# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Kumar Biradha' _publ_contact_author_name 'Kumar Biradha' _publ_contact_author_email KBIRADHA@CHEM.IITKGP.ERNET.IN _publ_section_title ; Halo---Halo interactions in assembling??-sheets into two-dimensional layers in the Bis-(4-halo-phenylamido)alkanes and their inter-halogen co-crystals ; # Attachment 'kb.cif' data_2I _database_code_depnum_ccdc_archive 'CCDC 696960' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 I2 N2 O2' _chemical_formula_weight 520.09 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.693(7) _cell_length_b 4.8374(19) _cell_length_c 9.883(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.391(10) _cell_angle_gamma 90.00 _cell_volume 834.5(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1819 _cell_measurement_theta_min 1.17 _cell_measurement_theta_max 27.00 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.070 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 3.776 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.642 _exptl_absorpt_correction_T_max 0.739 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 Bruker' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10095 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1819 _reflns_number_gt 1628 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 0.020(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1819 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 0.882 _refine_ls_restrained_S_all 0.882 _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 I1 I 0.425091(11) 0.68385(5) 0.14462(2) 0.05924(19) Uani 1 1 d . . . N11 N 0.13471(15) 0.3520(4) -0.2792(2) 0.0404(5) Uani 1 1 d . . . H11 H 0.1271 0.1787 -0.2955 0.048 Uiso 1 1 calc R . . C11 C 0.19897(14) 0.4242(5) -0.1810(2) 0.0338(5) Uani 1 1 d . . . C12 C 0.26736(19) 0.2857(6) -0.1813(3) 0.0464(7) Uani 1 1 d . . . H12 H 0.2702 0.1459 -0.2449 0.056 Uiso 1 1 calc R . . C13 C 0.33203(18) 0.3548(6) -0.0869(3) 0.0486(7) Uani 1 1 d . . . H13 H 0.3779 0.2606 -0.0865 0.058 Uiso 1 1 calc R . . C14 C 0.32711(14) 0.5651(5) 0.0060(2) 0.0378(5) Uani 1 1 d . . . C15 C 0.25942(18) 0.7000(6) 0.0091(3) 0.0459(7) Uani 1 1 d . . . H15 H 0.2568 0.8384 0.0735 0.055 Uiso 1 1 calc R . . C16 C 0.19472(16) 0.6303(6) -0.0840(3) 0.0426(6) Uani 1 1 d . . . H16 H 0.1486 0.7210 -0.0816 0.051 Uiso 1 1 calc R . . O21 O 0.08644(14) 0.7791(4) -0.3282(2) 0.0496(5) Uani 1 1 d . . . C21 C 0.08441(14) 0.5287(5) -0.3495(2) 0.0336(5) Uani 1 1 d . . . C22 C 0.02558(16) 0.3988(5) -0.4597(3) 0.0447(6) Uani 1 1 d . . . H22A H 0.0521 0.2942 -0.5214 0.054 Uiso 1 1 calc . . . H22B H -0.0053 0.2700 -0.4168 0.054 Uiso 1 1 calc . . . 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 I1 0.0393(2) 0.0700(3) 0.0597(2) -0.00576(8) -0.01783(13) -0.00585(7) N11 0.0445(13) 0.0248(8) 0.0452(11) -0.0058(8) -0.0123(10) -0.0030(8) C11 0.0351(12) 0.0293(10) 0.0332(10) 0.0032(9) -0.0055(9) -0.0033(9) C12 0.0468(17) 0.0411(14) 0.0451(15) -0.0125(11) -0.0113(13) 0.0086(11) C13 0.0353(14) 0.0545(15) 0.0506(15) -0.0050(12) -0.0087(12) 0.0091(11) C14 0.0318(11) 0.0417(12) 0.0356(10) 0.0034(9) -0.0073(9) -0.0065(9) C15 0.0408(16) 0.0548(17) 0.0388(13) -0.0149(10) -0.0039(12) 0.0016(11) C16 0.0316(13) 0.0504(13) 0.0434(13) -0.0112(11) -0.0013(10) 0.0048(11) O21 0.0582(14) 0.0244(8) 0.0560(12) -0.0014(8) -0.0214(10) -0.0030(8) C21 0.0345(12) 0.0285(10) 0.0342(10) 0.0010(9) -0.0055(9) -0.0061(9) C22 0.0457(15) 0.0289(11) 0.0513(14) -0.0019(11) -0.0166(12) -0.0058(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C14 2.106(2) . ? N11 C21 1.343(3) . ? N11 C11 1.413(3) . ? C11 C12 1.384(4) . ? C11 C16 1.394(4) . ? C12 C13 1.394(4) . ? C13 C14 1.383(4) . ? C14 C15 1.369(4) . ? C15 C16 1.388(4) . ? O21 C21 1.229(3) . ? C21 C22 1.515(3) . ? C22 C22 1.476(5) 3_564 ? 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 C21 N11 C11 126.08(19) . . ? C12 C11 C16 119.6(2) . . ? C12 C11 N11 119.0(2) . . ? C16 C11 N11 121.5(2) . . ? C11 C12 C13 120.3(2) . . ? C14 C13 C12 119.2(3) . . ? C15 C14 C13 121.0(2) . . ? C15 C14 I1 119.06(19) . . ? C13 C14 I1 119.9(2) . . ? C14 C15 C16 120.0(2) . . ? C15 C16 C11 119.9(2) . . ? O21 C21 N11 122.7(2) . . ? O21 C21 C22 122.0(2) . . ? N11 C21 C22 115.3(2) . . ? C22 C22 C21 113.7(3) 3_564 . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.748 _refine_diff_density_min -0.695 _refine_diff_density_rms 0.138 data_3I _database_code_depnum_ccdc_archive 'CCDC 696961' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 I2 N2 O2' _chemical_formula_weight 548.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.979(7) _cell_length_b 4.8064(18) _cell_length_c 10.089(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.319(10) _cell_angle_gamma 90.00 _cell_volume 918.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1993 _cell_measurement_theta_min 1.07 _cell_measurement_theta_max 27.00 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.981 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 3.436 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.668 _exptl_absorpt_correction_T_max 0.762 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 BRUKER' _diffrn_measurement_method Hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11406 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.07 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1993 _reflns_number_gt 1845 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+0.3876P] 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 0.0262(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1993 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0983 _refine_ls_wR_factor_gt 0.0837 _refine_ls_goodness_of_fit_ref 1.237 _refine_ls_restrained_S_all 1.237 _refine_ls_shift/su_max 0.004 _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 I1 I 0.431647(12) 0.68602(6) 0.15791(2) 0.05854(17) Uani 1 1 d . . . C11 C 0.22845(15) 0.4141(6) -0.1270(3) 0.0349(6) Uani 1 1 d . . . C12 C 0.22237(16) 0.6154(7) -0.0318(3) 0.0431(7) Uani 1 1 d . . . H12 H 0.1791 0.7014 -0.0222 0.052 Uiso 1 1 calc R . . C13 C 0.2801(2) 0.6912(7) 0.0499(3) 0.0467(8) Uani 1 1 d . . . H13 H 0.2758 0.8295 0.1133 0.056 Uiso 1 1 calc R . . C14 C 0.34417(15) 0.5617(6) 0.0373(3) 0.0383(6) Uani 1 1 d . . . C15 C 0.35041(19) 0.3541(7) -0.0549(4) 0.0485(7) Uani 1 1 d . . . H15 H 0.3933 0.2628 -0.0615 0.058 Uiso 1 1 calc R . . C16 C 0.2924(2) 0.2806(7) -0.1385(4) 0.0469(8) Uani 1 1 d . . . H16 H 0.2967 0.1420 -0.2018 0.056 Uiso 1 1 calc R . . N21 N 0.17083(16) 0.3344(5) -0.2132(3) 0.0418(6) Uani 1 1 d . . . H21 H 0.1643 0.1593 -0.2263 0.050 Uiso 1 1 calc R . . O21 O 0.12618(15) 0.7612(5) -0.2583(3) 0.0517(6) Uani 1 1 d . . . C21 C 0.12529(15) 0.5105(6) -0.2767(3) 0.0355(6) Uani 1 1 d . . . C22 C 0.0736(2) 0.3746(7) -0.3753(4) 0.0509(8) Uani 1 1 d . . . H22A H 0.0999 0.2694 -0.4380 0.061 Uiso 1 1 calc . . . H22B H 0.0452 0.2436 -0.3283 0.061 Uiso 1 1 calc . . . C23 C 0.02535(17) 0.5703(6) -0.4510(3) 0.0446(7) Uani 1 1 d . . . H23A H 0.0535 0.7018 -0.4982 0.053 Uiso 1 1 calc . . . H23B H -0.0013 0.6749 -0.3887 0.053 Uiso 1 1 calc . . . 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 I1 0.0397(2) 0.0726(3) 0.0604(2) -0.00420(10) -0.02151(13) -0.00721(9) C11 0.0346(14) 0.0328(12) 0.0359(13) 0.0019(10) -0.0105(11) -0.0015(11) C12 0.0316(15) 0.0526(16) 0.0441(15) -0.0106(13) -0.0072(12) 0.0043(13) C13 0.0425(19) 0.0562(19) 0.0400(16) -0.0134(13) -0.0100(14) 0.0020(13) C14 0.0340(14) 0.0473(15) 0.0321(12) 0.0028(11) -0.0102(10) -0.0055(12) C15 0.0330(16) 0.0579(18) 0.0533(18) -0.0056(15) -0.0091(14) 0.0090(13) C16 0.0446(19) 0.0472(16) 0.0467(17) -0.0127(13) -0.0150(14) 0.0090(13) N21 0.0451(16) 0.0295(11) 0.0485(14) -0.0044(9) -0.0175(12) -0.0018(9) O21 0.0601(16) 0.0303(9) 0.0608(15) -0.0009(10) -0.0299(13) -0.0024(10) C21 0.0372(14) 0.0315(12) 0.0363(13) 0.0002(10) -0.0095(11) -0.0036(10) C22 0.058(2) 0.0338(13) 0.0568(18) -0.0022(13) -0.0295(16) -0.0035(14) C23 0.0427(17) 0.0394(14) 0.0491(16) -0.0010(13) -0.0194(13) -0.0047(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C14 2.088(3) . ? C11 C12 1.373(4) . ? C11 C16 1.384(4) . ? C11 N21 1.411(4) . ? C12 C13 1.382(5) . ? C13 C14 1.378(5) . ? C14 C15 1.374(5) . ? C15 C16 1.393(5) . ? N21 C21 1.345(4) . ? O21 C21 1.219(4) . ? C21 C22 1.505(4) . ? C22 C23 1.492(5) . ? C23 C23 1.500(6) 3_564 ? 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 C12 C11 C16 119.7(3) . . ? C12 C11 N21 122.0(3) . . ? C16 C11 N21 118.4(3) . . ? C11 C12 C13 120.4(3) . . ? C14 C13 C12 120.0(3) . . ? C15 C14 C13 120.1(3) . . ? C15 C14 I1 120.4(2) . . ? C13 C14 I1 119.5(2) . . ? C14 C15 C16 119.8(3) . . ? C11 C16 C15 119.9(3) . . ? C21 N21 C11 125.2(2) . . ? O21 C21 N21 123.1(3) . . ? O21 C21 C22 122.1(3) . . ? N21 C21 C22 114.7(2) . . ? C23 C22 C21 115.0(3) . . ? C22 C23 C23 113.9(3) . 3_564 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.123 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.220 data_5I _database_code_depnum_ccdc_archive 'CCDC 696962' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 I2 N2 O2' _chemical_formula_weight 604.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 22.8808(17) _cell_length_b 4.7980(4) _cell_length_c 10.2227(8) _cell_angle_alpha 90.00 _cell_angle_beta 95.371(2) _cell_angle_gamma 90.00 _cell_volume 1117.34(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2415 _cell_measurement_theta_min 0.89 _cell_measurement_theta_max 26.99 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.796 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 588 _exptl_absorpt_coefficient_mu 2.834 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.625 _exptl_absorpt_correction_T_max 0.715 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 BRUKER' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13932 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 0.89 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2415 _reflns_number_gt 1977 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0580P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2415 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0938 _refine_ls_wR_factor_gt 0.0781 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.056998(10) 0.69105(6) 0.17721(3) 0.05915(14) Uani 1 1 d . . . N1 N 0.27230(13) 0.3221(5) -0.1199(3) 0.0422(6) Uani 1 1 d . . . H1 H 0.2771 0.1460 -0.1303 0.051 Uiso 1 1 calc R . . O1 O 0.31032(13) 0.7457(5) -0.1543(3) 0.0560(7) Uani 1 1 d . . . C1 C 0.31057(13) 0.4948(6) -0.1719(3) 0.0368(6) Uani 1 1 d . . . C2 C 0.35257(17) 0.3541(7) -0.2561(4) 0.0520(9) Uani 1 1 d . . . H2A H 0.3739 0.2118 -0.2038 0.062 Uiso 1 1 calc . . . H2B H 0.3298 0.2607 -0.3281 0.062 Uiso 1 1 calc . . . C3 C 0.39591(15) 0.5393(7) -0.3121(4) 0.0501(8) Uani 1 1 d . . . H3A H 0.4193 0.6307 -0.2405 0.060 Uiso 1 1 calc . . . H3B H 0.3749 0.6828 -0.3641 0.060 Uiso 1 1 calc . . . C4 C 0.43636(16) 0.3914(8) -0.3965(4) 0.0535(9) Uani 1 1 d . . . H4A H 0.4127 0.2935 -0.4656 0.064 Uiso 1 1 calc . . . H4B H 0.4582 0.2524 -0.3432 0.064 Uiso 1 1 calc . . . C5 C 0.47940(15) 0.5744(8) -0.4590(4) 0.0557(9) Uani 1 1 d . . . H5A H 0.4575 0.7108 -0.5139 0.067 Uiso 1 1 calc . . . H5B H 0.5025 0.6754 -0.3901 0.067 Uiso 1 1 calc . . . C11 C 0.22480(13) 0.4077(6) -0.0495(3) 0.0352(6) Uani 1 1 d . . . C12 C 0.17133(17) 0.2763(7) -0.0775(4) 0.0480(8) Uani 1 1 d . . . H12 H 0.1675 0.1362 -0.1406 0.058 Uiso 1 1 calc R . . C13 C 0.12331(15) 0.3527(7) -0.0115(4) 0.0477(8) Uani 1 1 d . . . H13 H 0.0873 0.2643 -0.0301 0.057 Uiso 1 1 calc R . . C14 C 0.12958(12) 0.5610(7) 0.0817(3) 0.0385(7) Uani 1 1 d . . . C15 C 0.18316(16) 0.6897(7) 0.1112(4) 0.0475(8) Uani 1 1 d . . . H15 H 0.1872 0.8293 0.1745 0.057 Uiso 1 1 calc R . . C16 C 0.23100(14) 0.6096(7) 0.0457(3) 0.0434(7) Uani 1 1 d . . . H16 H 0.2673 0.6932 0.0665 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.04047(18) 0.0699(2) 0.0717(2) -0.00297(11) 0.02942(13) 0.00812(10) N1 0.0427(15) 0.0285(12) 0.0599(17) -0.0051(11) 0.0288(13) 0.0007(10) O1 0.0667(18) 0.0271(11) 0.0813(19) -0.0010(11) 0.0435(15) -0.0002(10) C1 0.0356(15) 0.0330(15) 0.0445(16) 0.0014(12) 0.0176(13) 0.0023(12) C2 0.054(2) 0.0377(16) 0.070(2) -0.0054(15) 0.0390(18) -0.0002(14) C3 0.0455(18) 0.0452(18) 0.065(2) 0.0002(16) 0.0307(16) 0.0023(14) C4 0.050(2) 0.0490(17) 0.067(2) -0.0018(17) 0.0351(18) 0.0020(16) C5 0.051(2) 0.056(2) 0.066(2) -0.0013(18) 0.0350(18) 0.0023(17) C11 0.0331(14) 0.0331(13) 0.0418(15) 0.0028(12) 0.0165(12) 0.0028(12) C12 0.047(2) 0.0446(17) 0.056(2) -0.0129(15) 0.0197(17) -0.0072(15) C13 0.0321(16) 0.053(2) 0.060(2) -0.0068(15) 0.0166(15) -0.0060(13) C14 0.0309(14) 0.0444(16) 0.0431(16) 0.0048(13) 0.0179(13) 0.0053(12) C15 0.0427(19) 0.055(2) 0.0474(19) -0.0133(15) 0.0160(15) 0.0002(14) C16 0.0303(15) 0.0483(16) 0.0535(18) -0.0074(15) 0.0138(14) -0.0029(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C14 2.098(3) . ? N1 C1 1.350(4) . ? N1 C11 1.419(3) . ? O1 C1 1.217(4) . ? C1 C2 1.509(4) . ? C2 C3 1.485(4) . ? C3 C4 1.502(4) . ? C4 C5 1.506(5) . ? C5 C5 1.499(6) 3_664 ? C11 C16 1.371(5) . ? C11 C12 1.382(5) . ? C12 C13 1.391(5) . ? C13 C14 1.379(5) . ? C14 C15 1.380(5) . ? C15 C16 1.390(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C11 125.3(2) . . ? O1 C1 N1 122.4(3) . . ? O1 C1 C2 122.6(3) . . ? N1 C1 C2 114.9(2) . . ? C3 C2 C1 115.8(3) . . ? C2 C3 C4 114.1(3) . . ? C3 C4 C5 115.5(3) . . ? C5 C5 C4 115.4(4) 3_664 . ? C16 C11 C12 120.0(3) . . ? C16 C11 N1 122.1(3) . . ? C12 C11 N1 117.9(3) . . ? C11 C12 C13 120.2(3) . . ? C14 C13 C12 119.4(3) . . ? C13 C14 C15 120.5(3) . . ? C13 C14 I1 120.1(2) . . ? C15 C14 I1 119.4(2) . . ? C14 C15 C16 119.6(3) . . ? C11 C16 C15 120.2(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.666 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.187 data_2Br _database_code_depnum_ccdc_archive 'CCDC 696963' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Br2 N2 O2' _chemical_formula_weight 426.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.080(7) _cell_length_b 4.813(2) _cell_length_c 9.831(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.057(12) _cell_angle_gamma 90.00 _cell_volume 795.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1669 _cell_measurement_theta_min 1.21 _cell_measurement_theta_max 26.70 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.779 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 5.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.484 _exptl_absorpt_correction_T_max 0.600 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 BRuker' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9620 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 26.70 _reflns_number_total 1669 _reflns_number_gt 1150 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1669 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1427 _refine_ls_wR_factor_gt 0.1186 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.42827(3) 0.66130(11) 0.14852(5) 0.0782(3) Uani 1 1 d . . . N11 N 0.14023(18) 0.3517(5) -0.2765(3) 0.0417(7) Uani 1 1 d . . . H11 H 0.1331 0.1777 -0.2944 0.050 Uiso 1 1 calc R . . C11 C 0.20625(19) 0.4256(6) -0.1754(3) 0.0365(7) Uani 1 1 d . . . C12 C 0.2774(2) 0.2865(8) -0.1728(4) 0.0540(10) Uani 1 1 d . . . H12 H 0.2809 0.1455 -0.2361 0.065 Uiso 1 1 calc R . . C13 C 0.3435(2) 0.3567(8) -0.0760(5) 0.0575(10) Uani 1 1 d . . . H13 H 0.3914 0.2640 -0.0744 0.069 Uiso 1 1 calc R . . C14 C 0.3378(2) 0.5612(8) 0.0161(4) 0.0462(8) Uani 1 1 d . . . C15 C 0.2685(2) 0.6978(8) 0.0175(4) 0.0546(10) Uani 1 1 d . . . H15 H 0.2657 0.8362 0.0825 0.066 Uiso 1 1 calc R . . C16 C 0.2018(2) 0.6291(7) -0.0790(4) 0.0482(9) Uani 1 1 d . . . H16 H 0.1540 0.7211 -0.0784 0.058 Uiso 1 1 calc R . . O21 O 0.08887(16) 0.7796(5) -0.3257(3) 0.0511(7) Uani 1 1 d . . . C21 C 0.08730(18) 0.5305(6) -0.3475(3) 0.0358(7) Uani 1 1 d . . . C22 C 0.0271(2) 0.3981(6) -0.4585(4) 0.0464(9) Uani 1 1 d . . . H22A H -0.0045 0.2674 -0.4160 0.056 Uiso 1 1 calc . . . H22B H 0.0549 0.2941 -0.5200 0.056 Uiso 1 1 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0457(4) 0.1063(5) 0.0695(4) -0.0055(2) -0.0259(2) -0.0133(2) N11 0.0412(16) 0.0288(12) 0.0468(16) -0.0015(10) -0.0153(13) -0.0042(10) C11 0.0345(18) 0.0347(14) 0.0355(16) 0.0033(13) -0.0075(14) -0.0035(12) C12 0.047(2) 0.0545(19) 0.054(2) -0.0142(17) -0.0114(18) 0.0125(16) C13 0.035(2) 0.071(2) 0.061(2) -0.0001(19) -0.0071(18) 0.0085(17) C14 0.0324(18) 0.0601(19) 0.0405(18) 0.0020(16) -0.0096(14) -0.0078(15) C15 0.045(2) 0.066(2) 0.045(2) -0.0171(17) -0.0116(17) 0.0009(17) C16 0.036(2) 0.0587(19) 0.046(2) -0.0119(16) -0.0041(16) 0.0038(15) O21 0.0577(17) 0.0286(11) 0.0561(16) -0.0026(10) -0.0203(13) -0.0030(10) C21 0.0348(18) 0.0322(15) 0.0361(16) -0.0003(12) -0.0061(13) -0.0057(13) C22 0.044(2) 0.0331(14) 0.052(2) -0.0019(14) -0.0206(16) -0.0072(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 Br1 C14 1.900(3) . ? N11 C21 1.351(4) . ? N11 C11 1.412(4) . ? C11 C16 1.373(5) . ? C11 C12 1.384(5) . ? C12 C13 1.385(6) . ? C13 C14 1.352(5) . ? C14 C15 1.356(6) . ? C15 C16 1.390(5) . ? O21 C21 1.218(4) . ? C21 C22 1.504(4) . ? C22 C22 1.490(7) 3_564 ? 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 C21 N11 C11 125.7(2) . . ? C16 C11 C12 119.1(3) . . ? C16 C11 N11 122.1(3) . . ? C12 C11 N11 118.8(3) . . ? C13 C12 C11 120.1(3) . . ? C14 C13 C12 119.5(4) . . ? C15 C14 C13 121.6(3) . . ? C15 C14 Br1 118.5(3) . . ? C13 C14 Br1 119.9(3) . . ? C14 C15 C16 119.4(3) . . ? C11 C16 C15 120.2(3) . . ? O21 C21 N11 122.9(3) . . ? O21 C21 C22 122.4(3) . . ? N11 C21 C22 114.6(3) . . ? C21 C22 C22 113.5(3) . 3_564 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.70 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.655 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.084 data_3Br _database_code_depnum_ccdc_archive 'CCDC 696964' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 Br2 N2 O2' _chemical_formula_weight 454.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.9461(5) _cell_length_b 8.6603(9) _cell_length_c 10.7293(11) _cell_angle_alpha 90.812(3) _cell_angle_beta 100.267(3) _cell_angle_gamma 96.325(3) _cell_volume 449.21(8) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1896 _cell_measurement_theta_min 1.93 _cell_measurement_theta_max 27.00 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 226 _exptl_absorpt_coefficient_mu 4.524 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.448 _exptl_absorpt_correction_T_max 0.585 _exptl_absorpt_process_details SADASB _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 Bruker' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5915 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1896 _reflns_number_gt 1475 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0796P)^2^+0.2034P] 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 0.052(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1896 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1341 _refine_ls_wR_factor_gt 0.1258 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.24585(10) 0.10786(5) 0.89001(3) 0.0831(3) Uani 1 1 d . . . N11 N -0.1102(5) 0.3002(3) 0.3494(2) 0.0445(6) Uani 1 1 d . . . H11 H -0.2846 0.3029 0.3242 0.053 Uiso 1 1 calc R . . C11 C -0.0242(5) 0.2602(3) 0.4762(3) 0.0389(6) Uani 1 1 d . . . C12 C -0.1858(8) 0.1492(7) 0.5287(4) 0.0807(15) Uani 1 1 d . . . H12 H -0.3503 0.1027 0.4804 0.097 Uiso 1 1 calc R . . C13 C -0.1083(10) 0.1058(6) 0.6515(4) 0.0824(14) Uani 1 1 d . . . H13 H -0.2198 0.0305 0.6858 0.099 Uiso 1 1 calc R . . C14 C 0.1314(7) 0.1733(4) 0.7225(3) 0.0494(7) Uani 1 1 d . . . C15 C 0.2895(8) 0.2848(5) 0.6739(4) 0.0681(11) Uani 1 1 d . . . H15 H 0.4515 0.3324 0.7236 0.082 Uiso 1 1 calc R . . C16 C 0.2131(8) 0.3289(4) 0.5510(3) 0.0612(9) Uani 1 1 d . . . H16 H 0.3241 0.4062 0.5185 0.073 Uiso 1 1 calc R . . O21 O 0.3049(4) 0.3331(4) 0.2897(3) 0.0734(9) Uani 1 1 d . . . C21 C 0.0546(6) 0.3346(4) 0.2643(3) 0.0449(7) Uani 1 1 d . . . C22 C -0.0924(6) 0.3678(5) 0.1333(3) 0.0531(8) Uani 1 1 d . . . H22A H -0.1324 0.2717 0.0825 0.064 Uiso 1 1 calc . . . H22B H -0.2674 0.4051 0.1399 0.064 Uiso 1 1 calc . . . C23 C 0.0727(5) 0.4862(4) 0.0668(3) 0.0437(7) Uani 1 1 d . . . H23A H 0.2506 0.4509 0.0631 0.052 Uiso 1 1 calc . . . H23B H 0.1062 0.5837 0.1157 0.052 Uiso 1 1 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.1158(5) 0.0929(4) 0.0397(3) 0.0186(2) 0.0008(2) 0.0272(3) N11 0.0239(10) 0.0664(16) 0.0422(14) 0.0168(11) 0.0015(9) 0.0067(10) C11 0.0314(13) 0.0487(15) 0.0371(14) 0.0102(12) 0.0050(11) 0.0080(11) C12 0.052(2) 0.123(4) 0.053(2) 0.034(2) -0.0067(17) -0.030(2) C13 0.077(3) 0.107(3) 0.055(2) 0.038(2) 0.005(2) -0.021(2) C14 0.0604(19) 0.0540(17) 0.0342(15) 0.0079(13) 0.0039(13) 0.0157(14) C15 0.064(2) 0.080(3) 0.046(2) 0.0068(18) -0.0131(16) -0.0155(19) C16 0.062(2) 0.067(2) 0.0439(19) 0.0137(16) -0.0038(15) -0.0200(17) O21 0.0230(10) 0.141(3) 0.0571(16) 0.0414(16) 0.0051(10) 0.0132(12) C21 0.0295(14) 0.0662(18) 0.0384(16) 0.0193(13) 0.0031(11) 0.0052(12) C22 0.0318(14) 0.082(2) 0.0415(17) 0.0224(15) -0.0025(12) 0.0011(14) C23 0.0329(14) 0.0590(18) 0.0362(16) 0.0116(13) -0.0011(11) 0.0019(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C14 1.900(3) . ? N11 C21 1.344(4) . ? N11 C11 1.411(4) . ? C11 C16 1.369(4) . ? C11 C12 1.373(5) . ? C12 C13 1.375(6) . ? C13 C14 1.356(6) . ? C14 C15 1.345(5) . ? C15 C16 1.377(5) . ? O21 C21 1.221(4) . ? C21 C22 1.510(4) . ? C22 C23 1.507(4) . ? C23 C23 1.520(5) 2_565 ? 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 C21 N11 C11 126.2(2) . . ? C16 C11 C12 117.9(3) . . ? C16 C11 N11 122.9(3) . . ? C12 C11 N11 119.2(3) . . ? C13 C12 C11 121.1(3) . . ? C14 C13 C12 119.8(4) . . ? C15 C14 C13 120.1(3) . . ? C15 C14 Br1 120.1(3) . . ? C13 C14 Br1 119.8(3) . . ? C14 C15 C16 120.4(3) . . ? C15 C16 C11 120.7(3) . . ? O21 C21 N11 122.3(3) . . ? O21 C21 C22 122.2(3) . . ? N11 C21 C22 115.4(2) . . ? C23 C22 C21 113.1(2) . . ? C22 C23 C23 112.6(3) . 2_565 ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.771 _refine_diff_density_min -0.525 _refine_diff_density_rms 0.075 data_4Br _database_code_depnum_ccdc_archive 'CCDC 696965' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 Br2 N2 O2' _chemical_formula_weight 482.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.113(3) _cell_length_b 5.1003(7) _cell_length_c 17.945(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.259(4) _cell_angle_gamma 90.00 _cell_volume 1942.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2134 _cell_measurement_theta_min 1.92 _cell_measurement_theta_max 27.00 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 4.189 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.580 _exptl_absorpt_correction_T_max 0.688 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 Bruker' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12286 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2134 _reflns_number_gt 1577 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+0.7066P] 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 2134 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0838 _refine_ls_wR_factor_gt 0.0781 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.059513(13) 0.84577(7) 0.206437(18) 0.07735(16) Uani 1 1 d . . . O1 O 0.32070(8) 1.1498(3) 0.09292(11) 0.0529(4) Uani 1 1 d . . . N1 N 0.29745(8) 0.7236(3) 0.10520(10) 0.0373(4) Uani 1 1 d . . . H1 H 0.3093 0.5660 0.0997 0.045 Uiso 1 1 calc R . . C1 C 0.33558(10) 0.9199(4) 0.09461(12) 0.0353(4) Uani 1 1 d . . . C2 C 0.39875(10) 0.8315(4) 0.08721(13) 0.0410(5) Uani 1 1 d . . . H2A H 0.3950 0.6532 0.0677 0.049 Uiso 1 1 calc . . . H2B H 0.4288 0.8311 0.1383 0.049 Uiso 1 1 calc . . . C3 C 0.42357(10) 1.0035(4) 0.03389(13) 0.0397(5) Uani 1 1 d . . . H3A H 0.4279 1.1813 0.0538 0.048 Uiso 1 1 calc . . . H3B H 0.3932 1.0060 -0.0170 0.048 Uiso 1 1 calc . . . C4 C 0.48668(10) 0.9113(4) 0.02570(14) 0.0421(5) Uani 1 1 d . . . H4A H 0.4819 0.7357 0.0041 0.051 Uiso 1 1 calc . . . H4B H 0.5166 0.9025 0.0768 0.051 Uiso 1 1 calc . . . C11 C 0.24022(9) 0.7529(4) 0.12440(11) 0.0320(4) Uani 1 1 d . . . C12 C 0.19819(9) 0.9553(4) 0.09586(12) 0.0389(5) Uani 1 1 d . . . H12 H 0.2063 1.0750 0.0607 0.047 Uiso 1 1 calc R . . C13 C 0.14430(10) 0.9778(4) 0.11993(13) 0.0436(5) Uani 1 1 d . . . H13 H 0.1162 1.1141 0.1013 0.052 Uiso 1 1 calc R . . C14 C 0.13202(10) 0.8008(4) 0.17103(13) 0.0405(5) Uani 1 1 d . . . C16 C 0.22588(10) 0.5701(4) 0.17429(12) 0.0384(5) Uani 1 1 d . . . H16 H 0.2531 0.4302 0.1921 0.046 Uiso 1 1 calc R . . C15 C 0.17176(11) 0.5940(4) 0.19765(12) 0.0431(5) Uani 1 1 d . . . H15 H 0.1624 0.4712 0.2311 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.05043(19) 0.1094(3) 0.0885(3) -0.00672(17) 0.04616(16) 0.00350(15) O1 0.0483(9) 0.0273(8) 0.0958(13) 0.0021(7) 0.0410(9) 0.0037(6) N1 0.0364(9) 0.0250(8) 0.0577(11) 0.0015(7) 0.0248(8) 0.0041(7) C1 0.0340(10) 0.0312(11) 0.0469(11) 0.0004(9) 0.0213(9) 0.0000(8) C2 0.0370(11) 0.0363(11) 0.0569(13) 0.0052(9) 0.0251(10) 0.0061(9) C3 0.0318(10) 0.0361(11) 0.0574(13) 0.0036(9) 0.0225(9) 0.0026(9) C4 0.0348(11) 0.0384(11) 0.0605(13) 0.0024(10) 0.0255(10) 0.0029(9) C11 0.0299(10) 0.0292(9) 0.0402(10) -0.0045(8) 0.0150(8) -0.0024(8) C12 0.0351(11) 0.0349(10) 0.0494(12) 0.0055(9) 0.0164(9) 0.0013(9) C13 0.0329(10) 0.0388(11) 0.0604(14) 0.0017(10) 0.0154(10) 0.0065(9) C14 0.0305(10) 0.0500(13) 0.0459(11) -0.0084(10) 0.0188(9) -0.0039(9) C16 0.0372(11) 0.0324(10) 0.0469(11) 0.0053(9) 0.0142(9) 0.0020(9) C15 0.0423(12) 0.0488(12) 0.0424(11) 0.0037(9) 0.0189(9) -0.0076(10) _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 Br1 C14 1.897(2) . ? O1 C1 1.216(2) . ? N1 C1 1.356(3) . ? N1 C11 1.410(3) . ? C1 C2 1.509(3) . ? C2 C3 1.510(3) . ? C3 C4 1.518(3) . ? C4 C4 1.523(4) 5_675 ? C11 C12 1.387(3) . ? C11 C16 1.389(3) . ? C12 C13 1.381(3) . ? C13 C14 1.367(3) . ? C14 C15 1.370(3) . ? C16 C15 1.380(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C11 126.29(17) . . ? O1 C1 N1 122.76(19) . . ? O1 C1 C2 122.47(18) . . ? N1 C1 C2 114.76(17) . . ? C1 C2 C3 113.07(17) . . ? C2 C3 C4 112.87(17) . . ? C3 C4 C4 113.4(2) . 5_675 ? C12 C11 C16 119.14(19) . . ? C12 C11 N1 122.89(18) . . ? C16 C11 N1 117.97(18) . . ? C13 C12 C11 119.59(19) . . ? C14 C13 C12 120.4(2) . . ? C13 C14 C15 120.9(2) . . ? C13 C14 Br1 119.34(16) . . ? C15 C14 Br1 119.74(16) . . ? C15 C16 C11 120.7(2) . . ? C14 C15 C16 119.2(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.275 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.058 data_2Cl _database_code_depnum_ccdc_archive 'CCDC 696966' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Cl2 N2 O2' _chemical_formula_weight 337.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.4189(6) _cell_length_b 9.4168(6) _cell_length_c 9.7128(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.498(2) _cell_angle_gamma 90.00 _cell_volume 769.29(9) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1658 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 26.99 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.430 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.936 _exptl_absorpt_correction_T_max 0.956 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 Bruker' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9829 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0157 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 26.99 _reflns_number_total 1658 _reflns_number_gt 1514 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 0.066(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1658 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1643 _refine_ls_wR_factor_gt 0.1606 _refine_ls_goodness_of_fit_ref 1.485 _refine_ls_restrained_S_all 1.485 _refine_ls_shift/su_max 0.011 _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 Cl1 Cl 0.94019(5) 0.15775(5) 0.41447(5) 0.0620(3) Uani 1 1 d . . . N11 N 0.64819(13) 0.70904(13) 0.54699(11) 0.0335(4) Uani 1 1 d . . . H11 H 0.6385 0.7201 0.6341 0.040 Uiso 1 1 calc R . . C11 C 0.71401(14) 0.57884(14) 0.50570(13) 0.0305(4) Uani 1 1 d . . . C12 C 0.69423(17) 0.46249(17) 0.59121(14) 0.0379(4) Uani 1 1 d . . . H12 H 0.6344 0.4720 0.6689 0.045 Uiso 1 1 calc R . . C13 C 0.76195(18) 0.33321(17) 0.56260(17) 0.0414(4) Uani 1 1 d . . . H13 H 0.7487 0.2558 0.6205 0.050 Uiso 1 1 calc R . . C14 C 0.85006(16) 0.32061(17) 0.44614(16) 0.0385(4) Uani 1 1 d . . . C15 C 0.87036(17) 0.43334(17) 0.35950(15) 0.0400(4) Uani 1 1 d . . . H15 H 0.9293 0.4224 0.2814 0.048 Uiso 1 1 calc R . . C16 C 0.80287(17) 0.56386(17) 0.38846(14) 0.0362(4) Uani 1 1 d . . . H16 H 0.8167 0.6408 0.3302 0.043 Uiso 1 1 calc R . . O21 O 0.60447(16) 0.81761(13) 0.34081(11) 0.0506(4) Uani 1 1 d . . . C21 C 0.59865(16) 0.81822(16) 0.46617(13) 0.0334(4) Uani 1 1 d . . . C22 C 0.5316(2) 0.94103(17) 0.54540(14) 0.0433(4) Uani 1 1 d . . . H22A H 0.4466 0.9062 0.6006 0.052 Uiso 1 1 calc . . . H22B H 0.6143 0.9786 0.6078 0.052 Uiso 1 1 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0741(4) 0.0411(4) 0.0711(5) -0.00947(19) 0.0076(3) 0.02214(19) N11 0.0479(6) 0.0313(7) 0.0219(6) 0.0008(4) 0.0066(4) 0.0071(5) C11 0.0342(6) 0.0303(8) 0.0270(7) -0.0006(5) 0.0017(5) 0.0023(5) C12 0.0469(7) 0.0365(8) 0.0310(7) 0.0044(6) 0.0108(5) 0.0039(6) C13 0.0519(8) 0.0318(9) 0.0408(9) 0.0036(6) 0.0041(6) 0.0026(6) C14 0.0394(7) 0.0329(8) 0.0431(9) -0.0069(6) -0.0009(6) 0.0058(5) C15 0.0415(7) 0.0443(9) 0.0348(8) -0.0057(6) 0.0085(5) 0.0053(6) C16 0.0432(7) 0.0356(8) 0.0303(7) 0.0042(5) 0.0086(5) 0.0034(5) O21 0.0896(9) 0.0397(7) 0.0236(6) 0.0044(4) 0.0133(5) 0.0188(6) C21 0.0474(8) 0.0295(7) 0.0237(7) 0.0012(5) 0.0051(5) 0.0030(5) C22 0.0682(10) 0.0353(8) 0.0269(8) -0.0005(6) 0.0070(6) 0.0137(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 Cl1 C14 1.7444(15) . ? N11 C21 1.3486(18) . ? N11 C11 1.4108(17) . ? C11 C12 1.3893(19) . ? C11 C16 1.3966(19) . ? C12 C13 1.378(2) . ? C13 C14 1.385(2) . ? C14 C15 1.370(2) . ? C15 C16 1.388(2) . ? O21 C21 1.2208(17) . ? C21 C22 1.512(2) . ? C22 C22 1.501(3) 3_676 ? 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 C21 N11 C11 127.76(12) . . ? C12 C11 C16 119.35(13) . . ? C12 C11 N11 117.17(12) . . ? C16 C11 N11 123.41(12) . . ? C13 C12 C11 120.99(13) . . ? C12 C13 C14 118.79(14) . . ? C15 C14 C13 121.40(14) . . ? C15 C14 Cl1 120.40(12) . . ? C13 C14 Cl1 118.17(12) . . ? C14 C15 C16 119.90(13) . . ? C15 C16 C11 119.56(13) . . ? O21 C21 N11 123.52(13) . . ? O21 C21 C22 122.91(13) . . ? N11 C21 C22 113.56(11) . . ? C22 C22 C21 113.42(15) 3_676 . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.294 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.056 data_3Cl _database_code_depnum_ccdc_archive 'CCDC 696967' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 Cl2 N2 O2' _chemical_formula_weight 365.24 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.2555(7) _cell_length_b 10.9653(9) _cell_length_c 9.4726(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.294(2) _cell_angle_gamma 90.00 _cell_volume 852.33(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1854 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 26.98 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.394 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.933 _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 243(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 BRuker' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11032 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 26.98 _reflns_number_total 1854 _reflns_number_gt 1749 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.3105P] 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 1854 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.07972(4) 0.14205(3) 0.02237(3) 0.02784(13) Uani 1 1 d . . . O17 O 0.31163(11) 0.72135(8) -0.12688(9) 0.0236(2) Uani 1 1 d . . . N11 N 0.29351(13) 0.65610(9) 0.09911(10) 0.0183(2) Uani 1 1 d . . . H11 H 0.3062 0.6785 0.1866 0.022 Uiso 1 1 calc R . . C11 C 0.23944(13) 0.53498(10) 0.07175(11) 0.0162(2) Uani 1 1 d . . . C12 C 0.28972(14) 0.46495(11) -0.03854(12) 0.0194(2) Uani 1 1 d . . . H12 H 0.3565 0.4990 -0.1010 0.023 Uiso 1 1 calc R . . C13 C 0.23975(15) 0.34417(11) -0.05480(13) 0.0207(3) Uani 1 1 d . . . H13 H 0.2729 0.2969 -0.1279 0.025 Uiso 1 1 calc R . . C14 C 0.13987(14) 0.29487(11) 0.03926(12) 0.0193(2) Uani 1 1 d . . . C15 C 0.08659(15) 0.36358(10) 0.14756(13) 0.0200(3) Uani 1 1 d . . . H15 H 0.0182 0.3296 0.2087 0.024 Uiso 1 1 calc R . . C16 C 0.13684(14) 0.48396(11) 0.16355(12) 0.0180(2) Uani 1 1 d . . . H16 H 0.1019 0.5311 0.2360 0.022 Uiso 1 1 calc R . . C17 C 0.32737(13) 0.74052(10) 0.00191(12) 0.0176(2) Uani 1 1 d . . . C18 C 0.38554(15) 0.86132(10) 0.06609(13) 0.0204(3) Uani 1 1 d . . . H18A H 0.4634 0.8459 0.1485 0.025 Uiso 1 1 calc . . . H18B H 0.2935 0.9040 0.0983 0.025 Uiso 1 1 calc . . . C19 C 0.46458(15) 0.94267(10) -0.03634(12) 0.0193(2) Uani 1 1 d . . . H19A H 0.3841 0.9653 -0.1143 0.023 Uiso 1 1 calc . . . H19B H 0.5506 0.8979 -0.0754 0.023 Uiso 1 1 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0392(2) 0.01335(18) 0.0314(2) -0.00214(10) 0.00617(14) -0.00786(11) O17 0.0392(5) 0.0176(4) 0.0141(4) -0.0002(3) 0.0039(3) -0.0068(4) N11 0.0286(5) 0.0136(5) 0.0127(4) -0.0013(3) 0.0027(4) -0.0044(4) C11 0.0209(5) 0.0121(5) 0.0151(5) 0.0014(4) -0.0007(4) -0.0015(4) C12 0.0235(5) 0.0172(6) 0.0183(5) -0.0002(4) 0.0054(4) -0.0028(4) C13 0.0257(6) 0.0164(6) 0.0203(6) -0.0037(4) 0.0042(4) 0.0001(4) C14 0.0230(5) 0.0114(5) 0.0228(6) 0.0005(4) -0.0009(4) -0.0030(4) C15 0.0239(6) 0.0186(6) 0.0175(6) 0.0026(4) 0.0026(4) -0.0043(4) C16 0.0226(5) 0.0171(6) 0.0145(5) -0.0007(4) 0.0025(4) -0.0007(4) C17 0.0214(5) 0.0144(5) 0.0172(5) 0.0001(4) 0.0032(4) -0.0021(4) C18 0.0305(6) 0.0143(6) 0.0170(5) -0.0020(4) 0.0051(5) -0.0057(4) C19 0.0264(6) 0.0149(6) 0.0163(5) 0.0004(4) 0.0020(4) -0.0059(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 Cl1 C14 1.7500(12) . ? O17 C17 1.2306(14) . ? N11 C17 1.3562(14) . ? N11 C11 1.4159(14) . ? C11 C12 1.3960(16) . ? C11 C16 1.3958(15) . ? C12 C13 1.3906(16) . ? C13 C14 1.3882(17) . ? C14 C15 1.3830(17) . ? C15 C16 1.3869(16) . ? C17 C18 1.5136(15) . ? C18 C19 1.5172(16) . ? C19 C19 1.519(2) 3_675 ? 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 C17 N11 C11 126.89(10) . . ? C12 C11 C16 119.76(10) . . ? C12 C11 N11 122.64(10) . . ? C16 C11 N11 117.56(10) . . ? C13 C12 C11 119.86(11) . . ? C14 C13 C12 119.32(11) . . ? C15 C14 C13 121.57(11) . . ? C15 C14 Cl1 118.65(9) . . ? C13 C14 Cl1 119.78(9) . . ? C14 C15 C16 118.94(11) . . ? C15 C16 C11 120.54(11) . . ? O17 C17 N11 123.31(10) . . ? O17 C17 C18 122.82(10) . . ? N11 C17 C18 113.86(9) . . ? C17 C18 C19 113.42(9) . . ? C18 C19 C19 111.59(12) . 3_675 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.98 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.288 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.113 data_4Cl _database_code_depnum_ccdc_archive 'CCDC 696968' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 Cl2 N2 O2' _chemical_formula_weight 393.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.870(8) _cell_length_b 5.1043(19) _cell_length_c 17.683(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.685(10) _cell_angle_gamma 90.00 _cell_volume 1900.5(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2061 _cell_measurement_theta_min 1.93 _cell_measurement_theta_max 27.00 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.359 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.952 _exptl_absorpt_correction_T_max 0.963 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 Bruker' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12186 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2061 _reflns_number_gt 1727 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0618P)^2^+0.6333P] 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 2061 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.1063 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.05935(2) 0.83589(11) 0.20576(3) 0.0766(2) Uani 1 1 d . . . N11 N 0.29460(5) 0.7241(2) 0.10598(7) 0.0364(3) Uani 1 1 d . . . H11 H 0.3066 0.5668 0.1001 0.044 Uiso 1 1 calc R . . C11 C 0.23668(6) 0.7534(2) 0.12582(7) 0.0317(3) Uani 1 1 d . . . C12 C 0.19462(6) 0.9561(3) 0.09743(8) 0.0386(3) Uani 1 1 d . . . H12 H 0.2032 1.0768 0.0622 0.046 Uiso 1 1 calc R . . C13 C 0.13992(6) 0.9780(3) 0.12171(9) 0.0447(3) Uani 1 1 d . . . H13 H 0.1117 1.1145 0.1031 0.054 Uiso 1 1 calc R . . C14 C 0.12714(6) 0.7984(3) 0.17329(9) 0.0429(3) Uani 1 1 d . . . C15 C 0.16714(7) 0.5908(3) 0.19961(8) 0.0423(3) Uani 1 1 d . . . H15 H 0.1574 0.4666 0.2330 0.051 Uiso 1 1 calc R . . C16 C 0.22198(6) 0.5691(3) 0.17586(8) 0.0379(3) Uani 1 1 d . . . H16 H 0.2494 0.4295 0.1936 0.046 Uiso 1 1 calc R . . O21 O 0.31806(5) 1.15126(18) 0.09388(7) 0.0505(3) Uani 1 1 d . . . C21 C 0.33299(6) 0.9207(2) 0.09534(8) 0.0347(3) Uani 1 1 d . . . C22 C 0.39706(7) 0.8333(3) 0.08829(9) 0.0407(3) Uani 1 1 d . . . H22A H 0.3937 0.6551 0.0685 0.049 Uiso 1 1 calc . . . H22B H 0.4269 0.8331 0.1401 0.049 Uiso 1 1 calc . . . C23 C 0.42274(6) 1.0057(3) 0.03458(9) 0.0396(3) Uani 1 1 d . . . H23A H 0.4271 1.1832 0.0549 0.047 Uiso 1 1 calc . . . H23B H 0.3926 1.0090 -0.0169 0.047 Uiso 1 1 calc . . . C24 C 0.48658(6) 0.9133(3) 0.02645(9) 0.0415(3) Uani 1 1 d . . . H24A H 0.5165 0.9074 0.0781 0.050 Uiso 1 1 calc . . . H24B H 0.4821 0.7365 0.0055 0.050 Uiso 1 1 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0505(3) 0.1016(4) 0.0937(4) -0.0086(3) 0.0469(3) 0.0013(2) N11 0.0365(6) 0.0258(5) 0.0531(7) 0.0005(4) 0.0229(5) 0.0038(4) C11 0.0317(6) 0.0289(6) 0.0372(6) -0.0043(5) 0.0140(5) -0.0017(5) C12 0.0349(7) 0.0337(6) 0.0495(8) 0.0048(6) 0.0152(6) 0.0014(5) C13 0.0330(7) 0.0405(7) 0.0618(9) -0.0002(6) 0.0149(6) 0.0054(6) C14 0.0334(7) 0.0519(8) 0.0483(8) -0.0110(6) 0.0195(6) -0.0054(6) C15 0.0433(8) 0.0478(8) 0.0400(7) 0.0021(6) 0.0186(6) -0.0071(6) C16 0.0388(7) 0.0341(6) 0.0422(7) 0.0028(5) 0.0132(6) 0.0001(5) O21 0.0466(6) 0.0282(5) 0.0887(8) 0.0026(5) 0.0391(6) 0.0031(4) C21 0.0356(7) 0.0312(6) 0.0422(7) 0.0014(5) 0.0190(5) 0.0034(5) C22 0.0363(7) 0.0381(7) 0.0540(8) 0.0068(6) 0.0229(6) 0.0075(6) C23 0.0339(6) 0.0358(7) 0.0549(8) 0.0034(6) 0.0220(6) 0.0036(5) C24 0.0327(7) 0.0382(7) 0.0591(9) 0.0027(6) 0.0222(6) 0.0045(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C14 1.7391(15) . ? N11 C21 1.3537(17) . ? N11 C11 1.4106(17) . ? C11 C16 1.3874(18) . ? C11 C12 1.3854(18) . ? C12 C13 1.3804(19) . ? C13 C14 1.374(2) . ? C14 C15 1.373(2) . ? C15 C16 1.3783(19) . ? O21 C21 1.2196(16) . ? C21 C22 1.5074(18) . ? C22 C23 1.5102(19) . ? C23 C24 1.5170(18) . ? C24 C24 1.517(3) 5_675 ? 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 C21 N11 C11 126.05(11) . . ? C16 C11 C12 119.46(12) . . ? C16 C11 N11 117.73(11) . . ? C12 C11 N11 122.81(12) . . ? C13 C12 C11 119.61(13) . . ? C12 C13 C14 120.09(13) . . ? C15 C14 C13 120.97(13) . . ? C15 C14 Cl1 119.68(12) . . ? C13 C14 Cl1 119.35(12) . . ? C14 C15 C16 119.09(13) . . ? C15 C16 C11 120.71(13) . . ? O21 C21 N11 123.07(13) . . ? O21 C21 C22 122.23(12) . . ? N11 C21 C22 114.67(11) . . ? C21 C22 C23 113.06(11) . . ? C22 C23 C24 112.75(11) . . ? C24 C24 C23 113.35(14) 5_675 . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.159 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.062 data_2F _database_code_depnum_ccdc_archive 'CCDC 696969' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 F2 N2 O2' _chemical_formula_weight 304.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.7199(4) _cell_length_b 5.7814(3) _cell_length_c 32.4814(17) _cell_angle_alpha 90.00 _cell_angle_beta 94.019(2) _cell_angle_gamma 90.00 _cell_volume 1446.14(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3446 _cell_measurement_theta_min 1.26 _cell_measurement_theta_max 27.99 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 Bruker' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18570 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 27.99 _reflns_number_total 3446 _reflns_number_gt 2440 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0980P)^2^+0.2928P] 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 3446 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1817 _refine_ls_wR_factor_gt 0.1670 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.004 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 F14 F 0.05746(18) 0.3264(3) 0.23652(3) 0.0826(4) Uani 1 1 d . . . F24 F 0.46221(19) 1.1458(3) -0.23624(4) 0.0862(4) Uani 1 1 d . . . N11 N 0.23257(17) 0.4758(2) 0.07720(4) 0.0497(4) Uani 1 1 d . . . H11 H 0.3174 0.3912 0.0703 0.060 Uiso 1 1 calc R . . C11 C 0.17799(19) 0.4398(3) 0.11748(4) 0.0427(4) Uani 1 1 d . . . C12 C 0.2293(2) 0.2366(3) 0.13749(5) 0.0529(4) Uani 1 1 d . . . H12 H 0.2907 0.1256 0.1238 0.063 Uiso 1 1 calc R . . C13 C 0.1897(2) 0.1986(3) 0.17755(6) 0.0584(5) Uani 1 1 d . . . H13 H 0.2240 0.0628 0.1911 0.070 Uiso 1 1 calc R . . C14 C 0.0984(2) 0.3647(3) 0.19718(5) 0.0549(4) Uani 1 1 d . . . C15 C 0.0459(2) 0.5664(3) 0.17834(5) 0.0536(4) Uani 1 1 d . . . H15 H -0.0162 0.6757 0.1923 0.064 Uiso 1 1 calc R . . C16 C 0.0866(2) 0.6049(3) 0.13811(5) 0.0480(4) Uani 1 1 d . . . H16 H 0.0527 0.7419 0.1249 0.058 Uiso 1 1 calc R . . N21 N 0.25962(18) 1.0228(3) -0.07838(4) 0.0548(4) Uani 1 1 d . . . H21 H 0.1772 1.1096 -0.0708 0.066 Uiso 1 1 calc R . . C21 C 0.31582(19) 1.0538(3) -0.11914(5) 0.0456(4) Uani 1 1 d . . . C22 C 0.3993(2) 1.2551(3) -0.12938(6) 0.0573(4) Uani 1 1 d . . . H22 H 0.4220 1.3695 -0.1096 0.069 Uiso 1 1 calc R . . C23 C 0.4490(2) 1.2857(3) -0.16905(6) 0.0621(5) Uani 1 1 d . . . H23 H 0.5064 1.4197 -0.1762 0.074 Uiso 1 1 calc R . . C24 C 0.4123(2) 1.1160(3) -0.19748(5) 0.0562(4) Uani 1 1 d . . . C25 C 0.3294(3) 0.9165(3) -0.18827(5) 0.0591(5) Uani 1 1 d . . . H25 H 0.3063 0.8035 -0.2083 0.071 Uiso 1 1 calc R . . C26 C 0.2804(2) 0.8859(3) -0.14854(5) 0.0537(4) Uani 1 1 d . . . H26 H 0.2233 0.7512 -0.1416 0.064 Uiso 1 1 calc R . . O31 O 0.0397(3) 0.7408(4) 0.05313(5) 0.1287(9) Uani 1 1 d . . . O34 O 0.4503(2) 0.7470(3) -0.05911(4) 0.0910(6) Uani 1 1 d . . . C31 C 0.1688(3) 0.6242(4) 0.04894(6) 0.0697(6) Uani 1 1 d . . . C32 C 0.2649(3) 0.6360(4) 0.01002(6) 0.0824(8) Uani 1 1 d . . . H32A H 0.3877 0.6118 0.0171 0.099 Uiso 1 1 calc . . . H32B H 0.2245 0.5120 -0.0083 0.099 Uiso 1 1 calc . . . C33 C 0.2416(3) 0.8561(4) -0.01163(6) 0.0784(7) Uani 1 1 d . . . H33A H 0.2880 0.9786 0.0063 0.094 Uiso 1 1 calc . . . H33B H 0.1182 0.8842 -0.0170 0.094 Uiso 1 1 calc . . . C34 C 0.3269(2) 0.8687(3) -0.05180(5) 0.0581(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 F14 0.1056(10) 0.0993(10) 0.0456(6) 0.0117(6) 0.0250(6) -0.0079(8) F24 0.1076(10) 0.0993(10) 0.0558(7) 0.0186(6) 0.0343(6) 0.0069(8) N11 0.0489(7) 0.0583(8) 0.0441(7) 0.0042(6) 0.0187(6) 0.0213(6) C11 0.0391(7) 0.0502(8) 0.0397(7) 0.0008(6) 0.0097(6) 0.0063(6) C12 0.0555(9) 0.0488(9) 0.0557(9) 0.0031(7) 0.0132(7) 0.0120(7) C13 0.0655(11) 0.0531(10) 0.0571(10) 0.0143(8) 0.0077(8) 0.0014(8) C14 0.0588(10) 0.0675(11) 0.0394(8) 0.0023(8) 0.0112(7) -0.0105(8) C15 0.0584(10) 0.0600(10) 0.0442(8) -0.0076(7) 0.0162(7) 0.0034(8) C16 0.0520(9) 0.0499(9) 0.0432(8) 0.0008(7) 0.0113(6) 0.0100(7) N21 0.0530(8) 0.0682(9) 0.0453(7) 0.0046(6) 0.0173(6) 0.0291(7) C21 0.0407(7) 0.0541(9) 0.0428(8) 0.0025(7) 0.0092(6) 0.0163(7) C22 0.0579(10) 0.0551(10) 0.0591(10) -0.0057(8) 0.0053(8) 0.0022(8) C23 0.0599(10) 0.0585(11) 0.0691(12) 0.0106(9) 0.0144(9) -0.0035(8) C24 0.0581(10) 0.0648(11) 0.0472(9) 0.0115(8) 0.0147(7) 0.0093(8) C25 0.0737(12) 0.0587(10) 0.0456(9) -0.0031(7) 0.0095(8) -0.0004(9) C26 0.0598(10) 0.0517(9) 0.0506(9) 0.0034(7) 0.0119(7) -0.0010(8) O31 0.1302(14) 0.189(2) 0.0743(10) 0.0645(11) 0.0639(10) 0.1252(15) O34 0.0924(10) 0.1215(13) 0.0644(8) 0.0334(8) 0.0421(8) 0.0748(10) C31 0.0714(12) 0.0911(14) 0.0502(10) 0.0185(9) 0.0300(8) 0.0476(11) C32 0.0965(15) 0.0988(16) 0.0576(11) 0.0263(11) 0.0448(11) 0.0608(13) C33 0.0971(15) 0.0874(14) 0.0560(11) 0.0160(10) 0.0421(11) 0.0488(13) C34 0.0607(10) 0.0711(11) 0.0450(8) 0.0078(8) 0.0215(7) 0.0315(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 F14 C14 1.3557(18) . ? F24 C24 1.3532(18) . ? N11 C31 1.326(2) . ? N11 C11 1.4177(18) . ? C11 C16 1.387(2) . ? C11 C12 1.387(2) . ? C12 C13 1.375(2) . ? C13 C14 1.374(3) . ? C14 C15 1.365(3) . ? C15 C16 1.383(2) . ? N21 C34 1.321(2) . ? N21 C21 1.4331(19) . ? C21 C26 1.376(2) . ? C21 C22 1.382(2) . ? C22 C23 1.381(2) . ? C23 C24 1.364(3) . ? C24 C25 1.362(3) . ? C25 C26 1.381(2) . ? O31 C31 1.218(2) . ? O34 C34 1.2210(19) . ? C31 C32 1.512(2) . ? C32 C33 1.459(3) . ? C33 C34 1.504(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C31 N11 C11 127.88(13) . . ? C16 C11 C12 119.65(14) . . ? C16 C11 N11 122.61(14) . . ? C12 C11 N11 117.60(13) . . ? C13 C12 C11 120.24(15) . . ? C12 C13 C14 118.87(16) . . ? F14 C14 C15 118.71(16) . . ? F14 C14 C13 118.96(16) . . ? C15 C14 C13 122.33(15) . . ? C14 C15 C16 118.74(15) . . ? C15 C16 C11 120.17(15) . . ? C34 N21 C21 123.88(13) . . ? C26 C21 C22 120.03(15) . . ? C26 C21 N21 119.65(15) . . ? C22 C21 N21 120.28(15) . . ? C23 C22 C21 119.82(16) . . ? C24 C23 C22 118.77(17) . . ? F24 C24 C25 118.74(17) . . ? F24 C24 C23 118.65(17) . . ? C25 C24 C23 122.61(16) . . ? C24 C25 C26 118.51(17) . . ? C21 C26 C25 120.25(16) . . ? O31 C31 N11 123.20(16) . . ? O31 C31 C32 121.44(16) . . ? N11 C31 C32 115.35(14) . . ? C33 C32 C31 113.05(16) . . ? C32 C33 C34 114.46(16) . . ? O34 C34 N21 122.53(15) . . ? O34 C34 C33 122.39(16) . . ? N21 C34 C33 115.07(14) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.293 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.042 data_3F _database_code_depnum_ccdc_archive 'CCDC 696970' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 F2 N2 O2' _chemical_formula_weight 332.34 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.3328(8) _cell_length_b 9.5211(6) _cell_length_c 15.3985(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1661.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1814 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 27.00 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 Bruker' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20610 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1814 _reflns_number_gt 1373 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0817P)^2^+0.3604P] 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 1814 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1483 _refine_ls_wR_factor_gt 0.1377 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F14 F 0.20097(10) 0.05384(18) 0.69180(9) 0.0995(5) Uani 1 1 d . . . N11 N 0.67282(12) 0.10164(13) 0.60987(9) 0.0493(4) Uani 1 1 d . . . H11 H 0.6954 0.1868 0.6014 0.059 Uiso 1 1 calc R . . C11 C 0.55294(14) 0.08230(16) 0.63239(10) 0.0464(4) Uani 1 1 d . . . C12 C 0.48899(16) -0.03591(19) 0.60916(12) 0.0580(5) Uani 1 1 d . . . H12 H 0.5257 -0.1089 0.5795 0.070 Uiso 1 1 calc R . . C13 C 0.37045(17) -0.0452(2) 0.63012(13) 0.0684(5) Uani 1 1 d . . . H13 H 0.3272 -0.1247 0.6153 0.082 Uiso 1 1 calc R . . C14 C 0.31807(16) 0.0635(2) 0.67264(12) 0.0661(5) Uani 1 1 d . . . C15 C 0.37841(16) 0.1805(2) 0.69687(12) 0.0659(5) Uani 1 1 d . . . H15 H 0.3406 0.2530 0.7263 0.079 Uiso 1 1 calc R . . C16 C 0.49709(15) 0.18954(17) 0.67687(12) 0.0554(4) Uani 1 1 d . . . H16 H 0.5398 0.2685 0.6935 0.066 Uiso 1 1 calc R . . O21 O 0.73332(12) -0.12360(11) 0.60784(12) 0.0820(6) Uani 1 1 d . . . C21 C 0.75502(15) 0.00156(17) 0.60034(12) 0.0543(4) Uani 1 1 d . . . C22 C 0.87789(16) 0.05395(18) 0.58054(14) 0.0645(5) Uani 1 1 d . . . H22A H 0.8736 0.1524 0.5647 0.077 Uiso 1 1 calc . . . H22B H 0.9256 0.0468 0.6327 0.077 Uiso 1 1 calc . . . C23 C 0.93770(13) -0.02537(17) 0.50854(11) 0.0509(4) Uani 1 1 d . . . H23A H 0.8916 -0.0156 0.4558 0.061 Uiso 1 1 calc . . . H23B H 0.9400 -0.1243 0.5234 0.061 Uiso 1 1 calc . . . 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 F14 0.0434(6) 0.1693(15) 0.0859(9) -0.0120(9) 0.0099(5) 0.0047(7) N11 0.0483(8) 0.0301(6) 0.0694(9) 0.0005(5) 0.0123(6) 0.0001(5) C11 0.0441(8) 0.0414(8) 0.0537(8) 0.0060(6) 0.0053(6) 0.0058(6) C12 0.0494(10) 0.0519(10) 0.0726(11) -0.0034(8) 0.0107(8) -0.0012(7) C13 0.0520(11) 0.0815(14) 0.0717(11) 0.0007(10) 0.0049(9) -0.0114(9) C14 0.0397(9) 0.1031(15) 0.0555(10) 0.0041(10) 0.0039(7) 0.0085(10) C15 0.0550(11) 0.0814(13) 0.0612(10) -0.0032(9) 0.0049(8) 0.0256(10) C16 0.0553(10) 0.0492(9) 0.0615(10) -0.0022(7) 0.0018(7) 0.0118(7) O21 0.0540(8) 0.0310(7) 0.1611(16) 0.0018(7) 0.0304(8) 0.0012(5) C21 0.0464(9) 0.0349(8) 0.0815(11) -0.0053(7) 0.0178(8) -0.0008(6) C22 0.0509(10) 0.0451(9) 0.0976(14) -0.0175(9) 0.0242(9) -0.0082(7) C23 0.0408(9) 0.0493(9) 0.0627(9) -0.0050(7) 0.0053(7) -0.0015(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 F14 C14 1.363(2) . ? N11 C21 1.341(2) . ? N11 C11 1.414(2) . ? C11 C16 1.383(2) . ? C11 C12 1.386(2) . ? C12 C13 1.384(3) . ? C13 C14 1.361(3) . ? C14 C15 1.360(3) . ? C15 C16 1.382(2) . ? O21 C21 1.2223(19) . ? C21 C22 1.510(2) . ? C22 C23 1.503(2) . ? C23 C23 1.515(3) 5_756 ? 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 C21 N11 C11 127.00(13) . . ? C16 C11 C12 119.22(16) . . ? C16 C11 N11 117.71(15) . . ? C12 C11 N11 123.03(14) . . ? C13 C12 C11 119.96(18) . . ? C14 C13 C12 119.12(19) . . ? C13 C14 F14 118.5(2) . . ? C13 C14 C15 122.41(18) . . ? F14 C14 C15 119.06(19) . . ? C14 C15 C16 118.63(17) . . ? C15 C16 C11 120.65(17) . . ? O21 C21 N11 122.88(16) . . ? O21 C21 C22 121.78(15) . . ? N11 C21 C22 115.34(14) . . ? C23 C22 C21 113.51(14) . . ? C22 C23 C23 112.84(17) . 5_756 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.210 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.037 data_4F _database_code_depnum_ccdc_archive 'CCDC 696971' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 F2 N2 O2' _chemical_formula_weight 360.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.084(3) _cell_length_b 5.0326(7) _cell_length_c 39.311(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.792(4) _cell_angle_gamma 90.00 _cell_volume 3552.6(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3406 _cell_measurement_theta_min 1.04 _cell_measurement_theta_max 25.76 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.990 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 Bruker' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20696 _diffrn_reflns_av_R_equivalents 0.0523 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -48 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_theta_min 1.04 _diffrn_reflns_theta_max 25.76 _reflns_number_total 3406 _reflns_number_gt 2172 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+3.5009P] 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 3406 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0901 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1427 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _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 O11 O 0.54410(10) 0.1322(3) 0.56001(4) 0.0503(5) Uani 1 1 d . . . O12 O 0.79521(12) -0.2094(3) 0.36528(5) 0.0652(6) Uani 1 1 d . . . C11 C 0.54774(12) -0.1082(4) 0.55484(6) 0.0374(5) Uani 1 1 d . . . C12 C 0.57784(13) -0.2203(4) 0.52361(6) 0.0413(6) Uani 1 1 d . . . H12A H 0.6042 -0.3839 0.5300 0.050 Uiso 1 1 calc . . . H12B H 0.5362 -0.2646 0.5067 0.050 Uiso 1 1 calc . . . C13 C 0.62946(13) -0.0369(5) 0.50738(6) 0.0422(6) Uani 1 1 d . . . H13A H 0.6741 -0.0098 0.5232 0.051 Uiso 1 1 calc . . . H13B H 0.6054 0.1342 0.5033 0.051 Uiso 1 1 calc . . . C14 C 0.65131(13) -0.1421(4) 0.47384(6) 0.0413(6) Uani 1 1 d . . . H14A H 0.6760 -0.3121 0.4781 0.050 Uiso 1 1 calc . . . H14B H 0.6065 -0.1724 0.4582 0.050 Uiso 1 1 calc . . . C15 C 0.70205(14) 0.0403(5) 0.45679(6) 0.0428(6) Uani 1 1 d . . . H15A H 0.7478 0.0650 0.4720 0.051 Uiso 1 1 calc . . . H15B H 0.6782 0.2125 0.4534 0.051 Uiso 1 1 calc . . . C16 C 0.72137(13) -0.0605(4) 0.42264(6) 0.0425(6) Uani 1 1 d . . . H16A H 0.6758 -0.0813 0.4072 0.051 Uiso 1 1 calc . . . H16B H 0.7444 -0.2340 0.4259 0.051 Uiso 1 1 calc . . . C17 C 0.77350(13) 0.1228(4) 0.40635(6) 0.0414(6) Uani 1 1 d . . . H17A H 0.7506 0.2969 0.4034 0.050 Uiso 1 1 calc . . . H17B H 0.8191 0.1423 0.4218 0.050 Uiso 1 1 calc . . . C18 C 0.79269(13) 0.0270(4) 0.37219(6) 0.0404(5) Uani 1 1 d . . . F21 F 0.37407(11) -0.1480(4) 0.68850(4) 0.0884(6) Uani 1 1 d . . . N21 N 0.52337(10) -0.2909(3) 0.57582(4) 0.0396(5) Uani 1 1 d . . . H21 H 0.5311 -0.4543 0.5709 0.048 Uiso 1 1 calc R . . C21 C 0.48627(12) -0.2453(4) 0.60523(5) 0.0369(5) Uani 1 1 d . . . C22 C 0.50552(14) -0.0398(5) 0.62794(6) 0.0450(6) Uani 1 1 d . . . H22 H 0.5437 0.0765 0.6242 0.054 Uiso 1 1 calc R . . C23 C 0.46776(16) -0.0078(5) 0.65632(6) 0.0548(7) Uani 1 1 d . . . H23 H 0.4801 0.1299 0.6717 0.066 Uiso 1 1 calc R . . C24 C 0.41212(16) -0.1820(5) 0.66130(6) 0.0549(7) Uani 1 1 d . . . C25 C 0.39314(15) -0.3891(5) 0.63978(6) 0.0531(7) Uani 1 1 d . . . H25 H 0.3559 -0.5075 0.6441 0.064 Uiso 1 1 calc R . . C26 C 0.43066(14) -0.4191(5) 0.61135(6) 0.0472(6) Uani 1 1 d . . . H26 H 0.4182 -0.5583 0.5962 0.057 Uiso 1 1 calc R . . F31 F 0.90781(13) 0.1365(4) 0.22411(5) 0.1078(8) Uani 1 1 d . . . N31 N 0.80841(11) 0.2207(4) 0.35056(4) 0.0418(5) Uani 1 1 d . . . H31 H 0.8035 0.3815 0.3573 0.050 Uiso 1 1 calc R . . C31 C 0.83223(13) 0.1869(4) 0.31777(6) 0.0407(5) Uani 1 1 d . . . C32 C 0.88360(16) -0.0030(6) 0.31171(7) 0.0578(7) Uani 1 1 d . . . H32 H 0.9016 -0.1201 0.3290 0.069 Uiso 1 1 calc R . . C33 C 0.90863(18) -0.0203(6) 0.27986(7) 0.0696(9) Uani 1 1 d . . . H33 H 0.9433 -0.1488 0.2756 0.084 Uiso 1 1 calc R . . C34 C 0.88207(18) 0.1518(6) 0.25516(7) 0.0652(8) Uani 1 1 d . . . C35 C 0.83068(19) 0.3425(6) 0.26012(7) 0.0708(9) Uani 1 1 d . . . H35 H 0.8129 0.4580 0.2426 0.085 Uiso 1 1 calc R . . C36 C 0.80588(16) 0.3588(5) 0.29206(6) 0.0575(7) Uani 1 1 d . . . H36 H 0.7711 0.4875 0.2961 0.069 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O11 0.0722(12) 0.0294(9) 0.0539(10) -0.0044(7) 0.0264(9) 0.0000(8) O12 0.1101(16) 0.0292(9) 0.0653(12) -0.0043(8) 0.0475(11) -0.0037(10) C11 0.0392(13) 0.0326(12) 0.0414(12) -0.0005(10) 0.0088(10) 0.0007(10) C12 0.0507(14) 0.0333(12) 0.0423(12) -0.0064(10) 0.0148(11) -0.0016(10) C13 0.0475(14) 0.0386(13) 0.0428(12) -0.0066(10) 0.0148(11) -0.0056(11) C14 0.0496(14) 0.0377(12) 0.0389(12) -0.0041(10) 0.0140(10) -0.0052(11) C15 0.0523(14) 0.0359(12) 0.0426(12) -0.0033(10) 0.0154(11) -0.0047(11) C16 0.0531(15) 0.0360(12) 0.0408(12) -0.0033(10) 0.0155(11) -0.0050(11) C17 0.0509(14) 0.0350(12) 0.0404(12) -0.0018(10) 0.0144(11) -0.0023(11) C18 0.0491(14) 0.0315(12) 0.0431(12) -0.0038(10) 0.0158(11) -0.0017(10) F21 0.1227(16) 0.0852(13) 0.0694(11) -0.0054(10) 0.0616(11) 0.0081(12) N21 0.0539(12) 0.0267(9) 0.0417(10) -0.0027(8) 0.0196(9) -0.0001(8) C21 0.0430(13) 0.0319(11) 0.0371(12) 0.0011(9) 0.0104(10) 0.0044(10) C22 0.0548(15) 0.0392(13) 0.0421(13) -0.0042(10) 0.0102(11) -0.0036(11) C23 0.0773(19) 0.0468(15) 0.0418(13) -0.0084(12) 0.0141(13) 0.0088(14) C24 0.0716(18) 0.0542(16) 0.0441(14) 0.0022(12) 0.0289(13) 0.0129(14) C25 0.0595(16) 0.0481(15) 0.0562(15) 0.0071(13) 0.0254(13) -0.0022(13) C26 0.0578(16) 0.0390(13) 0.0471(13) -0.0017(11) 0.0164(12) -0.0051(12) F31 0.175(2) 0.0955(15) 0.0668(11) -0.0036(10) 0.0742(13) 0.0006(14) N31 0.0589(13) 0.0289(9) 0.0411(11) -0.0033(8) 0.0203(9) -0.0015(9) C31 0.0488(14) 0.0338(12) 0.0417(12) 0.0003(10) 0.0148(11) -0.0061(10) C32 0.0690(18) 0.0548(16) 0.0542(15) 0.0083(13) 0.0262(13) 0.0125(14) C33 0.089(2) 0.0548(17) 0.0741(19) -0.0006(16) 0.0490(17) 0.0088(16) C34 0.095(2) 0.0591(17) 0.0491(16) -0.0066(14) 0.0409(15) -0.0126(17) C35 0.103(2) 0.0659(19) 0.0468(16) 0.0136(14) 0.0218(16) 0.0029(18) C36 0.0743(19) 0.0484(15) 0.0535(15) 0.0050(13) 0.0231(13) 0.0079(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 O11 C11 1.230(3) . ? O12 C18 1.222(3) . ? C11 N21 1.344(3) . ? C11 C12 1.510(3) . ? C12 C13 1.507(3) . ? C13 C14 1.516(3) . ? C14 C15 1.510(3) . ? C15 C16 1.514(3) . ? C16 C17 1.514(3) . ? C17 C18 1.505(3) . ? C18 N31 1.346(3) . ? F21 C24 1.349(3) . ? N21 C21 1.422(3) . ? C21 C26 1.375(3) . ? C21 C22 1.384(3) . ? C22 C23 1.384(3) . ? C23 C24 1.366(4) . ? C24 C25 1.361(4) . ? C25 C26 1.383(3) . ? F31 C34 1.359(3) . ? N31 C31 1.417(3) . ? C31 C36 1.372(3) . ? C31 C32 1.373(3) . ? C32 C33 1.384(3) . ? C33 C34 1.346(4) . ? C34 C35 1.366(4) . ? C35 C36 1.385(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O11 C11 N21 122.9(2) . . ? O11 C11 C12 122.3(2) . . ? N21 C11 C12 114.78(19) . . ? C13 C12 C11 114.60(19) . . ? C12 C13 C14 113.12(19) . . ? C15 C14 C13 114.10(19) . . ? C14 C15 C16 113.95(19) . . ? C15 C16 C17 113.04(19) . . ? C18 C17 C16 113.76(19) . . ? O12 C18 N31 123.2(2) . . ? O12 C18 C17 121.9(2) . . ? N31 C18 C17 114.82(19) . . ? C11 N21 C21 127.50(18) . . ? C26 C21 C22 119.7(2) . . ? C26 C21 N21 117.7(2) . . ? C22 C21 N21 122.6(2) . . ? C23 C22 C21 119.8(2) . . ? C24 C23 C22 118.9(2) . . ? F21 C24 C25 118.4(3) . . ? F21 C24 C23 119.1(2) . . ? C25 C24 C23 122.6(2) . . ? C24 C25 C26 118.3(2) . . ? C21 C26 C25 120.7(2) . . ? C18 N31 C31 126.69(19) . . ? C36 C31 C32 119.6(2) . . ? C36 C31 N31 118.5(2) . . ? C32 C31 N31 121.7(2) . . ? C31 C32 C33 120.1(3) . . ? C34 C33 C32 119.0(3) . . ? C33 C34 F31 118.7(3) . . ? C33 C34 C35 122.7(2) . . ? F31 C34 C35 118.6(3) . . ? C34 C35 C36 118.0(3) . . ? C31 C36 C35 120.6(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.76 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.182 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.042 data_5F _database_code_depnum_ccdc_archive 'CCDC 696972' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 F2 N2 O2' _chemical_formula_weight 388.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.1488(12) _cell_length_b 5.0327(3) _cell_length_c 43.840(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.817(2) _cell_angle_gamma 90.00 _cell_volume 3945.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4263 _cell_measurement_theta_min 0.94 _cell_measurement_theta_max 27.00 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1648 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.987 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 BRUKER' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25190 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -56 _diffrn_reflns_limit_l_max 53 _diffrn_reflns_theta_min 0.94 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4263 _reflns_number_gt 2902 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0972P)^2^+1.8062P] 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 4263 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1700 _refine_ls_wR_factor_gt 0.1500 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 N1 N 0.50168(9) 0.3314(3) 0.09218(4) 0.0404(4) Uani 1 1 d . . . H1 H 0.5079 0.4951 0.0876 0.048 Uiso 1 1 calc R . . N2 N 0.82054(9) -0.2578(3) -0.15892(4) 0.0419(4) Uani 1 1 d . . . H2 H 0.8165 -0.4186 -0.1528 0.050 Uiso 1 1 calc R . . O1 O 0.52192(8) -0.0919(3) 0.07800(3) 0.0504(4) Uani 1 1 d . . . O2 O 0.80903(11) 0.1724(3) -0.14573(4) 0.0664(5) Uani 1 1 d . . . C1 C 0.52433(10) 0.1479(3) 0.07346(4) 0.0363(4) Uani 1 1 d . . . C2 C 0.54963(11) 0.2623(4) 0.04500(5) 0.0425(5) Uani 1 1 d . . . H2A H 0.5058 0.3092 0.0301 0.051 Uiso 1 1 calc . . . H2B H 0.5773 0.4246 0.0508 0.051 Uiso 1 1 calc . . . C3 C 0.59789(11) 0.0788(4) 0.02962(5) 0.0419(5) Uani 1 1 d . . . H3A H 0.5725 -0.0904 0.0256 0.050 Uiso 1 1 calc . . . H3B H 0.6443 0.0468 0.0437 0.050 Uiso 1 1 calc . . . C4 C 0.61574(11) 0.1877(4) -0.00061(4) 0.0408(5) Uani 1 1 d . . . H4A H 0.5692 0.2219 -0.0146 0.049 Uiso 1 1 calc . . . H4B H 0.6416 0.3561 0.0035 0.049 Uiso 1 1 calc . . . C5 C 0.66343(11) 0.0043(4) -0.01655(5) 0.0426(5) Uani 1 1 d . . . H5A H 0.7106 -0.0254 -0.0028 0.051 Uiso 1 1 calc . . . H5B H 0.6383 -0.1659 -0.0200 0.051 Uiso 1 1 calc . . . C6 C 0.67946(11) 0.1077(4) -0.04717(4) 0.0418(5) Uani 1 1 d . . . H6A H 0.7045 0.2781 -0.0437 0.050 Uiso 1 1 calc . . . H6B H 0.6324 0.1365 -0.0610 0.050 Uiso 1 1 calc . . . C7 C 0.72750(12) -0.0770(4) -0.06285(5) 0.0439(5) Uani 1 1 d . . . H7A H 0.7030 -0.2486 -0.0659 0.053 Uiso 1 1 calc . . . H7B H 0.7750 -0.1028 -0.0492 0.053 Uiso 1 1 calc . . . C8 C 0.74232(12) 0.0238(4) -0.09393(4) 0.0425(5) Uani 1 1 d . . . H8A H 0.6951 0.0437 -0.1079 0.051 Uiso 1 1 calc . . . H8B H 0.7656 0.1976 -0.0911 0.051 Uiso 1 1 calc . . . C9 C 0.79252(11) -0.1613(4) -0.10853(4) 0.0414(5) Uani 1 1 d . . . H9A H 0.8398 -0.1809 -0.0946 0.050 Uiso 1 1 calc . . . H9B H 0.7693 -0.3352 -0.1112 0.050 Uiso 1 1 calc . . . C10 C 0.80747(11) -0.0639(4) -0.13940(4) 0.0402(5) Uani 1 1 d . . . C11 C 0.46852(11) 0.2830(4) 0.11883(4) 0.0377(4) Uani 1 1 d . . . F11 F 0.36690(11) 0.1839(3) 0.19438(4) 0.0919(6) Uani 1 1 d . . . C12 C 0.41346(12) 0.4574(4) 0.12454(5) 0.0466(5) Uani 1 1 d . . . H12 H 0.3992 0.5971 0.1109 0.056 Uiso 1 1 calc R . . C13 C 0.37948(13) 0.4263(5) 0.15024(5) 0.0555(6) Uani 1 1 d . . . H13 H 0.3426 0.5436 0.1541 0.067 Uiso 1 1 calc R . . C14 C 0.40138(14) 0.2198(5) 0.16974(5) 0.0552(6) Uani 1 1 d . . . C15 C 0.45654(14) 0.0458(5) 0.16511(5) 0.0565(6) Uani 1 1 d . . . H15 H 0.4708 -0.0920 0.1790 0.068 Uiso 1 1 calc R . . C16 C 0.49073(12) 0.0789(4) 0.13935(5) 0.0465(5) Uani 1 1 d . . . H16 H 0.5285 -0.0364 0.1359 0.056 Uiso 1 1 calc R . . F21 F 0.90466(13) -0.1728(4) -0.27342(4) 0.1101(7) Uani 1 1 d . . . C21 C 0.84042(11) -0.2237(4) -0.18873(5) 0.0412(5) Uani 1 1 d . . . C22 C 0.89079(14) -0.0335(5) -0.19419(6) 0.0594(6) Uani 1 1 d . . . H22 H 0.9107 0.0835 -0.1785 0.071 Uiso 1 1 calc R . . C23 C 0.91193(16) -0.0159(5) -0.22304(6) 0.0712(8) Uani 1 1 d . . . H23 H 0.9457 0.1135 -0.2269 0.085 Uiso 1 1 calc R . . C24 C 0.88274(17) -0.1893(5) -0.24544(6) 0.0673(7) Uani 1 1 d . . . C25 C 0.83179(17) -0.3785(6) -0.24096(6) 0.0736(8) Uani 1 1 d . . . H25 H 0.8118 -0.4931 -0.2569 0.088 Uiso 1 1 calc R . . C26 C 0.81055(15) -0.3955(5) -0.21210(5) 0.0589(6) Uani 1 1 d . . . H26 H 0.7760 -0.5233 -0.2085 0.071 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0564(10) 0.0275(7) 0.0418(9) 0.0025(7) 0.0211(8) 0.0006(7) N2 0.0606(10) 0.0279(8) 0.0415(9) 0.0032(7) 0.0207(8) 0.0014(7) O1 0.0746(10) 0.0274(7) 0.0555(9) 0.0021(6) 0.0294(8) 0.0009(6) O2 0.1186(15) 0.0292(7) 0.0641(10) 0.0056(7) 0.0514(10) 0.0048(8) C1 0.0398(10) 0.0300(9) 0.0411(11) 0.0014(8) 0.0132(8) 0.0013(7) C2 0.0544(12) 0.0332(9) 0.0433(11) 0.0040(8) 0.0180(9) 0.0037(8) C3 0.0490(11) 0.0389(10) 0.0412(11) 0.0056(8) 0.0173(9) 0.0070(8) C4 0.0476(11) 0.0385(10) 0.0388(10) 0.0043(8) 0.0150(9) 0.0038(8) C5 0.0526(11) 0.0379(10) 0.0412(11) 0.0060(8) 0.0187(9) 0.0057(8) C6 0.0512(11) 0.0393(10) 0.0382(10) 0.0071(8) 0.0172(9) 0.0062(9) C7 0.0568(12) 0.0381(10) 0.0402(11) 0.0034(8) 0.0183(9) 0.0042(9) C8 0.0577(12) 0.0345(10) 0.0392(11) 0.0047(8) 0.0196(9) 0.0076(8) C9 0.0524(11) 0.0337(9) 0.0410(11) 0.0041(8) 0.0157(9) 0.0059(8) C10 0.0509(11) 0.0309(9) 0.0429(11) 0.0015(8) 0.0197(9) 0.0021(8) C11 0.0462(10) 0.0328(9) 0.0362(10) -0.0025(8) 0.0131(8) -0.0042(8) F11 0.1350(15) 0.0884(11) 0.0695(10) 0.0044(9) 0.0666(10) -0.0109(10) C12 0.0581(12) 0.0400(10) 0.0452(12) 0.0015(9) 0.0183(10) 0.0046(9) C13 0.0639(14) 0.0504(13) 0.0589(14) -0.0072(11) 0.0296(11) -0.0003(11) C14 0.0747(15) 0.0540(13) 0.0436(12) -0.0039(10) 0.0291(11) -0.0146(11) C15 0.0810(16) 0.0472(12) 0.0424(12) 0.0088(10) 0.0136(11) -0.0072(12) C16 0.0559(12) 0.0409(11) 0.0443(12) 0.0041(9) 0.0135(10) 0.0022(9) F21 0.187(2) 0.0950(13) 0.0681(11) 0.0048(9) 0.0783(13) 0.0019(13) C21 0.0529(12) 0.0342(10) 0.0404(11) 0.0014(8) 0.0187(9) 0.0056(8) C22 0.0762(15) 0.0522(13) 0.0565(14) -0.0068(11) 0.0307(12) -0.0119(11) C23 0.0955(19) 0.0559(14) 0.0754(18) 0.0028(13) 0.0525(16) -0.0083(13) C24 0.105(2) 0.0597(15) 0.0467(13) 0.0084(12) 0.0391(14) 0.0136(14) C25 0.108(2) 0.0683(17) 0.0491(14) -0.0132(12) 0.0279(14) -0.0046(15) C26 0.0785(16) 0.0512(13) 0.0521(14) -0.0077(11) 0.0252(12) -0.0100(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.345(2) . ? N1 C11 1.424(2) . ? N2 C10 1.346(2) . ? N2 C21 1.424(2) . ? O1 C1 1.225(2) . ? O2 C10 1.223(2) . ? C1 C2 1.515(2) . ? C2 C3 1.509(3) . ? C3 C4 1.519(3) . ? C4 C5 1.516(3) . ? C5 C6 1.513(3) . ? C6 C7 1.517(3) . ? C7 C8 1.520(3) . ? C8 C9 1.519(3) . ? C9 C10 1.507(2) . ? C11 C16 1.380(3) . ? C11 C12 1.384(3) . ? F11 C14 1.350(2) . ? C12 C13 1.382(3) . ? C13 C14 1.362(3) . ? C14 C15 1.371(3) . ? C15 C16 1.389(3) . ? F21 C24 1.355(3) . ? C21 C22 1.372(3) . ? C21 C26 1.379(3) . ? C22 C23 1.386(3) . ? C23 C24 1.353(4) . ? C24 C25 1.364(4) . ? C25 C26 1.387(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C11 126.79(15) . . ? C10 N2 C21 126.59(16) . . ? O1 C1 N1 123.66(17) . . ? O1 C1 C2 122.16(16) . . ? N1 C1 C2 114.10(15) . . ? C3 C2 C1 114.58(16) . . ? C2 C3 C4 113.28(16) . . ? C5 C4 C3 113.96(16) . . ? C6 C5 C4 114.27(16) . . ? C5 C6 C7 113.78(16) . . ? C6 C7 C8 113.86(16) . . ? C9 C8 C7 112.54(16) . . ? C10 C9 C8 113.05(15) . . ? O2 C10 N2 123.18(18) . . ? O2 C10 C9 122.36(17) . . ? N2 C10 C9 114.44(16) . . ? C16 C11 C12 119.60(18) . . ? C16 C11 N1 123.02(17) . . ? C12 C11 N1 117.33(17) . . ? C13 C12 C11 120.8(2) . . ? C14 C13 C12 118.4(2) . . ? F11 C14 C13 118.6(2) . . ? F11 C14 C15 118.9(2) . . ? C13 C14 C15 122.49(19) . . ? C14 C15 C16 118.9(2) . . ? C11 C16 C15 119.9(2) . . ? C22 C21 C26 119.8(2) . . ? C22 C21 N2 121.64(19) . . ? C26 C21 N2 118.50(18) . . ? C21 C22 C23 120.0(2) . . ? C24 C23 C22 119.1(2) . . ? C23 C24 F21 118.6(2) . . ? C23 C24 C25 122.5(2) . . ? F21 C24 C25 118.9(3) . . ? C24 C25 C26 118.4(2) . . ? C21 C26 C25 120.3(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.276 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.061 data_2IBr _database_code_depnum_ccdc_archive 'CCDC 696973' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Br I N2 O2' _chemical_formula_weight 473.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.459(5) _cell_length_b 4.8268(13) _cell_length_c 9.851(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.666(9) _cell_angle_gamma 90.00 _cell_volume 818.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1298 _cell_measurement_theta_min 1.18 _cell_measurement_theta_max 24.14 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.920 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 4.406 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.510 _exptl_absorpt_correction_T_max 0.640 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 Bruker' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7958 _diffrn_reflns_av_R_equivalents 0.0583 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 24.14 _reflns_number_total 1298 _reflns_number_gt 887 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0837P)^2^+0.8888P] 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 1298 _refine_ls_number_parameters 109 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1494 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.5698(3) 1.2029(11) 0.3537(6) 0.0622(11) Uani 0.50 1 d PD . . Br1 Br 0.5789(5) 1.1343(19) 0.3544(9) 0.0642(16) Uani 0.50 1 d PD . . N11 N 0.8631(3) 0.8513(10) 0.7780(6) 0.0438(14) Uani 1 1 d . . . H11 H 0.8703 0.6775 0.7947 0.053 Uiso 1 1 calc R . . C11 C 0.7980(4) 0.9260(12) 0.6786(7) 0.0376(15) Uani 1 1 d . . . C12 C 0.7284(5) 0.7911(16) 0.6778(9) 0.058(2) Uani 1 1 d . . . H12 H 0.7248 0.6540 0.7427 0.070 Uiso 1 1 calc R . . C13 C 0.6640(4) 0.8568(14) 0.5818(8) 0.0528(19) Uani 1 1 d . . . H13 H 0.6178 0.7600 0.5805 0.063 Uiso 1 1 calc R . . C14 C 0.6679(3) 1.0623(14) 0.4894(5) 0.0434(16) Uani 1 1 d D . . C15 C 0.7369(4) 1.1973(16) 0.4894(8) 0.0535(19) Uani 1 1 d . . . H15 H 0.7397 1.3372 0.4255 0.064 Uiso 1 1 calc R . . C16 C 0.8023(4) 1.1292(14) 0.5825(8) 0.0487(18) Uani 1 1 d . . . H16 H 0.8490 1.2203 0.5804 0.058 Uiso 1 1 calc R . . O21 O 0.9125(3) 1.2790(8) 0.8267(6) 0.0535(14) Uani 1 1 d . . . C21 C 0.9150(4) 1.0290(13) 0.8491(7) 0.0416(16) Uani 1 1 d . . . C22 C 0.9737(4) 0.8988(14) 0.9585(8) 0.0491(18) Uani 1 1 d . . . H22A H 0.9466 0.7937 1.0197 0.059 Uiso 1 1 calc . . . H22B H 1.0048 0.7697 0.9154 0.059 Uiso 1 1 calc . . . 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 I1 0.0531(13) 0.054(3) 0.0720(12) 0.0072(13) -0.0117(9) 0.0166(11) Br1 0.060(2) 0.054(4) 0.0698(18) -0.0005(19) -0.0177(13) 0.0256(15) N11 0.053(3) 0.020(3) 0.052(4) 0.002(2) -0.008(3) 0.003(2) C11 0.046(4) 0.019(3) 0.043(4) -0.002(3) -0.004(3) 0.001(3) C12 0.059(5) 0.044(4) 0.068(6) 0.013(4) 0.001(4) -0.007(4) C13 0.053(4) 0.051(5) 0.051(5) 0.002(4) -0.004(4) -0.008(3) C14 0.044(4) 0.039(3) 0.043(4) -0.003(3) -0.004(3) 0.007(3) C15 0.061(5) 0.057(5) 0.039(4) 0.008(4) -0.005(3) 0.000(4) C16 0.046(4) 0.050(4) 0.047(4) 0.013(3) -0.002(3) -0.007(3) O21 0.072(3) 0.016(2) 0.063(4) 0.002(2) -0.016(3) 0.005(2) C21 0.047(4) 0.033(4) 0.043(4) 0.001(3) 0.002(3) 0.005(3) C22 0.056(4) 0.027(3) 0.055(5) -0.001(3) -0.015(3) 0.003(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 I1 C14 2.1002(11) . ? Br1 C14 1.8999(11) . ? N11 C21 1.355(8) . ? N11 C11 1.417(8) . ? C11 C12 1.377(10) . ? C11 C16 1.374(9) . ? C12 C13 1.379(11) . ? C13 C14 1.355(9) . ? C14 C15 1.370(10) . ? C15 C16 1.379(10) . ? O21 C21 1.226(8) . ? C21 C22 1.494(10) . ? C22 C22 1.489(14) 3_777 ? 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 C21 N11 C11 125.9(5) . . ? C12 C11 C16 118.9(6) . . ? C12 C11 N11 119.2(6) . . ? C16 C11 N11 121.8(6) . . ? C11 C12 C13 120.8(7) . . ? C14 C13 C12 120.1(6) . . ? C13 C14 C15 119.4(5) . . ? C13 C14 Br1 118.5(6) . . ? C15 C14 Br1 121.9(6) . . ? C13 C14 I1 122.5(5) . . ? C15 C14 I1 118.0(5) . . ? Br1 C14 I1 8.8(4) . . ? C16 C15 C14 121.1(7) . . ? C11 C16 C15 119.6(7) . . ? O21 C21 N11 121.9(6) . . ? O21 C21 C22 122.9(6) . . ? N11 C21 C22 115.1(6) . . ? C22 C22 C21 113.9(7) 3_777 . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.14 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.892 _refine_diff_density_min -0.727 _refine_diff_density_rms 0.174 data_3IBr _database_code_depnum_ccdc_archive 'CCDC 696974' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 Br I N2 O2' _chemical_formula_weight 501.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.9243(9) _cell_length_b 4.8077(2) _cell_length_c 10.1235(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.5350(10) _cell_angle_gamma 90.00 _cell_volume 919.31(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1981 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 27.00 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.810 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 3.927 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.546 _exptl_absorpt_correction_T_max 0.676 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 BRUKER' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11569 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1981 _reflns_number_gt 1757 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+0.1670P] 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 1981 _refine_ls_number_parameters 118 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0922 _refine_ls_wR_factor_gt 0.0894 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.06626(11) 0.3092(6) 0.3336(3) 0.0535(2) Uani 0.50 1 d PD . . Br1 Br 0.0704(2) 0.3288(12) 0.3552(5) 0.0665(8) Uani 0.50 1 d PD . . C11 C 0.27034(13) 0.5862(5) 0.6265(2) 0.0411(5) Uani 1 1 d . . . C12 C 0.20613(17) 0.7191(6) 0.6361(3) 0.0542(7) Uani 1 1 d . . . H12 H 0.2017 0.8583 0.6989 0.065 Uiso 1 1 calc R . . C13 C 0.14802(16) 0.6463(6) 0.5525(3) 0.0567(7) Uani 1 1 d . . . H13 H 0.1052 0.7383 0.5593 0.068 Uiso 1 1 calc R . . C14 C 0.15340(10) 0.4378(5) 0.4593(2) 0.0470(5) Uani 1 1 d D . . C15 C 0.21846(16) 0.3085(6) 0.4492(3) 0.0542(7) Uani 1 1 d . . . H15 H 0.2230 0.1696 0.3864 0.065 Uiso 1 1 calc R . . C16 C 0.27660(14) 0.3831(6) 0.5311(3) 0.0510(6) Uani 1 1 d . . . H16 H 0.3200 0.2965 0.5221 0.061 Uiso 1 1 calc R . . N21 N 0.32837(13) 0.6656(4) 0.7131(3) 0.0481(5) Uani 1 1 d . . . H21 H 0.3351 0.8407 0.7261 0.058 Uiso 1 1 calc R . . O21 O 0.37313(13) 0.2392(4) 0.7576(2) 0.0604(6) Uani 1 1 d . . . C21 C 0.37387(13) 0.4888(5) 0.7769(2) 0.0419(5) Uani 1 1 d . . . C22 C 0.42571(18) 0.6246(6) 0.8761(3) 0.0591(8) Uani 1 1 d . . . H22A H 0.4539 0.7568 0.8297 0.071 Uiso 1 1 calc . . . H22B H 0.3992 0.7286 0.9386 0.071 Uiso 1 1 calc . . . C23 C 0.47434(15) 0.4314(5) 0.9515(3) 0.0518(6) Uani 1 1 d . . . H23A H 0.5007 0.3264 0.8891 0.062 Uiso 1 1 calc . . . H23B H 0.4462 0.3001 0.9986 0.062 Uiso 1 1 calc . . . 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 I1 0.0372(4) 0.0702(5) 0.0499(8) -0.0076(5) -0.0229(3) -0.0077(3) Br1 0.0446(6) 0.0932(12) 0.0579(16) -0.0115(8) -0.0289(6) -0.0105(5) C11 0.0404(12) 0.0382(10) 0.0433(12) 0.0022(9) -0.0091(10) -0.0032(9) C12 0.0494(16) 0.0552(14) 0.0560(17) -0.0132(12) -0.0121(13) 0.0082(12) C13 0.0399(14) 0.0663(16) 0.0624(18) -0.0073(13) -0.0095(13) 0.0071(12) C14 0.0381(12) 0.0559(13) 0.0458(13) 0.0052(11) -0.0085(10) -0.0054(10) C15 0.0461(16) 0.0649(17) 0.0498(16) -0.0138(12) -0.0107(13) 0.0011(11) C16 0.0384(13) 0.0613(14) 0.0521(15) -0.0115(12) -0.0076(11) 0.0041(11) N21 0.0506(13) 0.0350(9) 0.0561(13) -0.0041(8) -0.0177(11) -0.0016(8) O21 0.0698(14) 0.0362(8) 0.0709(14) -0.0019(9) -0.0308(11) -0.0037(9) C21 0.0432(12) 0.0357(10) 0.0454(12) 0.0006(9) -0.0094(10) -0.0034(9) C22 0.0653(19) 0.0406(11) 0.0673(18) -0.0033(12) -0.0301(15) -0.0050(12) C23 0.0500(15) 0.0455(12) 0.0570(15) -0.0019(11) -0.0197(12) -0.0049(10) _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 I1 C14 2.1125(19) . ? Br1 C14 1.910(2) . ? C11 C12 1.382(4) . ? C11 C16 1.383(4) . ? C11 N21 1.415(3) . ? C12 C13 1.390(4) . ? C13 C14 1.385(4) . ? C14 C15 1.389(4) . ? C15 C16 1.384(4) . ? N21 C21 1.346(3) . ? O21 C21 1.216(3) . ? C21 C22 1.509(4) . ? C22 C23 1.485(4) . ? C23 C23 1.492(5) 3_667 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 C11 C16 119.3(2) . . ? C12 C11 N21 118.9(2) . . ? C16 C11 N21 121.8(2) . . ? C11 C12 C13 120.5(3) . . ? C14 C13 C12 120.6(3) . . ? C13 C14 C15 118.5(2) . . ? C13 C14 Br1 118.8(3) . . ? C15 C14 Br1 122.6(3) . . ? C13 C14 I1 122.3(2) . . ? C15 C14 I1 119.2(2) . . ? Br1 C14 I1 4.0(3) . . ? C16 C15 C14 121.0(2) . . ? C15 C16 C11 120.1(2) . . ? C21 N21 C11 125.2(2) . . ? O21 C21 N21 123.1(2) . . ? O21 C21 C22 122.3(2) . . ? N21 C21 C22 114.6(2) . . ? C23 C22 C21 115.4(2) . . ? C22 C23 C23 114.8(3) . 3_667 ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.461 _refine_diff_density_min -0.698 _refine_diff_density_rms 0.118 data_3BrCl _database_code_depnum_ccdc_archive 'CCDC 696975' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 Br Cl N2 O2' _chemical_formula_weight 409.70 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' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.7510(6) _cell_length_b 11.2001(7) _cell_length_c 9.6534(6) _cell_angle_alpha 90.00 _cell_angle_beta 119.494(2) _cell_angle_gamma 90.00 _cell_volume 917.64(10) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1983 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 27.00 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 2.398 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.716 _exptl_absorpt_correction_T_max 0.788 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 Bruker' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11949 _diffrn_reflns_av_R_equivalents 0.1333 _diffrn_reflns_av_sigmaI/netI 0.0692 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1983 _reflns_number_gt 1197 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0812P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1983 _refine_ls_number_parameters 118 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1341 _refine_ls_wR_factor_gt 0.1263 _refine_ls_goodness_of_fit_ref 0.892 _refine_ls_restrained_S_all 0.905 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.5387(3) 0.2119(2) 0.8118(2) 0.0917(5) Uani 0.50 1 d PD . . Cl1 Cl 0.5317(7) 0.2051(5) 0.7513(5) 0.0928(13) Uani 0.50 1 d PD . . N11 N 0.0625(3) -0.18440(18) 0.4804(2) 0.0509(5) Uani 1 1 d . . . H11 H 0.0347 -0.1934 0.3816 0.061 Uiso 1 1 calc R . . C11 C 0.1724(3) -0.0920(2) 0.5602(3) 0.0507(6) Uani 1 1 d . . . C12 C 0.2338(3) -0.0344(3) 0.4774(3) 0.0704(8) Uani 1 1 d . . . H12 H 0.2019 -0.0566 0.3730 0.085 Uiso 1 1 calc R . . C13 C 0.3426(4) 0.0563(3) 0.5477(4) 0.0843(9) Uani 1 1 d . . . H13 H 0.3836 0.0948 0.4908 0.101 Uiso 1 1 calc R . . C14 C 0.3899(3) 0.0895(2) 0.7014(4) 0.0771(8) Uani 1 1 d D . . C15 C 0.3278(4) 0.0324(3) 0.7841(4) 0.0823(9) Uani 1 1 d . . . H15 H 0.3596 0.0550 0.8883 0.099 Uiso 1 1 calc R . . C16 C 0.2201(3) -0.0569(3) 0.7154(3) 0.0661(7) Uani 1 1 d . . . H16 H 0.1786 -0.0945 0.7725 0.079 Uiso 1 1 calc R . . O21 O 0.0215(3) -0.25693(19) 0.6747(2) 0.0793(6) Uani 1 1 d . . . C21 C -0.0043(3) -0.2598(2) 0.5372(3) 0.0527(6) Uani 1 1 d . . . C22 C -0.1145(3) -0.3501(2) 0.4212(3) 0.0607(7) Uani 1 1 d . . . H22A H -0.1069 -0.3472 0.3247 0.073 Uiso 1 1 calc . . . H22B H -0.2218 -0.3300 0.3933 0.073 Uiso 1 1 calc . . . C23 C -0.0779(3) -0.4763(2) 0.4885(3) 0.0572(6) Uani 1 1 d . . . H23A H -0.1619 -0.5292 0.4171 0.069 Uiso 1 1 calc . . . H23B H -0.0754 -0.4771 0.5902 0.069 Uiso 1 1 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0583(6) 0.0702(7) 0.1132(14) -0.0274(8) 0.0166(9) -0.0185(4) Cl1 0.0556(11) 0.0724(15) 0.105(3) -0.033(2) 0.005(2) -0.0192(9) N11 0.0732(13) 0.0447(12) 0.0404(9) 0.0002(8) 0.0322(9) 0.0014(10) C11 0.0577(13) 0.0420(14) 0.0519(12) 0.0039(10) 0.0266(11) 0.0073(11) C12 0.0799(18) 0.068(2) 0.0661(15) 0.0064(14) 0.0378(14) -0.0049(15) C13 0.0746(18) 0.072(2) 0.107(2) 0.0145(19) 0.0458(17) -0.0093(17) C14 0.0564(15) 0.0523(18) 0.102(2) -0.0079(16) 0.0229(15) -0.0042(13) C15 0.0774(19) 0.073(2) 0.0795(18) -0.0258(17) 0.0251(15) -0.0037(17) C16 0.0774(16) 0.0620(18) 0.0639(15) -0.0141(14) 0.0387(13) -0.0054(14) O21 0.1335(18) 0.0679(13) 0.0564(11) -0.0018(9) 0.0620(12) -0.0132(13) C21 0.0735(15) 0.0425(13) 0.0494(13) 0.0059(11) 0.0360(12) 0.0095(12) C22 0.0720(16) 0.0498(17) 0.0604(14) 0.0007(11) 0.0327(12) -0.0008(12) C23 0.0693(15) 0.0457(15) 0.0679(14) 0.0008(12) 0.0424(12) -0.0083(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Cl1 0.559(5) . ? Br1 C14 1.897(3) . ? Cl1 C14 1.779(4) . ? N11 C21 1.338(3) . ? N11 C11 1.414(3) . ? C11 C12 1.374(3) . ? C11 C16 1.389(3) . ? C12 C13 1.381(4) . ? C13 C14 1.371(4) . ? C14 C15 1.375(4) . ? C15 C16 1.363(4) . ? O21 C21 1.224(2) . ? C21 C22 1.499(4) . ? C22 C23 1.523(4) . ? C23 C23 1.518(5) 3_546 ? 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 Cl1 Br1 C14 69.4(6) . . ? Br1 Cl1 C14 93.6(7) . . ? C21 N11 C11 129.06(19) . . ? C12 C11 C16 118.9(2) . . ? C12 C11 N11 117.2(2) . . ? C16 C11 N11 123.8(2) . . ? C11 C12 C13 120.6(3) . . ? C14 C13 C12 120.0(3) . . ? C13 C14 C15 119.5(2) . . ? C13 C14 Cl1 107.1(3) . . ? C15 C14 Cl1 133.4(3) . . ? C13 C14 Br1 124.1(3) . . ? C15 C14 Br1 116.4(3) . . ? Cl1 C14 Br1 17.09(17) . . ? C16 C15 C14 120.8(3) . . ? C15 C16 C11 120.1(3) . . ? O21 C21 N11 123.1(2) . . ? O21 C21 C22 121.2(2) . . ? N11 C21 C22 115.74(19) . . ? C21 C22 C23 112.1(2) . . ? C22 C23 C23 113.2(2) . 3_546 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.398 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.070 data_4BrCl _database_code_depnum_ccdc_archive 'CCDC 696976' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 Br Cl N2 O2' _chemical_formula_weight 437.76 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 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 22.022(4) _cell_length_b 5.1048(10) _cell_length_c 17.836(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.024(5) _cell_angle_gamma 90.00 _cell_volume 1927.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2095 _cell_measurement_theta_min 1.92 _cell_measurement_theta_max 27.00 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 2.289 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.669 _exptl_absorpt_correction_T_max 0.777 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD APEX 2 Bruker' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12245 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2095 _reflns_number_gt 1492 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0499P)^2^+0.6068P] 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 2095 _refine_ls_number_parameters 127 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0890 _refine_ls_wR_factor_gt 0.0818 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.992 _refine_ls_shift/su_max 0.015 _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 Br1 Br 0.05628(14) 0.8427(9) 0.2068(2) 0.0719(4) Uani 0.50 1 d PD . . Cl1 Cl 0.0649(4) 0.845(2) 0.2069(6) 0.0856(18) Uani 0.50 1 d PD . . O1 O 0.31949(7) 1.1505(2) 0.09341(10) 0.0555(4) Uani 1 1 d . . . N1 N 0.29619(7) 0.7239(3) 0.10571(9) 0.0407(4) Uani 1 1 d . . . H1 H 0.3081 0.5664 0.1001 0.049 Uiso 1 1 calc R . . C1 C 0.33459(9) 0.9200(3) 0.09504(11) 0.0389(4) Uani 1 1 d . . . C2 C 0.39802(9) 0.8322(3) 0.08784(12) 0.0442(5) Uani 1 1 d . . . H2A H 0.3944 0.6541 0.0681 0.053 Uiso 1 1 calc . . . H2B H 0.4279 0.8313 0.1392 0.053 Uiso 1 1 calc . . . C3 C 0.42345(9) 1.0043(3) 0.03449(11) 0.0428(4) Uani 1 1 d . . . H3A H 0.3931 1.0082 -0.0166 0.051 Uiso 1 1 calc . . . H3B H 0.4280 1.1816 0.0548 0.051 Uiso 1 1 calc . . . C4 C 0.48652(10) 0.9124(4) 0.02595(12) 0.0452(5) Uani 1 1 d . . . H4A H 0.4817 0.7366 0.0045 0.054 Uiso 1 1 calc . . . H4B H 0.5165 0.9039 0.0773 0.054 Uiso 1 1 calc . . . C11 C 0.23880(9) 0.7531(3) 0.12508(10) 0.0347(4) Uani 1 1 d . . . C12 C 0.19680(9) 0.9557(3) 0.09656(11) 0.0420(4) Uani 1 1 d . . . H12 H 0.2051 1.0756 0.0614 0.050 Uiso 1 1 calc R . . C13 C 0.14268(9) 0.9785(4) 0.12065(12) 0.0477(5) Uani 1 1 d . . . H13 H 0.1146 1.1152 0.1022 0.057 Uiso 1 1 calc R . . C14 C 0.13014(9) 0.7996(4) 0.17186(11) 0.0450(5) Uani 1 1 d D . . C15 C 0.16988(10) 0.5928(4) 0.19831(11) 0.0456(5) Uani 1 1 d . . . H15 H 0.1603 0.4691 0.2316 0.055 Uiso 1 1 calc R . . C16 C 0.22418(9) 0.5704(4) 0.17501(11) 0.0414(4) Uani 1 1 d . . . H16 H 0.2515 0.4310 0.1930 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0451(7) 0.1015(9) 0.0833(8) -0.0097(6) 0.0414(6) 0.0012(7) Cl1 0.048(2) 0.121(3) 0.107(3) 0.0002(19) 0.0520(19) 0.0050(17) O1 0.0526(9) 0.0301(6) 0.0969(11) 0.0019(6) 0.0423(8) 0.0037(6) N1 0.0419(10) 0.0289(7) 0.0585(9) -0.0002(7) 0.0258(8) 0.0034(7) C1 0.0407(11) 0.0353(9) 0.0473(10) 0.0020(8) 0.0234(8) 0.0023(8) C2 0.0393(11) 0.0404(10) 0.0592(12) 0.0064(8) 0.0243(9) 0.0060(8) C3 0.0376(10) 0.0387(10) 0.0584(11) 0.0034(8) 0.0237(9) 0.0024(8) C4 0.0384(11) 0.0412(9) 0.0629(12) 0.0039(9) 0.0258(9) 0.0036(8) C11 0.0336(10) 0.0318(8) 0.0417(9) -0.0038(7) 0.0157(8) -0.0014(7) C12 0.0390(11) 0.0376(9) 0.0519(11) 0.0043(8) 0.0169(9) -0.0004(8) C13 0.0375(12) 0.0443(10) 0.0633(12) 0.0005(9) 0.0172(10) 0.0055(9) C14 0.0348(11) 0.0552(12) 0.0498(11) -0.0114(9) 0.0200(9) -0.0052(9) C15 0.0469(12) 0.0500(11) 0.0442(10) 0.0030(8) 0.0196(9) -0.0064(9) C16 0.0432(11) 0.0365(9) 0.0465(10) 0.0029(8) 0.0159(9) 0.0013(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C14 1.908(3) . ? Cl1 C14 1.733(5) . ? O1 C1 1.221(2) . ? N1 C1 1.358(2) . ? N1 C11 1.407(2) . ? C1 C2 1.506(3) . ? C2 C3 1.512(2) . ? C3 C4 1.513(3) . ? C4 C4 1.521(4) 5_675 ? C11 C16 1.387(2) . ? C11 C12 1.387(3) . ? C12 C13 1.379(3) . ? C13 C14 1.373(3) . ? C14 C15 1.369(3) . ? C15 C16 1.375(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C11 126.36(14) . . ? O1 C1 N1 122.54(18) . . ? O1 C1 C2 122.56(16) . . ? N1 C1 C2 114.88(15) . . ? C1 C2 C3 113.21(15) . . ? C4 C3 C2 113.14(16) . . ? C3 C4 C4 113.7(2) . 5_675 ? C16 C11 C12 119.16(17) . . ? C16 C11 N1 118.01(16) . . ? C12 C11 N1 122.82(15) . . ? C13 C12 C11 119.65(17) . . ? C14 C13 C12 120.07(18) . . ? C15 C14 C13 121.03(17) . . ? C15 C14 Cl1 119.5(5) . . ? C13 C14 Cl1 119.4(5) . . ? C15 C14 Br1 119.9(2) . . ? C13 C14 Br1 119.1(2) . . ? Cl1 C14 Br1 2.3(4) . . ? C14 C15 C16 119.11(17) . . ? C15 C16 C11 120.90(18) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.174 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.054 ##ENd