# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2011

data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       guozhiyong82@gmail.com
_publ_contact_author_name        Zhiyong
loop_
_publ_author_name
'Zhiyong Guo'
'Hui Xu'
'Banglin Chen'

data_Yb-BPT
_database_code_depnum_ccdc_archive 'CCDC 812200'
#TrackingRef 'Yb-BPT.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C15 H9 N0 O7 Yb'
_chemical_formula_sum            'C15 H9 N0 O7 Yb'
_chemical_formula_weight         474.26

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'
N N 0.0061 0.0033 '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'
Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(3)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   14.642(2)
_cell_length_b                   14.642(2)
_cell_length_c                   14.333(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3073.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4025
_cell_measurement_theta_min      1.29
_cell_measurement_theta_max      26.55

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.025
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             900
_exptl_absorpt_coefficient_mu    3.060
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7384
_exptl_absorpt_correction_T_max  0.7957
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            17227
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_sigmaI/netI    0.0754
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.39
_diffrn_reflns_theta_max         26.21
_reflns_number_total             4654
_reflns_number_gt                4025
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  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.
;

_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^)+(0.0707P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         4654
_refine_ls_number_parameters     214
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.004
_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
Yb1 Yb 0.63346(2) 0.41359(2) 0.48494(6) 0.01503(12) Uani 1 1 d D . .
O1 O 0.6142(5) 0.3623(5) 0.3384(5) 0.0248(16) Uani 1 1 d . . .
O2 O 0.6083(5) 0.4857(4) 0.2514(5) 0.0270(18) Uani 1 1 d . . .
O3 O 0.4591(5) 0.3273(5) -0.1240(5) 0.0275(17) Uani 1 1 d . . .
O4 O 0.4214(5) 0.4482(5) -0.0401(5) 0.0262(18) Uani 1 1 d . . .
O5 O 0.6492(5) -0.2203(4) 0.2183(5) 0.0282(18) Uani 1 1 d . . .
O6 O 0.5083(5) -0.2393(4) 0.1741(5) 0.0238(16) Uani 1 1 d . . .
O7 O 0.6234(5) 0.2728(5) 0.5438(6) 0.0297(18) Uani 1 1 d D . .
H7A H 0.649(8) 0.268(3) 0.609(3) 0.080 Uiso 1 1 d D . .
H7B H 0.665(6) 0.227(2) 0.512(6) 0.080 Uiso 1 1 d D . .
C1 C 0.5712(7) 0.3447(6) 0.1838(7) 0.020(2) Uani 1 1 d . . .
C2 C 0.5281(7) 0.3819(7) 0.1074(6) 0.0160(19) Uani 1 1 d . . .
H2 H 0.5186 0.4446 0.1043 0.080 Uiso 1 1 calc . . .
C3 C 0.4989(7) 0.3264(7) 0.0350(7) 0.021(2) Uani 1 1 d . . .
C4 C 0.5075(8) 0.2331(8) 0.0397(8) 0.033(3) Uani 1 1 d . . .
H4 H 0.4850 0.1966 -0.0081 0.080 Uiso 1 1 calc . . .
C5 C 0.5505(8) 0.1930(6) 0.1173(7) 0.026(2) Uani 1 1 d . . .
C6 C 0.5817(7) 0.2506(7) 0.1895(7) 0.023(2) Uani 1 1 d . . .
H6 H 0.6098 0.2253 0.2416 0.080 Uiso 1 1 calc . . .
C7 C 0.6008(7) 0.4009(6) 0.2625(6) 0.014(2) Uani 1 1 d . . .
C8 C 0.4563(7) 0.3697(7) -0.0504(8) 0.024(2) Uani 1 1 d . . .
C9 C 0.5593(8) 0.0935(7) 0.1272(7) 0.029(3) Uani 1 1 d . . .
C10 C 0.6391(8) 0.0573(7) 0.1623(9) 0.036(3) Uani 1 1 d . . .
H10 H 0.6890 0.0947 0.1747 0.080 Uiso 1 1 calc . . .
C11 C 0.6436(9) -0.0347(8) 0.1786(9) 0.038(3) Uani 1 1 d . . .
H11 H 0.6976 -0.0598 0.2012 0.080 Uiso 1 1 calc . . .
C12 C 0.5694(7) -0.0911(7) 0.1622(7) 0.024(2) Uani 1 1 d . . .
C13 C 0.4888(8) -0.0554(8) 0.1284(9) 0.036(3) Uani 1 1 d . . .
H13 H 0.4382 -0.0925 0.1186 0.080 Uiso 1 1 calc . . .
C14 C 0.4852(10) 0.0393(8) 0.1092(9) 0.045(3) Uani 1 1 d . . .
H14 H 0.4324 0.0647 0.0842 0.080 Uiso 1 1 calc . . .
C15 C 0.5761(7) -0.1891(7) 0.1879(7) 0.023(2) 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
Yb1 0.0152(2) 0.0216(2) 0.00823(17) -0.00110(17) -0.00005(17) 0.00041(16)
O1 0.046(5) 0.020(4) 0.008(4) -0.003(3) -0.001(3) -0.001(3)
O2 0.050(5) 0.016(3) 0.015(4) -0.007(3) -0.005(3) 0.001(3)
O3 0.047(5) 0.030(4) 0.005(3) -0.004(3) -0.009(3) 0.007(4)
O4 0.033(4) 0.024(4) 0.022(5) -0.001(3) -0.010(3) 0.006(3)
O5 0.037(4) 0.011(3) 0.037(5) 0.007(3) -0.015(4) -0.004(3)
O6 0.035(4) 0.013(3) 0.024(4) 0.008(3) -0.011(3) 0.004(3)
O7 0.026(4) 0.027(4) 0.036(5) 0.007(3) 0.003(3) 0.002(3)
C1 0.025(5) 0.013(5) 0.021(5) -0.001(4) -0.001(4) -0.006(4)
C2 0.028(5) 0.018(5) 0.002(4) 0.004(3) -0.002(3) 0.008(4)
C3 0.029(6) 0.023(5) 0.011(5) -0.003(4) -0.006(4) 0.009(4)
C4 0.045(7) 0.033(6) 0.020(6) 0.000(5) -0.015(5) 0.009(5)
C5 0.052(7) 0.008(5) 0.018(5) -0.002(4) -0.004(5) 0.000(4)
C6 0.040(6) 0.020(5) 0.010(5) -0.005(4) -0.014(4) 0.002(4)
C7 0.024(5) 0.008(4) 0.011(5) -0.003(3) -0.001(4) -0.001(4)
C8 0.017(6) 0.024(6) 0.031(6) 0.015(4) 0.000(4) -0.004(4)
C9 0.054(7) 0.014(5) 0.018(6) 0.003(4) -0.015(5) 0.002(5)
C10 0.037(7) 0.017(6) 0.053(8) 0.006(5) -0.015(6) 0.000(5)
C11 0.050(8) 0.021(6) 0.043(8) 0.001(5) -0.009(6) 0.002(5)
C12 0.024(6) 0.027(6) 0.022(6) -0.008(4) -0.012(4) 0.001(4)
C13 0.044(7) 0.024(6) 0.041(7) -0.001(5) -0.022(6) 0.005(5)
C14 0.074(10) 0.037(7) 0.023(6) -0.001(5) -0.024(6) -0.008(7)
C15 0.037(6) 0.014(5) 0.016(5) 0.005(4) -0.004(4) -0.012(4)

_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
Yb1 O2 2.200(7) 4_565 ?
Yb1 O3 2.205(7) 3_655 ?
Yb1 O4 2.206(7) 2_665 ?
Yb1 O7 2.233(8) . ?
Yb1 O1 2.248(7) . ?
Yb1 O5 2.342(6) 4_665 ?
Yb1 O6 2.353(6) 4_665 ?
Yb1 C15 2.689(10) 4_665 ?
Yb1 C8 3.141(11) 3_655 ?
O1 C7 1.243(11) . ?
O2 C7 1.256(11) . ?
O2 Yb1 2.200(7) 3_654 ?
O3 C8 1.225(13) . ?
O3 Yb1 2.205(7) 4_564 ?
O4 C8 1.266(13) . ?
O4 Yb1 2.206(7) 2_664 ?
O5 C15 1.243(12) . ?
O5 Yb1 2.342(6) 3_644 ?
O6 C15 1.250(12) . ?
O6 Yb1 2.353(6) 3_644 ?
O7 H7A 1.02(2) . ?
O7 H7B 1.02(2) . ?
C1 C2 1.376(14) . ?
C1 C6 1.388(13) . ?
C1 C7 1.462(13) . ?
C2 C3 1.386(14) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(15) . ?
C3 C8 1.512(14) . ?
C4 C5 1.406(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(13) . ?
C5 C9 1.469(14) . ?
C6 H6 0.9300 . ?
C8 Yb1 3.141(11) 4_564 ?
C9 C14 1.369(17) . ?
C9 C10 1.378(15) . ?
C10 C11 1.368(15) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(15) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(14) . ?
C12 C15 1.484(14) . ?
C13 C14 1.414(16) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 Yb1 2.689(10) 3_644 ?

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
O2 Yb1 O3 101.7(3) 4_565 3_655 ?
O2 Yb1 O4 78.1(3) 4_565 2_665 ?
O3 Yb1 O4 88.1(3) 3_655 2_665 ?
O2 Yb1 O7 76.1(3) 4_565 . ?
O3 Yb1 O7 87.1(3) 3_655 . ?
O4 Yb1 O7 152.1(3) 2_665 . ?
O2 Yb1 O1 85.9(3) 4_565 . ?
O3 Yb1 O1 172.0(3) 3_655 . ?
O4 Yb1 O1 96.3(3) 2_665 . ?
O7 Yb1 O1 92.1(3) . . ?
O2 Yb1 O5 148.5(3) 4_565 4_665 ?
O3 Yb1 O5 88.5(3) 3_655 4_665 ?
O4 Yb1 O5 132.5(2) 2_665 4_665 ?
O7 Yb1 O5 74.7(2) . 4_665 ?
O1 Yb1 O5 83.6(3) . 4_665 ?
O2 Yb1 O6 152.8(3) 4_565 4_665 ?
O3 Yb1 O6 89.2(3) 3_655 4_665 ?
O4 Yb1 O6 77.5(2) 2_665 4_665 ?
O7 Yb1 O6 129.9(3) . 4_665 ?
O1 Yb1 O6 85.2(3) . 4_665 ?
O5 Yb1 O6 55.2(2) 4_665 4_665 ?
O2 Yb1 C15 170.3(3) 4_565 4_665 ?
O3 Yb1 C15 87.8(3) 3_655 4_665 ?
O4 Yb1 C15 105.1(3) 2_665 4_665 ?
O7 Yb1 C15 102.2(3) . 4_665 ?
O1 Yb1 C15 84.6(3) . 4_665 ?
O5 Yb1 C15 27.5(3) 4_665 4_665 ?
O6 Yb1 C15 27.7(3) 4_665 4_665 ?
O2 Yb1 C8 84.8(3) 4_565 3_655 ?
O3 Yb1 C8 17.3(3) 3_655 3_655 ?
O4 Yb1 C8 88.3(3) 2_665 3_655 ?
O7 Yb1 C8 79.2(3) . 3_655 ?
O1 Yb1 C8 168.5(3) . 3_655 ?
O5 Yb1 C8 101.0(3) 4_665 3_655 ?
O6 Yb1 C8 106.1(3) 4_665 3_655 ?
C15 Yb1 C8 104.4(3) 4_665 3_655 ?
C7 O1 Yb1 133.3(6) . . ?
C7 O2 Yb1 166.5(8) . 3_654 ?
C8 O3 Yb1 130.3(7) . 4_564 ?
C8 O4 Yb1 176.5(7) . 2_664 ?
C15 O5 Yb1 92.0(5) . 3_644 ?
C15 O6 Yb1 91.2(6) . 3_644 ?
Yb1 O7 H7A 113.0(19) . . ?
Yb1 O7 H7B 113.2(19) . . ?
H7A O7 H7B 99(2) . . ?
C2 C1 C6 119.3(9) . . ?
C2 C1 C7 121.8(9) . . ?
C6 C1 C7 118.7(9) . . ?
C1 C2 C3 120.4(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 121.2(9) . . ?
C4 C3 C8 119.7(9) . . ?
C2 C3 C8 119.1(9) . . ?
C3 C4 C5 119.7(10) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 118.3(9) . . ?
C4 C5 C9 122.0(9) . . ?
C6 C5 C9 119.6(9) . . ?
C1 C6 C5 121.0(9) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
O1 C7 O2 123.2(8) . . ?
O1 C7 C1 117.8(8) . . ?
O2 C7 C1 119.0(8) . . ?
O3 C8 O4 125.0(10) . . ?
O3 C8 C3 118.0(9) . . ?
O4 C8 C3 117.0(10) . . ?
O3 C8 Yb1 32.4(5) . 4_564 ?
O4 C8 Yb1 92.7(6) . 4_564 ?
C3 C8 Yb1 150.2(7) . 4_564 ?
C14 C9 C10 121.1(10) . . ?
C14 C9 C5 119.2(10) . . ?
C10 C9 C5 119.4(10) . . ?
C11 C10 C9 118.9(11) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 121.3(11) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 120.3(10) . . ?
C13 C12 C15 120.7(9) . . ?
C11 C12 C15 118.9(9) . . ?
C12 C13 C14 118.1(11) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C9 C14 C13 120.2(11) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
O5 C15 O6 121.5(9) . . ?
O5 C15 C12 120.0(8) . . ?
O6 C15 C12 118.5(9) . . ?
O5 C15 Yb1 60.5(5) . 3_644 ?
O6 C15 Yb1 61.1(5) . 3_644 ?
C12 C15 Yb1 179.4(8) . 3_644 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.21
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.039
_refine_diff_density_min         -0.877
_refine_diff_density_rms         0.207