# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222

_publ_contact_author_name        'Chun-Yang Pan'
_publ_contact_author_email       PANCHUNY@GDUT.EDU.CN

_publ_section_title              
;
The First Ferroelectric Templated Borate: [Ni(en) 2pip][B5O6(OH)4]2
;
loop_
_publ_author_name
'Chun-Yang Pan'
'Sheng Hu'
'Da-Guang Li'
'Ping Ouyang'
'Feng-Hua Zhao'
;
Yu-Ying Zheng
;

# Attachment '1.CIF'

data_1
_database_code_depnum_ccdc_archive 'CCDC 721773'
#TrackingRef '1.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H34 B10 N6 Ni O40'
_chemical_formula_weight         701.18

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'
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'
Ni Ni 0.3393 1.1124 '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

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

_cell_length_a                   14.4598(17)
_cell_length_b                   11.7213(17)
_cell_length_c                   8.5302(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.875(10)
_cell_angle_gamma                90.00
_cell_volume                     1445.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1772
_cell_measurement_theta_min      3.2594
_cell_measurement_theta_max      27.4835

_exptl_crystal_description       prism
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             770
_exptl_absorpt_coefficient_mu    0.853
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8316
_exptl_absorpt_correction_T_max  1.0000

_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  'Smart CCD'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            5352
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2956
_reflns_number_gt                2579
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker XSCANS'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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.
;

_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^)+(0.1501P)^2^+1.1123P] 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    contrs
_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   0.47(3)
_refine_ls_number_reflns         2956
_refine_ls_number_parameters     205
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.2119
_refine_ls_wR_factor_gt          0.1947
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_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
Ni Ni 0.0000 0.15914(7) 0.5000 0.0349(3) Uani 1 2 d S . .
B1 B 0.3107(5) 0.7611(9) 1.0616(9) 0.050(2) Uani 1 1 d . . .
B2 B 0.3131(7) 0.5571(8) 1.0520(9) 0.048(2) Uani 1 1 d . . .
B3 B 0.2014(3) 0.6566(9) 0.8768(5) 0.0379(12) Uani 1 1 d . . .
B4 B 0.0392(3) 0.6601(12) 0.7779(5) 0.0414(11) Uani 1 1 d . . .
B5 B 0.1610(3) 0.6554(12) 0.5955(5) 0.0488(15) Uani 1 1 d . . .
O1 O 0.3448(4) 0.8522(6) 1.1222(6) 0.0650(17) Uani 1 1 d . . .
H1A H 0.3136 0.9073 1.0947 0.097 Uiso 1 1 calc R . .
O2 O 0.3507(4) 0.4600(6) 1.1172(7) 0.0668(19) Uani 1 1 d . . .
H2A H 0.3211 0.4042 1.0875 0.100 Uiso 1 1 calc R . .
O3 O -0.05344(17) 0.6577(8) 0.7984(3) 0.0492(9) Uani 1 1 d . . .
H3A H -0.0645 0.6589 0.8924 0.074 Uiso 1 1 calc R . .
O4 O 0.1885(2) 0.6580(8) 0.4444(3) 0.0562(10) Uani 1 1 d . . .
H4A H 0.1429 0.6576 0.3860 0.084 Uiso 1 1 calc R . .
O5 O 0.3509(2) 0.6606(8) 1.1029(4) 0.0576(10) Uani 1 1 d . . .
O6 O 0.2417(3) 0.5537(5) 0.9559(5) 0.0432(13) Uani 1 1 d . . .
O7 O 0.2378(3) 0.7594(4) 0.9485(5) 0.0384(11) Uani 1 1 d . . .
O8 O 0.10114(17) 0.6585(6) 0.8981(3) 0.0356(6) Uani 1 1 d . . .
O9 O 0.0686(2) 0.6530(9) 0.6273(3) 0.0690(15) Uani 1 1 d . . .
O10 O 0.22508(17) 0.6603(7) 0.7113(3) 0.0441(8) Uani 1 1 d . . .
C1 C -0.0616(10) 0.3492(10) 0.6793(12) 0.094(3) Uani 1 1 d . . .
H1B H -0.0913 0.3876 0.7658 0.113 Uiso 1 1 calc R . .
H1C H -0.0005 0.3819 0.6671 0.113 Uiso 1 1 calc R . .
N2 N -0.0539(4) 0.2309(6) 0.7120(7) 0.0625(15) Uani 1 1 d . . .
H2D H -0.1095 0.2007 0.7338 0.075 Uiso 1 1 calc R . .
H2E H -0.0151 0.2184 0.7936 0.075 Uiso 1 1 calc R . .
N1 N -0.1233(4) 0.2538(6) 0.4709(7) 0.0609(15) Uani 1 1 d . . .
H1D H -0.1365 0.2620 0.3681 0.073 Uiso 1 1 calc R . .
H1E H -0.1705 0.2160 0.5151 0.073 Uiso 1 1 calc R . .
C2 C -0.1133(7) 0.3646(12) 0.543(2) 0.129(7) Uani 1 1 d . . .
H2B H -0.0819 0.4165 0.4729 0.155 Uiso 1 1 calc R . .
H2C H -0.1735 0.3962 0.5667 0.155 Uiso 1 1 calc R . .
C4 C -0.1163(8) -0.0375(10) 0.5390(18) 0.103(4) Uani 1 1 d . . .
H4D H -0.1527 0.0249 0.5800 0.124 Uiso 1 1 calc R . .
H4E H -0.1557 -0.1007 0.5074 0.124 Uiso 1 1 calc R . .
C3 C -0.0428(10) -0.0693(15) 0.637(2) 0.166(9) Uani 1 1 d . . .
H4B H -0.0303 -0.1501 0.6243 0.199 Uiso 1 1 calc R . .
H4C H -0.0584 -0.0555 0.7452 0.199 Uiso 1 1 calc R . .
N3 N 0.0444(4) 0.0010(5) 0.5936(7) 0.0560(13) Uani 1 1 d . . .
H3B H 0.0548 0.0637 0.6431 0.067 Uiso 1 1 calc R . .

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
Ni 0.0218(4) 0.0544(5) 0.0282(4) 0.000 -0.0056(2) 0.000
B1 0.015(3) 0.088(7) 0.046(4) 0.021(4) -0.012(2) -0.010(3)
B2 0.058(5) 0.057(5) 0.029(3) 0.019(3) -0.020(3) -0.001(4)
B3 0.0214(17) 0.063(3) 0.029(2) 0.026(4) -0.0067(14) -0.004(4)
B4 0.0228(18) 0.078(4) 0.0238(18) 0.001(5) -0.0041(14) -0.009(5)
B5 0.0227(19) 0.099(5) 0.0245(19) -0.002(5) -0.0041(15) -0.020(5)
O1 0.079(4) 0.067(4) 0.048(3) -0.005(2) -0.048(3) -0.010(3)
O2 0.042(3) 0.066(4) 0.092(5) -0.004(3) -0.038(3) 0.006(3)
O3 0.0200(12) 0.105(3) 0.0222(12) 0.000(3) -0.0032(9) 0.003(3)
O4 0.0278(14) 0.119(3) 0.0223(12) -0.005(3) -0.0019(10) -0.019(4)
O5 0.0470(18) 0.068(2) 0.057(2) 0.009(3) -0.0343(15) -0.010(4)
O6 0.032(3) 0.063(3) 0.033(3) -0.011(2) -0.0156(18) 0.007(2)
O7 0.029(2) 0.054(3) 0.032(2) -0.0067(19) -0.0160(17) -0.003(2)
O8 0.0223(12) 0.0626(19) 0.0216(11) 0.000(2) -0.0056(8) -0.004(3)
O9 0.0206(13) 0.164(5) 0.0223(14) -0.019(4) -0.0053(10) 0.000(4)
O10 0.0184(11) 0.090(2) 0.0239(12) -0.007(3) -0.0040(9) -0.012(3)
C1 0.141(10) 0.064(6) 0.077(6) -0.023(4) -0.012(6) 0.014(6)
N2 0.053(3) 0.082(4) 0.053(3) -0.012(3) 0.008(2) 0.001(3)
N1 0.034(2) 0.083(4) 0.065(3) 0.001(3) -0.006(2) -0.001(3)
C2 0.039(5) 0.088(8) 0.26(2) -0.073(11) 0.011(7) 0.007(5)
C4 0.078(7) 0.063(6) 0.167(11) 0.025(7) -0.057(7) -0.034(5)
C3 0.139(12) 0.152(14) 0.204(13) 0.131(12) -0.120(11) -0.106(11)
N3 0.038(2) 0.064(4) 0.066(3) 0.014(3) -0.010(2) 0.002(2)

_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
Ni N1 2.112(6) 2_556 ?
Ni N1 2.112(6) . ?
Ni N3 2.114(6) 2_556 ?
Ni N3 2.114(6) . ?
Ni N2 2.151(5) . ?
Ni N2 2.151(5) 2_556 ?
B1 O1 1.282(11) . ?
B1 O5 1.357(13) . ?
B1 O7 1.418(8) . ?
B2 O6 1.310(9) . ?
B2 O2 1.375(11) . ?
B2 O5 1.397(13) . ?
B3 O7 1.448(11) . ?
B3 O10 1.459(5) . ?
B3 O8 1.463(5) . ?
B3 O6 1.496(10) . ?
B4 O8 1.352(5) . ?
B4 O3 1.353(5) . ?
B4 O9 1.362(5) . ?
B5 O10 1.345(5) . ?
B5 O4 1.355(5) . ?
B5 O9 1.368(5) . ?
O1 H1A 0.8200 . ?
O2 H2A 0.8200 . ?
O3 H3A 0.8200 . ?
O4 H4A 0.8200 . ?
C1 C2 1.39(2) . ?
C1 N2 1.418(13) . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
N2 H2D 0.9000 . ?
N2 H2E 0.9000 . ?
N1 C2 1.443(14) . ?
N1 H1D 0.9000 . ?
N1 H1E 0.9000 . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C4 C3 1.392(14) . ?
C4 N3 1.612(16) 2_556 ?
C4 H4D 0.9700 . ?
C4 H4E 0.9700 . ?
C3 N3 1.555(11) . ?
C3 H4B 0.9700 . ?
C3 H4C 0.9700 . ?
N3 C4 1.612(16) 2_556 ?
N3 H3B 0.8600 . ?

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
N1 Ni N1 116.6(4) 2_556 . ?
N1 Ni N3 139.1(2) 2_556 2_556 ?
N1 Ni N3 99.5(2) . 2_556 ?
N1 Ni N3 99.5(2) 2_556 . ?
N1 Ni N3 139.1(2) . . ?
N3 Ni N3 57.5(3) 2_556 . ?
N1 Ni N2 90.7(2) 2_556 . ?
N1 Ni N2 65.0(2) . . ?
N3 Ni N2 123.2(2) 2_556 . ?
N3 Ni N2 97.9(3) . . ?
N1 Ni N2 65.0(2) 2_556 2_556 ?
N1 Ni N2 90.7(2) . 2_556 ?
N3 Ni N2 97.9(3) 2_556 2_556 ?
N3 Ni N2 123.2(2) . 2_556 ?
N2 Ni N2 134.0(4) . 2_556 ?
O1 B1 O5 117.2(6) . . ?
O1 B1 O7 124.3(8) . . ?
O5 B1 O7 118.4(8) . . ?
O6 B2 O2 122.1(8) . . ?
O6 B2 O5 121.4(7) . . ?
O2 B2 O5 116.3(6) . . ?
O7 B3 O10 107.1(5) . . ?
O7 B3 O8 106.8(7) . . ?
O10 B3 O8 111.6(3) . . ?
O7 B3 O6 110.1(3) . . ?
O10 B3 O6 111.4(6) . . ?
O8 B3 O6 109.7(5) . . ?
O8 B4 O3 123.2(3) . . ?
O8 B4 O9 120.1(3) . . ?
O3 B4 O9 116.4(3) . . ?
O10 B5 O4 119.3(4) . . ?
O10 B5 O9 121.3(4) . . ?
O4 B5 O9 119.4(4) . . ?
B1 O1 H1A 109.5 . . ?
B2 O2 H2A 109.5 . . ?
B4 O3 H3A 109.5 . . ?
B5 O4 H4A 109.5 . . ?
B1 O5 B2 120.6(4) . . ?
B2 O6 B3 123.8(7) . . ?
B1 O7 B3 124.1(6) . . ?
B4 O8 B3 123.5(3) . . ?
B4 O9 B5 120.4(3) . . ?
B5 O10 B3 122.7(3) . . ?
C2 C1 N2 109.4(10) . . ?
C2 C1 H1B 109.8 . . ?
N2 C1 H1B 109.8 . . ?
C2 C1 H1C 109.8 . . ?
N2 C1 H1C 109.8 . . ?
H1B C1 H1C 108.2 . . ?
C1 N2 Ni 104.2(6) . . ?
C1 N2 H2D 110.9 . . ?
Ni N2 H2D 110.9 . . ?
C1 N2 H2E 110.9 . . ?
Ni N2 H2E 110.9 . . ?
H2D N2 H2E 108.9 . . ?
C2 N1 Ni 110.1(6) . . ?
C2 N1 H1D 109.6 . . ?
Ni N1 H1D 109.6 . . ?
C2 N1 H1E 109.6 . . ?
Ni N1 H1E 109.6 . . ?
H1D N1 H1E 108.2 . . ?
C1 C2 N1 106.8(12) . . ?
C1 C2 H2B 110.4 . . ?
N1 C2 H2B 110.4 . . ?
C1 C2 H2C 110.4 . . ?
N1 C2 H2C 110.4 . . ?
H2B C2 H2C 108.6 . . ?
C3 C4 N3 90.0(9) . 2_556 ?
C3 C4 H4D 113.6 . . ?
N3 C4 H4D 113.6 2_556 . ?
C3 C4 H4E 113.6 . . ?
N3 C4 H4E 113.6 2_556 . ?
H4D C4 H4E 110.9 . . ?
C4 C3 N3 109.4(9) . . ?
C4 C3 H4B 109.8 . . ?
N3 C3 H4B 109.8 . . ?
C4 C3 H4C 109.8 . . ?
N3 C3 H4C 109.8 . . ?
H4B C3 H4C 108.3 . . ?
C3 N3 C4 123.4(11) . 2_556 ?
C3 N3 Ni 108.1(6) . . ?
C4 N3 Ni 100.1(5) 2_556 . ?
C3 N3 H3B 118.3 . . ?
C4 N3 H3B 118.3 2_556 . ?
Ni N3 H3B 59.1 . . ?

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 H1A O6 0.82 1.94 2.750(9) 169.6 4_557
O2 H2A O7 0.82 1.92 2.731(9) 169.2 4_547
O3 H3A O8 0.82 1.87 2.689(3) 174.6 2_557
O4 H4A O3 0.82 2.02 2.825(4) 166.3 2_556
N2 H2D O10 0.90 2.44 3.301(7) 159.4 3_445
N2 H2E O5 0.90 2.61 3.413(7) 149.1 4_547
N1 H1D O1 0.90 2.36 3.217(8) 159.1 3_444
N1 H1D O5 0.90 2.56 3.339(8) 145.4 3_444
N1 H1E O4 0.90 2.22 2.949(7) 137.2 3_445
N1 H1E O10 0.90 2.36 3.216(7) 158.2 3_445
N3 H3B N1 0.86 2.63 3.225(9) 127.3 2_556

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.799
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.120