# 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
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Seong Huh.'
_publ_contact_author_email       SHUH@HUFS.AC.KR

_publ_section_title              
;
DABCO-functionalized metal-organic
framework bearing a C2h-symmetric terphenyl dicarboxylate linker
;
loop_
_publ_author_name
'Ja-Min Gu'
'Tae-Hwan Kwon'
'Ji-Hyun Park'
'Seong Huh.'

# Attachment 'k0976_GJM006.cif'

data_k0976twin_GJM006
_database_code_depnum_ccdc_archive 'CCDC 762032'
#TrackingRef 'k0976_GJM006.cif'

_audit_creation_method           SHELXL-97

#
# --- Checklist of Data Items for Deposition to CCDC ---
#
#
# 1. Name of contact person: Prof. Dr. Seong Huh
# 2. E-mail address of contact person: shuh@hufs.ac.kr
# 3. Author's names:
# Ja-Min Gu,
# Department of Chemistry and Protein Research Center for Bio-Industry,
# Hankuk University of Foreign Studies, Yongin 449-791, Korea
# Tae-Hwan Kwon,
# Department of Chemistry and Protein Research Center for Bio-Industry,
# Hankuk University of Foreign Studies, Yongin 449-791, Korea
# Ji-Hyun Park,
# Department of Chemistry and Protein Research Center for Bio-Industry,
# Hankuk University of Foreign Studies, Yongin 449-791, Korea
# Seong Huh,
# Department of Chemistry and Protein Research Center for Bio-Industry,
# Hankuk University of Foreign Studies, Yongin 449-791, Korea
# 4. Name of the journal to which the paper will be submitted:
# Chem. Commun.
# 5. Compound name:
# bis(3,3''-dicarboxylic-1,1':4',1''-terphenyl)
# (1,4-diazabicyclo[2,2,2]octane)zinc
# 6. Compound synonym: N.A.
# 7. Formula: C26 H24 N2 O4 Zn
# 8. Formula weight: 493.84
# 9. Colour: colorless
# 10. Melting point: N.A.
# 11. Unit cell parameters with standard deviations:
# a= 9.8933(12)
# b= 18.1647(15)
# c= 13.4537(16)
# alpha=90.00
# beta=94.792(4)
# gamma=90.00
# 12. Unit cell volume: 2409.3(5) A^3
# 13. Space group symbol: C 2/m, monoclinic
# 14. Z value: 4
# 15. Calculated density: 1.361 g/cm^3
# 16. Temperature of study: 150(1) K
# 17. R-factor: Please refer to EXP566R2.cif content.
# 18. Atomic coordinates with standard deviations:
# Please refer to k0976_GJM006.cif content.
# 19. Atomic displacement parameters with standard deviations:
# Please refer to k0976_GJM006.cif content.
# 20. Bond lengths with standard deviations:
# Please refer to k0976_GJM006.cif content.
# 21. Bond angles with standard deviations:
# Please refer to k0976_GJM006.cif content.
#
# CCDC No.:
#
# --- End ---

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 N2 O4 Zn'
_chemical_formula_sum            'C26 H24 N2 O4 Zn'
_chemical_formula_weight         493.84

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/m'
_symmetry_space_group_name_Hall  '-C 2y'

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

_cell_length_a                   9.8933(12)
_cell_length_b                   18.1647(15)
_cell_length_c                   13.4537(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.792(4)
_cell_angle_gamma                90.00
_cell_volume                     2409.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    7688
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    1.053
# Absorption correction

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_T_max  1.012
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(1)
_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  'Nonius KappaCCD'
_diffrn_measurement_method       '\f scans and \w scans with \k offsets'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7688
_diffrn_reflns_av_R_equivalents  0.086
_diffrn_reflns_av_sigmaI/netI    0.0901
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2191
_reflns_number_gt                1642
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        Denzo-SMN
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'

_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C.,
Polidori, G. & Camalli, M. (1994). <i>J. Appl. Cryst.</i> <b>27</b>, 435--?.

Blessing, R. H. (1995). <i>Acta Cryst.</i> A<b>51</b>, 33--38.

Nonius, B. V. (1997--2002). Collect. Data collection software, Delft, The
Netherlands.

Otwinowski, Z. & Minor, W. (1997). <i>Methods in Enzymology</i>, Vol. 276,
Macromolecular Crystallography, Part A edited by C. W. Carter & R. M. Sweet
pp. 307-326. London: Academic press.

Sheldrick, G. M. (2008). <i>Acta Cryst.</i> A<b>64</b>, 112--122.

Spek, A. L. (2003). <i>J. Appl. Cryst.</i> <b>36</b>, 7--13.
;

_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^)+(0.1649P)^2^+9.3340P] 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_number_reflns         2191
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0974
_refine_ls_wR_factor_ref         0.2799
_refine_ls_wR_factor_gt          0.2646
_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
Zn1 Zn 0.10207(13) 0.5000 0.58904(10) 0.0396(5) Uani 1 2 d S . .
O1 O 0.1588(7) 0.5792(3) 0.4925(5) 0.0546(15) Uani 1 1 d . . .
O2 O 0.0190(6) 0.5764(3) 0.3509(5) 0.0501(15) Uani 1 1 d . . .
N1 N 0.2818(15) 0.5000 0.6762(9) 0.067(3) Uani 1 2 d S . .
N2 N 0.5138(19) 0.5000 0.7851(16) 0.110(5) Uani 1 2 d S . .
C1 C 0.1267(8) 0.5984(4) 0.4032(7) 0.0431(19) Uani 1 1 d . . .
C2 C 0.2133(8) 0.6527(5) 0.3572(6) 0.0450(19) Uani 1 1 d . . .
C3 C 0.3143(10) 0.6894(5) 0.4173(7) 0.054(2) Uani 1 1 d . . .
H3 H 0.3287 0.6781 0.4864 0.065 Uiso 1 1 calc R . .
C4 C 0.3932(10) 0.7422(6) 0.3754(7) 0.063(3) Uani 1 1 d . . .
H4 H 0.4584 0.7689 0.4169 0.075 Uiso 1 1 calc R . .
C5 C 0.3785(10) 0.7565(5) 0.2739(7) 0.056(2) Uani 1 1 d . . .
H5 H 0.4349 0.7921 0.2461 0.067 Uiso 1 1 calc R . .
C6 C 0.2805(8) 0.7187(4) 0.2121(6) 0.0458(19) Uani 1 1 d . . .
C7 C 0.1984(8) 0.6660(5) 0.2548(6) 0.0453(19) Uani 1 1 d . . .
H7 H 0.1326 0.6395 0.2136 0.054 Uiso 1 1 calc R . .
C8 C 0.2644(8) 0.7347(5) 0.1032(6) 0.0438(19) Uani 1 1 d . . .
C12 C 0.3025(13) 0.4339(6) 0.7370(11) 0.089(4) Uani 1 1 d . . .
H12A H 0.2987 0.3903 0.6927 0.107 Uiso 1 1 calc R . .
H12B H 0.2277 0.4296 0.7811 0.107 Uiso 1 1 calc R . .
C11 C 0.4428(14) 0.4337(9) 0.8033(12) 0.108(5) Uani 1 1 d . . .
H11A H 0.4265 0.4303 0.8748 0.129 Uiso 1 1 calc R . .
H11B H 0.4976 0.3906 0.7862 0.129 Uiso 1 1 calc R . .
C13 C 0.4016(19) 0.5000 0.6122(15) 0.091(6) Uani 1 2 d S . .
H13A H 0.3955 0.5440 0.5687 0.110 Uiso 0.50 1 calc PR . .
H13B H 0.3955 0.4560 0.5687 0.110 Uiso 0.50 1 calc PR . .
C14 C 0.5455(19) 0.5000 0.675(2) 0.113(8) Uani 1 2 d S . .
H14A H 0.5983 0.4557 0.6602 0.136 Uiso 0.50 1 calc PR . .
H14B H 0.5983 0.5443 0.6602 0.136 Uiso 0.50 1 calc PR . .
C10 C 0.2398(18) 0.6784(10) 0.0333(12) 0.049(4) Uiso 0.501(12) 1 d P . 1
H10 H 0.2323 0.6290 0.0550 0.059 Uiso 0.501(12) 1 calc PR . 1
C9 C 0.2736(17) 0.8057(9) 0.0662(12) 0.045(4) Uiso 0.501(12) 1 d P . 1
H9 H 0.2901 0.8449 0.1123 0.055 Uiso 0.501(12) 1 calc PR . 1
C10A C 0.378(2) 0.7485(10) 0.0497(13) 0.050(4) Uiso 0.499(12) 1 d P . 2
H10A H 0.4661 0.7474 0.0831 0.060 Uiso 0.499(12) 1 calc PR . 2
C9A C 0.139(2) 0.7368(10) 0.0489(14) 0.057(5) Uiso 0.499(12) 1 d P . 2
H9A H 0.0603 0.7273 0.0829 0.068 Uiso 0.499(12) 1 calc PR . 2

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
Zn1 0.0354(7) 0.0357(7) 0.0478(8) 0.000 0.0033(5) 0.000
O1 0.052(4) 0.054(3) 0.059(4) 0.009(3) 0.014(3) -0.003(3)
O2 0.042(3) 0.039(3) 0.071(4) 0.004(3) 0.012(3) -0.002(3)
N1 0.085(9) 0.045(6) 0.071(8) 0.000 -0.007(7) 0.000
N2 0.079(11) 0.116(14) 0.135(16) 0.000 0.012(11) 0.000
C1 0.040(4) 0.024(3) 0.066(6) 0.003(3) 0.014(4) 0.004(3)
C2 0.038(4) 0.045(4) 0.051(5) -0.001(3) 0.005(4) 0.005(4)
C3 0.064(6) 0.047(5) 0.051(5) 0.008(4) 0.006(4) -0.011(4)
C4 0.039(5) 0.082(7) 0.066(6) -0.002(5) -0.006(4) -0.012(5)
C5 0.053(6) 0.056(5) 0.059(5) 0.007(4) 0.006(4) -0.022(4)
C6 0.036(4) 0.045(4) 0.056(5) 0.007(4) 0.000(4) -0.009(4)
C7 0.032(4) 0.046(4) 0.057(5) -0.006(4) 0.001(3) 0.006(3)
C8 0.037(4) 0.047(5) 0.047(5) 0.000(3) 0.001(4) -0.005(4)
C12 0.066(8) 0.065(7) 0.132(11) 0.016(7) -0.013(7) -0.006(6)
C11 0.071(8) 0.118(11) 0.129(12) 0.040(9) -0.020(8) -0.006(8)
C13 0.078(12) 0.097(13) 0.105(14) 0.000 0.049(11) 0.000
C14 0.050(10) 0.097(14) 0.19(3) 0.000 0.016(13) 0.000

_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
Zn1 O2 2.043(6) 2_556 ?
Zn1 O2 2.043(6) 5_566 ?
Zn1 N1 2.047(13) . ?
Zn1 O1 2.048(6) . ?
Zn1 O1 2.048(6) 6_565 ?
Zn1 Zn1 3.002(3) 5_566 ?
O1 C1 1.266(10) . ?
O2 C1 1.290(10) . ?
O2 Zn1 2.043(6) 5_566 ?
N1 C12 1.457(13) 6_565 ?
N1 C12 1.457(13) . ?
N1 C13 1.52(2) . ?
N2 C11 1.426(16) 6_565 ?
N2 C11 1.426(16) . ?
N2 C14 1.53(3) . ?
C1 C2 1.476(11) . ?
C2 C7 1.395(12) . ?
C2 C3 1.401(13) . ?
C3 C4 1.386(13) . ?
C4 C5 1.386(13) . ?
C5 C6 1.403(12) . ?
C6 C7 1.409(11) . ?
C6 C8 1.490(11) . ?
C8 C9 1.388(18) . ?
C8 C9A 1.39(2) . ?
C8 C10 1.396(18) . ?
C8 C10A 1.40(2) . ?
C12 C11 1.586(17) . ?
C13 C14 1.60(3) . ?
C10 C9 1.37(2) 7_565 ?
C9 C10 1.37(2) 7_565 ?
C10A C9A 1.35(3) 7_565 ?
C9A C10A 1.35(3) 7_565 ?

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 Zn1 O2 85.6(3) 2_556 5_566 ?
O2 Zn1 N1 106.5(3) 2_556 . ?
O2 Zn1 N1 106.5(3) 5_566 . ?
O2 Zn1 O1 88.5(2) 2_556 . ?
O2 Zn1 O1 158.2(3) 5_566 . ?
N1 Zn1 O1 95.3(3) . . ?
O2 Zn1 O1 158.2(3) 2_556 6_565 ?
O2 Zn1 O1 88.5(2) 5_566 6_565 ?
N1 Zn1 O1 95.3(3) . 6_565 ?
O1 Zn1 O1 89.3(4) . 6_565 ?
O2 Zn1 Zn1 86.46(18) 2_556 5_566 ?
O2 Zn1 Zn1 86.46(18) 5_566 5_566 ?
N1 Zn1 Zn1 162.1(4) . 5_566 ?
O1 Zn1 Zn1 72.3(2) . 5_566 ?
O1 Zn1 Zn1 72.3(2) 6_565 5_566 ?
C1 O1 Zn1 137.3(6) . . ?
C1 O2 Zn1 118.7(5) . 5_566 ?
C12 N1 C12 111.0(14) 6_565 . ?
C12 N1 C13 103.8(10) 6_565 . ?
C12 N1 C13 103.8(10) . . ?
C12 N1 Zn1 113.3(8) 6_565 . ?
C12 N1 Zn1 113.3(8) . . ?
C13 N1 Zn1 110.9(10) . . ?
C11 N2 C11 115.3(19) 6_565 . ?
C11 N2 C14 108.0(12) 6_565 . ?
C11 N2 C14 108.0(12) . . ?
O1 C1 O2 124.2(7) . . ?
O1 C1 C2 118.3(8) . . ?
O2 C1 C2 117.4(7) . . ?
C7 C2 C3 120.0(8) . . ?
C7 C2 C1 120.9(8) . . ?
C3 C2 C1 119.1(8) . . ?
C4 C3 C2 119.6(8) . . ?
C3 C4 C5 121.0(9) . . ?
C4 C5 C6 120.2(8) . . ?
C5 C6 C7 119.0(8) . . ?
C5 C6 C8 120.0(7) . . ?
C7 C6 C8 121.0(7) . . ?
C2 C7 C6 120.2(8) . . ?
C9 C8 C9A 82.5(11) . . ?
C9 C8 C10 116.9(11) . . ?
C9A C8 C10 64.4(11) . . ?
C9 C8 C10A 64.6(11) . . ?
C9A C8 C10A 116.3(12) . . ?
C10 C8 C10A 83.5(11) . . ?
C9 C8 C6 121.9(10) . . ?
C9A C8 C6 122.7(11) . . ?
C10 C8 C6 121.2(9) . . ?
C10A C8 C6 120.9(10) . . ?
N1 C12 C11 113.2(11) . . ?
N2 C11 C12 108.7(12) . . ?
N1 C13 C14 113.6(16) . . ?
N2 C14 C13 105.5(15) . . ?
C9 C10 C8 120.2(15) 7_565 . ?
C10 C9 C8 122.9(15) 7_565 . ?
C9A C10A C8 120.2(18) 7_565 . ?
C10A C9A C8 123.5(19) 7_565 . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.365
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.139

_vrf_PLAT601_k0976twin           
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of 137.00 A**3

RESPONSE:

During the
refinement of the structure, electron density peaks were located
that were believed to be highly disordered
solvent molecules (possibly DMF). Attempts
made to model the solvent molecule were not successful.
The SQUEEZE option in PLATON (Spek, 2003) indicated there was a
solvent cavity of volume 137 \%A^3^ containing approximately 57
electrons. In the final cycles of refinement, this contribution to the
electron density was removed from the observed data. The
density, the F(000) value, the molecular weight and the formula are
given without taking into account the results obtained with the
SQUEEZE option PLATON (Spek, 2003). Similar treatments of disordered
solvent molecules were carried out by St\"ahler et al. (2001),
Cox et al. (2003), Mohamed et al. (2003) and Athimoolam et al. (2005).
References:

Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13

Athimoolam, S., Kumar, J., Ramakrishnan, V. & Rajaram, R.K. (2005).
Acta Cryst. E61, m2014-m2017.

Cox, J.P., Kumarasammy, Y., Nahar, L., Sarkar D.S. & Shoeb, M.
(2003). Acta Cryst. E59, o975-o977.

Mohamed, A.A., Krause Bauer, A.J., Bruce, E.A. & Bruce M.R.M.
(2003). Acta Cryst. C59, m84-m86.

St\"ahler, R., N\"ather, C. & Bensch, W. (2001). Acta Cryst.
C57, 26-27.

;

_vrf_PLAT201_k0976twin           
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) ....... 2

RESPONSE:

Disordered atoms were refined with isotropic displacement
parameters

;