# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Arjan Kleij' _publ_contact_author_email AKLEIJ@ICIQ.ES _publ_section_title ; Olefin metathesis as a tool for multinuclear Co(III)salen catalyst construction: Access to cooperative catalysts ; loop_ _publ_author_name 'Arjan Kleij' 'Jordi Benet-Buchholz' 'Eduardo C. Escudero-Adan' 'Robert M. Haak' ; M.M.Belmonte ; # Attachment 'Structure_5c.cif' data_rmh51_0m _database_code_depnum_ccdc_archive 'CCDC 735901' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H45 Co N2 O7' _chemical_formula_weight 652.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.3743(4) _cell_length_b 11.5252(4) _cell_length_c 14.8043(6) _cell_angle_alpha 78.151(2) _cell_angle_beta 68.412(2) _cell_angle_gamma 62.374(2) _cell_volume 1597.42(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7133 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 29.15 _exptl_crystal_description Block _exptl_crystal_colour brown _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 0.588 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8200 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 16551 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 29.16 _reflns_number_total 8399 _reflns_number_gt 7273 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0500P)^2^+0.7166P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8399 _refine_ls_number_parameters 447 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0976 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.002 _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 Co1 Co 0.40528(2) 0.846645(18) 0.592703(14) 0.01184(6) Uani 1 1 d . A . O1 O 0.55213(11) 1.06086(11) 0.71389(8) 0.0180(2) Uani 1 1 d . A . O1W O 0.33878(12) 0.99872(11) 0.49303(8) 0.0144(2) Uani 1 1 d . . . H1W H 0.400(3) 0.991(2) 0.4429(19) 0.036(6) Uiso 1 1 d . . . H2W H 0.321(2) 1.066(2) 0.5119(17) 0.032(6) Uiso 1 1 d . . . C1 C 0.36800(15) 1.00886(14) 0.73258(10) 0.0143(3) Uani 1 1 d . A . O1A O 0.64479(14) 0.51200(12) 0.63048(10) 0.0312(3) Uani 1 1 d . . . C1A C 0.60284(18) 0.61874(15) 0.66286(12) 0.0203(3) Uani 1 1 d . . . C2A C 0.45422(17) 0.70801(15) 0.69511(12) 0.0200(3) Uani 1 1 d . . . H2A1 H 0.4320 0.7492 0.7553 0.024 Uiso 1 1 calc R . . H2A2 H 0.3977 0.6580 0.7100 0.024 Uiso 1 1 calc R . . N2 N 0.21731(13) 0.90899(13) 0.67176(9) 0.0158(2) Uani 1 1 d . . . O2 O 0.44257(11) 0.95665(10) 0.64791(7) 0.0148(2) Uani 1 1 d . . . C2 C 0.42461(15) 1.06683(14) 0.77247(11) 0.0150(3) Uani 1 1 d . . . O3 O 0.59226(11) 0.79224(10) 0.50784(8) 0.0150(2) Uani 1 1 d . . . C3 C 0.35354(17) 1.12200(15) 0.86200(11) 0.0189(3) Uani 1 1 d . A . H3 H 0.3952 1.1572 0.8875 0.023 Uiso 1 1 calc R . . N3 N 0.36350(13) 0.74289(12) 0.53684(10) 0.0163(2) Uani 1 1 d . . . C3A C 0.7061(2) 0.66037(17) 0.67118(15) 0.0278(4) Uani 1 1 d . . . H3A1 H 0.7228 0.6282 0.7339 0.042 Uiso 1 1 calc R . . H3A2 H 0.6681 0.7562 0.6665 0.042 Uiso 1 1 calc R . . H3A3 H 0.7943 0.6237 0.6185 0.042 Uiso 1 1 calc R . . O4 O 0.84558(11) 0.75665(11) 0.40317(8) 0.0186(2) Uani 1 1 d . A . C4 C 0.22034(17) 1.12736(16) 0.91665(11) 0.0209(3) Uani 1 1 d . . . C5 C 0.1452(2) 1.1903(2) 1.01468(13) 0.0293(4) Uani 1 1 d . A . H5A H 0.1072 1.2868 1.0044 0.035 Uiso 1 1 calc R . . H5B H 0.0656 1.1674 1.0501 0.035 Uiso 1 1 calc R . . C6 C 0.2397(2) 1.1468(2) 1.07507(13) 0.0322(4) Uani 1 1 d . . . H6 H 0.2856 1.0551 1.0874 0.039 Uiso 1 1 calc R A . C7 C 0.2658(2) 1.2223(2) 1.11294(14) 0.0360(4) Uani 1 1 d . A . H7A H 0.2225 1.3148 1.1028 0.043 Uiso 1 1 calc R . . H7B H 0.3279 1.1845 1.1505 0.043 Uiso 1 1 calc R . . C8 C 0.16224(17) 1.07544(16) 0.87888(11) 0.0190(3) Uani 1 1 d . A . H8 H 0.0718 1.0798 0.9145 0.023 Uiso 1 1 calc R . . C9 C 0.23433(16) 1.01543(14) 0.78788(11) 0.0158(3) Uani 1 1 d . . . C10 C 0.16198(16) 0.97139(15) 0.75067(11) 0.0171(3) Uani 1 1 d . A . H10 H 0.0673 0.9895 0.7866 0.020 Uiso 1 1 calc R . . C11 C 0.13243(17) 0.88615(17) 0.62843(12) 0.0148(4) Uani 0.893(4) 1 d P A 1 H11 H 0.1220 0.9485 0.5709 0.018 Uiso 0.893(4) 1 calc PR A 1 C11' C 0.1558(14) 0.8123(14) 0.6571(10) 0.013(3) Uani 0.107(4) 1 d PU A 2 H11A H 0.1851 0.7264 0.6944 0.015 Uiso 0.107(4) 1 calc PR A 2 C12 C -0.01269(16) 0.90126(16) 0.69256(11) 0.0183(3) Uani 1 1 d . . . H12A H -0.0700 0.9920 0.7149 0.022 Uiso 0.893(4) 1 calc PR A 1 H12B H -0.0059 0.8409 0.7505 0.022 Uiso 0.893(4) 1 calc PR A 1 H12C H -0.0386 0.9852 0.6585 0.022 Uiso 0.107(4) 1 d PR A 2 H12D H -0.0486 0.9127 0.7613 0.022 Uiso 0.107(4) 1 d PR A 2 C13 C -0.08220(18) 0.8705(2) 0.63580(14) 0.0191(4) Uani 0.893(4) 1 d P A 1 H13A H -0.1751 0.8768 0.6789 0.023 Uiso 0.893(4) 1 calc PR A 1 H13B H -0.0962 0.9359 0.5812 0.023 Uiso 0.893(4) 1 calc PR A 1 C13' C -0.0598(14) 0.8030(15) 0.6604(10) 0.012(3) Uani 0.107(4) 1 d PU A 2 H13C H -0.0277 0.7172 0.6959 0.015 Uiso 0.107(4) 1 calc PR A 2 H13D H -0.1631 0.8414 0.6802 0.015 Uiso 0.107(4) 1 calc PR A 2 C14 C 0.00689(19) 0.73375(19) 0.59632(15) 0.0203(4) Uani 0.893(4) 1 d P A 1 H14A H -0.0387 0.7182 0.5574 0.024 Uiso 0.893(4) 1 calc PR A 1 H14B H 0.0123 0.6683 0.6514 0.024 Uiso 0.893(4) 1 calc PR A 1 C14' C -0.0009(15) 0.7811(15) 0.5516(12) 0.017(3) Uani 0.107(4) 1 d PU A 2 H14C H -0.0334 0.7244 0.5349 0.020 Uiso 0.107(4) 1 calc PR A 2 H14D H -0.0286 0.8654 0.5137 0.020 Uiso 0.107(4) 1 calc PR A 2 C15 C 0.15591(16) 0.71415(16) 0.53254(12) 0.0202(3) Uani 1 1 d . . . H15A H 0.2126 0.6221 0.5130 0.024 Uiso 0.893(4) 1 calc PR A 1 H15B H 0.1526 0.7717 0.4730 0.024 Uiso 0.893(4) 1 calc PR A 1 H15C H 0.2018 0.6872 0.4667 0.024 Uiso 0.107(4) 1 d PR A 2 H15D H 0.1778 0.6369 0.5745 0.024 Uiso 0.107(4) 1 d PR A 2 C16 C 0.22239(17) 0.74781(17) 0.59088(13) 0.0156(4) Uani 0.893(4) 1 d P A 1 H16 H 0.2297 0.6847 0.6483 0.019 Uiso 0.893(4) 1 calc PR A 1 C16' C 0.2102(13) 0.7984(13) 0.5481(10) 0.009(3) Uani 0.107(4) 1 d PU A 2 H16A H 0.1778 0.8854 0.5126 0.011 Uiso 0.107(4) 1 calc PR A 2 C17 C 0.44481(16) 0.66981(14) 0.46320(11) 0.0164(3) Uani 1 1 d . A . H17 H 0.4096 0.6221 0.4436 0.020 Uiso 1 1 calc R . . C18 C 0.58502(15) 0.65480(13) 0.40831(11) 0.0146(3) Uani 1 1 d . . . C19 C 0.65501(16) 0.57952(14) 0.32433(11) 0.0168(3) Uani 1 1 d . A . H19 H 0.6093 0.5396 0.3078 0.020 Uiso 1 1 calc R . . C20 C 0.78710(17) 0.56278(15) 0.26616(11) 0.0182(3) Uani 1 1 d . . . C21 C 0.86252(18) 0.48461(16) 0.17464(12) 0.0226(3) Uani 1 1 d . A . H21A H 0.9433 0.5043 0.1353 0.027 Uiso 1 1 calc R . . H21B H 0.8994 0.3900 0.1936 0.027 Uiso 1 1 calc R . . C22 C 0.7733(2) 0.5118(2) 0.11312(15) 0.0355(4) Uani 1 1 d . . . H22 H 0.7264 0.6005 0.0934 0.043 Uiso 1 1 calc R A . C23 C 0.7543(3) 0.4236(3) 0.0840(2) 0.0553(6) Uani 1 1 d U A . H23A H 0.7992 0.3337 0.1021 0.066 Uiso 1 1 calc R . . H23B H 0.6954 0.4497 0.0448 0.066 Uiso 1 1 calc R . . C24 C 0.85422(16) 0.62034(15) 0.29312(11) 0.0177(3) Uani 1 1 d . A . H24 H 0.9467 0.6076 0.2547 0.021 Uiso 1 1 calc R . . C25 C 0.78876(15) 0.69459(14) 0.37389(11) 0.0154(3) Uani 1 1 d . . . C26 C 0.64972(15) 0.71656(13) 0.43441(11) 0.0141(3) Uani 1 1 d . A . C27 C 0.60665(17) 1.13213(16) 0.74204(12) 0.0203(3) Uani 1 1 d . . . H27A H 0.5355 1.2223 0.7553 0.030 Uiso 1 1 calc R A . H27B H 0.6894 1.1331 0.6894 0.030 Uiso 1 1 calc R . . H27C H 0.6325 1.0899 0.8008 0.030 Uiso 1 1 calc R . . C28 C 0.98626(16) 0.73472(16) 0.34932(13) 0.0227(3) Uani 1 1 d . . . H28A H 1.0484 0.6421 0.3567 0.034 Uiso 1 1 calc R A . H28B H 1.0125 0.7892 0.3737 0.034 Uiso 1 1 calc R . . H28C H 0.9946 0.7578 0.2804 0.034 Uiso 1 1 calc R . . O1S O 0.81544(15) 0.14926(15) 0.87501(12) 0.0413(3) Uani 1 1 d . . . C1S C 0.7057(2) 0.24027(19) 0.90798(14) 0.0289(4) Uani 1 1 d . . . C2S C 0.6057(2) 0.2314(2) 1.00521(16) 0.0402(5) Uani 1 1 d . . . H2SA H 0.6519 0.1508 1.0404 0.060 Uiso 1 1 calc R . . H2SB H 0.5246 0.2303 0.9969 0.060 Uiso 1 1 calc R . . H2SC H 0.5748 0.3074 1.0423 0.060 Uiso 1 1 calc R . . C3S C 0.6599(3) 0.3673(2) 0.85100(19) 0.0521(6) Uani 1 1 d . . . H3SA H 0.7132 0.3532 0.7819 0.078 Uiso 1 1 calc R . . H3SB H 0.6766 0.4307 0.8739 0.078 Uiso 1 1 calc R . . H3SC H 0.5600 0.4013 0.8598 0.078 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 Co1 0.00993(10) 0.01301(10) 0.01251(10) -0.00076(7) -0.00259(7) -0.00546(7) O1 0.0151(5) 0.0244(5) 0.0176(5) -0.0041(4) -0.0033(4) -0.0109(4) O1W 0.0149(5) 0.0153(5) 0.0128(5) -0.0014(4) -0.0024(4) -0.0074(4) C1 0.0148(7) 0.0157(6) 0.0126(6) 0.0003(5) -0.0052(6) -0.0062(5) O1A 0.0337(7) 0.0219(6) 0.0385(8) -0.0059(5) -0.0154(6) -0.0072(5) C1A 0.0248(8) 0.0188(7) 0.0179(7) 0.0015(6) -0.0099(6) -0.0084(6) C2A 0.0183(8) 0.0185(7) 0.0222(8) 0.0051(6) -0.0061(6) -0.0096(6) N2 0.0130(6) 0.0208(6) 0.0149(6) -0.0012(5) -0.0041(5) -0.0082(5) O2 0.0138(5) 0.0197(5) 0.0119(5) -0.0026(4) -0.0016(4) -0.0089(4) C2 0.0138(7) 0.0168(6) 0.0142(7) -0.0002(5) -0.0047(6) -0.0063(5) O3 0.0117(5) 0.0155(5) 0.0173(5) -0.0048(4) -0.0017(4) -0.0060(4) C3 0.0205(8) 0.0232(7) 0.0159(7) -0.0023(6) -0.0063(6) -0.0106(6) N3 0.0118(6) 0.0154(6) 0.0216(6) -0.0041(5) -0.0029(5) -0.0061(5) C3A 0.0278(9) 0.0242(8) 0.0379(10) 0.0038(7) -0.0186(8) -0.0121(7) O4 0.0117(5) 0.0216(5) 0.0228(6) -0.0055(4) -0.0018(4) -0.0082(4) C4 0.0209(8) 0.0266(8) 0.0140(7) -0.0052(6) -0.0017(6) -0.0103(6) C5 0.0280(9) 0.0462(11) 0.0174(8) -0.0137(7) 0.0027(7) -0.0212(8) C6 0.0457(12) 0.0382(10) 0.0139(8) -0.0013(7) -0.0056(8) -0.0217(9) C7 0.0326(11) 0.0580(13) 0.0235(9) -0.0098(9) -0.0019(8) -0.0261(10) C8 0.0158(7) 0.0261(8) 0.0139(7) -0.0035(6) -0.0007(6) -0.0098(6) C9 0.0151(7) 0.0188(7) 0.0127(6) -0.0012(5) -0.0033(6) -0.0071(6) C10 0.0138(7) 0.0233(7) 0.0141(7) -0.0013(6) -0.0017(6) -0.0098(6) C11 0.0128(8) 0.0169(8) 0.0149(8) -0.0027(6) -0.0034(6) -0.0064(6) C11' 0.013(3) 0.013(3) 0.015(3) -0.0017(19) -0.004(2) -0.007(2) C12 0.0126(7) 0.0254(7) 0.0167(7) -0.0035(6) -0.0020(6) -0.0088(6) C13 0.0124(8) 0.0254(10) 0.0203(9) -0.0032(7) -0.0035(7) -0.0091(7) C13' 0.011(3) 0.012(3) 0.015(3) -0.0007(19) -0.004(2) -0.006(2) C14 0.0154(8) 0.0270(9) 0.0224(10) -0.0049(8) -0.0036(7) -0.0123(7) C14' 0.016(3) 0.018(4) 0.016(4) -0.0002(19) -0.006(2) -0.007(2) C15 0.0142(7) 0.0259(8) 0.0226(8) -0.0079(6) -0.0015(6) -0.0107(6) C16 0.0121(8) 0.0170(8) 0.0168(9) -0.0033(7) -0.0015(6) -0.0068(6) C16' 0.010(3) 0.010(3) 0.008(3) -0.0001(19) -0.003(2) -0.004(2) C17 0.0140(7) 0.0147(6) 0.0216(7) -0.0030(5) -0.0051(6) -0.0066(5) C18 0.0125(7) 0.0137(6) 0.0160(7) -0.0015(5) -0.0027(6) -0.0053(5) C19 0.0163(7) 0.0159(6) 0.0183(7) -0.0027(5) -0.0047(6) -0.0068(6) C20 0.0184(7) 0.0171(7) 0.0161(7) -0.0027(5) -0.0038(6) -0.0057(6) C21 0.0198(8) 0.0243(8) 0.0193(8) -0.0072(6) -0.0009(6) -0.0072(6) C22 0.0298(10) 0.0426(11) 0.0276(10) -0.0147(8) -0.0057(8) -0.0074(8) C23 0.0461(12) 0.0678(13) 0.0593(13) -0.0305(11) -0.0120(10) -0.0225(10) C24 0.0115(7) 0.0180(7) 0.0192(7) -0.0017(6) -0.0014(6) -0.0049(5) C25 0.0125(7) 0.0144(6) 0.0187(7) -0.0013(5) -0.0040(6) -0.0057(5) C26 0.0119(7) 0.0128(6) 0.0160(7) -0.0001(5) -0.0040(6) -0.0044(5) C27 0.0192(8) 0.0256(8) 0.0221(8) -0.0022(6) -0.0082(6) -0.0127(6) C28 0.0127(7) 0.0254(8) 0.0288(9) -0.0028(6) -0.0031(6) -0.0091(6) O1S 0.0259(7) 0.0384(8) 0.0455(9) -0.0071(7) 0.0002(7) -0.0089(6) C1S 0.0249(9) 0.0332(9) 0.0307(9) -0.0042(7) -0.0072(8) -0.0140(8) C2S 0.0355(11) 0.0369(10) 0.0370(11) -0.0019(9) 0.0009(9) -0.0158(9) C3S 0.0456(14) 0.0456(13) 0.0432(13) 0.0058(10) -0.0054(11) -0.0115(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 Co1 N2 1.8806(13) . ? Co1 N3 1.8874(12) . ? Co1 O3 1.9013(11) . ? Co1 O2 1.9064(10) . ? Co1 C2A 1.9907(15) . ? Co1 O1W 2.0860(11) . ? O1 C2 1.3663(18) . ? O1 C27 1.4269(17) . ? O1W H1W 0.80(3) . ? O1W H2W 0.78(2) . ? C1 O2 1.3064(18) . ? C1 C9 1.411(2) . ? C1 C2 1.4320(19) . ? O1A C1A 1.225(2) . ? C1A C2A 1.463(2) . ? C1A C3A 1.509(2) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? N2 C10 1.2893(19) . ? N2 C11 1.4743(19) . ? N2 C11' 1.647(13) . ? C2 C3 1.377(2) . ? O3 C26 1.3067(17) . ? C3 C4 1.409(2) . ? C3 H3 0.9500 . ? N3 C17 1.291(2) . ? N3 C16 1.486(2) . ? N3 C16' 1.508(13) . ? C3A H3A1 0.9800 . ? C3A H3A2 0.9800 . ? C3A H3A3 0.9800 . ? O4 C25 1.3709(17) . ? O4 C28 1.4243(19) . ? C4 C8 1.372(2) . ? C4 C5 1.519(2) . ? C5 C6 1.493(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.312(3) . ? C6 H6 0.9500 . ? C7 H7A 0.9500 . ? C7 H7B 0.9500 . ? C8 C9 1.418(2) . ? C8 H8 0.9500 . ? C9 C10 1.440(2) . ? C10 H10 0.9500 . ? C11 C12 1.518(2) . ? C11 C16 1.527(2) . ? C11 H11 1.0000 . ? C11' C16' 1.515(19) . ? C11' C12 1.630(14) . ? C11' H11A 1.0000 . ? C12 C13 1.525(2) . ? C12 C13' 1.664(13) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 H12C 0.9599 . ? C12 H12D 0.9587 . ? C13 C14 1.521(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13' C14' 1.52(2) . ? C13' H13C 0.9900 . ? C13' H13D 0.9900 . ? C14 C15 1.540(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C14' C15 1.517(15) . ? C14' H14C 0.9900 . ? C14' H14D 0.9900 . ? C15 C16' 1.459(12) . ? C15 C16 1.536(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C15 H15C 0.9589 . ? C15 H15D 0.9597 . ? C16 H16 1.0000 . ? C16' H16A 1.0000 . ? C17 C18 1.443(2) . ? C17 H17 0.9500 . ? C18 C26 1.4162(19) . ? C18 C19 1.417(2) . ? C19 C20 1.372(2) . ? C19 H19 0.9500 . ? C20 C24 1.409(2) . ? C20 C21 1.521(2) . ? C21 C22 1.491(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.311(3) . ? C22 H22 0.9500 . ? C23 H23A 0.9500 . ? C23 H23B 0.9500 . ? C24 C25 1.375(2) . ? C24 H24 0.9500 . ? C25 C26 1.431(2) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? O1S C1S 1.202(2) . ? C1S C2S 1.490(3) . ? C1S C3S 1.495(3) . ? C2S H2SA 0.9800 . ? C2S H2SB 0.9800 . ? C2S H2SC 0.9800 . ? C3S H3SA 0.9800 . ? C3S H3SB 0.9800 . ? C3S H3SC 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Co1 N3 85.92(6) . . ? N2 Co1 O3 176.68(5) . . ? N3 Co1 O3 94.40(5) . . ? N2 Co1 O2 93.04(5) . . ? N3 Co1 O2 178.04(5) . . ? O3 Co1 O2 86.55(4) . . ? N2 Co1 C2A 88.58(6) . . ? N3 Co1 C2A 91.52(6) . . ? O3 Co1 C2A 94.71(6) . . ? O2 Co1 C2A 90.11(6) . . ? N2 Co1 O1W 87.10(5) . . ? N3 Co1 O1W 88.98(5) . . ? O3 Co1 O1W 89.61(5) . . ? O2 Co1 O1W 89.32(4) . . ? C2A Co1 O1W 175.61(6) . . ? C2 O1 C27 117.05(12) . . ? Co1 O1W H1W 111.1(17) . . ? Co1 O1W H2W 109.8(17) . . ? H1W O1W H2W 104(2) . . ? O2 C1 C9 125.54(13) . . ? O2 C1 C2 117.74(13) . . ? C9 C1 C2 116.71(13) . . ? O1A C1A C2A 121.99(15) . . ? O1A C1A C3A 119.72(16) . . ? C2A C1A C3A 118.28(14) . . ? C1A C2A Co1 110.60(11) . . ? C1A C2A H2A1 109.5 . . ? Co1 C2A H2A1 109.5 . . ? C1A C2A H2A2 109.5 . . ? Co1 C2A H2A2 109.5 . . ? H2A1 C2A H2A2 108.1 . . ? C10 N2 C11 121.76(13) . . ? C10 N2 C11' 120.3(5) . . ? C11 N2 C11' 30.5(5) . . ? C10 N2 Co1 127.09(10) . . ? C11 N2 Co1 111.02(10) . . ? C11' N2 Co1 106.6(5) . . ? C1 O2 Co1 124.63(9) . . ? O1 C2 C3 125.00(13) . . ? O1 C2 C1 113.72(13) . . ? C3 C2 C1 121.28(14) . . ? C26 O3 Co1 126.12(9) . . ? C2 C3 C4 121.36(14) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C17 N3 C16 121.01(13) . . ? C17 N3 C16' 114.1(5) . . ? C16 N3 C16' 30.0(6) . . ? C17 N3 Co1 126.88(11) . . ? C16 N3 Co1 112.05(10) . . ? C16' N3 Co1 112.8(5) . . ? C1A C3A H3A1 109.5 . . ? C1A C3A H3A2 109.5 . . ? H3A1 C3A H3A2 109.5 . . ? C1A C3A H3A3 109.5 . . ? H3A1 C3A H3A3 109.5 . . ? H3A2 C3A H3A3 109.5 . . ? C25 O4 C28 117.08(12) . . ? C8 C4 C3 118.47(14) . . ? C8 C4 C5 122.00(15) . . ? C3 C4 C5 119.54(14) . . ? C6 C5 C4 112.08(16) . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5B 109.2 . . ? C4 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 126.7(2) . . ? C7 C6 H6 116.7 . . ? C5 C6 H6 116.7 . . ? C6 C7 H7A 120.0 . . ? C6 C7 H7B 120.0 . . ? H7A C7 H7B 120.0 . . ? C4 C8 C9 121.40(15) . . ? C4 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C1 C9 C8 120.74(13) . . ? C1 C9 C10 121.35(13) . . ? C8 C9 C10 117.72(14) . . ? N2 C10 C9 124.30(14) . . ? N2 C10 H10 117.9 . . ? C9 C10 H10 117.9 . . ? N2 C11 C12 117.71(13) . . ? N2 C11 C16 104.76(13) . . ? C12 C11 C16 110.91(14) . . ? N2 C11 H11 107.7 . . ? C12 C11 H11 107.7 . . ? C16 C11 H11 107.7 . . ? C16' C11' C12 110.4(10) . . ? C16' C11' N2 103.2(9) . . ? C12 C11' N2 102.8(8) . . ? C16' C11' H11A 113.2 . . ? C12 C11' H11A 113.2 . . ? N2 C11' H11A 113.2 . . ? C11 C12 C13 109.90(13) . . ? C11 C12 C11' 30.6(5) . . ? C13 C12 C11' 110.6(5) . . ? C11 C12 C13' 111.4(5) . . ? C13 C12 C13' 27.0(5) . . ? C11' C12 C13' 98.0(7) . . ? C11 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? C11' C12 H12A 132.0 . . ? C13' C12 H12A 129.2 . . ? C11 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? C11' C12 H12B 81.4 . . ? C13' C12 H12B 84.6 . . ? H12A C12 H12B 108.2 . . ? C11 C12 H12C 81.6 . . ? C13 C12 H12C 85.4 . . ? C11' C12 H12C 112.1 . . ? C13' C12 H12C 112.4 . . ? H12A C12 H12C 47.3 . . ? H12B C12 H12C 155.4 . . ? C11 C12 H12D 124.8 . . ? C13 C12 H12D 124.4 . . ? C11' C12 H12D 111.5 . . ? C13' C12 H12D 112.6 . . ? H12A C12 H12D 62.6 . . ? H12B C12 H12D 45.6 . . ? H12C C12 H12D 109.9 . . ? C14 C13 C12 110.98(15) . . ? C14 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? C14 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C14' C13' C12 113.3(11) . . ? C14' C13' H13C 108.9 . . ? C12 C13' H13C 108.9 . . ? C14' C13' H13D 108.9 . . ? C12 C13' H13D 108.9 . . ? H13C C13' H13D 107.7 . . ? C13 C14 C15 112.51(14) . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C15 C14' C13' 103.5(11) . . ? C15 C14' H14C 111.1 . . ? C13' C14' H14C 111.1 . . ? C15 C14' H14D 111.1 . . ? C13' C14' H14D 111.1 . . ? H14C C14' H14D 109.0 . . ? C16' C15 C14' 113.0(8) . . ? C16' C15 C16 29.8(6) . . ? C14' C15 C16 120.6(6) . . ? C16' C15 C14 117.5(5) . . ? C14' C15 C14 29.2(6) . . ? C16 C15 C14 108.87(14) . . ? C16' C15 H15A 125.2 . . ? C14' C15 H15A 121.9 . . ? C16 C15 H15A 109.9 . . ? C14 C15 H15A 109.9 . . ? C16' C15 H15B 80.3 . . ? C14' C15 H15B 80.7 . . ? C16 C15 H15B 109.9 . . ? C14 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? C16' C15 H15C 108.5 . . ? C14' C15 H15C 109.3 . . ? C16 C15 H15C 123.9 . . ? C14 C15 H15C 127.2 . . ? H15A C15 H15C 55.1 . . ? H15B C15 H15C 53.3 . . ? C16' C15 H15D 109.5 . . ? C14' C15 H15D 108.6 . . ? C16 C15 H15D 80.0 . . ? C14 C15 H15D 80.5 . . ? H15A C15 H15D 52.8 . . ? H15B C15 H15D 161.1 . . ? H15C C15 H15D 107.8 . . ? N3 C16 C11 105.41(13) . . ? N3 C16 C15 115.52(14) . . ? C11 C16 C15 111.43(14) . . ? N3 C16 H16 108.1 . . ? C11 C16 H16 108.1 . . ? C15 C16 H16 108.1 . . ? C15 C16' N3 118.9(9) . . ? C15 C16' C11' 104.5(10) . . ? N3 C16' C11' 97.1(9) . . ? C15 C16' H16A 111.7 . . ? N3 C16' H16A 111.7 . . ? C11' C16' H16A 111.7 . . ? N3 C17 C18 125.17(13) . . ? N3 C17 H17 117.4 . . ? C18 C17 H17 117.4 . . ? C26 C18 C19 120.55(13) . . ? C26 C18 C17 121.84(13) . . ? C19 C18 C17 117.57(13) . . ? C20 C19 C18 121.70(13) . . ? C20 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? C19 C20 C24 118.23(14) . . ? C19 C20 C21 122.37(14) . . ? C24 C20 C21 119.40(14) . . ? C22 C21 C20 114.20(14) . . ? C22 C21 H21A 108.7 . . ? C20 C21 H21A 108.7 . . ? C22 C21 H21B 108.7 . . ? C20 C21 H21B 108.7 . . ? H21A C21 H21B 107.6 . . ? C23 C22 C21 125.6(2) . . ? C23 C22 H22 117.2 . . ? C21 C22 H22 117.2 . . ? C22 C23 H23A 120.0 . . ? C22 C23 H23B 120.0 . . ? H23A C23 H23B 120.0 . . ? C25 C24 C20 121.43(14) . . ? C25 C24 H24 119.3 . . ? C20 C24 H24 119.3 . . ? O4 C25 C24 124.81(14) . . ? O4 C25 C26 113.63(13) . . ? C24 C25 C26 121.54(13) . . ? O3 C26 C18 125.38(13) . . ? O3 C26 C25 118.12(12) . . ? C18 C26 C25 116.50(13) . . ? O1 C27 H27A 109.5 . . ? O1 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O1 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O4 C28 H28A 109.5 . . ? O4 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O4 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O1S C1S C2S 122.27(19) . . ? O1S C1S C3S 121.26(19) . . ? C2S C1S C3S 116.42(18) . . ? C1S C2S H2SA 109.5 . . ? C1S C2S H2SB 109.5 . . ? H2SA C2S H2SB 109.5 . . ? C1S C2S H2SC 109.5 . . ? H2SA C2S H2SC 109.5 . . ? H2SB C2S H2SC 109.5 . . ? C1S C3S H3SA 109.5 . . ? C1S C3S H3SB 109.5 . . ? H3SA C3S H3SB 109.5 . . ? C1S C3S H3SC 109.5 . . ? H3SA C3S H3SC 109.5 . . ? H3SB C3S H3SC 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1A C1A C2A Co1 -99.55(16) . . . . ? C3A C1A C2A Co1 81.08(16) . . . . ? N2 Co1 C2A C1A 175.92(12) . . . . ? N3 Co1 C2A C1A 90.05(12) . . . . ? O3 Co1 C2A C1A -4.50(12) . . . . ? O2 Co1 C2A C1A -91.04(11) . . . . ? O1W Co1 C2A C1A -173.5(7) . . . . ? N3 Co1 N2 C10 164.17(14) . . . . ? O3 Co1 N2 C10 -100.2(8) . . . . ? O2 Co1 N2 C10 -17.49(14) . . . . ? C2A Co1 N2 C10 72.54(14) . . . . ? O1W Co1 N2 C10 -106.65(13) . . . . ? N3 Co1 N2 C11 -20.00(11) . . . . ? O3 Co1 N2 C11 75.7(9) . . . . ? O2 Co1 N2 C11 158.34(10) . . . . ? C2A Co1 N2 C11 -111.63(11) . . . . ? O1W Co1 N2 C11 69.18(10) . . . . ? N3 Co1 N2 C11' 11.9(5) . . . . ? O3 Co1 N2 C11' 107.6(10) . . . . ? O2 Co1 N2 C11' -169.8(5) . . . . ? C2A Co1 N2 C11' -79.7(5) . . . . ? O1W Co1 N2 C11' 101.1(5) . . . . ? C9 C1 O2 Co1 -13.6(2) . . . . ? C2 C1 O2 Co1 167.67(9) . . . . ? N2 Co1 O2 C1 20.91(11) . . . . ? N3 Co1 O2 C1 78.5(15) . . . . ? O3 Co1 O2 C1 -162.39(11) . . . . ? C2A Co1 O2 C1 -67.68(12) . . . . ? O1W Co1 O2 C1 107.97(11) . . . . ? C27 O1 C2 C3 -8.6(2) . . . . ? C27 O1 C2 C1 171.56(12) . . . . ? O2 C1 C2 O1 0.87(18) . . . . ? C9 C1 C2 O1 -177.98(12) . . . . ? O2 C1 C2 C3 -178.95(13) . . . . ? C9 C1 C2 C3 2.2(2) . . . . ? N2 Co1 O3 C26 -90.5(8) . . . . ? N3 Co1 O3 C26 4.89(12) . . . . ? O2 Co1 O3 C26 -173.40(11) . . . . ? C2A Co1 O3 C26 96.78(12) . . . . ? O1W Co1 O3 C26 -84.06(11) . . . . ? O1 C2 C3 C4 178.18(14) . . . . ? C1 C2 C3 C4 -2.0(2) . . . . ? N2 Co1 N3 C17 174.10(14) . . . . ? O3 Co1 N3 C17 -2.59(14) . . . . ? O2 Co1 N3 C17 116.4(15) . . . . ? C2A Co1 N3 C17 -97.43(14) . . . . ? O1W Co1 N3 C17 86.93(14) . . . . ? N2 Co1 N3 C16 -8.68(11) . . . . ? O3 Co1 N3 C16 174.63(11) . . . . ? O2 Co1 N3 C16 -66.4(16) . . . . ? C2A Co1 N3 C16 79.79(11) . . . . ? O1W Co1 N3 C16 -95.84(11) . . . . ? N2 Co1 N3 C16' 23.8(6) . . . . ? O3 Co1 N3 C16' -152.9(6) . . . . ? O2 Co1 N3 C16' -33.9(17) . . . . ? C2A Co1 N3 C16' 112.3(6) . . . . ? O1W Co1 N3 C16' -63.4(6) . . . . ? C2 C3 C4 C8 0.3(2) . . . . ? C2 C3 C4 C5 -179.44(15) . . . . ? C8 C4 C5 C6 134.94(17) . . . . ? C3 C4 C5 C6 -45.3(2) . . . . ? C4 C5 C6 C7 123.8(2) . . . . ? C3 C4 C8 C9 1.1(2) . . . . ? C5 C4 C8 C9 -179.14(16) . . . . ? O2 C1 C9 C8 -179.54(14) . . . . ? C2 C1 C9 C8 -0.8(2) . . . . ? O2 C1 C9 C10 -4.6(2) . . . . ? C2 C1 C9 C10 174.11(13) . . . . ? C4 C8 C9 C1 -0.8(2) . . . . ? C4 C8 C9 C10 -175.92(15) . . . . ? C11 N2 C10 C9 -169.39(14) . . . . ? C11' N2 C10 C9 154.9(6) . . . . ? Co1 N2 C10 C9 6.0(2) . . . . ? C1 C9 C10 N2 8.9(2) . . . . ? C8 C9 C10 N2 -176.04(14) . . . . ? C10 N2 C11 C12 -17.7(2) . . . . ? C11' N2 C11 C12 79.1(9) . . . . ? Co1 N2 C11 C12 166.18(11) . . . . ? C10 N2 C11 C16 -141.45(15) . . . . ? C11' N2 C11 C16 -44.6(9) . . . . ? Co1 N2 C11 C16 42.46(15) . . . . ? C10 N2 C11' C16' 160.7(7) . . . . ? C11 N2 C11' C16' 58.7(10) . . . . ? Co1 N2 C11' C16' -44.7(10) . . . . ? C10 N2 C11' C12 45.9(9) . . . . ? C11 N2 C11' C12 -56.1(7) . . . . ? Co1 N2 C11' C12 -159.6(5) . . . . ? N2 C11 C12 C13 -178.60(14) . . . . ? C16 C11 C12 C13 -58.03(19) . . . . ? N2 C11 C12 C11' -81.5(9) . . . . ? C16 C11 C12 C11' 39.0(9) . . . . ? N2 C11 C12 C13' -149.8(6) . . . . ? C16 C11 C12 C13' -29.2(6) . . . . ? C16' C11' C12 C11 -56.0(10) . . . . ? N2 C11' C12 C11 53.5(7) . . . . ? C16' C11' C12 C13 38.5(11) . . . . ? N2 C11' C12 C13 148.0(5) . . . . ? C16' C11' C12 C13' 63.2(11) . . . . ? N2 C11' C12 C13' 172.7(8) . . . . ? C11 C12 C13 C14 56.7(2) . . . . ? C11' C12 C13 C14 24.0(6) . . . . ? C13' C12 C13 C14 -41.7(10) . . . . ? C11 C12 C13' C14' -32.9(13) . . . . ? C13 C12 C13' C14' 59.1(12) . . . . ? C11' C12 C13' C14' -61.3(13) . . . . ? C12 C13 C14 C15 -56.2(2) . . . . ? C12 C13' C14' C15 62.4(13) . . . . ? C13' C14' C15 C16' -65.8(13) . . . . ? C13' C14' C15 C16 -33.3(13) . . . . ? C13' C14' C15 C14 39.9(9) . . . . ? C13 C14 C15 C16' 23.7(7) . . . . ? C13 C14 C15 C14' -64.6(11) . . . . ? C13 C14 C15 C16 54.8(2) . . . . ? C17 N3 C16 C11 -149.00(14) . . . . ? C16' N3 C16 C11 -64.2(9) . . . . ? Co1 N3 C16 C11 33.59(16) . . . . ? C17 N3 C16 C15 -25.5(2) . . . . ? C16' N3 C16 C15 59.3(9) . . . . ? Co1 N3 C16 C15 157.06(12) . . . . ? N2 C11 C16 N3 -47.34(17) . . . . ? C12 C11 C16 N3 -175.31(13) . . . . ? N2 C11 C16 C15 -173.37(13) . . . . ? C12 C11 C16 C15 58.66(19) . . . . ? C16' C15 C16 N3 -63.1(10) . . . . ? C14' C15 C16 N3 -146.3(8) . . . . ? C14 C15 C16 N3 -175.84(14) . . . . ? C16' C15 C16 C11 57.1(10) . . . . ? C14' C15 C16 C11 -26.0(8) . . . . ? C14 C15 C16 C11 -55.60(19) . . . . ? C14' C15 C16' N3 176.9(10) . . . . ? C16 C15 C16' N3 65.1(10) . . . . ? C14 C15 C16' N3 144.9(7) . . . . ? C14' C15 C16' C11' 70.1(13) . . . . ? C16 C15 C16' C11' -41.7(9) . . . . ? C14 C15 C16' C11' 38.2(11) . . . . ? C17 N3 C16' C15 41.9(12) . . . . ? C16 N3 C16' C15 -68.9(11) . . . . ? Co1 N3 C16' C15 -163.8(7) . . . . ? C17 N3 C16' C11' 152.8(7) . . . . ? C16 N3 C16' C11' 42.0(8) . . . . ? Co1 N3 C16' C11' -52.9(10) . . . . ? C12 C11' C16' C15 -70.1(11) . . . . ? N2 C11' C16' C15 -179.4(7) . . . . ? C12 C11' C16' N3 167.5(7) . . . . ? N2 C11' C16' N3 58.2(10) . . . . ? C16 N3 C17 C18 -177.69(14) . . . . ? C16' N3 C17 C18 149.3(6) . . . . ? Co1 N3 C17 C18 -0.7(2) . . . . ? N3 C17 C18 C26 3.1(2) . . . . ? N3 C17 C18 C19 -174.56(14) . . . . ? C26 C18 C19 C20 0.6(2) . . . . ? C17 C18 C19 C20 178.24(13) . . . . ? C18 C19 C20 C24 1.4(2) . . . . ? C18 C19 C20 C21 -178.72(14) . . . . ? C19 C20 C21 C22 43.6(2) . . . . ? C24 C20 C21 C22 -136.52(17) . . . . ? C20 C21 C22 C23 -125.5(2) . . . . ? C19 C20 C24 C25 -1.8(2) . . . . ? C21 C20 C24 C25 178.35(14) . . . . ? C28 O4 C25 C24 -4.5(2) . . . . ? C28 O4 C25 C26 177.16(13) . . . . ? C20 C24 C25 O4 -178.06(13) . . . . ? C20 C24 C25 C26 0.2(2) . . . . ? Co1 O3 C26 C18 -4.0(2) . . . . ? Co1 O3 C26 C25 175.11(9) . . . . ? C19 C18 C26 O3 177.04(13) . . . . ? C17 C18 C26 O3 -0.5(2) . . . . ? C19 C18 C26 C25 -2.1(2) . . . . ? C17 C18 C26 C25 -179.69(13) . . . . ? O4 C25 C26 O3 0.96(19) . . . . ? C24 C25 C26 O3 -177.45(13) . . . . ? O4 C25 C26 C18 -179.81(12) . . . . ? C24 C25 C26 C18 1.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 29.16 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.657 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.063 # Attachment 'Dialdehyde_7_NEW.cif' data_rmh043_0m _database_code_depnum_ccdc_archive 'CCDC 735902' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 O6' _chemical_formula_weight 356.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 4.031(2) _cell_length_b 12.305(7) _cell_length_c 16.759(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.249(16) _cell_angle_gamma 90.00 _cell_volume 830.0(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 810 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 26.98 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8200 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 10529 _diffrn_reflns_av_R_equivalents 0.1316 _diffrn_reflns_av_sigmaI/netI 0.1268 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 31.61 _reflns_number_total 2765 _reflns_number_gt 1601 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0672P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2765 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1244 _refine_ls_R_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.1874 _refine_ls_wR_factor_gt 0.1571 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 C1 C 0.1460(4) 0.11689(15) 0.68728(13) 0.0171(4) Uani 1 1 d . . . C2 C 0.3166(4) 0.19719(16) 0.73290(12) 0.0168(4) Uani 1 1 d . . . C3 C 0.3229(4) 0.30268(16) 0.70518(12) 0.0171(4) Uani 1 1 d . . . H3 H 0.4397 0.3563 0.7363 0.020 Uiso 1 1 calc R . . C4 C 0.1607(4) 0.33296(15) 0.63192(12) 0.0159(4) Uani 1 1 d . . . C5 C -0.0106(4) 0.25424(16) 0.58814(13) 0.0182(4) Uani 1 1 d . . . H5 H -0.1246 0.2732 0.5390 0.022 Uiso 1 1 calc R . . C6 C -0.0192(4) 0.14634(15) 0.61509(13) 0.0176(4) Uani 1 1 d . . . C7 C 0.1763(4) 0.45035(16) 0.60491(13) 0.0189(4) Uani 1 1 d . . . H7A H 0.0114 0.4930 0.6333 0.023 Uiso 1 1 calc R . . H7B H 0.3992 0.4797 0.6206 0.023 Uiso 1 1 calc R . . C8 C 0.1109(4) 0.46593(16) 0.51675(13) 0.0176(4) Uani 1 1 d . . . H8 H 0.2381 0.4237 0.4821 0.021 Uiso 1 1 calc R . . C9 C 0.6370(5) 0.23862(17) 0.85318(13) 0.0230(5) Uani 1 1 d . . . H9A H 0.7310 0.2025 0.9014 0.034 Uiso 1 1 calc R . . H9B H 0.4831 0.2957 0.8683 0.034 Uiso 1 1 calc R . . H9C H 0.8165 0.2710 0.8241 0.034 Uiso 1 1 calc R . . C10 C -0.20432(18) 0.06590(6) 0.56791(5) 0.0221(4) Uani 1 1 d . . . H10 H -0.3207 0.0896 0.5202 0.027 Uiso 1 1 calc R . . O1 O 0.46281(18) 0.16085(6) 0.80331(5) 0.0226(4) Uani 1 1 d R . . O2 O 0.14956(18) 0.01364(6) 0.71539(5) 0.0230(3) Uani 1 1 d R . . H2 H 0.0250 -0.0216 0.6762 0.028 Uiso 1 1 d R . . O3 O -0.22145(18) -0.03132(6) 0.58540(5) 0.0279(4) Uani 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 C1 0.0232(7) 0.0087(9) 0.0200(11) 0.0010(8) 0.0068(7) 0.0007(6) C2 0.0207(7) 0.0140(9) 0.0157(10) 0.0018(8) 0.0021(7) 0.0015(6) C3 0.0196(7) 0.0132(9) 0.0185(10) -0.0002(8) 0.0021(7) 0.0006(6) C4 0.0177(7) 0.0116(9) 0.0185(10) 0.0025(8) 0.0026(6) 0.0011(6) C5 0.0191(7) 0.0153(10) 0.0202(11) 0.0021(8) 0.0013(6) -0.0008(6) C6 0.0198(7) 0.0125(9) 0.0209(11) -0.0006(8) 0.0046(7) -0.0017(6) C7 0.0239(8) 0.0122(9) 0.0206(11) 0.0023(8) 0.0012(7) -0.0019(7) C8 0.0224(7) 0.0109(9) 0.0197(10) 0.0002(8) 0.0038(7) -0.0029(6) C9 0.0287(8) 0.0185(10) 0.0214(12) -0.0046(9) -0.0024(7) 0.0034(7) C10 0.0255(8) 0.0170(10) 0.0241(12) -0.0004(9) 0.0038(7) -0.0043(7) O1 0.0328(7) 0.0149(7) 0.0196(8) 0.0021(6) -0.0040(6) 0.0018(5) O2 0.0346(7) 0.0097(7) 0.0248(9) 0.0015(6) 0.0017(6) -0.0017(5) O3 0.0394(7) 0.0146(8) 0.0300(10) -0.0003(7) 0.0027(6) -0.0076(6) _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 C1 O2 1.355(2) . ? C1 C6 1.395(3) . ? C1 C2 1.405(3) . ? C2 O1 1.364(2) . ? C2 C3 1.379(3) . ? C3 C4 1.408(3) . ? C3 H3 0.9500 . ? C4 C5 1.377(3) . ? C4 C7 1.516(3) . ? C5 C6 1.403(3) . ? C5 H5 0.9500 . ? C6 C10 1.447(2) . ? C7 C8 1.498(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C8 1.327(4) 3_566 ? C8 H8 0.9500 . ? C9 O1 1.429(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 O3 1.2346 . ? C10 H10 0.9500 . ? O2 H2 0.9138 . ? 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 O2 C1 C6 122.70(16) . . ? O2 C1 C2 118.35(17) . . ? C6 C1 C2 118.95(18) . . ? O1 C2 C3 125.78(17) . . ? O1 C2 C1 114.48(17) . . ? C3 C2 C1 119.74(18) . . ? C2 C3 C4 121.75(17) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 118.20(18) . . ? C5 C4 C7 122.63(18) . . ? C3 C4 C7 119.17(17) . . ? C4 C5 C6 120.99(19) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C1 C6 C5 120.35(17) . . ? C1 C6 C10 120.13(16) . . ? C5 C6 C10 119.51(17) . . ? C8 C7 C4 114.10(17) . . ? C8 C7 H7A 108.7 . . ? C4 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? C4 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C8 C8 C7 125.1(2) 3_566 . ? C8 C8 H8 117.5 3_566 . ? C7 C8 H8 117.5 . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O3 C10 C6 124.54(9) . . ? O3 C10 H10 117.7 . . ? C6 C10 H10 117.7 . . ? C2 O1 C9 117.41(14) . . ? C1 O2 H2 101.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 O1 -1.7(2) . . . . ? C6 C1 C2 O1 178.43(15) . . . . ? O2 C1 C2 C3 178.78(16) . . . . ? C6 C1 C2 C3 -1.1(3) . . . . ? O1 C2 C3 C4 -179.21(15) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? C2 C3 C4 C5 0.8(3) . . . . ? C2 C3 C4 C7 179.85(17) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? C7 C4 C5 C6 179.98(17) . . . . ? O2 C1 C6 C5 -178.98(15) . . . . ? C2 C1 C6 C5 0.9(3) . . . . ? O2 C1 C6 C10 1.8(2) . . . . ? C2 C1 C6 C10 -178.37(15) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? C4 C5 C6 C10 179.42(15) . . . . ? C5 C4 C7 C8 -22.4(2) . . . . ? C3 C4 C7 C8 158.53(16) . . . . ? C4 C7 C8 C8 127.5(2) . . . 3_566 ? C1 C6 C10 O3 -2.4(2) . . . . ? C5 C6 C10 O3 178.33(11) . . . . ? C3 C2 O1 C9 0.3(2) . . . . ? C1 C2 O1 C9 -179.21(15) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 31.61 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.376 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.085 # Attachment 'Structure_6.cif' data_rmh44_0m _database_code_depnum_ccdc_archive 'CCDC 735903' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 O4' _chemical_formula_weight 296.31 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' 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 4.4309(4) _cell_length_b 9.7243(8) _cell_length_c 16.3855(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.510(5) _cell_angle_gamma 90.00 _cell_volume 703.82(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1366 _cell_measurement_theta_min 4.98 _cell_measurement_theta_max 41.14 _exptl_crystal_description NEEDLE _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4819 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 4.29 _diffrn_reflns_theta_max 36.39 _reflns_number_total 2851 _reflns_number_gt 2460 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0747P)^2^+0.1875P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2851 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1384 _refine_ls_wR_factor_gt 0.1324 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 C1 C 0.5453(2) 0.34540(9) 0.68901(5) 0.01973(17) Uani 1 1 d . . . H1 H 0.4504 0.4065 0.6516 0.024 Uiso 1 1 calc R . . C2 C 0.47364(19) 0.35476(8) 0.77374(5) 0.01527(14) Uani 1 1 d . . . C3 C 0.2722(2) 0.45650(8) 0.79689(5) 0.01844(16) Uani 1 1 d . . . H3 H 0.1832 0.5163 0.7577 0.022 Uiso 1 1 calc R . . C4 C 0.2057(2) 0.46817(8) 0.87744(6) 0.02052(17) Uani 1 1 d . . . H4 H 0.0736 0.5360 0.8929 0.025 Uiso 1 1 calc R . . C5 C 0.60699(18) 0.26391(7) 0.83351(4) 0.01433(14) Uani 1 1 d . . . C6 C 0.3391(2) 0.37678(8) 0.93580(5) 0.01830(15) Uani 1 1 d . . . H6 H 0.2919 0.3847 0.9899 0.022 Uiso 1 1 calc R . . C7 C 0.53963(19) 0.27472(8) 0.91553(4) 0.01502(14) Uani 1 1 d . . . C8 C 0.6845(2) 0.17848(8) 0.97974(5) 0.01827(16) Uani 1 1 d . . . H8A H 0.9018 0.1779 0.9758 0.022 Uiso 1 1 calc R . . H8B H 0.6469 0.2128 1.0336 0.022 Uiso 1 1 calc R . . C9 C 0.56721(19) 0.03352(8) 0.97103(4) 0.01590(15) Uani 1 1 d . . . H9 H 0.5902 -0.0121 0.9220 0.019 Uiso 1 1 calc R . . O1 O 0.7240(2) 0.26155(7) 0.66348(4) 0.02554(16) Uani 1 1 d . . . O2 O 0.80343(16) 0.16545(6) 0.81338(4) 0.01858(14) Uani 1 1 d . . . H2 H 0.8226 0.1685 0.7640 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0247(4) 0.0180(3) 0.0163(3) 0.0020(2) 0.0005(3) -0.0045(3) C2 0.0156(4) 0.0137(3) 0.0164(3) 0.0024(2) 0.0004(2) -0.0022(2) C3 0.0174(4) 0.0144(3) 0.0233(3) 0.0034(2) 0.0002(3) -0.0003(2) C4 0.0202(4) 0.0149(3) 0.0270(4) 0.0001(3) 0.0055(3) 0.0009(2) C5 0.0142(3) 0.0124(3) 0.0165(3) 0.0015(2) 0.0021(2) -0.0018(2) C6 0.0196(4) 0.0163(3) 0.0195(3) -0.0010(2) 0.0052(3) -0.0028(2) C7 0.0157(4) 0.0141(3) 0.0154(3) 0.0015(2) 0.0022(2) -0.0027(2) C8 0.0208(4) 0.0171(3) 0.0165(3) 0.0034(2) -0.0004(3) -0.0037(2) C9 0.0181(4) 0.0150(3) 0.0150(3) 0.0018(2) 0.0036(2) -0.0011(2) O1 0.0351(4) 0.0236(3) 0.0188(3) -0.0004(2) 0.0077(3) -0.0009(2) O2 0.0208(3) 0.0160(3) 0.0196(2) 0.00229(18) 0.0058(2) 0.00296(18) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2325(12) . ? C1 C2 1.4511(12) . ? C2 C3 1.4045(12) . ? C2 C5 1.4135(10) . ? C3 C4 1.3794(13) . ? C4 C6 1.4019(12) . ? C5 O2 1.3521(10) . ? C5 C7 1.4034(11) . ? C6 C7 1.3895(12) . ? C7 C8 1.5129(11) . ? C8 C9 1.5053(11) . ? C9 C9 1.3303(15) 3_657 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 124.13(8) . . ? C3 C2 C5 119.54(7) . . ? C3 C2 C1 119.61(7) . . ? C5 C2 C1 120.84(8) . . ? C4 C3 C2 120.30(7) . . ? C3 C4 C6 119.35(8) . . ? O2 C5 C7 118.44(7) . . ? O2 C5 C2 121.04(7) . . ? C7 C5 C2 120.53(7) . . ? C7 C6 C4 122.21(8) . . ? C6 C7 C5 118.07(7) . . ? C6 C7 C8 121.33(7) . . ? C5 C7 C8 120.60(7) . . ? C9 C8 C7 112.88(6) . . ? C9 C9 C8 124.19(9) 3_657 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 178.40(8) . . . . ? O1 C1 C2 C5 -0.78(13) . . . . ? C5 C2 C3 C4 0.27(12) . . . . ? C1 C2 C3 C4 -178.93(8) . . . . ? C2 C3 C4 C6 -0.53(13) . . . . ? C3 C2 C5 O2 -179.54(7) . . . . ? C1 C2 C5 O2 -0.36(12) . . . . ? C3 C2 C5 C7 -0.01(12) . . . . ? C1 C2 C5 C7 179.17(7) . . . . ? C3 C4 C6 C7 0.55(13) . . . . ? C4 C6 C7 C5 -0.30(12) . . . . ? C4 C6 C7 C8 179.11(8) . . . . ? O2 C5 C7 C6 179.57(7) . . . . ? C2 C5 C7 C6 0.03(11) . . . . ? O2 C5 C7 C8 0.15(11) . . . . ? C2 C5 C7 C8 -179.39(7) . . . . ? C6 C7 C8 C9 109.82(9) . . . . ? C5 C7 C8 C9 -70.79(10) . . . . ? C7 C8 C9 C9 -120.91(11) . . . 3_657 ? _diffrn_measured_fraction_theta_max 0.831 _diffrn_reflns_theta_full 36.39 _diffrn_measured_fraction_theta_full 0.831 _refine_diff_density_max 0.573 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.064