# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Mamane, Victor' _publ_contact_author_email victor.mamane@srsmc.uhp-nancy.fr _publ_section_title ; Synthesis of new pentacyclic chromophores through a highly regio- and diastereoselective cascade process ; loop_ _publ_author_name Z.e.a.Chamas O.Dietz E.Aubert Y.Fort V.Mamane # Attachment '- Compound_1c.cif' data_vm594 _database_code_depnum_ccdc_archive 'CCDC 734891' #TrackingRef '- Compound_1c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 12-Hydroxy-11b-methyl-11b,12-dihydro-11a-aza-indeno[2,1-a]fluoren-11-one ; _chemical_name_common ;12-Hydroxy-11b-methyl-11b,12-dihydro-11a-aza-indeno(2,1- a)fluoren-11-one ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H15 N O2' _chemical_formula_sum 'C20 H15 N O2' _chemical_formula_weight 301.33 _chemical_absolute_configuration unk 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.03265(6) _cell_length_b 14.26965(12) _cell_length_c 16.47322(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1418.09(3) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 17436 _cell_measurement_theta_min 3.1064 _cell_measurement_theta_max 45.4199 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2702 _exptl_crystal_size_mid 0.2037 _exptl_crystal_size_min 0.1197 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.982 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'XCalibur Oxford Diffraction Kappa CCD' _diffrn_measurement_method oscillation _diffrn_detector_area_resol_mean 10.4508 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 30002 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 39.76 _reflns_number_total 4835 _reflns_number_gt 4522 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SIR_92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0595P)^2^+0.0879P] 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 4835 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0922 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O14 O 0.39233(12) 0.88802(5) 0.70431(4) 0.01763(12) Uani 1 1 d . . . H14 H 0.3113 0.9339 0.6926 0.026 Uiso 1 1 calc R . . O22 O 0.28925(11) 1.04712(5) 0.60933(4) 0.01546(11) Uani 1 1 d . . . N1 N 0.61107(12) 0.99861(5) 0.54467(4) 0.01148(10) Uani 1 1 d . . . C3 C 0.93297(14) 0.98333(6) 0.45984(5) 0.01282(12) Uani 1 1 d . . . H3 H 1.0282 1.0074 0.4189 0.015 Uiso 1 1 calc R . . C4 C 0.98825(14) 0.89717(6) 0.50199(5) 0.01244(12) Uani 1 1 d . . . H4 H 1.1071 0.8592 0.4833 0.015 Uiso 1 1 calc R . . C15 C 0.62415(14) 1.10563(5) 0.44083(4) 0.01211(12) Uani 1 1 d . . . C19 C 0.26889(15) 1.18465(6) 0.46056(5) 0.01469(13) Uani 1 1 d . . . H19 H 0.1358 1.1933 0.4905 0.018 Uiso 1 1 calc R . . C20 C 0.42705(14) 1.11943(5) 0.48435(5) 0.01211(11) Uani 1 1 d . . . C16 C 0.66851(16) 1.15823(6) 0.37130(5) 0.01587(14) Uani 1 1 d . . . H16 H 0.8015 1.1496 0.3414 0.019 Uiso 1 1 calc R . . C5 C 0.87021(13) 0.87106(5) 0.56799(4) 0.01112(11) Uani 1 1 d . . . C23 C 0.79555(15) 0.98957(6) 0.67749(5) 0.01401(13) Uani 1 1 d . . . H23C H 0.6803 1.0283 0.7025 0.021 Uiso 1 1 calc R . . H23B H 0.9150 1.0299 0.6573 0.021 Uiso 1 1 calc R . . H23A H 0.8551 0.9459 0.7179 0.021 Uiso 1 1 calc R . . C21 C 0.42419(14) 1.05361(5) 0.55363(5) 0.01173(11) Uani 1 1 d . . . C9 C 0.94477(17) 0.62472(6) 0.65361(5) 0.01686(14) Uani 1 1 d . . . H9 H 1.0422 0.5724 0.6546 0.020 Uiso 1 1 calc R . . C7 C 0.85777(14) 0.78068(5) 0.60962(5) 0.01195(11) Uani 1 1 d . . . C8 C 1.00408(15) 0.70487(6) 0.61027(5) 0.01492(13) Uani 1 1 d . . . H8 H 1.1409 0.7078 0.5818 0.018 Uiso 1 1 calc R . . C2 C 0.74434(14) 1.02896(5) 0.47954(4) 0.01146(11) Uani 1 1 d . . . C17 C 0.51059(18) 1.22393(7) 0.34735(5) 0.01918(15) Uani 1 1 d . . . H17 H 0.5372 1.2608 0.3003 0.023 Uiso 1 1 calc R . . C10 C 0.74331(17) 0.62039(6) 0.69577(5) 0.01679(14) Uani 1 1 d . . . H10 H 0.7065 0.5655 0.7255 0.020 Uiso 1 1 calc R . . C6 C 0.69566(13) 0.93411(5) 0.60651(4) 0.01079(11) Uani 1 1 d . . . C12 C 0.65514(14) 0.77550(5) 0.65121(5) 0.01210(12) Uani 1 1 d . . . C11 C 0.59605(16) 0.69584(6) 0.69455(5) 0.01486(13) Uani 1 1 d . . . H11 H 0.4588 0.6928 0.7227 0.018 Uiso 1 1 calc R . . C13 C 0.51798(14) 0.86207(5) 0.63567(5) 0.01206(12) Uani 1 1 d . . . H13 H 0.4142 0.8490 0.5897 0.014 Uiso 1 1 calc R . . C18 C 0.31338(17) 1.23699(6) 0.39094(5) 0.01801(15) Uani 1 1 d . . . H18 H 0.2087 1.2821 0.3728 0.022 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 O14 0.0165(3) 0.0175(2) 0.0189(3) 0.0014(2) 0.0082(2) 0.0012(2) O22 0.0127(3) 0.0173(2) 0.0164(2) 0.0017(2) 0.0054(2) 0.0012(2) N1 0.0103(2) 0.0123(2) 0.0118(2) 0.00131(18) 0.00252(19) 0.00124(19) C3 0.0113(3) 0.0141(3) 0.0130(2) -0.0005(2) 0.0028(2) -0.0003(2) C4 0.0107(3) 0.0138(3) 0.0128(2) -0.0014(2) 0.0019(2) 0.0006(2) C15 0.0132(3) 0.0118(3) 0.0113(2) 0.0000(2) 0.0012(2) -0.0006(2) C19 0.0139(3) 0.0136(3) 0.0166(3) 0.0013(2) -0.0005(3) 0.0010(2) C20 0.0121(3) 0.0113(2) 0.0129(3) 0.0001(2) 0.0008(2) -0.0006(2) C16 0.0171(3) 0.0172(3) 0.0133(3) 0.0023(2) 0.0022(3) -0.0002(3) C5 0.0100(3) 0.0116(2) 0.0117(2) -0.0013(2) 0.0007(2) 0.0002(2) C23 0.0142(3) 0.0148(3) 0.0131(3) -0.0032(2) 0.0002(2) -0.0013(2) C21 0.0105(3) 0.0116(2) 0.0131(2) -0.0002(2) 0.0016(2) -0.0005(2) C9 0.0217(4) 0.0131(3) 0.0158(3) -0.0006(2) -0.0020(3) 0.0037(3) C7 0.0123(3) 0.0114(2) 0.0122(2) -0.0014(2) -0.0005(2) 0.0006(2) C8 0.0155(3) 0.0140(3) 0.0153(3) -0.0014(2) -0.0007(3) 0.0029(2) C2 0.0112(3) 0.0118(2) 0.0114(2) -0.0004(2) 0.0022(2) -0.0010(2) C17 0.0219(4) 0.0206(3) 0.0150(3) 0.0054(3) 0.0013(3) 0.0019(3) C10 0.0227(4) 0.0131(3) 0.0146(3) 0.0017(2) -0.0022(3) 0.0004(3) C6 0.0103(3) 0.0110(2) 0.0110(2) -0.0003(2) 0.0013(2) 0.0001(2) C12 0.0128(3) 0.0117(3) 0.0118(2) 0.0000(2) -0.0002(2) -0.0008(2) C11 0.0174(3) 0.0137(3) 0.0135(3) 0.0015(2) -0.0003(2) -0.0018(3) C13 0.0106(3) 0.0127(3) 0.0130(3) 0.0004(2) 0.0018(2) -0.0009(2) C18 0.0197(4) 0.0170(3) 0.0173(3) 0.0036(3) -0.0007(3) 0.0026(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O14 C13 1.4108(10) . ? O14 H14 0.8400 . ? O22 C21 1.2302(10) . ? N1 C21 1.3816(11) . ? N1 C2 1.4089(10) . ? N1 C6 1.4646(10) . ? C3 C2 1.3506(11) . ? C3 C4 1.4510(11) . ? C3 H3 0.9500 . ? C4 C5 1.3520(11) . ? C4 H4 0.9500 . ? C15 C16 1.3952(11) . ? C15 C20 1.4024(11) . ? C15 C2 1.4593(11) . ? C19 C20 1.3894(12) . ? C19 C18 1.3947(12) . ? C19 H19 0.9500 . ? C20 C21 1.4780(11) . ? C16 C17 1.3936(13) . ? C16 H16 0.9500 . ? C5 C7 1.4626(11) . ? C5 C6 1.5235(11) . ? C23 C6 1.5351(11) . ? C23 H23C 0.9800 . ? C23 H23B 0.9800 . ? C23 H23A 0.9800 . ? C9 C8 1.3950(12) . ? C9 C10 1.4011(14) . ? C9 H9 0.9500 . ? C7 C8 1.3962(11) . ? C7 C12 1.4032(12) . ? C8 H8 0.9500 . ? C17 C18 1.4020(14) . ? C17 H17 0.9500 . ? C10 C11 1.3959(13) . ? C10 H10 0.9500 . ? C6 C13 1.5609(11) . ? C12 C11 1.3890(11) . ? C12 C13 1.5087(11) . ? C11 H11 0.9500 . ? C13 H13 1.0000 . ? C18 H18 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 C13 O14 H14 109.5 . . ? C21 N1 C2 111.86(6) . . ? C21 N1 C6 124.54(6) . . ? C2 N1 C6 121.60(7) . . ? C2 C3 C4 119.15(7) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 119.82(7) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C16 C15 C20 120.45(8) . . ? C16 C15 C2 131.82(8) . . ? C20 C15 C2 107.64(6) . . ? C20 C19 C18 117.29(8) . . ? C20 C19 H19 121.4 . . ? C18 C19 H19 121.4 . . ? C19 C20 C15 122.14(7) . . ? C19 C20 C21 129.46(7) . . ? C15 C20 C21 108.39(7) . . ? C17 C16 C15 117.59(8) . . ? C17 C16 H16 121.2 . . ? C15 C16 H16 121.2 . . ? C4 C5 C7 130.32(7) . . ? C4 C5 C6 122.43(7) . . ? C7 C5 C6 106.86(6) . . ? C6 C23 H23C 109.5 . . ? C6 C23 H23B 109.5 . . ? H23C C23 H23B 109.5 . . ? C6 C23 H23A 109.5 . . ? H23C C23 H23A 109.5 . . ? H23B C23 H23A 109.5 . . ? O22 C21 N1 125.23(7) . . ? O22 C21 C20 129.16(8) . . ? N1 C21 C20 105.61(6) . . ? C8 C9 C10 120.82(8) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C8 C7 C12 120.41(7) . . ? C8 C7 C5 130.87(7) . . ? C12 C7 C5 108.66(7) . . ? C9 C8 C7 118.49(8) . . ? C9 C8 H8 120.8 . . ? C7 C8 H8 120.8 . . ? C3 C2 N1 121.04(7) . . ? C3 C2 C15 132.45(7) . . ? N1 C2 C15 106.24(7) . . ? C16 C17 C18 121.64(8) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C11 C10 C9 120.72(8) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? N1 C6 C5 108.80(6) . . ? N1 C6 C23 110.03(6) . . ? C5 C6 C23 110.51(7) . . ? N1 C6 C13 112.87(6) . . ? C5 C6 C13 102.35(6) . . ? C23 C6 C13 112.01(6) . . ? C11 C12 C7 121.17(8) . . ? C11 C12 C13 128.07(8) . . ? C7 C12 C13 110.60(6) . . ? C12 C11 C10 118.38(8) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? O14 C13 C12 111.94(6) . . ? O14 C13 C6 116.28(6) . . ? C12 C13 C6 102.41(6) . . ? O14 C13 H13 108.6 . . ? C12 C13 H13 108.6 . . ? C6 C13 H13 108.6 . . ? C19 C18 C17 120.88(8) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? 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 C3 C4 C5 -9.87(12) . . . . ? C18 C19 C20 C15 -0.14(12) . . . . ? C18 C19 C20 C21 -178.79(8) . . . . ? C16 C15 C20 C19 0.29(12) . . . . ? C2 C15 C20 C19 -176.69(7) . . . . ? C16 C15 C20 C21 179.19(7) . . . . ? C2 C15 C20 C21 2.21(9) . . . . ? C20 C15 C16 C17 -0.09(12) . . . . ? C2 C15 C16 C17 176.04(9) . . . . ? C3 C4 C5 C7 164.71(8) . . . . ? C3 C4 C5 C6 -7.10(12) . . . . ? C2 N1 C21 O22 -174.04(8) . . . . ? C6 N1 C21 O22 -9.97(13) . . . . ? C2 N1 C21 C20 5.29(9) . . . . ? C6 N1 C21 C20 169.35(7) . . . . ? C19 C20 C21 O22 -6.47(15) . . . . ? C15 C20 C21 O22 174.73(8) . . . . ? C19 C20 C21 N1 174.23(8) . . . . ? C15 C20 C21 N1 -4.56(8) . . . . ? C4 C5 C7 C8 21.42(15) . . . . ? C6 C5 C7 C8 -165.80(8) . . . . ? C4 C5 C7 C12 -155.80(8) . . . . ? C6 C5 C7 C12 16.98(8) . . . . ? C10 C9 C8 C7 -0.19(13) . . . . ? C12 C7 C8 C9 -0.54(12) . . . . ? C5 C7 C8 C9 -177.49(8) . . . . ? C4 C3 C2 N1 5.41(12) . . . . ? C4 C3 C2 C15 -167.84(8) . . . . ? C21 N1 C2 C3 -178.83(7) . . . . ? C6 N1 C2 C3 16.57(11) . . . . ? C21 N1 C2 C15 -4.01(9) . . . . ? C6 N1 C2 C15 -168.62(7) . . . . ? C16 C15 C2 C3 -1.60(16) . . . . ? C20 C15 C2 C3 174.90(9) . . . . ? C16 C15 C2 N1 -175.58(9) . . . . ? C20 C15 C2 N1 0.93(8) . . . . ? C15 C16 C17 C18 -0.24(14) . . . . ? C8 C9 C10 C11 0.78(13) . . . . ? C21 N1 C6 C5 167.50(7) . . . . ? C2 N1 C6 C5 -29.91(9) . . . . ? C21 N1 C6 C23 -71.30(10) . . . . ? C2 N1 C6 C23 91.29(8) . . . . ? C21 N1 C6 C13 54.62(10) . . . . ? C2 N1 C6 C13 -142.79(7) . . . . ? C4 C5 C6 N1 25.41(10) . . . . ? C7 C5 C6 N1 -148.07(6) . . . . ? C4 C5 C6 C23 -95.50(9) . . . . ? C7 C5 C6 C23 91.02(7) . . . . ? C4 C5 C6 C13 145.06(8) . . . . ? C7 C5 C6 C13 -28.42(8) . . . . ? C8 C7 C12 C11 0.71(12) . . . . ? C5 C7 C12 C11 178.27(7) . . . . ? C8 C7 C12 C13 -175.08(7) . . . . ? C5 C7 C12 C13 2.49(9) . . . . ? C7 C12 C11 C10 -0.12(12) . . . . ? C13 C12 C11 C10 174.86(8) . . . . ? C9 C10 C11 C12 -0.61(13) . . . . ? C11 C12 C13 O14 39.26(11) . . . . ? C7 C12 C13 O14 -145.33(7) . . . . ? C11 C12 C13 C6 164.52(8) . . . . ? C7 C12 C13 C6 -20.07(8) . . . . ? N1 C6 C13 O14 -92.31(8) . . . . ? C5 C6 C13 O14 150.93(7) . . . . ? C23 C6 C13 O14 32.54(9) . . . . ? N1 C6 C13 C12 145.33(6) . . . . ? C5 C6 C13 C12 28.57(7) . . . . ? C23 C6 C13 C12 -89.82(7) . . . . ? C20 C19 C18 C17 -0.20(14) . . . . ? C16 C17 C18 C19 0.40(15) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 39.76 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.492 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.059 # Attachment '- Compound_1a.cif' data_vm604 _database_code_depnum_ccdc_archive 'CCDC 734892' #TrackingRef '- Compound_1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 12-Hydroxy-5-methyl-11b,12-dihydro-11a-aza-indeno[2,1-a]fluoren-11-one ; _chemical_name_common ;12-Hydroxy-5-methyl-11b,12-dihydro-11a-aza-indeno(2,1- a)fluoren-11-one ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H15 N O2' _chemical_formula_sum 'C20 H15 N O2' _chemical_formula_weight 301.33 _chemical_absolute_configuration unk 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.03310(7) _cell_length_b 15.7754(2) _cell_length_c 22.1253(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1407.69(4) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 18092 _cell_measurement_theta_min 3.6778 _cell_measurement_theta_max 45.3947 _exptl_crystal_description prism _exptl_crystal_colour 'yellow - green' _exptl_crystal_size_max 0.3050 _exptl_crystal_size_mid 0.2788 _exptl_crystal_size_min 0.1038 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'XCalibur Oxford Diffraction Kappa CCD' _diffrn_measurement_method oscillation _diffrn_detector_area_resol_mean 10.4508 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 23052 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 34.64 _reflns_number_total 3499 _reflns_number_gt 3353 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SIR_92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+0.5847P] 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 3499 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1248 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 1.209 _refine_ls_restrained_S_all 1.209 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O14 O -0.0805(3) 0.32034(7) 0.77839(5) 0.0165(2) Uani 1 1 d . . . H14 H -0.0543 0.3175 0.8160 0.025 Uiso 1 1 calc R . . O22 O 0.1447(4) 0.25887(8) 0.88737(5) 0.0198(3) Uani 1 1 d . . . N1 N 0.2726(4) 0.14469(8) 0.82573(5) 0.0125(2) Uani 1 1 d . . . C2 C 0.4098(4) 0.06303(9) 0.83182(6) 0.0122(2) Uani 1 1 d . . . C7 C 0.1020(4) 0.16655(9) 0.66468(6) 0.0123(2) Uani 1 1 d . . . C4 C 0.3553(4) 0.04047(9) 0.72279(6) 0.0128(2) Uani 1 1 d . . . C19 C 0.5068(5) 0.14609(10) 0.98443(7) 0.0166(3) Uani 1 1 d . . . H19 H 0.4496 0.1978 1.0038 0.020 Uiso 1 1 calc R . . C9 C -0.0709(5) 0.20660(11) 0.56464(7) 0.0179(3) Uani 1 1 d . . . H9 H -0.1110 0.1922 0.5236 0.021 Uiso 1 1 calc R . . C12 C 0.0423(4) 0.25029(9) 0.68390(6) 0.0125(2) Uani 1 1 d . . . C18 C 0.6688(5) 0.08174(11) 1.01554(7) 0.0195(3) Uani 1 1 d . . . H18 H 0.7252 0.0897 1.0568 0.023 Uiso 1 1 calc R . . C10 C -0.1326(5) 0.28898(11) 0.58434(7) 0.0192(3) Uani 1 1 d . . . H10 H -0.2131 0.3301 0.5566 0.023 Uiso 1 1 calc R . . C11 C -0.0767(5) 0.31145(10) 0.64455(7) 0.0161(3) Uani 1 1 d . . . H11 H -0.1194 0.3675 0.6582 0.019 Uiso 1 1 calc R . . C20 C 0.4317(4) 0.13195(9) 0.92391(6) 0.0133(2) Uani 1 1 d . . . C23 C 0.4631(5) -0.01230(10) 0.66963(7) 0.0168(3) Uani 1 1 d . . . H23A H 0.2704 -0.0415 0.6525 0.025 Uiso 1 1 calc R . . H23B H 0.6267 -0.0543 0.6829 0.025 Uiso 1 1 calc R . . H23C H 0.5625 0.0245 0.6389 0.025 Uiso 1 1 calc R . . C21 C 0.2664(4) 0.18818(9) 0.87975(6) 0.0138(3) Uani 1 1 d . . . C16 C 0.6717(5) -0.00877(10) 0.92628(7) 0.0166(3) Uani 1 1 d . . . H16 H 0.7260 -0.0608 0.9070 0.020 Uiso 1 1 calc R . . C17 C 0.7500(5) 0.00541(11) 0.98694(7) 0.0190(3) Uani 1 1 d . . . H17 H 0.8606 -0.0376 1.0092 0.023 Uiso 1 1 calc R . . C6 C 0.0891(4) 0.16834(9) 0.77162(6) 0.0118(2) Uani 1 1 d . . . H6 H -0.1517 0.1575 0.7791 0.014 Uiso 1 1 calc R . . C8 C 0.0488(5) 0.14478(10) 0.60414(6) 0.0156(3) Uani 1 1 d . . . H8 H 0.0933 0.0890 0.5902 0.019 Uiso 1 1 calc R . . C3 C 0.4447(4) 0.01166(9) 0.78330(6) 0.0139(3) Uani 1 1 d . . . H3 H 0.5287 -0.0441 0.7887 0.017 Uiso 1 1 calc R . . C15 C 0.5114(4) 0.05583(9) 0.89495(6) 0.0130(3) Uani 1 1 d . . . C13 C 0.1283(4) 0.26050(9) 0.74975(6) 0.0121(2) Uani 1 1 d . . . H13 H 0.3649 0.2785 0.7538 0.015 Uiso 1 1 calc R . . C5 C 0.1963(4) 0.11586(9) 0.71744(6) 0.0122(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O14 0.0205(6) 0.0133(4) 0.0159(4) -0.0037(4) -0.0009(5) 0.0045(4) O22 0.0294(7) 0.0145(5) 0.0154(4) -0.0045(4) -0.0005(5) 0.0050(5) N1 0.0166(6) 0.0103(4) 0.0107(4) -0.0013(4) 0.0004(4) 0.0008(4) C2 0.0140(6) 0.0101(5) 0.0126(5) 0.0004(4) 0.0022(5) -0.0005(5) C7 0.0120(6) 0.0129(5) 0.0119(5) -0.0006(4) 0.0014(5) -0.0012(5) C4 0.0154(6) 0.0110(5) 0.0120(5) -0.0012(4) 0.0013(5) -0.0006(5) C19 0.0199(7) 0.0170(6) 0.0129(5) -0.0015(5) -0.0001(5) -0.0010(6) C9 0.0213(8) 0.0205(6) 0.0119(5) 0.0013(5) -0.0006(6) -0.0032(6) C12 0.0118(6) 0.0128(5) 0.0130(5) -0.0001(4) 0.0000(5) -0.0006(5) C18 0.0247(8) 0.0209(7) 0.0130(5) 0.0004(5) -0.0019(6) -0.0005(6) C10 0.0237(8) 0.0186(6) 0.0152(6) 0.0035(5) -0.0015(6) -0.0009(6) C11 0.0174(7) 0.0145(6) 0.0164(6) 0.0017(5) -0.0014(6) 0.0002(6) C20 0.0149(6) 0.0134(5) 0.0114(5) -0.0005(4) 0.0008(5) -0.0011(5) C23 0.0228(8) 0.0138(5) 0.0140(5) -0.0033(5) 0.0036(6) 0.0009(6) C21 0.0161(7) 0.0141(6) 0.0112(5) -0.0019(4) 0.0012(5) -0.0010(5) C16 0.0190(7) 0.0153(6) 0.0154(6) 0.0016(5) 0.0016(6) 0.0013(6) C17 0.0229(8) 0.0187(6) 0.0152(6) 0.0040(5) -0.0008(6) 0.0007(6) C6 0.0136(6) 0.0116(5) 0.0101(5) -0.0010(4) 0.0008(5) -0.0005(5) C8 0.0189(7) 0.0160(6) 0.0120(5) -0.0014(4) 0.0010(5) -0.0015(6) C3 0.0179(7) 0.0108(5) 0.0131(5) -0.0008(4) 0.0022(5) -0.0002(5) C15 0.0145(7) 0.0126(5) 0.0119(5) 0.0005(4) 0.0011(5) -0.0004(5) C13 0.0127(6) 0.0105(5) 0.0133(5) -0.0010(4) 0.0000(5) -0.0005(5) C5 0.0140(6) 0.0113(5) 0.0113(5) -0.0010(4) 0.0006(5) -0.0009(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O14 C13 1.4147(19) . ? O14 H14 0.8400 . ? O22 C21 1.2300(19) . ? N1 C21 1.3783(18) . ? N1 C2 1.4087(19) . ? N1 C6 1.4561(19) . ? C2 C3 1.352(2) . ? C2 C15 1.460(2) . ? C7 C8 1.399(2) . ? C7 C12 1.409(2) . ? C7 C5 1.465(2) . ? C4 C5 1.356(2) . ? C4 C3 1.459(2) . ? C4 C23 1.505(2) . ? C19 C18 1.390(2) . ? C19 C20 1.391(2) . ? C19 H19 0.9500 . ? C9 C10 1.393(2) . ? C9 C8 1.396(2) . ? C9 H9 0.9500 . ? C12 C11 1.385(2) . ? C12 C13 1.506(2) . ? C18 C17 1.399(2) . ? C18 H18 0.9500 . ? C10 C11 1.397(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C20 C15 1.399(2) . ? C20 C21 1.478(2) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C16 C15 1.392(2) . ? C16 C17 1.397(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C6 C5 1.520(2) . ? C6 C13 1.540(2) . ? C6 H6 1.0000 . ? C8 H8 0.9500 . ? C3 H3 0.9500 . ? C13 H13 1.0000 . ? 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 C13 O14 H14 109.5 . . ? C21 N1 C2 112.30(12) . . ? C21 N1 C6 125.19(13) . . ? C2 N1 C6 120.84(12) . . ? C3 C2 N1 120.86(13) . . ? C3 C2 C15 133.13(14) . . ? N1 C2 C15 105.83(12) . . ? C8 C7 C12 119.54(14) . . ? C8 C7 C5 131.95(13) . . ? C12 C7 C5 108.40(12) . . ? C5 C4 C3 118.04(13) . . ? C5 C4 C23 123.60(13) . . ? C3 C4 C23 118.24(13) . . ? C18 C19 C20 117.53(15) . . ? C18 C19 H19 121.2 . . ? C20 C19 H19 121.2 . . ? C10 C9 C8 121.18(14) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C11 C12 C7 121.51(14) . . ? C11 C12 C13 127.82(13) . . ? C7 C12 C13 110.67(12) . . ? C19 C18 C17 120.98(15) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C9 C10 C11 120.42(15) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 118.60(14) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C19 C20 C15 121.91(14) . . ? C19 C20 C21 129.66(14) . . ? C15 C20 C21 108.42(12) . . ? C4 C23 H23A 109.5 . . ? C4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O22 C21 N1 125.26(14) . . ? O22 C21 C20 129.29(13) . . ? N1 C21 C20 105.44(12) . . ? C15 C16 C17 117.80(15) . . ? C15 C16 H16 121.1 . . ? C17 C16 H16 121.1 . . ? C16 C17 C18 121.29(16) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? N1 C6 C5 111.38(12) . . ? N1 C6 C13 116.62(12) . . ? C5 C6 C13 103.73(11) . . ? N1 C6 H6 108.3 . . ? C5 C6 H6 108.3 . . ? C13 C6 H6 108.3 . . ? C9 C8 C7 118.75(14) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C2 C3 C4 121.06(13) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C16 C15 C20 120.48(14) . . ? C16 C15 C2 131.59(14) . . ? C20 C15 C2 107.88(13) . . ? O14 C13 C12 111.57(13) . . ? O14 C13 C6 115.35(13) . . ? C12 C13 C6 100.33(11) . . ? O14 C13 H13 109.7 . . ? C12 C13 H13 109.7 . . ? C6 C13 H13 109.7 . . ? C4 C5 C7 132.12(13) . . ? C4 C5 C6 122.91(13) . . ? C7 C5 C6 104.92(12) . . ? 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 C21 N1 C2 C3 -178.25(16) . . . . ? C6 N1 C2 C3 15.8(2) . . . . ? C21 N1 C2 C15 -2.45(18) . . . . ? C6 N1 C2 C15 -168.43(14) . . . . ? C8 C7 C12 C11 1.7(3) . . . . ? C5 C7 C12 C11 -174.87(16) . . . . ? C8 C7 C12 C13 -177.73(14) . . . . ? C5 C7 C12 C13 5.69(19) . . . . ? C20 C19 C18 C17 -0.5(3) . . . . ? C8 C9 C10 C11 -0.3(3) . . . . ? C7 C12 C11 C10 -1.0(3) . . . . ? C13 C12 C11 C10 178.31(17) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C18 C19 C20 C15 0.6(3) . . . . ? C18 C19 C20 C21 -179.26(18) . . . . ? C2 N1 C21 O22 -176.25(17) . . . . ? C6 N1 C21 O22 -11.0(3) . . . . ? C2 N1 C21 C20 3.56(18) . . . . ? C6 N1 C21 C20 168.82(14) . . . . ? C19 C20 C21 O22 -3.6(3) . . . . ? C15 C20 C21 O22 176.47(18) . . . . ? C19 C20 C21 N1 176.59(17) . . . . ? C15 C20 C21 N1 -3.32(18) . . . . ? C15 C16 C17 C18 0.4(3) . . . . ? C19 C18 C17 C16 0.0(3) . . . . ? C21 N1 C6 C5 170.38(14) . . . . ? C2 N1 C6 C5 -25.53(19) . . . . ? C21 N1 C6 C13 51.6(2) . . . . ? C2 N1 C6 C13 -144.29(14) . . . . ? C10 C9 C8 C7 0.9(3) . . . . ? C12 C7 C8 C9 -1.6(3) . . . . ? C5 C7 C8 C9 174.01(18) . . . . ? N1 C2 C3 C4 2.8(3) . . . . ? C15 C2 C3 C4 -171.70(17) . . . . ? C5 C4 C3 C2 -8.5(2) . . . . ? C23 C4 C3 C2 167.80(16) . . . . ? C17 C16 C15 C20 -0.3(3) . . . . ? C17 C16 C15 C2 176.90(18) . . . . ? C19 C20 C15 C16 -0.2(3) . . . . ? C21 C20 C15 C16 179.67(15) . . . . ? C19 C20 C15 C2 -178.01(15) . . . . ? C21 C20 C15 C2 1.90(19) . . . . ? C3 C2 C15 C16 -2.2(3) . . . . ? N1 C2 C15 C16 -177.23(17) . . . . ? C3 C2 C15 C20 175.27(18) . . . . ? N1 C2 C15 C20 0.21(18) . . . . ? C11 C12 C13 O14 33.2(2) . . . . ? C7 C12 C13 O14 -147.41(14) . . . . ? C11 C12 C13 C6 155.88(17) . . . . ? C7 C12 C13 C6 -24.73(18) . . . . ? N1 C6 C13 O14 -83.84(18) . . . . ? C5 C6 C13 O14 153.33(13) . . . . ? N1 C6 C13 C12 156.17(13) . . . . ? C5 C6 C13 C12 33.34(16) . . . . ? C3 C4 C5 C7 173.10(17) . . . . ? C23 C4 C5 C7 -2.9(3) . . . . ? C3 C4 C5 C6 -4.0(2) . . . . ? C23 C4 C5 C6 -179.99(16) . . . . ? C8 C7 C5 C4 23.1(3) . . . . ? C12 C7 C5 C4 -160.92(18) . . . . ? C8 C7 C5 C6 -159.49(18) . . . . ? C12 C7 C5 C6 16.51(17) . . . . ? N1 C6 C5 C4 20.0(2) . . . . ? C13 C6 C5 C4 146.19(15) . . . . ? N1 C6 C5 C7 -157.77(13) . . . . ? C13 C6 C5 C7 -31.55(15) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 34.64 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.512 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.068 # Attachment '- Compound_1f.cif' data_VM629 _database_code_depnum_ccdc_archive 'CCDC 734893' #TrackingRef '- Compound_1f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C21 H17 N O4), C2 H3 N' _chemical_formula_sum 'C44 H37 N3 O8' _chemical_formula_weight 735.77 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 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 5.61290(10) _cell_length_b 19.2298(3) _cell_length_c 32.3685(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.1660(10) _cell_angle_gamma 90.00 _cell_volume 3488.36(10) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 22423 _cell_measurement_theta_min 3.5524 _cell_measurement_theta_max 77.2097 _exptl_crystal_description prism _exptl_crystal_colour orange-brown _exptl_crystal_size_max 0.3628 _exptl_crystal_size_mid 0.1350 _exptl_crystal_size_min 0.1099 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _exptl_absorpt_coefficient_mu 0.795 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.824 _exptl_absorpt_correction_T_max 0.929 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type ; 'SuperNova (Dual, Cu at zero, Cu active), detector: Atlas' ; _diffrn_measurement_method oscillation _diffrn_detector_area_resol_mean 10.4508 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37426 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0146 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 77.48 _reflns_number_total 7394 _reflns_number_gt 6875 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_structure_solution 'SIR_92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+1.9507P] 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 7394 _refine_ls_number_parameters 503 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O48 O 0.61178(18) 0.23282(5) 0.77575(3) 0.0275(2) Uani 1 1 d . . . O51 O 0.6499(2) 0.22738(6) 0.60894(3) 0.0339(3) Uani 1 1 d . . . O49 O 0.3128(2) 0.06354(6) 0.98910(3) 0.0349(3) Uani 1 1 d . . . O14 O 1.0123(2) 0.29182(6) 0.74211(3) 0.0319(2) Uani 1 1 d . . . H14 H 0.8989 0.2872 0.7578 0.048 Uiso 1 1 calc R . . O40 O 0.5111(2) 0.22300(6) 0.86156(3) 0.0352(3) Uani 1 1 d . . . H40 H 0.5844 0.2429 0.8430 0.053 Uiso 1 1 calc R . . O23 O 1.2828(2) 0.37477(6) 0.59394(3) 0.0346(3) Uani 1 1 d . . . O25 O 0.6701(2) 0.46334(7) 0.97034(3) 0.0408(3) Uani 1 1 d . . . O22 O 0.86506(19) 0.32693(6) 0.82686(3) 0.0318(2) Uani 1 1 d . . . N27 N 0.2860(2) 0.16011(6) 0.77029(4) 0.0239(2) Uani 1 1 d . . . C31 C 0.0531(2) 0.10317(7) 0.82155(4) 0.0233(3) Uani 1 1 d . . . N1 N 1.1602(2) 0.40913(7) 0.81672(4) 0.0303(3) Uani 1 1 d . . . C28 C 0.1240(2) 0.13460(7) 0.73895(4) 0.0231(3) Uani 1 1 d . . . C7 C 1.4362(2) 0.41682(7) 0.71793(5) 0.0258(3) Uani 1 1 d . . . C41 C 0.2202(2) 0.15583(7) 0.69996(4) 0.0234(3) Uani 1 1 d . . . C5 C 1.4381(2) 0.43095(7) 0.76208(5) 0.0258(3) Uani 1 1 d . . . C32 C 0.2167(2) 0.16354(7) 0.81288(4) 0.0234(3) Uani 1 1 d . . . H32 H 0.1279 0.2079 0.8168 0.028 Uiso 1 1 calc R . . C43 C 0.2860(3) 0.16848(8) 0.62791(4) 0.0273(3) Uani 1 1 d . . . H43 H 0.2360 0.1611 0.5997 0.033 Uiso 1 1 calc R . . C37 C 0.3893(3) 0.11194(8) 0.92140(4) 0.0275(3) Uani 1 1 d . . . H37 H 0.5331 0.1339 0.9312 0.033 Uiso 1 1 calc R . . C2 C 1.2765(3) 0.46321(8) 0.83976(5) 0.0288(3) Uani 1 1 d . . . C33 C 0.0959(2) 0.08633(7) 0.86523(4) 0.0242(3) Uani 1 1 d . . . C46 C 0.4321(2) 0.19263(7) 0.70910(4) 0.0229(3) Uani 1 1 d . . . C29 C -0.0592(2) 0.09347(7) 0.74857(4) 0.0249(3) Uani 1 1 d . . . H29 H -0.1720 0.0781 0.7276 0.030 Uiso 1 1 calc R . . C6 C 1.2643(2) 0.38056(8) 0.78019(5) 0.0281(3) Uani 1 1 d . . . H6 H 1.3559 0.3379 0.7889 0.034 Uiso 1 1 calc R . . C38 C 0.3056(2) 0.11870(7) 0.88040(4) 0.0247(3) Uani 1 1 d . . . C42 C 0.1453(3) 0.14418(8) 0.65903(4) 0.0266(3) Uani 1 1 d . . . H42 H 0.0007 0.1201 0.6523 0.032 Uiso 1 1 calc R . . C47 C 0.4650(2) 0.19906(7) 0.75465(4) 0.0224(3) Uani 1 1 d . . . C35 C 0.0477(3) 0.03811(8) 0.93280(5) 0.0296(3) Uani 1 1 d . . . H35 H -0.0389 0.0101 0.9510 0.035 Uiso 1 1 calc R . . C34 C -0.0331(3) 0.04508(7) 0.89183(5) 0.0273(3) Uani 1 1 d . . . H34 H -0.1747 0.0221 0.8818 0.033 Uiso 1 1 calc R . . C12 C 1.2353(2) 0.37701(7) 0.70651(4) 0.0245(3) Uani 1 1 d . . . C10 C 1.3225(3) 0.38522(8) 0.63551(5) 0.0283(3) Uani 1 1 d . . . C36 C 0.2562(3) 0.07198(8) 0.94771(4) 0.0280(3) Uani 1 1 d . . . C4 C 1.5404(3) 0.48294(8) 0.78453(5) 0.0306(3) Uani 1 1 d . . . H4 H 1.6625 0.5102 0.7734 0.037 Uiso 1 1 calc R . . C11 C 1.1748(3) 0.36042(7) 0.66549(4) 0.0257(3) Uani 1 1 d . . . H11 H 1.0377 0.3332 0.6581 0.031 Uiso 1 1 calc R . . C17 C 0.9955(3) 0.51397(9) 0.93962(5) 0.0374(4) Uani 1 1 d . . . H17 H 1.0049 0.5460 0.9620 0.045 Uiso 1 1 calc R . . C21 C 0.9766(3) 0.37993(8) 0.83699(5) 0.0279(3) Uani 1 1 d . . . C18 C 0.8167(3) 0.46275(8) 0.93809(5) 0.0335(3) Uani 1 1 d . . . C30 C -0.0832(2) 0.07282(7) 0.79108(4) 0.0254(3) Uani 1 1 d . . . H30 H -0.1950 0.0379 0.7975 0.031 Uiso 1 1 calc R . . C3 C 1.4648(3) 0.49732(8) 0.82552(5) 0.0309(3) Uani 1 1 d . . . H3 H 1.5476 0.5308 0.8425 0.037 Uiso 1 1 calc R . . C16 C 1.1572(3) 0.51867(8) 0.90936(5) 0.0360(4) Uani 1 1 d . . . H16 H 1.2772 0.5535 0.9107 0.043 Uiso 1 1 calc R . . C45 C 0.5752(3) 0.21659(7) 0.67881(4) 0.0254(3) Uani 1 1 d . . . H45 H 0.7193 0.2409 0.6857 0.031 Uiso 1 1 calc R . . C44 C 0.4999(3) 0.20360(8) 0.63770(4) 0.0267(3) Uani 1 1 d . . . C20 C 0.9609(3) 0.42146(7) 0.87514(4) 0.0275(3) Uani 1 1 d . . . C13 C 1.0923(3) 0.36032(7) 0.74362(4) 0.0252(3) Uani 1 1 d . . . H13 H 0.9507 0.3919 0.7433 0.030 Uiso 1 1 calc R . . C19 C 0.7958(3) 0.41587(8) 0.90536(5) 0.0298(3) Uani 1 1 d . . . H19 H 0.6740 0.3815 0.9038 0.036 Uiso 1 1 calc R . . C24 C 1.0653(3) 0.34147(9) 0.58039(5) 0.0346(3) Uani 1 1 d . . . H24B H 1.0609 0.2945 0.5921 0.052 Uiso 1 1 calc R . . H24C H 1.0554 0.3385 0.5501 0.052 Uiso 1 1 calc R . . H24A H 0.9299 0.3685 0.5896 0.052 Uiso 1 1 calc R . . C15 C 1.1417(3) 0.47110(8) 0.87651(4) 0.0292(3) Uani 1 1 d . . . C39 C 0.4212(3) 0.15868(8) 0.84658(4) 0.0258(3) Uani 1 1 d . . . H39 H 0.5546 0.1305 0.8360 0.031 Uiso 1 1 calc R . . C8 C 1.5835(3) 0.44104(8) 0.68754(5) 0.0302(3) Uani 1 1 d . . . H8 H 1.7210 0.4681 0.6949 0.036 Uiso 1 1 calc R . . C52 C 0.5840(3) 0.21502(10) 0.56641(5) 0.0367(4) Uani 1 1 d . . . H52B H 0.5612 0.1650 0.5619 0.055 Uiso 1 1 calc R . . H52C H 0.7105 0.2319 0.5493 0.055 Uiso 1 1 calc R . . H52A H 0.4350 0.2396 0.5588 0.055 Uiso 1 1 calc R . . C9 C 1.5255(3) 0.42494(8) 0.64663(5) 0.0314(3) Uani 1 1 d . . . H9 H 1.6245 0.4410 0.6257 0.038 Uiso 1 1 calc R . . N55 N 0.0819(4) 0.29418(13) 0.99832(6) 0.0697(6) Uani 1 1 d . . . C50 C 0.5211(3) 0.09843(10) 1.00583(5) 0.0374(4) Uani 1 1 d . . . H50A H 0.6607 0.0824 0.9916 0.056 Uiso 1 1 calc R . . H50B H 0.5434 0.0881 1.0354 0.056 Uiso 1 1 calc R . . H50C H 0.5021 0.1487 1.0019 0.056 Uiso 1 1 calc R . . C26 C 0.5063(3) 0.40680(9) 0.97330(5) 0.0402(4) Uani 1 1 d . . . H26C H 0.3976 0.4058 0.9486 0.060 Uiso 1 1 calc R . . H26A H 0.4142 0.4129 0.9979 0.060 Uiso 1 1 calc R . . H26B H 0.5950 0.3629 0.9755 0.060 Uiso 1 1 calc R . . C54 C 0.0364(3) 0.27248(10) 0.96601(6) 0.0420(4) Uani 1 1 d . . . C53 C -0.0271(4) 0.24509(10) 0.92529(6) 0.0523(5) Uani 1 1 d . . . H53C H -0.1903 0.2592 0.9168 0.079 Uiso 1 1 calc R . . H53A H -0.0174 0.1942 0.9259 0.079 Uiso 1 1 calc R . . H53B H 0.0833 0.2632 0.9055 0.079 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 O48 0.0260(5) 0.0332(5) 0.0233(5) -0.0030(4) 0.0016(4) -0.0072(4) O51 0.0342(6) 0.0474(7) 0.0202(5) 0.0033(4) 0.0027(4) -0.0016(5) O49 0.0381(6) 0.0437(6) 0.0234(5) 0.0047(4) 0.0055(4) 0.0009(5) O14 0.0318(5) 0.0390(6) 0.0254(5) -0.0022(4) 0.0069(4) -0.0114(5) O40 0.0377(6) 0.0435(6) 0.0242(5) 0.0007(5) 0.0001(4) -0.0187(5) O23 0.0353(6) 0.0414(6) 0.0281(5) 0.0022(5) 0.0092(4) -0.0001(5) O25 0.0498(7) 0.0457(7) 0.0269(6) -0.0081(5) 0.0016(5) 0.0087(6) O22 0.0343(6) 0.0357(6) 0.0258(5) -0.0083(4) 0.0067(4) -0.0112(5) N27 0.0230(6) 0.0263(6) 0.0222(6) -0.0013(4) 0.0007(4) -0.0030(4) C31 0.0195(6) 0.0233(6) 0.0275(7) -0.0009(5) 0.0055(5) 0.0016(5) N1 0.0366(7) 0.0306(6) 0.0234(6) -0.0010(5) -0.0014(5) -0.0088(5) C28 0.0226(6) 0.0232(6) 0.0234(6) -0.0042(5) -0.0014(5) 0.0020(5) C7 0.0217(6) 0.0217(6) 0.0339(8) 0.0021(5) 0.0000(5) 0.0045(5) C41 0.0217(6) 0.0226(6) 0.0258(7) -0.0016(5) 0.0003(5) 0.0029(5) C5 0.0207(6) 0.0226(7) 0.0339(8) 0.0028(5) -0.0012(5) 0.0029(5) C32 0.0209(6) 0.0280(7) 0.0214(6) -0.0027(5) 0.0029(5) -0.0011(5) C43 0.0308(7) 0.0297(7) 0.0210(6) -0.0023(5) -0.0032(5) 0.0062(6) C37 0.0246(7) 0.0321(7) 0.0260(7) -0.0002(6) 0.0034(5) 0.0011(6) C2 0.0355(8) 0.0238(7) 0.0257(7) 0.0008(5) -0.0099(6) -0.0028(6) C33 0.0230(6) 0.0237(6) 0.0263(7) -0.0022(5) 0.0051(5) 0.0035(5) C46 0.0237(6) 0.0227(6) 0.0222(6) -0.0013(5) -0.0003(5) 0.0031(5) C29 0.0215(6) 0.0255(7) 0.0276(7) -0.0048(5) -0.0002(5) -0.0009(5) C6 0.0227(7) 0.0285(7) 0.0332(8) -0.0078(6) 0.0018(6) 0.0003(5) C38 0.0226(6) 0.0265(7) 0.0254(7) -0.0007(5) 0.0047(5) 0.0026(5) C42 0.0243(7) 0.0283(7) 0.0268(7) -0.0037(6) -0.0026(5) 0.0020(5) C47 0.0220(6) 0.0223(6) 0.0231(6) -0.0004(5) 0.0030(5) 0.0011(5) C35 0.0315(7) 0.0272(7) 0.0311(7) 0.0036(6) 0.0113(6) 0.0021(6) C34 0.0263(7) 0.0249(7) 0.0314(7) -0.0012(6) 0.0065(6) 0.0001(5) C12 0.0244(7) 0.0200(6) 0.0291(7) 0.0028(5) 0.0014(5) 0.0039(5) C10 0.0291(7) 0.0279(7) 0.0284(7) 0.0026(6) 0.0055(6) 0.0070(6) C36 0.0306(7) 0.0302(7) 0.0238(7) 0.0016(6) 0.0059(5) 0.0064(6) C4 0.0273(7) 0.0261(7) 0.0378(8) 0.0044(6) -0.0041(6) -0.0042(6) C11 0.0250(7) 0.0246(7) 0.0278(7) 0.0020(5) 0.0025(5) 0.0018(5) C17 0.0552(10) 0.0314(8) 0.0242(7) -0.0058(6) -0.0104(7) 0.0050(7) C21 0.0269(7) 0.0267(7) 0.0301(7) -0.0025(6) 0.0013(6) 0.0005(6) C18 0.0424(9) 0.0343(8) 0.0229(7) -0.0021(6) -0.0059(6) 0.0109(7) C30 0.0210(6) 0.0247(7) 0.0309(7) -0.0025(5) 0.0036(5) -0.0009(5) C3 0.0331(8) 0.0244(7) 0.0341(8) 0.0008(6) -0.0097(6) -0.0045(6) C16 0.0490(9) 0.0283(8) 0.0291(8) -0.0014(6) -0.0122(7) -0.0036(7) C45 0.0241(7) 0.0275(7) 0.0247(7) -0.0002(5) 0.0007(5) 0.0014(5) C44 0.0280(7) 0.0289(7) 0.0234(7) 0.0020(5) 0.0021(5) 0.0064(6) C20 0.0319(7) 0.0251(7) 0.0248(7) -0.0001(5) -0.0065(6) 0.0031(6) C13 0.0290(7) 0.0227(6) 0.0237(7) -0.0004(5) -0.0005(5) 0.0006(5) C19 0.0332(8) 0.0296(7) 0.0258(7) -0.0021(6) -0.0040(6) 0.0047(6) C24 0.0384(8) 0.0390(9) 0.0268(7) -0.0004(6) 0.0047(6) 0.0018(7) C15 0.0372(8) 0.0247(7) 0.0247(7) 0.0022(5) -0.0091(6) 0.0002(6) C39 0.0236(7) 0.0319(7) 0.0220(6) -0.0012(5) 0.0020(5) -0.0016(5) C8 0.0220(7) 0.0270(7) 0.0417(8) 0.0040(6) 0.0028(6) 0.0015(5) C52 0.0424(9) 0.0471(9) 0.0206(7) 0.0021(6) 0.0025(6) 0.0029(7) C9 0.0252(7) 0.0318(8) 0.0382(8) 0.0073(6) 0.0097(6) 0.0038(6) N55 0.0675(12) 0.1017(17) 0.0387(10) 0.0094(10) -0.0078(9) -0.0171(12) C50 0.0408(9) 0.0491(10) 0.0225(7) -0.0011(7) 0.0037(6) 0.0018(7) C26 0.0506(10) 0.0406(9) 0.0299(8) 0.0013(7) 0.0076(7) 0.0117(8) C54 0.0345(9) 0.0516(10) 0.0394(9) 0.0114(8) -0.0025(7) -0.0007(7) C53 0.0710(14) 0.0369(9) 0.0478(11) -0.0057(8) -0.0085(10) 0.0144(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O48 C47 1.2264(17) . ? O51 C44 1.3677(18) . ? O51 C52 1.4256(18) . ? O49 C36 1.3691(17) . ? O49 C50 1.428(2) . ? O14 C13 1.3917(18) . ? O14 H14 0.8400 . ? O40 C39 1.4118(18) . ? O40 H40 0.8400 . ? O23 C10 1.3666(18) . ? O23 C24 1.426(2) . ? O25 C18 1.364(2) . ? O25 C26 1.431(2) . ? O22 C21 1.2312(18) . ? N27 C47 1.3723(18) . ? N27 C28 1.4123(17) . ? N27 C32 1.4542(17) . ? C31 C30 1.348(2) . ? C31 C33 1.4575(19) . ? C31 C32 1.5157(19) . ? N1 C21 1.372(2) . ? N1 C2 1.4178(18) . ? N1 C6 1.4554(19) . ? C28 C29 1.348(2) . ? C28 C41 1.4582(19) . ? C7 C12 1.396(2) . ? C7 C8 1.399(2) . ? C7 C5 1.454(2) . ? C41 C42 1.3860(19) . ? C41 C46 1.4012(19) . ? C5 C4 1.345(2) . ? C5 C6 1.516(2) . ? C32 C39 1.5421(19) . ? C32 H32 1.0000 . ? C43 C42 1.394(2) . ? C43 C44 1.399(2) . ? C43 H43 0.9500 . ? C37 C38 1.389(2) . ? C37 C36 1.394(2) . ? C37 H37 0.9500 . ? C2 C3 1.346(2) . ? C2 C15 1.453(2) . ? C33 C38 1.396(2) . ? C33 C34 1.401(2) . ? C46 C45 1.381(2) . ? C46 C47 1.4810(18) . ? C29 C30 1.445(2) . ? C29 H29 0.9500 . ? C6 C13 1.536(2) . ? C6 H6 1.0000 . ? C38 C39 1.5130(19) . ? C42 H42 0.9500 . ? C35 C34 1.384(2) . ? C35 C36 1.402(2) . ? C35 H35 0.9500 . ? C34 H34 0.9500 . ? C12 C11 1.390(2) . ? C12 C13 1.5152(19) . ? C10 C11 1.395(2) . ? C10 C9 1.402(2) . ? C4 C3 1.442(2) . ? C4 H4 0.9500 . ? C11 H11 0.9500 . ? C17 C16 1.374(3) . ? C17 C18 1.405(3) . ? C17 H17 0.9500 . ? C21 C20 1.477(2) . ? C18 C19 1.391(2) . ? C30 H30 0.9500 . ? C3 H3 0.9500 . ? C16 C15 1.402(2) . ? C16 H16 0.9500 . ? C45 C44 1.396(2) . ? C45 H45 0.9500 . ? C20 C19 1.388(2) . ? C20 C15 1.392(2) . ? C13 H13 1.0000 . ? C19 H19 0.9500 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C24 H24A 0.9800 . ? C39 H39 1.0000 . ? C8 C9 1.381(2) . ? C8 H8 0.9500 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C52 H52A 0.9800 . ? C9 H9 0.9500 . ? N55 C54 1.142(3) . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? C26 H26C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C54 C53 1.446(3) . ? C53 H53C 0.9800 . ? C53 H53A 0.9800 . ? C53 H53B 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 C44 O51 C52 117.71(13) . . ? C36 O49 C50 117.14(12) . . ? C13 O14 H14 109.5 . . ? C39 O40 H40 109.5 . . ? C10 O23 C24 117.33(12) . . ? C18 O25 C26 117.49(13) . . ? C47 N27 C28 112.33(11) . . ? C47 N27 C32 124.37(12) . . ? C28 N27 C32 120.10(11) . . ? C30 C31 C33 132.09(13) . . ? C30 C31 C32 121.43(13) . . ? C33 C31 C32 106.31(12) . . ? C21 N1 C2 112.64(13) . . ? C21 N1 C6 125.45(12) . . ? C2 N1 C6 120.69(13) . . ? C29 C28 N27 120.46(13) . . ? C29 C28 C41 133.50(13) . . ? N27 C28 C41 105.67(12) . . ? C12 C7 C8 119.78(14) . . ? C12 C7 C5 108.95(13) . . ? C8 C7 C5 130.99(14) . . ? C42 C41 C46 119.51(13) . . ? C42 C41 C28 132.44(13) . . ? C46 C41 C28 108.01(12) . . ? C4 C5 C7 130.49(14) . . ? C4 C5 C6 122.05(14) . . ? C7 C5 C6 106.89(12) . . ? N27 C32 C31 109.71(11) . . ? N27 C32 C39 116.11(11) . . ? C31 C32 C39 104.91(11) . . ? N27 C32 H32 108.6 . . ? C31 C32 H32 108.6 . . ? C39 C32 H32 108.6 . . ? C42 C43 C44 120.77(13) . . ? C42 C43 H43 119.6 . . ? C44 C43 H43 119.6 . . ? C38 C37 C36 118.08(14) . . ? C38 C37 H37 121.0 . . ? C36 C37 H37 121.0 . . ? C3 C2 N1 121.64(14) . . ? C3 C2 C15 133.13(14) . . ? N1 C2 C15 105.18(13) . . ? C38 C33 C34 119.37(13) . . ? C38 C33 C31 109.42(12) . . ? C34 C33 C31 131.21(13) . . ? C45 C46 C41 122.61(13) . . ? C45 C46 C47 129.32(13) . . ? C41 C46 C47 108.07(12) . . ? C28 C29 C30 119.58(13) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.2 . . ? N1 C6 C5 111.64(12) . . ? N1 C6 C13 117.28(12) . . ? C5 C6 C13 104.75(12) . . ? N1 C6 H6 107.6 . . ? C5 C6 H6 107.6 . . ? C13 C6 H6 107.6 . . ? C37 C38 C33 121.89(13) . . ? C37 C38 C39 127.06(13) . . ? C33 C38 C39 111.04(12) . . ? C41 C42 C43 118.84(13) . . ? C41 C42 H42 120.6 . . ? C43 C42 H42 120.6 . . ? O48 C47 N27 124.51(13) . . ? O48 C47 C46 129.90(13) . . ? N27 C47 C46 105.55(11) . . ? C34 C35 C36 120.55(14) . . ? C34 C35 H35 119.7 . . ? C36 C35 H35 119.7 . . ? C35 C34 C33 119.36(14) . . ? C35 C34 H34 120.3 . . ? C33 C34 H34 120.3 . . ? C11 C12 C7 122.02(13) . . ? C11 C12 C13 126.62(13) . . ? C7 C12 C13 111.22(13) . . ? O23 C10 C11 124.32(14) . . ? O23 C10 C9 114.76(13) . . ? C11 C10 C9 120.91(14) . . ? O49 C36 C37 124.03(14) . . ? O49 C36 C35 115.22(13) . . ? C37 C36 C35 120.73(14) . . ? C5 C4 C3 120.06(14) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C12 C11 C10 117.57(14) . . ? C12 C11 H11 121.2 . . ? C10 C11 H11 121.2 . . ? C16 C17 C18 121.29(15) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? O22 C21 N1 126.57(14) . . ? O22 C21 C20 128.12(14) . . ? N1 C21 C20 105.04(13) . . ? O25 C18 C19 124.01(16) . . ? O25 C18 C17 115.27(14) . . ? C19 C18 C17 120.72(16) . . ? C31 C30 C29 119.92(13) . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C2 C3 C4 119.86(14) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C17 C16 C15 118.82(16) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C46 C45 C44 117.36(13) . . ? C46 C45 H45 121.3 . . ? C44 C45 H45 121.3 . . ? O51 C44 C45 115.05(13) . . ? O51 C44 C43 124.07(13) . . ? C45 C44 C43 120.88(13) . . ? C19 C20 C15 122.98(14) . . ? C19 C20 C21 128.32(14) . . ? C15 C20 C21 108.69(13) . . ? O14 C13 C12 110.90(11) . . ? O14 C13 C6 117.06(12) . . ? C12 C13 C6 102.67(12) . . ? O14 C13 H13 108.6 . . ? C12 C13 H13 108.6 . . ? C6 C13 H13 108.6 . . ? C20 C19 C18 117.08(15) . . ? C20 C19 H19 121.5 . . ? C18 C19 H19 121.5 . . ? O23 C24 H24B 109.5 . . ? O23 C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O23 C24 H24A 109.5 . . ? H24B C24 H24A 109.5 . . ? H24C C24 H24A 109.5 . . ? C20 C15 C16 119.09(15) . . ? C20 C15 C2 108.31(13) . . ? C16 C15 C2 132.54(15) . . ? O40 C39 C38 110.87(11) . . ? O40 C39 C32 115.33(12) . . ? C38 C39 C32 102.14(11) . . ? O40 C39 H39 109.4 . . ? C38 C39 H39 109.4 . . ? C32 C39 H39 109.4 . . ? C9 C8 C7 118.81(14) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? O51 C52 H52B 109.5 . . ? O51 C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? O51 C52 H52A 109.5 . . ? H52B C52 H52A 109.5 . . ? H52C C52 H52A 109.5 . . ? C8 C9 C10 120.90(14) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? O49 C50 H50A 109.5 . . ? O49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? O49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? O25 C26 H26C 109.5 . . ? O25 C26 H26A 109.5 . . ? H26C C26 H26A 109.5 . . ? O25 C26 H26B 109.5 . . ? H26C C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N55 C54 C53 178.6(2) . . ? C54 C53 H53C 109.5 . . ? C54 C53 H53A 109.5 . . ? H53C C53 H53A 109.5 . . ? C54 C53 H53B 109.5 . . ? H53C C53 H53B 109.5 . . ? H53A C53 H53B 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 C47 N27 C28 C29 177.95(13) . . . . ? C32 N27 C28 C29 -21.40(19) . . . . ? C47 N27 C28 C41 4.03(15) . . . . ? C32 N27 C28 C41 164.68(12) . . . . ? C29 C28 C41 C42 4.8(3) . . . . ? N27 C28 C41 C42 177.57(15) . . . . ? C29 C28 C41 C46 -172.82(15) . . . . ? N27 C28 C41 C46 -0.04(15) . . . . ? C12 C7 C5 C4 -155.36(15) . . . . ? C8 C7 C5 C4 18.4(3) . . . . ? C12 C7 C5 C6 15.88(15) . . . . ? C8 C7 C5 C6 -170.34(14) . . . . ? C47 N27 C32 C31 -167.70(12) . . . . ? C28 N27 C32 C31 34.10(17) . . . . ? C47 N27 C32 C39 -49.02(18) . . . . ? C28 N27 C32 C39 152.78(13) . . . . ? C30 C31 C32 N27 -26.58(18) . . . . ? C33 C31 C32 N27 149.23(11) . . . . ? C30 C31 C32 C39 -151.97(13) . . . . ? C33 C31 C32 C39 23.85(14) . . . . ? C21 N1 C2 C3 178.51(14) . . . . ? C6 N1 C2 C3 10.5(2) . . . . ? C21 N1 C2 C15 -3.99(17) . . . . ? C6 N1 C2 C15 -172.02(13) . . . . ? C30 C31 C33 C38 160.87(15) . . . . ? C32 C31 C33 C38 -14.32(15) . . . . ? C30 C31 C33 C34 -18.7(3) . . . . ? C32 C31 C33 C34 166.14(14) . . . . ? C42 C41 C46 C45 -1.8(2) . . . . ? C28 C41 C46 C45 176.17(13) . . . . ? C42 C41 C46 C47 178.46(12) . . . . ? C28 C41 C46 C47 -3.56(15) . . . . ? N27 C28 C29 C30 -2.9(2) . . . . ? C41 C28 C29 C30 169.05(14) . . . . ? C21 N1 C6 C5 171.62(13) . . . . ? C2 N1 C6 C5 -21.97(19) . . . . ? C21 N1 C6 C13 50.8(2) . . . . ? C2 N1 C6 C13 -142.82(14) . . . . ? C4 C5 C6 N1 20.82(19) . . . . ? C7 C5 C6 N1 -151.33(12) . . . . ? C4 C5 C6 C13 148.73(14) . . . . ? C7 C5 C6 C13 -23.42(14) . . . . ? C36 C37 C38 C33 -0.6(2) . . . . ? C36 C37 C38 C39 -179.39(14) . . . . ? C34 C33 C38 C37 -0.8(2) . . . . ? C31 C33 C38 C37 179.64(13) . . . . ? C34 C33 C38 C39 178.18(12) . . . . ? C31 C33 C38 C39 -1.42(16) . . . . ? C46 C41 C42 C43 1.1(2) . . . . ? C28 C41 C42 C43 -176.25(14) . . . . ? C44 C43 C42 C41 0.4(2) . . . . ? C28 N27 C47 O48 171.83(13) . . . . ? C32 N27 C47 O48 12.2(2) . . . . ? C28 N27 C47 C46 -6.13(15) . . . . ? C32 N27 C47 C46 -165.80(12) . . . . ? C45 C46 C47 O48 8.4(2) . . . . ? C41 C46 C47 O48 -171.90(14) . . . . ? C45 C46 C47 N27 -173.81(14) . . . . ? C41 C46 C47 N27 5.90(15) . . . . ? C36 C35 C34 C33 0.1(2) . . . . ? C38 C33 C34 C35 1.0(2) . . . . ? C31 C33 C34 C35 -179.49(14) . . . . ? C8 C7 C12 C11 -0.2(2) . . . . ? C5 C7 C12 C11 174.41(13) . . . . ? C8 C7 C12 C13 -176.21(12) . . . . ? C5 C7 C12 C13 -1.62(15) . . . . ? C24 O23 C10 C11 5.6(2) . . . . ? C24 O23 C10 C9 -173.18(13) . . . . ? C50 O49 C36 C37 0.3(2) . . . . ? C50 O49 C36 C35 -178.64(13) . . . . ? C38 C37 C36 O49 -177.07(13) . . . . ? C38 C37 C36 C35 1.8(2) . . . . ? C34 C35 C36 O49 177.39(13) . . . . ? C34 C35 C36 C37 -1.6(2) . . . . ? C7 C5 C4 C3 162.65(14) . . . . ? C6 C5 C4 C3 -7.4(2) . . . . ? C7 C12 C11 C10 -0.2(2) . . . . ? C13 C12 C11 C10 175.23(13) . . . . ? O23 C10 C11 C12 -178.21(13) . . . . ? C9 C10 C11 C12 0.5(2) . . . . ? C2 N1 C21 O22 -170.31(15) . . . . ? C6 N1 C21 O22 -3.0(3) . . . . ? C2 N1 C21 C20 4.05(16) . . . . ? C6 N1 C21 C20 171.40(13) . . . . ? C26 O25 C18 C19 8.5(2) . . . . ? C26 O25 C18 C17 -171.71(14) . . . . ? C16 C17 C18 O25 179.17(14) . . . . ? C16 C17 C18 C19 -1.1(2) . . . . ? C33 C31 C30 C29 -168.89(14) . . . . ? C32 C31 C30 C29 5.7(2) . . . . ? C28 C29 C30 C31 10.5(2) . . . . ? N1 C2 C3 C4 5.0(2) . . . . ? C15 C2 C3 C4 -171.66(15) . . . . ? C5 C4 C3 C2 -6.4(2) . . . . ? C18 C17 C16 C15 -0.1(2) . . . . ? C41 C46 C45 C44 0.8(2) . . . . ? C47 C46 C45 C44 -179.53(13) . . . . ? C52 O51 C44 C45 179.33(13) . . . . ? C52 O51 C44 C43 -0.5(2) . . . . ? C46 C45 C44 O51 -178.97(12) . . . . ? C46 C45 C44 C43 0.8(2) . . . . ? C42 C43 C44 O51 178.32(13) . . . . ? C42 C43 C44 C45 -1.5(2) . . . . ? O22 C21 C20 C19 -9.6(3) . . . . ? N1 C21 C20 C19 176.13(14) . . . . ? O22 C21 C20 C15 171.72(15) . . . . ? N1 C21 C20 C15 -2.51(16) . . . . ? C11 C12 C13 O14 45.55(19) . . . . ? C7 C12 C13 O14 -138.65(12) . . . . ? C11 C12 C13 C6 171.34(13) . . . . ? C7 C12 C13 C6 -12.85(15) . . . . ? N1 C6 C13 O14 -92.46(16) . . . . ? C5 C6 C13 O14 143.14(12) . . . . ? N1 C6 C13 C12 145.84(13) . . . . ? C5 C6 C13 C12 21.45(14) . . . . ? C15 C20 C19 C18 0.0(2) . . . . ? C21 C20 C19 C18 -178.46(14) . . . . ? O25 C18 C19 C20 -179.18(14) . . . . ? C17 C18 C19 C20 1.1(2) . . . . ? C19 C20 C15 C16 -1.1(2) . . . . ? C21 C20 C15 C16 177.61(13) . . . . ? C19 C20 C15 C2 -178.57(13) . . . . ? C21 C20 C15 C2 0.15(16) . . . . ? C17 C16 C15 C20 1.1(2) . . . . ? C17 C16 C15 C2 177.85(16) . . . . ? C3 C2 C15 C20 179.27(16) . . . . ? N1 C2 C15 C20 2.19(16) . . . . ? C3 C2 C15 C16 2.3(3) . . . . ? N1 C2 C15 C16 -174.80(16) . . . . ? C37 C38 C39 O40 -41.7(2) . . . . ? C33 C38 C39 O40 139.39(12) . . . . ? C37 C38 C39 C32 -165.13(14) . . . . ? C33 C38 C39 C32 15.99(15) . . . . ? N27 C32 C39 O40 94.78(15) . . . . ? C31 C32 C39 O40 -143.95(12) . . . . ? N27 C32 C39 C38 -144.89(12) . . . . ? C31 C32 C39 C38 -23.62(14) . . . . ? C12 C7 C8 C9 0.2(2) . . . . ? C5 C7 C8 C9 -173.04(14) . . . . ? C7 C8 C9 C10 0.2(2) . . . . ? O23 C10 C9 C8 178.32(13) . . . . ? C11 C10 C9 C8 -0.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 77.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.473 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.046