# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Srinu Tothadi' 'Arijit Mukherjee' 'Gautam R. Desiraju' _publ_contact_author_email srinut.iisc@gmail.com _publ_contact_author_name 'Srinu Tothadi' data_26dht-44bp _database_code_depnum_ccdc_archive 'CCDC 836441' #TrackingRef '26dht-44bp btf-ch3cn2n(6).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 N2 O2 S' _chemical_formula_weight 362.43 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' 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4470(15) _cell_length_b 9.4240(19) _cell_length_c 14.075(3) _cell_angle_alpha 72.08(3) _cell_angle_beta 76.66(3) _cell_angle_gamma 89.64(3) _cell_volume 912.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2133 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 27.5 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.195 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9621 _exptl_absorpt_correction_T_max 0.9621 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9717 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4166 _reflns_number_gt 3373 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0986P)^2^+0.5182P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4166 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.2001 _refine_ls_wR_factor_gt 0.1769 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _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 S1 S 0.37695(17) 0.14734(14) 0.58180(11) 0.0538(5) Uani 0.495(4) 1 d P A 2 C39 C 0.5403(2) 0.19401(14) 0.36995(12) 0.0616(5) Uani 0.495(4) 1 d P A 2 C38 C 0.37695(17) 0.14734(14) 0.58180(11) 0.0538(5) Uani 0.505(4) 1 d P A 1 S2 S 0.5403(2) 0.19401(14) 0.36995(12) 0.0616(5) Uani 0.505(4) 1 d P A 1 C1 C 0.2327(3) 0.9977(2) 0.15554(17) 0.0275(4) Uani 1 1 d . . . C2 C 0.0688(3) 0.9067(2) 0.18184(16) 0.0259(4) Uani 1 1 d . . . C3 C 0.0716(3) 0.7545(2) 0.23543(16) 0.0259(4) Uani 1 1 d . . . C4 C 0.2327(3) 0.6937(3) 0.25931(18) 0.0316(5) Uani 1 1 d . . . C5 C 0.3931(3) 0.7863(3) 0.2312(2) 0.0366(5) Uani 1 1 d . . . C6 C 0.3948(3) 0.9386(3) 0.1795(2) 0.0346(5) Uani 1 1 d . . . C7 C -0.1029(3) 0.9718(3) 0.1526(2) 0.0348(5) Uani 1 1 d . . . H7A H -0.0782 1.0152 0.0776 0.052 Uiso 1 1 calc R . . H7B H -0.1393 1.0498 0.1845 0.052 Uiso 1 1 calc R . . H7C H -0.2031 0.8929 0.1765 0.052 Uiso 1 1 calc R . . C15 C 0.5884(4) 0.4173(3) 0.1092(2) 0.0439(6) Uani 1 1 d . . . C16 C 0.7593(4) 0.4934(3) 0.0849(2) 0.0432(6) Uani 1 1 d . . . C17 C 0.9061(3) 0.4607(2) 0.01482(16) 0.0272(5) Uani 1 1 d . . . C18 C 0.8700(4) 0.3505(3) -0.0255(2) 0.0405(6) Uani 1 1 d . . . C19 C 0.6946(4) 0.2799(3) 0.0032(2) 0.0408(6) Uani 1 1 d . . . C25 C 1.0249(5) 0.2854(3) 0.3161(2) 0.0498(7) Uani 1 1 d . . . C26 C 1.0465(4) 0.1368(3) 0.3648(2) 0.0467(7) Uani 1 1 d . . . C27 C 0.9897(3) 0.0793(2) 0.47180(18) 0.0287(5) Uani 1 1 d . . . C28 C 0.9126(4) 0.1783(3) 0.5231(2) 0.0366(5) Uani 1 1 d . . . C29 C 0.8963(4) 0.3245(3) 0.4677(2) 0.0401(6) Uani 1 1 d . . . C35 C 0.3885(4) 0.3161(4) 0.5053(3) 0.0579(8) Uani 1 1 d . . . H35 H 0.3429 0.3957 0.5301 0.069 Uiso 1 1 calc R A 1 C36 C 0.4660(4) 0.3396(3) 0.4043(3) 0.0587(8) Uani 1 1 d . A . H36 H 0.4770 0.4364 0.3553 0.070 Uiso 1 1 calc R B 1 C37 C 0.4812(3) 0.0785(3) 0.48895(19) 0.0321(5) Uani 1 1 d . . . N1 N 0.5534(3) 0.3106(2) 0.06991(15) 0.0340(4) Uani 1 1 d . . . N3 N 0.9511(3) 0.3798(2) 0.36541(18) 0.0384(5) Uani 1 1 d . . . O1 O 0.2242(2) 1.14601(18) 0.10577(14) 0.0350(4) Uani 1 1 d . . . O2 O -0.0902(2) 0.66806(18) 0.26125(13) 0.0318(4) Uani 1 1 d . . . H5 H 0.512(4) 0.742(3) 0.245(2) 0.045(8) Uiso 1 1 d . . . H4 H 0.231(4) 0.584(4) 0.296(2) 0.043(8) Uiso 1 1 d . . . H18 H 0.963(5) 0.323(4) -0.075(3) 0.057(9) Uiso 1 1 d . . . H19 H 0.673(4) 0.209(4) -0.025(2) 0.045(8) Uiso 1 1 d . . . H6 H 0.510(4) 1.008(3) 0.159(2) 0.043(8) Uiso 1 1 d . . . H15 H 0.483(5) 0.445(4) 0.162(3) 0.055(9) Uiso 1 1 d . . . H29 H 0.842(4) 0.397(4) 0.510(2) 0.049(8) Uiso 1 1 d . . . H16 H 0.766(4) 0.567(4) 0.121(2) 0.048(8) Uiso 1 1 d . . . H28 H 0.861(5) 0.154(4) 0.598(3) 0.063(10) Uiso 1 1 d . . . H25 H 1.075(5) 0.325(4) 0.242(3) 0.061(10) Uiso 1 1 d . . . H26 H 1.107(5) 0.075(4) 0.324(3) 0.069(11) Uiso 1 1 d . . . H2 H -0.069(6) 0.575(5) 0.292(3) 0.074(12) Uiso 1 1 d . . . H1 H 0.329(5) 1.189(4) 0.094(3) 0.053(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0496(7) 0.0434(7) 0.0769(9) -0.0269(6) -0.0213(6) 0.0067(5) C39 0.0607(9) 0.0397(7) 0.0815(10) -0.0068(6) -0.0280(7) 0.0052(5) C38 0.0496(7) 0.0434(7) 0.0769(9) -0.0269(6) -0.0213(6) 0.0067(5) S2 0.0607(9) 0.0397(7) 0.0815(10) -0.0068(6) -0.0280(7) 0.0052(5) C1 0.0243(10) 0.0225(10) 0.0333(11) -0.0060(8) -0.0061(8) 0.0002(8) C2 0.0215(9) 0.0258(10) 0.0281(10) -0.0056(8) -0.0051(8) -0.0003(8) C3 0.0234(10) 0.0248(10) 0.0283(10) -0.0081(8) -0.0042(8) -0.0027(8) C4 0.0316(11) 0.0240(10) 0.0390(12) -0.0071(9) -0.0118(9) 0.0031(8) C5 0.0271(11) 0.0302(12) 0.0534(14) -0.0090(11) -0.0170(10) 0.0045(9) C6 0.0242(11) 0.0298(11) 0.0486(14) -0.0082(10) -0.0118(9) -0.0024(9) C7 0.0232(10) 0.0311(11) 0.0437(13) -0.0032(10) -0.0072(9) 0.0006(9) C15 0.0325(13) 0.0442(15) 0.0565(16) -0.0226(13) -0.0040(11) -0.0034(11) C16 0.0339(13) 0.0444(14) 0.0568(16) -0.0285(13) -0.0039(11) -0.0063(11) C17 0.0298(11) 0.0238(10) 0.0260(10) -0.0028(8) -0.0094(8) -0.0040(8) C18 0.0404(13) 0.0426(14) 0.0389(13) -0.0196(11) -0.0009(10) -0.0120(11) C19 0.0407(13) 0.0389(13) 0.0437(13) -0.0174(11) -0.0050(11) -0.0141(11) C25 0.0647(19) 0.0284(13) 0.0434(15) -0.0013(11) -0.0017(13) 0.0009(12) C26 0.0640(18) 0.0269(12) 0.0411(14) -0.0082(11) -0.0004(12) 0.0050(12) C27 0.0250(10) 0.0218(11) 0.0393(12) -0.0086(9) -0.0092(9) -0.0019(8) C28 0.0426(13) 0.0278(12) 0.0420(13) -0.0121(10) -0.0141(11) 0.0089(10) C29 0.0431(14) 0.0282(12) 0.0516(15) -0.0125(11) -0.0165(11) 0.0086(10) C35 0.0388(15) 0.0494(17) 0.095(3) -0.0353(17) -0.0184(16) 0.0105(13) C36 0.0491(17) 0.0358(15) 0.087(2) -0.0049(15) -0.0274(16) 0.0026(12) C37 0.0239(10) 0.0336(12) 0.0433(13) -0.0147(10) -0.0133(9) 0.0031(9) N1 0.0322(10) 0.0281(10) 0.0375(10) -0.0036(8) -0.0091(8) -0.0068(8) N3 0.0346(10) 0.0231(9) 0.0519(12) -0.0030(9) -0.0112(9) -0.0012(8) O1 0.0255(8) 0.0228(8) 0.0489(10) -0.0002(7) -0.0089(7) -0.0036(6) O2 0.0257(8) 0.0247(8) 0.0390(9) -0.0036(7) -0.0050(6) -0.0048(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C35 1.613(4) . ? S1 C37 1.667(3) . ? C39 C36 1.643(4) . ? C39 C37 1.651(3) . ? C1 O1 1.366(3) . ? C1 C6 1.395(3) . ? C1 C2 1.404(3) . ? C2 C3 1.402(3) . ? C2 C7 1.503(3) . ? C3 O2 1.369(2) . ? C3 C4 1.393(3) . ? C4 C5 1.388(3) . ? C4 H4 1.00(3) . ? C5 C6 1.393(3) . ? C5 H5 1.01(3) . ? C6 H6 1.01(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C15 N1 1.340(3) . ? C15 C16 1.382(3) . ? C15 H15 1.04(3) . ? C16 C17 1.395(3) . ? C16 H16 0.98(3) . ? C17 C18 1.382(3) . ? C17 C17 1.494(4) 2_765 ? C18 C19 1.383(3) . ? C18 H18 0.96(4) . ? C19 N1 1.334(3) . ? C19 H19 0.91(3) . ? C25 N3 1.332(4) . ? C25 C26 1.384(4) . ? C25 H25 0.98(4) . ? C26 C27 1.396(4) . ? C26 H26 0.98(4) . ? C27 C28 1.392(3) . ? C27 C27 1.486(4) 2_756 ? C28 C29 1.379(3) . ? C28 H28 0.99(4) . ? C29 N3 1.335(4) . ? C29 H29 1.05(3) . ? C35 C36 1.354(5) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 C37 1.455(5) 2_656 ? O1 H1 0.83(4) . ? O2 H2 0.88(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C35 S1 C37 94.13(17) . . ? C36 C39 C37 93.33(18) . . ? O1 C1 C6 122.21(19) . . ? O1 C1 C2 116.49(19) . . ? C6 C1 C2 121.3(2) . . ? C3 C2 C1 117.89(19) . . ? C3 C2 C7 121.67(19) . . ? C1 C2 C7 120.44(19) . . ? O2 C3 C4 121.60(19) . . ? O2 C3 C2 116.96(19) . . ? C4 C3 C2 121.43(19) . . ? C5 C4 C3 119.3(2) . . ? C5 C4 H4 121.1(17) . . ? C3 C4 H4 119.6(17) . . ? C4 C5 C6 120.9(2) . . ? C4 C5 H5 119.5(18) . . ? C6 C5 H5 119.5(18) . . ? C5 C6 C1 119.1(2) . . ? C5 C6 H6 122.1(17) . . ? C1 C6 H6 118.8(17) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C15 C16 123.8(2) . . ? N1 C15 H15 119.0(18) . . ? C16 C15 H15 117.2(18) . . ? C15 C16 C17 119.5(2) . . ? C15 C16 H16 115.0(19) . . ? C17 C16 H16 125.5(19) . . ? C18 C17 C16 116.7(2) . . ? C18 C17 C17 121.3(3) . 2_765 ? C16 C17 C17 122.1(2) . 2_765 ? C17 C18 C19 120.0(2) . . ? C17 C18 H18 122(2) . . ? C19 C18 H18 118(2) . . ? N1 C19 C18 123.7(2) . . ? N1 C19 H19 117(2) . . ? C18 C19 H19 119(2) . . ? N3 C25 C26 123.9(3) . . ? N3 C25 H25 118(2) . . ? C26 C25 H25 118(2) . . ? C25 C26 C27 119.5(3) . . ? C25 C26 H26 119(2) . . ? C27 C26 H26 121(2) . . ? C28 C27 C26 116.5(2) . . ? C28 C27 C27 121.7(3) . 2_756 ? C26 C27 C27 121.9(3) . 2_756 ? C29 C28 C27 119.8(2) . . ? C29 C28 H28 114(2) . . ? C27 C28 H28 126(2) . . ? N3 C29 C28 123.8(2) . . ? N3 C29 H29 118.8(17) . . ? C28 C29 H29 117.3(17) . . ? C36 C35 S1 117.2(3) . . ? C36 C35 H35 121.4 . . ? S1 C35 H35 121.4 . . ? C35 C36 C39 117.3(3) . . ? C35 C36 H36 121.3 . . ? C39 C36 H36 121.3 . . ? C37 C37 C39 120.5(3) 2_656 . ? C37 C37 S1 121.5(3) 2_656 . ? C39 C37 S1 118.00(15) . . ? C19 N1 C15 116.3(2) . . ? C25 N3 C29 116.6(2) . . ? C1 O1 H1 108(2) . . ? C3 O2 H2 108(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -178.34(19) . . . . ? C6 C1 C2 C3 1.6(3) . . . . ? O1 C1 C2 C7 1.9(3) . . . . ? C6 C1 C2 C7 -178.2(2) . . . . ? C1 C2 C3 O2 179.35(19) . . . . ? C7 C2 C3 O2 -0.9(3) . . . . ? C1 C2 C3 C4 -2.0(3) . . . . ? C7 C2 C3 C4 177.8(2) . . . . ? O2 C3 C4 C5 179.9(2) . . . . ? C2 C3 C4 C5 1.3(3) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C4 C5 C6 C1 -0.2(4) . . . . ? O1 C1 C6 C5 179.4(2) . . . . ? C2 C1 C6 C5 -0.5(4) . . . . ? N1 C15 C16 C17 0.7(5) . . . . ? C15 C16 C17 C18 -0.8(4) . . . . ? C15 C16 C17 C17 179.9(3) . . . 2_765 ? C16 C17 C18 C19 0.8(4) . . . . ? C17 C17 C18 C19 -179.9(3) 2_765 . . . ? C17 C18 C19 N1 -0.7(4) . . . . ? N3 C25 C26 C27 -0.3(5) . . . . ? C25 C26 C27 C28 0.3(4) . . . . ? C25 C26 C27 C27 -179.7(3) . . . 2_756 ? C26 C27 C28 C29 -0.1(4) . . . . ? C27 C27 C28 C29 179.9(3) 2_756 . . . ? C27 C28 C29 N3 -0.1(4) . . . . ? C37 S1 C35 C36 1.2(3) . . . . ? S1 C35 C36 C39 0.0(4) . . . . ? C37 C39 C36 C35 -1.2(3) . . . . ? C36 C39 C37 C37 -178.3(3) . . . 2_656 ? C36 C39 C37 S1 2.05(19) . . . . ? C35 S1 C37 C37 178.3(3) . . . 2_656 ? C35 S1 C37 C39 -2.08(19) . . . . ? C18 C19 N1 C15 0.5(4) . . . . ? C16 C15 N1 C19 -0.5(4) . . . . ? C26 C25 N3 C29 0.1(4) . . . . ? C28 C29 N3 C25 0.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.525 _refine_diff_density_min -0.600 _refine_diff_density_rms 0.074 # Attachment '26dht-44bp- -2 3 CHCL3-DMS06.2.cif' data_26dht-44bp- _database_code_depnum_ccdc_archive 'CCDC 836442' #TrackingRef '26dht-44bp- -2 3 CHCL3-DMS06.2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H40 N6 O4' _chemical_formula_weight 716.82 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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4760(15) _cell_length_b 14.897(3) _cell_length_c 18.240(4) _cell_angle_alpha 110.15(3) _cell_angle_beta 90.76(3) _cell_angle_gamma 102.60(3) _cell_volume 1852.4(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4386 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.5 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.084 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9474 _exptl_absorpt_correction_T_max 0.9752 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19845 _diffrn_reflns_av_R_equivalents 0.0809 _diffrn_reflns_av_sigmaI/netI 0.1122 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 27.52 _reflns_number_total 8498 _reflns_number_gt 6368 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1734P)^2^+1.3936P] 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 8498 _refine_ls_number_parameters 493 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0822 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.2213 _refine_ls_wR_factor_gt 0.1890 _refine_ls_goodness_of_fit_ref 0.742 _refine_ls_restrained_S_all 0.742 _refine_ls_shift/su_max 0.086 _refine_ls_shift/su_mean 0.021 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 O3 O -0.41989(17) 0.25611(10) 0.46115(8) 0.0337(3) Uani 1 1 d . . . H3 H -0.4314 0.2940 0.4372 0.051 Uiso 1 1 calc R . . O4 O -0.72567(19) 0.10720(11) 0.62920(9) 0.0392(4) Uani 1 1 d . . . H4 H -0.8278 0.0965 0.6472 0.059 Uiso 1 1 calc R . . C001 C -0.5788(2) 0.23355(12) 0.49404(10) 0.0261(4) Uani 1 1 d . . . C002 C -0.5745(2) 0.18114(12) 0.54458(10) 0.0259(4) Uani 1 1 d . . . C003 C -0.7391(3) 0.26016(14) 0.47798(11) 0.0307(4) Uani 1 1 d . . . H003 H -0.7402 0.2960 0.4439 0.037 Uiso 1 1 calc R . . C004 C -0.7355(2) 0.15648(13) 0.57938(10) 0.0280(4) Uani 1 1 d . . . N2 N -1.9484(2) -0.06333(12) 0.81486(10) 0.0360(4) Uani 1 1 d . . . C005 C -0.8965(2) 0.18199(15) 0.56299(11) 0.0326(4) Uani 1 1 d . . . H005 H -1.0051 0.1642 0.5862 0.039 Uiso 1 1 calc R . . N1 N -1.0581(2) 0.06608(13) 0.69159(10) 0.0375(4) Uani 1 1 d . . . C006 C -0.4021(2) 0.15203(15) 0.56139(12) 0.0343(4) Uani 1 1 d . . . H00A H -0.4017 0.1460 0.6132 0.051 Uiso 1 1 calc R . . H00B H -0.2940 0.2024 0.5605 0.051 Uiso 1 1 calc R . . H00C H -0.3983 0.0887 0.5214 0.051 Uiso 1 1 calc R . . C007 C -0.8965(3) 0.23356(14) 0.51251(11) 0.0330(4) Uani 1 1 d . . . H007 H -1.0060 0.2509 0.5014 0.040 Uiso 1 1 calc R . . C008 C -1.4099(2) 0.01411(12) 0.74010(10) 0.0283(4) Uani 1 1 d . . . C009 C -1.5965(2) -0.01293(12) 0.76543(11) 0.0287(4) Uani 1 1 d . . . C010 C -1.3719(3) -0.02656(16) 0.66328(12) 0.0408(5) Uani 1 1 d . . . H010 H -1.4656 -0.0736 0.6252 0.049 Uiso 1 1 calc R . . C011 C -1.6328(3) 0.02633(16) 0.84286(12) 0.0415(5) Uani 1 1 d . . . H011 H -1.5378 0.0718 0.8812 0.050 Uiso 1 1 calc R . . C012 C -1.2645(3) 0.08105(17) 0.79259(12) 0.0441(5) Uani 1 1 d . . . H012 H -1.2822 0.1107 0.8463 0.053 Uiso 1 1 calc R . . C013 C -1.7444(3) -0.07773(18) 0.71294(13) 0.0471(6) Uani 1 1 d . . . H013 H -1.7285 -0.1063 0.6589 0.056 Uiso 1 1 calc R . . C014 C -1.0932(3) 0.10428(17) 0.76613(13) 0.0451(5) Uani 1 1 d . . . H014 H -0.9957 0.1499 0.8031 0.054 Uiso 1 1 calc R . . C015 C -1.1973(3) 0.00125(17) 0.64182(13) 0.0430(5) Uani 1 1 d . . . H015 H -1.1757 -0.0276 0.5885 0.052 Uiso 1 1 calc R . . C016 C -1.8073(3) -0.00078(17) 0.86434(13) 0.0451(5) Uani 1 1 d . . . H016 H -1.8276 0.0272 0.9179 0.054 Uiso 1 1 calc R . . C017 C -1.9149(3) -0.10044(17) 0.73982(13) 0.0455(5) Uani 1 1 d . . . H017 H -2.0136 -0.1449 0.7029 0.055 Uiso 1 1 calc R . . O2 O 0.39125(18) 0.74020(10) 0.03472(8) 0.0346(3) Uani 1 1 d . . . H2 H 0.4024 0.7068 0.0627 0.052 Uiso 1 1 calc R . . O1 O 0.71499(18) 0.88801(11) -0.12996(9) 0.0387(3) Uani 1 1 d . . . H1 H 0.8202 0.9010 -0.1449 0.058 Uiso 1 1 calc R . . C018 C 0.5533(2) 0.76174(13) 0.00371(10) 0.0270(4) Uani 1 1 d . . . C019 C 0.7192(2) 0.83884(13) -0.07956(11) 0.0288(4) Uani 1 1 d . . . C020 C 0.5544(2) 0.81249(13) -0.04825(10) 0.0276(4) Uani 1 1 d . . . C021 C 0.3825(3) 0.83890(17) -0.06914(13) 0.0410(5) Uani 1 1 d . . . H02A H 0.3749 0.9026 -0.0307 0.061 Uiso 1 1 calc R . . H02B H 0.2744 0.7882 -0.0687 0.061 Uiso 1 1 calc R . . H02C H 0.3861 0.8431 -0.1216 0.061 Uiso 1 1 calc R . . C022 C 0.8739(3) 0.76339(15) -0.00918(11) 0.0342(4) Uani 1 1 d . . . H022 H 0.9825 0.7467 0.0040 0.041 Uiso 1 1 calc R . . C023 C 0.8792(3) 0.81447(15) -0.06002(11) 0.0338(4) Uani 1 1 d . . . H023 H 0.9904 0.8328 -0.0815 0.041 Uiso 1 1 calc R . . C024 C 0.7122(3) 0.73604(14) 0.02302(11) 0.0322(4) Uani 1 1 d . . . H024 H 0.7097 0.7005 0.0575 0.039 Uiso 1 1 calc R . . N6 N 0.4011(2) 0.63409(14) 0.13045(10) 0.0389(4) Uani 1 1 d . . . N5 N 0.5519(2) 0.37148(14) 0.37581(10) 0.0387(4) Uani 1 1 d . . . C025 C 0.9553(2) 0.51165(13) 0.21892(10) 0.0279(4) Uani 1 1 d . . . C026 C 0.9539(3) 0.38835(15) 0.28491(12) 0.0385(4) Uani 1 1 d . . . H026 H 0.8904 0.3367 0.2391 0.046 Uiso 1 1 calc R . . C027 C 1.0019(2) 0.48488(13) 0.28707(10) 0.0275(4) Uani 1 1 d . . . C028 C 0.4590(2) 0.53005(14) 0.22773(10) 0.0278(4) Uani 1 1 d . . . C029 C 0.4390(3) 0.67889(16) 0.20797(12) 0.0402(5) Uani 1 1 d . . . H029 H 0.4472 0.7477 0.2298 0.048 Uiso 1 1 calc R . . C030 C 0.4915(2) 0.47492(13) 0.27891(10) 0.0282(4) Uani 1 1 d . . . C031 C 0.4670(3) 0.63063(15) 0.25835(11) 0.0347(4) Uani 1 1 d . . . H031 H 0.4915 0.6658 0.3133 0.042 Uiso 1 1 calc R . . N4 N 0.8651(2) 0.56181(15) 0.08977(11) 0.0423(4) Uani 1 1 d . . . C032 C 0.4617(3) 0.32528(16) 0.30428(13) 0.0414(5) Uani 1 1 d . . . H032 H 0.4178 0.2558 0.2868 0.050 Uiso 1 1 calc R . . C033 C 0.4288(3) 0.37299(14) 0.25432(12) 0.0365(4) Uani 1 1 d . . . H033 H 0.3643 0.3367 0.2039 0.044 Uiso 1 1 calc R . . C034 C 0.9243(3) 0.60371(15) 0.22916(12) 0.0362(4) Uani 1 1 d . . . H034 H 0.9336 0.6517 0.2803 0.043 Uiso 1 1 calc R . . N3 N 1.0916(3) 0.43610(15) 0.41699(11) 0.0445(4) Uani 1 1 d . . . C035 C 1.0928(3) 0.55599(14) 0.35639(11) 0.0323(4) Uani 1 1 d . . . H035 H 1.1266 0.6232 0.3612 0.039 Uiso 1 1 calc R . . C036 C 0.8797(3) 0.62427(17) 0.16358(13) 0.0437(5) Uani 1 1 d . . . H036 H 0.8579 0.6874 0.1718 0.052 Uiso 1 1 calc R . . C037 C 0.9376(3) 0.44587(15) 0.14266(11) 0.0357(4) Uani 1 1 d . . . H037 H 0.9552 0.3816 0.1325 0.043 Uiso 1 1 calc R . . C038 C 0.4179(3) 0.48316(15) 0.14703(11) 0.0329(4) Uani 1 1 d . . . H038 H 0.4095 0.4145 0.1234 0.039 Uiso 1 1 calc R . . C039 C 0.5859(2) 0.52315(14) 0.35346(10) 0.0301(4) Uani 1 1 d . . . H039 H 0.6319 0.5926 0.3725 0.036 Uiso 1 1 calc R . . C040 C 0.8941(3) 0.47415(18) 0.08085(12) 0.0419(5) Uani 1 1 d . . . H040 H 0.8846 0.4278 0.0290 0.050 Uiso 1 1 calc R . . C041 C 1.0007(3) 0.36892(17) 0.35090(13) 0.0455(5) Uani 1 1 d . . . H041 H 0.9650 0.3027 0.3487 0.055 Uiso 1 1 calc R . . C042 C 1.1342(3) 0.52840(17) 0.41874(12) 0.0401(5) Uani 1 1 d . . . H042 H 1.1968 0.5785 0.4655 0.048 Uiso 1 1 calc R . . C043 C 0.6123(3) 0.46915(15) 0.39965(11) 0.0336(4) Uani 1 1 d . . . H043 H 0.6761 0.5032 0.4505 0.040 Uiso 1 1 calc R . . C044 C 0.3895(3) 0.53719(16) 0.10125(11) 0.0367(4) Uani 1 1 d . . . H044 H 0.3602 0.5036 0.0463 0.044 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 O3 0.0268(6) 0.0389(8) 0.0431(8) 0.0252(6) 0.0092(5) 0.0057(5) O4 0.0286(7) 0.0529(9) 0.0515(9) 0.0367(7) 0.0109(6) 0.0106(6) C001 0.0243(8) 0.0247(8) 0.0295(8) 0.0110(7) 0.0044(6) 0.0037(6) C002 0.0210(8) 0.0259(8) 0.0332(9) 0.0133(7) 0.0036(6) 0.0058(6) C003 0.0297(9) 0.0335(9) 0.0333(9) 0.0159(7) 0.0039(7) 0.0100(7) C004 0.0243(8) 0.0308(9) 0.0313(9) 0.0143(7) 0.0038(7) 0.0061(7) N2 0.0336(8) 0.0324(8) 0.0480(10) 0.0202(7) 0.0164(7) 0.0098(7) C005 0.0230(8) 0.0414(10) 0.0384(10) 0.0194(8) 0.0081(7) 0.0090(7) N1 0.0324(8) 0.0374(9) 0.0466(10) 0.0220(8) 0.0120(7) 0.0044(7) C006 0.0226(8) 0.0429(11) 0.0463(11) 0.0256(9) 0.0063(7) 0.0095(7) C007 0.0257(9) 0.0394(10) 0.0383(10) 0.0159(8) 0.0030(7) 0.0128(8) C008 0.0305(9) 0.0222(8) 0.0336(9) 0.0121(7) 0.0099(7) 0.0055(7) C009 0.0319(9) 0.0216(8) 0.0343(9) 0.0113(7) 0.0107(7) 0.0074(7) C010 0.0337(10) 0.0433(11) 0.0362(10) 0.0071(9) 0.0112(8) 0.0014(9) C011 0.0368(10) 0.0450(12) 0.0342(10) 0.0073(9) 0.0101(8) 0.0031(9) C012 0.0391(11) 0.0445(12) 0.0359(11) 0.0061(9) 0.0109(8) -0.0030(9) C013 0.0365(11) 0.0517(13) 0.0373(11) 0.0032(9) 0.0123(9) -0.0012(9) C014 0.0352(11) 0.0447(12) 0.0462(12) 0.0142(10) 0.0069(9) -0.0060(9) C015 0.0397(11) 0.0491(12) 0.0373(11) 0.0134(9) 0.0160(9) 0.0071(9) C016 0.0432(12) 0.0518(13) 0.0369(11) 0.0124(9) 0.0171(9) 0.0093(10) C017 0.0335(10) 0.0433(12) 0.0486(12) 0.0082(10) 0.0107(9) -0.0006(9) O2 0.0284(7) 0.0412(8) 0.0426(8) 0.0266(6) 0.0079(5) 0.0062(6) O1 0.0278(7) 0.0526(9) 0.0506(9) 0.0360(7) 0.0107(6) 0.0105(6) C018 0.0260(8) 0.0264(8) 0.0301(9) 0.0120(7) 0.0050(6) 0.0060(7) C019 0.0257(8) 0.0314(9) 0.0327(9) 0.0153(7) 0.0050(7) 0.0071(7) C020 0.0217(8) 0.0306(9) 0.0344(9) 0.0160(7) 0.0039(7) 0.0069(7) C021 0.0239(9) 0.0568(13) 0.0572(13) 0.0369(11) 0.0073(8) 0.0123(9) C022 0.0269(9) 0.0430(11) 0.0381(10) 0.0167(8) 0.0036(7) 0.0154(8) C023 0.0241(8) 0.0420(11) 0.0391(10) 0.0169(8) 0.0083(7) 0.0115(8) C024 0.0358(10) 0.0337(9) 0.0326(9) 0.0162(8) 0.0024(7) 0.0121(8) N6 0.0335(8) 0.0539(11) 0.0403(9) 0.0308(8) 0.0060(7) 0.0097(8) N5 0.0333(8) 0.0510(11) 0.0429(9) 0.0309(8) 0.0083(7) 0.0090(7) C025 0.0217(8) 0.0340(9) 0.0301(9) 0.0142(7) 0.0018(6) 0.0064(7) C026 0.0410(11) 0.0363(10) 0.0404(11) 0.0154(8) 0.0030(8) 0.0108(8) C027 0.0222(8) 0.0340(9) 0.0292(9) 0.0133(7) 0.0044(6) 0.0091(7) C028 0.0222(8) 0.0366(9) 0.0266(8) 0.0146(7) 0.0034(6) 0.0052(7) C029 0.0431(11) 0.0424(11) 0.0434(11) 0.0233(9) 0.0070(9) 0.0133(9) C030 0.0241(8) 0.0365(9) 0.0271(8) 0.0150(7) 0.0057(6) 0.0069(7) C031 0.0372(10) 0.0383(10) 0.0317(9) 0.0154(8) 0.0043(7) 0.0102(8) N4 0.0364(9) 0.0561(11) 0.0408(10) 0.0275(9) -0.0011(7) 0.0073(8) C032 0.0401(11) 0.0391(11) 0.0491(12) 0.0243(9) 0.0048(9) 0.0039(9) C033 0.0371(10) 0.0353(10) 0.0358(10) 0.0153(8) -0.0005(8) 0.0019(8) C034 0.0364(10) 0.0362(10) 0.0366(10) 0.0140(8) -0.0006(8) 0.0084(8) N3 0.0472(10) 0.0587(12) 0.0402(10) 0.0282(9) 0.0041(8) 0.0206(9) C035 0.0316(9) 0.0352(10) 0.0309(9) 0.0138(8) 0.0026(7) 0.0061(7) C036 0.0426(11) 0.0451(12) 0.0502(12) 0.0267(10) -0.0012(9) 0.0089(9) C037 0.0362(10) 0.0378(10) 0.0331(10) 0.0124(8) 0.0032(8) 0.0094(8) C038 0.0293(9) 0.0401(10) 0.0292(9) 0.0146(8) 0.0008(7) 0.0045(8) C039 0.0285(9) 0.0366(10) 0.0269(9) 0.0129(7) 0.0038(7) 0.0084(7) C040 0.0412(11) 0.0570(13) 0.0277(10) 0.0166(9) 0.0022(8) 0.0098(10) C041 0.0543(13) 0.0400(11) 0.0528(13) 0.0261(10) 0.0074(10) 0.0169(10) C042 0.0366(10) 0.0533(13) 0.0320(10) 0.0172(9) -0.0002(8) 0.0107(9) C043 0.0298(9) 0.0475(11) 0.0304(9) 0.0218(8) 0.0042(7) 0.0096(8) C044 0.0321(9) 0.0535(12) 0.0282(9) 0.0211(9) 0.0017(7) 0.0067(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C001 1.367(2) . ? O3 H3 0.8400 . ? O4 C004 1.361(2) . ? O4 H4 0.8400 . ? C001 C003 1.399(2) . ? C001 C002 1.402(2) . ? C002 C004 1.405(2) . ? C002 C006 1.506(2) . ? C003 C007 1.388(3) . ? C003 H003 0.9500 . ? C004 C005 1.397(2) . ? N2 C016 1.327(3) . ? N2 C017 1.338(3) . ? C005 C007 1.388(3) . ? C005 H005 0.9500 . ? N1 C015 1.331(3) . ? N1 C014 1.335(3) . ? C006 H00A 0.9800 . ? C006 H00B 0.9800 . ? C006 H00C 0.9800 . ? C007 H007 0.9500 . ? C008 C010 1.383(3) . ? C008 C012 1.391(3) . ? C008 C009 1.491(3) . ? C009 C011 1.386(3) . ? C009 C013 1.393(3) . ? C010 C015 1.385(3) . ? C010 H010 0.9500 . ? C011 C016 1.383(3) . ? C011 H011 0.9500 . ? C012 C014 1.390(3) . ? C012 H012 0.9500 . ? C013 C017 1.387(3) . ? C013 H013 0.9500 . ? C014 H014 0.9500 . ? C015 H015 0.9500 . ? C016 H016 0.9500 . ? C017 H017 0.9500 . ? O2 C018 1.366(2) . ? O2 H2 0.8400 . ? O1 C019 1.362(2) . ? O1 H1 0.8400 . ? C018 C024 1.400(3) . ? C018 C020 1.401(2) . ? C019 C020 1.400(2) . ? C019 C023 1.399(3) . ? C020 C021 1.504(2) . ? C021 H02A 0.9800 . ? C021 H02B 0.9800 . ? C021 H02C 0.9800 . ? C022 C023 1.384(3) . ? C022 C024 1.393(3) . ? C022 H022 0.9500 . ? C023 H023 0.9500 . ? C024 H024 0.9500 . ? N6 C044 1.338(3) . ? N6 C029 1.335(3) . ? N5 C043 1.335(3) . ? N5 C032 1.336(3) . ? C025 C037 1.383(3) . ? C025 C034 1.390(3) . ? C025 C027 1.489(3) . ? C026 C027 1.390(3) . ? C026 C041 1.388(3) . ? C026 H026 0.9500 . ? C027 C035 1.387(3) . ? C028 C038 1.391(2) . ? C028 C031 1.394(3) . ? C028 C030 1.488(3) . ? C029 C031 1.386(3) . ? C029 H029 0.9500 . ? C030 C039 1.394(2) . ? C030 C033 1.393(3) . ? C031 H031 0.9500 . ? N4 C040 1.325(3) . ? N4 C036 1.334(3) . ? C032 C033 1.383(3) . ? C032 H032 0.9500 . ? C033 H033 0.9500 . ? C034 C036 1.387(3) . ? C034 H034 0.9500 . ? N3 C042 1.331(3) . ? N3 C041 1.329(3) . ? C035 C042 1.388(3) . ? C035 H035 0.9500 . ? C036 H036 0.9500 . ? C037 C040 1.390(3) . ? C037 H037 0.9500 . ? C038 C044 1.387(3) . ? C038 H038 0.9500 . ? C039 C043 1.389(2) . ? C039 H039 0.9500 . ? C040 H040 0.9500 . ? C041 H041 0.9500 . ? C042 H042 0.9500 . ? C043 H043 0.9500 . ? C044 H044 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 C001 O3 H3 109.5 . . ? C004 O4 H4 109.5 . . ? O3 C001 C003 122.20(16) . . ? O3 C001 C002 116.66(15) . . ? C003 C001 C002 121.14(16) . . ? C004 C002 C001 118.27(15) . . ? C004 C002 C006 120.69(16) . . ? C001 C002 C006 121.04(15) . . ? C007 C003 C001 119.16(17) . . ? C007 C003 H003 120.4 . . ? C001 C003 H003 120.4 . . ? O4 C004 C005 122.38(16) . . ? O4 C004 C002 116.76(15) . . ? C005 C004 C002 120.86(16) . . ? C016 N2 C017 116.16(18) . . ? C007 C005 C004 119.50(17) . . ? C007 C005 H005 120.2 . . ? C004 C005 H005 120.2 . . ? C015 N1 C014 116.40(17) . . ? C002 C006 H00A 109.5 . . ? C002 C006 H00B 109.5 . . ? H00A C006 H00B 109.5 . . ? C002 C006 H00C 109.5 . . ? H00A C006 H00C 109.5 . . ? H00B C006 H00C 109.5 . . ? C005 C007 C003 121.06(17) . . ? C005 C007 H007 119.5 . . ? C003 C007 H007 119.5 . . ? C010 C008 C012 116.45(18) . . ? C010 C008 C009 121.77(18) . . ? C012 C008 C009 121.78(17) . . ? C011 C009 C013 116.25(18) . . ? C011 C009 C008 121.52(18) . . ? C013 C009 C008 122.23(17) . . ? C008 C010 C015 120.1(2) . . ? C008 C010 H010 120.0 . . ? C015 C010 H010 120.0 . . ? C009 C011 C016 119.9(2) . . ? C009 C011 H011 120.0 . . ? C016 C011 H011 120.0 . . ? C008 C012 C014 119.68(19) . . ? C008 C012 H012 120.2 . . ? C014 C012 H012 120.2 . . ? C017 C013 C009 119.76(19) . . ? C017 C013 H013 120.1 . . ? C009 C013 H013 120.1 . . ? N1 C014 C012 123.6(2) . . ? N1 C014 H014 118.2 . . ? C012 C014 H014 118.2 . . ? N1 C015 C010 123.76(19) . . ? N1 C015 H015 118.1 . . ? C010 C015 H015 118.1 . . ? N2 C016 C011 124.18(19) . . ? N2 C016 H016 117.9 . . ? C011 C016 H016 117.9 . . ? N2 C017 C013 123.7(2) . . ? N2 C017 H017 118.2 . . ? C013 C017 H017 118.2 . . ? C018 O2 H2 109.5 . . ? C019 O1 H1 109.5 . . ? O2 C018 C024 122.40(16) . . ? O2 C018 C020 116.55(15) . . ? C024 C018 C020 121.04(16) . . ? O1 C019 C020 116.88(16) . . ? O1 C019 C023 122.19(16) . . ? C020 C019 C023 120.93(17) . . ? C019 C020 C018 118.50(16) . . ? C019 C020 C021 120.91(16) . . ? C018 C020 C021 120.59(16) . . ? C020 C021 H02A 109.5 . . ? C020 C021 H02B 109.5 . . ? H02A C021 H02B 109.5 . . ? C020 C021 H02C 109.5 . . ? H02A C021 H02C 109.5 . . ? H02B C021 H02C 109.5 . . ? C023 C022 C024 121.14(17) . . ? C023 C022 H022 119.4 . . ? C024 C022 H022 119.4 . . ? C022 C023 C019 119.40(17) . . ? C022 C023 H023 120.3 . . ? C019 C023 H023 120.3 . . ? C022 C024 C018 118.97(17) . . ? C022 C024 H024 120.5 . . ? C018 C024 H024 120.5 . . ? C044 N6 C029 116.98(17) . . ? C043 N5 C032 117.45(17) . . ? C037 C025 C034 116.80(17) . . ? C037 C025 C027 121.78(17) . . ? C034 C025 C027 121.41(17) . . ? C027 C026 C041 118.75(19) . . ? C027 C026 H026 120.6 . . ? C041 C026 H026 120.6 . . ? C035 C027 C026 116.94(17) . . ? C035 C027 C025 121.14(17) . . ? C026 C027 C025 121.90(17) . . ? C038 C028 C031 116.99(17) . . ? C038 C028 C030 121.33(17) . . ? C031 C028 C030 121.68(16) . . ? N6 C029 C031 123.62(19) . . ? N6 C029 H029 118.2 . . ? C031 C029 H029 118.2 . . ? C039 C030 C033 117.25(17) . . ? C039 C030 C028 121.36(17) . . ? C033 C030 C028 121.39(17) . . ? C029 C031 C028 119.41(18) . . ? C029 C031 H031 120.3 . . ? C028 C031 H031 120.3 . . ? C040 N4 C036 115.79(17) . . ? N5 C032 C033 123.65(19) . . ? N5 C032 H032 118.2 . . ? C033 C032 H032 118.2 . . ? C032 C033 C030 119.13(18) . . ? C032 C033 H033 120.4 . . ? C030 C033 H033 120.4 . . ? C036 C034 C025 118.91(19) . . ? C036 C034 H034 120.5 . . ? C025 C034 H034 120.5 . . ? C042 N3 C041 115.81(17) . . ? C027 C035 C042 119.61(19) . . ? C027 C035 H035 120.2 . . ? C042 C035 H035 120.2 . . ? N4 C036 C034 124.7(2) . . ? N4 C036 H036 117.7 . . ? C034 C036 H036 117.7 . . ? C025 C037 C040 119.78(19) . . ? C025 C037 H037 120.1 . . ? C040 C037 H037 120.1 . . ? C044 C038 C028 119.61(19) . . ? C044 C038 H038 120.2 . . ? C028 C038 H038 120.2 . . ? C043 C039 C030 119.62(18) . . ? C043 C039 H039 120.2 . . ? C030 C039 H039 120.2 . . ? N4 C040 C037 124.0(2) . . ? N4 C040 H040 118.0 . . ? C037 C040 H040 118.0 . . ? N3 C041 C026 124.8(2) . . ? N3 C041 H041 117.6 . . ? C026 C041 H041 117.6 . . ? N3 C042 C035 124.0(2) . . ? N3 C042 H042 118.0 . . ? C035 C042 H042 118.0 . . ? N5 C043 C039 122.89(18) . . ? N5 C043 H043 118.6 . . ? C039 C043 H043 118.6 . . ? N6 C044 C038 123.37(18) . . ? N6 C044 H044 118.3 . . ? C038 C044 H044 118.3 . . ? 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 O3 C001 C002 C004 -179.88(16) . . . . ? C003 C001 C002 C004 -0.5(3) . . . . ? O3 C001 C002 C006 0.2(3) . . . . ? C003 C001 C002 C006 179.62(17) . . . . ? O3 C001 C003 C007 179.03(17) . . . . ? C002 C001 C003 C007 -0.4(3) . . . . ? C001 C002 C004 O4 -178.84(16) . . . . ? C006 C002 C004 O4 1.1(3) . . . . ? C001 C002 C004 C005 1.1(3) . . . . ? C006 C002 C004 C005 -178.99(18) . . . . ? O4 C004 C005 C007 179.03(17) . . . . ? C002 C004 C005 C007 -0.9(3) . . . . ? C004 C005 C007 C003 0.1(3) . . . . ? C001 C003 C007 C005 0.6(3) . . . . ? C010 C008 C009 C011 178.47(18) . . . . ? C012 C008 C009 C011 -1.1(3) . . . . ? C010 C008 C009 C013 -2.3(3) . . . . ? C012 C008 C009 C013 178.14(19) . . . . ? C012 C008 C010 C015 -1.2(3) . . . . ? C009 C008 C010 C015 179.3(2) . . . . ? C013 C009 C011 C016 1.1(3) . . . . ? C008 C009 C011 C016 -179.7(2) . . . . ? C010 C008 C012 C014 0.8(3) . . . . ? C009 C008 C012 C014 -179.7(2) . . . . ? C011 C009 C013 C017 -0.9(3) . . . . ? C008 C009 C013 C017 179.8(2) . . . . ? C015 N1 C014 C012 -1.1(3) . . . . ? C008 C012 C014 N1 0.4(4) . . . . ? C014 N1 C015 C010 0.7(3) . . . . ? C008 C010 C015 N1 0.5(4) . . . . ? C017 N2 C016 C011 -0.6(3) . . . . ? C009 C011 C016 N2 -0.3(4) . . . . ? C016 N2 C017 C013 0.7(3) . . . . ? C009 C013 C017 N2 0.0(4) . . . . ? O1 C019 C020 C018 179.92(16) . . . . ? C023 C019 C020 C018 0.5(3) . . . . ? O1 C019 C020 C021 -0.7(3) . . . . ? C023 C019 C020 C021 179.87(18) . . . . ? O2 C018 C020 C019 178.02(16) . . . . ? C024 C018 C020 C019 -1.2(3) . . . . ? O2 C018 C020 C021 -1.3(3) . . . . ? C024 C018 C020 C021 179.44(18) . . . . ? C024 C022 C023 C019 -0.2(3) . . . . ? O1 C019 C023 C022 -179.21(18) . . . . ? C020 C019 C023 C022 0.2(3) . . . . ? C023 C022 C024 C018 -0.5(3) . . . . ? O2 C018 C024 C022 -177.97(17) . . . . ? C020 C018 C024 C022 1.2(3) . . . . ? C041 C026 C027 C035 -0.6(3) . . . . ? C041 C026 C027 C025 -179.50(18) . . . . ? C037 C025 C027 C035 152.65(18) . . . . ? C034 C025 C027 C035 -28.4(3) . . . . ? C037 C025 C027 C026 -28.5(3) . . . . ? C034 C025 C027 C026 150.38(19) . . . . ? C044 N6 C029 C031 0.3(3) . . . . ? C038 C028 C030 C039 159.95(17) . . . . ? C031 C028 C030 C039 -20.5(3) . . . . ? C038 C028 C030 C033 -20.1(3) . . . . ? C031 C028 C030 C033 159.52(19) . . . . ? N6 C029 C031 C028 1.1(3) . . . . ? C038 C028 C031 C029 -1.6(3) . . . . ? C030 C028 C031 C029 178.83(17) . . . . ? C043 N5 C032 C033 0.2(3) . . . . ? N5 C032 C033 C030 -0.2(3) . . . . ? C039 C030 C033 C032 0.3(3) . . . . ? C028 C030 C033 C032 -179.68(18) . . . . ? C037 C025 C034 C036 -0.5(3) . . . . ? C027 C025 C034 C036 -179.41(18) . . . . ? C026 C027 C035 C042 1.2(3) . . . . ? C025 C027 C035 C042 -179.96(17) . . . . ? C040 N4 C036 C034 0.9(3) . . . . ? C025 C034 C036 N4 -0.6(3) . . . . ? C034 C025 C037 C040 1.1(3) . . . . ? C027 C025 C037 C040 -179.92(18) . . . . ? C031 C028 C038 C044 0.7(3) . . . . ? C030 C028 C038 C044 -179.68(16) . . . . ? C033 C030 C039 C043 -0.4(3) . . . . ? C028 C030 C039 C043 179.55(16) . . . . ? C036 N4 C040 C037 -0.1(3) . . . . ? C025 C037 C040 N4 -0.9(3) . . . . ? C042 N3 C041 C026 2.0(3) . . . . ? C027 C026 C041 N3 -1.0(3) . . . . ? C041 N3 C042 C035 -1.4(3) . . . . ? C027 C035 C042 N3 -0.1(3) . . . . ? C032 N5 C043 C039 -0.3(3) . . . . ? C030 C039 C043 N5 0.5(3) . . . . ? C029 N6 C044 C038 -1.2(3) . . . . ? C028 C038 C044 N6 0.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.324 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.060 # Attachment '26dht-44bp- bp-2 2 1dioxane1 N 8.cif' data_26dht-44bp-bp-221dioxane1N8 _database_code_depnum_ccdc_archive 'CCDC 836443' #TrackingRef '26dht-44bp- bp-2 2 1dioxane1 N 8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H42 N4 O4' _chemical_formula_weight 714.84 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 Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.380(5) _cell_length_b 7.5320(15) _cell_length_c 19.030(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.93(3) _cell_angle_gamma 90.00 _cell_volume 3699.5(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3008 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 0.083 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9677 _exptl_absorpt_correction_T_max 0.9757 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18432 _diffrn_reflns_av_R_equivalents 0.0962 _diffrn_reflns_av_sigmaI/netI 0.0823 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.61 _reflns_number_total 4281 _reflns_number_gt 2962 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1120P)^2^+2.0269P] 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 4281 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1258 _refine_ls_R_factor_gt 0.0878 _refine_ls_wR_factor_ref 0.2559 _refine_ls_wR_factor_gt 0.2210 _refine_ls_goodness_of_fit_ref 1.169 _refine_ls_restrained_S_all 1.169 _refine_ls_shift/su_max 0.036 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C11 C -0.02807(15) 0.8652(5) 0.3309(2) 0.0506(9) Uani 1 1 d . . . H4 H -0.0622 0.8328 0.3077 0.061 Uiso 1 1 calc R . . C14 C 0.06984(16) 0.9596(5) 0.4001(2) 0.0569(10) Uani 1 1 d . . . H21 H 0.1037 0.9932 0.4243 0.068 Uiso 1 1 calc R . . C15 C 0.05703(14) 0.9655(5) 0.3262(2) 0.0489(9) Uani 1 1 d . . . H1 H 0.0821 1.0023 0.2999 0.059 Uiso 1 1 calc R . . C16 C 0.00719(13) 0.9174(4) 0.28957(18) 0.0412(8) Uani 1 1 d . . . C17 C 0.03451(16) 0.9060(5) 0.4392(2) 0.0555(10) Uani 1 1 d . . . H2 H 0.0440 0.9013 0.4902 0.067 Uiso 1 1 calc R . . C18 C -0.01444(17) 0.8594(5) 0.4051(2) 0.0602(11) Uani 1 1 d . . . H3 H -0.0391 0.8231 0.4322 0.072 Uiso 1 1 calc R . . N1 N 0.06735(12) 0.4180(4) 0.43144(15) 0.0438(7) Uani 1 1 d . . . C2 C 0.01412(12) 0.4251(4) 0.28832(15) 0.0316(7) Uani 1 1 d . . . C5 C -0.01081(13) 0.3779(4) 0.34335(16) 0.0370(7) Uani 1 1 d . . . H14 H -0.0465 0.3475 0.3329 0.044 Uiso 1 1 calc R . . C6 C 0.01696(14) 0.3757(5) 0.41306(17) 0.0437(8) Uani 1 1 d . . . H13 H -0.0005 0.3425 0.4500 0.052 Uiso 1 1 calc R . . C8 C 0.09079(14) 0.4645(4) 0.37858(18) 0.0421(8) Uani 1 1 d . . . H15 H 0.1265 0.4953 0.3907 0.050 Uiso 1 1 calc R . . C12 C 0.06609(13) 0.4704(4) 0.30720(17) 0.0378(7) Uani 1 1 d . . . H16 H 0.0845 0.5050 0.2715 0.045 Uiso 1 1 calc R . . N2 N 0.29364(10) 0.6183(3) 0.11464(14) 0.0370(6) Uani 1 1 d . . . C19 C 0.25954(12) 0.3270(4) 0.02403(15) 0.0313(7) Uani 1 1 d . . . C20 C 0.25835(13) 0.3246(4) 0.09638(16) 0.0381(7) Uani 1 1 d . . . H19 H 0.2462 0.2222 0.1169 0.046 Uiso 1 1 calc R . . C21 C 0.27931(14) 0.4800(4) -0.00109(17) 0.0424(8) Uani 1 1 d . . . H20 H 0.2815 0.4885 -0.0502 0.051 Uiso 1 1 calc R . . C22 C 0.29571(14) 0.6191(4) 0.04477(18) 0.0426(8) Uani 1 1 d . . . H17 H 0.3093 0.7214 0.0260 0.051 Uiso 1 1 calc R . . C23 C 0.27474(13) 0.4707(4) 0.13876(17) 0.0389(7) Uani 1 1 d . . . H18 H 0.2725 0.4662 0.1879 0.047 Uiso 1 1 calc R . . O1 O 0.19193(9) 0.4105(3) 0.29361(11) 0.0380(6) Uani 1 1 d . . . H8 H 0.1957 0.3037 0.3254 0.057 Uiso 1 1 d R . . O2 O 0.12923(9) 0.6452(3) 0.06275(12) 0.0441(6) Uani 1 1 d . . . H12 H 0.1105 0.6096 0.0191 0.066 Uiso 1 1 d R . . C1 C 0.16904(11) 0.3786(4) 0.22293(15) 0.0314(7) Uani 1 1 d . . . C3 C 0.16026(11) 0.5255(4) 0.17789(16) 0.0312(7) Uani 1 1 d . . . C4 C 0.13756(12) 0.4989(4) 0.10617(16) 0.0325(7) Uani 1 1 d . . . C7 C 0.15527(12) 0.2073(4) 0.19746(17) 0.0356(7) Uani 1 1 d . . . H9 H 0.1610 0.1081 0.2289 0.043 Uiso 1 1 calc R . . C9 C 0.12432(12) 0.3287(4) 0.07936(17) 0.0359(7) Uani 1 1 d . . . H11 H 0.1094 0.3119 0.0299 0.043 Uiso 1 1 calc R . . C10 C 0.13308(12) 0.1857(4) 0.12525(17) 0.0366(7) Uani 1 1 d . . . H10 H 0.1238 0.0700 0.1072 0.044 Uiso 1 1 calc R . . C13 C 0.17595(13) 0.7086(4) 0.20697(18) 0.0408(8) Uani 1 1 d . . . H5 H 0.1651 0.7969 0.1690 0.061 Uiso 1 1 calc R . . H6 H 0.2137 0.7134 0.2234 0.061 Uiso 1 1 calc R . . H7 H 0.1593 0.7342 0.2473 0.061 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 C11 0.045(2) 0.0380(18) 0.068(3) 0.0072(17) 0.0114(18) -0.0013(16) C14 0.049(2) 0.050(2) 0.067(3) 0.000(2) 0.0006(19) 0.0091(18) C15 0.044(2) 0.0396(19) 0.063(2) 0.0034(17) 0.0103(17) 0.0034(15) C16 0.0367(18) 0.0289(16) 0.057(2) 0.0019(14) 0.0078(15) 0.0019(13) C17 0.059(2) 0.052(2) 0.052(2) 0.0103(18) 0.0041(19) 0.0062(19) C18 0.064(3) 0.055(2) 0.063(3) 0.016(2) 0.014(2) 0.004(2) N1 0.0515(18) 0.0420(16) 0.0346(15) -0.0066(12) 0.0012(12) 0.0002(13) C2 0.0395(17) 0.0255(14) 0.0285(15) -0.0035(11) 0.0041(12) 0.0005(12) C5 0.0415(18) 0.0386(17) 0.0309(16) 0.0000(13) 0.0071(13) 0.0006(14) C6 0.051(2) 0.0464(19) 0.0331(17) -0.0011(14) 0.0074(15) -0.0015(16) C8 0.0429(19) 0.0404(18) 0.0397(18) -0.0058(15) 0.0012(14) -0.0044(15) C12 0.0396(18) 0.0356(16) 0.0367(17) -0.0003(13) 0.0042(13) -0.0025(14) N2 0.0400(15) 0.0351(14) 0.0332(14) -0.0067(11) 0.0011(11) 0.0001(11) C19 0.0347(16) 0.0283(15) 0.0294(15) -0.0027(12) 0.0035(12) 0.0011(12) C20 0.0414(18) 0.0386(17) 0.0331(16) -0.0039(13) 0.0048(13) -0.0071(14) C21 0.059(2) 0.0347(17) 0.0325(17) -0.0021(13) 0.0065(15) -0.0070(15) C22 0.058(2) 0.0294(16) 0.0397(18) -0.0022(14) 0.0095(15) -0.0041(15) C23 0.0380(17) 0.0433(18) 0.0344(17) -0.0054(14) 0.0052(13) -0.0035(14) O1 0.0471(13) 0.0302(11) 0.0319(12) 0.0053(9) -0.0026(9) 0.0001(9) O2 0.0550(15) 0.0359(12) 0.0365(12) 0.0091(9) -0.0021(10) -0.0007(10) C1 0.0308(15) 0.0314(15) 0.0309(15) 0.0012(12) 0.0043(12) 0.0020(12) C3 0.0303(15) 0.0274(14) 0.0348(16) 0.0018(12) 0.0042(12) 0.0022(12) C4 0.0353(16) 0.0304(15) 0.0308(15) 0.0059(12) 0.0045(12) 0.0023(12) C7 0.0374(17) 0.0280(15) 0.0393(17) 0.0045(13) 0.0035(13) 0.0003(13) C9 0.0342(16) 0.0373(17) 0.0336(16) 0.0005(13) 0.0013(12) -0.0009(13) C10 0.0378(17) 0.0304(15) 0.0404(17) -0.0016(13) 0.0051(13) -0.0016(13) C13 0.0471(19) 0.0303(16) 0.0412(18) 0.0032(14) 0.0000(14) 0.0016(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 C18 1.383(5) . ? C11 C16 1.393(5) . ? C11 H4 0.9500 . ? C14 C17 1.368(6) . ? C14 C15 1.377(5) . ? C14 H21 0.9500 . ? C15 C16 1.403(5) . ? C15 H1 0.9500 . ? C16 C16 1.475(7) 2 ? C17 C18 1.366(6) . ? C17 H2 0.9500 . ? C18 H3 0.9500 . ? N1 C8 1.332(4) . ? N1 C6 1.341(5) . ? C2 C12 1.386(4) . ? C2 C5 1.393(4) . ? C2 C2 1.494(6) 2 ? C5 C6 1.377(4) . ? C5 H14 0.9500 . ? C6 H13 0.9500 . ? C8 C12 1.381(4) . ? C8 H15 0.9500 . ? C12 H16 0.9500 . ? N2 C23 1.338(4) . ? N2 C22 1.342(4) . ? C19 C20 1.384(4) . ? C19 C21 1.390(4) . ? C19 C19 1.498(6) 7 ? C20 C23 1.379(4) . ? C20 H19 0.9500 . ? C21 C22 1.375(4) . ? C21 H20 0.9500 . ? C22 H17 0.9500 . ? C23 H18 0.9500 . ? O1 C1 1.377(3) . ? O1 H8 0.9996 . ? O2 C4 1.368(3) . ? O2 H12 0.9147 . ? C1 C3 1.390(4) . ? C1 C7 1.399(4) . ? C3 C4 1.387(4) . ? C3 C13 1.511(4) . ? C4 C9 1.397(4) . ? C7 C10 1.388(4) . ? C7 H9 0.9500 . ? C9 C10 1.376(4) . ? C9 H11 0.9500 . ? C10 H10 0.9500 . ? C13 H5 0.9800 . ? C13 H6 0.9800 . ? C13 H7 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 C18 C11 C16 121.5(4) . . ? C18 C11 H4 119.3 . . ? C16 C11 H4 119.3 . . ? C17 C14 C15 120.9(4) . . ? C17 C14 H21 119.5 . . ? C15 C14 H21 119.5 . . ? C14 C15 C16 120.4(4) . . ? C14 C15 H1 119.8 . . ? C16 C15 H1 119.8 . . ? C11 C16 C15 117.3(3) . . ? C11 C16 C16 121.1(4) . 2 ? C15 C16 C16 121.6(4) . 2 ? C18 C17 C14 120.0(4) . . ? C18 C17 H2 120.0 . . ? C14 C17 H2 120.0 . . ? C17 C18 C11 119.9(4) . . ? C17 C18 H3 120.0 . . ? C11 C18 H3 120.0 . . ? C8 N1 C6 117.1(3) . . ? C12 C2 C5 117.6(3) . . ? C12 C2 C2 121.3(3) . 2 ? C5 C2 C2 121.1(3) . 2 ? C6 C5 C2 119.2(3) . . ? C6 C5 H14 120.4 . . ? C2 C5 H14 120.4 . . ? N1 C6 C5 123.3(3) . . ? N1 C6 H13 118.3 . . ? C5 C6 H13 118.3 . . ? N1 C8 C12 123.6(3) . . ? N1 C8 H15 118.2 . . ? C12 C8 H15 118.2 . . ? C8 C12 C2 119.2(3) . . ? C8 C12 H16 120.4 . . ? C2 C12 H16 120.4 . . ? C23 N2 C22 116.0(3) . . ? C20 C19 C21 116.1(3) . . ? C20 C19 C19 121.6(3) . 7 ? C21 C19 C19 122.3(3) . 7 ? C23 C20 C19 120.2(3) . . ? C23 C20 H19 119.9 . . ? C19 C20 H19 119.9 . . ? C22 C21 C19 120.3(3) . . ? C22 C21 H20 119.8 . . ? C19 C21 H20 119.8 . . ? N2 C22 C21 123.6(3) . . ? N2 C22 H17 118.2 . . ? C21 C22 H17 118.2 . . ? N2 C23 C20 123.8(3) . . ? N2 C23 H18 118.1 . . ? C20 C23 H18 118.1 . . ? C1 O1 H8 114.8 . . ? C4 O2 H12 107.5 . . ? O1 C1 C3 116.5(3) . . ? O1 C1 C7 122.0(3) . . ? C3 C1 C7 121.5(3) . . ? C4 C3 C1 118.3(3) . . ? C4 C3 C13 121.5(3) . . ? C1 C3 C13 120.2(3) . . ? O2 C4 C3 117.4(3) . . ? O2 C4 C9 121.5(3) . . ? C3 C4 C9 121.1(3) . . ? C10 C7 C1 118.5(3) . . ? C10 C7 H9 120.7 . . ? C1 C7 H9 120.7 . . ? C10 C9 C4 119.3(3) . . ? C10 C9 H11 120.3 . . ? C4 C9 H11 120.3 . . ? C9 C10 C7 121.2(3) . . ? C9 C10 H10 119.4 . . ? C7 C10 H10 119.4 . . ? C3 C13 H5 109.5 . . ? C3 C13 H6 109.5 . . ? H5 C13 H6 109.5 . . ? C3 C13 H7 109.5 . . ? H5 C13 H7 109.5 . . ? H6 C13 H7 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 C17 C14 C15 C16 0.4(6) . . . . ? C18 C11 C16 C15 -0.5(5) . . . . ? C18 C11 C16 C16 177.9(3) . . . 2 ? C14 C15 C16 C11 0.3(5) . . . . ? C14 C15 C16 C16 -178.2(3) . . . 2 ? C15 C14 C17 C18 -0.8(6) . . . . ? C14 C17 C18 C11 0.5(6) . . . . ? C16 C11 C18 C17 0.2(6) . . . . ? C12 C2 C5 C6 -0.9(5) . . . . ? C2 C2 C5 C6 178.5(2) 2 . . . ? C8 N1 C6 C5 0.2(5) . . . . ? C2 C5 C6 N1 0.4(5) . . . . ? C6 N1 C8 C12 -0.2(5) . . . . ? N1 C8 C12 C2 -0.3(5) . . . . ? C5 C2 C12 C8 0.8(4) . . . . ? C2 C2 C12 C8 -178.5(2) 2 . . . ? C21 C19 C20 C23 1.9(5) . . . . ? C19 C19 C20 C23 -178.0(4) 7 . . . ? C20 C19 C21 C22 -0.8(5) . . . . ? C19 C19 C21 C22 179.1(4) 7 . . . ? C23 N2 C22 C21 0.6(5) . . . . ? C19 C21 C22 N2 -0.5(6) . . . . ? C22 N2 C23 C20 0.5(5) . . . . ? C19 C20 C23 N2 -1.8(5) . . . . ? O1 C1 C3 C4 179.6(3) . . . . ? C7 C1 C3 C4 -0.4(5) . . . . ? O1 C1 C3 C13 0.4(4) . . . . ? C7 C1 C3 C13 -179.6(3) . . . . ? C1 C3 C4 O2 180.0(3) . . . . ? C13 C3 C4 O2 -0.8(4) . . . . ? C1 C3 C4 C9 -0.7(5) . . . . ? C13 C3 C4 C9 178.4(3) . . . . ? O1 C1 C7 C10 -179.0(3) . . . . ? C3 C1 C7 C10 1.0(5) . . . . ? O2 C4 C9 C10 -179.5(3) . . . . ? C3 C4 C9 C10 1.2(5) . . . . ? C4 C9 C10 C7 -0.6(5) . . . . ? C1 C7 C10 C9 -0.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.61 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.243 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.067 # Attachment '26dht-44bp-pyrene_meoh5(6.7).cif' data_26dht-44bp-pyrene_meoh5(6.7) _database_code_depnum_ccdc_archive 'CCDC 836444' #TrackingRef '26dht-44bp-pyrene_meoh5(6.7).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C83 H64 N6 O6' _chemical_formula_weight 1241.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.509(6) _cell_length_b 8.755(6) _cell_length_c 24.70(2) _cell_angle_alpha 91.768(12) _cell_angle_beta 96.793(14) _cell_angle_gamma 93.035(13) _cell_volume 1609(2) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3417 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.5 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 0.081 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9839 _exptl_absorpt_correction_T_max 0.9839 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17140 _diffrn_reflns_av_R_equivalents 0.0749 _diffrn_reflns_av_sigmaI/netI 0.0902 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 0.83 _diffrn_reflns_theta_max 27.56 _reflns_number_total 7370 _reflns_number_gt 4555 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1104P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7370 _refine_ls_number_parameters 494 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1175 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.2283 _refine_ls_wR_factor_gt 0.1767 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5921(6) 0.6687(5) 0.42570(17) 0.0498(10) Uani 0.50 1 d P . . O3 O 0.6458(5) 0.2551(4) 0.54087(16) 0.0512(10) Uani 0.50 1 d P . . C1 C 0.5240(14) 0.5881(8) 0.4651(3) 0.0347(17) Uani 0.50 1 d P . . C2 C 0.6182(9) 0.4620(7) 0.4845(3) 0.0330(13) Uani 0.50 1 d P . . C3 C 0.5447(13) 0.3761(9) 0.5244(3) 0.0341(18) Uani 0.50 1 d P . . C4 C 0.3888(10) 0.4125(9) 0.5476(3) 0.0423(17) Uani 0.50 1 d P . . C5 C 0.3000(14) 0.5423(8) 0.5287(3) 0.0400(15) Uani 0.50 1 d P . . C6 C 0.3690(10) 0.6279(8) 0.4880(3) 0.0400(16) Uani 0.50 1 d P . . C7 C 0.7928(10) 0.4256(8) 0.4630(3) 0.0415(14) Uani 0.50 1 d P . . H1 H 0.488(9) 0.764(8) 0.419(3) 0.07(2) Uiso 0.50 1 d P . . H7B H 0.797(9) 0.474(8) 0.432(3) 0.07(2) Uiso 0.50 1 d P . . H7A H 0.893(11) 0.483(9) 0.481(3) 0.09(3) Uiso 0.50 1 d P . . H7C H 0.787(9) 0.334(8) 0.452(3) 0.06(2) Uiso 0.50 1 d P . . O8 O 0.5256(2) 0.80239(19) 0.14702(7) 0.0348(4) Uani 1 1 d . . . O10 O 0.2517(2) 1.21600(19) 0.05820(7) 0.0398(4) Uani 1 1 d . . . C8 C 0.3738(3) 0.8806(3) 0.13399(9) 0.0285(5) Uani 1 1 d . . . C9 C 0.3877(3) 1.0090(3) 0.10212(9) 0.0281(5) Uani 1 1 d . . . C10 C 0.2331(3) 1.0891(3) 0.08833(9) 0.0306(5) Uani 1 1 d . . . C11 C 0.0688(3) 1.0408(3) 0.10505(10) 0.0377(6) Uani 1 1 d . . . H11 H -0.0354 1.0955 0.0952 0.045 Uiso 1 1 calc R . . C12 C 0.0593(3) 0.9127(3) 0.13605(11) 0.0421(6) Uani 1 1 d . . . H12 H -0.0526 0.8793 0.1472 0.050 Uiso 1 1 calc R . . C13 C 0.2104(3) 0.8316(3) 0.15122(10) 0.0371(6) Uani 1 1 d . . . H13 H 0.2027 0.7443 0.1729 0.044 Uiso 1 1 calc R . . C14 C 0.5609(3) 1.0587(3) 0.08139(10) 0.0370(6) Uani 1 1 d . . . H14A H 0.5413 1.0647 0.0416 0.056 Uiso 1 1 calc R . . H14B H 0.6512 0.9844 0.0914 0.056 Uiso 1 1 calc R . . H14C H 0.6033 1.1596 0.0977 0.056 Uiso 1 1 calc R . . H8 H 0.487(5) 0.699(4) 0.1654(14) 0.078(10) Uiso 1 1 d . . . H10 H 0.133(5) 1.267(4) 0.0530(13) 0.072(10) Uiso 1 1 d . . . N1 N 0.4443(3) -0.0807(3) 0.37958(11) 0.0522(6) Uani 1 1 d . . . N2 N 0.4604(3) 0.5496(3) 0.20451(10) 0.0454(6) Uani 1 1 d . . . C22 C 0.3555(4) -0.0890(3) 0.32958(13) 0.0491(7) Uani 1 1 d . . . H22 H 0.2925 -0.1831 0.3176 0.059 Uiso 1 1 calc R . . C23 C 0.3484(3) 0.0297(3) 0.29389(12) 0.0414(6) Uani 1 1 d . . . H23 H 0.2830 0.0160 0.2586 0.050 Uiso 1 1 calc R . . C24 C 0.4384(3) 0.1696(3) 0.31036(10) 0.0337(5) Uani 1 1 d . . . C25 C 0.5302(4) 0.1795(3) 0.36282(11) 0.0439(6) Uani 1 1 d . . . H25 H 0.5938 0.2723 0.3762 0.053 Uiso 1 1 calc R . . C26 C 0.5286(4) 0.0544(3) 0.39530(13) 0.0536(8) Uani 1 1 d . . . H26 H 0.5913 0.0649 0.4311 0.064 Uiso 1 1 calc R . . C27 C 0.4054(4) 0.4086(3) 0.18520(12) 0.0480(7) Uani 1 1 d . . . H27 H 0.3725 0.3933 0.1470 0.058 Uiso 1 1 calc R . . C28 C 0.3939(4) 0.2836(3) 0.21790(11) 0.0415(6) Uani 1 1 d . . . H28 H 0.3531 0.1858 0.2021 0.050 Uiso 1 1 calc R . . C29 C 0.4420(3) 0.3016(3) 0.27388(10) 0.0325(5) Uani 1 1 d . . . C30 C 0.4963(3) 0.4491(3) 0.29406(11) 0.0370(6) Uani 1 1 d . . . H30 H 0.5283 0.4684 0.3321 0.044 Uiso 1 1 calc R . . C31 C 0.5035(4) 0.5670(3) 0.25863(12) 0.0429(6) Uani 1 1 d . . . H31 H 0.5413 0.6665 0.2734 0.052 Uiso 1 1 calc R . . N3 N 0.9303(3) 0.3552(2) 0.03704(8) 0.0350(5) Uani 1 1 d . . . C32 C 0.8189(3) 0.2963(3) -0.00517(11) 0.0416(6) Uani 1 1 d . . . H32 H 0.8571 0.2136 -0.0259 0.050 Uiso 1 1 calc R . . C33 C 0.6506(3) 0.3487(3) -0.02063(11) 0.0397(6) Uani 1 1 d . . . H33 H 0.5761 0.3009 -0.0509 0.048 Uiso 1 1 calc R . . C34 C 0.5903(3) 0.4707(2) 0.00787(9) 0.0287(5) Uani 1 1 d . . . C35 C 0.7068(3) 0.5328(3) 0.05184(10) 0.0402(6) Uani 1 1 d . . . H35 H 0.6729 0.6161 0.0732 0.048 Uiso 1 1 calc R . . C36 C 0.8718(3) 0.4726(3) 0.06432(11) 0.0419(6) Uani 1 1 d . . . H36 H 0.9492 0.5178 0.0944 0.050 Uiso 1 1 calc R . . C37 C 0.9368(4) 0.4858(4) 0.22564(16) 0.0617(9) Uani 1 1 d . . . H37 H 0.9287 0.5652 0.2003 0.074 Uiso 1 1 calc R . . C38 C 0.8682(4) 0.3418(4) 0.20993(13) 0.0534(7) Uani 1 1 d . . . H38 H 0.8144 0.3217 0.1735 0.064 Uiso 1 1 calc R . . C39 C 0.8758(3) 0.2228(3) 0.24687(11) 0.0435(6) Uani 1 1 d . . . C40 C 0.8013(4) 0.0707(3) 0.23187(12) 0.0485(7) Uani 1 1 d . . . H40 H 0.7438 0.0499 0.1958 0.058 Uiso 1 1 calc R . . C41 C 0.8105(4) -0.0422(3) 0.26704(12) 0.0461(7) Uani 1 1 d . . . H41 H 0.7613 -0.1415 0.2551 0.055 Uiso 1 1 calc R . . C42 C 0.8931(3) -0.0178(3) 0.32265(11) 0.0432(6) Uani 1 1 d . . . C43 C 0.9018(4) -0.1337(4) 0.36042(13) 0.0564(8) Uani 1 1 d . . . H43 H 0.8514 -0.2335 0.3499 0.068 Uiso 1 1 calc R . . C44 C 0.9841(4) -0.1031(5) 0.41319(15) 0.0657(9) Uani 1 1 d . . . H44 H 0.9879 -0.1819 0.4388 0.079 Uiso 1 1 calc R . . C45 C 1.0602(4) 0.0402(5) 0.42883(13) 0.0677(10) Uani 1 1 d . . . H45 H 1.1179 0.0578 0.4650 0.081 Uiso 1 1 calc R . . C46 C 1.0549(4) 0.1612(4) 0.39288(12) 0.0534(8) Uani 1 1 d . . . C47 C 1.1318(4) 0.3156(5) 0.40686(14) 0.0687(11) Uani 1 1 d . . . H47 H 1.1929 0.3374 0.4424 0.082 Uiso 1 1 calc R . . C48 C 1.1188(4) 0.4286(4) 0.37094(15) 0.0621(9) Uani 1 1 d . . . H48 H 1.1691 0.5282 0.3820 0.075 Uiso 1 1 calc R . . C49 C 1.0319(4) 0.4018(3) 0.31711(13) 0.0519(8) Uani 1 1 d . . . C50 C 0.9588(3) 0.2523(3) 0.30139(11) 0.0410(6) Uani 1 1 d . . . C51 C 0.9683(3) 0.1311(3) 0.33902(11) 0.0418(6) Uani 1 1 d . . . C59 C 1.0178(4) 0.5167(3) 0.27814(16) 0.0601(9) Uani 1 1 d . . . H59 H 1.0652 0.6176 0.2884 0.072 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.059(3) 0.041(2) 0.053(2) 0.026(2) 0.016(2) 0.0055(19) O3 0.051(2) 0.044(2) 0.060(2) 0.0172(19) 0.0054(19) 0.0158(19) C1 0.042(6) 0.028(4) 0.033(4) 0.001(3) 0.002(4) 0.001(4) C2 0.035(4) 0.031(3) 0.033(3) 0.004(3) 0.005(3) -0.002(3) C3 0.038(6) 0.031(4) 0.033(4) 0.006(3) 0.005(4) -0.005(4) C4 0.034(4) 0.057(5) 0.035(3) -0.005(3) 0.004(3) -0.006(3) C5 0.045(5) 0.043(4) 0.031(4) -0.006(3) 0.006(3) -0.007(4) C6 0.038(4) 0.040(4) 0.040(4) -0.001(3) -0.001(3) 0.004(3) C7 0.034(4) 0.044(4) 0.049(4) -0.003(3) 0.016(3) 0.004(3) O8 0.0291(8) 0.0369(9) 0.0386(9) 0.0065(7) 0.0010(7) 0.0078(7) O10 0.0281(9) 0.0359(9) 0.0569(11) 0.0181(8) 0.0043(8) 0.0069(7) C8 0.0271(11) 0.0295(11) 0.0290(11) -0.0004(9) 0.0016(9) 0.0063(9) C9 0.0241(11) 0.0325(12) 0.0274(11) -0.0005(9) 0.0025(9) 0.0018(9) C10 0.0282(11) 0.0285(11) 0.0351(12) 0.0038(10) 0.0023(9) 0.0034(10) C11 0.0257(12) 0.0380(13) 0.0514(15) 0.0066(12) 0.0077(11) 0.0094(10) C12 0.0308(13) 0.0436(15) 0.0553(16) 0.0094(12) 0.0165(11) 0.0048(11) C13 0.0380(13) 0.0358(13) 0.0401(13) 0.0096(11) 0.0122(11) 0.0055(11) C14 0.0256(11) 0.0418(14) 0.0438(14) 0.0103(11) 0.0022(10) 0.0025(10) N1 0.0473(14) 0.0405(13) 0.0731(17) 0.0210(12) 0.0182(13) 0.0056(11) N2 0.0406(12) 0.0425(13) 0.0551(14) 0.0154(11) 0.0073(10) 0.0110(10) C22 0.0422(15) 0.0315(14) 0.076(2) 0.0044(14) 0.0179(15) -0.0030(12) C23 0.0383(14) 0.0318(13) 0.0544(16) -0.0019(12) 0.0099(12) -0.0029(11) C24 0.0300(12) 0.0282(12) 0.0440(14) 0.0003(10) 0.0096(10) 0.0023(10) C25 0.0496(16) 0.0341(13) 0.0472(15) 0.0050(12) 0.0016(12) 0.0008(12) C26 0.0546(18) 0.0518(17) 0.0553(18) 0.0147(14) 0.0053(14) 0.0065(15) C27 0.0496(16) 0.0492(16) 0.0446(16) 0.0093(13) -0.0023(12) 0.0090(13) C28 0.0436(14) 0.0354(13) 0.0438(14) -0.0004(11) -0.0025(12) 0.0047(12) C29 0.0277(11) 0.0284(12) 0.0419(13) 0.0012(10) 0.0054(10) 0.0032(10) C30 0.0380(13) 0.0304(12) 0.0426(14) 0.0008(10) 0.0056(11) 0.0005(10) C31 0.0396(14) 0.0276(12) 0.0624(18) 0.0046(12) 0.0090(12) 0.0010(11) N3 0.0331(11) 0.0334(11) 0.0395(11) 0.0090(9) 0.0045(9) 0.0065(9) C32 0.0381(14) 0.0361(13) 0.0504(15) -0.0062(12) 0.0014(12) 0.0130(11) C33 0.0363(13) 0.0375(13) 0.0441(14) -0.0106(11) -0.0022(11) 0.0126(11) C34 0.0289(12) 0.0270(11) 0.0314(11) 0.0067(9) 0.0057(9) 0.0045(9) C35 0.0345(13) 0.0442(14) 0.0414(14) -0.0080(12) 0.0006(11) 0.0114(11) C36 0.0341(13) 0.0499(15) 0.0403(14) -0.0023(12) -0.0020(11) 0.0071(12) C37 0.0432(17) 0.0554(19) 0.089(2) 0.0070(18) 0.0182(16) -0.0003(15) C38 0.0424(16) 0.0610(19) 0.0582(18) 0.0051(15) 0.0129(13) -0.0004(14) C39 0.0314(13) 0.0483(16) 0.0514(16) -0.0075(13) 0.0132(11) -0.0035(12) C40 0.0427(15) 0.0556(17) 0.0457(15) -0.0140(14) 0.0079(12) -0.0079(13) C41 0.0407(14) 0.0436(15) 0.0529(16) -0.0152(13) 0.0118(12) -0.0129(12) C42 0.0313(13) 0.0477(15) 0.0525(16) -0.0018(13) 0.0162(11) -0.0015(12) C43 0.0481(17) 0.0602(19) 0.065(2) 0.0060(16) 0.0231(15) 0.0028(15) C44 0.0510(19) 0.087(3) 0.065(2) 0.0199(19) 0.0235(16) 0.0182(19) C45 0.0481(18) 0.112(3) 0.0448(18) -0.0046(19) 0.0076(14) 0.020(2) C46 0.0375(15) 0.076(2) 0.0470(16) -0.0124(16) 0.0077(12) 0.0118(15) C47 0.0403(16) 0.100(3) 0.061(2) -0.044(2) -0.0043(14) 0.0071(18) C48 0.0439(17) 0.0577(19) 0.081(2) -0.0274(18) -0.0001(16) 0.0008(15) C49 0.0291(13) 0.0500(17) 0.075(2) -0.0198(15) 0.0067(13) -0.0012(12) C50 0.0240(12) 0.0449(15) 0.0544(16) -0.0120(13) 0.0105(11) -0.0020(11) C51 0.0275(12) 0.0526(16) 0.0457(15) -0.0105(13) 0.0091(11) 0.0017(11) C59 0.0375(15) 0.0401(16) 0.105(3) -0.0076(17) 0.0202(17) 0.0004(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 0.989(8) 2_666 ? O1 C1 1.353(10) . ? O1 C3 1.736(10) 2_666 ? O1 H1 1.18(7) . ? O3 C6 1.268(9) 2_666 ? O3 C3 1.379(9) . ? O3 C1 1.920(10) 2_666 ? C1 C3 0.689(8) 2_666 ? C1 C4 0.758(8) 2_666 ? C1 C6 1.408(10) . ? C1 C2 1.408(10) . ? C1 C2 1.783(12) 2_666 ? C1 C5 1.788(14) 2_666 ? C1 O3 1.920(10) 2_666 ? C2 C5 0.731(8) 2_666 ? C2 C6 1.056(9) 2_666 ? C2 C4 1.374(11) 2_666 ? C2 C3 1.404(10) . ? C2 C7 1.517(8) . ? C2 C1 1.783(12) 2_666 ? C2 C3 1.922(12) 2_666 ? C3 C1 0.689(8) 2_666 ? C3 C6 0.751(8) 2_666 ? C3 C4 1.408(9) . ? C3 O1 1.736(10) 2_666 ? C3 C2 1.922(12) 2_666 ? C3 C5 1.981(12) 2_666 ? C4 C1 0.758(8) 2_666 ? C4 O1 0.989(8) 2_666 ? C4 C2 1.374(11) 2_666 ? C4 C5 1.412(11) . ? C4 C7 2.021(11) 2_666 ? C5 C2 0.731(8) 2_666 ? C5 C7 0.811(9) 2_666 ? C5 C6 1.403(10) . ? C5 C1 1.788(14) 2_666 ? C5 C3 1.981(12) 2_666 ? C6 C3 0.751(8) 2_666 ? C6 C2 1.056(9) 2_666 ? C6 O3 1.268(9) 2_666 ? C6 C7 1.866(11) 2_666 ? C7 C5 0.811(9) 2_666 ? C7 C6 1.866(11) 2_666 ? C7 C4 2.021(11) 2_666 ? C7 H7B 0.90(7) . ? C7 H7A 0.94(8) . ? C7 H7C 0.84(7) . ? O8 C8 1.372(3) . ? O8 H8 1.06(4) . ? O10 C10 1.367(3) . ? O10 H10 1.01(3) . ? C8 C13 1.396(3) . ? C8 C9 1.398(3) . ? C9 C10 1.401(3) . ? C9 C14 1.502(3) . ? C10 C11 1.395(3) . ? C11 C12 1.381(3) . ? C11 H11 0.9500 . ? C12 C13 1.390(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? N1 C22 1.330(4) . ? N1 C26 1.336(4) . ? N2 C27 1.336(4) . ? N2 C31 1.340(4) . ? C22 C23 1.382(4) . ? C22 H22 0.9500 . ? C23 C24 1.393(3) . ? C23 H23 0.9500 . ? C24 C25 1.392(4) . ? C24 C29 1.488(3) . ? C25 C26 1.377(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.385(4) . ? C27 H27 0.9500 . ? C28 C29 1.389(4) . ? C28 H28 0.9500 . ? C29 C30 1.393(3) . ? C30 C31 1.376(4) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? N3 C32 1.329(3) . ? N3 C36 1.334(3) . ? C32 C33 1.382(3) . ? C32 H32 0.9500 . ? C33 C34 1.387(3) . ? C33 H33 0.9500 . ? C34 C35 1.389(3) . ? C34 C34 1.488(4) 2_665 ? C35 C36 1.377(4) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 C38 1.363(4) . ? C37 C59 1.378(5) . ? C37 H37 0.9500 . ? C38 C39 1.405(4) . ? C38 H38 0.9500 . ? C39 C50 1.425(4) . ? C39 C40 1.437(4) . ? C40 C41 1.336(4) . ? C40 H40 0.9500 . ? C41 C42 1.443(4) . ? C41 H41 0.9500 . ? C42 C43 1.398(4) . ? C42 C51 1.421(4) . ? C43 C44 1.387(5) . ? C43 H43 0.9500 . ? C44 C45 1.376(5) . ? C44 H44 0.9500 . ? C45 C46 1.402(5) . ? C45 H45 0.9500 . ? C46 C51 1.420(4) . ? C46 C47 1.457(5) . ? C47 C48 1.349(5) . ? C47 H47 0.9500 . ? C48 C49 1.417(4) . ? C48 H48 0.9500 . ? C49 C59 1.413(5) . ? C49 C50 1.417(4) . ? C50 C51 1.431(4) . ? C59 H59 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 C4 O1 C1 33.4(4) 2_666 . ? C4 O1 C3 54.2(5) 2_666 2_666 ? C1 O1 C3 21.6(4) . 2_666 ? C4 O1 H1 134(3) 2_666 . ? C1 O1 H1 101(3) . . ? C3 O1 H1 80(3) 2_666 . ? C6 O3 C3 32.6(4) 2_666 . ? C6 O3 C1 47.1(4) 2_666 2_666 ? C3 O3 C1 15.1(4) . 2_666 ? C3 C1 C4 153.3(17) 2_666 2_666 ? C3 C1 O1 112.3(12) 2_666 . ? C4 C1 O1 46.0(8) 2_666 . ? C3 C1 C6 12.7(9) 2_666 . ? C4 C1 C6 166.0(12) 2_666 . ? O1 C1 C6 122.9(8) . . ? C3 C1 C2 129.5(14) 2_666 . ? C4 C1 C2 71.7(10) 2_666 . ? O1 C1 C2 117.2(9) . . ? C6 C1 C2 119.8(8) . . ? C3 C1 C2 46.9(10) 2_666 2_666 ? C4 C1 C2 153.7(10) 2_666 2_666 ? O1 C1 C2 159.1(7) . 2_666 ? C6 C1 C2 36.3(5) . 2_666 ? C2 C1 C2 83.5(6) . 2_666 ? C3 C1 C5 151.0(13) 2_666 2_666 ? C4 C1 C5 49.1(9) 2_666 2_666 ? O1 C1 C5 94.6(8) . 2_666 ? C6 C1 C5 142.4(7) . 2_666 ? C2 C1 C5 22.7(3) . 2_666 ? C2 C1 C5 106.1(6) 2_666 2_666 ? C3 C1 O3 31.4(9) 2_666 2_666 ? C4 C1 O3 126.4(10) 2_666 2_666 ? O1 C1 O3 81.6(4) . 2_666 ? C6 C1 O3 41.3(5) . 2_666 ? C2 C1 O3 160.9(8) . 2_666 ? C2 C1 O3 77.5(5) 2_666 2_666 ? C5 C1 O3 174.0(6) 2_666 2_666 ? C5 C2 C6 101.9(11) 2_666 2_666 ? C5 C2 C4 77.7(9) 2_666 2_666 ? C6 C2 C4 174.7(8) 2_666 2_666 ? C5 C2 C3 133.6(11) 2_666 . ? C6 C2 C3 31.7(4) 2_666 . ? C4 C2 C3 148.5(7) 2_666 . ? C5 C2 C1 109.2(11) 2_666 . ? C6 C2 C1 148.6(8) 2_666 . ? C4 C2 C1 31.6(4) 2_666 . ? C3 C2 C1 117.1(6) . . ? C5 C2 C7 10.9(7) 2_666 . ? C6 C2 C7 91.2(7) 2_666 . ? C4 C2 C7 88.5(6) 2_666 . ? C3 C2 C7 122.8(7) . . ? C1 C2 C7 120.1(7) . . ? C5 C2 C1 153.7(10) 2_666 2_666 ? C6 C2 C1 52.1(5) 2_666 2_666 ? C4 C2 C1 127.6(6) 2_666 2_666 ? C3 C2 C1 21.0(4) . 2_666 ? C1 C2 C1 96.5(6) . 2_666 ? C7 C2 C1 143.1(6) . 2_666 ? C5 C2 C3 124.6(10) 2_666 2_666 ? C6 C2 C3 132.7(7) 2_666 2_666 ? C4 C2 C3 47.1(4) 2_666 2_666 ? C3 C2 C3 101.5(5) . 2_666 ? C1 C2 C3 16.1(5) . 2_666 ? C7 C2 C3 135.5(6) . 2_666 ? C1 C2 C3 80.6(4) 2_666 2_666 ? C1 C3 C6 155.6(17) 2_666 2_666 ? C1 C3 O3 133.5(13) 2_666 . ? C6 C3 O3 65.5(10) 2_666 . ? C1 C3 C2 112.2(13) 2_666 . ? C6 C3 C2 47.6(8) 2_666 . ? O3 C3 C2 113.0(8) . . ? C1 C3 C4 14.0(9) 2_666 . ? C6 C3 C4 169.6(12) 2_666 . ? O3 C3 C4 122.8(7) . . ? C2 C3 C4 124.1(8) . . ? C1 C3 O1 46.1(10) 2_666 2_666 ? C6 C3 O1 152.1(11) 2_666 2_666 ? O3 C3 O1 88.1(4) . 2_666 ? C2 C3 O1 158.3(8) . 2_666 ? C4 C3 O1 34.7(4) . 2_666 ? C1 C3 C2 34.4(10) 2_666 2_666 ? C6 C3 C2 125.6(10) 2_666 2_666 ? O3 C3 C2 167.9(7) . 2_666 ? C2 C3 C2 78.5(5) . 2_666 ? C4 C3 C2 45.6(5) . 2_666 ? O1 C3 C2 80.1(6) 2_666 2_666 ? C1 C3 C5 127.2(13) 2_666 2_666 ? C6 C3 C5 32.2(8) 2_666 2_666 ? O3 C3 C5 97.5(6) . 2_666 ? C2 C3 C5 15.5(4) . 2_666 ? C4 C3 C5 139.5(7) . 2_666 ? O1 C3 C5 171.8(6) 2_666 2_666 ? C2 C3 C5 94.0(5) 2_666 2_666 ? C1 C4 O1 100.6(10) 2_666 2_666 ? C1 C4 C2 76.7(10) 2_666 2_666 ? O1 C4 C2 171.4(8) 2_666 2_666 ? C1 C4 C3 12.7(8) 2_666 . ? O1 C4 C3 91.0(7) 2_666 . ? C2 C4 C3 87.4(7) 2_666 . ? C1 C4 C5 107.0(11) 2_666 . ? O1 C4 C5 150.7(9) 2_666 . ? C2 C4 C5 30.4(3) 2_666 . ? C3 C4 C5 117.7(8) . . ? C1 C4 C7 125.2(10) 2_666 2_666 ? O1 C4 C7 132.9(8) 2_666 2_666 ? C2 C4 C7 48.6(4) 2_666 2_666 ? C3 C4 C7 135.9(7) . 2_666 ? C5 C4 C7 18.3(4) . 2_666 ? C2 C5 C7 159.4(13) 2_666 2_666 ? C2 C5 C6 47.4(8) 2_666 . ? C7 C5 C6 112.1(9) 2_666 . ? C2 C5 C4 71.9(10) 2_666 . ? C7 C5 C4 128.7(10) 2_666 . ? C6 C5 C4 119.2(9) . . ? C2 C5 C1 48.1(9) 2_666 2_666 ? C7 C5 C1 152.5(9) 2_666 2_666 ? C6 C5 C1 95.4(7) . 2_666 ? C4 C5 C1 23.9(4) . 2_666 ? C2 C5 C3 30.9(7) 2_666 2_666 ? C7 C5 C3 128.6(8) 2_666 2_666 ? C6 C5 C3 16.6(4) . 2_666 ? C4 C5 C3 102.8(7) . 2_666 ? C1 C5 C3 78.9(5) 2_666 2_666 ? C3 C6 C2 100.6(11) 2_666 2_666 ? C3 C6 O3 81.9(10) 2_666 2_666 ? C2 C6 O3 174.3(8) 2_666 2_666 ? C3 C6 C5 131.3(11) 2_666 . ? C2 C6 C5 30.6(5) 2_666 . ? O3 C6 C5 146.4(8) 2_666 . ? C3 C6 C1 11.7(8) 2_666 . ? C2 C6 C1 91.5(8) 2_666 . ? O3 C6 C1 91.6(7) 2_666 . ? C5 C6 C1 122.0(8) . . ? C3 C6 C7 154.8(10) 2_666 2_666 ? C2 C6 C7 54.4(5) 2_666 2_666 ? O3 C6 C7 122.7(6) 2_666 2_666 ? C5 C6 C7 23.7(4) . 2_666 ? C1 C6 C7 145.7(7) . 2_666 ? C5 C7 C2 9.8(6) 2_666 . ? C5 C7 C6 44.2(6) 2_666 2_666 ? C2 C7 C6 34.5(4) . 2_666 ? C5 C7 C4 33.1(7) 2_666 2_666 ? C2 C7 C4 42.8(4) . 2_666 ? C6 C7 C4 77.2(4) 2_666 2_666 ? C5 C7 H7B 98(4) 2_666 . ? C2 C7 H7B 107(4) . . ? C6 C7 H7B 140(4) 2_666 . ? C4 C7 H7B 67(4) 2_666 . ? C5 C7 H7A 111(5) 2_666 . ? C2 C7 H7A 113(5) . . ? C6 C7 H7A 111(5) 2_666 . ? C4 C7 H7A 101(5) 2_666 . ? H7B C7 H7A 93(6) . . ? C5 C7 H7C 116(5) 2_666 . ? C2 C7 H7C 110(5) . . ? C6 C7 H7C 89(5) 2_666 . ? C4 C7 H7C 131(5) 2_666 . ? H7B C7 H7C 101(6) . . ? H7A C7 H7C 128(7) . . ? C8 O8 H8 107.9(18) . . ? C10 O10 H10 109.2(19) . . ? O8 C8 C13 120.9(2) . . ? O8 C8 C9 117.8(2) . . ? C13 C8 C9 121.3(2) . . ? C8 C9 C10 118.2(2) . . ? C8 C9 C14 121.74(19) . . ? C10 C9 C14 120.1(2) . . ? O10 C10 C11 122.1(2) . . ? O10 C10 C9 116.9(2) . . ? C11 C10 C9 121.1(2) . . ? C12 C11 C10 119.3(2) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C13 121.3(2) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C8 118.8(2) . . ? C12 C13 H13 120.6 . . ? C8 C13 H13 120.6 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C22 N1 C26 115.8(2) . . ? C27 N2 C31 116.5(2) . . ? N1 C22 C23 124.6(3) . . ? N1 C22 H22 117.7 . . ? C23 C22 H22 117.7 . . ? C22 C23 C24 119.2(3) . . ? C22 C23 H23 120.4 . . ? C24 C23 H23 120.4 . . ? C25 C24 C23 116.5(2) . . ? C25 C24 C29 121.0(2) . . ? C23 C24 C29 122.5(2) . . ? C26 C25 C24 119.9(3) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? N1 C26 C25 124.0(3) . . ? N1 C26 H26 118.0 . . ? C25 C26 H26 118.0 . . ? N2 C27 C28 123.5(3) . . ? N2 C27 H27 118.3 . . ? C28 C27 H27 118.3 . . ? C27 C28 C29 119.8(2) . . ? C27 C28 H28 120.1 . . ? C29 C28 H28 120.1 . . ? C28 C29 C30 116.6(2) . . ? C28 C29 C24 121.7(2) . . ? C30 C29 C24 121.7(2) . . ? C31 C30 C29 119.7(2) . . ? C31 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? N2 C31 C30 123.8(2) . . ? N2 C31 H31 118.1 . . ? C30 C31 H31 118.1 . . ? C32 N3 C36 115.9(2) . . ? N3 C32 C33 123.7(2) . . ? N3 C32 H32 118.1 . . ? C33 C32 H32 118.1 . . ? C32 C33 C34 120.2(2) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C33 C34 C35 116.2(2) . . ? C33 C34 C34 121.3(3) . 2_665 ? C35 C34 C34 122.5(3) . 2_665 ? C36 C35 C34 119.5(2) . . ? C36 C35 H35 120.2 . . ? C34 C35 H35 120.2 . . ? N3 C36 C35 124.5(2) . . ? N3 C36 H36 117.8 . . ? C35 C36 H36 117.8 . . ? C38 C37 C59 120.3(3) . . ? C38 C37 H37 119.8 . . ? C59 C37 H37 119.8 . . ? C37 C38 C39 121.0(3) . . ? C37 C38 H38 119.5 . . ? C39 C38 H38 119.5 . . ? C38 C39 C50 119.6(3) . . ? C38 C39 C40 122.3(3) . . ? C50 C39 C40 118.1(3) . . ? C41 C40 C39 122.0(3) . . ? C41 C40 H40 119.0 . . ? C39 C40 H40 119.0 . . ? C40 C41 C42 121.9(3) . . ? C40 C41 H41 119.1 . . ? C42 C41 H41 119.1 . . ? C43 C42 C51 119.3(3) . . ? C43 C42 C41 122.9(3) . . ? C51 C42 C41 117.8(3) . . ? C44 C43 C42 120.1(3) . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? C45 C44 C43 120.7(3) . . ? C45 C44 H44 119.7 . . ? C43 C44 H44 119.7 . . ? C44 C45 C46 121.8(3) . . ? C44 C45 H45 119.1 . . ? C46 C45 H45 119.1 . . ? C45 C46 C51 117.7(3) . . ? C45 C46 C47 124.6(3) . . ? C51 C46 C47 117.6(3) . . ? C48 C47 C46 122.1(3) . . ? C48 C47 H47 119.0 . . ? C46 C47 H47 119.0 . . ? C47 C48 C49 121.4(3) . . ? C47 C48 H48 119.3 . . ? C49 C48 H48 119.3 . . ? C59 C49 C50 118.5(3) . . ? C59 C49 C48 123.0(3) . . ? C50 C49 C48 118.4(3) . . ? C49 C50 C39 119.0(3) . . ? C49 C50 C51 121.2(3) . . ? C39 C50 C51 119.8(2) . . ? C46 C51 C42 120.3(3) . . ? C46 C51 C50 119.2(3) . . ? C42 C51 C50 120.4(2) . . ? C37 C59 C49 121.6(3) . . ? C37 C59 H59 119.2 . . ? C49 C59 H59 119.2 . . ? 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 C4 O1 C1 C3 161.2(18) 2_666 . . 2_666 ? C3 O1 C1 C4 -161.2(18) 2_666 . . 2_666 ? C4 O1 C1 C6 169.2(14) 2_666 . . . ? C3 O1 C1 C6 8.0(9) 2_666 . . . ? C4 O1 C1 C2 -8.9(8) 2_666 . . . ? C3 O1 C1 C2 -170.1(18) 2_666 . . . ? C4 O1 C1 C2 164(2) 2_666 . . 2_666 ? C3 O1 C1 C2 3.3(11) 2_666 . . 2_666 ? C4 O1 C1 C5 -7.6(8) 2_666 . . 2_666 ? C3 O1 C1 C5 -168.8(15) 2_666 . . 2_666 ? C4 O1 C1 O3 167.8(10) 2_666 . . 2_666 ? C3 O1 C1 O3 6.6(11) 2_666 . . 2_666 ? C3 C1 C2 C5 -164.7(17) 2_666 . . 2_666 ? C4 C1 C2 C5 -3.3(12) 2_666 . . 2_666 ? O1 C1 C2 C5 3.4(12) . . . 2_666 ? C6 C1 C2 C5 -174.7(10) . . . 2_666 ? C2 C1 C2 C5 -174.2(11) 2_666 . . 2_666 ? O3 C1 C2 C5 -166.7(17) 2_666 . . 2_666 ? C3 C1 C2 C6 8(3) 2_666 . . 2_666 ? C4 C1 C2 C6 169.8(15) 2_666 . . 2_666 ? O1 C1 C2 C6 176.5(12) . . . 2_666 ? C6 C1 C2 C6 -2(2) . . . 2_666 ? C2 C1 C2 C6 -1.1(14) 2_666 . . 2_666 ? C5 C1 C2 C6 173(2) 2_666 . . 2_666 ? O3 C1 C2 C6 6(3) 2_666 . . 2_666 ? C3 C1 C2 C4 -161(2) 2_666 . . 2_666 ? O1 C1 C2 C4 6.7(6) . . . 2_666 ? C6 C1 C2 C4 -171.4(13) . . . 2_666 ? C2 C1 C2 C4 -170.9(10) 2_666 . . 2_666 ? C5 C1 C2 C4 3.3(12) 2_666 . . 2_666 ? O3 C1 C2 C4 -163(2) 2_666 . . 2_666 ? C3 C1 C2 C3 14(2) 2_666 . . . ? C4 C1 C2 C3 174.9(9) 2_666 . . . ? O1 C1 C2 C3 -178.3(6) . . . . ? C6 C1 C2 C3 3.5(11) . . . . ? C2 C1 C2 C3 4.0(6) 2_666 . . . ? C5 C1 C2 C3 178.2(14) 2_666 . . . ? O3 C1 C2 C3 12(2) 2_666 . . . ? C3 C1 C2 C7 -165.4(15) 2_666 . . . ? C4 C1 C2 C7 -4.1(10) 2_666 . . . ? O1 C1 C2 C7 2.7(10) . . . . ? C6 C1 C2 C7 -175.5(7) . . . . ? C2 C1 C2 C7 -175.0(8) 2_666 . . . ? C5 C1 C2 C7 -0.8(7) 2_666 . . . ? O3 C1 C2 C7 -167.4(16) 2_666 . . . ? C3 C1 C2 C1 9.5(15) 2_666 . . 2_666 ? C4 C1 C2 C1 170.9(10) 2_666 . . 2_666 ? O1 C1 C2 C1 177.6(8) . . . 2_666 ? C6 C1 C2 C1 -0.5(6) . . . 2_666 ? C2 C1 C2 C1 0.000(1) 2_666 . . 2_666 ? C5 C1 C2 C1 174.2(11) 2_666 . . 2_666 ? O3 C1 C2 C1 7.5(18) 2_666 . . 2_666 ? C4 C1 C2 C3 161(2) 2_666 . . 2_666 ? O1 C1 C2 C3 168(2) . . . 2_666 ? C6 C1 C2 C3 -10.0(12) . . . 2_666 ? C2 C1 C2 C3 -9.5(15) 2_666 . . 2_666 ? C5 C1 C2 C3 164.7(17) 2_666 . . 2_666 ? O3 C1 C2 C3 -2.0(11) 2_666 . . 2_666 ? C6 O3 C3 C1 -161(2) 2_666 . . 2_666 ? C1 O3 C3 C6 161(2) 2_666 . . 2_666 ? C6 O3 C3 C2 4.2(6) 2_666 . . . ? C1 O3 C3 C2 166(2) 2_666 . . . ? C6 O3 C3 C4 -172.9(14) 2_666 . . . ? C1 O3 C3 C4 -11.5(13) 2_666 . . . ? C6 O3 C3 O1 -170.6(10) 2_666 . . 2_666 ? C1 O3 C3 O1 -9.1(15) 2_666 . . 2_666 ? C6 O3 C3 C2 -158(3) 2_666 . . 2_666 ? C1 O3 C3 C2 3.4(19) 2_666 . . 2_666 ? C6 O3 C3 C5 3.5(7) 2_666 . . 2_666 ? C1 O3 C3 C5 165(2) 2_666 . . 2_666 ? C5 C2 C3 C1 166.4(16) 2_666 . . 2_666 ? C6 C2 C3 C1 163.6(18) 2_666 . . 2_666 ? C4 C2 C3 C1 -6(2) 2_666 . . 2_666 ? C1 C2 C3 C1 -11.3(18) . . . 2_666 ? C7 C2 C3 C1 167.7(12) . . . 2_666 ? C3 C2 C3 C1 -7.5(12) 2_666 . . 2_666 ? C5 C2 C3 C6 2.8(16) 2_666 . . 2_666 ? C4 C2 C3 C6 -169.8(15) 2_666 . . 2_666 ? C1 C2 C3 C6 -174.9(11) . . . 2_666 ? C7 C2 C3 C6 4.1(11) . . . 2_666 ? C1 C2 C3 C6 -163.6(18) 2_666 . . 2_666 ? C3 C2 C3 C6 -171.1(11) 2_666 . . 2_666 ? C5 C2 C3 O3 -2.4(16) 2_666 . . . ? C6 C2 C3 O3 -5.2(8) 2_666 . . . ? C4 C2 C3 O3 -175.0(10) 2_666 . . . ? C1 C2 C3 O3 179.9(5) . . . . ? C7 C2 C3 O3 -1.1(10) . . . . ? C1 C2 C3 O3 -168.8(17) 2_666 . . . ? C3 C2 C3 O3 -176.3(7) 2_666 . . . ? C5 C2 C3 C4 174.7(13) 2_666 . . . ? C6 C2 C3 C4 171.9(15) 2_666 . . . ? C4 C2 C3 C4 2(2) 2_666 . . . ? C1 C2 C3 C4 -3.0(12) . . . . ? C7 C2 C3 C4 176.0(7) . . . . ? C1 C2 C3 C4 8.3(9) 2_666 . . . ? C3 C2 C3 C4 0.8(7) 2_666 . . . ? C5 C2 C3 O1 163.3(15) 2_666 . . 2_666 ? C6 C2 C3 O1 161(2) 2_666 . . 2_666 ? C4 C2 C3 O1 -9(3) 2_666 . . 2_666 ? C1 C2 C3 O1 -14(2) . . . 2_666 ? C7 C2 C3 O1 164.6(14) . . . 2_666 ? C1 C2 C3 O1 -3.1(11) 2_666 . . 2_666 ? C3 C2 C3 O1 -10.6(17) 2_666 . . 2_666 ? C5 C2 C3 C2 173.9(15) 2_666 . . 2_666 ? C6 C2 C3 C2 171.1(11) 2_666 . . 2_666 ? C4 C2 C3 C2 1.3(12) 2_666 . . 2_666 ? C1 C2 C3 C2 -3.8(6) . . . 2_666 ? C7 C2 C3 C2 175.2(8) . . . 2_666 ? C1 C2 C3 C2 7.5(12) 2_666 . . 2_666 ? C3 C2 C3 C2 0.0 2_666 . . 2_666 ? C6 C2 C3 C5 -2.8(16) 2_666 . . 2_666 ? C4 C2 C3 C5 -173(2) 2_666 . . 2_666 ? C1 C2 C3 C5 -177.7(19) . . . 2_666 ? C7 C2 C3 C5 1.3(10) . . . 2_666 ? C1 C2 C3 C5 -166.4(16) 2_666 . . 2_666 ? C3 C2 C3 C5 -173.9(15) 2_666 . . 2_666 ? C6 C3 C4 C1 2(6) 2_666 . . 2_666 ? O3 C3 C4 C1 143(4) . . . 2_666 ? C2 C3 C4 C1 -33(3) . . . 2_666 ? O1 C3 C4 C1 139(3) 2_666 . . 2_666 ? C2 C3 C4 C1 -32(3) 2_666 . . 2_666 ? C5 C3 C4 C1 -31(3) 2_666 . . 2_666 ? C1 C3 C4 O1 -139(3) 2_666 . . 2_666 ? C6 C3 C4 O1 -137(6) 2_666 . . 2_666 ? O3 C3 C4 O1 4.1(10) . . . 2_666 ? C2 C3 C4 O1 -172.6(7) . . . 2_666 ? C2 C3 C4 O1 -171.5(7) 2_666 . . 2_666 ? C5 C3 C4 O1 -170.4(8) 2_666 . . 2_666 ? C1 C3 C4 C2 32(3) 2_666 . . 2_666 ? C6 C3 C4 C2 34(6) 2_666 . . 2_666 ? O3 C3 C4 C2 175.7(7) . . . 2_666 ? C2 C3 C4 C2 -1.1(10) . . . 2_666 ? O1 C3 C4 C2 171.5(7) 2_666 . . 2_666 ? C5 C3 C4 C2 1.1(11) 2_666 . . 2_666 ? C1 C3 C4 C5 34(3) 2_666 . . . ? C6 C3 C4 C5 36(7) 2_666 . . . ? O3 C3 C4 C5 177.8(6) . . . . ? C2 C3 C4 C5 1.1(12) . . . . ? O1 C3 C4 C5 173.7(10) 2_666 . . . ? C2 C3 C4 C5 2.1(5) 2_666 . . . ? C5 C3 C4 C5 3.2(14) 2_666 . . . ? C1 C3 C4 C7 36(4) 2_666 . . 2_666 ? C6 C3 C4 C7 38(7) 2_666 . . 2_666 ? O3 C3 C4 C7 179.4(5) . . . 2_666 ? C2 C3 C4 C7 2.6(14) . . . 2_666 ? O1 C3 C4 C7 175.2(11) 2_666 . . 2_666 ? C2 C3 C4 C7 3.7(6) 2_666 . . 2_666 ? C5 C3 C4 C7 4.8(16) 2_666 . . 2_666 ? C1 C4 C5 C2 3.2(12) 2_666 . . 2_666 ? O1 C4 C5 C2 162.8(16) 2_666 . . 2_666 ? C3 C4 C5 C2 -4.2(10) . . . 2_666 ? C7 C4 C5 C2 179.2(16) 2_666 . . 2_666 ? C1 C4 C5 C7 -175.9(12) 2_666 . . 2_666 ? O1 C4 C5 C7 -16(2) 2_666 . . 2_666 ? C2 C4 C5 C7 -179.2(16) 2_666 . . 2_666 ? C3 C4 C5 C7 176.6(10) . . . 2_666 ? C1 C4 C5 C6 7.8(11) 2_666 . . . ? O1 C4 C5 C6 167.4(13) 2_666 . . . ? C2 C4 C5 C6 4.6(7) 2_666 . . . ? C3 C4 C5 C6 0.4(10) . . . . ? C7 C4 C5 C6 -176.2(14) 2_666 . . . ? O1 C4 C5 C1 160(2) 2_666 . . 2_666 ? C2 C4 C5 C1 -3.2(12) 2_666 . . 2_666 ? C3 C4 C5 C1 -7.5(8) . . . 2_666 ? C7 C4 C5 C1 175.9(12) 2_666 . . 2_666 ? C1 C4 C5 C3 5.3(10) 2_666 . . 2_666 ? O1 C4 C5 C3 164.9(13) 2_666 . . 2_666 ? C2 C4 C5 C3 2.1(7) 2_666 . . 2_666 ? C3 C4 C5 C3 -2.2(9) . . . 2_666 ? C7 C4 C5 C3 -178.8(13) 2_666 . . 2_666 ? C2 C5 C6 C3 -2.7(16) 2_666 . . 2_666 ? C7 C5 C6 C3 174.5(14) 2_666 . . 2_666 ? C4 C5 C6 C3 -8.6(16) . . . 2_666 ? C1 C5 C6 C3 -5.4(14) 2_666 . . 2_666 ? C7 C5 C6 C2 177.2(15) 2_666 . . 2_666 ? C4 C5 C6 C2 -5.9(9) . . . 2_666 ? C1 C5 C6 C2 -2.7(9) 2_666 . . 2_666 ? C3 C5 C6 C2 2.7(16) 2_666 . . 2_666 ? C2 C5 C6 O3 -170.8(14) 2_666 . . 2_666 ? C7 C5 C6 O3 6.4(16) 2_666 . . 2_666 ? C4 C5 C6 O3 -176.7(9) . . . 2_666 ? C1 C5 C6 O3 -173.6(10) 2_666 . . 2_666 ? C3 C5 C6 O3 -168(2) 2_666 . . 2_666 ? C2 C5 C6 C1 6.2(11) 2_666 . . . ? C7 C5 C6 C1 -176.5(9) 2_666 . . . ? C4 C5 C6 C1 0.3(11) . . . . ? C1 C5 C6 C1 3.5(10) 2_666 . . . ? C3 C5 C6 C1 8.9(11) 2_666 . . . ? C2 C5 C6 C7 -177.2(14) 2_666 . . 2_666 ? C4 C5 C6 C7 176.8(12) . . . 2_666 ? C1 C5 C6 C7 -180.0(10) 2_666 . . 2_666 ? C3 C5 C6 C7 -174.5(14) 2_666 . . 2_666 ? C4 C1 C6 C3 -2(5) 2_666 . . 2_666 ? O1 C1 C6 C3 -36(4) . . . 2_666 ? C2 C1 C6 C3 142(4) . . . 2_666 ? C2 C1 C6 C3 142(4) 2_666 . . 2_666 ? C5 C1 C6 C3 139(4) 2_666 . . 2_666 ? O3 C1 C6 C3 -34(4) 2_666 . . 2_666 ? C3 C1 C6 C2 -142(4) 2_666 . . 2_666 ? C4 C1 C6 C2 -143(5) 2_666 . . 2_666 ? O1 C1 C6 C2 -177.2(7) . . . 2_666 ? C2 C1 C6 C2 0.8(11) . . . 2_666 ? C5 C1 C6 C2 -2.5(13) 2_666 . . 2_666 ? O3 C1 C6 C2 -175.2(8) 2_666 . . 2_666 ? C3 C1 C6 O3 34(4) 2_666 . . 2_666 ? C4 C1 C6 O3 32(5) 2_666 . . 2_666 ? O1 C1 C6 O3 -2.0(9) . . . 2_666 ? C2 C1 C6 O3 176.0(6) . . . 2_666 ? C2 C1 C6 O3 175.2(8) 2_666 . . 2_666 ? C5 C1 C6 O3 172.7(9) 2_666 . . 2_666 ? C3 C1 C6 C5 -145(4) 2_666 . . . ? C4 C1 C6 C5 -146(4) 2_666 . . . ? O1 C1 C6 C5 179.6(6) . . . . ? C2 C1 C6 C5 -2.3(11) . . . . ? C2 C1 C6 C5 -3.2(6) 2_666 . . . ? C5 C1 C6 C5 -5.7(16) 2_666 . . . ? O3 C1 C6 C5 -178.4(9) 2_666 . . . ? C3 C1 C6 C7 -147(4) 2_666 . . 2_666 ? C4 C1 C6 C7 -149(4) 2_666 . . 2_666 ? O1 C1 C6 C7 177.2(7) . . . 2_666 ? C2 C1 C6 C7 -4.8(16) . . . 2_666 ? C2 C1 C6 C7 -5.6(9) 2_666 . . 2_666 ? C5 C1 C6 C7 -8(2) 2_666 . . 2_666 ? O3 C1 C6 C7 179.2(14) 2_666 . . 2_666 ? C6 C2 C7 C5 -173(4) 2_666 . . 2_666 ? C4 C2 C7 C5 2(3) 2_666 . . 2_666 ? C3 C2 C7 C5 -175(4) . . . 2_666 ? C1 C2 C7 C5 4(3) . . . 2_666 ? C1 C2 C7 C5 -168(4) 2_666 . . 2_666 ? C3 C2 C7 C5 -2(3) 2_666 . . 2_666 ? C5 C2 C7 C6 173(4) 2_666 . . 2_666 ? C4 C2 C7 C6 174.7(8) 2_666 . . 2_666 ? C3 C2 C7 C6 -2.1(6) . . . 2_666 ? C1 C2 C7 C6 176.8(10) . . . 2_666 ? C1 C2 C7 C6 5.1(8) 2_666 . . 2_666 ? C3 C2 C7 C6 171.1(11) 2_666 . . 2_666 ? C5 C2 C7 C4 -2(3) 2_666 . . 2_666 ? C6 C2 C7 C4 -174.7(8) 2_666 . . 2_666 ? C3 C2 C7 C4 -176.8(9) . . . 2_666 ? C1 C2 C7 C4 2.1(5) . . . 2_666 ? C1 C2 C7 C4 -169.5(12) 2_666 . . 2_666 ? C3 C2 C7 C4 -3.6(6) 2_666 . . 2_666 ? O8 C8 C9 C10 179.62(19) . . . . ? C13 C8 C9 C10 0.8(3) . . . . ? O8 C8 C9 C14 1.5(3) . . . . ? C13 C8 C9 C14 -177.4(2) . . . . ? C8 C9 C10 O10 178.6(2) . . . . ? C14 C9 C10 O10 -3.3(3) . . . . ? C8 C9 C10 C11 -1.1(3) . . . . ? C14 C9 C10 C11 177.1(2) . . . . ? O10 C10 C11 C12 -179.1(2) . . . . ? C9 C10 C11 C12 0.5(4) . . . . ? C10 C11 C12 C13 0.5(4) . . . . ? C11 C12 C13 C8 -0.8(4) . . . . ? O8 C8 C13 C12 -178.7(2) . . . . ? C9 C8 C13 C12 0.1(4) . . . . ? C26 N1 C22 C23 1.1(4) . . . . ? N1 C22 C23 C24 -0.4(4) . . . . ? C22 C23 C24 C25 -0.2(4) . . . . ? C22 C23 C24 C29 178.2(2) . . . . ? C23 C24 C25 C26 0.1(4) . . . . ? C29 C24 C25 C26 -178.3(2) . . . . ? C22 N1 C26 C25 -1.3(4) . . . . ? C24 C25 C26 N1 0.7(5) . . . . ? C31 N2 C27 C28 -0.8(4) . . . . ? N2 C27 C28 C29 -0.4(4) . . . . ? C27 C28 C29 C30 1.4(4) . . . . ? C27 C28 C29 C24 -177.7(2) . . . . ? C25 C24 C29 C28 162.6(2) . . . . ? C23 C24 C29 C28 -15.7(4) . . . . ? C25 C24 C29 C30 -16.4(4) . . . . ? C23 C24 C29 C30 165.3(2) . . . . ? C28 C29 C30 C31 -1.3(4) . . . . ? C24 C29 C30 C31 177.8(2) . . . . ? C27 N2 C31 C30 0.9(4) . . . . ? C29 C30 C31 N2 0.2(4) . . . . ? C36 N3 C32 C33 -1.0(4) . . . . ? N3 C32 C33 C34 1.0(4) . . . . ? C32 C33 C34 C35 -0.7(4) . . . . ? C32 C33 C34 C34 -179.9(3) . . . 2_665 ? C33 C34 C35 C36 0.5(4) . . . . ? C34 C34 C35 C36 179.7(3) 2_665 . . . ? C32 N3 C36 C35 0.8(4) . . . . ? C34 C35 C36 N3 -0.6(4) . . . . ? C59 C37 C38 C39 1.0(4) . . . . ? C37 C38 C39 C50 -0.9(4) . . . . ? C37 C38 C39 C40 178.6(3) . . . . ? C38 C39 C40 C41 179.4(3) . . . . ? C50 C39 C40 C41 -1.1(4) . . . . ? C39 C40 C41 C42 1.1(4) . . . . ? C40 C41 C42 C43 179.0(3) . . . . ? C40 C41 C42 C51 -1.1(4) . . . . ? C51 C42 C43 C44 -0.3(4) . . . . ? C41 C42 C43 C44 179.6(3) . . . . ? C42 C43 C44 C45 -1.0(5) . . . . ? C43 C44 C45 C46 1.3(5) . . . . ? C44 C45 C46 C51 -0.3(4) . . . . ? C44 C45 C46 C47 179.6(3) . . . . ? C45 C46 C47 C48 -178.4(3) . . . . ? C51 C46 C47 C48 1.6(4) . . . . ? C46 C47 C48 C49 -1.1(5) . . . . ? C47 C48 C49 C59 -179.1(3) . . . . ? C47 C48 C49 C50 -0.4(4) . . . . ? C59 C49 C50 C39 0.7(4) . . . . ? C48 C49 C50 C39 -178.1(2) . . . . ? C59 C49 C50 C51 -179.8(2) . . . . ? C48 C49 C50 C51 1.4(4) . . . . ? C38 C39 C50 C49 0.1(4) . . . . ? C40 C39 C50 C49 -179.5(2) . . . . ? C38 C39 C50 C51 -179.5(2) . . . . ? C40 C39 C50 C51 1.0(4) . . . . ? C45 C46 C51 C42 -1.0(4) . . . . ? C47 C46 C51 C42 179.0(2) . . . . ? C45 C46 C51 C50 179.4(2) . . . . ? C47 C46 C51 C50 -0.5(4) . . . . ? C43 C42 C51 C46 1.3(4) . . . . ? C41 C42 C51 C46 -178.6(2) . . . . ? C43 C42 C51 C50 -179.1(2) . . . . ? C41 C42 C51 C50 1.0(4) . . . . ? C49 C50 C51 C46 -0.9(4) . . . . ? C39 C50 C51 C46 178.6(2) . . . . ? C49 C50 C51 C42 179.5(2) . . . . ? C39 C50 C51 C42 -1.0(4) . . . . ? C38 C37 C59 C49 -0.2(4) . . . . ? C50 C49 C59 C37 -0.6(4) . . . . ? C48 C49 C59 C37 178.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.381 _refine_diff_density_min -0.431 _refine_diff_density_rms 0.112 # Attachment '26dht_44bp_btp_e_211ploton .cif' data_26dht_44bp_btp_e_211ploton _database_code_depnum_ccdc_archive 'CCDC 836445' #TrackingRef '26dht_44bp_btp_e_211ploton .cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H28 N2 O4 S2' _chemical_formula_weight 568.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1250 0.1230 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.827(6) _cell_length_b 18.987(14) _cell_length_c 11.956(6) _cell_angle_alpha 90.00 _cell_angle_beta 126.99(3) _cell_angle_gamma 90.00 _cell_volume 1419.2(17) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4228 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 0.228 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9347 _exptl_absorpt_correction_T_max 0.9775 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14493 _diffrn_reflns_av_R_equivalents 0.1445 _diffrn_reflns_av_sigmaI/netI 0.0866 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3250 _reflns_number_gt 2807 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0988P)^2^+0.3055P] 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 3250 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.1836 _refine_ls_wR_factor_gt 0.1713 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.034 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N2 N 0.8889(2) 0.08653(8) 0.32023(15) 0.0278(3) Uani 1 1 d . . . C26 C 0.5824(2) 0.01799(8) 0.06707(15) 0.0200(3) Uani 1 1 d . . . C27 C 0.7622(3) -0.01694(9) 0.17717(18) 0.0302(4) Uani 1 1 d . . . H11 H 0.7843 -0.0651 0.1678 0.036 Uiso 1 1 calc R . . C30 C 0.5634(3) 0.08903(9) 0.08787(19) 0.0284(4) Uani 1 1 d . . . H9 H 0.4441 0.1157 0.0157 0.034 Uiso 1 1 calc R . . C31 C 0.7199(3) 0.12029(10) 0.21466(19) 0.0317(4) Uani 1 1 d . . . H10 H 0.7050 0.1688 0.2264 0.038 Uiso 1 1 calc R . . C32 C 0.9091(3) 0.01856(10) 0.30055(18) 0.0314(4) Uani 1 1 d . . . H40 H 1.0302 -0.0065 0.3750 0.038 Uiso 1 1 calc R . . O1 O 0.18839(19) 0.34712(6) 0.05555(12) 0.0254(3) Uani 1 1 d . . . H1 H 0.0674 0.3593 -0.0232 0.038 Uiso 1 1 d R . . O2 O 0.3634(2) 0.23965(7) 0.46910(13) 0.0292(3) Uani 1 1 d . . . H5 H 0.3052 0.2167 0.5000 0.044 Uiso 1 1 d R . . C1 C 0.1245(3) 0.32711(8) 0.13569(16) 0.0203(3) Uani 1 1 d . . . C2 C 0.2121(3) 0.27295(8) 0.34522(16) 0.0215(4) Uani 1 1 d . . . C3 C -0.0825(3) 0.33998(9) 0.09262(17) 0.0247(4) Uani 1 1 d . . . H2 H -0.1846 0.3621 0.0052 0.030 Uiso 1 1 calc R . . C4 C 0.2763(3) 0.29364(8) 0.26327(16) 0.0205(3) Uani 1 1 d . . . C6 C 0.0082(3) 0.28676(9) 0.30581(18) 0.0262(4) Uani 1 1 d . . . H4 H -0.0303 0.2736 0.3646 0.031 Uiso 1 1 calc R . . C8 C -0.1380(3) 0.32018(10) 0.17887(18) 0.0282(4) Uani 1 1 d . . . H3 H -0.2781 0.3297 0.1505 0.034 Uiso 1 1 calc R . . C11 C 0.5009(3) 0.28114(10) 0.31133(19) 0.0299(4) Uani 1 1 d . . . H45 H 0.6010 0.2869 0.4132 0.045 Uiso 1 1 calc R . . H46 H 0.5355 0.3151 0.2660 0.045 Uiso 1 1 calc R . . H47 H 0.5127 0.2332 0.2862 0.045 Uiso 1 1 calc R . . S1 S 0.09595(10) 0.09918(3) 0.11710(6) 0.0439(2) Uani 1 1 d . . . C13 C 0.0872(3) 0.01247(10) 0.0701(2) 0.0336(4) Uani 1 1 d . . . C14 C 0.2588(4) -0.02591(12) 0.1804(2) 0.0401(5) Uani 1 1 d . . . C15 C 0.3210(4) 0.08569(14) 0.2815(3) 0.0484(6) Uani 1 1 d . . . H25 H 0.3902 0.1211 0.3518 0.058 Uiso 1 1 calc R . . C16 C 0.3902(4) 0.01812(16) 0.3006(2) 0.0513(6) Uani 1 1 d . . . H24 H 0.5154 0.0015 0.3865 0.062 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 N2 0.0291(8) 0.0298(8) 0.0212(7) -0.0081(6) 0.0133(6) -0.0064(6) C26 0.0226(8) 0.0193(8) 0.0164(7) -0.0012(6) 0.0109(7) -0.0027(6) C27 0.0325(9) 0.0191(8) 0.0225(8) -0.0005(6) 0.0078(8) -0.0007(7) C30 0.0275(9) 0.0228(8) 0.0243(8) -0.0039(6) 0.0099(7) 0.0027(6) C31 0.0323(10) 0.0259(9) 0.0299(9) -0.0101(7) 0.0149(8) -0.0010(7) C32 0.0304(9) 0.0273(9) 0.0206(8) -0.0006(6) 0.0069(7) -0.0013(7) O1 0.0288(6) 0.0278(6) 0.0190(6) 0.0059(4) 0.0141(5) 0.0072(5) O2 0.0261(6) 0.0358(7) 0.0221(6) 0.0101(5) 0.0127(5) 0.0013(5) C1 0.0247(8) 0.0167(7) 0.0166(7) -0.0026(5) 0.0109(6) -0.0005(6) C2 0.0223(8) 0.0196(7) 0.0168(7) -0.0005(6) 0.0088(7) -0.0019(6) C3 0.0208(8) 0.0254(8) 0.0187(7) -0.0004(6) 0.0069(7) 0.0010(6) C4 0.0224(8) 0.0175(7) 0.0188(7) -0.0003(5) 0.0109(6) 0.0001(6) C6 0.0249(9) 0.0302(9) 0.0239(8) -0.0006(6) 0.0149(7) -0.0039(6) C8 0.0191(8) 0.0340(9) 0.0260(8) -0.0028(7) 0.0106(7) -0.0015(7) C11 0.0274(9) 0.0341(10) 0.0308(9) 0.0114(7) 0.0188(8) 0.0087(7) S1 0.0495(4) 0.0377(3) 0.0499(4) -0.0043(2) 0.0328(3) -0.0030(2) C13 0.0386(11) 0.0336(10) 0.0388(11) 0.0017(8) 0.0287(10) -0.0003(8) C14 0.0412(11) 0.0438(11) 0.0387(11) 0.0020(9) 0.0258(10) -0.0019(9) C15 0.0471(13) 0.0573(14) 0.0463(13) -0.0112(11) 0.0310(12) -0.0134(11) C16 0.0422(12) 0.0713(17) 0.0386(12) 0.0042(11) 0.0233(11) -0.0034(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C31 1.321(3) . ? N2 C32 1.338(3) . ? C26 C27 1.387(2) . ? C26 C30 1.396(3) . ? C26 C26 1.488(3) 3_655 ? C27 C32 1.382(2) . ? C27 H11 0.9500 . ? C30 C31 1.384(2) . ? C30 H9 0.9500 . ? C31 H10 0.9500 . ? C32 H40 0.9500 . ? O1 C1 1.374(2) . ? O1 H1 0.8742 . ? O2 C2 1.373(2) . ? O2 H5 0.8577 . ? C1 C3 1.395(3) . ? C1 C4 1.400(2) . ? C2 C6 1.391(3) . ? C2 C4 1.400(2) . ? C3 C8 1.390(2) . ? C3 H2 0.9500 . ? C4 C11 1.504(3) . ? C6 C8 1.388(2) . ? C6 H4 0.9500 . ? C8 H3 0.9500 . ? C11 H45 0.9800 . ? C11 H46 0.9800 . ? C11 H47 0.9800 . ? S1 C15 1.693(3) . ? S1 C13 1.728(2) . ? C13 C14 1.394(3) . ? C13 C13 1.464(4) 3 ? C14 C16 1.429(3) . ? C15 C16 1.358(4) . ? C15 H25 0.9500 . ? C16 H24 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 C31 N2 C32 117.15(15) . . ? C27 C26 C30 116.69(15) . . ? C27 C26 C26 122.02(18) . 3_655 ? C30 C26 C26 121.29(18) . 3_655 ? C32 C27 C26 119.81(17) . . ? C32 C27 H11 120.1 . . ? C26 C27 H11 120.1 . . ? C31 C30 C26 119.36(16) . . ? C31 C30 H9 120.3 . . ? C26 C30 H9 120.3 . . ? N2 C31 C30 123.78(17) . . ? N2 C31 H10 118.1 . . ? C30 C31 H10 118.1 . . ? N2 C32 C27 123.19(17) . . ? N2 C32 H40 118.4 . . ? C27 C32 H40 118.4 . . ? C1 O1 H1 102.2 . . ? C2 O2 H5 111.2 . . ? O1 C1 C3 121.54(15) . . ? O1 C1 C4 117.32(15) . . ? C3 C1 C4 121.14(15) . . ? O2 C2 C6 121.42(15) . . ? O2 C2 C4 116.41(15) . . ? C6 C2 C4 122.15(15) . . ? C8 C3 C1 119.40(16) . . ? C8 C3 H2 120.3 . . ? C1 C3 H2 120.3 . . ? C2 C4 C1 117.61(15) . . ? C2 C4 C11 121.18(15) . . ? C1 C4 C11 121.21(15) . . ? C8 C6 C2 118.68(16) . . ? C8 C6 H4 120.7 . . ? C2 C6 H4 120.7 . . ? C6 C8 C3 120.98(16) . . ? C6 C8 H3 119.5 . . ? C3 C8 H3 119.5 . . ? C4 C11 H45 109.5 . . ? C4 C11 H46 109.5 . . ? H45 C11 H46 109.5 . . ? C4 C11 H47 109.5 . . ? H45 C11 H47 109.5 . . ? H46 C11 H47 109.5 . . ? C15 S1 C13 92.49(12) . . ? C14 C13 C13 128.2(2) . 3 ? C14 C13 S1 111.31(16) . . ? C13 C13 S1 120.5(2) 3 . ? C13 C14 C16 110.3(2) . . ? C16 C15 S1 111.67(19) . . ? C16 C15 H25 124.2 . . ? S1 C15 H25 124.2 . . ? C15 C16 C14 114.2(2) . . ? C15 C16 H24 122.9 . . ? C14 C16 H24 122.9 . . ? 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 C30 C26 C27 C32 1.2(3) . . . . ? C26 C26 C27 C32 -178.96(19) 3_655 . . . ? C27 C26 C30 C31 -0.5(3) . . . . ? C26 C26 C30 C31 179.61(19) 3_655 . . . ? C32 N2 C31 C30 1.3(3) . . . . ? C26 C30 C31 N2 -0.7(3) . . . . ? C31 N2 C32 C27 -0.6(3) . . . . ? C26 C27 C32 N2 -0.7(3) . . . . ? O1 C1 C3 C8 -178.53(14) . . . . ? C4 C1 C3 C8 1.0(2) . . . . ? O2 C2 C4 C1 179.40(13) . . . . ? C6 C2 C4 C1 -2.2(2) . . . . ? O2 C2 C4 C11 -1.3(2) . . . . ? C6 C2 C4 C11 177.08(16) . . . . ? O1 C1 C4 C2 -179.82(13) . . . . ? C3 C1 C4 C2 0.6(2) . . . . ? O1 C1 C4 C11 0.9(2) . . . . ? C3 C1 C4 C11 -178.65(15) . . . . ? O2 C2 C6 C8 -179.60(15) . . . . ? C4 C2 C6 C8 2.1(3) . . . . ? C2 C6 C8 C3 -0.4(3) . . . . ? C1 C3 C8 C6 -1.1(3) . . . . ? C15 S1 C13 C14 -0.85(17) . . . . ? C15 S1 C13 C13 178.4(2) . . . 3 ? C13 C13 C14 C16 -178.6(2) 3 . . . ? S1 C13 C14 C16 0.6(2) . . . . ? C13 S1 C15 C16 0.89(19) . . . . ? S1 C15 C16 C14 -0.7(3) . . . . ? C13 C14 C16 C15 0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.592 _refine_diff_density_min -0.484 _refine_diff_density_rms 0.079 # Attachment 'Orcinol44Bipyridyl.cif' # CIF-file generated for datam in P-1 #============================================================================== data_Orcinol44Bipyridyl _database_code_depnum_ccdc_archive 'CCDC 836446' #TrackingRef 'Orcinol44Bipyridyl.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common Orcinol:4,4-Bipyridyl _chemical_melting_point ? _chemical_formula_moiety '3(C10 H8 N2), 2(C7 H8 O2)' _chemical_formula_structural ? _chemical_formula_sum 'C44 H40 N6 O4' _chemical_formula_iupac ? _chemical_formula_weight 716.82 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 8.8290(18) _cell_length_b 10.079(2) _cell_length_c 12.092(2) _cell_angle_alpha 67.68(3) _cell_angle_beta 77.45(3) _cell_angle_gamma 69.16(3) _cell_volume 926.1(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150 _cell_measurement_reflns_used 2156 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 27.5 _cell_special_details ; ; _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_size_rad ? _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 378 _exptl_absorpt_coefficient_mu 0.084 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9513 _exptl_absorpt_correction_T_max 0.9916 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_source_current 12.0 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Fiber _diffrn_detector CCD _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 9829 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_unetI/netI 0.106 _diffrn_reflns_theta_min 2.4 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 10.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.5419 2theta: 29.4698 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 10.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.5419 2theta: 29.4698 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 10.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.5419 2theta: 29.4698 ; _diffrn_orient_matrix_UB_11 -0.108156 _diffrn_orient_matrix_UB_12 0.031024 _diffrn_orient_matrix_UB_13 0.046482 _diffrn_orient_matrix_UB_21 -0.011856 _diffrn_orient_matrix_UB_22 -0.100151 _diffrn_orient_matrix_UB_23 -0.049919 _diffrn_orient_matrix_UB_31 0.040593 _diffrn_orient_matrix_UB_32 -0.010912 _diffrn_orient_matrix_UB_33 0.079357 _diffrn_orient_matrix_type d*Trek _diffrn_reflns_reduction_process ; ; _reflns_number_total 4209 _reflns_number_gt 2926 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs 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^)+(0.1079P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 4209 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0653 _refine_ls_wR_factor_ref 0.2191 _refine_ls_wR_factor_gt 0.1777 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.440 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.091 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N1 N Uani 0.8878(2) 0.2709(2) 0.51886(18) 1.000 0.0400(6) . . N2 N Uani 0.0987(2) 0.3429(2) 0.83776(17) 1.000 0.0360(6) . . C8 C Uani 0.8096(3) 0.1703(3) 0.5402(2) 1.000 0.0430(8) . . C9 C Uani 0.6553(3) 0.1797(3) 0.6003(2) 1.000 0.0380(7) . . C10 C Uani 0.5730(3) 0.3017(2) 0.64086(19) 1.000 0.0305(6) . . C11 C Uani 0.6520(3) 0.4096(3) 0.6164(2) 1.000 0.0369(7) . . C12 C Uani 0.8067(3) 0.3892(3) 0.5572(2) 1.000 0.0399(7) . . C13 C Uani 0.1506(3) 0.2635(3) 0.7621(2) 1.000 0.0374(7) . . C14 C Uani 0.3030(3) 0.2469(3) 0.6968(2) 1.000 0.0345(7) . . C15 C Uani 0.4088(3) 0.3144(2) 0.70913(19) 1.000 0.0293(6) . . C16 C Uani 0.3556(3) 0.3941(3) 0.7901(2) 1.000 0.0355(7) . . C17 C Uani 0.2014(3) 0.4057(3) 0.8511(2) 1.000 0.0394(7) . . N3 N Uani 0.1027(2) 0.9829(2) 0.14108(19) 1.000 0.0414(7) . . C18 C Uani 0.1898(3) 0.8993(3) 0.0728(3) 1.000 0.0464(9) . . C19 C Uani 0.3442(3) 0.9016(3) 0.0166(2) 1.000 0.0416(8) . . C20 C Uani 0.4168(2) 0.9970(2) 0.02912(19) 1.000 0.0285(6) . . C21 C Uani 0.3261(3) 1.0847(3) 0.0999(2) 1.000 0.0389(8) . . C22 C Uani 0.1721(3) 1.0741(3) 0.1530(2) 1.000 0.0440(8) . . O1 O Uani 0.21843(19) 0.53767(17) 0.08256(14) 1.000 0.0354(5) . . O2 O Uani 0.2191(2) 0.15786(18) 0.47551(14) 1.000 0.0370(5) . . C1 C Uani 0.5512(2) 0.2458(2) 0.25098(19) 1.000 0.0299(6) . . C2 C Uani 0.4652(2) 0.3653(2) 0.16051(18) 1.000 0.0284(6) . . C3 C Uani 0.2957(2) 0.4191(2) 0.17473(18) 1.000 0.0270(6) . . C4 C Uani 0.2099(2) 0.3508(2) 0.28068(18) 1.000 0.0276(6) . . C5 C Uani 0.2960(3) 0.2293(2) 0.37072(19) 1.000 0.0287(6) . . C6 C Uani 0.4665(3) 0.1775(2) 0.35611(19) 1.000 0.0294(6) . . C7 C Uani 0.7356(3) 0.1914(3) 0.2363(2) 1.000 0.0408(7) . . H8 H Uiso 0.86330 0.08710 0.51230 1.000 0.0520 calc R H9 H Uiso 0.60630 0.10420 0.61370 1.000 0.0460 calc R H11 H Uiso 0.59970 0.49600 0.64020 1.000 0.0440 calc R H12 H Uiso 0.85900 0.46280 0.54270 1.000 0.0480 calc R H13 H Uiso 0.08030 0.21650 0.75260 1.000 0.0450 calc R H14 H Uiso 0.33480 0.18980 0.64400 1.000 0.0410 calc R H16 H Uiso 0.42430 0.43980 0.80330 1.000 0.0430 calc R H17 H Uiso 0.16670 0.46120 0.90520 1.000 0.0470 calc R H18 H Uiso 0.14330 0.83400 0.06180 1.000 0.0560 calc R H19 H Uiso 0.40040 0.83820 -0.03020 1.000 0.0500 calc R H21 H Uiso 0.36890 1.15170 0.11220 1.000 0.0470 calc R H22 H Uiso 0.11280 1.13570 0.20070 1.000 0.0530 calc R H1O H Uiso 0.109(4) 0.586(4) 0.117(3) 1.000 0.064(9) . . H2 H Uiso 0.52260 0.41080 0.08810 1.000 0.0340 calc R H2O H Uiso 0.105(4) 0.203(4) 0.485(3) 1.000 0.071(10) . . H4 H Uiso 0.09440 0.38680 0.29100 1.000 0.0330 calc R H6 H Uiso 0.52440 0.09550 0.41820 1.000 0.0350 calc R H7A H Uiso 0.77400 0.22130 0.15070 1.000 0.0610 calc R H7B H Uiso 0.77360 0.08150 0.27170 1.000 0.0610 calc R H7C H Uiso 0.77840 0.23620 0.27700 1.000 0.0610 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0327(10) 0.0454(12) 0.0402(11) -0.0131(10) 0.0018(9) -0.0143(9) N2 0.0292(10) 0.0348(10) 0.0389(11) -0.0076(9) -0.0022(8) -0.0095(8) C8 0.0354(12) 0.0446(14) 0.0539(15) -0.0244(13) 0.0033(11) -0.0135(11) C9 0.0321(11) 0.0409(13) 0.0463(14) -0.0186(11) 0.0012(10) -0.0157(10) C10 0.0260(10) 0.0336(11) 0.0320(11) -0.0094(9) -0.0024(9) -0.0110(9) C11 0.0342(12) 0.0356(12) 0.0423(13) -0.0131(11) 0.0007(10) -0.0144(10) C12 0.0361(12) 0.0409(13) 0.0432(13) -0.0118(11) 0.0045(10) -0.0195(11) C13 0.0304(11) 0.0401(13) 0.0439(13) -0.0125(11) -0.0024(10) -0.0154(10) C14 0.0312(11) 0.0374(12) 0.0384(12) -0.0156(10) -0.0019(10) -0.0119(10) C15 0.0270(10) 0.0278(10) 0.0318(11) -0.0067(9) -0.0033(9) -0.0099(9) C16 0.0309(11) 0.0401(13) 0.0424(13) -0.0180(11) -0.0004(10) -0.0157(10) C17 0.0379(12) 0.0385(13) 0.0414(13) -0.0151(11) 0.0006(11) -0.0117(10) N3 0.0290(10) 0.0484(12) 0.0522(13) -0.0216(11) 0.0028(9) -0.0165(9) C18 0.0329(12) 0.0532(15) 0.0676(18) -0.0311(14) 0.0057(12) -0.0241(12) C19 0.0326(12) 0.0454(14) 0.0590(16) -0.0315(13) 0.0048(11) -0.0159(11) C20 0.0255(10) 0.0255(10) 0.0323(11) -0.0063(9) -0.0055(9) -0.0071(8) C21 0.0346(12) 0.0443(13) 0.0483(14) -0.0244(12) 0.0050(11) -0.0196(11) C22 0.0353(13) 0.0497(15) 0.0549(15) -0.0300(13) 0.0078(12) -0.0155(11) O1 0.0312(8) 0.0338(9) 0.0301(8) -0.0041(7) 0.0003(7) -0.0058(7) O2 0.0325(9) 0.0372(9) 0.0328(9) -0.0012(7) 0.0024(7) -0.0151(7) C1 0.0268(10) 0.0289(11) 0.0359(11) -0.0124(9) 0.0008(9) -0.0112(9) C2 0.0286(11) 0.0292(11) 0.0294(11) -0.0109(9) 0.0030(9) -0.0132(9) C3 0.0278(10) 0.0249(10) 0.0290(11) -0.0103(9) -0.0025(8) -0.0075(8) C4 0.0238(10) 0.0282(11) 0.0313(11) -0.0106(9) 0.0019(8) -0.0104(8) C5 0.0322(11) 0.0279(11) 0.0284(11) -0.0101(9) 0.0012(9) -0.0135(9) C6 0.0273(10) 0.0252(10) 0.0325(11) -0.0059(9) -0.0036(9) -0.0079(8) C7 0.0283(11) 0.0452(14) 0.0398(13) -0.0075(11) 0.0003(10) -0.0097(10) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 1.369(3) . . yes O2 C5 1.366(3) . . yes O1 H1O 0.99(4) . . no O2 H2O 0.95(4) . . no N1 C8 1.339(4) . . yes N1 C12 1.348(4) . . yes N2 C13 1.342(3) . . yes N2 C17 1.341(4) . . yes N3 C18 1.332(4) . . yes N3 C22 1.335(4) . . yes C8 C9 1.387(4) . . no C9 C10 1.396(4) . . no C10 C15 1.493(4) . . no C10 C11 1.401(4) . . no C11 C12 1.381(4) . . no C13 C14 1.393(4) . . no C14 C15 1.396(4) . . no C15 C16 1.398(3) . . no C16 C17 1.388(4) . . no C8 H8 0.9500 . . no C9 H9 0.9500 . . no C11 H11 0.9500 . . no C12 H12 0.9500 . . no C13 H13 0.9500 . . no C14 H14 0.9500 . . no C16 H16 0.9500 . . no C17 H17 0.9500 . . no C18 C19 1.389(4) . . no C19 C20 1.396(4) . . no C20 C20 1.496(3) . 2_675 no C20 C21 1.389(3) . . no C21 C22 1.394(4) . . no C18 H18 0.9500 . . no C19 H19 0.9500 . . no C21 H21 0.9500 . . no C22 H22 0.9500 . . no C1 C7 1.515(4) . . no C1 C2 1.391(3) . . no C1 C6 1.392(3) . . no C2 C3 1.395(3) . . no C3 C4 1.403(3) . . no C4 C5 1.396(3) . . no C5 C6 1.402(4) . . no C2 H2 0.9500 . . no C4 H4 0.9500 . . no C6 H6 0.9500 . . no C7 H7A 0.9800 . . no C7 H7B 0.9800 . . no C7 H7C 0.9800 . . no 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 C3 O1 H1O 107(2) . . . no C5 O2 H2O 115(2) . . . no C8 N1 C12 116.3(2) . . . yes C13 N2 C17 117.4(2) . . . yes C18 N3 C22 115.8(2) . . . yes N1 C8 C9 124.2(3) . . . yes C8 C9 C10 119.0(3) . . . no C11 C10 C15 121.8(2) . . . no C9 C10 C15 121.0(2) . . . no C9 C10 C11 117.2(2) . . . no C10 C11 C12 119.4(3) . . . no N1 C12 C11 123.8(3) . . . yes N2 C13 C14 122.9(3) . . . yes C13 C14 C15 119.8(2) . . . no C14 C15 C16 117.1(2) . . . no C10 C15 C16 120.6(2) . . . no C10 C15 C14 122.2(2) . . . no C15 C16 C17 119.3(3) . . . no N2 C17 C16 123.5(2) . . . yes C9 C8 H8 118.00 . . . no N1 C8 H8 118.00 . . . no C10 C9 H9 120.00 . . . no C8 C9 H9 121.00 . . . no C12 C11 H11 120.00 . . . no C10 C11 H11 120.00 . . . no C11 C12 H12 118.00 . . . no N1 C12 H12 118.00 . . . no N2 C13 H13 119.00 . . . no C14 C13 H13 119.00 . . . no C15 C14 H14 120.00 . . . no C13 C14 H14 120.00 . . . no C15 C16 H16 120.00 . . . no C17 C16 H16 120.00 . . . no N2 C17 H17 118.00 . . . no C16 C17 H17 118.00 . . . no N3 C18 C19 124.2(3) . . . yes C18 C19 C20 120.0(2) . . . no C20 C20 C21 122.0(2) 2_675 . . no C19 C20 C21 116.0(2) . . . no C19 C20 C20 122.0(2) . . 2_675 no C20 C21 C22 119.8(3) . . . no N3 C22 C21 124.2(3) . . . yes C19 C18 H18 118.00 . . . no N3 C18 H18 118.00 . . . no C18 C19 H19 120.00 . . . no C20 C19 H19 120.00 . . . no C20 C21 H21 120.00 . . . no C22 C21 H21 120.00 . . . no N3 C22 H22 118.00 . . . no C21 C22 H22 118.00 . . . no C2 C1 C7 120.45(19) . . . no C2 C1 C6 119.4(2) . . . no C6 C1 C7 120.1(2) . . . no C1 C2 C3 120.85(19) . . . no O1 C3 C2 117.95(18) . . . yes C2 C3 C4 119.89(19) . . . no O1 C3 C4 122.16(18) . . . yes C3 C4 C5 119.3(2) . . . no O2 C5 C4 121.9(2) . . . yes O2 C5 C6 117.8(2) . . . yes C4 C5 C6 120.3(2) . . . no C1 C6 C5 120.2(2) . . . no C1 C2 H2 120.00 . . . no C3 C2 H2 120.00 . . . no C3 C4 H4 120.00 . . . no C5 C4 H4 120.00 . . . no C1 C6 H6 120.00 . . . no C5 C6 H6 120.00 . . . no C1 C7 H7A 109.00 . . . no C1 C7 H7B 109.00 . . . no C1 C7 H7C 109.00 . . . no H7A C7 H7B 109.00 . . . no H7A C7 H7C 109.00 . . . no H7B C7 H7C 109.00 . . . no 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 C12 N1 C8 C9 -1.4(4) . . . . no C8 N1 C12 C11 0.5(4) . . . . no C17 N2 C13 C14 -1.2(4) . . . . no C13 N2 C17 C16 0.8(4) . . . . no C22 N3 C18 C19 0.6(4) . . . . no C18 N3 C22 C21 -0.4(4) . . . . no N1 C8 C9 C10 0.8(4) . . . . no C8 C9 C10 C15 -178.2(2) . . . . no C8 C9 C10 C11 0.9(3) . . . . no C9 C10 C15 C16 153.4(2) . . . . no C15 C10 C11 C12 177.3(2) . . . . no C11 C10 C15 C14 155.2(2) . . . . no C9 C10 C15 C14 -25.8(3) . . . . no C11 C10 C15 C16 -25.6(3) . . . . no C9 C10 C11 C12 -1.7(3) . . . . no C10 C11 C12 N1 1.1(4) . . . . no N2 C13 C14 C15 0.1(4) . . . . no C13 C14 C15 C16 1.3(4) . . . . no C13 C14 C15 C10 -179.5(2) . . . . no C10 C15 C16 C17 179.1(2) . . . . no C14 C15 C16 C17 -1.6(3) . . . . no C15 C16 C17 N2 0.6(4) . . . . no N3 C18 C19 C20 -0.6(4) . . . . no C18 C19 C20 C21 0.4(4) . . . . no C18 C19 C20 C20 179.7(2) . . . 2_675 no C20 C20 C21 C22 -179.5(2) 2_675 . . . no C19 C20 C20 C19 -180.0(2) . . 2_675 2_675 no C19 C20 C20 C21 0.7(3) . . 2_675 2_675 no C21 C20 C20 C19 -0.7(3) . . 2_675 2_675 no C21 C20 C20 C21 180.0(2) . . 2_675 2_675 no C19 C20 C21 C22 -0.2(3) . . . . no C20 C21 C22 N3 0.2(4) . . . . no C6 C1 C2 C3 1.2(3) . . . . no C7 C1 C2 C3 -178.0(2) . . . . no C2 C1 C6 C5 -0.3(3) . . . . no C7 C1 C6 C5 178.9(2) . . . . no C1 C2 C3 O1 179.60(19) . . . . no C1 C2 C3 C4 -1.0(3) . . . . no O1 C3 C4 C5 179.34(19) . . . . no C2 C3 C4 C5 0.0(3) . . . . no C3 C4 C5 O2 -179.7(2) . . . . no C3 C4 C5 C6 0.9(3) . . . . no O2 C5 C6 C1 179.8(2) . . . . no C4 C5 C6 C1 -0.8(3) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 N2 2.744(3) . 2_566 no O2 N1 2.747(3) . 1_455 no O2 C14 3.417(3) . . no O1 H2 2.7800 . 2_665 no O1 H17 2.7100 . 1_554 no O1 H18 2.7400 . . no O2 H14 2.6300 . . no O2 H6 2.8200 . 2_656 no O2 H8 2.7600 . 2_656 no N1 O2 2.747(3) . 1_655 no N2 C4 3.370(3) . 2_566 no N2 O1 2.744(3) . 2_566 no N3 C7 3.408(4) . 1_465 no N1 H2O 1.80(4) . 1_655 no N2 H4 2.7200 . 2_566 no N2 H1O 1.76(4) . 2_566 no N3 H13 2.7800 . 2_566 no C4 N2 3.370(3) . 2_566 no C7 N3 3.408(4) . 1_645 no C8 C22 3.591(3) . 2_666 no C9 C22 3.342(4) . 2_666 no C9 C21 3.589(3) . 2_666 no C14 O2 3.417(3) . . no C17 C21 3.499(4) . 1_546 no C21 C9 3.589(3) . 2_666 no C21 C17 3.499(4) . 1_564 no C22 C8 3.591(3) . 2_666 no C22 C9 3.342(4) . 2_666 no C1 H16 3.0600 . 2_666 no C1 H19 3.0000 . 2_665 no C2 H21 2.8600 . 1_545 no C2 H19 2.8300 . 2_665 no C2 H2 3.0000 . 2_665 no C2 H16 2.6800 . 2_666 no C2 H11 3.0800 . 2_666 no C3 H21 2.8900 . 1_545 no C3 H11 3.0800 . 2_666 no C5 H9 3.1000 . 2_656 no C6 H6 3.0400 . 2_656 no C6 H9 3.0000 . 2_656 no C8 H7C 3.0500 . . no C8 H2O 2.65(4) . 1_655 no C9 H14 2.7400 . . no C11 H16 2.7100 . . no C12 H2O 2.82(4) . 1_655 no C13 H1O 2.73(4) . 2_566 no C14 H9 2.7300 . . no C16 H11 2.7300 . . no C17 H1O 2.66(4) . 2_566 no C17 H4 3.0800 . 2_566 no C18 H13 3.0700 . 2_566 no C19 H21 2.6600 . 2_675 no C21 H19 2.6600 . 2_675 no H1O N2 1.76(4) . 2_566 no H1O C13 2.73(4) . 2_566 no H1O H18 2.4400 . . no H1O H4 2.3100 . . no H1O C17 2.66(4) . 2_566 no H2 H7A 2.4000 . . no H2 O1 2.7800 . 2_665 no H2 H2 2.2100 . 2_665 no H2 H16 2.5500 . 2_666 no H2 C2 3.0000 . 2_665 no H2O C8 2.65(4) . 1_455 no H2O N1 1.80(4) . 1_455 no H2O H4 2.3700 . . no H2O C12 2.82(4) . 1_455 no H4 C17 3.0800 . 2_566 no H4 H1O 2.3100 . . no H4 N2 2.7200 . 2_566 no H4 H2O 2.3700 . . no H6 H6 2.2700 . 2_656 no H6 H7B 2.5000 . . no H6 O2 2.8200 . 2_656 no H6 C6 3.0400 . 2_656 no H7A H2 2.4000 . . no H7B H6 2.5000 . . no H7C C8 3.0500 . . no H8 O2 2.7600 . 2_656 no H8 H8 2.4600 . 2_756 no H9 C6 3.0000 . 2_656 no H9 C14 2.7300 . . no H9 H14 2.2400 . . no H9 C5 3.1000 . 2_656 no H11 C16 2.7300 . . no H11 H16 2.2500 . . no H11 C3 3.0800 . 2_666 no H11 C2 3.0800 . 2_666 no H13 C18 3.0700 . 2_566 no H13 N3 2.7800 . 2_566 no H14 O2 2.6300 . . no H14 C9 2.7400 . . no H14 H9 2.2400 . . no H16 H11 2.2500 . . no H16 C11 2.7100 . . no H16 H2 2.5500 . 2_666 no H16 C1 3.0600 . 2_666 no H16 C2 2.6800 . 2_666 no H17 O1 2.7100 . 1_556 no H18 O1 2.7400 . . no H18 H1O 2.4400 . . no H19 C1 3.0000 . 2_665 no H19 H21 2.0800 . 2_675 no H19 C2 2.8300 . 2_665 no H19 C21 2.6600 . 2_675 no H21 C2 2.8600 . 1_565 no H21 H19 2.0800 . 2_675 no H21 C3 2.8900 . 1_565 no H21 C19 2.6600 . 2_675 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1O N2 0.99(4) 1.76(4) 2.744(3) 169(4) 2_566 yes O2 H2O N1 0.95(4) 1.80(4) 2.747(3) 173(3) 1_455 yes # Loop Mechanism for Extra Tables(s) #loop_ #_publ_manuscript_incl_extra_item #'_geom_extra_tableA_col_1' #'_geom_extra_tableA_col_2' #'_geom_extra_tableA_col_3' #'_geom_extra_table_head_A' #'_geom_table_footnote_A' #'_geom_extra_tableB_col_1' #'_geom_extra_tableB_col_2' #'_geom_extra_tableB_col_3' #'_geom_extra_table_head_B' #'_geom_table_footnote_B' # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 # ? ? ? # #loop_ #_geom_extra_tableB_col_1 #_geom_extra_tableB_col_2 #_geom_extra_tableB_col_3 # ? ? ? # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; #===END # Attachment 'mres_bipy_phenazine.cif' data_mres_bipy_phenazine _database_code_depnum_ccdc_archive 'CCDC 836447' #TrackingRef 'mres_bipy_phenazine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H32 N4 O4' _chemical_formula_weight 584.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.6576(9) _cell_length_b 19.710(2) _cell_length_c 11.6365(12) _cell_angle_alpha 90.00 _cell_angle_beta 125.572(7) _cell_angle_gamma 90.00 _cell_volume 1428.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12950 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9564 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14793 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 3280 _reflns_number_gt 2732 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.5808P] 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 3280 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.232 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.042 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.59943(19) -0.06409(6) 0.55706(12) 0.0243(3) Uani 1 1 d . . . C1 C 0.6817(2) -0.00661(7) 0.63159(15) 0.0228(3) Uani 1 1 d . . . C2 C 0.4177(2) -0.05817(7) 0.42559(14) 0.0224(3) Uani 1 1 d . . . C3 C 0.3228(2) -0.11706(7) 0.34022(16) 0.0273(3) Uani 1 1 d . . . H3 H 0.3866 -0.1602 0.3768 0.033 Uiso 1 1 calc R . . C4 C 0.1418(2) -0.11181(7) 0.20698(16) 0.0292(3) Uani 1 1 d . . . H4 H 0.0801 -0.1515 0.1507 0.035 Uiso 1 1 calc R . . C5 C 0.0430(2) -0.04794(8) 0.15031(15) 0.0286(3) Uani 1 1 d . . . H5 H -0.0836 -0.0455 0.0565 0.034 Uiso 1 1 calc R . . C6 C 0.8737(2) -0.00966(7) 0.77229(15) 0.0271(3) Uani 1 1 d . . . H6 H 0.9428 -0.0520 0.8114 0.033 Uiso 1 1 calc R . . N3 N -0.41424(18) -0.08456(6) 0.18620(12) 0.0237(3) Uani 1 1 d . . . C7 C -0.4169(2) -0.01759(7) 0.20134(15) 0.0271(3) Uani 1 1 d . . . H7 H -0.5326 0.0076 0.1253 0.033 Uiso 1 1 calc R . . C8 C -0.2607(2) 0.01737(7) 0.32148(14) 0.0248(3) Uani 1 1 d . . . H8 H -0.2720 0.0651 0.3269 0.030 Uiso 1 1 calc R . . C9 C -0.0871(2) -0.01753(6) 0.43433(13) 0.0173(3) Uani 1 1 d . . . C10 C -0.0848(2) -0.08729(7) 0.41853(14) 0.0265(3) Uani 1 1 d . . . H10 H 0.0295 -0.1138 0.4923 0.032 Uiso 1 1 calc R . . C11 C -0.2492(2) -0.11809(7) 0.29511(15) 0.0291(3) Uani 1 1 d . . . H11 H -0.2443 -0.1659 0.2875 0.035 Uiso 1 1 calc R . . O1 O 0.27804(15) -0.15324(5) 0.95205(9) 0.0210(2) Uani 1 1 d . . . H1O H 0.3864 -0.1307 1.0327 0.031 Uiso 1 1 d R . . O2 O 0.10814(15) -0.24751(5) 0.52443(9) 0.0232(2) Uani 1 1 d . . . H2O H 0.1729 -0.2754 0.4990 0.035 Uiso 1 1 d R . . C12 C -0.0384(2) -0.20937(7) 0.68737(14) 0.0222(3) Uani 1 1 d . . . H12A H -0.0436 -0.2417 0.7493 0.033 Uiso 1 1 calc R . . H12B H -0.1237 -0.2268 0.5904 0.033 Uiso 1 1 calc R . . H12C H -0.0972 -0.1657 0.6899 0.033 Uiso 1 1 calc R . . C13 C 0.1913(2) -0.19998(6) 0.73731(13) 0.0168(3) Uani 1 1 d . . . C14 C 0.2596(2) -0.21933(6) 0.65375(13) 0.0184(3) Uani 1 1 d . . . C15 C 0.4690(2) -0.20860(7) 0.69688(14) 0.0230(3) Uani 1 1 d . . . H15 H 0.5108 -0.2208 0.6371 0.028 Uiso 1 1 calc R . . C16 C 0.6159(2) -0.17988(7) 0.82794(15) 0.0254(3) Uani 1 1 d . . . H16 H 0.7596 -0.1727 0.8583 0.030 Uiso 1 1 calc R . . C17 C 0.5562(2) -0.16145(7) 0.91525(14) 0.0219(3) Uani 1 1 d . . . H17 H 0.6585 -0.1424 1.0056 0.026 Uiso 1 1 calc R . . C18 C 0.3449(2) -0.17114(6) 0.86927(13) 0.0171(3) 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 N1 0.0250(6) 0.0214(6) 0.0264(6) 0.0006(5) 0.0150(5) 0.0005(5) C1 0.0235(7) 0.0236(7) 0.0252(7) -0.0011(5) 0.0164(6) -0.0023(5) C2 0.0226(7) 0.0233(7) 0.0247(7) 0.0008(5) 0.0157(6) 0.0000(5) C3 0.0291(8) 0.0224(7) 0.0319(8) -0.0014(6) 0.0187(7) -0.0005(6) C4 0.0298(8) 0.0271(7) 0.0330(8) -0.0076(6) 0.0195(7) -0.0073(6) C5 0.0226(7) 0.0351(8) 0.0230(7) -0.0012(6) 0.0104(6) -0.0041(6) C6 0.0256(7) 0.0266(7) 0.0275(7) 0.0034(6) 0.0145(6) 0.0013(6) N3 0.0225(6) 0.0264(6) 0.0202(6) -0.0060(5) 0.0112(5) -0.0044(5) C7 0.0213(7) 0.0276(7) 0.0214(7) 0.0013(6) 0.0061(6) 0.0014(6) C8 0.0232(7) 0.0183(6) 0.0232(7) 0.0000(5) 0.0080(6) 0.0002(5) C9 0.0177(6) 0.0188(6) 0.0156(6) 0.0003(5) 0.0098(5) -0.0011(5) C10 0.0277(7) 0.0191(7) 0.0197(7) 0.0003(5) 0.0064(6) 0.0037(6) C11 0.0328(8) 0.0197(7) 0.0268(7) -0.0050(5) 0.0128(7) -0.0006(6) O1 0.0217(5) 0.0234(5) 0.0168(4) -0.0047(4) 0.0106(4) -0.0054(4) O2 0.0213(5) 0.0271(5) 0.0173(5) -0.0050(4) 0.0090(4) 0.0022(4) C12 0.0186(6) 0.0241(7) 0.0213(7) -0.0054(5) 0.0101(6) -0.0031(5) C13 0.0166(6) 0.0137(6) 0.0176(6) 0.0020(5) 0.0086(5) 0.0011(5) C14 0.0198(6) 0.0154(6) 0.0155(6) 0.0017(5) 0.0078(5) 0.0018(5) C15 0.0218(7) 0.0268(7) 0.0235(7) 0.0010(5) 0.0149(6) 0.0031(5) C16 0.0161(6) 0.0311(7) 0.0277(7) 0.0016(6) 0.0120(6) 0.0001(5) C17 0.0173(6) 0.0235(6) 0.0182(6) -0.0002(5) 0.0066(5) -0.0019(5) C18 0.0198(6) 0.0145(6) 0.0166(6) 0.0024(5) 0.0104(5) 0.0005(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3404(18) . ? N1 C2 1.3467(18) . ? C1 C6 1.430(2) . ? C1 C2 1.4363(19) 3_656 ? C2 C3 1.4220(19) . ? C2 C1 1.4363(19) 3_656 ? C3 C4 1.355(2) . ? C3 H3 0.9500 . ? C4 C5 1.418(2) . ? C4 H4 0.9500 . ? C5 C6 1.356(2) 3_656 ? C5 H5 0.9500 . ? C6 C5 1.356(2) 3_656 ? C6 H6 0.9500 . ? N3 C11 1.3327(19) . ? N3 C7 1.3335(18) . ? C7 C8 1.3836(19) . ? C7 H7 0.9500 . ? C8 C9 1.3903(18) . ? C8 H8 0.9500 . ? C9 C10 1.3886(18) . ? C9 C9 1.490(2) 3_556 ? C10 C11 1.3829(19) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? O1 C18 1.3742(15) . ? O1 H1O 0.9277 . ? O2 C14 1.3740(15) . ? O2 H2O 0.8982 . ? C12 C13 1.5092(18) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.3988(18) . ? C13 C18 1.4010(18) . ? C14 C15 1.3894(19) . ? C15 C16 1.384(2) . ? C15 H15 0.9500 . ? C16 C17 1.3833(19) . ? C16 H16 0.9500 . ? C17 C18 1.3908(18) . ? C17 H17 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 116.61(12) . . ? N1 C1 C6 119.24(13) . . ? N1 C1 C2 121.91(13) . 3_656 ? C6 C1 C2 118.85(12) . 3_656 ? N1 C2 C3 119.56(13) . . ? N1 C2 C1 121.48(12) . 3_656 ? C3 C2 C1 118.96(13) . 3_656 ? C4 C3 C2 120.27(13) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.91(14) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 121.12(14) 3_656 . ? C6 C5 H5 119.4 3_656 . ? C4 C5 H5 119.4 . . ? C5 C6 C1 119.89(13) 3_656 . ? C5 C6 H6 120.1 3_656 . ? C1 C6 H6 120.1 . . ? C11 N3 C7 116.35(12) . . ? N3 C7 C8 123.77(13) . . ? N3 C7 H7 118.1 . . ? C8 C7 H7 118.1 . . ? C7 C8 C9 119.83(13) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C10 C9 C8 116.33(12) . . ? C10 C9 C9 121.46(14) . 3_556 ? C8 C9 C9 122.20(14) . 3_556 ? C11 C10 C9 119.87(13) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? N3 C11 C10 123.83(13) . . ? N3 C11 H11 118.1 . . ? C10 C11 H11 118.1 . . ? C18 O1 H1O 110.7 . . ? C14 O2 H2O 109.4 . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C13 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 117.22(11) . . ? C14 C13 C12 121.50(11) . . ? C18 C13 C12 121.27(11) . . ? O2 C14 C15 121.25(12) . . ? O2 C14 C13 116.91(11) . . ? C15 C14 C13 121.80(12) . . ? C16 C15 C14 119.20(12) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C15 C16 C17 120.83(12) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C16 C17 C18 119.28(12) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? O1 C18 C17 121.31(12) . . ? O1 C18 C13 117.06(11) . . ? C17 C18 C13 121.63(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 C2 N1 C1 C6 179.57(12) . . . . ? C2 N1 C1 C2 -0.3(2) . . . 3_656 ? C1 N1 C2 C3 179.45(12) . . . . ? C1 N1 C2 C1 0.3(2) . . . 3_656 ? N1 C2 C3 C4 -179.01(13) . . . . ? C1 C2 C3 C4 0.2(2) 3_656 . . . ? C2 C3 C4 C5 -0.3(2) . . . . ? C3 C4 C5 C6 -0.2(2) . . . 3_656 ? N1 C1 C6 C5 -179.01(13) . . . 3_656 ? C2 C1 C6 C5 0.9(2) 3_656 . . 3_656 ? C11 N3 C7 C8 -0.1(2) . . . . ? N3 C7 C8 C9 0.9(2) . . . . ? C7 C8 C9 C10 -0.9(2) . . . . ? C7 C8 C9 C9 179.27(15) . . . 3_556 ? C8 C9 C10 C11 0.2(2) . . . . ? C9 C9 C10 C11 -179.97(15) 3_556 . . . ? C7 N3 C11 C10 -0.7(2) . . . . ? C9 C10 C11 N3 0.6(2) . . . . ? C18 C13 C14 O2 -179.93(10) . . . . ? C12 C13 C14 O2 -0.24(17) . . . . ? C18 C13 C14 C15 -2.05(18) . . . . ? C12 C13 C14 C15 177.65(12) . . . . ? O2 C14 C15 C16 179.81(12) . . . . ? C13 C14 C15 C16 2.0(2) . . . . ? C14 C15 C16 C17 -0.5(2) . . . . ? C15 C16 C17 C18 -0.9(2) . . . . ? C16 C17 C18 O1 -179.62(12) . . . . ? C16 C17 C18 C13 0.86(19) . . . . ? C14 C13 C18 O1 -178.94(10) . . . . ? C12 C13 C18 O1 1.36(17) . . . . ? C14 C13 C18 C17 0.60(18) . . . . ? C12 C13 C18 C17 -179.10(12) . . . . ? # Attachment 'orc_bipy_acridine.cif' data_orc_bipy_acridine _database_code_depnum_ccdc_archive 'CCDC 836448' #TrackingRef 'orc_bipy_acridine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C47 H41 N5 O4' _chemical_formula_weight 739.85 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 ? _symmetry_space_group_name_H-M 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 9.3265(7) _cell_length_b 10.3739(8) _cell_length_c 11.1923(8) _cell_angle_alpha 68.503(5) _cell_angle_beta 86.581(6) _cell_angle_gamma 69.849(5) _cell_volume 943.12(12) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9211 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 390 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9671 _exptl_absorpt_correction_T_max 0.9752 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10093 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4319 _reflns_number_gt 3679 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.2794P] 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 4319 _refine_ls_number_parameters 511 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1119 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.070 _refine_ls_shift/su_mean 0.017 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 O3 O -0.0120(3) 0.4223(3) 0.8078(3) 0.0288(7) Uani 1 1 d . . . H3O H -0.1081 0.4567 0.8030 0.043 Uiso 1 1 calc R . . O4 O -0.0813(3) 0.5557(4) 1.1810(3) 0.0340(7) Uani 1 1 d . . . H4O H -0.1716 0.5983 1.1474 0.051 Uiso 1 1 calc R . . C41 C 0.4316(5) 0.2789(6) 1.1020(6) 0.0427(13) Uani 1 1 d . . . H41A H 0.4659 0.3265 1.1502 0.064 Uiso 1 1 calc R . . H41B H 0.4886 0.2837 1.0250 0.064 Uiso 1 1 calc R . . H41C H 0.4500 0.1754 1.1565 0.064 Uiso 1 1 calc R . . C42 C 0.2622(5) 0.3581(5) 1.0625(4) 0.0297(9) Uani 1 1 d . . . C43 C 0.1657(5) 0.4247(4) 1.1372(5) 0.0269(9) Uani 1 1 d . . . H43 H 0.2063 0.4252 1.2129 0.032 Uiso 1 1 calc R . . C44 C 0.0097(5) 0.4911(4) 1.1030(4) 0.0278(9) Uani 1 1 d . . . C45 C -0.0523(5) 0.4896(5) 0.9931(5) 0.0264(9) Uani 1 1 d . . . H45 H -0.1596 0.5330 0.9711 0.032 Uiso 1 1 calc R . . C46 C 0.0448(4) 0.4238(4) 0.9162(4) 0.0249(9) Uani 1 1 d . . . C47 C 0.1977(5) 0.3594(5) 0.9501(4) 0.0301(10) Uani 1 1 d . . . H47 H 0.2630 0.3143 0.8973 0.036 Uiso 1 1 calc R . . N1 N 0.2119(5) 0.6834(4) 1.3134(4) 0.0356(9) Uani 1 1 d . . . C1 C -0.0516(5) 0.8540(7) 1.2314(5) 0.0393(12) Uani 1 1 d . . . H1 H -0.0846 0.7760 1.2343 0.047 Uiso 1 1 calc R . . C2 C -0.1517(6) 0.9906(7) 1.1939(6) 0.0451(13) Uani 1 1 d . . . H2 H -0.2567 1.0068 1.1782 0.054 Uiso 1 1 calc R . . C3 C -0.1068(6) 1.1136(6) 1.1766(6) 0.0457(14) Uani 1 1 d . . . H3 H -0.1806 1.2106 1.1448 0.055 Uiso 1 1 calc R . . C4 C 0.0419(5) 1.0940(5) 1.2054(5) 0.0366(11) Uani 1 1 d . . . H4 H 0.0717 1.1761 1.1946 0.044 Uiso 1 1 calc R . . C5 C 0.1521(5) 0.9455(4) 1.2524(4) 0.0230(8) Uani 1 1 d . . . C6 C 0.1070(5) 0.8211(5) 1.2681(5) 0.0300(10) Uani 1 1 d . . . C7 C 0.3028(5) 0.9250(5) 1.2847(4) 0.0255(9) Uani 1 1 d . . . H7 H 0.3340 1.0059 1.2756 0.031 Uiso 1 1 calc R . . C8 C 0.4049(5) 0.7800(5) 1.3307(5) 0.0305(10) Uani 1 1 d . . . C9 C 0.3572(6) 0.6589(5) 1.3441(5) 0.0328(10) Uani 1 1 d . . . C10 C 0.4695(6) 0.5173(5) 1.3897(5) 0.0393(12) Uani 1 1 d . . . H10 H 0.4403 0.4348 1.4007 0.047 Uiso 1 1 calc R . . C11 C 0.6170(7) 0.4933(6) 1.4188(6) 0.0461(13) Uani 1 1 d . . . H11 H 0.6901 0.3959 1.4460 0.055 Uiso 1 1 calc R . . C12 C 0.6630(7) 0.6132(7) 1.4085(6) 0.0470(14) Uani 1 1 d . . . H12 H 0.7654 0.5958 1.4340 0.056 Uiso 1 1 calc R . . C13 C 0.5589(6) 0.7555(6) 1.3615(5) 0.0399(12) Uani 1 1 d . . . H13 H 0.5908 0.8367 1.3499 0.048 Uiso 1 1 calc R . . O1 O -0.4080(4) 1.0514(4) 0.4163(3) 0.0374(8) Uani 1 1 d . . . H1O H -0.3182 1.0052 0.4506 0.056 Uiso 1 1 calc R . . O2 O -0.4779(4) 1.1856(4) 0.7888(3) 0.0349(8) Uani 1 1 d . . . H2O H -0.3878 1.1257 0.8101 0.052 Uiso 1 1 calc R . . C34 C -0.9202(5) 1.3231(6) 0.5023(5) 0.0403(12) Uani 1 1 d . . . H34A H -0.9739 1.2639 0.5635 0.061 Uiso 1 1 calc R . . H34B H -0.9428 1.3306 0.4151 0.061 Uiso 1 1 calc R . . H34C H -0.9546 1.4222 0.5055 0.061 Uiso 1 1 calc R . . C35 C -0.7496(4) 1.2501(4) 0.5372(4) 0.0268(9) Uani 1 1 d . . . C36 C -0.6922(4) 1.2506(5) 0.6462(4) 0.0257(9) Uani 1 1 d . . . H36 H -0.7577 1.2961 0.6986 0.031 Uiso 1 1 calc R . . C37 C -0.5316(4) 1.1810(4) 0.6795(4) 0.0254(9) Uani 1 1 d . . . C38 C -0.4353(4) 1.1139(4) 0.6039(4) 0.0234(8) Uani 1 1 d . . . H38 H -0.3284 1.0680 0.6275 0.028 Uiso 1 1 calc R . . C39 C -0.4957(5) 1.1141(4) 0.4939(4) 0.0239(8) Uani 1 1 d . . . C40 C -0.6541(5) 1.1803(5) 0.4605(4) 0.0275(9) Uani 1 1 d . . . H40 H -0.6964 1.1779 0.3866 0.033 Uiso 1 1 calc R . . N4 N -0.1649(5) 1.0339(5) 0.8457(4) 0.0384(10) Uani 1 1 d . . . N5 N 0.6226(4) 0.7031(5) 1.0706(4) 0.0341(9) Uani 1 1 d . . . C24 C -0.0860(5) 0.8867(5) 0.8731(5) 0.0323(10) Uani 1 1 d . . . H24 H -0.1403 0.8280 0.8639 0.039 Uiso 1 1 calc R . . C25 C 0.0625(5) 0.8213(5) 0.9117(5) 0.0319(10) Uani 1 1 d . . . H25 H 0.1100 0.7191 0.9268 0.038 Uiso 1 1 calc R . . C26 C 0.1520(5) 0.8989(4) 0.9311(4) 0.0236(9) Uani 1 1 d . . . C27 C 0.0683(6) 1.0509(5) 0.9020(6) 0.0432(13) Uani 1 1 d . . . H27 H 0.1177 1.1133 0.9115 0.052 Uiso 1 1 calc R . . C28 C -0.0817(6) 1.1073(6) 0.8608(6) 0.0467(14) Uani 1 1 d . . . H28 H -0.1320 1.2102 0.8406 0.056 Uiso 1 1 calc R . . C29 C 0.3151(4) 0.8335(5) 0.9767(4) 0.0243(9) Uani 1 1 d . . . C30 C 0.4008(5) 0.9166(5) 0.9723(5) 0.0314(10) Uani 1 1 d . . . H30 H 0.3582 1.0214 0.9359 0.038 Uiso 1 1 calc R . . C31 C 0.5557(5) 0.8446(6) 1.0229(5) 0.0376(11) Uani 1 1 d . . . H31 H 0.6139 0.9043 1.0217 0.045 Uiso 1 1 calc R . . C32 C 0.5387(6) 0.6215(6) 1.0734(5) 0.0396(12) Uani 1 1 d . . . H32 H 0.5866 0.5171 1.1077 0.048 Uiso 1 1 calc R . . C33 C 0.3872(5) 0.6786(5) 1.0301(5) 0.0339(11) Uani 1 1 d . . . H33 H 0.3319 0.6153 1.0358 0.041 Uiso 1 1 calc R . . N2 N -0.1139(4) 0.9063(5) 0.5287(4) 0.0351(9) Uani 1 1 d . . . N3 N 0.6745(4) 0.5755(5) 0.7527(4) 0.0348(10) Uani 1 1 d . . . C14 C -0.0421(5) 0.7558(5) 0.5804(5) 0.0348(10) Uani 1 1 d . . . H14 H -0.1004 0.6951 0.5852 0.042 Uiso 1 1 calc R . . C15 C 0.1057(5) 0.6898(5) 0.6244(5) 0.0350(11) Uani 1 1 d . . . H15 H 0.1492 0.5850 0.6583 0.042 Uiso 1 1 calc R . . C16 C 0.1985(5) 0.7755(5) 0.6209(4) 0.0263(9) Uani 1 1 d . . . C17 C 0.1267(5) 0.9258(5) 0.5701(5) 0.0365(12) Uani 1 1 d . . . H17 H 0.1819 0.9889 0.5660 0.044 Uiso 1 1 calc R . . C18 C -0.0272(5) 0.9865(6) 0.5244(5) 0.0371(12) Uani 1 1 d . . . H18 H -0.0729 1.0910 0.4880 0.045 Uiso 1 1 calc R . . C19 C 0.4415(4) 0.7875(5) 0.6859(4) 0.0321(10) Uani 1 1 d . . . H19 H 0.3917 0.8900 0.6685 0.038 Uiso 1 1 calc R . . C20 C 0.3642(4) 0.7024(5) 0.6711(4) 0.0260(9) Uani 1 1 d . . . C21 C 0.4383(5) 0.5579(5) 0.6956(6) 0.0397(13) Uani 1 1 d . . . H21 H 0.3853 0.4985 0.6857 0.048 Uiso 1 1 calc R . . C22 C 0.5953(6) 0.4959(6) 0.7360(7) 0.0492(15) Uani 1 1 d . . . H22 H 0.6474 0.3940 0.7521 0.059 Uiso 1 1 calc R . . C23 C 0.6009(5) 0.7145(6) 0.7290(5) 0.0385(12) Uani 1 1 d . . . H23 H 0.6558 0.7715 0.7408 0.046 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 O3 0.0226(14) 0.0305(16) 0.0304(17) -0.0131(13) -0.0054(13) -0.0026(12) O4 0.0201(14) 0.0386(18) 0.0412(19) -0.0247(15) -0.0008(13) 0.0035(13) C41 0.0180(19) 0.053(3) 0.047(3) -0.015(2) -0.0038(19) -0.0046(19) C42 0.031(2) 0.029(2) 0.025(2) -0.0034(17) -0.0055(17) -0.0108(17) C43 0.025(2) 0.0202(18) 0.033(2) -0.0074(17) -0.0076(17) -0.0068(16) C44 0.030(2) 0.0207(18) 0.033(2) -0.0138(17) 0.0083(17) -0.0067(16) C45 0.0173(17) 0.0255(19) 0.038(2) -0.0136(18) -0.0009(16) -0.0074(15) C46 0.0235(19) 0.0222(19) 0.027(2) -0.0107(17) 0.0033(16) -0.0040(15) C47 0.031(2) 0.028(2) 0.026(2) -0.0083(18) 0.0032(17) -0.0059(17) N1 0.049(2) 0.029(2) 0.034(2) -0.0136(17) 0.0076(18) -0.0172(18) C1 0.032(2) 0.059(3) 0.041(3) -0.023(2) 0.006(2) -0.028(2) C2 0.026(2) 0.062(4) 0.051(3) -0.022(3) 0.004(2) -0.019(2) C3 0.031(2) 0.044(3) 0.048(3) -0.016(3) -0.006(2) 0.004(2) C4 0.030(2) 0.028(2) 0.043(3) -0.007(2) 0.003(2) -0.0056(19) C5 0.0237(19) 0.0216(19) 0.023(2) -0.0078(16) 0.0031(15) -0.0074(15) C6 0.041(3) 0.032(2) 0.027(2) -0.0144(19) 0.0107(19) -0.023(2) C7 0.0251(19) 0.028(2) 0.028(2) -0.0121(17) 0.0036(16) -0.0120(17) C8 0.031(2) 0.033(2) 0.026(2) -0.0126(19) 0.0017(18) -0.0073(18) C9 0.039(2) 0.035(2) 0.029(2) -0.016(2) 0.0042(19) -0.015(2) C10 0.050(3) 0.029(2) 0.038(3) -0.015(2) 0.000(2) -0.010(2) C11 0.044(3) 0.039(3) 0.045(3) -0.011(2) 0.000(2) -0.007(2) C12 0.038(3) 0.061(4) 0.039(3) -0.019(3) -0.004(2) -0.011(3) C13 0.049(3) 0.040(3) 0.034(2) -0.013(2) 0.003(2) -0.020(2) O1 0.0322(17) 0.045(2) 0.0294(17) -0.0167(15) -0.0051(13) -0.0028(15) O2 0.0286(16) 0.0438(19) 0.0346(18) -0.0209(15) -0.0026(14) -0.0075(14) C34 0.026(2) 0.043(3) 0.039(3) -0.012(2) -0.0064(19) 0.0018(19) C35 0.0105(16) 0.0209(18) 0.039(2) -0.0056(17) 0.0000(16) 0.0006(14) C36 0.0137(17) 0.0250(19) 0.034(2) -0.0121(17) 0.0001(16) -0.0004(14) C37 0.0232(19) 0.024(2) 0.026(2) -0.0037(16) -0.0083(16) -0.0088(16) C38 0.0175(17) 0.0206(18) 0.023(2) -0.0039(15) -0.0051(14) 0.0012(14) C39 0.0213(18) 0.0214(18) 0.022(2) -0.0019(16) -0.0067(15) -0.0041(15) C40 0.024(2) 0.031(2) 0.0196(19) -0.0035(17) -0.0027(15) -0.0056(16) N4 0.033(2) 0.038(2) 0.038(2) -0.0114(19) -0.0117(18) -0.0063(18) N5 0.0120(15) 0.047(2) 0.044(2) -0.0275(19) 0.0031(14) 0.0001(14) C24 0.039(2) 0.024(2) 0.037(2) -0.0164(18) -0.0047(18) -0.0080(17) C25 0.044(2) 0.0210(19) 0.036(2) -0.0123(17) -0.0004(19) -0.0159(17) C26 0.028(2) 0.0202(18) 0.0157(17) -0.0021(15) 0.0007(14) -0.0046(15) C27 0.043(3) 0.025(2) 0.054(3) -0.007(2) -0.009(2) -0.008(2) C28 0.033(2) 0.023(2) 0.070(4) -0.009(2) -0.016(3) 0.0015(18) C29 0.0184(18) 0.027(2) 0.022(2) -0.0093(17) 0.0027(16) -0.0009(16) C30 0.0158(18) 0.031(2) 0.040(3) -0.0116(19) -0.0080(17) 0.0007(15) C31 0.0164(19) 0.054(3) 0.045(3) -0.021(2) -0.0017(18) -0.0119(19) C32 0.033(3) 0.031(2) 0.047(3) -0.009(2) 0.001(2) -0.0064(19) C33 0.030(2) 0.0174(19) 0.040(3) 0.0008(18) -0.003(2) -0.0020(17) N2 0.0307(19) 0.033(2) 0.031(2) -0.0045(16) 0.0004(16) -0.0058(15) N3 0.0175(16) 0.040(2) 0.044(2) -0.0142(19) -0.0049(16) -0.0063(16) C14 0.032(2) 0.027(2) 0.046(3) -0.016(2) 0.0051(19) -0.0086(17) C15 0.037(2) 0.028(2) 0.043(3) -0.013(2) 0.007(2) -0.0153(18) C16 0.026(2) 0.027(2) 0.024(2) -0.0064(17) 0.0018(17) -0.0101(17) C17 0.021(2) 0.041(3) 0.052(3) -0.020(2) 0.007(2) -0.0134(19) C18 0.019(2) 0.032(2) 0.047(3) -0.008(2) 0.002(2) 0.0016(17) C19 0.0148(17) 0.036(2) 0.033(2) -0.0058(18) -0.0037(16) 0.0005(15) C20 0.0160(18) 0.033(2) 0.029(2) -0.0114(18) -0.0004(15) -0.0088(16) C21 0.0163(19) 0.033(2) 0.070(4) -0.020(2) -0.008(2) -0.0047(17) C22 0.027(2) 0.038(3) 0.078(4) -0.022(3) -0.012(3) -0.002(2) C23 0.0201(19) 0.051(3) 0.041(3) -0.009(2) -0.0058(18) -0.0159(19) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C46 1.361(5) . ? O3 H3O 0.8400 . ? O4 C44 1.371(5) . ? O4 H4O 0.8400 . ? C41 C42 1.514(6) . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 C43 1.376(7) . ? C42 C47 1.420(6) . ? C43 C44 1.386(6) . ? C43 H43 0.9500 . ? C44 C45 1.397(6) . ? C45 C46 1.392(6) . ? C45 H45 0.9500 . ? C46 C47 1.359(6) . ? C47 H47 0.9500 . ? N1 C9 1.332(6) . ? N1 C6 1.349(6) . ? C1 C2 1.325(8) . ? C1 C6 1.448(6) . ? C1 H1 0.9500 . ? C2 C3 1.421(9) . ? C2 H2 0.9500 . ? C3 C4 1.370(7) . ? C3 H3 0.9500 . ? C4 C5 1.444(6) . ? C4 H4 0.9500 . ? C5 C7 1.396(5) . ? C5 C6 1.440(6) . ? C7 C8 1.393(6) . ? C7 H7 0.9500 . ? C8 C13 1.410(7) . ? C8 C9 1.428(7) . ? C9 C10 1.403(7) . ? C10 C11 1.348(7) . ? C10 H10 0.9500 . ? C11 C12 1.415(10) . ? C11 H11 0.9500 . ? C12 C13 1.380(8) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? O1 C39 1.345(5) . ? O1 H1O 0.8400 . ? O2 C37 1.371(5) . ? O2 H2O 0.8400 . ? C34 C35 1.512(6) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 C36 1.363(6) . ? C35 C40 1.405(6) . ? C36 C37 1.425(5) . ? C36 H36 0.9500 . ? C37 C38 1.384(6) . ? C38 C39 1.384(6) . ? C38 H38 0.9500 . ? C39 C40 1.404(5) . ? C40 H40 0.9500 . ? N4 C28 1.313(7) . ? N4 C24 1.370(6) . ? N5 C31 1.289(7) . ? N5 C32 1.328(7) . ? C24 C25 1.333(6) . ? C24 H24 0.9500 . ? C25 C26 1.416(6) . ? C25 H25 0.9500 . ? C26 C27 1.417(6) . ? C26 C29 1.471(5) . ? C27 C28 1.352(7) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C30 1.351(7) . ? C29 C33 1.411(6) . ? C30 C31 1.418(5) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 C33 1.369(6) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? N2 C18 1.333(7) . ? N2 C14 1.372(6) . ? N3 C23 1.297(7) . ? N3 C22 1.346(7) . ? C14 C15 1.340(6) . ? C14 H14 0.9500 . ? C15 C16 1.428(6) . ? C15 H15 0.9500 . ? C16 C17 1.371(6) . ? C16 C20 1.505(5) . ? C17 C18 1.396(6) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.373(7) . ? C19 C23 1.434(5) . ? C19 H19 0.9500 . ? C20 C21 1.344(6) . ? C21 C22 1.407(6) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23 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 C46 O3 H3O 109.5 . . ? C44 O4 H4O 109.5 . . ? C42 C41 H41A 109.5 . . ? C42 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C42 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C43 C42 C47 118.3(4) . . ? C43 C42 C41 121.0(4) . . ? C47 C42 C41 120.6(4) . . ? C42 C43 C44 120.4(4) . . ? C42 C43 H43 119.8 . . ? C44 C43 H43 119.8 . . ? O4 C44 C43 118.0(4) . . ? O4 C44 C45 121.4(4) . . ? C43 C44 C45 120.6(4) . . ? C44 C45 C46 119.3(4) . . ? C44 C45 H45 120.3 . . ? C46 C45 H45 120.4 . . ? C47 C46 O3 119.5(4) . . ? C47 C46 C45 119.8(4) . . ? O3 C46 C45 120.7(4) . . ? C46 C47 C42 121.5(4) . . ? C46 C47 H47 119.3 . . ? C42 C47 H47 119.3 . . ? C9 N1 C6 121.7(4) . . ? C2 C1 C6 121.4(5) . . ? C2 C1 H1 119.3 . . ? C6 C1 H1 119.3 . . ? C1 C2 C3 121.9(5) . . ? C1 C2 H2 119.0 . . ? C3 C2 H2 119.0 . . ? C4 C3 C2 120.8(5) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 118.5(5) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? C7 C5 C6 120.7(4) . . ? C7 C5 C4 118.5(4) . . ? C6 C5 C4 120.8(4) . . ? N1 C6 C5 119.6(4) . . ? N1 C6 C1 123.9(4) . . ? C5 C6 C1 116.5(4) . . ? C5 C7 C8 116.6(4) . . ? C5 C7 H7 121.7 . . ? C8 C7 H7 121.7 . . ? C7 C8 C13 118.2(4) . . ? C7 C8 C9 121.4(4) . . ? C13 C8 C9 120.4(4) . . ? N1 C9 C10 123.1(4) . . ? N1 C9 C8 119.9(4) . . ? C10 C9 C8 117.0(5) . . ? C11 C10 C9 122.9(5) . . ? C11 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? C10 C11 C12 119.9(5) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 119.9(5) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C8 119.8(5) . . ? C12 C13 H13 120.1 . . ? C8 C13 H13 120.1 . . ? C39 O1 H1O 109.5 . . ? C37 O2 H2O 109.5 . . ? C35 C34 H34A 109.5 . . ? C35 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C35 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C36 C35 C40 121.2(4) . . ? C36 C35 C34 118.3(4) . . ? C40 C35 C34 120.4(4) . . ? C35 C36 C37 118.3(4) . . ? C35 C36 H36 120.8 . . ? C37 C36 H36 120.8 . . ? O2 C37 C38 122.1(4) . . ? O2 C37 C36 116.6(4) . . ? C38 C37 C36 121.3(4) . . ? C37 C38 C39 119.6(4) . . ? C37 C38 H38 120.2 . . ? C39 C38 H38 120.2 . . ? O1 C39 C38 122.3(4) . . ? O1 C39 C40 117.7(4) . . ? C38 C39 C40 119.9(4) . . ? C39 C40 C35 119.6(4) . . ? C39 C40 H40 120.2 . . ? C35 C40 H40 120.2 . . ? C28 N4 C24 114.4(4) . . ? C31 N5 C32 117.1(4) . . ? C25 C24 N4 123.7(4) . . ? C25 C24 H24 118.2 . . ? N4 C24 H24 118.1 . . ? C24 C25 C26 122.2(4) . . ? C24 C25 H25 118.9 . . ? C26 C25 H25 118.9 . . ? C25 C26 C27 113.2(4) . . ? C25 C26 C29 125.3(4) . . ? C27 C26 C29 121.6(4) . . ? C28 C27 C26 120.0(5) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? N4 C28 C27 126.5(5) . . ? N4 C28 H28 116.7 . . ? C27 C28 H28 116.7 . . ? C30 C29 C33 117.3(4) . . ? C30 C29 C26 122.4(4) . . ? C33 C29 C26 120.2(4) . . ? C29 C30 C31 118.7(4) . . ? C29 C30 H30 120.6 . . ? C31 C30 H30 120.6 . . ? N5 C31 C30 124.1(5) . . ? N5 C31 H31 117.9 . . ? C30 C31 H31 117.9 . . ? N5 C32 C33 124.0(5) . . ? N5 C32 H32 118.0 . . ? C33 C32 H32 118.0 . . ? C32 C33 C29 118.7(5) . . ? C32 C33 H33 120.6 . . ? C29 C33 H33 120.7 . . ? C18 N2 C14 115.9(4) . . ? C23 N3 C22 117.4(4) . . ? C15 C14 N2 123.6(5) . . ? C15 C14 H14 118.2 . . ? N2 C14 H14 118.2 . . ? C14 C15 C16 120.6(4) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C17 C16 C15 115.9(4) . . ? C17 C16 C20 123.1(4) . . ? C15 C16 C20 121.1(4) . . ? C16 C17 C18 120.2(5) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? N2 C18 C17 123.9(5) . . ? N2 C18 H18 118.1 . . ? C17 C18 H18 118.1 . . ? C20 C19 C23 116.9(4) . . ? C20 C19 H19 121.5 . . ? C23 C19 H19 121.5 . . ? C21 C20 C19 120.1(4) . . ? C21 C20 C16 121.0(4) . . ? C19 C20 C16 118.8(4) . . ? C20 C21 C22 119.1(5) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? N3 C22 C21 122.5(5) . . ? N3 C22 H22 118.8 . . ? C21 C22 H22 118.8 . . ? N3 C23 C19 123.9(5) . . ? N3 C23 H23 118.0 . . ? C19 C23 H23 118.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C47 C42 C43 C44 0.0(7) . . . . ? C41 C42 C43 C44 -177.1(4) . . . . ? C42 C43 C44 O4 179.9(4) . . . . ? C42 C43 C44 C45 0.9(7) . . . . ? O4 C44 C45 C46 179.5(4) . . . . ? C43 C44 C45 C46 -1.6(7) . . . . ? C44 C45 C46 C47 1.3(7) . . . . ? C44 C45 C46 O3 -179.1(4) . . . . ? O3 C46 C47 C42 -179.9(4) . . . . ? C45 C46 C47 C42 -0.4(7) . . . . ? C43 C42 C47 C46 -0.3(7) . . . . ? C41 C42 C47 C46 176.8(5) . . . . ? C6 C1 C2 C3 5.7(9) . . . . ? C1 C2 C3 C4 -3.7(9) . . . . ? C2 C3 C4 C5 0.6(8) . . . . ? C3 C4 C5 C7 -178.5(5) . . . . ? C3 C4 C5 C6 0.3(7) . . . . ? C9 N1 C6 C5 -0.1(6) . . . . ? C9 N1 C6 C1 179.0(5) . . . . ? C7 C5 C6 N1 -0.6(6) . . . . ? C4 C5 C6 N1 -179.4(4) . . . . ? C7 C5 C6 C1 -179.8(4) . . . . ? C4 C5 C6 C1 1.5(6) . . . . ? C2 C1 C6 N1 176.4(5) . . . . ? C2 C1 C6 C5 -4.5(7) . . . . ? C6 C5 C7 C8 0.6(5) . . . . ? C4 C5 C7 C8 179.4(4) . . . . ? C5 C7 C8 C13 178.6(4) . . . . ? C5 C7 C8 C9 0.0(6) . . . . ? C6 N1 C9 C10 -179.1(5) . . . . ? C6 N1 C9 C8 0.7(6) . . . . ? C7 C8 C9 N1 -0.6(7) . . . . ? C13 C8 C9 N1 -179.2(4) . . . . ? C7 C8 C9 C10 179.2(4) . . . . ? C13 C8 C9 C10 0.6(7) . . . . ? N1 C9 C10 C11 178.9(5) . . . . ? C8 C9 C10 C11 -0.9(8) . . . . ? C9 C10 C11 C12 2.6(9) . . . . ? C10 C11 C12 C13 -3.9(9) . . . . ? C11 C12 C13 C8 3.6(8) . . . . ? C7 C8 C13 C12 179.4(5) . . . . ? C9 C8 C13 C12 -2.0(8) . . . . ? C40 C35 C36 C37 1.3(7) . . . . ? C34 C35 C36 C37 179.7(4) . . . . ? C35 C36 C37 O2 179.1(4) . . . . ? C35 C36 C37 C38 -0.2(7) . . . . ? O2 C37 C38 C39 -179.3(4) . . . . ? C36 C37 C38 C39 0.0(6) . . . . ? C37 C38 C39 O1 179.6(4) . . . . ? C37 C38 C39 C40 -0.9(6) . . . . ? O1 C39 C40 C35 -178.5(4) . . . . ? C38 C39 C40 C35 2.0(6) . . . . ? C36 C35 C40 C39 -2.2(7) . . . . ? C34 C35 C40 C39 179.4(4) . . . . ? C28 N4 C24 C25 0.0(8) . . . . ? N4 C24 C25 C26 1.5(8) . . . . ? C24 C25 C26 C27 -1.5(6) . . . . ? C24 C25 C26 C29 178.3(5) . . . . ? C25 C26 C27 C28 0.2(7) . . . . ? C29 C26 C27 C28 -179.7(5) . . . . ? C24 N4 C28 C27 -1.5(9) . . . . ? C26 C27 C28 N4 1.4(10) . . . . ? C25 C26 C29 C30 168.3(4) . . . . ? C27 C26 C29 C30 -11.9(7) . . . . ? C25 C26 C29 C33 -13.1(7) . . . . ? C27 C26 C29 C33 166.8(4) . . . . ? C33 C29 C30 C31 -1.1(7) . . . . ? C26 C29 C30 C31 177.6(4) . . . . ? C32 N5 C31 C30 -1.1(8) . . . . ? C29 C30 C31 N5 1.9(8) . . . . ? C31 N5 C32 C33 -0.5(8) . . . . ? N5 C32 C33 C29 1.2(8) . . . . ? C30 C29 C33 C32 -0.3(7) . . . . ? C26 C29 C33 C32 -179.0(4) . . . . ? C18 N2 C14 C15 -0.2(8) . . . . ? N2 C14 C15 C16 0.7(8) . . . . ? C14 C15 C16 C17 -0.2(7) . . . . ? C14 C15 C16 C20 179.5(5) . . . . ? C15 C16 C17 C18 -0.8(7) . . . . ? C20 C16 C17 C18 179.6(4) . . . . ? C14 N2 C18 C17 -0.9(8) . . . . ? C16 C17 C18 N2 1.4(8) . . . . ? C23 C19 C20 C21 -0.6(7) . . . . ? C23 C19 C20 C16 -177.5(4) . . . . ? C17 C16 C20 C21 -166.4(5) . . . . ? C15 C16 C20 C21 14.0(7) . . . . ? C17 C16 C20 C19 10.5(7) . . . . ? C15 C16 C20 C19 -169.1(4) . . . . ? C19 C20 C21 C22 -0.2(8) . . . . ? C16 C20 C21 C22 176.7(5) . . . . ? C23 N3 C22 C21 -0.6(9) . . . . ? C20 C21 C22 N3 0.8(10) . . . . ? C22 N3 C23 C19 -0.2(8) . . . . ? C20 C19 C23 N3 0.8(8) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.223 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.040 # Attachment 'orc_bipy_anthracene.cif' data_orc_bipy_anthracene _database_code_depnum_ccdc_archive 'CCDC 836449' #TrackingRef 'orc_bipy_anthracene.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H42 N4 O4' _chemical_formula_weight 738.86 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 ? _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2102(9) _cell_length_b 10.4824(11) _cell_length_c 11.2645(11) _cell_angle_alpha 68.340(5) _cell_angle_beta 88.208(6) _cell_angle_gamma 70.827(5) _cell_volume 949.65(16) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 18780 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 390 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9756 _exptl_absorpt_correction_T_max 0.9836 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10154 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 4345 _reflns_number_gt 3653 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.2992P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4345 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1188 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.269 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.038 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 C21 C 0.94491(16) 0.88561(15) 0.51528(13) 0.0286(3) Uani 1 1 d . . . H3 H 0.9921(19) 0.4841(18) 0.9052(16) 0.036(4) Uiso 1 1 d . . . H5 H 1.4136(18) 0.2647(17) 0.8257(15) 0.030(4) Uiso 1 1 d . . . H7 H 1.0234(17) 0.3797(17) 0.5859(15) 0.029(4) Uiso 1 1 d . . . H1O H 1.384(3) 0.323(2) 1.000(2) 0.060(6) Uiso 1 1 d . . . H2O H 1.415(3) 0.197(2) 0.653(2) 0.063(6) Uiso 1 1 d . . . H8 H 0.655(2) 0.284(2) 0.6723(17) 0.046(5) Uiso 1 1 d . . . H9 H 0.915(2) 0.1827(19) 0.7490(16) 0.040(5) Uiso 1 1 d . . . H11 H 0.8719(19) -0.2197(19) 0.8671(16) 0.036(4) Uiso 1 1 d . . . H12 H 0.612(2) -0.1038(19) 0.7841(16) 0.041(5) Uiso 1 1 d . . . H14 H 1.127(2) 0.084(2) 0.8795(16) 0.041(5) Uiso 1 1 d . . . H15 H 1.391(2) -0.0319(19) 0.9560(17) 0.043(5) Uiso 1 1 d . . . H16 H 1.3832(19) -0.4066(19) 0.9514(16) 0.041(5) Uiso 1 1 d . . . H17 H 1.1231(19) -0.3064(18) 0.8773(15) 0.036(4) Uiso 1 1 d . . . H24 H 0.471(2) 1.226(2) 0.3615(18) 0.051(5) Uiso 1 1 d . . . H18 H 1.435(2) 0.575(2) 0.6643(17) 0.048(5) Uiso 1 1 d . . . H19 H 1.171(2) 0.628(2) 0.6074(17) 0.046(5) Uiso 1 1 d . . . H23 H 0.646(2) 0.9835(19) 0.4405(16) 0.040(5) Uiso 1 1 d . . . H21 H 0.9059(18) 0.8068(18) 0.5241(15) 0.033(4) Uiso 1 1 d . . . C4 C 1.21262(14) 0.37581(13) 0.88025(12) 0.0240(3) Uani 1 1 d . . . C13 C 1.09311(14) -0.09804(14) 0.86859(11) 0.0235(3) Uani 1 1 d . . . C5 C 1.30186(14) 0.31026(13) 0.80293(12) 0.0237(3) Uani 1 1 d . . . C7 C 1.07113(15) 0.37759(14) 0.66493(13) 0.0254(3) Uani 1 1 d . . . C2 C 0.98251(14) 0.44279(14) 0.74268(13) 0.0264(3) Uani 1 1 d . . . C10 C 0.92728(14) -0.02975(14) 0.81778(12) 0.0238(3) Uani 1 1 d . . . C3 C 1.05315(15) 0.44145(15) 0.85079(13) 0.0270(3) Uani 1 1 d . . . C6 C 1.23092(14) 0.31116(14) 0.69506(12) 0.0242(3) Uani 1 1 d . . . C12 C 0.68036(16) -0.04522(17) 0.77804(14) 0.0321(3) Uani 1 1 d . . . C9 C 0.85813(16) 0.12078(15) 0.75817(14) 0.0304(3) Uani 1 1 d . . . C11 C 0.83421(15) -0.11363(16) 0.82711(14) 0.0290(3) Uani 1 1 d . . . C14 C 1.17570(16) -0.01872(15) 0.89316(13) 0.0285(3) Uani 1 1 d . . . C8 C 0.70336(16) 0.17962(16) 0.71234(14) 0.0337(3) Uani 1 1 d . . . C15 C 1.33034(16) -0.08685(16) 0.93779(14) 0.0326(3) Uani 1 1 d . . . C17 C 1.17302(16) -0.24408(16) 0.89292(15) 0.0321(3) Uani 1 1 d . . . C16 C 1.32809(17) -0.30297(17) 0.93799(16) 0.0363(3) Uani 1 1 d . . . C1 C 0.80938(16) 0.51465(18) 0.71166(16) 0.0378(4) Uani 1 1 d . . . H1A H 0.7822 0.5419 0.6201 0.057 Uiso 1 1 calc R . . H1B H 0.7751 0.6023 0.7322 0.057 Uiso 1 1 calc R . . H1C H 0.7586 0.4463 0.7625 0.057 Uiso 1 1 calc R . . N1 N 0.61395(13) 0.09949(14) 0.72126(11) 0.0323(3) Uani 1 1 d . . . N2 N 1.40842(13) -0.22725(14) 0.96054(12) 0.0330(3) Uani 1 1 d . . . O1 O 1.27755(11) 0.37868(11) 0.98615(9) 0.0304(2) Uani 1 1 d . . . O2 O 1.31270(11) 0.24905(11) 0.61605(10) 0.0331(2) Uani 1 1 d . . . C22 C 0.84283(15) 1.02897(15) 0.46542(12) 0.0266(3) Uani 1 1 d . . . C23 C 0.68288(17) 1.06435(18) 0.42977(15) 0.0342(3) Uani 1 1 d . . . C20 C 1.10065(15) 0.85309(15) 0.55024(12) 0.0273(3) Uani 1 1 d . . . C19 C 1.20778(18) 0.70705(16) 0.59958(14) 0.0345(3) Uani 1 1 d . . . C24 C 0.58571(18) 1.20427(18) 0.38449(16) 0.0405(4) Uani 1 1 d . . . C18 C 1.35894(19) 0.67993(18) 0.63023(16) 0.0407(4) 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 C21 0.0317(7) 0.0284(7) 0.0296(7) -0.0140(6) 0.0052(5) -0.0118(6) C4 0.0231(6) 0.0218(6) 0.0252(6) -0.0073(5) -0.0018(5) -0.0068(5) C13 0.0207(6) 0.0276(7) 0.0195(6) -0.0068(5) 0.0019(5) -0.0073(5) C5 0.0180(6) 0.0209(6) 0.0288(6) -0.0077(5) -0.0020(5) -0.0039(5) C7 0.0234(6) 0.0232(6) 0.0263(6) -0.0064(5) -0.0047(5) -0.0064(5) C2 0.0201(6) 0.0226(6) 0.0314(7) -0.0070(5) -0.0017(5) -0.0043(5) C10 0.0203(6) 0.0284(7) 0.0207(6) -0.0089(5) 0.0036(5) -0.0066(5) C3 0.0223(6) 0.0274(7) 0.0290(7) -0.0115(5) 0.0021(5) -0.0048(5) C6 0.0233(6) 0.0209(6) 0.0262(6) -0.0082(5) 0.0004(5) -0.0053(5) C12 0.0230(6) 0.0380(8) 0.0370(8) -0.0166(6) 0.0032(6) -0.0099(6) C9 0.0243(7) 0.0280(7) 0.0347(7) -0.0087(6) 0.0034(5) -0.0073(5) C11 0.0248(6) 0.0283(7) 0.0327(7) -0.0108(6) 0.0019(5) -0.0081(5) C14 0.0271(7) 0.0266(7) 0.0307(7) -0.0104(5) 0.0001(5) -0.0080(5) C8 0.0259(7) 0.0294(8) 0.0365(8) -0.0090(6) 0.0019(6) -0.0018(6) C15 0.0273(7) 0.0370(8) 0.0362(8) -0.0154(6) -0.0021(6) -0.0120(6) C17 0.0247(7) 0.0287(7) 0.0420(8) -0.0130(6) -0.0028(6) -0.0080(6) C16 0.0274(7) 0.0286(7) 0.0481(9) -0.0138(6) -0.0056(6) -0.0034(6) C1 0.0213(7) 0.0403(8) 0.0441(8) -0.0147(7) -0.0043(6) -0.0018(6) N1 0.0211(5) 0.0397(7) 0.0326(6) -0.0156(5) 0.0026(5) -0.0041(5) N2 0.0243(6) 0.0374(7) 0.0342(6) -0.0124(5) -0.0045(5) -0.0073(5) O1 0.0258(5) 0.0352(5) 0.0308(5) -0.0168(4) -0.0028(4) -0.0060(4) O2 0.0249(5) 0.0397(6) 0.0331(5) -0.0206(4) -0.0020(4) -0.0009(4) C22 0.0276(6) 0.0279(7) 0.0250(6) -0.0120(5) 0.0048(5) -0.0081(5) C23 0.0295(7) 0.0399(8) 0.0373(8) -0.0183(6) 0.0034(6) -0.0127(6) C20 0.0287(7) 0.0286(7) 0.0244(6) -0.0119(5) 0.0045(5) -0.0076(5) C19 0.0386(8) 0.0267(7) 0.0353(8) -0.0118(6) 0.0027(6) -0.0073(6) C24 0.0275(7) 0.0445(9) 0.0443(9) -0.0173(7) -0.0021(6) -0.0045(6) C18 0.0363(8) 0.0321(8) 0.0426(9) -0.0130(7) -0.0017(7) 0.0013(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C21 C22 1.3927(19) . ? C21 C20 1.3942(19) . ? C21 H21 0.977(17) . ? C4 O1 1.3655(15) . ? C4 C5 1.3901(18) . ? C4 C3 1.3925(17) . ? C13 C17 1.3867(19) . ? C13 C14 1.3946(18) . ? C13 C10 1.4856(17) . ? C5 C6 1.3930(18) . ? C5 H5 0.978(16) . ? C7 C2 1.3897(19) . ? C7 C6 1.3963(17) . ? C7 H7 0.995(16) . ? C2 C3 1.3919(19) . ? C2 C1 1.5112(17) . ? C10 C9 1.3895(19) . ? C10 C11 1.3929(19) . ? C3 H3 0.952(17) . ? C6 O2 1.3591(16) . ? C12 N1 1.3353(19) . ? C12 C11 1.3844(19) . ? C12 H12 0.997(18) . ? C9 C8 1.3828(19) . ? C9 H9 0.940(18) . ? C11 H11 0.973(17) . ? C14 C15 1.3795(19) . ? C14 H14 0.977(18) . ? C8 N1 1.334(2) . ? C8 H8 0.961(19) . ? C15 N2 1.3367(19) . ? C15 H15 0.995(18) . ? C17 C16 1.3834(19) . ? C17 H17 0.978(17) . ? C16 N2 1.3372(19) . ? C16 H16 0.991(17) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O1 H1O 0.95(2) . ? O2 H2O 0.94(2) . ? C22 C23 1.4273(19) . ? C22 C20 1.4445(19) 2_776 ? C23 C24 1.351(2) . ? C23 H23 0.980(18) . ? C20 C19 1.428(2) . ? C20 C22 1.4445(19) 2_776 ? C19 C18 1.355(2) . ? C19 H19 0.971(19) . ? C24 C18 1.419(2) 2_776 ? C24 H24 1.022(19) . ? C18 C24 1.419(2) 2_776 ? C18 H18 1.021(19) . ? 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 C22 C21 C20 121.57(13) . . ? C22 C21 H21 118.6(10) . . ? C20 C21 H21 119.8(9) . . ? O1 C4 C5 121.54(11) . . ? O1 C4 C3 118.07(12) . . ? C5 C4 C3 120.39(12) . . ? C17 C13 C14 117.00(12) . . ? C17 C13 C10 121.17(12) . . ? C14 C13 C10 121.83(12) . . ? C4 C5 C6 119.60(11) . . ? C4 C5 H5 118.9(9) . . ? C6 C5 H5 121.5(9) . . ? C2 C7 C6 120.01(12) . . ? C2 C7 H7 121.3(9) . . ? C6 C7 H7 118.7(9) . . ? C7 C2 C3 119.93(12) . . ? C7 C2 C1 120.66(12) . . ? C3 C2 C1 119.40(12) . . ? C9 C10 C11 116.95(12) . . ? C9 C10 C13 121.49(12) . . ? C11 C10 C13 121.56(12) . . ? C2 C3 C4 119.94(12) . . ? C2 C3 H3 119.9(10) . . ? C4 C3 H3 120.1(10) . . ? O2 C6 C5 122.01(11) . . ? O2 C6 C7 117.87(11) . . ? C5 C6 C7 120.12(12) . . ? N1 C12 C11 123.42(13) . . ? N1 C12 H12 116.1(10) . . ? C11 C12 H12 120.5(10) . . ? C8 C9 C10 119.52(13) . . ? C8 C9 H9 119.8(11) . . ? C10 C9 H9 120.6(11) . . ? C12 C11 C10 119.54(13) . . ? C12 C11 H11 117.3(10) . . ? C10 C11 H11 123.1(10) . . ? C15 C14 C13 119.41(13) . . ? C15 C14 H14 118.8(10) . . ? C13 C14 H14 121.8(10) . . ? N1 C8 C9 123.63(14) . . ? N1 C8 H8 116.5(11) . . ? C9 C8 H8 119.9(11) . . ? N2 C15 C14 123.93(13) . . ? N2 C15 H15 115.6(10) . . ? C14 C15 H15 120.4(10) . . ? C16 C17 C13 119.43(13) . . ? C16 C17 H17 118.9(10) . . ? C13 C17 H17 121.6(10) . . ? N2 C16 C17 123.91(14) . . ? N2 C16 H16 118.4(10) . . ? C17 C16 H16 117.7(10) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C8 N1 C12 116.93(12) . . ? C15 N2 C16 116.32(12) . . ? C4 O1 H1O 109.9(13) . . ? C6 O2 H2O 109.1(13) . . ? C21 C22 C23 122.38(13) . . ? C21 C22 C20 119.30(12) . 2_776 ? C23 C22 C20 118.32(12) . 2_776 ? C24 C23 C22 121.10(14) . . ? C24 C23 H23 121.2(10) . . ? C22 C23 H23 117.7(10) . . ? C21 C20 C19 122.47(13) . . ? C21 C20 C22 119.13(12) . 2_776 ? C19 C20 C22 118.40(13) . 2_776 ? C18 C19 C20 120.77(14) . . ? C18 C19 H19 120.6(11) . . ? C20 C19 H19 118.6(11) . . ? C23 C24 C18 120.58(14) . 2_776 ? C23 C24 H24 119.3(11) . . ? C18 C24 H24 120.1(11) 2_776 . ? C19 C18 C24 120.82(14) . 2_776 ? C19 C18 H18 119.9(10) . . ? C24 C18 H18 119.2(10) 2_776 . ? 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 C4 C5 C6 -179.36(12) . . . . ? C3 C4 C5 C6 0.32(19) . . . . ? C6 C7 C2 C3 -0.2(2) . . . . ? C6 C7 C2 C1 -179.78(12) . . . . ? C17 C13 C10 C9 -160.78(13) . . . . ? C14 C13 C10 C9 18.79(19) . . . . ? C17 C13 C10 C11 18.88(19) . . . . ? C14 C13 C10 C11 -161.55(13) . . . . ? C7 C2 C3 C4 0.5(2) . . . . ? C1 C2 C3 C4 -179.88(13) . . . . ? O1 C4 C3 C2 179.10(12) . . . . ? C5 C4 C3 C2 -0.6(2) . . . . ? C4 C5 C6 O2 179.82(12) . . . . ? C4 C5 C6 C7 0.02(19) . . . . ? C2 C7 C6 O2 -179.90(12) . . . . ? C2 C7 C6 C5 -0.09(19) . . . . ? C11 C10 C9 C8 0.3(2) . . . . ? C13 C10 C9 C8 -179.97(12) . . . . ? N1 C12 C11 C10 -0.2(2) . . . . ? C9 C10 C11 C12 -0.1(2) . . . . ? C13 C10 C11 C12 -179.81(12) . . . . ? C17 C13 C14 C15 0.9(2) . . . . ? C10 C13 C14 C15 -178.66(12) . . . . ? C10 C9 C8 N1 -0.3(2) . . . . ? C13 C14 C15 N2 -0.5(2) . . . . ? C14 C13 C17 C16 -0.8(2) . . . . ? C10 C13 C17 C16 178.82(13) . . . . ? C13 C17 C16 N2 0.1(2) . . . . ? C9 C8 N1 C12 0.0(2) . . . . ? C11 C12 N1 C8 0.2(2) . . . . ? C14 C15 N2 C16 -0.2(2) . . . . ? C17 C16 N2 C15 0.4(2) . . . . ? C20 C21 C22 C23 -179.64(13) . . . . ? C20 C21 C22 C20 -0.1(2) . . . 2_776 ? C21 C22 C23 C24 178.40(14) . . . . ? C20 C22 C23 C24 -1.1(2) 2_776 . . . ? C22 C21 C20 C19 -178.96(13) . . . . ? C22 C21 C20 C22 0.1(2) . . . 2_776 ? C21 C20 C19 C18 178.72(14) . . . . ? C22 C20 C19 C18 -0.4(2) 2_776 . . . ? C22 C23 C24 C18 0.8(2) . . . 2_776 ? C20 C19 C18 C24 0.7(2) . . . 2_776 ? # Attachment 'orc_bipy_phenazine.cif' data_orc_bipy_phenazine _database_code_depnum_ccdc_archive 'CCDC 836450' #TrackingRef 'orc_bipy_phenazine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H40 N6 O4' _chemical_formula_weight 740.84 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 ? _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4283(10) _cell_length_b 10.1821(10) _cell_length_c 11.1549(11) _cell_angle_alpha 69.876(5) _cell_angle_beta 86.613(6) _cell_angle_gamma 69.427(5) _cell_volume 939.04(16) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8553 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 390 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9586 _exptl_absorpt_correction_T_max 0.9915 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9968 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 4305 _reflns_number_gt 3306 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+0.3427P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4305 _refine_ls_number_parameters 333 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1291 _refine_ls_wR_factor_gt 0.1200 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.237 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.041 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 H5 H 0.422(2) 0.7687(19) -0.1666(15) 0.027(4) Uiso 1 1 d . . . H7 H -0.0139(19) 0.9935(19) -0.0996(16) 0.028(4) Uiso 1 1 d . . . H3 H 0.066(2) 0.872(2) -0.4196(18) 0.033(5) Uiso 1 1 d . . . H12 H 0.654(2) 0.393(2) -0.2252(19) 0.050(6) Uiso 1 1 d . . . H1C H -0.194(2) 0.989(2) -0.369(2) 0.053(6) Uiso 1 1 d . . . H17 H 1.152(2) 0.590(2) -0.133(2) 0.050(6) Uiso 1 1 d . . . H11 H 0.905(2) 0.278(2) -0.1473(19) 0.048(6) Uiso 1 1 d . . . H16 H 1.410(2) 0.475(2) -0.0689(19) 0.050(6) Uiso 1 1 d . . . H1O H 0.451(3) 0.697(3) -0.341(2) 0.066(7) Uiso 1 1 d . . . H22 H 0.319(2) 0.549(3) 0.555(2) 0.056(6) Uiso 1 1 d . . . H2O H 0.362(3) 0.831(2) 0.013(2) 0.055(6) Uiso 1 1 d . . . H8 H 0.673(2) 0.791(2) -0.2925(19) 0.048(6) Uiso 1 1 d . . . H23 H 0.508(2) 0.308(2) 0.620(2) 0.051(6) Uiso 1 1 d . . . H19 H -0.183(2) 0.872(3) 0.409(2) 0.062(7) Uiso 1 1 d . . . H1A H -0.227(2) 1.015(2) -0.237(2) 0.050(6) Uiso 1 1 d . . . H9 H 0.927(2) 0.694(2) -0.2237(19) 0.047(6) Uiso 1 1 d . . . H1B H -0.188(3) 1.130(3) -0.354(2) 0.069(7) Uiso 1 1 d . . . H14 H 1.146(3) 0.188(3) -0.114(2) 0.067(7) Uiso 1 1 d . . . H18 H -0.446(2) 0.904(3) 0.364(2) 0.059(6) Uiso 1 1 d . . . H15 H 1.400(3) 0.086(3) -0.052(2) 0.080(8) Uiso 1 1 d . . . O2 O 0.26107(13) 0.88096(13) -0.00421(11) 0.0311(3) Uani 1 1 d . . . O1 O 0.35270(13) 0.74656(14) -0.38181(11) 0.0340(3) Uani 1 1 d . . . C5 C 0.31343(16) 0.81215(16) -0.19216(15) 0.0254(3) Uani 1 1 d . . . N1 N 0.64318(14) 0.60029(16) -0.26526(14) 0.0335(3) Uani 1 1 d . . . C3 C 0.10297(16) 0.87564(16) -0.34135(15) 0.0250(3) Uani 1 1 d . . . C13 C 1.11484(17) 0.40147(17) -0.13109(14) 0.0259(3) Uani 1 1 d . . . C6 C 0.21244(16) 0.87839(16) -0.11611(14) 0.0244(3) Uani 1 1 d . . . C2 C 0.00320(16) 0.94486(16) -0.26602(15) 0.0251(3) Uani 1 1 d . . . C7 C 0.05736(17) 0.94511(16) -0.15259(15) 0.0260(3) Uani 1 1 d . . . C10 C 0.95106(16) 0.47001(17) -0.17579(14) 0.0245(3) Uani 1 1 d . . . N2 N 1.42721(15) 0.27017(16) -0.05409(15) 0.0385(4) Uani 1 1 d . . . C4 C 0.25842(16) 0.81046(16) -0.30442(15) 0.0251(3) Uani 1 1 d . . . C1 C -0.16415(18) 1.0238(2) -0.30779(19) 0.0352(4) Uani 1 1 d . . . C17 C 1.19824(18) 0.48460(19) -0.11818(16) 0.0318(4) Uani 1 1 d . . . C16 C 1.35148(19) 0.4154(2) -0.08023(17) 0.0348(4) Uani 1 1 d . . . C12 C 0.71439(19) 0.4529(2) -0.22215(18) 0.0358(4) Uani 1 1 d . . . C11 C 0.86556(18) 0.38395(19) -0.17675(17) 0.0325(4) Uani 1 1 d . . . C8 C 0.72495(19) 0.6828(2) -0.26315(19) 0.0396(4) Uani 1 1 d . . . C9 C 0.87668(19) 0.62423(19) -0.21987(18) 0.0362(4) Uani 1 1 d . . . C14 C 1.1930(2) 0.2505(2) -0.1041(2) 0.0511(6) Uani 1 1 d . . . C15 C 1.3460(2) 0.1918(2) -0.0672(3) 0.0622(7) Uani 1 1 d . . . N3 N 0.04105(16) 0.62571(16) 0.48820(14) 0.0342(3) Uani 1 1 d . . . C22 C 0.2966(2) 0.4608(2) 0.56199(17) 0.0383(4) Uani 1 1 d . . . C21 C 0.14317(19) 0.48565(19) 0.52936(15) 0.0314(4) Uani 1 1 d . . . C20 C -0.10177(19) 0.64061(19) 0.45926(15) 0.0321(4) Uani 1 1 d . . . C19 C -0.2157(2) 0.7860(2) 0.41639(19) 0.0420(4) Uani 1 1 d . . . C23 C 0.4016(2) 0.3212(2) 0.60060(19) 0.0454(5) Uani 1 1 d . . . C18 C -0.3607(2) 0.8034(2) 0.3888(2) 0.0481(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0236(6) 0.0350(6) 0.0335(6) -0.0151(5) -0.0060(5) -0.0047(5) O1 0.0202(6) 0.0412(7) 0.0371(7) -0.0193(5) -0.0015(5) -0.0004(5) C5 0.0151(7) 0.0230(7) 0.0335(8) -0.0066(6) -0.0034(6) -0.0036(6) N1 0.0191(6) 0.0387(8) 0.0378(8) -0.0137(6) 0.0015(5) -0.0040(6) C3 0.0215(7) 0.0238(7) 0.0264(8) -0.0052(6) -0.0036(6) -0.0066(6) C13 0.0216(7) 0.0273(8) 0.0246(8) -0.0056(6) -0.0012(6) -0.0067(6) C6 0.0223(7) 0.0211(7) 0.0280(8) -0.0065(6) -0.0024(6) -0.0069(6) C2 0.0179(7) 0.0218(7) 0.0300(8) -0.0034(6) -0.0026(6) -0.0052(6) C7 0.0202(7) 0.0241(7) 0.0294(8) -0.0084(6) 0.0011(6) -0.0036(6) C10 0.0200(7) 0.0277(8) 0.0226(7) -0.0071(6) 0.0016(5) -0.0063(6) N2 0.0232(7) 0.0365(8) 0.0496(9) -0.0112(7) -0.0115(6) -0.0045(6) C4 0.0203(7) 0.0205(7) 0.0304(8) -0.0066(6) -0.0002(6) -0.0043(6) C1 0.0185(8) 0.0409(10) 0.0376(10) -0.0113(8) -0.0052(7) -0.0015(7) C17 0.0268(8) 0.0282(8) 0.0380(9) -0.0085(7) -0.0037(7) -0.0088(7) C16 0.0275(8) 0.0366(9) 0.0398(10) -0.0103(7) -0.0059(7) -0.0124(7) C12 0.0229(8) 0.0372(9) 0.0483(11) -0.0166(8) -0.0011(7) -0.0092(7) C11 0.0241(8) 0.0278(8) 0.0426(10) -0.0109(7) -0.0010(7) -0.0063(7) C8 0.0239(8) 0.0297(9) 0.0554(12) -0.0088(8) -0.0006(7) -0.0032(7) C9 0.0246(8) 0.0264(8) 0.0525(11) -0.0080(7) -0.0003(7) -0.0080(7) C14 0.0287(9) 0.0260(9) 0.0929(17) -0.0135(10) -0.0193(10) -0.0061(8) C15 0.0308(10) 0.0274(10) 0.116(2) -0.0157(11) -0.0278(11) 0.0004(8) N3 0.0371(8) 0.0346(8) 0.0354(8) -0.0134(6) 0.0040(6) -0.0168(6) C22 0.0370(10) 0.0466(11) 0.0381(10) -0.0182(8) 0.0043(7) -0.0195(8) C21 0.0344(9) 0.0343(9) 0.0271(8) -0.0121(7) 0.0037(6) -0.0127(7) C20 0.0324(9) 0.0362(9) 0.0291(8) -0.0128(7) 0.0024(6) -0.0123(7) C19 0.0441(11) 0.0335(9) 0.0466(11) -0.0115(8) 0.0006(8) -0.0135(8) C23 0.0321(10) 0.0573(12) 0.0451(11) -0.0166(9) -0.0014(8) -0.0141(9) C18 0.0394(11) 0.0406(11) 0.0522(12) -0.0111(9) -0.0053(9) -0.0034(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C6 1.3665(18) . ? O2 H2O 0.90(2) . ? O1 C4 1.3594(18) . ? O1 H1O 0.94(3) . ? C5 C6 1.389(2) . ? C5 C4 1.391(2) . ? C5 H5 0.980(17) . ? N1 C12 1.330(2) . ? N1 C8 1.331(2) . ? C3 C2 1.391(2) . ? C3 C4 1.399(2) . ? C3 H3 0.977(18) . ? C13 C14 1.381(2) . ? C13 C17 1.386(2) . ? C13 C10 1.488(2) . ? C6 C7 1.395(2) . ? C2 C7 1.393(2) . ? C2 C1 1.513(2) . ? C7 H7 0.982(17) . ? C10 C11 1.386(2) . ? C10 C9 1.391(2) . ? N2 C16 1.329(2) . ? N2 C15 1.330(3) . ? C1 H1C 0.97(2) . ? C1 H1A 0.95(2) . ? C1 H1B 0.97(3) . ? C17 C16 1.384(2) . ? C17 H17 0.96(2) . ? C16 H16 0.99(2) . ? C12 C11 1.385(2) . ? C12 H12 0.98(2) . ? C11 H11 0.95(2) . ? C8 C9 1.385(2) . ? C8 H8 0.98(2) . ? C9 H9 0.97(2) . ? C14 C15 1.379(3) . ? C14 H14 0.93(3) . ? C15 H15 0.97(3) . ? N3 C21 1.345(2) . ? N3 C20 1.347(2) . ? C22 C23 1.351(3) . ? C22 C21 1.425(2) . ? C22 H22 0.97(2) . ? C21 C20 1.434(2) 2_566 ? C20 C19 1.425(2) . ? C20 C21 1.434(2) 2_566 ? C19 C18 1.355(3) . ? C19 H19 1.00(2) . ? C23 C18 1.417(3) 2_566 ? C23 H23 0.99(2) . ? C18 C23 1.417(3) 2_566 ? C18 H18 1.01(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O2 H2O 111.1(14) . . ? C4 O1 H1O 109.0(15) . . ? C6 C5 C4 119.41(13) . . ? C6 C5 H5 119.5(10) . . ? C4 C5 H5 121.1(10) . . ? C12 N1 C8 116.55(14) . . ? C2 C3 C4 119.55(14) . . ? C2 C3 H3 120.8(10) . . ? C4 C3 H3 119.6(10) . . ? C14 C13 C17 116.45(15) . . ? C14 C13 C10 121.00(15) . . ? C17 C13 C10 122.52(14) . . ? O2 C6 C5 121.45(13) . . ? O2 C6 C7 118.00(13) . . ? C5 C6 C7 120.55(14) . . ? C3 C2 C7 120.12(13) . . ? C3 C2 C1 120.52(14) . . ? C7 C2 C1 119.34(14) . . ? C2 C7 C6 119.77(14) . . ? C2 C7 H7 119.6(10) . . ? C6 C7 H7 120.6(10) . . ? C11 C10 C9 116.75(14) . . ? C11 C10 C13 121.86(14) . . ? C9 C10 C13 121.38(14) . . ? C16 N2 C15 115.58(15) . . ? O1 C4 C5 121.59(13) . . ? O1 C4 C3 117.84(14) . . ? C5 C4 C3 120.57(14) . . ? C2 C1 H1C 111.5(13) . . ? C2 C1 H1A 112.3(13) . . ? H1C C1 H1A 110.8(18) . . ? C2 C1 H1B 111.7(14) . . ? H1C C1 H1B 103.7(18) . . ? H1A C1 H1B 106.4(19) . . ? C16 C17 C13 119.90(15) . . ? C16 C17 H17 118.4(13) . . ? C13 C17 H17 121.7(13) . . ? N2 C16 C17 123.91(16) . . ? N2 C16 H16 116.4(12) . . ? C17 C16 H16 119.7(12) . . ? N1 C12 C11 123.59(17) . . ? N1 C12 H12 116.2(12) . . ? C11 C12 H12 120.2(12) . . ? C12 C11 C10 119.82(15) . . ? C12 C11 H11 116.7(13) . . ? C10 C11 H11 123.5(13) . . ? N1 C8 C9 124.07(16) . . ? N1 C8 H8 117.2(12) . . ? C9 C8 H8 118.7(12) . . ? C8 C9 C10 119.21(16) . . ? C8 C9 H9 117.8(12) . . ? C10 C9 H9 123.0(12) . . ? C15 C14 C13 119.40(18) . . ? C15 C14 H14 118.9(15) . . ? C13 C14 H14 121.6(15) . . ? N2 C15 C14 124.76(18) . . ? N2 C15 H15 116.9(15) . . ? C14 C15 H15 118.3(15) . . ? C21 N3 C20 116.47(15) . . ? C23 C22 C21 120.65(18) . . ? C23 C22 H22 123.4(13) . . ? C21 C22 H22 115.9(13) . . ? N3 C21 C22 119.80(16) . . ? N3 C21 C20 121.51(15) . 2_566 ? C22 C21 C20 118.69(16) . 2_566 ? N3 C20 C19 119.22(16) . . ? N3 C20 C21 122.02(15) . 2_566 ? C19 C20 C21 118.76(16) . 2_566 ? C18 C19 C20 120.27(19) . . ? C18 C19 H19 123.0(13) . . ? C20 C19 H19 116.7(13) . . ? C22 C23 C18 120.62(18) . 2_566 ? C22 C23 H23 118.9(13) . . ? C18 C23 H23 120.5(12) 2_566 . ? C19 C18 C23 120.99(18) . 2_566 ? C19 C18 H18 122.7(13) . . ? C23 C18 H18 116.3(13) 2_566 . ? 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 C4 C5 C6 O2 179.13(14) . . . . ? C4 C5 C6 C7 -1.1(2) . . . . ? C4 C3 C2 C7 -2.0(2) . . . . ? C4 C3 C2 C1 176.51(15) . . . . ? C3 C2 C7 C6 1.3(2) . . . . ? C1 C2 C7 C6 -177.18(15) . . . . ? O2 C6 C7 C2 -179.99(13) . . . . ? C5 C6 C7 C2 0.2(2) . . . . ? C14 C13 C10 C11 8.3(3) . . . . ? C17 C13 C10 C11 -173.79(16) . . . . ? C14 C13 C10 C9 -171.08(19) . . . . ? C17 C13 C10 C9 6.8(2) . . . . ? C6 C5 C4 O1 -179.79(14) . . . . ? C6 C5 C4 C3 0.4(2) . . . . ? C2 C3 C4 O1 -178.69(13) . . . . ? C2 C3 C4 C5 1.1(2) . . . . ? C14 C13 C17 C16 0.1(3) . . . . ? C10 C13 C17 C16 -177.86(15) . . . . ? C15 N2 C16 C17 0.3(3) . . . . ? C13 C17 C16 N2 -0.1(3) . . . . ? C8 N1 C12 C11 -0.1(3) . . . . ? N1 C12 C11 C10 -0.6(3) . . . . ? C9 C10 C11 C12 1.0(2) . . . . ? C13 C10 C11 C12 -178.41(15) . . . . ? C12 N1 C8 C9 0.2(3) . . . . ? N1 C8 C9 C10 0.2(3) . . . . ? C11 C10 C9 C8 -0.9(3) . . . . ? C13 C10 C9 C8 178.56(16) . . . . ? C17 C13 C14 C15 -0.3(3) . . . . ? C10 C13 C14 C15 177.7(2) . . . . ? C16 N2 C15 C14 -0.5(4) . . . . ? C13 C14 C15 N2 0.5(4) . . . . ? C20 N3 C21 C22 -179.94(15) . . . . ? C20 N3 C21 C20 0.4(3) . . . 2_566 ? C23 C22 C21 N3 -178.42(17) . . . . ? C23 C22 C21 C20 1.2(3) . . . 2_566 ? C21 N3 C20 C19 179.34(15) . . . . ? C21 N3 C20 C21 -0.4(3) . . . 2_566 ? N3 C20 C19 C18 -178.90(18) . . . . ? C21 C20 C19 C18 0.9(3) 2_566 . . . ? C21 C22 C23 C18 -0.9(3) . . . 2_566 ? C20 C19 C18 C23 -1.2(3) . . . 2_566 ? # Attachment 'orcinol 44bp--ch3cn3.cif' data_orcinol _database_code_depnum_ccdc_archive 'CCDC 836451' #TrackingRef 'orcinol 44bp--ch3cn3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H40 N6 O4' _chemical_formula_weight 716.82 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 b c 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' '-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 9.346(6) _cell_length_b 23.250(15) _cell_length_c 33.59(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7299(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 13427 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3024 _exptl_absorpt_coefficient_mu 0.085 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9667 _exptl_absorpt_correction_T_max 0.9831 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 55276 _diffrn_reflns_av_R_equivalents 0.1354 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 27.49 _reflns_number_total 8337 _reflns_number_gt 6722 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0863P)^2^+11.9541P] 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 8337 _refine_ls_number_parameters 493 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1216 _refine_ls_R_factor_gt 0.0996 _refine_ls_wR_factor_ref 0.2708 _refine_ls_wR_factor_gt 0.2561 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_restrained_S_all 1.186 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7380(4) 0.17314(15) 0.07211(10) 0.0290(7) Uani 1 1 d . . . C2 C 0.7332(4) 0.17058(16) 0.11334(10) 0.0309(7) Uani 1 1 d . . . H2 H 0.7410 0.1345 0.1265 0.037 Uiso 1 1 calc R . . C3 C 0.7169(4) 0.22044(16) 0.13537(10) 0.0294(7) Uani 1 1 d . . . C4 C 0.7048(4) 0.27324(15) 0.11606(10) 0.0299(7) Uani 1 1 d . . . H4 H 0.6939 0.3076 0.1311 0.036 Uiso 1 1 calc R . . C5 C 0.7087(4) 0.27553(15) 0.07461(10) 0.0295(7) Uani 1 1 d . . . C6 C 0.7252(4) 0.22541(14) 0.05267(9) 0.0264(7) Uani 1 1 d . . . H6 H 0.7276 0.2269 0.0244 0.032 Uiso 1 1 calc R . . C7 C 0.7104(5) 0.21710(18) 0.18013(10) 0.0395(9) Uani 1 1 d . . . H7A H 0.6146 0.2047 0.1884 0.059 Uiso 1 1 calc R . . H7B H 0.7310 0.2551 0.1915 0.059 Uiso 1 1 calc R . . H7C H 0.7814 0.1893 0.1897 0.059 Uiso 1 1 calc R . . C8 C 0.3980(4) -0.06045(15) 0.33418(10) 0.0299(7) Uani 1 1 d . . . C9 C 0.3763(4) -0.06322(15) 0.37491(10) 0.0305(7) Uani 1 1 d . . . H9 H 0.3512 -0.0987 0.3870 0.037 Uiso 1 1 calc R . . C10 C 0.3914(4) -0.01414(15) 0.39796(10) 0.0289(7) Uani 1 1 d . . . C11 C 0.4259(4) 0.03797(15) 0.37989(10) 0.0301(7) Uani 1 1 d . . . H11 H 0.4346 0.0718 0.3956 0.036 Uiso 1 1 calc R . . C12 C 0.4477(4) 0.04059(14) 0.33898(10) 0.0273(7) Uani 1 1 d . . . C13 C 0.4338(4) -0.00869(15) 0.31585(10) 0.0286(7) Uani 1 1 d . . . H13 H 0.4486 -0.0071 0.2879 0.034 Uiso 1 1 calc R . . C14 C 0.3743(4) -0.01774(17) 0.44241(10) 0.0377(8) Uani 1 1 d . . . H14A H 0.2958 -0.0441 0.4488 0.057 Uiso 1 1 calc R . . H14B H 0.3528 0.0205 0.4530 0.057 Uiso 1 1 calc R . . H14C H 0.4633 -0.0320 0.4543 0.057 Uiso 1 1 calc R . . C15 C 0.8444(4) 0.19158(18) 0.45541(11) 0.0385(9) Uani 1 1 d . . . H15 H 0.9317 0.1841 0.4689 0.046 Uiso 1 1 calc R . . C16 C 0.8507(4) 0.20803(17) 0.41615(11) 0.0354(8) Uani 1 1 d . . . H16 H 0.9404 0.2107 0.4030 0.043 Uiso 1 1 calc R . . C17 C 0.7253(4) 0.22066(15) 0.39587(10) 0.0293(7) Uani 1 1 d . . . C18 C 0.5976(4) 0.21516(18) 0.41679(11) 0.0383(9) Uani 1 1 d . . . H18 H 0.5088 0.2235 0.4043 0.046 Uiso 1 1 calc R . . C19 C 0.6019(4) 0.19743(19) 0.45587(11) 0.0407(9) Uani 1 1 d . . . H19 H 0.5136 0.1934 0.4696 0.049 Uiso 1 1 calc R . . C20 C 0.8410(5) 0.28623(18) 0.29892(12) 0.0422(9) Uani 1 1 d . . . H20 H 0.9203 0.3074 0.2890 0.051 Uiso 1 1 calc R . . C21 C 0.8421(4) 0.27018(16) 0.33832(10) 0.0346(8) Uani 1 1 d . . . H21 H 0.9204 0.2803 0.3549 0.042 Uiso 1 1 calc R . . C22 C 0.7271(4) 0.23887(15) 0.35370(10) 0.0297(7) Uani 1 1 d . . . C23 C 0.6156(4) 0.22567(16) 0.32779(11) 0.0356(8) Uani 1 1 d . . . H23 H 0.5346 0.2049 0.3370 0.043 Uiso 1 1 calc R . . C24 C 0.6244(5) 0.24309(19) 0.28884(12) 0.0449(10) Uani 1 1 d . . . H24 H 0.5482 0.2330 0.2715 0.054 Uiso 1 1 calc R . . C25 C 0.4742(5) 0.38155(18) 0.29055(11) 0.0408(9) Uani 1 1 d . . . H25 H 0.3907 0.3661 0.2784 0.049 Uiso 1 1 calc R . . C26 C 0.4893(4) 0.37564(17) 0.33123(10) 0.0355(8) Uani 1 1 d . . . H26 H 0.4173 0.3571 0.3465 0.043 Uiso 1 1 calc R . . C27 C 0.6118(4) 0.39733(15) 0.34951(10) 0.0312(7) Uani 1 1 d . . . C28 C 0.7101(4) 0.42582(17) 0.32559(11) 0.0374(8) Uani 1 1 d . . . H28 H 0.7939 0.4423 0.3369 0.045 Uiso 1 1 calc R . . C29 C 0.6847(5) 0.42990(17) 0.28537(12) 0.0439(10) Uani 1 1 d . . . H29 H 0.7527 0.4497 0.2695 0.053 Uiso 1 1 calc R . . C30 C 0.7955(5) 0.37318(19) 0.44721(13) 0.0481(10) Uani 1 1 d . . . H30 H 0.8902 0.3673 0.4566 0.058 Uiso 1 1 calc R . . C31 C 0.7745(5) 0.38199(18) 0.40716(12) 0.0404(9) Uani 1 1 d . . . H31 H 0.8541 0.3833 0.3896 0.048 Uiso 1 1 calc R . . C32 C 0.6372(4) 0.38890(15) 0.39245(10) 0.0312(7) Uani 1 1 d . . . C33 C 0.5253(4) 0.38773(17) 0.41960(10) 0.0370(8) Uani 1 1 d . . . H33 H 0.4292 0.3922 0.4109 0.044 Uiso 1 1 calc R . . C34 C 0.5556(5) 0.37996(19) 0.45932(11) 0.0471(10) Uani 1 1 d . . . H34 H 0.4782 0.3798 0.4777 0.056 Uiso 1 1 calc R . . C35 C 0.3891(5) 0.11055(18) 0.22182(12) 0.0417(9) Uani 1 1 d . . . H35 H 0.3265 0.1343 0.2369 0.050 Uiso 1 1 calc R . . C36 C 0.3576(4) 0.10151(17) 0.18233(12) 0.0394(9) Uani 1 1 d . . . H36 H 0.2751 0.1186 0.1708 0.047 Uiso 1 1 calc R . . C37 C 0.4481(4) 0.06696(15) 0.15941(10) 0.0314(7) Uani 1 1 d . . . C38 C 0.5679(4) 0.04407(16) 0.17831(11) 0.0335(8) Uani 1 1 d . . . H38 H 0.6340 0.0209 0.1640 0.040 Uiso 1 1 calc R . . C39 C 0.5889(4) 0.05555(17) 0.21796(11) 0.0370(8) Uani 1 1 d . . . H39 H 0.6707 0.0392 0.2304 0.044 Uiso 1 1 calc R . . C40 C 0.4904(5) 0.03277(18) 0.05034(12) 0.0422(9) Uani 1 1 d . . . H40 H 0.5662 0.0249 0.0323 0.051 Uiso 1 1 calc R . . C41 C 0.5237(4) 0.04230(17) 0.08995(11) 0.0379(8) Uani 1 1 d . . . H41 H 0.6202 0.0401 0.0987 0.045 Uiso 1 1 calc R . . C42 C 0.4158(4) 0.05507(16) 0.11680(11) 0.0328(8) Uani 1 1 d . . . C43 C 0.2773(5) 0.0572(2) 0.10217(13) 0.0485(11) Uani 1 1 d . . . H43 H 0.2000 0.0661 0.1195 0.058 Uiso 1 1 calc R . . C44 C 0.2524(5) 0.0465(2) 0.06254(13) 0.0537(12) Uani 1 1 d . . . H44 H 0.1564 0.0479 0.0533 0.064 Uiso 1 1 calc R . . N1 N 0.7216(3) 0.18555(14) 0.47568(8) 0.0337(7) Uani 1 1 d . . . N2 N 0.7339(5) 0.27358(16) 0.27366(10) 0.0501(9) Uani 1 1 d . . . N3 N 0.5698(4) 0.40757(14) 0.26728(9) 0.0431(8) Uani 1 1 d . . . N4 N 0.6877(5) 0.37257(15) 0.47350(10) 0.0477(9) Uani 1 1 d . . . N5 N 0.5029(4) 0.08793(14) 0.24035(9) 0.0390(8) Uani 1 1 d . . . N6 N 0.3558(4) 0.03418(17) 0.03621(11) 0.0492(9) Uani 1 1 d . . . O1 O 0.7588(3) 0.12355(11) 0.05184(7) 0.0389(6) Uani 1 1 d . . . H1 H 0.7478 0.1295 0.0274 0.058 Uiso 1 1 calc R . . O2 O 0.6957(3) 0.32776(10) 0.05680(7) 0.0365(6) Uani 1 1 d . . . H2A H 0.7045 0.3240 0.0321 0.055 Uiso 1 1 calc R . . O3 O 0.3860(3) -0.11022(11) 0.31290(8) 0.0413(7) Uani 1 1 d . . . H3 H 0.4048 -0.1037 0.2889 0.062 Uiso 1 1 calc R . . O4 O 0.4829(3) 0.09241(11) 0.32301(7) 0.0361(6) Uani 1 1 d . . . H4A H 0.5025 0.0883 0.2988 0.054 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 C1 0.0286(17) 0.0260(17) 0.0323(16) -0.0042(13) -0.0042(13) 0.0014(14) C2 0.0314(18) 0.0310(18) 0.0303(16) 0.0017(13) -0.0011(14) 0.0031(14) C3 0.0263(17) 0.0364(19) 0.0255(15) -0.0019(13) 0.0001(13) -0.0053(14) C4 0.0349(19) 0.0273(17) 0.0277(16) -0.0052(13) -0.0005(13) 0.0001(14) C5 0.0306(18) 0.0284(17) 0.0296(16) 0.0002(13) -0.0004(13) -0.0019(14) C6 0.0257(16) 0.0296(17) 0.0240(14) -0.0031(12) 0.0006(12) -0.0005(13) C7 0.047(2) 0.045(2) 0.0271(17) -0.0012(15) -0.0007(15) 0.0037(18) C8 0.0320(18) 0.0254(17) 0.0323(17) -0.0034(13) 0.0011(14) 0.0047(14) C9 0.0324(18) 0.0270(17) 0.0322(17) 0.0041(13) 0.0035(14) 0.0010(14) C10 0.0243(16) 0.0327(18) 0.0298(16) 0.0052(13) 0.0001(13) 0.0036(14) C11 0.0296(18) 0.0295(18) 0.0312(17) -0.0026(13) 0.0016(14) 0.0026(14) C12 0.0244(16) 0.0250(16) 0.0325(17) 0.0025(13) 0.0028(13) 0.0033(13) C13 0.0293(17) 0.0312(18) 0.0252(15) 0.0009(13) 0.0008(13) 0.0043(14) C14 0.044(2) 0.039(2) 0.0305(18) 0.0029(15) 0.0037(15) 0.0020(17) C15 0.0326(19) 0.047(2) 0.0360(19) 0.0106(16) -0.0039(15) 0.0004(17) C16 0.0288(18) 0.045(2) 0.0330(18) 0.0088(15) 0.0024(14) 0.0011(16) C17 0.0327(18) 0.0276(17) 0.0277(16) 0.0011(13) -0.0008(13) -0.0005(14) C18 0.0294(19) 0.053(2) 0.0328(18) 0.0017(16) -0.0009(15) 0.0023(17) C19 0.035(2) 0.055(3) 0.0329(19) 0.0054(17) 0.0052(15) 0.0011(18) C20 0.055(3) 0.036(2) 0.0357(19) 0.0046(15) 0.0054(18) -0.0026(18) C21 0.039(2) 0.036(2) 0.0287(17) 0.0009(14) 0.0004(14) -0.0008(16) C22 0.0355(19) 0.0249(16) 0.0287(16) 0.0000(13) -0.0008(14) 0.0038(14) C23 0.038(2) 0.0325(19) 0.0361(18) -0.0004(15) -0.0070(15) 0.0009(16) C24 0.055(3) 0.045(2) 0.0342(19) -0.0045(17) -0.0119(18) 0.001(2) C25 0.049(2) 0.043(2) 0.0301(18) 0.0005(16) -0.0030(16) 0.0066(19) C26 0.036(2) 0.042(2) 0.0288(17) 0.0026(15) 0.0033(15) -0.0016(16) C27 0.0384(19) 0.0291(17) 0.0260(16) 0.0033(13) 0.0041(14) 0.0060(15) C28 0.040(2) 0.036(2) 0.0369(19) 0.0041(15) 0.0067(16) -0.0026(16) C29 0.060(3) 0.034(2) 0.038(2) 0.0085(16) 0.0189(19) 0.0028(19) C30 0.053(3) 0.045(2) 0.046(2) 0.0041(18) -0.013(2) -0.006(2) C31 0.041(2) 0.041(2) 0.040(2) 0.0023(16) -0.0029(16) -0.0024(17) C32 0.039(2) 0.0244(17) 0.0301(17) 0.0024(13) 0.0030(14) -0.0036(15) C33 0.042(2) 0.039(2) 0.0293(17) 0.0057(15) 0.0029(15) -0.0026(17) C34 0.064(3) 0.048(2) 0.0294(19) 0.0059(16) 0.0072(19) -0.008(2) C35 0.047(2) 0.037(2) 0.041(2) 0.0033(16) 0.0139(18) 0.0068(18) C36 0.041(2) 0.036(2) 0.042(2) 0.0058(16) 0.0048(17) 0.0099(17) C37 0.0298(18) 0.0296(18) 0.0350(18) 0.0066(14) 0.0028(14) -0.0022(14) C38 0.0317(19) 0.0314(18) 0.0374(19) 0.0019(14) 0.0033(15) 0.0032(15) C39 0.037(2) 0.036(2) 0.0370(19) 0.0061(15) 0.0005(16) -0.0004(16) C40 0.043(2) 0.046(2) 0.039(2) -0.0038(17) -0.0016(17) 0.0001(18) C41 0.037(2) 0.039(2) 0.0375(19) -0.0023(15) -0.0019(15) 0.0018(17) C42 0.0323(19) 0.0315(18) 0.0345(18) 0.0057(14) -0.0017(14) -0.0033(15) C43 0.034(2) 0.064(3) 0.047(2) 0.009(2) -0.0012(18) -0.005(2) C44 0.038(2) 0.075(3) 0.048(2) 0.008(2) -0.0107(19) -0.009(2) N1 0.0353(16) 0.0376(17) 0.0283(14) 0.0004(12) 0.0007(12) 0.0009(13) N2 0.071(3) 0.046(2) 0.0335(17) 0.0002(15) -0.0049(17) 0.0051(19) N3 0.064(2) 0.0359(18) 0.0290(15) 0.0048(13) 0.0056(15) 0.0071(17) N4 0.073(3) 0.0362(19) 0.0339(17) 0.0063(14) -0.0108(17) -0.0067(18) N5 0.048(2) 0.0340(17) 0.0346(16) 0.0045(13) 0.0044(14) 0.0006(15) N6 0.052(2) 0.052(2) 0.0432(19) 0.0031(16) -0.0102(17) -0.0063(18) O1 0.0619(18) 0.0259(13) 0.0291(12) -0.0026(10) -0.0072(12) 0.0062(12) O2 0.0567(17) 0.0259(13) 0.0271(12) -0.0019(9) 0.0027(12) 0.0016(12) O3 0.0632(19) 0.0292(14) 0.0316(13) -0.0039(10) 0.0075(13) -0.0044(13) O4 0.0495(16) 0.0288(13) 0.0299(12) 0.0006(10) 0.0054(12) -0.0039(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.353(4) . ? C1 C6 1.385(5) . ? C1 C2 1.387(5) . ? C2 C3 1.384(5) . ? C2 H2 0.9500 . ? C3 C4 1.393(5) . ? C3 C7 1.507(5) . ? C4 C5 1.394(5) . ? C4 H4 0.9500 . ? C5 O2 1.359(4) . ? C5 C6 1.387(5) . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 O3 1.365(4) . ? C8 C9 1.384(5) . ? C8 C13 1.393(5) . ? C9 C10 1.386(5) . ? C9 H9 0.9500 . ? C10 C11 1.393(5) . ? C10 C14 1.504(5) . ? C11 C12 1.390(5) . ? C11 H11 0.9500 . ? C12 O4 1.359(4) . ? C12 C13 1.390(5) . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 N1 1.342(5) . ? C15 C16 1.374(5) . ? C15 H15 0.9500 . ? C16 C17 1.388(5) . ? C16 H16 0.9500 . ? C17 C18 1.391(5) . ? C17 C22 1.479(5) . ? C18 C19 1.376(5) . ? C18 H18 0.9500 . ? C19 N1 1.331(5) . ? C19 H19 0.9500 . ? C20 N2 1.345(6) . ? C20 C21 1.375(5) . ? C20 H20 0.9500 . ? C21 C22 1.397(5) . ? C21 H21 0.9500 . ? C22 C23 1.391(5) . ? C23 C24 1.372(5) . ? C23 H23 0.9500 . ? C24 N2 1.345(6) . ? C24 H24 0.9500 . ? C25 N3 1.332(5) . ? C25 C26 1.381(5) . ? C25 H25 0.9500 . ? C26 C27 1.394(5) . ? C26 H26 0.9500 . ? C27 C28 1.389(5) . ? C27 C32 1.475(5) . ? C28 C29 1.375(6) . ? C28 H28 0.9500 . ? C29 N3 1.339(6) . ? C29 H29 0.9500 . ? C30 N4 1.340(6) . ? C30 C31 1.375(6) . ? C30 H30 0.9500 . ? C31 C32 1.384(5) . ? C31 H31 0.9500 . ? C32 C33 1.388(5) . ? C33 C34 1.376(5) . ? C33 H33 0.9500 . ? C34 N4 1.335(6) . ? C34 H34 0.9500 . ? C35 N5 1.340(5) . ? C35 C36 1.375(6) . ? C35 H35 0.9500 . ? C36 C37 1.398(5) . ? C36 H36 0.9500 . ? C37 C38 1.393(5) . ? C37 C42 1.488(5) . ? C38 C39 1.372(5) . ? C38 H38 0.9500 . ? C39 N5 1.334(5) . ? C39 H39 0.9500 . ? C40 N6 1.346(5) . ? C40 C41 1.384(5) . ? C40 H40 0.9500 . ? C41 C42 1.385(5) . ? C41 H41 0.9500 . ? C42 C43 1.385(6) . ? C43 C44 1.374(6) . ? C43 H43 0.9500 . ? C44 N6 1.340(6) . ? C44 H44 0.9500 . ? O1 H1 0.8400 . ? O2 H2A 0.8400 . ? O3 H3 0.8400 . ? O4 H4A 0.8400 . ? 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 O1 C1 C6 121.5(3) . . ? O1 C1 C2 118.1(3) . . ? C6 C1 C2 120.4(3) . . ? C3 C2 C1 120.1(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 119.9(3) . . ? C2 C3 C7 119.7(3) . . ? C4 C3 C7 120.4(3) . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? O2 C5 C6 121.8(3) . . ? O2 C5 C4 118.1(3) . . ? C6 C5 C4 120.1(3) . . ? C1 C6 C5 119.8(3) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O3 C8 C9 117.8(3) . . ? O3 C8 C13 121.4(3) . . ? C9 C8 C13 120.8(3) . . ? C8 C9 C10 119.9(3) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C11 119.8(3) . . ? C9 C10 C14 119.9(3) . . ? C11 C10 C14 120.4(3) . . ? C12 C11 C10 120.2(3) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? O4 C12 C13 122.2(3) . . ? O4 C12 C11 117.7(3) . . ? C13 C12 C11 120.2(3) . . ? C12 C13 C8 119.2(3) . . ? C12 C13 H13 120.4 . . ? C8 C13 H13 120.4 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 C16 123.6(3) . . ? N1 C15 H15 118.2 . . ? C16 C15 H15 118.2 . . ? C15 C16 C17 119.6(3) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C16 C17 C18 117.2(3) . . ? C16 C17 C22 121.4(3) . . ? C18 C17 C22 121.4(3) . . ? C19 C18 C17 119.0(3) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? N1 C19 C18 124.3(4) . . ? N1 C19 H19 117.8 . . ? C18 C19 H19 117.8 . . ? N2 C20 C21 123.6(4) . . ? N2 C20 H20 118.2 . . ? C21 C20 H20 118.2 . . ? C20 C21 C22 119.4(4) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C23 C22 C21 117.4(3) . . ? C23 C22 C17 121.8(3) . . ? C21 C22 C17 120.8(3) . . ? C24 C23 C22 119.1(4) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? N2 C24 C23 124.2(4) . . ? N2 C24 H24 117.9 . . ? C23 C24 H24 117.9 . . ? N3 C25 C26 123.9(4) . . ? N3 C25 H25 118.1 . . ? C26 C25 H25 118.1 . . ? C25 C26 C27 118.9(4) . . ? C25 C26 H26 120.5 . . ? C27 C26 H26 120.5 . . ? C28 C27 C26 117.5(3) . . ? C28 C27 C32 121.5(3) . . ? C26 C27 C32 121.0(3) . . ? C29 C28 C27 119.1(4) . . ? C29 C28 H28 120.4 . . ? C27 C28 H28 120.4 . . ? N3 C29 C28 123.9(4) . . ? N3 C29 H29 118.0 . . ? C28 C29 H29 118.0 . . ? N4 C30 C31 122.6(4) . . ? N4 C30 H30 118.7 . . ? C31 C30 H30 118.7 . . ? C30 C31 C32 119.9(4) . . ? C30 C31 H31 120.0 . . ? C32 C31 H31 120.0 . . ? C31 C32 C33 117.5(3) . . ? C31 C32 C27 120.9(3) . . ? C33 C32 C27 121.6(3) . . ? C34 C33 C32 119.0(4) . . ? C34 C33 H33 120.5 . . ? C32 C33 H33 120.5 . . ? N4 C34 C33 123.6(4) . . ? N4 C34 H34 118.2 . . ? C33 C34 H34 118.2 . . ? N5 C35 C36 124.0(4) . . ? N5 C35 H35 118.0 . . ? C36 C35 H35 118.0 . . ? C35 C36 C37 119.3(4) . . ? C35 C36 H36 120.3 . . ? C37 C36 H36 120.3 . . ? C38 C37 C36 117.1(3) . . ? C38 C37 C42 122.0(3) . . ? C36 C37 C42 120.9(3) . . ? C39 C38 C37 118.9(3) . . ? C39 C38 H38 120.6 . . ? C37 C38 H38 120.6 . . ? N5 C39 C38 124.8(4) . . ? N5 C39 H39 117.6 . . ? C38 C39 H39 117.6 . . ? N6 C40 C41 123.0(4) . . ? N6 C40 H40 118.5 . . ? C41 C40 H40 118.5 . . ? C40 C41 C42 119.8(4) . . ? C40 C41 H41 120.1 . . ? C42 C41 H41 120.1 . . ? C41 C42 C43 117.2(4) . . ? C41 C42 C37 121.2(3) . . ? C43 C42 C37 121.6(4) . . ? C44 C43 C42 119.7(4) . . ? C44 C43 H43 120.1 . . ? C42 C43 H43 120.1 . . ? N6 C44 C43 123.8(4) . . ? N6 C44 H44 118.1 . . ? C43 C44 H44 118.1 . . ? C19 N1 C15 116.3(3) . . ? C24 N2 C20 116.3(3) . . ? C25 N3 C29 116.6(3) . . ? C34 N4 C30 117.3(3) . . ? C39 N5 C35 116.0(3) . . ? C44 N6 C40 116.5(4) . . ? C1 O1 H1 109.5 . . ? C5 O2 H2A 109.5 . . ? C8 O3 H3 109.5 . . ? C12 O4 H4A 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 O1 C1 C2 C3 177.8(3) . . . . ? C6 C1 C2 C3 -0.7(5) . . . . ? C1 C2 C3 C4 0.3(5) . . . . ? C1 C2 C3 C7 179.5(3) . . . . ? C2 C3 C4 C5 0.2(5) . . . . ? C7 C3 C4 C5 -179.0(3) . . . . ? C3 C4 C5 O2 179.6(3) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? O1 C1 C6 C5 -177.9(3) . . . . ? C2 C1 C6 C5 0.6(5) . . . . ? O2 C5 C6 C1 180.0(3) . . . . ? C4 C5 C6 C1 -0.1(5) . . . . ? O3 C8 C9 C10 178.1(3) . . . . ? C13 C8 C9 C10 -0.5(5) . . . . ? C8 C9 C10 C11 1.1(5) . . . . ? C8 C9 C10 C14 -177.3(3) . . . . ? C9 C10 C11 C12 -1.1(5) . . . . ? C14 C10 C11 C12 177.2(3) . . . . ? C10 C11 C12 O4 -179.2(3) . . . . ? C10 C11 C12 C13 0.6(5) . . . . ? O4 C12 C13 C8 179.8(3) . . . . ? C11 C12 C13 C8 0.0(5) . . . . ? O3 C8 C13 C12 -178.6(3) . . . . ? C9 C8 C13 C12 0.0(5) . . . . ? N1 C15 C16 C17 1.6(6) . . . . ? C15 C16 C17 C18 -0.8(6) . . . . ? C15 C16 C17 C22 179.6(4) . . . . ? C16 C17 C18 C19 -0.4(6) . . . . ? C22 C17 C18 C19 179.3(4) . . . . ? C17 C18 C19 N1 0.8(7) . . . . ? N2 C20 C21 C22 0.1(6) . . . . ? C20 C21 C22 C23 -0.2(5) . . . . ? C20 C21 C22 C17 179.7(3) . . . . ? C16 C17 C22 C23 148.5(4) . . . . ? C18 C17 C22 C23 -31.1(5) . . . . ? C16 C17 C22 C21 -31.4(5) . . . . ? C18 C17 C22 C21 149.0(4) . . . . ? C21 C22 C23 C24 0.8(5) . . . . ? C17 C22 C23 C24 -179.1(4) . . . . ? C22 C23 C24 N2 -1.3(6) . . . . ? N3 C25 C26 C27 -0.8(6) . . . . ? C25 C26 C27 C28 2.4(5) . . . . ? C25 C26 C27 C32 -176.1(3) . . . . ? C26 C27 C28 C29 -1.8(6) . . . . ? C32 C27 C28 C29 176.6(3) . . . . ? C27 C28 C29 N3 -0.4(6) . . . . ? N4 C30 C31 C32 -2.0(7) . . . . ? C30 C31 C32 C33 1.3(6) . . . . ? C30 C31 C32 C27 -178.9(4) . . . . ? C28 C27 C32 C31 -32.1(5) . . . . ? C26 C27 C32 C31 146.4(4) . . . . ? C28 C27 C32 C33 147.8(4) . . . . ? C26 C27 C32 C33 -33.8(5) . . . . ? C31 C32 C33 C34 0.1(6) . . . . ? C27 C32 C33 C34 -179.7(4) . . . . ? C32 C33 C34 N4 -1.0(6) . . . . ? N5 C35 C36 C37 -0.2(6) . . . . ? C35 C36 C37 C38 -0.8(6) . . . . ? C35 C36 C37 C42 178.6(4) . . . . ? C36 C37 C38 C39 1.2(5) . . . . ? C42 C37 C38 C39 -178.2(3) . . . . ? C37 C38 C39 N5 -0.6(6) . . . . ? N6 C40 C41 C42 -1.3(6) . . . . ? C40 C41 C42 C43 0.5(6) . . . . ? C40 C41 C42 C37 -178.5(4) . . . . ? C38 C37 C42 C41 -27.2(5) . . . . ? C36 C37 C42 C41 153.4(4) . . . . ? C38 C37 C42 C43 153.9(4) . . . . ? C36 C37 C42 C43 -25.5(6) . . . . ? C41 C42 C43 C44 0.4(6) . . . . ? C37 C42 C43 C44 179.4(4) . . . . ? C42 C43 C44 N6 -0.5(8) . . . . ? C18 C19 N1 C15 -0.1(6) . . . . ? C16 C15 N1 C19 -1.1(6) . . . . ? C23 C24 N2 C20 1.2(7) . . . . ? C21 C20 N2 C24 -0.6(6) . . . . ? C26 C25 N3 C29 -1.4(6) . . . . ? C28 C29 N3 C25 2.0(6) . . . . ? C33 C34 N4 C30 0.4(6) . . . . ? C31 C30 N4 C34 1.1(6) . . . . ? C38 C39 N5 C35 -0.4(6) . . . . ? C36 C35 N5 C39 0.8(6) . . . . ? C43 C44 N6 C40 -0.2(7) . . . . ? C41 C40 N6 C44 1.2(7) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.414 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.082 # Attachment 'orcinol 44bp-btp-ipa.cif' data_orcinol_44bp-btp-ipa _database_code_depnum_ccdc_archive 'CCDC 836452' #TrackingRef 'orcinol 44bp-btp-ipa.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 N2 O2 S' _chemical_formula_weight 363.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1250 0.1230 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.3357(12) _cell_length_b 12.3050(14) _cell_length_c 17.910(2) _cell_angle_alpha 90.00 _cell_angle_beta 116.558(7) _cell_angle_gamma 90.00 _cell_volume 1840.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4892 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 0.193 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9267 _exptl_absorpt_correction_T_max 0.9443 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19129 _diffrn_reflns_av_R_equivalents 0.0918 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4212 _reflns_number_gt 3744 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0813P)^2^+1.1672P] 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 4212 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1682 _refine_ls_wR_factor_gt 0.1605 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.5903(2) 0.57625(15) 0.37805(11) 0.0330(4) Uani 1 1 d . . . N2 N 1.3880(2) 0.77528(15) 0.56838(12) 0.0345(4) Uani 1 1 d . . . C12 C 1.1752(2) 0.68406(18) 0.45392(13) 0.0321(4) Uani 1 1 d . . . H16 H 1.1386 0.6499 0.4010 0.038 Uiso 1 1 calc R . . C13 C 0.9088(2) 0.65030(15) 0.45312(11) 0.0253(4) Uani 1 1 d . . . C14 C 0.8208(2) 0.64425(18) 0.36662(12) 0.0313(4) Uani 1 1 d . . . H12 H 0.8677 0.6654 0.3315 0.038 Uiso 1 1 calc R . . C15 C 1.0744(2) 0.69314(16) 0.49256(12) 0.0259(4) Uani 1 1 d . . . C16 C 1.1349(2) 0.74601(17) 0.56950(12) 0.0309(4) Uani 1 1 d . . . H19 H 1.0703 0.7550 0.5977 0.037 Uiso 1 1 calc R . . C17 C 0.6646(2) 0.60711(19) 0.33249(13) 0.0341(5) Uani 1 1 d . . . H13 H 0.6066 0.6032 0.2734 0.041 Uiso 1 1 calc R . . C18 C 1.3289(2) 0.72554(19) 0.49397(14) 0.0363(5) Uani 1 1 d . . . H17 H 1.3964 0.7184 0.4672 0.044 Uiso 1 1 calc R . . C19 C 0.6766(2) 0.58011(18) 0.46112(13) 0.0337(5) Uani 1 1 d . . . H14 H 0.6269 0.5571 0.4946 0.040 Uiso 1 1 calc R . . C20 C 0.8332(2) 0.61550(17) 0.50116(12) 0.0303(4) Uani 1 1 d . . . H15 H 0.8889 0.6163 0.5604 0.036 Uiso 1 1 calc R . . C21 C 1.2901(2) 0.78518(18) 0.60428(14) 0.0357(5) Uani 1 1 d . . . H18 H 1.3293 0.8212 0.6566 0.043 Uiso 1 1 calc R . . S1 S 0.81815(7) 0.96780(6) 0.54219(4) 0.0458(2) Uani 1 1 d . . . C1 C 0.9187(2) 0.97849(16) 0.48207(12) 0.0283(4) Uani 1 1 d . . . C2 C 0.8257(2) 0.94029(18) 0.39959(13) 0.0326(4) Uani 1 1 d . . . H1 H 0.8596 0.9375 0.3569 0.039 Uiso 1 1 calc R . . C3 C 0.6520(3) 0.9165(2) 0.46141(16) 0.0457(6) Uani 1 1 d . . . H3 H 0.5569 0.8973 0.4651 0.055 Uiso 1 1 calc R . . C4 C 0.6713(3) 0.9063(2) 0.39092(15) 0.0434(5) Uani 1 1 d . . . H2 H 0.5896 0.8791 0.3401 0.052 Uiso 1 1 calc R . . O1 O 0.70898(16) 0.81788(11) 0.65992(9) 0.0281(3) Uani 1 1 d . . . H10 H 0.6105 0.8050 0.6333 0.042 Uiso 1 1 d R . . O2 O 0.73675(16) 0.42834(11) 0.69229(9) 0.0320(3) Uani 1 1 d . . . H8 H 0.6366 0.4348 0.6685 0.048 Uiso 1 1 d R . . C5 C 0.7148(2) 0.62266(15) 0.67375(11) 0.0228(4) Uani 1 1 d . . . H9 H 0.6014 0.6194 0.6511 0.027 Uiso 1 1 calc R . . C6 C 0.9722(2) 0.53227(15) 0.73251(11) 0.0250(4) Uani 1 1 d . . . H7 H 1.0334 0.4673 0.7489 0.030 Uiso 1 1 calc R . . C7 C 0.9584(2) 0.72731(15) 0.71692(11) 0.0243(4) Uani 1 1 d . . . H11 H 1.0103 0.7955 0.7232 0.029 Uiso 1 1 calc R . . C8 C 0.8056(2) 0.52782(15) 0.69873(11) 0.0238(4) Uani 1 1 d . . . C9 C 0.7914(2) 0.72205(14) 0.68230(11) 0.0226(4) Uani 1 1 d . . . C10 C 1.0485(2) 0.63223(15) 0.74214(11) 0.0245(4) Uani 1 1 d . . . C11 C 1.2293(2) 0.63646(18) 0.77928(14) 0.0331(4) Uani 1 1 d . . . H4 H 1.2659 0.7110 0.7966 0.050 Uiso 1 1 calc R . . H5 H 1.2634 0.6129 0.7374 0.050 Uiso 1 1 calc R . . H6 H 1.2758 0.5881 0.8278 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0254(8) 0.0365(10) 0.0339(9) -0.0014(7) 0.0103(7) -0.0056(7) N2 0.0223(8) 0.0313(9) 0.0427(10) 0.0076(7) 0.0081(7) 0.0007(7) C12 0.0251(9) 0.0377(11) 0.0344(10) -0.0005(8) 0.0141(8) -0.0001(8) C13 0.0227(9) 0.0278(9) 0.0249(9) 0.0004(7) 0.0103(7) 0.0003(7) C14 0.0261(10) 0.0425(12) 0.0254(9) 0.0021(8) 0.0115(8) -0.0013(8) C15 0.0222(9) 0.0274(9) 0.0258(9) 0.0047(7) 0.0086(7) 0.0015(7) C16 0.0266(9) 0.0355(11) 0.0290(10) -0.0011(8) 0.0110(8) -0.0013(8) C17 0.0284(10) 0.0440(12) 0.0254(9) -0.0015(8) 0.0079(8) -0.0041(9) C18 0.0248(10) 0.0415(12) 0.0445(12) 0.0048(9) 0.0170(9) 0.0030(8) C19 0.0294(10) 0.0409(12) 0.0324(10) 0.0015(8) 0.0151(8) -0.0068(8) C20 0.0279(10) 0.0375(11) 0.0246(9) 0.0024(8) 0.0111(8) -0.0027(8) C21 0.0270(10) 0.0368(11) 0.0343(10) -0.0005(8) 0.0057(8) -0.0028(8) S1 0.0384(3) 0.0637(4) 0.0382(3) -0.0026(3) 0.0199(3) -0.0097(3) C1 0.0279(10) 0.0310(10) 0.0257(9) 0.0043(7) 0.0117(8) -0.0005(8) C2 0.0228(9) 0.0370(11) 0.0312(10) -0.0002(8) 0.0060(8) -0.0054(8) C3 0.0311(11) 0.0514(14) 0.0549(14) 0.0026(11) 0.0196(10) -0.0050(10) C4 0.0332(11) 0.0460(13) 0.0401(12) -0.0046(10) 0.0066(9) -0.0075(10) O1 0.0218(6) 0.0233(7) 0.0357(7) 0.0006(5) 0.0098(6) 0.0015(5) O2 0.0226(7) 0.0239(7) 0.0436(8) 0.0025(6) 0.0096(6) -0.0024(5) C5 0.0191(8) 0.0273(9) 0.0206(8) 0.0001(6) 0.0077(6) 0.0000(7) C6 0.0233(9) 0.0240(9) 0.0257(9) 0.0001(7) 0.0092(7) 0.0014(7) C7 0.0228(8) 0.0246(9) 0.0251(9) -0.0034(7) 0.0103(7) -0.0031(7) C8 0.0241(9) 0.0235(9) 0.0222(8) -0.0004(6) 0.0091(7) -0.0030(7) C9 0.0246(9) 0.0235(9) 0.0196(8) -0.0015(6) 0.0098(7) 0.0014(7) C10 0.0209(8) 0.0293(9) 0.0216(8) -0.0021(7) 0.0081(7) -0.0009(7) C11 0.0218(9) 0.0341(11) 0.0379(11) 0.0003(8) 0.0084(8) -0.0007(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C19 1.339(3) . ? N1 C17 1.341(3) . ? N2 C21 1.338(3) . ? N2 C18 1.341(3) . ? C12 C18 1.383(3) . ? C12 C15 1.400(3) . ? C12 H16 0.9500 . ? C13 C14 1.394(3) . ? C13 C20 1.402(3) . ? C13 C15 1.480(3) . ? C14 C17 1.383(3) . ? C14 H12 0.9500 . ? C15 C16 1.395(3) . ? C16 C21 1.383(3) . ? C16 H19 0.9500 . ? C17 H13 0.9500 . ? C18 H17 0.9500 . ? C19 C20 1.380(3) . ? C19 H14 0.9500 . ? C20 H15 0.9500 . ? C21 H18 0.9500 . ? S1 C3 1.700(3) . ? S1 C1 1.721(2) . ? C1 C2 1.418(3) . ? C1 C1 1.457(4) 3_776 ? C2 C4 1.441(3) . ? C2 H1 0.9500 . ? C3 C4 1.358(4) . ? C3 H3 0.9500 . ? C4 H2 0.9500 . ? O1 C9 1.366(2) . ? O1 H10 0.8400 . ? O2 C8 1.363(2) . ? O2 H8 0.8400 . ? C5 C9 1.390(3) . ? C5 C8 1.393(3) . ? C5 H9 0.9500 . ? C6 C10 1.393(3) . ? C6 C8 1.395(2) . ? C6 H7 0.9500 . ? C7 C10 1.393(3) . ? C7 C9 1.399(2) . ? C7 H11 0.9500 . ? C10 C11 1.513(2) . ? C11 H4 0.9800 . ? C11 H5 0.9800 . ? C11 H6 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 C19 N1 C17 116.63(17) . . ? C21 N2 C18 116.94(18) . . ? C18 C12 C15 119.0(2) . . ? C18 C12 H16 120.5 . . ? C15 C12 H16 120.5 . . ? C14 C13 C20 117.25(17) . . ? C14 C13 C15 121.35(17) . . ? C20 C13 C15 121.40(17) . . ? C17 C14 C13 119.33(18) . . ? C17 C14 H12 120.3 . . ? C13 C14 H12 120.3 . . ? C16 C15 C12 117.44(18) . . ? C16 C15 C13 120.86(17) . . ? C12 C15 C13 121.69(18) . . ? C21 C16 C15 119.19(19) . . ? C21 C16 H19 120.4 . . ? C15 C16 H19 120.4 . . ? N1 C17 C14 123.71(18) . . ? N1 C17 H13 118.1 . . ? C14 C17 H13 118.1 . . ? N2 C18 C12 123.7(2) . . ? N2 C18 H17 118.2 . . ? C12 C18 H17 118.2 . . ? N1 C19 C20 124.05(18) . . ? N1 C19 H14 118.0 . . ? C20 C19 H14 118.0 . . ? C19 C20 C13 118.99(18) . . ? C19 C20 H15 120.5 . . ? C13 C20 H15 120.5 . . ? N2 C21 C16 123.7(2) . . ? N2 C21 H18 118.1 . . ? C16 C21 H18 118.1 . . ? C3 S1 C1 92.35(11) . . ? C2 C1 C1 127.7(2) . 3_776 ? C2 C1 S1 112.01(15) . . ? C1 C1 S1 120.25(19) 3_776 . ? C1 C2 C4 109.03(19) . . ? C1 C2 H1 125.5 . . ? C4 C2 H1 125.5 . . ? C4 C3 S1 112.09(18) . . ? C4 C3 H3 124.0 . . ? S1 C3 H3 124.0 . . ? C3 C4 C2 114.5(2) . . ? C3 C4 H2 122.8 . . ? C2 C4 H2 122.8 . . ? C9 O1 H10 109.5 . . ? C8 O2 H8 109.5 . . ? C9 C5 C8 119.49(16) . . ? C9 C5 H9 120.3 . . ? C8 C5 H9 120.3 . . ? C10 C6 C8 119.85(17) . . ? C10 C6 H7 120.1 . . ? C8 C6 H7 120.1 . . ? C10 C7 C9 119.78(17) . . ? C10 C7 H11 120.1 . . ? C9 C7 H11 120.1 . . ? O2 C8 C5 121.93(16) . . ? O2 C8 C6 117.63(16) . . ? C5 C8 C6 120.44(17) . . ? O1 C9 C5 122.18(16) . . ? O1 C9 C7 117.37(16) . . ? C5 C9 C7 120.42(16) . . ? C6 C10 C7 120.00(17) . . ? C6 C10 C11 119.55(17) . . ? C7 C10 C11 120.45(17) . . ? C10 C11 H4 109.5 . . ? C10 C11 H5 109.5 . . ? H4 C11 H5 109.5 . . ? C10 C11 H6 109.5 . . ? H4 C11 H6 109.5 . . ? H5 C11 H6 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 C20 C13 C14 C17 1.4(3) . . . . ? C15 C13 C14 C17 -177.81(19) . . . . ? C18 C12 C15 C16 1.2(3) . . . . ? C18 C12 C15 C13 -179.89(19) . . . . ? C14 C13 C15 C16 149.8(2) . . . . ? C20 C13 C15 C16 -29.4(3) . . . . ? C14 C13 C15 C12 -29.1(3) . . . . ? C20 C13 C15 C12 151.7(2) . . . . ? C12 C15 C16 C21 -0.9(3) . . . . ? C13 C15 C16 C21 -179.84(19) . . . . ? C19 N1 C17 C14 -1.6(3) . . . . ? C13 C14 C17 N1 0.3(4) . . . . ? C21 N2 C18 C12 -0.6(3) . . . . ? C15 C12 C18 N2 -0.4(3) . . . . ? C17 N1 C19 C20 1.4(3) . . . . ? N1 C19 C20 C13 0.2(3) . . . . ? C14 C13 C20 C19 -1.6(3) . . . . ? C15 C13 C20 C19 177.57(19) . . . . ? C18 N2 C21 C16 0.9(3) . . . . ? C15 C16 C21 N2 -0.2(3) . . . . ? C3 S1 C1 C2 -1.26(18) . . . . ? C3 S1 C1 C1 179.5(2) . . . 3_776 ? C1 C1 C2 C4 -179.4(3) 3_776 . . . ? S1 C1 C2 C4 1.5(2) . . . . ? C1 S1 C3 C4 0.6(2) . . . . ? S1 C3 C4 C2 0.1(3) . . . . ? C1 C2 C4 C3 -1.1(3) . . . . ? C9 C5 C8 O2 179.53(16) . . . . ? C9 C5 C8 C6 0.3(3) . . . . ? C10 C6 C8 O2 -178.58(16) . . . . ? C10 C6 C8 C5 0.6(3) . . . . ? C8 C5 C9 O1 -179.15(16) . . . . ? C8 C5 C9 C7 -1.0(3) . . . . ? C10 C7 C9 O1 178.93(16) . . . . ? C10 C7 C9 C5 0.7(3) . . . . ? C8 C6 C10 C7 -1.0(3) . . . . ? C8 C6 C10 C11 179.65(17) . . . . ? C9 C7 C10 C6 0.3(3) . . . . ? C9 C7 C10 C11 179.68(17) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.497 _refine_diff_density_min -0.494 _refine_diff_density_rms 0.061 data_datam _database_code_depnum_ccdc_archive 'CCDC 836592' #TrackingRef 'web_deposit_cif_file_0_SrinuTothadi_1311597892.26dht_44bp_bp_dioxane_211.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H34 N2 O4' _chemical_formula_weight 558.65 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 Monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.737(4) _cell_length_b 19.791(10) _cell_length_c 9.508(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.170(7) _cell_angle_gamma 90.00 _cell_volume 1450.0(13) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4177 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.083 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9754 _exptl_absorpt_correction_T_max 0.9917 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15099 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_sigmaI/netI 0.0569 _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 -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.51 _reflns_number_total 6630 _reflns_number_gt 6082 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0818P)^2^+0.3795P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(12) _refine_ls_number_reflns 6630 _refine_ls_number_parameters 434 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.1620 _refine_ls_wR_factor_gt 0.1537 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.029 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3220(3) 0.43468(12) 0.0830(2) 0.0251(4) Uani 1 1 d . . . C2 C 0.4874(3) 0.42550(12) 0.0389(3) 0.0287(5) Uani 1 1 d . . . C3 C 0.5036(3) 0.39541(13) -0.0901(3) 0.0299(5) Uani 1 1 d . . . C4 C 0.3585(3) 0.37413(13) -0.1754(3) 0.0290(5) Uani 1 1 d . . . C5 C 0.1721(3) 0.41331(12) 0.0029(2) 0.0241(4) Uani 1 1 d . . . C6 C 0.1947(3) 0.38303(11) -0.1285(2) 0.0220(4) Uani 1 1 d . . . C7 C 0.6799(3) 0.50828(12) 0.5000(2) 0.0233(4) Uani 1 1 d . . . C8 C 0.7066(3) 0.53927(11) 0.3712(2) 0.0231(4) Uani 1 1 d . . . C9 C 0.8729(3) 0.54999(12) 0.3304(2) 0.0274(5) Uani 1 1 d . . . C10 C 1.0151(3) 0.53051(13) 0.4205(3) 0.0305(5) Uani 1 1 d . . . C11 C 0.9939(3) 0.49933(12) 0.5483(2) 0.0279(5) Uani 1 1 d . . . C12 C 0.8263(3) 0.48738(12) 0.5860(2) 0.0248(4) Uani 1 1 d . . . C13 C 0.7057(3) 0.22512(13) 0.3050(3) 0.0315(5) Uani 1 1 d . . . C14 C 0.7492(3) 0.19582(15) 0.1695(3) 0.0371(6) Uani 1 1 d . . . C15 C 0.7404(4) 0.2362(2) 0.0468(3) 0.0592(9) Uani 1 1 d . . . H47 H 0.7047 0.2819 0.0553 0.071 Uiso 1 1 calc R . . C16 C 0.7789(6) 0.2152(3) -0.0814(4) 0.0823(13) Uani 1 1 d . . . H16 H 0.7733 0.2453 -0.1595 0.099 Uiso 1 1 calc R . . C17 C 0.8232(5) 0.1534(3) -0.0946(5) 0.0785(12) Uani 1 1 d . . . H17 H 0.8483 0.1391 -0.1860 0.094 Uiso 1 1 calc R . . C18 C 0.8377(4) 0.1059(2) 0.0111(6) 0.0860(17) Uani 1 1 d . . . H46 H 0.8691 0.0604 -0.0060 0.103 Uiso 1 1 calc R . . C19 C 0.8013(4) 0.12988(19) 0.1551(5) 0.0640(11) Uani 1 1 d . . . H19 H 0.8138 0.1004 0.2341 0.077 Uiso 1 1 calc R . . C20 C 0.6449(4) 0.1849(2) 0.4083(3) 0.0582(9) Uani 1 1 d . . . H20 H 0.6282 0.1379 0.3923 0.070 Uiso 1 1 calc R . . C21 C 0.6078(5) 0.2135(5) 0.5363(4) 0.116(3) Uani 1 1 d . . . H45 H 0.5663 0.1852 0.6068 0.139 Uiso 1 1 calc R . . C22 C 0.6299(6) 0.2821(6) 0.5638(6) 0.146(4) Uani 1 1 d . . . H22 H 0.6045 0.3011 0.6513 0.175 Uiso 1 1 calc R . . C23 C 0.6888(5) 0.3203(3) 0.4613(6) 0.097(2) Uani 1 1 d . . . H48 H 0.7036 0.3674 0.4777 0.116 Uiso 1 1 calc R . . C24 C 0.7293(4) 0.29398(17) 0.3316(4) 0.0493(8) Uani 1 1 d . . . H24 H 0.7723 0.3226 0.2626 0.059 Uiso 1 1 calc R . . C25 C 0.3429(3) 0.09317(13) 0.0664(3) 0.0338(5) Uani 1 1 d . . . H25 H 0.3727 0.0466 0.0716 0.041 Uiso 1 1 calc R . . C26 C 0.2942(3) 0.12419(13) 0.1868(3) 0.0293(5) Uani 1 1 d . . . H26 H 0.2905 0.0991 0.2717 0.035 Uiso 1 1 calc R . . C27 C 0.2505(3) 0.19254(12) 0.1829(2) 0.0246(4) Uani 1 1 d . . . C28 C 0.2588(4) 0.22542(13) 0.0550(2) 0.0347(5) Uani 1 1 d . . . H28 H 0.2305 0.2720 0.0465 0.042 Uiso 1 1 calc R . . C29 C 0.3084(4) 0.19021(14) -0.0601(3) 0.0381(6) Uani 1 1 d . . . H29 H 0.3129 0.2138 -0.1467 0.046 Uiso 1 1 calc R . . C30 C 0.2018(3) 0.22815(11) 0.3120(2) 0.0228(4) Uani 1 1 d . . . C31 C 0.2248(3) 0.29797(13) 0.3268(3) 0.0284(5) Uani 1 1 d . . . C32 C 0.1811(3) 0.32955(13) 0.4484(3) 0.0316(5) Uani 1 1 d . . . C33 C 0.0970(3) 0.22908(13) 0.5418(2) 0.0293(5) Uani 1 1 d . . . C34 C 0.1354(3) 0.19340(12) 0.4221(2) 0.0270(4) Uani 1 1 d . . . C35 C -0.0050(3) 0.42068(13) 0.0539(2) 0.0309(5) Uani 1 1 d . . . H35A H 0.0062 0.4279 0.1563 0.046 Uiso 1 1 calc R . . H35B H -0.0724 0.3795 0.0317 0.046 Uiso 1 1 calc R . . H35C H -0.0644 0.4594 0.0070 0.046 Uiso 1 1 calc R . . C36 C 0.5003(3) 0.49505(13) 0.5432(3) 0.0308(5) Uani 1 1 d . . . H36A H 0.4227 0.5318 0.5090 0.046 Uiso 1 1 calc R . . H36B H 0.5045 0.4926 0.6464 0.046 Uiso 1 1 calc R . . H36C H 0.4570 0.4522 0.5023 0.046 Uiso 1 1 calc R . . N1 N 0.1190(3) 0.29587(11) 0.5563(2) 0.0301(4) Uani 1 1 d . . . N2 N 0.3504(3) 0.12478(12) -0.0565(2) 0.0313(4) Uani 1 1 d . . . O1 O 0.0470(2) 0.36328(9) -0.20908(17) 0.0278(4) Uani 1 1 d . . . H100 H 0.0745 0.3427 -0.2811 0.042 Uiso 1 1 calc R . . O2 O 0.7974(2) 0.45607(10) 0.70940(18) 0.0323(4) Uani 1 1 d . . . O3 O 0.2984(2) 0.46543(10) 0.20961(18) 0.0333(4) Uani 1 1 d . . . O4 O 0.5615(2) 0.55729(9) 0.28526(17) 0.0285(4) Uani 1 1 d . . . H1 H 0.359(4) 0.3562(17) -0.268(3) 0.035(8) Uiso 1 1 d . . . H2 H 0.588(4) 0.4430(15) 0.101(3) 0.028(7) Uiso 1 1 d . . . H3 H 0.890(4) 0.5717(15) 0.242(3) 0.031(7) Uiso 1 1 d . . . H11 H 0.260(4) 0.3291(14) 0.256(3) 0.030(7) Uiso 1 1 d . . . H12 H 0.205(4) 0.3786(16) 0.458(3) 0.043(8) Uiso 1 1 d . . . H18 H 0.612(4) 0.3908(15) -0.125(3) 0.031(7) Uiso 1 1 d . . . H21 H 1.128(4) 0.5424(16) 0.397(3) 0.040(8) Uiso 1 1 d . . . H23 H 0.591(5) 0.584(2) 0.201(4) 0.069(11) Uiso 1 1 d . . . H32 H 0.041(3) 0.2083(13) 0.619(3) 0.027(6) Uiso 1 1 d . . . H33 H 0.125(4) 0.1425(15) 0.420(3) 0.037(7) Uiso 1 1 d . . . H35 H 1.100(3) 0.4885(14) 0.619(3) 0.020(6) Uiso 1 1 d . . . H41 H 0.393(5) 0.4741(19) 0.245(4) 0.058(11) Uiso 1 1 d . . . H42 H 0.890(4) 0.4231(17) 0.735(3) 0.042(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0272(11) 0.0245(11) 0.0238(10) 0.0017(9) 0.0034(8) -0.0018(8) C2 0.0257(11) 0.0293(12) 0.0311(12) 0.0038(10) 0.0022(9) -0.0024(9) C3 0.0243(11) 0.0327(13) 0.0336(12) 0.0036(10) 0.0082(9) 0.0011(9) C4 0.0287(11) 0.0336(13) 0.0252(11) 0.0005(10) 0.0049(9) 0.0024(9) C5 0.0244(10) 0.0238(11) 0.0245(10) 0.0008(9) 0.0039(8) -0.0017(8) C6 0.0240(10) 0.0220(10) 0.0199(10) 0.0028(8) 0.0008(7) 0.0015(8) C7 0.0234(10) 0.0217(10) 0.0248(10) -0.0013(8) 0.0022(8) -0.0015(8) C8 0.0232(10) 0.0215(11) 0.0239(10) -0.0027(8) -0.0025(8) -0.0017(8) C9 0.0294(11) 0.0304(12) 0.0230(10) 0.0014(9) 0.0059(9) -0.0011(9) C10 0.0228(11) 0.0356(13) 0.0340(12) 0.0012(10) 0.0080(9) 0.0007(9) C11 0.0225(10) 0.0325(13) 0.0284(11) -0.0019(10) 0.0003(8) 0.0039(9) C12 0.0278(11) 0.0246(11) 0.0218(10) 0.0004(9) 0.0016(8) 0.0021(8) C13 0.0252(11) 0.0306(12) 0.0375(12) -0.0035(10) -0.0039(9) -0.0007(9) C14 0.0245(11) 0.0414(15) 0.0438(14) -0.0134(11) -0.0050(10) 0.0018(10) C15 0.0462(17) 0.090(3) 0.0408(15) -0.0008(16) -0.0014(12) -0.0002(17) C16 0.067(3) 0.120(4) 0.060(2) -0.007(2) 0.0059(19) 0.007(3) C17 0.055(2) 0.095(3) 0.084(3) -0.012(3) -0.006(2) -0.007(2) C18 0.0338(17) 0.056(2) 0.168(5) -0.059(3) 0.009(2) 0.0031(15) C19 0.0417(16) 0.0432(18) 0.103(3) -0.0311(19) -0.0179(17) 0.0079(14) C20 0.0390(16) 0.082(2) 0.0508(17) 0.0132(16) -0.0085(13) -0.0175(16) C21 0.0317(17) 0.281(9) 0.0343(18) 0.010(3) 0.0017(13) -0.013(3) C22 0.042(2) 0.322(12) 0.071(3) -0.101(5) -0.010(2) 0.056(4) C23 0.048(2) 0.120(4) 0.118(4) -0.092(4) -0.023(2) 0.033(2) C24 0.0369(14) 0.0347(15) 0.074(2) -0.0185(15) -0.0061(13) 0.0045(11) C25 0.0403(14) 0.0256(12) 0.0354(13) -0.0052(10) 0.0023(10) 0.0040(10) C26 0.0398(12) 0.0224(11) 0.0256(11) 0.0015(9) 0.0021(9) 0.0033(9) C27 0.0241(10) 0.0239(11) 0.0256(11) -0.0028(8) 0.0009(8) -0.0005(8) C28 0.0485(14) 0.0272(11) 0.0282(11) 0.0008(9) 0.0013(10) 0.0041(10) C29 0.0500(15) 0.0368(13) 0.0275(11) 0.0006(10) 0.0042(10) 0.0017(11) C30 0.0222(10) 0.0231(11) 0.0223(10) -0.0031(8) -0.0027(8) 0.0019(8) C31 0.0306(11) 0.0260(12) 0.0287(12) -0.0014(9) 0.0034(9) -0.0013(9) C32 0.0343(13) 0.0264(12) 0.0340(13) -0.0055(10) 0.0029(10) -0.0014(9) C33 0.0301(11) 0.0336(11) 0.0245(10) -0.0023(9) 0.0033(8) -0.0005(9) C34 0.0283(11) 0.0252(10) 0.0272(11) -0.0023(8) 0.0004(8) 0.0001(9) C35 0.0255(11) 0.0380(14) 0.0299(12) -0.0065(10) 0.0056(9) -0.0013(9) C36 0.0235(11) 0.0368(14) 0.0321(12) 0.0061(10) 0.0019(9) -0.0013(9) N1 0.0279(9) 0.0347(11) 0.0272(10) -0.0068(8) 0.0003(7) 0.0011(8) N2 0.0330(10) 0.0340(11) 0.0266(10) -0.0077(8) 0.0011(7) -0.0004(8) O1 0.0278(8) 0.0292(9) 0.0261(8) -0.0060(7) 0.0003(6) 0.0022(6) O2 0.0287(8) 0.0403(10) 0.0278(8) 0.0105(8) 0.0025(7) 0.0047(7) O3 0.0291(9) 0.0435(11) 0.0277(9) -0.0098(8) 0.0047(7) -0.0085(8) O4 0.0251(8) 0.0352(9) 0.0242(8) 0.0056(7) -0.0026(6) -0.0040(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O3 1.375(3) . ? C1 C2 1.395(3) . ? C1 C5 1.394(3) . ? C2 C3 1.379(4) . ? C2 H2 1.00(3) . ? C3 C4 1.390(4) . ? C3 H18 0.93(3) . ? C4 C6 1.392(3) . ? C4 H1 0.95(3) . ? C5 C6 1.410(3) . ? C5 C35 1.502(3) . ? C6 O1 1.374(3) . ? C7 C12 1.399(3) . ? C7 C8 1.402(3) . ? C7 C36 1.507(3) . ? C8 O4 1.375(3) . ? C8 C9 1.392(3) . ? C9 C10 1.387(4) . ? C9 H3 0.97(3) . ? C10 C11 1.385(3) . ? C10 H21 0.95(3) . ? C11 C12 1.396(3) . ? C11 H35 1.04(3) . ? C12 O2 1.363(3) . ? C13 C20 1.380(4) . ? C13 C24 1.395(4) . ? C13 C14 1.479(3) . ? C14 C19 1.376(5) . ? C14 C15 1.411(5) . ? C15 C16 1.347(5) . ? C15 H47 0.9500 . ? C16 C17 1.279(7) . ? C16 H16 0.9500 . ? C17 C18 1.374(7) . ? C17 H17 0.9500 . ? C18 C19 1.499(6) . ? C18 H46 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.395(7) . ? C20 H20 0.9500 . ? C21 C22 1.390(12) . ? C21 H45 0.9500 . ? C22 C23 1.346(11) . ? C22 H22 0.9500 . ? C23 C24 1.399(5) . ? C23 H48 0.9500 . ? C24 H24 0.9500 . ? C25 N2 1.331(4) . ? C25 C26 1.381(3) . ? C25 H25 0.9500 . ? C26 C27 1.394(3) . ? C26 H26 0.9500 . ? C27 C28 1.387(3) . ? C27 C30 1.492(3) . ? C28 C29 1.381(3) . ? C28 H28 0.9500 . ? C29 N2 1.335(4) . ? C29 H29 0.9500 . ? C30 C34 1.390(3) . ? C30 C31 1.399(3) . ? C31 C32 1.383(3) . ? C31 H11 0.97(3) . ? C32 N1 1.348(3) . ? C32 H12 0.99(3) . ? C33 N1 1.338(3) . ? C33 C34 1.394(3) . ? C33 H32 0.97(3) . ? C34 H33 1.01(3) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? O1 H100 0.8400 . ? O2 H42 0.98(3) . ? O3 H41 0.80(4) . ? O4 H23 1.00(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 C1 C2 121.2(2) . . ? O3 C1 C5 116.3(2) . . ? C2 C1 C5 122.4(2) . . ? C3 C2 C1 118.9(2) . . ? C3 C2 H2 123.3(16) . . ? C1 C2 H2 117.8(16) . . ? C2 C3 C4 121.1(2) . . ? C2 C3 H18 120.9(18) . . ? C4 C3 H18 117.9(17) . . ? C3 C4 C6 119.1(2) . . ? C3 C4 H1 125.8(18) . . ? C6 C4 H1 115.0(18) . . ? C1 C5 C6 116.8(2) . . ? C1 C5 C35 122.1(2) . . ? C6 C5 C35 121.1(2) . . ? O1 C6 C4 121.4(2) . . ? O1 C6 C5 116.88(19) . . ? C4 C6 C5 121.7(2) . . ? C12 C7 C8 117.7(2) . . ? C12 C7 C36 120.5(2) . . ? C8 C7 C36 121.8(2) . . ? O4 C8 C9 121.4(2) . . ? O4 C8 C7 117.1(2) . . ? C9 C8 C7 121.5(2) . . ? C10 C9 C8 119.2(2) . . ? C10 C9 H3 120.1(17) . . ? C8 C9 H3 120.7(17) . . ? C11 C10 C9 121.0(2) . . ? C11 C10 H21 119.8(19) . . ? C9 C10 H21 118.9(19) . . ? C10 C11 C12 119.1(2) . . ? C10 C11 H35 120.8(14) . . ? C12 C11 H35 119.9(14) . . ? O2 C12 C11 121.8(2) . . ? O2 C12 C7 116.8(2) . . ? C11 C12 C7 121.4(2) . . ? C20 C13 C24 118.8(3) . . ? C20 C13 C14 120.9(2) . . ? C24 C13 C14 120.3(3) . . ? C19 C14 C15 116.6(3) . . ? C19 C14 C13 123.4(3) . . ? C15 C14 C13 120.0(3) . . ? C16 C15 C14 125.1(4) . . ? C16 C15 H47 117.5 . . ? C14 C15 H47 117.5 . . ? C17 C16 C15 117.9(5) . . ? C17 C16 H16 121.0 . . ? C15 C16 H16 121.0 . . ? C16 C17 C18 126.0(5) . . ? C16 C17 H17 117.0 . . ? C18 C17 H17 117.0 . . ? C17 C18 C19 116.2(4) . . ? C17 C18 H46 121.9 . . ? C19 C18 H46 121.9 . . ? C14 C19 C18 118.2(4) . . ? C14 C19 H19 120.9 . . ? C18 C19 H19 120.9 . . ? C13 C20 C21 119.8(5) . . ? C13 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C20 C21 C22 121.9(5) . . ? C20 C21 H45 119.1 . . ? C22 C21 H45 119.1 . . ? C23 C22 C21 117.2(4) . . ? C23 C22 H22 121.4 . . ? C21 C22 H22 121.4 . . ? C22 C23 C24 123.1(5) . . ? C22 C23 H48 118.5 . . ? C24 C23 H48 118.5 . . ? C13 C24 C23 119.2(4) . . ? C13 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? N2 C25 C26 123.7(2) . . ? N2 C25 H25 118.1 . . ? C26 C25 H25 118.1 . . ? C25 C26 C27 119.5(2) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? C28 C27 C26 116.6(2) . . ? C28 C27 C30 122.35(18) . . ? C26 C27 C30 121.00(19) . . ? C29 C28 C27 119.8(2) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? N2 C29 C28 123.6(2) . . ? N2 C29 H29 118.2 . . ? C28 C29 H29 118.2 . . ? C34 C30 C31 117.7(2) . . ? C34 C30 C27 121.59(18) . . ? C31 C30 C27 120.67(19) . . ? C32 C31 C30 119.5(2) . . ? C32 C31 H11 113.4(16) . . ? C30 C31 H11 126.8(16) . . ? N1 C32 C31 122.9(2) . . ? N1 C32 H12 119.4(17) . . ? C31 C32 H12 117.5(17) . . ? N1 C33 C34 123.4(2) . . ? N1 C33 H32 113.7(15) . . ? C34 C33 H32 122.7(15) . . ? C30 C34 C33 119.0(2) . . ? C30 C34 H33 120.8(15) . . ? C33 C34 H33 119.9(15) . . ? C5 C35 H35A 109.5 . . ? C5 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C5 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C7 C36 H36A 109.5 . . ? C7 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C7 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C33 N1 C32 117.5(2) . . ? C25 N2 C29 116.7(2) . . ? C6 O1 H100 109.5 . . ? C12 O2 H42 110.1(18) . . ? C1 O3 H41 106(3) . . ? C8 O4 H23 112(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 O3 C1 C2 C3 -178.9(2) . . . . ? C5 C1 C2 C3 1.4(4) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C2 C3 C4 C6 -0.5(4) . . . . ? O3 C1 C5 C6 178.7(2) . . . . ? C2 C1 C5 C6 -1.6(3) . . . . ? O3 C1 C5 C35 -2.5(3) . . . . ? C2 C1 C5 C35 177.3(2) . . . . ? C3 C4 C6 O1 179.6(2) . . . . ? C3 C4 C6 C5 0.3(4) . . . . ? C1 C5 C6 O1 -178.6(2) . . . . ? C35 C5 C6 O1 2.5(3) . . . . ? C1 C5 C6 C4 0.7(3) . . . . ? C35 C5 C6 C4 -178.1(2) . . . . ? C12 C7 C8 O4 177.6(2) . . . . ? C36 C7 C8 O4 0.1(3) . . . . ? C12 C7 C8 C9 -1.0(3) . . . . ? C36 C7 C8 C9 -178.5(2) . . . . ? O4 C8 C9 C10 -179.6(2) . . . . ? C7 C8 C9 C10 -1.0(4) . . . . ? C8 C9 C10 C11 1.5(4) . . . . ? C9 C10 C11 C12 0.1(4) . . . . ? C10 C11 C12 O2 179.1(2) . . . . ? C10 C11 C12 C7 -2.2(4) . . . . ? C8 C7 C12 O2 -178.6(2) . . . . ? C36 C7 C12 O2 -1.0(3) . . . . ? C8 C7 C12 C11 2.6(3) . . . . ? C36 C7 C12 C11 -179.8(2) . . . . ? C20 C13 C14 C19 -27.4(4) . . . . ? C24 C13 C14 C19 151.2(3) . . . . ? C20 C13 C14 C15 153.5(3) . . . . ? C24 C13 C14 C15 -27.9(4) . . . . ? C19 C14 C15 C16 0.0(5) . . . . ? C13 C14 C15 C16 179.2(3) . . . . ? C14 C15 C16 C17 1.6(6) . . . . ? C15 C16 C17 C18 -0.9(7) . . . . ? C16 C17 C18 C19 -1.3(6) . . . . ? C15 C14 C19 C18 -2.2(4) . . . . ? C13 C14 C19 C18 178.6(3) . . . . ? C17 C18 C19 C14 2.8(5) . . . . ? C24 C13 C20 C21 0.2(4) . . . . ? C14 C13 C20 C21 178.8(3) . . . . ? C13 C20 C21 C22 0.2(6) . . . . ? C20 C21 C22 C23 0.0(7) . . . . ? C21 C22 C23 C24 -0.6(7) . . . . ? C20 C13 C24 C23 -0.7(4) . . . . ? C14 C13 C24 C23 -179.4(3) . . . . ? C22 C23 C24 C13 1.0(5) . . . . ? N2 C25 C26 C27 -0.3(4) . . . . ? C25 C26 C27 C28 0.1(3) . . . . ? C25 C26 C27 C30 -178.4(2) . . . . ? C26 C27 C28 C29 0.1(4) . . . . ? C30 C27 C28 C29 178.5(2) . . . . ? C27 C28 C29 N2 -0.1(4) . . . . ? C28 C27 C30 C34 157.1(2) . . . . ? C26 C27 C30 C34 -24.5(3) . . . . ? C28 C27 C30 C31 -24.0(3) . . . . ? C26 C27 C30 C31 154.4(2) . . . . ? C34 C30 C31 C32 -0.2(3) . . . . ? C27 C30 C31 C32 -179.0(2) . . . . ? C30 C31 C32 N1 1.2(4) . . . . ? C31 C30 C34 C33 -0.8(3) . . . . ? C27 C30 C34 C33 178.1(2) . . . . ? N1 C33 C34 C30 0.8(4) . . . . ? C34 C33 N1 C32 0.2(4) . . . . ? C31 C32 N1 C33 -1.2(4) . . . . ? C26 C25 N2 C29 0.3(4) . . . . ? C28 C29 N2 C25 0.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.609 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.053