data_110411a_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H19 Cl2 N3 O' _chemical_formula_weight 448.33 _chemical_absolute_configuration ad 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 24.184(5) _cell_length_b 12.837(3) _cell_length_c 7.0688(15) _cell_angle_alpha 90.00 _cell_angle_beta 92.193(4) _cell_angle_gamma 90.00 _cell_volume 2192.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 919 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 19.79 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.319 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8778 _exptl_absorpt_correction_T_max 0.9598 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5659 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0811 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.25 _reflns_number_total 3733 _reflns_number_gt 3036 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0451P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(8) _refine_ls_number_reflns 3733 _refine_ls_number_parameters 282 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 1.024 _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 C1 C 0.03350(17) -0.0246(4) 0.7614(5) 0.0385(11) Uani 1 1 d . . . C2 C 0.08122(16) -0.0822(4) 0.7362(5) 0.0357(10) Uani 1 1 d . . . H2 H 0.0793 -0.1551 0.7143 0.043 Uiso 1 1 calc R . . C3 C 0.13181(16) -0.0310(3) 0.7437(5) 0.0270(9) Uani 1 1 d . . . H3 H 0.1648 -0.0696 0.7277 0.032 Uiso 1 1 calc R . . C4 C 0.13486(14) 0.0752(3) 0.7741(4) 0.0226(8) Uani 1 1 d . . . C5 C 0.08650(15) 0.1305(3) 0.8010(5) 0.0282(9) Uani 1 1 d . . . H5 H 0.0883 0.2034 0.8239 0.034 Uiso 1 1 calc R . . C6 C 0.03552(15) 0.0805(4) 0.7947(5) 0.0331(10) Uani 1 1 d . . . H6 H 0.0025 0.1187 0.8133 0.040 Uiso 1 1 calc R . . C7 C 0.18858(14) 0.1276(3) 0.7715(5) 0.0203(8) Uani 1 1 d . . . C8 C 0.21369(14) 0.2079(3) 0.8619(5) 0.0202(8) Uani 1 1 d . . . C9 C 0.15947(15) 0.2967(3) 1.1103(5) 0.0254(8) Uani 1 1 d . . . C10 C 0.14608(15) 0.2049(3) 1.1998(5) 0.0272(9) Uani 1 1 d . . . H10 H 0.1643 0.1418 1.1693 0.033 Uiso 1 1 calc R . . C11 C 0.10564(16) 0.2056(4) 1.3351(5) 0.0354(10) Uani 1 1 d . . . H11 H 0.0962 0.1430 1.3976 0.042 Uiso 1 1 calc R . . C12 C 0.07954(19) 0.2972(5) 1.3776(6) 0.0494(12) Uani 1 1 d . . . H12 H 0.0515 0.2975 1.4682 0.059 Uiso 1 1 calc R . . C13 C 0.09382(19) 0.3886(4) 1.2893(6) 0.0490(12) Uani 1 1 d . . . H13 H 0.0762 0.4518 1.3221 0.059 Uiso 1 1 calc R . . C14 C 0.13374(17) 0.3894(4) 1.1528(5) 0.0367(10) Uani 1 1 d . . . H14 H 0.1431 0.4522 1.0903 0.044 Uiso 1 1 calc R . . C15 C 0.23623(15) 0.3768(3) 0.9223(5) 0.0252(8) Uani 1 1 d . . . C16 C 0.26797(15) 0.3416(3) 0.7481(5) 0.0230(9) Uani 1 1 d . . . C17 C 0.32290(16) 0.3983(3) 0.7372(5) 0.0335(10) Uani 1 1 d . . . H17A H 0.3161 0.4728 0.7169 0.050 Uiso 1 1 calc R . . H17B H 0.3435 0.3703 0.6318 0.050 Uiso 1 1 calc R . . H17C H 0.3445 0.3883 0.8559 0.050 Uiso 1 1 calc R . . C18 C 0.23148(16) 0.3646(3) 0.5693(5) 0.0311(10) Uani 1 1 d . . . H18A H 0.2225 0.4391 0.5645 0.047 Uiso 1 1 calc R . . H18B H 0.1972 0.3241 0.5732 0.047 Uiso 1 1 calc R . . H18C H 0.2515 0.3454 0.4565 0.047 Uiso 1 1 calc R . . C19 C 0.26962(15) 0.2218(3) 0.7882(5) 0.0208(8) Uani 1 1 d . . . C20 C 0.31654(14) 0.1903(3) 0.9244(5) 0.0219(8) Uani 1 1 d . . . C21 C 0.36998(16) 0.1776(3) 0.8591(5) 0.0271(9) Uani 1 1 d . . . H21 H 0.3767 0.1908 0.7298 0.032 Uiso 1 1 calc R . . C22 C 0.41276(16) 0.1466(3) 0.9779(5) 0.0333(10) Uani 1 1 d . . . H22 H 0.4487 0.1374 0.9305 0.040 Uiso 1 1 calc R . . C23 C 0.40376(16) 0.1287(3) 1.1667(6) 0.0347(10) Uani 1 1 d . . . C24 C 0.35156(16) 0.1407(3) 1.2378(5) 0.0338(10) Uani 1 1 d . . . H24 H 0.3455 0.1275 1.3676 0.041 Uiso 1 1 calc R . . C25 C 0.30829(15) 0.1722(3) 1.1173(5) 0.0245(8) Uani 1 1 d . . . H25 H 0.2725 0.1817 1.1656 0.029 Uiso 1 1 calc R . . Cl1 Cl -0.03008(5) -0.08794(12) 0.75187(16) 0.0602(4) Uani 1 1 d . . . Cl2 Cl 0.45774(5) 0.08903(14) 1.31739(17) 0.0749(5) Uani 1 1 d . . . N1 N 0.20066(12) 0.2939(2) 0.9696(4) 0.0214(7) Uani 1 1 d . . . N2 N 0.27037(12) 0.1477(2) 0.6271(4) 0.0240(7) Uani 1 1 d . . . N3 N 0.22664(12) 0.0929(2) 0.6293(4) 0.0241(7) Uani 1 1 d . . . O1 O 0.23947(11) 0.4588(2) 1.0029(4) 0.0375(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.032(2) 0.066(3) 0.018(2) -0.002(2) 0.0020(18) -0.020(2) C2 0.040(3) 0.039(3) 0.029(2) -0.0045(19) 0.0028(18) -0.016(2) C3 0.029(2) 0.027(2) 0.025(2) -0.0027(16) 0.0015(17) -0.0045(17) C4 0.023(2) 0.029(2) 0.0155(17) 0.0018(16) -0.0012(15) -0.0052(17) C5 0.025(2) 0.032(2) 0.027(2) 0.0036(17) 0.0014(16) -0.0015(17) C6 0.026(2) 0.051(3) 0.0227(19) -0.0037(19) 0.0028(16) -0.003(2) C7 0.0220(19) 0.020(2) 0.0191(18) 0.0010(15) 0.0018(15) 0.0002(15) C8 0.0206(19) 0.0178(19) 0.0223(19) 0.0013(15) 0.0009(15) 0.0000(15) C9 0.027(2) 0.030(2) 0.0198(19) -0.0040(17) 0.0021(16) 0.0041(17) C10 0.025(2) 0.033(2) 0.023(2) -0.0026(17) -0.0009(17) 0.0024(17) C11 0.031(2) 0.052(3) 0.023(2) 0.005(2) 0.0043(18) -0.005(2) C12 0.039(3) 0.077(4) 0.034(3) -0.002(3) 0.016(2) 0.011(3) C13 0.046(3) 0.054(3) 0.047(3) -0.005(2) 0.015(2) 0.017(2) C14 0.037(2) 0.039(3) 0.035(2) -0.003(2) 0.0049(19) 0.011(2) C15 0.025(2) 0.019(2) 0.031(2) 0.0014(17) -0.0043(16) -0.0015(15) C16 0.031(2) 0.018(2) 0.020(2) 0.0026(16) 0.0046(17) -0.0058(16) C17 0.039(2) 0.028(2) 0.033(2) 0.0055(19) -0.0040(18) -0.0121(19) C18 0.031(2) 0.033(2) 0.029(2) 0.0115(17) -0.0034(17) -0.0109(17) C19 0.025(2) 0.022(2) 0.0154(18) -0.0009(15) 0.0050(15) -0.0047(15) C20 0.024(2) 0.014(2) 0.027(2) -0.0029(15) 0.0032(16) -0.0024(15) C21 0.026(2) 0.030(2) 0.025(2) 0.0029(17) 0.0056(16) -0.0046(16) C22 0.027(2) 0.038(3) 0.035(2) 0.0015(19) 0.0032(18) -0.0001(18) C23 0.023(2) 0.047(3) 0.033(2) 0.008(2) -0.0010(17) 0.0029(19) C24 0.029(2) 0.049(3) 0.023(2) 0.0034(19) 0.0019(17) -0.0020(19) C25 0.021(2) 0.030(2) 0.023(2) -0.0025(16) 0.0062(15) -0.0021(16) Cl1 0.0378(6) 0.1003(11) 0.0426(6) -0.0061(7) 0.0034(5) -0.0404(7) Cl2 0.0289(6) 0.1450(15) 0.0504(7) 0.0391(9) -0.0039(5) 0.0107(8) N1 0.0237(16) 0.0159(16) 0.0248(16) -0.0019(13) 0.0051(13) 0.0004(13) N2 0.0253(17) 0.0251(19) 0.0221(16) -0.0029(13) 0.0058(13) -0.0031(14) N3 0.0242(17) 0.0269(19) 0.0214(15) -0.0037(14) 0.0053(13) 0.0004(14) O1 0.0416(17) 0.0212(16) 0.0497(18) -0.0067(13) 0.0022(14) -0.0018(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.371(6) . ? C1 C2 1.387(6) . ? C1 Cl1 1.738(4) . ? C2 C3 1.388(5) . ? C2 H2 0.9500 . ? C3 C4 1.382(5) . ? C3 H3 0.9500 . ? C4 C5 1.387(5) . ? C4 C7 1.464(5) . ? C5 C6 1.389(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.345(5) . ? C7 N3 1.458(4) . ? C8 N1 1.384(5) . ? C8 C19 1.479(5) . ? C9 C14 1.381(5) . ? C9 C10 1.382(5) . ? C9 N1 1.435(4) . ? C10 C11 1.394(5) . ? C10 H10 0.9500 . ? C11 C12 1.373(7) . ? C11 H11 0.9500 . ? C12 C13 1.380(7) . ? C12 H12 0.9500 . ? C13 C14 1.391(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 O1 1.198(4) . ? C15 N1 1.416(5) . ? C15 C16 1.543(5) . ? C16 C17 1.519(5) . ? C16 C18 1.542(5) . ? C16 C19 1.564(5) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 N2 1.484(4) . ? C19 C20 1.515(5) . ? C20 C21 1.398(5) . ? C20 C25 1.405(5) . ? C21 C22 1.367(5) . ? C21 H21 0.9500 . ? C22 C23 1.380(5) . ? C22 H22 0.9500 . ? C23 C24 1.385(5) . ? C23 Cl2 1.730(4) . ? C24 C25 1.384(5) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? N2 N3 1.271(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 C6 C1 C2 121.5(4) . . ? C6 C1 Cl1 119.5(3) . . ? C2 C1 Cl1 119.0(4) . . ? C1 C2 C3 118.7(4) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 121.0(4) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.1(3) . . ? C3 C4 C7 119.6(3) . . ? C5 C4 C7 121.4(3) . . ? C4 C5 C6 120.8(4) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 119.1(4) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C8 C7 N3 106.1(3) . . ? C8 C7 C4 136.9(3) . . ? N3 C7 C4 116.9(3) . . ? C7 C8 N1 139.9(3) . . ? C7 C8 C19 109.1(3) . . ? N1 C8 C19 109.1(3) . . ? C14 C9 C10 121.3(4) . . ? C14 C9 N1 120.2(3) . . ? C10 C9 N1 118.5(3) . . ? C9 C10 C11 119.4(4) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C12 C11 C10 119.8(4) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 120.3(4) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 120.8(5) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C9 C14 C13 118.3(4) . . ? C9 C14 H14 120.8 . . ? C13 C14 H14 120.8 . . ? O1 C15 N1 125.2(3) . . ? O1 C15 C16 127.7(3) . . ? N1 C15 C16 107.1(3) . . ? C17 C16 C18 109.9(3) . . ? C17 C16 C15 111.3(3) . . ? C18 C16 C15 108.1(3) . . ? C17 C16 C19 117.6(3) . . ? C18 C16 C19 110.3(3) . . ? C15 C16 C19 98.8(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C8 C19 N2 103.4(3) . . ? C8 C19 C20 114.7(3) . . ? N2 C19 C20 106.6(3) . . ? C8 C19 C16 99.5(3) . . ? N2 C19 C16 119.5(3) . . ? C20 C19 C16 113.0(3) . . ? C21 C20 C25 117.9(3) . . ? C21 C20 C19 120.1(3) . . ? C25 C20 C19 122.0(3) . . ? C22 C21 C20 121.3(3) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 119.9(4) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C22 C23 C24 120.8(4) . . ? C22 C23 Cl2 120.1(3) . . ? C24 C23 Cl2 119.1(3) . . ? C25 C24 C23 119.2(4) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C24 C25 C20 120.9(3) . . ? C24 C25 H25 119.5 . . ? C20 C25 H25 119.5 . . ? C8 N1 C15 108.4(3) . . ? C8 N1 C9 125.4(3) . . ? C15 N1 C9 126.1(3) . . ? N3 N2 C19 108.1(3) . . ? N2 N3 C7 112.7(3) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.292 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.052