# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _audit_creation_method maXus _publ_contact_author_name 'Prof Masami Sakamoto' _publ_contact_author_address ; Materials Technology Chiba Univ., Faculty of Engineering Yayoi-cho Inage-ku Chiba 263-8522 JAPAN ; _publ_contact_author_email SAKAMOTOM@FACULTY.CHIBA-U.JP _publ_section_title ; Absolute Asymmetric Synthesis by Nucleophilic Carbonyl Addition using Chiral Crystals of Achiral Amides ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All diagrams and calculations were performed using maXus (Bruker Nonius, Delft & MacScience, Japan). ; _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Waasmaier, D. & Kirfel, A. (1995). Acta Cryst. A51, 416-431. ; loop_ _publ_author_name 'Masami Sakamoto' 'Tsutomu Fujita' 'Shuichiro Kobaru' 'Takashi Mino' #=================================================== # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_compound_4 _database_code_depnum_ccdc_archive 'CCDC 215658' _audit_creation_method maXus _chemical_compound_source 'Local laboratory' _exptl_crystal_description Cube _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _cell_measurement_temperature 298 _refine_ls_hydrogen_treatment refxyz _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method '\q \w scans' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'maXus (Mackay et al., 1999)' _cell_measurement_reflns_used 21 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 loop_ _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 0.09510 _diffrn_orient_matrix_UB_12 -0.00408 _diffrn_orient_matrix_UB_13 -0.01513 _diffrn_orient_matrix_UB_21 0.00751 _diffrn_orient_matrix_UB_22 0.05780 _diffrn_orient_matrix_UB_23 0.00905 _diffrn_orient_matrix_UB_31 0.01047 _diffrn_orient_matrix_UB_32 -0.00444 _diffrn_orient_matrix_UB_33 0.13183 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 253.301 _diffrn_radiation_type ' CuK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z '-X+ 1/2,-Y,+Z+ 1/2' '+X+ 1/2,-Y+ 1/2,-Z' '-X,+Y+ 1/2,-Z+ 1/2' _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_cell_setting Orthorhombic _chemical_formula_moiety 'C16 H15 N O2 ' _chemical_formula_sum 'C16 H15 N O2 ' _chemical_name_systematic ; ? ; _cell_length_a 10.420(2) _cell_length_b 17.208(4) _cell_length_c 7.519(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1348.3(6) _diffrn_reflns_number 1511 _diffrn_reflns_theta_max 69.94 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_full 69.94 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_coefficient_mu 0.66 _exptl_crystal_F_000 536 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C ' 'C ' 0.0181 0.0091 'Waasmaier & Kirfel, 1995' 'H ' 'H ' 0.0000 0.0000 'Waasmaier & Kirfel, 1995' 'O ' 'O ' 0.0492 0.0322 'Waasmaier & Kirfel, 1995' 'N ' 'N ' 0.0311 0.0180 'Waasmaier & Kirfel, 1995' # Refinement statistics _reflns_d_resolution_low 2.11 _reflns_d_resolution_high 0.64 _reflns_limit_h_max 12 _reflns_limit_h_min 0 _reflns_limit_k_max 20 _reflns_limit_k_min 0 _reflns_limit_l_max 9 _reflns_limit_l_min 0 _refine_ls_matrix_type full _refine_ls_shift/su_max 0.032 _refine_ls_shift/su_mean 0.007 _reflns_number_total 1521 _refine_ls_R_factor_all 0.051 _refine_ls_wR_factor_all 0.151 _refine_ls_goodness_of_fit_all 0.845 _reflns_number_gt 1326 _reflns_threshold_expression 'I> 3.00 sigma(I)' _refine_ls_R_factor_gt 0.046 _refine_ls_wR_factor_gt 0.150 _refine_ls_goodness_of_fit_gt 0.722 _refine_ls_number_reflns 1326 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_number_constraints 15 _refine_ls_wR_factor_ref 0.150 _refine_ls_goodness_of_fit_ref 0.722 _refine_ls_abs_structure_details ; ; _refine_ls_structure_factor_coef F^2^ _refine_special_details ; Refinement on F^2^. ; _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ; w = 1 / ( s^2^(Fo^2^) + 0.10000 * Fo^2^) ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _computing_structure_refinement 'maXus(Mackay et al., 1999)' _computing_molecular_graphics 'Ortep (Johnson, 1976)' _computing_publication_material 'maXus(Mackay et al., 1999)' _atom_sites_solution_hydrogens geom _refine_diff_density_max 0.22 _refine_diff_density_min -0.24 _refine_diff_density_rms 0.06 #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type N1 0.4112(2) 0.07435(15) 0.6280(3) 0.0485(12) 1.00 Uij O2 0.4396(2) 0.04901(15) 0.3356(3) 0.0658(14) 1.00 Uij C3 0.5995(3) 0.20667(14) 0.3203(4) 0.0402(12) 1.00 Uij C4 0.6824(2) 0.14493(13) 0.4020(3) 0.0355(11) 1.00 Uij C5 0.8163(2) 0.15206(14) 0.4009(4) 0.0412(12) 1.00 Uij C6 0.6254(2) 0.08359(14) 0.4953(4) 0.0381(11) 1.00 Uij O7 0.5051(3) 0.22840(13) 0.4019(3) 0.0658(13) 1.00 Uij C8 0.8352(3) 0.03790(17) 0.5796(4) 0.0514(15) 1.00 Uij C9 0.6344(3) 0.24094(15) 0.1455(4) 0.0401(12) 1.00 Uij C10 0.7149(3) 0.20431(17) 0.0252(4) 0.0485(14) 1.00 Uij C11 0.8908(3) 0.09795(19) 0.4903(4) 0.0491(14) 1.00 Uij C12 0.4827(3) 0.06899(16) 0.4802(4) 0.0432(13) 1.00 Uij C13 0.5815(3) 0.31286(16) 0.0998(4) 0.0510(15) 1.00 Uij C14 0.7021(3) 0.03028(16) 0.5834(4) 0.0477(14) 1.00 Uij C15 0.7436(4) 0.2393(2) -0.1370(4) 0.0636(19) 1.00 Uij C16 0.2751(3) 0.0581(2) 0.6150(5) 0.0635(18) 1.00 Uij C17 0.4531(4) 0.1127(2) 0.7897(5) 0.066(2) 1.00 Uij C18 0.6918(4) 0.3094(2) -0.1792(5) 0.076(2) 1.00 Uij C19 0.6108(4) 0.3469(2) -0.0608(5) 0.070(2) 1.00 Uij H5 0.855752 0.194210 0.337679 0.046099 1.00 Uiso H8 0.887724 0.000239 0.639456 0.055984 1.00 Uiso H10 0.751975 0.154967 0.055336 0.053471 1.00 Uiso H11 0.982495 0.103319 0.490105 0.053355 1.00 Uiso H13 0.524796 0.338352 0.181777 0.057357 1.00 Uiso H14 0.663453 -0.012024 0.647078 0.054531 1.00 Uiso H15 0.797633 0.212752 -0.220626 0.068200 1.00 Uiso H16A 0.234910 0.064511 0.728942 0.073766 1.00 Uiso H16B 0.263434 0.005650 0.574795 0.073766 1.00 Uiso H16C 0.236864 0.093266 0.531123 0.073766 1.00 Uiso H17A 0.385750 0.109987 0.876582 0.072378 1.00 Uiso H17B 0.473311 0.166144 0.765998 0.072378 1.00 Uiso H17C 0.527947 0.086674 0.834255 0.072378 1.00 Uiso H18 0.714233 0.334137 -0.289377 0.081287 1.00 Uiso H19 0.573541 0.396047 -0.091674 0.073969 1.00 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0437(12) 0.0575(12) 0.0442(13) -.0011(10) 0.0103(10) 0.0029(11) O2 0.0414(11) 0.1018(18) 0.0542(12) -.0098(12) 0.0027(11) -.0238(13) C3 0.0401(12) 0.0409(11) 0.0396(13) 0.0035(10) 0.0021(12) -.0011(11) C4 0.0353(12) 0.0401(11) 0.0310(11) 0.0009(9) 0.0005(10) -.0006(10) C5 0.0364(13) 0.0477(13) 0.0397(13) -.0035(10) -.0006(12) -.0012(11) C6 0.0365(12) 0.0420(12) 0.0359(13) 0.0005(9) 0.0024(10) -.0015(11) O7 0.0644(13) 0.0731(13) 0.0598(13) 0.0322(11) 0.0210(12) 0.0167(11) C8 0.0507(15) 0.0576(15) 0.0460(15) 0.0155(13) -.0056(14) 0.0061(14) C9 0.0397(12) 0.0416(12) 0.0391(13) -.0027(10) -.0025(11) 0.0011(11) C10 0.0487(15) 0.0537(14) 0.0430(14) 0.0031(12) -.0030(13) 0.0019(12) C11 0.0326(12) 0.0706(17) 0.0441(15) 0.0027(11) -.0043(12) -.0069(14) C12 0.0388(14) 0.0444(12) 0.0465(14) -.0015(11) 0.0047(12) -.0027(11) C13 0.0534(16) 0.0450(13) 0.0547(16) 0.0008(12) -.0047(15) 0.0072(12) C14 0.0517(15) 0.0461(13) 0.0452(15) 0.0020(12) 0.0013(13) 0.0097(12) C15 0.0585(18) 0.091(2) 0.0412(15) 0.0011(17) 0.0047(15) 0.0038(15) C16 0.0451(16) 0.082(2) 0.063(2) -.0058(15) 0.0164(16) 0.0034(17) C17 0.0600(19) 0.091(2) 0.0468(17) 0.0015(18) 0.0056(16) -.0082(16) C18 0.077(2) 0.096(3) 0.055(2) -.006(2) 0.003(2) 0.034(2) C19 0.077(2) 0.0634(18) 0.070(2) -.0006(17) -.008(2) 0.0273(18) 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 C16 N1 C12 O2 -2.1(3) . . . . ? C16 N1 C12 C6 -178.2(4) . . . . ? C17 N1 C12 O2 -166.7(5) . . . . ? C17 N1 C12 C6 17.2(3) . . . . ? O7 C3 C4 C5 -135.3(4) . . . . ? O7 C3 C4 C6 38.4(3) . . . . ? C9 C3 C4 C5 43.6(3) . . . . ? C9 C3 C4 C6 -142.7(4) . . . . ? C4 C3 C9 C10 20.9(3) . . . . ? C4 C3 C9 C13 -160.2(4) . . . . ? O7 C3 C9 C10 -160.3(4) . . . . ? O7 C3 C9 C13 18.7(3) . . . . ? C5 C4 C3 O7 -135.3(4) . . . . ? C5 C4 C3 C9 43.6(3) . . . . ? C3 C4 C5 C11 174.4(4) . . . . ? C6 C4 C3 O7 38.4(3) . . . . ? C6 C4 C3 C9 -142.7(4) . . . . ? C3 C4 C6 C12 13.7(2) . . . . ? C3 C4 C6 C14 -174.5(4) . . . . ? C6 C4 C5 C11 0.8(3) . . . . ? C5 C4 C6 C12 -172.6(4) . . . . ? C5 C4 C6 C14 -0.8(2) . . . . ? C11 C5 C4 C3 174.4(4) . . . . ? C11 C5 C4 C6 0.8(3) . . . . ? C4 C5 C11 C8 -0.2(3) . . . . ? C4 C6 C12 N1 -118.3(3) . . . . ? C4 C6 C12 O2 65.4(3) . . . . ? C12 C6 C4 C3 13.7(2) . . . . ? C12 C6 C4 C5 -172.6(4) . . . . ? C14 C6 C4 C3 -174.5(4) . . . . ? C14 C6 C4 C5 -0.8(2) . . . . ? C4 C6 C14 C8 0.2(3) . . . . ? C14 C6 C12 N1 69.9(3) . . . . ? C14 C6 C12 O2 -106.4(4) . . . . ? C12 C6 C14 C8 172.1(4) . . . . ? C14 C8 C11 C5 -0.4(3) . . . . ? C11 C8 C14 C6 0.3(3) . . . . ? C10 C9 C3 C4 20.9(3) . . . . ? C10 C9 C3 O7 -160.3(4) . . . . ? C3 C9 C10 C15 179.7(4) . . . . ? C13 C9 C3 C4 -160.2(4) . . . . ? C13 C9 C3 O7 18.7(3) . . . . ? C3 C9 C13 C19 -179.9(4) . . . . ? C13 C9 C10 C15 0.8(3) . . . . ? C10 C9 C13 C19 -1.0(3) . . . . ? C15 C10 C9 C3 179.7(4) . . . . ? C15 C10 C9 C13 0.8(3) . . . . ? C9 C10 C15 C18 -0.5(3) . . . . ? C8 C11 C5 C4 -0.2(3) . . . . ? C5 C11 C8 C14 -0.4(3) . . . . ? O2 C12 N1 C16 -2.1(3) . . . . ? O2 C12 N1 C17 -166.7(5) . . . . ? N1 C12 C6 C4 -118.3(3) . . . . ? N1 C12 C6 C14 69.9(3) . . . . ? C6 C12 N1 C16 -178.2(4) . . . . ? C6 C12 N1 C17 17.2(3) . . . . ? O2 C12 C6 C4 65.4(3) . . . . ? O2 C12 C6 C14 -106.4(4) . . . . ? C19 C13 C9 C3 -179.9(4) . . . . ? C19 C13 C9 C10 -1.0(3) . . . . ? C9 C13 C19 C18 0.8(3) . . . . ? C8 C14 C6 C4 0.2(3) . . . . ? C6 C14 C8 C11 0.3(3) . . . . ? C8 C14 C6 C12 172.1(4) . . . . ? C18 C15 C10 C9 -0.5(3) . . . . ? C10 C15 C18 C19 0.4(4) . . . . ? C19 C18 C15 C10 0.4(4) . . . . ? C15 C18 C19 C13 -0.5(4) . . . . ? C18 C19 C13 C9 0.8(3) . . . . ? C13 C19 C18 C15 -0.5(4) . . . . ? _geom_special_details ; All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C12 1.341(6) . . ? N1 C16 1.449(7) . . ? N1 C17 1.451(8) . . ? O2 C12 1.226(7) . . ? C3 C4 1.500(6) . . ? C3 O7 1.218(6) . . ? C3 C9 1.486(7) . . ? C4 C5 1.401(6) . . ? C4 C6 1.400(6) . . ? C5 C11 1.386(7) . . ? C6 C12 1.512(6) . . ? C6 C14 1.386(7) . . ? C8 C11 1.362(8) . . ? C8 C14 1.393(8) . . ? C9 C10 1.386(7) . . ? C9 C13 1.398(6) . . ? C10 C15 1.393(8) . . ? C13 C19 1.376(8) . . ? C15 C18 1.359(9) . . ? C18 C19 1.385(10) . . ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N1 C16 118.3(5) . . . ? C12 N1 C17 124.0(5) . . . ? C16 N1 C17 116.0(5) . . . ? C4 C3 O7 118.4(5) . . . ? C4 C3 C9 120.2(4) . . . ? O7 C3 C9 121.4(4) . . . ? C3 C4 C5 120.6(4) . . . ? C3 C4 C6 119.7(4) . . . ? C5 C4 C6 119.4(4) . . . ? C4 C5 C11 119.8(4) . . . ? C4 C6 C12 120.3(4) . . . ? C4 C6 C14 119.6(4) . . . ? C12 C6 C14 119.6(4) . . . ? C11 C8 C14 120.3(5) . . . ? C3 C9 C10 123.0(4) . . . ? C3 C9 C13 118.2(5) . . . ? C10 C9 C13 118.7(5) . . . ? C9 C10 C15 120.3(5) . . . ? C5 C11 C8 120.7(4) . . . ? N1 C12 O2 123.4(4) . . . ? N1 C12 C6 118.2(5) . . . ? O2 C12 C6 118.3(4) . . . ? C9 C13 C19 120.3(6) . . . ? C6 C14 C8 120.2(5) . . . ? C10 C15 C18 120.2(6) . . . ? C15 C18 C19 120.3(6) . . . ? C13 C19 C18 120.1(6) . . . ? #=================================================== #=================================================== # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 215659' _audit_creation_method maXus _chemical_compound_source 'Local laboratory' _exptl_crystal_description Cube _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _cell_measurement_temperature 298 _refine_ls_hydrogen_treatment refxyz _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method '\q \w scans' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'maXus (Mackay et al., 1999)' _cell_measurement_reflns_used 21 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 loop_ _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 -0.05140 _diffrn_orient_matrix_UB_12 0.02748 _diffrn_orient_matrix_UB_13 0.07394 _diffrn_orient_matrix_UB_21 -0.01728 _diffrn_orient_matrix_UB_22 -0.06589 _diffrn_orient_matrix_UB_23 0.03425 _diffrn_orient_matrix_UB_31 0.07364 _diffrn_orient_matrix_UB_32 0.00376 _diffrn_orient_matrix_UB_33 0.05980 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 281.355 _diffrn_radiation_type ' CuK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z '-X+ 1/2,-Y,+Z+ 1/2' '+X+ 1/2,-Y+ 1/2,-Z' '-X,+Y+ 1/2,-Z+ 1/2' _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_cell_setting Orthorhombic _chemical_formula_moiety 'C18 H19 N O2 ' _chemical_formula_sum 'C18 H19 N O2 ' _chemical_name_systematic ; ? ; _cell_length_a 10.937(5) _cell_length_b 13.987(5) _cell_length_c 9.896(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1513.8(10) _diffrn_reflns_number 1667 _diffrn_reflns_theta_max 69.98 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_full 69.98 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_coefficient_mu 0.64 _exptl_crystal_F_000 600 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C ' 'C ' 0.0181 0.0091 'Waasmaier & Kirfel, 1995' 'H ' 'H ' 0.0000 0.0000 'Waasmaier & Kirfel, 1995' 'O ' 'O ' 0.0492 0.0322 'Waasmaier & Kirfel, 1995' 'N ' 'N ' 0.0311 0.0180 'Waasmaier & Kirfel, 1995' # Refinement statistics _reflns_d_resolution_low 2.08 _reflns_d_resolution_high 0.64 _reflns_limit_h_max 13 _reflns_limit_h_min 0 _reflns_limit_k_max 17 _reflns_limit_k_min 0 _reflns_limit_l_max 12 _reflns_limit_l_min 0 _refine_ls_matrix_type full _refine_ls_shift/su_max 0.038 _refine_ls_shift/su_mean 0.006 _reflns_number_total 1655 _refine_ls_R_factor_all 0.059 _refine_ls_wR_factor_all 0.346 _refine_ls_goodness_of_fit_all 0.497 _reflns_number_gt 1616 _reflns_threshold_expression 'I> 3.00 sigma(I)' _refine_ls_R_factor_gt 0.059 _refine_ls_wR_factor_gt 0.346 _refine_ls_goodness_of_fit_gt 0.462 _refine_ls_number_reflns 1616 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_wR_factor_ref 0.346 _refine_ls_goodness_of_fit_ref 0.462 _refine_ls_abs_structure_details ; ; _refine_ls_abs_structure_Rogers '_' _refine_ls_structure_factor_coef F^2^ _refine_special_details ; Refinement on F^2^. ; _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ; w = 1 / ( s^2^(Fo^2^) + 0.10000 * Fo^2^) ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _computing_structure_refinement 'maXus(Mackay et al., 1999)' _computing_molecular_graphics 'Ortep (Johnson, 1976)' _computing_publication_material 'maXus(Mackay et al., 1999)' _atom_sites_solution_hydrogens geom _refine_diff_density_max 0.30 _refine_diff_density_min -0.46 _refine_diff_density_rms 0.13 #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 -0.90320(16) -0.15514(10) -0.62177(17) 0.0493(8) 1.00 Uij C2 -0.84434(16) -0.22950(13) -0.63427(17) 0.0324(8) 1.00 Uij N3 -0.75289(13) -0.25531(11) -0.54826(17) 0.0347(7) 1.00 Uij C4 -0.88241(17) -0.29929(12) -0.74221(18) 0.0319(8) 1.00 Uij C5 -0.89493(17) -0.26903(13) -0.87655(18) 0.0342(8) 1.00 Uij C6 -0.92307(19) -0.11084(13) -1.0060(2) 0.0366(9) 1.00 Uij C7 -0.9476(2) -0.32986(15) -0.9703(2) 0.0429(10) 1.00 Uij O8 -0.74209(15) -0.15100(14) -0.8898(2) 0.0609(10) 1.00 Uij C9 -1.0507(2) -0.11602(15) -1.0045(2) 0.0409(9) 1.00 Uij C10 -0.92349(18) -0.39019(15) -0.7058(2) 0.0381(9) 1.00 Uij C11 -0.9746(2) -0.45086(15) -0.8014(3) 0.0450(10) 1.00 Uij C12 -0.72319(19) -0.19254(16) -0.4349(2) 0.0416(10) 1.00 Uij C13 -0.84600(18) -0.17347(14) -0.9202(2) 0.0380(9) 1.00 Uij C14 -0.66071(18) -0.32718(14) -0.5850(2) 0.0405(9) 1.00 Uij C15 -0.9861(2) -0.42088(16) -0.9344(2) 0.0468(10) 1.00 Uij C16 -0.8660(2) -0.04329(14) -1.0891(2) 0.0451(10) 1.00 Uij C17 -0.7163(2) -0.2447(2) -0.3019(2) 0.0532(12) 1.00 Uij C18 -0.9363(3) 0.01665(16) -1.1700(3) 0.0561(13) 1.00 Uij C19 -1.0627(3) 0.01138(16) -1.1653(3) 0.0570(13) 1.00 Uij C20 -0.5533(2) -0.28331(18) -0.6588(3) 0.0545(12) 1.00 Uij C21 -1.1197(2) -0.05365(16) -1.0823(3) 0.0512(12) 1.00 Uij H7 -0.963(3) -0.3075(19) -1.072(3) 0.049(7) 1.00 Uiso H9 -1.090328 -0.163062 -0.949165 0.047(7) 1.00 Uiso H10 -0.915(2) -0.4129(16) -0.608(3) 0.033(6) 1.00 Uiso H11 -0.997(3) -0.516(2) -0.767(3) 0.051(7) 1.00 Uiso H12A -0.789(3) -0.141(2) -0.427(3) 0.047(7) 1.00 Uiso H12B -0.644722 -0.163796 -0.450367 0.048(7) 1.00 Uiso H14A -0.699(2) -0.3766(17) -0.634(3) 0.037(6) 1.00 Uiso H14B -0.621(3) -0.357(2) -0.499(3) 0.072(10) 1.00 Uiso H15 -1.019708 -0.462639 -1.001835 0.088(12) 1.00 Uiso H16 -0.782(3) -0.030(2) -1.092(4) 0.064(9) 1.00 Uiso H17A -0.696294 -0.200652 -0.230824 0.061(9) 1.00 Uiso H17B -0.794352 -0.273299 -0.283814 0.066(9) 1.00 Uiso H17C -0.646(3) -0.299(2) -0.299(4) 0.077(11) 1.00 Uiso H18 -0.890(3) 0.062(2) -1.234(3) 0.055(7) 1.00 Uiso H19 -1.108(4) 0.054(3) -1.224(4) 0.092(12) 1.00 Uiso H20A -0.494918 -0.332246 -0.680275 0.056(8) 1.00 Uiso H20B -0.590(3) -0.253(3) -0.750(3) 0.068(9) 1.00 Uiso H20C -0.515(2) -0.2308(19) -0.603(3) 0.043(6) 1.00 Uiso H21 -1.207403 -0.054792 -1.078197 0.054(8) 1.00 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0573(9) 0.0401(7) 0.0506(9) 0.0170(7) -.0108(7) -.0059(6) C2 0.0348(8) 0.0325(8) 0.0299(8) 0.0009(7) -.0005(7) 0.0005(7) N3 0.0359(7) 0.0366(8) 0.0317(8) 0.0045(7) -.0064(6) -.0050(6) C4 0.0319(9) 0.0335(9) 0.0302(9) 0.0009(7) -.0016(6) 0.0012(7) C5 0.0342(8) 0.0371(9) 0.0313(9) 0.0004(7) -.0030(7) 0.0035(7) C6 0.0475(10) 0.0313(8) 0.0311(8) -.0040(8) -.0022(8) -.0024(7) C7 0.0494(11) 0.0445(11) 0.0349(10) -.0008(8) -.0084(9) 0.0001(8) O8 0.0474(8) 0.0685(11) 0.0666(12) -.0191(8) -.0181(9) 0.0221(9) C9 0.0464(10) 0.0390(9) 0.0374(9) -.0022(8) -.0026(8) 0.0015(8) C10 0.0420(9) 0.0361(9) 0.0363(9) -.0010(8) -.0029(8) 0.0059(8) C11 0.0452(9) 0.0348(9) 0.0552(12) -.0068(8) -.0026(9) 0.0022(9) C12 0.0461(10) 0.0444(9) 0.0343(10) -.0045(8) -.0042(8) -.0082(9) C13 0.0392(9) 0.0419(10) 0.0328(9) -.0053(8) -.0023(8) 0.0024(8) C14 0.0394(9) 0.0380(9) 0.0440(10) 0.0079(8) -.0081(9) -.0062(8) C15 0.0510(11) 0.0404(10) 0.0489(12) -.0026(8) -.0128(10) -.0073(9) C16 0.0580(12) 0.0356(9) 0.0417(10) -.0097(8) 0.0009(9) 0.0031(9) C17 0.0558(12) 0.0719(15) 0.0317(10) -.0021(12) -.0071(9) -.0024(11) C18 0.0839(16) 0.0367(10) 0.0479(12) -.0068(11) -.0043(13) 0.0095(9) C19 0.0835(16) 0.0378(10) 0.0496(13) 0.0100(11) -.0171(13) 0.0036(10) C20 0.0419(10) 0.0598(13) 0.0618(14) 0.0076(10) 0.0034(10) -.0122(13) C21 0.0553(12) 0.0444(10) 0.0538(12) 0.0066(10) -.0126(10) -.0041(11) 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 C2 N3 C12 0.5(2) . . . . ? O1 C2 N3 C14 -161.5(3) . . . . ? O1 C2 C4 C5 53.6(2) . . . . ? O1 C2 C4 C10 -116.5(2) . . . . ? N3 C2 C4 C5 -131.6(2) . . . . ? N3 C2 C4 C10 58.3(2) . . . . ? C4 C2 N3 C12 -174.0(2) . . . . ? C4 C2 N3 C14 24.1(2) . . . . ? C12 N3 C2 O1 0.5(2) . . . . ? C12 N3 C2 C4 -174.0(2) . . . . ? C2 N3 C12 C17 130.4(2) . . . . ? C14 N3 C2 O1 -161.5(3) . . . . ? C14 N3 C2 C4 24.1(2) . . . . ? C2 N3 C14 C20 87.2(2) . . . . ? C14 N3 C12 C17 -66.7(2) . . . . ? C12 N3 C14 C20 -75.1(2) . . . . ? C5 C4 C2 O1 53.6(2) . . . . ? C5 C4 C2 N3 -131.6(2) . . . . ? C2 C4 C5 C7 -170.2(3) . . . . ? C2 C4 C5 C13 12.9(2) . . . . ? C10 C4 C2 O1 -116.5(2) . . . . ? C10 C4 C2 N3 58.3(2) . . . . ? C2 C4 C10 C11 171.1(3) . . . . ? C10 C4 C5 C7 0.0(2) . . . . ? C5 C4 C10 C11 0.9(2) . . . . ? C10 C4 C5 C13 -177.0(3) . . . . ? C7 C5 C4 C2 -170.2(3) . . . . ? C7 C5 C4 C10 0.0(2) . . . . ? C4 C5 C7 C15 -1.3(2) . . . . ? C13 C5 C4 C2 12.9(2) . . . . ? C4 C5 C13 C6 -134.7(3) . . . . ? C4 C5 C13 O8 48.6(2) . . . . ? C13 C5 C4 C10 -177.0(3) . . . . ? C7 C5 C13 C6 48.3(2) . . . . ? C7 C5 C13 O8 -128.3(3) . . . . ? C13 C5 C7 C15 175.7(3) . . . . ? C9 C6 C13 C5 26.3(2) . . . . ? C9 C6 C13 O8 -157.2(3) . . . . ? C13 C6 C9 C21 177.4(3) . . . . ? C9 C6 C16 C18 -0.8(2) . . . . ? C16 C6 C9 C21 -1.3(2) . . . . ? C16 C6 C13 C5 -155.0(3) . . . . ? C16 C6 C13 O8 21.6(2) . . . . ? C13 C6 C16 C18 -179.6(3) . . . . ? C15 C7 C5 C4 -1.3(2) . . . . ? C5 C7 C15 C11 1.7(2) . . . . ? C15 C7 C5 C13 175.7(3) . . . . ? C21 C9 C6 C13 177.4(3) . . . . ? C21 C9 C6 C16 -1.3(2) . . . . ? C6 C9 C21 C19 2.5(2) . . . . ? C11 C10 C4 C2 171.1(3) . . . . ? C11 C10 C4 C5 0.9(2) . . . . ? C4 C10 C11 C15 -0.5(2) . . . . ? C15 C11 C10 C4 -0.5(2) . . . . ? C10 C11 C15 C7 -0.8(2) . . . . ? C17 C12 N3 C2 130.4(2) . . . . ? C17 C12 N3 C14 -66.7(2) . . . . ? C6 C13 C5 C4 -134.7(3) . . . . ? C6 C13 C5 C7 48.3(2) . . . . ? C5 C13 C6 C9 26.3(2) . . . . ? C5 C13 C6 C16 -155.0(3) . . . . ? O8 C13 C5 C4 48.6(2) . . . . ? O8 C13 C5 C7 -128.3(3) . . . . ? O8 C13 C6 C9 -157.2(3) . . . . ? O8 C13 C6 C16 21.6(2) . . . . ? C20 C14 N3 C2 87.2(2) . . . . ? C20 C14 N3 C12 -75.1(2) . . . . ? C11 C15 C7 C5 1.7(2) . . . . ? C7 C15 C11 C10 -0.8(2) . . . . ? C18 C16 C6 C9 -0.8(2) . . . . ? C18 C16 C6 C13 -179.6(3) . . . . ? C6 C16 C18 C19 1.9(2) . . . . ? C19 C18 C16 C6 1.9(2) . . . . ? C16 C18 C19 C21 -0.7(2) . . . . ? C18 C19 C21 C9 -1.4(2) . . . . ? C21 C19 C18 C16 -0.7(2) . . . . ? C19 C21 C9 C6 2.5(2) . . . . ? C9 C21 C19 C18 -1.4(2) . . . . ? _geom_special_details ; All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.229(7) . . ? C2 N3 1.362(7) . . ? C2 C4 1.506(7) . . ? N3 C12 1.461(8) . . ? N3 C14 1.469(7) . . ? C4 C5 1.402(7) . . ? C4 C10 1.396(8) . . ? C5 C7 1.384(8) . . ? C5 C13 1.503(8) . . ? C6 C9 1.397(9) . . ? C6 C13 1.483(9) . . ? C6 C16 1.399(8) . . ? C7 C15 1.387(9) . . ? O8 C13 1.217(7) . . ? C9 C21 1.387(9) . . ? C10 C11 1.389(9) . . ? C11 C15 1.387(10) . . ? C12 C17 1.507(10) . . ? C14 C20 1.513(10) . . ? C16 C18 1.391(10) . . ? C18 C19 1.385(12) . . ? C19 C21 1.375(11) . . ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C2 N3 123.1(5) . . . ? O1 C2 C4 118.4(5) . . . ? N3 C2 C4 118.3(4) . . . ? C2 N3 C12 118.9(5) . . . ? C2 N3 C14 122.0(5) . . . ? C12 N3 C14 116.6(4) . . . ? C2 C4 C5 120.3(4) . . . ? C2 C4 C10 119.8(5) . . . ? C5 C4 C10 119.2(5) . . . ? C4 C5 C7 119.4(5) . . . ? C4 C5 C13 120.4(5) . . . ? C7 C5 C13 120.1(5) . . . ? C9 C6 C13 122.1(6) . . . ? C9 C6 C16 119.1(6) . . . ? C13 C6 C16 118.8(6) . . . ? C5 C7 C15 121.3(6) . . . ? C6 C9 C21 120.4(6) . . . ? C4 C10 C11 120.7(5) . . . ? C10 C11 C15 119.9(6) . . . ? N3 C12 C17 113.0(5) . . . ? C5 C13 C6 119.2(5) . . . ? C5 C13 O8 119.4(6) . . . ? C6 C13 O8 121.3(6) . . . ? N3 C14 C20 112.0(5) . . . ? C7 C15 C11 119.5(6) . . . ? C6 C16 C18 119.9(7) . . . ? C16 C18 C19 120.1(7) . . . ? C18 C19 C21 120.5(7) . . . ? C9 C21 C19 120.0(7) . . . ? #=================================================== # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_compound_3 _database_code_depnum_ccdc_archive 'CCDC 215660' _audit_creation_method maXus _chemical_compound_source 'Local laboratory' _exptl_crystal_description Cube _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _cell_measurement_temperature 298 _refine_ls_hydrogen_treatment refxyz _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method '\q \w scans' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'maXus (Mackay et al., 1999)' _cell_measurement_reflns_used 21 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 loop_ _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 0.04082 _diffrn_orient_matrix_UB_12 -0.04576 _diffrn_orient_matrix_UB_13 0.03996 _diffrn_orient_matrix_UB_21 0.05619 _diffrn_orient_matrix_UB_22 0.03454 _diffrn_orient_matrix_UB_23 -0.02234 _diffrn_orient_matrix_UB_31 -0.00319 _diffrn_orient_matrix_UB_32 0.02254 _diffrn_orient_matrix_UB_33 0.11550 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 343.426 _diffrn_radiation_type ' CuK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z '-X+ 1/2,-Y,+Z+ 1/2' '+X+ 1/2,-Y+ 1/2,-Z' '-X,+Y+ 1/2,-Z+ 1/2' _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_cell_setting Orthorhombic _chemical_formula_moiety 'C23 H21 N O2 ' _chemical_formula_sum 'C23 H21 N O2 ' _chemical_name_systematic ; ? ; _cell_length_a 14.384(4) _cell_length_b 16.234(5) _cell_length_c 8.049(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1879.6(12) _diffrn_reflns_number 2072 _diffrn_reflns_theta_max 70.03 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_full 70.03 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_coefficient_mu 0.61 _exptl_crystal_F_000 728 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C ' 'C ' 0.0181 0.0091 'Waasmaier & Kirfel, 1995' 'H ' 'H ' 0.0000 0.0000 'Waasmaier & Kirfel, 1995' 'O ' 'O ' 0.0492 0.0322 'Waasmaier & Kirfel, 1995' 'N ' 'N ' 0.0311 0.0180 'Waasmaier & Kirfel, 1995' # Refinement statistics _reflns_d_resolution_low 2.32 _reflns_d_resolution_high 0.64 _reflns_limit_h_max 17 _reflns_limit_h_min 0 _reflns_limit_k_max 19 _reflns_limit_k_min 0 _reflns_limit_l_max 9 _reflns_limit_l_min 0 _refine_ls_matrix_type full _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.001 _reflns_number_total 2086 _refine_ls_R_factor_all 0.042 _refine_ls_wR_factor_all 0.098 _refine_ls_goodness_of_fit_all 0.724 _reflns_number_gt 1810 _reflns_threshold_expression 'I> 3.00 sigma(I)' _refine_ls_R_factor_gt 0.037 _refine_ls_wR_factor_gt 0.097 _refine_ls_goodness_of_fit_gt 0.599 _refine_ls_number_reflns 1810 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_number_constraints 21 _refine_ls_wR_factor_ref 0.097 _refine_ls_goodness_of_fit_ref 0.599 _refine_ls_abs_structure_details ; ; _refine_ls_abs_structure_Rogers '_' _refine_ls_structure_factor_coef F^2^ _refine_special_details ; Refinement on F^2^. ; _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ; w = 1 / ( s^2^(Fo^2^) + 0.10000 * Fo^2^) ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _computing_structure_refinement 'maXus(Mackay et al., 1999)' _computing_molecular_graphics 'Ortep (Johnson, 1976)' _computing_publication_material 'maXus(Mackay et al., 1999)' _atom_sites_solution_hydrogens geom _refine_diff_density_max 0.12 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.04 #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 -0.31829(13) -0.28191(11) -1.16404(19) 0.0567(9) 1.00 Uij N2 -0.28674(13) -0.24381(11) -0.9001(2) 0.0475(9) 1.00 Uij O3 -0.45328(13) -0.35878(11) -0.8863(3) 0.0707(10) 1.00 Uij C4 -0.18145(14) -0.23719(13) -0.6533(3) 0.0441(10) 1.00 Uij C5 -0.29477(14) -0.29995(13) -1.0223(3) 0.0449(10) 1.00 Uij C6 -0.16996(16) -0.24431(15) -0.4817(3) 0.0498(11) 1.00 Uij C7 -0.26637(15) -0.38749(14) -0.9829(3) 0.0454(10) 1.00 Uij C8 -0.33135(16) -0.44987(14) -0.9488(3) 0.0466(11) 1.00 Uij C9 -0.10968(18) -0.20552(17) -0.7469(3) 0.0570(13) 1.00 Uij C10 -0.29967(18) -0.52910(15) -0.9163(3) 0.0576(13) 1.00 Uij C11 -0.17252(17) -0.40722(16) -0.9906(3) 0.0570(12) 1.00 Uij C12 -0.08794(19) -0.21867(17) -0.4068(3) 0.0614(14) 1.00 Uij C13 -0.43236(17) -0.42753(14) -0.9344(3) 0.0509(11) 1.00 Uij C14 -0.27270(16) -0.26610(15) -0.7267(3) 0.0493(11) 1.00 Uij C15 -0.31489(18) -0.15924(14) -0.9328(3) 0.0590(13) 1.00 Uij C16 -0.50640(16) -0.48785(14) -0.9793(3) 0.0521(11) 1.00 Uij C17 -0.14254(19) -0.48633(19) -0.9615(4) 0.0667(15) 1.00 Uij C18 -0.2046(2) -0.54734(17) -0.9216(4) 0.0646(15) 1.00 Uij C19 -0.59546(18) -0.47353(17) -0.9141(4) 0.0684(15) 1.00 Uij C20 -0.02740(19) -0.1800(2) -0.6715(4) 0.0711(16) 1.00 Uij C21 -0.01758(19) -0.1862(2) -0.5011(4) 0.0711(16) 1.00 Uij C22 -0.4929(2) -0.55263(17) -1.0887(4) 0.0668(15) 1.00 Uij C23 -0.6679(2) -0.5245(2) -0.9601(5) 0.087(2) 1.00 Uij C24 -0.5665(3) -0.6025(2) -1.1326(5) 0.087(2) 1.00 Uij C25 -0.4190(2) -0.1458(2) -0.9073(5) 0.085(2) 1.00 Uij C26 -0.6536(3) -0.5879(2) -1.0684(6) 0.096(2) 1.00 Uij H6 -0.219594 -0.265903 -0.414876 0.054823 1.00 Uiso H9 -0.116023 -0.198921 -0.864897 0.061960 1.00 Uiso H10 -0.343311 -0.571765 -0.889085 0.062549 1.00 Uiso H11 -0.128003 -0.365304 -1.018032 0.062020 1.00 Uiso H12 -0.080041 -0.224697 -0.289033 0.066424 1.00 Uiso H14A -0.273690 -0.325045 -0.717371 0.054292 1.00 Uiso H14B -0.321441 -0.243085 -0.659693 0.054292 1.00 Uiso H15A -0.299802 -0.145649 -1.045683 0.063973 1.00 Uiso H15B -0.281895 -0.123131 -0.859007 0.063973 1.00 Uiso H17 -0.077680 -0.499847 -0.968234 0.071699 1.00 Uiso H18 -0.183381 -0.602158 -0.897862 0.069643 1.00 Uiso H19 -0.606038 -0.428805 -0.838423 0.073374 1.00 Uiso H20 0.022950 -0.160371 -0.739015 0.076099 1.00 Uiso H21 0.038173 -0.166698 -0.448681 0.076075 1.00 Uiso H22 -0.432275 -0.561568 -1.135319 0.071709 1.00 Uiso H23 -0.728471 -0.515474 -0.913215 0.091581 1.00 Uiso H24 -0.556402 -0.648474 -1.205247 0.092465 1.00 Uiso H25A -0.434862 -0.089466 -0.930044 0.089642 1.00 Uiso H25B -0.452760 -0.181297 -0.981106 0.089642 1.00 Uiso H25C -0.434852 -0.158780 -0.794430 0.089642 1.00 Uiso H26 -0.705249 -0.621406 -1.102014 0.100653 1.00 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0629(10) 0.0661(9) 0.0410(8) -.0003(8) -.0062(8) 0.0028(7) N2 0.0481(9) 0.0495(9) 0.0450(9) -.0080(8) -.0053(8) 0.0001(8) O3 0.0567(10) 0.0620(10) 0.0934(15) -.0087(8) 0.0237(10) -.0235(10) C4 0.0436(10) 0.0470(10) 0.0417(10) 0.0006(8) -.0020(9) -.0033(8) C5 0.0379(9) 0.0555(11) 0.0412(10) -.0084(9) -.0019(8) 0.0016(9) C6 0.0532(11) 0.0526(11) 0.0438(10) 0.0001(10) -.0022(10) -.0009(9) C7 0.0471(10) 0.0519(11) 0.0371(10) -.0051(9) -.0013(9) -.0010(9) C8 0.0506(11) 0.0522(11) 0.0372(10) -.0063(10) 0.0011(9) -.0018(8) C9 0.0482(11) 0.0760(16) 0.0466(11) -.0073(11) 0.0024(10) -.0001(12) C10 0.0631(13) 0.0554(12) 0.0541(13) -.0052(11) -.0007(12) 0.0028(11) C11 0.0459(11) 0.0669(14) 0.0583(13) -.0062(10) -.0031(11) 0.0015(11) C12 0.0674(16) 0.0679(14) 0.0490(12) 0.0023(12) -.0154(12) -.0007(12) C13 0.0524(12) 0.0540(12) 0.0463(12) -.0099(10) 0.0091(10) -.0008(10) C14 0.0478(11) 0.0597(12) 0.0404(10) -.0104(10) -.0008(9) -.0019(9) C15 0.0614(14) 0.0523(11) 0.0633(15) -.0031(11) -.0102(13) -.0004(11) C16 0.0525(12) 0.0510(11) 0.0527(12) -.0100(10) -.0003(10) 0.0087(10) C17 0.0527(13) 0.0764(16) 0.0710(18) 0.0079(12) -.0093(12) -.0012(14) C18 0.0670(15) 0.0621(13) 0.0648(15) 0.0093(12) -.0099(13) 0.0020(13) C19 0.0526(13) 0.0663(14) 0.0863(19) -.0071(11) 0.0055(13) 0.0141(16) C20 0.0475(12) 0.093(2) 0.0724(17) -.0139(14) 0.0026(12) 0.0047(17) C21 0.0507(13) 0.0878(18) 0.0748(17) -.0059(13) -.0194(14) -.0002(16) C22 0.0770(16) 0.0648(14) 0.0585(14) -.0141(14) -.0035(14) -.0017(13) C23 0.0550(14) 0.083(2) 0.122(3) -.0172(15) -.0045(18) 0.035(2) C24 0.110(3) 0.0730(17) 0.080(2) -.0283(19) -.027(2) 0.0019(16) C25 0.0703(18) 0.0864(19) 0.097(2) 0.0156(16) -.0104(18) -.009(2) C26 0.086(2) 0.083(2) 0.118(3) -.0409(18) -.037(2) 0.033(2) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 N2 C5 O1 170.4(3) . . . . ? C5 N2 C14 C4 116.7(3) . . . . ? C14 N2 C5 C7 -14.2(2) . . . . ? C15 N2 C5 O1 5.6(2) . . . . ? C15 N2 C5 C7 -179.0(3) . . . . ? C5 N2 C15 C25 84.7(3) . . . . ? C15 N2 C14 C4 -78.2(2) . . . . ? C14 N2 C15 C25 -81.1(3) . . . . ? C9 C4 C6 C12 0.9(2) . . . . ? C6 C4 C9 C20 -0.8(2) . . . . ? C6 C4 C14 N2 169.7(3) . . . . ? C14 C4 C6 C12 -179.8(3) . . . . ? C9 C4 C14 N2 -11.1(2) . . . . ? C14 C4 C9 C20 -180.0(4) . . . . ? O1 C5 N2 C14 170.4(3) . . . . ? O1 C5 N2 C15 5.6(2) . . . . ? O1 C5 C7 C8 -82.5(3) . . . . ? O1 C5 C7 C11 93.7(3) . . . . ? N2 C5 C7 C8 102.0(3) . . . . ? N2 C5 C7 C11 -81.9(3) . . . . ? C7 C5 N2 C14 -14.2(2) . . . . ? C7 C5 N2 C15 -179.0(3) . . . . ? C12 C6 C4 C9 0.9(2) . . . . ? C12 C6 C4 C14 -179.8(3) . . . . ? C4 C6 C12 C21 -0.1(3) . . . . ? C8 C7 C5 O1 -82.5(3) . . . . ? C8 C7 C5 N2 102.0(3) . . . . ? C5 C7 C8 C10 179.0(3) . . . . ? C5 C7 C8 C13 -6.1(2) . . . . ? C11 C7 C5 O1 93.7(3) . . . . ? C11 C7 C5 N2 -81.9(3) . . . . ? C5 C7 C11 C17 -177.9(4) . . . . ? C11 C7 C8 C10 2.9(2) . . . . ? C11 C7 C8 C13 177.8(3) . . . . ? C8 C7 C11 C17 -1.6(2) . . . . ? C10 C8 C7 C5 179.0(3) . . . . ? C10 C8 C7 C11 2.9(2) . . . . ? C7 C8 C10 C18 -1.7(2) . . . . ? C7 C8 C13 O3 -29.2(2) . . . . ? C13 C8 C7 C5 -6.1(2) . . . . ? C13 C8 C7 C11 177.8(3) . . . . ? C7 C8 C13 C16 150.3(3) . . . . ? C10 C8 C13 O3 145.6(3) . . . . ? C10 C8 C13 C16 -35.0(2) . . . . ? C13 C8 C10 C18 -176.4(4) . . . . ? C20 C9 C4 C6 -0.8(2) . . . . ? C20 C9 C4 C14 -180.0(4) . . . . ? C4 C9 C20 C21 -0.2(3) . . . . ? C18 C10 C8 C7 -1.7(2) . . . . ? C18 C10 C8 C13 -176.4(4) . . . . ? C8 C10 C18 C17 -0.8(3) . . . . ? C17 C11 C7 C5 -177.9(4) . . . . ? C17 C11 C7 C8 -1.6(2) . . . . ? C7 C11 C17 C18 -1.0(3) . . . . ? C21 C12 C6 C4 -0.1(3) . . . . ? C6 C12 C21 C20 -1.0(3) . . . . ? O3 C13 C8 C7 -29.2(2) . . . . ? O3 C13 C8 C10 145.6(3) . . . . ? O3 C13 C16 C19 -20.5(2) . . . . ? O3 C13 C16 C22 155.2(4) . . . . ? C16 C13 C8 C7 150.3(3) . . . . ? C16 C13 C8 C10 -35.0(2) . . . . ? C8 C13 C16 C19 160.1(3) . . . . ? C8 C13 C16 C22 -24.3(2) . . . . ? C4 C14 N2 C5 116.7(3) . . . . ? N2 C14 C4 C6 169.7(3) . . . . ? N2 C14 C4 C9 -11.1(2) . . . . ? C4 C14 N2 C15 -78.2(2) . . . . ? C25 C15 N2 C5 84.7(3) . . . . ? C25 C15 N2 C14 -81.1(3) . . . . ? C19 C16 C13 O3 -20.5(2) . . . . ? C19 C16 C13 C8 160.1(3) . . . . ? C13 C16 C19 C23 176.0(4) . . . . ? C22 C16 C13 O3 155.2(4) . . . . ? C22 C16 C13 C8 -24.3(2) . . . . ? C13 C16 C22 C24 -175.6(4) . . . . ? C22 C16 C19 C23 0.1(3) . . . . ? C19 C16 C22 C24 -0.1(3) . . . . ? C18 C17 C11 C7 -1.0(3) . . . . ? C11 C17 C18 C10 2.2(3) . . . . ? C17 C18 C10 C8 -0.8(3) . . . . ? C10 C18 C17 C11 2.2(3) . . . . ? C23 C19 C16 C13 176.0(4) . . . . ? C23 C19 C16 C22 0.1(3) . . . . ? C16 C19 C23 C26 -0.3(3) . . . . ? C21 C20 C9 C4 -0.2(3) . . . . ? C9 C20 C21 C12 1.1(3) . . . . ? C20 C21 C12 C6 -1.0(3) . . . . ? C12 C21 C20 C9 1.1(3) . . . . ? C24 C22 C16 C13 -175.6(4) . . . . ? C24 C22 C16 C19 -0.1(3) . . . . ? C16 C22 C24 C26 0.2(3) . . . . ? C26 C23 C19 C16 -0.3(3) . . . . ? C19 C23 C26 C24 0.5(4) . . . . ? C26 C24 C22 C16 0.2(3) . . . . ? C22 C24 C26 C23 -0.5(4) . . . . ? C24 C26 C23 C19 0.5(4) . . . . ? C23 C26 C24 C22 -0.5(4) . . . . ? _geom_special_details ; All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.226(5) . . ? N2 C5 1.345(5) . . ? N2 C14 1.457(5) . . ? N2 C15 1.455(5) . . ? O3 C13 1.219(5) . . ? C4 C6 1.396(6) . . ? C4 C9 1.377(6) . . ? C4 C14 1.514(5) . . ? C5 C7 1.512(5) . . ? C6 C12 1.389(6) . . ? C7 C8 1.405(5) . . ? C7 C11 1.389(6) . . ? C8 C10 1.389(6) . . ? C8 C13 1.502(6) . . ? C9 C20 1.393(7) . . ? C10 C18 1.400(7) . . ? C11 C17 1.375(7) . . ? C12 C21 1.370(8) . . ? C13 C16 1.491(6) . . ? C15 C25 1.527(8) . . ? C16 C19 1.404(6) . . ? C16 C22 1.385(7) . . ? C17 C18 1.371(7) . . ? C19 C23 1.381(8) . . ? C20 C21 1.383(8) . . ? C22 C24 1.379(8) . . ? C23 C26 1.364(10) . . ? C24 C26 1.375(11) . . ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N2 C14 123.0(3) . . . ? C5 N2 C15 118.9(3) . . . ? C14 N2 C15 116.5(3) . . . ? C6 C4 C9 118.9(4) . . . ? C6 C4 C14 117.6(4) . . . ? C9 C4 C14 123.5(4) . . . ? O1 C5 N2 122.8(4) . . . ? O1 C5 C7 119.6(3) . . . ? N2 C5 C7 117.4(3) . . . ? C4 C6 C12 120.3(4) . . . ? C5 C7 C8 122.6(4) . . . ? C5 C7 C11 118.0(4) . . . ? C8 C7 C11 119.3(4) . . . ? C7 C8 C10 119.1(4) . . . ? C7 C8 C13 119.0(4) . . . ? C10 C8 C13 121.8(4) . . . ? C4 C9 C20 120.6(4) . . . ? C8 C10 C18 120.7(4) . . . ? C7 C11 C17 120.8(4) . . . ? C6 C12 C21 120.2(4) . . . ? O3 C13 C8 119.0(4) . . . ? O3 C13 C16 120.1(4) . . . ? C8 C13 C16 120.9(4) . . . ? N2 C14 C4 114.6(3) . . . ? N2 C15 C25 112.6(4) . . . ? C13 C16 C19 116.9(4) . . . ? C13 C16 C22 123.5(4) . . . ? C19 C16 C22 119.4(4) . . . ? C11 C17 C18 120.7(4) . . . ? C10 C18 C17 119.4(4) . . . ? C16 C19 C23 119.3(6) . . . ? C9 C20 C21 119.8(5) . . . ? C12 C21 C20 120.1(5) . . . ? C16 C22 C24 120.0(5) . . . ? C19 C23 C26 120.6(6) . . . ? C22 C24 C26 120.2(6) . . . ? C23 C26 C24 120.5(5) . . . ? data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 215661' _audit_creation_method maXus _chemical_compound_source 'Local laboratory' _exptl_crystal_description Cube _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.15 _cell_measurement_temperature 298 _refine_ls_hydrogen_treatment refxyz _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method '\q \w scans' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'maXus (Mackay et al., 1999)' _cell_measurement_reflns_used 21 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 loop_ _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 -0.01089 _diffrn_orient_matrix_UB_12 -0.03425 _diffrn_orient_matrix_UB_13 0.06158 _diffrn_orient_matrix_UB_21 0.04787 _diffrn_orient_matrix_UB_22 -0.00022 _diffrn_orient_matrix_UB_23 0.03278 _diffrn_orient_matrix_UB_31 -0.01236 _diffrn_orient_matrix_UB_32 0.02921 _diffrn_orient_matrix_UB_33 0.07255 _cell_formula_units_Z 8 _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 405.497 _diffrn_radiation_type ' CuK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z '-X+ 1/2,-Y,+Z+ 1/2' '+X+ 1/2,+Y,-Z+ 1/2' '+X+ 1/2,-Y+ 1/2,-Z' '-X+ 1/2,+Y+ 1/2,+Z' '-X,+Y+ 1/2,-Z+ 1/2' '+X,-Y+ 1/2,+Z+ 1/2' _symmetry_space_group_name_H-M 'P b c a ' _symmetry_cell_setting Orthorhombic _chemical_formula_moiety 'C28 H23 N O2 ' _chemical_formula_sum 'C28 H23 N O2 ' _chemical_name_systematic ; ? ; _cell_length_a 19.753(5) _cell_length_b 22.214(7) _cell_length_c 9.936(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4360.(2) _diffrn_reflns_number 4640 _diffrn_reflns_theta_max 69.99 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_full 69.99 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_coefficient_mu 0.61 _exptl_crystal_F_000 1711 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C ' 'C ' 0.0181 0.0091 'Waasmaier & Kirfel, 1995' 'H ' 'H ' 0.0000 0.0000 'Waasmaier & Kirfel, 1995' 'O ' 'O ' 0.0492 0.0322 'Waasmaier & Kirfel, 1995' 'N ' 'N ' 0.0311 0.0180 'Waasmaier & Kirfel, 1995' # Refinement statistics _reflns_d_resolution_low 2.36 _reflns_d_resolution_high 0.64 _reflns_limit_h_max 24 _reflns_limit_h_min 0 _reflns_limit_k_max 26 _reflns_limit_k_min 0 _reflns_limit_l_max 12 _reflns_limit_l_min 0 _refine_ls_matrix_type full _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.006 _reflns_number_total 4437 _refine_ls_R_factor_all 0.070 _refine_ls_wR_factor_all 0.218 _refine_ls_goodness_of_fit_all 1.327 _reflns_number_gt 2926 _reflns_threshold_expression 'I> 3.00 sigma(I)' _refine_ls_R_factor_gt 0.051 _refine_ls_wR_factor_gt 0.217 _refine_ls_goodness_of_fit_gt 0.869 _refine_ls_number_reflns 2926 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_number_constraints 23 _refine_ls_wR_factor_ref 0.217 _refine_ls_goodness_of_fit_ref 0.869 _refine_ls_structure_factor_coef F^2^ _refine_special_details ; Refinement on F^2^. ; _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ; w = 1 / ( s^2^(Fo^2^) + 0.10000 * Fo^2^) ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _computing_structure_refinement 'maXus(Mackay et al., 1999)' _computing_molecular_graphics 'Ortep (Johnson, 1976)' _computing_publication_material 'maXus(Mackay et al., 1999)' _atom_sites_solution_hydrogens geom _refine_diff_density_max 0.19 _refine_diff_density_min -0.33 _refine_diff_density_rms 0.08 #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 0.25341(7) 0.12811(7) 0.32807(15) 0.0680(8) 1.00 Uij C2 0.23153(8) 0.07070(7) 0.59806(18) 0.0464(8) 1.00 Uij C3 0.20040(8) 0.12924(8) 0.39172(17) 0.0471(8) 1.00 Uij N4 0.15315(7) 0.17249(6) 0.37460(13) 0.0463(7) 1.00 Uij C5 0.28657(9) 0.11578(8) 0.62486(17) 0.0492(8) 1.00 Uij C6 0.18681(8) 0.07940(7) 0.49093(17) 0.0473(8) 1.00 Uij O7 0.27529(7) 0.16936(6) 0.61766(15) 0.0651(7) 1.00 Uij C8 0.35489(9) 0.09267(8) 0.66202(19) 0.0515(9) 1.00 Uij C9 0.09376(9) 0.17965(8) 0.45989(19) 0.0535(9) 1.00 Uij C10 0.17801(9) 0.28098(8) 0.35417(17) 0.0502(8) 1.00 Uij C11 0.13543(10) 0.03752(9) 0.4700(2) 0.0608(10) 1.00 Uij C12 0.23805(10) 0.29131(9) 0.4216(2) 0.0585(10) 1.00 Uij C13 0.16627(10) 0.22243(9) 0.28137(18) 0.0551(9) 1.00 Uij C14 0.37981(10) 0.03945(9) 0.6086(2) 0.0630(10) 1.00 Uij C15 0.02819(9) 0.18017(9) 0.3817(3) 0.0642(10) 1.00 Uij C16 0.24912(12) 0.34437(10) 0.4893(2) 0.0676(12) 1.00 Uij C17 0.17073(11) -0.01869(8) 0.6620(3) 0.0655(11) 1.00 Uij C18 0.22295(10) 0.02153(9) 0.6825(2) 0.0573(10) 1.00 Uij C19 0.12777(10) -0.01098(9) 0.5555(3) 0.0687(11) 1.00 Uij C20 0.20012(15) 0.38783(10) 0.4914(3) 0.0795(13) 1.00 Uij C21 0.39513(11) 0.12564(11) 0.7497(2) 0.0709(12) 1.00 Uij C22 -0.02484(12) 0.21591(12) 0.4260(4) 0.0957(16) 1.00 Uij C23 0.12881(11) 0.32509(10) 0.3567(2) 0.0664(11) 1.00 Uij C24 0.14013(13) 0.37819(11) 0.4261(3) 0.0832(14) 1.00 Uij C25 0.48287(11) 0.05216(16) 0.7289(3) 0.0943(17) 1.00 Uij C26 0.44402(12) 0.01986(12) 0.6414(3) 0.0805(14) 1.00 Uij C27 0.01931(13) 0.14578(11) 0.2671(3) 0.0885(15) 1.00 Uij C28 -0.09393(17) 0.17970(19) 0.2453(6) 0.151(3) 1.00 Uij C29 -0.04211(18) 0.14602(15) 0.2001(5) 0.133(2) 1.00 Uij C30 0.45846(13) 0.10469(16) 0.7829(3) 0.0926(17) 1.00 Uij C31 -0.08635(15) 0.21560(18) 0.3537(6) 0.142(3) 1.00 Uij H9A 0.091690 0.146777 0.522490 0.059344 1.00 Uiso H9B 0.096990 0.216909 0.508404 0.059344 1.00 Uiso H11 0.104999 0.042729 0.395617 0.066138 1.00 Uiso H12 0.272532 0.260860 0.421134 0.063570 1.00 Uiso H13A 0.205966 0.213461 0.229368 0.061257 1.00 Uiso H13B 0.128246 0.227388 0.222230 0.061257 1.00 Uiso H14 0.352145 0.016566 0.547864 0.070482 1.00 Uiso H16 0.291167 0.351048 0.535423 0.073321 1.00 Uiso H17 0.164742 -0.052395 0.721275 0.071084 1.00 Uiso H18 0.253280 0.015614 0.756863 0.062716 1.00 Uiso H19 0.092059 -0.039553 0.540798 0.072814 1.00 Uiso H20 0.207865 0.425094 0.537837 0.083346 1.00 Uiso H21 0.378271 0.163022 0.784710 0.078109 1.00 Uiso H22 -0.018354 0.240577 0.504309 0.108034 1.00 Uiso H23 0.086943 0.318598 0.309811 0.070872 1.00 Uiso H24 0.105443 0.408421 0.429364 0.089367 1.00 Uiso H25 0.527462 0.038633 0.752570 0.096255 1.00 Uiso H26 0.461012 -0.016816 0.603067 0.086361 1.00 Uiso H27 0.056590 0.122379 0.233884 0.094878 1.00 Uiso H28 -0.136656 0.179218 0.199295 0.147622 1.00 Uiso H29 -0.048786 0.121712 0.121357 0.141300 1.00 Uiso H30 0.486181 0.126142 0.846119 0.099451 1.00 Uiso H31 -0.124147 0.239804 0.381287 0.135286 1.00 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0523(7) 0.0882(10) 0.0636(8) 0.0154(7) 0.0137(6) 0.0080(7) C2 0.0431(8) 0.0443(9) 0.0519(9) 0.0052(6) 0.0002(7) -.0033(7) C3 0.0411(8) 0.0580(10) 0.0421(8) 0.0009(7) -.0010(7) -.0066(7) N4 0.0452(7) 0.0524(8) 0.0413(8) 0.0015(6) 0.0026(6) -.0003(6) C5 0.0537(10) 0.0468(9) 0.0470(9) 0.0014(7) -.0024(7) -.0012(7) C6 0.0444(8) 0.0475(9) 0.0500(9) 0.0048(7) 0.0004(7) -.0080(7) O7 0.0725(9) 0.0458(7) 0.0770(9) 0.0022(6) -.0135(7) -.0025(6) C8 0.0470(9) 0.0551(10) 0.0523(10) -.0051(7) -.0022(7) 0.0046(8) C9 0.0525(10) 0.0482(9) 0.0597(10) 0.0027(7) 0.0139(8) -.0046(8) C10 0.0535(9) 0.0525(9) 0.0445(8) -.0003(7) 0.0034(7) 0.0086(7) C11 0.0520(10) 0.0582(11) 0.0721(12) -.0026(8) -.0078(9) -.0086(10) C12 0.0536(10) 0.0617(11) 0.0602(11) 0.0022(8) 0.0010(8) 0.0093(9) C13 0.0587(10) 0.0641(10) 0.0425(9) 0.0026(8) 0.0019(8) 0.0025(8) C14 0.0538(10) 0.0597(11) 0.0754(13) 0.0020(8) 0.0048(10) 0.0051(10) C15 0.0451(9) 0.0462(9) 0.1014(16) 0.0005(7) 0.0070(10) 0.0146(10) C16 0.0692(13) 0.0637(12) 0.0698(13) -.0119(10) -.0120(11) 0.0092(10) C17 0.0577(11) 0.0464(10) 0.0924(15) 0.0036(8) 0.0120(11) 0.0074(10) C18 0.0539(10) 0.0520(10) 0.0660(11) 0.0082(8) 0.0001(9) 0.0082(9) C19 0.0546(11) 0.0512(11) 0.1002(16) -.0077(8) 0.0043(11) -.0089(11) C20 0.1001(18) 0.0517(12) 0.0865(16) -.0003(11) -.0180(14) 0.0008(10) C21 0.0576(11) 0.0847(14) 0.0704(13) -.0107(10) -.0095(10) -.0074(12) C22 0.0611(12) 0.0795(16) 0.147(3) 0.0229(11) 0.0368(15) 0.0386(16) C23 0.0638(12) 0.0621(12) 0.0733(13) 0.0093(9) -.0121(10) 0.0054(10) C24 0.0912(16) 0.0589(12) 0.0996(18) 0.0207(11) -.0161(15) -.0008(12) C25 0.0438(12) 0.139(3) 0.100(2) 0.0111(14) 0.0000(12) 0.0415(19) C26 0.0583(13) 0.0808(15) 0.1025(18) 0.0125(11) 0.0142(12) 0.0268(14) C27 0.0701(14) 0.0672(14) 0.128(2) 0.0001(11) -.0379(15) -.0031(15) C28 0.0566(16) 0.113(3) 0.282(7) -.0256(19) -.046(3) 0.094(4) C29 0.094(2) 0.0893(19) 0.216(5) -.0240(17) -.083(3) 0.032(2) C30 0.0566(13) 0.138(3) 0.0836(17) -.0164(15) -.0175(12) 0.0029(17) C31 0.0509(15) 0.111(3) 0.264(6) 0.0221(16) 0.038(2) 0.092(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 C2 C6 C3 8.63(15) . . . . ? C6 C2 C5 O7 42.0(2) . . . . ? C6 C2 C5 C8 -138.7(2) . . . . ? C5 C2 C6 C11 -178.7(2) . . . . ? C18 C2 C5 O7 -135.3(2) . . . . ? C18 C2 C5 C8 44.0(2) . . . . ? C5 C2 C18 C17 177.2(3) . . . . ? C18 C2 C6 C3 -174.0(2) . . . . ? C18 C2 C6 C11 -1.4(2) . . . . ? C6 C2 C18 C17 -0.1(2) . . . . ? O1 C3 N4 C9 -171.9(3) . . . . ? O1 C3 N4 C13 -3.3(2) . . . . ? O1 C3 C6 C2 60.2(2) . . . . ? O1 C3 C6 C11 -112.3(2) . . . . ? N4 C3 C6 C2 -121.2(2) . . . . ? C6 C3 N4 C9 9.59(15) . . . . ? N4 C3 C6 C11 66.3(2) . . . . ? C6 C3 N4 C13 178.2(2) . . . . ? C9 N4 C3 O1 -171.9(3) . . . . ? C9 N4 C3 C6 9.59(15) . . . . ? C3 N4 C9 C15 -125.6(2) . . . . ? C13 N4 C3 O1 -3.3(2) . . . . ? C13 N4 C3 C6 178.2(2) . . . . ? C3 N4 C13 C10 -108.9(2) . . . . ? C9 N4 C13 C10 60.6(2) . . . . ? C13 N4 C9 C15 65.4(2) . . . . ? O7 C5 C2 C6 42.0(2) . . . . ? O7 C5 C2 C18 -135.3(2) . . . . ? C8 C5 C2 C6 -138.7(2) . . . . ? C2 C5 C8 C14 34.1(2) . . . . ? C8 C5 C2 C18 44.0(2) . . . . ? C2 C5 C8 C21 -147.3(2) . . . . ? O7 C5 C8 C14 -146.6(3) . . . . ? O7 C5 C8 C21 32.0(2) . . . . ? C2 C6 C3 O1 60.2(2) . . . . ? C2 C6 C3 N4 -121.2(2) . . . . ? C3 C6 C2 C5 8.63(15) . . . . ? C3 C6 C2 C18 -174.0(2) . . . . ? C11 C6 C2 C5 -178.7(2) . . . . ? C11 C6 C2 C18 -1.4(2) . . . . ? C2 C6 C11 C19 1.5(2) . . . . ? C11 C6 C3 O1 -112.3(2) . . . . ? C11 C6 C3 N4 66.3(2) . . . . ? C3 C6 C11 C19 174.0(3) . . . . ? C14 C8 C5 C2 34.1(2) . . . . ? C14 C8 C5 O7 -146.6(3) . . . . ? C5 C8 C14 C26 178.1(3) . . . . ? C21 C8 C5 C2 -147.3(2) . . . . ? C21 C8 C5 O7 32.0(2) . . . . ? C5 C8 C21 C30 -179.3(3) . . . . ? C21 C8 C14 C26 -0.6(2) . . . . ? C14 C8 C21 C30 -0.6(2) . . . . ? C15 C9 N4 C3 -125.6(2) . . . . ? C15 C9 N4 C13 65.4(2) . . . . ? N4 C9 C15 C22 -145.9(3) . . . . ? N4 C9 C15 C27 34.3(2) . . . . ? C12 C10 C13 N4 73.9(2) . . . . ? C13 C10 C12 C16 -179.5(3) . . . . ? C23 C10 C12 C16 -0.4(2) . . . . ? C12 C10 C23 C24 -0.2(2) . . . . ? C23 C10 C13 N4 -105.1(2) . . . . ? C13 C10 C23 C24 178.9(3) . . . . ? C19 C11 C6 C2 1.5(2) . . . . ? C19 C11 C6 C3 174.0(3) . . . . ? C6 C11 C19 C17 -0.1(2) . . . . ? C16 C12 C10 C13 -179.5(3) . . . . ? C10 C12 C16 C20 0.4(2) . . . . ? C16 C12 C10 C23 -0.4(2) . . . . ? C10 C13 N4 C3 -108.9(2) . . . . ? C10 C13 N4 C9 60.6(2) . . . . ? N4 C13 C10 C12 73.9(2) . . . . ? N4 C13 C10 C23 -105.1(2) . . . . ? C26 C14 C8 C5 178.1(3) . . . . ? C26 C14 C8 C21 -0.6(2) . . . . ? C8 C14 C26 C25 1.4(2) . . . . ? C22 C15 C9 N4 -145.9(3) . . . . ? C9 C15 C22 C31 -179.1(4) . . . . ? C27 C15 C9 N4 34.3(2) . . . . ? C9 C15 C27 C29 178.1(4) . . . . ? C22 C15 C27 C29 -1.6(3) . . . . ? C27 C15 C22 C31 0.7(3) . . . . ? C20 C16 C12 C10 0.4(2) . . . . ? C12 C16 C20 C24 0.1(2) . . . . ? C19 C17 C18 C2 1.6(2) . . . . ? C18 C17 C19 C11 -1.4(2) . . . . ? C17 C18 C2 C5 177.2(3) . . . . ? C17 C18 C2 C6 -0.1(2) . . . . ? C2 C18 C17 C19 1.6(2) . . . . ? C17 C19 C11 C6 -0.1(2) . . . . ? C11 C19 C17 C18 -1.4(2) . . . . ? C24 C20 C16 C12 0.1(2) . . . . ? C16 C20 C24 C23 -0.7(2) . . . . ? C30 C21 C8 C5 -179.3(3) . . . . ? C30 C21 C8 C14 -0.6(2) . . . . ? C8 C21 C30 C25 1.1(3) . . . . ? C31 C22 C15 C9 -179.1(4) . . . . ? C31 C22 C15 C27 0.7(3) . . . . ? C15 C22 C31 C28 1.9(4) . . . . ? C24 C23 C10 C12 -0.2(2) . . . . ? C24 C23 C10 C13 178.9(3) . . . . ? C10 C23 C24 C20 0.7(2) . . . . ? C20 C24 C23 C10 0.7(2) . . . . ? C23 C24 C20 C16 -0.7(2) . . . . ? C30 C25 C26 C14 -1.0(3) . . . . ? C26 C25 C30 C21 -0.3(3) . . . . ? C25 C26 C14 C8 1.4(2) . . . . ? C14 C26 C25 C30 -1.0(3) . . . . ? C29 C27 C15 C9 178.1(4) . . . . ? C29 C27 C15 C22 -1.6(3) . . . . ? C15 C27 C29 C28 0.1(4) . . . . ? C29 C28 C31 C22 -3.5(4) . . . . ? C31 C28 C29 C27 2.5(4) . . . . ? C28 C29 C27 C15 0.1(4) . . . . ? C27 C29 C28 C31 2.5(4) . . . . ? C25 C30 C21 C8 1.1(3) . . . . ? C21 C30 C25 C26 -0.3(3) . . . . ? C28 C31 C22 C15 1.9(4) . . . . ? C22 C31 C28 C29 -3.5(4) . . . . ? _geom_special_details ; All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.224(3) . . ? C2 C5 1.502(3) . . ? C2 C6 1.397(3) . . ? C2 C18 1.388(3) . . ? C3 N4 1.350(3) . . ? C3 C6 1.506(3) . . ? N4 C9 1.456(3) . . ? N4 C13 1.468(3) . . ? C5 O7 1.213(3) . . ? C5 C8 1.490(3) . . ? C6 C11 1.392(3) . . ? C8 C14 1.386(4) . . ? C8 C21 1.388(4) . . ? C9 C15 1.510(4) . . ? C10 C12 1.381(4) . . ? C10 C13 1.506(3) . . ? C10 C23 1.380(4) . . ? C11 C19 1.380(4) . . ? C12 C16 1.375(4) . . ? C14 C26 1.380(4) . . ? C15 C22 1.386(4) . . ? C15 C27 1.382(5) . . ? C16 C20 1.367(5) . . ? C17 C18 1.380(4) . . ? C17 C19 1.368(4) . . ? C20 C24 1.368(5) . . ? C21 C30 1.375(5) . . ? C22 C31 1.411(7) . . ? C23 C24 1.384(5) . . ? C25 C26 1.363(6) . . ? C25 C30 1.372(6) . . ? C27 C29 1.384(5) . . ? C28 C29 1.345(9) . . ? C28 C31 1.349(10) . . ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C2 C6 120.0(2) . . . ? C5 C2 C18 120.4(2) . . . ? C6 C2 C18 119.5(2) . . . ? O1 C3 N4 122.8(2) . . . ? O1 C3 C6 118.4(2) . . . ? N4 C3 C6 118.8(2) . . . ? C3 N4 C9 124.2(2) . . . ? C3 N4 C13 119.7(2) . . . ? C9 N4 C13 115.3(2) . . . ? C2 C5 O7 120.7(2) . . . ? C2 C5 C8 118.0(2) . . . ? O7 C5 C8 121.2(2) . . . ? C2 C6 C3 119.2(2) . . . ? C2 C6 C11 118.8(2) . . . ? C3 C6 C11 121.6(2) . . . ? C5 C8 C14 121.4(2) . . . ? C5 C8 C21 119.5(2) . . . ? C14 C8 C21 119.1(3) . . . ? N4 C9 C15 113.1(2) . . . ? C12 C10 C13 120.6(2) . . . ? C12 C10 C23 118.5(2) . . . ? C13 C10 C23 120.9(2) . . . ? C6 C11 C19 120.7(3) . . . ? C10 C12 C16 121.1(3) . . . ? N4 C13 C10 112.1(2) . . . ? C8 C14 C26 120.3(3) . . . ? C9 C15 C22 119.3(3) . . . ? C9 C15 C27 121.9(2) . . . ? C22 C15 C27 118.8(3) . . . ? C12 C16 C20 120.0(3) . . . ? C18 C17 C19 119.8(3) . . . ? C2 C18 C17 120.8(2) . . . ? C11 C19 C17 120.4(2) . . . ? C16 C20 C24 119.7(3) . . . ? C8 C21 C30 119.5(3) . . . ? C15 C22 C31 119.1(5) . . . ? C10 C23 C24 120.0(3) . . . ? C20 C24 C23 120.6(3) . . . ? C26 C25 C30 119.9(3) . . . ? C14 C26 C25 120.1(3) . . . ? C15 C27 C29 120.4(4) . . . ? C29 C28 C31 120.7(5) . . . ? C27 C29 C28 120.6(6) . . . ? C21 C30 C25 120.9(3) . . . ? C22 C31 C28 120.3(4) . . . ?