 0.0380(8) 0.0508(10) 0.0345(9) 0.0044(7) 0.0015(6) -0.0007(7) O1 0.0509(8) 0.0304(7) 0.0373(7) 0.0041(5) 0.0071(6) 0.0067(5) O2 0.0400(8) 0.0924(13) 0.0437(8) 0.0136(8) -0.0028(6) -0.0011(7) F1 0.0556(7) 0.0343(6) 0.0412(6) 0.0018(5) 0.0108(5) 0.0026(5) F2 0.0409(6) 0.0695(9) 0.0414(7) 0.0066(6) -0.0003(5) -0.0044(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.326(2) . ? C1 C2 1.379(3) . ? C1 H1 0.9300 . ? C2 N2 1.333(3) . ? C2 H2 0.9300 . ? C3 N2 1.340(2) . ? C3 C4 1.386(3) . ? C3 H3 0.9300 . ? C4 N1 1.335(2) . ? C4 C5 1.500(2) . ? C5 O1 1.223(2) . ? C5 N3 1.351(2) . ? C6 C11 1.394(2) . ? C6 C7 1.394(2) . ? C6 N3 1.402(2) . ? C7 F1 1.365(2) . ? C7 C8 1.368(3) . ? C8 C9 1.386(3) . ? C8 H8 0.9300 . ? C9 C10 1.378(3) . ? C9 H9 0.9300 . ? C10 C11 1.391(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 N4 1.328(3) . ? C12 C13 1.385(3) . ? C12 H12 0.9300 . ? C13 N5 1.330(3) . ? C13 H13 0.9300 . ? C14 N5 1.337(3) . ? C14 C15 1.382(3) . ? C14 H14 0.9300 . ? C15 N4 1.338(2) . ? C15 C16 1.502(3) . ? C16 O2 1.215(2) . ? C16 N6 1.357(2) . ? C17 C18 1.388(3) . ? C17 C22 1.395(3) . ? C17 N6 1.403(2) . ? C18 F2 1.366(2) . ? C18 C19 1.369(3) . ? C19 C20 1.382(3) . ? C19 H19 0.9300 . ? C20 C21 1.380(3) . ? C20 H20 0.9300 . ? C21 C22 1.384(3) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? N3 H3A 0.8600 . ? N6 H6A 0.8600 . ? 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 N1 C1 C2 121.57(19) . . ? N1 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? N2 C2 C1 123.20(18) . . ? N2 C2 H2 118.4 . . ? C1 C2 H2 118.4 . . ? N2 C3 C4 121.67(19) . . ? N2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? N1 C4 C3 122.33(16) . . ? N1 C4 C5 117.53(15) . . ? C3 C4 C5 120.13(16) . . ? O1 C5 N3 125.54(16) . . ? O1 C5 C4 121.67(16) . . ? N3 C5 C4 112.80(15) . . ? C11 C6 C7 117.29(16) . . ? C11 C6 N3 125.25(16) . . ? C7 C6 N3 117.46(15) . . ? F1 C7 C8 119.40(16) . . ? F1 C7 C6 117.03(15) . . ? C8 C7 C6 123.56(17) . . ? C7 C8 C9 118.23(17) . . ? C7 C8 H8 120.9 . . ? C9 C8 H8 120.9 . . ? C10 C9 C8 120.01(17) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 121.18(18) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C10 C11 C6 119.71(17) . . ? C10 C11 H11 120.1 . . ? C6 C11 H11 120.1 . . ? N4 C12 C13 121.7(2) . . ? N4 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? N5 C13 C12 122.7(2) . . ? N5 C13 H13 118.6 . . ? C12 C13 H13 118.6 . . ? N5 C14 C15 122.08(19) . . ? N5 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? N4 C15 C14 121.98(18) . . ? N4 C15 C16 117.94(17) . . ? C14 C15 C16 120.08(17) . . ? O2 C16 N6 125.30(18) . . ? O2 C16 C15 121.76(18) . . ? N6 C16 C15 112.94(16) . . ? C18 C17 C22 117.30(17) . . ? C18 C17 N6 117.53(16) . . ? C22 C17 N6 125.17(17) . . ? F2 C18 C19 119.28(17) . . ? F2 C18 C17 117.06(16) . . ? C19 C18 C17 123.66(17) . . ? C18 C19 C20 118.09(19) . . ? C18 C19 H19 121.0 . . ? C20 C19 H19 121.0 . . ? C21 C20 C19 120.08(19) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C22 121.15(19) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? C21 C22 C17 119.72(19) . . ? C21 C22 H22 120.1 . . ? C17 C22 H22 120.1 . . ? C1 N1 C4 116.04(17) . . ? C2 N2 C3 115.16(17) . . ? C5 N3 C6 128.89(15) . . ? C5 N3 H3A 115.6 . . ? C6 N3 H3A 115.6 . . ? C12 N4 C15 116.05(18) . . ? C13 N5 C14 115.47(18) . . ? C16 N6 C17 128.58(16) . . ? C16 N6 H6A 115.7 . . ? C17 N6 H6A 115.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -1.7(3) . . . . ? N2 C3 C4 N1 -1.2(3) . . . . ? N2 C3 C4 C5 177.73(15) . . . . ? N1 C4 C5 O1 -176.79(15) . . . . ? C3 C4 C5 O1 4.2(2) . . . . ? N1 C4 C5 N3 3.5(2) . . . . ? C3 C4 C5 N3 -175.52(15) . . . . ? C11 C6 C7 F1 -178.50(14) . . . . ? N3 C6 C7 F1 1.2(2) . . . . ? C11 C6 C7 C8 0.8(2) . . . . ? N3 C6 C7 C8 -179.41(15) . . . . ? F1 C7 C8 C9 179.46(15) . . . . ? C6 C7 C8 C9 0.1(3) . . . . ? C7 C8 C9 C10 -0.9(3) . . . . ? C8 C9 C10 C11 0.8(3) . . . . ? C9 C10 C11 C6 0.3(3) . . . . ? C7 C6 C11 C10 -1.0(2) . . . . ? N3 C6 C11 C10 179.26(16) . . . . ? N4 C12 C13 N5 -0.7(4) . . . . ? N5 C14 C15 N4 -0.8(3) . . . . ? N5 C14 C15 C16 178.97(19) . . . . ? N4 C15 C16 O2 -179.88(19) . . . . ? C14 C15 C16 O2 0.3(3) . . . . ? N4 C15 C16 N6 0.0(3) . . . . ? C14 C15 C16 N6 -179.78(18) . . . . ? C22 C17 C18 F2 179.63(17) . . . . ? N6 C17 C18 F2 0.0(3) . . . . ? C22 C17 C18 C19 0.7(3) . . . . ? N6 C17 C18 C19 -178.88(19) . . . . ? F2 C18 C19 C20 -179.65(18) . . . . ? C17 C18 C19 C20 -0.8(3) . . . . ? C18 C19 C20 C21 0.4(3) . . . . ? C19 C20 C21 C22 0.0(3) . . . . ? C20 C21 C22 C17 0.0(3) . . . . ? C18 C17 C22 C21 -0.3(3) . . . . ? N6 C17 C22 C21 179.3(2) . . . . ? C2 C1 N1 C4 1.3(3) . . . . ? C3 C4 N1 C1 0.1(2) . . . . ? C5 C4 N1 C1 -178.91(15) . . . . ? C1 C2 N2 C3 0.5(3) . . . . ? C4 C3 N2 C2 0.9(3) . . . . ? O1 C5 N3 C6 -1.8(3) . . . . ? C4 C5 N3 C6 177.93(14) . . . . ? C11 C6 N3 C5 -0.6(3) . . . . ? C7 C6 N3 C5 179.64(15) . . . . ? C13 C12 N4 C15 -0.6(3) . . . . ? C14 C15 N4 C12 1.3(3) . . . . ? C16 C15 N4 C12 -178.52(19) . . . . ? C12 C13 N5 C14 1.1(3) . . . . ? C15 C14 N5 C13 -0.4(3) . . . . ? O2 C16 N6 C17 2.5(3) . . . . ? C15 C16 N6 C17 -177.41(18) . . . . ? C18 C17 N6 C16 173.59(19) . . . . ? C22 C17 N6 C16 -6.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.234 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.079 data_d:\determination\solution\c271\khc271 _database_code_depnum_ccdc_archive 'CCDC 919732' #TrackingRef '3-Brb-Mojaddad.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 Br1 N3 O1' _chemical_formula_sum 'C11 H8 Br1 N3 O1' _chemical_formula_weight 278.10 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.8510(3) _cell_length_b 22.8635(18) _cell_length_c 11.9533(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.229(7) _cell_angle_gamma 90.00 _cell_volume 1051.66(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6754 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 28.00 _exptl_crystal_description Block _exptl_crystal_colour Colorlress _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.757 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 3.888 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4266 _exptl_absorpt_correction_T_max 0.5772 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6754 _diffrn_reflns_av_R_equivalents 0.1193 _diffrn_reflns_av_sigmaI/netI 0.1206 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 27.99 _reflns_number_total 2523 _reflns_number_gt 1489 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0399P)^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 2523 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1195 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.1166 _refine_ls_wR_factor_gt 0.1014 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _refine_ls_shift/su_max 0.007 _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 C1 C 0.5730(16) 0.7544(2) -0.0111(4) 0.0325(13) Uani 1 1 d . . . H1 H 0.6817 0.7469 -0.0777 0.039 Uiso 1 1 calc R . . C2 C 0.5283(18) 0.8120(3) 0.0228(5) 0.0389(15) Uani 1 1 d . . . H2 H 0.5998 0.8419 -0.0236 0.047 Uiso 1 1 calc R . . C3 C 0.2790(16) 0.7809(3) 0.1800(4) 0.0344(14) Uani 1 1 d . . . H3 H 0.1777 0.7886 0.2478 0.041 Uiso 1 1 calc R . . C4 C 0.3132(15) 0.7237(3) 0.1453(4) 0.0286(12) Uani 1 1 d . . . C5 C 0.1750(15) 0.6744(2) 0.2155(4) 0.0275(12) Uani 1 1 d . . . C6 C 0.1333(15) 0.5657(2) 0.2132(4) 0.0259(12) Uani 1 1 d . . . C7 C 0.2115(15) 0.5176(2) 0.1466(4) 0.0269(11) Uani 1 1 d . . . H7 H 0.3167 0.5226 0.0786 0.032 Uiso 1 1 calc R . . C8 C 0.1287(15) 0.4624(2) 0.1845(4) 0.0291(12) Uani 1 1 d . . . C9 C -0.0271(15) 0.4534(2) 0.2837(4) 0.0297(12) Uani 1 1 d . . . H9 H -0.0808 0.4158 0.3073 0.036 Uiso 1 1 calc R . . C10 C -0.1029(15) 0.5016(3) 0.3482(4) 0.0330(13) Uani 1 1 d . . . H10 H -0.2117 0.4963 0.4156 0.040 Uiso 1 1 calc R . . C11 C -0.0202(16) 0.5575(3) 0.3146(4) 0.0302(13) Uani 1 1 d . . . H11 H -0.0674 0.5894 0.3598 0.036 Uiso 1 1 calc R . . N1 N 0.4637(13) 0.7099(2) 0.0497(3) 0.0301(11) Uani 1 1 d . . . N2 N 0.3891(14) 0.8258(2) 0.1179(4) 0.0371(12) Uani 1 1 d . . . N3 N 0.2301(12) 0.62093(18) 0.1715(3) 0.0266(10) Uani 1 1 d . . . H3B H 0.3386 0.6204 0.1100 0.032 Uiso 1 1 calc R . . O1 O 0.0255(12) 0.68462(18) 0.3017(3) 0.0382(10) Uani 1 1 d . . . Br1 Br 0.24779(16) 0.39654(3) 0.09580(4) 0.03228(18) 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 C1 0.039(4) 0.033(3) 0.026(3) 0.002(2) 0.004(2) 0.000(3) C2 0.047(4) 0.032(3) 0.037(3) 0.008(3) -0.003(3) -0.006(3) C3 0.037(4) 0.038(3) 0.029(3) -0.005(2) 0.006(2) 0.004(3) C4 0.030(3) 0.029(3) 0.027(2) -0.004(2) 0.000(2) 0.001(3) C5 0.029(3) 0.033(3) 0.020(2) -0.002(2) 0.000(2) 0.004(3) C6 0.030(3) 0.026(3) 0.022(2) 0.001(2) -0.001(2) -0.004(2) C7 0.031(3) 0.029(3) 0.020(2) 0.002(2) 0.003(2) -0.003(2) C8 0.027(3) 0.034(3) 0.026(2) -0.001(2) -0.004(2) 0.001(3) C9 0.032(3) 0.029(3) 0.028(3) 0.002(2) -0.002(2) -0.005(2) C10 0.030(3) 0.044(4) 0.025(3) 0.007(2) -0.001(2) -0.009(3) C11 0.037(3) 0.034(3) 0.020(2) -0.002(2) 0.004(2) -0.001(3) N1 0.034(3) 0.030(3) 0.026(2) 0.0004(18) 0.0047(19) 0.000(2) N2 0.045(3) 0.028(3) 0.039(3) -0.002(2) 0.007(2) -0.003(2) N3 0.034(3) 0.025(2) 0.0214(19) -0.0015(16) 0.0067(18) 0.0021(19) O1 0.050(3) 0.036(2) 0.0290(18) -0.0022(17) 0.0140(18) 0.000(2) Br1 0.0363(3) 0.0283(3) 0.0324(3) -0.0026(3) 0.00245(19) 0.0000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.327(7) . ? C1 C2 1.391(8) . ? C1 H1 0.9300 . ? C2 N2 1.314(8) . ? C2 H2 0.9300 . ? C3 N2 1.345(7) . ? C3 C4 1.380(8) . ? C3 H3 0.9300 . ? C4 N1 1.339(7) . ? C4 C5 1.514(8) . ? C5 O1 1.222(6) . ? C5 N3 1.351(6) . ? C6 C11 1.382(7) . ? C6 C7 1.397(8) . ? C6 N3 1.413(7) . ? C7 C8 1.383(8) . ? C7 H7 0.9300 . ? C8 C9 1.365(8) . ? C8 Br1 1.908(6) . ? C9 C10 1.383(8) . ? C9 H9 0.9300 . ? C10 C11 1.381(8) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? N3 H3B 0.8600 . ? 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 N1 C1 C2 121.3(5) . . ? N1 C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? N2 C2 C1 122.6(6) . . ? N2 C2 H2 118.7 . . ? C1 C2 H2 118.7 . . ? N2 C3 C4 121.5(5) . . ? N2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? N1 C4 C3 121.9(5) . . ? N1 C4 C5 118.1(5) . . ? C3 C4 C5 120.0(5) . . ? O1 C5 N3 126.0(5) . . ? O1 C5 C4 120.8(5) . . ? N3 C5 C4 113.2(5) . . ? C11 C6 C7 120.1(5) . . ? C11 C6 N3 123.9(5) . . ? C7 C6 N3 115.9(4) . . ? C8 C7 C6 118.3(5) . . ? C8 C7 H7 120.8 . . ? C6 C7 H7 120.8 . . ? C9 C8 C7 122.5(5) . . ? C9 C8 Br1 119.2(4) . . ? C7 C8 Br1 118.3(4) . . ? C8 C9 C10 118.3(5) . . ? C8 C9 H9 120.9 . . ? C10 C9 H9 120.9 . . ? C11 C10 C9 121.3(5) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C6 119.5(5) . . ? C10 C11 H11 120.3 . . ? C6 C11 H11 120.3 . . ? C1 N1 C4 116.4(5) . . ? C2 N2 C3 116.2(5) . . ? C5 N3 C6 128.6(5) . . ? C5 N3 H3B 115.7 . . ? C6 N3 H3B 115.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 2.6(10) . . . . ? N2 C3 C4 N1 1.5(9) . . . . ? N2 C3 C4 C5 -177.9(5) . . . . ? N1 C4 C5 O1 -177.6(5) . . . . ? C3 C4 C5 O1 1.7(8) . . . . ? N1 C4 C5 N3 1.2(7) . . . . ? C3 C4 C5 N3 -179.4(5) . . . . ? C11 C6 C7 C8 0.6(8) . . . . ? N3 C6 C7 C8 178.7(5) . . . . ? C6 C7 C8 C9 0.3(8) . . . . ? C6 C7 C8 Br1 -178.2(4) . . . . ? C7 C8 C9 C10 -0.2(8) . . . . ? Br1 C8 C9 C10 178.3(4) . . . . ? C8 C9 C10 C11 -0.8(8) . . . . ? C9 C10 C11 C6 1.7(9) . . . . ? C7 C6 C11 C10 -1.6(9) . . . . ? N3 C6 C11 C10 -179.5(5) . . . . ? C2 C1 N1 C4 -0.8(8) . . . . ? C3 C4 N1 C1 -1.2(8) . . . . ? C5 C4 N1 C1 178.2(5) . . . . ? C1 C2 N2 C3 -2.3(9) . . . . ? C4 C3 N2 C2 0.3(9) . . . . ? O1 C5 N3 C6 -0.3(9) . . . . ? C4 C5 N3 C6 -179.1(5) . . . . ? C11 C6 N3 C5 -4.8(9) . . . . ? C7 C6 N3 C5 177.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.531 _refine_diff_density_min -0.682 _refine_diff_density_rms 0.114 data_d:\determination\solution\khc269\khc269 _database_code_depnum_ccdc_archive 'CCDC 919733' #TrackingRef '3-Cl-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 Cl1 N3 O1' _chemical_formula_sum 'C11 H8 Cl1 N3 O1' _chemical_formula_weight 233.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.1207(7) _cell_length_b 11.0228(7) _cell_length_c 18.8469(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.255(6) _cell_angle_gamma 90.00 _cell_volume 2102.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 14993 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.00 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.343 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.840 _exptl_absorpt_correction_T_max 0.920 _exptl_absorpt_process_details 'SADABS (Sheldric, 1998a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'APEX2 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5241 _diffrn_reflns_av_R_equivalents 0.0917 _diffrn_reflns_av_sigmaI/netI 0.1145 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5081 _reflns_number_gt 4782 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.1128P)^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 5081 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0919 _refine_ls_R_factor_gt 0.0817 _refine_ls_wR_factor_ref 0.1411 _refine_ls_wR_factor_gt 0.1111 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 C1 C 0.4493(8) 0.4591(7) -0.0901(4) 0.0259(18) Uani 1 1 d . . . H1 H 0.4980 0.5288 -0.0992 0.031 Uiso 1 1 calc R . . C2 C 0.4808(8) 0.3522(8) -0.1262(4) 0.030(2) Uani 1 1 d . . . H2 H 0.5539 0.3518 -0.1560 0.036 Uiso 1 1 calc R . . C3 C 0.3079(9) 0.2574(7) -0.0752(5) 0.030(2) Uani 1 1 d . . . H3 H 0.2532 0.1902 -0.0701 0.037 Uiso 1 1 calc R . . C4 C 0.2809(8) 0.3613(7) -0.0365(4) 0.0236(17) Uani 1 1 d . . . C5 C 0.1691(7) 0.3579(7) 0.0173(4) 0.0217(17) Uani 1 1 d . . . C6 C 0.0501(8) 0.4889(7) 0.1035(4) 0.0208(17) Uani 1 1 d . . . C7 C -0.0479(8) 0.4037(7) 0.1205(4) 0.0248(17) Uani 1 1 d . . . H7 H -0.0530 0.3284 0.0985 0.030 Uiso 1 1 calc R . . C8 C -0.1379(7) 0.4398(7) 0.1731(4) 0.0241(18) Uani 1 1 d . . . C9 C -0.1342(9) 0.5473(8) 0.2072(4) 0.032(2) Uani 1 1 d . . . H9 H -0.1960 0.5659 0.2419 0.039 Uiso 1 1 calc R . . C10 C -0.0352(9) 0.6305(7) 0.1892(5) 0.032(2) Uani 1 1 d . . . H10 H -0.0317 0.7060 0.2111 0.038 Uiso 1 1 calc R . . C11 C 0.0577(8) 0.5988(8) 0.1384(4) 0.0278(18) Uani 1 1 d . . . H11 H 0.1258 0.6524 0.1277 0.033 Uiso 1 1 calc R . . C12 C 0.7967(8) 0.0468(8) 0.0125(5) 0.035(2) Uani 1 1 d . . . H12 H 0.8540 -0.0188 0.0086 0.042 Uiso 1 1 calc R . . C13 C 0.8273(8) 0.1534(8) -0.0211(5) 0.030(2) Uani 1 1 d . . . H13 H 0.9049 0.1570 -0.0472 0.037 Uiso 1 1 calc R . . C14 C 0.6412(9) 0.2400(8) 0.0201(4) 0.031(2) Uani 1 1 d . . . H14 H 0.5839 0.3057 0.0237 0.037 Uiso 1 1 calc R . . C15 C 0.6084(8) 0.1346(7) 0.0545(4) 0.0252(18) Uani 1 1 d . . . C16 C 0.4820(8) 0.1281(7) 0.0984(4) 0.0226(17) Uani 1 1 d . . . C17 C 0.3446(8) -0.0137(7) 0.1672(4) 0.0227(17) Uani 1 1 d . . . C18 C 0.2230(8) 0.0494(7) 0.1579(4) 0.0236(17) Uani 1 1 d . . . H18 H 0.2150 0.1133 0.1260 0.028 Uiso 1 1 calc R . . C19 C 0.1165(8) 0.0111(8) 0.1989(4) 0.0275(19) Uani 1 1 d . . . C20 C 0.1271(8) -0.0808(8) 0.2487(4) 0.030(2) Uani 1 1 d . . . H20 H 0.0556 -0.1015 0.2771 0.036 Uiso 1 1 calc R . . C21 C 0.2489(9) -0.1422(7) 0.2554(4) 0.0274(19) Uani 1 1 d . . . H21 H 0.2568 -0.2062 0.2873 0.033 Uiso 1 1 calc R . . C22 C 0.3563(8) -0.1083(7) 0.2152(4) 0.0249(17) Uani 1 1 d . . . H22 H 0.4363 -0.1489 0.2203 0.030 Uiso 1 1 calc R . . N1 N 0.3509(7) 0.4641(6) -0.0426(3) 0.0253(15) Uani 1 1 d . . . N2 N 0.4096(8) 0.2507(7) -0.1195(4) 0.0361(19) Uani 1 1 d . . . N3 N 0.1458(7) 0.4629(6) 0.0510(3) 0.0241(15) Uani 1 1 d . . . H3A H 0.1957 0.5226 0.0391 0.029 Uiso 1 1 calc R . . N4 N 0.6853(7) 0.0343(6) 0.0512(4) 0.0288(16) Uani 1 1 d . . . N5 N 0.7505(7) 0.2536(7) -0.0181(4) 0.0323(18) Uani 1 1 d . . . N6 N 0.4562(6) 0.0172(6) 0.1259(3) 0.0252(15) Uani 1 1 d . . . H6A H 0.5125 -0.0394 0.1175 0.030 Uiso 1 1 calc R . . Cl1 Cl -0.2614(2) 0.3307(2) 0.19524(12) 0.0338(6) Uani 1 1 d . . . Cl2 Cl -0.0365(2) 0.0872(2) 0.18674(13) 0.0430(7) Uani 1 1 d . . . O1 O 0.1085(6) 0.2632(5) 0.0262(3) 0.0332(14) Uani 1 1 d . . . O2 O 0.4153(6) 0.2205(5) 0.1055(4) 0.0372(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.025(4) 0.023(4) 0.030(4) 0.002(3) 0.008(4) 0.004(3) C2 0.016(4) 0.046(5) 0.028(4) 0.003(4) 0.012(3) 0.001(4) C3 0.032(5) 0.023(4) 0.036(5) 0.001(4) 0.015(4) 0.007(4) C4 0.022(4) 0.024(4) 0.025(4) -0.003(3) 0.007(3) -0.004(3) C5 0.018(4) 0.019(4) 0.028(4) 0.008(3) 0.008(3) 0.005(3) C6 0.020(4) 0.029(4) 0.014(4) 0.006(3) 0.001(3) -0.004(3) C7 0.025(4) 0.022(4) 0.028(4) -0.003(3) 0.006(3) -0.004(3) C8 0.022(3) 0.033(4) 0.027(4) 0.012(3) 0.017(3) 0.002(3) C9 0.027(4) 0.039(5) 0.032(5) -0.006(4) 0.015(4) 0.004(4) C10 0.042(5) 0.018(4) 0.035(5) 0.001(4) 0.011(4) -0.002(4) C11 0.026(4) 0.033(4) 0.024(4) -0.002(4) 0.010(3) -0.001(4) C12 0.019(4) 0.036(5) 0.049(6) 0.004(4) 0.009(4) 0.003(4) C13 0.024(4) 0.025(4) 0.043(5) 0.001(4) 0.015(4) -0.009(4) C14 0.034(5) 0.026(4) 0.032(5) -0.001(4) 0.006(4) 0.002(4) C15 0.020(4) 0.026(4) 0.030(4) 0.000(3) 0.002(3) 0.005(3) C16 0.026(4) 0.026(4) 0.016(4) -0.005(3) -0.001(3) 0.000(3) C17 0.023(4) 0.024(4) 0.022(4) 0.003(3) 0.007(3) 0.000(3) C18 0.023(4) 0.024(4) 0.024(4) 0.004(3) 0.010(3) 0.012(3) C19 0.024(4) 0.028(4) 0.031(4) 0.000(4) 0.011(4) 0.006(3) C20 0.023(4) 0.036(5) 0.033(4) -0.008(4) 0.018(4) -0.014(4) C21 0.047(5) 0.021(4) 0.015(4) -0.004(3) 0.015(3) -0.002(4) C22 0.020(4) 0.023(4) 0.032(4) 0.000(3) 0.007(3) 0.001(3) N1 0.025(4) 0.023(4) 0.028(4) 0.000(3) 0.002(3) 0.004(3) N2 0.035(4) 0.032(4) 0.041(4) -0.003(3) 0.018(4) 0.006(3) N3 0.024(3) 0.020(3) 0.028(4) 0.001(3) 0.009(3) -0.003(3) N4 0.025(4) 0.030(4) 0.032(4) 0.000(3) 0.016(3) -0.001(3) N5 0.032(4) 0.034(4) 0.032(4) 0.003(3) 0.018(3) -0.003(3) N6 0.022(3) 0.026(4) 0.028(4) 0.004(3) 0.011(3) 0.004(3) Cl1 0.0230(10) 0.0345(11) 0.0439(12) 0.0063(10) 0.0179(9) -0.0007(9) Cl2 0.0213(10) 0.0581(15) 0.0497(14) 0.0135(12) 0.0141(10) 0.0085(11) O1 0.024(3) 0.033(3) 0.043(3) -0.001(3) 0.018(3) -0.003(3) O2 0.029(3) 0.025(3) 0.057(4) 0.001(3) 0.018(3) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.342(10) . ? C1 C2 1.398(11) . ? C1 H1 0.9300 . ? C2 N2 1.337(11) . ? C2 H2 0.9300 . ? C3 N2 1.330(10) . ? C3 C4 1.386(11) . ? C3 H3 0.9300 . ? C4 N1 1.341(10) . ? C4 C5 1.523(10) . ? C5 O1 1.222(9) . ? C5 N3 1.343(10) . ? C6 C11 1.381(11) . ? C6 C7 1.404(11) . ? C6 N3 1.417(9) . ? C7 C8 1.406(10) . ? C7 H7 0.9300 . ? C8 C9 1.349(12) . ? C8 Cl1 1.786(7) . ? C9 C10 1.400(12) . ? C9 H9 0.9300 . ? C10 C11 1.390(11) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 N4 1.353(10) . ? C12 C13 1.371(12) . ? C12 H12 0.9300 . ? C13 N5 1.352(11) . ? C13 H13 0.9300 . ? C14 N5 1.331(10) . ? C14 C15 1.372(12) . ? C14 H14 0.9300 . ? C15 N4 1.353(10) . ? C15 C16 1.528(10) . ? C16 O2 1.230(10) . ? C16 N6 1.353(10) . ? C17 C22 1.384(11) . ? C17 N6 1.417(9) . ? C17 C18 1.424(11) . ? C18 C19 1.394(10) . ? C18 H18 0.9300 . ? C19 C20 1.386(12) . ? C19 Cl2 1.775(8) . ? C20 C21 1.411(12) . ? C20 H20 0.9300 . ? C21 C22 1.379(11) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? N3 H3A 0.8600 . ? N6 H6A 0.8600 . ? 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 N1 C1 C2 122.1(7) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? N2 C2 C1 122.3(7) . . ? N2 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? N2 C3 C4 122.1(8) . . ? N2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? N1 C4 C3 123.2(7) . . ? N1 C4 C5 118.1(7) . . ? C3 C4 C5 118.6(7) . . ? O1 C5 N3 125.6(7) . . ? O1 C5 C4 119.2(7) . . ? N3 C5 C4 115.3(7) . . ? C11 C6 C7 121.1(7) . . ? C11 C6 N3 118.2(7) . . ? C7 C6 N3 120.7(7) . . ? C6 C7 C8 115.6(7) . . ? C6 C7 H7 122.2 . . ? C8 C7 H7 122.2 . . ? C9 C8 C7 124.6(7) . . ? C9 C8 Cl1 119.9(6) . . ? C7 C8 Cl1 115.5(6) . . ? C8 C9 C10 118.6(7) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? C11 C10 C9 119.3(8) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C6 C11 C10 120.8(8) . . ? C6 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? N4 C12 C13 121.8(8) . . ? N4 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? N5 C13 C12 123.3(7) . . ? N5 C13 H13 118.3 . . ? C12 C13 H13 118.3 . . ? N5 C14 C15 123.7(8) . . ? N5 C14 H14 118.2 . . ? C15 C14 H14 118.2 . . ? N4 C15 C14 122.0(7) . . ? N4 C15 C16 118.0(7) . . ? C14 C15 C16 120.0(7) . . ? O2 C16 N6 126.8(7) . . ? O2 C16 C15 118.8(7) . . ? N6 C16 C15 114.4(7) . . ? C22 C17 N6 118.3(7) . . ? C22 C17 C18 121.3(7) . . ? N6 C17 C18 120.3(7) . . ? C19 C18 C17 117.0(7) . . ? C19 C18 H18 121.5 . . ? C17 C18 H18 121.5 . . ? C20 C19 C18 122.7(8) . . ? C20 C19 Cl2 119.8(6) . . ? C18 C19 Cl2 117.5(6) . . ? C19 C20 C21 118.4(7) . . ? C19 C20 H20 120.8 . . ? C21 C20 H20 120.8 . . ? C22 C21 C20 120.8(8) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C21 C22 C17 119.8(8) . . ? C21 C22 H22 120.1 . . ? C17 C22 H22 120.1 . . ? C4 N1 C1 114.5(7) . . ? C3 N2 C2 115.6(7) . . ? C5 N3 C6 128.8(7) . . ? C5 N3 H3A 115.6 . . ? C6 N3 H3A 115.6 . . ? C12 N4 C15 115.0(7) . . ? C14 N5 C13 114.2(7) . . ? C16 N6 C17 125.7(7) . . ? C16 N6 H6A 117.1 . . ? C17 N6 H6A 117.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 4.6(14) . . . . ? N2 C3 C4 N1 2.8(14) . . . . ? N2 C3 C4 C5 -175.2(8) . . . . ? N1 C4 C5 O1 -176.4(8) . . . . ? C3 C4 C5 O1 1.7(12) . . . . ? N1 C4 C5 N3 4.1(11) . . . . ? C3 C4 C5 N3 -177.8(8) . . . . ? C11 C6 C7 C8 1.8(12) . . . . ? N3 C6 C7 C8 -179.7(7) . . . . ? C6 C7 C8 C9 -0.7(13) . . . . ? C6 C7 C8 Cl1 -179.5(6) . . . . ? C7 C8 C9 C10 0.6(14) . . . . ? Cl1 C8 C9 C10 179.3(7) . . . . ? C8 C9 C10 C11 -1.6(14) . . . . ? C7 C6 C11 C10 -2.9(13) . . . . ? N3 C6 C11 C10 178.5(8) . . . . ? C9 C10 C11 C6 2.7(14) . . . . ? N4 C12 C13 N5 0.3(15) . . . . ? N5 C14 C15 N4 -1.0(14) . . . . ? N5 C14 C15 C16 178.8(8) . . . . ? N4 C15 C16 O2 175.6(8) . . . . ? C14 C15 C16 O2 -4.2(12) . . . . ? N4 C15 C16 N6 -4.3(11) . . . . ? C14 C15 C16 N6 175.9(8) . . . . ? C22 C17 C18 C19 -0.4(12) . . . . ? N6 C17 C18 C19 178.0(7) . . . . ? C17 C18 C19 C20 2.5(12) . . . . ? C17 C18 C19 Cl2 -178.9(6) . . . . ? C18 C19 C20 C21 -3.5(13) . . . . ? Cl2 C19 C20 C21 177.9(6) . . . . ? C19 C20 C21 C22 2.5(12) . . . . ? C20 C21 C22 C17 -0.5(12) . . . . ? N6 C17 C22 C21 -178.9(7) . . . . ? C18 C17 C22 C21 -0.5(12) . . . . ? C3 C4 N1 C1 0.7(12) . . . . ? C5 C4 N1 C1 178.7(7) . . . . ? C2 C1 N1 C4 -4.2(12) . . . . ? C4 C3 N2 C2 -2.5(13) . . . . ? C1 C2 N2 C3 -1.0(13) . . . . ? O1 C5 N3 C6 0.6(14) . . . . ? C4 C5 N3 C6 -179.8(7) . . . . ? C11 C6 N3 C5 170.2(8) . . . . ? C7 C6 N3 C5 -8.3(13) . . . . ? C13 C12 N4 C15 -0.6(13) . . . . ? C14 C15 N4 C12 0.9(12) . . . . ? C16 C15 N4 C12 -179.0(7) . . . . ? C15 C14 N5 C13 0.7(13) . . . . ? C12 C13 N5 C14 -0.4(13) . . . . ? O2 C16 N6 C17 1.4(14) . . . . ? C15 C16 N6 C17 -178.7(7) . . . . ? C22 C17 N6 C16 -153.0(8) . . . . ? C18 C17 N6 C16 28.6(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.682 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.116 data_d:\determination\solution\khc28-2\3f- _database_code_depnum_ccdc_archive 'CCDC 919734' #TrackingRef '3-Fa-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 F1 N3 O1' _chemical_formula_sum 'C11 H8 F1 N3 O1' _chemical_formula_weight 217.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.8921(1) _cell_length_b 27.1491(4) _cell_length_c 6.4010(2) _cell_angle_alpha 90 _cell_angle_beta 109.455(2) _cell_angle_gamma 90 _cell_volume 965.47(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3399 _cell_measurement_theta_min 1.48 _cell_measurement_theta_max 28.00 _exptl_crystal_description Block _exptl_crystal_colour Colorles _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.968 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3399 _diffrn_reflns_av_R_equivalents 0.1012 _diffrn_reflns_av_sigmaI/netI 0.1020 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2302 _reflns_number_gt 2202 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] 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 1702 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1093 _refine_ls_R_factor_gt 0.0710 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1209 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.020 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 C1 C 0.82005(9) 0.44552(2) 1.23400(9) 0.02753(15) Uani 1 1 d . . . H1 H 0.9849 0.4483 1.3006 0.033 Uiso 1 1 calc R . . C2 C 0.67127(11) 0.46604(2) 1.33870(11) 0.02817(18) Uani 1 1 d . . . H2 H 0.7407 0.4811 1.4730 0.034 Uiso 1 1 calc R . . C3 C 0.34568(12) 0.44095(2) 1.05564(10) 0.02685(15) Uani 1 1 d . . . H3 H 0.1808 0.4390 0.9873 0.032 Uiso 1 1 calc R . . C4 C 0.49435(13) 0.41936(2) 0.95311(10) 0.02299(13) Uani 1 1 d . . . C5 C 0.38266(13) 0.39272(2) 0.73703(9) 0.02361(14) Uani 1 1 d . . . C6 C 0.49298(12) 0.34348(2) 0.45782(9) 0.02229(13) Uani 1 1 d . . . C7 C 0.26384(11) 0.339560(19) 0.30044(9) 0.02438(14) Uani 1 1 d . . . H7 H 0.1323 0.3544 0.3205 0.029 Uiso 1 1 calc R . . C8 C 0.23957(10) 0.31239(2) 0.11077(8) 0.02505(14) Uani 1 1 d . . . C9 C 0.42583(12) 0.28880(2) 0.06858(9) 0.02661(15) Uani 1 1 d . . . H9 H 0.4014 0.2713 -0.0590 0.032 Uiso 1 1 calc R . . C10 C 0.65292(10) 0.29280(2) 0.22931(9) 0.02686(16) Uani 1 1 d . . . H10 H 0.7828 0.2773 0.2093 0.032 Uiso 1 1 calc R . . C11 C 0.68717(11) 0.320023(19) 0.42093(8) 0.02541(14) Uani 1 1 d . . . H11 H 0.8396 0.3225 0.5242 0.030 Uiso 1 1 calc R . . N1 N 0.73408(9) 0.421860(17) 1.03989(8) 0.02547(14) Uani 1 1 d . . . N2 N 0.43247(9) 0.46447(2) 1.25012(8) 0.02920(13) Uani 1 1 d . . . N3 N 0.54231(8) 0.371139(19) 0.65540(7) 0.02460(13) Uani 1 1 d . . . H3A H 0.6910 0.3746 0.7321 0.030 Uiso 1 1 calc R . . O1 O 0.16385(8) 0.391508(16) 0.65059(7) 0.03261(12) Uani 1 1 d . . . F1 F 0.01634(6) 0.309256(13) -0.04428(5) 0.03304(10) 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 C1 0.0262(4) 0.0262(3) 0.0258(3) -0.0049(3) 0.0032(3) 0.0005(3) C2 0.0328(5) 0.0261(4) 0.0249(4) -0.0054(3) 0.0089(3) -0.0015(3) C3 0.0271(4) 0.0283(5) 0.0255(3) -0.0018(3) 0.0093(3) -0.0021(3) C4 0.0271(3) 0.0211(3) 0.0210(3) 0.0015(2) 0.0086(3) -0.0006(3) C5 0.0259(3) 0.0256(3) 0.0195(4) 0.0008(2) 0.0079(3) -0.0016(3) C6 0.0269(3) 0.0210(3) 0.0180(3) 0.0002(3) 0.0064(3) -0.0021(3) C7 0.0259(4) 0.0241(3) 0.0229(3) 0.0024(3) 0.0081(3) 0.0008(3) C8 0.0253(4) 0.0272(4) 0.0185(3) 0.0029(3) 0.0034(3) -0.0041(3) C9 0.0338(4) 0.0257(4) 0.0220(3) -0.0036(3) 0.0117(3) -0.0045(3) C10 0.0271(4) 0.0291(4) 0.0273(3) -0.0012(3) 0.0131(3) 0.0000(3) C11 0.0236(3) 0.0297(4) 0.0229(3) -0.0003(3) 0.0078(3) -0.0035(3) N1 0.0269(3) 0.0259(3) 0.0240(3) -0.0033(2) 0.0062(3) 0.0005(2) N2 0.0309(4) 0.0293(3) 0.0293(3) -0.0056(3) 0.0127(3) -0.0031(3) N3 0.0229(3) 0.0282(3) 0.0206(3) -0.0033(2) 0.0046(2) -0.0006(2) O1 0.0251(3) 0.0444(3) 0.0281(3) -0.0008(2) 0.0060(2) -0.0009(2) F1 0.0266(2) 0.0448(2) 0.02214(17) -0.00635(18) 0.00112(17) -0.00209(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 C1 N1 1.3393(7) . ? C1 C2 1.3847(9) . ? C1 H1 0.9300 . ? C2 N2 1.3310(9) . ? C2 H2 0.9300 . ? C3 N2 1.3397(8) . ? C3 C4 1.3873(10) . ? C3 H3 0.9300 . ? C4 N1 1.3363(9) . ? C4 C5 1.5043(8) . ? C5 O1 1.2224(9) . ? C5 N3 1.3523(9) . ? C6 C7 1.3939(9) . ? C6 C11 1.3966(9) . ? C6 N3 1.4153(7) . ? C7 C8 1.3867(7) . ? C7 H7 0.9300 . ? C8 F1 1.3611(7) . ? C8 C9 1.3729(9) . ? C9 C10 1.3941(9) . ? C9 H9 0.9100 . ? C10 C11 1.3880(7) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? N3 H3A 0.8600 . ? 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 N1 C1 C2 122.47(5) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? N2 C2 C1 122.04(6) . . ? N2 C2 H2 119.1 . . ? C1 C2 H2 118.1 . . ? N2 C3 C4 122.36(6) . . ? N2 C3 H3 118.5 . . ? C4 C3 H3 118.5 . . ? N1 C4 C3 121.90(6) . . ? N1 C4 C5 119.00(6) . . ? C3 C4 C5 119.10(7) . . ? O1 C5 N3 125.31(5) . . ? O1 C5 C4 120.11(6) . . ? N3 C5 C4 114.58(6) . . ? C7 C6 C11 119.60(5) . . ? C7 C6 N3 123.21(6) . . ? C11 C6 N3 117.20(5) . . ? C6 C7 C8 117.77(6) . . ? C6 C7 H7 121.1 . . ? C8 C7 H7 121.1 . . ? F1 C8 C9 117.97(5) . . ? F1 C8 C7 117.68(5) . . ? C9 C8 C7 124.35(5) . . ? C8 C9 C10 116.88(5) . . ? C8 C9 H9 121.8 . . ? C10 C9 H9 121.8 . . ? C9 C10 C11 121.04(6) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C10 C11 C6 120.40(5) . . ? C10 C11 H11 119.5 . . ? C6 C11 H11 119.5 . . ? C4 N1 C1 115.52(5) . . ? C2 N2 C3 115.68(6) . . ? C5 N3 C6 127.80(5) . . ? C5 N3 H3A 115.8 . . ? C6 N3 H3A 115.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -1.57(9) . . . . ? N2 C3 C4 N1 -1.76(10) . . . . ? N2 C3 C4 C5 178.74(5) . . . . ? N1 C4 C5 O1 -177.33(6) . . . . ? C3 C4 C5 O1 2.18(9) . . . . ? N1 C4 C5 N3 3.26(8) . . . . ? C3 C4 C5 N3 -177.23(6) . . . . ? C11 C6 C7 C8 -0.49(9) . . . . ? N3 C6 C7 C8 178.38(6) . . . . ? C6 C7 C8 F1 -178.98(5) . . . . ? C6 C7 C8 C9 0.54(9) . . . . ? F1 C8 C9 C10 179.64(5) . . . . ? C7 C8 C9 C10 0.12(10) . . . . ? C8 C9 C10 C11 -0.84(10) . . . . ? C9 C10 C11 C6 0.90(10) . . . . ? C7 C6 C11 C10 -0.20(10) . . . . ? N3 C6 C11 C10 -179.13(5) . . . . ? C3 C4 N1 C1 1.46(8) . . . . ? C5 C4 N1 C1 -179.04(6) . . . . ? C2 C1 N1 C4 0.10(8) . . . . ? C1 C2 N2 C3 1.28(8) . . . . ? C4 C3 N2 C2 0.29(9) . . . . ? O1 C5 N3 C6 0.30(11) . . . . ? C4 C5 N3 C6 179.67(5) . . . . ? C7 C6 N3 C5 8.36(10) . . . . ? C11 C6 N3 C5 -172.84(5) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.574 _refine_diff_density_min -0.602 _refine_diff_density_rms 0.012 data_d:\determination\solution\3-f\3-f _database_code_depnum_ccdc_archive 'CCDC 919735' #TrackingRef '3-Fb-New.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 F1 N3 O1' _chemical_formula_sum 'C11 H8 F1 N3 O1' _chemical_formula_weight 217.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 11.7158(11) _cell_length_b 3.8018(4) _cell_length_c 10.9082(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.377(7) _cell_angle_gamma 90.00 _cell_volume 477.92(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3005 _cell_measurement_theta_min 3.54 _cell_measurement_theta_max 28.00 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3005 _diffrn_reflns_av_R_equivalents 0.0701 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 27.99 _reflns_number_total 1815 _reflns_number_gt 1314 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0429P)^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 SHELXL _refine_ls_extinction_coef 0.063(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(1) _refine_ls_number_reflns 1815 _refine_ls_number_parameters 146 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0907 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1052 _refine_ls_wR_factor_gt 0.0973 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.060 _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 C1 C -0.1164(3) -0.2277(13) 0.5782(3) 0.0319(10) Uani 1 1 d . . . H1 H -0.1497 -0.2172 0.6493 0.038 Uiso 1 1 calc R . . C2 C -0.1806(3) -0.3650(11) 0.4697(3) 0.0295(10) Uani 1 1 d . . . H2 H -0.2555 -0.4444 0.4705 0.035 Uiso 1 1 calc R . . C3 C -0.0298(3) -0.2662(12) 0.3707(3) 0.0295(10) Uani 1 1 d . . . H3 H 0.0038 -0.2757 0.2998 0.035 Uiso 1 1 calc R . . C4 C 0.0341(3) -0.1280(11) 0.4787(3) 0.0229(8) Uani 1 1 d . . . C5 C 0.1549(3) 0.0041(11) 0.4791(3) 0.0228(8) Uani 1 1 d . . . C6 C 0.3321(3) 0.1920(11) 0.6235(3) 0.0249(9) Uani 1 1 d . . . C7 C 0.4127(3) 0.0907(10) 0.5512(3) 0.0236(8) Uani 1 1 d . . . H7 H 0.3900 -0.0265 0.4759 0.028 Uiso 1 1 calc R . . C8 C 0.5268(3) 0.1694(10) 0.5947(3) 0.0237(9) Uani 1 1 d . . . C9 C 0.5658(3) 0.3469(11) 0.7030(3) 0.0276(10) Uani 1 1 d . . . H9 H 0.6441 0.3967 0.7289 0.033 Uiso 1 1 calc R . . C10 C 0.4839(3) 0.4498(11) 0.7729(3) 0.0286(9) Uani 1 1 d . . . H10 H 0.5076 0.5719 0.8470 0.034 Uiso 1 1 calc R . . C11 C 0.3683(3) 0.3747(10) 0.7346(3) 0.0253(9) Uani 1 1 d . . . H11 H 0.3143 0.4452 0.7826 0.030 Uiso 1 1 calc R . . N1 N -0.0088(3) -0.1103(10) 0.5837(3) 0.0282(8) Uani 1 1 d . . . N2 N -0.1384(3) -0.3874(10) 0.3638(3) 0.0335(9) Uani 1 1 d . . . N3 N 0.2136(2) 0.0923(8) 0.5924(2) 0.0265(8) Uani 1 1 d . . . H3A H 0.1752 0.0877 0.6526 0.032 Uiso 1 1 calc R . . O1 O 0.1926(2) 0.0224(8) 0.3817(2) 0.0341(7) Uani 1 1 d . . . F1 F 0.60656(17) 0.0616(7) 0.52553(16) 0.0347(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.024(2) 0.047(3) 0.0274(19) 0.002(2) 0.0125(16) -0.002(2) C2 0.0171(19) 0.038(3) 0.0335(19) 0.002(2) 0.0054(16) -0.0031(19) C3 0.028(2) 0.037(3) 0.0243(17) -0.0014(18) 0.0055(15) 0.000(2) C4 0.0220(19) 0.023(2) 0.0245(16) 0.0035(15) 0.0057(14) 0.0029(16) C5 0.0208(18) 0.025(2) 0.0225(16) 0.0015(15) 0.0037(14) 0.0024(16) C6 0.0190(18) 0.027(3) 0.0301(18) 0.0043(16) 0.0089(14) -0.0009(17) C7 0.0261(18) 0.024(2) 0.0206(15) 0.0001(16) 0.0051(14) 0.0010(18) C8 0.023(2) 0.024(2) 0.0252(18) 0.0058(16) 0.0062(16) 0.0033(17) C9 0.024(2) 0.030(3) 0.0277(19) 0.0058(17) -0.0004(15) -0.0028(18) C10 0.028(2) 0.031(3) 0.0261(17) 0.0039(18) 0.0019(16) -0.005(2) C11 0.031(2) 0.026(2) 0.0200(16) 0.0016(15) 0.0063(14) -0.0013(17) N1 0.0236(19) 0.034(2) 0.0278(15) 0.0010(14) 0.0059(13) -0.0020(16) N2 0.0233(18) 0.043(2) 0.0349(18) -0.0032(16) 0.0055(14) -0.0017(17) N3 0.0241(17) 0.035(2) 0.0231(14) -0.0014(14) 0.0105(12) -0.0022(15) O1 0.0251(15) 0.052(2) 0.0251(12) 0.0009(13) 0.0051(11) -0.0058(14) F1 0.0238(12) 0.0459(18) 0.0359(11) -0.0004(11) 0.0092(9) 0.0029(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.328(5) . ? C1 C2 1.385(6) . ? C1 H1 0.9300 . ? C2 N2 1.339(4) . ? C2 H2 0.9300 . ? C3 N2 1.343(5) . ? C3 C4 1.380(5) . ? C3 H3 0.9300 . ? C4 N1 1.334(4) . ? C4 C5 1.501(5) . ? C5 O1 1.224(3) . ? C5 N3 1.344(4) . ? C6 C7 1.390(4) . ? C6 C11 1.395(5) . ? C6 N3 1.420(5) . ? C7 C8 1.369(5) . ? C7 H7 0.9300 . ? C8 F1 1.365(4) . ? C8 C9 1.366(5) . ? C9 C10 1.385(5) . ? C9 H9 0.9300 . ? C10 C11 1.374(5) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? N3 H3A 0.8600 . ? 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 N1 C1 C2 122.0(3) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? N2 C2 C1 122.2(3) . . ? N2 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? N2 C3 C4 122.8(3) . . ? N2 C3 H3 118.6 . . ? C4 C3 H3 118.6 . . ? N1 C4 C3 121.4(3) . . ? N1 C4 C5 118.8(3) . . ? C3 C4 C5 119.8(3) . . ? O1 C5 N3 125.4(3) . . ? O1 C5 C4 120.2(3) . . ? N3 C5 C4 114.3(3) . . ? C7 C6 C11 120.0(3) . . ? C7 C6 N3 121.7(3) . . ? C11 C6 N3 118.1(3) . . ? C8 C7 C6 117.7(3) . . ? C8 C7 H7 121.2 . . ? C6 C7 H7 121.2 . . ? F1 C8 C9 118.1(3) . . ? F1 C8 C7 117.8(3) . . ? C9 C8 C7 124.1(3) . . ? C8 C9 C10 117.3(3) . . ? C8 C9 H9 121.3 . . ? C10 C9 H9 121.3 . . ? C11 C10 C9 121.2(3) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C6 119.7(3) . . ? C10 C11 H11 120.1 . . ? C6 C11 H11 120.1 . . ? C1 N1 C4 116.4(3) . . ? C2 N2 C3 115.0(3) . . ? C5 N3 C6 127.0(3) . . ? C5 N3 H3A 116.5 . . ? C6 N3 H3A 116.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -0.2(7) . . . . ? N2 C3 C4 N1 0.7(6) . . . . ? N2 C3 C4 C5 -179.7(4) . . . . ? N1 C4 C5 O1 -173.1(4) . . . . ? C3 C4 C5 O1 7.3(6) . . . . ? N1 C4 C5 N3 7.4(5) . . . . ? C3 C4 C5 N3 -172.3(4) . . . . ? C11 C6 C7 C8 1.5(5) . . . . ? N3 C6 C7 C8 -173.7(4) . . . . ? C6 C7 C8 F1 178.2(3) . . . . ? C6 C7 C8 C9 -1.4(5) . . . . ? F1 C8 C9 C10 -179.1(4) . . . . ? C7 C8 C9 C10 0.5(5) . . . . ? C8 C9 C10 C11 0.2(6) . . . . ? C9 C10 C11 C6 -0.1(6) . . . . ? C7 C6 C11 C10 -0.8(6) . . . . ? N3 C6 C11 C10 174.6(4) . . . . ? C2 C1 N1 C4 0.7(6) . . . . ? C3 C4 N1 C1 -1.0(6) . . . . ? C5 C4 N1 C1 179.4(4) . . . . ? C1 C2 N2 C3 -0.2(6) . . . . ? C4 C3 N2 C2 -0.1(6) . . . . ? O1 C5 N3 C6 -6.1(7) . . . . ? C4 C5 N3 C6 173.5(4) . . . . ? C7 C6 N3 C5 -24.0(6) . . . . ? C11 C6 N3 C5 160.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.208 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.052 data_d:\determination\solution\hrk309\hrk309h _database_code_depnum_ccdc_archive 'CCDC 919736' #TrackingRef '4-Br-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 Br N3 O' _chemical_formula_sum 'C11 H8 Br N3 O' _chemical_formula_weight 278.10 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.85750(10) _cell_length_b 7.37670(10) _cell_length_c 13.3668(2) _cell_angle_alpha 101.5900(10) _cell_angle_beta 96.7470(10) _cell_angle_gamma 110.5470(10) _cell_volume 518.550(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9778 _cell_measurement_theta_min 3.18 _cell_measurement_theta_max 28.00 _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.490 _exptl_crystal_size_mid 0.182 _exptl_crystal_size_min 0.068 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.781 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 3.943 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.430 _exptl_absorpt_correction_T_max 0.770 _exptl_absorpt_process_details 'SADABS (Sheldric, 1998a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'APEX2 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9778 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2471 _reflns_number_gt 2291 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; 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^)+(0.0374P)^2^+0.0395P] 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 2471 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0600 _refine_ls_wR_factor_gt 0.0590 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.013 _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 C1 C 0.0206(3) 0.2849(3) 0.63829(15) 0.0275(4) Uani 1 1 d . . . H1 H 0.1695 0.3079 0.6122 0.033 Uiso 1 1 calc R . . C2 C -0.1956(4) 0.2590(3) 0.57216(14) 0.0269(4) Uani 1 1 d . . . H2 H -0.1903 0.2633 0.5019 0.032 Uiso 1 1 calc R . . C3 C -0.4060(3) 0.2226(2) 0.70292(14) 0.0228(3) Uani 1 1 d . . . H3 H -0.5543 0.2016 0.7293 0.027 Uiso 1 1 calc R . . C4 C -0.1894(3) 0.2468(2) 0.76909(13) 0.0193(3) Uani 1 1 d . . . C5 C -0.1998(3) 0.2367(2) 0.88029(13) 0.0202(3) Uani 1 1 d . . . C6 C 0.0694(3) 0.2555(2) 1.04295(13) 0.0195(3) Uani 1 1 d . . . C7 C -0.1145(3) 0.1931(2) 1.10055(14) 0.0232(3) Uani 1 1 d . . . H7 H -0.2851 0.1512 1.0693 0.028 Uiso 1 1 calc R . . C8 C -0.0471(3) 0.1926(2) 1.20354(14) 0.0243(3) Uani 1 1 d . . . H8 H -0.1718 0.1502 1.2428 0.029 Uiso 1 1 calc R . . C9 C 0.2012(3) 0.2536(2) 1.24915(13) 0.0204(3) Uani 1 1 d . . . C10 C 0.3849(3) 0.3142(2) 1.19273(14) 0.0237(3) Uani 1 1 d . . . H10 H 0.5551 0.3551 1.2244 0.028 Uiso 1 1 calc R . . C11 C 0.3195(3) 0.3148(2) 1.09012(14) 0.0235(3) Uani 1 1 d . . . H11 H 0.4454 0.3558 1.0512 0.028 Uiso 1 1 calc R . . N1 N 0.0256(3) 0.2787(2) 0.73763(12) 0.0233(3) Uani 1 1 d . . . N2 N -0.4111(3) 0.2281(2) 0.60358(12) 0.0254(3) Uani 1 1 d . . . N3 N 0.0184(3) 0.2571(2) 0.93758(12) 0.0219(3) Uani 1 1 d . . . H3B H 0.1435 0.2733 0.9051 0.026 Uiso 1 1 calc R . . O1 O -0.3931(2) 0.2125(2) 0.91138(11) 0.0287(3) Uani 1 1 d . . . Br1 Br 0.29591(3) 0.25278(2) 1.389945(13) 0.02641(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0235(9) 0.0425(9) 0.0201(9) 0.0112(7) 0.0075(7) 0.0141(7) C2 0.0293(9) 0.0400(9) 0.0154(8) 0.0099(7) 0.0059(7) 0.0162(7) C3 0.0214(8) 0.0287(7) 0.0206(9) 0.0082(6) 0.0048(7) 0.0112(6) C4 0.0210(8) 0.0204(6) 0.0163(8) 0.0045(5) 0.0027(6) 0.0084(6) C5 0.0230(8) 0.0213(7) 0.0169(8) 0.0050(6) 0.0044(6) 0.0089(6) C6 0.0233(8) 0.0215(6) 0.0145(8) 0.0044(5) 0.0038(6) 0.0097(6) C7 0.0193(8) 0.0299(8) 0.0198(8) 0.0090(6) 0.0028(7) 0.0078(6) C8 0.0255(8) 0.0304(8) 0.0194(9) 0.0104(6) 0.0071(7) 0.0107(7) C9 0.0274(9) 0.0212(6) 0.0133(8) 0.0038(6) 0.0031(6) 0.0108(6) C10 0.0195(8) 0.0307(8) 0.0191(8) 0.0043(6) 0.0009(7) 0.0097(6) C11 0.0197(8) 0.0313(8) 0.0196(8) 0.0066(6) 0.0053(7) 0.0096(6) N1 0.0191(7) 0.0329(7) 0.0177(7) 0.0076(5) 0.0030(6) 0.0096(6) N2 0.0242(8) 0.0351(7) 0.0193(8) 0.0086(6) 0.0018(6) 0.0144(6) N3 0.0217(7) 0.0306(7) 0.0153(7) 0.0074(5) 0.0057(6) 0.0111(6) O1 0.0235(7) 0.0455(7) 0.0215(7) 0.0133(5) 0.0084(5) 0.0147(5) Br1 0.03390(12) 0.03161(10) 0.01443(10) 0.00630(6) 0.00206(7) 0.01420(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 C1 N1 1.335(2) . ? C1 C2 1.386(3) . ? C1 H1 0.9500 . ? C2 N2 1.335(3) . ? C2 H2 0.9500 . ? C3 N2 1.334(2) . ? C3 C4 1.392(2) . ? C3 H3 0.9500 . ? C4 N1 1.332(2) . ? C4 C5 1.510(2) . ? C5 O1 1.218(2) . ? C5 N3 1.353(2) . ? C6 C7 1.398(2) . ? C6 C11 1.399(2) . ? C6 N3 1.408(2) . ? C7 C8 1.388(3) . ? C7 H7 0.9500 . ? C8 C9 1.382(3) . ? C8 H8 0.9500 . ? C9 C10 1.384(2) . ? C9 Br1 1.9005(17) . ? C10 C11 1.381(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? N3 H3B 0.8800 . ? 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 N1 C1 C2 121.86(16) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? N2 C2 C1 122.42(16) . . ? N2 C2 H2 118.8 . . ? C1 C2 H2 118.8 . . ? N2 C3 C4 121.87(16) . . ? N2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? N1 C4 C3 122.23(16) . . ? N1 C4 C5 119.18(15) . . ? C3 C4 C5 118.59(15) . . ? O1 C5 N3 125.66(16) . . ? O1 C5 C4 120.24(15) . . ? N3 C5 C4 114.09(14) . . ? C7 C6 C11 119.19(16) . . ? C7 C6 N3 123.79(15) . . ? C11 C6 N3 116.99(15) . . ? C8 C7 C6 119.83(16) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C7 120.15(16) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 120.59(16) . . ? C8 C9 Br1 120.58(13) . . ? C10 C9 Br1 118.83(13) . . ? C11 C10 C9 119.65(16) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C6 120.58(16) . . ? C10 C11 H11 119.7 . . ? C6 C11 H11 119.7 . . ? C4 N1 C1 115.88(16) . . ? C3 N2 C2 115.72(16) . . ? C5 N3 C6 127.84(14) . . ? C5 N3 H3B 116.1 . . ? C6 N3 H3B 116.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 0.7(3) . . . . ? N2 C3 C4 N1 0.7(2) . . . . ? N2 C3 C4 C5 -179.46(14) . . . . ? N1 C4 C5 O1 178.22(14) . . . . ? C3 C4 C5 O1 -1.7(2) . . . . ? N1 C4 C5 N3 -1.6(2) . . . . ? C3 C4 C5 N3 178.48(14) . . . . ? C11 C6 C7 C8 0.6(2) . . . . ? N3 C6 C7 C8 178.66(15) . . . . ? C6 C7 C8 C9 0.0(2) . . . . ? C7 C8 C9 C10 -0.5(2) . . . . ? C7 C8 C9 Br1 -179.78(12) . . . . ? C8 C9 C10 C11 0.4(2) . . . . ? Br1 C9 C10 C11 179.66(12) . . . . ? C9 C10 C11 C6 0.3(2) . . . . ? C7 C6 C11 C10 -0.8(2) . . . . ? N3 C6 C11 C10 -178.92(14) . . . . ? C3 C4 N1 C1 -0.4(2) . . . . ? C5 C4 N1 C1 179.75(14) . . . . ? C2 C1 N1 C4 -0.3(3) . . . . ? C4 C3 N2 C2 -0.3(2) . . . . ? C1 C2 N2 C3 -0.4(3) . . . . ? O1 C5 N3 C6 -0.2(3) . . . . ? C4 C5 N3 C6 179.66(13) . . . . ? C7 C6 N3 C5 13.0(3) . . . . ? C11 C6 N3 C5 -168.92(15) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.501 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.071 data_d:\determination\solution\khc41\khc41 _database_code_depnum_ccdc_archive 'CCDC 919737' #TrackingRef '4-Cl-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 Cl1 N3 O1' _chemical_formula_sum 'C11 H8 Cl1 N3 O1' _chemical_formula_weight 233.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8668(5) _cell_length_b 7.2831(7) _cell_length_c 13.1604(10) _cell_angle_alpha 101.762(7) _cell_angle_beta 96.668(6) _cell_angle_gamma 110.602(6) _cell_volume 504.37(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4999 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 28.00 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.357 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9414 _exptl_absorpt_correction_T_max 0.9696 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4999 _diffrn_reflns_av_R_equivalents 0.0897 _diffrn_reflns_av_sigmaI/netI 0.0854 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2420 _reflns_number_gt 1656 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0715P)^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 2420 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1012 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1458 _refine_ls_wR_factor_gt 0.1321 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _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 C1 C 0.4831(6) 0.2299(5) 0.8666(2) 0.0305(7) Uani 1 1 d . . . H1 H 0.3400 0.2120 0.8940 0.037 Uiso 1 1 calc R . . C2 C 0.7010(6) 0.2529(5) 0.9322(2) 0.0287(7) Uani 1 1 d . . . H2 H 0.6983 0.2501 1.0024 0.034 Uiso 1 1 calc R . . C3 C 0.9042(5) 0.2819(4) 0.7974(2) 0.0234(6) Uani 1 1 d . . . H3 H 1.0473 0.2994 0.7700 0.028 Uiso 1 1 calc R . . C4 C 0.6876(5) 0.2603(4) 0.7317(2) 0.0212(6) Uani 1 1 d . . . C5 C 0.6969(5) 0.2662(4) 0.6186(2) 0.0212(6) Uani 1 1 d . . . C6 C 0.4241(5) 0.2436(4) 0.4527(2) 0.0196(6) Uani 1 1 d . . . C7 C 0.6057(5) 0.3024(5) 0.3935(2) 0.0250(6) Uani 1 1 d . . . H7 H 0.7725 0.3427 0.4243 0.030 Uiso 1 1 calc R . . C8 C 0.5386(5) 0.3012(5) 0.2883(2) 0.0267(6) Uani 1 1 d . . . H8 H 0.6603 0.3406 0.2488 0.032 Uiso 1 1 calc R . . C9 C 0.2901(5) 0.2410(4) 0.2426(2) 0.0222(6) Uani 1 1 d . . . C10 C 0.1085(5) 0.1831(5) 0.3012(2) 0.0251(6) Uani 1 1 d . . . H10 H -0.0580 0.1435 0.2704 0.030 Uiso 1 1 calc R . . C11 C 0.1750(5) 0.1842(5) 0.4058(2) 0.0249(6) Uani 1 1 d . . . H11 H 0.0526 0.1449 0.4450 0.030 Uiso 1 1 calc R . . N1 N 0.4757(4) 0.2331(4) 0.76549(17) 0.0245(5) Uani 1 1 d . . . N2 N 0.9120(5) 0.2783(4) 0.89887(19) 0.0281(6) Uani 1 1 d . . . N3 N 0.4768(4) 0.2445(4) 0.56037(17) 0.0237(5) Uani 1 1 d . . . H3B H 0.3554 0.2295 0.5930 0.028 Uiso 1 1 calc R . . O1 O 0.8871(4) 0.2883(4) 0.58567(16) 0.0310(5) Uani 1 1 d . . . Cl1 Cl 0.20374(15) 0.23869(13) 0.11161(5) 0.0310(2) 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 C1 0.0215(15) 0.048(2) 0.0221(14) 0.0125(13) 0.0067(11) 0.0115(13) C2 0.0279(16) 0.0447(19) 0.0152(12) 0.0101(12) 0.0038(11) 0.0149(14) C3 0.0180(13) 0.0327(16) 0.0227(13) 0.0106(11) 0.0061(10) 0.0112(12) C4 0.0193(14) 0.0245(14) 0.0196(13) 0.0068(11) 0.0040(10) 0.0075(11) C5 0.0190(13) 0.0259(15) 0.0183(12) 0.0075(11) 0.0042(10) 0.0072(11) C6 0.0199(13) 0.0228(14) 0.0169(12) 0.0057(10) 0.0029(10) 0.0094(11) C7 0.0190(14) 0.0356(16) 0.0219(13) 0.0114(12) 0.0043(10) 0.0102(12) C8 0.0237(15) 0.0361(17) 0.0235(14) 0.0142(12) 0.0087(11) 0.0107(13) C9 0.0255(15) 0.0289(15) 0.0157(12) 0.0082(11) 0.0043(10) 0.0134(12) C10 0.0193(14) 0.0355(16) 0.0197(13) 0.0061(11) 0.0020(10) 0.0107(12) C11 0.0196(14) 0.0347(16) 0.0211(13) 0.0084(11) 0.0069(10) 0.0098(12) N1 0.0198(12) 0.0384(14) 0.0164(11) 0.0103(10) 0.0046(9) 0.0107(10) N2 0.0238(13) 0.0395(15) 0.0216(12) 0.0096(11) 0.0019(9) 0.0130(11) N3 0.0185(12) 0.0377(14) 0.0160(11) 0.0093(10) 0.0041(8) 0.0106(10) O1 0.0233(11) 0.0516(14) 0.0246(10) 0.0171(10) 0.0099(8) 0.0169(10) Cl1 0.0373(4) 0.0414(4) 0.0156(3) 0.0102(3) 0.0021(3) 0.0162(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.331(3) . ? C1 C2 1.394(4) . ? C1 H1 0.9300 . ? C2 N2 1.325(4) . ? C2 H2 0.9300 . ? C3 N2 1.337(4) . ? C3 C4 1.391(4) . ? C3 H3 0.9300 . ? C4 N1 1.332(4) . ? C4 C5 1.504(4) . ? C5 O1 1.214(3) . ? C5 N3 1.363(4) . ? C6 C7 1.390(4) . ? C6 C11 1.393(4) . ? C6 N3 1.414(3) . ? C7 C8 1.393(4) . ? C7 H7 0.9300 . ? C8 C9 1.385(4) . ? C8 H8 0.9300 . ? C9 C10 1.384(4) . ? C9 Cl1 1.734(3) . ? C10 C11 1.384(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? N3 H3B 0.8600 . ? 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 N1 C1 C2 121.4(3) . . ? N1 C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? N2 C2 C1 122.9(3) . . ? N2 C2 H2 118.6 . . ? C1 C2 H2 118.6 . . ? N2 C3 C4 121.7(3) . . ? N2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? N1 C4 C3 122.3(2) . . ? N1 C4 C5 119.8(2) . . ? C3 C4 C5 117.9(2) . . ? O1 C5 N3 125.2(2) . . ? O1 C5 C4 121.0(2) . . ? N3 C5 C4 113.8(2) . . ? C7 C6 C11 119.4(2) . . ? C7 C6 N3 123.7(2) . . ? C11 C6 N3 116.9(2) . . ? C6 C7 C8 120.1(3) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C9 C8 C7 119.8(3) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C10 C9 C8 120.3(2) . . ? C10 C9 Cl1 119.4(2) . . ? C8 C9 Cl1 120.3(2) . . ? C9 C10 C11 120.0(3) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C6 120.4(3) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? C1 N1 C4 116.1(2) . . ? C2 N2 C3 115.6(2) . . ? C5 N3 C6 127.8(2) . . ? C5 N3 H3B 116.1 . . ? C6 N3 H3B 116.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -0.2(5) . . . . ? N2 C3 C4 N1 -0.6(5) . . . . ? N2 C3 C4 C5 -179.9(3) . . . . ? N1 C4 C5 O1 -179.1(3) . . . . ? C3 C4 C5 O1 0.3(4) . . . . ? N1 C4 C5 N3 0.8(4) . . . . ? C3 C4 C5 N3 -179.8(2) . . . . ? C11 C6 C7 C8 -0.2(5) . . . . ? N3 C6 C7 C8 -178.7(3) . . . . ? C6 C7 C8 C9 0.0(5) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C7 C8 C9 Cl1 -180.0(2) . . . . ? C8 C9 C10 C11 -0.3(5) . . . . ? Cl1 C9 C10 C11 179.9(2) . . . . ? C9 C10 C11 C6 0.1(5) . . . . ? C7 C6 C11 C10 0.1(5) . . . . ? N3 C6 C11 C10 178.7(3) . . . . ? C2 C1 N1 C4 -0.3(5) . . . . ? C3 C4 N1 C1 0.7(4) . . . . ? C5 C4 N1 C1 -180.0(3) . . . . ? C1 C2 N2 C3 0.4(5) . . . . ? C4 C3 N2 C2 0.0(4) . . . . ? O1 C5 N3 C6 -0.2(5) . . . . ? C4 C5 N3 C6 179.9(3) . . . . ? C7 C6 N3 C5 -12.2(5) . . . . ? C11 C6 N3 C5 169.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.530 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.079 data_d:\determination\solution\c268\new _database_code_depnum_ccdc_archive 'CCDC 919738' #TrackingRef '4-F-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 F1 N3 O1' _chemical_formula_sum 'C11 H8 F1 N3 O1' _chemical_formula_weight 217.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.9760(4) _cell_length_b 23.928(2) _cell_length_c 13.3223(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.047(6) _cell_angle_gamma 90.00 _cell_volume 1902.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 12418 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 28.00 _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9891 _exptl_absorpt_correction_T_max 0.9910 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12418 _diffrn_reflns_av_R_equivalents 0.0919 _diffrn_reflns_av_sigmaI/netI 0.1111 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4562 _reflns_number_gt 3918 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0317P)^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 4562 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0921 _refine_ls_R_factor_gt 0.0751 _refine_ls_wR_factor_ref 0.1112 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 C1 C 0.5116(9) 0.3109(2) 0.5711(4) 0.0308(14) Uani 1 1 d . . . H1 H 0.3704 0.2949 0.5745 0.037 Uiso 1 1 calc R . . C2 C 0.6883(9) 0.2769(2) 0.5485(4) 0.0319(14) Uani 1 1 d . . . H2 H 0.6625 0.2390 0.5370 0.038 Uiso 1 1 calc R . . C3 C 0.9182(9) 0.3518(2) 0.5610(4) 0.0267(13) Uani 1 1 d . . . H3 H 1.0596 0.3677 0.5583 0.032 Uiso 1 1 calc R . . C4 C 0.7416(9) 0.3859(2) 0.5837(4) 0.0222(12) Uani 1 1 d . . . C5 C 0.7804(10) 0.4474(2) 0.6019(4) 0.0234(13) Uani 1 1 d . . . C6 C 0.5730(8) 0.5341(2) 0.6372(4) 0.0210(12) Uani 1 1 d . . . C7 C 0.7468(9) 0.5726(2) 0.6248(4) 0.0263(13) Uani 1 1 d . . . H7 H 0.8821 0.5606 0.6008 0.032 Uiso 1 1 calc R . . C8 C 0.7165(10) 0.6279(2) 0.6481(4) 0.0294(13) Uani 1 1 d . . . H8 H 0.8320 0.6535 0.6416 0.035 Uiso 1 1 calc R . . C9 C 0.5136(9) 0.6451(2) 0.6811(4) 0.0271(13) Uani 1 1 d . . . C10 C 0.3396(9) 0.6092(2) 0.6927(4) 0.0265(13) Uani 1 1 d . . . H10 H 0.2037 0.6219 0.7149 0.032 Uiso 1 1 calc R . . C11 C 0.3711(9) 0.5532(2) 0.6703(4) 0.0266(13) Uani 1 1 d . . . H11 H 0.2546 0.5281 0.6778 0.032 Uiso 1 1 calc R . . C12 C 0.9962(10) 0.6344(2) 0.9108(4) 0.0305(14) Uani 1 1 d . . . H12 H 1.1371 0.6505 0.9066 0.037 Uiso 1 1 calc R . . C13 C 0.8196(9) 0.6677(2) 0.9345(4) 0.0256(13) Uani 1 1 d . . . H13 H 0.8456 0.7055 0.9470 0.031 Uiso 1 1 calc R . . C14 C 0.5878(9) 0.5935(2) 0.9231(4) 0.0259(13) Uani 1 1 d . . . H14 H 0.4464 0.5776 0.9264 0.031 Uiso 1 1 calc R . . C15 C 0.7651(9) 0.5595(2) 0.9006(4) 0.0242(13) Uani 1 1 d . . . C16 C 0.7221(10) 0.4988(2) 0.8801(4) 0.0238(13) Uani 1 1 d . . . C17 C 0.9297(9) 0.4115(2) 0.8423(4) 0.0192(12) Uani 1 1 d . . . C18 C 0.7573(9) 0.3735(2) 0.8541(4) 0.0244(13) Uani 1 1 d . . . H18 H 0.6203 0.3857 0.8758 0.029 Uiso 1 1 calc R . . C19 C 0.7896(10) 0.3166(2) 0.8333(4) 0.0286(13) Uani 1 1 d . . . H19 H 0.6755 0.2909 0.8419 0.034 Uiso 1 1 calc R . . C20 C 0.9911(10) 0.2996(2) 0.8002(4) 0.0310(14) Uani 1 1 d . . . C21 C 1.1661(10) 0.3364(2) 0.7899(4) 0.0300(14) Uani 1 1 d . . . H21 H 1.3033 0.3236 0.7693 0.036 Uiso 1 1 calc R . . C22 C 1.1355(9) 0.3927(2) 0.8106(4) 0.0267(13) Uani 1 1 d . . . H22 H 1.2522 0.4178 0.8033 0.032 Uiso 1 1 calc R . . N1 N 0.5328(8) 0.36504(17) 0.5882(3) 0.0263(11) Uani 1 1 d . . . N2 N 0.8967(8) 0.29708(18) 0.5427(3) 0.0288(11) Uani 1 1 d . . . N3 N 0.5921(8) 0.47615(18) 0.6169(3) 0.0269(12) Uani 1 1 d . . . H3B H 0.4693 0.4573 0.6138 0.032 Uiso 1 1 calc R . . N4 N 0.9718(8) 0.57927(19) 0.8934(3) 0.0290(12) Uani 1 1 d . . . N5 N 0.6109(8) 0.64789(17) 0.9403(3) 0.0284(12) Uani 1 1 d . . . N6 N 0.9107(7) 0.46892(17) 0.8644(3) 0.0258(11) Uani 1 1 d . . . H6 H 1.0343 0.4874 0.8685 0.031 Uiso 1 1 calc R . . O1 O 0.9701(6) 0.46587(15) 0.6044(3) 0.0327(10) Uani 1 1 d . . . O2 O 0.5346(6) 0.47906(15) 0.8802(3) 0.0324(10) Uani 1 1 d . . . F1 F 0.4893(6) 0.70003(12) 0.7056(3) 0.0410(9) Uani 1 1 d . . . F2 F 1.0205(6) 0.24490(12) 0.7782(3) 0.0422(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 C1 0.024(3) 0.021(3) 0.047(4) 0.000(2) 0.003(3) 0.001(2) C2 0.034(4) 0.017(3) 0.045(4) -0.004(2) 0.001(3) 0.000(3) C3 0.029(3) 0.018(3) 0.033(3) 0.002(2) 0.004(3) 0.004(2) C4 0.024(3) 0.015(3) 0.027(3) 0.000(2) 0.001(2) -0.002(2) C5 0.035(3) 0.020(3) 0.016(3) 0.002(2) 0.001(2) -0.004(3) C6 0.021(3) 0.021(3) 0.021(3) 0.002(2) 0.002(2) -0.001(2) C7 0.022(3) 0.022(3) 0.035(3) 0.004(2) 0.007(3) -0.001(2) C8 0.025(3) 0.022(3) 0.041(3) 0.008(2) -0.002(3) -0.008(2) C9 0.023(3) 0.022(3) 0.036(3) -0.001(2) -0.003(3) 0.005(2) C10 0.019(3) 0.027(3) 0.034(3) -0.004(2) 0.003(2) 0.009(2) C11 0.023(3) 0.022(3) 0.035(3) 0.001(2) 0.007(3) 0.002(2) C12 0.030(3) 0.020(3) 0.041(3) -0.006(2) 0.002(3) -0.006(3) C13 0.031(3) 0.014(3) 0.032(3) 0.003(2) -0.002(3) -0.007(2) C14 0.023(3) 0.027(3) 0.027(3) 0.004(2) 0.002(2) -0.006(2) C15 0.025(3) 0.023(3) 0.025(3) 0.002(2) 0.006(3) 0.000(2) C16 0.030(3) 0.024(3) 0.018(3) 0.004(2) 0.002(2) 0.000(3) C17 0.025(3) 0.011(2) 0.022(3) -0.0005(19) 0.001(2) -0.003(2) C18 0.021(3) 0.023(3) 0.030(3) 0.002(2) 0.005(2) 0.002(2) C19 0.035(3) 0.018(3) 0.032(3) -0.001(2) 0.001(3) -0.001(2) C20 0.039(4) 0.019(3) 0.034(3) -0.006(2) -0.003(3) 0.005(3) C21 0.030(3) 0.028(3) 0.032(3) -0.005(2) 0.002(3) -0.002(3) C22 0.024(3) 0.024(3) 0.032(3) -0.004(2) 0.001(3) -0.008(2) N1 0.025(3) 0.016(2) 0.037(3) -0.0043(19) -0.001(2) -0.001(2) N2 0.027(3) 0.020(2) 0.039(3) 0.001(2) -0.002(2) 0.009(2) N3 0.026(3) 0.016(2) 0.038(3) -0.0063(19) 0.004(2) -0.005(2) N4 0.027(3) 0.030(3) 0.031(3) -0.001(2) 0.007(2) 0.002(2) N5 0.033(3) 0.016(2) 0.036(3) -0.003(2) 0.008(2) -0.001(2) N6 0.020(3) 0.020(2) 0.037(3) -0.003(2) -0.001(2) -0.006(2) O1 0.023(2) 0.021(2) 0.055(3) -0.0035(18) 0.004(2) -0.0034(17) O2 0.029(2) 0.024(2) 0.045(2) -0.0003(17) 0.0037(19) -0.0021(19) F1 0.042(2) 0.0172(17) 0.064(2) -0.0084(16) 0.0026(18) 0.0094(15) F2 0.044(2) 0.0183(17) 0.064(2) -0.0080(16) 0.0040(18) 0.0039(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.321(6) . ? C1 C2 1.379(7) . ? C1 H1 0.9300 . ? C2 N2 1.342(7) . ? C2 H2 0.9300 . ? C3 N2 1.336(6) . ? C3 C4 1.380(7) . ? C3 H3 0.9300 . ? C4 N1 1.348(7) . ? C4 C5 1.507(7) . ? C5 O1 1.215(6) . ? C5 N3 1.343(7) . ? C6 C11 1.384(6) . ? C6 C7 1.403(7) . ? C6 N3 1.420(6) . ? C7 C8 1.374(7) . ? C7 H7 0.9300 . ? C8 C9 1.375(7) . ? C8 H8 0.9300 . ? C9 C10 1.363(7) . ? C9 F1 1.364(6) . ? C10 C11 1.388(7) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 N4 1.347(7) . ? C12 C13 1.372(7) . ? C12 H12 0.9300 . ? C13 N5 1.341(6) . ? C13 H13 0.9300 . ? C14 N5 1.328(6) . ? C14 C15 1.381(7) . ? C14 H14 0.9300 . ? C15 N4 1.331(7) . ? C15 C16 1.497(7) . ? C16 O2 1.216(6) . ? C16 N6 1.361(6) . ? C17 C18 1.390(7) . ? C17 C22 1.396(7) . ? C17 N6 1.410(6) . ? C18 C19 1.405(7) . ? C18 H18 0.9300 . ? C19 C20 1.366(7) . ? C19 H19 0.9300 . ? C20 F2 1.355(6) . ? C20 C21 1.379(7) . ? C21 C22 1.389(7) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? N3 H3B 0.8600 . ? N6 H6 0.8600 . ? 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 N1 C1 C2 123.3(5) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? N2 C2 C1 121.6(5) . . ? N2 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? N2 C3 C4 123.5(5) . . ? N2 C3 H3 118.2 . . ? C4 C3 H3 118.2 . . ? N1 C4 C3 120.8(5) . . ? N1 C4 C5 119.3(5) . . ? C3 C4 C5 120.0(5) . . ? O1 C5 N3 126.6(5) . . ? O1 C5 C4 119.7(5) . . ? N3 C5 C4 113.7(5) . . ? C11 C6 C7 119.0(5) . . ? C11 C6 N3 117.6(5) . . ? C7 C6 N3 123.4(4) . . ? C8 C7 C6 119.8(5) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 119.3(5) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C10 C9 F1 119.2(5) . . ? C10 C9 C8 122.6(5) . . ? F1 C9 C8 118.1(5) . . ? C9 C10 C11 118.0(5) . . ? C9 C10 H10 121.0 . . ? C11 C10 H10 121.0 . . ? C6 C11 C10 121.2(5) . . ? C6 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? N4 C12 C13 122.1(5) . . ? N4 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? N5 C13 C12 122.5(5) . . ? N5 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? N5 C14 C15 122.8(5) . . ? N5 C14 H14 118.6 . . ? C15 C14 H14 118.6 . . ? N4 C15 C14 122.1(5) . . ? N4 C15 C16 118.9(5) . . ? C14 C15 C16 119.0(5) . . ? O2 C16 N6 124.5(5) . . ? O2 C16 C15 121.7(5) . . ? N6 C16 C15 113.8(5) . . ? C18 C17 C22 119.5(5) . . ? C18 C17 N6 123.1(4) . . ? C22 C17 N6 117.4(4) . . ? C17 C18 C19 120.2(5) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C20 C19 C18 119.0(5) . . ? C20 C19 H19 120.5 . . ? C18 C19 H19 120.5 . . ? F2 C20 C19 118.9(5) . . ? F2 C20 C21 119.2(5) . . ? C19 C20 C21 121.9(5) . . ? C20 C21 C22 119.4(5) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C21 C22 C17 120.1(5) . . ? C21 C22 H22 120.0 . . ? C17 C22 H22 120.0 . . ? C1 N1 C4 115.8(5) . . ? C3 N2 C2 115.0(5) . . ? C5 N3 C6 127.3(5) . . ? C5 N3 H3B 116.4 . . ? C6 N3 H3B 116.4 . . ? C15 N4 C12 115.4(5) . . ? C14 N5 C13 115.2(5) . . ? C16 N6 C17 128.4(5) . . ? C16 N6 H6 115.8 . . ? C17 N6 H6 115.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 0.2(9) . . . . ? N2 C3 C4 N1 -0.3(8) . . . . ? N2 C3 C4 C5 -179.1(5) . . . . ? N1 C4 C5 O1 175.3(5) . . . . ? C3 C4 C5 O1 -5.8(8) . . . . ? N1 C4 C5 N3 -2.9(7) . . . . ? C3 C4 C5 N3 176.0(5) . . . . ? C11 C6 C7 C8 1.7(8) . . . . ? N3 C6 C7 C8 -178.7(5) . . . . ? C6 C7 C8 C9 -1.5(8) . . . . ? C7 C8 C9 C10 0.5(9) . . . . ? C7 C8 C9 F1 178.8(5) . . . . ? F1 C9 C10 C11 -178.0(5) . . . . ? C8 C9 C10 C11 0.3(9) . . . . ? C7 C6 C11 C10 -0.9(8) . . . . ? N3 C6 C11 C10 179.4(5) . . . . ? C9 C10 C11 C6 -0.1(8) . . . . ? N4 C12 C13 N5 -1.1(9) . . . . ? N5 C14 C15 N4 -0.8(8) . . . . ? N5 C14 C15 C16 -178.6(5) . . . . ? N4 C15 C16 O2 -176.0(5) . . . . ? C14 C15 C16 O2 1.9(8) . . . . ? N4 C15 C16 N6 5.6(7) . . . . ? C14 C15 C16 N6 -176.5(5) . . . . ? C22 C17 C18 C19 -0.6(8) . . . . ? N6 C17 C18 C19 -178.2(5) . . . . ? C17 C18 C19 C20 -0.9(8) . . . . ? C18 C19 C20 F2 -178.6(5) . . . . ? C18 C19 C20 C21 2.2(9) . . . . ? F2 C20 C21 C22 178.8(5) . . . . ? C19 C20 C21 C22 -2.1(9) . . . . ? C20 C21 C22 C17 0.5(8) . . . . ? C18 C17 C22 C21 0.8(8) . . . . ? N6 C17 C22 C21 178.5(5) . . . . ? C2 C1 N1 C4 -0.9(8) . . . . ? C3 C4 N1 C1 0.9(8) . . . . ? C5 C4 N1 C1 179.8(5) . . . . ? C4 C3 N2 C2 -0.4(8) . . . . ? C1 C2 N2 C3 0.4(8) . . . . ? O1 C5 N3 C6 1.0(9) . . . . ? C4 C5 N3 C6 179.1(5) . . . . ? C11 C6 N3 C5 -167.0(5) . . . . ? C7 C6 N3 C5 13.4(8) . . . . ? C14 C15 N4 C12 0.8(8) . . . . ? C16 C15 N4 C12 178.6(5) . . . . ? C13 C12 N4 C15 0.1(8) . . . . ? C15 C14 N5 C13 -0.2(8) . . . . ? C12 C13 N5 C14 1.1(8) . . . . ? O2 C16 N6 C17 2.4(9) . . . . ? C15 C16 N6 C17 -179.2(5) . . . . ? C18 C17 N6 C16 -14.3(8) . . . . ? C22 C17 N6 C16 168.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.258 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.060 data_d:\determination\solution\h\new _database_code_depnum_ccdc_archive 'CCDC 919739' #TrackingRef '4-H-Mojadad.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H9 N3 O1' _chemical_formula_sum 'C11 H9 N3 O1' _chemical_formula_weight 199.21 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 5.9838(8) _cell_length_b 7.5827(11) _cell_length_c 11.0466(12) _cell_angle_alpha 83.440(10) _cell_angle_beta 85.331(10) _cell_angle_gamma 69.289(11) _cell_volume 465.31(10) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4523 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 28.00 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4523 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0737 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2223 _reflns_number_gt 1228 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0374P)^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 2223 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0903 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0804 _refine_ls_wR_factor_gt 0.0713 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.002 _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 C1 C 1.0243(3) 0.6101(2) 0.18340(13) 0.0393(4) Uani 1 1 d . . . H1 H 0.8904 0.6059 0.1483 0.047 Uiso 1 1 calc R . . C2 C 1.2399(3) 0.5617(2) 0.11684(13) 0.0383(4) Uani 1 1 d . . . H2 H 1.2462 0.5257 0.0386 0.046 Uiso 1 1 calc R . . C3 C 1.4170(3) 0.6167(2) 0.27407(13) 0.0382(4) Uani 1 1 d . . . H3 H 1.5510 0.6209 0.3091 0.046 Uiso 1 1 calc R . . C4 C 1.2012(3) 0.6647(2) 0.34109(13) 0.0333(3) Uani 1 1 d . . . C5 C 1.1918(3) 0.7220(2) 0.46748(13) 0.0348(4) Uani 1 1 d . . . C6 C 0.9071(2) 0.8217(2) 0.64512(12) 0.0330(4) Uani 1 1 d . . . C7 C 1.0708(3) 0.8140(2) 0.72934(13) 0.0373(4) Uani 1 1 d . . . H7 H 1.2336 0.7715 0.7085 0.045 Uiso 1 1 calc R . . C8 C 0.9898(3) 0.8703(2) 0.84484(13) 0.0397(4) Uani 1 1 d . . . H8 H 1.0995 0.8647 0.9014 0.048 Uiso 1 1 calc R . . C9 C 0.7490(3) 0.9343(2) 0.87706(14) 0.0430(4) Uani 1 1 d . . . H9 H 0.6964 0.9714 0.9549 0.052 Uiso 1 1 calc R . . C10 C 0.5870(3) 0.9430(3) 0.79269(14) 0.0446(4) Uani 1 1 d . . . H10 H 0.4243 0.9870 0.8138 0.054 Uiso 1 1 calc R . . C11 C 0.6633(3) 0.8871(2) 0.67748(13) 0.0384(4) Uani 1 1 d . . . H11 H 0.5524 0.8929 0.6214 0.046 Uiso 1 1 calc R . . N1 N 1.0020(2) 0.66248(19) 0.29627(10) 0.0369(3) Uani 1 1 d . . . N2 N 1.4391(2) 0.5648(2) 0.16105(11) 0.0404(3) Uani 1 1 d . . . N3 N 0.9739(2) 0.76320(18) 0.52616(10) 0.0366(3) Uani 1 1 d . . . H3A H 0.8626 0.7525 0.4862 0.044 Uiso 1 1 calc R . . O1 O 1.37045(18) 0.72909(17) 0.51012(9) 0.0442(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 C1 0.0380(8) 0.0467(10) 0.0353(8) -0.0095(7) -0.0027(7) -0.0152(7) C2 0.0422(9) 0.0429(10) 0.0300(8) -0.0101(7) -0.0016(7) -0.0130(7) C3 0.0345(8) 0.0457(10) 0.0335(9) -0.0091(7) -0.0015(7) -0.0111(7) C4 0.0338(7) 0.0348(9) 0.0310(8) -0.0047(6) -0.0011(6) -0.0112(6) C5 0.0366(8) 0.0370(9) 0.0310(8) -0.0066(6) -0.0008(7) -0.0121(7) C6 0.0357(8) 0.0341(9) 0.0303(8) -0.0067(7) 0.0011(6) -0.0132(7) C7 0.0348(8) 0.0437(10) 0.0328(8) -0.0059(7) -0.0019(7) -0.0119(7) C8 0.0413(9) 0.0497(11) 0.0318(8) -0.0076(7) -0.0023(7) -0.0190(8) C9 0.0450(9) 0.0577(12) 0.0317(8) -0.0141(8) 0.0073(7) -0.0235(8) C10 0.0350(8) 0.0599(12) 0.0423(9) -0.0151(8) 0.0060(7) -0.0190(8) C11 0.0359(8) 0.0471(10) 0.0361(9) -0.0094(7) -0.0014(7) -0.0177(7) N1 0.0361(7) 0.0432(8) 0.0328(7) -0.0091(6) 0.0000(6) -0.0143(6) N2 0.0359(7) 0.0491(9) 0.0338(8) -0.0108(6) 0.0014(6) -0.0105(6) N3 0.0355(7) 0.0469(9) 0.0300(7) -0.0110(6) -0.0012(5) -0.0151(6) O1 0.0388(6) 0.0615(8) 0.0361(6) -0.0136(5) -0.0023(5) -0.0190(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.3338(19) . ? C1 C2 1.3828(19) . ? C1 H1 0.9300 . ? C2 N2 1.333(2) . ? C2 H2 0.9300 . ? C3 N2 1.3341(18) . ? C3 C4 1.3858(19) . ? C3 H3 0.9300 . ? C4 N1 1.3339(19) . ? C4 C5 1.500(2) . ? C5 O1 1.2229(17) . ? C5 N3 1.3560(18) . ? C6 C7 1.387(2) . ? C6 C11 1.3953(19) . ? C6 N3 1.4162(18) . ? C7 C8 1.386(2) . ? C7 H7 0.9300 . ? C8 C9 1.378(2) . ? C8 H8 0.9300 . ? C9 C10 1.379(2) . ? C9 H9 0.9300 . ? C10 C11 1.378(2) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? N3 H3A 0.8600 . ? 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 N1 C1 C2 122.20(14) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? N2 C2 C1 122.25(13) . . ? N2 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? N2 C3 C4 122.30(14) . . ? N2 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? N1 C4 C3 121.98(14) . . ? N1 C4 C5 119.16(13) . . ? C3 C4 C5 118.87(13) . . ? O1 C5 N3 125.00(14) . . ? O1 C5 C4 120.66(13) . . ? N3 C5 C4 114.35(13) . . ? C7 C6 C11 119.57(13) . . ? C7 C6 N3 123.36(13) . . ? C11 C6 N3 117.06(13) . . ? C8 C7 C6 119.51(14) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C9 C8 C7 120.98(15) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 119.26(14) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C11 C10 C9 120.82(14) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C6 119.85(15) . . ? C10 C11 H11 120.1 . . ? C6 C11 H11 120.1 . . ? C1 N1 C4 115.71(13) . . ? C2 N2 C3 115.55(13) . . ? C5 N3 C6 128.00(13) . . ? C5 N3 H3A 116.0 . . ? C6 N3 H3A 116.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -0.2(3) . . . . ? N2 C3 C4 N1 -0.3(2) . . . . ? N2 C3 C4 C5 -179.84(16) . . . . ? N1 C4 C5 O1 -178.51(16) . . . . ? C3 C4 C5 O1 1.1(2) . . . . ? N1 C4 C5 N3 1.4(2) . . . . ? C3 C4 C5 N3 -178.98(16) . . . . ? C11 C6 C7 C8 0.4(2) . . . . ? N3 C6 C7 C8 -178.55(15) . . . . ? C6 C7 C8 C9 -0.2(2) . . . . ? C7 C8 C9 C10 -0.2(3) . . . . ? C8 C9 C10 C11 0.5(3) . . . . ? C9 C10 C11 C6 -0.3(3) . . . . ? C7 C6 C11 C10 -0.2(2) . . . . ? N3 C6 C11 C10 178.88(15) . . . . ? C2 C1 N1 C4 -0.2(2) . . . . ? C3 C4 N1 C1 0.4(2) . . . . ? C5 C4 N1 C1 180.00(14) . . . . ? C1 C2 N2 C3 0.3(2) . . . . ? C4 C3 N2 C2 -0.1(2) . . . . ? O1 C5 N3 C6 0.1(3) . . . . ? C4 C5 N3 C6 -179.80(15) . . . . ? C7 C6 N3 C5 -11.8(3) . . . . ? C11 C6 N3 C5 169.20(15) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.131 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.033