# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email dtyler@uoregon.edu _publ_contact_author_name 'David Tyler' loop_ _publ_author_name 'David Tyler' 'Charles Swor' data_char2 _database_code_depnum_ccdc_archive 'CCDC 821007' #TrackingRef '- char2.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H64 Cl4 Fe2 O16 P8' _chemical_formula_weight 1110.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.7855(4) _cell_length_b 13.0809(7) _cell_length_c 10.4136(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.3930(10) _cell_angle_gamma 90.00 _cell_volume 1059.61(10) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1821 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 24.85 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.740 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 1.303 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8917 _exptl_absorpt_correction_T_max 0.9497 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11961 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2428 _reflns_number_gt 1974 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The H atoms at the O atoms involved in H-bonds were refined with restrictions; the value of 0.967 A was used in the refinement as a target for O-H bond distances. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+0.1047P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2428 _refine_ls_number_parameters 188 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0831 _refine_ls_wR_factor_gt 0.0761 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.123 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.0000 0.5000 0.5000 0.01080(14) Uani 1 2 d S . . Cl1 Cl 0.28683(8) 0.53956(5) 0.56463(6) 0.01713(16) Uani 1 1 d . . . P1 P 0.05350(9) 0.33210(5) 0.52489(6) 0.01275(16) Uani 1 1 d . . . P2 P -0.05509(9) 0.49542(5) 0.70847(6) 0.01293(16) Uani 1 1 d . . . O1 O -0.0584(3) 0.13479(14) 0.49167(19) 0.0205(4) Uani 1 1 d D . . O2 O 0.3966(3) 0.31753(16) 0.5826(2) 0.0275(5) Uani 1 1 d D . . O3 O -0.1116(3) 0.67600(15) 0.8188(2) 0.0241(5) Uani 1 1 d D . . O4 O -0.2957(3) 0.47215(15) 0.89042(19) 0.0210(5) Uani 1 1 d D . . C1 C 0.0326(4) 0.2929(2) 0.6945(3) 0.0179(6) Uani 1 1 d . . . C2 C 0.0568(4) 0.3855(2) 0.7824(3) 0.0171(6) Uani 1 1 d . . . C3 C -0.0864(4) 0.2355(2) 0.4436(3) 0.0177(6) Uani 1 1 d . . . C4 C 0.2695(4) 0.2843(2) 0.4892(3) 0.0196(6) Uani 1 1 d . . . C5 C 0.0126(4) 0.5960(2) 0.8228(3) 0.0175(6) Uani 1 1 d . . . C6 C -0.2790(4) 0.4759(2) 0.7543(3) 0.0180(6) Uani 1 1 d . . . H1O H 0.033(3) 0.111(3) 0.455(3) 0.045(11) Uiso 1 1 d D . . H2O H 0.401(4) 0.3867(14) 0.578(3) 0.039(10) Uiso 1 1 d D . . H3O H -0.054(5) 0.731(2) 0.858(4) 0.068(13) Uiso 1 1 d D . . H4O H -0.308(5) 0.5360(17) 0.921(3) 0.051(12) Uiso 1 1 d D . . H1A H 0.117(3) 0.240(2) 0.714(3) 0.015(7) Uiso 1 1 d . . . H1B H -0.078(4) 0.270(2) 0.694(3) 0.016(8) Uiso 1 1 d . . . H2A H 0.183(4) 0.407(2) 0.791(3) 0.027(8) Uiso 1 1 d . . . H2B H 0.013(3) 0.372(2) 0.867(3) 0.015(7) Uiso 1 1 d . . . H3A H -0.200(4) 0.253(3) 0.463(3) 0.039(10) Uiso 1 1 d . . . H3B H -0.070(3) 0.237(2) 0.355(3) 0.018(8) Uiso 1 1 d . . . H4A H 0.301(3) 0.305(2) 0.407(3) 0.013(7) Uiso 1 1 d . . . H4B H 0.271(3) 0.212(2) 0.491(2) 0.011(7) Uiso 1 1 d . . . H5A H 0.020(4) 0.565(2) 0.906(3) 0.021(8) Uiso 1 1 d . . . H5B H 0.127(4) 0.622(2) 0.802(3) 0.025(8) Uiso 1 1 d . . . H6A H -0.343(4) 0.527(2) 0.717(3) 0.017(8) Uiso 1 1 d . . . H6B H -0.315(4) 0.411(2) 0.719(3) 0.025(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0115(3) 0.0101(3) 0.0108(3) -0.0001(2) 0.0012(2) 0.0001(2) Cl1 0.0129(3) 0.0164(3) 0.0220(4) -0.0008(3) -0.0004(3) -0.0006(3) P1 0.0141(3) 0.0109(3) 0.0133(3) 0.0002(3) 0.0015(3) 0.0005(3) P2 0.0147(4) 0.0120(3) 0.0122(4) -0.0004(3) 0.0021(3) -0.0002(3) O1 0.0225(11) 0.0107(9) 0.0290(11) -0.0002(8) 0.0103(9) 0.0015(8) O2 0.0197(11) 0.0175(12) 0.0445(14) 0.0042(10) -0.0100(9) 0.0019(9) O3 0.0217(11) 0.0176(11) 0.0329(12) -0.0091(9) 0.0001(9) 0.0013(9) O4 0.0282(12) 0.0162(11) 0.0196(10) -0.0012(8) 0.0123(9) -0.0015(9) C1 0.0212(15) 0.0159(14) 0.0170(14) 0.0029(11) 0.0030(12) 0.0006(12) C2 0.0227(16) 0.0157(14) 0.0132(14) 0.0022(11) 0.0027(11) 0.0021(11) C3 0.0208(15) 0.0124(14) 0.0199(15) -0.0015(11) 0.0005(12) -0.0024(11) C4 0.0199(15) 0.0173(15) 0.0217(16) 0.0035(12) 0.0041(12) 0.0044(12) C5 0.0228(16) 0.0156(14) 0.0142(14) -0.0018(11) 0.0008(12) -0.0008(12) C6 0.0209(15) 0.0140(14) 0.0194(15) 0.0024(12) 0.0047(12) -0.0005(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 P2 2.2312(7) 3_566 ? Fe1 P2 2.2312(7) . ? Fe1 P1 2.2484(7) 3_566 ? Fe1 P1 2.2484(7) . ? Fe1 Cl1 2.3626(6) . ? Fe1 Cl1 2.3626(6) 3_566 ? P1 C4 1.846(3) . ? P1 C3 1.850(3) . ? P1 C1 1.853(3) . ? P2 C2 1.834(3) . ? P2 C5 1.837(3) . ? P2 C6 1.844(3) . ? O1 C3 1.422(3) . ? O1 H1O 0.879(18) . ? O2 C4 1.426(3) . ? O2 H2O 0.906(18) . ? O3 C5 1.424(3) . ? O3 H3O 0.935(19) . ? O4 C6 1.430(3) . ? O4 H4O 0.899(18) . ? C1 C2 1.525(4) . ? C1 H1A 0.97(3) . ? C1 H1B 0.91(3) . ? C2 H2A 1.03(3) . ? C2 H2B 0.98(3) . ? C3 H3A 0.95(3) . ? C3 H3B 0.94(3) . ? C4 H4A 0.94(3) . ? C4 H4B 0.95(3) . ? C5 H5A 0.96(3) . ? C5 H5B 0.98(3) . ? C6 H6A 0.91(3) . ? C6 H6B 0.96(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P2 Fe1 P2 180.0 3_566 . ? P2 Fe1 P1 84.48(2) 3_566 3_566 ? P2 Fe1 P1 95.52(2) . 3_566 ? P2 Fe1 P1 95.52(2) 3_566 . ? P2 Fe1 P1 84.48(2) . . ? P1 Fe1 P1 180.00(3) 3_566 . ? P2 Fe1 Cl1 93.07(2) 3_566 . ? P2 Fe1 Cl1 86.93(2) . . ? P1 Fe1 Cl1 89.27(2) 3_566 . ? P1 Fe1 Cl1 90.73(2) . . ? P2 Fe1 Cl1 86.93(2) 3_566 3_566 ? P2 Fe1 Cl1 93.07(2) . 3_566 ? P1 Fe1 Cl1 90.73(2) 3_566 3_566 ? P1 Fe1 Cl1 89.27(2) . 3_566 ? Cl1 Fe1 Cl1 180.0 . 3_566 ? C4 P1 C3 101.55(14) . . ? C4 P1 C1 102.43(14) . . ? C3 P1 C1 99.99(14) . . ? C4 P1 Fe1 118.24(10) . . ? C3 P1 Fe1 120.80(9) . . ? C1 P1 Fe1 110.92(9) . . ? C2 P2 C5 99.86(13) . . ? C2 P2 C6 102.74(13) . . ? C5 P2 C6 100.39(13) . . ? C2 P2 Fe1 108.80(9) . . ? C5 P2 Fe1 123.35(10) . . ? C6 P2 Fe1 118.52(10) . . ? C3 O1 H1O 107(2) . . ? C4 O2 H2O 107(2) . . ? C5 O3 H3O 104(2) . . ? C6 O4 H4O 109(2) . . ? C2 C1 P1 109.82(19) . . ? C2 C1 H1A 112.0(16) . . ? P1 C1 H1A 108.2(16) . . ? C2 C1 H1B 110.9(18) . . ? P1 C1 H1B 101.9(17) . . ? H1A C1 H1B 113(2) . . ? C1 C2 P2 109.0(2) . . ? C1 C2 H2A 111.7(16) . . ? P2 C2 H2A 104.9(16) . . ? C1 C2 H2B 111.3(17) . . ? P2 C2 H2B 110.2(16) . . ? H2A C2 H2B 110(2) . . ? O1 C3 P1 113.16(19) . . ? O1 C3 H3A 106(2) . . ? P1 C3 H3A 106(2) . . ? O1 C3 H3B 109.9(17) . . ? P1 C3 H3B 109.7(17) . . ? H3A C3 H3B 112(3) . . ? O2 C4 P1 111.8(2) . . ? O2 C4 H4A 109.8(16) . . ? P1 C4 H4A 111.1(16) . . ? O2 C4 H4B 106.6(16) . . ? P1 C4 H4B 110.0(16) . . ? H4A C4 H4B 107(2) . . ? O3 C5 P2 109.32(19) . . ? O3 C5 H5A 110.7(18) . . ? P2 C5 H5A 106.8(18) . . ? O3 C5 H5B 111.2(18) . . ? P2 C5 H5B 109.6(17) . . ? H5A C5 H5B 109(2) . . ? O4 C6 P2 112.8(2) . . ? O4 C6 H6A 111.9(18) . . ? P2 C6 H6A 107.4(18) . . ? O4 C6 H6B 108.2(18) . . ? P2 C6 H6B 106.8(18) . . ? H6A C6 H6B 110(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag P2 Fe1 P1 C4 59.41(11) 3_566 . . . ? P2 Fe1 P1 C4 -120.59(11) . . . . ? P1 Fe1 P1 C4 -31(100) 3_566 . . . ? Cl1 Fe1 P1 C4 -33.74(11) . . . . ? Cl1 Fe1 P1 C4 146.26(11) 3_566 . . . ? P2 Fe1 P1 C3 -66.38(12) 3_566 . . . ? P2 Fe1 P1 C3 113.62(12) . . . . ? P1 Fe1 P1 C3 -157(100) 3_566 . . . ? Cl1 Fe1 P1 C3 -159.53(12) . . . . ? Cl1 Fe1 P1 C3 20.47(12) 3_566 . . . ? P2 Fe1 P1 C1 177.25(11) 3_566 . . . ? P2 Fe1 P1 C1 -2.75(11) . . . . ? P1 Fe1 P1 C1 87(100) 3_566 . . . ? Cl1 Fe1 P1 C1 84.10(11) . . . . ? Cl1 Fe1 P1 C1 -95.90(11) 3_566 . . . ? P2 Fe1 P2 C2 -159(100) 3_566 . . . ? P1 Fe1 P2 C2 -156.76(10) 3_566 . . . ? P1 Fe1 P2 C2 23.24(10) . . . . ? Cl1 Fe1 P2 C2 -67.79(10) . . . . ? Cl1 Fe1 P2 C2 112.21(10) 3_566 . . . ? P2 Fe1 P2 C5 -43(100) 3_566 . . . ? P1 Fe1 P2 C5 -40.62(12) 3_566 . . . ? P1 Fe1 P2 C5 139.38(12) . . . . ? Cl1 Fe1 P2 C5 48.35(11) . . . . ? Cl1 Fe1 P2 C5 -131.65(11) 3_566 . . . ? P2 Fe1 P2 C6 85(100) 3_566 . . . ? P1 Fe1 P2 C6 86.49(11) 3_566 . . . ? P1 Fe1 P2 C6 -93.51(11) . . . . ? Cl1 Fe1 P2 C6 175.46(11) . . . . ? Cl1 Fe1 P2 C6 -4.54(11) 3_566 . . . ? C4 P1 C1 C2 104.2(2) . . . . ? C3 P1 C1 C2 -151.5(2) . . . . ? Fe1 P1 C1 C2 -22.8(2) . . . . ? P1 C1 C2 P2 41.2(2) . . . . ? C5 P2 C2 C1 -174.4(2) . . . . ? C6 P2 C2 C1 82.5(2) . . . . ? Fe1 P2 C2 C1 -44.0(2) . . . . ? C4 P1 C3 O1 60.1(2) . . . . ? C1 P1 C3 O1 -44.9(2) . . . . ? Fe1 P1 C3 O1 -166.69(15) . . . . ? C3 P1 C4 O2 -154.9(2) . . . . ? C1 P1 C4 O2 -51.9(2) . . . . ? Fe1 P1 C4 O2 70.4(2) . . . . ? C2 P2 C5 O3 -154.9(2) . . . . ? C6 P2 C5 O3 -49.8(2) . . . . ? Fe1 P2 C5 O3 84.7(2) . . . . ? C2 P2 C6 O4 58.7(2) . . . . ? C5 P2 C6 O4 -44.0(2) . . . . ? Fe1 P2 C6 O4 178.62(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3O O2 0.935(19) 1.76(2) 2.673(3) 164(4) 2_556 O2 H2O Cl1 0.906(18) 2.19(2) 3.031(2) 154(3) . O1 H1O O4 0.879(18) 1.87(2) 2.726(3) 165(3) 4_665 O4 H4O O1 0.899(18) 1.91(2) 2.728(3) 149(3) 2_456 O4 H4O O3 0.899(18) 2.64(3) 3.132(3) 116(3) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.482 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.092 # Attachment '- char5.cif' data_char5 _database_code_depnum_ccdc_archive 'CCDC 821008' #TrackingRef '- char5.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H22 B2 O4 P2' _chemical_formula_weight 241.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.092(3) _cell_length_b 6.2042(11) _cell_length_c 11.757(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.688(3) _cell_angle_gamma 90.00 _cell_volume 1296.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 974 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 24.43 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.323 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9179 _exptl_absorpt_correction_T_max 0.9936 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6768 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_sigmaI/netI 0.0461 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1408 _reflns_number_gt 1138 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The H atoms at the O atoms involved in H-bonds were refined with restrictions; the value of 0.967 A was used in the refinement as a target for O-H bond distances. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+0.0393P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1408 _refine_ls_number_parameters 108 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.39399(3) 0.18832(9) 0.96237(5) 0.0191(2) Uani 1 1 d . . . O1 O 0.29337(9) 0.4245(3) 0.81849(14) 0.0273(4) Uani 1 1 d D . . O2 O 0.31262(11) -0.1572(3) 0.86847(16) 0.0319(5) Uani 1 1 d D . . B1 B 0.40483(19) 0.3741(5) 1.0936(3) 0.0292(7) Uani 1 1 d . . . C1 C 0.36346(16) 0.3192(4) 0.8220(2) 0.0264(6) Uani 1 1 d . . . C2 C 0.32352(15) -0.0200(4) 0.9667(2) 0.0248(6) Uani 1 1 d . . . C3 C 0.47891(14) 0.0479(4) 0.9433(2) 0.0228(5) Uani 1 1 d . . . H1O H 0.3013(13) 0.564(3) 0.840(2) 0.023(7) Uiso 1 1 d D . . H2O H 0.2741(15) -0.108(6) 0.813(2) 0.067(11) Uiso 1 1 d D . . H1B H 0.408(2) 0.253(6) 1.167(3) 0.072(11) Uiso 1 1 d . . . H2B H 0.3527(18) 0.486(5) 1.080(3) 0.059(10) Uiso 1 1 d . . . H3B H 0.4544(19) 0.472(6) 1.093(3) 0.060(10) Uiso 1 1 d . . . H1A H 0.3992(16) 0.419(5) 0.812(2) 0.035(8) Uiso 1 1 d . . . H1C H 0.3567(16) 0.199(5) 0.766(2) 0.041(8) Uiso 1 1 d . . . H2A H 0.3404(15) -0.108(5) 1.033(2) 0.033(7) Uiso 1 1 d . . . H2C H 0.2782(17) 0.046(5) 0.976(2) 0.040(8) Uiso 1 1 d . . . H3A H 0.5092(17) 0.156(5) 0.915(2) 0.039(8) Uiso 1 1 d . . . H3C H 0.4669(13) -0.058(4) 0.892(2) 0.015(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0198(4) 0.0173(3) 0.0186(4) -0.0001(2) -0.0001(2) 0.0019(2) O1 0.0284(10) 0.0188(9) 0.0299(9) -0.0007(7) -0.0068(7) 0.0035(7) O2 0.0364(11) 0.0197(9) 0.0327(11) -0.0038(7) -0.0115(8) 0.0004(8) B1 0.0323(17) 0.0262(15) 0.0273(15) -0.0058(12) 0.0009(13) 0.0026(13) C1 0.0298(15) 0.0241(13) 0.0233(13) 0.0025(11) -0.0001(10) 0.0017(11) C2 0.0240(14) 0.0208(12) 0.0281(14) 0.0005(10) 0.0010(11) -0.0003(10) C3 0.0234(13) 0.0237(12) 0.0205(13) -0.0006(11) 0.0023(10) 0.0043(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C3 1.816(2) . ? P1 C2 1.823(3) . ? P1 C1 1.830(3) . ? P1 B1 1.907(3) . ? O1 C1 1.420(3) . ? O1 H1O 0.908(17) . ? O2 C2 1.419(3) . ? O2 H2O 0.913(18) . ? B1 H1B 1.13(4) . ? B1 H2B 1.16(3) . ? B1 H3B 1.08(3) . ? C1 H1A 0.92(3) . ? C1 H1C 0.99(3) . ? C2 H2A 0.96(3) . ? C2 H2C 0.94(3) . ? C3 C3 1.529(5) 5_657 ? C3 H3A 0.96(3) . ? C3 H3C 0.89(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 P1 C2 105.99(13) . . ? C3 P1 C1 102.83(12) . . ? C2 P1 C1 104.13(13) . . ? C3 P1 B1 115.33(13) . . ? C2 P1 B1 111.93(13) . . ? C1 P1 B1 115.46(14) . . ? C1 O1 H1O 109.7(15) . . ? C2 O2 H2O 111(2) . . ? P1 B1 H1B 101.2(19) . . ? P1 B1 H2B 106.9(16) . . ? H1B B1 H2B 116(3) . . ? P1 B1 H3B 107.2(17) . . ? H1B B1 H3B 116(3) . . ? H2B B1 H3B 109(2) . . ? O1 C1 P1 110.42(18) . . ? O1 C1 H1A 109.5(17) . . ? P1 C1 H1A 108.2(17) . . ? O1 C1 H1C 109.2(17) . . ? P1 C1 H1C 104.0(16) . . ? H1A C1 H1C 115(2) . . ? O2 C2 P1 113.25(18) . . ? O2 C2 H2A 107.4(17) . . ? P1 C2 H2A 107.9(17) . . ? O2 C2 H2C 111.2(18) . . ? P1 C2 H2C 108.8(18) . . ? H2A C2 H2C 108(2) . . ? C3 C3 P1 112.1(2) 5_657 . ? C3 C3 H3A 110.3(18) 5_657 . ? P1 C3 H3A 105.0(17) . . ? C3 C3 H3C 108.9(16) 5_657 . ? P1 C3 H3C 109.4(15) . . ? H3A C3 H3C 111(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 P1 C1 O1 175.43(18) . . . . ? C2 P1 C1 O1 65.0(2) . . . . ? B1 P1 C1 O1 -58.1(2) . . . . ? C3 P1 C2 O2 -55.2(2) . . . . ? C1 P1 C2 O2 52.9(2) . . . . ? B1 P1 C2 O2 178.29(18) . . . . ? C2 P1 C3 C3 -79.3(3) . . . 5_657 ? C1 P1 C3 C3 171.6(3) . . . 5_657 ? B1 P1 C3 C3 45.1(3) . . . 5_657 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O O2 0.908(17) 1.764(17) 2.670(2) 174(2) 1_565 O2 H2O O1 0.913(18) 1.80(2) 2.684(2) 163(3) 4_546 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.155 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.076