# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Bielawski, Christopher' _publ_contact_author_email bielawski@mail.cm.utexas.edu _publ_section_title ; Ammonia N\^aH Activation by a N,N'\^aDiamidocarbene ; loop_ _publ_author_name T.Hudnall J.Moerdyk C.Bielawski # Attachment '- cif.cif' data_2-HCl _database_code_depnum_ccdc_archive 'CCDC 770147' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6-KetoMes-HCl _chemical_melting_point ? _chemical_formula_moiety N,N-(Mes)2-4,6-dioxo-5,5-(Me)2-2-HCl _chemical_formula_sum 'C24 H29 Cl N2 O2' _chemical_formula_weight 412.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.3918(12) _cell_length_b 17.082(2) _cell_length_c 15.992(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.394(2) _cell_angle_gamma 90.00 _cell_volume 2239.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19164 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3926 _reflns_number_gt 3412 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1075P)^2^+1.8398P] 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 3926 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1772 _refine_ls_wR_factor_gt 0.1696 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 Cl1 Cl 0.01898(8) 0.69732(3) 0.08906(4) 0.0452(2) Uani 1 1 d . . . N1 N 0.2242(2) 0.76716(10) 0.22372(11) 0.0263(4) Uani 1 1 d . . . O1 O 0.2156(2) 0.82908(10) 0.34770(11) 0.0411(4) Uani 1 1 d . . . C1 C 0.2153(3) 0.69828(12) 0.17286(14) 0.0286(5) Uani 1 1 d . . . H1A H 0.3048 0.7010 0.1424 0.034 Uiso 1 1 calc R . . O2 O 0.2312(2) 0.55602(10) 0.33897(11) 0.0419(4) Uani 1 1 d . . . N2 N 0.2328(2) 0.62605(10) 0.21909(12) 0.0281(4) Uani 1 1 d . . . C2 C 0.2027(3) 0.76829(13) 0.30704(14) 0.0292(5) Uani 1 1 d . . . C3 C 0.1578(3) 0.69135(13) 0.34425(15) 0.0329(5) Uani 1 1 d . . . C4 C 0.2116(3) 0.61870(13) 0.30198(14) 0.0302(5) Uani 1 1 d . . . C5 C -0.0317(4) 0.68945(17) 0.3275(3) 0.0597(9) Uani 1 1 d . . . H5A H -0.0760 0.6909 0.2669 0.089 Uiso 1 1 calc R . . H5B H -0.0699 0.7340 0.3541 0.089 Uiso 1 1 calc R . . H5C H -0.0662 0.6423 0.3511 0.089 Uiso 1 1 calc R . . C6 C 0.2346(5) 0.68916(16) 0.44048(18) 0.0606(9) Uani 1 1 d . . . H6A H 0.3513 0.6904 0.4487 0.091 Uiso 1 1 calc R . . H6B H 0.2021 0.6420 0.4649 0.091 Uiso 1 1 calc R . . H6C H 0.1984 0.7337 0.4680 0.091 Uiso 1 1 calc R . . C7 C 0.2469(3) 0.84140(13) 0.18276(13) 0.0278(5) Uani 1 1 d . . . C8 C 0.1130(3) 0.89036(13) 0.15385(14) 0.0305(5) Uani 1 1 d . . . C9 C 0.1395(3) 0.95938(14) 0.11184(15) 0.0354(5) Uani 1 1 d . . . H9A H 0.0517 0.9924 0.0915 0.043 Uiso 1 1 calc R . . C10 C 0.2930(3) 0.98017(14) 0.09946(15) 0.0378(6) Uani 1 1 d . . . C11 C 0.4241(3) 0.93203(15) 0.13306(16) 0.0389(6) Uani 1 1 d . . . H11A H 0.5280 0.9468 0.1276 0.047 Uiso 1 1 calc R . . C12 C 0.4046(3) 0.86210(14) 0.17488(15) 0.0338(5) Uani 1 1 d . . . C13 C -0.0560(3) 0.87293(14) 0.16828(17) 0.0389(6) Uani 1 1 d . . . H13A H -0.0547 0.8239 0.1977 0.058 Uiso 1 1 calc R . . H13B H -0.1318 0.8701 0.1141 0.058 Uiso 1 1 calc R . . H13C H -0.0886 0.9138 0.2022 0.058 Uiso 1 1 calc R . . C14 C 0.3166(4) 1.05379(17) 0.05031(19) 0.0527(7) Uani 1 1 d . . . H14A H 0.4295 1.0588 0.0481 0.079 Uiso 1 1 calc R . . H14B H 0.2835 1.0986 0.0786 0.079 Uiso 1 1 calc R . . H14C H 0.2516 1.0505 -0.0068 0.079 Uiso 1 1 calc R . . C15 C 0.5526(3) 0.81333(16) 0.2127(2) 0.0485(7) Uani 1 1 d . . . H15A H 0.6483 0.8374 0.2003 0.073 Uiso 1 1 calc R . . H15B H 0.5399 0.7618 0.1882 0.073 Uiso 1 1 calc R . . H15C H 0.5637 0.8098 0.2736 0.073 Uiso 1 1 calc R . . C16 C 0.2678(3) 0.55612(13) 0.17388(14) 0.0304(5) Uani 1 1 d . . . C17 C 0.4287(3) 0.54285(14) 0.16626(15) 0.0354(5) Uani 1 1 d . . . C18 C 0.4612(3) 0.47665(17) 0.12134(17) 0.0449(6) Uani 1 1 d . . . H18A H 0.5675 0.4674 0.1155 0.054 Uiso 1 1 calc R . . C19 C 0.3394(3) 0.42432(16) 0.08527(17) 0.0465(7) Uani 1 1 d . . . C20 C 0.1815(3) 0.43841(15) 0.09654(17) 0.0435(6) Uani 1 1 d . . . H20A H 0.0997 0.4029 0.0738 0.052 Uiso 1 1 calc R . . C21 C 0.1415(3) 0.50339(14) 0.14040(15) 0.0352(5) Uani 1 1 d . . . C22 C 0.5686(3) 0.59561(17) 0.20752(18) 0.0462(6) Uani 1 1 d . . . H22A H 0.6682 0.5765 0.1947 0.069 Uiso 1 1 calc R . . H22B H 0.5780 0.5960 0.2684 0.069 Uiso 1 1 calc R . . H22C H 0.5482 0.6478 0.1856 0.069 Uiso 1 1 calc R . . C23 C 0.3786(4) 0.3531(2) 0.0375(2) 0.0681(10) Uani 1 1 d . . . H23A H 0.4925 0.3533 0.0363 0.102 Uiso 1 1 calc R . . H23B H 0.3148 0.3540 -0.0200 0.102 Uiso 1 1 calc R . . H23C H 0.3535 0.3066 0.0660 0.102 Uiso 1 1 calc R . . C24 C -0.0316(3) 0.51315(15) 0.15167(19) 0.0421(6) Uani 1 1 d . . . H24A H -0.0974 0.4708 0.1238 0.063 Uiso 1 1 calc R . . H24B H -0.0748 0.5619 0.1268 0.063 Uiso 1 1 calc R . . H24C H -0.0326 0.5130 0.2116 0.063 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0510(4) 0.0371(4) 0.0398(4) 0.0012(2) -0.0070(3) -0.0051(3) N1 0.0253(9) 0.0255(10) 0.0291(9) 0.0010(7) 0.0084(7) -0.0029(7) O1 0.0573(11) 0.0323(9) 0.0350(9) -0.0050(7) 0.0126(8) -0.0013(8) C1 0.0267(11) 0.0304(12) 0.0294(11) -0.0003(8) 0.0075(9) -0.0036(8) O2 0.0568(11) 0.0299(9) 0.0406(10) 0.0082(7) 0.0144(8) 0.0049(8) N2 0.0288(9) 0.0256(9) 0.0313(10) 0.0006(7) 0.0092(7) 0.0012(7) C2 0.0262(11) 0.0311(12) 0.0310(11) 0.0009(9) 0.0079(9) 0.0019(9) C3 0.0389(13) 0.0301(12) 0.0337(12) 0.0048(9) 0.0168(10) 0.0031(9) C4 0.0280(11) 0.0312(12) 0.0323(12) 0.0031(9) 0.0083(9) -0.0003(9) C5 0.0455(17) 0.0437(16) 0.102(3) 0.0093(15) 0.0439(18) 0.0021(12) C6 0.112(3) 0.0414(16) 0.0327(15) 0.0047(11) 0.0251(16) 0.0102(16) C7 0.0298(11) 0.0264(11) 0.0282(11) -0.0004(9) 0.0084(9) -0.0061(9) C8 0.0316(12) 0.0289(11) 0.0314(11) -0.0014(9) 0.0074(9) -0.0038(9) C9 0.0432(13) 0.0288(12) 0.0343(12) 0.0021(9) 0.0083(10) -0.0012(10) C10 0.0543(15) 0.0310(12) 0.0306(12) -0.0020(10) 0.0147(11) -0.0116(11) C11 0.0388(13) 0.0418(14) 0.0401(13) -0.0035(11) 0.0175(11) -0.0147(11) C12 0.0309(12) 0.0364(12) 0.0357(12) -0.0045(10) 0.0109(9) -0.0082(10) C13 0.0312(12) 0.0335(13) 0.0530(15) 0.0068(11) 0.0116(11) 0.0029(10) C14 0.0714(19) 0.0432(15) 0.0480(16) 0.0110(12) 0.0232(14) -0.0114(14) C15 0.0285(13) 0.0501(16) 0.0677(19) 0.0041(13) 0.0121(12) -0.0066(11) C16 0.0333(12) 0.0278(11) 0.0302(11) -0.0009(9) 0.0071(9) 0.0033(9) C17 0.0332(12) 0.0381(13) 0.0342(12) -0.0007(10) 0.0061(9) 0.0050(10) C18 0.0368(13) 0.0535(16) 0.0437(14) -0.0065(12) 0.0073(11) 0.0138(12) C19 0.0489(15) 0.0458(15) 0.0401(14) -0.0098(12) -0.0008(11) 0.0156(12) C20 0.0435(14) 0.0360(13) 0.0457(14) -0.0095(11) -0.0027(11) 0.0036(11) C21 0.0350(12) 0.0312(12) 0.0375(13) 0.0014(10) 0.0035(10) 0.0029(10) C22 0.0302(12) 0.0525(16) 0.0558(16) -0.0062(13) 0.0090(11) 0.0011(11) C23 0.067(2) 0.067(2) 0.063(2) -0.0286(17) -0.0024(16) 0.0243(17) C24 0.0354(13) 0.0329(13) 0.0568(16) -0.0002(11) 0.0076(11) -0.0042(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.888(2) . ? N1 C2 1.383(3) . ? N1 C1 1.423(3) . ? N1 C7 1.458(3) . ? O1 C2 1.218(3) . ? C1 N2 1.430(3) . ? C1 H1A 0.9800 . ? O2 C4 1.217(3) . ? N2 C4 1.381(3) . ? N2 C16 1.459(3) . ? C2 C3 1.523(3) . ? C3 C4 1.527(3) . ? C3 C6 1.536(4) . ? C3 C5 1.555(4) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.397(3) . ? C7 C12 1.402(3) . ? C8 C9 1.398(3) . ? C8 C13 1.515(3) . ? C9 C10 1.391(4) . ? C9 H9A 0.9300 . ? C10 C11 1.386(4) . ? C10 C14 1.518(3) . ? C11 C12 1.396(3) . ? C11 H11A 0.9300 . ? C12 C15 1.510(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.400(3) . ? C16 C21 1.407(3) . ? C17 C18 1.398(3) . ? C17 C22 1.514(4) . ? C18 C19 1.387(4) . ? C18 H18A 0.9300 . ? C19 C20 1.396(4) . ? C19 C23 1.510(4) . ? C20 C21 1.392(3) . ? C20 H20A 0.9300 . ? C21 C24 1.511(3) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C1 124.11(18) . . ? C2 N1 C7 118.51(18) . . ? C1 N1 C7 117.26(16) . . ? N1 C1 N2 115.53(18) . . ? N1 C1 Cl1 110.08(15) . . ? N2 C1 Cl1 109.67(14) . . ? N1 C1 H1A 107.1 . . ? N2 C1 H1A 107.1 . . ? Cl1 C1 H1A 107.1 . . ? C4 N2 C1 123.71(18) . . ? C4 N2 C16 118.87(18) . . ? C1 N2 C16 117.37(17) . . ? O1 C2 N1 120.8(2) . . ? O1 C2 C3 121.9(2) . . ? N1 C2 C3 117.31(19) . . ? C2 C3 C4 114.02(18) . . ? C2 C3 C6 109.1(2) . . ? C4 C3 C6 108.9(2) . . ? C2 C3 C5 106.27(19) . . ? C4 C3 C5 107.2(2) . . ? C6 C3 C5 111.5(3) . . ? O2 C4 N2 121.0(2) . . ? O2 C4 C3 121.5(2) . . ? N2 C4 C3 117.55(19) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 121.8(2) . . ? C8 C7 N1 119.73(18) . . ? C12 C7 N1 118.48(19) . . ? C7 C8 C9 117.7(2) . . ? C7 C8 C13 123.0(2) . . ? C9 C8 C13 119.3(2) . . ? C10 C9 C8 122.1(2) . . ? C10 C9 H9A 119.0 . . ? C8 C9 H9A 119.0 . . ? C11 C10 C9 118.4(2) . . ? C11 C10 C14 120.7(2) . . ? C9 C10 C14 120.9(2) . . ? C10 C11 C12 121.9(2) . . ? C10 C11 H11A 119.0 . . ? C12 C11 H11A 119.0 . . ? C11 C12 C7 118.0(2) . . ? C11 C12 C15 119.6(2) . . ? C7 C12 C15 122.4(2) . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 121.7(2) . . ? C17 C16 N2 118.5(2) . . ? C21 C16 N2 119.8(2) . . ? C18 C17 C16 118.3(2) . . ? C18 C17 C22 119.2(2) . . ? C16 C17 C22 122.5(2) . . ? C19 C18 C17 121.8(2) . . ? C19 C18 H18A 119.1 . . ? C17 C18 H18A 119.1 . . ? C18 C19 C20 118.1(2) . . ? C18 C19 C23 120.6(3) . . ? C20 C19 C23 121.3(3) . . ? C21 C20 C19 122.8(2) . . ? C21 C20 H20A 118.6 . . ? C19 C20 H20A 118.6 . . ? C20 C21 C16 117.3(2) . . ? C20 C21 C24 119.4(2) . . ? C16 C21 C24 123.3(2) . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.420 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.057 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 770148' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '6-KetoMes carbene' _chemical_melting_point ? _chemical_formula_moiety N,N-(Mes)2-4,6-dioxo-5,5-(Me)2-2-ylidene _chemical_formula_sum 'C24 H28 N2 O2' _chemical_formula_weight 376.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 P2(1)/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 17.7632(14) _cell_length_b 16.2017(12) _cell_length_c 7.6426(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.686(2) _cell_angle_gamma 90.00 _cell_volume 2179.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.147 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18370 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3830 _reflns_number_gt 3133 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0693P)^2^+1.9940P] 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 3830 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1640 _refine_ls_wR_factor_gt 0.1543 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.18817(10) 0.45198(11) 0.9473(2) 0.0348(4) Uani 1 1 d . . . N2 N 0.29640(10) 0.53006(11) 0.9391(2) 0.0358(4) Uani 1 1 d . . . C7 C 0.34878(12) 0.56983(14) 0.8337(3) 0.0367(5) Uani 1 1 d . . . O1 O 0.14125(10) 0.42439(12) 1.2051(2) 0.0522(5) Uani 1 1 d . . . C16 C 0.12370(12) 0.40815(14) 0.8493(3) 0.0361(5) Uani 1 1 d . . . C18 C -0.00033(13) 0.41032(15) 0.6846(3) 0.0403(5) Uani 1 1 d . . . H18A H -0.0436 0.4392 0.6379 0.048 Uiso 1 1 calc R . . C19 C 0.00300(13) 0.32584(15) 0.6558(3) 0.0410(6) Uani 1 1 d . . . C20 C 0.06822(14) 0.28334(15) 0.7268(3) 0.0449(6) Uani 1 1 d . . . H20A H 0.0709 0.2267 0.7085 0.054 Uiso 1 1 calc R . . C17 C 0.05965(13) 0.45312(14) 0.7819(3) 0.0372(5) Uani 1 1 d . . . O2 O 0.36365(11) 0.58462(14) 1.1863(2) 0.0654(6) Uani 1 1 d . . . C12 C 0.33415(13) 0.65113(15) 0.7775(3) 0.0399(5) Uani 1 1 d . . . C2 C 0.19060(13) 0.45591(14) 1.1322(3) 0.0375(5) Uani 1 1 d . . . C1 C 0.23781(13) 0.48671(14) 0.8462(3) 0.0382(5) Uani 1 1 d . . . C21 C 0.12941(13) 0.32322(14) 0.8243(3) 0.0414(6) Uani 1 1 d . . . C8 C 0.41194(13) 0.52603(15) 0.7937(3) 0.0409(6) Uani 1 1 d . . . C4 C 0.31058(13) 0.54240(15) 1.1228(3) 0.0408(6) Uani 1 1 d . . . C11 C 0.38611(14) 0.68875(16) 0.6803(3) 0.0464(6) Uani 1 1 d . . . H11A H 0.3777 0.7429 0.6426 0.056 Uiso 1 1 calc R . . C23 C -0.06297(15) 0.28042(17) 0.5516(4) 0.0527(7) Uani 1 1 d . . . H23A H -0.0507 0.2229 0.5451 0.079 Uiso 1 1 calc R . . H23B H -0.0725 0.3029 0.4345 0.079 Uiso 1 1 calc R . . H23C H -0.1074 0.2867 0.6092 0.079 Uiso 1 1 calc R . . C9 C 0.46118(13) 0.56629(17) 0.6939(3) 0.0465(6) Uani 1 1 d . . . H9A H 0.5030 0.5377 0.6634 0.056 Uiso 1 1 calc R . . C10 C 0.44986(14) 0.64763(17) 0.6384(3) 0.0475(6) Uani 1 1 d . . . C3 C 0.25776(13) 0.50034(14) 1.2354(3) 0.0389(5) Uani 1 1 d . . . C22 C 0.05449(15) 0.54514(15) 0.8130(4) 0.0505(6) Uani 1 1 d . . . H22A H 0.1005 0.5639 0.8818 0.076 Uiso 1 1 calc R . . H22B H 0.0122 0.5564 0.8754 0.076 Uiso 1 1 calc R . . H22C H 0.0475 0.5734 0.7016 0.076 Uiso 1 1 calc R . . C15 C 0.26384(15) 0.69630(17) 0.8153(4) 0.0534(7) Uani 1 1 d . . . H15A H 0.2349 0.6614 0.8829 0.080 Uiso 1 1 calc R . . H15B H 0.2335 0.7107 0.7061 0.080 Uiso 1 1 calc R . . H15C H 0.2783 0.7456 0.8811 0.080 Uiso 1 1 calc R . . C24 C 0.19990(15) 0.27590(17) 0.8998(4) 0.0591(8) Uani 1 1 d . . . H24A H 0.1936 0.2186 0.8694 0.089 Uiso 1 1 calc R . . H24B H 0.2077 0.2817 1.0259 0.089 Uiso 1 1 calc R . . H24C H 0.2431 0.2975 0.8518 0.089 Uiso 1 1 calc R . . C13 C 0.42586(16) 0.43804(17) 0.8545(4) 0.0562(7) Uani 1 1 d . . . H13A H 0.4716 0.4180 0.8150 0.084 Uiso 1 1 calc R . . H13B H 0.3838 0.4042 0.8061 0.084 Uiso 1 1 calc R . . H13C H 0.4311 0.4359 0.9811 0.084 Uiso 1 1 calc R . . C14 C 0.50503(18) 0.6912(2) 0.5361(4) 0.0735(9) Uani 1 1 d . . . H14A H 0.4877 0.7465 0.5098 0.110 Uiso 1 1 calc R . . H14B H 0.5082 0.6620 0.4279 0.110 Uiso 1 1 calc R . . H14C H 0.5543 0.6927 0.6053 0.110 Uiso 1 1 calc R . . C6 C 0.22697(18) 0.56564(19) 1.3546(4) 0.0638(8) Uani 1 1 d . . . H6A H 0.1976 0.6058 1.2824 0.096 Uiso 1 1 calc R . . H6B H 0.2687 0.5925 1.4248 0.096 Uiso 1 1 calc R . . H6C H 0.1954 0.5392 1.4306 0.096 Uiso 1 1 calc R . . C5 C 0.30489(17) 0.4360(2) 1.3514(4) 0.0685(9) Uani 1 1 d . . . H5A H 0.3240 0.3954 1.2774 0.103 Uiso 1 1 calc R . . H5B H 0.2734 0.4097 1.4275 0.103 Uiso 1 1 calc R . . H5C H 0.3466 0.4630 1.4216 0.103 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 0.0349(10) 0.0342(10) 0.0336(10) -0.0049(8) -0.0009(8) -0.0030(8) N2 0.0338(10) 0.0394(10) 0.0331(10) -0.0047(8) 0.0002(8) -0.0029(8) C7 0.0343(11) 0.0429(13) 0.0313(11) -0.0044(10) -0.0007(9) -0.0035(10) O1 0.0496(10) 0.0638(12) 0.0430(10) -0.0009(8) 0.0054(8) -0.0169(9) C16 0.0360(11) 0.0377(12) 0.0337(11) -0.0035(9) 0.0013(9) -0.0046(9) C18 0.0359(12) 0.0454(13) 0.0379(12) 0.0016(10) -0.0012(10) -0.0009(10) C19 0.0426(13) 0.0437(13) 0.0361(12) -0.0033(10) 0.0029(10) -0.0095(10) C20 0.0503(14) 0.0343(12) 0.0486(14) -0.0084(10) 0.0005(11) -0.0048(11) C17 0.0385(12) 0.0359(12) 0.0367(12) -0.0014(10) 0.0027(10) -0.0015(10) O2 0.0628(12) 0.0908(15) 0.0409(10) -0.0130(10) 0.0012(9) -0.0397(11) C12 0.0386(12) 0.0432(13) 0.0363(12) -0.0032(10) -0.0007(10) -0.0011(10) C2 0.0389(12) 0.0350(12) 0.0373(12) -0.0018(10) 0.0002(10) -0.0003(10) C1 0.0363(12) 0.0391(12) 0.0379(12) -0.0047(10) 0.0004(10) -0.0001(10) C21 0.0425(13) 0.0382(13) 0.0419(13) -0.0056(10) 0.0000(10) 0.0002(10) C8 0.0373(12) 0.0463(14) 0.0372(12) -0.0049(10) -0.0014(10) 0.0013(10) C4 0.0410(13) 0.0448(13) 0.0351(12) -0.0057(10) -0.0007(10) -0.0046(11) C11 0.0471(14) 0.0468(14) 0.0430(13) 0.0037(11) -0.0026(11) -0.0047(11) C23 0.0507(15) 0.0535(15) 0.0510(15) -0.0073(12) -0.0038(12) -0.0140(12) C9 0.0359(12) 0.0643(17) 0.0394(13) -0.0062(12) 0.0050(10) 0.0036(11) C10 0.0429(13) 0.0618(16) 0.0365(12) 0.0013(12) 0.0010(10) -0.0066(12) C3 0.0411(13) 0.0412(13) 0.0324(11) -0.0023(10) -0.0021(10) -0.0055(10) C22 0.0491(14) 0.0383(13) 0.0610(16) -0.0017(12) -0.0045(12) 0.0017(11) C15 0.0497(15) 0.0477(15) 0.0629(17) 0.0028(13) 0.0072(13) 0.0078(12) C24 0.0545(16) 0.0477(15) 0.0697(18) -0.0129(13) -0.0122(14) 0.0096(12) C13 0.0545(16) 0.0513(16) 0.0627(17) -0.0013(13) 0.0075(13) 0.0113(13) C14 0.0606(18) 0.093(2) 0.070(2) 0.0193(18) 0.0211(16) -0.0050(17) C6 0.0690(19) 0.0660(19) 0.0593(17) -0.0255(15) 0.0190(15) -0.0207(15) C5 0.0550(17) 0.0698(19) 0.073(2) 0.0223(16) -0.0198(15) -0.0106(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.369(3) . ? N1 C2 1.409(3) . ? N1 C16 1.466(3) . ? N2 C1 1.372(3) . ? N2 C4 1.407(3) . ? N2 C7 1.459(3) . ? C7 C8 1.395(3) . ? C7 C12 1.399(3) . ? O1 C2 1.212(3) . ? C16 C17 1.391(3) . ? C16 C21 1.395(3) . ? C18 C19 1.389(3) . ? C18 C17 1.399(3) . ? C18 H18A 0.9300 . ? C19 C20 1.394(3) . ? C19 C23 1.516(3) . ? C20 C21 1.392(3) . ? C20 H20A 0.9300 . ? C17 C22 1.514(3) . ? O2 C4 1.212(3) . ? C12 C11 1.400(3) . ? C12 C15 1.509(3) . ? C2 C3 1.520(3) . ? C21 C24 1.515(3) . ? C8 C9 1.397(3) . ? C8 C13 1.509(4) . ? C4 C3 1.517(3) . ? C11 C10 1.388(4) . ? C11 H11A 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C9 C10 1.391(4) . ? C9 H9A 0.9300 . ? C10 C14 1.508(4) . ? C3 C5 1.541(4) . ? C3 C6 1.543(4) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? 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 127.72(18) . . ? C1 N1 C16 115.40(17) . . ? C2 N1 C16 116.84(18) . . ? C1 N2 C4 127.65(19) . . ? C1 N2 C7 115.85(18) . . ? C4 N2 C7 116.47(18) . . ? C8 C7 C12 122.2(2) . . ? C8 C7 N2 119.1(2) . . ? C12 C7 N2 118.6(2) . . ? C17 C16 C21 122.5(2) . . ? C17 C16 N1 118.69(19) . . ? C21 C16 N1 118.8(2) . . ? C19 C18 C17 121.8(2) . . ? C19 C18 H18A 119.1 . . ? C17 C18 H18A 119.1 . . ? C18 C19 C20 118.4(2) . . ? C18 C19 C23 121.0(2) . . ? C20 C19 C23 120.6(2) . . ? C21 C20 C19 121.9(2) . . ? C21 C20 H20A 119.1 . . ? C19 C20 H20A 119.1 . . ? C16 C17 C18 117.7(2) . . ? C16 C17 C22 121.4(2) . . ? C18 C17 C22 120.9(2) . . ? C7 C12 C11 117.7(2) . . ? C7 C12 C15 121.5(2) . . ? C11 C12 C15 120.8(2) . . ? O1 C2 N1 121.0(2) . . ? O1 C2 C3 121.8(2) . . ? N1 C2 C3 117.3(2) . . ? N1 C1 N2 114.83(19) . . ? C20 C21 C16 117.7(2) . . ? C20 C21 C24 121.0(2) . . ? C16 C21 C24 121.2(2) . . ? C7 C8 C9 117.6(2) . . ? C7 C8 C13 121.1(2) . . ? C9 C8 C13 121.4(2) . . ? O2 C4 N2 120.4(2) . . ? O2 C4 C3 122.2(2) . . ? N2 C4 C3 117.43(19) . . ? C10 C11 C12 122.0(2) . . ? C10 C11 H11A 119.0 . . ? C12 C11 H11A 119.0 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C10 C9 C8 122.2(2) . . ? C10 C9 H9A 118.9 . . ? C8 C9 H9A 118.9 . . ? C11 C10 C9 118.3(2) . . ? C11 C10 C14 120.1(3) . . ? C9 C10 C14 121.6(3) . . ? C4 C3 C2 114.84(18) . . ? C4 C3 C5 107.5(2) . . ? C2 C3 C5 107.9(2) . . ? C4 C3 C6 108.8(2) . . ? C2 C3 C6 108.4(2) . . ? C5 C3 C6 109.4(2) . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.380 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.046 #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 770149' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6-KetoMes-NH3 _chemical_melting_point ? _chemical_formula_moiety N,N-(Mes)2-4,6-dioxo-5,5-(Me)2-2-H-NH2 _chemical_formula_sum 'C24.50 H32 Cl N3 O2' _chemical_formula_weight 435.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/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 15.7619(11) _cell_length_b 25.7674(18) _cell_length_c 11.6636(9) _cell_angle_alpha 90.00 _cell_angle_beta 92.970(2) _cell_angle_gamma 90.00 _cell_volume 4730.7(6) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1864 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20564 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4162 _reflns_number_gt 3375 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0842P)^2^+7.4016P] 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 4162 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0700 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1637 _refine_ls_wR_factor_gt 0.1528 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 N1 N 0.21831(11) 0.12263(7) 0.39795(15) 0.0273(4) Uani 1 1 d . . . O1 O 0.10438(11) 0.17032(6) 0.44026(16) 0.0456(5) Uani 1 1 d . . . O2 O 0.14973(10) 0.00795(7) 0.61189(14) 0.0386(4) Uani 1 1 d . . . N2 N 0.24236(11) 0.03821(7) 0.48598(15) 0.0276(4) Uani 1 1 d . . . C4 C 0.16694(13) 0.03954(8) 0.53831(18) 0.0280(5) Uani 1 1 d . . . C2 C 0.14217(13) 0.12875(8) 0.44457(18) 0.0297(5) Uani 1 1 d . . . C3 C 0.10274(13) 0.08088(9) 0.49718(19) 0.0305(5) Uani 1 1 d . . . C16 C 0.30097(13) -0.00427(8) 0.51162(18) 0.0291(5) Uani 1 1 d . . . C7 C 0.25574(13) 0.16568(8) 0.33771(19) 0.0285(5) Uani 1 1 d . . . C12 C 0.31355(13) 0.19799(8) 0.3982(2) 0.0309(5) Uani 1 1 d . . . C8 C 0.23394(14) 0.17320(9) 0.2210(2) 0.0348(5) Uani 1 1 d . . . C17 C 0.37348(14) 0.00503(9) 0.58314(19) 0.0336(5) Uani 1 1 d . . . C11 C 0.35440(15) 0.23627(9) 0.3366(2) 0.0379(6) Uani 1 1 d . . . H11A H 0.3935 0.2579 0.3752 0.046 Uiso 1 1 calc R . . C15 C 0.32965(16) 0.19431(9) 0.5265(2) 0.0389(6) Uani 1 1 d . . . H15A H 0.2773 0.1869 0.5618 0.058 Uiso 1 1 calc R . . H15B H 0.3522 0.2266 0.5554 0.058 Uiso 1 1 calc R . . H15C H 0.3697 0.1670 0.5441 0.058 Uiso 1 1 calc R . . C18 C 0.43066(15) -0.03613(10) 0.6021(2) 0.0397(6) Uani 1 1 d . . . H18A H 0.4806 -0.0302 0.6462 0.048 Uiso 1 1 calc R . . C21 C 0.28435(15) -0.05323(9) 0.46292(19) 0.0342(5) Uani 1 1 d . . . C9 C 0.27686(16) 0.21181(9) 0.1637(2) 0.0415(6) Uani 1 1 d . . . H9A H 0.2640 0.2169 0.0858 0.050 Uiso 1 1 calc R . . C1 C 0.27030(15) 0.07498(9) 0.39943(19) 0.0339(5) Uani 1 1 d . . . H1A H 0.3275 0.0858 0.4264 0.041 Uiso 1 1 calc R . . C10 C 0.33838(16) 0.24300(9) 0.2192(2) 0.0410(6) Uani 1 1 d . . . C19 C 0.41577(16) -0.08511(10) 0.5580(2) 0.0431(6) Uani 1 1 d . . . C5 C 0.04476(15) 0.05660(10) 0.3992(2) 0.0428(6) Uani 1 1 d . . . H5A H 0.0792 0.0442 0.3395 0.064 Uiso 1 1 calc R . . H5B H 0.0060 0.0824 0.3684 0.064 Uiso 1 1 calc R . . H5C H 0.0132 0.0282 0.4292 0.064 Uiso 1 1 calc R . . C20 C 0.34209(16) -0.09299(10) 0.4887(2) 0.0425(6) Uani 1 1 d . . . H20A H 0.3312 -0.1259 0.4587 0.051 Uiso 1 1 calc R . . C6 C 0.04925(17) 0.09696(11) 0.5974(2) 0.0489(7) Uani 1 1 d . . . H6A H 0.0852 0.1130 0.6561 0.073 Uiso 1 1 calc R . . H6B H 0.0228 0.0668 0.6282 0.073 Uiso 1 1 calc R . . H6C H 0.0063 0.1211 0.5706 0.073 Uiso 1 1 calc R . . C24 C 0.20617(18) -0.06369(10) 0.3872(2) 0.0469(6) Uani 1 1 d . . . H24A H 0.2068 -0.0991 0.3614 0.070 Uiso 1 1 calc R . . H24B H 0.2053 -0.0409 0.3220 0.070 Uiso 1 1 calc R . . H24C H 0.1565 -0.0578 0.4297 0.070 Uiso 1 1 calc R . . C13 C 0.16404(17) 0.14268(10) 0.1585(2) 0.0448(6) Uani 1 1 d . . . H13A H 0.1468 0.1602 0.0884 0.067 Uiso 1 1 calc R . . H13B H 0.1164 0.1399 0.2061 0.067 Uiso 1 1 calc R . . H13C H 0.1845 0.1086 0.1411 0.067 Uiso 1 1 calc R . . C22 C 0.38952(17) 0.05574(10) 0.6448(2) 0.0469(6) Uani 1 1 d . . . H22A H 0.4028 0.0492 0.7248 0.070 Uiso 1 1 calc R . . H22B H 0.3397 0.0771 0.6367 0.070 Uiso 1 1 calc R . . H22C H 0.4363 0.0733 0.6123 0.070 Uiso 1 1 calc R . . C14 C 0.3851(2) 0.28344(12) 0.1531(3) 0.0634(9) Uani 1 1 d . . . H14A H 0.4250 0.3012 0.2041 0.095 Uiso 1 1 calc R . . H14B H 0.3451 0.3079 0.1197 0.095 Uiso 1 1 calc R . . H14C H 0.4149 0.2669 0.0933 0.095 Uiso 1 1 calc R . . C23 C 0.4758(2) -0.12990(13) 0.5863(3) 0.0644(9) Uani 1 1 d . . . H23A H 0.5267 -0.1169 0.6248 0.097 Uiso 1 1 calc R . . H23B H 0.4897 -0.1470 0.5166 0.097 Uiso 1 1 calc R . . H23C H 0.4488 -0.1541 0.6353 0.097 Uiso 1 1 calc R . . Cl1 Cl 0.06940(8) 0.28495(6) 0.17497(11) 0.1157(5) Uani 1 1 d . . . C25 C 0.0000 0.2474(2) 0.2500 0.0786(15) Uani 1 2 d S . . H25A H 0.0320 0.2254 0.3029 0.118 Uiso 1 1 d R . . N3 N 0.28050(16) 0.04997(9) 0.29390(18) 0.0487(6) Uani 1 1 d G . . H3A H 0.3158 0.0687 0.2477 0.073 Uiso 1 1 d G . . H3B H 0.2272 0.0421 0.2606 0.073 Uiso 1 1 d G . . 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 0.0278(9) 0.0238(9) 0.0303(9) 0.0006(7) 0.0007(7) -0.0011(7) O1 0.0402(10) 0.0333(9) 0.0641(12) 0.0056(8) 0.0096(8) 0.0088(8) O2 0.0347(9) 0.0440(10) 0.0374(9) 0.0134(8) 0.0055(7) -0.0016(7) N2 0.0264(9) 0.0282(9) 0.0281(9) 0.0047(7) 0.0012(7) 0.0014(7) C4 0.0271(11) 0.0312(11) 0.0253(11) -0.0014(9) -0.0020(8) -0.0040(9) C2 0.0285(11) 0.0297(12) 0.0302(11) -0.0022(9) -0.0038(9) 0.0006(9) C3 0.0249(10) 0.0339(12) 0.0327(11) 0.0017(9) 0.0019(9) 0.0008(9) C16 0.0271(11) 0.0318(12) 0.0289(11) 0.0064(9) 0.0042(9) 0.0030(9) C7 0.0275(11) 0.0246(11) 0.0334(12) 0.0028(9) 0.0021(9) 0.0010(9) C12 0.0288(11) 0.0249(11) 0.0389(12) -0.0018(9) -0.0001(9) 0.0024(9) C8 0.0365(13) 0.0313(12) 0.0361(13) 0.0041(10) -0.0020(10) -0.0013(10) C17 0.0316(12) 0.0407(13) 0.0286(11) 0.0069(10) 0.0029(9) -0.0015(10) C11 0.0335(12) 0.0281(12) 0.0520(15) -0.0026(10) 0.0016(11) -0.0048(10) C15 0.0413(13) 0.0346(13) 0.0402(13) -0.0048(10) -0.0042(10) -0.0023(10) C18 0.0279(12) 0.0550(16) 0.0360(13) 0.0119(11) 0.0010(10) 0.0077(11) C21 0.0360(12) 0.0339(12) 0.0326(12) 0.0046(10) 0.0017(9) 0.0011(10) C9 0.0507(15) 0.0378(13) 0.0358(13) 0.0102(10) -0.0001(11) -0.0019(11) C1 0.0351(12) 0.0314(12) 0.0359(12) 0.0064(10) 0.0084(10) 0.0038(10) C10 0.0432(14) 0.0300(12) 0.0502(15) 0.0075(11) 0.0058(11) -0.0009(10) C19 0.0368(13) 0.0487(15) 0.0446(14) 0.0133(12) 0.0098(11) 0.0146(11) C5 0.0320(12) 0.0461(14) 0.0490(15) 0.0084(12) -0.0121(11) -0.0081(11) C20 0.0478(14) 0.0342(13) 0.0459(14) 0.0042(11) 0.0070(11) 0.0068(11) C6 0.0444(14) 0.0513(16) 0.0526(16) 0.0024(13) 0.0187(12) 0.0085(12) C24 0.0544(16) 0.0340(13) 0.0509(16) 0.0005(11) -0.0112(12) -0.0026(12) C13 0.0520(15) 0.0445(14) 0.0365(13) 0.0062(11) -0.0110(11) -0.0097(12) C22 0.0453(15) 0.0504(15) 0.0436(15) 0.0051(12) -0.0119(12) -0.0036(12) C14 0.075(2) 0.0488(17) 0.067(2) 0.0166(15) 0.0081(16) -0.0192(15) C23 0.0516(17) 0.065(2) 0.077(2) 0.0140(16) 0.0083(15) 0.0278(15) Cl1 0.0996(8) 0.1489(12) 0.0983(9) 0.0329(8) 0.0035(7) 0.0003(8) C25 0.102(4) 0.063(3) 0.067(3) 0.000 -0.030(3) 0.000 N3 0.0658(15) 0.0424(13) 0.0393(12) 0.0026(10) 0.0168(11) 0.0056(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.352(3) . ? N1 C7 1.454(3) . ? N1 C1 1.476(3) . ? O1 C2 1.225(3) . ? O2 C4 1.223(3) . ? N2 C4 1.365(3) . ? N2 C16 1.453(3) . ? N2 C1 1.469(3) . ? C4 C3 1.529(3) . ? C2 C3 1.524(3) . ? C3 C6 1.533(3) . ? C3 C5 1.557(3) . ? C16 C17 1.400(3) . ? C16 C21 1.403(3) . ? C7 C12 1.398(3) . ? C7 C8 1.400(3) . ? C12 C11 1.397(3) . ? C12 C15 1.508(3) . ? C8 C9 1.393(3) . ? C8 C13 1.510(3) . ? C17 C18 1.402(3) . ? C17 C22 1.507(4) . ? C11 C10 1.390(4) . ? C11 H11A 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C18 C19 1.379(4) . ? C18 H18A 0.9300 . ? C21 C20 1.393(3) . ? C21 C24 1.503(3) . ? C9 C10 1.393(4) . ? C9 H9A 0.9300 . ? C1 N3 1.406(3) . ? C1 H1A 0.9800 . ? C10 C14 1.510(3) . ? C19 C20 1.395(4) . ? C19 C23 1.518(4) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C20 H20A 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? Cl1 C25 1.731(3) . ? C25 Cl1 1.731(3) 2 ? C25 H25A 0.9605 . ? N3 H3A 0.9298 . ? N3 H3B 0.9301 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C7 119.73(17) . . ? C2 N1 C1 126.60(18) . . ? C7 N1 C1 113.66(16) . . ? C4 N2 C16 119.09(17) . . ? C4 N2 C1 126.18(18) . . ? C16 N2 C1 114.67(16) . . ? O2 C4 N2 121.8(2) . . ? O2 C4 C3 121.09(19) . . ? N2 C4 C3 117.06(18) . . ? O1 C2 N1 121.7(2) . . ? O1 C2 C3 121.09(19) . . ? N1 C2 C3 117.15(18) . . ? C2 C3 C4 114.39(17) . . ? C2 C3 C6 109.87(19) . . ? C4 C3 C6 109.29(19) . . ? C2 C3 C5 105.40(18) . . ? C4 C3 C5 107.71(18) . . ? C6 C3 C5 110.1(2) . . ? C17 C16 C21 121.7(2) . . ? C17 C16 N2 118.96(19) . . ? C21 C16 N2 119.38(19) . . ? C12 C7 C8 121.9(2) . . ? C12 C7 N1 118.72(19) . . ? C8 C7 N1 119.35(19) . . ? C11 C12 C7 117.8(2) . . ? C11 C12 C15 119.8(2) . . ? C7 C12 C15 122.3(2) . . ? C9 C8 C7 117.7(2) . . ? C9 C8 C13 120.0(2) . . ? C7 C8 C13 122.2(2) . . ? C16 C17 C18 117.6(2) . . ? C16 C17 C22 123.0(2) . . ? C18 C17 C22 119.3(2) . . ? C10 C11 C12 122.0(2) . . ? C10 C11 H11A 119.0 . . ? C12 C11 H11A 119.0 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C19 C18 C17 122.6(2) . . ? C19 C18 H18A 118.7 . . ? C17 C18 H18A 118.7 . . ? C20 C21 C16 117.9(2) . . ? C20 C21 C24 120.1(2) . . ? C16 C21 C24 122.0(2) . . ? C8 C9 C10 122.2(2) . . ? C8 C9 H9A 118.9 . . ? C10 C9 H9A 118.9 . . ? N3 C1 N2 110.98(19) . . ? N3 C1 N1 117.37(19) . . ? N2 C1 N1 111.02(17) . . ? N3 C1 H1A 105.5 . . ? N2 C1 H1A 105.5 . . ? N1 C1 H1A 105.5 . . ? C11 C10 C9 118.2(2) . . ? C11 C10 C14 121.4(2) . . ? C9 C10 C14 120.5(2) . . ? C18 C19 C20 118.0(2) . . ? C18 C19 C23 121.5(3) . . ? C20 C19 C23 120.4(3) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C21 C20 C19 122.2(2) . . ? C21 C20 H20A 118.9 . . ? C19 C20 H20A 118.9 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? Cl1 C25 Cl1 112.1(3) . 2 ? Cl1 C25 H25A 109.2 . . ? Cl1 C25 H25A 109.2 2 . ? C1 N3 H3A 111.6 . . ? C1 N3 H3B 108.9 . . ? H3A N3 H3B 115.2 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.680 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.047 #===END data_7 _database_code_depnum_ccdc_archive 'CCDC 770150' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6-KetoMes-OEt _chemical_melting_point ? _chemical_formula_moiety N,N-(Mes)2-4,6-dioxo-5,5-(Me)2-2-H-OCH2CH3 _chemical_formula_sum 'C26 H34 N2 O3' _chemical_formula_weight 422.55 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.690(3) _cell_length_b 8.4031(16) _cell_length_c 18.318(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.840(4) _cell_angle_gamma 90.00 _cell_volume 2412.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18117 _diffrn_reflns_av_R_equivalents 0.1109 _diffrn_reflns_av_sigmaI/netI 0.0876 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 24.00 _reflns_number_total 3782 _reflns_number_gt 2327 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0007P)^2^+3.9774P] 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 3782 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1223 _refine_ls_R_factor_gt 0.0749 _refine_ls_wR_factor_ref 0.1623 _refine_ls_wR_factor_gt 0.1384 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.76239(16) 0.1417(3) 0.15108(14) 0.0442(7) Uani 1 1 d . . . N1 N 0.66281(18) 0.2351(3) 0.06098(17) 0.0350(7) Uani 1 1 d . . . C1 C 0.7478(2) 0.2542(4) 0.0943(2) 0.0342(9) Uani 1 1 d . . . H1A H 0.7510 0.3605 0.1164 0.041 Uiso 1 1 calc R . . N2 N 0.81388(17) 0.2441(3) 0.04160(16) 0.0335(7) Uani 1 1 d . . . O2 O 0.57130(17) 0.1729(4) -0.03333(16) 0.0575(8) Uani 1 1 d . . . C2 C 0.6440(2) 0.1748(4) -0.0074(2) 0.0390(9) Uani 1 1 d . . . O3 O 0.86246(17) 0.1708(3) -0.06774(15) 0.0503(7) Uani 1 1 d . . . C3 C 0.7170(2) 0.1038(5) -0.0476(2) 0.0416(10) Uani 1 1 d . . . C4 C 0.8038(2) 0.1767(4) -0.0264(2) 0.0387(9) Uani 1 1 d . . . C5 C 0.6990(3) 0.1199(6) -0.1299(2) 0.0693(14) Uani 1 1 d . . . H5A H 0.6960 0.2306 -0.1427 0.104 Uiso 1 1 calc R . . H5B H 0.6458 0.0692 -0.1435 0.104 Uiso 1 1 calc R . . H5C H 0.7441 0.0701 -0.1551 0.104 Uiso 1 1 calc R . . C6 C 0.7222(3) -0.0761(5) -0.0262(3) 0.0637(13) Uani 1 1 d . . . H6A H 0.7335 -0.0856 0.0256 0.096 Uiso 1 1 calc R . . H6B H 0.7672 -0.1262 -0.0514 0.096 Uiso 1 1 calc R . . H6C H 0.6689 -0.1271 -0.0396 0.096 Uiso 1 1 calc R . . C7 C 0.5932(2) 0.2863(5) 0.1041(2) 0.0383(9) Uani 1 1 d . . . C8 C 0.5676(2) 0.4461(5) 0.1013(2) 0.0422(10) Uani 1 1 d . . . C9 C 0.5006(3) 0.4929(5) 0.1435(2) 0.0529(11) Uani 1 1 d . . . H9A H 0.4836 0.5990 0.1429 0.064 Uiso 1 1 calc R . . C10 C 0.4585(3) 0.3855(6) 0.1864(2) 0.0538(12) Uani 1 1 d . . . C11 C 0.4848(3) 0.2269(6) 0.1870(2) 0.0545(12) Uani 1 1 d . . . H11A H 0.4569 0.1541 0.2157 0.065 Uiso 1 1 calc R . . C12 C 0.5515(2) 0.1741(5) 0.1460(2) 0.0428(10) Uani 1 1 d . . . C13 C 0.6079(3) 0.5654(5) 0.0516(2) 0.0570(12) Uani 1 1 d . . . H13A H 0.5819 0.6677 0.0575 0.085 Uiso 1 1 calc R . . H13B H 0.5994 0.5315 0.0017 0.085 Uiso 1 1 calc R . . H13C H 0.6679 0.5727 0.0641 0.085 Uiso 1 1 calc R . . C14 C 0.3835(3) 0.4351(7) 0.2314(3) 0.0810(17) Uani 1 1 d . . . H14A H 0.3734 0.5471 0.2254 0.122 Uiso 1 1 calc R . . H14B H 0.3966 0.4122 0.2820 0.122 Uiso 1 1 calc R . . H14C H 0.3334 0.3772 0.2150 0.122 Uiso 1 1 calc R . . C15 C 0.5731(3) -0.0016(5) 0.1448(3) 0.0571(12) Uani 1 1 d . . . H15A H 0.6202 -0.0187 0.1142 0.086 Uiso 1 1 calc R . . H15B H 0.5245 -0.0605 0.1259 0.086 Uiso 1 1 calc R . . H15C H 0.5883 -0.0370 0.1936 0.086 Uiso 1 1 calc R . . C16 C 0.8987(2) 0.2919(4) 0.06912(19) 0.0349(9) Uani 1 1 d . . . C17 C 0.9569(2) 0.1741(5) 0.0923(2) 0.0415(10) Uani 1 1 d . . . C18 C 1.0362(2) 0.2244(5) 0.1212(2) 0.0479(11) Uani 1 1 d . . . H18A H 1.0766 0.1482 0.1356 0.058 Uiso 1 1 calc R . . C19 C 1.0573(2) 0.3852(5) 0.1292(2) 0.0463(10) Uani 1 1 d . . . C20 C 0.9984(2) 0.4967(5) 0.1043(2) 0.0436(10) Uani 1 1 d . . . H20A H 1.0124 0.6041 0.1080 0.052 Uiso 1 1 calc R . . C21 C 0.9182(2) 0.4538(4) 0.0734(2) 0.0362(9) Uani 1 1 d . . . C22 C 0.9372(3) -0.0018(4) 0.0868(3) 0.0562(12) Uani 1 1 d . . . H22A H 0.9855 -0.0617 0.1057 0.084 Uiso 1 1 calc R . . H22B H 0.9250 -0.0298 0.0366 0.084 Uiso 1 1 calc R . . H22C H 0.8885 -0.0255 0.1147 0.084 Uiso 1 1 calc R . . C23 C 1.1446(3) 0.4339(6) 0.1615(2) 0.0649(13) Uani 1 1 d . . . H23A H 1.1483 0.5479 0.1632 0.097 Uiso 1 1 calc R . . H23B H 1.1880 0.3929 0.1315 0.097 Uiso 1 1 calc R . . H23C H 1.1525 0.3917 0.2100 0.097 Uiso 1 1 calc R . . C24 C 0.8579(2) 0.5807(4) 0.0449(2) 0.0457(10) Uani 1 1 d . . . H24A H 0.8061 0.5323 0.0259 0.069 Uiso 1 1 calc R . . H24B H 0.8838 0.6389 0.0068 0.069 Uiso 1 1 calc R . . H24C H 0.8454 0.6520 0.0839 0.069 Uiso 1 1 calc R . . C25 C 0.7976(3) 0.2030(6) 0.2199(2) 0.0669(14) Uani 1 1 d . . . H25A H 0.8253 0.3040 0.2114 0.080 Uiso 1 1 calc R . . H25B H 0.8405 0.1297 0.2397 0.080 Uiso 1 1 calc R . . C26 C 0.7327(4) 0.2256(7) 0.2732(3) 0.098(2) Uani 1 1 d . . . H26A H 0.7589 0.2666 0.3178 0.147 Uiso 1 1 calc R . . H26B H 0.7059 0.1255 0.2826 0.147 Uiso 1 1 calc R . . H26C H 0.6906 0.2996 0.2542 0.147 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 0.0393(16) 0.0526(17) 0.0403(16) 0.0059(14) -0.0027(12) -0.0043(13) N1 0.0265(16) 0.0368(17) 0.0416(19) -0.0038(15) 0.0023(14) 0.0017(14) C1 0.0254(19) 0.037(2) 0.041(2) -0.0043(18) 0.0031(17) -0.0010(17) N2 0.0253(16) 0.0340(17) 0.0411(19) -0.0024(15) 0.0014(14) 0.0015(14) O2 0.0347(17) 0.080(2) 0.0565(19) -0.0152(16) -0.0077(14) 0.0061(15) C2 0.038(2) 0.035(2) 0.044(2) -0.0010(19) 0.0022(19) 0.0014(18) O3 0.0394(16) 0.0626(19) 0.0500(18) -0.0076(15) 0.0128(14) 0.0019(14) C3 0.038(2) 0.045(2) 0.042(2) -0.0076(19) 0.0055(18) -0.0042(19) C4 0.038(2) 0.034(2) 0.045(3) -0.0002(19) 0.003(2) 0.0050(18) C5 0.050(3) 0.112(4) 0.046(3) -0.014(3) 0.000(2) -0.011(3) C6 0.058(3) 0.042(3) 0.092(4) -0.011(2) 0.015(3) -0.002(2) C7 0.026(2) 0.044(2) 0.045(2) -0.0041(19) 0.0009(17) 0.0010(18) C8 0.030(2) 0.047(2) 0.049(3) -0.004(2) 0.0002(18) 0.0054(19) C9 0.041(2) 0.056(3) 0.062(3) -0.013(2) 0.003(2) 0.010(2) C10 0.034(2) 0.077(3) 0.050(3) -0.015(3) 0.003(2) 0.006(2) C11 0.037(2) 0.072(3) 0.055(3) 0.000(2) 0.006(2) -0.011(2) C12 0.029(2) 0.051(3) 0.048(3) -0.002(2) -0.0005(19) -0.0044(19) C13 0.051(3) 0.044(3) 0.075(3) 0.007(2) 0.005(2) 0.008(2) C14 0.049(3) 0.124(5) 0.072(4) -0.029(3) 0.019(3) 0.009(3) C15 0.044(3) 0.048(3) 0.079(3) 0.010(2) 0.004(2) -0.007(2) C16 0.027(2) 0.039(2) 0.039(2) -0.0026(18) 0.0034(17) -0.0010(17) C17 0.031(2) 0.042(2) 0.053(3) 0.005(2) 0.0038(19) 0.0004(18) C18 0.035(2) 0.055(3) 0.053(3) 0.012(2) 0.001(2) 0.007(2) C19 0.035(2) 0.063(3) 0.041(2) -0.002(2) 0.0032(19) -0.010(2) C20 0.041(2) 0.044(2) 0.046(3) -0.004(2) 0.0084(19) -0.006(2) C21 0.034(2) 0.037(2) 0.038(2) -0.0008(18) 0.0071(17) -0.0015(18) C22 0.041(2) 0.040(2) 0.088(4) 0.005(2) 0.004(2) 0.008(2) C23 0.043(3) 0.088(4) 0.063(3) -0.003(3) -0.009(2) -0.010(3) C24 0.048(3) 0.037(2) 0.053(3) 0.0044(19) 0.008(2) -0.0004(19) C25 0.063(3) 0.092(4) 0.045(3) 0.003(3) -0.010(2) -0.014(3) C26 0.120(5) 0.121(5) 0.056(4) -0.021(3) 0.021(3) -0.059(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.415(4) . ? O1 C25 1.446(5) . ? N1 C2 1.369(5) . ? N1 C7 1.445(4) . ? N1 C1 1.448(4) . ? C1 N2 1.455(4) . ? C1 H1A 0.9800 . ? N2 C4 1.370(5) . ? N2 C16 1.456(4) . ? O2 C2 1.214(4) . ? C2 C3 1.515(5) . ? O3 C4 1.222(4) . ? C3 C4 1.526(5) . ? C3 C5 1.525(5) . ? C3 C6 1.563(5) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C12 1.399(5) . ? C7 C8 1.401(5) . ? C8 C9 1.392(5) . ? C8 C13 1.514(5) . ? C9 C10 1.386(6) . ? C9 H9A 0.9300 . ? C10 C11 1.396(6) . ? C10 C14 1.527(5) . ? C11 C12 1.390(5) . ? C11 H11A 0.9300 . ? C12 C15 1.516(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C21 1.396(5) . ? C16 C17 1.398(5) . ? C17 C18 1.394(5) . ? C17 C22 1.512(5) . ? C18 C19 1.397(5) . ? C18 H18A 0.9300 . ? C19 C20 1.378(5) . ? C19 C23 1.520(5) . ? C20 C21 1.401(5) . ? C20 H20A 0.9300 . ? C21 C24 1.502(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.457(6) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? 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 O1 C25 116.3(3) . . ? C2 N1 C7 118.4(3) . . ? C2 N1 C1 125.4(3) . . ? C7 N1 C1 116.2(3) . . ? O1 C1 N1 110.4(3) . . ? O1 C1 N2 110.7(3) . . ? N1 C1 N2 112.6(3) . . ? O1 C1 H1A 107.6 . . ? N1 C1 H1A 107.6 . . ? N2 C1 H1A 107.6 . . ? C4 N2 C1 125.0(3) . . ? C4 N2 C16 119.4(3) . . ? C1 N2 C16 115.1(3) . . ? O2 C2 N1 121.3(3) . . ? O2 C2 C3 121.5(4) . . ? N1 C2 C3 117.2(3) . . ? C2 C3 C4 113.8(3) . . ? C2 C3 C5 109.8(3) . . ? C4 C3 C5 109.6(3) . . ? C2 C3 C6 106.9(3) . . ? C4 C3 C6 106.9(3) . . ? C5 C3 C6 109.8(4) . . ? O3 C4 N2 121.5(3) . . ? O3 C4 C3 121.1(4) . . ? N2 C4 C3 117.4(3) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C7 C8 121.7(3) . . ? C12 C7 N1 119.1(3) . . ? C8 C7 N1 119.2(3) . . ? C9 C8 C7 118.3(4) . . ? C9 C8 C13 119.7(4) . . ? C7 C8 C13 121.9(3) . . ? C10 C9 C8 121.7(4) . . ? C10 C9 H9A 119.2 . . ? C8 C9 H9A 119.2 . . ? C9 C10 C11 118.5(4) . . ? C9 C10 C14 122.0(4) . . ? C11 C10 C14 119.5(4) . . ? C12 C11 C10 122.1(4) . . ? C12 C11 H11A 119.0 . . ? C10 C11 H11A 119.0 . . ? C7 C12 C11 117.8(4) . . ? C7 C12 C15 122.6(4) . . ? C11 C12 C15 119.6(4) . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C21 C16 C17 122.4(3) . . ? C21 C16 N2 118.8(3) . . ? C17 C16 N2 118.8(3) . . ? C18 C17 C16 117.2(4) . . ? C18 C17 C22 119.8(3) . . ? C16 C17 C22 122.9(3) . . ? C17 C18 C19 122.4(4) . . ? C17 C18 H18A 118.8 . . ? C19 C18 H18A 118.8 . . ? C20 C19 C18 118.1(4) . . ? C20 C19 C23 121.5(4) . . ? C18 C19 C23 120.3(4) . . ? C19 C20 C21 122.2(4) . . ? C19 C20 H20A 118.9 . . ? C21 C20 H20A 118.9 . . ? C16 C21 C20 117.6(3) . . ? C16 C21 C24 122.7(3) . . ? C20 C21 C24 119.7(3) . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O1 C25 C26 112.4(4) . . ? O1 C25 H25A 109.1 . . ? C26 C25 H25A 109.1 . . ? O1 C25 H25B 109.1 . . ? C26 C25 H25B 109.1 . . ? H25A C25 H25B 107.9 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.331 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.051 #===END data_9 _database_code_depnum_ccdc_archive 'CCDC 770151' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6-KetoMes-ether-dimer _chemical_melting_point ? _chemical_formula_moiety Bis-N,N-(Mes)2-4,6-dioxo-5,5-(Me)2-2)2-O-C7H8 _chemical_formula_sum 'C55 H66 N4 O5' _chemical_formula_weight 863.12 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 P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 13.884(3) _cell_length_b 15.417(3) _cell_length_c 24.502(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.35(3) _cell_angle_gamma 90.00 _cell_volume 5175.0(18) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.385 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.108 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ccd area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17760 _diffrn_reflns_av_R_equivalents 0.1121 _diffrn_reflns_av_sigmaI/netI 0.1975 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 9109 _reflns_number_gt 3220 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0100P)^2^+0.9000P] 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 9109 _refine_ls_number_parameters 578 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2052 _refine_ls_R_factor_gt 0.0823 _refine_ls_wR_factor_ref 0.1888 _refine_ls_wR_factor_gt 0.1618 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.015 _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 -0.7264(2) -0.2598(2) 0.32901(14) 0.0659(11) Uani 1 1 d . . . O2 O -0.8099(2) -0.0591(2) 0.19123(14) 0.0535(10) Uani 1 1 d . . . O5 O -0.5000 -0.1517(2) 0.2500 0.0357(11) Uani 1 2 d S . . N1 N -0.6500(3) -0.0668(2) 0.23280(14) 0.0378(10) Uani 1 1 d . . . N2 N -0.6136(3) -0.1633(2) 0.31019(15) 0.0410(10) Uani 1 1 d . . . C19 C -0.7007(4) -0.2074(3) 0.2970(2) 0.0451(13) Uani 1 1 d . . . C20 C -0.3664(3) 0.0156(3) 0.29360(19) 0.0371(12) Uani 1 1 d . . . C25 C -0.2394(3) -0.1909(3) 0.2599(2) 0.0430(13) Uani 1 1 d . . . C30 C -0.3761(3) 0.0938(3) 0.2643(2) 0.0407(12) Uani 1 1 d . . . C36 C -0.5736(3) -0.1034(3) 0.27352(18) 0.0382(12) Uani 1 1 d . . . H36A H -0.5412 -0.0559 0.2960 0.046 Uiso 1 1 d R . . C40 C -0.2550(4) -0.1000(3) 0.2800(2) 0.0455(13) Uani 1 1 d . . . C41 C -0.6344(3) 0.0170(3) 0.1490(2) 0.0438(13) Uani 1 1 d . . . C44 C -0.3971(4) 0.1718(3) 0.3464(2) 0.0532(14) Uani 1 1 d . . . C47 C -0.4440(3) -0.1840(3) 0.13596(19) 0.0462(13) Uani 1 1 d . . . C50 C -0.7278(4) -0.2547(3) 0.19811(19) 0.0585(15) Uani 1 1 d . . . H50A H -0.6607 -0.2444 0.1953 0.088 Uiso 1 1 d R . . H50B H -0.7674 -0.2466 0.1626 0.088 Uiso 1 1 d R . . H50C H -0.7353 -0.3130 0.2105 0.088 Uiso 1 1 d R . . C55 C -0.3925(3) 0.1709(3) 0.2911(2) 0.0474(13) Uani 1 1 d . . . H55A H -0.4003 0.2223 0.2711 0.057 Uiso 1 1 d R . . C60 C -0.6168(3) 0.0955(4) 0.1241(2) 0.0529(14) Uani 1 1 d . . . H60A H -0.6158 0.0965 0.0863 0.064 Uiso 1 1 d R . . C66 C -0.4966(4) -0.2604(3) 0.1293(2) 0.0510(14) Uani 1 1 d . . . C67 C -0.3665(3) 0.0969(3) 0.20332(19) 0.0495(13) Uani 1 1 d . . . H67A H -0.3470 0.1541 0.1940 0.074 Uiso 1 1 d R . . H67B H -0.4281 0.0829 0.1812 0.074 Uiso 1 1 d R . . H67C H -0.3183 0.0557 0.1962 0.074 Uiso 1 1 d R . . C76 C -0.4366(3) -0.1282(3) 0.0912(2) 0.0502(14) Uani 1 1 d . . . C82 C -0.1316(3) -0.2031(3) 0.2563(2) 0.0636(16) Uani 1 1 d . . . H82A H -0.1109 -0.1594 0.2329 0.095 Uiso 1 1 d R . . H82B H -0.1229 -0.2594 0.2410 0.095 Uiso 1 1 d R . . H82C H -0.0935 -0.1991 0.2925 0.095 Uiso 1 1 d R . . C85 C -0.5104(4) -0.3279(3) 0.3268(2) 0.0609(15) Uani 1 1 d . . . H85A H -0.5114 -0.3009 0.2914 0.091 Uiso 1 1 d R . . H85B H -0.5690 -0.3612 0.3263 0.091 Uiso 1 1 d R . . H85C H -0.4547 -0.3654 0.3345 0.091 Uiso 1 1 d R . . C87 C -0.5056(4) -0.1467(4) 0.4602(2) 0.0662(16) Uani 1 1 d . . . H87A H -0.5074 -0.1102 0.4903 0.079 Uiso 1 1 d R . . C91 C -0.3400(3) -0.0623(3) 0.38781(19) 0.0590(15) Uani 1 1 d . . . H91A H -0.3591 -0.0528 0.4233 0.088 Uiso 1 1 d R . . H91B H -0.2709 -0.0720 0.3925 0.088 Uiso 1 1 d R . . H91C H -0.3736 -0.1121 0.3707 0.088 Uiso 1 1 d R . . C97 C -0.3707(4) -0.0491(3) 0.0953(2) 0.0672(16) Uani 1 1 d . . . H97A H -0.3170 -0.0572 0.1248 0.101 Uiso 1 1 d R . . H97B H -0.4071 0.0012 0.1025 0.101 Uiso 1 1 d R . . H97C H -0.3462 -0.0414 0.0611 0.101 Uiso 1 1 d R . . C99 C -0.5827(5) 0.2562(4) 0.1253(2) 0.086(2) Uani 1 1 d . . . C100 C -0.5527(4) -0.2747(4) 0.0780(3) 0.0726(17) Uani 1 1 d . . . H10M H -0.5913 -0.3244 0.0732 0.087 Uiso 1 1 d R . . C107 C -0.5533(4) -0.2179(5) 0.0332(2) 0.0743(19) Uani 1 1 d . . . C111 C -0.3800(5) -0.2342(4) 0.5223(2) 0.120(3) Uani 1 1 d . . . H11J H -0.3969 -0.1974 0.5491 0.180 Uiso 1 1 d R . . H11K H -0.3152 -0.2246 0.5192 0.180 Uiso 1 1 d R . . H11L H -0.3867 -0.2911 0.5334 0.180 Uiso 1 1 d R . . H10P H -0.4216 0.2485 0.4109 0.180 Uiso 1 1 d R . . H10Q H -0.4748 0.2817 0.3571 0.180 Uiso 1 1 d R . . H10R H -0.3678 0.2972 0.3727 0.180 Uiso 1 1 d R . . O6 O -0.2079(2) -0.4784(2) 0.33954(14) 0.0682(11) Uani 1 1 d . . . O7 O -0.3138(2) -0.6813(2) 0.20729(14) 0.0530(10) Uani 1 1 d . . . O10 O 0.0000 -0.5915(2) 0.2500 0.0322(10) Uani 1 2 d S . . N5 N 0.1010(3) -0.5770(2) 0.18374(14) 0.0386(10) Uani 1 1 d . . . N6 N 0.1515(3) -0.6772(2) 0.25909(14) 0.0343(9) Uani 1 1 d . . . C22 C 0.1384(3) -0.7600(3) 0.28560(19) 0.0364(12) Uani 1 1 d . . . C24 C -0.0691(3) -0.6396(3) 0.27793(17) 0.0355(11) Uani 1 1 d . . . H24A H -0.0338 -0.6866 0.2996 0.043 Uiso 1 1 d R . . C26 C -0.0357(3) -0.5597(3) 0.36794(19) 0.0435(13) Uani 1 1 d . . . C27 C 0.1256(3) -0.8363(3) 0.25449(18) 0.0348(11) Uani 1 1 d . . . C33 C -0.2569(3) -0.5503(3) 0.25256(19) 0.0425(12) Uani 1 1 d . . . C38 C -0.1492(3) -0.7617(3) 0.1566(2) 0.0431(13) Uani 1 1 d . . . C45 C -0.1274(3) -0.8381(3) 0.30669(17) 0.0444(13) Uani 1 1 d . . . H45A H -0.1766 -0.7987 0.3150 0.067 Uiso 1 1 d R . . H45B H -0.0649 -0.8211 0.3265 0.067 Uiso 1 1 d R . . H45C H -0.1424 -0.8958 0.3174 0.067 Uiso 1 1 d R . . C46 C -0.2446(4) -0.6427(3) 0.23283(19) 0.0425(13) Uani 1 1 d . . . C48 C 0.0391(4) -0.6158(3) 0.08771(19) 0.0475(14) Uani 1 1 d . . . C53 C -0.1357(3) -0.8411(3) 0.1324(2) 0.0497(14) Uani 1 1 d . . . H53A H -0.1416 -0.8436 0.0941 0.060 Uiso 1 1 d R . . C54 C -0.1140(3) -0.9170(3) 0.1621(2) 0.0506(14) Uani 1 1 d . . . C56 C -0.0230(4) -0.4852(3) 0.12651(19) 0.0461(13) Uani 1 1 d . . . C58 C 0.1118(3) -0.9127(3) 0.2814(2) 0.0417(12) Uani 1 1 d . . . H58A H 0.0994 -0.9633 0.2607 0.050 Uiso 1 1 d R . . C65 C 0.1780(3) -0.6837(3) 0.37881(18) 0.0541(14) Uani 1 1 d . . . H65A H 0.1664 -0.6941 0.4157 0.081 Uiso 1 1 d R . . H65B H 0.1408 -0.6344 0.3638 0.081 Uiso 1 1 d R . . H65C H 0.2461 -0.6725 0.3794 0.081 Uiso 1 1 d R . . C69 C 0.1885(4) -0.5322(3) 0.1941(2) 0.0486(14) Uani 1 1 d . . . C74 C 0.0898(4) -0.4742(3) 0.4223(2) 0.0573(15) Uani 1 1 d . . . H74A H 0.1316 -0.4267 0.4259 0.069 Uiso 1 1 d R . . C75 C 0.2281(4) -0.4876(3) 0.29213(19) 0.0626(15) Uani 1 1 d . . . H75A H 0.1627 -0.4996 0.2978 0.094 Uiso 1 1 d R . . H75B H 0.2321 -0.4288 0.2801 0.094 Uiso 1 1 d R . . H75C H 0.2721 -0.4959 0.3261 0.094 Uiso 1 1 d R . . C77 C -0.3609(3) -0.5347(3) 0.2612(2) 0.0655(16) Uani 1 1 d . . . H77A H -0.3780 -0.5758 0.2875 0.098 Uiso 1 1 d R . . H77B H -0.4036 -0.5418 0.2266 0.098 Uiso 1 1 d R . . H77C H -0.3672 -0.4769 0.2747 0.098 Uiso 1 1 d R . . C81 C 0.0116(4) -0.4141(3) 0.33031(19) 0.0571(15) Uani 1 1 d . . . H81A H -0.0017 -0.4393 0.2942 0.086 Uiso 1 1 d R . . H81B H 0.0705 -0.3810 0.3338 0.086 Uiso 1 1 d R . . H81C H -0.0414 -0.3769 0.3356 0.086 Uiso 1 1 d R . . C86 C 0.0309(4) -0.6003(4) 0.4606(2) 0.0651(17) Uani 1 1 d . . . H86A H 0.0316 -0.6377 0.4905 0.078 Uiso 1 1 d R . . C101 C -0.1130(4) -0.6877(3) 0.4115(2) 0.0735(18) Uani 1 1 d . . . H10A H -0.1669 -0.6773 0.3826 0.110 Uiso 1 1 d R . . H10B H -0.1359 -0.6896 0.4462 0.110 Uiso 1 1 d R . . H10C H -0.0834 -0.7418 0.4052 0.110 Uiso 1 1 d R . . C103 C -0.0957(4) -0.5320(4) 0.0347(2) 0.0619(16) Uani 1 1 d . . . C104 C -0.0917(4) -1.0029(3) 0.1339(2) 0.0789(18) Uani 1 1 d . . . H10D H -0.1255 -1.0036 0.0966 0.118 Uiso 1 1 d R . . H10E H -0.1130 -1.0507 0.1537 0.118 Uiso 1 1 d R . . H10F H -0.0230 -1.0076 0.1338 0.118 Uiso 1 1 d R . . C112 C 0.1736(4) -0.5223(4) 0.5166(2) 0.098(2) Uani 1 1 d . . . H11A H 0.1460 -0.5359 0.5489 0.147 Uiso 1 1 d R . . H11B H 0.1971 -0.4639 0.5190 0.147 Uiso 1 1 d R . . H11C H 0.2266 -0.5610 0.5141 0.147 Uiso 1 1 d R . . C113 C -0.1570(8) -0.8857(5) 0.4787(3) 0.111(3) Uani 1 1 d . . . H11P H -0.1899 -0.9182 0.4495 0.133 Uiso 1 1 d R . . C115 C -0.0566(7) -0.8879(4) 0.4898(3) 0.089(2) Uani 1 1 d . . . H11Q H -0.0220 -0.9209 0.4679 0.107 Uiso 1 1 d R . . C120 C -0.0080(6) -0.8413(6) 0.5337(4) 0.097(2) Uani 1 1 d . . . C121 C -0.0596(9) -0.7901(5) 0.5670(3) 0.112(3) Uani 1 1 d . . . H12C H -0.0286 -0.7568 0.5964 0.134 Uiso 1 1 d R . . C122 C -0.1630(10) -0.7901(5) 0.5563(3) 0.123(3) Uani 1 1 d . . . H12D H -0.1997 -0.7595 0.5784 0.148 Uiso 1 1 d R . . C124 C -0.2106(6) -0.8366(6) 0.5124(4) 0.117(3) Uani 1 1 d . . . H12E H -0.2783 -0.8350 0.5036 0.140 Uiso 1 1 d R . . C131 C 0.0990(6) -0.8359(6) 0.5502(4) 0.195(5) Uani 1 1 d . . . H13D H 0.1241 -0.8909 0.5429 0.292 Uiso 1 1 d R . . H13E H 0.1187 -0.8222 0.5880 0.292 Uiso 1 1 d R . . H13F H 0.1240 -0.7936 0.5283 0.292 Uiso 1 1 d 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 0.057(2) 0.072(3) 0.065(3) 0.008(2) 0.000(2) -0.028(2) O2 0.032(2) 0.048(2) 0.073(3) -0.0004(19) -0.0152(18) 0.0102(17) O5 0.030(3) 0.030(2) 0.045(3) 0.000 -0.001(2) 0.000 N1 0.030(2) 0.035(2) 0.045(3) -0.001(2) -0.0045(19) -0.0043(19) N2 0.043(3) 0.040(2) 0.037(2) 0.004(2) -0.004(2) 0.000(2) C19 0.045(3) 0.038(3) 0.052(4) -0.003(3) 0.005(3) -0.011(3) C20 0.026(3) 0.039(3) 0.042(3) 0.000(3) -0.006(2) -0.006(2) C25 0.031(3) 0.039(3) 0.055(3) 0.007(3) -0.006(2) 0.010(2) C30 0.024(3) 0.039(3) 0.055(3) 0.000(3) -0.006(2) -0.002(2) C36 0.032(3) 0.038(3) 0.039(3) 0.005(3) -0.010(2) 0.005(2) C40 0.043(3) 0.043(3) 0.051(3) 0.012(3) 0.007(3) 0.002(3) C41 0.028(3) 0.047(3) 0.054(4) -0.002(3) 0.000(2) 0.011(2) C44 0.052(4) 0.045(4) 0.061(4) -0.012(3) 0.004(3) -0.002(3) C47 0.046(3) 0.055(4) 0.034(3) -0.005(3) -0.003(3) 0.008(3) C50 0.070(4) 0.039(3) 0.061(4) -0.005(3) -0.005(3) 0.003(3) C55 0.039(3) 0.035(3) 0.066(4) -0.005(3) 0.003(3) 0.000(2) C60 0.041(3) 0.067(4) 0.049(3) 0.017(3) 0.002(3) 0.003(3) C66 0.049(3) 0.047(4) 0.053(4) -0.016(3) -0.001(3) 0.001(3) C67 0.038(3) 0.042(3) 0.065(4) -0.001(3) -0.001(3) -0.005(2) C76 0.043(3) 0.056(4) 0.048(4) -0.004(3) -0.002(3) 0.008(3) C82 0.038(3) 0.067(4) 0.082(4) -0.003(3) -0.002(3) 0.015(3) C85 0.063(4) 0.050(4) 0.067(4) 0.008(3) 0.005(3) 0.007(3) C87 0.071(4) 0.083(5) 0.040(4) 0.008(3) -0.003(3) -0.014(4) C91 0.043(3) 0.066(4) 0.061(4) 0.009(3) -0.011(3) -0.007(3) C97 0.076(4) 0.069(4) 0.058(4) 0.003(3) 0.015(3) 0.006(3) C99 0.111(5) 0.060(4) 0.087(5) 0.025(4) 0.016(4) -0.013(4) C100 0.064(4) 0.072(4) 0.078(5) -0.033(4) 0.001(4) 0.000(3) C107 0.069(4) 0.100(6) 0.047(4) -0.028(4) -0.010(3) 0.021(4) C111 0.112(6) 0.168(7) 0.064(5) 0.028(5) -0.035(4) -0.006(5) O6 0.072(3) 0.074(3) 0.055(2) -0.015(2) 0.000(2) 0.038(2) O7 0.035(2) 0.048(2) 0.072(2) 0.0020(19) -0.0063(18) -0.0075(18) O10 0.036(3) 0.028(2) 0.032(2) 0.000 0.003(2) 0.000 N5 0.046(3) 0.034(2) 0.033(2) -0.002(2) 0.001(2) -0.006(2) N6 0.030(2) 0.029(2) 0.041(2) 0.0040(19) -0.0038(19) -0.0003(19) C22 0.024(3) 0.037(3) 0.046(3) 0.005(3) -0.003(2) 0.006(2) C24 0.040(3) 0.030(3) 0.034(3) -0.002(2) 0.002(2) 0.001(2) C26 0.047(3) 0.052(4) 0.029(3) -0.001(3) -0.001(2) 0.011(3) C27 0.028(3) 0.037(3) 0.036(3) 0.005(3) -0.003(2) 0.001(2) C33 0.040(3) 0.040(3) 0.043(3) -0.003(3) -0.005(3) 0.003(3) C38 0.039(3) 0.036(3) 0.051(4) -0.009(3) -0.002(3) -0.008(2) C45 0.037(3) 0.036(3) 0.056(3) 0.000(3) -0.004(2) -0.003(2) C46 0.038(3) 0.041(3) 0.047(3) 0.012(3) 0.002(3) -0.002(3) C48 0.061(4) 0.052(4) 0.029(3) -0.005(3) 0.004(3) -0.022(3) C53 0.039(3) 0.060(4) 0.048(3) -0.011(3) 0.000(3) -0.004(3) C54 0.035(3) 0.038(3) 0.077(4) -0.022(3) 0.005(3) -0.003(3) C56 0.057(4) 0.041(3) 0.039(3) 0.008(3) 0.004(3) -0.011(3) C58 0.039(3) 0.031(3) 0.053(4) 0.003(3) 0.002(3) 0.007(2) C65 0.058(3) 0.057(4) 0.042(3) 0.002(3) -0.007(3) 0.010(3) C69 0.051(4) 0.050(4) 0.045(3) -0.007(3) 0.009(3) -0.010(3) C74 0.067(4) 0.063(4) 0.038(3) -0.010(3) -0.003(3) 0.001(3) C75 0.073(4) 0.051(3) 0.058(4) -0.007(3) -0.005(3) -0.006(3) C77 0.038(3) 0.073(4) 0.084(4) 0.009(3) 0.005(3) 0.017(3) C81 0.073(4) 0.047(3) 0.050(3) -0.009(3) 0.008(3) 0.004(3) C86 0.083(5) 0.077(5) 0.035(3) 0.010(3) 0.009(3) 0.040(4) C101 0.106(5) 0.062(4) 0.056(4) 0.016(3) 0.021(3) -0.013(4) C103 0.069(4) 0.072(4) 0.041(4) 0.011(3) 0.000(3) -0.012(4) C104 0.078(4) 0.058(4) 0.100(5) -0.032(4) 0.012(4) -0.003(3) C112 0.085(5) 0.157(7) 0.040(4) -0.027(4) -0.023(3) 0.039(4) C113 0.125(8) 0.099(6) 0.106(7) 0.007(5) 0.012(6) -0.027(6) C115 0.109(7) 0.086(5) 0.070(5) 0.014(4) 0.005(5) 0.004(5) C120 0.110(7) 0.086(6) 0.085(6) 0.024(5) -0.014(5) -0.003(5) C121 0.154(9) 0.076(6) 0.093(7) 0.012(5) -0.019(7) -0.009(7) C122 0.208(12) 0.092(7) 0.071(6) 0.023(5) 0.027(7) -0.005(8) C124 0.095(6) 0.141(8) 0.114(7) 0.042(6) 0.014(6) -0.018(6) C131 0.085(6) 0.237(11) 0.233(11) 0.082(9) -0.061(7) 0.025(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C19 1.219(5) . ? O2 C40 1.224(5) 2_455 ? O5 C36 1.456(4) 2_455 ? O5 C36 1.456(4) . ? N1 C40 1.402(5) 2_455 ? N1 C36 1.447(5) . ? N1 C20 1.461(5) 2_455 ? N2 C19 1.378(5) . ? N2 C36 1.461(5) . ? N2 C47 1.462(5) 2_455 ? C19 C25 1.525(6) 2_455 ? C20 C30 1.399(6) . ? C20 C41 1.405(6) 2_455 ? C20 N1 1.461(5) 2_455 ? C25 C40 1.512(6) . ? C25 C19 1.525(6) 2_455 ? C25 C82 1.525(6) . ? C25 C50 1.545(6) 2_455 ? C30 C55 1.394(6) . ? C30 C67 1.521(6) . ? C36 H36A 0.9805 . ? C40 O2 1.224(5) 2_455 ? C40 N1 1.402(5) 2_455 ? C41 C60 1.394(6) . ? C41 C20 1.405(6) 2_455 ? C41 C91 1.527(6) 2_455 ? C44 C60 1.377(6) 2_455 ? C44 C55 1.368(6) . ? C44 C99 1.521(7) 2_455 ? C47 C66 1.382(6) . ? C47 C76 1.410(6) . ? C47 N2 1.462(5) 2_455 ? C50 C25 1.545(6) 2_455 ? C50 H50A 0.9594 . ? C50 H50B 0.9597 . ? C50 H50C 0.9593 . ? C55 H55A 0.9294 . ? C60 C44 1.377(6) 2_455 ? C60 H60A 0.9288 . ? C66 C100 1.385(7) . ? C66 C85 1.488(6) 2_455 ? C67 H67A 0.9600 . ? C67 H67B 0.9601 . ? C67 H67C 0.9599 . ? C76 C87 1.408(6) 2_455 ? C76 C97 1.519(6) . ? C82 H82A 0.9588 . ? C82 H82B 0.9596 . ? C82 H82C 0.9594 . ? C85 C66 1.488(6) 2_455 ? C85 H85A 0.9602 . ? C85 H85B 0.9598 . ? C85 H85C 0.9595 . ? C87 C107 1.363(7) 2_455 ? C87 C76 1.408(6) 2_455 ? C87 H87A 0.9298 . ? C91 C41 1.527(6) 2_455 ? C91 H91A 0.9598 . ? C91 H91B 0.9598 . ? C91 H91C 0.9589 . ? C97 H97A 0.9593 . ? C97 H97B 0.9585 . ? C97 H97C 0.9612 . ? C99 C44 1.521(7) 2_455 ? C100 C107 1.404(7) . ? C100 H10M 0.9305 . ? C107 C87 1.363(7) 2_455 ? C107 C111 1.537(7) 2_455 ? C111 C107 1.537(7) 2_455 ? C111 H11J 0.9271 . ? C111 H11K 0.9274 . ? C111 H11L 0.9277 . ? O6 C69 1.229(5) 2 ? O7 C46 1.213(5) . ? O10 C24 1.467(4) 2 ? O10 C24 1.467(4) . ? N5 C69 1.385(5) . ? N5 C26 1.457(5) 2 ? N5 C24 1.464(5) 2 ? N6 C46 1.382(5) 2 ? N6 C24 1.460(5) 2 ? N6 C22 1.457(5) . ? C22 C27 1.397(6) . ? C22 C38 1.400(6) 2 ? C24 N6 1.460(5) 2 ? C24 N5 1.464(5) 2 ? C24 H24A 0.9809 . ? C26 C48 1.396(6) 2 ? C26 C56 1.402(6) 2 ? C26 N5 1.457(5) 2 ? C27 C58 1.379(6) . ? C27 C45 1.503(5) 2 ? C33 C46 1.522(6) . ? C33 C69 1.511(6) 2 ? C33 C77 1.512(6) . ? C33 C75 1.560(6) 2 ? C38 C53 1.385(6) . ? C38 C22 1.400(6) 2 ? C38 C65 1.499(6) 2 ? C45 C27 1.503(5) 2 ? C45 H45A 0.9601 . ? C45 H45B 0.9595 . ? C45 H45C 0.9602 . ? C46 N6 1.382(5) 2 ? C48 C26 1.396(6) 2 ? C48 C86 1.425(7) 2 ? C48 C101 1.508(6) 2 ? C53 C54 1.386(6) . ? C53 H53A 0.9294 . ? C54 C58 1.380(6) 2 ? C54 C104 1.547(6) . ? C56 C74 1.399(6) 2 ? C56 C26 1.402(6) 2 ? C56 C81 1.514(6) 2 ? C58 C54 1.380(6) 2 ? C58 H58A 0.9305 . ? C65 C38 1.499(6) 2 ? C65 H65A 0.9573 . ? C65 H65B 0.9587 . ? C65 H65C 0.9584 . ? C69 O6 1.229(5) 2 ? C69 C33 1.511(6) 2 ? C74 C103 1.372(7) 2 ? C74 C56 1.399(6) 2 ? C74 H74A 0.9296 . ? C75 C33 1.560(6) 2 ? C75 H75A 0.9582 . ? C75 H75B 0.9579 . ? C75 H75C 0.9581 . ? C77 H77A 0.9604 . ? C77 H77B 0.9599 . ? C77 H77C 0.9594 . ? C81 C56 1.514(6) 2 ? C81 H81A 0.9573 . ? C81 H81B 0.9565 . ? C81 H81C 0.9577 . ? C86 C103 1.378(7) 2 ? C86 C48 1.425(7) 2 ? C86 H86A 0.9306 . ? C101 C48 1.508(6) 2 ? C101 H10A 0.9559 . ? C101 H10B 0.9538 . ? C101 H10C 0.9547 . ? C103 C86 1.378(7) 2 ? C103 C74 1.372(7) 2 ? C103 C112 1.527(7) 2 ? C104 H10D 0.9574 . ? C104 H10E 0.9558 . ? C104 H10F 0.9563 . ? C112 C103 1.527(7) 2 ? C112 H11A 0.9567 . ? C112 H11B 0.9569 . ? C112 H11C 0.9560 . ? C113 C124 1.418(9) . ? C113 C115 1.376(9) . ? C113 H11P 0.9305 . ? C115 C120 1.375(9) . ? C115 H11Q 0.9289 . ? C120 C121 1.411(9) . ? C120 C131 1.477(9) . ? C121 C122 1.418(10) . ? C121 H12C 0.9300 . ? C122 C124 1.370(9) . ? C122 H12D 0.9296 . ? C124 H12E 0.9299 . ? C131 H13D 0.9451 . ? C131 H13E 0.9460 . ? C131 H13F 0.9464 . ? 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 C36 O5 C36 118.5(4) 2_455 . ? C40 N1 C36 124.8(4) 2_455 . ? C40 N1 C20 115.2(4) 2_455 2_455 ? C36 N1 C20 119.6(4) . 2_455 ? C19 N2 C36 125.1(4) . . ? C19 N2 C47 115.7(4) . 2_455 ? C36 N2 C47 119.0(4) . 2_455 ? O1 C19 N2 120.9(5) . . ? O1 C19 C25 121.7(5) . 2_455 ? N2 C19 C25 117.3(4) . 2_455 ? C30 C20 C41 119.1(4) . 2_455 ? C30 C20 N1 122.1(4) . 2_455 ? C41 C20 N1 118.7(4) 2_455 2_455 ? C40 C25 C19 111.6(4) . 2_455 ? C40 C25 C82 109.1(4) . . ? C19 C25 C82 108.7(4) 2_455 . ? C40 C25 C50 107.4(4) . 2_455 ? C19 C25 C50 109.1(4) 2_455 2_455 ? C82 C25 C50 111.0(4) . 2_455 ? C55 C30 C20 120.1(4) . . ? C55 C30 C67 118.9(4) . . ? C20 C30 C67 121.0(4) . . ? N1 C36 N2 111.1(3) . . ? N1 C36 O5 114.2(3) . . ? N2 C36 O5 106.4(3) . . ? N1 C36 H36A 108.3 . . ? N2 C36 H36A 108.2 . . ? O5 C36 H36A 108.5 . . ? O2 C40 N1 121.3(5) 2_455 2_455 ? O2 C40 C25 122.2(5) 2_455 . ? N1 C40 C25 116.3(4) 2_455 . ? C60 C41 C20 118.5(5) . 2_455 ? C60 C41 C91 118.5(5) . 2_455 ? C20 C41 C91 122.8(5) 2_455 2_455 ? C60 C44 C55 119.1(5) 2_455 . ? C60 C44 C99 120.8(5) 2_455 2_455 ? C55 C44 C99 120.1(5) . 2_455 ? C66 C47 C76 122.2(5) . . ? C66 C47 N2 119.5(5) . 2_455 ? C76 C47 N2 118.1(5) . 2_455 ? C25 C50 H50A 109.7 2_455 . ? C25 C50 H50B 109.5 2_455 . ? H50A C50 H50B 109.4 . . ? C25 C50 H50C 109.2 2_455 . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.4 . . ? C44 C55 C30 120.9(5) . . ? C44 C55 H55A 119.6 . . ? C30 C55 H55A 119.5 . . ? C44 C60 C41 122.1(5) 2_455 . ? C44 C60 H60A 119.1 2_455 . ? C41 C60 H60A 118.8 . . ? C100 C66 C47 116.8(5) . . ? C100 C66 C85 120.4(5) . 2_455 ? C47 C66 C85 122.7(5) . 2_455 ? C30 C67 H67A 109.5 . . ? C30 C67 H67B 109.6 . . ? H67A C67 H67B 109.4 . . ? C30 C67 H67C 109.4 . . ? H67A C67 H67C 109.5 . . ? H67B C67 H67C 109.4 . . ? C47 C76 C87 118.0(5) . 2_455 ? C47 C76 C97 123.9(5) . . ? C87 C76 C97 118.1(5) 2_455 . ? C25 C82 H82A 109.9 . . ? C25 C82 H82B 108.8 . . ? H82A C82 H82B 109.5 . . ? C25 C82 H82C 109.7 . . ? H82A C82 H82C 109.5 . . ? H82B C82 H82C 109.5 . . ? C66 C85 H85A 109.8 2_455 . ? C66 C85 H85B 109.8 2_455 . ? H85A C85 H85B 109.5 . . ? C66 C85 H85C 108.8 2_455 . ? H85A C85 H85C 109.4 . . ? H85B C85 H85C 109.5 . . ? C107 C87 C76 120.9(6) 2_455 2_455 ? C107 C87 H87A 119.0 2_455 . ? C76 C87 H87A 120.1 2_455 . ? C41 C91 H91A 109.9 2_455 . ? C41 C91 H91B 109.1 2_455 . ? H91A C91 H91B 109.5 . . ? C41 C91 H91C 109.4 2_455 . ? H91A C91 H91C 109.5 . . ? H91B C91 H91C 109.5 . . ? C76 C97 H97A 109.3 . . ? C76 C97 H97B 109.4 . . ? H97A C97 H97B 109.6 . . ? C76 C97 H97C 109.7 . . ? H97A C97 H97C 109.4 . . ? H97B C97 H97C 109.4 . . ? C66 C100 C107 122.8(6) . . ? C66 C100 H10M 118.2 . . ? C107 C100 H10M 119.0 . . ? C87 C107 C100 118.8(6) 2_455 . ? C87 C107 C111 120.0(6) 2_455 2_455 ? C100 C107 C111 121.1(7) . 2_455 ? C107 C111 H11J 109.9 2_455 . ? C107 C111 H11K 110.7 2_455 . ? H11J C111 H11K 108.8 . . ? C107 C111 H11L 109.8 2_455 . ? H11J C111 H11L 108.8 . . ? H11K C111 H11L 108.8 . . ? C24 O10 C24 119.2(4) 2 . ? C69 N5 C26 118.1(4) . 2 ? C69 N5 C24 124.0(4) . 2 ? C26 N5 C24 117.9(4) 2 2 ? C46 N6 C24 123.8(4) 2 2 ? C46 N6 C22 117.1(4) 2 . ? C24 N6 C22 118.9(3) 2 . ? C27 C22 C38 121.3(4) . 2 ? C27 C22 N6 120.5(4) . . ? C38 C22 N6 117.8(4) 2 . ? N6 C24 N5 111.9(3) 2 2 ? N6 C24 O10 114.6(3) 2 . ? N5 C24 O10 104.8(3) 2 . ? N6 C24 H24A 108.4 2 . ? N5 C24 H24A 108.4 2 . ? O10 C24 H24A 108.6 . . ? C48 C26 C56 121.7(5) 2 2 ? C48 C26 N5 117.9(5) 2 2 ? C56 C26 N5 120.3(4) 2 2 ? C58 C27 C22 118.2(4) . . ? C58 C27 C45 119.2(4) . 2 ? C22 C27 C45 122.6(4) . 2 ? C46 C33 C69 111.1(4) . 2 ? C46 C33 C77 110.6(4) . . ? C69 C33 C77 109.2(4) 2 . ? C46 C33 C75 107.6(4) . 2 ? C69 C33 C75 107.2(4) 2 2 ? C77 C33 C75 111.1(4) . 2 ? C53 C38 C22 116.7(4) . 2 ? C53 C38 C65 120.2(4) . 2 ? C22 C38 C65 123.1(4) 2 2 ? C27 C45 H45A 109.1 2 . ? C27 C45 H45B 109.8 2 . ? H45A C45 H45B 109.6 . . ? C27 C45 H45C 109.3 2 . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? O7 C46 N6 121.9(4) . 2 ? O7 C46 C33 120.2(4) . . ? N6 C46 C33 117.7(4) 2 . ? C26 C48 C86 116.0(5) 2 2 ? C26 C48 C101 123.7(5) 2 2 ? C86 C48 C101 120.3(5) 2 2 ? C54 C53 C38 123.7(5) . . ? C54 C53 H53A 118.1 . . ? C38 C53 H53A 118.2 . . ? C53 C54 C58 116.9(4) . 2 ? C53 C54 C104 122.0(5) . . ? C58 C54 C104 121.1(5) 2 . ? C74 C56 C26 118.5(5) 2 2 ? C74 C56 C81 119.3(5) 2 2 ? C26 C56 C81 122.2(4) 2 2 ? C54 C58 C27 122.6(5) 2 . ? C54 C58 H58A 118.5 2 . ? C27 C58 H58A 118.8 . . ? C38 C65 H65A 110.0 2 . ? C38 C65 H65B 109.7 2 . ? H65A C65 H65B 109.5 . . ? C38 C65 H65C 108.9 2 . ? H65A C65 H65C 109.4 . . ? H65B C65 H65C 109.3 . . ? O6 C69 N5 119.7(5) 2 . ? O6 C69 C33 121.9(5) 2 2 ? N5 C69 C33 118.4(4) . 2 ? C103 C74 C56 121.7(5) 2 2 ? C103 C74 H74A 118.6 2 . ? C56 C74 H74A 119.7 2 . ? C33 C75 H75A 109.8 2 . ? C33 C75 H75B 109.6 2 . ? H75A C75 H75B 109.4 . . ? C33 C75 H75C 109.2 2 . ? H75A C75 H75C 109.4 . . ? H75B C75 H75C 109.4 . . ? C33 C77 H77A 109.6 . . ? C33 C77 H77B 108.9 . . ? H77A C77 H77B 109.5 . . ? C33 C77 H77C 109.8 . . ? H77A C77 H77C 109.5 . . ? H77B C77 H77C 109.4 . . ? C56 C81 H81A 109.6 2 . ? C56 C81 H81B 109.4 2 . ? H81A C81 H81B 109.5 . . ? C56 C81 H81C 109.6 2 . ? H81A C81 H81C 109.4 . . ? H81B C81 H81C 109.4 . . ? C103 C86 C48 123.0(5) 2 2 ? C103 C86 H86A 119.0 2 . ? C48 C86 H86A 118.0 2 . ? C48 C101 H10A 109.6 2 . ? C48 C101 H10B 109.6 2 . ? H10A C101 H10B 109.3 . . ? C48 C101 H10C 109.5 2 . ? H10A C101 H10C 109.3 . . ? H10B C101 H10C 109.4 . . ? C86 C103 C74 118.5(5) 2 2 ? C86 C103 C112 120.6(6) 2 2 ? C74 C103 C112 121.0(6) 2 2 ? C54 C104 H10D 109.5 . . ? C54 C104 H10E 109.4 . . ? H10D C104 H10E 109.3 . . ? C54 C104 H10F 109.8 . . ? H10D C104 H10F 109.4 . . ? H10E C104 H10F 109.4 . . ? C103 C112 H11A 109.5 2 . ? C103 C112 H11B 109.4 2 . ? H11A C112 H11B 109.4 . . ? C103 C112 H11C 109.6 2 . ? H11A C112 H11C 109.4 . . ? H11B C112 H11C 109.5 . . ? C124 C113 C115 120.6(8) . . ? C124 C113 H11P 119.7 . . ? C115 C113 H11P 119.6 . . ? C113 C115 C120 119.6(8) . . ? C113 C115 H11Q 120.1 . . ? C120 C115 H11Q 120.3 . . ? C115 C120 C121 120.9(8) . . ? C115 C120 C131 126.0(10) . . ? C121 C120 C131 113.1(10) . . ? C122 C121 C120 119.1(8) . . ? C122 C121 H12C 118.1 . . ? C120 C121 H12C 122.8 . . ? C124 C122 C121 119.4(9) . . ? C124 C122 H12D 118.9 . . ? C121 C122 H12D 121.7 . . ? C122 C124 C113 120.3(9) . . ? C122 C124 H12E 120.6 . . ? C113 C124 H12E 119.1 . . ? C120 C131 H13D 106.5 . . ? C120 C131 H13E 113.5 . . ? H13D C131 H13E 109.2 . . ? C120 C131 H13F 109.2 . . ? H13D C131 H13F 109.3 . . ? H13E C131 H13F 109.2 . . ? 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 C36 N2 C19 O1 176.1(4) . . . . ? C47 N2 C19 O1 0.2(7) 2_455 . . . ? C36 N2 C19 C25 -1.2(6) . . . 2_455 ? C47 N2 C19 C25 -177.2(4) 2_455 . . 2_455 ? C41 C20 C30 C55 -5.0(6) 2_455 . . . ? N1 C20 C30 C55 179.4(4) 2_455 . . . ? C41 C20 C30 C67 173.5(4) 2_455 . . . ? N1 C20 C30 C67 -2.1(6) 2_455 . . . ? C40 N1 C36 N2 -15.9(6) 2_455 . . . ? C20 N1 C36 N2 157.1(4) 2_455 . . . ? C40 N1 C36 O5 104.4(5) 2_455 . . . ? C20 N1 C36 O5 -82.6(5) 2_455 . . . ? C19 N2 C36 N1 24.7(6) . . . . ? C47 N2 C36 N1 -159.5(4) 2_455 . . . ? C19 N2 C36 O5 -100.1(4) . . . . ? C47 N2 C36 O5 75.7(5) 2_455 . . . ? C36 O5 C36 N1 76.7(3) 2_455 . . . ? C36 O5 C36 N2 -160.4(4) 2_455 . . . ? C19 C25 C40 O2 -146.7(4) 2_455 . . 2_455 ? C82 C25 C40 O2 -26.6(6) . . . 2_455 ? C50 C25 C40 O2 93.8(5) 2_455 . . 2_455 ? C19 C25 C40 N1 37.5(5) 2_455 . . 2_455 ? C82 C25 C40 N1 157.7(4) . . . 2_455 ? C50 C25 C40 N1 -82.0(5) 2_455 . . 2_455 ? C60 C44 C55 C30 1.4(7) 2_455 . . . ? C99 C44 C55 C30 -178.7(4) 2_455 . . . ? C20 C30 C55 C44 1.6(7) . . . . ? C67 C30 C55 C44 -177.0(4) . . . . ? C20 C41 C60 C44 -2.7(7) 2_455 . . 2_455 ? C91 C41 C60 C44 173.5(4) 2_455 . . 2_455 ? C76 C47 C66 C100 -8.2(7) . . . . ? N2 C47 C66 C100 177.6(4) 2_455 . . . ? C76 C47 C66 C85 167.7(5) . . . 2_455 ? N2 C47 C66 C85 -6.5(7) 2_455 . . 2_455 ? C66 C47 C76 C87 7.6(7) . . . 2_455 ? N2 C47 C76 C87 -178.1(4) 2_455 . . 2_455 ? C66 C47 C76 C97 -172.9(5) . . . . ? N2 C47 C76 C97 1.5(7) 2_455 . . . ? C47 C66 C100 C107 3.4(8) . . . . ? C85 C66 C100 C107 -172.6(5) 2_455 . . . ? C66 C100 C107 C87 1.8(8) . . . 2_455 ? C66 C100 C107 C111 -177.3(5) . . . 2_455 ? C46 N6 C22 C27 -105.4(5) 2 . . . ? C24 N6 C22 C27 69.2(5) 2 . . . ? C46 N6 C22 C38 68.1(5) 2 . . 2 ? C24 N6 C22 C38 -117.3(4) 2 . . 2 ? C24 O10 C24 N6 -76.3(3) 2 . . 2 ? C24 O10 C24 N5 160.8(4) 2 . . 2 ? C38 C22 C27 C58 7.9(6) 2 . . . ? N6 C22 C27 C58 -178.9(4) . . . . ? C38 C22 C27 C45 -171.5(4) 2 . . 2 ? N6 C22 C27 C45 1.7(6) . . . 2 ? C69 C33 C46 O7 148.6(4) 2 . . . ? C77 C33 C46 O7 27.2(6) . . . . ? C75 C33 C46 O7 -94.3(5) 2 . . . ? C69 C33 C46 N6 -36.8(6) 2 . . 2 ? C77 C33 C46 N6 -158.2(4) . . . 2 ? C75 C33 C46 N6 80.3(5) 2 . . 2 ? C22 C38 C53 C54 0.9(7) 2 . . . ? C65 C38 C53 C54 -176.5(4) 2 . . . ? C38 C53 C54 C58 4.0(7) . . . 2 ? C38 C53 C54 C104 -175.2(4) . . . . ? C22 C27 C58 C54 -2.6(6) . . . 2 ? C45 C27 C58 C54 176.8(4) 2 . . 2 ? C26 N5 C69 O6 1.4(7) 2 . . 2 ? C24 N5 C69 O6 -177.3(4) 2 . . 2 ? C26 N5 C69 C33 -179.6(4) 2 . . 2 ? C24 N5 C69 C33 1.6(6) 2 . . 2 ? C124 C113 C115 C120 -0.5(11) . . . . ? C113 C115 C120 C121 -1.1(10) . . . . ? C113 C115 C120 C131 -178.8(7) . . . . ? C115 C120 C121 C122 2.9(11) . . . . ? C131 C120 C121 C122 -179.1(7) . . . . ? C120 C121 C122 C124 -3.0(11) . . . . ? C121 C122 C124 C113 1.4(11) . . . . ? C115 C113 C124 C122 0.4(11) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.286 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.060