# Supplementary Material (ESI) for Photochemical & Photobiological Sciences # This journal is (c) The Royal Society of Chemistry and Owner Societies 2009 data_global _journal_coden_Cambridge 171 loop_ _publ_author_name 'Annaleise Howard-Jones' 'Virgile Adam' 'J Baldwin' 'Dominique Bourgeois' 'Andrew Cowley' _publ_contact_author_name 'Annaleise Howard-Jones' _publ_contact_author_email AHOWARDJONES@MED.USYD.EDU.AU _publ_section_title ; Cryophotolysis of caged oxygen compounds for use in low temperature biological studies ; # Attachment 'arc940-vrf.cif' data_arc940 _database_code_depnum_ccdc_archive 'CCDC 729932' # start Validation Reply Form _vrf_PLAT430_arc940 ; PROBLEM: Short Inter D...A Contact O13 .. N12 .. 1.26 Ang. RESPONSE: The disorder in the nitrate groups and its effect on the hydrogen bonding network is fully discussed in the manuscript. ; _vrf_PLAT432_arc940 ; PROBLEM: Short Inter X...Y Contact O23 .. C43 .. 1.40 Ang. RESPONSE: The disorder in the nitrate groups and its effect on the hydrogen bonding network is fully discussed in the manuscript. ; # end Validation Reply Form #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_special_details ; Geometric restraints were been applied to the disordered counterions and solvent. The nitrate ions N10-O18 were restrained to have N-O bond lengths of 1.24(2) \%A and O-N-O angles of 120(2) \%. The molecules of EtOH O22-C44 were restrined to have O-C bond lengths of 1.42(2) \%A, C-C bond lengths of 1.48(2) \%A and O-C-C angles of 112 \%. The hydrogen atom of the coordinted OH group O3, H1 was located in a difference Fourier map and its coordinates and isotropic displacement parameter subsequently refined. Other hydrogen atoms were positioned geometrically, with those of the disordered solvent placed by assuming the shortest possible hydrogen bonds to be linear. ; #============================================================= _cell_length_a 11.9774(2) _cell_angle_alpha 81.9962(8) _cell_length_b 13.4851(3) _cell_angle_beta 71.1326(8) _cell_length_c 14.5529(3) _cell_angle_gamma 88.4819(11) _cell_volume 2202.14(8) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'Co ' 0.3494 0.9721 12.2841 4.2791 7.3409 0.2784 4.0034 13.5359 2.3488 71.1692 1.0118 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C42 H42 Co2 N11 O14.50 ' _chemical_formula_moiety ' C40 H33 Co2 N8 O3, 3(N O3), 1.5(H2 O), C2 H6 O ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 1050.73 _cell_measurement_reflns_used 21797 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' block ' _exptl_crystal_colour ' black ' _exptl_crystal_size_min 0.18 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_max 0.32 _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1082 _exptl_absorpt_coefficient_mu 0.837 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.77 _exptl_absorpt_correction_T_max 0.86 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 21797 _reflns_number_total 9758 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_theta_min 5.097 _diffrn_reflns_theta_max 27.465 _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.000 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -14 _reflns_limit_h_max 15 _reflns_limit_k_min -17 _reflns_limit_k_max 17 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _refine_diff_density_min -0.65 _refine_diff_density_max 1.11 _refine_ls_number_reflns 6939 _refine_ls_number_restraints 30 _refine_ls_number_parameters 618 #_refine_ls_R_factor_ref 0.0432 _refine_ls_wR_factor_ref 0.0522 _refine_ls_goodness_of_fit_ref 1.1213 #_reflns_number_all 9758 _refine_ls_R_factor_all 0.0656 _refine_ls_wR_factor_all 0.0597 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 6939 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_gt 0.0522 _refine_ls_shift/su_max 0.023850 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.23 0.641 0.814 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_disorder_assembly _atom_site_refinement_disorder_group Co1 Co 0.23890(3) 0.34966(3) 0.20012(3) 0.0197 1.0000 Uani . . . . . Co2 Co 0.31433(3) 0.22926(3) 0.38149(3) 0.0191 1.0000 Uani . . . . . N1 N 0.1943(2) 0.47225(16) 0.25769(17) 0.0216 1.0000 Uani . . . . . C1 C 0.1316(3) 0.4793(2) 0.3513(2) 0.0253 1.0000 Uani . . . . . C2 C 0.1200(3) 0.5695(2) 0.3885(2) 0.0308 1.0000 Uani . . . . . C3 C 0.1776(3) 0.6544(2) 0.3285(2) 0.0326 1.0000 Uani . . . . . C4 C 0.2397(3) 0.6479(2) 0.2311(2) 0.0337 1.0000 Uani . . . . . C5 C 0.2444(3) 0.5558(2) 0.1976(2) 0.0260 1.0000 Uani . . . . . C6 C 0.2961(3) 0.5404(2) 0.0945(2) 0.0257 1.0000 Uani . . . . . C7 C 0.3344(3) 0.6182(2) 0.0175(2) 0.0310 1.0000 Uani . . . . . C8 C 0.3688(3) 0.5965(2) -0.0776(2) 0.0313 1.0000 Uani . . . . . C9 C 0.3661(3) 0.4981(3) -0.0934(2) 0.0340 1.0000 Uani . . . . . C10 C 0.3283(3) 0.4234(2) -0.0138(2) 0.0304 1.0000 Uani . . . . . N2 N 0.2926(2) 0.44368(18) 0.07918(17) 0.0244 1.0000 Uani . . . . . N3 N 0.2859(2) 0.23581(17) 0.12904(17) 0.0230 1.0000 Uani . . . . . C11 C 0.3975(3) 0.2070(2) 0.0910(2) 0.0268 1.0000 Uani . . . . . C12 C 0.4266(3) 0.1356(2) 0.0274(2) 0.0311 1.0000 Uani . . . . . C13 C 0.3383(3) 0.0933(2) 0.0025(2) 0.0355 1.0000 Uani . . . . . C14 C 0.2230(3) 0.1216(2) 0.0434(2) 0.0331 1.0000 Uani . . . . . C15 C 0.1987(3) 0.1936(2) 0.1065(2) 0.0258 1.0000 Uani . . . . . C16 C 0.0811(3) 0.2336(2) 0.1497(2) 0.0261 1.0000 Uani . . . . . C17 C -0.0237(3) 0.1908(3) 0.1503(2) 0.0358 1.0000 Uani . . . . . C18 C -0.1297(3) 0.2383(3) 0.1903(3) 0.0426 1.0000 Uani . . . . . C19 C -0.1272(3) 0.3267(3) 0.2265(3) 0.0404 1.0000 Uani . . . . . C20 C -0.0206(3) 0.3645(3) 0.2262(2) 0.0324 1.0000 Uani . . . . . N4 N 0.0820(2) 0.31927(18) 0.18903(17) 0.0250 1.0000 Uani . . . . . N5 N 0.3258(2) 0.10159(16) 0.33181(16) 0.0207 1.0000 Uani . . . . . C21 C 0.2489(2) 0.0613(2) 0.2977(2) 0.0239 1.0000 Uani . . . . . C22 C 0.2736(3) -0.0241(2) 0.2522(2) 0.0281 1.0000 Uani . . . . . C23 C 0.3828(3) -0.0679(2) 0.2394(2) 0.0318 1.0000 Uani . . . . . C24 C 0.4625(3) -0.0273(2) 0.2754(2) 0.0306 1.0000 Uani . . . . . C25 C 0.4316(2) 0.0572(2) 0.3223(2) 0.0235 1.0000 Uani . . . . . C26 C 0.5023(2) 0.1023(2) 0.3716(2) 0.0248 1.0000 Uani . . . . . C27 C 0.6111(3) 0.0680(2) 0.3753(3) 0.0337 1.0000 Uani . . . . . C28 C 0.6643(3) 0.1112(3) 0.4321(3) 0.0376 1.0000 Uani . . . . . C29 C 0.6062(3) 0.1849(2) 0.4859(3) 0.0360 1.0000 Uani . . . . . C30 C 0.4993(3) 0.2177(2) 0.4775(2) 0.0292 1.0000 Uani . . . . . N6 N 0.4487(2) 0.17877(17) 0.41944(17) 0.0237 1.0000 Uani . . . . . N7 N 0.3126(2) 0.35203(17) 0.43700(17) 0.0231 1.0000 Uani . . . . . C31 C 0.3841(3) 0.4330(2) 0.3949(2) 0.0286 1.0000 Uani . . . . . C32 C 0.3780(3) 0.5173(2) 0.4407(3) 0.0367 1.0000 Uani . . . . . C33 C 0.2944(4) 0.5187(3) 0.5314(3) 0.0417 1.0000 Uani . . . . . C34 C 0.2221(3) 0.4362(2) 0.5767(2) 0.0356 1.0000 Uani . . . . . C35 C 0.2346(3) 0.3525(2) 0.5282(2) 0.0242 1.0000 Uani . . . . . C36 C 0.1689(2) 0.2575(2) 0.5710(2) 0.0237 1.0000 Uani . . . . . C37 C 0.0899(3) 0.2403(2) 0.6656(2) 0.0302 1.0000 Uani . . . . . C38 C 0.0345(3) 0.1468(3) 0.6992(2) 0.0337 1.0000 Uani . . . . . C39 C 0.0590(3) 0.0745(2) 0.6379(2) 0.0310 1.0000 Uani . . . . . C40 C 0.1393(2) 0.0961(2) 0.5445(2) 0.0242 1.0000 Uani . . . . . N8 N 0.1946(2) 0.18558(17) 0.51141(17) 0.0215 1.0000 Uani . . . . . O1 O 0.38422(17) 0.36783(14) 0.21676(14) 0.0241 1.0000 Uani . . . . . O2 O 0.42325(17) 0.27929(14) 0.26007(14) 0.0228 1.0000 Uani . . . . . O3 O 0.19559(19) 0.27301(15) 0.32600(15) 0.0219 1.0000 Uani . . . . . N9 N -0.0780(2) 0.19504(18) 0.46360(18) 0.0251 1.0000 Uani . . . . . O4 O -0.0182(2) 0.1508(2) 0.39484(19) 0.0488 1.0000 Uani . . . . . O5 O -0.0594(4) 0.2855(2) 0.4565(2) 0.0841 1.0000 Uani . . . . . O6 O -0.1524(2) 0.15030(19) 0.53642(17) 0.0381 1.0000 Uani . . . . . N10 N 0.3880(8) 0.3028(5) -0.2520(5) 0.0480(19) 0.5000 Uiso D . . 1 -1 O7 O 0.3801(5) 0.3931(5) -0.2850(5) 0.0547(14) 0.5000 Uiso D . . 1 -1 O8 O 0.3025(7) 0.2732(6) -0.1749(5) 0.0709(18) 0.5000 Uiso D . . 1 -1 O9 O 0.4648(9) 0.2601(7) -0.3119(7) 0.096(3) 0.5000 Uiso D . . 1 -1 N11 N 0.2399(6) -0.1255(5) -0.0146(6) 0.0384(15) 0.5000 Uiso D . . 1 -1 O10 O 0.2284(6) -0.1486(4) 0.0779(5) 0.0450(14) 0.5000 Uiso D . . 1 -1 O11 O 0.3268(5) -0.1520(4) -0.0799(4) 0.0399(11) 0.5000 Uiso D . . 1 -1 O12 O 0.1599(4) -0.0768(4) -0.0367(4) 0.0398(11) 0.5000 Uiso D . . 1 -1 N12 N -0.4280(8) -0.3008(6) 0.2520(5) 0.049(2) 0.5000 Uiso D . . 1 -1 O13 O -0.3749(9) -0.3462(9) 0.3071(8) 0.103(3) 0.5000 Uiso D . . 1 -1 O14 O -0.3680(7) -0.2617(6) 0.1715(6) 0.076(2) 0.5000 Uiso D . . 1 -1 O15 O -0.5229(8) -0.2743(7) 0.2946(6) 0.087(2) 0.5000 Uiso D . . 1 -1 N13 N -0.2189(5) 0.1292(5) -0.0227(6) 0.0361(15) 0.5000 Uiso D . . 1 -1 O16 O -0.2751(6) 0.1509(4) -0.0791(4) 0.0463(14) 0.5000 Uiso D . . 1 -1 O17 O -0.2699(7) 0.1351(6) 0.0633(6) 0.0629(17) 0.5000 Uiso D . . 1 -1 O18 O -0.1157(7) 0.0972(6) -0.0500(6) 0.0754(19) 0.5000 Uiso D . . 1 -1 O19 O 0.2431(6) 0.0672(6) -0.2071(5) 0.0573(17) 0.5000 Uiso . . . 1 -1 O20 O -0.0536(6) -0.0286(5) 0.0891(5) 0.0647(16) 0.5000 Uiso . . . 1 -1 O21 O -0.2647(6) -0.1028(6) 0.2317(6) 0.0588(18) 0.5000 Uiso . . . 1 -1 O22 O 0.1272(8) 0.4265(7) -0.1895(6) 0.058(3) 0.5000 Uiso D . . 1 -1 C41 C 0.0552(9) 0.4067(9) -0.0916(7) 0.073(3) 0.5000 Uiso D . . 1 -1 C42 C -0.0443(9) 0.3680(8) -0.0716(7) 0.062(2) 0.5000 Uiso D . . 1 -1 O23 O -0.1414(7) -0.4046(6) 0.1891(6) 0.048(2) 0.5000 Uiso D . . 1 -1 C43 C -0.0876(8) -0.3493(7) 0.0965(6) 0.056(2) 0.5000 Uiso D . . 1 -1 C44 C 0.0232(10) -0.3135(10) 0.0793(9) 0.075(3) 0.5000 Uiso D . . 1 -1 H1 H 0.137(4) 0.256(3) 0.350(3) 0.034(11) 1.0000 Uiso . . . . . H2 H 0.2598 0.1251 -0.1980 0.0688 0.5000 Uiso . . . 1 -1 H3 H 0.2182 0.0241 -0.1561 0.0688 0.5000 Uiso . . . 1 -1 H4 H 0.0125 -0.0435 0.0501 0.0776 0.5000 Uiso . . . 1 -1 H5 H -0.0729 0.0106 0.0459 0.0776 0.5000 Uiso . . . 1 -1 H6 H -0.2007 -0.0803 0.1884 0.0706 0.5000 Uiso . . . 1 -1 H7 H -0.2953 -0.1498 0.2139 0.0706 0.5000 Uiso . . . 1 -1 H8 H 0.1778 0.3823 -0.1853 0.0697 0.5000 Uiso . . . 1 -1 H9 H -0.2093 -0.3876 0.2234 0.0571 0.5000 Uiso . . . 1 -1 H11 H 0.0923 0.4178 0.3954 0.0295 1.0000 Uiso . . . . . H21 H 0.0705 0.5734 0.4578 0.0361 1.0000 Uiso . . . . . H31 H 0.1745 0.7192 0.3551 0.0392 1.0000 Uiso . . . . . H41 H 0.2804 0.7084 0.1858 0.0398 1.0000 Uiso . . . . . H71 H 0.3369 0.6888 0.0307 0.0352 1.0000 Uiso . . . . . H81 H 0.3953 0.6514 -0.1342 0.0350 1.0000 Uiso . . . . . H91 H 0.3912 0.4808 -0.1617 0.0396 1.0000 Uiso . . . . . H101 H 0.3276 0.3522 -0.0258 0.0352 1.0000 Uiso . . . . . H111 H 0.4613 0.2378 0.1089 0.0313 1.0000 Uiso . . . . . H121 H 0.5104 0.1151 0.0000 0.0363 1.0000 Uiso . . . . . H131 H 0.3576 0.0429 -0.0444 0.0428 1.0000 Uiso . . . . . H141 H 0.1576 0.0906 0.0276 0.0415 1.0000 Uiso . . . . . H171 H -0.0229 0.1270 0.1226 0.0441 1.0000 Uiso . . . . . H181 H -0.2062 0.2084 0.1925 0.0526 1.0000 Uiso . . . . . H191 H -0.2017 0.3636 0.2529 0.0501 1.0000 Uiso . . . . . H201 H -0.0202 0.4278 0.2548 0.0399 1.0000 Uiso . . . . . H211 H 0.1710 0.0938 0.3054 0.0284 1.0000 Uiso . . . . . H221 H 0.2137 -0.0537 0.2289 0.0339 1.0000 Uiso . . . . . H231 H 0.4036 -0.1281 0.2046 0.0383 1.0000 Uiso . . . . . H241 H 0.5411 -0.0584 0.2678 0.0370 1.0000 Uiso . . . . . H271 H 0.6506 0.0130 0.3377 0.0416 1.0000 Uiso . . . . . H281 H 0.7439 0.0892 0.4342 0.0481 1.0000 Uiso . . . . . H291 H 0.6412 0.2141 0.5303 0.0466 1.0000 Uiso . . . . . H301 H 0.4580 0.2719 0.5155 0.0368 1.0000 Uiso . . . . . H311 H 0.4434 0.4320 0.3284 0.0351 1.0000 Uiso . . . . . H321 H 0.4330 0.5758 0.4087 0.0454 1.0000 Uiso . . . . . H331 H 0.2861 0.5799 0.5646 0.0508 1.0000 Uiso . . . . . H341 H 0.1619 0.4365 0.6429 0.0426 1.0000 Uiso . . . . . H371 H 0.0730 0.2942 0.7087 0.0360 1.0000 Uiso . . . . . H381 H -0.0224 0.1322 0.7672 0.0389 1.0000 Uiso . . . . . H391 H 0.0192 0.0071 0.6605 0.0372 1.0000 Uiso . . . . . H401 H 0.1567 0.0433 0.5003 0.0295 1.0000 Uiso . . . . . H411 H 0.0435 0.4720 -0.0649 0.0874 0.5000 Uiso . . . 1 -1 H412 H 0.0997 0.3608 -0.0564 0.0874 0.5000 Uiso . . . 1 -1 H421 H -0.0839 0.3589 0.0011 0.0740 0.5000 Uiso . . . 1 -1 H422 H -0.0927 0.4125 -0.1041 0.0740 0.5000 Uiso . . . 1 -1 H423 H -0.0364 0.3013 -0.0956 0.0740 0.5000 Uiso . . . 1 -1 H431 H -0.0840 -0.3936 0.0459 0.0677 0.5000 Uiso . . . 1 -1 H432 H -0.1386 -0.2908 0.0889 0.0677 0.5000 Uiso . . . 1 -1 H441 H 0.0529 -0.2756 0.0116 0.0895 0.5000 Uiso . . . 1 -1 H442 H 0.0765 -0.3707 0.0852 0.0895 0.5000 Uiso . . . 1 -1 H443 H 0.0219 -0.2679 0.1282 0.0895 0.5000 Uiso . . . 1 -1 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 0.02235(19) 0.01794(17) 0.01833(18) -0.00394(13) -0.00535(14) 0.00044(13) Co2 0.02060(18) 0.01708(17) 0.02063(18) -0.00462(13) -0.00719(14) 0.00097(13) N1 0.0253(11) 0.0173(10) 0.0211(11) -0.0036(8) -0.0058(9) 0.0029(8) C1 0.0281(14) 0.0242(13) 0.0216(13) -0.0048(11) -0.0049(11) 0.0031(11) C2 0.0345(16) 0.0295(15) 0.0262(15) -0.0075(12) -0.0058(12) 0.0051(12) C3 0.0438(18) 0.0192(13) 0.0350(16) -0.0105(12) -0.0106(14) 0.0045(12) C4 0.0468(18) 0.0212(13) 0.0315(16) -0.0052(12) -0.0095(14) -0.0008(12) C5 0.0303(14) 0.0206(12) 0.0248(14) -0.0025(10) -0.0058(11) 0.0004(11) C6 0.0305(14) 0.0227(13) 0.0225(13) -0.0030(11) -0.0067(11) 0.0007(11) C7 0.0334(16) 0.0235(13) 0.0311(15) 0.0011(12) -0.0056(12) -0.0009(11) C8 0.0285(15) 0.0319(15) 0.0271(15) 0.0049(12) -0.0037(12) -0.0019(12) C9 0.0371(17) 0.0399(17) 0.0219(14) -0.0030(12) -0.0057(12) -0.0025(13) C10 0.0380(16) 0.0290(14) 0.0209(14) -0.0037(11) -0.0044(12) -0.0030(12) N2 0.0285(12) 0.0243(11) 0.0207(11) -0.0042(9) -0.0080(9) 0.0020(9) N3 0.0281(12) 0.0213(11) 0.0202(11) -0.0038(9) -0.0079(9) -0.0012(9) C11 0.0276(14) 0.0248(13) 0.0257(14) -0.0054(11) -0.0047(11) 0.0009(11) C12 0.0365(16) 0.0261(14) 0.0280(15) -0.0072(12) -0.0055(12) 0.0021(12) C13 0.0493(19) 0.0285(15) 0.0293(16) -0.0122(12) -0.0102(14) 0.0007(13) C14 0.0426(18) 0.0293(15) 0.0318(16) -0.0118(12) -0.0149(14) -0.0030(13) C15 0.0318(15) 0.0239(13) 0.0230(13) -0.0028(11) -0.0105(11) -0.0020(11) C16 0.0287(14) 0.0293(14) 0.0227(13) -0.0030(11) -0.0116(11) -0.0024(11) C17 0.0356(17) 0.0453(18) 0.0294(16) -0.0072(14) -0.0130(13) -0.0064(14) C18 0.0296(16) 0.065(2) 0.0366(18) -0.0058(16) -0.0153(14) -0.0090(15) C19 0.0285(16) 0.063(2) 0.0332(17) -0.0125(16) -0.0133(13) 0.0072(15) C20 0.0285(15) 0.0428(18) 0.0287(15) -0.0084(13) -0.0119(12) 0.0054(13) N4 0.0278(12) 0.0268(12) 0.0204(11) -0.0025(9) -0.0084(9) 0.0021(9) N5 0.0226(11) 0.0189(10) 0.0195(10) -0.0037(8) -0.0050(9) 0.0018(8) C21 0.0245(13) 0.0224(13) 0.0242(13) -0.0036(11) -0.0067(11) -0.0016(10) C22 0.0319(15) 0.0233(13) 0.0296(15) -0.0057(11) -0.0094(12) -0.0038(11) C23 0.0359(16) 0.0237(14) 0.0362(16) -0.0107(12) -0.0095(13) 0.0038(12) C24 0.0310(15) 0.0250(14) 0.0365(16) -0.0094(12) -0.0098(13) 0.0054(11) C25 0.0240(13) 0.0214(13) 0.0256(14) -0.0041(11) -0.0084(11) 0.0020(10) C26 0.0252(13) 0.0234(13) 0.0259(14) -0.0032(11) -0.0086(11) 0.0023(11) C27 0.0290(15) 0.0324(15) 0.0425(18) -0.0079(13) -0.0148(13) 0.0071(12) C28 0.0325(16) 0.0353(16) 0.052(2) -0.0058(15) -0.0244(15) 0.0058(13) C29 0.0402(18) 0.0331(16) 0.0432(18) -0.0048(14) -0.0254(15) 0.0006(13) C30 0.0317(15) 0.0279(14) 0.0325(15) -0.0064(12) -0.0154(12) -0.0011(12) N6 0.0261(12) 0.0200(11) 0.0260(12) -0.0038(9) -0.0096(9) 0.0004(9) N7 0.0239(11) 0.0229(11) 0.0248(11) -0.0060(9) -0.0101(9) 0.0007(9) C31 0.0334(15) 0.0234(13) 0.0309(15) -0.0040(11) -0.0124(12) -0.0052(11) C32 0.0468(19) 0.0259(15) 0.0408(18) -0.0090(13) -0.0165(15) -0.0066(13) C33 0.061(2) 0.0277(15) 0.0378(18) -0.0133(13) -0.0142(16) -0.0063(15) C34 0.053(2) 0.0292(15) 0.0247(15) -0.0107(12) -0.0093(14) -0.0012(14) C35 0.0307(14) 0.0205(12) 0.0252(13) -0.0056(10) -0.0130(11) 0.0012(10) C36 0.0267(13) 0.0241(13) 0.0222(13) -0.0028(10) -0.0108(11) 0.0030(10) C37 0.0323(15) 0.0340(15) 0.0237(14) -0.0071(12) -0.0068(12) -0.0003(12) C38 0.0309(16) 0.0395(17) 0.0268(15) -0.0017(13) -0.0046(12) -0.0048(13) C39 0.0341(16) 0.0292(15) 0.0298(15) 0.0016(12) -0.0125(12) -0.0038(12) C40 0.0258(14) 0.0211(12) 0.0269(14) -0.0024(10) -0.0107(11) 0.0000(10) N8 0.0222(11) 0.0202(10) 0.0244(11) -0.0040(9) -0.0108(9) 0.0045(8) O1 0.0255(10) 0.0203(9) 0.0262(10) -0.0037(8) -0.0075(8) -0.0003(7) O2 0.0223(9) 0.0200(9) 0.0248(10) -0.0025(7) -0.0061(7) 0.0020(7) O3 0.0199(10) 0.0216(9) 0.0229(10) -0.0014(7) -0.0058(8) -0.0015(8) N9 0.0225(11) 0.0272(12) 0.0280(12) -0.0081(10) -0.0098(10) -0.0001(9) O4 0.0546(16) 0.0467(15) 0.0407(14) -0.0198(12) -0.0049(12) 0.0178(12) O5 0.154(4) 0.0382(15) 0.0394(16) -0.0158(13) 0.0046(19) -0.0420(19) O6 0.0314(12) 0.0472(14) 0.0319(12) 0.0010(10) -0.0068(9) -0.0121(10) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Co1 . N1 . 1.942(2) yes Co1 . N2 . 1.952(2) yes Co1 . N3 . 1.940(2) yes Co1 . N4 . 1.995(2) yes Co1 . O1 . 1.860(2) yes Co1 . O3 . 1.892(2) yes Co2 . N5 . 1.943(2) yes Co2 . N6 . 1.942(2) yes Co2 . N7 . 1.938(2) yes Co2 . N8 . 1.990(2) yes Co2 . O2 . 1.8717(19) yes Co2 . O3 . 1.894(2) yes N1 . C1 . 1.341(4) yes N1 . C5 . 1.348(4) yes C1 . C2 . 1.384(4) yes C1 . H11 . 1.000 no C2 . C3 . 1.387(4) yes C2 . H21 . 1.000 no C3 . C4 . 1.385(4) yes C3 . H31 . 1.000 no C4 . C5 . 1.389(4) yes C4 . H41 . 1.000 no C5 . C6 . 1.468(4) yes C6 . C7 . 1.390(4) yes C6 . N2 . 1.358(4) yes C7 . C8 . 1.381(5) yes C7 . H71 . 1.000 no C8 . C9 . 1.382(5) yes C8 . H81 . 1.000 no C9 . C10 . 1.386(4) yes C9 . H91 . 1.000 no C10 . N2 . 1.346(4) yes C10 . H101 . 1.000 no N3 . C11 . 1.341(4) yes N3 . C15 . 1.353(4) yes C11 . C12 . 1.388(4) yes C11 . H111 . 1.000 no C12 . C13 . 1.384(5) yes C12 . H121 . 1.000 no C13 . C14 . 1.383(5) yes C13 . H131 . 1.000 no C14 . C15 . 1.389(4) yes C14 . H141 . 1.000 no C15 . C16 . 1.467(4) yes C16 . C17 . 1.392(4) yes C16 . N4 . 1.360(4) yes C17 . C18 . 1.393(5) yes C17 . H171 . 1.000 no C18 . C19 . 1.375(6) yes C18 . H181 . 1.000 no C19 . C20 . 1.386(5) yes C19 . H191 . 1.000 no C20 . N4 . 1.341(4) yes C20 . H201 . 1.000 no N5 . C21 . 1.337(4) yes N5 . C25 . 1.361(4) yes C21 . C22 . 1.386(4) yes C21 . H211 . 1.000 no C22 . C23 . 1.388(4) yes C22 . H221 . 1.000 no C23 . C24 . 1.385(4) yes C23 . H231 . 1.000 no C24 . C25 . 1.390(4) yes C24 . H241 . 1.000 no C25 . C26 . 1.465(4) yes C26 . C27 . 1.387(4) yes C26 . N6 . 1.355(4) yes C27 . C28 . 1.386(5) yes C27 . H271 . 1.000 no C28 . C29 . 1.383(5) yes C28 . H281 . 1.000 no C29 . C30 . 1.381(4) yes C29 . H291 . 1.000 no C30 . N6 . 1.353(4) yes C30 . H301 . 1.000 no N7 . C31 . 1.351(4) yes N7 . C35 . 1.355(4) yes C31 . C32 . 1.385(4) yes C31 . H311 . 1.000 no C32 . C33 . 1.377(5) yes C32 . H321 . 1.000 no C33 . C34 . 1.378(5) yes C33 . H331 . 1.000 no C34 . C35 . 1.392(4) yes C34 . H341 . 1.000 no C35 . C36 . 1.470(4) yes C36 . C37 . 1.388(4) yes C36 . N8 . 1.354(4) yes C37 . C38 . 1.390(5) yes C37 . H371 . 1.000 no C38 . C39 . 1.375(5) yes C38 . H381 . 1.000 no C39 . C40 . 1.384(4) yes C39 . H391 . 1.000 no C40 . N8 . 1.342(4) yes C40 . H401 . 1.000 no O1 . O2 . 1.412(3) yes O3 . H1 . 0.70(4) no N9 . O4 . 1.245(3) yes N9 . O5 . 1.231(4) yes N9 . O6 . 1.233(3) yes N10 . O7 . 1.258(9) yes N10 . O8 . 1.272(9) yes N10 . O9 . 1.238(10) yes N11 . O10 . 1.302(9) yes N11 . O11 . 1.244(9) yes N11 . O12 . 1.249(7) yes N12 . O13 . 1.263(11) yes N12 . O14 . 1.212(9) yes N12 . O15 . 1.178(10) yes N13 . O16 . 1.222(9) yes N13 . O17 . 1.215(9) yes N13 . O18 . 1.254(9) yes O19 . H2 . 0.850 no O19 . H3 . 0.850 no O20 . H4 . 0.850 no O20 . H5 . 0.850 no O21 . H6 . 0.850 no O21 . H7 . 0.850 no O22 . C41 . 1.399(11) yes O22 . H8 . 0.850 no C41 . C42 . 1.242(12) yes C41 . H411 . 1.000 no C41 . H412 . 1.000 no C42 . H421 . 1.000 no C42 . H422 . 1.000 no C42 . H423 . 1.000 no O23 . C43 . 1.404(10) yes O23 . H9 . 0.850 no C43 . C44 . 1.358(12) yes C43 . H431 . 1.000 no C43 . H432 . 1.000 no C44 . H441 . 1.000 no C44 . H442 . 1.000 no C44 . H443 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 . Co1 . N2 . 82.28(10) yes N1 . Co1 . N3 . 173.84(9) yes N2 . Co1 . N3 . 91.71(10) yes N1 . Co1 . N4 . 96.68(10) yes N2 . Co1 . N4 . 96.00(10) yes N3 . Co1 . N4 . 82.56(10) yes N1 . Co1 . O1 . 85.81(9) yes N2 . Co1 . O1 . 88.27(9) yes N3 . Co1 . O1 . 95.39(9) yes N4 . Co1 . O1 . 175.30(9) yes N1 . Co1 . O3 . 90.95(9) yes N2 . Co1 . O3 . 171.35(9) yes N3 . Co1 . O3 . 95.16(9) yes N4 . Co1 . O3 . 90.11(9) yes O1 . Co1 . O3 . 85.86(9) yes N5 . Co2 . N6 . 82.35(10) yes N5 . Co2 . N7 . 174.91(10) yes N6 . Co2 . N7 . 92.66(10) yes N5 . Co2 . N8 . 96.85(9) yes N6 . Co2 . N8 . 95.31(10) yes N7 . Co2 . N8 . 82.53(10) yes N5 . Co2 . O2 . 86.69(9) yes N6 . Co2 . O2 . 86.81(9) yes N7 . Co2 . O2 . 94.09(9) yes N8 . Co2 . O2 . 176.08(9) yes N5 . Co2 . O3 . 92.01(9) yes N6 . Co2 . O3 . 171.50(9) yes N7 . Co2 . O3 . 93.06(9) yes N8 . Co2 . O3 . 91.66(9) yes O2 . Co2 . O3 . 86.51(9) yes Co1 . N1 . C1 . 126.57(19) yes Co1 . N1 . C5 . 113.97(18) yes C1 . N1 . C5 . 119.0(2) yes N1 . C1 . C2 . 121.8(3) yes N1 . C1 . H11 . 119.109 no C2 . C1 . H11 . 119.109 no C1 . C2 . C3 . 119.3(3) yes C1 . C2 . H21 . 120.334 no C3 . C2 . H21 . 120.334 no C2 . C3 . C4 . 119.0(3) yes C2 . C3 . H31 . 120.522 no C4 . C3 . H31 . 120.523 no C3 . C4 . C5 . 118.7(3) yes C3 . C4 . H41 . 120.645 no C5 . C4 . H41 . 120.646 no N1 . C5 . C4 . 122.0(3) yes N1 . C5 . C6 . 113.5(2) yes C4 . C5 . C6 . 124.4(3) yes C5 . C6 . C7 . 123.6(3) yes C5 . C6 . N2 . 114.0(2) yes C7 . C6 . N2 . 122.1(3) yes C6 . C7 . C8 . 119.0(3) yes C6 . C7 . H71 . 120.516 no C8 . C7 . H71 . 120.516 no C7 . C8 . C9 . 119.1(3) yes C7 . C8 . H81 . 120.440 no C9 . C8 . H81 . 120.440 no C8 . C9 . C10 . 119.4(3) yes C8 . C9 . H91 . 120.286 no C10 . C9 . H91 . 120.286 no C9 . C10 . N2 . 122.0(3) yes C9 . C10 . H101 . 118.979 no N2 . C10 . H101 . 118.979 no Co1 . N2 . C6 . 113.45(18) yes Co1 . N2 . C10 . 128.1(2) yes C6 . N2 . C10 . 118.4(2) yes Co1 . N3 . C11 . 124.87(19) yes Co1 . N3 . C15 . 114.82(19) yes C11 . N3 . C15 . 119.6(2) yes N3 . C11 . C12 . 121.7(3) yes N3 . C11 . H111 . 119.175 no C12 . C11 . H111 . 119.175 no C11 . C12 . C13 . 119.2(3) yes C11 . C12 . H121 . 120.424 no C13 . C12 . H121 . 120.424 no C12 . C13 . C14 . 119.1(3) yes C12 . C13 . H131 . 120.474 no C14 . C13 . H131 . 120.473 no C13 . C14 . C15 . 119.4(3) yes C13 . C14 . H141 . 120.280 no C15 . C14 . H141 . 120.280 no N3 . C15 . C14 . 121.0(3) yes N3 . C15 . C16 . 114.6(2) yes C14 . C15 . C16 . 124.3(3) yes C15 . C16 . C17 . 124.5(3) yes C15 . C16 . N4 . 114.0(2) yes C17 . C16 . N4 . 121.5(3) yes C16 . C17 . C18 . 119.1(3) yes C16 . C17 . H171 . 120.464 no C18 . C17 . H171 . 120.464 no C17 . C18 . C19 . 118.8(3) yes C17 . C18 . H181 . 120.579 no C19 . C18 . H181 . 120.579 no C18 . C19 . C20 . 119.6(3) yes C18 . C19 . H191 . 120.217 no C20 . C19 . H191 . 120.217 no C19 . C20 . N4 . 122.3(3) yes C19 . C20 . H201 . 118.862 no N4 . C20 . H201 . 118.862 no Co1 . N4 . C16 . 112.77(19) yes Co1 . N4 . C20 . 128.0(2) yes C16 . N4 . C20 . 118.7(3) yes Co2 . N5 . C21 . 127.33(19) yes Co2 . N5 . C25 . 113.05(18) yes C21 . N5 . C25 . 119.2(2) yes N5 . C21 . C22 . 122.2(3) yes N5 . C21 . H211 . 118.924 no C22 . C21 . H211 . 118.924 no C21 . C22 . C23 . 119.0(3) yes C21 . C22 . H221 . 120.520 no C23 . C22 . H221 . 120.520 no C22 . C23 . C24 . 119.3(3) yes C22 . C23 . H231 . 120.366 no C24 . C23 . H231 . 120.366 no C23 . C24 . C25 . 119.0(3) yes C23 . C24 . H241 . 120.477 no C25 . C24 . H241 . 120.477 no N5 . C25 . C24 . 121.4(3) yes N5 . C25 . C26 . 113.7(2) yes C24 . C25 . C26 . 124.8(3) yes C25 . C26 . C27 . 124.4(3) yes C25 . C26 . N6 . 113.7(2) yes C27 . C26 . N6 . 121.8(3) yes C26 . C27 . C28 . 118.8(3) yes C26 . C27 . H271 . 120.582 no C28 . C27 . H271 . 120.582 no C27 . C28 . C29 . 119.5(3) yes C27 . C28 . H281 . 120.261 no C29 . C28 . H281 . 120.262 no C28 . C29 . C30 . 119.0(3) yes C28 . C29 . H291 . 120.476 no C30 . C29 . H291 . 120.476 no C29 . C30 . N6 . 122.0(3) yes C29 . C30 . H301 . 119.025 no N6 . C30 . H301 . 119.024 no Co2 . N6 . C26 . 113.18(19) yes Co2 . N6 . C30 . 127.6(2) yes C26 . N6 . C30 . 118.7(3) yes Co2 . N7 . C31 . 126.1(2) yes Co2 . N7 . C35 . 115.11(18) yes C31 . N7 . C35 . 118.8(2) yes N7 . C31 . C32 . 122.2(3) yes N7 . C31 . H311 . 118.912 no C32 . C31 . H311 . 118.912 no C31 . C32 . C33 . 118.5(3) yes C31 . C32 . H321 . 120.759 no C33 . C32 . H321 . 120.758 no C32 . C33 . C34 . 120.3(3) yes C32 . C33 . H331 . 119.848 no C34 . C33 . H331 . 119.848 no C33 . C34 . C35 . 118.6(3) yes C33 . C34 . H341 . 120.684 no C35 . C34 . H341 . 120.684 no N7 . C35 . C34 . 121.5(3) yes N7 . C35 . C36 . 114.4(2) yes C34 . C35 . C36 . 124.0(3) yes C35 . C36 . C37 . 123.6(3) yes C35 . C36 . N8 . 114.4(2) yes C37 . C36 . N8 . 121.9(3) yes C36 . C37 . C38 . 118.7(3) yes C36 . C37 . H371 . 120.648 no C38 . C37 . H371 . 120.648 no C37 . C38 . C39 . 119.2(3) yes C37 . C38 . H381 . 120.376 no C39 . C38 . H381 . 120.376 no C38 . C39 . C40 . 119.2(3) yes C38 . C39 . H391 . 120.382 no C40 . C39 . H391 . 120.383 no C39 . C40 . N8 . 122.3(3) yes C39 . C40 . H401 . 118.868 no N8 . C40 . H401 . 118.868 no Co2 . N8 . C36 . 113.44(18) yes Co2 . N8 . C40 . 127.97(19) yes C36 . N8 . C40 . 118.6(2) yes Co1 . O1 . O2 . 112.25(14) yes Co2 . O2 . O1 . 112.02(14) yes Co1 . O3 . Co2 . 119.42(12) yes Co1 . O3 . H1 . 121(3) no Co2 . O3 . H1 . 119(3) no O4 . N9 . O5 . 117.3(3) yes O4 . N9 . O6 . 121.7(3) yes O5 . N9 . O6 . 121.0(3) yes O7 . N10 . O8 . 112.7(7) yes O7 . N10 . O9 . 111.2(7) yes O8 . N10 . O9 . 134.5(8) yes O10 . N11 . O11 . 121.6(6) yes O10 . N11 . O12 . 118.1(7) yes O11 . N11 . O12 . 120.3(7) yes O13 . N12 . O14 . 117.4(9) yes O13 . N12 . O15 . 113.7(8) yes O14 . N12 . O15 . 124.2(8) yes O16 . N13 . O17 . 116.7(6) yes O16 . N13 . O18 . 122.5(8) yes O17 . N13 . O18 . 120.6(7) yes H2 . O19 . H3 . 116.267 no H4 . O20 . H5 . 95.016 no H6 . O21 . H7 . 112.023 no C41 . O22 . H8 . 96.042 no O22 . C41 . C42 . 119.6(9) yes O22 . C41 . H411 . 106.869 no C42 . C41 . H411 . 106.874 no O22 . C41 . H412 . 106.869 no C42 . C41 . H412 . 106.873 no H411 . C41 . H412 . 109.467 no C41 . C42 . H421 . 109.466 no C41 . C42 . H422 . 109.466 no H421 . C42 . H422 . 109.476 no C41 . C42 . H423 . 109.466 no H421 . C42 . H423 . 109.477 no H422 . C42 . H423 . 109.476 no C43 . O23 . H9 . 118.592 no O23 . C43 . C44 . 116.1(8) yes O23 . C43 . H431 . 107.780 no C44 . C43 . H431 . 107.778 no O23 . C43 . H432 . 107.780 no C44 . C43 . H432 . 107.778 no H431 . C43 . H432 . 109.466 no C43 . C44 . H441 . 109.468 no C43 . C44 . H442 . 109.467 no H441 . C44 . H442 . 109.474 no C43 . C44 . H443 . 109.468 no H441 . C44 . H443 . 109.476 no H442 . C44 . H443 . 109.476 no loop_ _geom_hbond_atom_site_label_d _geom_hbond_atom_site_label_h _geom_hbond_atom_site_label_a _geom_hbond_distance_dh _geom_hbond_distance_ha _geom_hbond_distance_da _geom_hbond_angle_dha _geom_hbond_publ_flag O3 H1 O4 0.70(4) 2.23(4) 2.895(4) 157(4) yes O3 H1 O5 0.70(4) 2.42(4) 3.045(5) 149(4) yes O19 H2 O8 0.85 2.17 3.022(11) 180 no O19 H3 O12 0.85 1.99 2.842(9) 180 no O20 H4 O12 0.85 1.89 2.744(8) 180 no O20 H5 O18 0.85 1.88 2.734(10) 180 no O21 H6 O20 0.85 1.95 2.804(10) 180 no O21 H7 O14 0.85 2.02 2.873(11) 180 no O22 H8 O8 0.85 2.09 2.944(12) 180 no O23 H9 O13 0.85 2.07 2.923(13) 180 no #The first two entries in this list are a bifurcated hydrogen bond