# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Ren-Gen Xiong'
_publ_contact_author_email       ?

_publ_section_title              
;
The First Metal-Organic Framework (MOF) of Imazethapyr
and Its SHG, Piezoelectric and Ferroelectric Properties
;
loop_
_publ_author_name
'Ren-Gen Xiong.'
'Da-Wei Fu.'
'Wen Zhang.'

# Attachment '260331A.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 684877'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H34 Cd N6 O6'
_chemical_formula_sum            'C30 H34 Cd N6 O6'
_chemical_formula_weight         687.03

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'
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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Fdd2 '
_symmetry_space_group_name_Hall  'F 2 -2d '

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

_cell_length_a                   23.8317(12)
_cell_length_b                   12.7975(7)
_cell_length_c                   20.1510(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6145.8(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2668
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      21.63

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2816
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart 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            9307
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         28.23
_reflns_number_total             2956
_reflns_number_gt                2660
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_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^)+(0.05P)^2^] 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    constr
_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   0.05(3)
_refine_ls_number_reflns         2956
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
C1 C 0.1498(2) 0.3848(3) 0.8944(3) 0.0420(11) Uani 1 1 d . . .
H1 H 0.1729 0.4375 0.9105 0.050 Uiso 1 1 calc R . .
C2 C 0.0988(2) 0.4132(4) 0.8681(3) 0.0424(11) Uani 1 1 d . . .
C3 C 0.06402(19) 0.3328(4) 0.8472(3) 0.0394(11) Uani 1 1 d . . .
H3 H 0.0288 0.3493 0.8304 0.047 Uiso 1 1 calc R . .
C4 C 0.08009(18) 0.2274(3) 0.8504(2) 0.0312(9) Uani 1 1 d . . .
C5 C 0.13448(16) 0.2098(3) 0.8759(2) 0.0301(9) Uani 1 1 d . . .
C6 C 0.16054(17) 0.1060(3) 0.8863(2) 0.0302(8) Uani 1 1 d . . .
C7 C 0.17745(19) -0.0689(4) 0.8810(3) 0.0423(11) Uani 1 1 d . . .
C8 C 0.2203(2) -0.0087(3) 0.9235(3) 0.0362(10) Uani 1 1 d . . .
C9 C 0.0822(2) 0.5280(4) 0.8661(4) 0.0615(18) Uani 1 1 d . . .
H9A H 0.1104 0.5663 0.8414 0.074 Uiso 1 1 calc R . .
H9B H 0.0469 0.5346 0.8425 0.074 Uiso 1 1 calc R . .
C10 C 0.0762(3) 0.5759(4) 0.9324(3) 0.0659(17) Uani 1 1 d . . .
H10A H 0.0495 0.5367 0.9580 0.099 Uiso 1 1 calc R . .
H10B H 0.0632 0.6466 0.9277 0.099 Uiso 1 1 calc R . .
H10C H 0.1118 0.5757 0.9546 0.099 Uiso 1 1 calc R . .
C11 C 0.03891(19) 0.1525(3) 0.8266(2) 0.0387(10) Uani 1 1 d . . .
C12 C 0.1456(2) -0.1504(4) 0.9227(3) 0.0589(15) Uani 1 1 d . . .
H12A H 0.1353 -0.1202 0.9645 0.088 Uiso 1 1 calc R . .
H12B H 0.1694 -0.2099 0.9302 0.088 Uiso 1 1 calc R . .
H12C H 0.1125 -0.1720 0.8994 0.088 Uiso 1 1 calc R . .
C13 C 0.2078(2) -0.1157(4) 0.8209(3) 0.0539(14) Uani 1 1 d . . .
H13 H 0.2370 -0.1621 0.8383 0.065 Uiso 1 1 calc R . .
C14 C 0.2371(3) -0.0344(6) 0.7795(4) 0.0702(18) Uani 1 1 d . . .
H14A H 0.2599 -0.0683 0.7466 0.105 Uiso 1 1 calc R . .
H14B H 0.2605 0.0079 0.8075 0.105 Uiso 1 1 calc R . .
H14C H 0.2098 0.0089 0.7580 0.105 Uiso 1 1 calc R . .
C15 C 0.1681(3) -0.1840(5) 0.7794(4) 0.074(2) Uani 1 1 d . . .
H15A H 0.1381 -0.1418 0.7623 0.111 Uiso 1 1 calc R . .
H15B H 0.1528 -0.2384 0.8069 0.111 Uiso 1 1 calc R . .
H15C H 0.1885 -0.2147 0.7433 0.111 Uiso 1 1 calc R . .
Cd1 Cd 0.2500 0.2500 0.96506(3) 0.02701(11) Uani 1 2 d S . .
N1 N 0.16801(15) 0.2879(3) 0.8983(2) 0.0382(9) Uani 1 1 d . . .
N2 N 0.20736(14) 0.0969(3) 0.92347(19) 0.0313(7) Uani 1 1 d . . .
N3 N 0.14107(18) 0.0179(3) 0.8613(2) 0.0429(11) Uani 1 1 d . . .
O1 O 0.25946(14) -0.0505(2) 0.9521(2) 0.0474(13) Uani 1 1 d . . .
O2 O 0.05681(12) 0.0790(2) 0.78864(17) 0.0404(7) Uani 1 1 d . . .
O3 O -0.01111(15) 0.1640(3) 0.8416(2) 0.0596(11) 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 0.047(3) 0.026(2) 0.052(3) -0.005(2) -0.012(2) -0.0019(18)
C2 0.045(3) 0.034(2) 0.048(3) -0.006(2) -0.012(2) 0.007(2)
C3 0.031(2) 0.042(2) 0.045(3) 0.000(2) -0.006(2) 0.0115(18)
C4 0.031(2) 0.037(2) 0.025(2) -0.0017(18) -0.0020(18) -0.0003(17)
C5 0.029(2) 0.0280(19) 0.033(2) -0.0069(18) -0.0046(17) 0.0020(15)
C6 0.028(2) 0.032(2) 0.030(2) -0.0001(18) -0.0047(16) 0.0024(16)
C7 0.042(3) 0.038(2) 0.048(3) -0.002(2) -0.017(2) 0.0107(19)
C8 0.038(2) 0.035(2) 0.036(3) -0.0025(19) -0.006(2) 0.0037(17)
C9 0.053(3) 0.033(2) 0.098(5) -0.009(3) -0.020(3) 0.008(2)
C10 0.071(4) 0.053(3) 0.074(4) -0.033(3) -0.003(3) 0.017(3)
C11 0.036(2) 0.041(2) 0.039(3) 0.000(2) -0.010(2) 0.0007(19)
C12 0.061(3) 0.043(3) 0.073(4) 0.004(3) -0.010(3) -0.015(2)
C13 0.062(3) 0.051(3) 0.049(3) -0.012(3) -0.010(3) 0.015(3)
C14 0.075(4) 0.079(4) 0.057(4) -0.011(4) 0.020(3) 0.009(4)
C15 0.071(4) 0.073(4) 0.078(5) -0.041(4) -0.045(4) 0.014(3)
Cd1 0.02225(16) 0.03030(18) 0.02849(18) 0.000 0.000 0.00230(19)
N1 0.0348(19) 0.0324(18) 0.047(2) -0.0030(18) -0.0096(17) 0.0033(16)
N2 0.0325(18) 0.0301(18) 0.0313(19) -0.0027(15) -0.0065(15) 0.0009(14)
N3 0.044(2) 0.0279(17) 0.057(3) -0.0052(18) -0.021(2) 0.0015(16)
O1 0.046(2) 0.0366(15) 0.060(4) 0.0030(18) -0.0223(19) 0.0044(13)
O2 0.0390(16) 0.0380(16) 0.0444(19) -0.0097(15) -0.0149(14) 0.0037(13)
O3 0.0362(19) 0.066(2) 0.077(3) -0.016(2) -0.0001(18) -0.0042(16)

_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 N1 1.316(6) . ?
C1 C2 1.374(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(7) . ?
C2 C9 1.522(6) . ?
C3 C4 1.404(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.412(6) . ?
C4 C11 1.453(6) . ?
C5 N1 1.357(5) . ?
C5 C6 1.481(6) . ?
C6 N3 1.319(5) . ?
C6 N2 1.349(5) . ?
C7 N3 1.464(5) . ?
C7 C13 1.532(7) . ?
C7 C12 1.539(7) . ?
C7 C8 1.539(7) . ?
C8 O1 1.222(6) . ?
C8 N2 1.386(5) . ?
C9 C10 1.478(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O3 1.239(6) . ?
C11 O2 1.285(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.506(9) . ?
C13 C15 1.535(7) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
Cd1 O2 2.248(3) 4 ?
Cd1 O2 2.248(3) 3 ?
Cd1 N2 2.361(3) . ?
Cd1 N2 2.361(3) 14 ?
Cd1 N1 2.421(4) . ?
Cd1 N1 2.421(4) 14 ?
O2 Cd1 2.248(3) 11_454 ?

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 C1 C2 124.3(4) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C1 C2 C3 116.7(4) . . ?
C1 C2 C9 119.7(4) . . ?
C3 C2 C9 123.6(4) . . ?
C2 C3 C4 122.4(4) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 114.8(4) . . ?
C3 C4 C11 115.7(4) . . ?
C5 C4 C11 129.4(4) . . ?
N1 C5 C4 123.0(4) . . ?
N1 C5 C6 111.5(3) . . ?
C4 C5 C6 125.4(4) . . ?
N3 C6 N2 115.4(4) . . ?
N3 C6 C5 124.4(4) . . ?
N2 C6 C5 120.2(4) . . ?
N3 C7 C13 111.2(4) . . ?
N3 C7 C12 111.8(4) . . ?
C13 C7 C12 113.5(4) . . ?
N3 C7 C8 99.4(3) . . ?
C13 C7 C8 108.8(4) . . ?
C12 C7 C8 111.2(4) . . ?
O1 C8 N2 126.7(4) . . ?
O1 C8 C7 123.3(4) . . ?
N2 C8 C7 110.0(4) . . ?
C10 C9 C2 113.7(5) . . ?
C10 C9 H9A 108.8 . . ?
C2 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C2 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 O2 123.5(4) . . ?
O3 C11 C4 119.4(4) . . ?
O2 C11 C4 117.1(4) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C7 112.8(5) . . ?
C14 C13 C15 112.3(6) . . ?
C7 C13 C15 111.2(5) . . ?
C14 C13 H13 106.7 . . ?
C7 C13 H13 106.7 . . ?
C15 C13 H13 106.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 Cd1 O2 97.45(18) 4 3 ?
O2 Cd1 N2 110.36(12) 4 . ?
O2 Cd1 N2 96.92(12) 3 . ?
O2 Cd1 N2 96.92(12) 4 14 ?
O2 Cd1 N2 110.36(12) 3 14 ?
N2 Cd1 N2 138.41(19) . 14 ?
O2 Cd1 N1 77.89(13) 4 . ?
O2 Cd1 N1 160.48(12) 3 . ?
N2 Cd1 N1 67.77(12) . . ?
N2 Cd1 N1 89.08(13) 14 . ?
O2 Cd1 N1 160.48(12) 4 14 ?
O2 Cd1 N1 77.89(13) 3 14 ?
N2 Cd1 N1 89.08(13) . 14 ?
N2 Cd1 N1 67.77(12) 14 14 ?
N1 Cd1 N1 112.5(2) . 14 ?
C1 N1 C5 118.6(4) . . ?
C1 N1 Cd1 119.2(3) . . ?
C5 N1 Cd1 120.8(3) . . ?
C6 N2 C8 105.5(3) . . ?
C6 N2 Cd1 118.8(3) . . ?
C8 N2 Cd1 135.5(3) . . ?
C6 N3 C7 109.7(4) . . ?
C11 O2 Cd1 121.4(3) . 11_454 ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        28.23
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.074