# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2007 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 642790' _audit_creation_date 2007-06-07T14:57:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; [Co(N-acetyl-(-)-ephedrine)~2~].2H~2~O ; _chemical_formula_moiety 'C24 H32 Co N2 O6, 2(H2 O)' _chemical_formula_sum 'C24 H36 Co1 N2 O8' _chemical_formula_weight 539.49 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_Int_Tables_number 1 loop_ _symmetry_equiv_pos_as_xyz x,y,z _cell_length_a 7.2132(2) _cell_length_b 8.9996(3) _cell_length_c 10.9360(4) _cell_angle_alpha 71.2063(16) _cell_angle_beta 81.2558(17) _cell_angle_gamma 81.4946(18) _cell_volume 660.54(4) _cell_formula_units_Z 1 _cell_measurement_temperature 293 _cell_measurement_reflns_used 2440 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 285 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.698 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8112 _exptl_absorpt_correction_T_max 0.8698 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.542213E-1 _diffrn_orient_matrix_ub_12 -0.106659 _diffrn_orient_matrix_ub_13 -0.59442E-2 _diffrn_orient_matrix_ub_21 -0.812556E-1 _diffrn_orient_matrix_ub_22 -0.505523E-1 _diffrn_orient_matrix_ub_23 0.812432E-1 _diffrn_orient_matrix_ub_31 -0.101756 _diffrn_orient_matrix_ub_32 0.8331E-3 _diffrn_orient_matrix_ub_33 -0.530227E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0407 _diffrn_reflns_number 4589 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.404 _diffrn_reflns_theta_max 27.496 _diffrn_reflns_theta_full 25.847 _diffrn_measured_fraction_theta_full 0.955 _diffrn_measured_fraction_theta_max 0.941 _reflns_number_total 4589 _reflns_number_gt 4375 _reflns_threshold_expression I>3.0\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 97 (Sheldrick, 1997)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 F _refine_ls_matrix_type full _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: 0.636 1.72 0.207 0.552 0.159 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method None _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.82(4) _refine_ls_number_reflns 4375 _refine_ls_number_parameters 425 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0369 _refine_ls_wR_factor_gt 0.0369 _refine_ls_wR_factor_all 0.0446 _refine_ls_goodness_of_fit_ref 1.0848 _refine_ls_restrained_S_all 1.149 _refine_ls_shift/su_max 0.000139 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack (1983), 1730 Friedel-pairs' _refine_ls_abs_structure_Flack 0.032(10) _refine_diff_density_max 0.53 _refine_diff_density_min -0.66 _refine_diff_density_rms 0.199 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Co 0.3494 0.9721 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group C3 C 0.5019(4) 0.4738(3) 0.6521(2) 0.0353 Uani 1 . . C4 C 0.5013(5) 0.3244(3) 0.6120(3) 0.0368 Uani 1 . . C5 C 0.2045(4) 0.4110(4) 0.5140(3) 0.0435 Uani 1 . . C6 C 0.1401(4) 0.5863(4) 0.4953(3) 0.0398 Uani 1 . . C7 C 0.3745(4) 0.8162(3) 0.1294(2) 0.0348 Uani 1 . . C8 C 0.5756(4) 0.8608(3) 0.1121(3) 0.036 Uani 1 . . C9 C 0.8449(4) 0.7615(4) 0.2483(3) 0.0383 Uani 1 . . C10 C 0.8950(4) 0.5880(3) 0.2556(3) 0.0346 Uani 1 . . C11 C 0.4444(6) 0.2502(4) 0.4218(3) 0.0496 Uani 1 . . C12 C 0.5853(5) 0.9392(4) 0.3042(3) 0.0459 Uani 1 . . C13 C 0.5639(4) 0.4361(3) 0.7864(2) 0.0396 Uani 1 . . C14 C 0.4363(5) 0.3699(3) 0.8933(3) 0.0499 Uani 1 . . C15 C 0.4837(6) 0.3314(4) 1.0184(3) 0.0632 Uani 1 . . C16 C 0.6578(6) 0.3557(4) 1.0401(3) 0.0627 Uani 1 . . C17 C 0.7845(6) 0.4196(5) 0.9362(3) 0.062 Uani 1 . . C18 C 0.7379(5) 0.4608(5) 0.8089(3) 0.0543 Uani 1 . . C19 C 0.2825(4) 0.8696(3) 0.0049(2) 0.0374 Uani 1 . . C20 C 0.1762(4) 1.0163(3) -0.0286(3) 0.0421 Uani 1 . . C21 C 0.0955(5) 1.0698(3) -0.1442(3) 0.0515 Uani 1 . . C22 C 0.1172(5) 0.9807(4) -0.2266(3) 0.0579 Uani 1 . . C23 C 0.2197(6) 0.8335(5) -0.1920(4) 0.0642 Uani 1 . . C24 C 0.3020(6) 0.7780(4) -0.0775(3) 0.0535 Uani 1 . . C25 C 0.6988(5) 0.2408(4) 0.6002(3) 0.0516 Uani 1 . . C26 C 0.7054(4) 0.7904(4) 0.0162(3) 0.0485 Uani 1 . . H1 H 0.734(6) 0.565(5) 0.554(4) 0.0579 Uiso 1 . . H2 H 0.262(6) 0.608(4) 0.194(3) 0.05 Uiso 1 . . H3 H 0.374(5) 0.525(4) 0.657(3) 0.0409 Uiso 1 . . H4 H 0.418(5) 0.246(4) 0.689(3) 0.0422 Uiso 1 . . H7 H 0.295(5) 0.865(4) 0.185(3) 0.0422 Uiso 1 . . H8 H 0.570(5) 0.970(4) 0.074(3) 0.0411 Uiso 1 . . H14 H 0.312(6) 0.366(4) 0.884(4) 0.0573 Uiso 1 . . H15 H 0.373(6) 0.313(5) 1.091(4) 0.0707 Uiso 1 . . H16 H 0.684(6) 0.327(5) 1.121(5) 0.0727 Uiso 1 . . H17 H 0.894(8) 0.438(5) 0.952(5) 0.0784 Uiso 1 . . H18 H 0.827(6) 0.504(5) 0.738(4) 0.0707 Uiso 1 . . H20 H 0.157(5) 1.078(4) 0.032(3) 0.0485 Uiso 1 . . H21 H 0.009(5) 1.178(4) -0.169(4) 0.0594 Uiso 1 . . H22 H 0.059(6) 1.025(5) -0.312(4) 0.0674 Uiso 1 . . H23 H 0.246(8) 0.762(6) -0.248(5) 0.0834 Uiso 1 . . H24 H 0.384(6) 0.668(5) -0.066(4) 0.0654 Uiso 1 . . H51 H 0.150(5) 0.357(4) 0.609(3) 0.0493 Uiso 1 . . H52 H 0.142(5) 0.363(4) 0.455(3) 0.0485 Uiso 1 . . H71 H 1.016(13) 0.159(11) 0.301(6) 0.1639 Uiso 1 . . H72 H 1.074(14) 0.305(7) 0.231(8) 0.1639 Uiso 1 . . H81 H 0.113(12) 0.891(8) 0.444(8) 0.1701 Uiso 1 . . H82 H -0.028(13) 0.913(9) 0.538(7) 0.1699 Uiso 1 . . H91 H 0.873(5) 0.764(4) 0.330(3) 0.047 Uiso 1 . . H92 H 0.914(5) 0.840(4) 0.168(3) 0.0468 Uiso 1 . . H111 H 0.406(5) 0.158(4) 0.472(3) 0.0711 Uiso 1 . . H112 H 0.576(8) 0.236(4) 0.397(4) 0.0702 Uiso 1 . . H113 H 0.387(6) 0.278(4) 0.353(5) 0.0709 Uiso 1 . . H121 H 0.606(7) 0.894(5) 0.392(2) 0.0758 Uiso 1 . . H122 H 0.679(7) 1.029(6) 0.248(4) 0.0756 Uiso 1 . . H123 H 0.448(7) 0.982(5) 0.299(4) 0.0746 Uiso 1 . . H251 H 0.700(7) 0.126(6) 0.593(4) 0.0799 Uiso 1 . . H252 H 0.765(6) 0.223(5) 0.681(4) 0.0806 Uiso 1 . . H253 H 0.770(7) 0.319(5) 0.514(4) 0.0804 Uiso 1 . . H261 H 0.699(4) 0.667(6) 0.052(3) 0.0764 Uiso 1 . . H262 H 0.847(7) 0.811(4) 0.008(3) 0.076 Uiso 1 . . H263 H 0.660(4) 0.831(4) -0.063(4) 0.0756 Uiso 1 . . N1 N 0.4093(4) 0.3742(3) 0.4877(2) 0.0342 Uani 1 . . N2 N 0.6396(4) 0.8097(3) 0.2463(2) 0.0329 Uani 1 . . O1 O 0.6066(3) 0.5840(3) 0.5501(2) 0.0367 Uani 1 . . O2 O 0.3868(3) 0.6474(2) 0.1884(2) 0.0352 Uani 1 . . O3 O 0.2568(3) 0.6852(3) 0.4365(2) 0.0411 Uani 1 . . O4 O 0.7650(3) 0.4974(3) 0.3014(2) 0.0376 Uani 1 . . O5 O -0.0242(4) 0.6211(3) 0.5361(2) 0.0564 Uani 1 . . O6 O 1.0595(3) 0.5400(3) 0.2225(2) 0.0456 Uani 1 . . O7 O 1.0787(7) 0.2094(5) 0.2193(4) 0.1042 Uani 1 . . O8 O 0.0390(8) 0.9703(5) 0.4662(4) 0.1119 Uani 1 . . Co1 Co 0.51378(18) 0.59576(13) 0.36358(11) 0.0311 Uani 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 C3 0.0343(11) 0.0384(10) 0.0315(10) -0.0095(8) -0.0033(8) -0.0020(8) C4 0.0416(14) 0.0336(11) 0.0320(11) -0.0045(9) -0.0086(9) -0.0015(9) C5 0.0347(13) 0.0498(14) 0.0431(14) -0.0048(11) -0.0085(10) -0.0126(10) C6 0.0287(13) 0.0550(15) 0.0327(11) -0.0079(10) -0.0076(9) -0.0039(10) C7 0.0329(11) 0.0349(10) 0.0342(10) -0.0072(8) -0.0078(8) 0.0004(8) C8 0.0357(14) 0.0344(12) 0.0350(11) -0.0039(9) -0.0081(9) -0.0053(9) C9 0.0313(12) 0.0405(12) 0.0425(13) -0.0098(10) -0.0061(9) -0.0069(9) C10 0.0258(12) 0.0433(13) 0.0339(11) -0.0108(9) -0.0048(8) -0.0015(9) C11 0.064(2) 0.0450(17) 0.0441(16) -0.0166(14) -0.0065(14) -0.0125(15) C12 0.0525(19) 0.0402(15) 0.0509(17) -0.0209(14) -0.0145(13) 0.0020(13) C13 0.0432(13) 0.0400(11) 0.0336(10) -0.0092(8) -0.0073(9) 0.0006(9) C14 0.0612(17) 0.0506(13) 0.0372(11) -0.0093(10) -0.0041(11) -0.0146(11) C15 0.095(3) 0.0574(15) 0.0348(12) -0.0076(11) -0.0041(13) -0.0203(15) C16 0.100(3) 0.0552(15) 0.0336(12) -0.0114(11) -0.0182(13) -0.0060(15) C17 0.063(2) 0.082(2) 0.0496(16) -0.0273(16) -0.0223(14) 0.0004(16) C18 0.0474(16) 0.079(2) 0.0387(13) -0.0202(14) -0.0079(11) -0.0057(14) C19 0.0329(11) 0.0401(10) 0.0365(10) -0.0059(8) -0.0106(8) -0.0020(8) C20 0.0400(12) 0.0383(11) 0.0445(12) -0.0068(9) -0.0100(9) -0.0013(8) C21 0.0507(14) 0.0461(13) 0.0506(14) -0.0021(11) -0.0168(11) -0.0001(10) C22 0.0633(18) 0.0621(16) 0.0427(13) -0.0034(11) -0.0230(12) -0.0003(13) C23 0.075(2) 0.072(2) 0.0547(17) -0.0287(15) -0.0258(15) 0.0064(16) C24 0.0641(19) 0.0528(16) 0.0462(14) -0.0202(12) -0.0195(12) 0.0107(13) C25 0.0533(16) 0.0479(14) 0.0554(14) -0.0201(12) -0.0197(12) 0.0125(11) C26 0.0400(14) 0.0696(17) 0.0360(11) -0.0157(11) -0.0010(10) -0.0104(11) N1 0.0336(12) 0.0348(11) 0.0325(10) -0.0059(8) -0.0054(8) -0.0063(8) N2 0.0329(11) 0.0333(10) 0.0331(10) -0.0093(8) -0.0077(8) -0.0032(8) O1 0.0314(9) 0.0420(9) 0.0349(8) -0.0077(7) -0.0062(6) -0.0047(7) O2 0.0312(9) 0.0342(8) 0.0360(8) -0.0017(6) -0.0101(6) -0.0046(6) O3 0.0305(10) 0.0444(11) 0.0423(10) -0.0082(8) -0.0024(8) 0.0016(8) O4 0.0289(10) 0.0352(9) 0.0452(10) -0.0084(8) -0.0017(7) -0.0037(7) O5 0.0285(10) 0.0801(15) 0.0533(12) -0.0169(10) 0.0038(8) 0.0002(9) O6 0.0286(10) 0.0516(10) 0.0559(11) -0.0159(9) -0.0036(8) -0.0049(7) O7 0.130(4) 0.085(2) 0.105(3) -0.0472(19) -0.012(2) 0.005(2) O8 0.157(4) 0.0767(19) 0.104(3) -0.0406(19) -0.023(3) 0.021(2) Co1 0.02533(13) 0.03400(13) 0.03094(13) -0.00577(8) -0.00369(8) -0.00270(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C3 C4 1.544(3) . . yes C3 C13 1.519(3) . . yes C3 H3 0.97(4) . . no C3 O1 1.432(3) . . yes C4 C25 1.517(4) . . yes C4 H4 1.07(3) . . no C4 N1 1.511(4) . . yes C5 C6 1.533(5) . . yes C5 H51 1.03(3) . . no C5 H52 1.07(3) . . no C5 N1 1.470(4) . . yes C6 O3 1.266(4) . . yes C6 O5 1.234(4) . . yes C7 C8 1.530(3) . . yes C7 C19 1.511(3) . . yes C7 H7 0.94(3) . . no C7 O2 1.441(3) . . yes C8 C26 1.527(4) . . yes C8 H8 0.94(3) . . no C8 N2 1.512(4) . . yes C9 C10 1.528(4) . . yes C9 H91 0.95(4) . . no C9 H92 1.04(3) . . no C9 N2 1.481(4) . . yes C10 O4 1.271(3) . . yes C10 O6 1.243(4) . . yes C11 H111 0.89(3) . . no C11 H112 0.95(5) . . no C11 H113 0.86(5) . . no C11 N1 1.485(4) . . yes C12 H121 0.945(19) . . no C12 H122 1.10(5) . . no C12 H123 1.01(5) . . no C12 N2 1.475(4) . . yes C13 C14 1.398(3) . . yes C13 C18 1.377(4) . . yes C14 C15 1.382(4) . . yes C14 H14 0.93(4) . . no C15 C16 1.374(6) . . yes C15 H15 1.03(4) . . no C16 C17 1.369(5) . . yes C16 H16 0.88(5) . . no C17 C18 1.400(5) . . yes C17 H17 0.88(5) . . no C18 H18 0.95(4) . . no C19 C20 1.393(3) . . yes C19 C24 1.384(4) . . yes C20 C21 1.385(4) . . yes C20 H20 0.98(3) . . no C21 C22 1.366(4) . . yes C21 H21 1.06(3) . . no C22 C23 1.385(5) . . yes C22 H22 1.02(4) . . no C23 C24 1.380(5) . . yes C23 H23 1.00(5) . . no C24 H24 1.05(5) . . no C25 H251 1.06(5) . . no C25 H252 1.02(4) . . no C25 H253 1.09(5) . . no C26 H261 1.06(5) . . no C26 H262 1.05(5) . . no C26 H263 0.92(5) . . no H1 O1 0.92(5) . . no H2 O2 1.00(4) . . no H71 O7 0.94(5) . . no H72 O7 0.91(5) . . no H81 O8 0.90(5) . . no H82 O8 0.90(5) . . no N1 Co1 2.185(2) . . yes N2 Co1 2.179(2) . . yes O1 Co1 2.2079(19) . . yes O2 Co1 2.1354(18) . . yes O3 Co1 2.059(2) . . yes O4 Co1 2.0173(19) . . yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 C3 C13 112.50(18) . . . yes C4 C3 H3 108.9(18) . . . no C13 C3 H3 106.0(18) . . . no C4 C3 O1 108.60(18) . . . yes C13 C3 O1 115.20(19) . . . yes H3 C3 O1 105.2(18) . . . no C3 C4 C25 111.2(2) . . . yes C3 C4 H4 106.8(17) . . . no C25 C4 H4 107.6(18) . . . no C3 C4 N1 107.4(2) . . . yes C25 C4 N1 113.4(2) . . . yes H4 C4 N1 110.3(18) . . . no C6 C5 H51 102.9(19) . . . no C6 C5 H52 113.8(19) . . . no H51 C5 H52 106(3) . . . no C6 C5 N1 114.4(2) . . . yes H51 C5 N1 114(2) . . . no H52 C5 N1 105.7(18) . . . no C5 C6 O3 118.1(3) . . . yes C5 C6 O5 117.3(3) . . . yes O3 C6 O5 124.6(3) . . . yes C8 C7 C19 113.86(18) . . . yes C8 C7 H7 111(2) . . . no C19 C7 H7 105(2) . . . no C8 C7 O2 106.00(19) . . . yes C19 C7 O2 112.37(18) . . . yes H7 C7 O2 109(2) . . . no C7 C8 C26 111.8(2) . . . yes C7 C8 H8 107(2) . . . no C26 C8 H8 105.7(19) . . . no C7 C8 N2 106.7(2) . . . yes C26 C8 N2 113.8(2) . . . yes H8 C8 N2 111.7(19) . . . no C10 C9 H91 103(2) . . . no C10 C9 H92 114.2(18) . . . no H91 C9 H92 114(3) . . . no C10 C9 N2 112.0(2) . . . yes H91 C9 N2 106(2) . . . no H92 C9 N2 108(2) . . . no C9 C10 O4 117.3(2) . . . yes C9 C10 O6 119.8(2) . . . yes O4 C10 O6 122.9(3) . . . yes H111 C11 H112 109(3) . . . no H111 C11 H113 107(3) . . . no H112 C11 H113 108(3) . . . no H111 C11 N1 113(2) . . . no H112 C11 N1 108(2) . . . no H113 C11 N1 111(3) . . . no H121 C12 H122 114(4) . . . no H121 C12 H123 109(4) . . . no H122 C12 H123 112(3) . . . no H121 C12 N2 105(3) . . . no H122 C12 N2 104(2) . . . no H123 C12 N2 112(3) . . . no C3 C13 C14 117.5(2) . . . yes C3 C13 C18 124.1(2) . . . yes C14 C13 C18 118.4(2) . . . yes C13 C14 C15 120.6(3) . . . yes C13 C14 H14 121(2) . . . no C15 C14 H14 118(2) . . . no C14 C15 C16 120.7(3) . . . yes C14 C15 H15 116(2) . . . no C16 C15 H15 122(2) . . . no C15 C16 C17 119.3(3) . . . yes C15 C16 H16 118(3) . . . no C17 C16 H16 123(3) . . . no C16 C17 C18 120.8(3) . . . yes C16 C17 H17 118(3) . . . no C18 C17 H17 121(3) . . . no C17 C18 C13 120.3(3) . . . yes C17 C18 H18 120(3) . . . no C13 C18 H18 119(3) . . . no C7 C19 C20 118.9(2) . . . yes C7 C19 C24 122.1(2) . . . yes C20 C19 C24 119.0(2) . . . yes C19 C20 C21 119.9(2) . . . yes C19 C20 H20 118(2) . . . no C21 C20 H20 122(2) . . . no C20 C21 C22 121.2(3) . . . yes C20 C21 H21 121(2) . . . no C22 C21 H21 118(2) . . . no C21 C22 C23 118.9(3) . . . yes C21 C22 H22 119(2) . . . no C23 C22 H22 122(2) . . . no C22 C23 C24 120.9(3) . . . yes C22 C23 H23 124(3) . . . no C24 C23 H23 115(3) . . . no C19 C24 C23 120.1(3) . . . yes C19 C24 H24 127(2) . . . no C23 C24 H24 113(2) . . . no C4 C25 H251 113(3) . . . no C4 C25 H252 112(3) . . . no H251 C25 H252 105(3) . . . no C4 C25 H253 104(2) . . . no H251 C25 H253 112(3) . . . no H252 C25 H253 112(3) . . . no C8 C26 H261 106.7(14) . . . no C8 C26 H262 113.7(14) . . . no H261 C26 H262 107.8(16) . . . no C8 C26 H263 108.4(15) . . . no H261 C26 H263 110.0(16) . . . no H262 C26 H263 110.1(16) . . . no C4 N1 C11 112.1(2) . . . yes C4 N1 C5 110.5(2) . . . yes C11 N1 C5 108.7(2) . . . yes C4 N1 Co1 107.73(16) . . . yes C11 N1 Co1 112.00(18) . . . yes C5 N1 Co1 105.60(17) . . . yes C8 N2 C9 113.9(2) . . . yes C8 N2 C12 109.2(2) . . . yes C9 N2 C12 109.5(2) . . . yes C8 N2 Co1 108.86(16) . . . yes C9 N2 Co1 103.45(15) . . . yes C12 N2 Co1 111.83(18) . . . yes C3 O1 H1 113(2) . . . no C3 O1 Co1 108.01(14) . . . yes H1 O1 Co1 116(2) . . . no H2 O2 C7 110(2) . . . no H2 O2 Co1 118(2) . . . no C7 O2 Co1 106.88(14) . . . yes C6 O3 Co1 116.3(2) . . . yes C10 O4 Co1 116.47(18) . . . yes H71 O7 H72 97(8) . . . no H82 O8 H81 99(5) . . . no N1 Co1 N2 175.36(11) . . . yes N1 Co1 O1 80.01(8) . . . yes N2 Co1 O1 96.88(7) . . . yes N1 Co1 O2 104.32(7) . . . yes N2 Co1 O2 79.39(8) . . . yes O1 Co1 O2 168.39(6) . . . yes N1 Co1 O3 81.10(9) . . . yes N2 Co1 O3 102.12(8) . . . yes O1 Co1 O3 84.75(8) . . . yes O2 Co1 O3 85.30(8) . . . yes N1 Co1 O4 95.94(8) . . . yes N2 Co1 O4 80.75(8) . . . yes O1 Co1 O4 93.36(8) . . . yes O2 Co1 O4 96.85(8) . . . yes O3 Co1 O4 176.72(9) . . . yes _chemical_name_common (Co(N-acetyl-(-)-ephedrine)!2$).2H!2$O data_2 _database_code_depnum_ccdc_archive 'CCDC 642791' _audit_creation_date 2007-06-11T13:40:18-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; [Co(N-acetyl-(+)-pseudoephedrine)~2~].2H~2~O ; _chemical_formula_moiety 'C24 H32 Co N2 O6, 2(H2 O)' _chemical_formula_sum 'C24 H36 Co1 N2 O8' _chemical_formula_weight 539.49 _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M 'P 3' _symmetry_space_group_name_Hall 'P 3' loop_ _symmetry_equiv_pos_as_xyz x,y,z -y,x-y,z -x+y,-x,z _cell_length_a 17.440(6) _cell_length_b 17.440(6) _cell_length_c 7.085(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 1866.0(12) _cell_formula_units_Z 3 _cell_measurement_temperature 293 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour pink _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.44 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 855 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.741 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6905 _exptl_absorpt_correction_T_max 0.8948 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Unknown _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_reflns_av_unetI/netI 0.0615 _diffrn_reflns_number 10999 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.348 _diffrn_reflns_theta_max 28.636 _diffrn_reflns_theta_full 25.2 _diffrn_measured_fraction_theta_full 0.819 _diffrn_measured_fraction_theta_max 0.679 _reflns_number_total 3981 _reflns_number_gt 2614 _reflns_threshold_expression I>2.5\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_structure_solution 'SHELXS 97 (Sheldrick, 1997)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 F _refine_ls_matrix_type full _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: 0.442 0.125 0.235 0.116E-01 0.607E-01 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method None _refine_ls_number_reflns 2614 _refine_ls_number_parameters 317 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.038 _refine_ls_wR_factor_gt 0.038 _refine_ls_wR_factor_all 0.0498 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.000195 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack (1983), 1808 Friedel-pairs' _refine_ls_abs_structure_Flack 0.00(2) _refine_diff_density_max 0.22 _refine_diff_density_min -0.44 _refine_diff_density_rms 0.064 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Co 0.3494 0.9721 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group C3 C 0.9342(3) 0.3583(3) 0.1741(8) 0.0282 Uani 1 . . C4 C 0.9252(3) 0.3690(3) -0.0355(8) 0.0255 Uani 1 . . C5 C 0.8659(4) 0.2753(3) -0.3093(9) 0.0317 Uani 1 . . C6 C 0.9259(3) 0.2338(3) -0.3193(9) 0.0286 Uani 1 . . C7 C 0.6985(3) -0.0118(3) -0.0158(7) 0.0262 Uani 1 . . C8 C 0.7743(3) -0.0203(3) 0.0671(8) 0.0283 Uani 1 . . C9 C 0.7947(4) 0.0572(3) 0.3684(8) 0.031 Uani 1 . . C10 C 0.7425(3) 0.1043(3) 0.3804(9) 0.0298 Uani 1 . . C11 C 0.7623(3) 0.2864(4) -0.0962(9) 0.034 Uani 1 . . C12 C 0.9214(3) 0.0688(4) 0.2038(10) 0.0413 Uani 1 . . C13 C 1.0168(3) 0.4388(3) 0.2495(7) 0.0247 Uani 1 . . C14 C 1.0100(3) 0.4982(3) 0.3674(8) 0.0307 Uani 1 . . C15 C 1.0849(4) 0.5745(3) 0.4268(8) 0.0331 Uani 1 . . C16 C 1.1672(4) 0.5931(3) 0.3659(9) 0.0342 Uani 1 . . C17 C 1.1746(3) 0.5343(3) 0.2506(8) 0.0312 Uani 1 . . C18 C 1.1001(3) 0.4576(3) 0.1890(8) 0.0294 Uani 1 . . C19 C 0.6357(3) -0.0927(3) -0.1268(8) 0.0262 Uani 1 . . C20 C 0.5466(3) -0.1386(3) -0.0767(9) 0.0306 Uani 1 . . C21 C 0.4886(3) -0.2192(3) -0.1604(10) 0.0391 Uani 1 . . C22 C 0.5191(4) -0.2539(3) -0.2940(9) 0.0397 Uani 1 . . C23 C 0.6077(4) -0.2080(4) -0.3488(9) 0.041 Uani 1 . . C24 C 0.6646(4) -0.1286(3) -0.2670(8) 0.0322 Uani 1 . . C25 C 0.9251(4) 0.4540(3) -0.0836(9) 0.0365 Uani 1 . . C26 C 0.7410(4) -0.1092(3) 0.1717(10) 0.0414 Uani 1 . . H1 H 0.9507 0.2748 0.3053 0.0411 Uiso 1 . . H2 H 0.723 0.0733 -0.2313 0.0479 Uiso 1 . . H3 H 0.8811 0.3504 0.2389 0.0327 Uiso 1 . . H4 H 0.9767 0.373 -0.0995 0.0286 Uiso 1 . . H7 H 0.6648 -0.0063 0.0884 0.029 Uiso 1 . . H8 H 0.8097 -0.02 -0.0412 0.036 Uiso 1 . . H14 H 0.9543 0.4869 0.4074 0.0381 Uiso 1 . . H15 H 1.0793 0.6132 0.5081 0.0402 Uiso 1 . . H16 H 1.2177 0.6451 0.4045 0.037 Uiso 1 . . H17 H 1.231 0.5468 0.2105 0.0401 Uiso 1 . . H18 H 1.1061 0.4186 0.1091 0.0361 Uiso 1 . . H20 H 0.5253 -0.1152 0.0148 0.0352 Uiso 1 . . H21 H 0.4282 -0.2497 -0.1232 0.0394 Uiso 1 . . H22 H 0.4798 -0.3089 -0.3493 0.0441 Uiso 1 . . H23 H 0.6288 -0.2305 -0.4417 0.0558 Uiso 1 . . H24 H 0.7233 -0.0983 -0.3054 0.042 Uiso 1 . . H51 H 0.8104 0.2334 -0.3667 0.0359 Uiso 1 . . H52 H 0.8918 0.3307 -0.3765 0.0358 Uiso 1 . . H71 H -0.0283 0.0651 0.7145 0.151 Uiso 1 . . H72 H 0.0326 0.1534 0.6825 0.151 Uiso 1 . . H81 H 0.7241 0.4215 0.4056 0.1612 Uiso 1 . . H82 H 0.819 0.4655 0.3914 0.1611 Uiso 1 . . H91 H 0.7574 -0.0037 0.4074 0.0358 Uiso 1 . . H92 H 0.8427 0.0858 0.4555 0.0363 Uiso 1 . . H111 H 0.752 0.2981 0.0322 0.0589 Uiso 1 . . H112 H 0.7632 0.3305 -0.1801 0.0589 Uiso 1 . . H113 H 0.7154 0.2288 -0.1335 0.0586 Uiso 1 . . H121 H 0.9159 0.0175 0.2688 0.0558 Uiso 1 . . H122 H 0.959 0.1219 0.2756 0.0561 Uiso 1 . . H123 H 0.9463 0.0734 0.0785 0.0559 Uiso 1 . . H251 H 0.8886 0.4624 0.0067 0.0556 Uiso 1 . . H252 H 0.9843 0.5023 -0.0746 0.0559 Uiso 1 . . H253 H 0.9035 0.4514 -0.21 0.0559 Uiso 1 . . H261 H 0.785 -0.1053 0.2583 0.0548 Uiso 1 . . H262 H 0.6883 -0.1235 0.2417 0.0545 Uiso 1 . . H263 H 0.7284 -0.1548 0.0807 0.0547 Uiso 1 . . N1 N 0.8471(3) 0.2869(3) -0.1118(7) 0.026 Uani 1 . . N2 N 0.8328(3) 0.0598(3) 0.1811(7) 0.0279 Uani 1 . . O1 O 0.9391(2) 0.2787(2) 0.1930(6) 0.0277 Uani 1 . . O2 O 0.7362(3) 0.0695(2) -0.1209(6) 0.0347 Uani 1 . . O3 O 0.9275(2) 0.1904(2) -0.1775(6) 0.0321 Uani 1 . . O4 O 0.7502(2) 0.1555(2) 0.2450(6) 0.0321 Uani 1 . . O5 O 0.9689(3) 0.2440(2) -0.4661(6) 0.0371 Uani 1 . . O6 O 0.6967(2) 0.0927(2) 0.5260(6) 0.0374 Uani 1 . . O7 O 0.0226(4) 0.1021(4) 0.6828(13) 0.1346 Uani 1 . . O8 O 0.7678(4) 0.4141(4) 0.4295(14) 0.1364 Uani 1 . . Co1 Co 0.84053(4) 0.17428(4) 0.0366(2) 0.0246 Uani 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 C3 0.027(2) 0.027(2) 0.029(4) -0.003(2) -0.005(2) 0.012(2) C4 0.026(2) 0.024(2) 0.025(3) -0.006(2) 0.000(2) 0.0113(19) C5 0.034(3) 0.029(2) 0.030(4) -0.004(3) -0.005(3) 0.013(2) C6 0.034(3) 0.031(3) 0.021(4) -0.004(3) -0.004(3) 0.017(2) C7 0.026(2) 0.022(2) 0.029(3) -0.003(2) -0.004(2) 0.0101(18) C8 0.027(2) 0.030(2) 0.030(3) -0.001(2) 0.001(2) 0.016(2) C9 0.045(3) 0.034(3) 0.012(3) 0.001(2) -0.010(3) 0.018(2) C10 0.025(2) 0.019(2) 0.025(4) -0.004(2) -0.004(3) -0.0039(19) C11 0.031(3) 0.037(3) 0.034(4) -0.002(3) -0.007(3) 0.016(2) C12 0.033(3) 0.034(3) 0.055(5) -0.008(3) -0.009(3) 0.016(2) C13 0.030(2) 0.028(2) 0.016(3) 0.002(2) 0.000(2) 0.0136(19) C14 0.036(3) 0.029(3) 0.029(4) 0.007(2) 0.002(3) 0.017(2) C15 0.051(3) 0.023(2) 0.024(4) -0.005(2) -0.003(3) 0.017(2) C16 0.040(3) 0.026(2) 0.023(4) 0.005(2) -0.011(3) 0.005(2) C17 0.031(3) 0.038(3) 0.025(4) 0.000(3) -0.008(2) 0.018(2) C18 0.036(3) 0.031(3) 0.023(3) -0.009(2) -0.002(2) 0.018(2) C19 0.031(2) 0.027(2) 0.020(3) 0.001(2) -0.004(2) 0.013(2) C20 0.034(3) 0.034(3) 0.027(3) 0.008(2) -0.003(2) 0.019(2) C21 0.027(3) 0.025(2) 0.043(4) 0.005(3) -0.009(3) -0.004(2) C22 0.054(3) 0.028(3) 0.028(4) -0.008(3) -0.015(3) 0.013(2) C23 0.065(4) 0.041(3) 0.025(4) -0.002(3) 0.003(3) 0.032(3) C24 0.037(3) 0.032(3) 0.028(3) 0.002(3) 0.002(2) 0.018(2) C25 0.037(3) 0.026(2) 0.042(5) -0.001(3) -0.006(3) 0.013(2) C26 0.045(3) 0.024(2) 0.054(5) 0.003(3) -0.015(3) 0.016(2) N1 0.027(2) 0.029(2) 0.021(3) 0.001(2) 0.001(2) 0.0126(18) N2 0.028(2) 0.025(2) 0.029(4) -0.003(2) -0.006(2) 0.0119(18) O1 0.0345(19) 0.0257(18) 0.021(2) -0.0025(17) -0.0092(17) 0.0139(15) O2 0.049(2) 0.0180(17) 0.027(3) 0.0030(17) -0.013(2) 0.0095(17) O3 0.0356(19) 0.0318(18) 0.029(3) 0.0029(19) 0.0041(18) 0.0172(16) O4 0.037(2) 0.0374(19) 0.025(3) 0.0000(19) 0.0025(18) 0.0204(16) O5 0.047(2) 0.044(2) 0.021(3) 0.001(2) 0.003(2) 0.0227(19) O6 0.0308(19) 0.042(2) 0.028(3) 0.000(2) 0.001(2) 0.0096(17) O7 0.077(4) 0.074(4) 0.270(11) -0.051(5) -0.030(5) 0.051(3) O8 0.076(4) 0.054(3) 0.272(11) 0.015(5) 0.036(5) 0.028(3) Co1 0.0264(4) 0.0199(3) 0.0236(3) -0.0006(3) -0.0009(3) 0.0088(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C3 C4 1.515(7) . . yes C3 C13 1.520(7) . . yes C3 H3 0.981 . . no C3 O1 1.438(6) . . yes C4 C25 1.522(7) . . yes C4 H4 0.977 . . no C4 N1 1.499(6) . . yes C5 C6 1.544(7) . . yes C5 H51 0.964 . . no C5 H52 0.962 . . no C5 N1 1.474(7) . . yes C6 O3 1.266(7) . . yes C6 O5 1.241(7) . . yes C7 C8 1.519(6) . . yes C7 C19 1.505(6) . . yes C7 H7 0.978 . . no C7 O2 1.436(6) . . yes C8 C26 1.545(7) . . yes C8 H8 0.983 . . no C8 N2 1.489(6) . . yes C9 C10 1.503(7) . . yes C9 H91 0.968 . . no C9 H92 0.955 . . no C9 N2 1.475(7) . . yes C10 O4 1.271(7) . . yes C10 O6 1.258(7) . . yes C11 H111 0.969 . . no C11 H112 0.966 . . no C11 H113 0.962 . . no C11 N1 1.478(6) . . yes C12 H121 0.968 . . no C12 H122 0.969 . . no C12 H123 0.974 . . no C12 N2 1.482(7) . . yes C13 C14 1.381(7) . . yes C13 C18 1.386(7) . . yes C14 C15 1.384(7) . . yes C14 H14 0.935 . . no C15 C16 1.373(8) . . yes C15 H15 0.929 . . no C16 C17 1.367(8) . . yes C16 H16 0.935 . . no C17 C18 1.389(7) . . yes C17 H17 0.938 . . no C18 H18 0.931 . . no C19 C20 1.393(7) . . yes C19 C24 1.395(7) . . yes C20 C21 1.389(8) . . yes C20 H20 0.936 . . no C21 C22 1.367(9) . . yes C21 H21 0.95 . . no C22 C23 1.393(8) . . yes C22 H22 0.941 . . no C23 C24 1.365(8) . . yes C23 H23 0.931 . . no C24 H24 0.928 . . no C25 H251 0.963 . . no C25 H252 0.953 . . no C25 H253 0.963 . . no C26 H261 0.958 . . no C26 H262 0.962 . . no C26 H263 0.961 . . no H1 O1 0.832 . . no H2 O2 0.827 . . no H71 O7 0.826 . . no H72 O7 0.821 . . no H81 O8 0.852 . . no H82 O8 0.935 . . no N1 Co1 2.180(5) . . yes N2 Co1 2.187(5) . . yes O1 Co1 2.089(4) . . yes O2 Co1 2.138(4) . . yes O3 Co1 2.063(4) . . yes O4 Co1 2.063(4) . . yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 C3 C13 109.8(4) . . . yes C4 C3 H3 109 . . . no C13 C3 H3 110.9 . . . no C4 C3 O1 105.7(4) . . . yes C13 C3 O1 112.0(4) . . . yes H3 C3 O1 109.2 . . . no C3 C4 C25 113.0(4) . . . yes C3 C4 H4 108.3 . . . no C25 C4 H4 106 . . . no C3 C4 N1 109.6(4) . . . yes C25 C4 N1 114.0(4) . . . yes H4 C4 N1 105.4 . . . no C6 C5 H51 106.6 . . . no C6 C5 H52 111.1 . . . no H51 C5 H52 110 . . . no C6 C5 N1 110.9(5) . . . yes H51 C5 N1 107.2 . . . no H52 C5 N1 110.9 . . . no C5 C6 O3 117.8(5) . . . yes C5 C6 O5 118.2(5) . . . yes O3 C6 O5 124.0(5) . . . yes C8 C7 C19 111.8(4) . . . yes C8 C7 H7 108.2 . . . no C19 C7 H7 107.1 . . . no C8 C7 O2 107.8(4) . . . yes C19 C7 O2 114.4(4) . . . yes H7 C7 O2 107.3 . . . no C7 C8 C26 112.0(4) . . . yes C7 C8 H8 105.8 . . . no C26 C8 H8 107.4 . . . no C7 C8 N2 109.8(4) . . . yes C26 C8 N2 114.7(5) . . . yes H8 C8 N2 106.5 . . . no C10 C9 H91 108.9 . . . no C10 C9 H92 106.9 . . . no H91 C9 H92 108.8 . . . no C10 C9 N2 114.8(5) . . . yes H91 C9 N2 109.6 . . . no H92 C9 N2 107.6 . . . no C9 C10 O4 117.5(5) . . . yes C9 C10 O6 117.9(5) . . . yes O4 C10 O6 124.5(5) . . . yes H111 C11 H112 110 . . . no H111 C11 H113 109 . . . no H112 C11 H113 109.1 . . . no H111 C11 N1 111.1 . . . no H112 C11 N1 109.4 . . . no H113 C11 N1 108.2 . . . no H121 C12 H122 110 . . . no H121 C12 H123 110.1 . . . no H122 C12 H123 109.8 . . . no H121 C12 N2 109.7 . . . no H122 C12 N2 109.2 . . . no H123 C12 N2 107.9 . . . no C3 C13 C14 120.6(4) . . . yes C3 C13 C18 120.4(4) . . . yes C14 C13 C18 118.8(5) . . . yes C13 C14 C15 120.7(5) . . . yes C13 C14 H14 119.8 . . . no C15 C14 H14 119.5 . . . no C14 C15 C16 120.3(5) . . . yes C14 C15 H15 119.7 . . . no C16 C15 H15 120.1 . . . no C15 C16 C17 119.3(5) . . . yes C15 C16 H16 120.2 . . . no C17 C16 H16 120.4 . . . no C16 C17 C18 121.1(5) . . . yes C16 C17 H17 119.1 . . . no C18 C17 H17 119.8 . . . no C17 C18 C13 119.7(5) . . . yes C17 C18 H18 120.1 . . . no C13 C18 H18 120.2 . . . no C7 C19 C20 119.0(5) . . . yes C7 C19 C24 122.5(4) . . . yes C20 C19 C24 118.2(5) . . . yes C19 C20 C21 120.8(6) . . . yes C19 C20 H20 119.9 . . . no C21 C20 H20 119.3 . . . no C20 C21 C22 119.7(5) . . . yes C20 C21 H21 119.4 . . . no C22 C21 H21 120.9 . . . no C21 C22 C23 120.3(5) . . . yes C21 C22 H22 119.5 . . . no C23 C22 H22 120.2 . . . no C22 C23 C24 119.9(6) . . . yes C22 C23 H23 120.9 . . . no C24 C23 H23 119.3 . . . no C19 C24 C23 121.1(5) . . . yes C19 C24 H24 119.7 . . . no C23 C24 H24 119.2 . . . no C4 C25 H251 108.7 . . . no C4 C25 H252 108.5 . . . no H251 C25 H252 109.2 . . . no C4 C25 H253 110.6 . . . no H251 C25 H253 110.6 . . . no H252 C25 H253 109.3 . . . no C8 C26 H261 110.5 . . . no C8 C26 H262 109.8 . . . no H261 C26 H262 108.5 . . . no C8 C26 H263 109 . . . no H261 C26 H263 109.3 . . . no H262 C26 H263 109.7 . . . no C4 N1 C11 114.0(4) . . . yes C4 N1 C5 108.3(4) . . . yes C11 N1 C5 111.1(5) . . . yes C4 N1 Co1 107.4(3) . . . yes C11 N1 Co1 110.9(3) . . . yes C5 N1 Co1 104.4(3) . . . yes C8 N2 C12 110.3(4) . . . yes C8 N2 C9 111.9(4) . . . yes C12 N2 C9 109.6(5) . . . yes C8 N2 Co1 107.7(3) . . . yes C12 N2 Co1 111.7(3) . . . yes C9 N2 Co1 105.7(3) . . . yes C3 O1 H1 107.5 . . . no C3 O1 Co1 111.8(3) . . . yes H1 O1 Co1 124.4 . . . no C7 O2 H2 124.2 . . . no C7 O2 Co1 110.3(3) . . . yes H2 O2 Co1 125.2 . . . no C6 O3 Co1 115.5(3) . . . yes C10 O4 Co1 117.1(3) . . . yes H71 O7 H72 114.3 . . . no H82 O8 H81 107.2 . . . no N2 Co1 N1 179.0(2) . . . yes N2 Co1 O2 79.97(15) . . . yes N1 Co1 O2 99.05(16) . . . yes N2 Co1 O1 101.29(15) . . . yes N1 Co1 O1 79.70(16) . . . yes O2 Co1 O1 177.71(17) . . . yes N2 Co1 O3 100.05(16) . . . yes N1 Co1 O3 79.55(17) . . . yes O2 Co1 O3 89.20(16) . . . yes O1 Co1 O3 92.45(16) . . . yes N2 Co1 O4 80.01(17) . . . yes N1 Co1 O4 100.37(16) . . . yes O2 Co1 O4 88.96(17) . . . yes O1 Co1 O4 89.38(15) . . . yes O3 Co1 O4 178.12(19) . . . yes _chemical_name_common (Co(N-acetyl-(+)-pseudoephedrine)!2$).2H!2$O data_3 _database_code_depnum_ccdc_archive 'CCDC 642792' _audit_creation_date 2007-02-09T12:46:45-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; [Co(N-(-)-acetyl-phenylephrine)~2~].2H~2~O ; _chemical_name_common (Co(N-(-)-acetyl-phenylephrine)!2$).2H!2$O _chemical_formula_moiety 'C22 H28 Co1 N2 O8, 2(H2 O)' _chemical_formula_sum 'C22 H32 Co1 N2 O10' _chemical_formula_weight 543.44 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_Int_Tables_number 1 loop_ _symmetry_equiv_pos_as_xyz x,y,z _cell_length_a 7.3617(2) _cell_length_b 7.3785(2) _cell_length_c 11.3521(3) _cell_angle_alpha 84.9280(13) _cell_angle_beta 75.9946(14) _cell_angle_gamma 84.7652(12) _cell_volume 594.40(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293 _cell_measurement_reflns_used 2447 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 285 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.782 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9034 _exptl_absorpt_correction_T_max 0.9248 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.708522E-1 _diffrn_orient_matrix_ub_12 0.439249E-1 _diffrn_orient_matrix_ub_13 0.554962E-1 _diffrn_orient_matrix_ub_21 -0.107405 _diffrn_orient_matrix_ub_22 -0.243844E-1 _diffrn_orient_matrix_ub_23 0.710706E-1 _diffrn_orient_matrix_ub_31 0.560981E-1 _diffrn_orient_matrix_ub_32 -0.126831 _diffrn_orient_matrix_ub_33 0.12275E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0674 _diffrn_reflns_number 4432 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.445 _diffrn_reflns_theta_max 27.537 _diffrn_reflns_theta_full 25.058 _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.948 _reflns_number_total 4432 _reflns_number_gt 3424 _reflns_threshold_expression I>3.0\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 97 (Sheldrick, 1997)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.00P)^2^ + 0.01P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method 'Larson (1970), Equation 22' _refine_ls_extinction_coef 42(7) _refine_ls_number_reflns 3424 _refine_ls_number_parameters 318 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0402 _refine_ls_wR_factor_gt 0.0402 _refine_ls_wR_factor_all 0.0596 _refine_ls_goodness_of_fit_ref 1.0054 _refine_ls_restrained_S_all 1.121 _refine_ls_shift/su_max 0.000087 _refine_ls_shift/su_mean 0.002 _refine_ls_abs_structure_details 'Flack (1983), 4432 Friedel-pairs' _refine_ls_abs_structure_Flack 0.027(16) _refine_diff_density_max 0.33 _refine_diff_density_min -0.48 _refine_diff_density_rms 0.121 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Co 0.3494 0.9721 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group C3 C 0.1828(6) 0.0404(5) 0.5334(3) 0.0302 Uani 1 . . C4 C 0.2214(6) 0.2347(5) 0.5417(4) 0.0311 Uani 1 . . C5 C 0.3041(7) 0.5108(6) 0.4166(4) 0.0289 Uani 1 . . C6 C 0.1348(7) 0.5544(6) 0.3626(5) 0.0276 Uani 1 . . C7 C 0.4619(6) 0.2636(5) 0.0206(3) 0.0297 Uani 1 . . C8 C 0.2620(6) 0.2291(6) 0.0225(4) 0.0307 Uani 1 . . C9 C 0.2632(7) -0.0845(6) 0.1148(4) 0.0285 Uani 1 . . C10 C 0.4215(7) -0.1387(6) 0.1781(4) 0.0243 Uani 1 . . C11 C 0.5483(7) 0.2700(7) 0.4321(5) 0.0389 Uani 1 . . C12 C -0.0237(7) 0.1125(7) 0.1492(5) 0.0365 Uani 1 . . C13 C 0.0437(7) -0.0237(6) 0.6476(4) 0.0299 Uani 1 . . C14 C 0.1127(7) -0.1140(6) 0.7411(4) 0.0341 Uani 1 . . C15 C -0.0078(8) -0.1691(6) 0.8506(4) 0.0341 Uani 1 . . C16 C -0.1982(8) -0.1327(7) 0.8680(5) 0.036 Uani 1 . . C17 C -0.2696(8) -0.0400(7) 0.7737(5) 0.04 Uani 1 . . C18 C -0.1471(8) 0.0150(7) 0.6642(5) 0.0397 Uani 1 . . C19 C 0.5663(7) 0.3711(6) -0.0917(4) 0.0295 Uani 1 . . C20 C 0.4785(7) 0.4600(6) -0.1782(5) 0.0381 Uani 1 . . C21 C 0.5870(8) 0.5410(7) -0.2854(4) 0.0352 Uani 1 . . C22 C 0.7779(8) 0.5338(7) -0.3054(5) 0.0363 Uani 1 . . C23 C 0.8652(8) 0.4493(7) -0.2186(5) 0.0372 Uani 1 . . C24 C 0.7597(7) 0.3686(6) -0.1126(4) 0.0362 Uani 1 . . H1 H 0.0989 -0.0587 0.4085 0.0485 Uiso 1 . . H2 H 0.4635 0.4536 0.1213 0.0484 Uiso 1 . . H3 H 0.3007 -0.0369 0.5238 0.0389 Uiso 1 . . H7 H 0.534 0.1426 0.0265 0.0344 Uiso 1 . . H8 H 0.5562 0.6663 -0.4311 0.0771 Uiso 1 . . H14 H 0.2423 -0.1401 0.7313 0.0409 Uiso 1 . . H16 H -0.279 -0.1728 0.9412 0.0421 Uiso 1 . . H17 H -0.3994 -0.0135 0.7853 0.0476 Uiso 1 . . H18 H -0.1957 0.0771 0.6018 0.045 Uiso 1 . . H20 H 0.3471 0.4661 -0.167 0.0467 Uiso 1 . . H22 H 0.8494 0.5883 -0.3767 0.0409 Uiso 1 . . H23 H 0.9956 0.4473 -0.2314 0.0438 Uiso 1 . . H24 H 0.8195 0.3116 -0.0541 0.0446 Uiso 1 . . H41 H 0.1042 0.3126 0.5545 0.0407 Uiso 1 . . H42 H 0.279 0.2432 0.6106 0.0407 Uiso 1 . . H51 H 0.2808 0.5618 0.4963 0.0386 Uiso 1 . . H52 H 0.411 0.5641 0.3616 0.0386 Uiso 1 . . H71 H -0.0065 -0.3012 0.9913 0.0881 Uiso 1 . . H81 H 0.1869 0.3466 0.0272 0.0401 Uiso 1 . . H82 H 0.2588 0.1746 -0.0524 0.0401 Uiso 1 . . H91 H 0.1667 -0.1671 0.1478 0.038 Uiso 1 . . H92 H 0.3103 -0.1021 0.0274 0.038 Uiso 1 . . H101 H 0.779 0.7616 0.3971 0.0708 Uiso 1 . . H102 H 0.6377 0.843 0.3602 0.0707 Uiso 1 . . H111 H 0.5744 0.1398 0.4463 0.0579 Uiso 1 . . H112 H 0.5771 0.3317 0.4947 0.0581 Uiso 1 . . H113 H 0.6277 0.3112 0.3552 0.0584 Uiso 1 . . H121 H -0.0756 0.041 0.2236 0.0528 Uiso 1 . . H122 H -0.0543 0.0663 0.0805 0.0531 Uiso 1 . . H123 H -0.0713 0.239 0.1568 0.0524 Uiso 1 . . H901 H 0.9256 0.5551 0.1949 0.0868 Uiso 1 . . H902 H 0.7671 0.649 0.1577 0.0868 Uiso 1 . . N1 N 0.3485(5) 0.3104(5) 0.4285(4) 0.0256 Uani 1 . . N2 N 0.1827(6) 0.1056(5) 0.1298(4) 0.0249 Uani 1 . . O1 O 0.1093(5) 0.0433(4) 0.4263(3) 0.0319 Uani 1 . . O2 O 0.4599(5) 0.3445(4) 0.1336(3) 0.0324 Uani 1 . . O3 O 0.0889(5) 0.4341(4) 0.3043(3) 0.0311 Uani 1 . . O4 O 0.4557(5) -0.0307(4) 0.2493(3) 0.0289 Uani 1 . . O5 O 0.0503(5) 0.7099(4) 0.3769(3) 0.0345 Uani 1 . . O6 O 0.5052(5) -0.2916(4) 0.1588(3) 0.0348 Uani 1 . . O7 O 0.0749(6) -0.2673(6) 0.9337(4) 0.0568 Uani 1 . . O8 O 0.4888(5) 0.6258(6) -0.3668(4) 0.0517 Uani 1 . . O9 O 0.8731(6) 0.5959(6) 0.1418(4) 0.0594 Uani 1 . . O10 O 0.6648(5) 0.7848(5) 0.4176(4) 0.051 Uani 1 . . Co1 Co 0.27147(13) 0.20195(12) 0.27967(9) 0.0259 Uani 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 C3 0.035(2) 0.0246(19) 0.031(2) -0.0011(16) -0.0095(17) -0.0006(17) C4 0.042(3) 0.029(2) 0.0217(19) -0.0020(17) -0.0061(18) -0.0028(19) C5 0.035(3) 0.022(2) 0.030(2) -0.0024(16) -0.0088(18) 0.0005(18) C6 0.026(3) 0.027(3) 0.027(2) 0.0068(18) -0.0021(19) -0.004(2) C7 0.043(2) 0.025(2) 0.0219(18) -0.0019(15) -0.0079(17) -0.0039(18) C8 0.040(3) 0.031(2) 0.0223(19) 0.0028(17) -0.0105(18) -0.0081(19) C9 0.036(3) 0.024(2) 0.029(2) 0.0014(17) -0.0121(19) -0.0091(18) C10 0.032(3) 0.020(2) 0.020(2) -0.0026(17) -0.0029(18) -0.0049(19) C11 0.035(3) 0.036(3) 0.051(3) -0.006(2) -0.020(2) 0.002(2) C12 0.032(3) 0.037(3) 0.040(3) -0.001(2) -0.007(2) -0.001(2) C13 0.039(3) 0.025(2) 0.026(2) -0.0024(17) -0.0066(19) -0.0033(18) C14 0.035(3) 0.038(3) 0.030(2) -0.0007(19) -0.0058(19) -0.008(2) C15 0.044(3) 0.036(3) 0.024(3) -0.0011(19) -0.009(2) -0.005(2) C16 0.044(3) 0.033(3) 0.029(3) -0.006(2) 0.000(2) -0.009(2) C17 0.033(3) 0.036(3) 0.045(3) -0.001(2) 0.001(2) 0.002(2) C18 0.052(4) 0.032(2) 0.031(2) 0.0020(19) -0.008(2) 0.006(2) C19 0.035(3) 0.027(2) 0.025(2) -0.0031(17) -0.0036(19) -0.003(2) C20 0.036(3) 0.042(3) 0.035(3) 0.002(2) -0.008(2) -0.002(2) C21 0.046(3) 0.034(2) 0.025(3) -0.0004(19) -0.010(2) -0.003(2) C22 0.042(3) 0.038(3) 0.025(2) 0.003(2) 0.000(2) -0.002(2) C23 0.039(3) 0.039(3) 0.033(3) -0.008(2) -0.007(2) -0.001(2) C24 0.041(3) 0.034(2) 0.035(3) 0.005(2) -0.015(2) -0.003(2) N1 0.025(2) 0.024(2) 0.026(2) 0.0016(16) -0.0027(17) -0.0021(17) N2 0.030(2) 0.0218(19) 0.025(2) 0.0019(16) -0.0116(17) 0.0000(17) O1 0.047(2) 0.0240(17) 0.0254(19) -0.0037(14) -0.0068(15) -0.0081(15) O2 0.047(2) 0.0265(18) 0.0255(19) -0.0014(14) -0.0103(16) -0.0093(15) O3 0.040(2) 0.0245(18) 0.034(2) -0.0036(15) -0.0182(16) 0.0007(16) O4 0.035(2) 0.0260(18) 0.0292(19) -0.0045(14) -0.0132(15) -0.0007(15) O5 0.0365(19) 0.0209(16) 0.047(2) -0.0058(13) -0.0113(15) 0.0026(14) O6 0.0360(19) 0.0282(18) 0.0393(18) -0.0045(13) -0.0092(15) 0.0060(15) O7 0.050(2) 0.084(3) 0.036(2) 0.0135(19) -0.0135(17) -0.011(2) O8 0.043(2) 0.077(3) 0.0307(19) 0.0181(17) -0.0090(16) -0.0021(18) O9 0.048(3) 0.088(3) 0.036(2) 0.015(2) -0.0114(19) 0.012(2) O10 0.037(2) 0.073(3) 0.038(2) 0.0168(19) -0.0085(18) -0.0030(19) Co1 0.0336(3) 0.0221(2) 0.0219(2) -0.00119(16) -0.00723(17) -0.00079(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C3 C4 1.502(5) . . yes C3 C13 1.513(6) . . yes C3 H3 0.983 . . no C3 O1 1.443(5) . . yes C4 H41 0.979 . . no C4 H42 0.985 . . no C4 N1 1.492(5) . . yes C5 C6 1.514(7) . . yes C5 H51 0.982 . . no C5 H52 0.97 . . no C5 N1 1.486(5) . . yes C6 O3 1.268(6) . . yes C6 O5 1.258(6) . . yes C7 C8 1.511(6) . . yes C7 C19 1.517(6) . . yes C7 H7 1.002 . . no C7 O2 1.459(5) . . yes C8 H81 0.984 . . no C8 H82 0.978 . . no C8 N2 1.487(5) . . yes C9 C10 1.518(7) . . yes C9 H91 0.962 . . no C9 H92 0.985 . . no C9 N2 1.479(6) . . yes C10 O4 1.265(6) . . yes C10 O6 1.246(5) . . yes C11 H111 0.969 . . no C11 H112 0.952 . . no C11 H113 0.967 . . no C11 N1 1.483(6) . . yes C12 H121 0.97 . . no C12 H122 0.96 . . no C12 H123 0.97 . . no C12 N2 1.478(7) . . yes C13 C14 1.380(7) . . yes C13 C18 1.378(7) . . yes C14 C15 1.393(7) . . yes C14 H14 0.937 . . no C15 C16 1.372(8) . . yes C15 O7 1.364(6) . . yes C16 C17 1.402(8) . . yes C16 H16 0.94 . . no C17 C18 1.399(8) . . yes C17 H17 0.937 . . no C18 H18 0.935 . . no C19 C20 1.389(7) . . yes C19 C24 1.384(7) . . yes C20 C21 1.402(7) . . yes C20 H20 0.942 . . no C21 C22 1.365(8) . . yes C21 O8 1.380(6) . . yes C22 C23 1.377(8) . . yes C22 H22 0.932 . . no C23 C24 1.382(7) . . yes C23 H23 0.935 . . no C24 H24 0.933 . . no H1 O1 0.811 . . no H2 O2 0.807 . . no H8 O8 0.825 . . no H71 O7 0.811 . . no H101 O10 0.823 . . no H102 O10 0.805 . . no H901 O9 0.814 . . no H902 O9 0.827 . . no N1 Co1 2.145(4) . . yes N2 Co1 2.160(4) . . yes O1 Co1 2.125(3) . . yes O2 Co1 2.151(3) . . yes O3 Co1 2.074(3) . . yes O4 Co1 2.087(3) . . yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 C3 C13 109.7(3) . . . yes C4 C3 H3 109.3 . . . no C13 C3 H3 109.9 . . . no C4 C3 O1 104.9(3) . . . yes C13 C3 O1 112.2(3) . . . yes H3 C3 O1 110.6 . . . no C3 C4 H41 110.2 . . . no C3 C4 H42 109.9 . . . no H41 C4 H42 108.5 . . . no C3 C4 N1 112.5(3) . . . yes H41 C4 N1 106.9 . . . no H42 C4 N1 108.6 . . . no C6 C5 H51 110 . . . no C6 C5 H52 108.3 . . . no H51 C5 H52 109.8 . . . no C6 C5 N1 110.7(4) . . . yes H51 C5 N1 110.2 . . . no H52 C5 N1 107.8 . . . no C5 C6 O3 118.3(4) . . . yes C5 C6 O5 117.6(5) . . . yes O3 C6 O5 124.1(5) . . . yes C8 C7 C19 115.8(4) . . . yes C8 C7 H7 108 . . . no C19 C7 H7 107.5 . . . no C8 C7 O2 107.6(3) . . . yes C19 C7 O2 113.0(3) . . . yes H7 C7 O2 104.1 . . . no C7 C8 H81 108.4 . . . no C7 C8 H82 109.5 . . . no H81 C8 H82 109.2 . . . no C7 C8 N2 110.6(3) . . . yes H81 C8 N2 109.3 . . . no H82 C8 N2 109.8 . . . no C10 C9 H91 106.9 . . . no C10 C9 H92 108.6 . . . no H91 C9 H92 108.3 . . . no C10 C9 N2 114.5(4) . . . yes H91 C9 N2 109.4 . . . no H92 C9 N2 109 . . . no C9 C10 O4 118.8(4) . . . yes C9 C10 O6 116.7(4) . . . yes O4 C10 O6 124.5(5) . . . yes H111 C11 H112 109.3 . . . no H111 C11 H113 109.1 . . . no H112 C11 H113 108.2 . . . no H111 C11 N1 110.1 . . . no H112 C11 N1 110.7 . . . no H113 C11 N1 109.4 . . . no H121 C12 H122 111 . . . no H121 C12 H123 109.6 . . . no H122 C12 H123 110.1 . . . no H121 C12 N2 109.3 . . . no H122 C12 N2 109.1 . . . no H123 C12 N2 107.7 . . . no C3 C13 C14 118.2(4) . . . yes C3 C13 C18 122.5(4) . . . yes C14 C13 C18 119.2(4) . . . yes C13 C14 C15 120.9(5) . . . yes C13 C14 H14 120.1 . . . no C15 C14 H14 119 . . . no C14 C15 C16 120.4(5) . . . yes C14 C15 O7 115.9(5) . . . yes C16 C15 O7 123.6(5) . . . yes C15 C16 C17 119.0(5) . . . yes C15 C16 H16 120.1 . . . no C17 C16 H16 120.9 . . . no C16 C17 C18 120.0(5) . . . yes C16 C17 H17 119.4 . . . no C18 C17 H17 120.5 . . . no C17 C18 C13 120.4(5) . . . yes C17 C18 H18 119.6 . . . no C13 C18 H18 120.1 . . . no C7 C19 C20 123.0(5) . . . yes C7 C19 C24 118.1(4) . . . yes C20 C19 C24 118.8(4) . . . yes C19 C20 C21 119.6(5) . . . yes C19 C20 H20 121.5 . . . no C21 C20 H20 118.9 . . . no C20 C21 C22 120.6(5) . . . yes C20 C21 O8 115.9(5) . . . yes C22 C21 O8 123.4(5) . . . yes C21 C22 C23 119.9(5) . . . yes C21 C22 H22 120.3 . . . no C23 C22 H22 119.8 . . . no C22 C23 C24 120.0(5) . . . yes C22 C23 H23 119.8 . . . no C24 C23 H23 120.2 . . . no C19 C24 C23 121.1(5) . . . yes C19 C24 H24 119.3 . . . no C23 C24 H24 119.6 . . . no C4 N1 C5 108.4(3) . . . yes C4 N1 C11 111.0(4) . . . yes C5 N1 C11 110.2(4) . . . yes C4 N1 Co1 106.3(3) . . . yes C5 N1 Co1 106.0(3) . . . yes C11 N1 Co1 114.6(3) . . . yes C8 N2 C9 111.6(4) . . . yes C8 N2 C12 109.7(4) . . . yes C9 N2 C12 110.0(4) . . . yes C8 N2 Co1 105.2(3) . . . yes C9 N2 Co1 107.2(3) . . . yes C12 N2 Co1 113.0(3) . . . yes C3 O1 H1 112 . . . no C3 O1 Co1 110.7(2) . . . yes H1 O1 Co1 112.6 . . . no C7 O2 H2 109.6 . . . no C7 O2 Co1 108.1(2) . . . yes H2 O2 Co1 126.5 . . . no C6 O3 Co1 115.3(3) . . . yes C10 O4 Co1 115.8(3) . . . yes C15 O7 H71 108.8 . . . no C21 O8 H8 114 . . . no H902 O9 H901 122 . . . no H101 O10 H102 105.2 . . . no N2 Co1 O2 81.95(15) . . . yes N2 Co1 N1 176.81(17) . . . yes O2 Co1 N1 97.93(13) . . . yes N2 Co1 O1 99.70(14) . . . yes O2 Co1 O1 174.17(16) . . . yes N1 Co1 O1 80.73(15) . . . yes N2 Co1 O4 80.93(14) . . . yes O2 Co1 O4 88.47(13) . . . yes N1 Co1 O4 102.26(14) . . . yes O1 Co1 O4 86.28(13) . . . yes N2 Co1 O3 97.64(14) . . . yes O2 Co1 O3 90.39(13) . . . yes N1 Co1 O3 79.17(15) . . . yes O1 Co1 O3 94.91(13) . . . yes O4 Co1 O3 178.28(18) . . . yes data_publish4 _database_code_depnum_ccdc_archive 'CCDC 642793' # Attachment 'Co7(+).cif' _audit_creation_date 2007-02-08T14:46:45-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; [Co(N-acetyl-(+)-ephedrine)~2~] ; _chemical_name_common 'Compound X' _chemical_formula_moiety 'C24 H32 Co1 N2 O6' _chemical_formula_sum 'C24 H32 Co1 N2 O6' _chemical_formula_weight 503.46 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'C 2 c b' _symmetry_space_group_name_Hall 'C -2bc 2' _symmetry_Int_Tables_number 41 loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,y+1/2,z x,-y,-z x+1/2,-y+1/2,-z x,-y+1/2,z+1/2 x+1/2,-y+1,z+1/2 x,y+1/2,-z+1/2 x+1/2,y+1,-z+1/2 _cell_length_a 8.6971(2) _cell_length_b 26.2558(8) _cell_length_c 10.6396(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2429.55(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 1579 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'light green' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1060 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.747 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8611 _exptl_absorpt_correction_T_max 0.942 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.769215E-1 _diffrn_orient_matrix_ub_12 -0.241382E-1 _diffrn_orient_matrix_ub_13 -0.364968E-1 _diffrn_orient_matrix_ub_21 0.225985E-1 _diffrn_orient_matrix_ub_22 -0.249348E-1 _diffrn_orient_matrix_ub_23 0.686027E-1 _diffrn_orient_matrix_ub_31 -0.824196E-1 _diffrn_orient_matrix_ub_32 0.156911E-1 _diffrn_orient_matrix_ub_33 0.528723E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.039 _diffrn_reflns_number 2619 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.551 _diffrn_reflns_theta_max 27.44 _diffrn_reflns_theta_full 25.245 _diffrn_measured_fraction_theta_full 0.968 _diffrn_measured_fraction_theta_max 0.942 _reflns_number_total 2522 _reflns_number_gt 1799 _reflns_threshold_expression I>3.0\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 97 (Sheldrick, 1997)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 F _refine_ls_matrix_type full _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: 0.545 0.451 0.234 0.637E-01 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method None _refine_ls_number_reflns 1799 _refine_ls_number_parameters 199 _refine_ls_number_restraints 70 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0379 _refine_ls_wR_factor_gt 0.0379 _refine_ls_wR_factor_all 0.2346 _refine_ls_goodness_of_fit_ref 1.0262 _refine_ls_restrained_S_all 1.142 _refine_ls_shift/su_max 0.000142 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' _refine_ls_abs_structure_Flack 0.52(2) _refine_diff_density_max 0.19 _refine_diff_density_min -0.25 _refine_diff_density_rms 0.194 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Co 0.3494 0.9721 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group C7 C 0.8742(4) 0.10406(11) 0.5656(3) 0.0362 Uani 1 . . C8 C 0.7195(4) 0.11246(11) 0.5001(3) 0.0378 Uani 1 . . C9 C 0.5753(4) 0.06341(12) 0.6593(3) 0.0423 Uani 1 . . C10 C 0.6818(3) 0.03152(10) 0.7419(3) 0.0378 Uani 1 . . C12 C 0.4812(4) 0.06758(15) 0.4442(4) 0.0524 Uani 1 . . C19 C 0.9796(4) 0.15025(11) 0.5634(3) 0.0417 Uani 1 . . C20 C 0.9569(5) 0.18914(12) 0.6490(4) 0.0634 Uani 1 . . C21 C 1.0552(6) 0.23112(14) 0.6491(5) 0.0853 Uani 1 . . C22 C 1.1748(6) 0.23416(16) 0.5649(5) 0.0894 Uani 1 . . C23 C 1.1972(5) 0.19587(17) 0.4807(4) 0.0826 Uani 1 . . C24 C 1.1001(5) 0.15398(14) 0.4797(3) 0.061 Uani 1 . . C26 C 0.7414(4) 0.12342(14) 0.3616(3) 0.051 Uani 1 . . H2 H 1.020(3) 0.0526(14) 0.545(3) 0.0482 Uiso 1 . . H7 H 0.855(2) 0.0963(8) 0.6541(16) 0.04 Uiso 1 . . H8 H 0.669(2) 0.1418(7) 0.5419(19) 0.0417 Uiso 1 . . H20 H 0.8761(19) 0.1876(7) 0.7077(15) 0.0696 Uiso 1 . . H21 H 1.041(2) 0.2568(7) 0.7078(15) 0.0942 Uiso 1 . . H22 H 1.242(2) 0.2621(7) 0.5662(16) 0.0999 Uiso 1 . . H23 H 1.279(2) 0.1982(7) 0.4230(15) 0.0929 Uiso 1 . . H24 H 1.116(2) 0.1279(7) 0.4218(15) 0.068 Uiso 1 . . H91 H 0.473(2) 0.0475(8) 0.661(2) 0.0464 Uiso 1 . . H92 H 0.572(3) 0.0981(7) 0.6917(19) 0.0455 Uiso 1 . . H121 H 0.409(3) 0.0414(9) 0.473(3) 0.0723 Uiso 1 . . H122 H 0.433(3) 0.1010(8) 0.450(3) 0.0732 Uiso 1 . . H123 H 0.513(3) 0.0601(11) 0.3578(18) 0.0722 Uiso 1 . . H261 H 0.770(4) 0.0922(8) 0.320(2) 0.0702 Uiso 1 . . H262 H 0.823(3) 0.1485(9) 0.351(2) 0.07 Uiso 1 . . H263 H 0.648(2) 0.1369(10) 0.327(2) 0.0702 Uiso 1 . . N2 N 0.6205(3) 0.06616(13) 0.5241(3) 0.0366 Uani 1 . . O2 O 0.9412(3) 0.06055(10) 0.50751(19) 0.0346 Uani 1 . . O4 O 0.7685(4) -0.00017(7) 0.68848(15) 0.0368 Uani 1 . . O6 O 0.6771(3) 0.03768(9) 0.85760(19) 0.0526 Uani 1 . . Co1 Co 0.77666(15) 0 0.5 0.0298 Uani 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 C7 0.0429(18) 0.0320(14) 0.0337(16) -0.0017(12) -0.0014(14) 0.0018(12) C8 0.0383(16) 0.0355(13) 0.0397(16) -0.0019(12) -0.0053(13) 0.0072(10) C9 0.0362(17) 0.0498(17) 0.0411(16) -0.0070(13) 0.0058(13) 0.0043(14) C10 0.0307(16) 0.0475(16) 0.0351(14) -0.0015(12) 0.0039(12) -0.0026(13) C12 0.037(2) 0.070(2) 0.0501(19) -0.0007(17) -0.0116(16) 0.0063(17) C19 0.0423(19) 0.0350(15) 0.0480(17) 0.0039(13) -0.0076(15) 0.0018(13) C20 0.073(3) 0.0455(18) 0.072(2) -0.0133(17) -0.011(2) 0.0042(19) C21 0.101(4) 0.042(2) 0.113(4) -0.021(2) -0.029(3) 0.001(2) C22 0.086(4) 0.047(2) 0.135(5) 0.007(3) -0.021(4) -0.020(2) C23 0.072(3) 0.065(3) 0.111(4) 0.011(3) 0.010(3) -0.023(2) C24 0.065(2) 0.0469(19) 0.071(2) 0.0026(16) 0.0057(19) -0.0148(18) C26 0.058(3) 0.0505(17) 0.0442(18) 0.0069(13) -0.0078(15) 0.0069(15) N2 0.0225(16) 0.0468(16) 0.0404(15) 0.0001(12) -0.0019(11) 0.0077(13) O2 0.0322(12) 0.0321(12) 0.0394(13) -0.0009(9) -0.0066(9) 0.0043(10) O4 0.0395(11) 0.0399(8) 0.0312(7) -0.0029(8) 0.0048(15) 0.0039(10) O6 0.0406(13) 0.0838(17) 0.0335(12) -0.0096(10) 0.0021(9) 0.0086(13) Co1 0.0272(2) 0.0346(2) 0.02753(19) -0.0022(2) 0 0 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C7 C8 1.531(4) . . yes C7 C19 1.520(4) . . yes C7 H7 0.977(17) . . no C7 O2 1.423(4) . . yes C8 C26 1.513(4) . . yes C8 H8 0.994(17) . . no C8 N2 1.511(5) . . yes C9 C10 1.527(4) . . yes C9 H91 0.985(18) . . no C9 H92 0.974(17) . . no C9 N2 1.493(4) . . yes C10 O4 1.259(4) . . yes C10 O6 1.242(3) . . yes C12 H121 0.977(18) . . no C12 H122 0.974(18) . . no C12 H123 0.979(18) . . no C12 N2 1.481(5) . . yes C19 C20 1.382(4) . . yes C19 C24 1.378(5) . . yes C20 C21 1.395(6) . . yes C20 H20 0.941(18) . . no C21 C22 1.376(7) . . yes C21 H21 0.928(18) . . no C22 C23 1.361(7) . . yes C22 H22 0.937(18) . . no C23 C24 1.387(5) . . yes C23 H23 0.939(19) . . no C24 H24 0.931(18) . . no C26 H261 0.964(18) . . no C26 H262 0.977(18) . . no C26 H263 0.960(18) . . no H2 O2 0.823(18) . . no N2 Co1 2.220(3) . . yes O2 Co1 2.140(3) . . yes O4 Co1 2.0066(16) . . yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 C7 C19 114.1(2) . . . yes C8 C7 H7 108.5(13) . . . no C19 C7 H7 106.5(12) . . . no C8 C7 O2 106.1(2) . . . yes C19 C7 O2 112.8(3) . . . yes H7 C7 O2 108.8(12) . . . no C7 C8 C26 111.1(3) . . . yes C7 C8 H8 107.5(13) . . . no C26 C8 H8 110.1(12) . . . no C7 C8 N2 107.9(2) . . . yes C26 C8 N2 112.9(3) . . . yes H8 C8 N2 107.1(13) . . . no C10 C9 H91 107.8(12) . . . no C10 C9 H92 109.0(13) . . . no H91 C9 H92 111.3(15) . . . no C10 C9 N2 114.9(2) . . . yes H91 C9 N2 106.3(13) . . . no H92 C9 N2 107.6(13) . . . no C9 C10 O4 117.8(3) . . . yes C9 C10 O6 118.6(3) . . . yes O4 C10 O6 123.6(3) . . . yes H121 C12 H122 109.7(16) . . . no H121 C12 H123 109.2(16) . . . no H122 C12 H123 111.2(16) . . . no H121 C12 N2 109.2(15) . . . no H122 C12 N2 109.7(15) . . . no H123 C12 N2 107.8(15) . . . no C7 C19 C20 119.5(3) . . . yes C7 C19 C24 121.7(3) . . . yes C20 C19 C24 118.8(3) . . . yes C19 C20 C21 119.8(4) . . . yes C19 C20 H20 120.8(12) . . . no C21 C20 H20 119.4(12) . . . no C20 C21 C22 120.6(4) . . . yes C20 C21 H21 119.5(13) . . . no C22 C21 H21 119.9(13) . . . no C21 C22 C23 119.6(4) . . . yes C21 C22 H22 120.4(13) . . . no C23 C22 H22 119.9(13) . . . no C22 C23 C24 120.2(5) . . . yes C22 C23 H23 119.4(13) . . . no C24 C23 H23 120.4(13) . . . no C23 C24 C19 121.0(4) . . . yes C23 C24 H24 119.6(12) . . . no C19 C24 H24 119.4(12) . . . no C8 C26 H261 108.7(13) . . . no C8 C26 H262 109.3(14) . . . no H261 C26 H262 109.7(16) . . . no C8 C26 H263 109.4(14) . . . no H261 C26 H263 110.7(16) . . . no H262 C26 H263 109.1(15) . . . no C8 N2 C9 110.6(3) . . . yes C8 N2 C12 110.4(3) . . . yes C9 N2 C12 109.8(3) . . . yes C8 N2 Co1 105.17(19) . . . yes C9 N2 Co1 103.56(19) . . . yes C12 N2 Co1 117.0(2) . . . yes C7 O2 H2 109(3) . . . no C7 O2 Co1 109.8(2) . . . yes H2 O2 Co1 113(3) . . . no C10 O4 Co1 118.1(2) . . . yes N2 Co1 N2 104.57(16) 3_556 . . yes N2 Co1 O2 79.83(8) 3_556 . 3_556 yes N2 Co1 O2 174.02(11) . . 3_556 yes N2 Co1 O2 174.02(11) 3_556 . . yes N2 Co1 O2 79.83(8) . . . yes O2 Co1 O2 96.09(14) 3_556 . . yes N2 Co1 O4 95.28(11) 3_556 . . yes N2 Co1 O4 82.24(11) . . . yes O2 Co1 O4 93.40(9) 3_556 . . yes O2 Co1 O4 89.30(10) . . . yes N2 Co1 O4 82.24(11) 3_556 . 3_556 yes N2 Co1 O4 95.28(11) . . 3_556 yes O2 Co1 O4 89.30(10) 3_556 . 3_556 yes O2 Co1 O4 93.40(9) . . 3_556 yes O4 Co1 O4 176.0(2) . . 3_556 yes data_5 _database_code_depnum_ccdc_archive 'CCDC 642794' _audit_creation_date 2007-06-08T12:56:17-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; [Ni(N-acetyl-(+)-ephedrine)~2~].2H~2~O ; _chemical_formula_moiety 'C24 H32 N2 Ni O6, 2(H2 O)' _chemical_formula_sum 'C24 H36 N2 Ni1 O8' _chemical_formula_weight 539.27 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_Int_Tables_number 1 loop_ _symmetry_equiv_pos_as_xyz x,y,z _cell_length_a 7.2510(2) _cell_length_b 8.9808(3) _cell_length_c 10.9121(4) _cell_angle_alpha 70.3550(15) _cell_angle_beta 81.6001(14) _cell_angle_gamma 81.6535(14) _cell_volume 658.53(4) _cell_formula_units_Z 1 _cell_measurement_temperature 293 _cell_measurement_reflns_used 8832 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'light blue' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.36 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 286 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.785 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8547 _exptl_absorpt_correction_T_max 0.889 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.13818 _diffrn_orient_matrix_ub_12 0.277033E-1 _diffrn_orient_matrix_ub_13 -0.36496E-2 _diffrn_orient_matrix_ub_21 -0.181849E-1 _diffrn_orient_matrix_ub_22 -0.241032E-1 _diffrn_orient_matrix_ub_23 0.970918E-1 _diffrn_orient_matrix_ub_31 0.147928E-1 _diffrn_orient_matrix_ub_32 0.113049 _diffrn_orient_matrix_ub_33 -0.01151 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_unetI/netI 0.0576 _diffrn_reflns_number 8611 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.503 _diffrn_reflns_theta_max 27.499 _diffrn_reflns_theta_full 26.124 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.984 _reflns_number_total 4953 _reflns_number_gt 4374 _reflns_threshold_expression I>3.0\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 97 (Sheldrick, 1997)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 F _refine_ls_matrix_type full _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: 2.14 -0.454 1.93 -0.396 0.404 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method None _refine_ls_number_reflns 4374 _refine_ls_number_parameters 318 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.0562 _refine_ls_wR_factor_gt 0.0562 _refine_ls_wR_factor_all 0.0672 _refine_ls_goodness_of_fit_ref 1.0838 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000129 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack (1983), 1982 Friedel-pairs' _refine_ls_abs_structure_Flack 0.052(14) _refine_diff_density_max 0.82 _refine_diff_density_min -0.51 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Ni 0.3393 1.1124 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group C3 C 0.6578(6) 0.3856(4) 0.5964(3) 0.0338 Uani 1 . . C4 C 0.4596(7) 0.3372(5) 0.6163(4) 0.0362 Uani 1 . . C5 C 0.1886(7) 0.4359(6) 0.4783(6) 0.0401 Uani 1 . . C6 C 0.1402(7) 0.6090(6) 0.4708(5) 0.0325 Uani 1 . . C7 C 0.5170(6) 0.7180(4) 0.0778(3) 0.0361 Uani 1 . . C8 C 0.5227(8) 0.8673(6) 0.1165(5) 0.0397 Uani 1 . . C9 C 0.8163(8) 0.7769(7) 0.2173(5) 0.0459 Uani 1 . . C10 C 0.8779(8) 0.6031(7) 0.2351(5) 0.0451 Uani 1 . . C11 C 0.4478(8) 0.2572(7) 0.4249(5) 0.0478 Uani 1 . . C12 C 0.5807(9) 0.9396(6) 0.3070(5) 0.0464 Uani 1 . . C13 C 0.7491(6) 0.3327(5) 0.7233(4) 0.0369 Uani 1 . . C14 C 0.8511(6) 0.1825(5) 0.7593(4) 0.0428 Uani 1 . . C15 C 0.9319(7) 0.1277(6) 0.8769(4) 0.0552 Uani 1 . . C16 C 0.9178(8) 0.2200(7) 0.9545(5) 0.0635 Uani 1 . . C17 C 0.8199(10) 0.3691(8) 0.9201(6) 0.0654 Uani 1 . . C18 C 0.7321(9) 0.4245(7) 0.8032(6) 0.0533 Uani 1 . . C19 C 0.4500(6) 0.7573(5) -0.0569(4) 0.0399 Uani 1 . . C20 C 0.2754(9) 0.7299(8) -0.0759(5) 0.0566 Uani 1 . . C21 C 0.2287(10) 0.7696(8) -0.2032(6) 0.0644 Uani 1 . . C22 C 0.3512(10) 0.8407(6) -0.3099(4) 0.068 Uani 1 . . C23 C 0.5251(9) 0.8653(6) -0.2913(4) 0.0605 Uani 1 . . C24 C 0.5754(8) 0.8251(5) -0.1647(4) 0.05 Uani 1 . . C25 C 0.3297(6) 0.4056(6) 0.7125(4) 0.0485 Uani 1 . . C26 C 0.3268(7) 0.9553(6) 0.1261(4) 0.0523 Uani 1 . . H1 H 0.747(9) 0.571(7) 0.547(5) 0.0478 Uiso 1 . . H2 H 0.290(10) 0.606(7) 0.202(6) 0.0557 Uiso 1 . . H3 H 0.7429 0.3263 0.5504 0.048 Uiso 1 . . H4 H 0.4662 0.2214 0.6538 0.0404 Uiso 1 . . H7 H 0.6451 0.6677 0.0708 0.0407 Uiso 1 . . H8 H 0.6022 0.9401 0.0478 0.0453 Uiso 1 . . H14 H 0.8649 0.1186 0.7049 0.0484 Uiso 1 . . H15 H 0.9973 0.0272 0.902 0.0601 Uiso 1 . . H16 H 0.9733 0.1824 1.0327 0.0726 Uiso 1 . . H17 H 0.8111 0.431 0.9739 0.0819 Uiso 1 . . H18 H 0.6628 0.5236 0.7807 0.0639 Uiso 1 . . H20 H 0.1898 0.6892 -0.0048 0.072 Uiso 1 . . H21 H 0.1122 0.7485 -0.2171 0.0797 Uiso 1 . . H22 H 0.3146 0.8719 -0.3941 0.0792 Uiso 1 . . H23 H 0.6117 0.906 -0.3626 0.07 Uiso 1 . . H24 H 0.6931 0.8419 -0.1531 0.0603 Uiso 1 . . H51 H 0.16 0.3886 0.5685 0.0565 Uiso 1 . . H52 H 0.1389 0.4141 0.4102 0.0564 Uiso 1 . . H71 H -0.0435 0.9119 0.4512 0.159 Uiso 1 . . H72 H -0.1619 1.0346 0.4745 0.1586 Uiso 1 . . H81 H 1.1111 0.1647 0.266 0.288 Uiso 1 . . H82 H 0.9711 0.2598 0.2929 0.288 Uiso 1 . . H91 H 0.8789 0.8066 0.2768 0.0539 Uiso 1 . . H92 H 0.857 0.841 0.1282 0.0546 Uiso 1 . . H111 H 0.5757 0.2103 0.4423 0.0714 Uiso 1 . . H112 H 0.3647 0.1749 0.4678 0.0715 Uiso 1 . . H113 H 0.4381 0.2941 0.3326 0.0718 Uiso 1 . . H121 H 0.6543 0.9095 0.379 0.07 Uiso 1 . . H122 H 0.6194 1.0394 0.2466 0.0696 Uiso 1 . . H123 H 0.45 0.9522 0.3394 0.0695 Uiso 1 . . H251 H 0.2177 0.3485 0.7489 0.0712 Uiso 1 . . H252 H 0.3992 0.3967 0.784 0.0713 Uiso 1 . . H253 H 0.2918 0.5139 0.6664 0.0707 Uiso 1 . . H261 H 0.2486 0.886 0.1928 0.0799 Uiso 1 . . H262 H 0.3319 1.052 0.1456 0.0799 Uiso 1 . . H263 H 0.2761 0.9795 0.0423 0.08 Uiso 1 . . N1 N 0.3941(6) 0.3875(4) 0.4799(4) 0.0318 Uani 1 . . N2 N 0.6134(6) 0.8150(5) 0.2415(4) 0.0353 Uani 1 . . O1 O 0.6428(5) 0.5562(4) 0.5370(3) 0.0335 Uani 1 . . O2 O 0.4128(5) 0.6088(4) 0.1823(3) 0.0373 Uani 1 . . O3 O 0.2694(5) 0.7000(4) 0.4272(3) 0.0359 Uani 1 . . O4 O 0.7609(5) 0.5029(4) 0.2940(4) 0.0419 Uani 1 . . O5 O -0.0255(5) 0.6546(4) 0.5043(4) 0.0437 Uani 1 . . O6 O 1.0426(6) 0.5662(6) 0.1977(5) 0.0674 Uani 1 . . O7 O -0.0745(9) 0.9783(6) 0.5085(6) 0.1061 Uani 1 . . O8 O 0.985(3) 0.165(2) 0.3122(16) 0.298(8) Uiso 1 . . Ni1 Ni 0.51287(18) 0.59777(14) 0.36361(11) 0.0299 Uani 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 C3 0.0337(19) 0.0325(16) 0.0341(16) -0.0074(13) -0.0101(14) -0.0010(14) C4 0.038(2) 0.033(2) 0.033(2) 0.0012(15) -0.0114(16) -0.0078(16) C5 0.027(2) 0.043(2) 0.051(3) -0.0145(19) -0.0073(18) -0.0052(17) C6 0.025(2) 0.040(2) 0.0322(19) -0.0084(16) -0.0040(15) -0.0054(16) C7 0.034(2) 0.0397(17) 0.0305(16) -0.0089(14) -0.0034(14) 0.0018(15) C8 0.043(3) 0.039(2) 0.034(2) -0.0095(17) -0.0049(17) 0.0016(18) C9 0.032(2) 0.060(3) 0.038(2) -0.0002(19) -0.0038(17) -0.015(2) C10 0.029(2) 0.067(3) 0.032(2) -0.010(2) -0.0009(17) 0.000(2) C11 0.045(3) 0.047(3) 0.054(3) -0.018(3) -0.008(2) -0.005(2) C12 0.068(4) 0.036(3) 0.038(2) -0.012(2) -0.013(2) -0.007(2) C13 0.0303(18) 0.0406(18) 0.0358(17) -0.0056(14) -0.0121(14) 0.0011(14) C14 0.036(2) 0.0381(18) 0.047(2) -0.0042(15) -0.0057(16) -0.0032(15) C15 0.052(3) 0.049(2) 0.050(2) 0.0051(19) -0.018(2) -0.0002(19) C16 0.058(3) 0.079(3) 0.047(2) -0.009(2) -0.025(2) 0.006(3) C17 0.076(4) 0.073(4) 0.052(3) -0.026(3) -0.027(3) 0.011(3) C18 0.058(3) 0.048(3) 0.053(3) -0.014(2) -0.021(2) 0.008(2) C19 0.044(2) 0.0390(18) 0.0337(17) -0.0087(14) -0.0063(15) 0.0003(16) C20 0.049(3) 0.085(4) 0.037(2) -0.020(2) -0.004(2) -0.009(3) C21 0.064(4) 0.086(4) 0.048(3) -0.023(3) -0.019(2) -0.003(3) C22 0.117(5) 0.055(3) 0.032(2) -0.0117(18) -0.024(2) 0.001(3) C23 0.093(4) 0.050(2) 0.034(2) -0.0071(17) -0.002(2) -0.014(2) C24 0.063(3) 0.049(2) 0.0364(19) -0.0093(16) -0.0046(18) -0.0103(19) C25 0.034(2) 0.071(3) 0.041(2) -0.0181(19) 0.0015(16) -0.0123(19) C26 0.054(3) 0.050(2) 0.055(2) -0.0216(19) -0.021(2) 0.016(2) N1 0.029(2) 0.0326(18) 0.0326(18) -0.0074(15) -0.0088(15) -0.0022(15) N2 0.033(2) 0.038(2) 0.0351(19) -0.0098(16) -0.0059(16) -0.0078(16) O1 0.0249(15) 0.0333(14) 0.0381(16) -0.0037(11) -0.0075(12) -0.0039(11) O2 0.0281(16) 0.0443(17) 0.0372(15) -0.0090(12) -0.0047(12) -0.0053(13) O3 0.0262(18) 0.0401(17) 0.0401(17) -0.0113(14) -0.0034(13) -0.0034(14) O4 0.030(2) 0.0429(19) 0.047(2) -0.0106(16) -0.0014(15) 0.0032(15) O5 0.0226(16) 0.0502(17) 0.059(2) -0.0203(15) -0.0040(13) -0.0001(12) O6 0.029(2) 0.100(3) 0.062(2) -0.021(2) 0.0052(16) 0.0050(19) O7 0.130(5) 0.080(3) 0.120(4) -0.048(3) -0.023(4) 0.000(3) Ni1 0.0238(2) 0.03247(19) 0.03039(18) -0.00604(13) -0.00375(13) -0.00236(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C3 C4 1.526(6) . . yes C3 C13 1.522(5) . . yes C3 H3 0.955 . . no C3 O1 1.443(5) . . yes C4 C25 1.531(7) . . yes C4 H4 0.978 . . no C4 N1 1.529(6) . . yes C5 C6 1.521(7) . . yes C5 H51 0.937 . . no C5 H52 0.958 . . no C5 N1 1.491(6) . . yes C6 O3 1.266(6) . . yes C6 O5 1.255(6) . . yes C7 C8 1.543(6) . . yes C7 C19 1.526(5) . . yes C7 H7 0.976 . . no C7 O2 1.430(5) . . yes C8 C26 1.530(7) . . yes C8 H8 0.987 . . no C8 N2 1.502(7) . . yes C9 C10 1.514(9) . . yes C9 H91 0.968 . . no C9 H92 0.976 . . no C9 N2 1.467(7) . . yes C10 O4 1.271(7) . . yes C10 O6 1.240(7) . . yes C11 H111 0.979 . . no C11 H112 0.971 . . no C11 H113 0.958 . . no C11 N1 1.467(6) . . yes C12 H121 0.955 . . no C12 H122 0.969 . . no C12 H123 0.966 . . no C12 N2 1.494(6) . . yes C13 C14 1.400(5) . . yes C13 C18 1.370(7) . . yes C14 C15 1.394(6) . . yes C14 H14 0.941 . . no C15 C16 1.355(8) . . yes C15 H15 0.928 . . no C16 C17 1.379(8) . . yes C16 H16 0.934 . . no C17 C18 1.413(8) . . yes C17 H17 0.926 . . no C18 H18 0.93 . . no C19 C20 1.381(8) . . yes C19 C24 1.395(6) . . yes C20 C21 1.394(8) . . yes C20 H20 0.926 . . no C21 C22 1.384(9) . . yes C21 H21 0.936 . . no C22 C23 1.367(9) . . yes C22 H22 0.932 . . no C23 C24 1.395(6) . . yes C23 H23 0.931 . . no C24 H24 0.921 . . no C25 H251 0.984 . . no C25 H252 0.964 . . no C25 H253 0.953 . . no C26 H261 0.957 . . no C26 H262 0.968 . . no C26 H263 0.98 . . no H1 O1 0.82(7) . . no H2 O2 0.89(7) . . no H71 O7 0.984 . . no H72 O7 0.803 . . no H81 O8 0.977 . . no H82 O8 0.798 . . no N1 Ni1 2.112(4) . . yes N2 Ni1 2.120(4) . . yes O1 Ni1 2.133(3) . . yes O2 Ni1 2.171(3) . . yes O3 Ni1 2.010(3) . . yes O4 Ni1 2.032(3) . . yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 C3 C13 112.7(3) . . . yes C4 C3 H3 111.4 . . . no C13 C3 H3 98.7 . . . no C4 C3 O1 106.4(3) . . . yes C13 C3 O1 111.7(3) . . . yes H3 C3 O1 116.1 . . . no C4 C3 Ni1 79.3(2) . . . yes C13 C3 Ni1 158.2(2) . . . yes H3 C3 Ni1 93.2 . . . no O1 C3 Ni1 46.52(18) . . . yes C3 C4 C25 112.3(4) . . . yes C3 C4 H4 108.2 . . . no C25 C4 H4 107 . . . no C3 C4 N1 106.1(3) . . . yes C25 C4 N1 114.2(4) . . . yes H4 C4 N1 108.8 . . . no C6 C5 H51 98.7 . . . no C6 C5 H52 111.3 . . . no H51 C5 H52 126.5 . . . no C6 C5 N1 111.7(4) . . . yes H51 C5 N1 94.9 . . . no H52 C5 N1 112.2 . . . no C6 C5 Ni1 72.0(3) . . . yes H51 C5 Ni1 124 . . . no H52 C5 Ni1 107.4 . . . no N1 C5 Ni1 46.2(2) . . . yes C5 C6 O3 117.6(4) . . . yes C5 C6 O5 118.5(4) . . . yes O3 C6 O5 123.8(5) . . . yes C5 C6 Ni1 76.7(3) . . . yes O5 C6 Ni1 164.2(4) . . . yes C8 C7 C19 112.8(3) . . . yes C8 C7 H7 107.9 . . . no C19 C7 H7 105.6 . . . no C8 C7 O2 108.0(3) . . . yes C19 C7 O2 115.1(4) . . . yes H7 C7 O2 107.2 . . . no C7 C8 C26 111.0(4) . . . yes C7 C8 H8 108.6 . . . no C26 C8 H8 107.8 . . . no C7 C8 N2 107.5(4) . . . yes C26 C8 N2 113.5(4) . . . yes H8 C8 N2 108.3 . . . no C10 C9 H91 107.5 . . . no C10 C9 H92 109.5 . . . no H91 C9 H92 108 . . . no C10 C9 N2 114.6(4) . . . yes H91 C9 N2 109 . . . no H92 C9 N2 108 . . . no C9 C10 O4 118.1(5) . . . yes C9 C10 O6 117.9(6) . . . yes O4 C10 O6 123.9(6) . . . yes C9 C10 Ni1 76.9(3) . . . yes O6 C10 Ni1 164.1(5) . . . yes H111 C11 H112 107.7 . . . no H111 C11 H113 110.1 . . . no H112 C11 H113 109.4 . . . no H111 C11 N1 110.3 . . . no H112 C11 N1 108.5 . . . no H113 C11 N1 110.7 . . . no H121 C12 H122 107.3 . . . no H121 C12 H123 108.7 . . . no H122 C12 H123 110.6 . . . no H121 C12 N2 110 . . . no H122 C12 N2 110.2 . . . no H123 C12 N2 110 . . . no C3 C13 C14 117.7(3) . . . yes C3 C13 C18 122.7(4) . . . yes C14 C13 C18 119.7(4) . . . yes C13 C14 C15 119.4(4) . . . yes C13 C14 H14 120.5 . . . no C15 C14 H14 120.1 . . . no C14 C15 C16 120.8(4) . . . yes C14 C15 H15 119.7 . . . no C16 C15 H15 119.5 . . . no C15 C16 C17 120.7(4) . . . yes C15 C16 H16 120.1 . . . no C17 C16 H16 119.2 . . . no C16 C17 C18 119.2(5) . . . yes C16 C17 H17 119.9 . . . no C18 C17 H17 120.9 . . . no C17 C18 C13 120.2(5) . . . yes C17 C18 H18 119.7 . . . no C13 C18 H18 120.1 . . . no C7 C19 C20 123.7(4) . . . yes C7 C19 C24 116.6(4) . . . yes C20 C19 C24 119.7(4) . . . yes C19 C20 C21 119.0(5) . . . yes C19 C20 H20 120.1 . . . no C21 C20 H20 120.9 . . . no C20 C21 C22 121.2(6) . . . yes C20 C21 H21 119.6 . . . no C22 C21 H21 119.2 . . . no C21 C22 C23 119.8(5) . . . yes C21 C22 H22 119.9 . . . no C23 C22 H22 120.3 . . . no C22 C23 C24 119.9(5) . . . yes C22 C23 H23 120.4 . . . no C24 C23 H23 119.7 . . . no C19 C24 C23 120.3(5) . . . yes C19 C24 H24 120.5 . . . no C23 C24 H24 119.2 . . . no C4 C25 H251 112.9 . . . no C4 C25 H252 107.9 . . . no H251 C25 H252 108.1 . . . no C4 C25 H253 107.4 . . . no H251 C25 H253 109.3 . . . no H252 C25 H253 111.3 . . . no C8 C26 H261 108.5 . . . no C8 C26 H262 110.7 . . . no H261 C26 H262 110.7 . . . no C8 C26 H263 107.9 . . . no H261 C26 H263 108.4 . . . no H262 C26 H263 110.5 . . . no C4 N1 C5 113.4(4) . . . yes C4 N1 C11 109.2(4) . . . yes C5 N1 C11 110.1(4) . . . yes C4 N1 Ni1 108.4(3) . . . yes C5 N1 Ni1 103.2(3) . . . yes C11 N1 Ni1 112.4(3) . . . yes C8 N2 C12 112.0(4) . . . yes C8 N2 C9 110.9(4) . . . yes C12 N2 C9 108.3(4) . . . yes C8 N2 Ni1 108.2(3) . . . yes C12 N2 Ni1 112.3(3) . . . yes C9 N2 Ni1 105.0(3) . . . yes C3 O1 H1 98(4) . . . no C3 O1 Ni1 104.1(2) . . . yes H1 O1 Ni1 131(4) . . . no C7 O2 H2 130(4) . . . no C7 O2 Ni1 107.4(3) . . . yes H2 O2 Ni1 104(4) . . . no C6 O3 Ni1 114.6(3) . . . yes C10 O4 Ni1 114.4(3) . . . yes H71 O7 H72 99.2 . . . no H81 O8 H82 93.1 . . . no O2 Ni1 O1 170.72(12) . . . yes O2 Ni1 N2 81.34(15) . . . yes O1 Ni1 N2 101.60(14) . . . yes O2 Ni1 N1 95.91(14) . . . yes O1 Ni1 N1 81.59(15) . . . yes N2 Ni1 N1 175.91(19) . . . yes O2 Ni1 O4 85.69(14) . . . yes O1 Ni1 O4 85.95(14) . . . yes N2 Ni1 O4 82.91(15) . . . yes N1 Ni1 O4 99.96(15) . . . yes O2 Ni1 O3 93.60(13) . . . yes O1 Ni1 O3 94.91(13) . . . yes N2 Ni1 O3 94.87(15) . . . yes N1 Ni1 O3 82.25(14) . . . yes O4 Ni1 O3 177.74(18) . . . yes O2 Ni1 C6 87.76(13) . . . yes O1 Ni1 C6 98.50(13) . . . yes N2 Ni1 C6 117.35(15) . . . yes N1 Ni1 C6 59.32(14) . . . yes O4 Ni1 C6 157.47(15) . . . yes O2 Ni1 C10 88.16(15) . . . yes O1 Ni1 C10 85.88(14) . . . yes N2 Ni1 C10 59.29(17) . . . yes N1 Ni1 C10 123.85(16) . . . yes O4 Ni1 C10 24.35(17) . . . yes O2 Ni1 C5 82.94(14) . . . yes O1 Ni1 C5 98.84(14) . . . yes N2 Ni1 C5 145.45(15) . . . yes N1 Ni1 C5 30.64(14) . . . yes O4 Ni1 C5 126.29(14) . . . yes O2 Ni1 C3 143.56(11) . . . yes O1 Ni1 C3 29.40(11) . . . yes N2 Ni1 C3 127.18(14) . . . yes N1 Ni1 C3 56.60(13) . . . yes O4 Ni1 C3 77.38(13) . . . yes O3 Ni1 C6 24.42(14) . . . yes O3 Ni1 C10 153.56(16) . . . yes C6 Ni1 C10 175.11(17) . . . yes O3 Ni1 C5 55.67(15) . . . yes C6 Ni1 C5 31.29(13) . . . yes C10 Ni1 C5 150.35(17) . . . yes O3 Ni1 C3 104.37(12) . . . yes C6 Ni1 C3 95.67(12) . . . yes C10 Ni1 C3 89.21(13) . . . yes C5 Ni1 C3 81.63(13) . . . yes _chemical_name_common (Ni(N-acetyl-(+)-ephedrine)!2$).2H!2$O data_6 _database_code_depnum_ccdc_archive 'CCDC 642795' _audit_creation_date 2007-06-07T16:03:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; [Ni(N-acetyl-(-)-ephedrine)~2~].2H~2~O ; _chemical_formula_moiety 'C24 H32 N2 Ni O6, 2(H2 O)' _chemical_formula_sum 'C24 H36 N2 Ni1 O8' _chemical_formula_weight 539.27 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_Int_Tables_number 1 loop_ _symmetry_equiv_pos_as_xyz x,y,z _cell_length_a 7.2261(3) _cell_length_b 8.9289(3) _cell_length_c 10.9475(4) _cell_angle_alpha 70.6653(16) _cell_angle_beta 81.6681(14) _cell_angle_gamma 82.4279(17) _cell_volume 656.81(4) _cell_formula_units_Z 1 _cell_measurement_temperature 293 _cell_measurement_reflns_used 2637 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'light blue' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 286 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.787 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.939 _exptl_absorpt_correction_T_max 0.9614 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.320859E-1 _diffrn_orient_matrix_ub_12 0.117493 _diffrn_orient_matrix_ub_13 -0.369325E-1 _diffrn_orient_matrix_ub_21 0.127493 _diffrn_orient_matrix_ub_22 0.194562E-1 _diffrn_orient_matrix_ub_23 0.135782E-1 _diffrn_orient_matrix_ub_31 0.493618E-1 _diffrn_orient_matrix_ub_32 -0.43089E-2 _diffrn_orient_matrix_ub_33 -0.890728E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0631 _diffrn_reflns_number 5043 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.3 _diffrn_reflns_theta_max 27.316 _diffrn_reflns_theta_full 25.404 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.986 _reflns_number_total 5043 _reflns_number_gt 4081 _reflns_threshold_expression I>3.0\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 97 (Sheldrick, 1997)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 F _refine_ls_matrix_type full _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: 0.546 0.673 0.783E-01 0.221 -0.403E-01 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method None _refine_ls_number_reflns 4081 _refine_ls_number_parameters 425 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.051 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0414 _refine_ls_wR_factor_gt 0.0414 _refine_ls_wR_factor_all 0.07 _refine_ls_goodness_of_fit_ref 1.0612 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000096 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack (1983), 2120 Friedel-pairs' _refine_ls_abs_structure_Flack 0.011(14) _refine_diff_density_max 0.37 _refine_diff_density_min -0.49 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Ni 0.3393 1.1124 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group C3 C 0.5067(5) 0.4750(4) 0.6482(3) 0.035 Uani 1 . . C4 C 0.5024(8) 0.3243(6) 0.6109(4) 0.0372 Uani 1 . . C5 C 0.2088(7) 0.4124(7) 0.5112(5) 0.0423 Uani 1 . . C6 C 0.1462(7) 0.5874(7) 0.4922(5) 0.0417 Uani 1 . . C7 C 0.3694(6) 0.8118(4) 0.1323(4) 0.0356 Uani 1 . . C8 C 0.5694(7) 0.8585(6) 0.1152(5) 0.036 Uani 1 . . C9 C 0.8413(7) 0.7610(6) 0.2503(5) 0.0392 Uani 1 . . C10 C 0.8867(7) 0.5872(6) 0.2565(5) 0.0361 Uani 1 . . C11 C 0.4436(9) 0.2520(7) 0.4188(5) 0.0455 Uani 1 . . C12 C 0.5840(9) 0.9373(7) 0.3069(6) 0.0496 Uani 1 . . C13 C 0.5698(6) 0.4369(5) 0.7835(4) 0.0394 Uani 1 . . C14 C 0.4439(7) 0.3693(5) 0.8903(4) 0.0481 Uani 1 . . C15 C 0.4917(9) 0.3298(6) 1.0170(4) 0.061 Uani 1 . . C16 C 0.6631(8) 0.3566(6) 1.0372(4) 0.0607 Uani 1 . . C17 C 0.7910(9) 0.4226(8) 0.9332(5) 0.0637 Uani 1 . . C18 C 0.7444(8) 0.4630(9) 0.8047(5) 0.0586 Uani 1 . . C19 C 0.2787(5) 0.8648(5) 0.0073(4) 0.0391 Uani 1 . . C20 C 0.1746(6) 1.0134(5) -0.0266(4) 0.0426 Uani 1 . . C21 C 0.0945(7) 1.0685(5) -0.1440(4) 0.0525 Uani 1 . . C22 C 0.1142(7) 0.9787(6) -0.2251(4) 0.0589 Uani 1 . . C23 C 0.2134(10) 0.8305(8) -0.1900(5) 0.0674 Uani 1 . . C24 C 0.2963(9) 0.7723(7) -0.0743(6) 0.0546 Uani 1 . . C25 C 0.6971(7) 0.2387(6) 0.6004(5) 0.0518 Uani 1 . . C26 C 0.7000(7) 0.7919(6) 0.0181(4) 0.0512 Uani 1 . . H1 H 0.739(8) 0.570(7) 0.553(5) 0.0557 Uiso 1 . . H2 H 0.281(6) 0.610(6) 0.203(5) 0.0502 Uiso 1 . . H3 H 0.381(6) 0.533(5) 0.664(4) 0.0406 Uiso 1 . . H4 H 0.430(6) 0.259(5) 0.683(4) 0.0416 Uiso 1 . . H7 H 0.285(6) 0.867(5) 0.192(4) 0.042 Uiso 1 . . H8 H 0.567(6) 0.979(5) 0.071(4) 0.0424 Uiso 1 . . H14 H 0.326(7) 0.358(6) 0.885(5) 0.0568 Uiso 1 . . H15 H 0.376(7) 0.315(6) 1.091(5) 0.0703 Uiso 1 . . H16 H 0.698(7) 0.324(6) 1.127(5) 0.073 Uiso 1 . . H17 H 0.905(9) 0.438(7) 0.944(6) 0.0779 Uiso 1 . . H18 H 0.834(8) 0.509(6) 0.737(5) 0.0692 Uiso 1 . . H20 H 0.153(6) 1.077(5) 0.038(4) 0.0483 Uiso 1 . . H21 H 0.013(7) 1.175(6) -0.168(5) 0.0593 Uiso 1 . . H22 H 0.054(8) 1.018(6) -0.299(5) 0.0669 Uiso 1 . . H23 H 0.241(9) 0.776(8) -0.252(6) 0.0819 Uiso 1 . . H24 H 0.375(7) 0.689(5) -0.058(5) 0.0655 Uiso 1 . . H51 H 0.152(6) 0.358(5) 0.605(3) 0.0485 Uiso 1 . . H52 H 0.144(7) 0.377(5) 0.451(4) 0.0482 Uiso 1 . . H71 H 1.042(15) 0.156(12) 0.299(6) 0.161 Uiso 1 . . H72 H 1.071(15) 0.313(6) 0.215(10) 0.1611 Uiso 1 . . H81 H 0.122(13) 0.895(10) 0.454(10) 0.1722 Uiso 1 . . H82 H -0.050(13) 0.935(14) 0.532(9) 0.172 Uiso 1 . . H91 H 0.877(6) 0.761(5) 0.332(4) 0.0471 Uiso 1 . . H92 H 0.920(6) 0.841(5) 0.170(4) 0.0473 Uiso 1 . . H111 H 0.396(8) 0.145(7) 0.479(5) 0.0718 Uiso 1 . . H112 H 0.575(5) 0.242(7) 0.393(5) 0.0716 Uiso 1 . . H113 H 0.360(8) 0.287(7) 0.346(5) 0.0715 Uiso 1 . . H121 H 0.612(6) 0.895(6) 0.396(3) 0.0734 Uiso 1 . . H122 H 0.665(6) 1.023(5) 0.256(4) 0.0737 Uiso 1 . . H123 H 0.453(4) 0.977(6) 0.305(4) 0.0732 Uiso 1 . . H251 H 0.692(6) 0.130(7) 0.588(4) 0.0788 Uiso 1 . . H252 H 0.758(7) 0.227(5) 0.684(6) 0.0789 Uiso 1 . . H253 H 0.777(7) 0.313(7) 0.524(5) 0.0789 Uiso 1 . . H261 H 0.699(6) 0.671(8) 0.055(5) 0.0757 Uiso 1 . . H262 H 0.831(9) 0.828(5) 0.003(4) 0.076 Uiso 1 . . H263 H 0.641(7) 0.831(5) -0.068(5) 0.076 Uiso 1 . . N1 N 0.4103(6) 0.3776(5) 0.4850(4) 0.0324 Uani 1 . . N2 N 0.6346(6) 0.8073(5) 0.2499(4) 0.0358 Uani 1 . . O1 O 0.6128(5) 0.5871(4) 0.5450(3) 0.0396 Uani 1 . . O2 O 0.3859(5) 0.6395(4) 0.1916(3) 0.0353 Uani 1 . . O3 O 0.2656(5) 0.6887(5) 0.4354(3) 0.0399 Uani 1 . . O4 O 0.7561(5) 0.4957(4) 0.3013(4) 0.0376 Uani 1 . . O5 O -0.0182(5) 0.6228(5) 0.5335(4) 0.0576 Uani 1 . . O6 O 1.0512(5) 0.5394(5) 0.2241(4) 0.0461 Uani 1 . . O7 O 1.0796(10) 0.2094(7) 0.2178(6) 0.1056 Uani 1 . . O8 O 0.0411(11) 0.9709(7) 0.4676(6) 0.1123 Uani 1 . . Ni1 Ni 0.5130(2) 0.59677(18) 0.36463(14) 0.0321 Uani 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 C3 0.0302(19) 0.0397(18) 0.0331(18) -0.0090(15) -0.0031(13) -0.0038(15) C4 0.045(3) 0.035(2) 0.0266(19) -0.0035(16) -0.0090(17) 0.0012(18) C5 0.029(2) 0.052(3) 0.041(2) -0.004(2) -0.0045(18) -0.0124(18) C6 0.027(3) 0.061(3) 0.031(2) -0.007(2) -0.0040(17) -0.003(2) C7 0.0343(19) 0.0348(18) 0.0352(18) -0.0064(15) -0.0115(14) 0.0014(15) C8 0.036(2) 0.035(2) 0.034(2) -0.0032(17) -0.0112(16) -0.0057(17) C9 0.028(2) 0.043(2) 0.047(3) -0.009(2) -0.0126(18) -0.0061(17) C10 0.028(2) 0.043(2) 0.036(2) -0.0106(18) -0.0063(17) -0.0006(18) C11 0.056(4) 0.043(3) 0.041(3) -0.017(2) -0.005(3) -0.010(3) C12 0.060(4) 0.039(3) 0.054(3) -0.021(3) -0.014(3) 0.002(3) C13 0.046(2) 0.0365(18) 0.0345(18) -0.0086(14) -0.0115(15) 0.0015(16) C14 0.056(3) 0.047(2) 0.039(2) -0.0084(17) -0.0034(18) -0.0115(19) C15 0.092(4) 0.057(3) 0.031(2) -0.0084(18) -0.003(2) -0.013(2) C16 0.092(4) 0.055(2) 0.036(2) -0.0110(19) -0.022(2) -0.001(2) C17 0.063(3) 0.089(4) 0.046(3) -0.026(3) -0.026(2) 0.003(3) C18 0.045(3) 0.095(4) 0.040(3) -0.027(3) -0.002(2) -0.010(3) C19 0.036(2) 0.0425(19) 0.0349(18) -0.0061(15) -0.0106(14) 0.0000(15) C20 0.040(2) 0.045(2) 0.0393(19) -0.0057(16) -0.0106(15) -0.0026(16) C21 0.053(2) 0.045(2) 0.051(2) -0.0013(18) -0.0162(19) 0.0007(18) C22 0.064(3) 0.066(3) 0.038(2) -0.001(2) -0.022(2) 0.001(2) C23 0.082(4) 0.079(4) 0.049(3) -0.027(3) -0.023(3) 0.000(3) C24 0.064(3) 0.052(3) 0.047(3) -0.013(2) -0.027(2) 0.012(2) C25 0.051(3) 0.049(2) 0.058(3) -0.023(2) -0.015(2) 0.0111(19) C26 0.041(2) 0.069(3) 0.041(2) -0.015(2) 0.0021(17) -0.010(2) N1 0.0280(19) 0.035(2) 0.0340(19) -0.0092(15) -0.0064(15) -0.0032(15) N2 0.036(2) 0.039(2) 0.0327(19) -0.0099(16) -0.0084(16) -0.0034(16) O1 0.0361(17) 0.0430(18) 0.0372(16) -0.0070(13) -0.0064(13) -0.0069(14) O2 0.0284(16) 0.0357(15) 0.0360(16) -0.0005(12) -0.0075(12) -0.0071(12) O3 0.034(2) 0.044(2) 0.0353(17) -0.0065(15) -0.0042(15) 0.0031(16) O4 0.0299(19) 0.0361(18) 0.0468(18) -0.0129(15) -0.0031(15) -0.0045(15) O5 0.0313(19) 0.081(2) 0.054(2) -0.0196(18) 0.0040(14) 0.0018(16) O6 0.0285(17) 0.0570(19) 0.0514(19) -0.0151(15) -0.0046(13) -0.0039(13) O7 0.128(5) 0.092(3) 0.106(4) -0.048(3) -0.010(3) 0.000(3) O8 0.155(6) 0.083(3) 0.100(4) -0.036(3) -0.026(4) 0.019(3) Ni1 0.0276(2) 0.0343(2) 0.0318(2) -0.00680(15) -0.00426(15) -0.00255(15) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C3 C4 1.535(6) . . yes C3 C13 1.530(5) . . yes C3 H3 1.00(4) . . no C3 O1 1.438(5) . . yes C4 C25 1.518(6) . . yes C4 H4 0.95(5) . . no C4 N1 1.522(6) . . yes C5 C6 1.522(8) . . yes C5 H51 1.03(3) . . no C5 H52 1.01(5) . . no C5 N1 1.455(6) . . yes C6 O3 1.275(6) . . yes C6 O5 1.247(6) . . yes C6 Ni1 2.809(5) . . yes C7 C8 1.525(6) . . yes C7 C19 1.508(5) . . yes C7 H7 1.03(3) . . no C7 O2 1.454(5) . . yes C8 C26 1.534(7) . . yes C8 H8 1.03(4) . . no C8 N2 1.518(6) . . yes C9 C10 1.524(7) . . yes C9 H91 0.96(5) . . no C9 H92 1.07(5) . . no C9 N2 1.497(6) . . yes C10 O4 1.266(6) . . yes C10 O6 1.252(6) . . yes C10 Ni1 2.789(5) . . yes C11 H111 1.04(6) . . no C11 H112 0.95(3) . . no C11 H113 1.01(6) . . no C11 N1 1.502(6) . . yes C12 H121 0.97(3) . . no C12 H122 0.99(3) . . no C12 H123 0.97(3) . . no C12 N2 1.473(7) . . yes C13 C14 1.389(6) . . yes C13 C18 1.378(7) . . yes C14 C15 1.397(6) . . yes C14 H14 0.89(5) . . no C15 C16 1.354(8) . . yes C15 H15 1.06(5) . . no C16 C17 1.376(8) . . yes C16 H16 0.99(6) . . no C17 C18 1.411(8) . . yes C17 H17 0.89(6) . . no C18 H18 0.93(6) . . no C19 C20 1.398(5) . . yes C19 C24 1.387(7) . . yes C20 C21 1.396(6) . . yes C20 H20 1.03(4) . . no C21 C22 1.363(7) . . yes C21 H21 1.02(5) . . no C22 C23 1.380(8) . . yes C22 H22 0.92(6) . . no C23 C24 1.391(8) . . yes C23 H23 0.95(6) . . no C24 H24 0.86(3) . . no C25 H251 1.03(6) . . no C25 H252 1.04(6) . . no C25 H253 1.03(7) . . no C26 H261 1.02(7) . . no C26 H262 1.02(6) . . no C26 H263 1.02(6) . . no H1 O1 0.92(6) . . no H2 O2 0.81(4) . . no H71 O7 0.88(4) . . no H72 O7 0.91(5) . . no H81 O8 0.87(5) . . no H82 O8 0.90(5) . . no N1 Ni1 2.124(4) . . yes N2 Ni1 2.106(4) . . yes O1 Ni1 2.170(3) . . yes O2 Ni1 2.124(3) . . yes O3 Ni1 2.026(3) . . yes O4 Ni1 2.006(3) . . yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 C3 C13 112.3(3) . . . yes C4 C3 H3 116(3) . . . no C13 C3 H3 98(2) . . . no C4 C3 O1 109.1(3) . . . yes C13 C3 O1 115.0(3) . . . yes H3 C3 O1 106(2) . . . no C3 C4 C25 111.6(4) . . . yes C3 C4 H4 103(3) . . . no C25 C4 H4 108(3) . . . no C3 C4 N1 106.2(3) . . . yes C25 C4 N1 113.7(4) . . . yes H4 C4 N1 113(3) . . . no C6 C5 H51 102(2) . . . no C6 C5 H52 108(3) . . . no H51 C5 H52 107(4) . . . no C6 C5 N1 114.5(4) . . . yes H51 C5 N1 116(3) . . . no H52 C5 N1 108(3) . . . no C5 C6 O3 117.9(4) . . . yes C5 C6 O5 118.0(5) . . . yes O3 C6 O5 124.1(5) . . . yes C5 C6 Ni1 77.1(3) . . . yes O5 C6 Ni1 164.5(4) . . . yes C8 C7 C19 113.8(3) . . . yes C8 C7 H7 109(3) . . . no C19 C7 H7 105(2) . . . no C8 C7 O2 104.6(3) . . . yes C19 C7 O2 112.6(3) . . . yes H7 C7 O2 112(3) . . . no C7 C8 C26 112.5(4) . . . yes C7 C8 H8 108(2) . . . no C26 C8 H8 103(2) . . . no C7 C8 N2 107.1(4) . . . yes C26 C8 N2 113.9(4) . . . yes H8 C8 N2 112(2) . . . no C10 C9 H91 103(3) . . . no C10 C9 H92 113(2) . . . no H91 C9 H92 110(3) . . . no C10 C9 N2 110.9(4) . . . yes H91 C9 N2 108(3) . . . no H92 C9 N2 112(2) . . . no C9 C10 O4 117.6(4) . . . yes C9 C10 O6 119.3(5) . . . yes O4 C10 O6 123.0(5) . . . yes C9 C10 Ni1 77.0(3) . . . yes O6 C10 Ni1 162.9(4) . . . yes H111 C11 H112 112(4) . . . no H111 C11 H113 104(4) . . . no H112 C11 H113 116(4) . . . no H111 C11 N1 112(3) . . . no H112 C11 N1 107(4) . . . no H113 C11 N1 107(3) . . . no H121 C12 H122 111(3) . . . no H121 C12 H123 109(3) . . . no H122 C12 H123 110(3) . . . no H121 C12 N2 107(3) . . . no H122 C12 N2 106(3) . . . no H123 C12 N2 113(3) . . . no C3 C13 C14 117.5(4) . . . yes C3 C13 C18 123.8(4) . . . yes C14 C13 C18 118.7(4) . . . yes C13 C14 C15 120.9(4) . . . yes C13 C14 H14 124(3) . . . no C15 C14 H14 115(3) . . . no C14 C15 C16 120.1(4) . . . yes C14 C15 H15 115(3) . . . no C16 C15 H15 122(3) . . . no C15 C16 C17 120.2(4) . . . yes C15 C16 H16 120(3) . . . no C17 C16 H16 120(3) . . . no C16 C17 C18 120.3(6) . . . yes C16 C17 H17 122(4) . . . no C18 C17 H17 118(4) . . . no C17 C18 C13 119.8(5) . . . yes C17 C18 H18 118(3) . . . no C13 C18 H18 122(3) . . . no C7 C19 C20 118.1(3) . . . yes C7 C19 C24 122.4(4) . . . yes C20 C19 C24 119.5(4) . . . yes C19 C20 C21 119.5(4) . . . yes C19 C20 H20 119(2) . . . no C21 C20 H20 122(2) . . . no C20 C21 C22 121.0(4) . . . yes C20 C21 H21 120(3) . . . no C22 C21 H21 118(3) . . . no C21 C22 C23 119.4(4) . . . yes C21 C22 H22 118(3) . . . no C23 C22 H22 123(3) . . . no C22 C23 C24 121.2(5) . . . yes C22 C23 H23 118(4) . . . no C24 C23 H23 120(4) . . . no C23 C24 C19 119.4(5) . . . yes C23 C24 H24 122(4) . . . no C19 C24 H24 118(4) . . . no C4 C25 H251 111(2) . . . no C4 C25 H252 108(2) . . . no H251 C25 H252 112(3) . . . no C4 C25 H253 107(2) . . . no H251 C25 H253 112(3) . . . no H252 C25 H253 106(3) . . . no C8 C26 H261 106(2) . . . no C8 C26 H262 113(2) . . . no H261 C26 H262 112(3) . . . no C8 C26 H263 107(2) . . . no H261 C26 H263 109(3) . . . no H262 C26 H263 110(3) . . . no C4 N1 C11 111.5(4) . . . yes C4 N1 C5 110.4(4) . . . yes C11 N1 C5 108.7(4) . . . yes C4 N1 Ni1 108.1(3) . . . yes C11 N1 Ni1 112.3(3) . . . yes C5 N1 Ni1 105.7(3) . . . yes C8 N2 C9 113.4(4) . . . yes C8 N2 C12 109.5(4) . . . yes C9 N2 C12 109.2(4) . . . yes C8 N2 Ni1 108.7(3) . . . yes C9 N2 Ni1 103.8(3) . . . yes C12 N2 Ni1 112.2(3) . . . yes C3 O1 H1 112(3) . . . no C3 O1 Ni1 106.5(3) . . . yes H1 O1 Ni1 119(3) . . . no C7 O2 H2 108(4) . . . no C7 O2 Ni1 105.1(2) . . . yes H2 O2 Ni1 115(4) . . . no C6 O3 Ni1 114.7(3) . . . yes C10 O4 Ni1 115.0(3) . . . yes H72 O7 H71 105(9) . . . no H82 O8 H81 113(11) . . . no O1 Ni1 O2 170.50(14) . . . yes O1 Ni1 N1 81.69(14) . . . yes O2 Ni1 N1 102.02(14) . . . yes O1 Ni1 N2 95.72(14) . . . yes O2 Ni1 N2 81.06(14) . . . yes N1 Ni1 N2 175.76(19) . . . yes O1 Ni1 O3 85.42(13) . . . yes O2 Ni1 O3 86.40(13) . . . yes N1 Ni1 O3 82.59(15) . . . yes N2 Ni1 O3 100.59(15) . . . yes O1 Ni1 O4 93.57(13) . . . yes O2 Ni1 O4 94.82(13) . . . yes N1 Ni1 O4 94.72(14) . . . yes N2 Ni1 O4 82.06(15) . . . yes O3 Ni1 O4 177.24(18) . . . yes O1 Ni1 C10 88.06(13) . . . yes O2 Ni1 C10 97.80(13) . . . yes N1 Ni1 C10 117.27(15) . . . yes N2 Ni1 C10 59.12(15) . . . yes O3 Ni1 C10 157.94(16) . . . yes O1 Ni1 C6 88.41(14) . . . yes O2 Ni1 C6 86.11(13) . . . yes N1 Ni1 C6 59.06(16) . . . yes N2 Ni1 C6 124.40(16) . . . yes O3 Ni1 C6 24.35(15) . . . yes O4 Ni1 C10 24.29(14) . . . yes O4 Ni1 C6 153.17(16) . . . yes C10 Ni1 C6 175.29(16) . . . yes _chemical_name_common (Ni(N-acetyl-(-)-ephedrine)!2$).2H!2$O data_7 _database_code_depnum_ccdc_archive 'CCDC 642796' _audit_creation_date 2007-06-22T17:05:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; [Ni(N-acetyl-(+)-pseudoephedrine)~2~].2H~2~O ; _chemical_formula_moiety 'C24 H32 N2 Ni O6, 2(H2 O)' _chemical_formula_sum 'C24 H36 N2 Ni1 O8' _chemical_formula_weight 539.27 _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M 'P 3' _symmetry_space_group_name_Hall 'P 3' loop_ _symmetry_equiv_pos_as_xyz x,y,z -y,x-y,z -x+y,-x,z _cell_length_a 17.611(12) _cell_length_b 17.611(12) _cell_length_c 7.158(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 1923(2) _cell_formula_units_Z 3 _cell_measurement_temperature 293 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 858 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.806 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9375 _exptl_absorpt_correction_T_max 0.9605 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Unknown _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.074 _diffrn_reflns_av_unetI/netI 0.0773 _diffrn_reflns_number 23449 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.534 _diffrn_reflns_theta_max 27.107 _diffrn_reflns_theta_full 26.294 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 5490 _reflns_number_gt 2896 _reflns_threshold_expression I>3.0\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_structure_solution 'SHELXS 97 (Sheldrick, 1997)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 F _refine_ls_matrix_type full _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: 2.77 -2.51 3.01 -0.921 0.707 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method None _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0058(10) _refine_ls_number_reflns 2896 _refine_ls_number_parameters 317 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.031 _refine_ls_wR_factor_ref 0.0346 _refine_ls_wR_factor_gt 0.0346 _refine_ls_wR_factor_all 0.0607 _refine_ls_goodness_of_fit_ref 1.0815 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000439 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack (1983), 2670 Friedel-pairs' _refine_ls_abs_structure_Flack 0.018(19) _refine_diff_density_max 0.25 _refine_diff_density_min -0.39 _refine_diff_density_rms 0.065 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Ni 0.3393 1.1124 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group C3 C 0.9349(3) 0.3544(2) 0.1797(6) 0.0246 Uani 1 . . C4 C 0.9242(3) 0.3649(3) -0.0307(6) 0.0262 Uani 1 . . C5 C 0.8654(4) 0.2711(3) -0.3028(7) 0.0327 Uani 1 . . C6 C 0.9257(3) 0.2312(3) -0.3143(7) 0.0334 Uani 1 . . C7 C 0.6977(3) -0.0095(3) -0.0163(5) 0.025 Uani 1 . . C8 C 0.7752(3) -0.0175(3) 0.0601(7) 0.0308 Uani 1 . . C9 C 0.7962(4) 0.0595(4) 0.3659(7) 0.0378 Uani 1 . . C10 C 0.7433(3) 0.1070(3) 0.3724(8) 0.0315 Uani 1 . . C11 C 0.7622(3) 0.2823(4) -0.0903(8) 0.041 Uani 1 . . C12 C 0.9227(3) 0.0720(4) 0.1938(9) 0.0465 Uani 1 . . C13 C 1.0168(3) 0.4353(3) 0.2538(6) 0.0272 Uani 1 . . C14 C 1.0102(3) 0.4941(3) 0.3737(6) 0.0315 Uani 1 . . C15 C 1.0844(3) 0.5715(3) 0.4276(7) 0.038 Uani 1 . . C16 C 1.1666(3) 0.5903(3) 0.3651(7) 0.039 Uani 1 . . C17 C 1.1755(3) 0.5322(3) 0.2451(7) 0.0358 Uani 1 . . C18 C 1.1001(3) 0.4539(3) 0.1918(7) 0.0305 Uani 1 . . C19 C 0.6352(3) -0.0904(3) -0.1297(7) 0.0274 Uani 1 . . C20 C 0.5466(3) -0.1363(3) -0.0767(7) 0.0312 Uani 1 . . C21 C 0.4885(4) -0.2168(3) -0.1625(8) 0.0416 Uani 1 . . C22 C 0.5180(4) -0.2518(3) -0.2952(8) 0.0455 Uani 1 . . C23 C 0.6052(4) -0.2063(4) -0.3529(8) 0.0469 Uani 1 . . C24 C 0.6635(4) -0.1258(3) -0.2698(7) 0.0368 Uani 1 . . C25 C 0.9230(4) 0.4504(3) -0.0748(8) 0.0371 Uani 1 . . C26 C 0.7428(4) -0.1051(3) 0.1658(9) 0.0445 Uani 1 . . H1 H 0.9522 0.2708 0.3075 0.0411 Uiso 1 . . H2 H 0.7229 0.0764 -0.2318 0.0479 Uiso 1 . . H3 H 0.8817 0.3465 0.2444 0.0327 Uiso 1 . . H4 H 0.9757 0.369 -0.0947 0.0286 Uiso 1 . . H7 H 0.6639 -0.0041 0.0879 0.029 Uiso 1 . . H8 H 0.8107 -0.0171 -0.0482 0.036 Uiso 1 . . H14 H 0.9545 0.4829 0.4137 0.0381 Uiso 1 . . H15 H 1.0788 0.6102 0.5089 0.0402 Uiso 1 . . H16 H 1.2171 0.6423 0.4037 0.037 Uiso 1 . . H17 H 1.2319 0.5447 0.205 0.0401 Uiso 1 . . H18 H 1.1062 0.4148 0.1118 0.0361 Uiso 1 . . H20 H 0.5253 -0.1129 0.0148 0.0352 Uiso 1 . . H21 H 0.4281 -0.2473 -0.1253 0.0395 Uiso 1 . . H22 H 0.4787 -0.3067 -0.3506 0.0441 Uiso 1 . . H23 H 0.6262 -0.2288 -0.4458 0.0558 Uiso 1 . . H24 H 0.7222 -0.0955 -0.3082 0.042 Uiso 1 . . H51 H 0.8099 0.2292 -0.3602 0.0359 Uiso 1 . . H52 H 0.8913 0.3264 -0.3699 0.0358 Uiso 1 . . H71 H -0.0176 0.0586 0.6965 0.151 Uiso 1 . . H72 H 0.0274 0.1529 0.6645 0.151 Uiso 1 . . H81 H 0.7184 0.4236 0.4139 0.1612 Uiso 1 . . H82 H 0.8193 0.4639 0.3996 0.1611 Uiso 1 . . H91 H 0.7589 -0.0014 0.4049 0.0358 Uiso 1 . . H92 H 0.8442 0.0881 0.453 0.0363 Uiso 1 . . H111 H 0.7518 0.294 0.0381 0.0589 Uiso 1 . . H112 H 0.763 0.3264 -0.1742 0.0589 Uiso 1 . . H113 H 0.7152 0.2247 -0.1276 0.0586 Uiso 1 . . H121 H 0.9172 0.0206 0.2588 0.0558 Uiso 1 . . H122 H 0.9603 0.1251 0.2656 0.0561 Uiso 1 . . H123 H 0.9476 0.0766 0.0685 0.0559 Uiso 1 . . H251 H 0.8865 0.4587 0.0154 0.0556 Uiso 1 . . H252 H 0.9821 0.4986 -0.0658 0.0559 Uiso 1 . . H253 H 0.9013 0.4477 -0.2012 0.0559 Uiso 1 . . H261 H 0.7868 -0.1012 0.2524 0.0548 Uiso 1 . . H262 H 0.6901 -0.1195 0.2358 0.0545 Uiso 1 . . H263 H 0.7302 -0.1508 0.0748 0.0547 Uiso 1 . . N1 N 0.8463(3) 0.2820(3) -0.1035(6) 0.0278 Uani 1 . . N2 N 0.8336(3) 0.0626(3) 0.1762(6) 0.0294 Uani 1 . . O1 O 0.9405(2) 0.2746(2) 0.1953(5) 0.0286 Uani 1 . . O2 O 0.7361(3) 0.0725(2) -0.1215(6) 0.0416 Uani 1 . . O3 O 0.9271(2) 0.1878(2) -0.1690(5) 0.0335 Uani 1 . . O4 O 0.7504(2) 0.1581(2) 0.2412(5) 0.0321 Uani 1 . . O5 O 0.9695(2) 0.2408(2) -0.4604(5) 0.042 Uani 1 . . O6 O 0.6962(2) 0.0939(2) 0.5209(5) 0.0394 Uani 1 . . O7 O 0.0273(4) 0.1056(5) 0.6647(13) 0.1521 Uani 1 . . O8 O 0.7681(4) 0.4125(3) 0.4377(14) 0.1472 Uani 1 . . Ni1 Ni 0.83982(5) 0.17360(4) 0.03774(18) 0.026 Uani 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 C3 0.030(2) 0.018(2) 0.022(2) -0.0010(17) -0.0037(18) 0.0089(19) C4 0.029(2) 0.020(2) 0.028(2) -0.0033(18) -0.0036(18) 0.0109(19) C5 0.038(3) 0.028(2) 0.027(3) -0.006(2) -0.010(2) 0.013(2) C6 0.039(3) 0.028(3) 0.023(3) -0.002(2) -0.011(2) 0.009(2) C7 0.027(2) 0.024(2) 0.019(2) -0.0012(17) -0.0034(17) 0.0091(18) C8 0.031(2) 0.025(2) 0.033(2) -0.0028(19) -0.002(2) 0.011(2) C9 0.044(3) 0.032(3) 0.030(3) 0.007(2) -0.003(2) 0.014(2) C10 0.029(3) 0.027(3) 0.029(3) -0.004(2) 0.005(2) 0.007(2) C11 0.037(3) 0.037(3) 0.044(3) 0.006(2) 0.001(2) 0.015(2) C12 0.029(3) 0.037(3) 0.075(4) -0.004(3) -0.012(3) 0.018(2) C13 0.030(2) 0.024(2) 0.025(2) 0.0003(18) -0.0045(19) 0.0117(19) C14 0.035(3) 0.036(3) 0.026(2) -0.001(2) 0.000(2) 0.020(2) C15 0.052(3) 0.026(3) 0.032(3) 0.001(2) -0.004(2) 0.016(2) C16 0.035(3) 0.035(3) 0.030(3) 0.003(2) -0.007(2) 0.005(2) C17 0.026(2) 0.049(3) 0.028(3) 0.002(2) -0.006(2) 0.015(2) C18 0.034(3) 0.034(3) 0.026(3) -0.005(2) -0.004(2) 0.019(2) C19 0.030(2) 0.022(2) 0.028(3) -0.0015(18) -0.005(2) 0.012(2) C20 0.034(2) 0.031(2) 0.028(2) 0.0041(19) 0.000(2) 0.015(2) C21 0.034(3) 0.027(3) 0.047(4) 0.005(2) -0.008(3) 0.003(2) C22 0.060(4) 0.026(3) 0.037(3) -0.009(2) -0.016(3) 0.011(3) C23 0.074(4) 0.044(3) 0.030(3) -0.012(2) -0.004(3) 0.035(3) C24 0.037(3) 0.035(3) 0.032(3) -0.006(2) -0.001(2) 0.013(2) C25 0.048(3) 0.024(2) 0.037(3) -0.003(2) -0.018(2) 0.016(2) C26 0.042(3) 0.022(2) 0.062(4) 0.001(2) -0.013(3) 0.011(2) N1 0.025(2) 0.027(2) 0.030(3) 0.0003(19) -0.0026(18) 0.0120(18) N2 0.023(2) 0.028(2) 0.033(2) -0.0060(19) -0.0061(18) 0.0103(18) O1 0.0332(19) 0.0238(18) 0.0263(19) 0.0002(15) -0.0053(15) 0.0124(15) O2 0.057(3) 0.0210(18) 0.033(2) 0.0056(15) -0.0134(19) 0.0087(18) O3 0.040(2) 0.0339(19) 0.028(2) 0.0001(16) 0.0037(16) 0.0202(17) O4 0.039(2) 0.0313(18) 0.027(2) 0.0023(16) -0.0017(16) 0.0182(16) O5 0.051(2) 0.051(2) 0.022(2) 0.0042(17) 0.0053(17) 0.0237(19) O6 0.036(2) 0.041(2) 0.032(2) -0.0065(17) -0.0075(17) 0.0133(17) O7 0.089(5) 0.095(5) 0.297(11) -0.069(6) -0.046(6) 0.065(4) O8 0.069(4) 0.045(3) 0.318(10) 0.013(5) 0.034(5) 0.021(3) Ni1 0.0295(4) 0.0211(3) 0.0240(2) 0.0000(2) -0.0017(2) 0.0101(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C3 C4 1.541(6) . . yes C3 C13 1.529(6) . . yes C3 H3 0.991 . . no C3 O1 1.460(5) . . yes C4 C25 1.548(6) . . yes C4 H4 0.986 . . no C4 N1 1.510(6) . . yes C5 C6 1.542(7) . . yes C5 H51 0.974 . . no C5 H52 0.972 . . no C5 N1 1.500(7) . . yes C6 O3 1.297(6) . . yes C6 O5 1.260(6) . . yes C6 Ni1 2.852(6) . . yes C7 C8 1.542(6) . . yes C7 C19 1.527(6) . . yes C7 H7 0.988 . . no C7 O2 1.461(5) . . yes C8 C26 1.549(7) . . yes C8 H8 0.993 . . no C8 N2 1.512(6) . . yes C9 C10 1.533(8) . . yes C9 H91 0.977 . . no C9 H92 0.965 . . no C9 N2 1.498(7) . . yes C10 O4 1.263(6) . . yes C10 O6 1.296(6) . . yes C10 Ni1 2.831(6) . . yes C11 H111 0.979 . . no C11 H112 0.976 . . no C11 H113 0.972 . . no C11 N1 1.487(7) . . yes C12 H121 0.978 . . no C12 H122 0.978 . . no C12 H123 0.984 . . no C12 N2 1.500(6) . . yes C13 C14 1.395(6) . . yes C13 C18 1.406(7) . . yes C14 C15 1.390(7) . . yes C14 H14 0.944 . . no C15 C16 1.388(7) . . yes C15 H15 0.938 . . no C16 C17 1.404(8) . . yes C16 H16 0.944 . . no C17 C18 1.407(7) . . yes C17 H17 0.947 . . no C18 H18 0.94 . . no C19 C20 1.404(6) . . yes C19 C24 1.397(6) . . yes C20 C21 1.409(7) . . yes C20 H20 0.946 . . no C21 C22 1.367(8) . . yes C21 H21 0.959 . . no C22 C23 1.393(8) . . yes C22 H22 0.95 . . no C23 C24 1.401(8) . . yes C23 H23 0.94 . . no C24 H24 0.937 . . no C25 H251 0.973 . . no C25 H252 0.962 . . no C25 H253 0.973 . . no C26 H261 0.968 . . no C26 H262 0.971 . . no C26 H263 0.97 . . no H1 O1 0.84 . . no H2 O2 0.835 . . no H71 O7 0.841 . . no H72 O7 0.833 . . no H81 O8 1.003 . . no H82 O8 0.944 . . no N1 Ni1 2.113(4) . . yes N2 Ni1 2.145(5) . . yes O1 Ni1 2.104(3) . . yes O2 Ni1 2.134(4) . . yes O3 Ni1 2.057(4) . . yes O4 Ni1 2.060(4) . . yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 C3 C13 110.0(3) . . . yes C4 C3 H3 108 . . . no C13 C3 H3 110.7 . . . no C4 C3 O1 105.2(3) . . . yes C13 C3 O1 112.6(3) . . . yes H3 C3 O1 110.1 . . . no C3 C4 C25 112.3(4) . . . yes C3 C4 H4 107.3 . . . no C25 C4 H4 107.1 . . . no C3 C4 N1 109.1(3) . . . yes C25 C4 N1 115.0(4) . . . yes H4 C4 N1 105.5 . . . no C6 C5 H51 107 . . . no C6 C5 H52 110.2 . . . no H51 C5 H52 109.9 . . . no C6 C5 N1 111.1(4) . . . yes H51 C5 N1 107.1 . . . no H52 C5 N1 111.4 . . . no C5 C6 O3 116.4(5) . . . yes C5 C6 O5 119.9(5) . . . yes O3 C6 O5 123.7(5) . . . yes C5 C6 Ni1 75.6(3) . . . yes O5 C6 Ni1 164.1(4) . . . yes C8 C7 C19 111.2(3) . . . yes C8 C7 H7 110.1 . . . no C19 C7 H7 107.7 . . . no C8 C7 O2 106.2(4) . . . yes C19 C7 O2 114.2(3) . . . yes H7 C7 O2 107.3 . . . no C7 C8 C26 111.2(4) . . . yes C7 C8 H8 107.8 . . . no C26 C8 H8 107.7 . . . no C7 C8 N2 109.3(4) . . . yes C26 C8 N2 113.6(4) . . . yes H8 C8 N2 107 . . . no C10 C9 H91 109.3 . . . no C10 C9 H92 108 . . . no H91 C9 H92 108.8 . . . no C10 C9 N2 112.5(4) . . . yes H91 C9 N2 110 . . . no H92 C9 N2 108.2 . . . no C9 C10 O4 119.7(4) . . . yes C9 C10 O6 116.0(5) . . . yes O4 C10 O6 124.2(5) . . . yes C9 C10 Ni1 78.3(3) . . . yes O6 C10 Ni1 165.0(4) . . . yes H111 C11 H112 110 . . . no H111 C11 H113 109 . . . no H112 C11 H113 109.1 . . . no H111 C11 N1 110.5 . . . no H112 C11 N1 110.2 . . . no H113 C11 N1 108 . . . no H121 C12 H122 109.9 . . . no H121 C12 H123 110.1 . . . no H122 C12 H123 109.9 . . . no H121 C12 N2 108.9 . . . no H122 C12 N2 108.6 . . . no H123 C12 N2 109.4 . . . no C3 C13 C14 121.1(4) . . . yes C3 C13 C18 119.7(4) . . . yes C14 C13 C18 119.1(4) . . . yes C13 C14 C15 120.9(5) . . . yes C13 C14 H14 119.7 . . . no C15 C14 H14 119.4 . . . no C14 C15 C16 120.1(5) . . . yes C14 C15 H15 119.7 . . . no C16 C15 H15 120.2 . . . no C15 C16 C17 120.4(5) . . . yes C15 C16 H16 120.1 . . . no C17 C16 H16 119.5 . . . no C16 C17 C18 119.1(5) . . . yes C16 C17 H17 120.1 . . . no C18 C17 H17 120.8 . . . no C17 C18 C13 120.4(4) . . . yes C17 C18 H18 119.1 . . . no C13 C18 H18 120.5 . . . no C7 C19 C20 117.9(4) . . . yes C7 C19 C24 123.1(4) . . . yes C20 C19 C24 118.6(4) . . . yes C19 C20 C21 120.0(5) . . . yes C19 C20 H20 120.4 . . . no C21 C20 H20 119.6 . . . no C20 C21 C22 120.6(5) . . . yes C20 C21 H21 119.1 . . . no C22 C21 H21 120.4 . . . no C21 C22 C23 120.3(5) . . . yes C21 C22 H22 120.1 . . . no C23 C22 H22 119.6 . . . no C22 C23 C24 119.7(5) . . . yes C22 C23 H23 121.4 . . . no C24 C23 H23 118.9 . . . no C23 C24 C19 120.8(5) . . . yes C23 C24 H24 119.6 . . . no C19 C24 H24 119.6 . . . no C4 C25 H251 110 . . . no C4 C25 H252 108 . . . no H251 C25 H252 109.2 . . . no C4 C25 H253 109.7 . . . no H251 C25 H253 110.7 . . . no H252 C25 H253 109.3 . . . no C8 C26 H261 111 . . . no C8 C26 H262 109.8 . . . no H261 C26 H262 108.4 . . . no C8 C26 H263 108.4 . . . no H261 C26 H263 109.3 . . . no H262 C26 H263 109.8 . . . no C4 N1 C5 107.4(4) . . . yes C4 N1 C11 113.6(4) . . . yes C5 N1 C11 110.4(4) . . . yes C4 N1 Ni1 108.7(3) . . . yes C5 N1 Ni1 104.6(3) . . . yes C11 N1 Ni1 111.7(3) . . . yes C8 N2 C12 109.5(4) . . . yes C8 N2 C9 112.5(4) . . . yes C12 N2 C9 110.2(4) . . . yes C8 N2 Ni1 107.3(3) . . . yes C12 N2 Ni1 111.4(3) . . . yes C9 N2 Ni1 105.9(3) . . . yes C3 O1 H1 106.7 . . . no C3 O1 Ni1 109.8(2) . . . yes H1 O1 Ni1 125.5 . . . no C7 O2 H2 123.9 . . . no C7 O2 Ni1 109.2(3) . . . yes H2 O2 Ni1 126.4 . . . no C6 O3 Ni1 114.6(3) . . . yes C10 O4 Ni1 114.7(3) . . . yes H71 O7 H72 121 . . . no H81 O8 H82 105.7 . . . no N2 Ni1 O2 81.62(15) . . . yes N2 Ni1 N1 178.9(2) . . . yes O2 Ni1 N1 97.77(17) . . . yes N2 Ni1 O1 99.22(15) . . . yes O2 Ni1 O1 178.79(19) . . . yes N1 Ni1 O1 81.40(15) . . . yes N2 Ni1 O4 82.21(15) . . . yes O2 Ni1 O4 89.32(17) . . . yes N1 Ni1 O4 98.66(16) . . . yes O1 Ni1 O4 89.93(14) . . . yes N2 Ni1 O3 97.96(16) . . . yes O2 Ni1 O3 89.60(16) . . . yes N1 Ni1 O3 81.16(16) . . . yes O1 Ni1 O3 91.15(16) . . . yes O4 Ni1 O3 178.87(18) . . . yes N2 Ni1 C10 58.97(16) . . . yes O2 Ni1 C10 91.15(17) . . . yes N1 Ni1 C10 121.96(15) . . . yes O1 Ni1 C10 88.55(16) . . . yes O4 Ni1 C10 23.91(14) . . . yes N2 Ni1 C6 120.58(16) . . . yes O2 Ni1 C6 84.56(16) . . . yes N1 Ni1 C6 58.45(17) . . . yes O1 Ni1 C6 95.73(15) . . . yes O4 Ni1 C6 155.00(14) . . . yes O3 Ni1 C10 156.48(15) . . . yes O3 Ni1 C6 24.43(14) . . . yes C10 Ni1 C6 175.69(18) . . . yes _chemical_name_common (Ni(N-acetyl-(+)-pseudoephedrine)!2$).2H!2$O data_publish8 _database_code_depnum_ccdc_archive 'CCDC 642797' # Attachment 'Ni6(-).cif' _audit_creation_date 2007-02-09T12:39:03-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; [Ni(N-(-)-acetyl-phenylephrine)~2~].2H~2~O ; _chemical_formula_moiety 'C22 H28 N2 Ni O8, 2(H2 O)' _chemical_formula_sum 'C22 H32 N2 Ni1 O10' _chemical_formula_weight 543.21 _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z _cell_length_a 7.369(2) _cell_length_b 7.3700(19) _cell_length_c 11.279(3) _cell_angle_alpha 76.023(14) _cell_angle_beta 85.64(2) _cell_angle_gamma 84.945(18) _cell_volume 591.2(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description unknown _exptl_crystal_colour unknown _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 286 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.881 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7219 _exptl_absorpt_correction_T_max 0.8024 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Unknown _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0327 _diffrn_reflns_number 3189 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.864 _diffrn_reflns_theta_max 26.988 _diffrn_reflns_theta_full 26.988 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 3189 _reflns_number_gt 3097 _reflns_threshold_expression I>3.0\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_structure_solution 'SHELXS 97 (Sheldrick, 1997)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method None _refine_ls_number_reflns 3097 _refine_ls_number_parameters 317 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0312 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0413 _refine_ls_wR_factor_gt 0.0413 _refine_ls_wR_factor_all 0.0429 _refine_ls_goodness_of_fit_ref 1.0076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.00022 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' _refine_ls_abs_structure_Flack 0.013(14) _refine_diff_density_max 0.362 _refine_diff_density_min -0.619 _refine_diff_density_rms 0.069 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Ni 0.3393 1.1124 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group C3 C 0.5759(4) 0.3879(4) 0.7550(2) 0.0273 Uani 1 . . C4 C 0.3808(4) 0.3466(4) 0.7448(2) 0.0274 Uani 1 . . C5 C 0.1084(4) 0.2626(4) 0.8695(3) 0.0254 Uani 1 . . C6 C 0.0635(4) 0.4329(4) 0.9231(3) 0.023 Uani 1 . . C7 C 0.3534(4) 0.1039(4) 1.2614(2) 0.0263 Uani 1 . . C8 C 0.3855(5) 0.3058(4) 1.2590(2) 0.028 Uani 1 . . C9 C 0.6975(4) 0.3040(4) 1.1681(3) 0.0281 Uani 1 . . C10 C 0.7516(5) 0.1437(4) 1.1035(3) 0.0247 Uani 1 . . C11 C 0.3481(5) 0.0190(5) 0.8561(4) 0.0356 Uani 1 . . C12 C 0.5011(5) 0.5919(4) 1.1310(3) 0.0333 Uani 1 . . C13 C 0.6397(4) 0.5259(4) 0.6395(3) 0.0274 Uani 1 . . C14 C 0.7290(5) 0.4531(4) 0.5467(3) 0.0321 Uani 1 . . C15 C 0.7845(6) 0.5749(5) 0.4351(3) 0.0345 Uani 1 . . C16 C 0.7472(6) 0.7648(5) 0.4179(3) 0.0368 Uani 1 . . C17 C 0.6554(6) 0.8376(5) 0.5110(3) 0.0376 Uani 1 . . C18 C 0.6019(5) 0.7184(5) 0.6221(3) 0.035 Uani 1 . . C19 C 0.2461(4) 0.0009(4) 1.3740(3) 0.0262 Uani 1 . . C20 C 0.1592(5) 0.0881(4) 1.4601(3) 0.031 Uani 1 . . C21 C 0.0776(6) -0.0171(5) 1.5680(3) 0.0326 Uani 1 . . C22 C 0.0846(5) -0.2100(5) 1.5900(3) 0.032 Uani 1 . . C23 C 0.1683(5) -0.2984(5) 1.5007(3) 0.0352 Uani 1 . . C24 C 0.2478(5) -0.1939(5) 1.3941(3) 0.0338 Uani 1 . . H1 H 0.6778 0.4726 0.8728 0.043 Uiso 1 . . H2 H 0.1621 0.1027 1.1584 0.043 Uiso 1 . . H3 H 0.6558 0.2745 0.7652 0.0321 Uiso 1 . . H7 H 0.4742 0.0359 1.2606 0.032 Uiso 1 . . H8 H -0.057 0.0052 1.7075 0.0698 Uiso 1 . . H14 H 0.7527 0.326 0.5574 0.0382 Uiso 1 . . H16 H 0.7864 0.8445 0.3452 0.0407 Uiso 1 . . H17 H 0.6305 0.965 0.4981 0.0441 Uiso 1 . . H18 H 0.5388 0.768 0.6825 0.0411 Uiso 1 . . H20 H 0.1549 0.2169 1.4477 0.0372 Uiso 1 . . H22 H 0.0303 -0.2793 1.6616 0.0368 Uiso 1 . . H23 H 0.1688 -0.4278 1.5133 0.0409 Uiso 1 . . H24 H 0.3028 -0.2535 1.3361 0.0408 Uiso 1 . . H41 H 0.3763 0.2891 0.6763 0.0321 Uiso 1 . . H42 H 0.3045 0.4615 0.7292 0.0319 Uiso 1 . . H51 H 0.0602 0.2891 0.7878 0.0319 Uiso 1 . . H52 H 0.0499 0.1583 0.9236 0.0321 Uiso 1 . . H71 H 0.9434 0.5594 0.2979 0.079 Uiso 1 . . H81 H 0.269 0.3766 1.2567 0.0326 Uiso 1 . . H82 H 0.4441 0.3091 1.3335 0.033 Uiso 1 . . H91 H 0.7799 0.4006 1.1364 0.0349 Uiso 1 . . H92 H 0.7142 0.2557 1.2566 0.0349 Uiso 1 . . H101 H 0.8271 0.7863 0.8894 0.0708 Uiso 1 . . H102 H 0.7947 0.9519 0.9204 0.0708 Uiso 1 . . H111 H 0.3057 -0.058 0.9331 0.0539 Uiso 1 . . H112 H 0.2874 -0.0085 0.7891 0.0538 Uiso 1 . . H113 H 0.4789 -0.0037 0.8448 0.0535 Uiso 1 . . H121 H 0.5707 0.6427 1.0557 0.0495 Uiso 1 . . H122 H 0.555 0.6245 1.1994 0.0498 Uiso 1 . . H123 H 0.3752 0.6404 1.1255 0.0497 Uiso 1 . . H901 H 0.0099 0.8044 1.1333 0.0804 Uiso 1 . . H902 H 0.051 0.6703 1.0592 0.0798 Uiso 1 . . N1 N 0.3073(4) 0.2185(4) 0.8585(2) 0.0239 Uani 1 . . N2 N 0.5079(4) 0.3838(4) 1.1506(2) 0.0229 Uani 1 . . O1 O 0.5701(4) 0.4653(3) 0.8615(2) 0.029 Uani 1 . . O2 O 0.2733(4) 0.1044(3) 1.1473(2) 0.0283 Uani 1 . . O3 O 0.1849(3) 0.4792(3) 0.9817(2) 0.0287 Uani 1 . . O4 O 0.6427(4) 0.1105(3) 1.0330(2) 0.0282 Uani 1 . . O5 O -0.0909(3) 0.5171(3) 0.9095(2) 0.0326 Uani 1 . . O6 O 0.9057(4) 0.0627(3) 1.1245(2) 0.0327 Uani 1 . . O7 O 0.8789(5) 0.4910(4) 0.3529(3) 0.0528 Uani 1 . . O8 O -0.0058(5) 0.0795(4) 1.6494(3) 0.0481 Uani 1 . . O9 O 0.0159(5) 0.6928(4) 1.1436(3) 0.0553 Uani 1 . . O10 O 0.8342(5) 0.9035(4) 0.8645(3) 0.0487 Uani 1 . . Ni1 Ni 0.41414(11) 0.29577(8) 1.00432(6) 0.0214 Uani 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 C3 0.0258(13) 0.0313(12) 0.0240(12) -0.0058(10) 0.0008(10) -0.0020(11) C4 0.0258(15) 0.0343(14) 0.0217(12) -0.0062(10) 0.0008(11) -0.0036(12) C5 0.0210(14) 0.0289(13) 0.0284(14) -0.0104(11) -0.0004(11) -0.0035(11) C6 0.0198(14) 0.0234(12) 0.0252(13) -0.0050(10) 0.0024(11) -0.0039(11) C7 0.0220(12) 0.0359(13) 0.0213(11) -0.0080(10) -0.0004(10) -0.0014(11) C8 0.0290(15) 0.0360(14) 0.0200(11) -0.0105(10) 0.0042(11) -0.0025(12) C9 0.0233(15) 0.0345(15) 0.0292(15) -0.0128(12) -0.0016(12) -0.0027(12) C10 0.0231(14) 0.0284(13) 0.0200(12) -0.0021(10) 0.0030(11) -0.0012(11) C11 0.0344(18) 0.0312(15) 0.0431(18) -0.0136(13) -0.0039(15) 0.0023(14) C12 0.0364(18) 0.0234(13) 0.0418(18) -0.0114(12) -0.0006(14) -0.0017(13) C13 0.0220(14) 0.0352(15) 0.0235(13) -0.0029(11) -0.0010(11) -0.0043(12) C14 0.0394(19) 0.0311(14) 0.0254(13) -0.0072(11) 0.0038(13) -0.0034(13) C15 0.0365(18) 0.0437(17) 0.0247(15) -0.0089(12) 0.0010(13) -0.0103(15) C16 0.0333(18) 0.0446(19) 0.0280(17) 0.0014(13) -0.0023(14) -0.0059(15) C17 0.0371(18) 0.0332(16) 0.0382(17) -0.0019(13) -0.0025(15) 0.0027(15) C18 0.0324(17) 0.0398(18) 0.0313(15) -0.0096(13) 0.0042(13) 0.0042(14) C19 0.0252(15) 0.0320(15) 0.0200(12) -0.0036(10) -0.0020(11) -0.0013(12) C20 0.0371(18) 0.0266(14) 0.0287(15) -0.0065(11) 0.0021(13) -0.0028(13) C21 0.0323(16) 0.0435(17) 0.0221(14) -0.0102(12) 0.0036(12) -0.0008(14) C22 0.0336(19) 0.0352(15) 0.0241(14) -0.0019(11) -0.0018(13) -0.0004(13) C23 0.0376(18) 0.0321(15) 0.0345(16) -0.0057(12) -0.0011(14) -0.0026(13) C24 0.0354(16) 0.0347(15) 0.0333(14) -0.0138(12) 0.0020(13) -0.0004(14) N1 0.0263(14) 0.0243(12) 0.0220(13) -0.0069(10) -0.0010(11) -0.0023(11) N2 0.0205(12) 0.0269(12) 0.0219(12) -0.0083(10) 0.0032(10) -0.0026(10) O1 0.0242(12) 0.0408(12) 0.0225(11) -0.0065(9) -0.0027(10) -0.0062(10) O2 0.0258(12) 0.0372(11) 0.0230(11) -0.0082(9) -0.0010(10) -0.0064(10) O3 0.0245(12) 0.0351(12) 0.0302(12) -0.0154(10) -0.0064(10) 0.0030(10) O4 0.0274(12) 0.0312(12) 0.0274(11) -0.0117(9) -0.0008(10) 0.0035(10) O5 0.0222(11) 0.0338(11) 0.0435(13) -0.0126(9) -0.0058(10) 0.0023(9) O6 0.0250(12) 0.0348(11) 0.0365(12) -0.0076(9) -0.0027(10) 0.0063(9) O7 0.081(2) 0.0478(14) 0.0307(13) -0.0139(11) 0.0152(14) -0.0113(15) O8 0.067(2) 0.0419(13) 0.0325(13) -0.0104(10) 0.0159(13) -0.0018(13) O9 0.085(3) 0.0386(14) 0.0379(16) -0.0089(12) 0.0141(17) 0.0023(16) O10 0.072(2) 0.0340(13) 0.0372(16) -0.0106(11) 0.0181(15) 0.0011(14) Ni1 0.01921(15) 0.02662(14) 0.01899(13) -0.00689(9) -0.00146(10) 0.00027(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C3 C4 1.514(4) . . yes C3 C13 1.517(4) . . yes C3 H3 0.967 . . no C3 O1 1.445(4) . . yes C4 H41 0.97 . . no C4 H42 0.961 . . no C4 N1 1.493(4) . . yes C5 C6 1.520(4) . . yes C5 H51 0.982 . . no C5 H52 0.97 . . no C5 N1 1.476(4) . . yes C6 O3 1.268(4) . . yes C6 O5 1.249(4) . . yes C6 Ni1 2.827(4) . . yes C7 C8 1.521(4) . . yes C7 C19 1.517(4) . . yes C7 H7 0.983 . . no C7 O2 1.456(3) . . yes C8 H81 0.964 . . no C8 H82 0.979 . . no C8 N2 1.491(4) . . yes C9 C10 1.541(4) . . yes C9 H91 0.961 . . no C9 H92 0.989 . . no C9 N2 1.476(4) . . yes C10 O4 1.250(4) . . yes C10 O6 1.247(4) . . yes C10 Ni1 2.832(4) . . yes C11 H111 0.962 . . no C11 H112 0.976 . . no C11 H113 0.968 . . no C11 N1 1.481(4) . . yes C12 H121 0.969 . . no C12 H122 0.982 . . no C12 H123 0.965 . . no C12 N2 1.493(4) . . yes C13 C14 1.386(4) . . yes C13 C18 1.391(5) . . yes C14 C15 1.414(5) . . yes C14 H14 0.918 . . no C15 C16 1.372(6) . . yes C15 O7 1.352(5) . . yes C16 C17 1.396(6) . . yes C16 H16 0.928 . . no C17 C18 1.397(5) . . yes C17 H17 0.919 . . no C18 H18 0.925 . . no C19 C20 1.379(4) . . yes C19 C24 1.397(4) . . yes C20 C21 1.400(5) . . yes C20 H20 0.923 . . no C21 C22 1.380(5) . . yes C21 O8 1.371(4) . . yes C22 C23 1.404(5) . . yes C22 H22 0.928 . . no C23 C24 1.381(5) . . yes C23 H23 0.929 . . no C24 H24 0.923 . . no H1 O1 0.822 . . no H2 O2 0.821 . . no H8 O8 0.835 . . no H71 O7 0.843 . . no H101 O10 0.846 . . no H102 O10 0.82 . . no H901 O9 0.8 . . no H902 O9 1.016 . . no N1 Ni1 2.092(3) . . yes N2 Ni1 2.096(3) . . yes O1 Ni1 2.116(2) . . yes O2 Ni1 2.138(2) . . yes O3 Ni1 2.059(2) . . yes O4 Ni1 2.066(3) . . yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 C3 C13 109.6(2) . . . yes C4 C3 H3 110.7 . . . no C13 C3 H3 108.6 . . . no C4 C3 O1 104.7(2) . . . yes C13 C3 O1 112.0(2) . . . yes H3 C3 O1 111.2 . . . no C3 C4 H41 108.8 . . . no C3 C4 H42 109.8 . . . no H41 C4 H42 108.2 . . . no C3 C4 N1 112.1(2) . . . yes H41 C4 N1 109.2 . . . no H42 C4 N1 108.7 . . . no C6 C5 H51 108.9 . . . no C6 C5 H52 107.4 . . . no H51 C5 H52 110.3 . . . no C6 C5 N1 111.2(3) . . . yes H51 C5 N1 108.8 . . . no H52 C5 N1 110.3 . . . no C5 C6 O3 117.7(3) . . . yes C5 C6 O5 118.8(3) . . . yes O3 C6 O5 123.5(3) . . . yes C5 C6 Ni1 76.17(18) . . . yes O5 C6 Ni1 164.4(3) . . . yes C8 C7 C19 115.3(2) . . . yes C8 C7 H7 106.8 . . . no C19 C7 H7 106.5 . . . no C8 C7 O2 107.4(2) . . . yes C19 C7 O2 113.3(2) . . . yes H7 C7 O2 107.1 . . . no C7 C8 H81 108.3 . . . no C7 C8 H82 109.1 . . . no H81 C8 H82 109.3 . . . no C7 C8 N2 109.7(2) . . . yes H81 C8 N2 111.4 . . . no H82 C8 N2 108.9 . . . no C10 C9 H91 107.5 . . . no C10 C9 H92 108.4 . . . no H91 C9 H92 108.5 . . . no C10 C9 N2 113.8(3) . . . yes H91 C9 N2 109.4 . . . no H92 C9 N2 109.1 . . . no C9 C10 O4 118.3(3) . . . yes C9 C10 O6 115.5(3) . . . yes O4 C10 O6 126.1(3) . . . yes C9 C10 Ni1 77.06(19) . . . yes O6 C10 Ni1 166.3(3) . . . yes H111 C11 H112 110.2 . . . no H111 C11 H113 109.5 . . . no H112 C11 H113 110.2 . . . no H111 C11 N1 108.7 . . . no H112 C11 N1 109.8 . . . no H113 C11 N1 108.4 . . . no H121 C12 H122 109.2 . . . no H121 C12 H123 110.4 . . . no H122 C12 H123 110.5 . . . no H121 C12 N2 108.7 . . . no H122 C12 N2 109.7 . . . no H123 C12 N2 108.4 . . . no C3 C13 C14 117.6(3) . . . yes C3 C13 C18 122.3(3) . . . yes C14 C13 C18 120.0(3) . . . yes C13 C14 C15 120.0(3) . . . yes C13 C14 H14 120.3 . . . no C15 C14 H14 119.7 . . . no C14 C15 C16 120.0(3) . . . yes C14 C15 O7 115.5(3) . . . yes C16 C15 O7 124.5(3) . . . yes C15 C16 C17 119.9(3) . . . yes C15 C16 H16 119.7 . . . no C17 C16 H16 120.4 . . . no C16 C17 C18 120.5(3) . . . yes C16 C17 H17 119 . . . no C18 C17 H17 120.6 . . . no C17 C18 C13 119.6(3) . . . yes C17 C18 H18 119.7 . . . no C13 C18 H18 120.6 . . . no C7 C19 C20 123.3(3) . . . yes C7 C19 C24 117.3(3) . . . yes C20 C19 C24 119.2(3) . . . yes C19 C20 C21 120.6(3) . . . yes C19 C20 H20 120.4 . . . no C21 C20 H20 119 . . . no C20 C21 C22 120.3(3) . . . yes C20 C21 O8 117.3(3) . . . yes C22 C21 O8 122.5(3) . . . yes C21 C22 C23 119.1(3) . . . yes C21 C22 H22 120 . . . no C23 C22 H22 120.8 . . . no C22 C23 C24 120.4(3) . . . yes C22 C23 H23 119.6 . . . no C24 C23 H23 120 . . . no C19 C24 C23 120.4(3) . . . yes C19 C24 H24 120 . . . no C23 C24 H24 119.6 . . . no C4 N1 C11 111.7(3) . . . yes C4 N1 C5 107.9(2) . . . yes C11 N1 C5 110.5(3) . . . yes C4 N1 Ni1 106.03(19) . . . yes C11 N1 Ni1 114.5(2) . . . yes C5 N1 Ni1 105.89(19) . . . yes C12 N2 C8 109.2(2) . . . yes C12 N2 C9 109.8(3) . . . yes C8 N2 C9 111.0(3) . . . yes C12 N2 Ni1 113.4(2) . . . yes C8 N2 Ni1 105.8(2) . . . yes C9 N2 Ni1 107.58(19) . . . yes C3 O1 H1 104.4 . . . no C3 O1 Ni1 108.48(18) . . . yes H1 O1 Ni1 117.3 . . . no C7 O2 H2 109.6 . . . no C7 O2 Ni1 107.30(18) . . . yes H2 O2 Ni1 125.4 . . . no C6 O3 Ni1 114.2(2) . . . yes C10 O4 Ni1 115.0(2) . . . yes C15 O7 H71 116.7 . . . no C21 O8 H8 109.6 . . . no H902 O9 H901 104.3 . . . no H101 O10 H102 107.8 . . . no O2 Ni1 O1 174.98(12) . . . yes O2 Ni1 N2 83.24(10) . . . yes O1 Ni1 N2 97.88(10) . . . yes O2 Ni1 N1 96.55(10) . . . yes O1 Ni1 N1 82.62(11) . . . yes N2 Ni1 N1 176.71(13) . . . yes O2 Ni1 O4 87.99(10) . . . yes O1 Ni1 O4 87.30(11) . . . yes N2 Ni1 O4 82.59(11) . . . yes N1 Ni1 O4 100.68(10) . . . yes O2 Ni1 O3 90.68(11) . . . yes O1 Ni1 O3 94.07(10) . . . yes N2 Ni1 O3 96.00(10) . . . yes N1 Ni1 O3 80.72(11) . . . yes O4 Ni1 O3 178.17(12) . . . yes O2 Ni1 C6 85.55(10) . . . yes O1 Ni1 C6 98.13(10) . . . yes N2 Ni1 C6 118.66(10) . . . yes N1 Ni1 C6 58.07(10) . . . yes O4 Ni1 C6 156.74(10) . . . yes O2 Ni1 C10 90.03(10) . . . yes O1 Ni1 C10 86.35(10) . . . yes N2 Ni1 C10 59.52(10) . . . yes N1 Ni1 C10 123.77(10) . . . yes O4 Ni1 C10 23.59(10) . . . yes O3 Ni1 C6 24.15(9) . . . yes O3 Ni1 C10 155.23(9) . . . yes C6 Ni1 C10 175.44(10) . . . yes