# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_audit_block_doi                 10.5517/cc13ndw1
_database_code_depnum_ccdc_archive 'CCDC 1032513'
_audit_update_record             
;
2014-11-04 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '[Fe(H2bpta)]n'
_chemical_name_common            'Compound 1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H8 Fe O8'
_chemical_formula_sum            'C16 H8 Fe O8'
_chemical_formula_weight         384.07

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcn
_symmetry_space_group_name_Hall  '-P 2n 2ab'

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

_cell_length_a                   15.772(2)
_cell_length_b                   9.1710(14)
_cell_length_c                   9.6050(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1389.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    1.134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6923
_exptl_absorpt_correction_T_max  0.7272
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3422
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         25.05
_reflns_number_total             1221
_reflns_number_gt                1026
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0513P)²+0.8176P] 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         1221
_refine_ls_number_parameters     115
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0983
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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
Fe1 Fe 0.5000 0.04736(6) -0.2500 0.0145(2) Uani 1 2 d S . .
O1 O 0.46857(13) 0.2030(2) -0.0982(2) 0.0223(5) Uani 1 1 d . . .
O2 O 0.52612(11) 0.1131(2) 0.0962(2) 0.0170(5) Uani 1 1 d . . .
O3 O 0.17431(12) 0.3629(3) 0.0028(2) 0.0390(7) Uani 1 1 d U . .
H3A H 0.1246 0.3799 -0.0162 0.058 Uiso 1 1 calc R . .
O4 O 0.13676(12) 0.4544(2) 0.2093(2) 0.0273(6) Uani 1 1 d . . .
C1 C 0.47445(16) 0.1972(3) 0.0306(3) 0.0142(6) Uani 1 1 d . . .
C2 C 0.42064(17) 0.2944(3) 0.1177(3) 0.0159(7) Uani 1 1 d . . .
C3 C 0.33524(18) 0.3072(3) 0.0850(3) 0.0196(7) Uani 1 1 d . . .
H3 H 0.3139 0.2594 0.0071 0.023 Uiso 1 1 calc R . .
C4 C 0.28113(17) 0.3906(3) 0.1674(3) 0.0185(7) Uani 1 1 d . . .
C5 C 0.31290(19) 0.4607(4) 0.2832(4) 0.0264(8) Uani 1 1 d . . .
H5 H 0.2769 0.5140 0.3405 0.032 Uiso 1 1 calc R . .
C6 C 0.39900(19) 0.4516(4) 0.3143(4) 0.0264(8) Uani 1 1 d . . .
H6 H 0.4203 0.5023 0.3905 0.032 Uiso 1 1 calc R . .
C7 C 0.45374(16) 0.3679(3) 0.2334(3) 0.0163(7) Uani 1 1 d . . .
C8 C 0.19004(18) 0.4046(4) 0.1300(3) 0.0208(7) 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
Fe1 0.0121(3) 0.0202(4) 0.0111(4) 0.000 0.0006(2) 0.000
O1 0.0274(11) 0.0262(12) 0.0132(12) -0.0008(10) -0.0008(9) 0.0086(10)
O2 0.0115(9) 0.0215(11) 0.0178(11) 0.0005(10) 0.0017(8) 0.0029(9)
O3 0.0113(10) 0.076(2) 0.0294(15) -0.0107(14) -0.0056(9) 0.0108(13)
O4 0.0144(10) 0.0374(14) 0.0301(14) -0.0063(11) 0.0041(10) 0.0056(10)
C1 0.0087(12) 0.0179(15) 0.0161(17) 0.0001(13) 0.0012(11) -0.0019(12)
C2 0.0134(13) 0.0204(16) 0.0140(16) 0.0023(13) -0.0010(11) -0.0012(12)
C3 0.0190(14) 0.0246(16) 0.0151(17) 0.0014(14) -0.0037(12) -0.0015(13)
C4 0.0130(13) 0.0231(16) 0.0194(18) 0.0003(14) 0.0000(12) 0.0050(13)
C5 0.0151(14) 0.039(2) 0.025(2) -0.0117(15) 0.0026(13) 0.0026(15)
C6 0.0231(16) 0.035(2) 0.0209(18) -0.0107(15) -0.0046(14) 0.0015(15)
C7 0.0120(14) 0.0161(16) 0.0208(17) 0.0038(13) 0.0003(12) -0.0019(12)
C8 0.0153(14) 0.0263(16) 0.0208(18) 0.0010(14) -0.0010(13) -0.0016(13)

_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
Fe1 O1 2.100(2) . ?
Fe1 O1 2.100(2) 3_654 ?
Fe1 O2 2.126(2) 7 ?
Fe1 O2 2.126(2) 5_655 ?
Fe1 O4 2.192(2) 4 ?
Fe1 O4 2.192(2) 2_554 ?
O1 C1 1.242(3) . ?
O2 C1 1.286(3) . ?
O2 Fe1 2.126(2) 5_655 ?
O3 C8 1.305(4) . ?
O3 H3A 0.8200 . ?
O4 C8 1.222(4) . ?
O4 Fe1 2.192(2) 2 ?
C1 C2 1.488(4) . ?
C2 C3 1.388(4) . ?
C2 C7 1.400(4) . ?
C3 C4 1.393(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(4) . ?
C4 C8 1.486(4) . ?
C5 C6 1.393(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(4) . ?
C6 H6 0.9300 . ?
C7 C7 1.494(5) 3_655 ?

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 Fe1 O1 94.36(12) . 3_654 ?
O1 Fe1 O2 177.47(8) . 7 ?
O1 Fe1 O2 86.67(8) 3_654 7 ?
O1 Fe1 O2 86.67(8) . 5_655 ?
O1 Fe1 O2 177.47(7) 3_654 5_655 ?
O2 Fe1 O2 92.39(11) 7 5_655 ?
O1 Fe1 O4 96.51(8) . 4 ?
O1 Fe1 O4 84.07(8) 3_654 4 ?
O2 Fe1 O4 85.88(8) 7 4 ?
O2 Fe1 O4 93.53(8) 5_655 4 ?
O1 Fe1 O4 84.07(8) . 2_554 ?
O1 Fe1 O4 96.51(8) 3_654 2_554 ?
O2 Fe1 O4 93.53(8) 7 2_554 ?
O2 Fe1 O4 85.88(8) 5_655 2_554 ?
O4 Fe1 O4 179.15(12) 4 2_554 ?
C1 O1 Fe1 130.2(2) . . ?
C1 O2 Fe1 129.22(17) . 5_655 ?
C8 O3 H3A 109.5 . . ?
C8 O4 Fe1 141.7(2) . 2 ?
O1 C1 O2 124.1(3) . . ?
O1 C1 C2 119.5(3) . . ?
O2 C1 C2 116.5(3) . . ?
C3 C2 C7 120.1(3) . . ?
C3 C2 C1 118.5(3) . . ?
C7 C2 C1 121.4(2) . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 C8 120.4(3) . . ?
C3 C4 C8 120.2(3) . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C2 118.5(2) . . ?
C6 C7 C7 119.1(3) . 3_655 ?
C2 C7 C7 122.2(3) . 3_655 ?
O4 C8 O3 124.2(3) . . ?
O4 C8 C4 123.1(3) . . ?
O3 C8 C4 112.6(3) . . ?

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 Fe1 O1 C1 -149.2(3) 3_654 . . . ?
O2 Fe1 O1 C1 96.7(18) 7 . . . ?
O2 Fe1 O1 C1 28.5(2) 5_655 . . . ?
O4 Fe1 O1 C1 -64.7(3) 4 . . . ?
O4 Fe1 O1 C1 114.7(3) 2_554 . . . ?
Fe1 O1 C1 O2 23.8(4) . . . . ?
Fe1 O1 C1 C2 -157.56(19) . . . . ?
Fe1 O2 C1 O1 -123.4(3) 5_655 . . . ?
Fe1 O2 C1 C2 57.9(3) 5_655 . . . ?
O1 C1 C2 C3 45.6(4) . . . . ?
O2 C1 C2 C3 -135.7(3) . . . . ?
O1 C1 C2 C7 -136.8(3) . . . . ?
O2 C1 C2 C7 41.9(4) . . . . ?
C7 C2 C3 C4 -1.1(5) . . . . ?
C1 C2 C3 C4 176.6(3) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C2 C3 C4 C8 179.3(3) . . . . ?
C3 C4 C5 C6 2.1(5) . . . . ?
C8 C4 C5 C6 -177.5(3) . . . . ?
C4 C5 C6 C7 -2.5(5) . . . . ?
C5 C6 C7 C2 1.1(5) . . . . ?
C5 C6 C7 C7 176.8(3) . . . 3_655 ?
C3 C2 C7 C6 0.7(4) . . . . ?
C1 C2 C7 C6 -176.9(3) . . . . ?
C3 C2 C7 C7 -174.9(3) . . . 3_655 ?
C1 C2 C7 C7 7.5(4) . . . 3_655 ?
Fe1 O4 C8 O3 25.4(6) 2 . . . ?
Fe1 O4 C8 C4 -157.2(2) 2 . . . ?
C5 C4 C8 O4 -13.3(5) . . . . ?
C3 C4 C8 O4 167.1(3) . . . . ?
C5 C4 C8 O3 164.4(3) . . . . ?
C3 C4 C8 O3 -15.2(4) . . . . ?

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
O3 H3A O2 0.82 1.73 2.533(3) 164.1 4_455

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.066
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_audit_block_doi                 10.5517/cc13ndx2
_database_code_depnum_ccdc_archive 'CCDC 1032514'
_audit_update_record             
;
2014-11-04 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'compound 2'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H8 Ni O8'
_chemical_formula_sum            'C16 H8 Ni O8'
_chemical_formula_weight         386.93

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn
_symmetry_space_group_name_Hall  '-P 2n 2ab'

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

_cell_length_a                   15.680(3)
_cell_length_b                   9.1490(18)
_cell_length_c                   9.4150(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1350.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    25679
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.903
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    1.486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8656
_exptl_absorpt_correction_T_max  0.8656
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.72000
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'synchrotron, 3W1A at BSRF'
_diffrn_radiation_monochromator  'double crystal monochromator'
_diffrn_measurement_device_type  mar555
_diffrn_measurement_method       'oscillation mode'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6613
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         30.50
_reflns_number_total             1978
_reflns_number_gt                1735
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       mar555
_computing_cell_refinement       'HKL 2000'
_computing_data_reduction        'HKL 2000'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0323P)²+0.9192P] 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         1978
_refine_ls_number_parameters     115
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   1.278
_refine_ls_restrained_S_all      1.318
_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
Ni1 Ni 0.5000 0.04655(3) -0.2500 0.00275(9) Uani 1 2 d SU . .
O1 O 0.46919(7) 0.20349(12) -0.10290(11) 0.0064(2) Uani 1 1 d . . .
O2 O 0.52446(7) 0.10795(11) 0.09620(11) 0.0045(2) Uani 1 1 d . . .
O3 O 0.17068(8) 0.36217(14) 0.00499(12) 0.0126(2) Uani 1 1 d U . .
H3A H 0.1204 0.3850 -0.0167 0.019 Uiso 1 1 calc R . .
O4 O 0.13342(8) 0.45575(12) 0.21746(13) 0.0082(2) Uani 1 1 d U . .
C1 C 0.47361(10) 0.19380(16) 0.02934(16) 0.0049(3) Uani 1 1 d . . .
C2 C 0.41832(10) 0.29128(16) 0.11864(15) 0.0043(3) Uani 1 1 d . . .
C3 C 0.33191(10) 0.30347(16) 0.08620(15) 0.0051(3) Uani 1 1 d . . .
H3 H 0.3093 0.2544 0.0056 0.006 Uiso 1 1 calc R . .
C4 C 0.27837(10) 0.38799(16) 0.17235(15) 0.0057(3) Uani 1 1 d . . .
C5 C 0.31214(10) 0.46098(17) 0.28982(17) 0.0081(3) Uani 1 1 d . . .
H5 H 0.2758 0.5168 0.3496 0.010 Uiso 1 1 calc R . .
C6 C 0.39899(10) 0.45213(17) 0.31949(17) 0.0081(3) Uani 1 1 d . . .
H6 H 0.4218 0.5045 0.3979 0.010 Uiso 1 1 calc R . .
C7 C 0.45296(10) 0.36707(16) 0.23507(14) 0.0048(3) Uani 1 1 d . . .
C8 C 0.18664(10) 0.40440(17) 0.13449(16) 0.0065(3) 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
Ni1 0.00040(16) 0.00504(13) 0.00280(13) 0.000 0.00011(8) 0.000
O1 0.0068(6) 0.0080(5) 0.0044(5) -0.0005(4) 0.0002(4) 0.0026(4)
O2 0.0010(5) 0.0072(5) 0.0053(4) 0.0018(4) 0.0001(4) 0.0011(4)
O3 0.0042(5) 0.0250(6) 0.0086(5) -0.0036(4) -0.0022(4) 0.0028(4)
O4 0.0019(5) 0.0118(5) 0.0108(5) -0.0024(4) 0.0013(4) 0.0014(4)
C1 0.0011(7) 0.0070(6) 0.0065(6) 0.0001(5) 0.0005(5) -0.0007(5)
C2 0.0019(7) 0.0061(6) 0.0048(6) 0.0001(5) -0.0002(5) 0.0007(5)
C3 0.0024(7) 0.0078(6) 0.0051(6) -0.0004(5) -0.0008(5) 0.0002(5)
C4 0.0032(7) 0.0077(6) 0.0061(6) 0.0002(5) -0.0005(5) 0.0007(5)
C5 0.0035(8) 0.0117(7) 0.0091(6) -0.0040(5) -0.0003(5) 0.0023(5)
C6 0.0050(8) 0.0105(6) 0.0089(6) -0.0043(5) -0.0015(5) 0.0006(5)
C7 0.0023(7) 0.0064(6) 0.0057(6) 0.0008(5) -0.0004(5) -0.0004(5)
C8 0.0038(7) 0.0086(6) 0.0070(6) 0.0003(5) -0.0004(5) 0.0001(5)

_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
Ni1 O1 2.0525(11) 3_654 ?
Ni1 O1 2.0526(11) . ?
Ni1 O2 2.0595(11) 7 ?
Ni1 O2 2.0595(11) 5_655 ?
Ni1 O4 2.1145(13) 4 ?
Ni1 O4 2.1145(13) 2_554 ?
O1 C1 1.2501(18) . ?
O2 C1 1.2841(18) . ?
O2 Ni1 2.0596(11) 5_655 ?
O3 C8 1.3032(19) . ?
O3 H3A 0.8400 . ?
O4 C8 1.2358(19) . ?
O4 Ni1 2.1144(13) 2 ?
C1 C2 1.501(2) . ?
C2 C3 1.393(2) . ?
C2 C7 1.4062(19) . ?
C3 C4 1.400(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(2) . ?
C4 C8 1.489(2) . ?
C5 C6 1.393(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.398(2) . ?
C6 H6 0.9500 . ?
C7 C7 1.502(3) 3_655 ?

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 Ni1 O1 91.22(6) 3_654 . ?
O1 Ni1 O2 87.82(5) 3_654 7 ?
O1 Ni1 O2 176.66(4) . 7 ?
O1 Ni1 O2 176.66(4) 3_654 5_655 ?
O1 Ni1 O2 87.82(4) . 5_655 ?
O2 Ni1 O2 93.32(6) 7 5_655 ?
O1 Ni1 O4 82.64(5) 3_654 4 ?
O1 Ni1 O4 98.17(5) . 4 ?
O2 Ni1 O4 84.88(4) 7 4 ?
O2 Ni1 O4 94.33(5) 5_655 4 ?
O1 Ni1 O4 98.16(5) 3_654 2_554 ?
O1 Ni1 O4 82.64(5) . 2_554 ?
O2 Ni1 O4 94.33(5) 7 2_554 ?
O2 Ni1 O4 84.88(4) 5_655 2_554 ?
O4 Ni1 O4 178.86(6) 4 2_554 ?
C1 O1 Ni1 127.54(10) . . ?
C1 O2 Ni1 130.46(10) . 5_655 ?
C8 O3 H3A 109.5 . . ?
C8 O4 Ni1 139.11(11) . 2 ?
O1 C1 O2 124.47(14) . . ?
O1 C1 C2 118.93(13) . . ?
O2 C1 C2 116.57(13) . . ?
C3 C2 C7 120.46(14) . . ?
C3 C2 C1 119.10(13) . . ?
C7 C2 C1 120.43(14) . . ?
C2 C3 C4 120.02(14) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.71(14) . . ?
C5 C4 C8 120.51(13) . . ?
C3 C4 C8 119.74(13) . . ?
C6 C5 C4 120.13(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.70(14) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C2 118.94(14) . . ?
C6 C7 C7 119.23(13) . 3_655 ?
C2 C7 C7 121.69(14) . 3_655 ?
O4 C8 O3 125.05(15) . . ?
O4 C8 C4 122.63(14) . . ?
O3 C8 C4 112.31(13) . . ?

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 Ni1 O1 C1 -151.33(15) 3_654 . . . ?
O2 Ni1 O1 C1 135.4(7) 7 . . . ?
O2 Ni1 O1 C1 25.47(14) 5_655 . . . ?
O4 Ni1 O1 C1 -68.59(14) 4 . . . ?
O4 Ni1 O1 C1 110.59(14) 2_554 . . . ?
Ni1 O1 C1 O2 25.9(2) . . . . ?
Ni1 O1 C1 C2 -156.13(10) . . . . ?
Ni1 O2 C1 O1 -126.29(14) 5_655 . . . ?
Ni1 O2 C1 C2 55.67(18) 5_655 . . . ?
O1 C1 C2 C3 47.9(2) . . . . ?
O2 C1 C2 C3 -133.98(15) . . . . ?
O1 C1 C2 C7 -133.33(15) . . . . ?
O2 C1 C2 C7 44.8(2) . . . . ?
C7 C2 C3 C4 -2.0(2) . . . . ?
C1 C2 C3 C4 176.81(13) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C2 C3 C4 C8 178.07(14) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C8 C4 C5 C6 -176.11(14) . . . . ?
C4 C5 C6 C7 -1.9(2) . . . . ?
C5 C6 C7 C2 0.5(2) . . . . ?
C5 C6 C7 C7 176.42(13) . . . 3_655 ?
C3 C2 C7 C6 1.4(2) . . . . ?
C1 C2 C7 C6 -177.38(13) . . . . ?
C3 C2 C7 C7 -174.37(12) . . . 3_655 ?
C1 C2 C7 C7 6.84(19) . . . 3_655 ?
Ni1 O4 C8 O3 23.5(3) 2 . . . ?
Ni1 O4 C8 C4 -158.28(12) 2 . . . ?
C5 C4 C8 O4 -15.3(2) . . . . ?
C3 C4 C8 O4 167.33(15) . . . . ?
C5 C4 C8 O3 163.18(14) . . . . ?
C3 C4 C8 O3 -14.2(2) . . . . ?

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
O3 H3A O2 0.84 1.68 2.4978(17) 163.0 4_455

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.093
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_audit_block_doi                 10.5517/cc13ndy3
_database_code_depnum_ccdc_archive 'CCDC 1032515'
_audit_update_record             
;
2014-11-04 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'compound 3'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H8 Cu O8'
_chemical_formula_sum            'C16 H8 Cu O8'
_chemical_formula_weight         391.76

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcn
_symmetry_space_group_name_Hall  '-P 2n 2ab'

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

_cell_length_a                   16.160(3)
_cell_length_b                   9.4550(19)
_cell_length_c                   8.9840(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1372.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    25049
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             788
_exptl_absorpt_coefficient_mu    1.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8532
_exptl_absorpt_correction_T_max  0.8532
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.72000
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'synchrotron, 3W1A at BSRF'
_diffrn_radiation_monochromator  'double crystal monochromator'
_diffrn_measurement_device_type  mar555
_diffrn_measurement_method       'oscillation mode'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6733
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         31.13
_reflns_number_total             2068
_reflns_number_gt                1768
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       mar555
_computing_cell_refinement       'HKL 2000'
_computing_data_reduction        'HKL 2000'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0681P)²+0.4602P] 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         2068
_refine_ls_number_parameters     115
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.111
_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
Cu1 Cu 0.5000 0.03507(3) -0.2500 0.00349(12) Uani 1 2 d SU . .
O1 O 0.46425(8) 0.18424(13) -0.11100(13) 0.0064(2) Uani 1 1 d . . .
O2 O 0.52690(7) 0.10810(12) 0.09648(13) 0.0041(2) Uani 1 1 d . . .
O3 O 0.17842(8) 0.34056(14) -0.00802(14) 0.0110(3) Uani 1 1 d U . .
H3A H 0.1305 0.3640 -0.0344 0.016 Uiso 1 1 calc R . .
O4 O 0.14767(8) 0.47055(13) 0.19437(17) 0.0098(3) Uani 1 1 d . . .
C1 C 0.47363(9) 0.18431(16) 0.02751(18) 0.0040(3) Uani 1 1 d . . .
C2 C 0.42090(10) 0.28387(17) 0.11587(18) 0.0042(3) Uani 1 1 d . . .
C3 C 0.33729(10) 0.29586(17) 0.0790(2) 0.0058(3) Uani 1 1 d . . .
H3 H 0.3152 0.2419 -0.0009 0.007 Uiso 1 1 calc R . .
C4 C 0.28618(9) 0.38716(17) 0.15927(19) 0.0055(3) Uani 1 1 d . . .
C5 C 0.31899(12) 0.46867(18) 0.2742(2) 0.0088(3) Uani 1 1 d . . .
H5 H 0.2843 0.5311 0.3286 0.011 Uiso 1 1 calc R . .
C6 C 0.40289(10) 0.45842(17) 0.3091(2) 0.0082(3) Uani 1 1 d . . .
H6 H 0.4252 0.5154 0.3864 0.010 Uiso 1 1 calc R . .
C7 C 0.45463(10) 0.36543(18) 0.23192(18) 0.0046(3) Uani 1 1 d . . .
C8 C 0.19690(10) 0.40360(17) 0.11906(19) 0.0061(3) 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
Cu1 0.00425(17) 0.00475(16) 0.00146(19) 0.000 0.00099(8) 0.000
O1 0.0090(5) 0.0069(5) 0.0033(6) -0.0015(4) 0.0005(4) 0.0029(4)
O2 0.0023(5) 0.0061(5) 0.0038(6) 0.0026(4) 0.0005(4) 0.0007(4)
O3 0.0044(5) 0.0185(6) 0.0100(6) -0.0043(5) -0.0037(4) 0.0025(4)
O4 0.0040(5) 0.0127(6) 0.0126(7) -0.0019(5) 0.0012(5) 0.0020(4)
C1 0.0021(6) 0.0054(6) 0.0044(7) 0.0003(5) -0.0004(5) -0.0010(5)
C2 0.0036(6) 0.0057(6) 0.0033(8) 0.0007(5) -0.0001(5) 0.0006(5)
C3 0.0036(6) 0.0082(7) 0.0057(8) 0.0005(6) -0.0004(5) 0.0003(5)
C4 0.0022(6) 0.0075(7) 0.0068(8) 0.0014(6) -0.0004(5) 0.0017(5)
C5 0.0049(7) 0.0131(8) 0.0084(8) -0.0045(6) 0.0005(6) 0.0027(5)
C6 0.0057(7) 0.0118(8) 0.0070(9) -0.0052(6) -0.0023(6) 0.0008(5)
C7 0.0026(6) 0.0077(7) 0.0036(7) 0.0009(5) -0.0008(5) -0.0005(5)
C8 0.0034(6) 0.0077(7) 0.0073(8) 0.0012(6) -0.0004(5) 0.0006(5)

_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
Cu1 O1 1.9704(12) . ?
Cu1 O1 1.9704(12) 3_654 ?
Cu1 O2 1.9808(12) 7 ?
Cu1 O2 1.9808(12) 5_655 ?
Cu1 O4 2.4386(14) 4 ?
Cu1 O4 2.4386(14) 2_554 ?
O1 C1 1.254(2) . ?
O2 C1 1.2823(19) . ?
O2 Cu1 1.9808(12) 5_655 ?
O3 C8 1.322(2) . ?
O3 H3A 0.8400 . ?
O4 C8 1.221(2) . ?
O4 Cu1 2.4386(14) 2 ?
C1 C2 1.497(2) . ?
C2 C3 1.396(2) . ?
C2 C7 1.407(2) . ?
C3 C4 1.396(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(2) . ?
C4 C8 1.495(2) . ?
C5 C6 1.395(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(2) . ?
C6 H6 0.9500 . ?
C7 C7 1.502(3) 3_655 ?

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 Cu1 O1 88.59(7) . 3_654 ?
O1 Cu1 O2 174.16(5) . 7 ?
O1 Cu1 O2 89.06(5) 3_654 7 ?
O1 Cu1 O2 89.06(5) . 5_655 ?
O1 Cu1 O2 174.16(5) 3_654 5_655 ?
O2 Cu1 O2 93.78(7) 7 5_655 ?
O1 Cu1 O4 99.94(5) . 4 ?
O1 Cu1 O4 81.87(5) 3_654 4 ?
O2 Cu1 O4 85.01(5) 7 4 ?
O2 Cu1 O4 93.27(5) 5_655 4 ?
O1 Cu1 O4 81.87(5) . 2_554 ?
O1 Cu1 O4 99.94(5) 3_654 2_554 ?
O2 Cu1 O4 93.27(5) 7 2_554 ?
O2 Cu1 O4 85.01(5) 5_655 2_554 ?
O4 Cu1 O4 177.50(6) 4 2_554 ?
C1 O1 Cu1 126.45(11) . . ?
C1 O2 Cu1 124.97(10) . 5_655 ?
C8 O3 H3A 109.5 . . ?
C8 O4 Cu1 137.71(12) . 2 ?
O1 C1 O2 124.09(15) . . ?
O1 C1 C2 117.24(14) . . ?
O2 C1 C2 118.63(14) . . ?
C3 C2 C7 120.44(15) . . ?
C3 C2 C1 118.42(14) . . ?
C7 C2 C1 121.13(14) . . ?
C4 C3 C2 120.02(16) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.00(15) . . ?
C5 C4 C8 119.25(15) . . ?
C3 C4 C8 120.69(15) . . ?
C4 C5 C6 119.87(16) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 120.91(16) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C2 118.73(15) . . ?
C6 C7 C7 118.48(15) . 3_655 ?
C2 C7 C7 122.59(15) . 3_655 ?
O4 C8 O3 124.39(15) . . ?
O4 C8 C4 123.27(16) . . ?
O3 C8 C4 112.32(14) . . ?

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 Cu1 O1 C1 -139.12(16) 3_654 . . . ?
O2 Cu1 O1 C1 154.6(4) 7 . . . ?
O2 Cu1 O1 C1 35.54(14) 5_655 . . . ?
O4 Cu1 O1 C1 -57.62(14) 4 . . . ?
O4 Cu1 O1 C1 120.63(14) 2_554 . . . ?
Cu1 O1 C1 O2 20.0(2) . . . . ?
Cu1 O1 C1 C2 -162.17(11) . . . . ?
Cu1 O2 C1 O1 -120.36(15) 5_655 . . . ?
Cu1 O2 C1 C2 61.88(18) 5_655 . . . ?
O1 C1 C2 C3 43.1(2) . . . . ?
O2 C1 C2 C3 -138.96(16) . . . . ?
O1 C1 C2 C7 -135.87(16) . . . . ?
O2 C1 C2 C7 42.0(2) . . . . ?
C7 C2 C3 C4 -1.3(2) . . . . ?
C1 C2 C3 C4 179.73(15) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C2 C3 C4 C8 178.66(15) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C8 C4 C5 C6 -177.53(17) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
C5 C6 C7 C2 1.2(3) . . . . ?
C5 C6 C7 C7 176.31(17) . . . 3_655 ?
C3 C2 C7 C6 -0.1(2) . . . . ?
C1 C2 C7 C6 178.92(15) . . . . ?
C3 C2 C7 C7 -174.91(15) . . . 3_655 ?
C1 C2 C7 C7 4.1(2) . . . 3_655 ?
Cu1 O4 C8 O3 31.8(3) 2 . . . ?
Cu1 O4 C8 C4 -149.85(14) 2 . . . ?
C5 C4 C8 O4 -10.4(3) . . . . ?
C3 C4 C8 O4 172.31(16) . . . . ?
C5 C4 C8 O3 168.09(15) . . . . ?
C3 C4 C8 O3 -9.2(2) . . . . ?

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
O3 H3A O2 0.84 1.78 2.6196(17) 173.1 4_455

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        31.13
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.572
_refine_diff_density_min         -1.211
_refine_diff_density_rms         0.126
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_audit_block_doi                 10.5517/cc13ndz4
_database_code_depnum_ccdc_archive 'CCDC 1032516'
_audit_update_record             
;
2014-11-04 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'compound 4'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H8 Zn O8'
_chemical_formula_sum            'C16 H8 O8 Zn'
_chemical_formula_weight         393.59

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'
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           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn
_symmetry_space_group_name_Hall  '-P 2n 2ab'

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

_cell_length_a                   15.147(3)
_cell_length_b                   8.8340(18)
_cell_length_c                   9.0620(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1212.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    2.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6810
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.72000
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'synchrotron, 3W1A at BSRF'
_diffrn_radiation_monochromator  'double crystal monochromator'
_diffrn_measurement_device_type  mar555
_diffrn_measurement_method       'oscillation mode'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5983
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.54
_diffrn_reflns_theta_max         30.72
_reflns_number_total             1796
_reflns_number_gt                1691
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       mar555
_computing_cell_refinement       'HKL 2000'
_computing_data_reduction        'HKL 2000'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0774P)²+12.3561P] 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         1796
_refine_ls_number_parameters     105
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1709
_refine_ls_wR_factor_gt          0.1689
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.122
_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 0.5000 0.04721(6) -0.2500 0.0033(2) Uani 1 2 d S . .
O1 O 0.46804(17) 0.2018(3) -0.1023(3) 0.0062(5) Uani 1 1 d . . .
O2 O 0.52542(16) 0.1107(3) 0.0959(3) 0.0044(5) Uani 1 1 d . . .
O3 O 0.17303(18) 0.3594(3) 0.0027(3) 0.0105(5) Uani 1 1 d U . .
H3A H 0.118(4) 0.380(6) -0.036(6) 0.013 Uiso 1 1 d . . .
O4 O 0.13639(17) 0.4579(3) 0.2122(3) 0.0076(5) Uani 1 1 d . . .
C1 C 0.4740(2) 0.1942(4) 0.0294(4) 0.0047(6) Uani 1 1 d . . .
C2 C 0.42169(12) 0.2895(2) 0.1147(2) 0.0050(6) Uani 1 1 d G . .
C3 C 0.33238(13) 0.3007(2) 0.0812(2) 0.0060(6) Uani 1 1 d GU . .
H3 H 0.3090 0.2479 -0.0014 0.007 Uiso 1 1 calc R . .
C4 C 0.27727(10) 0.3891(3) 0.1685(2) 0.0067(6) Uani 1 1 d G . .
C5 C 0.31147(13) 0.4663(3) 0.2892(2) 0.0088(6) Uani 1 1 d G . .
H5 H 0.2738 0.5267 0.3489 0.011 Uiso 1 1 calc R . .
C6 C 0.40079(14) 0.4552(3) 0.3227(2) 0.0085(6) Uani 1 1 d G . .
H6 H 0.4242 0.5079 0.4053 0.010 Uiso 1 1 calc R . .
C7 C 0.45590(10) 0.3668(3) 0.2355(2) 0.0053(6) Uani 1 1 d G . .
C8 C 0.1887(2) 0.4044(4) 0.1309(4) 0.0058(6) 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
Zn1 0.0023(3) 0.0049(3) 0.0026(3) 0.000 0.00034(16) 0.000
O1 0.0089(11) 0.0072(11) 0.0026(10) -0.0011(8) 0.0001(8) 0.0025(9)
O2 0.0025(10) 0.0055(10) 0.0052(10) 0.0020(8) 0.0006(8) 0.0013(8)
O3 0.0053(10) 0.0185(12) 0.0078(10) -0.0028(9) -0.0018(8) 0.0011(9)
O4 0.0026(11) 0.0099(12) 0.0103(11) -0.0023(9) 0.0005(9) 0.0001(8)
C1 0.0033(13) 0.0049(13) 0.0060(14) -0.0002(11) 0.0001(11) -0.0009(11)
C2 0.0044(13) 0.0060(14) 0.0047(13) 0.0013(11) -0.0012(11) -0.0016(11)
C3 0.0030(11) 0.0085(12) 0.0064(11) 0.0012(10) -0.0005(10) 0.0013(10)
C4 0.0062(13) 0.0076(14) 0.0063(13) 0.0004(11) 0.0011(11) 0.0011(12)
C5 0.0061(15) 0.0126(16) 0.0076(14) -0.0020(12) -0.0012(12) 0.0019(12)
C6 0.0039(15) 0.0102(15) 0.0115(15) -0.0031(12) -0.0003(12) 0.0018(11)
C7 0.0036(16) 0.0067(14) 0.0056(13) 0.0013(11) 0.0007(11) -0.0005(11)
C8 0.0041(13) 0.0062(13) 0.0072(14) 0.0010(11) 0.0000(11) 0.0010(11)

_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 1.973(2) 3_654 ?
Zn1 O1 1.973(2) . ?
Zn1 O2 2.011(2) 7 ?
Zn1 O2 2.011(2) 5_655 ?
Zn1 O4 2.095(3) 4 ?
Zn1 O4 2.095(3) 2_554 ?
O1 C1 1.199(4) . ?
O2 C1 1.230(4) . ?
O2 Zn1 2.011(2) 5_655 ?
O3 C8 1.251(4) . ?
O3 H3A 0.93(6) . ?
O4 C8 1.181(4) . ?
O4 Zn1 2.095(3) 2 ?
C1 C2 1.391(4) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 C8 1.391(4) . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 C7 1.3900 . ?
C6 H6 0.9500 . ?
C7 C7 1.362(3) 3_655 ?

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 92.38(15) 3_654 . ?
O1 Zn1 O2 87.82(11) 3_654 7 ?
O1 Zn1 O2 176.78(10) . 7 ?
O1 Zn1 O2 176.78(10) 3_654 5_655 ?
O1 Zn1 O2 87.82(11) . 5_655 ?
O2 Zn1 O2 92.16(14) 7 5_655 ?
O1 Zn1 O4 83.34(11) 3_654 4 ?
O1 Zn1 O4 98.40(11) . 4 ?
O2 Zn1 O4 84.82(10) 7 4 ?
O2 Zn1 O4 93.45(10) 5_655 4 ?
O1 Zn1 O4 98.39(11) 3_654 2_554 ?
O1 Zn1 O4 83.34(11) . 2_554 ?
O2 Zn1 O4 93.45(10) 7 2_554 ?
O2 Zn1 O4 84.82(10) 5_655 2_554 ?
O4 Zn1 O4 177.52(14) 4 2_554 ?
C1 O1 Zn1 128.2(2) . . ?
C1 O2 Zn1 129.4(2) . 5_655 ?
C8 O3 H3A 117(4) . . ?
C8 O4 Zn1 139.1(3) . 2 ?
O1 C1 O2 124.7(3) . . ?
O1 C1 C2 118.4(3) . . ?
O2 C1 C2 116.8(3) . . ?
C3 C2 C7 120.0 . . ?
C3 C2 C1 118.45(19) . . ?
C7 C2 C1 121.48(19) . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 C8 120.3(2) . . ?
C3 C4 C8 119.7(2) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.0 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C7 C7 C6 118.6(2) 3_655 . ?
C7 C7 C2 121.2(2) 3_655 . ?
C6 C7 C2 120.0 . . ?
O4 C8 O3 125.4(3) . . ?
O4 C8 C4 122.3(3) . . ?
O3 C8 C4 112.3(3) . . ?

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 -148.6(4) 3_654 . . . ?
O2 Zn1 O1 C1 117.9(18) 7 . . . ?
O2 Zn1 O1 C1 28.2(3) 5_655 . . . ?
O4 Zn1 O1 C1 -65.0(3) 4 . . . ?
O4 Zn1 O1 C1 113.3(3) 2_554 . . . ?
Zn1 O1 C1 O2 24.1(5) . . . . ?
Zn1 O1 C1 C2 -158.2(2) . . . . ?
Zn1 O2 C1 O1 -123.9(3) 5_655 . . . ?
Zn1 O2 C1 C2 58.4(4) 5_655 . . . ?
O1 C1 C2 C3 47.6(4) . . . . ?
O2 C1 C2 C3 -134.5(3) . . . . ?
O1 C1 C2 C7 -135.6(3) . . . . ?
O2 C1 C2 C7 42.3(4) . . . . ?
C7 C2 C3 C4 0.0 . . . . ?
C1 C2 C3 C4 176.9(2) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C2 C3 C4 C8 177.5(3) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C8 C4 C5 C6 -177.5(3) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 C6 C7 C7 175.3(2) . . . 3_655 ?
C5 C6 C7 C2 0.0 . . . . ?
C3 C2 C7 C7 -175.2(2) . . . 3_655 ?
C1 C2 C7 C7 8.1(3) . . . 3_655 ?
C3 C2 C7 C6 0.0 . . . . ?
C1 C2 C7 C6 -176.8(3) . . . . ?
Zn1 O4 C8 O3 26.0(6) 2 . . . ?
Zn1 O4 C8 C4 -156.0(3) 2 . . . ?
C5 C4 C8 O4 -14.5(4) . . . . ?
C3 C4 C8 O4 168.0(3) . . . . ?
C5 C4 C8 O3 163.8(2) . . . . ?
C3 C4 C8 O3 -13.7(4) . . . . ?

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
O3 H3A O2 0.93(6) 1.50(6) 2.422(4) 171(6) 4_455

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        30.72
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         2.293
_refine_diff_density_min         -2.039
_refine_diff_density_rms         0.213
