# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2014 ####################################################################### # # 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_lyf-pr2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H13 O8 P2 Pr' _chemical_formula_sum 'C8 H13 O8 P2 Pr' _chemical_formula_weight 440.03 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.198(2) _cell_length_b 8.3508(17) _cell_length_c 13.632(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.50(3) _cell_angle_gamma 90.00 _cell_volume 1300.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10828 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.51 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 4.023 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3946 _exptl_absorpt_correction_T_max 0.5313 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12188 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2970 _reflns_number_gt 2637 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)' _computing_cell_refinement 'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)' _computing_data_reduction 'CrystalClear (Rigaku/MSC, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXL-97 _refine_special_details ; dfix 0.85 0.01 o2 h21 Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0081P)^2^+5.4085P] 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 2970 _refine_ls_number_parameters 175 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0592 _refine_ls_wR_factor_gt 0.0576 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8708(3) 0.4972(5) 0.6649(3) 0.0256(8) Uani 1 1 d . . . C2 C 0.9063(4) 0.4134(5) 0.7591(3) 0.0325(9) Uani 1 1 d . . . H2 H 0.9275 0.3062 0.7608 0.039 Uiso 1 1 calc R . . C3 C 0.9100(4) 0.4900(6) 0.8505(3) 0.0348(10) Uani 1 1 d . . . H3 H 0.9350 0.4345 0.9136 0.042 Uiso 1 1 calc R . . C4 C 0.8764(4) 0.6492(5) 0.8481(3) 0.0306(9) Uani 1 1 d . . . H4 H 0.8794 0.6992 0.9099 0.037 Uiso 1 1 calc R . . C5 C 0.8383(3) 0.7353(5) 0.7548(3) 0.0241(8) Uani 1 1 d . . . C6 C 0.8388(3) 0.6580(5) 0.6640(3) 0.0261(8) Uani 1 1 d . . . H6 H 0.8173 0.7150 0.6015 0.031 Uiso 1 1 calc R . . C7 C 0.8566(3) 0.4147(5) 0.5623(3) 0.0275(8) Uani 1 1 d . . . H7A H 0.9038 0.3182 0.5758 0.033 Uiso 1 1 calc R . . H7B H 0.8841 0.4850 0.5191 0.033 Uiso 1 1 calc R . . C8 C 0.7880(3) 0.9006(5) 0.7476(3) 0.0251(8) Uani 1 1 d . . . H8A H 0.8114 0.9637 0.6985 0.030 Uiso 1 1 calc R . . H8B H 0.8188 0.9521 0.8156 0.030 Uiso 1 1 calc R . . O1 O 0.6309(3) 0.5119(4) 0.4758(2) 0.0339(7) Uani 1 1 d . . . O2 O 0.7067(3) 0.2908(3) 0.3879(2) 0.0280(6) Uani 1 1 d D . . H21 H 0.665(4) 0.342(6) 0.334(2) 0.042 Uiso 1 1 d D . . O3 O 0.6685(3) 0.2361(3) 0.5544(2) 0.0263(6) Uani 1 1 d . . . O4 O 0.5811(3) 0.8395(4) 0.5912(2) 0.0287(6) Uani 1 1 d . . . O5 O 0.5969(3) 0.7798(3) 0.7771(2) 0.0250(6) Uani 1 1 d . . . O6 O 0.5900(2) 1.0665(3) 0.7154(2) 0.0226(6) Uani 1 1 d . . . O7 O 0.6754(3) 0.9541(3) 0.4445(2) 0.0311(7) Uani 1 1 d . . . H71 H 0.6762 1.0344 0.4831 0.047 Uiso 1 1 d R . . H72 H 0.6699 0.9863 0.3838 0.047 Uiso 1 1 d R . . O8 O 0.3921(3) 0.5349(3) 0.2973(2) 0.0285(6) Uani 1 1 d . . . H81 H 0.4173 0.4477 0.2806 0.043 Uiso 1 1 d R . . H82 H 0.3263 0.5187 0.3033 0.043 Uiso 1 1 d R . . P1 P 0.70514(8) 0.36372(11) 0.49311(7) 0.01812(18) Uani 1 1 d . . . P2 P 0.62869(8) 0.89376(10) 0.70460(7) 0.01532(17) Uani 1 1 d . . . Pr1 Pr 0.519416(17) 0.74652(2) 0.416400(14) 0.01600(7) Uani 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 C1 0.0158(18) 0.0272(19) 0.033(2) -0.0077(17) 0.0082(15) -0.0015(15) C2 0.023(2) 0.028(2) 0.042(2) -0.0010(19) 0.0053(18) 0.0056(17) C3 0.031(2) 0.039(2) 0.029(2) 0.0047(19) 0.0032(17) 0.0056(19) C4 0.024(2) 0.038(2) 0.026(2) -0.0058(18) 0.0049(16) 0.0006(18) C5 0.0169(17) 0.0261(19) 0.0288(19) -0.0041(16) 0.0075(14) -0.0038(15) C6 0.0187(18) 0.030(2) 0.030(2) -0.0030(17) 0.0083(15) -0.0009(16) C7 0.0212(19) 0.029(2) 0.036(2) -0.0069(17) 0.0152(17) -0.0009(16) C8 0.0229(19) 0.0232(18) 0.0306(19) -0.0068(16) 0.0113(16) -0.0053(15) O1 0.0395(18) 0.0304(15) 0.0270(14) -0.0012(13) 0.0058(13) 0.0173(14) O2 0.0424(18) 0.0248(14) 0.0188(13) 0.0014(11) 0.0135(12) 0.0101(12) O3 0.0299(15) 0.0277(14) 0.0251(13) -0.0012(12) 0.0142(11) -0.0050(12) O4 0.0313(16) 0.0399(17) 0.0156(12) -0.0069(12) 0.0090(11) -0.0056(13) O5 0.0365(16) 0.0187(13) 0.0270(14) 0.0071(11) 0.0202(12) 0.0044(11) O6 0.0289(15) 0.0168(12) 0.0211(12) 0.0016(10) 0.0076(11) 0.0043(11) O7 0.0465(19) 0.0263(14) 0.0279(14) -0.0079(12) 0.0223(13) -0.0108(13) O8 0.0290(16) 0.0254(14) 0.0359(16) -0.0098(12) 0.0176(13) -0.0059(12) P1 0.0212(5) 0.0178(4) 0.0167(4) 0.0009(4) 0.0083(3) 0.0038(4) P2 0.0207(4) 0.0137(4) 0.0131(4) 0.0002(3) 0.0079(3) 0.0000(3) Pr1 0.02078(10) 0.01470(10) 0.01338(10) -0.00039(7) 0.00704(7) 0.00235(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.392(6) . ? C1 C6 1.397(6) . ? C1 C7 1.514(5) . ? C2 C3 1.387(6) . ? C2 H2 0.9300 . ? C3 C4 1.388(6) . ? C3 H3 0.9300 . ? C4 C5 1.392(6) . ? C4 H4 0.9300 . ? C5 C6 1.398(5) . ? C5 C8 1.500(5) . ? C6 H6 0.9300 . ? C7 P1 1.807(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 P2 1.824(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? O1 P1 1.503(3) . ? O1 Pr1 2.360(3) . ? O2 P1 1.564(3) . ? O2 H21 0.849(10) . ? O3 P1 1.514(3) . ? O3 Pr1 2.465(3) 3_666 ? O4 P2 1.517(3) . ? O4 Pr1 2.365(3) . ? O5 P2 1.517(3) . ? O5 Pr1 2.410(3) 4_576 ? O6 P2 1.541(3) . ? O6 Pr1 2.402(3) 3_676 ? O7 Pr1 2.502(3) . ? O7 H71 0.8499 . ? O7 H72 0.8500 . ? O8 Pr1 2.531(3) . ? O8 H81 0.8517 . ? O8 H82 0.8462 . ? Pr1 O6 2.402(3) 3_676 ? Pr1 O5 2.410(3) 4_575 ? Pr1 O3 2.465(3) 3_666 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.1(4) . . ? C2 C1 C7 121.5(4) . . ? C6 C1 C7 119.2(4) . . ? C3 C2 C1 119.9(4) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.3(4) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 121.2(4) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 117.9(4) . . ? C4 C5 C8 122.2(4) . . ? C6 C5 C8 119.7(4) . . ? C1 C6 C5 121.6(4) . . ? C1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C1 C7 P1 110.7(3) . . ? C1 C7 H7A 109.5 . . ? P1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? P1 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C5 C8 P2 110.9(3) . . ? C5 C8 H8A 109.5 . . ? P2 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? P2 C8 H8B 109.5 . . ? H8A C8 H8B 108.0 . . ? P1 O1 Pr1 168.72(19) . . ? P1 O2 H21 114(4) . . ? P1 O3 Pr1 121.22(16) . 3_666 ? P2 O4 Pr1 176.10(19) . . ? P2 O5 Pr1 146.18(16) . 4_576 ? P2 O6 Pr1 130.21(15) . 3_676 ? Pr1 O7 H71 119.0 . . ? Pr1 O7 H72 105.9 . . ? H71 O7 H72 109.4 . . ? Pr1 O8 H81 124.8 . . ? Pr1 O8 H82 116.0 . . ? H81 O8 H82 109.5 . . ? O1 P1 O3 112.86(18) . . ? O1 P1 O2 112.10(16) . . ? O3 P1 O2 109.41(16) . . ? O1 P1 C7 109.75(19) . . ? O3 P1 C7 108.87(19) . . ? O2 P1 C7 103.39(18) . . ? O5 P2 O4 112.46(17) . . ? O5 P2 O6 111.63(15) . . ? O4 P2 O6 110.88(16) . . ? O5 P2 C8 107.29(18) . . ? O4 P2 C8 108.73(18) . . ? O6 P2 C8 105.50(17) . . ? O1 Pr1 O4 89.15(10) . . ? O1 Pr1 O6 153.97(9) . 3_676 ? O4 Pr1 O6 115.97(10) . 3_676 ? O1 Pr1 O5 81.76(10) . 4_575 ? O4 Pr1 O5 138.59(10) . 4_575 ? O6 Pr1 O5 74.82(9) 3_676 4_575 ? O1 Pr1 O3 116.75(11) . 3_666 ? O4 Pr1 O3 78.66(10) . 3_666 ? O6 Pr1 O3 77.18(9) 3_676 3_666 ? O5 Pr1 O3 140.95(10) 4_575 3_666 ? O1 Pr1 O7 101.94(11) . . ? O4 Pr1 O7 70.22(10) . . ? O6 Pr1 O7 81.82(10) 3_676 . ? O5 Pr1 O7 72.36(9) 4_575 . ? O3 Pr1 O7 129.39(9) 3_666 . ? O1 Pr1 O8 77.92(10) . . ? O4 Pr1 O8 141.54(10) . . ? O6 Pr1 O8 85.33(10) 3_676 . ? O5 Pr1 O8 75.68(9) 4_575 . ? O3 Pr1 O8 75.43(9) 3_666 . ? O7 Pr1 O8 147.66(9) . . ? 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 O8 H82 O3 0.85 2.81 3.057(4) 99.1 3_666 O8 H81 O6 0.85 2.56 3.111(4) 123.4 4_575 O8 H81 O5 0.85 2.04 2.836(4) 155.3 3_666 O7 H72 O8 0.85 2.35 3.178(4) 164.5 2_655 O7 H71 O3 0.85 1.96 2.807(4) 172.3 1_565 O2 H21 O6 0.849(10) 1.731(13) 2.575(4) 172(5) 4_575 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.352 _refine_diff_density_min -0.967 _refine_diff_density_rms 0.119 _database_code_depnum_ccdc_archive 'CCDC 934429'