# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_andc

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '1-aminonaphthalene-3,7-dicarboxylic acid'
_chemical_name_common            H2NDC-NH2
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C22 H27 N3 O6'
_chemical_formula_sum            'C22 H27 N3 O6'
_chemical_formula_weight         429.47

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   7.3194(7)
_cell_length_b                   10.4461(11)
_cell_length_c                   14.5397(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.358(3)
_cell_angle_gamma                90.00
_cell_volume                     1099.89(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    465
_cell_measurement_theta_min      2.409
_cell_measurement_theta_max      18.868

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.809548
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_special_details           
; 
SADABS 
Ratio of minimum to maximum apparent transmission:  0.809548
Lambda/2 correction factor = 0.0015 
;

_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  'Bruker APEX CCD'
_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            5872
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_sigmaI/netI    0.0677
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         24.73
_reflns_number_total             1876
_reflns_number_gt                1221
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELX-TL XP'
_computing_publication_material  'SHELX-TL XCIF'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0613P)²+2.9233P] where P=(Fo²+2Fc²)/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         1876
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0886
_refine_ls_wR_factor_ref         0.2264
_refine_ls_wR_factor_gt          0.2015
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
O1 O 0.2754(6) 0.1929(3) 0.7915(2) 0.0602(12) Uani 1 1 d . . .
O2 O 0.1400(5) 0.0077(3) 0.8151(2) 0.0480(10) Uani 1 1 d . . .
H2O H 0.1873 0.0214 0.8703 0.072 Uiso 1 1 calc R . .
N1 N 0.0761(9) 0.2767(6) 0.4499(4) 0.0228(16) Uani 0.50 1 d P A 1
H1A H 0.1193 0.3503 0.4731 0.027 Uiso 0.50 1 calc PR A 1
H1B H 0.0382 0.2694 0.3898 0.027 Uiso 0.50 1 calc PR A 1
C1 C 0.0014(6) 0.0525(4) 0.4693(3) 0.0274(10) Uani 1 1 d . . .
C2 C 0.0680(6) 0.1745(4) 0.5066(3) 0.0295(10) Uani 1 1 d . . .
H2 H 0.0709 0.2463 0.4667 0.035 Uiso 0.50 1 calc PR A 2
C3 C 0.1271(6) 0.1860(4) 0.6001(3) 0.0332(11) Uani 1 1 d . A .
H3 H 0.1724 0.2661 0.6247 0.040 Uiso 1 1 calc R . .
C4 C 0.1218(6) 0.0813(4) 0.6603(3) 0.0313(11) Uani 1 1 d . . .
C5 C 0.0584(6) -0.0357(4) 0.6266(3) 0.0297(10) Uani 1 1 d . . .
H5 H 0.0548 -0.1056 0.6681 0.036 Uiso 1 1 calc R . .
C6 C 0.1873(7) 0.1003(4) 0.7615(3) 0.0368(12) Uani 1 1 d . A .
O3 O -0.2377(5) -0.0277(3) 1.0092(2) 0.0515(10) Uani 1 1 d . . .
N2 N -0.2354(7) -0.1407(5) 0.8746(4) 0.0634(14) Uani 1 1 d . . .
C7 C -0.1941(8) -0.1250(6) 0.9621(4) 0.0557(16) Uani 1 1 d . . .
C8 C -0.0793(8) -0.2410(5) 1.0050(4) 0.0514(14) Uani 1 1 d . . .
H8A H 0.0521 -0.2177 1.0235 0.062 Uiso 1 1 calc R . .
H8B H -0.1292 -0.2755 1.0597 0.062 Uiso 1 1 calc R . .
C9 C -0.1027(9) -0.3360(6) 0.9248(5) 0.073(2) Uani 1 1 d . . .
H9A H -0.1988 -0.4000 0.9327 0.087 Uiso 1 1 calc R . .
H9B H 0.0148 -0.3811 0.9207 0.087 Uiso 1 1 calc R . .
C10 C -0.1612(9) -0.2542(6) 0.8372(4) 0.0616(17) Uani 1 1 d . . .
H10A H -0.0540 -0.2334 0.8055 0.074 Uiso 1 1 calc R . .
H10B H -0.2561 -0.2985 0.7929 0.074 Uiso 1 1 calc R . .
C11 C -0.3320(10) -0.0475(7) 0.8135(5) 0.080(2) Uani 1 1 d . . .
H11A H -0.3723 0.0230 0.8502 0.120 Uiso 1 1 calc R . .
H11B H -0.4399 -0.0875 0.7769 0.120 Uiso 1 1 calc R . .
H11C H -0.2497 -0.0142 0.7716 0.120 Uiso 1 1 calc R . .


_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
O1 C6 1.208(5) . ?
O2 C6 1.319(6) . ?
O2 H2O 0.8400 . ?
N1 C2 1.355(7) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
C1 C5 1.411(6) 3_556 ?
C1 C1 1.416(8) 3_556 ?
C1 C2 1.441(6) . ?
C2 C3 1.372(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(6) . ?
C4 C6 1.493(6) . ?
C5 C1 1.411(6) 3_556 ?
C5 H5 0.9500 . ?
O3 C7 1.291(7) . ?
N2 C7 1.276(7) . ?
N2 C11 1.433(7) . ?
N2 C10 1.443(7) . ?
C7 C8 1.553(8) . ?
C8 C9 1.522(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.542(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
C6 O2 H2O 109.5 . . ?
C2 N1 H1A 120.0 . . ?
C2 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C5 C1 C1 119.7(5) 3_556 3_556 ?
C5 C1 C2 121.4(4) 3_556 . ?
C1 C1 C2 118.9(5) 3_556 . ?
N1 C2 C3 120.0(5) . . ?
N1 C2 C1 120.7(4) . . ?
C3 C2 C1 119.4(4) . . ?
N1 C2 H2 1.2 . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 121.1(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 C6 120.9(4) . . ?
C3 C4 C6 118.4(4) . . ?
C4 C5 C1 120.3(4) . 3_556 ?
C4 C5 H5 119.9 . . ?
C1 C5 H5 119.9 3_556 . ?
O1 C6 O2 123.0(4) . . ?
O1 C6 C4 122.8(4) . . ?
O2 C6 C4 114.2(4) . . ?
C7 N2 C11 123.7(6) . . ?
C7 N2 C10 115.8(6) . . ?
C11 N2 C10 120.2(6) . . ?
N2 C7 O3 126.1(6) . . ?
N2 C7 C8 109.6(6) . . ?
O3 C7 C8 124.2(5) . . ?
C9 C8 C7 101.9(5) . . ?
C9 C8 H8A 111.4 . . ?
C7 C8 H8A 111.4 . . ?
C9 C8 H8B 111.4 . . ?
C7 C8 H8B 111.4 . . ?
H8A C8 H8B 109.2 . . ?
C8 C9 C10 105.0(5) . . ?
C8 C9 H9A 110.7 . . ?
C10 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
C10 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
N2 C10 C9 102.6(5) . . ?
N2 C10 H10A 111.2 . . ?
C9 C10 H10A 111.2 . . ?
N2 C10 H10B 111.2 . . ?
C9 C10 H10B 111.2 . . ?
H10A C10 H10B 109.2 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 N1 -0.5(7) 3_556 . . . ?
C1 C1 C2 N1 178.8(6) 3_556 . . . ?
C5 C1 C2 C3 -179.1(4) 3_556 . . . ?
C1 C1 C2 C3 0.1(8) 3_556 . . . ?
N1 C2 C3 C4 -179.4(5) . . . . ?
C1 C2 C3 C4 -0.7(7) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
C2 C3 C4 C6 -179.7(4) . . . . ?
C3 C4 C5 C1 0.4(7) . . . 3_556 ?
C6 C4 C5 C1 -179.4(4) . . . 3_556 ?
C5 C4 C6 O1 165.6(5) . . . . ?
C3 C4 C6 O1 -14.2(7) . . . . ?
C5 C4 C6 O2 -14.6(7) . . . . ?
C3 C4 C6 O2 165.6(4) . . . . ?
C11 N2 C7 O3 2.9(9) . . . . ?
C10 N2 C7 O3 176.4(5) . . . . ?
C11 N2 C7 C8 -176.3(5) . . . . ?
C10 N2 C7 C8 -2.8(7) . . . . ?
N2 C7 C8 C9 -11.7(6) . . . . ?
O3 C7 C8 C9 169.1(5) . . . . ?
C7 C8 C9 C10 20.2(6) . . . . ?
C7 N2 C10 C9 15.9(7) . . . . ?
C11 N2 C10 C9 -170.3(5) . . . . ?
C8 C9 C10 N2 -21.9(6) . . . . ?

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
O2 H2O O3 0.84 1.74 2.560(5) 165.6 3_557

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.73
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.064

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: NMP'
_database_code_depnum_ccdc_archive 'CCDC 1015820'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_m205nh

# start Validation Reply Form
_vrf_PLAT602_m205nh              
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure ! Info 
RESPONSE: When the MOF crystals were prepared by solvothermal methods,
solvent molecules were occluded in the large pores of the MOF.
The crystal used for this X-ray work was evacuated under vacuum,
and thus the occluded solvent molecules were removed, producing
large void pores. Therefore, it was not necessary to apply a PLATON SQUEEZE
treatment during the refinement process.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        MOF-205-NH2
_chemical_name_common            MOF-205-NH2
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H27 N O13 Zn4'
_chemical_formula_sum            'C48 H27 N O13 Zn4'
_chemical_formula_weight         1087.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.3190 1.4280 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           cubic
_symmetry_space_group_name_H-M   'P m -3 n'
_symmetry_space_group_IT_number  223
_symmetry_space_group_name_Hall  '-P 4n 2 3'

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

_cell_length_a                   30.310(4)
_cell_length_b                   30.310(4)
_cell_length_c                   30.310(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     27847(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'truncated cube'
_exptl_crystal_colour            'light brown'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3276
_exptl_absorpt_coefficient_mu    0.507
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.70000
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'PLSII 2D-SMC bending magnet'
_diffrn_radiation_monochromator  'Si(111) double crystal monochromator'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            295560
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0107
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         29.99
_reflns_number_total             7452
_reflns_number_gt                6308
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       HKL3000
_computing_cell_refinement       'PAL ADSC Quantum-210 ADX Program'
_computing_data_reduction        HKL3000
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELX-TL XP'
_computing_publication_material  'SHELX-TL XCIF'

_refine_special_details          'The organic linkers are disordered.'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0637P)²+5.7334P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.0119(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7452
_refine_ls_number_parameters     125
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1471
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.002
_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 0.5000 0.051912(10) 0.787468(7) 0.06569(13) Uani 1 2 d S . .
O1 O 0.44885(5) 0.08768(6) 0.77581(5) 0.1030(5) Uani 1 1 d . . .
O2 O 0.5000 0.03639(9) 0.84962(5) 0.1051(7) Uani 1 2 d S . .
O3 O 0.5000 0.0000 0.7500 0.0564(6) Uani 1 8 d S . .
C1 C 0.41715(6) 0.08285(6) 0.7500 0.0800(7) Uani 1 2 d S A .
C2 C 0.38268(7) 0.11732(7) 0.7500 0.0936(9) Uani 1 2 d SD . .
C3 C 0.39055(19) 0.15965(18) 0.7661(3) 0.114(2) Uani 0.696(13) 1 d PD A 1
H3 H 0.4186 0.1662 0.7776 0.137 Uiso 0.696(13) 1 calc PR A 1
C4 C 0.3588(2) 0.1922(2) 0.7658(3) 0.126(3) Uani 0.696(13) 1 d PD A 1
H4 H 0.3654 0.2207 0.7763 0.151 Uiso 0.696(13) 1 calc PR A 1
C3' C 0.3736(5) 0.1381(7) 0.7880(4) 0.118(6) Uani 0.304(13) 1 d PD A 2
H3' H 0.3885 0.1308 0.8143 0.142 Uiso 0.304(13) 1 calc PR A 2
C4' C 0.3417(6) 0.1705(7) 0.7874(4) 0.125(6) Uani 0.304(13) 1 d PD A 2
H4' H 0.3359 0.1855 0.8138 0.150 Uiso 0.304(13) 1 calc PR A 2
C5 C 0.31744(8) 0.18256(8) 0.7500 0.1184(14) Uani 1 2 d SD . .
C6 C 0.28297(8) 0.21703(8) 0.7500 0.1279(16) Uani 1 2 d S A .
C7 C 0.2500 0.21780(8) 0.71780(8) 0.1317(16) Uani 1 2 d S . .
H7 H 0.2500 0.1959 0.6959 0.158 Uiso 1 2 calc SR A .
C8 C 0.5000 0.0000 0.86848(10) 0.1078(18) Uani 1 4 d S . .
C9 C 0.5000 0.01258(13) 0.91776(13) 0.0689(13) Uani 0.50 2 d SPD . .
C10 C 0.5000 0.0545(2) 0.93717(15) 0.116(3) Uani 0.50 2 d SPD C .
H10 H 0.5000 0.0800 0.9194 0.139 Uiso 0.50 2 calc SPR . .
C11 C 0.5000 0.0582(2) 0.98270(15) 0.124(3) Uani 0.50 2 d SPD . .
H11 H 0.5000 0.0864 0.9956 0.149 Uiso 0.25 2 calc SPR B 1
C12 C 0.5000 0.02067(14) 1.01001(10) 0.0791(14) Uani 0.50 2 d SPD . .
C13 C 0.5000 -0.0238(2) 0.94303(13) 0.0827(16) Uani 0.50 2 d SPD . .
H13 H 0.5000 -0.0518 0.9296 0.099 Uiso 0.50 2 calc SPR . .
N1 N 0.5000 0.1012(3) 1.0000 0.243(10) Uani 0.50 4 d SP C 2
H1A H 0.5000 0.1238 0.9823 0.291 Uiso 0.25 2 calc SPR C 2
H1B H 0.5000 0.1052 1.0284 0.291 Uiso 0.25 2 calc SPR C 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
Zn1 O1 1.9246(15) 28_655 ?
Zn1 O1 1.9246(15) . ?
Zn1 O3 1.9405(3) . ?
Zn1 O2 1.9417(18) . ?
Zn1 Zn1 3.1469(7) 2_655 ?
O1 C1 1.2476(18) . ?
O2 C8 1.242(3) . ?
O3 Zn1 1.9405(3) 2_655 ?
O3 Zn1 1.9405(3) 14_556 ?
O3 Zn1 1.9405(3) 13_546 ?
C1 O1 1.2476(18) 14_556 ?
C1 C2 1.478(4) . ?
C2 C3' 1.343(7) . ?
C2 C3' 1.343(7) 14_556 ?
C2 C3 1.393(4) 14_556 ?
C2 C3 1.393(4) . ?
C3 C4 1.378(5) . ?
C3 H3 0.9400 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9400 . ?
C3' C4' 1.377(10) . ?
C3' H3' 0.9400 . ?
C4' C5 1.399(9) . ?
C4' H4' 0.9400 . ?
C5 C4 1.375(5) 14_556 ?
C5 C4' 1.399(9) 14_556 ?
C5 C6 1.477(4) . ?
C6 C7 1.397(2) 8_656 ?
C6 C7 1.397(2) . ?
C7 C6 1.397(2) 11_566 ?
C7 H7 0.9400 . ?
C8 O2 1.242(3) 2_655 ?
C8 C9 1.541(5) . ?
C8 C9 1.541(5) 2_655 ?
C9 C13 1.343(6) . ?
C9 C10 1.401(7) . ?
C10 C11 1.384(6) . ?
C10 H10 0.9400 . ?
C11 N1 1.403(10) . ?
C11 C12 1.408(6) . ?
C11 H11 0.9400 . ?
C12 C12 1.392(8) 25_657 ?
C12 C13 1.427(5) 25_657 ?
C13 C12 1.427(5) 25_657 ?
C13 H13 0.9400 . ?
N1 H1A 0.8700 . ?
N1 H1B 0.8700 . ?

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
O1 Zn1 O1 107.33(12) 28_655 . ?
O1 Zn1 O3 110.44(4) 28_655 . ?
O1 Zn1 O3 110.44(4) . . ?
O1 Zn1 O2 108.34(7) 28_655 . ?
O1 Zn1 O2 108.34(7) . . ?
O3 Zn1 O2 111.80(8) . . ?
C1 O1 Zn1 132.03(15) . . ?
C8 O2 Zn1 131.4(2) . . ?
Zn1 O3 Zn1 108.359(17) 2_655 . ?
Zn1 O3 Zn1 110.030(9) 2_655 14_556 ?
Zn1 O3 Zn1 110.030(8) . 14_556 ?
Zn1 O3 Zn1 110.030(8) 2_655 13_546 ?
Zn1 O3 Zn1 110.030(9) . 13_546 ?
Zn1 O3 Zn1 108.359(17) 14_556 13_546 ?
O1 C1 O1 125.0(3) . 14_556 ?
O1 C1 C2 117.49(13) . . ?
O1 C1 C2 117.49(13) 14_556 . ?
C3' C2 C3' 123.0(9) . 14_556 ?
C3' C2 C3 101.1(5) . 14_556 ?
C3' C2 C3 101.1(5) 14_556 . ?
C3 C2 C3 116.0(4) 14_556 . ?
C3' C2 C1 118.5(4) . . ?
C3' C2 C1 118.5(4) 14_556 . ?
C3 C2 C1 122.0(2) 14_556 . ?
C3 C2 C1 122.0(2) . . ?
C4 C3 C2 122.6(4) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C5 C4 C3 119.0(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C2 C3' C4' 117.7(8) . . ?
C2 C3' H3' 121.1 . . ?
C4' C3' H3' 121.1 . . ?
C3' C4' C5 124.6(8) . . ?
C3' C4' H4' 117.7 . . ?
C5 C4' H4' 117.7 . . ?
C4 C5 C4 120.7(4) . 14_556 ?
C4 C5 C6 119.6(2) . . ?
C4 C5 C6 119.6(2) 14_556 . ?
C4' C5 C6 123.9(4) . . ?
C4' C5 C6 123.9(4) 14_556 . ?
C7 C6 C7 117.7(4) 8_656 . ?
C7 C6 C5 121.17(18) 8_656 . ?
C7 C6 C5 121.17(18) . . ?
C6 C7 C6 122.3(4) . 11_566 ?
C6 C7 H7 118.8 . . ?
C6 C7 H7 118.8 11_566 . ?
O2 C8 O2 125.2(3) 2_655 . ?
O2 C8 C9 131.7(2) 2_655 . ?
O2 C8 C9 103.08(19) . . ?
O2 C8 C9 103.1(2) 2_655 2_655 ?
O2 C8 C9 131.7(2) . 2_655 ?
C9 C9 C13 114.0(5) 2_655 2_655 ?
C9 C9 C10 155.2(3) 2_655 . ?
C13 C9 C10 120.4(4) . . ?
C13 C9 C8 170.3(6) 2_655 . ?
C13 C9 C8 110.4(3) . . ?
C10 C9 C8 129.2(4) . . ?
C11 C10 C9 119.5(5) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 N1 116.6(5) . . ?
C10 C11 C12 121.4(5) . . ?
N1 C11 C12 122.0(4) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C12 C12 C11 118.1(4) 25_657 . ?
C12 C12 C13 119.7(5) 25_657 25_657 ?
C11 C12 C13 122.2(4) . 25_657 ?
C12 C12 C10 122.7(2) 2_655 26_557 ?
C11 C12 C13 122.5(4) 26_557 26_557 ?
C9 C13 C12 120.9(5) . 25_657 ?
C9 C13 C12 122.1(4) . 2_655 ?
C9 C13 H13 119.5 . . ?
C12 C13 H13 119.5 25_657 . ?
C12 C13 H13 118.4 2_655 . ?
C11 N1 H1A 120.0 . . ?
C11 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Zn1 O1 C1 121.63(15) 28_655 . . . ?
O3 Zn1 O1 C1 1.2(2) . . . . ?
O2 Zn1 O1 C1 -121.58(18) . . . . ?
Zn1 Zn1 O1 C1 -36.3(2) 2_655 . . . ?
O1 Zn1 O2 C8 -121.93(6) 28_655 . . . ?
O1 Zn1 O2 C8 121.93(6) . . . . ?
O3 Zn1 O2 C8 0.0 . . . . ?
Zn1 Zn1 O2 C8 0.0 2_655 . . . ?
O1 Zn1 O3 Zn1 120.71(6) 28_655 . . 2_655 ?
O1 Zn1 O3 Zn1 -120.71(6) . . . 2_655 ?
O2 Zn1 O3 Zn1 0.0 . . . 2_655 ?
O1 Zn1 O3 Zn1 -118.95(7) 28_655 . . 14_556 ?
O1 Zn1 O3 Zn1 -0.38(6) . . . 14_556 ?
O2 Zn1 O3 Zn1 120.338(5) . . . 14_556 ?
Zn1 Zn1 O3 Zn1 120.338(5) 2_655 . . 14_556 ?
O1 Zn1 O3 Zn1 0.38(6) 28_655 . . 13_546 ?
O1 Zn1 O3 Zn1 118.95(7) . . . 13_546 ?
O2 Zn1 O3 Zn1 -120.338(5) . . . 13_546 ?
Zn1 Zn1 O3 Zn1 -120.338(5) 2_655 . . 13_546 ?
Zn1 O1 C1 O1 -0.68(12) . . . 14_556 ?
Zn1 O1 C1 C2 179.32(12) . . . . ?
O1 C1 C2 C3' -32.8(12) . . . . ?
O1 C1 C2 C3' 147.2(12) 14_556 . . . ?
O1 C1 C2 C3' 147.2(12) . . . 14_556 ?
O1 C1 C2 C3' -32.8(12) 14_556 . . 14_556 ?
O1 C1 C2 C3 -159.4(5) . . . 14_556 ?
O1 C1 C2 C3 20.6(5) 14_556 . . 14_556 ?
O1 C1 C2 C3 20.6(5) . . . . ?
O1 C1 C2 C3 -159.4(5) 14_556 . . . ?
C3' C2 C3 C4 -80.6(8) . . . . ?
C3' C2 C3 C4 45.2(8) 14_556 . . . ?
C3 C2 C3 C4 -0.8(4) 14_556 . . . ?
C1 C2 C3 C4 179.2(4) . . . . ?
C2 C3 C4 C5 1.5(8) . . . . ?
C3' C2 C3' C4' -0.7(9) 14_556 . . . ?
C3 C2 C3' C4' -44.6(13) 14_556 . . . ?
C3 C2 C3' C4' 71.0(12) . . . . ?
C1 C2 C3' C4' 179.3(9) . . . . ?
C2 C3' C4' C5 1(2) . . . . ?
C3 C4 C5 C4 -0.7(4) . . . 14_556 ?
C3 C4 C5 C4' 69.5(7) . . . . ?
C3 C4 C5 C4' -43.2(7) . . . 14_556 ?
C3 C4 C5 C6 179.3(4) . . . . ?
C3' C4' C5 C4 -80.9(14) . . . . ?
C3' C4' C5 C4 44.1(14) . . . 14_556 ?
C3' C4' C5 C4' -0.8(10) . . . 14_556 ?
C3' C4' C5 C6 179.2(10) . . . . ?
C4 C5 C6 C7 -31.1(5) . . . 8_656 ?
C4 C5 C6 C7 148.9(5) 14_556 . . 8_656 ?
C4' C5 C6 C7 22.3(13) . . . 8_656 ?
C4' C5 C6 C7 -157.7(13) 14_556 . . 8_656 ?
C4 C5 C6 C7 148.9(5) . . . . ?
C4 C5 C6 C7 -31.1(5) 14_556 . . . ?
C4' C5 C6 C7 -157.7(13) . . . . ?
C4' C5 C6 C7 22.3(13) 14_556 . . . ?
C7 C6 C7 C6 0.0 8_656 . . 11_566 ?
C5 C6 C7 C6 180.000(1) . . . 11_566 ?
Zn1 O2 C8 O2 0.000(1) . . . 2_655 ?
Zn1 O2 C8 C9 180.0 . . . . ?
Zn1 O2 C8 C9 180.0 . . . 2_655 ?
O2 C8 C9 C10 180.000(2) 2_655 . . . ?
O2 C8 C9 C10 0.000(2) . . . . ?
C9 C8 C9 C10 180.000(2) 2_655 . . . ?
C9 C9 C10 C11 0.000(4) 2_655 . . . ?
C13 C9 C10 C11 0.000(2) 2_655 . . . ?
C13 C9 C10 C11 0.000(2) . . . . ?
C8 C9 C10 C11 180.000(2) . . . . ?
C9 C10 C11 N1 180.000(2) . . . . ?
C9 C10 C11 C12 0.000(2) . . . . ?
C10 C11 C12 C12 0.000(2) . . . 26_557 ?
N1 C11 C12 C12 180.000(2) . . . 26_557 ?
C10 C11 C12 C11 180.000(2) . . . 26_557 ?
N1 C11 C12 C11 0.000(2) . . . 26_557 ?
C10 C11 C12 C12 0.000(3) . . . 2_655 ?
N1 C11 C12 C12 180.000(3) . . . 2_655 ?
C10 C11 C12 C12 0.000(2) . . . 25_657 ?
N1 C11 C12 C12 180.000(2) . . . 25_657 ?
C10 C11 C12 C13 180.000(2) . . . 25_657 ?
N1 C11 C12 C13 0.000(2) . . . 25_657 ?
C10 C11 C12 C10 180.000(2) . . . 26_557 ?
N1 C11 C12 C10 0.000(2) . . . 26_557 ?
C10 C11 C12 C13 180.000(6) . . . 26_557 ?
N1 C11 C12 C13 0.000(6) . . . 26_557 ?
C10 C11 C12 C13 0.000(2) . . . 2_655 ?
N1 C11 C12 C13 180.000(2) . . . 2_655 ?
C9 C9 C13 C12 180.000(3) 2_655 . . 25_657 ?
C13 C9 C13 C12 0.000(2) 2_655 . . 25_657 ?
C10 C9 C13 C12 0.000(2) . . . 25_657 ?
C8 C9 C13 C12 180.000(1) . . . 25_657 ?
C9 C9 C13 C12 180.000(3) 2_655 . . 2_655 ?
C13 C9 C13 C12 0.000(2) 2_655 . . 2_655 ?
C10 C9 C13 C12 0.000(2) . . . 2_655 ?
C8 C9 C13 C12 180.0 . . . 2_655 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.042

_exptl_crystal_recrystallization_method 'solvothermal reaction'
_chemical_properties_physical    Moisture-sensitive
_exptl_crystal_preparation       'gas adsorption'
_database_code_depnum_ccdc_archive 'CCDC 1015821'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_m205no

# start Validation Reply Form
_vrf_PLAT602_m205no              
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure ! Info 
RESPONSE: When the MOF crystals were prepared by solvothermal methods,
solvent molecules were occluded in the large pores of the MOF.
The crystal used for this X-ray work was evacuated under vacuum,
and thus the occluded solvent molecules were removed, producing
large void pores. Therefore, it was not necessary to apply a PLATON SQUEEZE
treatment during the refinement process.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        MOF-205-NO2
_chemical_name_common            MOF-205-NO2
_chemical_melting_point          none
_chemical_formula_moiety         'C48 H25 N O15 Zn4'
_chemical_formula_sum            'C48 H25 N O15 Zn4'
_chemical_formula_weight         1117.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.3190 1.4280 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           cubic
_symmetry_space_group_name_H-M   'P m -3 n'
_symmetry_space_group_IT_number  223
_symmetry_space_group_name_Hall  '-P 4n 2 3'

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

_cell_length_a                   30.312(4)
_cell_length_b                   30.312(4)
_cell_length_c                   30.312(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     27851(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'truncated cube'
_exptl_crystal_colour            'light brown'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3360
_exptl_absorpt_coefficient_mu    0.508
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.70000
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'PLSII 2D-SMC bending magnet'
_diffrn_radiation_monochromator  'Si(111) double crystal monochromator'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            291703
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_sigmaI/netI    0.0123
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         30.00
_reflns_number_total             7451
_reflns_number_gt                6385
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       HKL3000
_computing_cell_refinement       'PAL ADSC Quantum-210 ADX Program'
_computing_data_reduction        HKL3000
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELX-TL XP'
_computing_publication_material  'SHELX-TL XCIF'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0709P)²+6.6108P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.0203(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7451
_refine_ls_number_parameters     131
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1738
_refine_ls_wR_factor_gt          0.1695
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.131
_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
Zn1 Zn 0.0000 0.447871(12) 0.712798(8) 0.06748(15) Uani 1 2 d S . .
O1 O 0.05128(6) 0.41237(7) 0.72407(6) 0.1054(6) Uani 1 1 d . . .
O2 O 0.0000 0.46358(11) 0.65039(6) 0.1065(8) Uani 1 2 d S . .
O3 O 0.0000 0.5000 0.7500 0.0586(7) Uani 1 8 d S . .
C1 C 0.08288(7) 0.41712(7) 0.7500 0.0820(8) Uani 1 2 d S A .
C2 C 0.11731(8) 0.38269(8) 0.7500 0.0956(10) Uani 1 2 d SD . .
C3 C 0.1097(2) 0.3404(2) 0.7337(4) 0.115(3) Uani 0.679(17) 1 d PD A 1
H3 H 0.0818 0.3339 0.7220 0.139 Uiso 0.679(17) 1 calc PR A 1
C4 C 0.1412(2) 0.3076(3) 0.7341(4) 0.127(3) Uani 0.679(17) 1 d PD A 1
H4 H 0.1345 0.2792 0.7237 0.152 Uiso 0.679(17) 1 calc PR A 1
C3' C 0.1258(6) 0.3614(8) 0.7121(5) 0.125(7) Uani 0.321(17) 1 d PD A 2
H3' H 0.1107 0.3684 0.6860 0.150 Uiso 0.321(17) 1 calc PR A 2
C4' C 0.1575(7) 0.3289(8) 0.7130(4) 0.129(7) Uani 0.321(17) 1 d PD A 2
H4' H 0.1627 0.3132 0.6868 0.155 Uiso 0.321(17) 1 calc PR A 2
C5 C 0.18256(9) 0.31744(9) 0.7500 0.1202(15) Uani 1 2 d SD . .
C6 C 0.21698(9) 0.28302(9) 0.7500 0.1302(18) Uani 1 2 d S A .
C7 C 0.21790(9) 0.2500 0.71790(9) 0.1343(19) Uani 1 2 d S . .
H7 H 0.1960 0.2500 0.6960 0.161 Uiso 1 2 calc SR A .
C8 C 0.0000 0.5000 0.63181(12) 0.109(2) Uani 1 4 d S . .
C9 C 0.0000 0.48751(15) 0.58238(14) 0.0696(15) Uani 0.50 2 d SPD . .
C10 C 0.0000 0.4452(2) 0.56281(18) 0.117(3) Uani 0.50 2 d SP . .
H10 H 0.0000 0.4197 0.5804 0.140 Uiso 0.50 2 calc SPR . .
C11 C 0.0000 0.4420(2) 0.51764(18) 0.123(3) Uani 0.50 2 d SPD . .
H11 H 0.0000 0.4138 0.5047 0.148 Uiso 0.25 2 calc SPR B 1
C12 C 0.0000 0.47931(15) 0.48988(11) 0.0810(16) Uani 0.50 2 d SPD . .
C13 C 0.0000 0.5240(2) 0.55696(15) 0.0849(18) Uani 0.50 2 d SPD . .
H13 H 0.0000 0.5519 0.5703 0.102 Uiso 0.50 2 calc SPR . .
N1 N 0.0000 0.3954(4) 0.5000 0.248(12) Uani 0.50 4 d SP . 2
O4 O 0.0000 0.3766(5) 0.5251(4) 0.58(2) Uani 0.50 2 d SP . 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
Zn1 O1 1.9212(17) 28 ?
Zn1 O1 1.9212(17) . ?
Zn1 O3 1.9413(4) . ?
Zn1 O2 1.951(2) . ?
O1 C1 1.247(2) . ?
O2 C8 1.239(3) . ?
O3 Zn1 1.9413(4) 14_556 ?
O3 Zn1 1.9413(4) 2_565 ?
O3 Zn1 1.9413(4) 13_456 ?
C1 O1 1.247(2) 14_556 ?
C1 C2 1.476(4) . ?
C2 C3' 1.342(8) 14_556 ?
C2 C3' 1.342(8) . ?
C2 C3 1.392(5) 14_556 ?
C2 C3 1.392(5) . ?
C3 C4 1.378(7) . ?
C3 H3 0.9400 . ?
C4 C5 1.377(6) . ?
C4 H4 0.9400 . ?
C3' C4' 1.374(16) . ?
C3' H3' 0.9400 . ?
C4' C5 1.398(10) . ?
C4' H4' 0.9400 . ?
C5 C4 1.377(6) 14_556 ?
C5 C4' 1.398(10) 14_556 ?
C5 C6 1.476(5) . ?
C6 C7 1.396(3) 11_566 ?
C6 C7 1.396(3) . ?
C7 C6 1.396(3) 8_656 ?
C7 H7 0.9400 . ?
C8 O2 1.239(3) 2_565 ?
C8 C9 1.545(5) . ?
C8 C9 1.545(5) 2_565 ?
C9 C13 1.347(7) . ?
C9 C10 1.412(8) . ?
C10 C11 1.373(7) . ?
C10 H10 0.9400 . ?
C11 C12 1.409(7) . ?
C11 N1 1.510(13) . ?
C11 H11 0.9400 . ?
C12 C12 1.396(8) 25_566 ?
C12 C13 1.423(5) 25_566 ?
C13 C12 1.423(5) 25_566 ?
C13 C12 1.962(7) 26_556 ?
C13 H13 0.9400 . ?
N1 O4 0.950(12) 26_556 ?
N1 O4 0.950(12) . ?
N1 C11 1.510(13) 26_556 ?

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
O1 Zn1 O1 108.02(13) 28 . ?
O1 Zn1 O3 110.64(5) 28 . ?
O1 Zn1 O3 110.64(5) . . ?
O1 Zn1 O2 108.01(8) 28 . ?
O1 Zn1 O2 108.01(8) . . ?
O3 Zn1 O2 111.39(9) . . ?
C1 O1 Zn1 131.97(18) . . ?
C8 O2 Zn1 131.2(2) . . ?
Zn1 O3 Zn1 109.721(10) 14_556 . ?
Zn1 O3 Zn1 109.721(10) 14_556 2_565 ?
Zn1 O3 Zn1 108.972(19) . 2_565 ?
Zn1 O3 Zn1 108.972(19) 14_556 13_456 ?
Zn1 O3 Zn1 109.721(10) . 13_456 ?
Zn1 O3 Zn1 109.721(10) 2_565 13_456 ?
O1 C1 O1 125.0(3) 14_556 . ?
O1 C1 C2 117.48(15) 14_556 . ?
O1 C1 C2 117.48(15) . . ?
C3' C2 C3' 123.1(12) 14_556 . ?
C3 C2 C3 115.5(5) 14_556 . ?
C3' C2 C1 118.4(6) 14_556 . ?
C3' C2 C1 118.4(6) . . ?
C3 C2 C1 122.3(2) 14_556 . ?
C3 C2 C1 122.3(2) . . ?
C4 C3 C2 123.1(5) . . ?
C4 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
C5 C4 C3 118.5(5) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C2 C3' C4' 117.5(10) . . ?
C2 C3' H3' 121.3 . . ?
C4' C3' H3' 121.3 . . ?
C3' C4' C5 125.0(9) . . ?
C3' C4' H4' 117.5 . . ?
C5 C4' H4' 117.5 . . ?
C4 C5 C4 121.1(6) 14_556 . ?
C4' C5 C4' 111.8(10) 14_556 . ?
C4 C5 C6 119.4(3) 14_556 . ?
C4 C5 C6 119.4(3) . . ?
C4' C5 C6 124.1(5) 14_556 . ?
C4' C5 C6 124.1(5) . . ?
C7 C6 C7 117.2(4) 11_566 . ?
C7 C6 C5 121.4(2) 11_566 . ?
C7 C6 C5 121.4(2) . . ?
C6 C7 C6 122.8(4) . 8_656 ?
C6 C7 H7 118.6 . . ?
C6 C7 H7 118.6 8_656 . ?
O2 C8 O2 126.0(3) 2_565 . ?
O2 C8 C9 131.2(3) 2_565 . ?
O2 C8 C9 102.8(2) . . ?
O2 C8 C9 102.8(2) 2_565 2_565 ?
O2 C8 C9 131.2(3) . 2_565 ?
C13 C9 C10 120.3(5) . . ?
C13 C9 C8 110.7(4) . . ?
C10 C9 C8 129.0(4) . . ?
C11 C10 C9 118.9(6) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 122.6(6) . . ?
C10 C11 N1 114.8(5) . . ?
C12 C11 N1 122.6(4) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C12 C12 C11 117.3(4) 25_566 . ?
C12 C12 C13 120.1(5) 25_566 25_566 ?
C11 C12 C13 122.7(5) . 25_566 ?
C9 C13 C12 120.9(5) . 25_566 ?
C9 C13 H13 119.5 . . ?
C12 C13 H13 119.5 25_566 . ?
C12 C13 H13 159.2 26_556 . ?
O4 N1 O4 106(2) 26_556 . ?
O4 N1 C11 147.6(13) 26_556 . ?
O4 N1 C11 106.1(11) . . ?
O4 N1 C11 106.1(11) 26_556 26_556 ?
O4 N1 C11 147.6(13) . 26_556 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Zn1 O1 C1 -121.26(17) 28 . . . ?
O3 Zn1 O1 C1 0.0(2) . . . . ?
O2 Zn1 O1 C1 122.1(2) . . . . ?
O1 Zn1 O2 C8 121.70(7) 28 . . . ?
O1 Zn1 O2 C8 -121.70(7) . . . . ?
O3 Zn1 O2 C8 0.0 . . . . ?
O1 Zn1 O3 Zn1 119.69(7) 28 . . 14_556 ?
O1 Zn1 O3 Zn1 0.00(7) . . . 14_556 ?
O2 Zn1 O3 Zn1 -120.152(6) . . . 14_556 ?
O1 Zn1 O3 Zn1 -120.16(7) 28 . . 2_565 ?
O1 Zn1 O3 Zn1 120.16(7) . . . 2_565 ?
O2 Zn1 O3 Zn1 0.0 . . . 2_565 ?
O1 Zn1 O3 Zn1 0.00(7) 28 . . 13_456 ?
O1 Zn1 O3 Zn1 -119.69(7) . . . 13_456 ?
O2 Zn1 O3 Zn1 120.152(6) . . . 13_456 ?
Zn1 O1 C1 O1 0.01(13) . . . 14_556 ?
Zn1 O1 C1 C2 -179.99(13) . . . . ?
O1 C1 C2 C3' 31.3(15) 14_556 . . 14_556 ?
O1 C1 C2 C3' -148.7(15) . . . 14_556 ?
O1 C1 C2 C3' -148.7(15) 14_556 . . . ?
O1 C1 C2 C3' 31.3(15) . . . . ?
O1 C1 C2 C3 -20.5(6) 14_556 . . 14_556 ?
O1 C1 C2 C3 159.5(6) . . . 14_556 ?
O1 C1 C2 C3 159.5(6) 14_556 . . . ?
O1 C1 C2 C3 -20.5(6) . . . . ?
C3' C2 C3 C4 -43.9(10) 14_556 . . . ?
C3' C2 C3 C4 81.8(10) . . . . ?
C3 C2 C3 C4 1.1(5) 14_556 . . . ?
C1 C2 C3 C4 -178.9(5) . . . . ?
C2 C3 C4 C5 -2.1(10) . . . . ?
C3' C2 C3' C4' 1.1(11) 14_556 . . . ?
C3 C2 C3' C4' 43.9(14) 14_556 . . . ?
C3 C2 C3' C4' -70.6(14) . . . . ?
C1 C2 C3' C4' -178.9(11) . . . . ?
C2 C3' C4' C5 -2(2) . . . . ?
C3 C4 C5 C4 1.0(5) . . . 14_556 ?
C3 C4 C5 C4' 42.3(8) . . . 14_556 ?
C3 C4 C5 C4' -69.1(9) . . . . ?
C3 C4 C5 C6 -179.0(5) . . . . ?
C3' C4' C5 C4 -42.7(16) . . . 14_556 ?
C3' C4' C5 C4 82.5(16) . . . . ?
C3' C4' C5 C4' 1.2(12) . . . 14_556 ?
C3' C4' C5 C6 -178.8(12) . . . . ?
C4 C5 C6 C7 31.0(7) 14_556 . . 11_566 ?
C4 C5 C6 C7 -149.0(7) . . . 11_566 ?
C4' C5 C6 C7 -20.7(15) 14_556 . . 11_566 ?
C4' C5 C6 C7 159.3(15) . . . 11_566 ?
C4 C5 C6 C7 -149.0(7) 14_556 . . . ?
C4 C5 C6 C7 31.0(7) . . . . ?
C4' C5 C6 C7 159.3(15) 14_556 . . . ?
C4' C5 C6 C7 -20.7(15) . . . . ?
C7 C6 C7 C6 0.000(2) 11_566 . . 8_656 ?
C5 C6 C7 C6 180.000(1) . . . 8_656 ?
Zn1 O2 C8 O2 0.000(2) . . . 2_565 ?
Zn1 O2 C8 C9 180.000(1) . . . . ?
Zn1 O2 C8 C9 180.000(1) . . . 2_565 ?
O2 C8 C9 C13 0.000(2) 2_565 . . . ?
O2 C8 C9 C13 180.000(2) . . . . ?
C9 C8 C9 C13 0.000(2) 2_565 . . . ?
O2 C8 C9 C10 180.000(2) 2_565 . . . ?
O2 C8 C9 C10 0.000(2) . . . . ?
C9 C8 C9 C10 180.000(3) 2_565 . . . ?
C13 C9 C10 C11 0.000(2) . . . . ?
C8 C9 C10 C11 180.000(2) . . . . ?
C9 C10 C11 C12 0.000(2) . . . . ?
C9 C10 C11 N1 180.000(2) . . . . ?
C10 C11 C12 C12 0.000(2) . . . 25_566 ?
N1 C11 C12 C12 180.000(1) . . . 25_566 ?
C10 C11 C12 C13 180.000(2) . . . 25_566 ?
N1 C11 C12 C13 0.000(2) . . . 25_566 ?
C10 C9 C13 C12 0.000(2) . . . 25_566 ?
C8 C9 C13 C12 180.000(1) . . . 25_566 ?
C10 C9 C13 C12 0.000(1) . . . 26_556 ?
C8 C9 C13 C12 180.000(1) . . . 26_556 ?
C10 C11 N1 O4 180.000(7) . . . 26_556 ?
C12 C11 N1 O4 0.000(7) . . . 26_556 ?
C10 C11 N1 O4 0.000(4) . . . . ?
C12 C11 N1 O4 180.000(3) . . . . ?
C10 C11 N1 C11 180.000(4) . . . 26_556 ?
C12 C11 N1 C11 0.000(2) . . . 26_556 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.047

_exptl_crystal_recrystallization_method 'solvothermal reaction'
_chemical_properties_physical    Moisture-sensitive
_exptl_crystal_preparation       'gas adsorption'
_database_code_depnum_ccdc_archive 'CCDC 1015822'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
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#  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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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ndc2
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1-Nitronaphthlanene-3,7-dicarboxylic acid 
;
_chemical_name_common            H2NDC-NO2
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 N O6, C3 H7 N O'
_chemical_formula_sum            'C15 H14 N2 O7'
_chemical_formula_weight         334.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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/c'
_symmetry_space_group_IT_number  15
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   23.991(5)
_cell_length_b                   5.7460(10)
_cell_length_c                   21.791(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.07(3)
_cell_angle_gamma                90.00
_cell_volume                     2886.6(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.70000
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'PLSII 2D-SMC bending magnet'
_diffrn_radiation_monochromator  'Si(111) double crystal monochromator'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7410
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4283
_reflns_number_gt                3902
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       HKL3000
_computing_cell_refinement       'PAL ADSC Quantum-210 ADX Program'
_computing_data_reduction        HKL3000
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELX-TL XP'
_computing_publication_material  'SHELX-TL XCIF'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1317P)²+0.8679P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.212(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4283
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.2108
_refine_ls_wR_factor_gt          0.1770
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_restrained_S_all      1.234
_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
O1 O 0.00554(4) 0.35903(19) 0.08963(5) 0.0273(3) Uani 1 1 d . . .
O2 O 0.08017(4) 0.24549(17) 0.17125(4) 0.0235(3) Uani 1 1 d . . .
H2 H 0.0578 0.1342 0.1725 0.035 Uiso 1 1 calc R . .
O3 O 0.25149(4) 1.54244(18) 0.05170(4) 0.0254(3) Uani 1 1 d . . .
O4 O 0.18230(4) 1.60060(18) -0.03998(4) 0.0265(3) Uani 1 1 d . . .
H4 H 0.2049 1.7075 -0.0442 0.040 Uiso 1 1 calc R . .
O5 O 0.24093(4) 0.80328(18) 0.24881(4) 0.0265(3) Uani 1 1 d . . .
O6 O 0.27834(4) 0.89522(18) 0.17203(4) 0.0241(3) Uani 1 1 d . . .
O7 O -0.01150(4) 0.90583(18) 0.32294(5) 0.0259(3) Uani 1 1 d . . .
N1 N 0.23710(4) 0.83927(18) 0.19214(5) 0.0191(3) Uani 1 1 d . . .
N2 N 0.08198(5) 0.8463(2) 0.32115(5) 0.0222(3) Uani 1 1 d . . .
C1 C 0.07276(5) 0.7201(2) 0.06085(5) 0.0193(3) Uani 1 1 d . . .
H1 H 0.0362 0.6874 0.0316 0.023 Uiso 1 1 calc R . .
C2 C 0.09237(5) 0.5830(2) 0.11408(5) 0.0180(3) Uani 1 1 d . . .
C3 C 0.14695(5) 0.6285(2) 0.15801(5) 0.0183(3) Uani 1 1 d . . .
H3 H 0.1606 0.5355 0.1952 0.022 Uiso 1 1 calc R . .
C4 C 0.17987(5) 0.8089(2) 0.14598(5) 0.0173(3) Uani 1 1 d . . .
C5 C 0.19304(5) 1.1524(2) 0.07878(5) 0.0185(3) Uani 1 1 d . . .
H5 H 0.2300 1.1891 0.1068 0.022 Uiso 1 1 calc R . .
C6 C 0.17012(5) 1.2885(2) 0.02549(5) 0.0187(3) Uani 1 1 d . . .
C7 C 0.11494(5) 1.2401(2) -0.01697(5) 0.0218(3) Uani 1 1 d . . .
H7 H 0.0996 1.3364 -0.0532 0.026 Uiso 1 1 calc R . .
C8 C 0.08383(5) 1.0533(2) -0.00537(5) 0.0213(3) Uani 1 1 d . . .
H8 H 0.0469 1.0198 -0.0339 0.026 Uiso 1 1 calc R . .
C9 C 0.10605(5) 0.9089(2) 0.04883(5) 0.0186(3) Uani 1 1 d . . .
C10 C 0.16168(5) 0.9586(2) 0.09178(5) 0.0173(3) Uani 1 1 d . . .
C11 C 0.05504(5) 0.3855(2) 0.12359(5) 0.0199(3) Uani 1 1 d . . .
C12 C 0.20502(5) 1.4889(2) 0.01370(5) 0.0197(3) Uani 1 1 d . . .
C13 C 0.03858(5) 0.9764(2) 0.32795(6) 0.0225(3) Uani 1 1 d . . .
H13 H 0.0463 1.1366 0.3374 0.027 Uiso 1 1 calc R . .
C14 C 0.07480(7) 0.6007(3) 0.30721(8) 0.0307(3) Uani 1 1 d . . .
H14A H 0.0381 0.5476 0.3138 0.046 Uiso 1 1 calc R . .
H14B H 0.1070 0.5145 0.3357 0.046 Uiso 1 1 calc R . .
H14C H 0.0745 0.5732 0.2627 0.046 Uiso 1 1 calc R . .
C15 C 0.13793(7) 0.9462(3) 0.32391(10) 0.0402(4) Uani 1 1 d . . .
H15A H 0.1374 1.1130 0.3331 0.060 Uiso 1 1 calc R . .
H15B H 0.1463 0.9237 0.2828 0.060 Uiso 1 1 calc R . .
H15C H 0.1679 0.8697 0.3577 0.060 Uiso 1 1 calc R . .


_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
O1 C11 1.2225(15) . ?
O2 C11 1.3202(15) . ?
O2 H2 0.8400 . ?
O3 C12 1.2296(15) . ?
O4 C12 1.3131(14) . ?
O4 H4 0.8400 . ?
O5 N1 1.2301(14) . ?
O6 N1 1.2307(14) . ?
O7 C13 1.2438(16) . ?
N1 C4 1.4706(15) . ?
N2 C13 1.3233(16) . ?
N2 C14 1.4439(18) . ?
N2 C15 1.4458(19) . ?
C1 C2 1.3729(16) . ?
C1 C9 1.4140(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.4162(16) . ?
C2 C11 1.4953(16) . ?
C3 C4 1.3718(16) . ?
C3 H3 0.9500 . ?
C4 C10 1.4281(15) . ?
C5 C6 1.3815(16) . ?
C5 C10 1.4162(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.4169(17) . ?
C6 C12 1.4877(16) . ?
C7 C8 1.3703(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.4208(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.4307(16) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C11 O2 H2 109.5 . . ?
C12 O4 H4 109.5 . . ?
O5 N1 O6 123.87(11) . . ?
O5 N1 C4 117.57(10) . . ?
O6 N1 C4 118.55(10) . . ?
C13 N2 C14 121.61(12) . . ?
C13 N2 C15 121.42(13) . . ?
C14 N2 C15 116.89(12) . . ?
C2 C1 C9 121.17(11) . . ?
C2 C1 H1 119.4 . . ?
C9 C1 H1 119.4 . . ?
C1 C2 C3 120.12(11) . . ?
C1 C2 C11 118.30(10) . . ?
C3 C2 C11 121.57(10) . . ?
C4 C3 C2 118.93(10) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C10 123.56(10) . . ?
C3 C4 N1 115.90(10) . . ?
C10 C4 N1 120.53(10) . . ?
C6 C5 C10 120.22(10) . . ?
C6 C5 H5 119.9 . . ?
C10 C5 H5 119.9 . . ?
C5 C6 C7 121.36(11) . . ?
C5 C6 C12 118.10(10) . . ?
C7 C6 C12 120.53(10) . . ?
C8 C7 C6 119.44(11) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 120.83(11) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C1 C9 C8 120.05(11) . . ?
C1 C9 C10 120.28(10) . . ?
C8 C9 C10 119.65(11) . . ?
C5 C10 C4 125.55(10) . . ?
C5 C10 C9 118.50(10) . . ?
C4 C10 C9 115.92(10) . . ?
O1 C11 O2 123.78(11) . . ?
O1 C11 C2 121.96(11) . . ?
O2 C11 C2 114.26(10) . . ?
O3 C12 O4 123.58(11) . . ?
O3 C12 C6 121.74(11) . . ?
O4 C12 C6 114.67(10) . . ?
O7 C13 N2 125.22(12) . . ?
O7 C13 H13 117.4 . . ?
N2 C13 H13 117.4 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C3 -0.38(18) . . . . ?
C9 C1 C2 C11 -179.69(10) . . . . ?
C1 C2 C3 C4 -0.79(17) . . . . ?
C11 C2 C3 C4 178.50(10) . . . . ?
C2 C3 C4 C10 1.31(18) . . . . ?
C2 C3 C4 N1 -177.39(10) . . . . ?
O5 N1 C4 C3 -37.33(15) . . . . ?
O6 N1 C4 C3 141.55(11) . . . . ?
O5 N1 C4 C10 143.92(11) . . . . ?
O6 N1 C4 C10 -37.20(16) . . . . ?
C10 C5 C6 C7 0.61(17) . . . . ?
C10 C5 C6 C12 -179.50(10) . . . . ?
C5 C6 C7 C8 -0.65(18) . . . . ?
C12 C6 C7 C8 179.46(11) . . . . ?
C6 C7 C8 C9 0.44(19) . . . . ?
C2 C1 C9 C8 -177.68(11) . . . . ?
C2 C1 C9 C10 1.06(18) . . . . ?
C7 C8 C9 C1 178.54(11) . . . . ?
C7 C8 C9 C10 -0.21(18) . . . . ?
C6 C5 C10 C4 -178.18(10) . . . . ?
C6 C5 C10 C9 -0.36(17) . . . . ?
C3 C4 C10 C5 177.24(11) . . . . ?
N1 C4 C10 C5 -4.12(17) . . . . ?
C3 C4 C10 C9 -0.64(17) . . . . ?
N1 C4 C10 C9 178.01(10) . . . . ?
C1 C9 C10 C5 -178.58(10) . . . . ?
C8 C9 C10 C5 0.16(17) . . . . ?
C1 C9 C10 C4 -0.55(16) . . . . ?
C8 C9 C10 C4 178.19(10) . . . . ?
C1 C2 C11 O1 -8.25(18) . . . . ?
C3 C2 C11 O1 172.45(12) . . . . ?
C1 C2 C11 O2 171.80(10) . . . . ?
C3 C2 C11 O2 -7.50(16) . . . . ?
C5 C6 C12 O3 -4.10(18) . . . . ?
C7 C6 C12 O3 175.80(12) . . . . ?
C5 C6 C12 O4 175.61(10) . . . . ?
C7 C6 C12 O4 -4.50(17) . . . . ?
C14 N2 C13 O7 -0.5(2) . . . . ?
C15 N2 C13 O7 176.11(14) . . . . ?

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
O2 H2 O7 0.84 1.74 2.5796(14) 178.6 2_545
O4 H4 O3 0.84 1.81 2.6494(14) 174.5 7_585

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.778
_refine_diff_density_min         -0.929
_refine_diff_density_rms         0.212

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
_database_code_depnum_ccdc_archive 'CCDC 1015823'
