# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_Cpx3
_database_code_depnum_ccdc_archive 'CCDC 984612'

_audit_update_record             
;
2014-02-01 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N2 O8 Zn'
_chemical_formula_sum            'C14 H16 N2 O8 Zn'
_chemical_formula_weight         405.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   7.0534(4)
_cell_length_b                   13.3638(8)
_cell_length_c                   16.8646(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1589.66(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5609
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      28.33

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    1.593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6640
_exptl_absorpt_correction_T_max  0.9538
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           ?

_diffrn_ambient_temperature      123(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 ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20767
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         27.50
_reflns_number_total             1828
_reflns_number_gt                1528
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'


_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)+(0.0343P)²+0.5450P] 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         1828
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0653
_refine_ls_wR_factor_gt          0.0612
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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 0.5000 0.0000 0.01320(9) Uani 1 2 d S . .
O1 O -0.08888(16) 0.34978(8) -0.00854(6) 0.0162(2) Uani 1 1 d . . .
H1 H -0.079(3) 0.3148(16) -0.0510(13) 0.039(6) Uiso 1 1 d . . .
O1W O 0.27781(16) 0.45243(8) -0.03237(7) 0.0175(2) Uani 1 1 d . . .
H1W H 0.341(3) 0.4303(18) 0.0053(13) 0.041(7) Uiso 1 1 d . . .
H2W H 0.338(3) 0.4995(16) -0.0495(14) 0.034(6) Uiso 1 1 d . . .
O2 O -0.0635(2) 0.24427(8) 0.36028(7) 0.0318(3) Uani 1 1 d . . .
O3 O 0.00641(15) 0.39308(8) 0.41153(7) 0.0189(2) Uani 1 1 d . . .
N1 N 0.02489(17) 0.45044(9) 0.11799(8) 0.0141(3) Uani 1 1 d . . .
C1 C -0.0521(2) 0.28921(11) 0.05889(9) 0.0170(3) Uani 1 1 d . . .
H1A H 0.0604 0.2468 0.0489 0.020 Uiso 1 1 calc R . .
H1B H -0.1618 0.2447 0.0689 0.020 Uiso 1 1 calc R . .
C2 C -0.01740(19) 0.35405(11) 0.13029(9) 0.0138(3) Uani 1 1 d . . .
C3 C -0.0292(2) 0.31426(11) 0.20641(9) 0.0154(3) Uani 1 1 d . . .
H3 H -0.0586 0.2455 0.2137 0.018 Uiso 1 1 calc R . .
C4 C 0.00226(19) 0.37528(11) 0.27134(9) 0.0139(3) Uani 1 1 d . . .
C5 C 0.0470(2) 0.47525(11) 0.25824(9) 0.0160(3) Uani 1 1 d . . .
H5 H 0.0704 0.5189 0.3016 0.019 Uiso 1 1 calc R . .
C6 C 0.0569(2) 0.51014(10) 0.18127(9) 0.0172(3) Uani 1 1 d . . .
H6 H 0.0873 0.5785 0.1725 0.021 Uiso 1 1 calc R . .
C7 C -0.0188(2) 0.33436(11) 0.35486(9) 0.0158(3) Uani 1 1 d . . .


_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 N1 2.1045(13) 5_565 ?
Zn1 N1 2.1046(13) . ?
Zn1 O1 2.1081(11) . ?
Zn1 O1 2.1081(11) 5_565 ?
Zn1 O1W 2.1311(11) 5_565 ?
Zn1 O1W 2.1311(11) . ?
O1 C1 1.4199(17) . ?
O1 H1 0.86(2) . ?
O1W H1W 0.83(2) . ?
O1W H2W 0.81(2) . ?
O2 C7 1.2478(18) . ?
O3 C7 1.2494(18) . ?
N1 C2 1.3384(19) . ?
N1 C6 1.3514(19) . ?
C1 C2 1.504(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.392(2) . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 C7 1.518(2) . ?
C5 C6 1.381(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Zn1 N1 180.0 5_565 . ?
N1 Zn1 O1 102.14(4) 5_565 . ?
N1 Zn1 O1 77.86(4) . . ?
N1 Zn1 O1 77.86(4) 5_565 5_565 ?
N1 Zn1 O1 102.14(4) . 5_565 ?
O1 Zn1 O1 180.0 . 5_565 ?
N1 Zn1 O1W 94.10(4) 5_565 5_565 ?
N1 Zn1 O1W 85.89(4) . 5_565 ?
O1 Zn1 O1W 91.61(4) . 5_565 ?
O1 Zn1 O1W 88.39(4) 5_565 5_565 ?
N1 Zn1 O1W 85.89(4) 5_565 . ?
N1 Zn1 O1W 94.11(4) . . ?
O1 Zn1 O1W 88.39(4) . . ?
O1 Zn1 O1W 91.61(4) 5_565 . ?
O1W Zn1 O1W 180.0 5_565 . ?
C1 O1 Zn1 115.71(9) . . ?
C1 O1 H1 110.0(14) . . ?
Zn1 O1 H1 123.6(14) . . ?
Zn1 O1W H1W 113.9(16) . . ?
Zn1 O1W H2W 110.0(15) . . ?
H1W O1W H2W 105(2) . . ?
C2 N1 C6 118.89(13) . . ?
C2 N1 Zn1 115.52(10) . . ?
C6 N1 Zn1 125.08(10) . . ?
O1 C1 C2 110.03(12) . . ?
O1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
O1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C3 121.59(13) . . ?
N1 C2 C1 117.83(13) . . ?
C3 C2 C1 120.58(13) . . ?
C4 C3 C2 119.69(13) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 118.49(13) . . ?
C3 C4 C7 120.43(13) . . ?
C5 C4 C7 121.04(13) . . ?
C6 C5 C4 119.02(14) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
N1 C6 C5 122.31(13) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
O2 C7 O3 125.87(14) . . ?
O2 C7 C4 116.12(13) . . ?
O3 C7 C4 118.00(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
N1 Zn1 O1 C1 167.75(10) 5_565 . . . ?
N1 Zn1 O1 C1 -12.26(10) . . . . ?
O1 Zn1 O1 C1 -85.1(19) 5_565 . . . ?
O1W Zn1 O1 C1 -97.71(10) 5_565 . . . ?
O1W Zn1 O1 C1 82.29(10) . . . . ?
N1 Zn1 N1 C2 157.0(9) 5_565 . . . ?
O1 Zn1 N1 C2 2.14(10) . . . . ?
O1 Zn1 N1 C2 -177.86(10) 5_565 . . . ?
O1W Zn1 N1 C2 94.67(10) 5_565 . . . ?
O1W Zn1 N1 C2 -85.33(10) . . . . ?
N1 Zn1 N1 C6 -14.7(9) 5_565 . . . ?
O1 Zn1 N1 C6 -169.55(13) . . . . ?
O1 Zn1 N1 C6 10.45(13) 5_565 . . . ?
O1W Zn1 N1 C6 -77.01(13) 5_565 . . . ?
O1W Zn1 N1 C6 102.99(13) . . . . ?
Zn1 O1 C1 C2 18.94(15) . . . . ?
C6 N1 C2 C3 0.1(2) . . . . ?
Zn1 N1 C2 C3 -172.18(10) . . . . ?
C6 N1 C2 C1 -179.91(14) . . . . ?
Zn1 N1 C2 C1 7.86(16) . . . . ?
O1 C1 C2 N1 -17.56(18) . . . . ?
O1 C1 C2 C3 162.48(13) . . . . ?
N1 C2 C3 C4 0.4(2) . . . . ?
C1 C2 C3 C4 -179.65(13) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C2 C3 C4 C7 177.17(12) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C7 C4 C5 C6 -177.30(14) . . . . ?
C2 N1 C6 C5 -0.2(2) . . . . ?
Zn1 N1 C6 C5 171.23(12) . . . . ?
C4 C5 C6 N1 -0.1(2) . . . . ?
C3 C4 C7 O2 0.6(2) . . . . ?
C5 C4 C7 O2 178.41(15) . . . . ?
C3 C4 C7 O3 -178.24(13) . . . . ?
C5 C4 C7 O3 -0.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_Cpx4
_database_code_depnum_ccdc_archive 'CCDC 984613'
_audit_update_record             
;
2014-02-01 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N2 O8 Zn, 2(H2 O)'
_chemical_formula_sum            'C14 H20 N2 O10 Zn'
_chemical_formula_weight         441.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_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                   13.6211(6)
_cell_length_b                   7.7315(4)
_cell_length_c                   16.8791(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.7790(10)
_cell_angle_gamma                90.00
_cell_volume                     1726.41(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7277
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      28.22

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    1.482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7559
_exptl_absorpt_correction_T_max  0.8659
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15177
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         28.27
_reflns_number_total             2152
_reflns_number_gt                1944
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0300P)²+1.1905P] 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         2152
_refine_ls_number_parameters     138
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0601
_refine_ls_wR_factor_gt          0.0583
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.085
_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 0.0000 0.62050(3) 0.2500 0.02257(8) Uani 1 2 d S . .
O1 O -0.11686(8) 0.81390(16) 0.25497(6) 0.0304(2) Uani 1 1 d D . .
H7 H -0.1706(12) 0.828(3) 0.2188(10) 0.036 Uiso 1 1 d D . .
O2 O 0.26682(9) 0.50504(18) 0.55042(7) 0.0440(3) Uani 1 1 d . . .
O3 O 0.21423(9) 0.64706(18) 0.64721(6) 0.0399(3) Uani 1 1 d . . .
O1W O 0.11063(9) 0.43189(16) 0.26220(7) 0.0350(3) Uani 1 1 d D . .
H1W1 H 0.1038(16) 0.338(2) 0.2820(12) 0.042 Uiso 1 1 d D . .
H2W1 H 0.1380(15) 0.410(3) 0.2257(11) 0.042 Uiso 1 1 d D . .
O2W O 0.08375(11) 0.12707(18) 0.32918(8) 0.0461(3) Uani 1 1 d D . .
H1W2 H 0.1314(15) 0.097(3) 0.3690(12) 0.055 Uiso 1 1 d D . .
H2W2 H 0.0775(17) 0.050(3) 0.2928(12) 0.055 Uiso 1 1 d D . .
N1 N 0.01942(9) 0.67073(16) 0.37400(7) 0.0223(2) Uani 1 1 d . . .
C1 C -0.14223(12) 0.8193(2) 0.33153(9) 0.0346(4) Uani 1 1 d . . .
H1A H -0.1997 0.7446 0.3305 0.042 Uiso 1 1 calc R . .
H1B H -0.1607 0.9364 0.3428 0.042 Uiso 1 1 calc R . .
C2 C -0.05335(10) 0.76056(19) 0.39723(8) 0.0248(3) Uani 1 1 d . . .
C3 C -0.04871(12) 0.7968(2) 0.47814(9) 0.0312(3) Uani 1 1 d . . .
H3 H -0.1009 0.8562 0.4930 0.037 Uiso 1 1 calc R . .
C4 C 0.03500(11) 0.7431(2) 0.53663(8) 0.0291(3) Uani 1 1 d . . .
H4 H 0.0400 0.7675 0.5914 0.035 Uiso 1 1 calc R . .
C5 C 0.11117(10) 0.65302(18) 0.51344(8) 0.0235(3) Uani 1 1 d . . .
C6 C 0.09968(10) 0.61803(19) 0.43135(8) 0.0235(3) Uani 1 1 d . . .
H6 H 0.1499 0.5552 0.4153 0.028 Uiso 1 1 calc R . .
C7 C 0.20550(11) 0.5959(2) 0.57473(9) 0.0280(3) Uani 1 1 d . . .


_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 O1W 2.0716(12) 2 ?
Zn1 O1W 2.0716(12) . ?
Zn1 N1 2.0827(11) . ?
Zn1 N1 2.0827(11) 2 ?
Zn1 O1 2.2000(11) 2 ?
Zn1 O1 2.2000(11) . ?
O1 C1 1.4156(18) . ?
O1 H7 0.841(15) . ?
O2 C7 1.2338(19) . ?
O3 C7 1.2642(18) . ?
O1W H1W1 0.814(14) . ?
O1W H2W1 0.811(14) . ?
O2W H1W2 0.848(15) . ?
O2W H2W2 0.845(15) . ?
N1 C6 1.3394(17) . ?
N1 C2 1.3430(18) . ?
C1 C2 1.504(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.381(2) . ?
C3 C4 1.382(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3836(19) . ?
C5 C7 1.5110(19) . ?
C6 H6 0.9300 . ?

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
O1W Zn1 O1W 90.52(7) 2 . ?
O1W Zn1 N1 98.42(5) 2 . ?
O1W Zn1 N1 96.66(5) . . ?
O1W Zn1 N1 96.66(5) 2 2 ?
O1W Zn1 N1 98.42(5) . 2 ?
N1 Zn1 N1 158.51(7) . 2 ?
O1W Zn1 O1 172.04(4) 2 2 ?
O1W Zn1 O1 88.08(5) . 2 ?
N1 Zn1 O1 89.53(4) . 2 ?
N1 Zn1 O1 75.81(4) 2 2 ?
O1W Zn1 O1 88.08(5) 2 . ?
O1W Zn1 O1 172.04(4) . . ?
N1 Zn1 O1 75.81(4) . . ?
N1 Zn1 O1 89.53(4) 2 . ?
O1 Zn1 O1 94.37(6) 2 . ?
C1 O1 Zn1 113.03(9) . . ?
C1 O1 H7 107.4(13) . . ?
Zn1 O1 H7 125.0(13) . . ?
Zn1 O1W H1W1 121.2(15) . . ?
Zn1 O1W H2W1 121.9(15) . . ?
H1W1 O1W H2W1 104(2) . . ?
H1W2 O2W H2W2 108(2) . . ?
C6 N1 C2 118.58(12) . . ?
C6 N1 Zn1 123.78(9) . . ?
C2 N1 Zn1 117.64(9) . . ?
O1 C1 C2 109.60(12) . . ?
O1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
O1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C3 122.04(13) . . ?
N1 C2 C1 117.48(12) . . ?
C3 C2 C1 120.47(13) . . ?
C2 C3 C4 118.76(14) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.77(13) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 117.96(13) . . ?
C4 C5 C7 121.81(13) . . ?
C6 C5 C7 120.23(13) . . ?
N1 C6 C5 122.86(13) . . ?
N1 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
O2 C7 O3 125.80(14) . . ?
O2 C7 C5 118.13(13) . . ?
O3 C7 C5 116.08(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
O1 H7 O3 0.841(15) 1.748(15) 2.5884(15) 177(2) 8_465
O1W H1W1 O2W 0.814(14) 1.863(14) 2.6764(19) 178(2) .
O1W H2W1 O3 0.811(14) 1.918(14) 2.7269(16) 175(2) 6_565
O2W H1W2 O2 0.848(15) 1.870(16) 2.7103(17) 171(2) 7_556
O2W H2W2 O1 0.845(15) 2.116(17) 2.8963(18) 153(2) 2_545

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1013140'
_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 Co N2 O8'
_chemical_formula_sum            'C14 H16 Co N2 O8'
_chemical_formula_weight         399.22

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   7.1867(3)
_cell_length_b                   13.3223(6)
_cell_length_c                   16.8797(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1616.12(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9867
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      37.68

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             820
_exptl_absorpt_coefficient_mu    1.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7320
_exptl_absorpt_correction_T_max  0.8254
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            33694
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         37.81
_reflns_number_total             4334
_reflns_number_gt                3448
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0461P)²+0.5280P] 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       0.0217(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4334
_refine_ls_number_parameters     128
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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
Co1 Co 0.5000 0.0000 0.5000 0.02319(7) Uani 1 2 d S . .
O1 O 0.57497(17) 0.15078(6) 0.49281(4) 0.03208(19) Uani 1 1 d D . .
H1 H 0.564(3) 0.1860(15) 0.4522(10) 0.060(6) Uiso 1 1 d D . .
O2 O 0.5661(2) 0.25538(7) 0.86184(5) 0.0610(4) Uani 1 1 d . . .
O3 O 0.49602(13) 0.10695(7) 0.91252(5) 0.0351(2) Uani 1 1 d . . .
O1W O 0.22719(14) 0.04083(7) 0.47169(5) 0.03530(19) Uani 1 1 d D . .
H2W H 0.161(2) -0.0078(12) 0.4535(12) 0.049(5) Uiso 1 1 d D . .
H1W H 0.171(3) 0.0632(16) 0.5107(10) 0.052(6) Uiso 1 1 d D . .
N1 N 0.47867(13) 0.04952(7) 0.61944(5) 0.02489(16) Uani 1 1 d . . .
C1 C 0.5471(2) 0.21145(8) 0.56035(6) 0.0320(2) Uani 1 1 d . . .
H1A H 0.4396 0.2543 0.5523 0.038 Uiso 1 1 calc R . .
H1B H 0.6549 0.2540 0.5686 0.038 Uiso 1 1 calc R . .
C2 C 0.51693(15) 0.14642(7) 0.63199(5) 0.02319(17) Uani 1 1 d . . .
C3 C 0.52906(17) 0.18632(7) 0.70789(5) 0.0268(2) Uani 1 1 d . . .
H3 H 0.5556 0.2541 0.7150 0.032 Uiso 1 1 calc R . .
C4 C 0.50146(14) 0.12469(7) 0.77285(5) 0.02303(16) Uani 1 1 d . . .
C5 C 0.46029(19) 0.02415(8) 0.75959(6) 0.0293(2) Uani 1 1 d . . .
H5 H 0.4398 -0.0191 0.8019 0.035 Uiso 1 1 calc R . .
C6 C 0.4502(2) -0.01050(8) 0.68259(6) 0.0317(2) Uani 1 1 d . . .
H6 H 0.4228 -0.0778 0.6740 0.038 Uiso 1 1 calc R . .
C7 C 0.52106(17) 0.16556(8) 0.85595(6) 0.0278(2) Uani 1 1 d . . .


_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
Co1 O1 2.0833(8) . ?
Co1 O1 2.0833(8) 5_656 ?
Co1 O1W 2.0900(10) 5_656 ?
Co1 O1W 2.0900(10) . ?
Co1 N1 2.1268(8) . ?
Co1 N1 2.1268(8) 5_656 ?
O1 C1 1.4118(12) . ?
O1 H1 0.834(15) . ?
O2 C7 1.2436(14) . ?
O3 C7 1.2465(13) . ?
O1W H2W 0.860(14) . ?
O1W H1W 0.828(14) . ?
N1 C2 1.3367(13) . ?
N1 C6 1.3482(14) . ?
C1 C2 1.5033(13) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.3899(13) . ?
C3 C4 1.3843(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.3898(14) . ?
C4 C7 1.5112(13) . ?
C5 C6 1.3811(14) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?

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 Co1 O1 180.00(4) . 5_656 ?
O1 Co1 O1W 91.24(4) . 5_656 ?
O1 Co1 O1W 88.76(4) 5_656 5_656 ?
O1 Co1 O1W 88.76(4) . . ?
O1 Co1 O1W 91.24(4) 5_656 . ?
O1W Co1 O1W 180.0 5_656 . ?
O1 Co1 N1 76.98(3) . . ?
O1 Co1 N1 103.02(3) 5_656 . ?
O1W Co1 N1 86.08(4) 5_656 . ?
O1W Co1 N1 93.92(4) . . ?
O1 Co1 N1 103.02(3) . 5_656 ?
O1 Co1 N1 76.98(3) 5_656 5_656 ?
O1W Co1 N1 93.92(4) 5_656 5_656 ?
O1W Co1 N1 86.08(4) . 5_656 ?
N1 Co1 N1 180.0 . 5_656 ?
C1 O1 Co1 117.92(6) . . ?
C1 O1 H1 109.1(15) . . ?
Co1 O1 H1 124.4(16) . . ?
Co1 O1W H2W 113.8(13) . . ?
Co1 O1W H1W 111.8(14) . . ?
H2W O1W H1W 107(2) . . ?
C2 N1 C6 118.59(8) . . ?
C2 N1 Co1 115.78(6) . . ?
C6 N1 Co1 125.21(7) . . ?
O1 C1 C2 109.88(8) . . ?
O1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
O1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C3 121.90(9) . . ?
N1 C2 C1 117.31(8) . . ?
C3 C2 C1 120.80(9) . . ?
C4 C3 C2 119.63(9) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 118.33(8) . . ?
C3 C4 C7 120.55(9) . . ?
C5 C4 C7 121.10(8) . . ?
C6 C5 C4 119.01(9) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
N1 C6 C5 122.54(9) . . ?
N1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
O2 C7 O3 125.39(10) . . ?
O2 C7 C4 116.43(9) . . ?
O3 C7 C4 118.16(9) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        37.81
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1013141'
_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N2 Ni O8'
_chemical_formula_sum            'C14 H16 N2 Ni O8'
_chemical_formula_weight         399.00

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'
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   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   7.1353(4)
_cell_length_b                   13.2866(8)
_cell_length_c                   16.8095(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1593.61(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      3.066
_cell_measurement_theta_max      42.90

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    1.265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7427
_exptl_absorpt_correction_T_max  0.9280
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            45407
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         40.25
_reflns_number_total             5008
_reflns_number_gt                3552
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0411P)²+0.4543P] 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         5008
_refine_ls_number_parameters     127
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
Ni1 Ni 1.0000 0.0000 0.5000 0.02100(5) Uani 1 2 d S . .
O1 O 0.91687(13) 0.14849(5) 0.49016(4) 0.02869(15) Uani 1 1 d D . .
H1 H 0.926(3) 0.1838(13) 0.4488(9) 0.059(5) Uiso 1 1 d D . .
O2 O 0.9469(2) 0.25497(7) 0.85978(5) 0.0666(4) Uani 1 1 d . . .
O3 O 1.00482(12) 0.10512(7) 0.91076(4) 0.03420(17) Uani 1 1 d . . .
O1W O 1.27108(12) 0.04420(6) 0.47071(5) 0.03114(15) Uani 1 1 d D . .
H2W H 1.334(2) -0.0049(11) 0.4539(11) 0.051(5) Uiso 1 1 d D . .
H1W H 1.329(2) 0.0632(14) 0.5089(9) 0.049(5) Uiso 1 1 d D . .
N1 N 1.02401(12) 0.04777(6) 0.61662(4) 0.02321(14) Uani 1 1 d . . .
C1 C 0.95406(19) 0.20973(7) 0.55726(5) 0.0314(2) Uani 1 1 d . . .
H1A H 0.8489 0.2544 0.5667 0.038 Uiso 1 1 calc R . .
H1B H 1.0642 0.2507 0.5473 0.038 Uiso 1 1 calc R . .
C2 C 0.98607(13) 0.14499(6) 0.62913(5) 0.02235(15) Uani 1 1 d . . .
C3 C 0.97599(15) 0.18526(7) 0.70536(5) 0.02617(18) Uani 1 1 d . . .
H3 H 0.9501 0.2533 0.7125 0.031 Uiso 1 1 calc R . .
C4 C 1.00473(13) 0.12360(7) 0.77049(5) 0.02259(15) Uani 1 1 d . . .
C5 C 1.04595(17) 0.02286(7) 0.75715(5) 0.02851(18) Uani 1 1 d . . .
H5 H 1.0675 -0.0204 0.7996 0.034 Uiso 1 1 calc R . .
C6 C 1.0544(2) -0.01210(7) 0.67986(6) 0.0306(2) Uani 1 1 d . . .
H6 H 1.0822 -0.0796 0.6712 0.037 Uiso 1 1 calc R . .
C7 C 0.98536(15) 0.16440(7) 0.85409(5) 0.02745(18) Uani 1 1 d . . .


_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 2.0669(7) 5_756 ?
Ni1 O1 2.0669(7) . ?
Ni1 N1 2.0677(7) 5_756 ?
Ni1 N1 2.0677(7) . ?
Ni1 O1W 2.0805(9) . ?
Ni1 O1W 2.0805(9) 5_756 ?
O1 C1 1.4158(12) . ?
O1 H1 0.841(14) . ?
O2 C7 1.2379(13) . ?
O3 C7 1.2437(12) . ?
O1W H2W 0.839(13) . ?
O1W H1W 0.803(13) . ?
N1 C2 1.3364(11) . ?
N1 C6 1.3454(12) . ?
C1 C2 1.5006(12) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.3906(12) . ?
C3 C4 1.3827(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.3886(13) . ?
C4 C7 1.5125(12) . ?
C5 C6 1.3810(13) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?

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 180.00(3) 5_756 . ?
O1 Ni1 N1 78.85(3) 5_756 5_756 ?
O1 Ni1 N1 101.15(3) . 5_756 ?
O1 Ni1 N1 101.15(3) 5_756 . ?
O1 Ni1 N1 78.85(3) . . ?
N1 Ni1 N1 180.0 5_756 . ?
O1 Ni1 O1W 91.24(3) 5_756 . ?
O1 Ni1 O1W 88.76(3) . . ?
N1 Ni1 O1W 86.52(3) 5_756 . ?
N1 Ni1 O1W 93.48(3) . . ?
O1 Ni1 O1W 88.76(3) 5_756 5_756 ?
O1 Ni1 O1W 91.24(3) . 5_756 ?
N1 Ni1 O1W 93.48(3) 5_756 5_756 ?
N1 Ni1 O1W 86.52(3) . 5_756 ?
O1W Ni1 O1W 180.0 . 5_756 ?
C1 O1 Ni1 115.53(6) . . ?
C1 O1 H1 108.8(13) . . ?
Ni1 O1 H1 125.2(13) . . ?
Ni1 O1W H2W 110.8(12) . . ?
Ni1 O1W H1W 112.1(13) . . ?
H2W O1W H1W 103.9(19) . . ?
C2 N1 C6 118.68(7) . . ?
C2 N1 Ni1 115.41(6) . . ?
C6 N1 Ni1 125.52(6) . . ?
O1 C1 C2 109.91(7) . . ?
O1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
O1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C3 121.83(8) . . ?
N1 C2 C1 117.27(7) . . ?
C3 C2 C1 120.90(8) . . ?
C4 C3 C2 119.60(8) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 118.33(8) . . ?
C3 C4 C7 120.64(8) . . ?
C5 C4 C7 120.99(8) . . ?
C6 C5 C4 119.04(8) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
N1 C6 C5 122.50(8) . . ?
N1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
O2 C7 O3 125.53(9) . . ?
O2 C7 C4 116.13(8) . . ?
O3 C7 C4 118.32(9) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        40.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1013142'
_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N2 Ni O8, 2(H2 O)'
_chemical_formula_sum            'C14 H20 N2 Ni O10'
_chemical_formula_weight         435.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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   C2/c
_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                   13.3910(4)
_cell_length_b                   7.7123(2)
_cell_length_c                   16.9892(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.4560(10)
_cell_angle_gamma                90.00
_cell_volume                     1699.02(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8587
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      34.88

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    1.203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8892
_exptl_absorpt_correction_T_max  0.9423
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            22722
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         34.96
_reflns_number_total             3736
_reflns_number_gt                3266
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0398P)²+0.6435P] 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         3736
_refine_ls_number_parameters     138
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0746
_refine_ls_wR_factor_gt          0.0715
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.14535(2) 0.2500 0.01937(5) Uani 1 2 d S . .
O1 O 0.61070(6) 0.33325(11) 0.24457(5) 0.02713(16) Uani 1 1 d D . .
H11 H 0.6677(11) 0.3430(19) 0.2812(9) 0.033 Uiso 1 1 d D . .
O2 O 0.22946(8) -0.00630(15) -0.05083(6) 0.0452(2) Uani 1 1 d . . .
O3 O 0.28294(7) 0.13282(14) -0.14742(5) 0.0378(2) Uani 1 1 d . . .
O1W O 0.61132(7) -0.04176(12) 0.26000(5) 0.03183(17) Uani 1 1 d D . .
H1W1 H 0.6373(13) -0.063(2) 0.2220(9) 0.038 Uiso 1 1 d D . .
H2W1 H 0.5976(14) -0.1350(18) 0.2795(11) 0.038 Uiso 1 1 d D . .
O2W O 0.58392(10) 0.65345(15) 0.32793(7) 0.0463(3) Uani 1 1 d D . .
H1W2 H 0.5730(15) 0.577(2) 0.2895(11) 0.056 Uiso 1 1 d D . .
H2W2 H 0.6325(14) 0.619(3) 0.3666(11) 0.056 Uiso 1 1 d D . .
N1 N 0.47779(6) 0.17508(12) 0.12655(5) 0.02189(15) Uani 1 1 d . . .
C1 C 0.64009(9) 0.32970(18) 0.16989(7) 0.0335(3) Uani 1 1 d . . .
H1A H 0.6989 0.2535 0.1746 0.040 Uiso 1 1 calc R . .
H1B H 0.6598 0.4452 0.1568 0.040 Uiso 1 1 calc R . .
C2 C 0.55124(8) 0.26591(14) 0.10369(6) 0.02477(18) Uani 1 1 d . . .
C3 C 0.54733(9) 0.29819(18) 0.02288(6) 0.0314(2) Uani 1 1 d . . .
H3 H 0.6001 0.3586 0.0084 0.038 Uiso 1 1 calc R . .
C4 C 0.46305(9) 0.23858(16) -0.03606(6) 0.0292(2) Uani 1 1 d . . .
H4 H 0.4585 0.2592 -0.0908 0.035 Uiso 1 1 calc R . .
C5 C 0.38585(7) 0.14821(14) -0.01287(6) 0.02299(17) Uani 1 1 d . . .
C6 C 0.39682(7) 0.11717(14) 0.06917(6) 0.02319(18) Uani 1 1 d . . .
H6 H 0.3461 0.0538 0.0850 0.028 Uiso 1 1 calc R . .
C7 C 0.29155(8) 0.08493(16) -0.07444(6) 0.02692(19) Uani 1 1 d . . .


_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 O1W 2.0511(8) 2_655 ?
Ni1 O1W 2.0511(8) . ?
Ni1 N1 2.0563(8) 2_655 ?
Ni1 N1 2.0563(8) . ?
Ni1 O1 2.0914(8) 2_655 ?
Ni1 O1 2.0914(8) . ?
O1 C1 1.4193(15) . ?
O1 H11 0.860(14) . ?
O2 C7 1.2303(15) . ?
O3 C7 1.2710(13) . ?
O1W H1W1 0.823(14) . ?
O1W H2W1 0.831(13) . ?
O2W H1W2 0.865(15) . ?
O2W H2W2 0.843(15) . ?
N1 C6 1.3407(11) . ?
N1 C2 1.3415(13) . ?
C1 C2 1.5015(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.3833(15) . ?
C3 C4 1.3870(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.3831(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.3854(13) . ?
C5 C7 1.5059(13) . ?
C6 H6 0.9300 . ?

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
O1W Ni1 O1W 90.57(6) 2_655 . ?
O1W Ni1 N1 94.59(4) 2_655 2_655 ?
O1W Ni1 N1 94.41(3) . 2_655 ?
O1W Ni1 N1 94.41(3) 2_655 . ?
O1W Ni1 N1 94.59(4) . . ?
N1 Ni1 N1 167.20(5) 2_655 . ?
O1W Ni1 O1 89.01(4) 2_655 2_655 ?
O1W Ni1 O1 172.88(3) . 2_655 ?
N1 Ni1 O1 78.54(3) 2_655 2_655 ?
N1 Ni1 O1 92.53(3) . 2_655 ?
O1W Ni1 O1 172.88(3) 2_655 . ?
O1W Ni1 O1 89.01(4) . . ?
N1 Ni1 O1 92.53(3) 2_655 . ?
N1 Ni1 O1 78.54(3) . . ?
O1 Ni1 O1 92.28(5) 2_655 . ?
C1 O1 Ni1 112.57(6) . . ?
C1 O1 H11 104.8(12) . . ?
Ni1 O1 H11 122.7(11) . . ?
Ni1 O1W H1W1 120.9(12) . . ?
Ni1 O1W H2W1 114.4(13) . . ?
H1W1 O1W H2W1 108.8(17) . . ?
H1W2 O2W H2W2 109.1(19) . . ?
C6 N1 C2 118.80(8) . . ?
C6 N1 Ni1 126.10(7) . . ?
C2 N1 Ni1 115.07(6) . . ?
O1 C1 C2 109.34(9) . . ?
O1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
O1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
N1 C2 C3 122.17(9) . . ?
N1 C2 C1 117.09(9) . . ?
C3 C2 C1 120.73(10) . . ?
C2 C3 C4 118.64(10) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 119.51(9) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 118.33(9) . . ?
C4 C5 C7 121.48(9) . . ?
C6 C5 C7 120.19(9) . . ?
N1 C6 C5 122.50(9) . . ?
N1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
O2 C7 O3 125.46(10) . . ?
O2 C7 C5 118.46(9) . . ?
O3 C7 C5 116.08(10) . . ?

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
O1W Ni1 O1 C1 -15.0(3) 2_655 . . . ?
O1W Ni1 O1 C1 71.64(8) . . . . ?
N1 Ni1 O1 C1 166.01(8) 2_655 . . . ?
N1 Ni1 O1 C1 -23.25(8) . . . . ?
O1 Ni1 O1 C1 -115.37(8) 2_655 . . . ?
O1W Ni1 N1 C6 14.76(9) 2_655 . . . ?
O1W Ni1 N1 C6 105.69(9) . . . . ?
N1 Ni1 N1 C6 -119.78(9) 2_655 . . . ?
O1 Ni1 N1 C6 -74.44(9) 2_655 . . . ?
O1 Ni1 N1 C6 -166.26(9) . . . . ?
O1W Ni1 N1 C2 -167.30(8) 2_655 . . . ?
O1W Ni1 N1 C2 -76.37(8) . . . . ?
N1 Ni1 N1 C2 58.15(8) 2_655 . . . ?
O1 Ni1 N1 C2 103.50(8) 2_655 . . . ?
O1 Ni1 N1 C2 11.68(8) . . . . ?
Ni1 O1 C1 C2 29.42(12) . . . . ?
C6 N1 C2 C3 -1.54(17) . . . . ?
Ni1 N1 C2 C3 -179.64(10) . . . . ?
C6 N1 C2 C1 179.47(10) . . . . ?
Ni1 N1 C2 C1 1.37(13) . . . . ?
O1 C1 C2 N1 -20.58(15) . . . . ?
O1 C1 C2 C3 160.42(11) . . . . ?
N1 C2 C3 C4 1.86(19) . . . . ?
C1 C2 C3 C4 -179.18(12) . . . . ?
C2 C3 C4 C5 -0.35(19) . . . . ?
C3 C4 C5 C6 -1.35(17) . . . . ?
C3 C4 C5 C7 178.39(11) . . . . ?
C2 N1 C6 C5 -0.29(16) . . . . ?
Ni1 N1 C6 C5 177.57(8) . . . . ?
C4 C5 C6 N1 1.73(16) . . . . ?
C7 C5 C6 N1 -178.01(10) . . . . ?
C4 C5 C7 O2 174.38(12) . . . . ?
C6 C5 C7 O2 -5.89(17) . . . . ?
C4 C5 C7 O3 -6.13(16) . . . . ?
C6 C5 C7 O3 173.61(10) . . . . ?

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
O2W H1W2 O1 0.865(15) 2.136(17) 2.9132(14) 149.3(18) .
O1 H11 O3 0.860(14) 1.718(14) 2.5774(11) 178.2(17) 8_556
O1W H1W1 O3 0.823(14) 1.927(14) 2.7401(13) 169.7(17) 5_655
O1W H2W1 O2W 0.831(13) 1.857(14) 2.6839(15) 173.1(19) 1_545
O2W H1W2 O2W 0.865(15) 2.580(19) 3.015(2) 112.3(16) 2_655
O2W H2W2 O2 0.843(15) 1.872(15) 2.7063(14) 170(2) 8_556

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        34.96
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1013143'

_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 Cu N4 O12, 2(H2 O)'
_chemical_formula_sum            'C14 H18 Cu N4 O14'
_chemical_formula_weight         529.86

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   8.5580(4)
_cell_length_b                   10.3042(5)
_cell_length_c                   12.2558(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.0080(10)
_cell_angle_gamma                90.00
_cell_volume                     1027.81(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8039
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      28.35

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             542
_exptl_absorpt_coefficient_mu    1.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6573
_exptl_absorpt_correction_T_max  0.8941
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           ?

_diffrn_ambient_temperature      123(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 ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14171
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0123
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         27.86
_reflns_number_total             2456
_reflns_number_gt                2262
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0770P)²+2.8571P] 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         2456
_refine_ls_number_parameters     163
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1470
_refine_ls_wR_factor_gt          0.1445
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.0000 0.5000 0.0000 0.01873(18) Uani 1 2 d S . .
O1W O 0.7207(3) 0.3528(2) 0.1591(2) 0.0273(5) Uani 1 1 d D . .
H1W H 0.719(5) 0.280(2) 0.130(3) 0.033 Uiso 1 1 d D . .
H2W H 0.616(3) 0.377(4) 0.130(3) 0.033 Uiso 1 1 d D . .
O1 O 0.0534(3) 0.49319(19) -0.14554(19) 0.0216(4) Uani 1 1 d D . .
H1O H 0.132(4) 0.542(3) -0.145(3) 0.026 Uiso 1 1 d D . .
O2 O 0.3004(4) -0.1070(3) -0.0634(2) 0.0440(7) Uani 1 1 d . . .
O3 O 0.2487(5) -0.1340(3) 0.1055(3) 0.0498(8) Uani 1 1 d D . .
H3O H 0.262(7) -0.218(2) 0.103(5) 0.060 Uiso 1 1 d D . .
O4 O 0.2538(3) 0.6146(2) 0.0967(2) 0.0280(5) Uani 1 1 d . . .
O5 O 0.4110(4) 0.4509(3) 0.1089(5) 0.0791(14) Uani 1 1 d . . .
O6 O 0.5145(4) 0.6393(4) 0.1487(4) 0.0754(13) Uani 1 1 d . . .
N1 N 0.0879(3) 0.3214(2) 0.0180(2) 0.0187(5) Uani 1 1 d . . .
N2 N 0.3955(3) 0.5679(3) 0.1178(3) 0.0300(6) Uani 1 1 d . . .
C1 C 0.0934(4) 0.3652(3) -0.1750(2) 0.0218(6) Uani 1 1 d . . .
H1A H 0.1919 0.3693 -0.2010 0.026 Uiso 1 1 calc R . .
H1B H 0.0012 0.3307 -0.2388 0.026 Uiso 1 1 calc R . .
C2 C 0.1262(3) 0.2763(3) -0.0731(2) 0.0185(5) Uani 1 1 d . . .
C3 C 0.1891(4) 0.1519(3) -0.0742(2) 0.0234(6) Uani 1 1 d . . .
H3 H 0.2176 0.1215 -0.1387 0.028 Uiso 1 1 calc R . .
C4 C 0.2090(4) 0.0736(3) 0.0207(3) 0.0261(6) Uani 1 1 d . . .
C5 C 0.1714(4) 0.1210(3) 0.1154(3) 0.0268(6) Uani 1 1 d . . .
H5 H 0.1867 0.0687 0.1817 0.032 Uiso 1 1 calc R . .
C6 C 0.1112(4) 0.2460(3) 0.1112(2) 0.0238(6) Uani 1 1 d . . .
H6 H 0.0857 0.2795 0.1759 0.029 Uiso 1 1 calc R . .
C7 C 0.2637(6) -0.0645(3) 0.0177(3) 0.0396(9) Uani 1 1 d . . .


_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 N1 1.975(2) . ?
Cu1 N1 1.975(2) 3_565 ?
Cu1 O1 1.975(2) 3_565 ?
Cu1 O1 1.975(2) . ?
Cu1 O4 2.434(2) 3_565 ?
Cu1 O4 2.434(2) . ?
O1W H1W 0.831(19) . ?
O1W H2W 0.892(19) . ?
O1 C1 1.436(3) . ?
O1 H1O 0.837(19) . ?
O2 C7 1.213(5) . ?
O3 C7 1.332(5) . ?
O3 H3O 0.88(2) . ?
O4 N2 1.255(4) . ?
O5 N2 1.221(5) . ?
O6 N2 1.218(4) . ?
N1 C2 1.340(3) . ?
N1 C6 1.344(4) . ?
C1 C2 1.503(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.392(4) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(4) . ?
C4 C7 1.501(4) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 180.0 . 3_565 ?
N1 Cu1 O1 96.82(9) . 3_565 ?
N1 Cu1 O1 83.18(9) 3_565 3_565 ?
N1 Cu1 O1 83.18(9) . . ?
N1 Cu1 O1 96.82(9) 3_565 . ?
O1 Cu1 O1 180.0 3_565 . ?
N1 Cu1 O4 81.61(9) . 3_565 ?
N1 Cu1 O4 98.39(9) 3_565 3_565 ?
O1 Cu1 O4 92.06(9) 3_565 3_565 ?
O1 Cu1 O4 87.94(9) . 3_565 ?
N1 Cu1 O4 98.39(9) . . ?
N1 Cu1 O4 81.61(9) 3_565 . ?
O1 Cu1 O4 87.94(9) 3_565 . ?
O1 Cu1 O4 92.06(9) . . ?
O4 Cu1 O4 180.0 3_565 . ?
H1W O1W H2W 102(4) . . ?
C1 O1 Cu1 113.53(16) . . ?
C1 O1 H1O 107(3) . . ?
Cu1 O1 H1O 113(3) . . ?
C7 O3 H3O 117(4) . . ?
N2 O4 Cu1 125.1(2) . . ?
C2 N1 C6 119.9(2) . . ?
C2 N1 Cu1 114.35(18) . . ?
C6 N1 Cu1 125.79(19) . . ?
O6 N2 O5 121.4(3) . . ?
O6 N2 O4 119.6(3) . . ?
O5 N2 O4 119.0(3) . . ?
O1 C1 C2 110.4(2) . . ?
O1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
O1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
N1 C2 C3 121.4(3) . . ?
N1 C2 C1 116.8(2) . . ?
C3 C2 C1 121.8(2) . . ?
C4 C3 C2 118.6(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 C7 119.4(3) . . ?
C5 C4 C7 120.6(3) . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
N1 C6 C5 121.7(3) . . ?
N1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
O2 C7 O3 125.6(3) . . ?
O2 C7 C4 121.6(3) . . ?
O3 C7 C4 112.4(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
N1 Cu1 O1 C1 11.4(2) . . . . ?
N1 Cu1 O1 C1 -168.6(2) 3_565 . . . ?
O1 Cu1 O1 C1 -78(18) 3_565 . . . ?
O4 Cu1 O1 C1 -70.4(2) 3_565 . . . ?
O4 Cu1 O1 C1 109.6(2) . . . . ?
N1 Cu1 O4 N2 16.9(2) . . . . ?
N1 Cu1 O4 N2 -163.1(2) 3_565 . . . ?
O1 Cu1 O4 N2 113.5(2) 3_565 . . . ?
O1 Cu1 O4 N2 -66.5(2) . . . . ?
O4 Cu1 O4 N2 -83(6) 3_565 . . . ?
N1 Cu1 N1 C2 13(69) 3_565 . . . ?
O1 Cu1 N1 C2 174.6(2) 3_565 . . . ?
O1 Cu1 N1 C2 -5.4(2) . . . . ?
O4 Cu1 N1 C2 83.5(2) 3_565 . . . ?
O4 Cu1 N1 C2 -96.5(2) . . . . ?
N1 Cu1 N1 C6 -167(69) 3_565 . . . ?
O1 Cu1 N1 C6 -5.7(3) 3_565 . . . ?
O1 Cu1 N1 C6 174.3(3) . . . . ?
O4 Cu1 N1 C6 -96.8(3) 3_565 . . . ?
O4 Cu1 N1 C6 83.2(3) . . . . ?
Cu1 O4 N2 O6 167.6(3) . . . . ?
Cu1 O4 N2 O5 -13.7(5) . . . . ?
Cu1 O1 C1 C2 -14.5(3) . . . . ?
C6 N1 C2 C3 0.4(4) . . . . ?
Cu1 N1 C2 C3 -179.8(2) . . . . ?
C6 N1 C2 C1 178.8(3) . . . . ?
Cu1 N1 C2 C1 -1.4(3) . . . . ?
O1 C1 C2 N1 10.5(4) . . . . ?
O1 C1 C2 C3 -171.2(3) . . . . ?
N1 C2 C3 C4 1.1(4) . . . . ?
C1 C2 C3 C4 -177.1(3) . . . . ?
C2 C3 C4 C5 -2.0(5) . . . . ?
C2 C3 C4 C7 175.1(3) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C7 C4 C5 C6 -175.7(3) . . . . ?
C2 N1 C6 C5 -1.2(5) . . . . ?
Cu1 N1 C6 C5 179.1(2) . . . . ?
C4 C5 C6 N1 0.4(5) . . . . ?
C3 C4 C7 O2 4.5(6) . . . . ?
C5 C4 C7 O2 -178.5(4) . . . . ?
C3 C4 C7 O3 -168.5(3) . . . . ?
C5 C4 C7 O3 8.5(5) . . . . ?

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
O1W H2W O5 0.892(19) 1.85(2) 2.724(4) 164(4) .
O1W H2W N2 0.892(19) 2.70(3) 3.470(4) 146(3) .
O1W H1W O2 0.831(19) 1.94(2) 2.773(3) 176(4) 3_655
O1 H1O O1W 0.837(19) 1.71(2) 2.546(3) 174(4) 3_665
O3 H3O O4 0.88(2) 1.73(2) 2.594(4) 170(5) 1_545
O3 H3O N2 0.88(2) 2.46(3) 3.305(4) 161(5) 1_545
O3 H3O O6 0.88(2) 2.53(4) 3.189(5) 133(5) 1_545

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.86
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         2.473
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.111
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1013144'
_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 Cu N2 O8, 2(N O3)'
_chemical_formula_sum            'C14 H18 Cu N4 O14'
_chemical_formula_weight         529.86

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'
Cu Cu 0.3201 1.2651 '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           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.256(6)
_cell_length_b                   7.425(6)
_cell_length_c                   9.897(8)
_cell_angle_alpha                89.716(17)
_cell_angle_beta                 77.622(17)
_cell_angle_gamma                86.150(19)
_cell_volume                     519.6(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7196
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      28.3

_exptl_crystal_description       platelet
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             271
_exptl_absorpt_coefficient_mu    1.133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7275
_exptl_absorpt_correction_T_max  0.9455
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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 ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12033
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         26.36
_reflns_number_total             2115
_reflns_number_gt                1954
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0467P)²+0.2330P] 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         2115
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_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 0.5000 0.0000 0.03134(15) Uani 1 2 d S . .
O1 O 0.4072(3) 0.2517(2) -0.01658(17) 0.0396(4) Uani 1 1 d . . .
H1 H 0.328(4) 0.245(4) -0.056(3) 0.047(9) Uiso 1 1 d . . .
O2 O 0.3182(3) 0.8498(3) 0.5081(2) 0.0559(5) Uani 1 1 d . . .
H2 H 0.305(5) 0.915(5) 0.578(4) 0.065(10) Uiso 1 1 d . . .
O3 O 0.2153(3) 0.6455(3) 0.66875(18) 0.0645(6) Uani 1 1 d . . .
O1w O 0.2351(3) 0.6465(4) -0.0503(2) 0.0690(8) Uani 1 1 d . . .
H1W H 0.155(5) 0.683(5) 0.000(4) 0.060(10) Uiso 1 1 d . . .
H2W H 0.224(6) 0.650(6) -0.126(5) 0.087(13) Uiso 1 1 d . . .
O5 O -0.0039(3) 0.0977(3) 0.7258(2) 0.0655(6) Uani 1 1 d . . .
O6 O 0.2952(3) 0.0750(3) 0.7217(2) 0.0552(5) Uani 1 1 d . . .
O4 O 0.1043(3) 0.2103(4) 0.8893(2) 0.0812(8) Uani 1 1 d . . .
N1 N 0.3805(2) 0.4690(2) 0.19786(17) 0.0288(4) Uani 1 1 d . . .
N2 N 0.1292(3) 0.1244(3) 0.7784(2) 0.0406(5) Uani 1 1 d . . .
C1 C 0.3610(4) 0.1650(3) 0.1142(3) 0.0466(6) Uani 1 1 d . . .
H1A H 0.4645 0.0798 0.1241 0.056 Uiso 1 1 calc R . .
H1B H 0.2493 0.0985 0.1187 0.056 Uiso 1 1 calc R . .
C2 C 0.3248(3) 0.3011(3) 0.2301(2) 0.0336(5) Uani 1 1 d . . .
C3 C 0.2443(4) 0.2529(4) 0.3638(3) 0.0447(6) Uani 1 1 d . . .
H3 H 0.2035 0.1377 0.3833 0.054 Uiso 1 1 calc R . .
C4 C 0.2261(4) 0.3801(4) 0.4672(2) 0.0444(6) Uani 1 1 d . . .
H4 H 0.1743 0.3508 0.5583 0.053 Uiso 1 1 calc R . .
C5 C 0.2853(3) 0.5532(3) 0.4354(2) 0.0337(5) Uani 1 1 d . . .
C6 C 0.3610(3) 0.5938(3) 0.2988(2) 0.0310(4) Uani 1 1 d . . .
H6 H 0.3989 0.7094 0.2765 0.037 Uiso 1 1 calc R . .
C7 C 0.2685(3) 0.6868(4) 0.5497(2) 0.0407(5) Uani 1 1 d . . .


_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 N1 1.983(2) . ?
Cu1 N1 1.983(2) 2_665 ?
Cu1 O1 2.024(2) 2_665 ?
Cu1 O1 2.024(2) . ?
Cu1 O1w 2.291(3) . ?
Cu1 O1w 2.291(3) 2_665 ?
O1 C1 1.427(3) . ?
O1 H1 0.76(3) . ?
O2 C7 1.324(4) . ?
O2 H2 0.83(4) . ?
O3 C7 1.203(3) . ?
O1w H1W 0.72(4) . ?
O1w H2W 0.77(5) . ?
O5 N2 1.218(3) . ?
O6 N2 1.247(3) . ?
O4 N2 1.245(3) . ?
N1 C6 1.344(3) . ?
N1 C2 1.352(3) . ?
C1 C2 1.501(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.383(3) . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 C7 1.488(3) . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 180.00(10) . 2_665 ?
N1 Cu1 O1 97.65(7) . 2_665 ?
N1 Cu1 O1 82.35(7) 2_665 2_665 ?
N1 Cu1 O1 82.35(7) . . ?
N1 Cu1 O1 97.65(7) 2_665 . ?
O1 Cu1 O1 180.0 2_665 . ?
N1 Cu1 O1w 93.72(9) . . ?
N1 Cu1 O1w 86.28(9) 2_665 . ?
O1 Cu1 O1w 86.31(11) 2_665 . ?
O1 Cu1 O1w 93.69(11) . . ?
N1 Cu1 O1w 86.28(9) . 2_665 ?
N1 Cu1 O1w 93.72(9) 2_665 2_665 ?
O1 Cu1 O1w 93.69(11) 2_665 2_665 ?
O1 Cu1 O1w 86.31(11) . 2_665 ?
O1w Cu1 O1w 180.00(13) . 2_665 ?
C1 O1 Cu1 112.05(14) . . ?
C1 O1 H1 111(2) . . ?
Cu1 O1 H1 117(2) . . ?
C7 O2 H2 108(2) . . ?
Cu1 O1w H1W 125(3) . . ?
Cu1 O1w H2W 119(3) . . ?
H1W O1w H2W 115(4) . . ?
C6 N1 C2 119.45(19) . . ?
C6 N1 Cu1 126.25(16) . . ?
C2 N1 Cu1 114.20(14) . . ?
O5 N2 O4 120.6(2) . . ?
O5 N2 O6 122.1(2) . . ?
O4 N2 O6 117.2(2) . . ?
O1 C1 C2 110.8(2) . . ?
O1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
N1 C2 C3 122.3(2) . . ?
N1 C2 C1 116.82(19) . . ?
C3 C2 C1 120.8(2) . . ?
C4 C3 C2 118.2(2) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 C7 122.3(2) . . ?
C4 C5 C7 118.9(2) . . ?
N1 C6 C5 121.2(2) . . ?
N1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O3 C7 O2 124.5(2) . . ?
O3 C7 C5 121.3(3) . . ?
O2 C7 C5 114.2(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
O1 H1 O4 0.76(3) 1.85(3) 2.601(3) 166(3) 1_554
O2 H2 O6 0.83(4) 1.84(4) 2.672(3) 174(3) 1_565
O1w H1W O4 0.72(4) 2.07(4) 2.778(3) 168(4) 2_566
O1w H2W O3 0.77(5) 2.04(5) 2.815(4) 175(4) 1_554

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.080
####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1013145'
_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C14 H12 Cu N2 O6, 2(C1.50 H3.50 N0.50 O0.50), 2(H O0.50)'
_chemical_formula_sum            'C17 H21 Cu N3 O8'
_chemical_formula_weight         458.91

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   7.451(2)
_cell_length_b                   10.916(3)
_cell_length_c                   12.454(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.955(6)
_cell_angle_gamma                90.00
_cell_volume                     968.9(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2190
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      24.36

_exptl_crystal_description       platelet
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             474
_exptl_absorpt_coefficient_mu    1.178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8913
_exptl_absorpt_correction_T_max  0.9327
_exptl_absorpt_process_details   'SADABS, (Sheldrick 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15551
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_sigmaI/netI    0.0711
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2231
_reflns_number_gt                1435
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.1374P)²+0.4715P] 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         2231
_refine_ls_number_parameters     163
_refine_ls_number_restraints     46
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2294
_refine_ls_wR_factor_gt          0.1907
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.5000 1.0000 0.0281(3) Uani 1 2 d S . .
O3 O -0.4936(6) 0.2230(5) 0.6756(4) 0.0548(13) Uani 1 1 d . . .
O2 O -0.3284(6) 0.1316(4) 0.5761(3) 0.0410(10) Uani 1 1 d . . .
O1 O 0.2609(5) 0.5803(4) 0.9495(3) 0.0394(10) Uani 1 1 d D . .
H1 H 0.176(7) 0.626(5) 0.911(5) 0.047 Uiso 1 1 d D . .
N1 N -0.0186(6) 0.4167(4) 0.8535(3) 0.0304(10) Uani 1 1 d . . .
C1 C 0.3022(8) 0.4890(6) 0.8807(5) 0.0413(14) Uani 1 1 d . . .
H1A H 0.3943 0.4335 0.9270 0.050 Uiso 1 1 calc R . .
H1B H 0.3578 0.5272 0.8277 0.050 Uiso 1 1 calc R . .
C2 C 0.1323(7) 0.4160(5) 0.8163(5) 0.0340(12) Uani 1 1 d . . .
C3 C 0.1335(8) 0.3486(6) 0.7218(5) 0.0423(14) Uani 1 1 d . . .
H3A H 0.2390 0.3491 0.6962 0.051 Uiso 1 1 calc R . .
C4 C -0.0199(8) 0.2820(6) 0.6668(5) 0.0425(14) Uani 1 1 d . . .
H4A H -0.0195 0.2369 0.6036 0.051 Uiso 1 1 calc R . .
C5 C -0.1782(7) 0.2814(5) 0.7053(5) 0.0334(12) Uani 1 1 d . . .
C6 C -0.1710(7) 0.3521(5) 0.7983(5) 0.0330(12) Uani 1 1 d . . .
H6A H -0.2764 0.3553 0.8238 0.040 Uiso 1 1 calc R . .
C7 C -0.3491(8) 0.2079(5) 0.6476(5) 0.0367(13) Uani 1 1 d . . .
O4 O 0.360(2) 0.5813(16) 0.6204(13) 0.117(4) Uani 0.50 1 d PDU A -1
N2 N 0.441(3) 0.480(2) 0.4866(19) 0.117(4) Uani 0.50 1 d PDU A -1
C8 C 0.577(4) 0.439(4) 0.433(2) 0.128(11) Uani 0.50 1 d PDU A -1
H8A H 0.5162 0.3909 0.3683 0.192 Uiso 0.50 1 calc PR A -1
H8B H 0.6710 0.3906 0.4847 0.192 Uiso 0.50 1 calc PR A -1
H8C H 0.6360 0.5090 0.4102 0.192 Uiso 0.50 1 calc PR A -1
C9 C 0.257(3) 0.425(2) 0.4473(16) 0.105(6) Uani 0.50 1 d PDU . -1
H9A H 0.2482 0.3792 0.3800 0.158 Uiso 0.50 1 calc PR . -1
H9B H 0.1634 0.4879 0.4317 0.158 Uiso 0.50 1 calc PR . -1
H9C H 0.2387 0.3711 0.5039 0.158 Uiso 0.50 1 calc PR . -1
C10 C 0.487(4) 0.548(3) 0.576(3) 0.110(8) Uani 0.50 1 d PDU A -1
H10 H 0.6110 0.5726 0.6072 0.132 Uiso 0.50 1 calc PR A -1
O5 O -0.017(4) 0.653(3) 0.594(2) 0.186(10) Uani 0.50 1 d PD . .
H5A H -0.10(3) 0.62(3) 0.62(4) 0.223 Uiso 0.50 1 d PD . .
H5B H 0.08(2) 0.61(3) 0.61(3) 0.223 Uiso 0.50 1 d PD . .


_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 O2 1.972(4) 2_456 ?
Cu1 O2 1.972(4) 4_666 ?
Cu1 N1 2.006(4) 3_567 ?
Cu1 N1 2.006(4) . ?
Cu1 O1 2.378(4) . ?
Cu1 O1 2.378(4) 3_567 ?
O3 C7 1.235(7) . ?
O2 C7 1.262(7) . ?
O2 Cu1 1.972(4) 2_446 ?
O1 C1 1.405(7) . ?
O1 H1 0.84(2) . ?
N1 C2 1.336(7) . ?
N1 C6 1.343(7) . ?
C1 C2 1.513(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.390(8) . ?
C3 C4 1.359(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.396(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.380(7) . ?
C5 C7 1.499(8) . ?
C6 H6A 0.9300 . ?
O4 C10 1.279(17) . ?
N2 C10 1.297(17) . ?
N2 C8 1.439(17) . ?
N2 C9 1.445(16) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O5 1.92(4) 3_566 ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9300 . ?
O5 C9 1.92(4) 3_566 ?
O5 H5A 0.841(15) . ?
O5 H5B 0.841(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.00(16) 2_456 4_666 ?
O2 Cu1 N1 88.27(17) 2_456 3_567 ?
O2 Cu1 N1 91.73(17) 4_666 3_567 ?
O2 Cu1 N1 91.73(17) 2_456 . ?
O2 Cu1 N1 88.27(17) 4_666 . ?
N1 Cu1 N1 179.999(1) 3_567 . ?
O2 Cu1 O1 94.00(16) 2_456 . ?
O2 Cu1 O1 86.00(16) 4_666 . ?
N1 Cu1 O1 103.21(16) 3_567 . ?
N1 Cu1 O1 76.79(16) . . ?
O2 Cu1 O1 86.00(16) 2_456 3_567 ?
O2 Cu1 O1 94.00(16) 4_666 3_567 ?
N1 Cu1 O1 76.79(16) 3_567 3_567 ?
N1 Cu1 O1 103.21(16) . 3_567 ?
O1 Cu1 O1 180.0 . 3_567 ?
C7 O2 Cu1 128.6(4) . 2_446 ?
C1 O1 Cu1 104.0(3) . . ?
C1 O1 H1 109(5) . . ?
Cu1 O1 H1 80(5) . . ?
C2 N1 C6 119.4(5) . . ?
C2 N1 Cu1 118.5(3) . . ?
C6 N1 Cu1 121.8(4) . . ?
O1 C1 C2 113.5(4) . . ?
O1 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
O1 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
N1 C2 C3 120.8(5) . . ?
N1 C2 C1 118.1(5) . . ?
C3 C2 C1 121.1(5) . . ?
C4 C3 C2 119.8(5) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 117.1(5) . . ?
C6 C5 C7 121.4(5) . . ?
C4 C5 C7 121.5(5) . . ?
N1 C6 C5 122.9(5) . . ?
N1 C6 H6A 118.5 . . ?
C5 C6 H6A 118.5 . . ?
O3 C7 O2 125.7(5) . . ?
O3 C7 C5 118.8(5) . . ?
O2 C7 C5 115.4(5) . . ?
C10 N2 C8 122(2) . . ?
C10 N2 C9 121.1(18) . . ?
C8 N2 C9 116.1(18) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 O5 175.7(19) . 3_566 ?
N2 C9 H9A 109.5 . . ?
O5 C9 H9A 73.3 3_566 . ?
N2 C9 H9B 109.5 . . ?
O5 C9 H9B 72.0 3_566 . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
O5 C9 H9C 66.3 3_566 . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 N2 119(2) . . ?
O4 C10 H10 120.3 . . ?
N2 C10 H10 120.3 . . ?
H5A O5 H5B 110.00 . . ?

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
O2 Cu1 O1 C1 -116.6(4) 2_456 . . . ?
O2 Cu1 O1 C1 63.4(3) 4_666 . . . ?
N1 Cu1 O1 C1 154.3(3) 3_567 . . . ?
N1 Cu1 O1 C1 -25.7(3) . . . . ?
O1 Cu1 O1 C1 37(26) 3_567 . . . ?
O2 Cu1 N1 C2 111.1(4) 2_456 . . . ?
O2 Cu1 N1 C2 -68.9(4) 4_666 . . . ?
N1 Cu1 N1 C2 96(6) 3_567 . . . ?
O1 Cu1 N1 C2 17.4(4) . . . . ?
O1 Cu1 N1 C2 -162.6(4) 3_567 . . . ?
O2 Cu1 N1 C6 -75.5(4) 2_456 . . . ?
O2 Cu1 N1 C6 104.5(4) 4_666 . . . ?
N1 Cu1 N1 C6 -90(6) 3_567 . . . ?
O1 Cu1 N1 C6 -169.2(5) . . . . ?
O1 Cu1 N1 C6 10.8(5) 3_567 . . . ?
Cu1 O1 C1 C2 29.8(5) . . . . ?
C6 N1 C2 C3 -0.5(8) . . . . ?
Cu1 N1 C2 C3 173.1(5) . . . . ?
C6 N1 C2 C1 -179.7(5) . . . . ?
Cu1 N1 C2 C1 -6.1(7) . . . . ?
O1 C1 C2 N1 -19.9(8) . . . . ?
O1 C1 C2 C3 160.9(6) . . . . ?
N1 C2 C3 C4 -0.4(9) . . . . ?
C1 C2 C3 C4 178.8(6) . . . . ?
C2 C3 C4 C5 0.0(10) . . . . ?
C3 C4 C5 C6 1.2(9) . . . . ?
C3 C4 C5 C7 -179.3(6) . . . . ?
C2 N1 C6 C5 1.8(8) . . . . ?
Cu1 N1 C6 C5 -171.5(4) . . . . ?
C4 C5 C6 N1 -2.1(9) . . . . ?
C7 C5 C6 N1 178.3(5) . . . . ?
Cu1 O2 C7 O3 -8.3(9) 2_446 . . . ?
Cu1 O2 C7 C5 169.1(4) 2_446 . . . ?
C6 C5 C7 O3 9.0(9) . . . . ?
C4 C5 C7 O3 -170.5(6) . . . . ?
C6 C5 C7 O2 -168.6(5) . . . . ?
C4 C5 C7 O2 11.9(8) . . . . ?
C10 N2 C9 O5 -51(29) . . . 3_566 ?
C8 N2 C9 O5 119(27) . . . 3_566 ?
C8 N2 C10 O4 -180(2) . . . . ?
C9 N2 C10 O4 -10(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.84(2) 1.81(2) 2.648(6) 179(7) 2_456
O1 H1 O2 0.84(2) 2.64(6) 3.194(5) 125(5) 2_456
O5 H5B O4 0.841(15) 2.05(12) 2.84(3) 152.00 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.705
_refine_diff_density_min         -1.186
_refine_diff_density_rms         0.149
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1013146'

_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 Cl Cu N2 O6, H2 O'
_chemical_formula_sum            'C14 H15 Cl Cu N2 O7'
_chemical_formula_weight         422.27

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'
Cl Cl 0.1484 0.1585 '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           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7474(7)
_cell_length_b                   9.0283(8)
_cell_length_c                   11.6264(10)
_cell_angle_alpha                81.603(2)
_cell_angle_beta                 80.274(2)
_cell_angle_gamma                81.512(2)
_cell_volume                     786.61(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5253
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      28.17

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             430
_exptl_absorpt_coefficient_mu    1.601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5669
_exptl_absorpt_correction_T_max  0.8563
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           ?

_diffrn_ambient_temperature      153(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 ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11032
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2852
_reflns_number_gt                2564
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0407P)²+0.6132P] 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         2852
_refine_ls_number_parameters     241
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001

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 0.51644(3) 0.50025(3) 0.75175(2) 0.01450(11) Uani 1 1 d . . .
Cl1 Cl 0.78018(7) 0.58504(7) 0.70352(5) 0.01820(15) Uani 1 1 d . . .
O1 O 0.2921(2) 0.5284(2) 0.87557(15) 0.0223(4) Uani 1 1 d D . .
H1O H 0.203(3) 0.583(3) 0.868(3) 0.027 Uiso 1 1 d D . .
O1W O 0.0281(2) 0.7354(2) 0.83902(16) 0.0241(4) Uani 1 1 d D . .
H2W H 0.055(4) 0.821(2) 0.831(3) 0.029 Uiso 1 1 d D . .
H1W H -0.023(4) 0.726(3) 0.786(2) 0.029 Uiso 1 1 d D . .
O2 O 0.8420(2) -0.0154(2) 1.18166(15) 0.0246(4) Uani 1 1 d . . .
O3 O 0.5649(2) -0.0716(2) 1.21941(15) 0.0229(4) Uani 1 1 d . . .
O4 O 0.4178(2) 0.34407(19) 0.66852(15) 0.0169(4) Uani 1 1 d D . .
H4O H 0.415(4) 0.261(2) 0.695(2) 0.020 Uiso 1 1 d D . .
O5 O -0.0183(2) 0.8414(2) 0.35500(15) 0.0208(4) Uani 1 1 d D . .
H5O H -0.062(4) 0.893(3) 0.303(2) 0.025 Uiso 1 1 d D . .
O6 O 0.1210(2) 1.0428(2) 0.35404(16) 0.0249(4) Uani 1 1 d . . .
N1 N 0.5755(2) 0.3455(2) 0.88196(16) 0.0143(4) Uani 1 1 d . . .
N2 N 0.4003(2) 0.6369(2) 0.63098(16) 0.0131(4) Uani 1 1 d . . .
C1 C 0.2679(3) 0.4029(3) 0.9623(2) 0.0172(5) Uani 1 1 d . . .
H1A H 0.1855 0.3411 0.9410 0.021 Uiso 1 1 calc R . .
H1B H 0.2176 0.4375 1.0394 0.021 Uiso 1 1 calc R . .
C2 C 0.4455(3) 0.3110(3) 0.96930(19) 0.0141(5) Uani 1 1 d . . .
C3 C 0.4729(3) 0.1962(3) 1.06081(19) 0.0140(5) Uani 1 1 d . . .
H3 H 0.3784 0.1720 1.1210 0.017 Uiso 1 1 calc R . .
C4 C 0.6411(3) 0.1175(3) 1.06239(19) 0.0149(5) Uani 1 1 d . . .
C5 C 0.7736(3) 0.1527(3) 0.9698(2) 0.0183(5) Uani 1 1 d . . .
H5 H 0.8889 0.0989 0.9678 0.022 Uiso 1 1 calc R . .
C6 C 0.7368(3) 0.2650(3) 0.8816(2) 0.0181(5) Uani 1 1 d . . .
H6 H 0.8277 0.2871 0.8182 0.022 Uiso 1 1 calc R . .
C7 C 0.6838(3) -0.0007(3) 1.1633(2) 0.0162(5) Uani 1 1 d . . .
C8 C 0.2658(3) 0.4134(3) 0.6197(2) 0.0157(5) Uani 1 1 d . . .
H8A H 0.1586 0.4018 0.6785 0.019 Uiso 1 1 calc R . .
H8B H 0.2551 0.3650 0.5505 0.019 Uiso 1 1 calc R . .
C9 C 0.2835(3) 0.5776(3) 0.58370(19) 0.0126(5) Uani 1 1 d . . .
C10 C 0.1818(3) 0.6649(3) 0.50564(19) 0.0139(5) Uani 1 1 d . . .
H10 H 0.0996 0.6212 0.4731 0.017 Uiso 1 1 calc R . .
C11 C 0.2005(3) 0.8158(3) 0.47536(19) 0.0133(5) Uani 1 1 d . . .
C12 C 0.3211(3) 0.8772(3) 0.5251(2) 0.0155(5) Uani 1 1 d . . .
H12 H 0.3355 0.9811 0.5064 0.019 Uiso 1 1 calc R . .
C13 C 0.4187(3) 0.7848(3) 0.6017(2) 0.0158(5) Uani 1 1 d . . .
H13 H 0.5018 0.8261 0.6351 0.019 Uiso 1 1 calc R . .
C14 C 0.0976(3) 0.9136(3) 0.3882(2) 0.0164(5) Uani 1 1 d . . .


_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 N1 1.9698(19) . ?
Cu1 N2 1.9739(19) . ?
Cu1 O1 2.0707(17) . ?
Cu1 O4 2.1154(16) . ?
Cu1 Cl1 2.2416(6) . ?
O1 C1 1.415(3) . ?
O1 H1O 0.798(17) . ?
O1W H2W 0.816(18) . ?
O1W H1W 0.806(18) . ?
O2 C7 1.264(3) . ?
O3 C7 1.237(3) . ?
O4 C8 1.416(3) . ?
O4 H4O 0.773(17) . ?
O5 C14 1.321(3) . ?
O5 H5O 0.798(17) . ?
O6 C14 1.206(3) . ?
N1 C2 1.341(3) . ?
N1 C6 1.350(3) . ?
N2 C9 1.343(3) . ?
N2 C13 1.352(3) . ?
C1 C2 1.506(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.393(3) . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(3) . ?
C4 C7 1.513(3) . ?
C5 C6 1.367(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.501(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.384(3) . ?
C10 C11 1.379(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(3) . ?
C11 C14 1.499(3) . ?
C12 C13 1.372(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N2 165.90(8) . . ?
N1 Cu1 O1 78.20(7) . . ?
N2 Cu1 O1 91.32(7) . . ?
N1 Cu1 O4 92.29(7) . . ?
N2 Cu1 O4 78.97(7) . . ?
O1 Cu1 O4 94.25(7) . . ?
N1 Cu1 Cl1 97.68(6) . . ?
N2 Cu1 Cl1 96.41(6) . . ?
O1 Cu1 Cl1 138.59(6) . . ?
O4 Cu1 Cl1 127.16(5) . . ?
C1 O1 Cu1 114.86(14) . . ?
C1 O1 H1O 113(2) . . ?
Cu1 O1 H1O 128(2) . . ?
H2W O1W H1W 109(3) . . ?
C8 O4 Cu1 110.24(14) . . ?
C8 O4 H4O 115(2) . . ?
Cu1 O4 H4O 123(2) . . ?
C14 O5 H5O 109(2) . . ?
C2 N1 C6 119.0(2) . . ?
C2 N1 Cu1 118.08(15) . . ?
C6 N1 Cu1 122.64(16) . . ?
C9 N2 C13 119.25(19) . . ?
C9 N2 Cu1 115.50(15) . . ?
C13 N2 Cu1 124.97(15) . . ?
O1 C1 C2 107.82(18) . . ?
O1 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
O1 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.5 . . ?
N1 C2 C3 121.9(2) . . ?
N1 C2 C1 116.1(2) . . ?
C3 C2 C1 122.0(2) . . ?
C4 C3 C2 118.8(2) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 C7 119.7(2) . . ?
C3 C4 C7 121.7(2) . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N1 C6 C5 122.1(2) . . ?
N1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
O3 C7 O2 126.6(2) . . ?
O3 C7 C4 118.7(2) . . ?
O2 C7 C4 114.6(2) . . ?
O4 C8 C9 108.30(18) . . ?
O4 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
O4 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
N2 C9 C10 121.3(2) . . ?
N2 C9 C8 117.52(19) . . ?
C10 C9 C8 121.1(2) . . ?
C11 C10 C9 119.5(2) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 119.0(2) . . ?
C10 C11 C14 121.4(2) . . ?
C12 C11 C14 119.5(2) . . ?
C13 C12 C11 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
N2 C13 C12 122.1(2) . . ?
N2 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
O6 C14 O5 125.4(2) . . ?
O6 C14 C11 122.6(2) . . ?
O5 C14 C11 112.0(2) . . ?

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
N1 Cu1 O1 C1 -20.38(16) . . . . ?
N2 Cu1 O1 C1 150.12(16) . . . . ?
O4 Cu1 O1 C1 71.08(16) . . . . ?
Cl1 Cu1 O1 C1 -108.64(16) . . . . ?
N1 Cu1 O4 C8 141.25(15) . . . . ?
N2 Cu1 O4 C8 -27.60(14) . . . . ?
O1 Cu1 O4 C8 62.91(14) . . . . ?
Cl1 Cu1 O4 C8 -117.32(13) . . . . ?
N2 Cu1 N1 C2 -29.8(4) . . . . ?
O1 Cu1 N1 C2 12.89(16) . . . . ?
O4 Cu1 N1 C2 -80.97(17) . . . . ?
Cl1 Cu1 N1 C2 151.05(16) . . . . ?
N2 Cu1 N1 C6 144.6(3) . . . . ?
O1 Cu1 N1 C6 -172.7(2) . . . . ?
O4 Cu1 N1 C6 93.43(19) . . . . ?
Cl1 Cu1 N1 C6 -34.54(19) . . . . ?
N1 Cu1 N2 C9 -35.0(4) . . . . ?
O1 Cu1 N2 C9 -76.53(16) . . . . ?
O4 Cu1 N2 C9 17.54(15) . . . . ?
Cl1 Cu1 N2 C9 144.22(15) . . . . ?
N1 Cu1 N2 C13 139.0(3) . . . . ?
O1 Cu1 N2 C13 97.43(19) . . . . ?
O4 Cu1 N2 C13 -168.50(19) . . . . ?
Cl1 Cu1 N2 C13 -41.82(18) . . . . ?
Cu1 O1 C1 C2 22.9(2) . . . . ?
C6 N1 C2 C3 1.1(3) . . . . ?
Cu1 N1 C2 C3 175.71(17) . . . . ?
C6 N1 C2 C1 -178.5(2) . . . . ?
Cu1 N1 C2 C1 -3.9(3) . . . . ?
O1 C1 C2 N1 -12.7(3) . . . . ?
O1 C1 C2 C3 167.7(2) . . . . ?
N1 C2 C3 C4 1.4(3) . . . . ?
C1 C2 C3 C4 -179.1(2) . . . . ?
C2 C3 C4 C5 -2.6(3) . . . . ?
C2 C3 C4 C7 175.5(2) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C7 C4 C5 C6 -176.7(2) . . . . ?
C2 N1 C6 C5 -2.3(3) . . . . ?
Cu1 N1 C6 C5 -176.64(18) . . . . ?
C4 C5 C6 N1 1.0(4) . . . . ?
C5 C4 C7 O3 -153.0(2) . . . . ?
C3 C4 C7 O3 28.9(3) . . . . ?
C5 C4 C7 O2 27.5(3) . . . . ?
C3 C4 C7 O2 -150.7(2) . . . . ?
Cu1 O4 C8 C9 31.0(2) . . . . ?
C13 N2 C9 C10 0.0(3) . . . . ?
Cu1 N2 C9 C10 174.35(17) . . . . ?
C13 N2 C9 C8 -179.3(2) . . . . ?
Cu1 N2 C9 C8 -5.0(3) . . . . ?
O4 C8 C9 N2 -18.5(3) . . . . ?
O4 C8 C9 C10 162.2(2) . . . . ?
N2 C9 C10 C11 0.1(3) . . . . ?
C8 C9 C10 C11 179.4(2) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C9 C10 C11 C14 177.9(2) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C14 C11 C12 C13 -177.7(2) . . . . ?
C9 N2 C13 C12 0.2(3) . . . . ?
Cu1 N2 C13 C12 -173.53(17) . . . . ?
C11 C12 C13 N2 -0.6(3) . . . . ?
C10 C11 C14 O6 -174.5(2) . . . . ?
C12 C11 C14 O6 3.9(3) . . . . ?
C10 C11 C14 O5 5.5(3) . . . . ?
C12 C11 C14 O5 -176.1(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
O1 H1O O1W 0.798(17) 1.819(19) 2.606(2) 169(3) .
O1W H2W O2 0.816(18) 2.012(18) 2.820(3) 171(3) 2_667
O1W H1W Cl1 0.806(18) 2.51(2) 3.2297(19) 150(3) 1_455
O1W H1W O6 0.806(18) 2.56(3) 3.044(2) 120(3) 2_576
O4 H4O O3 0.773(17) 1.846(18) 2.607(2) 168(3) 2_657
O5 H5O O2 0.798(17) 1.750(18) 2.543(2) 173(3) 1_464

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1013147'

_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 Cu N2 O8'
_chemical_formula_sum            'C14 H16 Cu N2 O8'
_chemical_formula_weight         403.83

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'
Cu Cu 0.3201 1.2651 '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           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   6.9918(5)
_cell_length_b                   13.1602(9)
_cell_length_c                   17.1546(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1578.45(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4952
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.28

_exptl_crystal_description       prism
_exptl_crystal_colour            light-blue
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             828
_exptl_absorpt_coefficient_mu    1.432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5846
_exptl_absorpt_correction_T_max  0.8941
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           ?

_diffrn_ambient_temperature      100(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 ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15498
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1805
_reflns_number_gt                1501
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0308P)²+1.2118P] 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         1805
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.5000 0.0000 0.01012(10) Uani 1 2 d S . .
O1 O 0.60340(19) 0.33383(8) -0.00724(6) 0.0151(3) Uani 1 1 d . . .
H1O H 0.588(3) 0.3008(15) -0.0429(12) 0.018 Uiso 1 1 d . . .
O1W O 0.23462(18) 0.45118(9) -0.02240(7) 0.0142(2) Uani 1 1 d . . .
H1W H 0.176(3) 0.4373(15) 0.0142(12) 0.017 Uiso 1 1 d . . .
H2W H 0.174(3) 0.4941(14) -0.0469(12) 0.017 Uiso 1 1 d . . .
O2 O 0.5482(2) 0.26190(9) 0.36051(7) 0.0283(3) Uani 1 1 d . . .
O3 O 0.50520(17) 0.42154(9) 0.40067(6) 0.0176(3) Uani 1 1 d . . .
N1 N 0.48763(19) 0.45184(10) 0.11073(7) 0.0113(3) Uani 1 1 d . . .
C1 C 0.5548(3) 0.28041(11) 0.06158(9) 0.0154(3) Uani 1 1 d . . .
H1A H 0.6593 0.2329 0.0754 0.018 Uiso 1 1 calc R . .
H1B H 0.4373 0.2401 0.0526 0.018 Uiso 1 1 calc R . .
C2 C 0.5225(2) 0.35375(11) 0.12755(9) 0.0110(3) Uani 1 1 d . . .
C3 C 0.5288(2) 0.32004(11) 0.20463(9) 0.0124(3) Uani 1 1 d . . .
H3 H 0.5523 0.2504 0.2156 0.015 Uiso 1 1 calc R . .
C4 C 0.5009(2) 0.38795(11) 0.26504(8) 0.0113(3) Uani 1 1 d . . .
C5 C 0.4648(2) 0.48921(11) 0.24663(10) 0.0136(3) Uani 1 1 d . . .
H5 H 0.4445 0.5377 0.2868 0.016 Uiso 1 1 calc R . .
C6 C 0.4589(3) 0.51813(12) 0.16952(10) 0.0146(3) Uani 1 1 d . . .
H6 H 0.4337 0.5873 0.1573 0.018 Uiso 1 1 calc R . .
C7 C 0.5183(2) 0.35351(12) 0.34931(9) 0.0133(3) Uani 1 1 d . . .


_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 O1W 2.0008(13) . ?
Cu1 O1W 2.0008(13) 5_665 ?
Cu1 N1 2.0043(13) . ?
Cu1 N1 2.0043(13) 5_665 ?
Cu1 O1 2.3065(11) 5_665 ?
Cu1 O1 2.3066(11) . ?
O1 C1 1.4154(18) . ?
O1 H1O 0.76(2) . ?
O1W H1W 0.77(2) . ?
O1W H2W 0.82(2) . ?
O2 C7 1.239(2) . ?
O3 C7 1.2595(19) . ?
N1 C2 1.3450(19) . ?
N1 C6 1.349(2) . ?
C1 C2 1.505(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.395(2) . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(2) . ?
C4 C7 1.520(2) . ?
C5 C6 1.377(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?

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
O1W Cu1 O1W 180.00(6) . 5_665 ?
O1W Cu1 N1 92.32(5) . . ?
O1W Cu1 N1 87.68(5) 5_665 . ?
O1W Cu1 N1 87.68(5) . 5_665 ?
O1W Cu1 N1 92.32(5) 5_665 5_665 ?
N1 Cu1 N1 180.0 . 5_665 ?
O1W Cu1 O1 91.38(5) . 5_665 ?
O1W Cu1 O1 88.62(5) 5_665 5_665 ?
N1 Cu1 O1 103.61(5) . 5_665 ?
N1 Cu1 O1 76.40(5) 5_665 5_665 ?
O1W Cu1 O1 88.62(5) . . ?
O1W Cu1 O1 91.38(5) 5_665 . ?
N1 Cu1 O1 76.39(5) . . ?
N1 Cu1 O1 103.60(5) 5_665 . ?
O1 Cu1 O1 180.0 5_665 . ?
C1 O1 Cu1 110.54(9) . . ?
C1 O1 H1O 110.6(15) . . ?
Cu1 O1 H1O 122.8(15) . . ?
Cu1 O1W H1W 114.5(15) . . ?
Cu1 O1W H2W 110.9(14) . . ?
H1W O1W H2W 108(2) . . ?
C2 N1 C6 119.17(13) . . ?
C2 N1 Cu1 119.94(10) . . ?
C6 N1 Cu1 120.71(11) . . ?
O1 C1 C2 110.17(12) . . ?
O1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
O1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
N1 C2 C3 120.94(14) . . ?
N1 C2 C1 118.78(13) . . ?
C3 C2 C1 120.27(14) . . ?
C4 C3 C2 120.03(14) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 118.30(14) . . ?
C3 C4 C7 120.60(14) . . ?
C5 C4 C7 121.04(14) . . ?
C6 C5 C4 119.20(14) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
N1 C6 C5 122.35(14) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
O2 C7 O3 126.56(15) . . ?
O2 C7 C4 116.83(14) . . ?
O3 C7 C4 116.59(14) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1013148'
_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 Cl Cu N2 O6'
_chemical_formula_sum            'C14 H13 Cl Cu N2 O6'
_chemical_formula_weight         404.25

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'
Cl Cl 0.1484 0.1585 '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           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5935(3)
_cell_length_b                   7.7855(4)
_cell_length_c                   14.6720(7)
_cell_angle_alpha                83.0350(10)
_cell_angle_beta                 86.3830(10)
_cell_angle_gamma                61.4210(10)
_cell_volume                     756.08(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9174
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      30.45

_exptl_crystal_description       platelet
_exptl_crystal_colour            light-blue
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             410
_exptl_absorpt_coefficient_mu    1.656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7892
_exptl_absorpt_correction_T_max  0.9367
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            33421
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0120
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         30.50
_reflns_number_total             4605
_reflns_number_gt                4255
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0320P)²+0.3348P] 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         4605
_refine_ls_number_parameters     229
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0647
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
Cu1 Cu 0.29063(3) 0.36729(2) 0.259735(10) 0.02672(5) Uani 1 1 d . . .
Cl1 Cl 0.16847(6) 0.15880(6) 0.26147(2) 0.03861(9) Uani 1 1 d . . .
O1 O 0.62475(17) 0.24973(17) 0.25221(7) 0.0339(2) Uani 1 1 d D . .
H21 H 0.676(3) 0.132(2) 0.2555(14) 0.039(5) Uiso 1 1 d D . .
O2 O 0.23354(18) 0.13958(17) 0.70180(7) 0.0368(2) Uani 1 1 d . . .
O3 O -0.00586(17) 0.24379(18) 0.59822(7) 0.0383(2) Uani 1 1 d . . .
O4 O 0.24750(17) 0.64664(16) 0.26159(7) 0.0324(2) Uani 1 1 d D . .
H22 H 0.165(3) 0.697(3) 0.3005(14) 0.061(7) Uiso 1 1 d D . .
O5 O 0.2824(2) 0.10535(19) -0.07366(8) 0.0488(3) Uani 1 1 d . . .
O6 O 0.2993(3) 0.3247(2) -0.18134(8) 0.0545(4) Uani 1 1 d D . .
H23 H 0.292(5) 0.254(4) -0.2150(18) 0.092(10) Uiso 1 1 d D . .
N1 N 0.36179(17) 0.30687(17) 0.39207(7) 0.0258(2) Uani 1 1 d . . .
N2 N 0.25522(18) 0.45327(17) 0.12677(7) 0.0266(2) Uani 1 1 d . . .
C1 C 0.6714(2) 0.2992(3) 0.33446(11) 0.0366(3) Uani 1 1 d . . .
H1A H 0.6506 0.4331 0.3251 0.044 Uiso 1 1 calc R . .
H1B H 0.8116 0.2127 0.3492 0.044 Uiso 1 1 calc R . .
C2 C 0.5429(2) 0.2807(2) 0.41342(9) 0.0279(2) Uani 1 1 d . . .
C3 C 0.6085(2) 0.2348(2) 0.50325(10) 0.0344(3) Uani 1 1 d . . .
H3 H 0.7334 0.2195 0.5171 0.041 Uiso 1 1 calc R . .
C4 C 0.4868(2) 0.2121(2) 0.57223(9) 0.0325(3) Uani 1 1 d . . .
H4 H 0.5297 0.1795 0.6329 0.039 Uiso 1 1 calc R . .
C5 C 0.2995(2) 0.23832(19) 0.55017(8) 0.0256(2) Uani 1 1 d . . .
C6 C 0.2423(2) 0.2875(2) 0.45894(8) 0.0264(2) Uani 1 1 d . . .
H6 H 0.1163 0.3079 0.4436 0.032 Uiso 1 1 calc R . .
C7 C 0.1641(2) 0.20601(19) 0.62173(8) 0.0278(2) Uani 1 1 d . . .
C8 C 0.1947(3) 0.7631(2) 0.17530(9) 0.0337(3) Uani 1 1 d . . .
H8A H 0.2769 0.8278 0.1631 0.040 Uiso 1 1 calc R . .
H8B H 0.0554 0.8637 0.1768 0.040 Uiso 1 1 calc R . .
C9 C 0.2250(2) 0.63626(19) 0.10060(9) 0.0267(2) Uani 1 1 d . . .
C10 C 0.2180(2) 0.7060(2) 0.00854(10) 0.0336(3) Uani 1 1 d . . .
H10 H 0.2000 0.8324 -0.0085 0.040 Uiso 1 1 calc R . .
C11 C 0.2380(2) 0.5854(2) -0.05740(9) 0.0333(3) Uani 1 1 d . . .
H11 H 0.2321 0.6299 -0.1195 0.040 Uiso 1 1 calc R . .
C12 C 0.2670(2) 0.3965(2) -0.02976(8) 0.0276(2) Uani 1 1 d . . .
C13 C 0.2758(2) 0.3352(2) 0.06282(9) 0.0283(2) Uani 1 1 d . . .
H13 H 0.2965 0.2084 0.0815 0.034 Uiso 1 1 calc R . .
C14 C 0.2836(2) 0.2582(2) -0.09612(9) 0.0321(3) Uani 1 1 d . . .


_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 N2 1.9758(11) . ?
Cu1 N1 1.9876(11) . ?
Cu1 O4 2.0420(11) . ?
Cu1 Cl1 2.2188(4) . ?
Cu1 O1 2.2482(11) . ?
O1 C1 1.4238(19) . ?
O1 H21 0.803(14) . ?
O2 C7 1.2631(16) . ?
O3 C7 1.2408(18) . ?
O4 C8 1.4225(17) . ?
O4 H22 0.803(16) . ?
O5 C14 1.2001(19) . ?
O6 C14 1.3148(18) . ?
O6 H23 0.805(18) . ?
N1 C6 1.3385(16) . ?
N1 C2 1.3420(17) . ?
N2 C9 1.3400(17) . ?
N2 C13 1.3431(17) . ?
C1 C2 1.5057(19) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.3825(19) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3846(17) . ?
C5 C7 1.5067(18) . ?
C6 H6 0.9300 . ?
C8 C9 1.4973(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.3876(18) . ?
C10 C11 1.381(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.3788(17) . ?
C12 C14 1.4938(19) . ?
C13 H13 0.9300 . ?

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
N2 Cu1 N1 168.26(5) . . ?
N2 Cu1 O4 80.96(4) . . ?
N1 Cu1 O4 90.57(4) . . ?
N2 Cu1 Cl1 96.22(3) . . ?
N1 Cu1 Cl1 95.15(3) . . ?
O4 Cu1 Cl1 150.34(4) . . ?
N2 Cu1 O1 93.26(4) . . ?
N1 Cu1 O1 78.67(4) . . ?
O4 Cu1 O1 90.84(4) . . ?
Cl1 Cu1 O1 118.83(3) . . ?
C1 O1 Cu1 104.05(8) . . ?
C1 O1 H21 107.4(14) . . ?
Cu1 O1 H21 107.8(14) . . ?
C8 O4 Cu1 114.49(8) . . ?
C8 O4 H22 111.7(18) . . ?
Cu1 O4 H22 107.9(18) . . ?
C14 O6 H23 108(2) . . ?
C6 N1 C2 119.45(11) . . ?
C6 N1 Cu1 123.84(9) . . ?
C2 N1 Cu1 116.69(9) . . ?
C9 N2 C13 119.56(11) . . ?
C9 N2 Cu1 116.33(9) . . ?
C13 N2 Cu1 123.88(9) . . ?
O1 C1 C2 111.25(12) . . ?
O1 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
N1 C2 C3 121.35(12) . . ?
N1 C2 C1 116.53(12) . . ?
C3 C2 C1 122.11(13) . . ?
C2 C3 C4 119.35(13) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 119.35(12) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 118.12(12) . . ?
C6 C5 C7 120.00(12) . . ?
C4 C5 C7 121.82(11) . . ?
N1 C6 C5 122.35(12) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
O3 C7 O2 124.50(13) . . ?
O3 C7 C5 118.31(11) . . ?
O2 C7 C5 117.18(13) . . ?
O4 C8 C9 110.03(11) . . ?
O4 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
O4 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N2 C9 C10 121.48(12) . . ?
N2 C9 C8 116.86(11) . . ?
C10 C9 C8 121.65(12) . . ?
C11 C10 C9 119.11(13) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 119.10(12) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 118.86(12) . . ?
C13 C12 C14 118.34(12) . . ?
C11 C12 C14 122.78(12) . . ?
N2 C13 C12 121.87(12) . . ?
N2 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
O5 C14 O6 124.57(14) . . ?
O5 C14 C12 123.62(13) . . ?
O6 C14 C12 111.81(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H21 O2 0.803(14) 1.918(15) 2.6973(16) 163(2) 2_656
O4 H22 O3 0.803(16) 1.814(17) 2.6033(15) 167(2) 2_566
O4 H22 O2 0.803(16) 2.67(2) 3.2487(17) 131(2) 2_566
O6 H23 O2 0.805(18) 1.787(19) 2.5813(17) 169(3) 1_554

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1013149'
_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Zn (H2 O)2 (C13 H10 N O3)2'
_chemical_formula_sum            'C26 H24 N2 O8 Zn'
_chemical_formula_weight         557.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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_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                   28.325(2)
_cell_length_b                   7.1216(6)
_cell_length_c                   12.6168(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.533(14)
_cell_angle_gamma                90.00
_cell_volume                     2315.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2748
_cell_measurement_theta_min      3.8459
_cell_measurement_theta_max      76.4772

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    1.973
_exptl_absorpt_correction_T_min  0.7562
_exptl_absorpt_correction_T_max  0.9432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis PRO (Agilent, 2012)'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  
'Agilent Technologies SuperNova Dual diffractometer with Atlas detector'
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measurement_method       'ω scan'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7792
_diffrn_reflns_av_R_equivalents  0.0929
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         6.45
_diffrn_reflns_theta_max         76.64
_reflns_number_total             2402
_reflns_number_gt                1991
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0883P)²+0.4233P] 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         2402
_refine_ls_number_parameters     180
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1594
_refine_ls_wR_factor_gt          0.1459
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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 0.60800(8) 0.2500 0.0135(2) Uani 1 2 d S . .
O1 O 0.00215(8) 0.4018(3) 0.1276(2) 0.0179(5) Uani 1 1 d D . .
H1 H -0.0219(13) 0.322(5) 0.106(4) 0.037(13) Uiso 1 1 d D . .
O2 O 0.41412(9) 0.3629(4) 0.3760(3) 0.0306(6) Uani 1 1 d . . .
O3 O 0.43344(8) 0.3679(3) 0.5681(2) 0.0230(5) Uani 1 1 d . . .
O1w O 0.00549(8) 0.8129(3) 0.3717(2) 0.0174(5) Uani 1 1 d D . .
H2 H -0.0231(10) 0.831(7) 0.375(4) 0.032(12) Uiso 1 1 d D . .
H3 H 0.021(2) 0.915(4) 0.378(5) 0.052(17) Uiso 1 1 d D . .
N1 N 0.07963(9) 0.5559(4) 0.3039(2) 0.0141(5) Uani 1 1 d . . .
C1 C 0.05102(11) 0.3486(5) 0.1354(3) 0.0218(7) Uani 1 1 d . . .
H1A H 0.0540 0.3826 0.0624 0.026 Uiso 1 1 calc R . .
H1B H 0.0549 0.2108 0.1452 0.026 Uiso 1 1 calc R . .
C2 C 0.09353(11) 0.4440(4) 0.2369(3) 0.0150(6) Uani 1 1 d . . .
C3 C 0.14549(11) 0.4125(4) 0.2585(3) 0.0160(6) Uani 1 1 d . . .
H3A H 0.1540 0.3351 0.2077 0.019 Uiso 1 1 calc R . .
C4 C 0.18459(11) 0.4953(4) 0.3551(3) 0.0149(6) Uani 1 1 d . . .
C5 C 0.16957(11) 0.6076(4) 0.4260(3) 0.0172(6) Uani 1 1 d . . .
H5 H 0.1951 0.6646 0.4936 0.021 Uiso 1 1 calc R . .
C6 C 0.11712(11) 0.6359(4) 0.3976(3) 0.0177(6) Uani 1 1 d . . .
H6 H 0.1074 0.7146 0.4460 0.021 Uiso 1 1 calc R . .
C7 C 0.24031(11) 0.4642(4) 0.3817(3) 0.0155(6) Uani 1 1 d . . .
C8 C 0.27678(11) 0.4522(5) 0.4974(3) 0.0177(6) Uani 1 1 d . . .
H8 H 0.2658 0.4635 0.5588 0.021 Uiso 1 1 calc R . .
C9 C 0.32927(11) 0.4238(4) 0.5235(3) 0.0181(6) Uani 1 1 d . . .
H9 H 0.3539 0.4165 0.6023 0.022 Uiso 1 1 calc R . .
C10 C 0.34534(11) 0.4060(4) 0.4334(3) 0.0176(6) Uani 1 1 d . . .
C11 C 0.30898(13) 0.4187(5) 0.3182(3) 0.0217(7) Uani 1 1 d . . .
H11 H 0.3199 0.4070 0.2568 0.026 Uiso 1 1 calc R . .
C12 C 0.25688(12) 0.4483(5) 0.2921(3) 0.0211(7) Uani 1 1 d . . .
H12 H 0.2325 0.4576 0.2131 0.025 Uiso 1 1 calc R . .
C13 C 0.40237(12) 0.3756(4) 0.4610(3) 0.0196(6) Uani 1 1 d . . .


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 O1w 2.077(2) . ?
Zn1 O1w 2.077(2) 2 ?
Zn1 N1 2.101(2) 2 ?
Zn1 N1 2.101(2) . ?
Zn1 O1 2.150(2) . ?
Zn1 O1 2.150(2) 2 ?
O1 C1 1.399(3) . ?
O1 H1 0.841(10) . ?
O2 C13 1.251(5) . ?
O3 C13 1.271(4) . ?
O1w H2 0.839(10) . ?
O1w H3 0.842(10) . ?
N1 C2 1.334(4) . ?
N1 C6 1.344(4) . ?
C1 C2 1.507(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.399(4) . ?
C3 C4 1.392(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.391(5) . ?
C4 C7 1.488(4) . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.397(4) . ?
C7 C12 1.398(5) . ?
C8 C9 1.398(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(5) . ?
C10 C13 1.520(4) . ?
C11 C12 1.388(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
O1w Zn1 O1w 90.72(13) . 2 ?
O1w Zn1 N1 95.97(9) . 2 ?
O1w Zn1 N1 98.28(9) 2 2 ?
O1w Zn1 N1 98.28(9) . . ?
O1w Zn1 N1 95.97(9) 2 . ?
N1 Zn1 N1 159.67(14) 2 . ?
O1w Zn1 O1 174.36(8) . . ?
O1w Zn1 O1 87.97(10) 2 . ?
N1 Zn1 O1 89.65(9) 2 . ?
N1 Zn1 O1 76.41(9) . . ?
O1w Zn1 O1 87.97(10) . 2 ?
O1w Zn1 O1 174.36(8) 2 2 ?
N1 Zn1 O1 76.41(9) 2 2 ?
N1 Zn1 O1 89.65(9) . 2 ?
O1 Zn1 O1 93.85(13) . 2 ?
C1 O1 Zn1 117.18(18) . . ?
C1 O1 H1 119(3) . . ?
Zn1 O1 H1 116(4) . . ?
Zn1 O1w H2 112(3) . . ?
Zn1 O1w H3 124(4) . . ?
H2 O1w H3 110(5) . . ?
C2 N1 C6 118.5(3) . . ?
C2 N1 Zn1 117.4(2) . . ?
C6 N1 Zn1 124.0(2) . . ?
O1 C1 C2 110.9(3) . . ?
O1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
N1 C2 C3 122.4(3) . . ?
N1 C2 C1 117.8(3) . . ?
C3 C2 C1 119.9(3) . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C5 C4 C3 117.5(3) . . ?
C5 C4 C7 121.3(3) . . ?
C3 C4 C7 121.2(3) . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
N1 C6 C5 122.3(3) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C8 C7 C12 119.3(3) . . ?
C8 C7 C4 120.0(3) . . ?
C12 C7 C4 120.7(3) . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 C13 120.2(3) . . ?
C9 C10 C13 120.1(3) . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 120.1(3) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
O2 C13 O3 126.5(3) . . ?
O2 C13 C10 116.7(3) . . ?
O3 C13 C10 116.8(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
O1w Zn1 O1 C1 91.7(2) 2 . . . ?
N1 Zn1 O1 C1 -170.0(2) 2 . . . ?
N1 Zn1 O1 C1 -4.9(2) . . . . ?
O1 Zn1 O1 C1 -93.6(2) 2 . . . ?
O1w Zn1 N1 C2 -172.2(2) . . . . ?
O1w Zn1 N1 C2 -80.5(2) 2 . . . ?
N1 Zn1 N1 C2 53.8(2) 2 . . . ?
O1 Zn1 N1 C2 5.9(2) . . . . ?
O1 Zn1 N1 C2 100.0(2) 2 . . . ?
O1w Zn1 N1 C6 4.2(3) . . . . ?
O1w Zn1 N1 C6 95.8(3) 2 . . . ?
N1 Zn1 N1 C6 -129.8(3) 2 . . . ?
O1 Zn1 N1 C6 -177.7(3) . . . . ?
O1 Zn1 N1 C6 -83.7(3) 2 . . . ?
Zn1 O1 C1 C2 3.3(4) . . . . ?
C6 N1 C2 C3 -2.2(5) . . . . ?
Zn1 N1 C2 C3 174.3(2) . . . . ?
C6 N1 C2 C1 177.3(3) . . . . ?
Zn1 N1 C2 C1 -6.1(4) . . . . ?
O1 C1 C2 N1 1.8(4) . . . . ?
O1 C1 C2 C3 -178.7(3) . . . . ?
N1 C2 C3 C4 2.0(5) . . . . ?
C1 C2 C3 C4 -177.5(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C2 C3 C4 C7 179.5(3) . . . . ?
C3 C4 C5 C6 -1.3(5) . . . . ?
C7 C4 C5 C6 179.0(3) . . . . ?
C2 N1 C6 C5 0.7(5) . . . . ?
Zn1 N1 C6 C5 -175.6(2) . . . . ?
C4 C5 C6 N1 1.1(5) . . . . ?
C5 C4 C7 C8 35.2(4) . . . . ?
C3 C4 C7 C8 -144.6(3) . . . . ?
C5 C4 C7 C12 -144.3(3) . . . . ?
C3 C4 C7 C12 36.0(5) . . . . ?
C12 C7 C8 C9 -0.3(5) . . . . ?
C4 C7 C8 C9 -179.8(3) . . . . ?
C7 C8 C9 C10 -0.4(5) . . . . ?
C8 C9 C10 C11 0.6(5) . . . . ?
C8 C9 C10 C13 179.8(3) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C13 C10 C11 C12 -179.4(3) . . . . ?
C10 C11 C12 C7 -0.5(5) . . . . ?
C8 C7 C12 C11 0.7(5) . . . . ?
C4 C7 C12 C11 -179.8(3) . . . . ?
C11 C10 C13 O2 -0.1(5) . . . . ?
C9 C10 C13 O2 -179.3(3) . . . . ?
C11 C10 C13 O3 179.1(3) . . . . ?
C9 C10 C13 O3 0.0(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
O1 H1 O3 0.84(1) 1.78(1) 2.613(3) 173(5) 8_455
O1w H2 O2 0.84(1) 1.80(1) 2.635(3) 177(5) 3_455
O1w H3 O3 0.84(1) 1.94(2) 2.766(3) 166(6) 7_566

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        76.64
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.909
_refine_diff_density_min         -0.959
_refine_diff_density_rms         0.120
####################################################################### 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1013150'

_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 N2 O8 Zn'
_chemical_formula_sum            'C26 H24 N2 O8 Zn'
_chemical_formula_weight         557.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_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                   25.0244(9)
_cell_length_b                   7.5228(3)
_cell_length_c                   12.9729(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.7859(7)
_cell_angle_gamma                90.00
_cell_volume                     2325.47(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5734
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      28.27

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    1.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8080
_exptl_absorpt_correction_T_max  0.9162
_exptl_absorpt_process_details   'SADABS, (Sheldrick 1996)'

_exptl_special_details           ?

_diffrn_ambient_temperature      296(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 ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10557
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2666
_reflns_number_gt                2433
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep3 (Farrugia, 1997)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0398P)²+2.4455P] 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         2666
_refine_ls_number_parameters     178
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0790
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.121
_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 0.0000 0.68778(4) 0.2500 0.03120(11) Uani 1 2 d S . .
O1 O -0.01278(6) 0.6935(3) 0.08146(13) 0.0562(5) Uani 1 1 d D . .
H1 H -0.0424(10) 0.726(4) 0.036(2) 0.067 Uiso 1 1 d D . .
O2 O 0.39021(6) 0.7246(3) 0.44379(13) 0.0661(6) Uani 1 1 d . . .
O3 O 0.44219(6) 0.6838(2) 0.33632(12) 0.0425(3) Uani 1 1 d . . .
O1W O 0.0000 0.9632(4) 0.2500 0.0986(13) Uani 1 2 d SDU . .
H1W H 0.0126(18) 1.017(5) 0.208(3) 0.118 Uiso 1 1 d D . .
O2W O 0.0000 0.4095(3) 0.2500 0.0874(11) Uani 1 2 d SDU . .
H2W H -0.0169(17) 0.347(4) 0.281(3) 0.105 Uiso 1 1 d D . .
N1 N 0.08142(6) 0.6758(2) 0.24039(12) 0.0301(3) Uani 1 1 d . . .
C1 C 0.03472(7) 0.7343(3) 0.05004(15) 0.0407(5) Uani 1 1 d . . .
H1A H 0.0339 0.8589 0.0302 0.049 Uiso 1 1 calc R . .
H1B H 0.0347 0.6637 -0.0125 0.049 Uiso 1 1 calc R . .
C2 C 0.08701(7) 0.6959(2) 0.14220(14) 0.0294(4) Uani 1 1 d . . .
C3 C 0.13866(7) 0.6838(3) 0.12391(14) 0.0332(4) Uani 1 1 d . . .
H3A H 0.1412 0.7007 0.0545 0.040 Uiso 1 1 calc R . .
C4 C 0.18662(7) 0.6466(2) 0.20875(14) 0.0296(4) Uani 1 1 d . . .
C5 C 0.17972(7) 0.6242(3) 0.31004(15) 0.0390(4) Uani 1 1 d . . .
H5A H 0.2106 0.5981 0.3694 0.047 Uiso 1 1 calc R . .
C6 C 0.12761(8) 0.6402(3) 0.32306(15) 0.0395(5) Uani 1 1 d . . .
H6A H 0.1241 0.6259 0.3919 0.047 Uiso 1 1 calc R . .
C7 C 0.24247(7) 0.6284(3) 0.19245(14) 0.0296(3) Uani 1 1 d . . .
C8 C 0.24746(8) 0.5733(3) 0.09346(15) 0.0416(5) Uani 1 1 d . . .
H8A H 0.2154 0.5477 0.0365 0.050 Uiso 1 1 calc R . .
C9 C 0.29980(8) 0.5563(3) 0.07896(16) 0.0464(5) Uani 1 1 d . . .
H9A H 0.3026 0.5188 0.0125 0.056 Uiso 1 1 calc R . .
C10 C 0.34767(7) 0.5945(3) 0.16227(15) 0.0375(4) Uani 1 1 d . . .
H10A H 0.3827 0.5844 0.1517 0.045 Uiso 1 1 calc R . .
C11 C 0.34376(7) 0.6482(2) 0.26187(14) 0.0290(3) Uani 1 1 d . . .
C12 C 0.29120(7) 0.6649(2) 0.27612(14) 0.0295(4) Uani 1 1 d . . .
H12A H 0.2886 0.7013 0.3429 0.035 Uiso 1 1 calc R . .
C13 C 0.39578(7) 0.6890(3) 0.35438(15) 0.0340(4) Uani 1 1 d . . .


_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 O1W 2.072(3) . ?
Zn1 N1 2.0809(14) . ?
Zn1 N1 2.0810(14) 2 ?
Zn1 O2W 2.094(3) . ?
Zn1 O1 2.1113(16) 2 ?
Zn1 O1 2.1113(16) . ?
O1 C1 1.403(2) . ?
O1 H1 0.829(18) . ?
O2 C13 1.239(2) . ?
O3 C13 1.253(2) . ?
O1W H1W 0.811(19) . ?
O2W H2W 0.811(19) . ?
N1 C2 1.332(2) . ?
N1 C6 1.342(2) . ?
C1 C2 1.506(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.387(2) . ?
C3 C4 1.387(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.387(2) . ?
C4 C7 1.482(2) . ?
C5 C6 1.370(2) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C12 1.390(2) . ?
C7 C8 1.391(2) . ?
C8 C9 1.385(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.377(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.385(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.389(2) . ?
C11 C13 1.508(2) . ?
C12 H12A 0.9300 . ?

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
O1W Zn1 N1 92.49(4) . . ?
O1W Zn1 N1 92.49(4) . 2 ?
N1 Zn1 N1 175.02(9) . 2 ?
O1W Zn1 O2W 180.000(1) . . ?
N1 Zn1 O2W 87.51(4) . . ?
N1 Zn1 O2W 87.51(4) 2 . ?
O1W Zn1 O1 88.84(6) . 2 ?
N1 Zn1 O1 102.80(6) . 2 ?
N1 Zn1 O1 77.31(6) 2 2 ?
O2W Zn1 O1 91.16(6) . 2 ?
O1W Zn1 O1 88.84(6) . . ?
N1 Zn1 O1 77.30(6) . . ?
N1 Zn1 O1 102.80(6) 2 . ?
O2W Zn1 O1 91.16(6) . . ?
O1 Zn1 O1 177.67(11) 2 . ?
C1 O1 Zn1 115.55(12) . . ?
C1 O1 H1 113(2) . . ?
Zn1 O1 H1 124(2) . . ?
Zn1 O1W H1W 120(3) . . ?
Zn1 O2W H2W 125(3) . . ?
C2 N1 C6 118.08(15) . . ?
C2 N1 Zn1 116.31(11) . . ?
C6 N1 Zn1 125.51(12) . . ?
O1 C1 C2 109.58(15) . . ?
O1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
O1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C3 122.13(16) . . ?
N1 C2 C1 117.47(15) . . ?
C3 C2 C1 120.40(16) . . ?
C2 C3 C4 120.23(16) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C3 C4 C5 116.65(16) . . ?
C3 C4 C7 122.03(16) . . ?
C5 C4 C7 121.31(15) . . ?
C6 C5 C4 120.31(16) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
N1 C6 C5 122.60(16) . . ?
N1 C6 H6A 118.7 . . ?
C5 C6 H6A 118.7 . . ?
C12 C7 C8 118.37(15) . . ?
C12 C7 C4 120.72(15) . . ?
C8 C7 C4 120.91(16) . . ?
C9 C8 C7 120.55(17) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C10 C9 C8 120.42(17) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C9 C10 C11 120.05(16) . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C10 C11 C12 119.35(16) . . ?
C10 C11 C13 120.78(15) . . ?
C12 C11 C13 119.87(15) . . ?
C11 C12 C7 121.25(16) . . ?
C11 C12 H12A 119.4 . . ?
C7 C12 H12A 119.4 . . ?
O2 C13 O3 123.87(18) . . ?
O2 C13 C11 118.18(16) . . ?
O3 C13 C11 117.95(17) . . ?

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
O1W Zn1 O1 C1 76.52(16) . . . . ?
N1 Zn1 O1 C1 -16.30(16) . . . . ?
N1 Zn1 O1 C1 168.81(16) 2 . . . ?
O2W Zn1 O1 C1 -103.48(16) . . . . ?
O1 Zn1 O1 C1 76.45(17) 2 . . . ?
O1W Zn1 N1 C2 -81.45(13) . . . . ?
N1 Zn1 N1 C2 98.54(13) 2 . . . ?
O2W Zn1 N1 C2 98.55(13) . . . . ?
O1 Zn1 N1 C2 -170.82(13) 2 . . . ?
O1 Zn1 N1 C2 6.80(13) . . . . ?
O1W Zn1 N1 C6 102.36(17) . . . . ?
N1 Zn1 N1 C6 -77.66(17) 2 . . . ?
O2W Zn1 N1 C6 -77.64(17) . . . . ?
O1 Zn1 N1 C6 12.99(19) 2 . . . ?
O1 Zn1 N1 C6 -169.40(18) . . . . ?
Zn1 O1 C1 C2 21.6(2) . . . . ?
C6 N1 C2 C3 -0.9(3) . . . . ?
Zn1 N1 C2 C3 -177.41(14) . . . . ?
C6 N1 C2 C1 179.52(19) . . . . ?
Zn1 N1 C2 C1 3.0(2) . . . . ?
O1 C1 C2 N1 -16.2(3) . . . . ?
O1 C1 C2 C3 164.27(19) . . . . ?
N1 C2 C3 C4 1.1(3) . . . . ?
C1 C2 C3 C4 -179.32(19) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C4 C7 178.62(17) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C7 C4 C5 C6 -179.5(2) . . . . ?
C2 N1 C6 C5 0.0(3) . . . . ?
Zn1 N1 C6 C5 176.13(17) . . . . ?
C4 C5 C6 N1 0.7(4) . . . . ?
C3 C4 C7 C12 152.95(19) . . . . ?
C5 C4 C7 C12 -28.1(3) . . . . ?
C3 C4 C7 C8 -27.5(3) . . . . ?
C5 C4 C7 C8 151.4(2) . . . . ?
C12 C7 C8 C9 -0.3(3) . . . . ?
C4 C7 C8 C9 -179.8(2) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C11 0.9(4) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C9 C10 C11 C13 179.4(2) . . . . ?
C10 C11 C12 C7 0.2(3) . . . . ?
C13 C11 C12 C7 179.95(17) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
C4 C7 C12 C11 179.90(17) . . . . ?
C10 C11 C13 O2 -175.1(2) . . . . ?
C12 C11 C13 O2 5.1(3) . . . . ?
C10 C11 C13 O3 4.4(3) . . . . ?
C12 C11 C13 O3 -175.34(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.829(18) 1.784(19) 2.610(2) 174(3) 8_465
O1 H1 O3 0.829(18) 2.59(3) 3.170(2) 128(3) 8_465
O1W H1W O3 0.811(19) 1.90(2) 2.663(2) 157(4) 4
O2W H2W O3 0.811(19) 1.88(2) 2.687(2) 173(4) 3_445

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 1013151'
_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 N2 O8 Zn, H2 O'
_chemical_formula_sum            'C26 H26 N2 O9 Zn'
_chemical_formula_weight         575.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_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                   26.264(2)
_cell_length_b                   8.4871(8)
_cell_length_c                   12.0334(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.801(2)
_cell_angle_gamma                90.00
_cell_volume                     2434.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4245
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.33

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1192
_exptl_absorpt_coefficient_mu    1.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7398
_exptl_absorpt_correction_T_max  0.9194
_exptl_absorpt_process_details   'SADABS, (Sheldrick 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7396
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2777
_reflns_number_gt                2542
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex II (Bruker, 2011)'
_computing_cell_refinement       'Apex II (Bruker, 2011)'
_computing_data_reduction        'Apex II (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0543P)²+1.5654P] 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         2777
_refine_ls_number_parameters     192
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0850
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.038
_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 0.5000 0.60441(3) 0.2500 0.02680(10) Uani 1 2 d S . .
O1 O 0.51778(5) 0.63716(17) 0.09840(11) 0.0352(3) Uani 1 1 d D . .
H1 H 0.5434(8) 0.607(3) 0.079(2) 0.053 Uiso 1 1 d D . .
O2 O 0.10533(5) 1.07485(19) 0.06700(13) 0.0437(3) Uani 1 1 d . . .
O3 O 0.13921(6) 0.9206(2) 0.23127(14) 0.0512(4) Uani 1 1 d . . .
O1W O 0.43975(5) 0.42323(17) 0.18534(12) 0.0364(3) Uani 1 1 d D . .
H11 H 0.4168(8) 0.417(3) 0.2170(18) 0.055 Uiso 1 1 d D . .
H12 H 0.4228(9) 0.413(3) 0.1095(9) 0.055 Uiso 1 1 d D . .
O2W O 0.4872(6) 0.1040(7) 0.247(2) 0.131(4) Uani 0.50 1 d PDU A -1
H21 H 0.465(4) 0.180(9) 0.212(10) 0.197 Uiso 0.50 1 d PD B -1
H22 H 0.491(6) 0.101(14) 0.321(5) 0.197 Uiso 0.50 1 d PD C -1
N1 N 0.43639(5) 0.76580(18) 0.13607(12) 0.0287(3) Uani 1 1 d . . .
C1 C 0.48892(7) 0.7541(2) 0.01216(17) 0.0366(4) Uani 1 1 d . . .
H1A H 0.4763 0.7114 -0.0699 0.044 Uiso 1 1 calc R . .
H1B H 0.5139 0.8416 0.0198 0.044 Uiso 1 1 calc R . .
C2 C 0.43924(6) 0.8110(2) 0.03283(15) 0.0291(3) Uani 1 1 d . . .
C3 C 0.39755(8) 0.9030(2) -0.05290(19) 0.0402(4) Uani 1 1 d . . .
H3 H 0.4008 0.9372 -0.1230 0.048 Uiso 1 1 calc R . .
C4 C 0.35120(8) 0.9431(3) -0.03289(18) 0.0404(4) Uani 1 1 d . . .
H4 H 0.3231 1.0047 -0.0899 0.049 Uiso 1 1 calc R . .
C5 C 0.34622(7) 0.8919(2) 0.07236(16) 0.0292(3) Uani 1 1 d . . .
C6 C 0.39118(6) 0.8060(2) 0.15518(15) 0.0302(3) Uani 1 1 d . . .
H6 H 0.3899 0.7745 0.2280 0.036 Uiso 1 1 calc R . .
C7 C 0.29492(7) 0.9203(2) 0.09260(15) 0.0287(3) Uani 1 1 d . . .
C8 C 0.28280(7) 0.8261(2) 0.17403(17) 0.0372(4) Uani 1 1 d . . .
H8 H 0.3077 0.7470 0.2175 0.045 Uiso 1 1 calc R . .
C9 C 0.23422(7) 0.8493(3) 0.19064(17) 0.0371(4) Uani 1 1 d . . .
H9 H 0.2272 0.7869 0.2463 0.044 Uiso 1 1 calc R . .
C10 C 0.19581(6) 0.9647(2) 0.12512(15) 0.0290(3) Uani 1 1 d . . .
C11 C 0.20702(7) 1.0562(2) 0.04270(18) 0.0358(4) Uani 1 1 d . . .
H11A H 0.1814 1.1325 -0.0031 0.043 Uiso 1 1 calc R . .
C12 C 0.25627(7) 1.0350(2) 0.02792(18) 0.0378(4) Uani 1 1 d . . .
H12A H 0.2635 1.0991 -0.0265 0.045 Uiso 1 1 calc R . .
C13 C 0.14279(7) 0.9870(2) 0.14316(15) 0.0322(4) Uani 1 1 d . . .


_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 2.0827(12) . ?
Zn1 O1 2.0828(12) 6_656 ?
Zn1 O1W 2.1074(13) . ?
Zn1 O1W 2.1075(13) 6_656 ?
Zn1 N1 2.1507(14) 6_656 ?
Zn1 N1 2.1507(14) . ?
O1 C1 1.406(2) . ?
O1 H1 0.841(10) . ?
O2 C13 1.268(2) . ?
O3 C13 1.239(2) . ?
O1W H11 0.839(10) . ?
O1W H12 0.836(9) . ?
O2W H21 0.852(10) . ?
O2W H22 0.853(10) . ?
N1 C2 1.332(2) . ?
N1 C6 1.3445(19) . ?
C1 C2 1.507(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.388(2) . ?
C3 C4 1.379(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(2) . ?
C5 C7 1.486(2) . ?
C6 H6 0.9300 . ?
C7 C12 1.386(2) . ?
C7 C8 1.401(3) . ?
C8 C9 1.386(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.390(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(3) . ?
C10 C13 1.508(2) . ?
C11 C12 1.389(2) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?

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 164.66(8) . 6_656 ?
O1 Zn1 O1W 100.57(5) . . ?
O1 Zn1 O1W 90.64(5) 6_656 . ?
O1 Zn1 O1W 90.64(5) . 6_656 ?
O1 Zn1 O1W 100.57(5) 6_656 6_656 ?
O1W Zn1 O1W 86.29(8) . 6_656 ?
O1 Zn1 N1 94.23(5) . 6_656 ?
O1 Zn1 N1 75.90(5) 6_656 6_656 ?
O1W Zn1 N1 164.22(5) . 6_656 ?
O1W Zn1 N1 88.11(5) 6_656 6_656 ?
O1 Zn1 N1 75.89(5) . . ?
O1 Zn1 N1 94.23(5) 6_656 . ?
O1W Zn1 N1 88.12(5) . . ?
O1W Zn1 N1 164.22(5) 6_656 . ?
N1 Zn1 N1 100.88(8) 6_656 . ?
C1 O1 Zn1 119.42(9) . . ?
C1 O1 H1 104.6(17) . . ?
Zn1 O1 H1 135.0(18) . . ?
Zn1 O1W H11 116.7(16) . . ?
Zn1 O1W H12 117.0(17) . . ?
H11 O1W H12 109.6(15) . . ?
H21 O2W H22 106.8(18) . . ?
C2 N1 C6 119.06(14) . . ?
C2 N1 Zn1 116.44(10) . . ?
C6 N1 Zn1 123.93(11) . . ?
O1 C1 C2 109.91(13) . . ?
O1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
O1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C3 121.32(14) . . ?
N1 C2 C1 116.95(14) . . ?
C3 C2 C1 121.71(15) . . ?
C4 C3 C2 119.22(17) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.47(17) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 116.04(15) . . ?
C6 C5 C7 121.57(15) . . ?
C4 C5 C7 122.33(15) . . ?
N1 C6 C5 123.78(15) . . ?
N1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
C12 C7 C8 117.76(15) . . ?
C12 C7 C5 121.51(16) . . ?
C8 C7 C5 120.67(15) . . ?
C9 C8 C7 120.87(16) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.76(17) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 118.66(15) . . ?
C11 C10 C13 121.25(16) . . ?
C9 C10 C13 120.08(16) . . ?
C10 C11 C12 120.52(16) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C7 C12 C11 121.41(17) . . ?
C7 C12 H12A 119.3 . . ?
C11 C12 H12A 119.3 . . ?
O3 C13 O2 124.88(15) . . ?
O3 C13 C10 118.17(16) . . ?
O2 C13 C10 116.95(15) . . ?

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 -42.12(13) 6_656 . . . ?
O1W Zn1 O1 C1 94.25(14) . . . . ?
O1W Zn1 O1 C1 -179.41(14) 6_656 . . . ?
N1 Zn1 O1 C1 -91.25(14) 6_656 . . . ?
N1 Zn1 O1 C1 8.92(13) . . . . ?
O1 Zn1 N1 C2 -2.02(12) . . . . ?
O1 Zn1 N1 C2 166.08(13) 6_656 . . . ?
O1W Zn1 N1 C2 -103.41(13) . . . . ?
O1W Zn1 N1 C2 -34.2(3) 6_656 . . . ?
N1 Zn1 N1 C2 89.65(13) 6_656 . . . ?
O1 Zn1 N1 C6 169.18(15) . . . . ?
O1 Zn1 N1 C6 -22.72(14) 6_656 . . . ?
O1W Zn1 N1 C6 67.78(14) . . . . ?
O1W Zn1 N1 C6 137.01(18) 6_656 . . . ?
N1 Zn1 N1 C6 -99.16(14) 6_656 . . . ?
Zn1 O1 C1 C2 -13.3(2) . . . . ?
C6 N1 C2 C3 2.3(3) . . . . ?
Zn1 N1 C2 C3 173.95(14) . . . . ?
C6 N1 C2 C1 -176.15(16) . . . . ?
Zn1 N1 C2 C1 -4.5(2) . . . . ?
O1 C1 C2 N1 11.2(2) . . . . ?
O1 C1 C2 C3 -167.24(17) . . . . ?
N1 C2 C3 C4 -2.6(3) . . . . ?
C1 C2 C3 C4 175.77(19) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 2.6(3) . . . . ?
C3 C4 C5 C7 -174.53(19) . . . . ?
C2 N1 C6 C5 0.6(3) . . . . ?
Zn1 N1 C6 C5 -170.38(13) . . . . ?
C4 C5 C6 N1 -3.0(3) . . . . ?
C7 C5 C6 N1 174.14(16) . . . . ?
C6 C5 C7 C12 164.28(18) . . . . ?
C4 C5 C7 C12 -18.7(3) . . . . ?
C6 C5 C7 C8 -18.8(3) . . . . ?
C4 C5 C7 C8 158.20(19) . . . . ?
C12 C7 C8 C9 -1.1(3) . . . . ?
C5 C7 C8 C9 -178.18(18) . . . . ?
C7 C8 C9 C10 1.2(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C8 C9 C10 C13 179.25(17) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C13 C10 C11 C12 179.48(17) . . . . ?
C8 C7 C12 C11 -0.2(3) . . . . ?
C5 C7 C12 C11 176.87(17) . . . . ?
C10 C11 C12 C7 1.4(3) . . . . ?
C11 C10 C13 O3 -168.44(19) . . . . ?
C9 C10 C13 O3 12.4(3) . . . . ?
C11 C10 C13 O2 10.7(3) . . . . ?
C9 C10 C13 O2 -168.53(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.841(10) 1.712(12) 2.5374(17) 166(3) 3_545
O1W H11 O3 0.839(10) 1.822(11) 2.6558(19) 172(2) 8_546
O1W H12 O2 0.836(9) 1.937(10) 2.758(2) 167(2) 7_565
O2W H21 O1W 0.852(10) 2.15(5) 2.944(9) 155(11) .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_15
_database_code_depnum_ccdc_archive 'CCDC 1013152'

_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 Co N2 O8'
_chemical_formula_sum            'C26 H24 Co N2 O8'
_chemical_formula_weight         551.40

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_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                   25.051(11)
_cell_length_b                   7.425(3)
_cell_length_c                   12.951(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.721(8)
_cell_angle_gamma                90.00
_cell_volume                     2294.8(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    525
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      20.27

_exptl_crystal_description       block
_exptl_crystal_colour            light-orange
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1140
_exptl_absorpt_coefficient_mu    0.806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9841
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'


_exptl_special_details           ?

_diffrn_ambient_temperature      123(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 ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15227
_diffrn_reflns_av_R_equivalents  0.1697
_diffrn_reflns_av_sigmaI/netI    0.1228
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         27.51
_reflns_number_total             2637
_reflns_number_gt                1495
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0412P)²+0.0000P] 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         2637
_refine_ls_number_parameters     178
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1329
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.987
_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
Co1 Co 0.5000 0.18094(12) 0.2500 0.0170(2) Uani 1 2 d S . .
O1 O 0.51135(10) 0.1856(5) 0.4165(2) 0.0304(7) Uani 1 1 d D . .
H1O H 0.5410(12) 0.225(5) 0.460(3) 0.036 Uiso 1 1 d D . .
O2 O 0.10840(11) 0.2242(4) 0.0528(2) 0.0344(9) Uani 1 1 d . . .
O3 O 0.05586(9) 0.1787(4) 0.16064(19) 0.0222(6) Uani 1 1 d . . .
O1W O 0.5000 0.4549(7) 0.2500 0.0557(15) Uani 1 2 d SD . .
H1W1 H 0.516(2) 0.502(6) 0.209(4) 0.067 Uiso 1 1 d D . .
O2W O 0.5000 -0.0928(6) 0.2500 0.0454(14) Uani 1 2 d SD . .
H1W2 H 0.5223(16) -0.159(5) 0.234(4) 0.054 Uiso 1 1 d D . .
N1 N 0.41759(11) 0.1728(4) 0.2590(2) 0.0166(7) Uani 1 1 d . . .
C1 C 0.46376(14) 0.2324(5) 0.4494(3) 0.0220(10) Uani 1 1 d . . .
H1A H 0.4652 0.3619 0.4683 0.026 Uiso 1 1 calc R . .
H1B H 0.4638 0.1619 0.5143 0.026 Uiso 1 1 calc R . .
C2 C 0.41124(15) 0.1928(5) 0.3577(3) 0.0178(8) Uani 1 1 d . . .
C3 C 0.36011(14) 0.1832(6) 0.3761(3) 0.0201(8) Uani 1 1 d . . .
H3 H 0.3577 0.2025 0.4470 0.024 Uiso 1 1 calc R . .
C4 C 0.31187(15) 0.1454(5) 0.2912(3) 0.0173(9) Uani 1 1 d . . .
C5 C 0.31917(16) 0.1229(5) 0.1893(3) 0.0228(10) Uani 1 1 d . . .
H5 H 0.2876 0.0974 0.1285 0.027 Uiso 1 1 calc R . .
C6 C 0.37101(15) 0.1370(5) 0.1760(3) 0.0235(10) Uani 1 1 d . . .
H6 H 0.3745 0.1209 0.1055 0.028 Uiso 1 1 calc R . .
C7 C 0.25586(15) 0.1292(5) 0.3067(3) 0.0173(9) Uani 1 1 d . . .
C8 C 0.25057(15) 0.0736(5) 0.4060(3) 0.0235(10) Uani 1 1 d . . .
H8 H 0.2833 0.0471 0.4642 0.028 Uiso 1 1 calc R . .
C9 C 0.19843(15) 0.0564(6) 0.4213(3) 0.0253(10) Uani 1 1 d . . .
H9 H 0.1957 0.0196 0.4897 0.030 Uiso 1 1 calc R . .
C10 C 0.15041(16) 0.0929(6) 0.3371(3) 0.0223(9) Uani 1 1 d . . .
H10 H 0.1146 0.0810 0.3475 0.027 Uiso 1 1 calc R . .
C11 C 0.15470(15) 0.1474(5) 0.2367(3) 0.0196(9) Uani 1 1 d . . .
C12 C 0.20726(14) 0.1656(5) 0.2227(3) 0.0178(8) Uani 1 1 d . . .
H12 H 0.2100 0.2036 0.1545 0.021 Uiso 1 1 calc R . .
C13 C 0.10262(15) 0.1870(6) 0.1428(3) 0.0202(8) Uani 1 1 d . . .


_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
Co1 O2W 2.033(5) . ?
Co1 O1W 2.034(5) . ?
Co1 O1 2.088(3) . ?
Co1 O1 2.088(3) 2_655 ?
Co1 N1 2.104(3) . ?
Co1 N1 2.104(3) 2_655 ?
O1 C1 1.426(4) . ?
O1 H1O 0.836(18) . ?
O2 C13 1.249(4) . ?
O3 C13 1.262(4) . ?
O1W H1W1 0.839(19) . ?
O2W H1W2 0.821(18) . ?
N1 C2 1.344(4) . ?
N1 C6 1.351(4) . ?
C1 C2 1.509(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.374(5) . ?
C3 C4 1.392(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(5) . ?
C4 C7 1.481(5) . ?
C5 C6 1.365(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.390(5) . ?
C7 C8 1.395(5) . ?
C8 C9 1.385(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.397(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(5) . ?
C11 C13 1.517(5) . ?
C12 H12 0.9500 . ?

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
O2W Co1 O1W 180.000(1) . . ?
O2W Co1 O1 90.95(10) . . ?
O1W Co1 O1 89.05(10) . . ?
O2W Co1 O1 90.95(10) . 2_655 ?
O1W Co1 O1 89.05(10) . 2_655 ?
O1 Co1 O1 178.1(2) . 2_655 ?
O2W Co1 N1 88.35(9) . . ?
O1W Co1 N1 91.65(9) . . ?
O1 Co1 N1 76.75(10) . . ?
O1 Co1 N1 103.31(10) 2_655 . ?
O2W Co1 N1 88.35(9) . 2_655 ?
O1W Co1 N1 91.65(9) . 2_655 ?
O1 Co1 N1 103.31(10) . 2_655 ?
O1 Co1 N1 76.75(10) 2_655 2_655 ?
N1 Co1 N1 176.70(19) . 2_655 ?
C1 O1 Co1 116.7(2) . . ?
C1 O1 H1O 111(3) . . ?
Co1 O1 H1O 121(3) . . ?
Co1 O1W H1W1 115(4) . . ?
Co1 O2W H1W2 127(3) . . ?
C2 N1 C6 117.1(3) . . ?
C2 N1 Co1 116.9(2) . . ?
C6 N1 Co1 125.9(2) . . ?
O1 C1 C2 109.0(3) . . ?
O1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
O1 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
N1 C2 C3 123.1(3) . . ?
N1 C2 C1 116.3(3) . . ?
C3 C2 C1 120.6(3) . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 116.0(3) . . ?
C3 C4 C7 122.7(3) . . ?
C5 C4 C7 121.3(3) . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
N1 C6 C5 122.6(4) . . ?
N1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C12 C7 C8 118.2(3) . . ?
C12 C7 C4 121.2(3) . . ?
C8 C7 C4 120.6(3) . . ?
C9 C8 C7 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 120.1(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 119.7(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 C13 119.7(3) . . ?
C10 C11 C13 120.7(3) . . ?
C11 C12 C7 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
O2 C13 O3 124.0(3) . . ?
O2 C13 C11 118.4(3) . . ?
O3 C13 C11 117.6(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
O2W Co1 O1 C1 -105.3(3) . . . . ?
O1W Co1 O1 C1 74.7(3) . . . . ?
O1 Co1 O1 C1 74.7(3) 2_655 . . . ?
N1 Co1 O1 C1 -17.3(3) . . . . ?
N1 Co1 O1 C1 166.1(3) 2_655 . . . ?
O2W Co1 N1 C2 98.0(3) . . . . ?
O1W Co1 N1 C2 -82.0(3) . . . . ?
O1 Co1 N1 C2 6.6(3) . . . . ?
O1 Co1 N1 C2 -171.5(3) 2_655 . . . ?
N1 Co1 N1 C2 98.0(3) 2_655 . . . ?
O2W Co1 N1 C6 -77.1(3) . . . . ?
O1W Co1 N1 C6 102.9(3) . . . . ?
O1 Co1 N1 C6 -168.5(3) . . . . ?
O1 Co1 N1 C6 13.4(3) 2_655 . . . ?
N1 Co1 N1 C6 -77.1(3) 2_655 . . . ?
Co1 O1 C1 C2 23.6(4) . . . . ?
C6 N1 C2 C3 -1.8(6) . . . . ?
Co1 N1 C2 C3 -177.4(3) . . . . ?
C6 N1 C2 C1 179.9(3) . . . . ?
Co1 N1 C2 C1 4.4(5) . . . . ?
O1 C1 C2 N1 -17.8(5) . . . . ?
O1 C1 C2 C3 163.9(4) . . . . ?
N1 C2 C3 C4 2.2(7) . . . . ?
C1 C2 C3 C4 -179.6(4) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
C2 C3 C4 C7 178.5(4) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C7 C4 C5 C6 -179.6(4) . . . . ?
C2 N1 C6 C5 0.7(6) . . . . ?
Co1 N1 C6 C5 175.8(3) . . . . ?
C4 C5 C6 N1 0.0(6) . . . . ?
C3 C4 C7 C12 153.1(4) . . . . ?
C5 C4 C7 C12 -27.1(6) . . . . ?
C3 C4 C7 C8 -28.1(6) . . . . ?
C5 C4 C7 C8 151.8(4) . . . . ?
C12 C7 C8 C9 -0.6(6) . . . . ?
C4 C7 C8 C9 -179.4(4) . . . . ?
C7 C8 C9 C10 0.6(6) . . . . ?
C8 C9 C10 C11 -0.1(6) . . . . ?
C9 C10 C11 C12 -0.5(6) . . . . ?
C9 C10 C11 C13 179.6(4) . . . . ?
C10 C11 C12 C7 0.5(6) . . . . ?
C13 C11 C12 C7 -179.6(3) . . . . ?
C8 C7 C12 C11 0.0(6) . . . . ?
C4 C7 C12 C11 178.8(4) . . . . ?
C12 C11 C13 O2 4.6(6) . . . . ?
C10 C11 C13 O2 -175.5(4) . . . . ?
C12 C11 C13 O3 -176.1(4) . . . . ?
C10 C11 C13 O3 3.8(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
O1 H1O O2 0.836(18) 1.79(2) 2.620(4) 171(4) 8_556
O1 H1O O3 0.836(18) 2.61(4) 3.180(4) 126(4) 8_556
O1W H1W1 O3 0.839(19) 1.86(3) 2.654(4) 157(5) 3
O2W H1W2 O3 0.821(18) 1.88(2) 2.676(4) 164(5) 3_545

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.098
####################################################################### 
# 
# 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_16
_database_code_depnum_ccdc_archive 'CCDC 1013153'

_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 N2 Ni O8'
_chemical_formula_sum            'C26 H24 N2 Ni O8'
_chemical_formula_weight         551.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_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                   24.917(4)
_cell_length_b                   7.3870(11)
_cell_length_c                   12.944(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.482(4)
_cell_angle_gamma                90.00
_cell_volume                     2272.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    679
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      20.39

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9644
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           ?

_diffrn_ambient_temperature      173(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 ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11008
_diffrn_reflns_av_R_equivalents  0.1516
_diffrn_reflns_av_sigmaI/netI    0.1066
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2071
_reflns_number_gt                1239
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0526P)²+0.0000P] 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         2071
_refine_ls_number_parameters     178
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.18189(14) 0.2500 0.0256(3) Uani 1 2 d S . .
O1W O 0.5000 0.4553(9) 0.2500 0.085(2) Uani 1 2 d SD . .
H1W H 0.515(3) 0.512(8) 0.208(5) 0.102 Uiso 1 1 d D . .
O1 O 0.48671(13) 0.1841(6) 0.0845(3) 0.0446(10) Uani 1 1 d D . .
H1O H 0.4588(16) 0.244(6) 0.044(4) 0.054 Uiso 1 1 d D . .
O2 O 0.94382(12) 0.1796(5) 0.3398(2) 0.0320(8) Uani 1 1 d . . .
O2W O 0.5000 -0.0920(9) 0.2500 0.079(2) Uani 1 2 d SD . .
H2W H 0.486(3) -0.165(7) 0.286(5) 0.095 Uiso 1 1 d D . .
O3 O 0.89072(14) 0.2200(6) 0.4480(3) 0.0493(12) Uani 1 1 d . . .
N1 N 0.58081(15) 0.1734(5) 0.2420(3) 0.0250(9) Uani 1 1 d . . .
C1 C 0.53447(19) 0.2321(7) 0.0523(4) 0.0321(13) Uani 1 1 d . . .
H1A H 0.5328 0.3623 0.0336 0.038 Uiso 1 1 calc R . .
H1B H 0.5347 0.1618 -0.0126 0.038 Uiso 1 1 calc R . .
C2 C 0.58738(18) 0.1937(7) 0.1431(4) 0.0244(11) Uani 1 1 d . . .
C3 C 0.63875(18) 0.1818(7) 0.1259(4) 0.0285(11) Uani 1 1 d . . .
H3 H 0.6415 0.1990 0.0549 0.034 Uiso 1 1 calc R . .
C4 C 0.68679(18) 0.1454(6) 0.2099(4) 0.0248(12) Uani 1 1 d . . .
C5 C 0.6798(2) 0.1210(7) 0.3118(4) 0.0315(13) Uani 1 1 d . . .
H5 H 0.7114 0.0939 0.3725 0.038 Uiso 1 1 calc R . .
C6 C 0.6273(2) 0.1364(7) 0.3242(4) 0.0351(14) Uani 1 1 d . . .
H6 H 0.6235 0.1201 0.3945 0.042 Uiso 1 1 calc R . .
C7 C 0.74314(19) 0.1270(6) 0.1944(4) 0.0251(12) Uani 1 1 d . . .
C8 C 0.7486(2) 0.0742(7) 0.0944(4) 0.0337(13) Uani 1 1 d . . .
H8 H 0.7159 0.0500 0.0356 0.040 Uiso 1 1 calc R . .
C9 C 0.80121(19) 0.0567(8) 0.0802(4) 0.0342(13) Uani 1 1 d . . .
H9 H 0.8043 0.0192 0.0120 0.041 Uiso 1 1 calc R . .
C10 C 0.8490(2) 0.0930(7) 0.1636(4) 0.0298(12) Uani 1 1 d . . .
H10 H 0.8849 0.0811 0.1529 0.036 Uiso 1 1 calc R . .
C11 C 0.84474(19) 0.1473(6) 0.2641(4) 0.0255(12) Uani 1 1 d . . .
C12 C 0.79202(18) 0.1635(7) 0.2781(3) 0.0239(11) Uani 1 1 d . . .
H12 H 0.7891 0.2005 0.3466 0.029 Uiso 1 1 calc R . .
C13 C 0.89653(19) 0.1863(7) 0.3574(4) 0.0278(11) Uani 1 1 d . . .


_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 O1W 2.020(6) . ?
Ni1 O2W 2.023(7) . ?
Ni1 N1 2.048(3) 2_655 ?
Ni1 N1 2.048(3) . ?
Ni1 O1 2.067(3) 2_655 ?
Ni1 O1 2.068(3) . ?
O1W H1W 0.87(2) . ?
O1 C1 1.419(5) . ?
O1 H1O 0.85(2) . ?
O2 C13 1.267(5) . ?
O2W H2W 0.84(2) . ?
O3 C13 1.249(5) . ?
N1 C6 1.345(6) . ?
N1 C2 1.346(5) . ?
C1 C2 1.506(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.366(6) . ?
C3 C4 1.380(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(6) . ?
C4 C7 1.483(6) . ?
C5 C6 1.371(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.392(6) . ?
C7 C8 1.397(6) . ?
C8 C9 1.384(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.372(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(6) . ?
C11 C13 1.507(6) . ?
C12 H12 0.9500 . ?

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
O1W Ni1 O2W 180.000(1) . . ?
O1W Ni1 N1 91.75(12) . 2_655 ?
O2W Ni1 N1 88.25(12) . 2_655 ?
O1W Ni1 N1 91.75(12) . . ?
O2W Ni1 N1 88.25(12) . . ?
N1 Ni1 N1 176.5(2) 2_655 . ?
O1W Ni1 O1 89.54(14) . 2_655 ?
O2W Ni1 O1 90.46(14) . 2_655 ?
N1 Ni1 O1 78.55(13) 2_655 2_655 ?
N1 Ni1 O1 101.48(13) . 2_655 ?
O1W Ni1 O1 89.54(14) . . ?
O2W Ni1 O1 90.46(14) . . ?
N1 Ni1 O1 101.48(13) 2_655 . ?
N1 Ni1 O1 78.55(13) . . ?
O1 Ni1 O1 179.1(3) 2_655 . ?
Ni1 O1W H1W 119(5) . . ?
C1 O1 Ni1 114.7(3) . . ?
C1 O1 H1O 107(4) . . ?
Ni1 O1 H1O 119(4) . . ?
Ni1 O2W H2W 130(5) . . ?
C6 N1 C2 116.9(4) . . ?
C6 N1 Ni1 126.3(3) . . ?
C2 N1 Ni1 116.5(3) . . ?
O1 C1 C2 109.8(4) . . ?
O1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
O1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C3 122.4(4) . . ?
N1 C2 C1 115.8(4) . . ?
C3 C2 C1 121.9(4) . . ?
C2 C3 C4 121.1(4) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 116.5(4) . . ?
C3 C4 C7 122.9(4) . . ?
C5 C4 C7 120.6(4) . . ?
C6 C5 C4 119.6(5) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N1 C6 C5 123.4(4) . . ?
N1 C6 H6 118.3 . . ?
C5 C6 H6 118.3 . . ?
C12 C7 C8 118.0(4) . . ?
C12 C7 C4 121.3(4) . . ?
C8 C7 C4 120.7(4) . . ?
C9 C8 C7 120.6(5) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.9(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 119.2(4) . . ?
C12 C11 C13 119.8(4) . . ?
C10 C11 C13 121.0(4) . . ?
C11 C12 C7 121.6(4) . . ?
C11 C12 H12 119.2 . . ?
C7 C12 H12 119.2 . . ?
O3 C13 O2 123.6(4) . . ?
O3 C13 C11 118.5(4) . . ?
O2 C13 C11 117.9(4) . . ?

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
O1W Ni1 O1 C1 74.3(3) . . . . ?
O2W Ni1 O1 C1 -105.7(3) . . . . ?
N1 Ni1 O1 C1 165.9(3) 2_655 . . . ?
N1 Ni1 O1 C1 -17.6(4) . . . . ?
O1 Ni1 O1 C1 74.3(4) 2_655 . . . ?
O1W Ni1 N1 C6 103.3(4) . . . . ?
O2W Ni1 N1 C6 -76.7(4) . . . . ?
N1 Ni1 N1 C6 -76.7(4) 2_655 . . . ?
O1 Ni1 N1 C6 13.4(4) 2_655 . . . ?
O1 Ni1 N1 C6 -167.5(4) . . . . ?
O1W Ni1 N1 C2 -82.0(3) . . . . ?
O2W Ni1 N1 C2 98.0(3) . . . . ?
N1 Ni1 N1 C2 98.0(3) 2_655 . . . ?
O1 Ni1 N1 C2 -171.9(4) 2_655 . . . ?
O1 Ni1 N1 C2 7.2(4) . . . . ?
Ni1 O1 C1 C2 23.8(5) . . . . ?
C6 N1 C2 C3 -1.5(7) . . . . ?
Ni1 N1 C2 C3 -176.7(4) . . . . ?
C6 N1 C2 C1 179.1(4) . . . . ?
Ni1 N1 C2 C1 3.8(6) . . . . ?
O1 C1 C2 N1 -18.0(6) . . . . ?
O1 C1 C2 C3 162.6(5) . . . . ?
N1 C2 C3 C4 1.0(8) . . . . ?
C1 C2 C3 C4 -179.6(4) . . . . ?
C2 C3 C4 C5 0.3(8) . . . . ?
C2 C3 C4 C7 178.5(5) . . . . ?
C3 C4 C5 C6 -0.9(7) . . . . ?
C7 C4 C5 C6 -179.2(5) . . . . ?
C2 N1 C6 C5 0.8(7) . . . . ?
Ni1 N1 C6 C5 175.5(4) . . . . ?
C4 C5 C6 N1 0.4(8) . . . . ?
C3 C4 C7 C12 153.5(5) . . . . ?
C5 C4 C7 C12 -28.3(7) . . . . ?
C3 C4 C7 C8 -25.7(7) . . . . ?
C5 C4 C7 C8 152.4(5) . . . . ?
C12 C7 C8 C9 0.9(7) . . . . ?
C4 C7 C8 C9 -179.9(5) . . . . ?
C7 C8 C9 C10 -0.8(8) . . . . ?
C8 C9 C10 C11 0.3(8) . . . . ?
C9 C10 C11 C12 0.1(8) . . . . ?
C9 C10 C11 C13 179.4(5) . . . . ?
C10 C11 C12 C7 0.0(7) . . . . ?
C13 C11 C12 C7 -179.3(4) . . . . ?
C8 C7 C12 C11 -0.5(7) . . . . ?
C4 C7 C12 C11 -179.7(4) . . . . ?
C12 C11 C13 O3 5.1(7) . . . . ?
C10 C11 C13 O3 -174.2(5) . . . . ?
C12 C11 C13 O2 -176.2(5) . . . . ?
C10 C11 C13 O2 4.5(7) . . . . ?

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
O1W H1W O2 0.87(2) 1.82(3) 2.652(5) 160(7) 4_655
O1 H1O O3 0.85(2) 1.80(3) 2.609(5) 157(5) 8_455
O1 H1O O2 0.85(2) 2.62(5) 3.186(5) 125(4) 8_455
O2W H2W O2 0.84(2) 1.84(3) 2.671(5) 168(7) 3_445

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.092
####################################################################### 
# 
# 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_17
_database_code_depnum_ccdc_archive 'CCDC 1013154'

_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 Mn N2 O6'
_chemical_formula_sum            'C26 H20 Mn N2 O6'
_chemical_formula_weight         511.38

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.904(2)
_cell_length_b                   10.165(2)
_cell_length_c                   12.286(3)
_cell_angle_alpha                77.470(3)
_cell_angle_beta                 68.167(3)
_cell_angle_gamma                85.302(3)
_cell_volume                     1120.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4230
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.5

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             526
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8833
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           ?

_diffrn_ambient_temperature      153(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 ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20302
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.68
_reflns_number_total             4246
_reflns_number_gt                3197
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0533P)²+0.4901P] 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         4246
_refine_ls_number_parameters     322
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
Mn1 Mn 1.41206(5) 0.27301(4) 1.48462(3) 0.02749(14) Uani 1 1 d . . .
O1 O 1.3824(2) 0.0772(2) 1.45010(17) 0.0371(5) Uani 1 1 d D . .
H1O H 1.433(3) 0.032(3) 1.396(2) 0.044 Uiso 1 1 d D . .
O2 O 0.6112(2) 0.2858(2) 2.33957(17) 0.0435(5) Uani 1 1 d . . .
O3 O 0.7886(2) 0.4324(2) 2.29086(17) 0.0421(5) Uani 1 1 d . . .
O4 O 1.3156(2) 0.4694(2) 1.51941(17) 0.0391(5) Uani 1 1 d D . .
H4O H 1.297(3) 0.505(3) 1.583(2) 0.047 Uiso 1 1 d D . .
O5 O 1.5006(2) 0.0406(2) 0.72775(17) 0.0424(6) Uani 1 1 d . . .
O6 O 1.4991(2) 0.2464(2) 0.61855(16) 0.0366(5) Uani 1 1 d . . .
N1 N 1.2036(3) 0.1738(2) 1.63213(19) 0.0300(5) Uani 1 1 d . . .
N2 N 1.3161(3) 0.3674(2) 1.34252(19) 0.0289(5) Uani 1 1 d . . .
C1 C 1.2498(4) 0.0073(3) 1.5084(3) 0.0414(8) Uani 1 1 d . . .
H1A H 1.2687 -0.0906 1.5275 0.050 Uiso 1 1 calc R . .
H1B H 1.1932 0.0223 1.4552 0.050 Uiso 1 1 calc R . .
C2 C 1.1643(3) 0.0562(3) 1.6218(2) 0.0327(7) Uani 1 1 d . . .
C3 C 1.0513(3) -0.0183(3) 1.7112(3) 0.0365(7) Uani 1 1 d . . .
H3 H 1.0226 -0.1001 1.7006 0.044 Uiso 1 1 calc R . .
C4 C 0.9805(3) 0.0267(3) 1.8160(2) 0.0333(7) Uani 1 1 d . . .
H4 H 0.9042 -0.0252 1.8790 0.040 Uiso 1 1 calc R . .
C5 C 1.0206(3) 0.1485(3) 1.8299(2) 0.0251(6) Uani 1 1 d . . .
C6 C 1.1321(3) 0.2183(3) 1.7339(2) 0.0285(6) Uani 1 1 d . . .
H6 H 1.1599 0.3027 1.7404 0.034 Uiso 1 1 calc R . .
C7 C 0.9487(3) 0.1992(3) 1.9422(2) 0.0249(6) Uani 1 1 d . . .
C8 C 0.8089(3) 0.1578(3) 2.0177(3) 0.0354(7) Uani 1 1 d . . .
H8 H 0.7593 0.0983 1.9954 0.042 Uiso 1 1 calc R . .
C9 C 0.7403(3) 0.2008(3) 2.1238(2) 0.0356(7) Uani 1 1 d . . .
H9 H 0.6455 0.1688 2.1745 0.043 Uiso 1 1 calc R . .
C10 C 0.8078(3) 0.2900(3) 2.1573(2) 0.0265(6) Uani 1 1 d . . .
C11 C 0.9462(3) 0.3332(3) 2.0822(2) 0.0298(6) Uani 1 1 d . . .
H11 H 0.9937 0.3957 2.1033 0.036 Uiso 1 1 calc R . .
C12 C 1.0171(3) 0.2876(3) 1.9769(2) 0.0290(6) Uani 1 1 d . . .
H12 H 1.1133 0.3169 1.9279 0.035 Uiso 1 1 calc R . .
C13 C 0.7311(3) 0.3403(3) 2.2719(2) 0.0316(7) Uani 1 1 d . . .
C14 C 1.2252(4) 0.5389(3) 1.4590(3) 0.0383(7) Uani 1 1 d . . .
H14A H 1.2481 0.6363 1.4363 0.046 Uiso 1 1 calc R . .
H14B H 1.1220 0.5275 1.5130 0.046 Uiso 1 1 calc R . .
C15 C 1.2484(3) 0.4852(3) 1.3489(2) 0.0320(7) Uani 1 1 d . . .
C16 C 1.2042(3) 0.5548(3) 1.2582(3) 0.0380(7) Uani 1 1 d . . .
H16 H 1.1526 0.6374 1.2659 0.046 Uiso 1 1 calc R . .
C17 C 1.2353(3) 0.5039(3) 1.1564(3) 0.0367(7) Uani 1 1 d . . .
H17 H 1.2052 0.5512 1.0936 0.044 Uiso 1 1 calc R . .
C18 C 1.3110(3) 0.3827(3) 1.1457(2) 0.0268(6) Uani 1 1 d . . .
C19 C 1.3462(3) 0.3181(3) 1.2435(2) 0.0283(6) Uani 1 1 d . . .
H19 H 1.3947 0.2336 1.2399 0.034 Uiso 1 1 calc R . .
C20 C 1.3567(3) 0.3267(3) 1.0360(2) 0.0244(6) Uani 1 1 d . . .
C21 C 1.3842(3) 0.4122(3) 0.9246(2) 0.0276(6) Uani 1 1 d . . .
H21 H 1.3740 0.5068 0.9197 0.033 Uiso 1 1 calc R . .
C22 C 1.4261(3) 0.3610(3) 0.8212(2) 0.0277(6) Uani 1 1 d . . .
H22 H 1.4436 0.4207 0.7462 0.033 Uiso 1 1 calc R . .
C23 C 1.4426(3) 0.2237(3) 0.8261(2) 0.0250(6) Uani 1 1 d . . .
C24 C 1.4175(3) 0.1390(3) 0.9367(2) 0.0273(6) Uani 1 1 d . . .
H24 H 1.4300 0.0445 0.9412 0.033 Uiso 1 1 calc R . .
C25 C 1.3746(3) 0.1894(3) 1.0400(2) 0.0274(6) Uani 1 1 d . . .
H25 H 1.3572 0.1293 1.1148 0.033 Uiso 1 1 calc R . .
C26 C 1.4842(3) 0.1648(3) 0.7157(2) 0.0291(6) Uani 1 1 d . . .


_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
Mn1 O6 2.0855(19) 1_556 ?
Mn1 O2 2.100(2) 1_654 ?
Mn1 O1 2.187(2) . ?
Mn1 O4 2.198(2) . ?
Mn1 N2 2.287(2) . ?
Mn1 N1 2.309(2) . ?
O1 C1 1.405(4) . ?
O1 H1O 0.868(18) . ?
O2 C13 1.258(4) . ?
O2 Mn1 2.100(2) 1_456 ?
O3 C13 1.240(3) . ?
O4 C14 1.419(3) . ?
O4 H4O 0.879(18) . ?
O5 C26 1.243(3) . ?
O6 C26 1.262(3) . ?
O6 Mn1 2.0855(19) 1_554 ?
N1 C2 1.332(4) . ?
N1 C6 1.344(3) . ?
N2 C15 1.326(3) . ?
N2 C19 1.338(3) . ?
C1 C2 1.503(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.377(4) . ?
C3 C4 1.375(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(4) . ?
C5 C7 1.482(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(4) . ?
C7 C12 1.388(4) . ?
C8 C9 1.375(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(4) . ?
C10 C13 1.508(4) . ?
C11 C12 1.383(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 C15 1.500(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.380(4) . ?
C16 C17 1.377(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.394(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(4) . ?
C18 C20 1.477(4) . ?
C19 H19 0.9500 . ?
C20 C25 1.385(4) . ?
C20 C21 1.395(4) . ?
C21 C22 1.385(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.387(3) . ?
C23 C26 1.506(4) . ?
C24 C25 1.378(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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
O6 Mn1 O2 96.76(8) 1_556 1_654 ?
O6 Mn1 O1 109.84(8) 1_556 . ?
O2 Mn1 O1 87.07(8) 1_654 . ?
O6 Mn1 O4 93.23(8) 1_556 . ?
O2 Mn1 O4 114.13(9) 1_654 . ?
O1 Mn1 O4 146.95(9) . . ?
O6 Mn1 N2 162.96(8) 1_556 . ?
O2 Mn1 N2 84.79(8) 1_654 . ?
O1 Mn1 N2 87.17(8) . . ?
O4 Mn1 N2 70.86(7) . . ?
O6 Mn1 N1 86.42(8) 1_556 . ?
O2 Mn1 N1 157.50(9) 1_654 . ?
O1 Mn1 N1 71.00(8) . . ?
O4 Mn1 N1 87.80(8) . . ?
N2 Mn1 N1 98.66(8) . . ?
C1 O1 Mn1 121.62(17) . . ?
C1 O1 H1O 104(2) . . ?
Mn1 O1 H1O 134(2) . . ?
C13 O2 Mn1 153.5(2) . 1_456 ?
C14 O4 Mn1 121.10(16) . . ?
C14 O4 H4O 106(2) . . ?
Mn1 O4 H4O 130(2) . . ?
C26 O6 Mn1 137.17(19) . 1_554 ?
C2 N1 C6 118.5(2) . . ?
C2 N1 Mn1 117.21(18) . . ?
C6 N1 Mn1 123.69(19) . . ?
C15 N2 C19 118.6(2) . . ?
C15 N2 Mn1 119.10(17) . . ?
C19 N2 Mn1 121.41(18) . . ?
O1 C1 C2 109.6(2) . . ?
O1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
O1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C3 121.7(3) . . ?
N1 C2 C1 117.1(3) . . ?
C3 C2 C1 121.2(3) . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 116.4(2) . . ?
C6 C5 C7 121.9(2) . . ?
C4 C5 C7 121.6(2) . . ?
N1 C6 C5 123.8(3) . . ?
N1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
C8 C7 C12 117.5(2) . . ?
C8 C7 C5 120.3(2) . . ?
C12 C7 C5 122.2(2) . . ?
C9 C8 C7 121.7(3) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 118.2(2) . . ?
C11 C10 C13 121.1(3) . . ?
C9 C10 C13 120.7(3) . . ?
C10 C11 C12 121.4(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C7 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
O3 C13 O2 125.5(3) . . ?
O3 C13 C10 118.2(3) . . ?
O2 C13 C10 116.3(3) . . ?
O4 C14 C15 110.2(2) . . ?
O4 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
O4 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N2 C15 C16 121.6(2) . . ?
N2 C15 C14 116.1(2) . . ?
C16 C15 C14 122.2(3) . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 116.1(2) . . ?
C19 C18 C20 121.0(2) . . ?
C17 C18 C20 122.8(2) . . ?
N2 C19 C18 124.1(2) . . ?
N2 C19 H19 118.0 . . ?
C18 C19 H19 118.0 . . ?
C25 C20 C21 118.2(2) . . ?
C25 C20 C18 121.5(2) . . ?
C21 C20 C18 120.3(2) . . ?
C22 C21 C20 120.9(2) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 120.5(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 118.5(2) . . ?
C22 C23 C26 121.7(2) . . ?
C24 C23 C26 119.7(2) . . ?
C25 C24 C23 121.2(2) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C20 120.7(2) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?
O5 C26 O6 125.7(3) . . ?
O5 C26 C23 117.5(2) . . ?
O6 C26 C23 116.8(2) . . ?

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
O6 Mn1 O1 C1 93.2(2) 1_556 . . . ?
O2 Mn1 O1 C1 -170.7(2) 1_654 . . . ?
O4 Mn1 O1 C1 -38.5(3) . . . . ?
N2 Mn1 O1 C1 -85.8(2) . . . . ?
N1 Mn1 O1 C1 14.4(2) . . . . ?
O6 Mn1 O4 C14 -174.5(2) 1_556 . . . ?
O2 Mn1 O4 C14 86.6(2) 1_654 . . . ?
O1 Mn1 O4 C14 -39.3(3) . . . . ?
N2 Mn1 O4 C14 11.7(2) . . . . ?
N1 Mn1 O4 C14 -88.2(2) . . . . ?
O6 Mn1 N1 C2 -115.8(2) 1_556 . . . ?
O2 Mn1 N1 C2 -16.8(3) 1_654 . . . ?
O1 Mn1 N1 C2 -3.41(19) . . . . ?
O4 Mn1 N1 C2 150.8(2) . . . . ?
N2 Mn1 N1 C2 80.6(2) . . . . ?
O6 Mn1 N1 C6 55.1(2) 1_556 . . . ?
O2 Mn1 N1 C6 154.1(2) 1_654 . . . ?
O1 Mn1 N1 C6 167.5(2) . . . . ?
O4 Mn1 N1 C6 -38.3(2) . . . . ?
N2 Mn1 N1 C6 -108.6(2) . . . . ?
O6 Mn1 N2 C15 -23.7(4) 1_556 . . . ?
O2 Mn1 N2 C15 -119.8(2) 1_654 . . . ?
O1 Mn1 N2 C15 152.9(2) . . . . ?
O4 Mn1 N2 C15 -2.0(2) . . . . ?
N1 Mn1 N2 C15 82.6(2) . . . . ?
O6 Mn1 N2 C19 145.6(3) 1_556 . . . ?
O2 Mn1 N2 C19 49.6(2) 1_654 . . . ?
O1 Mn1 N2 C19 -37.8(2) . . . . ?
O4 Mn1 N2 C19 167.3(2) . . . . ?
N1 Mn1 N2 C19 -108.0(2) . . . . ?
Mn1 O1 C1 C2 -21.6(3) . . . . ?
C6 N1 C2 C3 1.4(4) . . . . ?
Mn1 N1 C2 C3 172.7(2) . . . . ?
C6 N1 C2 C1 -178.0(2) . . . . ?
Mn1 N1 C2 C1 -6.6(3) . . . . ?
O1 C1 C2 N1 17.4(4) . . . . ?
O1 C1 C2 C3 -162.0(3) . . . . ?
N1 C2 C3 C4 -2.6(5) . . . . ?
C1 C2 C3 C4 176.8(3) . . . . ?
C2 C3 C4 C5 1.7(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C3 C4 C5 C7 -178.9(3) . . . . ?
C2 N1 C6 C5 0.7(4) . . . . ?
Mn1 N1 C6 C5 -170.0(2) . . . . ?
C4 C5 C6 N1 -1.5(4) . . . . ?
C7 C5 C6 N1 177.6(2) . . . . ?
C6 C5 C7 C8 156.6(3) . . . . ?
C4 C5 C7 C8 -24.3(4) . . . . ?
C6 C5 C7 C12 -24.0(4) . . . . ?
C4 C5 C7 C12 155.1(3) . . . . ?
C12 C7 C8 C9 -0.8(4) . . . . ?
C5 C7 C8 C9 178.6(3) . . . . ?
C7 C8 C9 C10 1.6(5) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C8 C9 C10 C13 178.2(3) . . . . ?
C9 C10 C11 C12 -1.0(4) . . . . ?
C13 C10 C11 C12 -179.9(2) . . . . ?
C10 C11 C12 C7 1.8(4) . . . . ?
C8 C7 C12 C11 -0.9(4) . . . . ?
C5 C7 C12 C11 179.7(2) . . . . ?
Mn1 O2 C13 O3 12.1(6) 1_456 . . . ?
Mn1 O2 C13 C10 -166.5(3) 1_456 . . . ?
C11 C10 C13 O3 7.7(4) . . . . ?
C9 C10 C13 O3 -171.3(3) . . . . ?
C11 C10 C13 O2 -173.6(2) . . . . ?
C9 C10 C13 O2 7.4(4) . . . . ?
Mn1 O4 C14 C15 -18.5(3) . . . . ?
C19 N2 C15 C16 2.3(4) . . . . ?
Mn1 N2 C15 C16 171.9(2) . . . . ?
C19 N2 C15 C14 -176.7(3) . . . . ?
Mn1 N2 C15 C14 -7.1(3) . . . . ?
O4 C14 C15 N2 15.8(4) . . . . ?
O4 C14 C15 C16 -163.2(3) . . . . ?
N2 C15 C16 C17 -2.4(5) . . . . ?
C14 C15 C16 C17 176.5(3) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C16 C17 C18 C19 2.1(4) . . . . ?
C16 C17 C18 C20 -175.8(3) . . . . ?
C15 N2 C19 C18 0.1(4) . . . . ?
Mn1 N2 C19 C18 -169.3(2) . . . . ?
C17 C18 C19 N2 -2.3(4) . . . . ?
C20 C18 C19 N2 175.7(3) . . . . ?
C19 C18 C20 C25 29.6(4) . . . . ?
C17 C18 C20 C25 -152.5(3) . . . . ?
C19 C18 C20 C21 -149.9(3) . . . . ?
C17 C18 C20 C21 28.0(4) . . . . ?
C25 C20 C21 C22 0.9(4) . . . . ?
C18 C20 C21 C22 -179.5(2) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C21 C22 C23 C26 178.3(2) . . . . ?
C22 C23 C24 C25 1.0(4) . . . . ?
C26 C23 C24 C25 -177.8(3) . . . . ?
C23 C24 C25 C20 -0.6(4) . . . . ?
C21 C20 C25 C24 -0.4(4) . . . . ?
C18 C20 C25 C24 -179.9(2) . . . . ?
Mn1 O6 C26 O5 56.6(4) 1_554 . . . ?
Mn1 O6 C26 C23 -123.3(3) 1_554 . . . ?
C22 C23 C26 O5 178.1(3) . . . . ?
C24 C23 C26 O5 -3.1(4) . . . . ?
C22 C23 C26 O6 -2.0(4) . . . . ?
C24 C23 C26 O6 176.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O5 0.868(18) 1.715(19) 2.564(3) 165(3) 2_857
O4 H4O O3 0.879(18) 1.70(2) 2.559(3) 164(3) 2_769

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.060

##End of data17=================================================================



