# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Viktor O. Iaroshenko' _publ_contact_author_email iva108@googlemail.com loop_ _publ_author_name 'Viktor O. Iaroshenko' 'Ingo Knepper' 'Muhammad Zahid' 'Sergii Dudkin' 'Rene Kuzora' ; A.Villinger ; 'Peter Langer' data_av_ikp193 _database_code_depnum_ccdc_archive 'CCDC 834862' #TrackingRef 'Ingo-Knepper-av_ikp193.cif' _audit_author_name 'Villinger, A.' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 N2 O' _chemical_formula_sum 'C14 H10 N2 O' _chemical_formula_weight 222.24 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' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 3.78060(10) _cell_length_b 24.0853(8) _cell_length_c 11.7506(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.413(2) _cell_angle_gamma 90.00 _cell_volume 1061.03(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5850 _cell_measurement_theta_min 6.163 _cell_measurement_theta_max 65.015 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9355 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer' _diffrn_measurement_method 'phi and psi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11312 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 28.49 _reflns_number_total 2658 _reflns_number_gt 2328 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker Apex v2.0-2' _computing_cell_refinement 'Bruker Apex v2.0-2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL-97 #============================================================================== # REFINEMENT DATA _refine_special_details ; All H atoms (with exception of H1a) were positioned geometrically and refined using a riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) = 1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles of all methyl groups were allowed to refine. 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^ > 2\s(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^)+(0.0521P)^2^+1.0677P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2658 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1405 _refine_ls_wR_factor_gt 0.1375 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 O1 O 0.3750(4) 0.30201(5) 0.56182(10) 0.0264(3) Uani 1 1 d . . . N1 N 0.0929(4) 0.24295(6) 0.86447(12) 0.0185(3) Uani 1 1 d . . . N2 N 0.0114(4) 0.33159(6) 0.93322(12) 0.0223(3) Uani 1 1 d . . . C1 C 0.2830(4) 0.28301(7) 0.65292(13) 0.0189(3) Uani 1 1 d . . . C2 C 0.2530(4) 0.22541(7) 0.67770(14) 0.0199(3) Uani 1 1 d . . . H2 H 0.2988 0.1990 0.6214 0.024 Uiso 1 1 calc R . . C3 C 0.1601(4) 0.20686(7) 0.78026(13) 0.0177(3) Uani 1 1 d . . . C4 C 0.1023(4) 0.29919(7) 0.84729(13) 0.0177(3) Uani 1 1 d . . . C5 C 0.1956(4) 0.32058(7) 0.74360(13) 0.0181(3) Uani 1 1 d . . . C6 C 0.0113(5) 0.38595(7) 0.91569(15) 0.0245(4) Uani 1 1 d . . . H6 H -0.0552 0.4092 0.9747 0.029 Uiso 1 1 calc R . . C7 C 0.1018(5) 0.41170(7) 0.81657(15) 0.0252(4) Uani 1 1 d . . . H7 H 0.0982 0.4510 0.8092 0.030 Uiso 1 1 calc R . . C8 C 0.1965(5) 0.37835(7) 0.73007(15) 0.0230(4) Uani 1 1 d . . . H8 H 0.2617 0.3944 0.6619 0.028 Uiso 1 1 calc R . . C9 C 0.1248(4) 0.14660(7) 0.80243(14) 0.0190(3) Uani 1 1 d . . . C10 C -0.0365(5) 0.11272(7) 0.71349(15) 0.0248(4) Uani 1 1 d . . . H10 H -0.1231 0.1286 0.6412 0.030 Uiso 1 1 calc R . . C11 C -0.0701(5) 0.05608(8) 0.73067(17) 0.0295(4) Uani 1 1 d . . . H11 H -0.1812 0.0333 0.6703 0.035 Uiso 1 1 calc R . . C12 C 0.0583(5) 0.03259(7) 0.83579(18) 0.0302(4) Uani 1 1 d . . . H12 H 0.0341 -0.0062 0.8476 0.036 Uiso 1 1 calc R . . C13 C 0.2219(5) 0.06587(8) 0.92348(17) 0.0281(4) Uani 1 1 d . . . H13 H 0.3121 0.0496 0.9951 0.034 Uiso 1 1 calc R . . C14 C 0.2551(5) 0.12278(7) 0.90771(14) 0.0224(3) Uani 1 1 d . . . H14 H 0.3662 0.1453 0.9684 0.027 Uiso 1 1 calc R . . H1A H 0.021(7) 0.2310(11) 0.933(2) 0.045(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0356(7) 0.0271(6) 0.0187(6) 0.0025(5) 0.0120(5) 0.0012(5) N1 0.0205(7) 0.0230(7) 0.0131(6) 0.0006(5) 0.0057(5) 0.0003(5) N2 0.0251(7) 0.0259(7) 0.0162(7) -0.0021(5) 0.0046(5) 0.0020(6) C1 0.0172(7) 0.0251(8) 0.0148(7) 0.0002(6) 0.0031(5) 0.0012(6) C2 0.0205(8) 0.0232(8) 0.0166(7) -0.0021(6) 0.0047(6) 0.0012(6) C3 0.0152(7) 0.0219(7) 0.0162(7) -0.0004(6) 0.0023(5) -0.0001(6) C4 0.0151(7) 0.0234(8) 0.0147(7) -0.0006(6) 0.0020(5) 0.0006(6) C5 0.0153(7) 0.0235(8) 0.0154(7) 0.0003(6) 0.0017(5) -0.0002(6) C6 0.0265(9) 0.0265(8) 0.0205(8) -0.0054(6) 0.0031(6) 0.0037(7) C7 0.0280(9) 0.0209(8) 0.0266(9) 0.0008(6) 0.0033(7) 0.0021(6) C8 0.0243(8) 0.0240(8) 0.0210(8) 0.0035(6) 0.0042(6) -0.0005(6) C9 0.0171(7) 0.0210(7) 0.0196(7) -0.0006(6) 0.0053(6) 0.0009(6) C10 0.0241(8) 0.0265(8) 0.0234(8) -0.0015(7) 0.0013(6) -0.0007(7) C11 0.0304(10) 0.0260(9) 0.0322(10) -0.0063(7) 0.0044(8) -0.0042(7) C12 0.0335(10) 0.0204(8) 0.0389(10) 0.0012(7) 0.0131(8) 0.0005(7) C13 0.0302(9) 0.0273(9) 0.0280(9) 0.0057(7) 0.0076(7) 0.0057(7) C14 0.0234(8) 0.0249(8) 0.0190(8) 0.0004(6) 0.0036(6) 0.0027(6) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.254(2) . ? N1 C3 1.365(2) . ? N1 C4 1.371(2) . ? N1 H1A 0.92(3) . ? N2 C6 1.325(2) . ? N2 C4 1.355(2) . ? C1 C2 1.425(2) . ? C1 C5 1.468(2) . ? C2 C3 1.373(2) . ? C2 H2 0.9500 . ? C3 C9 1.484(2) . ? C4 C5 1.409(2) . ? C5 C8 1.401(2) . ? C6 C7 1.401(2) . ? C6 H6 0.9500 . ? C7 C8 1.378(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C14 1.395(2) . ? C9 C10 1.402(2) . ? C10 C11 1.387(3) . ? C10 H10 0.9500 . ? C11 C12 1.388(3) . ? C11 H11 0.9500 . ? C12 C13 1.386(3) . ? C12 H12 0.9500 . ? C13 C14 1.391(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? 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 C3 N1 C4 120.77(14) . . ? C3 N1 H1A 122.1(16) . . ? C4 N1 H1A 116.9(16) . . ? C6 N2 C4 116.63(15) . . ? O1 C1 C2 124.61(15) . . ? O1 C1 C5 120.53(15) . . ? C2 C1 C5 114.86(14) . . ? C3 C2 C1 122.17(15) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? N1 C3 C2 121.44(15) . . ? N1 C3 C9 117.78(14) . . ? C2 C3 C9 120.77(14) . . ? N2 C4 N1 116.46(14) . . ? N2 C4 C5 123.34(15) . . ? N1 C4 C5 120.19(14) . . ? C8 C5 C4 117.77(15) . . ? C8 C5 C1 121.74(15) . . ? C4 C5 C1 120.49(14) . . ? N2 C6 C7 124.85(16) . . ? N2 C6 H6 117.6 . . ? C7 C6 H6 117.6 . . ? C8 C7 C6 118.02(16) . . ? C8 C7 H7 121.0 . . ? C6 C7 H7 121.0 . . ? C7 C8 C5 119.38(16) . . ? C7 C8 H8 120.3 . . ? C5 C8 H8 120.3 . . ? C14 C9 C10 119.46(16) . . ? C14 C9 C3 121.92(15) . . ? C10 C9 C3 118.60(15) . . ? C11 C10 C9 120.20(17) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 120.15(17) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 119.80(17) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 120.66(17) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C13 C14 C9 119.72(16) . . ? C13 C14 H14 120.1 . . ? C9 C14 H14 120.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 178.24(16) . . . . ? C5 C1 C2 C3 -2.0(2) . . . . ? C4 N1 C3 C2 2.6(2) . . . . ? C4 N1 C3 C9 -176.55(14) . . . . ? C1 C2 C3 N1 -0.3(2) . . . . ? C1 C2 C3 C9 178.87(15) . . . . ? C6 N2 C4 N1 -178.31(15) . . . . ? C6 N2 C4 C5 0.4(2) . . . . ? C3 N1 C4 N2 176.22(14) . . . . ? C3 N1 C4 C5 -2.5(2) . . . . ? N2 C4 C5 C8 0.6(2) . . . . ? N1 C4 C5 C8 179.20(15) . . . . ? N2 C4 C5 C1 -178.52(14) . . . . ? N1 C4 C5 C1 0.1(2) . . . . ? O1 C1 C5 C8 2.8(2) . . . . ? C2 C1 C5 C8 -177.04(15) . . . . ? O1 C1 C5 C4 -178.15(15) . . . . ? C2 C1 C5 C4 2.0(2) . . . . ? C4 N2 C6 C7 -0.9(3) . . . . ? N2 C6 C7 C8 0.4(3) . . . . ? C6 C7 C8 C5 0.6(3) . . . . ? C4 C5 C8 C7 -1.0(2) . . . . ? C1 C5 C8 C7 178.05(15) . . . . ? N1 C3 C9 C14 -42.9(2) . . . . ? C2 C3 C9 C14 137.89(17) . . . . ? N1 C3 C9 C10 138.74(16) . . . . ? C2 C3 C9 C10 -40.5(2) . . . . ? C14 C9 C10 C11 0.8(3) . . . . ? C3 C9 C10 C11 179.20(16) . . . . ? C9 C10 C11 C12 -0.5(3) . . . . ? C10 C11 C12 C13 -0.3(3) . . . . ? C11 C12 C13 C14 0.8(3) . . . . ? C12 C13 C14 C9 -0.4(3) . . . . ? C10 C9 C14 C13 -0.4(3) . . . . ? C3 C9 C14 C13 -178.70(16) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.439 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.058 # Attachment 'Ingo-Knepper-av_ikp194.cif' #============================================================================= data_av_ikp194 _database_code_depnum_ccdc_archive 'CCDC 834863' #TrackingRef 'Ingo-Knepper-av_ikp194.cif' _audit_author_name 'Villinger, A.' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 N2 O' _chemical_formula_sum 'C21 H16 N2 O' _chemical_formula_weight 312.36 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' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 7.0872(2) _cell_length_b 17.7874(5) _cell_length_c 25.4096(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.4850(10) _cell_angle_gamma 90.00 _cell_volume 3202.13(15) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8459 _cell_measurement_theta_min 4.853 _cell_measurement_theta_max 59.674 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.82 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9367 _exptl_absorpt_correction_T_max 0.9920 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer' _diffrn_measurement_method 'phi and psi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32931 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0553 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 30.00 _reflns_number_total 9203 _reflns_number_gt 6105 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker Apex v2.0-2' _computing_cell_refinement 'Bruker Apex v2.0-2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL-97 #============================================================================== # REFINEMENT DATA _refine_special_details ; All H atoms were positioned geometrically and refined using a riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) = 1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles of all methyl groups were allowed to refine. 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^ > 2\s(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^)+(0.0470P)^2^+0.5689P] 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 9203 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0951 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1237 _refine_ls_wR_factor_gt 0.1094 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 O1 O 0.51129(17) 0.75353(6) 0.49805(4) 0.0331(3) Uani 1 1 d . . . N1 N 0.44141(18) 0.76632(6) 0.33692(4) 0.0248(3) Uani 1 1 d . . . N2 N 0.38103(19) 0.89457(6) 0.34022(4) 0.0295(3) Uani 1 1 d . . . C1 C 0.4937(2) 0.75744(8) 0.44925(5) 0.0250(3) Uani 1 1 d . . . C2 C 0.5160(2) 0.69481(8) 0.41459(5) 0.0267(3) Uani 1 1 d . . . H2 H 0.5518 0.6477 0.4293 0.032 Uiso 1 1 calc R . . C3 C 0.4883(2) 0.69975(8) 0.36145(5) 0.0250(3) Uani 1 1 d . . . C4 C 0.4234(2) 0.83110(7) 0.36697(5) 0.0235(3) Uani 1 1 d . . . C5 C 0.4470(2) 0.82821(8) 0.42206(5) 0.0241(3) Uani 1 1 d . . . C6 C 0.3579(2) 0.95662(8) 0.36846(6) 0.0332(4) Uani 1 1 d . . . H6 H 0.3287 1.0018 0.3500 0.040 Uiso 1 1 calc R . . C7 C 0.3736(2) 0.96007(8) 0.42307(6) 0.0336(4) Uani 1 1 d . . . H7 H 0.3532 1.0059 0.4413 0.040 Uiso 1 1 calc R . . C8 C 0.4193(2) 0.89526(8) 0.44986(5) 0.0293(3) Uani 1 1 d . . . H8 H 0.4321 0.8958 0.4872 0.035 Uiso 1 1 calc R . . C9 C 0.5087(3) 0.63086(8) 0.32838(5) 0.0297(3) Uani 1 1 d . . . C10 C 0.3547(3) 0.58264(9) 0.32143(6) 0.0426(5) Uani 1 1 d . . . H10 H 0.2366 0.5950 0.3361 0.051 Uiso 1 1 calc R . . C11 C 0.3748(4) 0.51649(10) 0.29298(6) 0.0568(6) Uani 1 1 d . . . H11 H 0.2704 0.4835 0.2882 0.068 Uiso 1 1 calc R . . C12 C 0.5459(4) 0.49863(9) 0.27170(6) 0.0558(6) Uani 1 1 d . . . H12 H 0.5593 0.4534 0.2523 0.067 Uiso 1 1 calc R . . C13 C 0.6974(3) 0.54621(10) 0.27859(7) 0.0513(5) Uani 1 1 d . . . H13 H 0.8150 0.5336 0.2638 0.062 Uiso 1 1 calc R . . C14 C 0.6803(3) 0.61267(9) 0.30694(6) 0.0393(4) Uani 1 1 d . . . H14 H 0.7855 0.6453 0.3115 0.047 Uiso 1 1 calc R . . C15 C 0.3825(2) 0.76851(8) 0.28087(5) 0.0271(3) Uani 1 1 d . . . H15A H 0.2752 0.8038 0.2767 0.033 Uiso 1 1 calc R . . H15B H 0.3365 0.7180 0.2704 0.033 Uiso 1 1 calc R . . C16 C 0.5346(2) 0.79181(7) 0.24370(5) 0.0236(3) Uani 1 1 d . . . C17 C 0.4839(2) 0.80454(8) 0.19099(5) 0.0285(3) Uani 1 1 d . . . H17 H 0.3560 0.7989 0.1795 0.034 Uiso 1 1 calc R . . C18 C 0.6187(3) 0.82532(8) 0.15528(5) 0.0333(4) Uani 1 1 d . . . H18 H 0.5828 0.8335 0.1195 0.040 Uiso 1 1 calc R . . C19 C 0.8053(3) 0.83419(8) 0.17143(6) 0.0352(4) Uani 1 1 d . . . H19 H 0.8975 0.8488 0.1470 0.042 Uiso 1 1 calc R . . C20 C 0.8560(3) 0.82153(9) 0.22360(6) 0.0357(4) Uani 1 1 d . . . H20 H 0.9839 0.8274 0.2350 0.043 Uiso 1 1 calc R . . C21 C 0.7215(2) 0.80028(8) 0.25949(5) 0.0304(3) Uani 1 1 d . . . H21 H 0.7582 0.7915 0.2952 0.037 Uiso 1 1 calc R . . O2 O 0.02820(16) 0.73450(6) 0.34986(3) 0.0324(3) Uani 1 1 d . . . N3 N -0.05940(18) 0.77767(6) 0.50668(4) 0.0229(3) Uani 1 1 d . . . N4 N -0.12454(19) 0.90354(6) 0.48968(4) 0.0273(3) Uani 1 1 d . . . C22 C 0.0041(2) 0.74765(7) 0.39735(5) 0.0240(3) Uani 1 1 d . . . C23 C 0.0227(2) 0.69228(8) 0.43801(5) 0.0257(3) Uani 1 1 d . . . H23 H 0.0595 0.6428 0.4286 0.031 Uiso 1 1 calc R . . C24 C -0.0099(2) 0.70726(7) 0.48959(5) 0.0230(3) Uani 1 1 d . . . C25 C -0.0770(2) 0.83585(7) 0.47016(5) 0.0212(3) Uani 1 1 d . . . C26 C -0.0475(2) 0.82248(7) 0.41651(5) 0.0221(3) Uani 1 1 d . . . C27 C -0.1446(2) 0.95938(8) 0.45530(6) 0.0308(3) Uani 1 1 d . . . H27 H -0.1783 1.0074 0.4685 0.037 Uiso 1 1 calc R . . C28 C -0.1198(2) 0.95263(8) 0.40129(6) 0.0310(3) Uani 1 1 d . . . H28 H -0.1368 0.9946 0.3785 0.037 Uiso 1 1 calc R . . C29 C -0.0702(2) 0.88359(8) 0.38207(5) 0.0273(3) Uani 1 1 d . . . H29 H -0.0512 0.8772 0.3455 0.033 Uiso 1 1 calc R . . C30 C 0.0089(2) 0.64414(7) 0.52843(5) 0.0258(3) Uani 1 1 d . . . C31 C 0.1798(3) 0.63089(8) 0.55491(6) 0.0350(4) Uani 1 1 d . . . H31 H 0.2827 0.6644 0.5508 0.042 Uiso 1 1 calc R . . C32 C 0.1992(3) 0.56810(9) 0.58750(6) 0.0419(4) Uani 1 1 d . . . H32 H 0.3157 0.5590 0.6057 0.050 Uiso 1 1 calc R . . C33 C 0.0501(3) 0.51917(9) 0.59343(6) 0.0401(4) Uani 1 1 d . . . H33 H 0.0639 0.4766 0.6158 0.048 Uiso 1 1 calc R . . C34 C -0.1184(3) 0.53210(9) 0.56699(6) 0.0405(4) Uani 1 1 d . . . H34 H -0.2205 0.4981 0.5709 0.049 Uiso 1 1 calc R . . C35 C -0.1400(3) 0.59449(8) 0.53466(6) 0.0339(4) Uani 1 1 d . . . H35 H -0.2572 0.6033 0.5167 0.041 Uiso 1 1 calc R . . C36 C -0.1175(2) 0.79103(8) 0.56107(5) 0.0253(3) Uani 1 1 d . . . H36A H -0.1616 0.7429 0.5759 0.030 Uiso 1 1 calc R . . H36B H -0.2260 0.8261 0.5602 0.030 Uiso 1 1 calc R . . C37 C 0.0341(2) 0.82286(7) 0.59747(5) 0.0239(3) Uani 1 1 d . . . C38 C -0.0159(2) 0.84339(8) 0.64844(5) 0.0305(3) Uani 1 1 d . . . H38 H -0.1436 0.8393 0.6585 0.037 Uiso 1 1 calc R . . C39 C 0.1194(3) 0.86967(8) 0.68429(5) 0.0353(4) Uani 1 1 d . . . H39 H 0.0839 0.8830 0.7189 0.042 Uiso 1 1 calc R . . C40 C 0.3053(3) 0.87666(8) 0.67005(6) 0.0355(4) Uani 1 1 d . . . H40 H 0.3977 0.8948 0.6946 0.043 Uiso 1 1 calc R . . C41 C 0.3556(2) 0.85689(8) 0.61956(6) 0.0326(3) Uani 1 1 d . . . H41 H 0.4831 0.8619 0.6095 0.039 Uiso 1 1 calc R . . C42 C 0.2210(2) 0.82982(8) 0.58359(5) 0.0273(3) Uani 1 1 d . . . H42 H 0.2575 0.8160 0.5492 0.033 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 O1 0.0351(7) 0.0445(6) 0.0195(4) -0.0004(4) -0.0002(5) -0.0052(5) N1 0.0289(7) 0.0258(6) 0.0195(5) 0.0007(4) -0.0006(5) -0.0024(5) N2 0.0316(8) 0.0277(6) 0.0293(6) 0.0028(5) 0.0017(6) -0.0023(6) C1 0.0189(8) 0.0333(7) 0.0229(6) 0.0009(5) 0.0019(6) -0.0059(6) C2 0.0275(9) 0.0284(7) 0.0242(6) 0.0029(5) -0.0003(6) -0.0027(6) C3 0.0258(8) 0.0266(7) 0.0225(6) 0.0008(5) 0.0014(6) -0.0033(6) C4 0.0193(7) 0.0267(6) 0.0246(6) 0.0000(5) 0.0034(6) -0.0030(6) C5 0.0175(7) 0.0315(7) 0.0234(6) -0.0023(5) 0.0029(6) -0.0059(6) C6 0.0323(10) 0.0278(7) 0.0395(8) 0.0017(6) 0.0027(7) -0.0027(7) C7 0.0317(10) 0.0295(7) 0.0399(8) -0.0071(6) 0.0066(7) -0.0050(7) C8 0.0246(8) 0.0356(8) 0.0278(7) -0.0056(6) 0.0051(6) -0.0083(7) C9 0.0435(10) 0.0248(7) 0.0207(6) 0.0024(5) -0.0035(7) -0.0024(7) C10 0.0616(13) 0.0360(8) 0.0304(7) 0.0004(6) 0.0035(8) -0.0174(9) C11 0.103(2) 0.0318(9) 0.0352(8) 0.0012(7) -0.0026(11) -0.0278(11) C12 0.114(2) 0.0239(8) 0.0290(8) -0.0001(6) -0.0036(11) 0.0061(10) C13 0.0779(17) 0.0374(9) 0.0384(9) -0.0052(7) -0.0002(10) 0.0191(10) C14 0.0493(12) 0.0328(8) 0.0359(8) -0.0038(6) -0.0006(8) 0.0060(8) C15 0.0321(9) 0.0288(7) 0.0200(6) 0.0009(5) -0.0046(6) -0.0022(6) C16 0.0297(9) 0.0196(6) 0.0214(6) -0.0016(5) -0.0004(6) 0.0014(6) C17 0.0333(9) 0.0284(7) 0.0235(6) -0.0011(5) -0.0023(7) 0.0031(7) C18 0.0438(11) 0.0347(8) 0.0215(6) 0.0006(6) 0.0017(7) 0.0054(8) C19 0.0391(10) 0.0361(8) 0.0308(7) -0.0012(6) 0.0107(8) 0.0015(8) C20 0.0287(9) 0.0433(9) 0.0352(8) -0.0033(7) 0.0010(7) 0.0028(7) C21 0.0325(9) 0.0345(7) 0.0241(6) -0.0003(6) -0.0027(7) 0.0016(7) O2 0.0371(7) 0.0393(6) 0.0208(4) -0.0025(4) 0.0014(5) -0.0013(5) N3 0.0247(7) 0.0251(5) 0.0189(5) 0.0006(4) 0.0013(5) -0.0024(5) N4 0.0265(7) 0.0256(6) 0.0298(6) -0.0020(5) -0.0004(5) -0.0013(5) C22 0.0203(8) 0.0288(7) 0.0229(6) -0.0017(5) -0.0008(6) -0.0032(6) C23 0.0277(8) 0.0242(6) 0.0254(6) -0.0015(5) 0.0012(6) -0.0003(6) C24 0.0221(8) 0.0230(6) 0.0240(6) 0.0013(5) -0.0006(6) -0.0032(6) C25 0.0171(7) 0.0235(6) 0.0230(6) 0.0005(5) -0.0007(6) -0.0030(6) C26 0.0169(7) 0.0261(6) 0.0232(6) 0.0019(5) -0.0001(6) -0.0038(6) C27 0.0275(9) 0.0233(7) 0.0414(8) 0.0007(6) 0.0003(7) -0.0002(6) C28 0.0282(9) 0.0275(7) 0.0371(8) 0.0092(6) -0.0022(7) -0.0024(6) C29 0.0232(8) 0.0329(7) 0.0257(6) 0.0045(5) -0.0007(6) -0.0051(6) C30 0.0325(9) 0.0239(6) 0.0209(6) 0.0007(5) -0.0004(6) -0.0012(6) C31 0.0345(10) 0.0304(7) 0.0398(8) 0.0069(6) -0.0056(8) -0.0040(7) C32 0.0454(12) 0.0366(9) 0.0431(9) 0.0085(7) -0.0122(9) 0.0028(8) C33 0.0602(13) 0.0271(7) 0.0327(7) 0.0074(6) -0.0056(9) -0.0017(8) C34 0.0523(12) 0.0320(8) 0.0371(8) 0.0074(6) -0.0023(9) -0.0140(8) C35 0.0351(10) 0.0360(8) 0.0303(7) 0.0060(6) -0.0047(7) -0.0071(7) C36 0.0251(8) 0.0296(7) 0.0213(6) 0.0001(5) 0.0053(6) -0.0028(6) C37 0.0295(9) 0.0212(6) 0.0210(6) 0.0022(5) 0.0010(6) 0.0001(6) C38 0.0362(10) 0.0302(7) 0.0253(6) -0.0021(5) 0.0054(7) 0.0001(7) C39 0.0500(12) 0.0327(8) 0.0232(6) -0.0038(6) -0.0012(7) 0.0024(8) C40 0.0435(11) 0.0300(7) 0.0324(7) -0.0002(6) -0.0110(8) -0.0002(7) C41 0.0292(9) 0.0312(7) 0.0371(7) 0.0016(6) -0.0032(7) -0.0010(7) C42 0.0309(9) 0.0264(7) 0.0247(6) 0.0007(5) 0.0025(6) -0.0001(6) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2449(15) . ? N1 C3 1.3750(17) . ? N1 C4 1.3900(17) . ? N1 C15 1.4743(16) . ? N2 C6 1.3289(18) . ? N2 C4 1.3476(17) . ? C1 C2 1.4315(19) . ? C1 C5 1.4695(19) . ? C2 C3 1.3623(17) . ? C2 H2 0.9500 . ? C3 C9 1.4949(19) . ? C4 C5 1.4066(17) . ? C5 C8 1.4027(19) . ? C6 C7 1.391(2) . ? C6 H6 0.9500 . ? C7 C8 1.373(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C14 1.384(2) . ? C9 C10 1.396(2) . ? C10 C11 1.390(2) . ? C10 H10 0.9500 . ? C11 C12 1.378(3) . ? C11 H11 0.9500 . ? C12 C13 1.374(3) . ? C12 H12 0.9500 . ? C13 C14 1.391(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.509(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C21 1.383(2) . ? C16 C17 1.3962(18) . ? C17 C18 1.385(2) . ? C17 H17 0.9500 . ? C18 C19 1.384(2) . ? C18 H18 0.9500 . ? C19 C20 1.383(2) . ? C19 H19 0.9500 . ? C20 C21 1.389(2) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? O2 C22 1.2453(15) . ? N3 C24 1.3741(17) . ? N3 C25 1.3934(16) . ? N3 C36 1.4716(16) . ? N4 C27 1.3281(17) . ? N4 C25 1.3484(17) . ? C22 C23 1.4310(18) . ? C22 C26 1.4667(18) . ? C23 C24 1.3629(18) . ? C23 H23 0.9500 . ? C24 C30 1.4987(18) . ? C25 C26 1.4050(17) . ? C26 C29 1.4022(18) . ? C27 C28 1.393(2) . ? C27 H27 0.9500 . ? C28 C29 1.371(2) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 C35 1.388(2) . ? C30 C31 1.390(2) . ? C31 C32 1.395(2) . ? C31 H31 0.9500 . ? C32 C33 1.380(3) . ? C32 H32 0.9500 . ? C33 C34 1.374(3) . ? C33 H33 0.9500 . ? C34 C35 1.387(2) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 C37 1.509(2) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C42 1.385(2) . ? C37 C38 1.3998(18) . ? C38 C39 1.386(2) . ? C38 H38 0.9500 . ? C39 C40 1.381(3) . ? C39 H39 0.9500 . ? C40 C41 1.386(2) . ? C40 H40 0.9500 . ? C41 C42 1.390(2) . ? C41 H41 0.9500 . ? C42 H42 0.9500 . ? 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 C3 N1 C4 119.32(11) . . ? C3 N1 C15 121.31(11) . . ? C4 N1 C15 118.75(11) . . ? C6 N2 C4 116.90(12) . . ? O1 C1 C2 124.02(13) . . ? O1 C1 C5 122.12(12) . . ? C2 C1 C5 113.86(11) . . ? C3 C2 C1 122.98(13) . . ? C3 C2 H2 118.5 . . ? C1 C2 H2 118.5 . . ? C2 C3 N1 122.12(12) . . ? C2 C3 C9 119.40(12) . . ? N1 C3 C9 118.48(11) . . ? N2 C4 N1 116.10(11) . . ? N2 C4 C5 123.50(12) . . ? N1 C4 C5 120.40(12) . . ? C8 C5 C4 117.09(13) . . ? C8 C5 C1 121.63(12) . . ? C4 C5 C1 121.26(12) . . ? N2 C6 C7 124.60(14) . . ? N2 C6 H6 117.7 . . ? C7 C6 H6 117.7 . . ? C8 C7 C6 117.98(13) . . ? C8 C7 H7 121.0 . . ? C6 C7 H7 121.0 . . ? C7 C8 C5 119.91(13) . . ? C7 C8 H8 120.0 . . ? C5 C8 H8 120.0 . . ? C14 C9 C10 119.93(15) . . ? C14 C9 C3 120.76(14) . . ? C10 C9 C3 119.23(16) . . ? C11 C10 C9 119.7(2) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C12 C11 C10 120.19(19) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 120.02(16) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.7(2) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C9 C14 C13 119.45(18) . . ? C9 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? N1 C15 C16 115.03(13) . . ? N1 C15 H15A 108.5 . . ? C16 C15 H15A 108.5 . . ? N1 C15 H15B 108.5 . . ? C16 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? C21 C16 C17 118.79(14) . . ? C21 C16 C15 122.86(12) . . ? C17 C16 C15 118.34(14) . . ? C18 C17 C16 120.46(15) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C19 C18 C17 120.45(14) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C20 C19 C18 119.23(16) . . ? C20 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? C19 C20 C21 120.54(16) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C16 C21 C20 120.53(13) . . ? C16 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C24 N3 C25 119.05(10) . . ? C24 N3 C36 121.60(11) . . ? C25 N3 C36 118.89(11) . . ? C27 N4 C25 116.70(12) . . ? O2 C22 C23 123.91(12) . . ? O2 C22 C26 122.25(12) . . ? C23 C22 C26 113.83(11) . . ? C24 C23 C22 123.02(12) . . ? C24 C23 H23 118.5 . . ? C22 C23 H23 118.5 . . ? C23 C24 N3 122.22(12) . . ? C23 C24 C30 118.19(12) . . ? N3 C24 C30 119.58(11) . . ? N4 C25 N3 115.92(11) . . ? N4 C25 C26 123.58(12) . . ? N3 C25 C26 120.50(11) . . ? C29 C26 C25 117.17(12) . . ? C29 C26 C22 121.47(12) . . ? C25 C26 C22 121.35(11) . . ? N4 C27 C28 124.72(13) . . ? N4 C27 H27 117.6 . . ? C28 C27 H27 117.6 . . ? C29 C28 C27 117.92(13) . . ? C29 C28 H28 121.0 . . ? C27 C28 H28 121.0 . . ? C28 C29 C26 119.91(13) . . ? C28 C29 H29 120.0 . . ? C26 C29 H29 120.0 . . ? C35 C30 C31 119.49(13) . . ? C35 C30 C24 119.78(14) . . ? C31 C30 C24 120.48(14) . . ? C30 C31 C32 119.61(16) . . ? C30 C31 H31 120.2 . . ? C32 C31 H31 120.2 . . ? C33 C32 C31 120.38(17) . . ? C33 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? C34 C33 C32 119.94(14) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C33 C34 C35 120.32(16) . . ? C33 C34 H34 119.8 . . ? C35 C34 H34 119.8 . . ? C34 C35 C30 120.26(16) . . ? C34 C35 H35 119.9 . . ? C30 C35 H35 119.9 . . ? N3 C36 C37 115.08(12) . . ? N3 C36 H36A 108.5 . . ? C37 C36 H36A 108.5 . . ? N3 C36 H36B 108.5 . . ? C37 C36 H36B 108.5 . . ? H36A C36 H36B 107.5 . . ? C42 C37 C38 118.59(14) . . ? C42 C37 C36 123.21(12) . . ? C38 C37 C36 118.15(14) . . ? C39 C38 C37 120.58(16) . . ? C39 C38 H38 119.7 . . ? C37 C38 H38 119.7 . . ? C40 C39 C38 120.43(14) . . ? C40 C39 H39 119.8 . . ? C38 C39 H39 119.8 . . ? C39 C40 C41 119.33(15) . . ? C39 C40 H40 120.3 . . ? C41 C40 H40 120.3 . . ? C40 C41 C42 120.53(16) . . ? C40 C41 H41 119.7 . . ? C42 C41 H41 119.7 . . ? C37 C42 C41 120.54(13) . . ? C37 C42 H42 119.7 . . ? C41 C42 H42 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 177.15(15) . . . . ? C5 C1 C2 C3 -2.7(2) . . . . ? C1 C2 C3 N1 1.8(2) . . . . ? C1 C2 C3 C9 -178.02(15) . . . . ? C4 N1 C3 C2 0.7(2) . . . . ? C15 N1 C3 C2 -170.14(15) . . . . ? C4 N1 C3 C9 -179.47(14) . . . . ? C15 N1 C3 C9 9.7(2) . . . . ? C6 N2 C4 N1 178.12(14) . . . . ? C6 N2 C4 C5 -1.2(2) . . . . ? C3 N1 C4 N2 178.66(13) . . . . ? C15 N1 C4 N2 -10.2(2) . . . . ? C3 N1 C4 C5 -2.0(2) . . . . ? C15 N1 C4 C5 169.10(13) . . . . ? N2 C4 C5 C8 1.8(2) . . . . ? N1 C4 C5 C8 -177.51(14) . . . . ? N2 C4 C5 C1 -179.85(14) . . . . ? N1 C4 C5 C1 0.9(2) . . . . ? O1 C1 C5 C8 -0.2(2) . . . . ? C2 C1 C5 C8 179.72(14) . . . . ? O1 C1 C5 C4 -178.48(14) . . . . ? C2 C1 C5 C4 1.4(2) . . . . ? C4 N2 C6 C7 -0.4(2) . . . . ? N2 C6 C7 C8 1.2(3) . . . . ? C6 C7 C8 C5 -0.5(2) . . . . ? C4 C5 C8 C7 -0.8(2) . . . . ? C1 C5 C8 C7 -179.21(14) . . . . ? C2 C3 C9 C14 -91.42(18) . . . . ? N1 C3 C9 C14 88.77(18) . . . . ? C2 C3 C9 C10 85.34(19) . . . . ? N1 C3 C9 C10 -94.47(17) . . . . ? C14 C9 C10 C11 0.0(2) . . . . ? C3 C9 C10 C11 -176.74(14) . . . . ? C9 C10 C11 C12 -0.1(2) . . . . ? C10 C11 C12 C13 0.0(3) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C10 C9 C14 C13 0.0(2) . . . . ? C3 C9 C14 C13 176.72(13) . . . . ? C12 C13 C14 C9 0.0(2) . . . . ? C3 N1 C15 C16 -99.82(16) . . . . ? C4 N1 C15 C16 89.26(16) . . . . ? N1 C15 C16 C21 8.75(19) . . . . ? N1 C15 C16 C17 -171.93(12) . . . . ? C21 C16 C17 C18 0.0(2) . . . . ? C15 C16 C17 C18 -179.39(13) . . . . ? C16 C17 C18 C19 -0.4(2) . . . . ? C17 C18 C19 C20 0.5(2) . . . . ? C18 C19 C20 C21 -0.1(2) . . . . ? C17 C16 C21 C20 0.4(2) . . . . ? C15 C16 C21 C20 179.72(13) . . . . ? C19 C20 C21 C16 -0.3(2) . . . . ? O2 C22 C23 C24 -177.94(15) . . . . ? C26 C22 C23 C24 1.8(2) . . . . ? C22 C23 C24 N3 -1.5(2) . . . . ? C22 C23 C24 C30 178.32(14) . . . . ? C25 N3 C24 C23 0.0(2) . . . . ? C36 N3 C24 C23 172.14(14) . . . . ? C25 N3 C24 C30 -179.82(13) . . . . ? C36 N3 C24 C30 -7.7(2) . . . . ? C27 N4 C25 N3 -179.04(13) . . . . ? C27 N4 C25 C26 0.4(2) . . . . ? C24 N3 C25 N4 -179.54(13) . . . . ? C36 N3 C25 N4 8.14(19) . . . . ? C24 N3 C25 C26 1.0(2) . . . . ? C36 N3 C25 C26 -171.34(13) . . . . ? N4 C25 C26 C29 -0.3(2) . . . . ? N3 C25 C26 C29 179.17(13) . . . . ? N4 C25 C26 C22 -179.99(14) . . . . ? N3 C25 C26 C22 -0.5(2) . . . . ? O2 C22 C26 C29 -0.7(2) . . . . ? C23 C22 C26 C29 179.49(14) . . . . ? O2 C22 C26 C25 178.98(14) . . . . ? C23 C22 C26 C25 -0.8(2) . . . . ? C25 N4 C27 C28 -0.1(2) . . . . ? N4 C27 C28 C29 -0.3(2) . . . . ? C27 C28 C29 C26 0.5(2) . . . . ? C25 C26 C29 C28 -0.2(2) . . . . ? C22 C26 C29 C28 179.51(14) . . . . ? C23 C24 C30 C35 -82.41(19) . . . . ? N3 C24 C30 C35 97.44(17) . . . . ? C23 C24 C30 C31 91.89(17) . . . . ? N3 C24 C30 C31 -88.26(18) . . . . ? C35 C30 C31 C32 -0.2(2) . . . . ? C24 C30 C31 C32 -174.55(14) . . . . ? C30 C31 C32 C33 0.2(2) . . . . ? C31 C32 C33 C34 0.2(3) . . . . ? C32 C33 C34 C35 -0.5(3) . . . . ? C33 C34 C35 C30 0.5(2) . . . . ? C31 C30 C35 C34 -0.1(2) . . . . ? C24 C30 C35 C34 174.28(14) . . . . ? C24 N3 C36 C37 99.71(15) . . . . ? C25 N3 C36 C37 -88.17(16) . . . . ? N3 C36 C37 C42 -8.44(19) . . . . ? N3 C36 C37 C38 174.27(12) . . . . ? C42 C37 C38 C39 -0.4(2) . . . . ? C36 C37 C38 C39 177.02(13) . . . . ? C37 C38 C39 C40 0.6(2) . . . . ? C38 C39 C40 C41 -0.2(2) . . . . ? C39 C40 C41 C42 -0.4(2) . . . . ? C38 C37 C42 C41 -0.2(2) . . . . ? C36 C37 C42 C41 -177.50(13) . . . . ? C40 C41 C42 C37 0.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.229 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.047 # Attachment 'Ingo-Knepper-is_ikp207.cif' #============================================================================= data_is_ikp207 _database_code_depnum_ccdc_archive 'CCDC 834864' #TrackingRef 'Ingo-Knepper-is_ikp207.cif' _audit_author_name 'Villinger, A.' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H22 N2 O' _chemical_formula_sum 'C17 H22 N2 O' _chemical_formula_weight 270.37 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' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/m' _symmetry_space_group_name_Hall '-C 2y' _symmetry_Int_Tables_number 12 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' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 18.4597(18) _cell_length_b 7.1537(7) _cell_length_c 11.0986(12) _cell_angle_alpha 90.00 _cell_angle_beta 98.355(6) _cell_angle_gamma 90.00 _cell_volume 1450.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6329 _cell_measurement_theta_min 5.371 _cell_measurement_theta_max 61.168 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.67 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9499 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer' _diffrn_measurement_method 'phi and psi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15903 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2273 _reflns_number_gt 1920 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker Apex v2.0-2' _computing_cell_refinement 'Bruker Apex v2.0-2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL-97 #============================================================================== # REFINEMENT DATA _refine_special_details ; All H atoms were positioned geometrically and refined using a riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) = 1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles of all methyl groups were allowed to refine. 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^ > 2\s(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^)+(0.0830P)^2^+0.2720P] 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 2273 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1267 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.24608(5) 0.0000 0.65617(8) 0.0199(2) Uani 1 2 d S . . N2 N 0.34503(5) 0.0000 0.81289(9) 0.0279(2) Uani 1 2 d S . . O1 O 0.38584(5) 0.0000 0.39795(8) 0.0357(2) Uani 1 2 d S . . C1 C 0.21990(6) 0.0000 0.53344(9) 0.0185(2) Uani 1 2 d S . . C2 C 0.26576(6) 0.0000 0.44715(10) 0.0217(2) Uani 1 2 d S . . H2 H 0.2446 0.0000 0.3638 0.026 Uiso 1 2 calc SR . . C3 C 0.34341(6) 0.0000 0.47557(10) 0.0238(2) Uani 1 2 d S . . C4 C 0.37034(6) 0.0000 0.60590(10) 0.0220(2) Uani 1 2 d S . . C5 C 0.44525(6) 0.0000 0.64846(11) 0.0276(3) Uani 1 2 d S . . H5 H 0.4795 0.0000 0.5923 0.033 Uiso 1 2 calc SR . . C6 C 0.46964(6) 0.0000 0.77121(12) 0.0309(3) Uani 1 2 d S . . H6 H 0.5204 0.0000 0.8019 0.037 Uiso 1 2 calc SR . . C7 C 0.41677(6) 0.0000 0.84901(11) 0.0319(3) Uani 1 2 d S . . H7 H 0.4333 0.0000 0.9342 0.038 Uiso 1 2 calc SR . . C8 C 0.32148(6) 0.0000 0.69255(9) 0.0210(2) Uani 1 2 d S . . C9 C 0.13804(6) 0.0000 0.49460(9) 0.0212(2) Uani 1 2 d S . . H9A H 0.1174 0.1115 0.5300 0.025 Uiso 0.50 1 calc PR . . H9B H 0.1174 -0.1115 0.5300 0.025 Uiso 0.50 1 calc PR . . C10 C 0.11243(6) 0.0000 0.35774(10) 0.0260(2) Uani 1 2 d S . . H10A H 0.1318 0.1120 0.3208 0.031 Uiso 0.50 1 calc PR . . H10B H 0.1318 -0.1120 0.3208 0.031 Uiso 0.50 1 calc PR . . C11 C 0.02914(7) 0.0000 0.33109(13) 0.0372(3) Uani 1 2 d S . . H11A H 0.0137 0.0093 0.2430 0.056 Uiso 0.50 1 calc PR . . H11B H 0.0099 0.1069 0.3717 0.056 Uiso 0.50 1 calc PR . . H11C H 0.0102 -0.1162 0.3614 0.056 Uiso 0.50 1 calc PR . . C12 C 0.19502(5) 0.0000 0.74929(9) 0.0203(2) Uani 1 2 d S . . H12 H 0.1446 0.0000 0.7021 0.024 Uiso 1 2 calc SR . . C13 C 0.20031(4) 0.17784(12) 0.82578(7) 0.0263(2) Uani 1 1 d . . . H13A H 0.1932 0.2884 0.7717 0.032 Uiso 1 1 calc R . . H13B H 0.2495 0.1866 0.8747 0.032 Uiso 1 1 calc R . . C14 C 0.14189(5) 0.17520(14) 0.91022(8) 0.0321(2) Uani 1 1 d . . . H14A H 0.1478 0.2868 0.9635 0.039 Uiso 1 1 calc R . . H14B H 0.0928 0.1812 0.8608 0.039 Uiso 1 1 calc R . . C15 C 0.14713(8) 0.0000 0.98865(11) 0.0370(3) Uani 1 2 d S . . H15A H 0.1943 0.0000 1.0441 0.044 Uiso 1 2 calc SR . . H15B H 0.1071 0.0000 1.0391 0.044 Uiso 1 2 calc SR . . 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 0.0179(4) 0.0257(4) 0.0167(4) 0.000 0.0043(3) 0.000 N2 0.0204(4) 0.0434(6) 0.0199(4) 0.000 0.0027(3) 0.000 O1 0.0276(4) 0.0574(6) 0.0249(4) 0.000 0.0131(3) 0.000 C1 0.0210(5) 0.0174(4) 0.0172(4) 0.000 0.0032(3) 0.000 C2 0.0239(5) 0.0236(5) 0.0183(5) 0.000 0.0053(4) 0.000 C3 0.0251(5) 0.0258(5) 0.0221(5) 0.000 0.0089(4) 0.000 C4 0.0201(5) 0.0249(5) 0.0219(5) 0.000 0.0063(4) 0.000 C5 0.0210(5) 0.0348(6) 0.0283(6) 0.000 0.0082(4) 0.000 C6 0.0183(5) 0.0436(7) 0.0304(6) 0.000 0.0026(4) 0.000 C7 0.0213(5) 0.0505(8) 0.0234(5) 0.000 0.0013(4) 0.000 C8 0.0187(5) 0.0253(5) 0.0195(5) 0.000 0.0043(4) 0.000 C9 0.0202(5) 0.0239(5) 0.0195(5) 0.000 0.0026(4) 0.000 C10 0.0263(5) 0.0305(6) 0.0206(5) 0.000 0.0009(4) 0.000 C11 0.0279(6) 0.0495(8) 0.0317(6) 0.000 -0.0045(5) 0.000 C12 0.0179(4) 0.0271(5) 0.0164(4) 0.000 0.0043(3) 0.000 C13 0.0289(4) 0.0263(4) 0.0244(4) -0.0016(3) 0.0065(3) 0.0024(3) C14 0.0294(4) 0.0431(5) 0.0246(4) -0.0060(3) 0.0064(3) 0.0092(3) C15 0.0368(7) 0.0544(8) 0.0220(5) 0.000 0.0115(5) 0.000 #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.3777(13) . ? N1 C8 1.3917(13) . ? N1 C12 1.4965(12) . ? N2 C7 1.3266(14) . ? N2 C8 1.3432(14) . ? O1 C3 1.2456(13) . ? C1 C2 1.3673(14) . ? C1 C9 1.5099(14) . ? C2 C3 1.4224(15) . ? C2 H2 0.9500 . ? C3 C4 1.4596(15) . ? C4 C5 1.3947(15) . ? C4 C8 1.4110(14) . ? C5 C6 1.3714(17) . ? C5 H5 0.9500 . ? C6 C7 1.3939(16) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C9 C10 1.5239(15) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5228(17) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.5247(10) . ? C12 C13 1.5247(10) 6 ? C12 H12 1.0000 . ? C13 C14 1.5282(11) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.5210(12) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C14 1.5210(12) 6 ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C8 118.64(9) . . ? C1 N1 C12 121.14(8) . . ? C8 N1 C12 120.22(8) . . ? C7 N2 C8 117.72(10) . . ? C2 C1 N1 121.91(10) . . ? C2 C1 C9 119.73(9) . . ? N1 C1 C9 118.36(9) . . ? C1 C2 C3 123.46(10) . . ? C1 C2 H2 118.3 . . ? C3 C2 H2 118.3 . . ? O1 C3 C2 124.15(11) . . ? O1 C3 C4 121.84(10) . . ? C2 C3 C4 114.01(9) . . ? C5 C4 C8 118.02(10) . . ? C5 C4 C3 120.92(9) . . ? C8 C4 C3 121.07(10) . . ? C6 C5 C4 120.18(10) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 117.20(11) . . ? C5 C6 H6 121.4 . . ? C7 C6 H6 121.4 . . ? N2 C7 C6 124.81(11) . . ? N2 C7 H7 117.6 . . ? C6 C7 H7 117.6 . . ? N2 C8 N1 117.01(9) . . ? N2 C8 C4 122.08(10) . . ? N1 C8 C4 120.91(9) . . ? C1 C9 C10 115.93(9) . . ? C1 C9 H9A 108.3 . . ? C10 C9 H9A 108.3 . . ? C1 C9 H9B 108.3 . . ? C10 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C11 C10 C9 110.60(10) . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 C13 112.88(5) . . ? N1 C12 C13 112.88(5) . 6 ? C13 C12 C13 113.12(9) . 6 ? N1 C12 H12 105.7 . . ? C13 C12 H12 105.7 . . ? C13 C12 H12 105.7 6 . ? C12 C13 C14 109.72(7) . . ? C12 C13 H13A 109.7 . . ? C14 C13 H13A 109.7 . . ? C12 C13 H13B 109.7 . . ? C14 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? C15 C14 C13 111.67(8) . . ? C15 C14 H14A 109.3 . . ? C13 C14 H14A 109.3 . . ? C15 C14 H14B 109.3 . . ? C13 C14 H14B 109.3 . . ? H14A C14 H14B 107.9 . . ? C14 C15 C14 110.98(10) 6 . ? C14 C15 H15A 109.4 6 . ? C14 C15 H15A 109.4 . . ? C14 C15 H15B 109.4 6 . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C1 C2 0.0 . . . . ? C12 N1 C1 C2 180.0 . . . . ? C8 N1 C1 C9 180.0 . . . . ? C12 N1 C1 C9 0.0 . . . . ? N1 C1 C2 C3 0.0 . . . . ? C9 C1 C2 C3 180.0 . . . . ? C1 C2 C3 O1 180.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? O1 C3 C4 C5 0.0 . . . . ? C2 C3 C4 C5 180.0 . . . . ? O1 C3 C4 C8 180.0 . . . . ? C2 C3 C4 C8 0.0 . . . . ? C8 C4 C5 C6 0.0 . . . . ? C3 C4 C5 C6 180.0 . . . . ? C4 C5 C6 C7 0.0 . . . . ? C8 N2 C7 C6 0.0 . . . . ? C5 C6 C7 N2 0.0 . . . . ? C7 N2 C8 N1 180.0 . . . . ? C7 N2 C8 C4 0.0 . . . . ? C1 N1 C8 N2 180.0 . . . . ? C12 N1 C8 N2 0.0 . . . . ? C1 N1 C8 C4 0.0 . . . . ? C12 N1 C8 C4 180.0 . . . . ? C5 C4 C8 N2 0.0 . . . . ? C3 C4 C8 N2 180.0 . . . . ? C5 C4 C8 N1 180.0 . . . . ? C3 C4 C8 N1 0.0 . . . . ? C2 C1 C9 C10 0.0 . . . . ? N1 C1 C9 C10 180.0 . . . . ? C1 C9 C10 C11 180.0 . . . . ? C1 N1 C12 C13 -115.08(6) . . . . ? C8 N1 C12 C13 64.92(6) . . . . ? C1 N1 C12 C13 115.08(6) . . . 6 ? C8 N1 C12 C13 -64.92(6) . . . 6 ? N1 C12 C13 C14 174.80(7) . . . . ? C13 C12 C13 C14 -55.49(11) 6 . . . ? C12 C13 C14 C15 55.15(10) . . . . ? C13 C14 C15 C14 -56.32(13) . . . 6 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.370 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.050 # Attachment 'Ingo-Knepper-is_ikp272.cif' #============================================================================= data_is_ikp272 _database_code_depnum_ccdc_archive 'CCDC 834865' #TrackingRef 'Ingo-Knepper-is_ikp272.cif' _audit_author_name 'Villinger, A.' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H19 Br N2 O' _chemical_formula_sum 'C20 H19 Br N2 O' _chemical_formula_weight 383.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.2174(3) _cell_length_b 19.7268(7) _cell_length_c 10.0151(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.322(2) _cell_angle_gamma 90.00 _cell_volume 1707.69(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5267 _cell_measurement_theta_min 4.804 _cell_measurement_theta_max 59.184 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.95 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 2.416 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2074 _exptl_absorpt_correction_T_max 0.9096 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer' _diffrn_measurement_method 'phi and psi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20001 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4968 _reflns_number_gt 3720 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker Apex v2.0-2' _computing_cell_refinement 'Bruker Apex v2.0-2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL-97 #============================================================================== # REFINEMENT DATA _refine_special_details ; All H atoms were positioned geometrically and refined using a riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) = 1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles of all methyl groups were allowed to refine. 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^ > 2\s(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^)+(0.0367P)^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 4968 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0781 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.18278(2) 0.017574(10) 0.28576(2) 0.03043(7) Uani 1 1 d . . . N1 N 0.61331(16) 0.03922(7) 0.24764(14) 0.0182(3) Uani 1 1 d . . . N2 N 0.82905(17) -0.03049(7) 0.29436(15) 0.0231(3) Uani 1 1 d . . . O1 O 0.38214(15) -0.10787(7) 0.38824(13) 0.0311(3) Uani 1 1 d . . . C1 C 0.46490(18) 0.05023(9) 0.24662(16) 0.0177(3) Uani 1 1 d . . . C2 C 0.3867(2) 0.00146(9) 0.29222(17) 0.0202(3) Uani 1 1 d . . . C3 C 0.45062(19) -0.06380(9) 0.34462(16) 0.0214(4) Uani 1 1 d . . . C4 C 0.60585(19) -0.07374(9) 0.34033(16) 0.0196(3) Uani 1 1 d . . . C5 C 0.68446(19) -0.02294(9) 0.29557(16) 0.0191(3) Uani 1 1 d . . . C6 C 0.6824(2) -0.13580(9) 0.38269(17) 0.0245(4) Uani 1 1 d . . . H6 H 0.6322 -0.1720 0.4118 0.029 Uiso 1 1 calc R . . C7 C 0.8293(2) -0.14394(9) 0.38195(18) 0.0267(4) Uani 1 1 d . . . H7 H 0.8831 -0.1855 0.4110 0.032 Uiso 1 1 calc R . . C8 C 0.8980(2) -0.08969(10) 0.33743(18) 0.0266(4) Uani 1 1 d . . . H8 H 1.0005 -0.0954 0.3379 0.032 Uiso 1 1 calc R . . C9 C 0.39270(18) 0.11727(9) 0.19374(16) 0.0182(3) Uani 1 1 d . . . C10 C 0.4134(2) 0.17095(9) 0.28805(18) 0.0243(4) Uani 1 1 d . . . H10 H 0.4692 0.1644 0.3866 0.029 Uiso 1 1 calc R . . C11 C 0.3525(2) 0.23423(10) 0.23818(19) 0.0296(4) Uani 1 1 d . . . H11 H 0.3661 0.2708 0.3030 0.035 Uiso 1 1 calc R . . C12 C 0.2722(2) 0.24433(10) 0.09458(19) 0.0290(4) Uani 1 1 d . . . H12 H 0.2320 0.2878 0.0606 0.035 Uiso 1 1 calc R . . C13 C 0.2509(2) 0.19076(10) 0.00131(19) 0.0292(4) Uani 1 1 d . . . H13 H 0.1954 0.1975 -0.0972 0.035 Uiso 1 1 calc R . . C14 C 0.3098(2) 0.12705(10) 0.04975(17) 0.0248(4) Uani 1 1 d . . . H14 H 0.2935 0.0903 -0.0151 0.030 Uiso 1 1 calc R . . C15 C 0.69361(19) 0.09335(9) 0.19522(16) 0.0200(3) Uani 1 1 d . . . H15 H 0.6186 0.1319 0.1678 0.024 Uiso 1 1 calc R . . C16 C 0.8369(2) 0.12210(9) 0.30881(17) 0.0242(4) Uani 1 1 d . . . H16A H 0.9206 0.0878 0.3359 0.029 Uiso 1 1 calc R . . H16B H 0.8129 0.1342 0.3948 0.029 Uiso 1 1 calc R . . C17 C 0.8888(2) 0.18508(10) 0.2485(2) 0.0310(4) Uani 1 1 d . . . H17A H 0.8090 0.2208 0.2315 0.037 Uiso 1 1 calc R . . H17B H 0.9860 0.2026 0.3191 0.037 Uiso 1 1 calc R . . C18 C 0.9151(2) 0.16946(10) 0.10974(19) 0.0307(4) Uani 1 1 d . . . H18A H 0.9412 0.2119 0.0705 0.037 Uiso 1 1 calc R . . H18B H 1.0041 0.1382 0.1294 0.037 Uiso 1 1 calc R . . C19 C 0.7739(2) 0.13750(11) -0.00041(19) 0.0325(4) Uani 1 1 d . . . H19A H 0.7988 0.1251 -0.0858 0.039 Uiso 1 1 calc R . . H19B H 0.6883 0.1708 -0.0295 0.039 Uiso 1 1 calc R . . C20 C 0.7222(2) 0.07430(10) 0.05895(17) 0.0275(4) Uani 1 1 d . . . H20A H 0.6262 0.0560 -0.0118 0.033 Uiso 1 1 calc R . . H20B H 0.8033 0.0389 0.0794 0.033 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 0.02329(10) 0.02870(12) 0.04389(12) 0.00376(9) 0.01748(8) 0.00007(8) N1 0.0202(7) 0.0150(7) 0.0205(7) 0.0031(6) 0.0083(5) -0.0002(6) N2 0.0218(7) 0.0197(8) 0.0280(8) 0.0034(6) 0.0089(6) 0.0012(6) O1 0.0309(7) 0.0255(7) 0.0392(7) 0.0088(6) 0.0151(6) -0.0053(6) C1 0.0186(8) 0.0177(9) 0.0163(7) -0.0007(6) 0.0055(6) 0.0002(7) C2 0.0201(8) 0.0199(9) 0.0209(8) -0.0005(6) 0.0076(6) -0.0015(6) C3 0.0237(9) 0.0201(9) 0.0203(8) 0.0010(7) 0.0074(7) -0.0042(7) C4 0.0225(8) 0.0166(8) 0.0183(7) 0.0002(6) 0.0054(6) -0.0014(7) C5 0.0222(8) 0.0180(8) 0.0160(7) 0.0006(6) 0.0052(6) 0.0018(7) C6 0.0325(10) 0.0163(9) 0.0243(8) 0.0029(7) 0.0094(7) -0.0011(7) C7 0.0310(10) 0.0168(9) 0.0298(9) 0.0033(7) 0.0073(8) 0.0051(8) C8 0.0245(9) 0.0232(10) 0.0307(9) 0.0010(8) 0.0079(7) 0.0033(8) C9 0.0179(8) 0.0171(8) 0.0216(8) 0.0022(6) 0.0095(6) -0.0002(6) C10 0.0294(9) 0.0236(10) 0.0209(8) -0.0012(7) 0.0102(7) 0.0003(8) C11 0.0364(11) 0.0199(10) 0.0369(10) -0.0059(8) 0.0185(8) 0.0021(8) C12 0.0320(10) 0.0209(10) 0.0396(10) 0.0069(8) 0.0192(8) 0.0072(8) C13 0.0322(10) 0.0283(11) 0.0265(9) 0.0072(8) 0.0093(8) 0.0061(8) C14 0.0284(10) 0.0220(9) 0.0222(8) -0.0005(7) 0.0067(7) 0.0026(8) C15 0.0227(9) 0.0154(8) 0.0230(8) 0.0048(7) 0.0094(7) 0.0001(7) C16 0.0287(9) 0.0214(9) 0.0226(8) -0.0003(7) 0.0088(7) -0.0033(8) C17 0.0322(11) 0.0220(10) 0.0367(10) 0.0002(8) 0.0094(8) -0.0075(8) C18 0.0315(10) 0.0238(10) 0.0423(11) 0.0089(9) 0.0198(9) -0.0023(8) C19 0.0420(12) 0.0320(12) 0.0285(9) 0.0057(8) 0.0185(9) -0.0037(9) C20 0.0361(11) 0.0258(10) 0.0224(8) -0.0013(7) 0.0125(8) -0.0074(8) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.8852(17) . ? N1 C1 1.382(2) . ? N1 C5 1.395(2) . ? N1 C15 1.495(2) . ? N2 C8 1.328(2) . ? N2 C5 1.345(2) . ? O1 C3 1.240(2) . ? C1 C2 1.372(2) . ? C1 C9 1.493(2) . ? C2 C3 1.437(2) . ? C3 C4 1.460(2) . ? C4 C5 1.399(2) . ? C4 C6 1.403(2) . ? C6 C7 1.366(2) . ? C6 H6 0.9500 . ? C7 C8 1.393(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.387(2) . ? C9 C14 1.391(2) . ? C10 C11 1.389(3) . ? C10 H10 0.9500 . ? C11 C12 1.384(2) . ? C11 H11 0.9500 . ? C12 C13 1.379(3) . ? C12 H12 0.9500 . ? C13 C14 1.388(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.522(2) . ? C15 C20 1.524(2) . ? C15 H15 1.0000 . ? C16 C17 1.529(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.523(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.520(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.527(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 119.13(14) . . ? C1 N1 C15 119.66(14) . . ? C5 N1 C15 121.20(13) . . ? C8 N2 C5 117.26(15) . . ? C2 C1 N1 121.37(16) . . ? C2 C1 C9 121.23(15) . . ? N1 C1 C9 117.41(14) . . ? C1 C2 C3 123.62(16) . . ? C1 C2 Br1 120.21(13) . . ? C3 C2 Br1 116.17(12) . . ? O1 C3 C2 124.24(16) . . ? O1 C3 C4 122.71(17) . . ? C2 C3 C4 113.04(15) . . ? C5 C4 C6 117.39(16) . . ? C5 C4 C3 122.37(16) . . ? C6 C4 C3 120.23(16) . . ? N2 C5 N1 116.30(15) . . ? N2 C5 C4 123.28(15) . . ? N1 C5 C4 120.41(15) . . ? C7 C6 C4 119.75(17) . . ? C7 C6 H6 120.1 . . ? C4 C6 H6 120.1 . . ? C6 C7 C8 118.23(17) . . ? C6 C7 H7 120.9 . . ? C8 C7 H7 120.9 . . ? N2 C8 C7 124.07(18) . . ? N2 C8 H8 118.0 . . ? C7 C8 H8 118.0 . . ? C10 C9 C14 119.74(16) . . ? C10 C9 C1 119.72(14) . . ? C14 C9 C1 120.50(15) . . ? C9 C10 C11 119.89(16) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 120.44(17) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 119.50(18) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.73(17) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C13 C14 C9 119.69(17) . . ? C13 C14 H14 120.2 . . ? C9 C14 H14 120.2 . . ? N1 C15 C16 114.25(13) . . ? N1 C15 C20 113.52(14) . . ? C16 C15 C20 112.70(14) . . ? N1 C15 H15 105.1 . . ? C16 C15 H15 105.1 . . ? C20 C15 H15 105.1 . . ? C15 C16 C17 108.48(14) . . ? C15 C16 H16A 110.0 . . ? C17 C16 H16A 110.0 . . ? C15 C16 H16B 110.0 . . ? C17 C16 H16B 110.0 . . ? H16A C16 H16B 108.4 . . ? C18 C17 C16 111.52(16) . . ? C18 C17 H17A 109.3 . . ? C16 C17 H17A 109.3 . . ? C18 C17 H17B 109.3 . . ? C16 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? C19 C18 C17 112.27(15) . . ? C19 C18 H18A 109.1 . . ? C17 C18 H18A 109.1 . . ? C19 C18 H18B 109.1 . . ? C17 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C18 C19 C20 111.11(15) . . ? C18 C19 H19A 109.4 . . ? C20 C19 H19A 109.4 . . ? C18 C19 H19B 109.4 . . ? C20 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C15 C20 C19 108.76(15) . . ? C15 C20 H20A 109.9 . . ? C19 C20 H20A 109.9 . . ? C15 C20 H20B 109.9 . . ? C19 C20 H20B 109.9 . . ? H20A C20 H20B 108.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 0.3(2) . . . . ? C15 N1 C1 C2 179.18(14) . . . . ? C5 N1 C1 C9 -179.66(13) . . . . ? C15 N1 C1 C9 -0.7(2) . . . . ? N1 C1 C2 C3 0.3(2) . . . . ? C9 C1 C2 C3 -179.76(15) . . . . ? N1 C1 C2 Br1 -178.73(11) . . . . ? C9 C1 C2 Br1 1.2(2) . . . . ? C1 C2 C3 O1 178.79(16) . . . . ? Br1 C2 C3 O1 -2.1(2) . . . . ? C1 C2 C3 C4 -1.8(2) . . . . ? Br1 C2 C3 C4 177.33(11) . . . . ? O1 C3 C4 C5 -177.75(15) . . . . ? C2 C3 C4 C5 2.8(2) . . . . ? O1 C3 C4 C6 1.9(3) . . . . ? C2 C3 C4 C6 -177.56(15) . . . . ? C8 N2 C5 N1 -178.94(14) . . . . ? C8 N2 C5 C4 0.4(2) . . . . ? C1 N1 C5 N2 -179.82(14) . . . . ? C15 N1 C5 N2 1.3(2) . . . . ? C1 N1 C5 C4 0.8(2) . . . . ? C15 N1 C5 C4 -178.12(14) . . . . ? C6 C4 C5 N2 -1.4(2) . . . . ? C3 C4 C5 N2 178.21(15) . . . . ? C6 C4 C5 N1 177.90(15) . . . . ? C3 C4 C5 N1 -2.4(2) . . . . ? C5 C4 C6 C7 1.4(2) . . . . ? C3 C4 C6 C7 -178.22(15) . . . . ? C4 C6 C7 C8 -0.5(3) . . . . ? C5 N2 C8 C7 0.6(3) . . . . ? C6 C7 C8 N2 -0.6(3) . . . . ? C2 C1 C9 C10 91.2(2) . . . . ? N1 C1 C9 C10 -88.89(19) . . . . ? C2 C1 C9 C14 -91.3(2) . . . . ? N1 C1 C9 C14 88.66(19) . . . . ? C14 C9 C10 C11 -0.6(3) . . . . ? C1 C9 C10 C11 177.00(16) . . . . ? C9 C10 C11 C12 -0.5(3) . . . . ? C10 C11 C12 C13 0.9(3) . . . . ? C11 C12 C13 C14 -0.3(3) . . . . ? C12 C13 C14 C9 -0.8(3) . . . . ? C10 C9 C14 C13 1.2(3) . . . . ? C1 C9 C14 C13 -176.35(16) . . . . ? C1 N1 C15 C16 115.70(16) . . . . ? C5 N1 C15 C16 -65.39(19) . . . . ? C1 N1 C15 C20 -113.17(17) . . . . ? C5 N1 C15 C20 65.74(19) . . . . ? N1 C15 C16 C17 -169.49(14) . . . . ? C20 C15 C16 C17 59.0(2) . . . . ? C15 C16 C17 C18 -55.3(2) . . . . ? C16 C17 C18 C19 54.8(2) . . . . ? C17 C18 C19 C20 -54.9(2) . . . . ? N1 C15 C20 C19 168.69(15) . . . . ? C16 C15 C20 C19 -59.4(2) . . . . ? C18 C19 C20 C15 55.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.662 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.068 # Attachment 'Ingo-Knepper-rk_ikp165.cif' #============================================================================= data_rk_1kp165 _database_code_depnum_ccdc_archive 'CCDC 834866' #TrackingRef 'Ingo-Knepper-rk_ikp165.cif' _audit_author_name 'Villinger, A., Kuzora, R.' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H8 Cl N O' _chemical_formula_sum 'C14 H8 Cl N O' _chemical_formula_weight 241.66 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' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 11.4766(8) _cell_length_b 3.8102(2) _cell_length_c 25.7302(16) _cell_angle_alpha 90.00 _cell_angle_beta 94.941(4) _cell_angle_gamma 90.00 _cell_volume 1120.95(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4896 _cell_measurement_theta_min 4.565 _cell_measurement_theta_max 64.805 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.320 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9158 _exptl_absorpt_correction_T_max 0.9657 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex Kappa II-CCD-diffractometer' _diffrn_measurement_method 'phi and psi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14319 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3266 _reflns_number_gt 2521 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker Apex v2.0-2' _computing_cell_refinement 'Bruker Apex v2.0-2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL-97 #============================================================================== # REFINEMENT DATA _refine_special_details ; All H atoms were positioned geometrically and refined using a riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) = 1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles of all methyl groups were allowed to refine. 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^ > 2\s(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^)+(0.0522P)^2^+0.1515P] 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 3266 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0991 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.11521(3) 0.63207(9) 0.122634(13) 0.03213(11) Uani 1 1 d . . . N1 N 0.10479(9) 0.3597(3) 0.21377(4) 0.0298(3) Uani 1 1 d . . . O1 O 0.48040(8) 0.5888(3) 0.16196(4) 0.0399(3) Uani 1 1 d . . . C9 C 0.29132(11) 0.1307(3) -0.00037(5) 0.0229(2) Uani 1 1 d . . . C5 C 0.29964(10) 0.3824(3) 0.18592(4) 0.0200(2) Uani 1 1 d . . . C8 C 0.33112(11) 0.2544(4) 0.05037(5) 0.0254(3) Uani 1 1 d . . . C10 C 0.36319(12) 0.1357(3) -0.04133(5) 0.0274(3) Uani 1 1 d . . . H10 H 0.4408 0.2227 -0.0359 0.033 Uiso 1 1 calc R . . C13 C 0.13564(12) -0.1150(4) -0.05796(5) 0.0316(3) Uani 1 1 d . . . H13 H 0.0577 -0.1996 -0.0638 0.038 Uiso 1 1 calc R . . C1 C 0.17892(10) 0.4350(3) 0.17902(5) 0.0226(2) Uani 1 1 d . . . C4 C 0.34320(10) 0.2490(3) 0.23410(5) 0.0223(2) Uani 1 1 d . . . H4 H 0.4249 0.2143 0.2414 0.027 Uiso 1 1 calc R . . C7 C 0.35730(11) 0.3565(3) 0.09394(5) 0.0264(3) Uani 1 1 d . . . C3 C 0.26746(12) 0.1670(4) 0.27122(5) 0.0279(3) Uani 1 1 d . . . H3 H 0.2959 0.0747 0.3042 0.034 Uiso 1 1 calc R . . C12 C 0.20754(14) -0.1100(4) -0.09833(5) 0.0334(3) Uani 1 1 d . . . H12 H 0.1789 -0.1915 -0.1319 0.040 Uiso 1 1 calc R . . C6 C 0.38650(10) 0.4604(3) 0.14723(5) 0.0241(3) Uani 1 1 d . . . C11 C 0.32103(13) 0.0132(4) -0.09011(5) 0.0334(3) Uani 1 1 d . . . H11 H 0.3702 0.0138 -0.1180 0.040 Uiso 1 1 calc R . . C14 C 0.17702(11) 0.0030(4) -0.00901(5) 0.0280(3) Uani 1 1 d . . . H14 H 0.1277 -0.0026 0.0188 0.034 Uiso 1 1 calc R . . C2 C 0.14927(12) 0.2226(4) 0.25914(5) 0.0320(3) Uani 1 1 d . . . H2 H 0.0969 0.1605 0.2843 0.038 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 Cl1 0.02924(17) 0.03251(19) 0.03220(18) 0.00104(13) -0.01142(12) 0.00468(13) N1 0.0203(5) 0.0359(6) 0.0332(6) -0.0052(5) 0.0022(4) -0.0020(4) O1 0.0277(5) 0.0638(7) 0.0277(5) -0.0036(5) 0.0004(4) -0.0181(5) C9 0.0278(6) 0.0206(6) 0.0199(6) 0.0018(4) -0.0003(5) 0.0025(5) C5 0.0196(5) 0.0194(5) 0.0203(5) -0.0036(4) -0.0019(4) -0.0022(4) C8 0.0269(6) 0.0248(6) 0.0244(6) 0.0012(5) 0.0015(5) -0.0001(5) C10 0.0281(6) 0.0291(7) 0.0251(6) 0.0023(5) 0.0033(5) 0.0005(5) C13 0.0303(6) 0.0296(7) 0.0332(7) -0.0007(6) -0.0065(5) -0.0033(5) C1 0.0216(5) 0.0207(6) 0.0246(6) -0.0038(5) -0.0038(4) -0.0004(4) C4 0.0200(5) 0.0243(6) 0.0219(6) -0.0011(5) -0.0024(4) -0.0006(5) C7 0.0259(6) 0.0295(7) 0.0239(6) -0.0003(5) 0.0026(5) -0.0036(5) C3 0.0313(6) 0.0311(7) 0.0212(6) 0.0014(5) 0.0007(5) -0.0045(5) C12 0.0474(8) 0.0289(7) 0.0222(6) -0.0039(5) -0.0063(6) 0.0055(6) C6 0.0224(6) 0.0278(6) 0.0216(6) -0.0010(5) -0.0007(4) -0.0028(5) C11 0.0426(8) 0.0369(8) 0.0216(6) 0.0011(6) 0.0072(5) 0.0055(6) C14 0.0284(6) 0.0307(7) 0.0250(6) 0.0000(5) 0.0030(5) -0.0001(5) C2 0.0287(6) 0.0388(8) 0.0293(7) -0.0014(6) 0.0072(5) -0.0064(6) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 1.7380(12) . ? N1 C1 1.3178(17) . ? N1 C2 1.3393(18) . ? O1 C6 1.2140(15) . ? C9 C10 1.3934(18) . ? C9 C14 1.3989(18) . ? C9 C8 1.4256(17) . ? C5 C4 1.3923(16) . ? C5 C1 1.3960(16) . ? C5 C6 1.4980(17) . ? C8 C7 1.2001(18) . ? C10 C11 1.3865(19) . ? C10 H10 0.9500 . ? C13 C12 1.381(2) . ? C13 C14 1.3824(18) . ? C13 H13 0.9500 . ? C4 C3 1.3816(17) . ? C4 H4 0.9500 . ? C7 C6 1.4387(17) . ? C3 C2 1.3816(19) . ? C3 H3 0.9500 . ? C12 C11 1.383(2) . ? C12 H12 0.9500 . ? C11 H11 0.9500 . ? C14 H14 0.9500 . ? C2 H2 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 117.16(11) . . ? C10 C9 C14 119.51(11) . . ? C10 C9 C8 121.63(12) . . ? C14 C9 C8 118.86(11) . . ? C4 C5 C1 116.23(11) . . ? C4 C5 C6 117.11(10) . . ? C1 C5 C6 126.66(11) . . ? C7 C8 C9 175.75(13) . . ? C11 C10 C9 119.80(12) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C12 C13 C14 120.00(13) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? N1 C1 C5 125.04(11) . . ? N1 C1 Cl1 114.25(9) . . ? C5 C1 Cl1 120.64(10) . . ? C3 C4 C5 119.94(11) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C8 C7 C6 176.79(14) . . ? C2 C3 C4 118.28(12) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C13 C12 C11 120.35(12) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? O1 C6 C7 122.42(11) . . ? O1 C6 C5 119.74(11) . . ? C7 C6 C5 117.71(10) . . ? C12 C11 C10 120.22(13) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C14 C9 120.13(12) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? N1 C2 C3 123.30(12) . . ? N1 C2 H2 118.4 . . ? C3 C2 H2 118.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C9 C8 C7 171.1(19) . . . . ? C14 C9 C8 C7 -9(2) . . . . ? C14 C9 C10 C11 -0.23(19) . . . . ? C8 C9 C10 C11 -179.94(13) . . . . ? C2 N1 C1 C5 0.1(2) . . . . ? C2 N1 C1 Cl1 -176.92(10) . . . . ? C4 C5 C1 N1 -1.86(19) . . . . ? C6 C5 C1 N1 179.24(12) . . . . ? C4 C5 C1 Cl1 174.95(9) . . . . ? C6 C5 C1 Cl1 -3.96(18) . . . . ? C1 C5 C4 C3 1.89(18) . . . . ? C6 C5 C4 C3 -179.10(11) . . . . ? C9 C8 C7 C6 61(4) . . . . ? C5 C4 C3 C2 -0.29(19) . . . . ? C14 C13 C12 C11 -0.1(2) . . . . ? C8 C7 C6 O1 131(2) . . . . ? C8 C7 C6 C5 -44(3) . . . . ? C4 C5 C6 O1 -39.33(18) . . . . ? C1 C5 C6 O1 139.57(14) . . . . ? C4 C5 C6 C7 136.59(12) . . . . ? C1 C5 C6 C7 -44.51(18) . . . . ? C13 C12 C11 C10 -0.6(2) . . . . ? C9 C10 C11 C12 0.7(2) . . . . ? C12 C13 C14 C9 0.6(2) . . . . ? C10 C9 C14 C13 -0.4(2) . . . . ? C8 C9 C14 C13 179.28(12) . . . . ? C1 N1 C2 C3 1.8(2) . . . . ? C4 C3 C2 N1 -1.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.363 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.047 #===================== End of CIF submission ================================= # Attachment 'Ingo-Knepper-rk_ikp169.cif' #============================================================================= data_rk_ikp169 _database_code_depnum_ccdc_archive 'CCDC 834867' #TrackingRef 'Ingo-Knepper-rk_ikp169.cif' _audit_author_name 'Villinger, A., Kuzora, R.' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 N2 O1, H1 O0.5' _chemical_formula_sum 'C22 H19 N2 O1.50' _chemical_formula_weight 335.39 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' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 8.6083(6) _cell_length_b 26.5181(19) _cell_length_c 7.4938(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.838(4) _cell_angle_gamma 90.00 _cell_volume 1690.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5309 _cell_measurement_theta_min 5.690 _cell_measurement_theta_max 62.150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9634 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex Kappa II-CCD-diffractometer' _diffrn_measurement_method 'phi and psi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20776 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4921 _reflns_number_gt 3391 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker Apex v2.0-2' _computing_cell_refinement 'Bruker Apex v2.0-2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL-97 #============================================================================== # REFINEMENT DATA _refine_special_details ; All H atoms were positioned geometrically and refined using a riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) = 1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles of all methyl groups were allowed to refine. 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^ > 2\s(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^)+(0.0601P)^2^+0.2215P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4921 _refine_ls_number_parameters 243 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1177 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.70589(13) 0.42436(4) 0.56691(14) 0.0352(2) Uani 1 1 d . . . N2 N 0.45988(11) 0.39038(3) 0.57037(12) 0.0265(2) Uani 1 1 d . . . O1 O 0.27638(12) 0.46853(4) 0.11458(13) 0.0511(3) Uani 1 1 d . . . C1 C 0.55627(14) 0.42204(4) 0.48863(14) 0.0270(2) Uani 1 1 d . . . C2 C 0.80114(18) 0.45323(5) 0.48804(19) 0.0429(3) Uani 1 1 d . . . H2 H 0.9080 0.4554 0.5429 0.051 Uiso 1 1 calc R . . C3 C 0.75523(18) 0.48047(5) 0.33070(18) 0.0424(3) Uani 1 1 d . . . H3 H 0.8292 0.4997 0.2776 0.051 Uiso 1 1 calc R . . C4 C 0.60167(17) 0.47886(4) 0.25484(16) 0.0357(3) Uani 1 1 d . . . H4 H 0.5663 0.4978 0.1488 0.043 Uiso 1 1 calc R . . C5 C 0.49558(15) 0.44926(4) 0.33282(15) 0.0294(3) Uani 1 1 d . . . C6 C 0.33070(16) 0.44541(5) 0.25533(15) 0.0347(3) Uani 1 1 d . . . C7 C 0.23969(15) 0.41372(5) 0.35314(16) 0.0343(3) Uani 1 1 d . . . H7 H 0.1301 0.4107 0.3122 0.041 Uiso 1 1 calc R . . C8 C 0.30414(14) 0.38756(4) 0.50358(15) 0.0287(2) Uani 1 1 d . . . C9 C 0.20159(14) 0.35626(5) 0.60290(16) 0.0331(3) Uani 1 1 d . . . C10 C 0.12035(19) 0.37896(6) 0.7251(2) 0.0525(4) Uani 1 1 d . . . H10 H 0.1350 0.4139 0.7503 0.063 Uiso 1 1 calc R . . C11 C 0.0173(2) 0.35146(7) 0.8121(3) 0.0655(5) Uani 1 1 d . . . H11 H -0.0396 0.3677 0.8947 0.079 Uiso 1 1 calc R . . C12 C -0.00256(18) 0.30116(7) 0.7792(2) 0.0575(5) Uani 1 1 d . . . H12 H -0.0738 0.2824 0.8382 0.069 Uiso 1 1 calc R . . C13 C 0.08031(19) 0.27770(6) 0.6611(2) 0.0531(4) Uani 1 1 d . . . H13 H 0.0688 0.2424 0.6410 0.064 Uiso 1 1 calc R . . C14 C 0.18086(17) 0.30510(6) 0.57058(18) 0.0427(3) Uani 1 1 d . . . H14 H 0.2357 0.2888 0.4862 0.051 Uiso 1 1 calc R . . C15 C 0.52963(14) 0.36030(4) 0.72790(14) 0.0264(2) Uani 1 1 d . . . H15A H 0.6372 0.3500 0.7120 0.032 Uiso 1 1 calc R . . H15B H 0.4666 0.3293 0.7338 0.032 Uiso 1 1 calc R . . C16 C 0.53724(16) 0.38895(4) 0.90507(15) 0.0330(3) Uani 1 1 d . . . H16A H 0.6163 0.4162 0.9102 0.040 Uiso 1 1 calc R . . H16B H 0.4338 0.4045 0.9120 0.040 Uiso 1 1 calc R . . C17 C 0.58084(14) 0.35374(4) 1.06268(14) 0.0275(2) Uani 1 1 d . . . C18 C 0.47067(15) 0.32023(5) 1.11186(16) 0.0328(3) Uani 1 1 d . . . H18 H 0.3672 0.3197 1.0458 0.039 Uiso 1 1 calc R . . C19 C 0.51020(16) 0.28759(5) 1.25638(17) 0.0365(3) Uani 1 1 d . . . H19 H 0.4341 0.2647 1.2880 0.044 Uiso 1 1 calc R . . C20 C 0.65860(17) 0.28829(5) 1.35369(17) 0.0388(3) Uani 1 1 d . . . H20 H 0.6854 0.2661 1.4533 0.047 Uiso 1 1 calc R . . C21 C 0.76849(16) 0.32130(5) 1.30605(17) 0.0391(3) Uani 1 1 d . . . H21 H 0.8716 0.3219 1.3730 0.047 Uiso 1 1 calc R . . C22 C 0.72970(15) 0.35371(5) 1.16103(16) 0.0322(3) Uani 1 1 d . . . H22 H 0.8068 0.3762 1.1291 0.039 Uiso 1 1 calc R . . O2 O -0.0273(4) 0.46046(13) -0.0369(5) 0.0803(10) Uani 0.50 1 d P . . H1A H -0.073(6) 0.485(2) -0.060(7) 0.089(17) Uiso 0.50 1 d P . . H1B H 0.063(7) 0.470(2) 0.033(8) 0.101(16) Uiso 0.50 1 d P . . 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 0.0398(6) 0.0360(6) 0.0285(5) 0.0023(4) 0.0013(4) -0.0055(4) N2 0.0321(5) 0.0277(5) 0.0195(4) 0.0046(4) 0.0032(4) 0.0048(4) O1 0.0537(6) 0.0663(7) 0.0341(5) 0.0250(5) 0.0088(5) 0.0222(5) C1 0.0370(6) 0.0241(5) 0.0206(5) -0.0001(4) 0.0065(4) 0.0034(4) C2 0.0468(8) 0.0426(7) 0.0380(7) 0.0008(6) 0.0023(6) -0.0145(6) C3 0.0591(9) 0.0337(7) 0.0358(7) -0.0004(5) 0.0120(6) -0.0149(6) C4 0.0603(9) 0.0239(6) 0.0244(6) 0.0020(4) 0.0110(6) 0.0014(5) C5 0.0442(7) 0.0246(5) 0.0203(5) 0.0011(4) 0.0083(5) 0.0080(5) C6 0.0438(7) 0.0382(7) 0.0231(5) 0.0066(5) 0.0086(5) 0.0169(5) C7 0.0329(6) 0.0435(7) 0.0262(6) 0.0060(5) 0.0035(5) 0.0120(5) C8 0.0320(6) 0.0321(6) 0.0224(5) 0.0017(4) 0.0055(4) 0.0090(5) C9 0.0286(6) 0.0408(7) 0.0291(6) 0.0100(5) 0.0023(5) 0.0067(5) C10 0.0578(10) 0.0448(8) 0.0625(10) 0.0169(7) 0.0330(8) 0.0162(7) C11 0.0588(11) 0.0751(12) 0.0720(12) 0.0281(9) 0.0396(9) 0.0196(9) C12 0.0382(8) 0.0778(12) 0.0548(10) 0.0339(9) 0.0022(7) -0.0081(8) C13 0.0544(9) 0.0565(9) 0.0429(8) 0.0119(7) -0.0100(7) -0.0185(7) C14 0.0454(8) 0.0486(8) 0.0317(7) 0.0007(6) -0.0018(6) -0.0074(6) C15 0.0335(6) 0.0250(5) 0.0199(5) 0.0040(4) 0.0013(4) 0.0048(4) C16 0.0505(8) 0.0270(6) 0.0212(5) 0.0026(4) 0.0046(5) 0.0063(5) C17 0.0399(7) 0.0253(5) 0.0182(5) -0.0007(4) 0.0068(4) 0.0061(5) C18 0.0355(7) 0.0332(6) 0.0294(6) 0.0007(5) 0.0040(5) 0.0038(5) C19 0.0479(8) 0.0305(6) 0.0341(6) 0.0048(5) 0.0161(6) 0.0035(5) C20 0.0552(9) 0.0368(7) 0.0255(6) 0.0082(5) 0.0098(6) 0.0147(6) C21 0.0383(7) 0.0475(8) 0.0301(6) 0.0023(5) 0.0009(5) 0.0119(6) C22 0.0361(7) 0.0346(6) 0.0269(6) -0.0010(5) 0.0085(5) 0.0023(5) O2 0.0499(17) 0.083(2) 0.099(2) -0.0259(17) -0.0153(15) 0.0290(15) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.3253(17) . ? N1 C1 1.3322(16) . ? N2 C8 1.3592(15) . ? N2 C1 1.3873(15) . ? N2 C15 1.4739(13) . ? O1 C6 1.2472(14) . ? C1 C5 1.4035(15) . ? C2 C3 1.387(2) . ? C2 H2 0.9500 . ? C3 C4 1.357(2) . ? C3 H3 0.9500 . ? C4 C5 1.3985(17) . ? C4 H4 0.9500 . ? C5 C6 1.4522(19) . ? C6 C7 1.4260(18) . ? C7 C8 1.3667(16) . ? C7 H7 0.9500 . ? C8 C9 1.4914(17) . ? C9 C10 1.3737(18) . ? C9 C14 1.385(2) . ? C10 C11 1.386(2) . ? C10 H10 0.9500 . ? C11 C12 1.362(3) . ? C11 H11 0.9500 . ? C12 C13 1.369(2) . ? C12 H12 0.9500 . ? C13 C14 1.385(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.5223(15) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.5070(15) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C22 1.3766(17) . ? C17 C18 1.3900(17) . ? C18 C19 1.3873(17) . ? C18 H18 0.9500 . ? C19 C20 1.370(2) . ? C19 H19 0.9500 . ? C20 C21 1.376(2) . ? C20 H20 0.9500 . ? C21 C22 1.3856(17) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? O2 H1A 0.77(6) . ? O2 H1B 0.90(7) . ? 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 C2 N1 C1 116.93(11) . . ? C8 N2 C1 119.58(9) . . ? C8 N2 C15 121.50(9) . . ? C1 N2 C15 118.91(9) . . ? N1 C1 N2 115.91(10) . . ? N1 C1 C5 123.62(11) . . ? N2 C1 C5 120.47(11) . . ? N1 C2 C3 124.39(13) . . ? N1 C2 H2 117.8 . . ? C3 C2 H2 117.8 . . ? C4 C3 C2 118.13(12) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C3 C4 C5 119.96(12) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C1 116.92(12) . . ? C4 C5 C6 122.23(11) . . ? C1 C5 C6 120.83(11) . . ? O1 C6 C7 124.07(13) . . ? O1 C6 C5 121.33(12) . . ? C7 C6 C5 114.60(10) . . ? C8 C7 C6 122.53(12) . . ? C8 C7 H7 118.7 . . ? C6 C7 H7 118.7 . . ? N2 C8 C7 121.89(11) . . ? N2 C8 C9 118.22(10) . . ? C7 C8 C9 119.86(11) . . ? C10 C9 C14 118.74(13) . . ? C10 C9 C8 119.33(12) . . ? C14 C9 C8 121.89(11) . . ? C9 C10 C11 120.74(15) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 120.12(16) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 119.89(14) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 120.36(15) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C9 120.12(14) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? N2 C15 C16 112.71(9) . . ? N2 C15 H15A 109.0 . . ? C16 C15 H15A 109.0 . . ? N2 C15 H15B 109.0 . . ? C16 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C17 C16 C15 110.28(9) . . ? C17 C16 H16A 109.6 . . ? C15 C16 H16A 109.6 . . ? C17 C16 H16B 109.6 . . ? C15 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? C22 C17 C18 118.33(10) . . ? C22 C17 C16 121.28(11) . . ? C18 C17 C16 120.39(11) . . ? C19 C18 C17 120.69(12) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C20 C19 C18 120.25(12) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 119.50(11) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C20 C21 C22 120.39(12) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C17 C22 C21 120.84(12) . . ? C17 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? H1A O2 H1B 105(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 N2 178.07(11) . . . . ? C2 N1 C1 C5 -1.80(17) . . . . ? C8 N2 C1 N1 177.12(10) . . . . ? C15 N2 C1 N1 -3.17(14) . . . . ? C8 N2 C1 C5 -3.02(15) . . . . ? C15 N2 C1 C5 176.70(9) . . . . ? C1 N1 C2 C3 -0.4(2) . . . . ? N1 C2 C3 C4 2.1(2) . . . . ? C2 C3 C4 C5 -1.62(19) . . . . ? C3 C4 C5 C1 -0.36(17) . . . . ? C3 C4 C5 C6 -178.81(11) . . . . ? N1 C1 C5 C4 2.18(16) . . . . ? N2 C1 C5 C4 -177.67(10) . . . . ? N1 C1 C5 C6 -179.34(11) . . . . ? N2 C1 C5 C6 0.80(16) . . . . ? C4 C5 C6 O1 0.07(18) . . . . ? C1 C5 C6 O1 -178.32(11) . . . . ? C4 C5 C6 C7 -179.76(11) . . . . ? C1 C5 C6 C7 1.85(16) . . . . ? O1 C6 C7 C8 177.70(12) . . . . ? C5 C6 C7 C8 -2.48(17) . . . . ? C1 N2 C8 C7 2.46(16) . . . . ? C15 N2 C8 C7 -177.25(10) . . . . ? C1 N2 C8 C9 -175.36(10) . . . . ? C15 N2 C8 C9 4.93(15) . . . . ? C6 C7 C8 N2 0.40(19) . . . . ? C6 C7 C8 C9 178.19(11) . . . . ? N2 C8 C9 C10 95.47(15) . . . . ? C7 C8 C9 C10 -82.40(17) . . . . ? N2 C8 C9 C14 -87.07(15) . . . . ? C7 C8 C9 C14 95.06(15) . . . . ? C14 C9 C10 C11 -1.2(2) . . . . ? C8 C9 C10 C11 176.34(15) . . . . ? C9 C10 C11 C12 1.1(3) . . . . ? C10 C11 C12 C13 0.5(3) . . . . ? C11 C12 C13 C14 -1.9(2) . . . . ? C12 C13 C14 C9 1.8(2) . . . . ? C10 C9 C14 C13 -0.2(2) . . . . ? C8 C9 C14 C13 -177.72(12) . . . . ? C8 N2 C15 C16 -93.99(13) . . . . ? C1 N2 C15 C16 86.30(12) . . . . ? N2 C15 C16 C17 169.52(10) . . . . ? C15 C16 C17 C22 104.34(13) . . . . ? C15 C16 C17 C18 -75.49(14) . . . . ? C22 C17 C18 C19 -0.07(17) . . . . ? C16 C17 C18 C19 179.76(10) . . . . ? C17 C18 C19 C20 0.54(18) . . . . ? C18 C19 C20 C21 -0.55(19) . . . . ? C19 C20 C21 C22 0.12(19) . . . . ? C18 C17 C22 C21 -0.36(17) . . . . ? C16 C17 C22 C21 179.81(11) . . . . ? C20 C21 C22 C17 0.35(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.251 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.043 #===================== End of CIF submission ================================= # Attachment 'Sergii-Dudkin-rk_sd120.cif' #============================================================================= data_is_ag045 _database_code_depnum_ccdc_archive 'CCDC 834868' #TrackingRef 'Sergii-Dudkin-rk_sd120.cif' _audit_author_name 'Villinger, A., Kuzora, R.' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H24 Cl N3 O2' _chemical_formula_sum 'C27 H24 Cl N3 O2' _chemical_formula_weight 457.94 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' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9870(4) _cell_length_b 10.6502(4) _cell_length_c 11.9022(5) _cell_angle_alpha 94.557(2) _cell_angle_beta 114.488(2) _cell_angle_gamma 93.883(2) _cell_volume 1141.35(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5389 _cell_measurement_theta_min 4.501 _cell_measurement_theta_max 60.422 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9672 _exptl_absorpt_correction_T_max 0.9786 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex Kappa II-CCD-diffractometer' _diffrn_measurement_method 'phi and psi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25092 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0461 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6633 _reflns_number_gt 4591 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker Apex v2.0-2' _computing_cell_refinement 'Bruker Apex v2.0-2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL-97 #============================================================================== # REFINEMENT DATA _refine_special_details ; All H atoms were positioned geometrically and refined using a riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) = 1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles of all methyl groups were allowed to refine. 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^ > 2\s(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^)+(0.0614P)^2^+0.0052P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6633 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1160 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 -0.00750(4) 0.16378(3) 0.45378(3) 0.03123(10) Uani 1 1 d . . . N1 N -0.13337(13) 0.11552(11) 0.20875(11) 0.0262(3) Uani 1 1 d . . . N2 N -0.15679(14) 0.16307(11) 0.09929(11) 0.0322(3) Uani 1 1 d . . . N3 N 0.25292(14) 0.65695(11) 0.47380(13) 0.0300(3) Uani 1 1 d . . . O1 O 0.05267(12) 0.52337(9) 0.27220(10) 0.0352(3) Uani 1 1 d . . . O2 O 0.25392(13) 1.15845(10) 0.21145(11) 0.0386(3) Uani 1 1 d . . . C1 C -0.04533(15) 0.19878(13) 0.30739(13) 0.0232(3) Uani 1 1 d . . . C2 C -0.00870(15) 0.30641(12) 0.26427(13) 0.0238(3) Uani 1 1 d . . . C3 C -0.08151(16) 0.27758(13) 0.13361(13) 0.0288(3) Uani 1 1 d . . . C4 C -0.0778(2) 0.35576(16) 0.03590(15) 0.0452(4) Uani 1 1 d . . . H4A H -0.1376 0.3093 -0.0465 0.068 Uiso 1 1 calc R . . H4B H 0.0247 0.3734 0.0466 0.068 Uiso 1 1 calc R . . H4C H -0.1180 0.4358 0.0435 0.068 Uiso 1 1 calc R . . C5 C -0.20177(16) -0.00821(13) 0.20605(13) 0.0261(3) Uani 1 1 d . . . C6 C -0.35343(17) -0.02748(15) 0.16212(15) 0.0347(3) Uani 1 1 d . . . H6 H -0.4118 0.0404 0.1355 0.042 Uiso 1 1 calc R . . C7 C -0.41946(19) -0.14753(16) 0.15741(17) 0.0424(4) Uani 1 1 d . . . H7 H -0.5240 -0.1624 0.1273 0.051 Uiso 1 1 calc R . . C8 C -0.3339(2) -0.24615(16) 0.19639(15) 0.0423(4) Uani 1 1 d . . . H8 H -0.3798 -0.3281 0.1938 0.051 Uiso 1 1 calc R . . C9 C -0.1829(2) -0.22557(15) 0.23870(15) 0.0394(4) Uani 1 1 d . . . H9 H -0.1246 -0.2936 0.2646 0.047 Uiso 1 1 calc R . . C10 C -0.11510(17) -0.10601(14) 0.24387(15) 0.0337(3) Uani 1 1 d . . . H10 H -0.0106 -0.0915 0.2730 0.040 Uiso 1 1 calc R . . C11 C 0.07746(15) 0.42895(13) 0.33166(14) 0.0258(3) Uani 1 1 d . . . C12 C 0.18406(15) 0.43579(12) 0.45665(13) 0.0253(3) Uani 1 1 d . . . H12 H 0.1976 0.3610 0.4968 0.030 Uiso 1 1 calc R . . C13 C 0.26897(15) 0.54747(13) 0.52216(13) 0.0237(3) Uani 1 1 d . . . C14 C 0.38404(15) 0.54912(12) 0.65175(13) 0.0237(3) Uani 1 1 d . . . C15 C 0.51680(16) 0.50045(14) 0.67449(14) 0.0301(3) Uani 1 1 d . . . H15 H 0.5337 0.4625 0.6072 0.036 Uiso 1 1 calc R . . C16 C 0.62527(17) 0.50694(16) 0.79521(15) 0.0359(4) Uani 1 1 d . . . H16 H 0.7168 0.4745 0.8103 0.043 Uiso 1 1 calc R . . C17 C 0.60025(18) 0.56051(15) 0.89339(14) 0.0361(4) Uani 1 1 d . . . H17 H 0.6743 0.5646 0.9761 0.043 Uiso 1 1 calc R . . C18 C 0.4676(2) 0.60805(16) 0.87107(15) 0.0402(4) Uani 1 1 d . . . H18 H 0.4500 0.6442 0.9386 0.048 Uiso 1 1 calc R . . C19 C 0.36047(18) 0.60322(15) 0.75120(15) 0.0351(4) Uani 1 1 d . . . H19 H 0.2699 0.6371 0.7364 0.042 Uiso 1 1 calc R . . C20 C 0.34336(17) 0.77727(13) 0.53317(15) 0.0343(3) Uani 1 1 d . . . H20A H 0.4494 0.7637 0.5672 0.041 Uiso 1 1 calc R . . H20B H 0.3213 0.8098 0.6032 0.041 Uiso 1 1 calc R . . C21 C 0.31401(15) 0.87372(13) 0.44224(14) 0.0278(3) Uani 1 1 d . . . C22 C 0.31675(16) 1.00045(13) 0.48310(14) 0.0294(3) Uani 1 1 d . . . H22 H 0.3327 1.0239 0.5667 0.035 Uiso 1 1 calc R . . C23 C 0.29669(16) 1.09235(13) 0.40420(15) 0.0301(3) Uani 1 1 d . . . H23 H 0.2999 1.1784 0.4341 0.036 Uiso 1 1 calc R . . C24 C 0.27185(16) 1.06035(13) 0.28172(15) 0.0283(3) Uani 1 1 d . . . C25 C 0.26655(17) 0.93413(13) 0.23778(15) 0.0322(3) Uani 1 1 d . . . H25 H 0.2479 0.9106 0.1535 0.039 Uiso 1 1 calc R . . C26 C 0.28914(17) 0.84300(13) 0.31962(15) 0.0329(3) Uani 1 1 d . . . H26 H 0.2874 0.7570 0.2903 0.039 Uiso 1 1 calc R . . C27 C 0.2188(2) 1.12798(16) 0.08300(16) 0.0442(4) Uani 1 1 d . . . H27A H 0.2998 1.0875 0.0743 0.066 Uiso 1 1 calc R . . H27B H 0.2052 1.2057 0.0425 0.066 Uiso 1 1 calc R . . H27C H 0.1274 1.0698 0.0438 0.066 Uiso 1 1 calc R . . H28 H 0.183(2) 0.6514(18) 0.3991(19) 0.048(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0377(2) 0.03178(19) 0.02423(18) 0.00402(14) 0.01394(15) -0.00239(15) N1 0.0294(6) 0.0221(6) 0.0210(6) 0.0049(5) 0.0049(5) -0.0024(5) N2 0.0391(7) 0.0270(6) 0.0211(6) 0.0071(5) 0.0039(5) -0.0040(5) N3 0.0283(7) 0.0217(6) 0.0297(7) 0.0037(5) 0.0027(6) -0.0031(5) O1 0.0383(6) 0.0229(5) 0.0320(6) 0.0078(4) 0.0024(5) -0.0013(4) O2 0.0575(7) 0.0230(5) 0.0422(7) 0.0072(5) 0.0275(6) 0.0023(5) C1 0.0222(6) 0.0238(6) 0.0228(7) 0.0038(5) 0.0083(6) 0.0029(5) C2 0.0221(6) 0.0218(6) 0.0250(7) 0.0062(5) 0.0067(6) 0.0032(5) C3 0.0303(7) 0.0250(7) 0.0248(7) 0.0072(6) 0.0051(6) -0.0006(6) C4 0.0628(12) 0.0328(8) 0.0271(8) 0.0101(7) 0.0073(8) -0.0087(8) C5 0.0308(7) 0.0239(7) 0.0206(7) 0.0014(5) 0.0091(6) -0.0047(6) C6 0.0305(8) 0.0331(8) 0.0381(9) -0.0016(7) 0.0138(7) 0.0000(6) C7 0.0358(9) 0.0439(10) 0.0459(10) -0.0101(8) 0.0215(8) -0.0155(7) C8 0.0586(11) 0.0325(8) 0.0327(9) -0.0018(7) 0.0210(8) -0.0196(8) C9 0.0506(10) 0.0261(7) 0.0315(8) 0.0085(7) 0.0076(8) -0.0012(7) C10 0.0310(8) 0.0287(7) 0.0333(8) 0.0082(6) 0.0056(7) -0.0013(6) C11 0.0254(7) 0.0208(6) 0.0292(7) 0.0046(6) 0.0095(6) 0.0016(5) C12 0.0275(7) 0.0191(6) 0.0265(7) 0.0050(5) 0.0080(6) 0.0032(5) C13 0.0213(6) 0.0233(6) 0.0263(7) 0.0029(5) 0.0096(6) 0.0035(5) C14 0.0248(7) 0.0201(6) 0.0242(7) 0.0024(5) 0.0089(6) -0.0007(5) C15 0.0321(8) 0.0343(8) 0.0253(7) 0.0049(6) 0.0128(6) 0.0063(6) C16 0.0281(8) 0.0414(9) 0.0350(9) 0.0109(7) 0.0090(7) 0.0057(7) C17 0.0402(9) 0.0333(8) 0.0227(7) 0.0030(6) 0.0024(7) -0.0036(7) C18 0.0540(11) 0.0391(9) 0.0279(8) -0.0009(7) 0.0182(8) 0.0069(8) C19 0.0380(9) 0.0376(8) 0.0320(8) 0.0021(7) 0.0165(7) 0.0107(7) C20 0.0327(8) 0.0235(7) 0.0342(8) 0.0018(6) 0.0035(7) -0.0064(6) C21 0.0243(7) 0.0229(7) 0.0329(8) 0.0026(6) 0.0097(6) -0.0024(5) C22 0.0286(7) 0.0261(7) 0.0319(8) -0.0019(6) 0.0131(6) -0.0027(6) C23 0.0322(8) 0.0189(6) 0.0420(9) -0.0009(6) 0.0195(7) 0.0006(6) C24 0.0282(7) 0.0212(6) 0.0402(8) 0.0055(6) 0.0187(7) 0.0016(5) C25 0.0399(9) 0.0250(7) 0.0343(8) 0.0004(6) 0.0190(7) 0.0014(6) C26 0.0385(8) 0.0196(7) 0.0377(9) -0.0011(6) 0.0144(7) 0.0014(6) C27 0.0607(12) 0.0339(9) 0.0420(10) 0.0103(7) 0.0252(9) -0.0001(8) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 1.7012(14) . ? N1 C1 1.3457(18) . ? N1 N2 1.3699(16) . ? N1 C5 1.4344(17) . ? N2 C3 1.3272(18) . ? N3 C13 1.3312(18) . ? N3 C20 1.4586(18) . ? N3 H28 0.87(2) . ? O1 C11 1.2549(17) . ? O2 C24 1.3650(17) . ? O2 C27 1.424(2) . ? C1 C2 1.3797(18) . ? C2 C3 1.413(2) . ? C2 C11 1.4820(19) . ? C3 C4 1.494(2) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.376(2) . ? C5 C10 1.382(2) . ? C6 C7 1.384(2) . ? C6 H6 0.9500 . ? C7 C8 1.385(3) . ? C7 H7 0.9500 . ? C8 C9 1.372(2) . ? C8 H8 0.9500 . ? C9 C10 1.386(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.418(2) . ? C12 C13 1.3818(19) . ? C12 H12 0.9500 . ? C13 C14 1.4911(19) . ? C14 C15 1.3849(19) . ? C14 C19 1.389(2) . ? C15 C16 1.388(2) . ? C15 H15 0.9500 . ? C16 C17 1.382(2) . ? C16 H16 0.9500 . ? C17 C18 1.380(2) . ? C17 H17 0.9500 . ? C18 C19 1.378(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.506(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C26 1.383(2) . ? C21 C22 1.392(2) . ? C22 C23 1.377(2) . ? C22 H22 0.9500 . ? C23 C24 1.383(2) . ? C23 H23 0.9500 . ? C24 C25 1.393(2) . ? C25 C26 1.393(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? 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 N2 111.28(11) . . ? C1 N1 C5 129.13(12) . . ? N2 N1 C5 119.59(11) . . ? C3 N2 N1 104.61(12) . . ? C13 N3 C20 125.98(13) . . ? C13 N3 H28 113.7(13) . . ? C20 N3 H28 120.3(13) . . ? C24 O2 C27 117.37(12) . . ? N1 C1 C2 108.32(12) . . ? N1 C1 Cl1 119.86(10) . . ? C2 C1 Cl1 131.69(11) . . ? C1 C2 C3 103.48(12) . . ? C1 C2 C11 131.00(13) . . ? C3 C2 C11 125.43(12) . . ? N2 C3 C2 112.31(12) . . ? N2 C3 C4 119.11(13) . . ? C2 C3 C4 128.53(13) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C10 121.48(14) . . ? C6 C5 N1 118.90(13) . . ? C10 C5 N1 119.60(13) . . ? C5 C6 C7 118.81(15) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C6 C7 C8 120.37(16) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 120.05(15) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 120.31(15) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C5 C10 C9 118.98(15) . . ? C5 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? O1 C11 C12 122.80(13) . . ? O1 C11 C2 116.82(13) . . ? C12 C11 C2 120.37(12) . . ? C13 C12 C11 122.31(13) . . ? C13 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? N3 C13 C12 122.35(13) . . ? N3 C13 C14 117.21(12) . . ? C12 C13 C14 120.44(12) . . ? C15 C14 C19 119.19(14) . . ? C15 C14 C13 120.79(12) . . ? C19 C14 C13 119.99(12) . . ? C14 C15 C16 120.22(14) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 120.03(14) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C18 C17 C16 119.85(15) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C19 C18 C17 120.23(15) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C14 120.46(14) . . ? C18 C19 H19 119.8 . . ? C14 C19 H19 119.8 . . ? N3 C20 C21 111.17(13) . . ? N3 C20 H20A 109.4 . . ? C21 C20 H20A 109.4 . . ? N3 C20 H20B 109.4 . . ? C21 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? C26 C21 C22 117.84(14) . . ? C26 C21 C20 122.85(13) . . ? C22 C21 C20 119.27(14) . . ? C23 C22 C21 121.06(14) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C22 C23 C24 120.52(13) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? O2 C24 C23 115.92(12) . . ? O2 C24 C25 124.38(14) . . ? C23 C24 C25 119.70(14) . . ? C24 C25 C26 118.80(15) . . ? C24 C25 H25 120.6 . . ? C26 C25 H25 120.6 . . ? C21 C26 C25 122.06(13) . . ? C21 C26 H26 119.0 . . ? C25 C26 H26 119.0 . . ? O2 C27 H27A 109.5 . . ? O2 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O2 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 C3 -0.30(16) . . . . ? C5 N1 N2 C3 179.05(13) . . . . ? N2 N1 C1 C2 0.53(16) . . . . ? C5 N1 C1 C2 -178.74(13) . . . . ? N2 N1 C1 Cl1 176.91(10) . . . . ? C5 N1 C1 Cl1 -2.4(2) . . . . ? N1 C1 C2 C3 -0.50(15) . . . . ? Cl1 C1 C2 C3 -176.30(11) . . . . ? N1 C1 C2 C11 176.12(13) . . . . ? Cl1 C1 C2 C11 0.3(2) . . . . ? N1 N2 C3 C2 -0.03(17) . . . . ? N1 N2 C3 C4 177.63(14) . . . . ? C1 C2 C3 N2 0.34(17) . . . . ? C11 C2 C3 N2 -176.54(13) . . . . ? C1 C2 C3 C4 -177.05(15) . . . . ? C11 C2 C3 C4 6.1(2) . . . . ? C1 N1 C5 C6 112.24(17) . . . . ? N2 N1 C5 C6 -66.98(18) . . . . ? C1 N1 C5 C10 -69.7(2) . . . . ? N2 N1 C5 C10 111.12(16) . . . . ? C10 C5 C6 C7 0.7(2) . . . . ? N1 C5 C6 C7 178.80(14) . . . . ? C5 C6 C7 C8 0.0(2) . . . . ? C6 C7 C8 C9 -0.7(3) . . . . ? C7 C8 C9 C10 0.7(3) . . . . ? C6 C5 C10 C9 -0.8(2) . . . . ? N1 C5 C10 C9 -178.87(14) . . . . ? C8 C9 C10 C5 0.1(2) . . . . ? C1 C2 C11 O1 -156.24(14) . . . . ? C3 C2 C11 O1 19.7(2) . . . . ? C1 C2 C11 C12 24.9(2) . . . . ? C3 C2 C11 C12 -159.14(14) . . . . ? O1 C11 C12 C13 -0.2(2) . . . . ? C2 C11 C12 C13 178.64(13) . . . . ? C20 N3 C13 C12 -176.03(14) . . . . ? C20 N3 C13 C14 3.8(2) . . . . ? C11 C12 C13 N3 2.3(2) . . . . ? C11 C12 C13 C14 -177.51(12) . . . . ? N3 C13 C14 C15 -105.06(16) . . . . ? C12 C13 C14 C15 74.80(19) . . . . ? N3 C13 C14 C19 73.07(18) . . . . ? C12 C13 C14 C19 -107.07(16) . . . . ? C19 C14 C15 C16 -0.6(2) . . . . ? C13 C14 C15 C16 177.53(13) . . . . ? C14 C15 C16 C17 0.9(2) . . . . ? C15 C16 C17 C18 -0.3(2) . . . . ? C16 C17 C18 C19 -0.5(3) . . . . ? C17 C18 C19 C14 0.8(3) . . . . ? C15 C14 C19 C18 -0.2(2) . . . . ? C13 C14 C19 C18 -178.40(14) . . . . ? C13 N3 C20 C21 168.53(14) . . . . ? N3 C20 C21 C26 -38.1(2) . . . . ? N3 C20 C21 C22 144.15(14) . . . . ? C26 C21 C22 C23 -0.6(2) . . . . ? C20 C21 C22 C23 177.23(13) . . . . ? C21 C22 C23 C24 0.6(2) . . . . ? C27 O2 C24 C23 -176.11(14) . . . . ? C27 O2 C24 C25 3.9(2) . . . . ? C22 C23 C24 O2 -179.76(13) . . . . ? C22 C23 C24 C25 0.2(2) . . . . ? O2 C24 C25 C26 178.90(14) . . . . ? C23 C24 C25 C26 -1.1(2) . . . . ? C22 C21 C26 C25 -0.3(2) . . . . ? C20 C21 C26 C25 -178.04(14) . . . . ? C24 C25 C26 C21 1.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.321 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.049 #===================== End of CIF submission =================================