# 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\c135\khc135 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H12 Br1 N1 O1' _chemical_formula_weight 326.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.5791(16) _cell_length_b 7.683(3) _cell_length_c 16.223(4) _cell_angle_alpha 89.07(2) _cell_angle_beta 83.89(2) _cell_angle_gamma 84.51(3) _cell_volume 688.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7723 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 29.19 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 2.980 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.560 _exptl_absorpt_correction_T_max 0.649 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 7723 _diffrn_reflns_av_R_equivalents 0.1031 _diffrn_reflns_av_sigmaI/netI 0.0912 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 29.19 _reflns_number_total 3697 _reflns_number_gt 2247 _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^)+(0.0393P)^2^+0.6712P] 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 3697 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1319 _refine_ls_R_factor_gt 0.0754 _refine_ls_wR_factor_ref 0.1571 _refine_ls_wR_factor_gt 0.1368 _refine_ls_goodness_of_fit_ref 1.179 _refine_ls_restrained_S_all 1.179 _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 1.5153(8) 0.3136(6) -0.1411(3) 0.0360(9) Uani 1 1 d . . . H1 H 1.6440 0.3644 -0.1223 0.043 Uiso 1 1 calc R . . C2 C 1.4957(8) 0.3077(5) -0.2271(3) 0.0351(9) Uani 1 1 d . . . C3 C 1.6644(9) 0.3780(6) -0.2864(3) 0.0430(11) Uani 1 1 d . . . H3 H 1.7919 0.4320 -0.2687 0.052 Uiso 1 1 calc R . . C4 C 1.6442(10) 0.3685(7) -0.3689(3) 0.0527(13) Uani 1 1 d . . . H4 H 1.7566 0.4162 -0.4070 0.063 Uiso 1 1 calc R . . C5 C 1.4544(10) 0.2867(7) -0.3963(3) 0.0523(13) Uani 1 1 d . . . H5 H 1.4423 0.2795 -0.4528 0.063 Uiso 1 1 calc R . . C6 C 1.2859(9) 0.2171(7) -0.3411(3) 0.0474(12) Uani 1 1 d . . . H6 H 1.1600 0.1640 -0.3605 0.057 Uiso 1 1 calc R . . C7 C 1.3016(8) 0.2251(6) -0.2551(3) 0.0358(9) Uani 1 1 d . . . C8 C 1.1325(8) 0.1544(6) -0.1958(3) 0.0405(10) Uani 1 1 d . . . H8 H 1.0048 0.1004 -0.2134 0.049 Uiso 1 1 calc R . . C9 C 1.1543(8) 0.1644(6) -0.1130(3) 0.0381(10) Uani 1 1 d . . . H9 H 1.0411 0.1173 -0.0749 0.046 Uiso 1 1 calc R . . C10 C 1.3467(8) 0.2453(6) -0.0846(3) 0.0356(9) Uani 1 1 d . . . C11 C 1.3803(8) 0.2537(6) 0.0056(3) 0.0402(10) Uani 1 1 d . . . C12 C 1.1462(8) 0.2500(6) 0.1458(3) 0.0352(9) Uani 1 1 d . . . C13 C 1.3236(8) 0.1706(6) 0.1912(3) 0.0381(10) Uani 1 1 d . . . H13 H 1.4714 0.1254 0.1643 0.046 Uiso 1 1 calc R . . C14 C 1.2806(8) 0.1588(6) 0.2762(3) 0.0404(10) Uani 1 1 d . . . H14 H 1.4005 0.1074 0.3069 0.049 Uiso 1 1 calc R . . C15 C 1.0604(9) 0.2232(6) 0.3157(3) 0.0410(11) Uani 1 1 d . . . C16 C 0.8825(9) 0.3026(6) 0.2716(3) 0.0418(11) Uani 1 1 d . . . H16 H 0.7346 0.3469 0.2988 0.050 Uiso 1 1 calc R . . C17 C 0.9263(8) 0.3159(6) 0.1859(3) 0.0399(10) Uani 1 1 d . . . H17 H 0.8072 0.3694 0.1555 0.048 Uiso 1 1 calc R . . N1 N 1.1709(7) 0.2578(5) 0.0580(2) 0.0418(9) Uani 1 1 d . . . H1B H 1.0384 0.2662 0.0349 0.050 Uiso 1 1 calc R . . O1 O 1.5801(6) 0.2580(5) 0.0305(2) 0.0560(9) Uani 1 1 d . . . Br1 Br 1.00053(12) 0.20314(9) 0.43281(3) 0.0673(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 0.033(2) 0.040(3) 0.035(2) 0.0007(18) -0.0050(17) -0.0038(19) C2 0.035(2) 0.029(2) 0.039(2) 0.0018(17) -0.0018(18) 0.0034(18) C3 0.041(3) 0.047(3) 0.042(2) 0.002(2) -0.0020(19) -0.009(2) C4 0.051(3) 0.064(3) 0.041(2) 0.009(2) 0.007(2) -0.005(3) C5 0.060(3) 0.071(4) 0.024(2) -0.004(2) -0.005(2) 0.001(3) C6 0.046(3) 0.057(3) 0.040(2) -0.008(2) -0.009(2) -0.002(2) C7 0.031(2) 0.034(2) 0.042(2) 0.0006(18) -0.0071(18) -0.0002(18) C8 0.032(2) 0.040(3) 0.051(3) 0.000(2) -0.0088(19) -0.005(2) C9 0.032(2) 0.042(3) 0.041(2) 0.0000(19) -0.0020(18) -0.0072(19) C10 0.035(2) 0.034(2) 0.037(2) 0.0003(18) -0.0048(18) 0.0004(19) C11 0.037(3) 0.042(3) 0.041(2) 0.0048(19) -0.0006(19) -0.001(2) C12 0.034(2) 0.038(2) 0.034(2) -0.0010(18) -0.0032(17) -0.0048(19) C13 0.027(2) 0.044(3) 0.042(2) -0.0007(19) -0.0032(18) 0.0048(19) C14 0.038(3) 0.042(3) 0.042(2) 0.006(2) -0.013(2) -0.001(2) C15 0.050(3) 0.043(3) 0.033(2) 0.0029(19) -0.0057(19) -0.013(2) C16 0.039(3) 0.043(3) 0.042(2) -0.003(2) 0.0010(19) 0.001(2) C17 0.034(2) 0.048(3) 0.038(2) -0.0008(19) -0.0073(18) -0.002(2) N1 0.034(2) 0.057(3) 0.0340(18) 0.0026(17) -0.0041(15) -0.0009(18) O1 0.0361(19) 0.091(3) 0.0435(18) 0.0051(18) -0.0098(15) -0.0137(18) Br1 0.0811(5) 0.0866(5) 0.0337(3) 0.0048(2) -0.0007(2) -0.0129(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 C10 1.376(6) . ? C1 C2 1.414(6) . ? C1 H1 0.9300 . ? C2 C3 1.411(6) . ? C2 C7 1.424(6) . ? C3 C4 1.358(6) . ? C3 H3 0.9300 . ? C4 C5 1.396(7) . ? C4 H4 0.9300 . ? C5 C6 1.368(7) . ? C5 H5 0.9300 . ? C6 C7 1.410(6) . ? C6 H6 0.9300 . ? C7 C8 1.414(6) . ? C8 C9 1.366(6) . ? C8 H8 0.9300 . ? C9 C10 1.412(6) . ? C9 H9 0.9300 . ? C10 C11 1.498(6) . ? C11 O1 1.229(5) . ? C11 N1 1.368(6) . ? C12 C17 1.381(6) . ? C12 C13 1.385(6) . ? C12 N1 1.417(5) . ? C13 C14 1.379(6) . ? C13 H13 0.9300 . ? C14 C15 1.375(7) . ? C14 H14 0.9300 . ? C15 C16 1.375(6) . ? C15 Br1 1.900(4) . ? C16 C17 1.390(6) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? N1 H1B 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 C10 C1 C2 121.1(4) . . ? C10 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C3 C2 C1 122.3(4) . . ? C3 C2 C7 118.8(4) . . ? C1 C2 C7 118.9(4) . . ? C4 C3 C2 121.3(5) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 119.8(5) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 121.0(4) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 120.6(4) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C6 C7 C8 122.6(4) . . ? C6 C7 C2 118.5(4) . . ? C8 C7 C2 118.9(4) . . ? C9 C8 C7 120.9(4) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 120.7(4) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C1 C10 C9 119.6(4) . . ? C1 C10 C11 118.3(4) . . ? C9 C10 C11 122.1(4) . . ? O1 C11 N1 122.7(4) . . ? O1 C11 C10 122.6(4) . . ? N1 C11 C10 114.7(4) . . ? C17 C12 C13 119.8(4) . . ? C17 C12 N1 116.8(4) . . ? C13 C12 N1 123.3(4) . . ? C14 C13 C12 119.9(4) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C15 C14 C13 119.9(4) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C16 C15 C14 120.9(4) . . ? C16 C15 Br1 119.3(4) . . ? C14 C15 Br1 119.7(3) . . ? C15 C16 C17 119.2(4) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C12 C17 C16 120.2(4) . . ? C12 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C11 N1 C12 127.7(4) . . ? C11 N1 H1B 116.1 . . ? C12 N1 H1B 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 C10 C1 C2 C3 179.4(4) . . . . ? C10 C1 C2 C7 -1.8(6) . . . . ? C1 C2 C3 C4 178.9(5) . . . . ? C7 C2 C3 C4 0.1(7) . . . . ? C2 C3 C4 C5 -0.4(8) . . . . ? C3 C4 C5 C6 0.6(8) . . . . ? C4 C5 C6 C7 -0.5(8) . . . . ? C5 C6 C7 C8 -179.7(5) . . . . ? C5 C6 C7 C2 0.2(7) . . . . ? C3 C2 C7 C6 0.0(6) . . . . ? C1 C2 C7 C6 -178.9(4) . . . . ? C3 C2 C7 C8 179.9(4) . . . . ? C1 C2 C7 C8 1.1(6) . . . . ? C6 C7 C8 C9 179.8(5) . . . . ? C2 C7 C8 C9 -0.2(6) . . . . ? C7 C8 C9 C10 -0.1(7) . . . . ? C2 C1 C10 C9 1.5(6) . . . . ? C2 C1 C10 C11 179.2(4) . . . . ? C8 C9 C10 C1 -0.5(7) . . . . ? C8 C9 C10 C11 -178.1(4) . . . . ? C1 C10 C11 O1 -26.8(7) . . . . ? C9 C10 C11 O1 150.8(5) . . . . ? C1 C10 C11 N1 152.7(4) . . . . ? C9 C10 C11 N1 -29.8(6) . . . . ? C17 C12 C13 C14 -0.4(7) . . . . ? N1 C12 C13 C14 -176.1(4) . . . . ? C12 C13 C14 C15 1.1(7) . . . . ? C13 C14 C15 C16 -1.2(7) . . . . ? C13 C14 C15 Br1 179.0(3) . . . . ? C14 C15 C16 C17 0.7(7) . . . . ? Br1 C15 C16 C17 -179.5(4) . . . . ? C13 C12 C17 C16 -0.1(7) . . . . ? N1 C12 C17 C16 175.8(4) . . . . ? C15 C16 C17 C12 0.0(7) . . . . ? O1 C11 N1 C12 -6.8(8) . . . . ? C10 C11 N1 C12 173.8(4) . . . . ? C17 C12 N1 C11 158.0(5) . . . . ? C13 C12 N1 C11 -26.2(7) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 29.19 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.401 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.080 _database_code_depnum_ccdc_archive 'CCDC 947151' ####################################################################### # # 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\544\new _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H12 Cl1 N1 O1' _chemical_formula_weight 281.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 5.5931(12) _cell_length_b 7.6167(19) _cell_length_c 15.880(4) _cell_angle_alpha 88.41(2) _cell_angle_beta 83.971(18) _cell_angle_gamma 84.915(19) _cell_volume 670.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7557 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 29.25 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.279 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.910 _exptl_absorpt_correction_T_max 0.942 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 7557 _diffrn_reflns_av_R_equivalents 0.0951 _diffrn_reflns_av_sigmaI/netI 0.0995 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 29.25 _reflns_number_total 3611 _reflns_number_gt 2512 _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^)+(0.1000P)^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 0.055(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3611 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1012 _refine_ls_R_factor_gt 0.0954 _refine_ls_wR_factor_ref 0.1542 _refine_ls_wR_factor_gt 0.1231 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.166 _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 0.5143(7) 0.8162(5) 0.3562(3) 0.0473(9) Uani 1 1 d . . . H1 H 0.6431 0.8668 0.3756 0.057 Uiso 1 1 calc R . . C2 C 0.4969(7) 0.8122(5) 0.2676(3) 0.0450(9) Uani 1 1 d . . . C3 C 0.6665(8) 0.8851(6) 0.2070(3) 0.0532(10) Uani 1 1 d . . . H3 H 0.7938 0.9398 0.2251 0.064 Uiso 1 1 calc R . . C4 C 0.6453(8) 0.8760(6) 0.1224(3) 0.0620(12) Uani 1 1 d . . . H4 H 0.7582 0.9245 0.0834 0.074 Uiso 1 1 calc R . . C5 C 0.4555(9) 0.7944(6) 0.0938(3) 0.0622(12) Uani 1 1 d . . . H5 H 0.4431 0.7889 0.0360 0.075 Uiso 1 1 calc R . . C6 C 0.2871(8) 0.7222(6) 0.1506(3) 0.0556(11) Uani 1 1 d . . . H6 H 0.1621 0.6674 0.1310 0.067 Uiso 1 1 calc R . . C7 C 0.3031(7) 0.7309(5) 0.2392(3) 0.0468(9) Uani 1 1 d . . . C8 C 0.1335(7) 0.6582(6) 0.2992(3) 0.0525(10) Uani 1 1 d . . . H8 H 0.0073 0.6028 0.2808 0.063 Uiso 1 1 calc R . . C9 C 0.1521(7) 0.6679(5) 0.3844(3) 0.0490(9) Uani 1 1 d . . . H9 H 0.0365 0.6218 0.4232 0.059 Uiso 1 1 calc R . . C10 C 0.3463(7) 0.7475(5) 0.4134(3) 0.0476(9) Uani 1 1 d . . . C11 C 0.3818(8) 0.7555(5) 0.5062(3) 0.0510(10) Uani 1 1 d . . . C12 C 0.1465(7) 0.7460(5) 0.6489(3) 0.0476(9) Uani 1 1 d . . . C13 C -0.0741(8) 0.8112(5) 0.6910(3) 0.0520(10) Uani 1 1 d . . . H13 H -0.1930 0.8654 0.6599 0.062 Uiso 1 1 calc R . . C14 C -0.1183(8) 0.7963(5) 0.7781(3) 0.0530(10) Uani 1 1 d . . . H14 H -0.2655 0.8397 0.8058 0.064 Uiso 1 1 calc R . . C15 C 0.0611(8) 0.7156(5) 0.8231(3) 0.0496(10) Uani 1 1 d . . . C16 C 0.2788(8) 0.6516(6) 0.7830(3) 0.0564(11) Uani 1 1 d . . . H16 H 0.3973 0.5982 0.8145 0.068 Uiso 1 1 calc R . . C17 C 0.3225(7) 0.6664(5) 0.6961(3) 0.0511(10) Uani 1 1 d . . . H17 H 0.4705 0.6229 0.6691 0.061 Uiso 1 1 calc R . . N1 N 0.1717(6) 0.7562(5) 0.5592(2) 0.0542(9) Uani 1 1 d . . . H1B H 0.0401 0.7638 0.5353 0.065 Uiso 1 1 calc R . . O1 O 0.5798(6) 0.7584(5) 0.5309(2) 0.0677(9) Uani 1 1 d . . . Cl1 Cl 0.0050(3) 0.69563(19) 0.93309(8) 0.0773(5) 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 0.044(2) 0.047(2) 0.052(2) -0.0039(17) -0.0043(17) -0.0054(16) C2 0.044(2) 0.039(2) 0.052(2) -0.0026(16) -0.0065(17) -0.0005(16) C3 0.052(2) 0.047(2) 0.060(3) -0.0012(19) -0.0037(19) -0.0073(18) C4 0.062(3) 0.073(3) 0.049(2) 0.004(2) 0.005(2) -0.007(2) C5 0.071(3) 0.070(3) 0.044(2) -0.007(2) -0.004(2) 0.001(2) C6 0.054(2) 0.064(3) 0.050(2) -0.004(2) -0.0096(19) -0.004(2) C7 0.048(2) 0.044(2) 0.049(2) -0.0033(17) -0.0089(17) -0.0014(16) C8 0.047(2) 0.051(2) 0.062(3) -0.0061(19) -0.0105(19) -0.0111(18) C9 0.046(2) 0.047(2) 0.054(2) 0.0003(18) -0.0026(18) -0.0083(17) C10 0.046(2) 0.045(2) 0.051(2) -0.0061(17) -0.0047(17) -0.0038(17) C11 0.052(2) 0.051(2) 0.050(2) 0.0009(18) -0.0046(19) -0.0065(18) C12 0.052(2) 0.042(2) 0.050(2) -0.0028(17) -0.0065(18) -0.0073(17) C13 0.057(2) 0.047(2) 0.054(2) -0.0005(18) -0.0121(19) -0.0036(18) C14 0.052(2) 0.050(2) 0.056(3) -0.0076(19) 0.0002(19) -0.0068(19) C15 0.057(2) 0.051(2) 0.043(2) -0.0026(17) -0.0037(18) -0.0122(19) C16 0.063(3) 0.050(2) 0.056(3) 0.0004(19) -0.011(2) -0.005(2) C17 0.049(2) 0.050(2) 0.053(2) -0.0012(18) -0.0015(18) -0.0041(18) N1 0.0523(19) 0.064(2) 0.0464(19) -0.0013(16) -0.0079(15) -0.0020(16) O1 0.0543(18) 0.096(3) 0.0551(19) 0.0009(17) -0.0075(15) -0.0191(16) Cl1 0.0933(10) 0.0918(10) 0.0465(6) 0.0011(6) 0.0002(6) -0.0154(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 C10 1.366(6) . ? C1 C2 1.421(6) . ? C1 H1 0.9300 . ? C2 C7 1.414(5) . ? C2 C3 1.416(6) . ? C3 C4 1.365(6) . ? C3 H3 0.9300 . ? C4 C5 1.397(7) . ? C4 H4 0.9300 . ? C5 C6 1.374(6) . ? C5 H5 0.9300 . ? C6 C7 1.423(6) . ? C6 H6 0.9300 . ? C7 C8 1.410(6) . ? C8 C9 1.373(6) . ? C8 H8 0.9300 . ? C9 C10 1.414(6) . ? C9 H9 0.9300 . ? C10 C11 1.510(6) . ? C11 O1 1.215(5) . ? C11 N1 1.372(5) . ? C12 C17 1.386(6) . ? C12 C13 1.397(6) . ? C12 N1 1.417(5) . ? C13 C14 1.383(6) . ? C13 H13 0.9300 . ? C14 C15 1.383(6) . ? C14 H14 0.9300 . ? C15 C16 1.369(6) . ? C15 Cl1 1.747(4) . ? C16 C17 1.380(6) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? N1 H1B 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 C10 C1 C2 121.6(4) . . ? C10 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? C7 C2 C3 118.9(4) . . ? C7 C2 C1 118.4(4) . . ? C3 C2 C1 122.6(4) . . ? C4 C3 C2 120.8(4) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 120.6(4) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 120.4(4) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 120.3(4) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C2 119.2(4) . . ? C8 C7 C6 121.8(4) . . ? C2 C7 C6 118.9(4) . . ? C9 C8 C7 121.0(4) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 120.2(4) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C1 C10 C9 119.6(4) . . ? C1 C10 C11 117.8(4) . . ? C9 C10 C11 122.6(4) . . ? O1 C11 N1 123.6(4) . . ? O1 C11 C10 122.5(4) . . ? N1 C11 C10 113.9(4) . . ? C17 C12 C13 118.8(4) . . ? C17 C12 N1 123.6(4) . . ? C13 C12 N1 117.5(4) . . ? C14 C13 C12 121.0(4) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C15 C14 C13 118.6(4) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? C16 C15 C14 121.3(4) . . ? C16 C15 Cl1 120.1(3) . . ? C14 C15 Cl1 118.7(3) . . ? C15 C16 C17 120.1(4) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C12 120.3(4) . . ? C16 C17 H17 119.9 . . ? C12 C17 H17 119.9 . . ? C11 N1 C12 127.5(4) . . ? C11 N1 H1B 116.2 . . ? C12 N1 H1B 116.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C7 -1.5(5) . . . . ? C10 C1 C2 C3 179.0(4) . . . . ? C7 C2 C3 C4 -0.6(6) . . . . ? C1 C2 C3 C4 179.0(4) . . . . ? C2 C3 C4 C5 0.0(7) . . . . ? C3 C4 C5 C6 0.1(7) . . . . ? C4 C5 C6 C7 0.5(7) . . . . ? C3 C2 C7 C8 -180.0(4) . . . . ? C1 C2 C7 C8 0.5(5) . . . . ? C3 C2 C7 C6 1.1(5) . . . . ? C1 C2 C7 C6 -178.5(4) . . . . ? C5 C6 C7 C8 -180.0(4) . . . . ? C5 C6 C7 C2 -1.0(6) . . . . ? C2 C7 C8 C9 1.1(6) . . . . ? C6 C7 C8 C9 180.0(4) . . . . ? C7 C8 C9 C10 -1.6(6) . . . . ? C2 C1 C10 C9 1.0(6) . . . . ? C2 C1 C10 C11 179.2(3) . . . . ? C8 C9 C10 C1 0.6(6) . . . . ? C8 C9 C10 C11 -177.5(4) . . . . ? C1 C10 C11 O1 -27.2(6) . . . . ? C9 C10 C11 O1 150.9(4) . . . . ? C1 C10 C11 N1 153.8(4) . . . . ? C9 C10 C11 N1 -28.1(6) . . . . ? C17 C12 C13 C14 -0.4(6) . . . . ? N1 C12 C13 C14 176.0(4) . . . . ? C12 C13 C14 C15 0.1(6) . . . . ? C13 C14 C15 C16 0.2(6) . . . . ? C13 C14 C15 Cl1 -179.7(3) . . . . ? C14 C15 C16 C17 -0.2(7) . . . . ? Cl1 C15 C16 C17 179.6(3) . . . . ? C15 C16 C17 C12 0.0(7) . . . . ? C13 C12 C17 C16 0.3(6) . . . . ? N1 C12 C17 C16 -175.9(4) . . . . ? O1 C11 N1 C12 -5.5(7) . . . . ? C10 C11 N1 C12 173.4(4) . . . . ? C17 C12 N1 C11 -26.4(7) . . . . ? C13 C12 N1 C11 157.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 29.25 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.301 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.078 _database_code_depnum_ccdc_archive 'CCDC 947152' ####################################################################### # # 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\547\new-kh547 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H12 F1 N1 O1' _chemical_formula_weight 265.28 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 5.6099(14) _cell_length_b 7.6163(19) _cell_length_c 14.943(3) _cell_angle_alpha 88.730(19) _cell_angle_beta 84.005(19) _cell_angle_gamma 85.28(2) _cell_volume 632.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7128 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 29.17 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.097 _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 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 7128 _diffrn_reflns_av_R_equivalents 0.0974 _diffrn_reflns_av_sigmaI/netI 0.0871 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 29.17 _reflns_number_total 3398 _reflns_number_gt 2092 _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^)+(0.1020P)^2^+0.0425P] 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 3398 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1070 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.2027 _refine_ls_wR_factor_gt 0.1718 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.003 _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 -0.0133(4) 0.1837(3) 0.14911(13) 0.0337(4) Uani 1 1 d . . . H1 H -0.1410 0.1313 0.1287 0.040 Uiso 1 1 calc R . . C2 C 0.0034(4) 0.1923(2) 0.24297(13) 0.0324(4) Uani 1 1 d . . . C3 C -0.1684(4) 0.1211(3) 0.30718(15) 0.0399(5) Uani 1 1 d . . . H3 H -0.2941 0.0644 0.2879 0.048 Uiso 1 1 calc R . . C4 C -0.1506(5) 0.1354(3) 0.39679(16) 0.0486(6) Uani 1 1 d . . . H4 H -0.2659 0.0903 0.4383 0.058 Uiso 1 1 calc R . . C5 C 0.0412(5) 0.2178(3) 0.42707(16) 0.0494(6) Uani 1 1 d . . . H5 H 0.0525 0.2257 0.4885 0.059 Uiso 1 1 calc R . . C6 C 0.2101(4) 0.2860(3) 0.36723(15) 0.0423(5) Uani 1 1 d . . . H6 H 0.3350 0.3410 0.3882 0.051 Uiso 1 1 calc R . . C7 C 0.1980(4) 0.2741(3) 0.27271(13) 0.0333(4) Uani 1 1 d . . . C8 C 0.3686(4) 0.3434(3) 0.20844(14) 0.0374(5) Uani 1 1 d . . . H8 H 0.4960 0.3981 0.2278 0.045 Uiso 1 1 calc R . . C9 C 0.3512(4) 0.3322(3) 0.11885(15) 0.0388(5) Uani 1 1 d . . . H9 H 0.4672 0.3773 0.0776 0.047 Uiso 1 1 calc R . . C10 C 0.1562(4) 0.2517(3) 0.08791(13) 0.0330(4) Uani 1 1 d . . . C11 C 0.1236(4) 0.2433(3) -0.01003(14) 0.0365(5) Uani 1 1 d . . . C12 C 0.3569(4) 0.2516(3) -0.16172(13) 0.0326(4) Uani 1 1 d . . . C13 C 0.1785(4) 0.3335(3) -0.21002(14) 0.0366(5) Uani 1 1 d . . . H13 H 0.0322 0.3770 -0.1805 0.044 Uiso 1 1 calc R . . C14 C 0.2220(4) 0.3491(3) -0.30271(15) 0.0398(5) Uani 1 1 d . . . H14 H 0.1049 0.4032 -0.3361 0.048 Uiso 1 1 calc R . . C15 C 0.4401(4) 0.2837(3) -0.34487(14) 0.0409(5) Uani 1 1 d . . . C16 C 0.6180(4) 0.2021(3) -0.29872(15) 0.0408(5) Uani 1 1 d . . . H16 H 0.7636 0.1587 -0.3289 0.049 Uiso 1 1 calc R . . C17 C 0.5758(4) 0.1859(3) -0.20642(15) 0.0384(5) Uani 1 1 d . . . H17 H 0.6939 0.1309 -0.1738 0.046 Uiso 1 1 calc R . . N1 N 0.3317(3) 0.2417(3) -0.06630(12) 0.0407(4) Uani 1 1 d . . . H1B H 0.4630 0.2337 -0.0409 0.049 Uiso 1 1 calc R . . O1 O -0.0757(3) 0.2388(3) -0.03611(11) 0.0530(5) Uani 1 1 d . . . F1 F 0.4824(3) 0.3009(2) -0.43592(9) 0.0647(5) 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 0.0318(10) 0.0397(10) 0.0303(10) -0.0021(8) -0.0042(8) -0.0048(8) C2 0.0304(10) 0.0342(9) 0.0322(10) 0.0000(7) -0.0036(7) 0.0003(8) C3 0.0340(11) 0.0466(12) 0.0384(11) 0.0044(9) -0.0011(9) -0.0047(9) C4 0.0475(14) 0.0599(14) 0.0356(12) 0.0078(10) 0.0053(10) -0.0012(11) C5 0.0534(15) 0.0645(15) 0.0291(11) -0.0011(10) -0.0045(10) 0.0039(12) C6 0.0431(12) 0.0515(12) 0.0337(11) -0.0042(9) -0.0117(9) -0.0016(10) C7 0.0310(10) 0.0362(10) 0.0328(10) -0.0020(7) -0.0069(8) 0.0022(8) C8 0.0325(10) 0.0425(11) 0.0385(11) -0.0021(8) -0.0064(8) -0.0064(9) C9 0.0369(11) 0.0449(11) 0.0352(11) 0.0040(8) -0.0040(8) -0.0082(9) C10 0.0306(10) 0.0386(10) 0.0293(10) -0.0016(7) -0.0034(7) 0.0000(8) C11 0.0367(11) 0.0421(11) 0.0313(10) 0.0005(8) -0.0046(8) -0.0056(8) C12 0.0324(10) 0.0361(10) 0.0297(10) -0.0023(7) -0.0029(8) -0.0046(8) C13 0.0299(10) 0.0449(11) 0.0340(10) -0.0014(8) -0.0013(8) 0.0010(8) C14 0.0375(12) 0.0481(12) 0.0349(11) 0.0029(9) -0.0097(9) -0.0027(9) C15 0.0471(13) 0.0484(12) 0.0276(10) -0.0034(8) -0.0020(9) -0.0077(10) C16 0.0292(10) 0.0527(13) 0.0390(12) -0.0077(9) 0.0040(8) -0.0008(9) C17 0.0304(10) 0.0457(11) 0.0388(11) -0.0019(9) -0.0051(8) 0.0010(8) N1 0.0345(10) 0.0600(11) 0.0277(9) 0.0007(8) -0.0055(7) -0.0005(8) O1 0.0393(9) 0.0874(13) 0.0347(9) 0.0015(8) -0.0080(7) -0.0138(9) F1 0.0666(11) 0.0973(12) 0.0281(7) -0.0012(7) 0.0014(7) -0.0018(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 C10 1.374(3) . ? C1 C2 1.419(3) . ? C1 H1 0.9300 . ? C2 C7 1.416(3) . ? C2 C3 1.419(3) . ? C3 C4 1.361(3) . ? C3 H3 0.9300 . ? C4 C5 1.408(4) . ? C4 H4 0.9300 . ? C5 C6 1.360(4) . ? C5 H5 0.9300 . ? C6 C7 1.426(3) . ? C6 H6 0.9300 . ? C7 C8 1.409(3) . ? C8 C9 1.358(3) . ? C8 H8 0.9300 . ? C9 C10 1.419(3) . ? C9 H9 0.9300 . ? C10 C11 1.497(3) . ? C11 O1 1.225(3) . ? C11 N1 1.365(3) . ? C12 C13 1.393(3) . ? C12 C17 1.395(3) . ? C12 N1 1.419(3) . ? C13 C14 1.385(3) . ? C13 H13 0.9300 . ? C14 C15 1.377(3) . ? C14 H14 0.9300 . ? C15 F1 1.362(2) . ? C15 C16 1.371(3) . ? C16 C17 1.379(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? N1 H1B 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 C10 C1 C2 121.09(19) . . ? C10 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C7 C2 C3 119.51(19) . . ? C7 C2 C1 118.57(18) . . ? C3 C2 C1 121.92(19) . . ? C4 C3 C2 120.4(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.5(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 120.8(2) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C2 119.12(19) . . ? C8 C7 C6 122.7(2) . . ? C2 C7 C6 118.21(19) . . ? C9 C8 C7 121.4(2) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C10 120.17(19) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C1 C10 C9 119.61(19) . . ? C1 C10 C11 118.31(19) . . ? C9 C10 C11 122.04(18) . . ? O1 C11 N1 123.7(2) . . ? O1 C11 C10 121.7(2) . . ? N1 C11 C10 114.63(18) . . ? C13 C12 C17 120.24(19) . . ? C13 C12 N1 122.19(18) . . ? C17 C12 N1 117.44(18) . . ? C14 C13 C12 119.1(2) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C15 C14 C13 119.3(2) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? F1 C15 C16 118.4(2) . . ? F1 C15 C14 119.0(2) . . ? C16 C15 C14 122.6(2) . . ? C15 C16 C17 118.4(2) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? C16 C17 C12 120.4(2) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? C11 N1 C12 127.66(18) . . ? C11 N1 H1B 116.2 . . ? C12 N1 H1B 116.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C7 0.6(3) . . . . ? C10 C1 C2 C3 -179.30(19) . . . . ? C7 C2 C3 C4 1.8(3) . . . . ? C1 C2 C3 C4 -178.4(2) . . . . ? C2 C3 C4 C5 -1.2(4) . . . . ? C3 C4 C5 C6 0.6(4) . . . . ? C4 C5 C6 C7 -0.6(4) . . . . ? C3 C2 C7 C8 179.62(18) . . . . ? C1 C2 C7 C8 -0.3(3) . . . . ? C3 C2 C7 C6 -1.7(3) . . . . ? C1 C2 C7 C6 178.47(19) . . . . ? C5 C6 C7 C8 179.8(2) . . . . ? C5 C6 C7 C2 1.1(3) . . . . ? C2 C7 C8 C9 -0.5(3) . . . . ? C6 C7 C8 C9 -179.2(2) . . . . ? C7 C8 C9 C10 1.0(3) . . . . ? C2 C1 C10 C9 -0.1(3) . . . . ? C2 C1 C10 C11 -178.13(18) . . . . ? C8 C9 C10 C1 -0.7(3) . . . . ? C8 C9 C10 C11 177.3(2) . . . . ? C1 C10 C11 O1 26.4(3) . . . . ? C9 C10 C11 O1 -151.6(2) . . . . ? C1 C10 C11 N1 -153.82(19) . . . . ? C9 C10 C11 N1 28.2(3) . . . . ? C17 C12 C13 C14 -0.2(3) . . . . ? N1 C12 C13 C14 175.54(19) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? C13 C14 C15 F1 -179.45(19) . . . . ? C13 C14 C15 C16 0.3(4) . . . . ? F1 C15 C16 C17 179.5(2) . . . . ? C14 C15 C16 C17 -0.3(3) . . . . ? C15 C16 C17 C12 -0.1(3) . . . . ? C13 C12 C17 C16 0.3(3) . . . . ? N1 C12 C17 C16 -175.67(19) . . . . ? O1 C11 N1 C12 6.5(4) . . . . ? C10 C11 N1 C12 -173.31(19) . . . . ? C13 C12 N1 C11 26.6(3) . . . . ? C17 C12 N1 C11 -157.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 29.17 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.283 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.063 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N1 H1B O1 0.8600 2.6000 3.400(3) 155.00 1_655 yes C13 H13 O1 0.9300 2.4200 2.936(3) 115.00 . yes _database_code_depnum_ccdc_archive 'CCDC 947153' ####################################################################### # # 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\c133\khc133 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H12 I1 N1 O1' _chemical_formula_weight 373.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 32.1685(16) _cell_length_b 10.7211(4) _cell_length_c 8.2676(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.678(4) _cell_angle_gamma 90.00 _cell_volume 2837.4(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 11361 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 29.18 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.747 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 2.251 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.590 _exptl_absorpt_correction_T_max 0.800 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 11361 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 29.18 _reflns_number_total 3823 _reflns_number_gt 2769 _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^)+(0.0526P)^2^+5.5822P] 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 3823 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1292 _refine_ls_wR_factor_gt 0.1177 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.007 _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 0.16497(12) 0.9702(3) -0.4197(4) 0.0371(8) Uani 1 1 d . . . H1 H 0.1755 1.0465 -0.4503 0.045 Uiso 1 1 calc R . . C2 C 0.12328(12) 0.9394(4) -0.4699(4) 0.0365(7) Uani 1 1 d . . . C3 C 0.09621(13) 1.0205(4) -0.5651(5) 0.0462(9) Uani 1 1 d . . . H3 H 0.1062 1.0967 -0.5985 0.055 Uiso 1 1 calc R . . C4 C 0.05572(15) 0.9884(5) -0.6085(6) 0.0585(12) Uani 1 1 d . . . H4 H 0.0380 1.0426 -0.6699 0.070 Uiso 1 1 calc R . . C5 C 0.04138(12) 0.8749(4) -0.5604(5) 0.0420(9) Uani 1 1 d . . . H5 H 0.0136 0.8545 -0.5913 0.050 Uiso 1 1 calc R . . C6 C 0.06491(14) 0.7921(4) -0.4718(5) 0.0499(10) Uani 1 1 d . . . H6 H 0.0537 0.7162 -0.4432 0.060 Uiso 1 1 calc R . . C7 C 0.10732(12) 0.8221(4) -0.4222(5) 0.0391(8) Uani 1 1 d . . . C8 C 0.13434(13) 0.7413(4) -0.3275(5) 0.0421(8) Uani 1 1 d . . . H8 H 0.1243 0.6646 -0.2962 0.051 Uiso 1 1 calc R . . C9 C 0.17451(13) 0.7721(4) -0.2809(5) 0.0426(8) Uani 1 1 d . . . H9 H 0.1917 0.7164 -0.2195 0.051 Uiso 1 1 calc R . . C10 C 0.19066(11) 0.8896(3) -0.3257(4) 0.0361(7) Uani 1 1 d . . . C11 C 0.23410(12) 0.9321(4) -0.2721(5) 0.0412(8) Uani 1 1 d . . . C12 C 0.30498(12) 0.8558(3) -0.1808(4) 0.0368(8) Uani 1 1 d . . . C13 C 0.31812(13) 0.9475(4) -0.0682(5) 0.0433(9) Uani 1 1 d . . . H13 H 0.2988 1.0023 -0.0305 0.052 Uiso 1 1 calc R . . C14 C 0.35960(13) 0.9569(4) -0.0129(5) 0.0457(9) Uani 1 1 d . . . H14 H 0.3684 1.0183 0.0622 0.055 Uiso 1 1 calc R . . C15 C 0.38838(12) 0.8755(4) -0.0684(5) 0.0423(9) Uani 1 1 d . . . C16 C 0.37572(13) 0.7836(4) -0.1797(5) 0.0439(9) Uani 1 1 d . . . H16 H 0.3951 0.7288 -0.2165 0.053 Uiso 1 1 calc R . . C17 C 0.33396(12) 0.7741(4) -0.2357(5) 0.0405(8) Uani 1 1 d . . . H17 H 0.3252 0.7125 -0.3106 0.049 Uiso 1 1 calc R . . N1 N 0.26242(10) 0.8388(3) -0.2373(4) 0.0437(7) Uani 1 1 d . . . H1B H 0.2537 0.7633 -0.2509 0.052 Uiso 1 1 calc R . . O1 O 0.24351(9) 1.0423(3) -0.2602(4) 0.0544(8) Uani 1 1 d . . . I1 I 0.451559(9) 0.89260(3) 0.01893(5) 0.06833(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 0.0403(18) 0.0305(17) 0.0407(19) 0.0018(15) 0.0047(15) -0.0014(14) C2 0.0397(18) 0.0379(18) 0.0320(17) -0.0036(15) 0.0042(14) 0.0019(15) C3 0.048(2) 0.045(2) 0.044(2) 0.0083(18) -0.0008(17) -0.0010(17) C4 0.050(2) 0.073(3) 0.049(2) 0.007(2) -0.0122(19) 0.011(2) C5 0.0319(17) 0.055(2) 0.0380(19) 0.0013(17) 0.0002(14) 0.0005(16) C6 0.045(2) 0.049(2) 0.056(2) -0.002(2) 0.0061(19) -0.0091(18) C7 0.0429(19) 0.0336(18) 0.0415(19) -0.0044(16) 0.0079(15) -0.0037(15) C8 0.048(2) 0.0292(18) 0.050(2) 0.0036(16) 0.0094(17) -0.0034(15) C9 0.045(2) 0.0345(19) 0.049(2) 0.0073(17) 0.0054(17) 0.0046(15) C10 0.0344(16) 0.0351(17) 0.0387(18) -0.0001(15) 0.0039(13) 0.0005(14) C11 0.0393(18) 0.0377(19) 0.046(2) 0.0024(16) 0.0022(16) 0.0022(15) C12 0.0391(18) 0.0317(17) 0.0390(19) 0.0016(14) 0.0001(15) 0.0013(14) C13 0.044(2) 0.0369(19) 0.049(2) -0.0041(17) 0.0036(17) 0.0090(16) C14 0.048(2) 0.037(2) 0.049(2) -0.0025(17) -0.0068(17) -0.0004(16) C15 0.0367(18) 0.041(2) 0.049(2) 0.0101(17) 0.0000(15) -0.0006(15) C16 0.042(2) 0.043(2) 0.047(2) -0.0012(17) 0.0094(16) 0.0077(16) C17 0.044(2) 0.0338(18) 0.043(2) -0.0081(16) 0.0026(16) 0.0017(15) N1 0.0377(16) 0.0313(16) 0.061(2) -0.0050(15) -0.0011(14) 0.0015(13) O1 0.0462(16) 0.0310(15) 0.084(2) 0.0055(14) -0.0052(15) -0.0026(12) I1 0.03895(17) 0.0694(2) 0.0936(3) 0.00253(19) -0.00867(14) -0.00462(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C10 1.381(5) . ? C1 C2 1.404(5) . ? C1 H1 0.9300 . ? C2 C3 1.414(5) . ? C2 C7 1.428(5) . ? C3 C4 1.361(6) . ? C3 H3 0.9300 . ? C4 C5 1.373(7) . ? C4 H4 0.9300 . ? C5 C6 1.337(6) . ? C5 H5 0.9300 . ? C6 C7 1.422(6) . ? C6 H6 0.9300 . ? C7 C8 1.409(6) . ? C8 C9 1.352(6) . ? C8 H8 0.9300 . ? C9 C10 1.426(5) . ? C9 H9 0.9300 . ? C10 C11 1.495(5) . ? C11 O1 1.221(5) . ? C11 N1 1.365(5) . ? C12 C17 1.388(5) . ? C12 C13 1.390(6) . ? C12 N1 1.414(5) . ? C13 C14 1.371(6) . ? C13 H13 0.9300 . ? C14 C15 1.383(6) . ? C14 H14 0.9300 . ? C15 C16 1.381(6) . ? C15 I1 2.097(4) . ? C16 C17 1.381(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? N1 H1B 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 C10 C1 C2 121.3(3) . . ? C10 C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? C1 C2 C3 122.5(4) . . ? C1 C2 C7 119.0(3) . . ? C3 C2 C7 118.5(4) . . ? C4 C3 C2 120.8(4) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.2(4) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 124.0(4) . . ? C6 C5 H5 118.0 . . ? C4 C5 H5 118.0 . . ? C5 C6 C7 118.9(4) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C8 C7 C6 122.9(4) . . ? C8 C7 C2 118.4(3) . . ? C6 C7 C2 118.7(4) . . ? C9 C8 C7 121.8(4) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C8 C9 C10 120.3(4) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C1 C10 C9 119.1(3) . . ? C1 C10 C11 117.8(3) . . ? C9 C10 C11 123.2(3) . . ? O1 C11 N1 122.5(4) . . ? O1 C11 C10 122.4(4) . . ? N1 C11 C10 115.1(3) . . ? C17 C12 C13 119.7(3) . . ? C17 C12 N1 118.0(3) . . ? C13 C12 N1 122.2(3) . . ? C14 C13 C12 119.8(4) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.3(4) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 120.5(4) . . ? C16 C15 I1 120.2(3) . . ? C14 C15 I1 119.2(3) . . ? C17 C16 C15 119.3(4) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C12 120.4(4) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? C11 N1 C12 125.4(3) . . ? C11 N1 H1B 117.3 . . ? C12 N1 H1B 117.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 179.5(4) . . . . ? C10 C1 C2 C7 0.1(5) . . . . ? C1 C2 C3 C4 -178.6(4) . . . . ? C7 C2 C3 C4 0.9(6) . . . . ? C2 C3 C4 C5 -0.8(7) . . . . ? C3 C4 C5 C6 0.1(7) . . . . ? C4 C5 C6 C7 0.5(7) . . . . ? C5 C6 C7 C8 179.4(4) . . . . ? C5 C6 C7 C2 -0.5(6) . . . . ? C1 C2 C7 C8 -0.7(5) . . . . ? C3 C2 C7 C8 179.9(4) . . . . ? C1 C2 C7 C6 179.2(4) . . . . ? C3 C2 C7 C6 -0.2(5) . . . . ? C6 C7 C8 C9 -179.6(4) . . . . ? C2 C7 C8 C9 0.3(6) . . . . ? C7 C8 C9 C10 0.7(6) . . . . ? C2 C1 C10 C9 0.9(6) . . . . ? C2 C1 C10 C11 -177.6(3) . . . . ? C8 C9 C10 C1 -1.3(6) . . . . ? C8 C9 C10 C11 177.1(4) . . . . ? C1 C10 C11 O1 24.5(6) . . . . ? C9 C10 C11 O1 -153.9(4) . . . . ? C1 C10 C11 N1 -155.6(4) . . . . ? C9 C10 C11 N1 26.0(5) . . . . ? C17 C12 C13 C14 0.4(6) . . . . ? N1 C12 C13 C14 177.6(4) . . . . ? C12 C13 C14 C15 -0.1(6) . . . . ? C13 C14 C15 C16 -0.2(6) . . . . ? C13 C14 C15 I1 -180.0(3) . . . . ? C14 C15 C16 C17 0.2(6) . . . . ? I1 C15 C16 C17 -180.0(3) . . . . ? C15 C16 C17 C12 0.0(6) . . . . ? C13 C12 C17 C16 -0.3(6) . . . . ? N1 C12 C17 C16 -177.6(4) . . . . ? O1 C11 N1 C12 1.6(7) . . . . ? C10 C11 N1 C12 -178.3(3) . . . . ? C17 C12 N1 C11 -143.4(4) . . . . ? C13 C12 N1 C11 39.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.18 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.907 _refine_diff_density_min -0.720 _refine_diff_density_rms 0.099 _database_code_depnum_ccdc_archive 'CCDC 947154' ####################################################################### # # 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\c141\khc141 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H11 Br N2 O' _chemical_formula_weight 327.17 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 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 6.364(3) _cell_length_b 17.187(9) _cell_length_c 12.649(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.71(4) _cell_angle_gamma 90.00 _cell_volume 1349.5(12) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 15345 _cell_measurement_theta_min 2.03 _cell_measurement_theta_max 29.66 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.610 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 3.042 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.490 _exptl_absorpt_correction_T_max 0.590 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 15345 _diffrn_reflns_av_R_equivalents 0.0951 _diffrn_reflns_av_sigmaI/netI 0.1064 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 29.66 _reflns_number_total 3647 _reflns_number_gt 2106 _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^)+(0.0373P)^2^+0.9759P] 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 3647 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0951 _refine_ls_R_factor_gt 0.0843 _refine_ls_wR_factor_ref 0.1639 _refine_ls_wR_factor_gt 0.1432 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.150 _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 1.9723(7) -0.2287(2) 0.5196(3) 0.0410(10) Uani 1 1 d . . . C2 C 2.0996(8) -0.2535(3) 0.4486(4) 0.0515(11) Uani 1 1 d . . . H2 H 2.0644 -0.2379 0.3765 0.062 Uiso 1 1 calc R . . C3 C 2.2746(9) -0.3002(3) 0.4838(5) 0.0619(13) Uani 1 1 d . . . H3 H 2.3586 -0.3152 0.4358 0.074 Uiso 1 1 calc R . . C4 C 2.3291(9) -0.3258(3) 0.5929(5) 0.0669(15) Uani 1 1 d . . . H4 H 2.4467 -0.3585 0.6161 0.080 Uiso 1 1 calc R . . C5 C 2.2080(9) -0.3023(3) 0.6635(5) 0.0616(14) Uani 1 1 d . . . H5 H 2.2450 -0.3187 0.7353 0.074 Uiso 1 1 calc R . . C6 C 2.0276(8) -0.2536(3) 0.6294(3) 0.0466(11) Uani 1 1 d . . . C7 C 1.8983(10) -0.2279(3) 0.6979(4) 0.0625(14) Uani 1 1 d . . . H7 H 1.9310 -0.2425 0.7705 0.075 Uiso 1 1 calc R . . C8 C 1.7239(9) -0.1814(3) 0.6600(4) 0.0558(12) Uani 1 1 d . . . H8 H 1.6364 -0.1643 0.7052 0.067 Uiso 1 1 calc R . . C9 C 1.6816(7) -0.1604(2) 0.5494(4) 0.0445(10) Uani 1 1 d . . . C10 C 1.4857(8) -0.1115(3) 0.5059(4) 0.0496(11) Uani 1 1 d . . . C11 C 1.2848(8) -0.0534(3) 0.3317(4) 0.0463(11) Uani 1 1 d . . . C12 C 1.0982(8) -0.0331(3) 0.3652(4) 0.0564(12) Uani 1 1 d . . . H12 H 1.0812 -0.0474 0.4338 0.068 Uiso 1 1 calc R . . C13 C 0.9376(8) 0.0084(3) 0.2963(4) 0.0561(12) Uani 1 1 d . . . H13 H 0.8126 0.0221 0.3184 0.067 Uiso 1 1 calc R . . C14 C 0.9643(8) 0.0293(3) 0.1942(4) 0.0538(12) Uani 1 1 d . . . C15 C 1.1474(8) 0.0084(3) 0.1596(4) 0.0524(11) Uani 1 1 d . . . H15 H 1.1630 0.0216 0.0904 0.063 Uiso 1 1 calc R . . C16 C 1.3062(7) -0.0321(3) 0.2287(4) 0.0497(11) Uani 1 1 d . . . H16 H 1.4308 -0.0457 0.2060 0.060 Uiso 1 1 calc R . . N1 N 1.7990(6) -0.1823(2) 0.4805(3) 0.0439(9) Uani 1 1 d . . . N2 N 1.4545(6) -0.0955(2) 0.3974(3) 0.0505(9) Uani 1 1 d . . . H2B H 1.5504 -0.1134 0.3655 0.061 Uiso 1 1 calc R . . O1 O 1.3699(6) -0.0898(2) 0.5641(3) 0.0718(10) Uani 1 1 d . . . Br1 Br 0.74080(10) 0.08642(4) 0.10190(5) 0.0767(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 0.040(2) 0.039(2) 0.043(2) -0.0019(18) 0.0072(18) -0.0071(18) C2 0.055(3) 0.053(3) 0.047(3) 0.000(2) 0.013(2) 0.005(2) C3 0.058(3) 0.057(3) 0.074(4) -0.004(3) 0.022(3) 0.007(2) C4 0.056(3) 0.056(3) 0.085(4) 0.012(3) 0.007(3) 0.005(2) C5 0.061(3) 0.060(3) 0.059(3) 0.016(3) 0.001(3) -0.002(2) C6 0.054(3) 0.044(2) 0.042(2) 0.000(2) 0.012(2) -0.010(2) C7 0.080(4) 0.068(3) 0.037(2) 0.006(2) 0.007(3) -0.010(3) C8 0.067(3) 0.059(3) 0.048(3) -0.007(2) 0.024(2) -0.005(3) C9 0.046(3) 0.040(2) 0.048(3) -0.0091(19) 0.011(2) -0.0058(18) C10 0.051(3) 0.049(3) 0.052(3) -0.008(2) 0.017(2) -0.005(2) C11 0.047(3) 0.040(2) 0.054(3) -0.006(2) 0.015(2) 0.0002(19) C12 0.056(3) 0.059(3) 0.060(3) 0.001(2) 0.024(2) 0.004(2) C13 0.042(3) 0.060(3) 0.071(3) -0.004(3) 0.023(2) 0.005(2) C14 0.047(3) 0.039(2) 0.072(3) 0.001(2) 0.007(2) 0.001(2) C15 0.046(3) 0.054(3) 0.061(3) 0.003(2) 0.020(2) 0.001(2) C16 0.041(3) 0.053(3) 0.061(3) -0.006(2) 0.022(2) 0.002(2) N1 0.047(2) 0.044(2) 0.042(2) -0.0057(16) 0.0139(17) -0.0006(16) N2 0.047(2) 0.053(2) 0.058(2) 0.0015(19) 0.0243(18) 0.0067(18) O1 0.066(2) 0.089(3) 0.065(2) -0.017(2) 0.0246(19) 0.016(2) Br1 0.0551(3) 0.0831(4) 0.0909(5) 0.0172(3) 0.0136(3) 0.0163(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 1.363(5) . ? C1 C2 1.401(7) . ? C1 C6 1.422(6) . ? C2 C3 1.365(7) . ? C2 H2 0.9300 . ? C3 C4 1.418(8) . ? C3 H3 0.9300 . ? C4 C5 1.363(8) . ? C4 H4 0.9300 . ? C5 C6 1.409(7) . ? C5 H5 0.9300 . ? C6 C7 1.393(7) . ? C7 C8 1.365(8) . ? C7 H7 0.9300 . ? C8 C9 1.413(7) . ? C8 H8 0.9300 . ? C9 N1 1.320(6) . ? C9 C10 1.504(7) . ? C10 O1 1.210(6) . ? C10 N2 1.370(6) . ? C11 C16 1.389(6) . ? C11 C12 1.390(7) . ? C11 N2 1.409(6) . ? C12 C13 1.386(7) . ? C12 H12 0.9300 . ? C13 C14 1.386(7) . ? C13 H13 0.9300 . ? C14 C15 1.380(7) . ? C14 Br1 1.902(5) . ? C15 C16 1.371(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? N2 H2B 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 118.8(4) . . ? N1 C1 C6 122.5(4) . . ? C2 C1 C6 118.7(4) . . ? C3 C2 C1 121.0(5) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 120.5(5) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.6(5) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 121.0(5) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C7 C6 C5 123.4(5) . . ? C7 C6 C1 117.3(4) . . ? C5 C6 C1 119.2(5) . . ? C8 C7 C6 120.9(5) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 117.5(5) . . ? C7 C8 H8 121.3 . . ? C9 C8 H8 121.3 . . ? N1 C9 C8 124.6(4) . . ? N1 C9 C10 117.5(4) . . ? C8 C9 C10 117.9(4) . . ? O1 C10 N2 125.0(5) . . ? O1 C10 C9 121.1(5) . . ? N2 C10 C9 113.9(4) . . ? C16 C11 C12 119.1(4) . . ? C16 C11 N2 117.9(4) . . ? C12 C11 N2 123.0(4) . . ? C13 C12 C11 119.9(5) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 119.7(5) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.8(4) . . ? C15 C14 Br1 120.6(4) . . ? C13 C14 Br1 118.5(4) . . ? C16 C15 C14 119.1(5) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C11 121.4(4) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? C9 N1 C1 117.2(4) . . ? C10 N2 C11 128.1(4) . . ? C10 N2 H2B 116.0 . . ? C11 N2 H2B 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 C3 -179.8(4) . . . . ? C6 C1 C2 C3 -0.5(7) . . . . ? C1 C2 C3 C4 1.2(8) . . . . ? C2 C3 C4 C5 -1.3(8) . . . . ? C3 C4 C5 C6 0.8(8) . . . . ? C4 C5 C6 C7 180.0(5) . . . . ? C4 C5 C6 C1 -0.2(7) . . . . ? N1 C1 C6 C7 -0.8(6) . . . . ? C2 C1 C6 C7 179.9(4) . . . . ? N1 C1 C6 C5 179.3(4) . . . . ? C2 C1 C6 C5 0.0(6) . . . . ? C5 C6 C7 C8 -179.3(5) . . . . ? C1 C6 C7 C8 0.9(7) . . . . ? C6 C7 C8 C9 -0.4(8) . . . . ? C7 C8 C9 N1 -0.2(7) . . . . ? C7 C8 C9 C10 178.0(4) . . . . ? N1 C9 C10 O1 179.5(4) . . . . ? C8 C9 C10 O1 1.2(7) . . . . ? N1 C9 C10 N2 -0.2(6) . . . . ? C8 C9 C10 N2 -178.5(4) . . . . ? C16 C11 C12 C13 -0.5(7) . . . . ? N2 C11 C12 C13 -180.0(4) . . . . ? C11 C12 C13 C14 0.0(7) . . . . ? C12 C13 C14 C15 1.0(7) . . . . ? C12 C13 C14 Br1 -179.9(4) . . . . ? C13 C14 C15 C16 -1.5(7) . . . . ? Br1 C14 C15 C16 179.4(3) . . . . ? C14 C15 C16 C11 1.0(7) . . . . ? C12 C11 C16 C15 0.1(7) . . . . ? N2 C11 C16 C15 179.5(4) . . . . ? C8 C9 N1 C1 0.2(6) . . . . ? C10 C9 N1 C1 -177.9(4) . . . . ? C2 C1 N1 C9 179.6(4) . . . . ? C6 C1 N1 C9 0.3(6) . . . . ? O1 C10 N2 C11 -1.5(8) . . . . ? C9 C10 N2 C11 178.2(4) . . . . ? C16 C11 N2 C10 168.3(4) . . . . ? C12 C11 N2 C10 -12.2(7) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 29.66 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.356 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.079 _database_code_depnum_ccdc_archive 'CCDC 947155' ####################################################################### # # 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\c195\khc195-2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H11 Cl1 N2 O1' _chemical_formula_weight 282.72 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 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 14.176(3) _cell_length_b 6.0252(11) _cell_length_c 15.551(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.311(19) _cell_angle_gamma 90.00 _cell_volume 1314.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 14567 _cell_measurement_theta_min 1.81 _cell_measurement_theta_max 29.67 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.286 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.915 _exptl_absorpt_correction_T_max 0.956 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2T' _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 14567 _diffrn_reflns_av_R_equivalents 0.0901 _diffrn_reflns_av_sigmaI/netI 0.0101 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 29.67 _reflns_number_total 3562 _reflns_number_gt 2980 _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^)+(0.0168P)^2^+0.5650P] 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 3562 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1020 _refine_ls_R_factor_gt 0.0826 _refine_ls_wR_factor_ref 0.1423 _refine_ls_wR_factor_gt 0.1223 _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_restrained_S_all 1.160 _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 1.28361(17) -1.0225(5) 0.60275(18) 0.0423(6) Uani 1 1 d . . . C2 C 1.29542(18) -1.1848(5) 0.66915(19) 0.0491(7) Uani 1 1 d . . . H2 H 1.2589 -1.1781 0.7142 0.059 Uiso 1 1 calc R . . C3 C 1.3605(2) -1.3516(6) 0.6671(2) 0.0573(8) Uani 1 1 d . . . H3 H 1.3676 -1.4588 0.7105 0.069 Uiso 1 1 calc R . . C4 C 1.4167(2) -1.3621(6) 0.5998(2) 0.0625(9) Uani 1 1 d . . . H4 H 1.4620 -1.4738 0.6000 0.075 Uiso 1 1 calc R . . C5 C 1.4055(2) -1.2109(6) 0.5343(2) 0.0610(9) Uani 1 1 d . . . H5 H 1.4423 -1.2218 0.4895 0.073 Uiso 1 1 calc R . . C6 C 1.33854(19) -1.0373(5) 0.53351(19) 0.0494(7) Uani 1 1 d . . . C7 C 1.3220(2) -0.8765(6) 0.46710(19) 0.0567(8) Uani 1 1 d . . . H7 H 1.3560 -0.8817 0.4203 0.068 Uiso 1 1 calc R . . C8 C 1.2568(2) -0.7148(5) 0.47152(18) 0.0518(7) Uani 1 1 d . . . H8 H 1.2447 -0.6095 0.4276 0.062 Uiso 1 1 calc R . . C9 C 1.20741(17) -0.7088(5) 0.54390(18) 0.0437(7) Uani 1 1 d . . . C10 C 1.13910(18) -0.5193(5) 0.55053(18) 0.0441(7) Uani 1 1 d . . . C11 C 1.03203(16) -0.3698(5) 0.64988(17) 0.0417(6) Uani 1 1 d . . . C12 C 1.01108(18) -0.1654(5) 0.60912(18) 0.0469(7) Uani 1 1 d . . . H12 H 1.0396 -0.1262 0.5611 0.056 Uiso 1 1 calc R . . C13 C 0.94816(19) -0.0220(5) 0.64006(19) 0.0494(7) Uani 1 1 d . . . H13 H 0.9341 0.1134 0.6124 0.059 Uiso 1 1 calc R . . C14 C 0.90611(17) -0.0768(5) 0.71121(19) 0.0462(7) Uani 1 1 d . . . C15 C 0.92580(19) -0.2792(5) 0.7526(2) 0.0537(8) Uani 1 1 d . . . H15 H 0.8968 -0.3172 0.8005 0.064 Uiso 1 1 calc R . . C16 C 0.98855(18) -0.4228(5) 0.72201(19) 0.0522(8) Uani 1 1 d . . . H16 H 1.0022 -0.5579 0.7500 0.063 Uiso 1 1 calc R . . N1 N 1.21894(13) -0.8561(4) 0.60747(14) 0.0419(5) Uani 1 1 d . . . N2 N 1.09511(14) -0.5255(4) 0.62214(15) 0.0468(6) Uani 1 1 d . . . H2B H 1.1074 -0.6397 0.6550 0.056 Uiso 1 1 calc R . . O1 O 1.12830(15) -0.3745(4) 0.49508(13) 0.0613(6) Uani 1 1 d . . . Cl1 Cl 0.82532(6) 0.10415(15) 0.74849(6) 0.0684(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 0.0377(12) 0.0436(16) 0.0440(15) -0.0070(13) 0.0001(11) -0.0053(11) C2 0.0463(14) 0.0522(19) 0.0470(16) -0.0006(15) 0.0002(12) -0.0008(13) C3 0.0571(16) 0.0490(19) 0.0617(19) -0.0008(16) -0.0054(15) 0.0009(15) C4 0.0580(17) 0.055(2) 0.071(2) -0.0137(19) -0.0023(16) 0.0108(16) C5 0.0620(17) 0.063(2) 0.059(2) -0.0131(18) 0.0126(15) 0.0086(16) C6 0.0490(14) 0.0505(18) 0.0470(17) -0.0099(14) 0.0017(13) -0.0032(13) C7 0.0642(17) 0.065(2) 0.0442(17) -0.0078(16) 0.0172(14) -0.0007(17) C8 0.0632(17) 0.0524(19) 0.0398(16) 0.0012(14) 0.0072(14) -0.0009(15) C9 0.0412(13) 0.0486(17) 0.0392(15) -0.0040(13) -0.0008(12) -0.0056(12) C10 0.0445(13) 0.0458(17) 0.0396(15) -0.0019(13) -0.0024(12) -0.0047(12) C11 0.0370(12) 0.0419(16) 0.0441(15) 0.0029(13) -0.0014(11) -0.0001(12) C12 0.0499(14) 0.0446(17) 0.0463(16) 0.0103(14) 0.0074(12) -0.0010(13) C13 0.0523(15) 0.0407(16) 0.0535(18) 0.0078(14) 0.0023(14) 0.0010(13) C14 0.0405(13) 0.0430(17) 0.0546(17) -0.0013(14) 0.0049(12) 0.0006(12) C15 0.0512(15) 0.058(2) 0.0552(18) 0.0077(16) 0.0189(14) -0.0026(14) C16 0.0512(15) 0.0477(18) 0.0582(19) 0.0155(15) 0.0097(14) 0.0046(14) N1 0.0386(11) 0.0452(14) 0.0403(12) -0.0022(11) 0.0002(9) -0.0026(10) N2 0.0456(11) 0.0459(14) 0.0497(14) 0.0103(12) 0.0092(11) 0.0067(10) O1 0.0800(14) 0.0563(14) 0.0474(12) 0.0122(11) 0.0083(11) 0.0117(12) Cl1 0.0662(5) 0.0567(5) 0.0871(6) -0.0042(5) 0.0271(4) 0.0091(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.368(3) . ? C1 C2 1.415(4) . ? C1 C6 1.420(4) . ? C2 C3 1.367(4) . ? C2 H2 0.9300 . ? C3 C4 1.406(5) . ? C3 H3 0.9300 . ? C4 C5 1.359(5) . ? C4 H4 0.9300 . ? C5 C6 1.411(4) . ? C5 H5 0.9300 . ? C6 C7 1.411(4) . ? C7 C8 1.352(4) . ? C7 H7 0.9300 . ? C8 C9 1.409(4) . ? C8 H8 0.9300 . ? C9 N1 1.321(3) . ? C9 C10 1.510(4) . ? C10 O1 1.221(3) . ? C10 N2 1.353(4) . ? C11 C16 1.393(4) . ? C11 C12 1.397(4) . ? C11 N2 1.406(4) . ? C12 C13 1.378(4) . ? C12 H12 0.9300 . ? C13 C14 1.371(4) . ? C13 H13 0.9300 . ? C14 C15 1.388(4) . ? C14 Cl1 1.740(3) . ? C15 C16 1.374(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? N2 H2B 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 118.5(3) . . ? N1 C1 C6 122.2(3) . . ? C2 C1 C6 119.3(3) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.5(3) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 120.7(3) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 120.5(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 123.7(3) . . ? C7 C6 C1 117.4(3) . . ? C5 C6 C1 118.9(3) . . ? C8 C7 C6 120.0(3) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 118.8(3) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? N1 C9 C8 124.0(3) . . ? N1 C9 C10 117.9(2) . . ? C8 C9 C10 118.1(3) . . ? O1 C10 N2 125.1(3) . . ? O1 C10 C9 120.6(3) . . ? N2 C10 C9 114.3(3) . . ? C16 C11 C12 118.5(3) . . ? C16 C11 N2 118.0(3) . . ? C12 C11 N2 123.5(3) . . ? C13 C12 C11 120.0(3) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 120.6(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 120.3(3) . . ? C13 C14 Cl1 120.1(2) . . ? C15 C14 Cl1 119.6(2) . . ? C16 C15 C14 119.3(3) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C11 121.2(3) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? C9 N1 C1 117.6(2) . . ? C10 N2 C11 128.6(3) . . ? C10 N2 H2B 115.7 . . ? C11 N2 H2B 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 C3 -179.1(2) . . . . ? C6 C1 C2 C3 1.2(4) . . . . ? C1 C2 C3 C4 0.6(4) . . . . ? C2 C3 C4 C5 -1.9(5) . . . . ? C3 C4 C5 C6 1.3(5) . . . . ? C4 C5 C6 C7 -179.0(3) . . . . ? C4 C5 C6 C1 0.5(4) . . . . ? N1 C1 C6 C7 -2.0(4) . . . . ? C2 C1 C6 C7 177.8(3) . . . . ? N1 C1 C6 C5 178.5(2) . . . . ? C2 C1 C6 C5 -1.8(4) . . . . ? C5 C6 C7 C8 -179.7(3) . . . . ? C1 C6 C7 C8 0.8(4) . . . . ? C6 C7 C8 C9 1.0(4) . . . . ? C7 C8 C9 N1 -1.9(4) . . . . ? C7 C8 C9 C10 176.4(2) . . . . ? N1 C9 C10 O1 177.5(2) . . . . ? C8 C9 C10 O1 -1.0(4) . . . . ? N1 C9 C10 N2 -1.3(3) . . . . ? C8 C9 C10 N2 -179.7(2) . . . . ? C16 C11 C12 C13 -0.4(4) . . . . ? N2 C11 C12 C13 179.8(2) . . . . ? C11 C12 C13 C14 0.5(4) . . . . ? C12 C13 C14 C15 -0.6(4) . . . . ? C12 C13 C14 Cl1 -179.0(2) . . . . ? C13 C14 C15 C16 0.6(4) . . . . ? Cl1 C14 C15 C16 179.0(2) . . . . ? C14 C15 C16 C11 -0.6(4) . . . . ? C12 C11 C16 C15 0.5(4) . . . . ? N2 C11 C16 C15 -179.7(3) . . . . ? C8 C9 N1 C1 0.8(4) . . . . ? C10 C9 N1 C1 -177.5(2) . . . . ? C2 C1 N1 C9 -178.6(2) . . . . ? C6 C1 N1 C9 1.2(4) . . . . ? O1 C10 N2 C11 -2.3(4) . . . . ? C9 C10 N2 C11 176.3(2) . . . . ? C16 C11 N2 C10 174.0(3) . . . . ? C12 C11 N2 C10 -6.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 29.67 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.212 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 947156' ####################################################################### # # 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\c404\khc404 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H11 F1 N2 O1' _chemical_formula_weight 266.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.9506(3) _cell_length_b 14.5932(14) _cell_length_c 17.6779(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1277.14(17) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 14109 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 29.21 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.098 _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 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 14109 _diffrn_reflns_av_R_equivalents 0.0912 _diffrn_reflns_av_sigmaI/netI 0.0845 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 29.21 _reflns_number_total 3437 _reflns_number_gt 2198 _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^)+(0.0527P)^2^+0.0759P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(17) _refine_ls_number_reflns 3437 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1199 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.1559 _refine_ls_wR_factor_gt 0.1387 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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 -0.0611(6) 0.24632(17) 0.86498(14) 0.0451(6) Uani 1 1 d . . . C2 C -0.2287(6) 0.28216(19) 0.92194(15) 0.0520(6) Uani 1 1 d . . . H2 H -0.2180 0.2590 0.9709 0.062 Uiso 1 1 calc R . . C3 C -0.4074(6) 0.3509(2) 0.90580(17) 0.0597(7) Uani 1 1 d . . . H3 H -0.5183 0.3738 0.9438 0.072 Uiso 1 1 calc R . . C4 C -0.4254(7) 0.3873(2) 0.83269(18) 0.0642(8) Uani 1 1 d . . . H4 H -0.5462 0.4346 0.8227 0.077 Uiso 1 1 calc R . . C5 C -0.2688(7) 0.3543(2) 0.77665(18) 0.0662(8) Uani 1 1 d . . . H5 H -0.2825 0.3792 0.7284 0.079 Uiso 1 1 calc R . . C6 C -0.0834(6) 0.28209(18) 0.79022(15) 0.0523(6) Uani 1 1 d . . . C7 C 0.0807(8) 0.2429(2) 0.73467(16) 0.0652(8) Uani 1 1 d . . . H7 H 0.0705 0.2638 0.6850 0.078 Uiso 1 1 calc R . . C8 C 0.2552(7) 0.1745(2) 0.75286(17) 0.0621(8) Uani 1 1 d . . . H8 H 0.3634 0.1474 0.7161 0.074 Uiso 1 1 calc R . . C9 C 0.2677(6) 0.14587(18) 0.82820(14) 0.0485(6) Uani 1 1 d . . . C10 C 0.4715(6) 0.07272(18) 0.84851(15) 0.0508(7) Uani 1 1 d . . . C11 C 0.6349(5) -0.01424(17) 0.96095(16) 0.0508(7) Uani 1 1 d . . . C12 C 0.8393(6) -0.0628(2) 0.92575(18) 0.0621(8) Uani 1 1 d . . . H12 H 0.8796 -0.0523 0.8751 0.075 Uiso 1 1 calc R . . C13 C 0.9833(7) -0.1272(2) 0.96675(19) 0.0705(9) Uani 1 1 d . . . H13 H 1.1225 -0.1600 0.9441 0.085 Uiso 1 1 calc R . . C14 C 0.9189(7) -0.1418(2) 1.04066(19) 0.0683(8) Uani 1 1 d . . . C15 C 0.7243(7) -0.0935(2) 1.07726(18) 0.0685(9) Uani 1 1 d . . . H15 H 0.6891 -0.1033 1.1283 0.082 Uiso 1 1 calc R . . C16 C 0.5799(7) -0.0292(2) 1.03641(18) 0.0636(8) Uani 1 1 d . . . H16 H 0.4444 0.0044 1.0601 0.076 Uiso 1 1 calc R . . N1 N 0.1156(4) 0.17855(14) 0.88265(12) 0.0463(5) Uani 1 1 d . . . N2 N 0.4764(5) 0.05156(15) 0.92270(13) 0.0560(6) Uani 1 1 d . . . H2B H 0.3677 0.0825 0.9507 0.067 Uiso 1 1 calc R . . O1 O 0.6169(5) 0.03877(15) 0.80052(11) 0.0720(7) Uani 1 1 d . . . F1 F 1.0571(6) -0.20710(15) 1.07974(12) 0.1034(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 0.0439(14) 0.0450(13) 0.0465(14) -0.0003(11) -0.0082(12) -0.0083(12) C2 0.0531(16) 0.0544(14) 0.0486(14) 0.0017(12) 0.0005(15) -0.0032(13) C3 0.0578(17) 0.0559(16) 0.0655(18) -0.0059(14) 0.0014(16) -0.0012(16) C4 0.0654(19) 0.0534(16) 0.0739(19) 0.0019(15) -0.0079(19) 0.0065(15) C5 0.078(2) 0.0605(17) 0.0601(18) 0.0117(14) -0.0156(17) 0.0065(17) C6 0.0559(16) 0.0524(14) 0.0488(14) 0.0048(12) -0.0085(15) -0.0023(14) C7 0.082(2) 0.0733(19) 0.0403(14) 0.0052(13) -0.0022(17) 0.0060(19) C8 0.072(2) 0.0685(18) 0.0455(15) -0.0033(13) 0.0068(16) 0.0093(17) C9 0.0526(15) 0.0475(13) 0.0455(14) -0.0027(11) -0.0036(13) -0.0068(13) C10 0.0559(18) 0.0480(14) 0.0483(15) -0.0095(12) -0.0015(14) -0.0066(13) C11 0.0519(16) 0.0426(12) 0.0580(16) -0.0053(11) -0.0049(14) -0.0011(12) C12 0.063(2) 0.0635(18) 0.0599(17) -0.0069(14) -0.0069(15) 0.0057(15) C13 0.077(2) 0.0621(18) 0.073(2) -0.0160(15) -0.0178(18) 0.0231(16) C14 0.078(2) 0.0553(16) 0.071(2) -0.0031(15) -0.0261(19) 0.0101(17) C15 0.079(2) 0.0662(18) 0.0607(17) 0.0085(14) -0.0077(18) 0.0030(18) C16 0.0652(18) 0.0633(17) 0.0624(18) 0.0015(14) 0.0036(18) 0.0086(16) N1 0.0503(12) 0.0477(11) 0.0408(11) -0.0009(9) -0.0051(11) -0.0045(10) N2 0.0589(16) 0.0524(13) 0.0569(14) -0.0009(10) 0.0038(13) 0.0096(11) O1 0.0864(17) 0.0749(13) 0.0546(11) -0.0127(10) 0.0021(12) 0.0209(13) F1 0.135(2) 0.0861(13) 0.0890(14) 0.0017(11) -0.0378(15) 0.0414(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.357(3) . ? C1 C2 1.405(4) . ? C1 C6 1.425(3) . ? C2 C3 1.368(4) . ? C2 H2 0.9300 . ? C3 C4 1.400(4) . ? C3 H3 0.9300 . ? C4 C5 1.347(5) . ? C4 H4 0.9300 . ? C5 C6 1.418(4) . ? C5 H5 0.9300 . ? C6 C7 1.397(4) . ? C7 C8 1.359(4) . ? C7 H7 0.9300 . ? C8 C9 1.397(4) . ? C8 H8 0.9300 . ? C9 N1 1.312(3) . ? C9 C10 1.512(4) . ? C10 O1 1.218(3) . ? C10 N2 1.348(3) . ? C11 C16 1.379(4) . ? C11 C12 1.383(4) . ? C11 N2 1.412(3) . ? C12 C13 1.384(4) . ? C12 H12 0.9300 . ? C13 C14 1.362(4) . ? C13 H13 0.9300 . ? C14 C15 1.358(5) . ? C14 F1 1.361(4) . ? C15 C16 1.383(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? N2 H2B 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 119.1(2) . . ? N1 C1 C6 122.0(2) . . ? C2 C1 C6 118.8(2) . . ? C3 C2 C1 120.4(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.8(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.9(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C7 C6 C5 124.2(3) . . ? C7 C6 C1 117.2(3) . . ? C5 C6 C1 118.6(3) . . ? C8 C7 C6 120.3(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 118.3(3) . . ? C7 C8 H8 120.9 . . ? C9 C8 H8 120.9 . . ? N1 C9 C8 124.4(3) . . ? N1 C9 C10 117.7(2) . . ? C8 C9 C10 117.8(3) . . ? O1 C10 N2 125.0(3) . . ? O1 C10 C9 121.1(2) . . ? N2 C10 C9 113.9(2) . . ? C16 C11 C12 119.9(3) . . ? C16 C11 N2 117.5(2) . . ? C12 C11 N2 122.6(3) . . ? C11 C12 C13 119.3(3) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C14 C13 C12 119.2(3) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C15 C14 F1 118.6(3) . . ? C15 C14 C13 122.8(3) . . ? F1 C14 C13 118.6(3) . . ? C14 C15 C16 118.1(3) . . ? C14 C15 H15 121.0 . . ? C16 C15 H15 121.0 . . ? C11 C16 C15 120.7(3) . . ? C11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C9 N1 C1 117.8(2) . . ? C10 N2 C11 129.2(2) . . ? C10 N2 H2B 115.4 . . ? C11 N2 H2B 115.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 179.6(2) . . . . ? C6 C1 C2 C3 -0.8(4) . . . . ? C1 C2 C3 C4 -0.5(4) . . . . ? C2 C3 C4 C5 0.9(5) . . . . ? C3 C4 C5 C6 0.1(5) . . . . ? C4 C5 C6 C7 178.4(3) . . . . ? C4 C5 C6 C1 -1.4(5) . . . . ? N1 C1 C6 C7 1.5(4) . . . . ? C2 C1 C6 C7 -178.2(3) . . . . ? N1 C1 C6 C5 -178.6(3) . . . . ? C2 C1 C6 C5 1.7(4) . . . . ? C5 C6 C7 C8 179.3(3) . . . . ? C1 C6 C7 C8 -0.9(4) . . . . ? C6 C7 C8 C9 -0.9(5) . . . . ? C7 C8 C9 N1 2.3(5) . . . . ? C7 C8 C9 C10 -177.3(3) . . . . ? N1 C9 C10 O1 179.2(3) . . . . ? C8 C9 C10 O1 -1.2(4) . . . . ? N1 C9 C10 N2 -1.8(3) . . . . ? C8 C9 C10 N2 177.8(3) . . . . ? C16 C11 C12 C13 1.1(4) . . . . ? N2 C11 C12 C13 -179.1(3) . . . . ? C11 C12 C13 C14 0.5(5) . . . . ? C12 C13 C14 C15 -2.4(5) . . . . ? C12 C13 C14 F1 178.2(3) . . . . ? F1 C14 C15 C16 -178.2(3) . . . . ? C13 C14 C15 C16 2.4(5) . . . . ? C12 C11 C16 C15 -1.1(5) . . . . ? N2 C11 C16 C15 179.1(3) . . . . ? C14 C15 C16 C11 -0.7(5) . . . . ? C8 C9 N1 C1 -1.7(4) . . . . ? C10 C9 N1 C1 177.9(2) . . . . ? C2 C1 N1 C9 179.4(2) . . . . ? C6 C1 N1 C9 -0.3(4) . . . . ? O1 C10 N2 C11 -2.7(5) . . . . ? C9 C10 N2 C11 178.4(2) . . . . ? C16 C11 N2 C10 -173.2(3) . . . . ? C12 C11 N2 C10 7.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 29.21 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.165 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.041 _database_code_depnum_ccdc_archive 'CCDC 947157' ####################################################################### # # 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\538\kh538 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H11 I1 N2 O1' _chemical_formula_weight 374.17 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 6.548(2) _cell_length_b 17.029(5) _cell_length_c 12.714(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.06(3) _cell_angle_gamma 90.00 _cell_volume 1386.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 15272 _cell_measurement_theta_min 2.03 _cell_measurement_theta_max 29.21 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.793 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 2.306 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4120 _exptl_absorpt_correction_T_max 0.5021 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 15272 _diffrn_reflns_av_R_equivalents 0.0859 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 29.21 _reflns_number_total 3695 _reflns_number_gt 3040 _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^)+(0.0604P)^2^+0.2565P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3695 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.157 _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 -0.9744(4) -0.22883(15) 0.4717(2) 0.0419(5) Uani 1 1 d . . . C2 C -1.0999(5) -0.25162(19) 0.5443(3) 0.0526(7) Uani 1 1 d . . . H2 H -1.0666 -0.2349 0.6155 0.063 Uiso 1 1 calc R . . C3 C -1.2712(6) -0.2985(2) 0.5094(4) 0.0626(8) Uani 1 1 d . . . H3 H -1.3534 -0.3133 0.5575 0.075 Uiso 1 1 calc R . . C4 C -1.3247(5) -0.3246(2) 0.4030(4) 0.0636(9) Uani 1 1 d . . . H4 H -1.4407 -0.3567 0.3813 0.076 Uiso 1 1 calc R . . C5 C -1.2064(6) -0.3028(2) 0.3304(3) 0.0603(8) Uani 1 1 d . . . H5 H -1.2439 -0.3193 0.2592 0.072 Uiso 1 1 calc R . . C6 C -1.0276(5) -0.25512(17) 0.3638(2) 0.0494(6) Uani 1 1 d . . . C7 C -0.8989(6) -0.2319(2) 0.2934(3) 0.0561(7) Uani 1 1 d . . . H7 H -0.9297 -0.2476 0.2218 0.067 Uiso 1 1 calc R . . C8 C -0.7283(6) -0.1860(2) 0.3312(3) 0.0541(7) Uani 1 1 d . . . H8 H -0.6417 -0.1699 0.2860 0.065 Uiso 1 1 calc R . . C9 C -0.6865(4) -0.16358(16) 0.4401(2) 0.0436(6) Uani 1 1 d . . . C10 C -0.4936(5) -0.11485(17) 0.4827(2) 0.0458(6) Uani 1 1 d . . . C11 C -0.2977(4) -0.05727(16) 0.6536(3) 0.0451(6) Uani 1 1 d . . . C12 C -0.1144(5) -0.03809(19) 0.6204(3) 0.0514(7) Uani 1 1 d . . . H12 H -0.0981 -0.0522 0.5520 0.062 Uiso 1 1 calc R . . C13 C 0.0448(5) 0.00220(19) 0.6892(3) 0.0524(7) Uani 1 1 d . . . H13 H 0.1668 0.0149 0.6666 0.063 Uiso 1 1 calc R . . C14 C 0.0217(4) 0.02327(16) 0.7910(3) 0.0469(6) Uani 1 1 d . . . C15 C -0.1586(5) 0.00441(19) 0.8257(3) 0.0517(7) Uani 1 1 d . . . H15 H -0.1733 0.0185 0.8945 0.062 Uiso 1 1 calc R . . C16 C -0.3172(5) -0.03556(19) 0.7576(3) 0.0508(6) Uani 1 1 d . . . H16 H -0.4385 -0.0482 0.7810 0.061 Uiso 1 1 calc R . . N1 N -0.8024(4) -0.18319(13) 0.5091(2) 0.0436(5) Uani 1 1 d . . . N2 N -0.4646(4) -0.09756(15) 0.5886(2) 0.0492(6) Uani 1 1 d . . . H2B H -0.5610 -0.1133 0.6203 0.059 Uiso 1 1 calc R . . O1 O -0.3788(4) -0.09571(16) 0.4233(2) 0.0651(7) Uani 1 1 d . . . I1 I 0.26354(4) 0.085193(15) 0.89186(2) 0.06606(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0389(12) 0.0375(11) 0.0490(15) 0.0030(10) 0.0080(11) 0.0024(9) C2 0.0465(15) 0.0541(15) 0.0593(18) 0.0018(13) 0.0155(13) -0.0052(12) C3 0.0486(17) 0.0563(17) 0.086(3) 0.0034(16) 0.0215(17) -0.0074(14) C4 0.0443(17) 0.0503(16) 0.093(3) -0.0069(16) 0.0078(17) -0.0078(13) C5 0.0506(17) 0.0616(18) 0.063(2) -0.0158(15) -0.0018(14) 0.0008(14) C6 0.0455(15) 0.0472(14) 0.0533(17) -0.0013(12) 0.0051(12) 0.0062(12) C7 0.0593(19) 0.0652(18) 0.0427(16) -0.0027(12) 0.0080(14) 0.0038(14) C8 0.0567(18) 0.0612(17) 0.0478(16) 0.0038(13) 0.0189(14) 0.0022(14) C9 0.0405(13) 0.0427(12) 0.0478(15) 0.0066(10) 0.0099(11) 0.0035(10) C10 0.0422(13) 0.0447(13) 0.0512(15) 0.0092(11) 0.0114(11) 0.0007(11) C11 0.0388(14) 0.0420(12) 0.0566(17) 0.0014(11) 0.0146(12) -0.0028(10) C12 0.0445(15) 0.0572(16) 0.0568(17) -0.0012(13) 0.0206(13) -0.0064(12) C13 0.0420(14) 0.0558(15) 0.0633(19) 0.0016(13) 0.0198(13) -0.0070(12) C14 0.0391(13) 0.0451(13) 0.0569(17) 0.0024(11) 0.0108(12) 0.0006(10) C15 0.0468(15) 0.0553(15) 0.0556(17) -0.0040(12) 0.0169(13) -0.0006(12) C16 0.0405(14) 0.0572(15) 0.0595(18) -0.0010(13) 0.0215(13) -0.0029(12) N1 0.0415(12) 0.0405(10) 0.0504(13) 0.0035(9) 0.0128(10) -0.0001(9) N2 0.0415(12) 0.0536(13) 0.0550(14) -0.0021(10) 0.0159(11) -0.0099(10) O1 0.0580(15) 0.0806(16) 0.0609(15) 0.0096(11) 0.0219(12) -0.0181(12) I1 0.04714(16) 0.07565(19) 0.0740(2) -0.01416(10) 0.00946(11) -0.00814(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 1.369(4) . ? C1 C2 1.413(4) . ? C1 C6 1.416(4) . ? C2 C3 1.374(5) . ? C2 H2 0.9300 . ? C3 C4 1.396(6) . ? C3 H3 0.9300 . ? C4 C5 1.375(6) . ? C4 H4 0.9300 . ? C5 C6 1.415(5) . ? C5 H5 0.9300 . ? C6 C7 1.408(4) . ? C7 C8 1.365(5) . ? C7 H7 0.9300 . ? C8 C9 1.407(5) . ? C8 H8 0.9300 . ? C9 N1 1.316(4) . ? C9 C10 1.514(4) . ? C10 O1 1.216(4) . ? C10 N2 1.352(4) . ? C11 C12 1.392(4) . ? C11 C16 1.404(5) . ? C11 N2 1.404(4) . ? C12 C13 1.393(5) . ? C12 H12 0.9300 . ? C13 C14 1.381(5) . ? C13 H13 0.9300 . ? C14 C15 1.382(4) . ? C14 I1 2.102(3) . ? C15 C16 1.384(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? N2 H2B 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 118.5(3) . . ? N1 C1 C6 122.2(3) . . ? C2 C1 C6 119.2(3) . . ? C3 C2 C1 119.7(3) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 121.4(3) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 120.2(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 122.6(3) . . ? C7 C6 C1 117.9(3) . . ? C5 C6 C1 119.5(3) . . ? C8 C7 C6 119.4(3) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 118.6(3) . . ? C7 C8 H8 120.7 . . ? C9 C8 H8 120.7 . . ? N1 C9 C8 124.4(3) . . ? N1 C9 C10 117.1(3) . . ? C8 C9 C10 118.5(3) . . ? O1 C10 N2 125.7(3) . . ? O1 C10 C9 120.2(3) . . ? N2 C10 C9 114.1(2) . . ? C12 C11 C16 118.5(3) . . ? C12 C11 N2 123.4(3) . . ? C16 C11 N2 118.1(3) . . ? C11 C12 C13 120.3(3) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 120.1(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 120.5(3) . . ? C13 C14 I1 119.1(2) . . ? C15 C14 I1 120.4(2) . . ? C14 C15 C16 119.5(3) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C11 121.0(3) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? C9 N1 C1 117.4(3) . . ? C10 N2 C11 128.5(3) . . ? C10 N2 H2B 115.7 . . ? C11 N2 H2B 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 C3 -178.9(3) . . . . ? C6 C1 C2 C3 -0.2(4) . . . . ? C1 C2 C3 C4 0.1(5) . . . . ? C2 C3 C4 C5 -0.6(6) . . . . ? C3 C4 C5 C6 1.2(5) . . . . ? C4 C5 C6 C7 179.1(3) . . . . ? C4 C5 C6 C1 -1.3(5) . . . . ? N1 C1 C6 C7 -1.0(4) . . . . ? C2 C1 C6 C7 -179.6(3) . . . . ? N1 C1 C6 C5 179.4(3) . . . . ? C2 C1 C6 C5 0.8(4) . . . . ? C5 C6 C7 C8 -179.8(3) . . . . ? C1 C6 C7 C8 0.6(5) . . . . ? C6 C7 C8 C9 0.2(5) . . . . ? C7 C8 C9 N1 -0.7(5) . . . . ? C7 C8 C9 C10 178.1(3) . . . . ? N1 C9 C10 O1 179.1(3) . . . . ? C8 C9 C10 O1 0.2(4) . . . . ? N1 C9 C10 N2 0.1(4) . . . . ? C8 C9 C10 N2 -178.8(3) . . . . ? C16 C11 C12 C13 -0.4(5) . . . . ? N2 C11 C12 C13 179.8(3) . . . . ? C11 C12 C13 C14 0.1(5) . . . . ? C12 C13 C14 C15 0.3(5) . . . . ? C12 C13 C14 I1 -179.3(2) . . . . ? C13 C14 C15 C16 -0.3(5) . . . . ? I1 C14 C15 C16 179.2(2) . . . . ? C14 C15 C16 C11 0.0(5) . . . . ? C12 C11 C16 C15 0.3(5) . . . . ? N2 C11 C16 C15 -179.9(3) . . . . ? C8 C9 N1 C1 0.3(4) . . . . ? C10 C9 N1 C1 -178.5(2) . . . . ? C2 C1 N1 C9 179.2(3) . . . . ? C6 C1 N1 C9 0.5(4) . . . . ? O1 C10 N2 C11 -2.3(5) . . . . ? C9 C10 N2 C11 176.5(3) . . . . ? C12 C11 N2 C10 -10.0(5) . . . . ? C16 C11 N2 C10 170.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 29.21 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.692 _refine_diff_density_min -0.860 _refine_diff_density_rms 0.143 _database_code_depnum_ccdc_archive 'CCDC 948750'