# 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
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#
# Cambridge Crystallographic Data Centre
# CCDC
#
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#
# 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
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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'