# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_Zn_2901
_database_code_depnum_ccdc_archive 'CCDC 1411032'

_audit_update_record             
;
2015-07-06 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
_publcif_datablock.id            {444121af-3233-440f-982f-c4a436da0e85}
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 Fe N2 O4 Zn, H2 O'
_chemical_formula_sum            'C11 H9 Fe0.50 N O2.50 Zn0.50'
_chemical_formula_weight         255.80

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'
Fe Fe -1.1336 3.1974 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.7568(9)
_cell_length_b                   15.0687(10)
_cell_length_c                   11.1422(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1973.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6582
_cell_measurement_theta_min      2.9301
_cell_measurement_theta_max      73.6191

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    7.730
_shelx_estimated_absorpt_T_min   0.371
_shelx_estimated_absorpt_T_max   0.699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65705
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_reflns_number            13774
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.936
_diffrn_reflns_theta_max         73.778
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1988
_reflns_number_gt                1765
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;

_computing_structure_solution    'Superflip (Palatinus L., Chapuis G. (2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+0.3242P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    hetero-mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00023(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1988
_refine_ls_number_parameters     147
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.7500 0.5000 0.12260(3) 0.01618(13) Uani 1 2 d S T P . .
Fe1 Fe 0.5000 0.5000 0.5000 0.01787(14) Uani 1 2 d S . P . .
N1 N 0.74852(11) 0.40186(12) -0.00915(13) 0.0187(4) Uani 1 1 d . . . . .
C1 C 0.83896(15) 0.35134(11) -0.03426(14) 0.0212(3) Uani 1 1 d . . . . .
H1 H 0.9047 0.3565 0.0148 0.025 Uiso 1 1 calc R U . . .
C2 C 0.84051(15) 0.29187(11) -0.12898(14) 0.0206(3) Uani 1 1 d . . . . .
H2 H 0.9071 0.2584 -0.1458 0.025 Uiso 1 1 calc R U . . .
C3 C 0.74344(13) 0.28170(11) -0.19926(15) 0.0181(4) Uani 1 1 d . . . . .
C4 C 0.64840(14) 0.33292(12) -0.17151(15) 0.0240(4) Uani 1 1 d . . . . .
H4 H 0.5801 0.3268 -0.2163 0.029 Uiso 1 1 calc R U . . .
C5 C 0.65501(15) 0.39305(11) -0.07752(15) 0.0235(4) Uani 1 1 d . . . . .
H5 H 0.5909 0.4294 -0.0608 0.028 Uiso 1 1 calc R U . . .
C6 C 0.51777(14) 0.42077(10) 0.35269(14) 0.0191(3) Uani 1 1 d . . . . .
C7 C 0.40267(14) 0.45085(11) 0.36287(14) 0.0213(3) Uani 1 1 d . . . . .
H7 H 0.3599 0.4865 0.3021 0.026 Uiso 1 1 calc R U . . .
C8 C 0.35978(15) 0.42006(11) 0.47528(16) 0.0253(4) Uani 1 1 d . . . . .
H8 H 0.2818 0.4316 0.5076 0.030 Uiso 1 1 calc R U . . .
C9 C 0.44706(16) 0.37188(11) 0.53444(16) 0.0244(4) Uani 1 1 d . . . . .
H9 H 0.4412 0.3436 0.6154 0.029 Uiso 1 1 calc R U . . .
C10 C 0.54494(15) 0.37149(11) 0.45887(15) 0.0206(3) Uani 1 1 d . . . . .
H10 H 0.6195 0.3426 0.4771 0.025 Uiso 1 1 calc R U . . .
C11 C 0.60061(14) 0.44349(10) 0.25807(13) 0.0179(3) Uani 1 1 d . . . . .
O1 O 0.69923(10) 0.41016(7) 0.26427(9) 0.0201(3) Uani 1 1 d . . . . .
O2 O 0.57445(12) 0.49761(6) 0.17487(12) 0.0205(3) Uani 1 1 d . . . . .
O1W O 0.83019(16) 0.2500 0.2500 0.0313(4) Uani 1 2 d DS T P . .
H1W H 0.7798(18) 0.2950(13) 0.256(2) 0.047 Uiso 1 1 d D U . . .


_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 2.0838(16) . yes
Zn1 N1 2.0839(16) 2_665 no
Zn1 O2 2.1448(14) . yes
Zn1 O2 2.1448(14) 2_665 no
Zn1 O1 2.1636(11) 2_665 ?
Zn1 O1 2.1636(11) . yes
Zn1 O1 2.1636(11) 1 ?
Zn1 C11 2.4674(16) 2_665 ?
Zn1 C11 2.4675(16) . ?
Fe1 C6 2.0403(15) . ?
Fe1 C6 2.0404(15) 5_666 ?
Fe1 C7 2.0476(16) . ?
Fe1 C7 2.0476(16) 5_666 ?
Fe1 C10 2.0589(16) 5_666 ?
Fe1 C10 2.0589(16) . ?
Fe1 C8 2.0602(17) 5_666 ?
Fe1 C8 2.0603(17) . ?
Fe1 C9 2.0644(16) . ?
Fe1 C9 2.0644(17) 5_666 ?
N1 C1 1.337(2) . yes
N1 C5 1.344(2) . yes
C1 C2 1.385(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.393(2) . ?
C3 C3 1.480(3) 3_554 ?
C4 C5 1.387(2) . ?
C6 C7 1.432(2) . ?
C6 C10 1.433(2) . ?
C6 C11 1.476(2) . ?
C7 C8 1.428(2) . ?
C8 C9 1.419(3) . ?
C9 C10 1.426(3) . ?
C11 O1 1.265(2) 1 ?
C11 O1 1.265(2) . yes
C11 O2 1.272(2) . yes
O1 O1 0.000(3) 1 ?

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 90.43(9) . 2_665 yes
N1 Zn1 O2 99.86(5) . . yes
N1 Zn1 O2 102.19(5) 2_665 . yes
N1 Zn1 O2 102.20(5) . 2_665 ?
N1 Zn1 O2 99.86(5) 2_665 2_665 ?
O2 Zn1 O2 148.49(7) . 2_665 yes
N1 Zn1 O1 163.82(5) . 2_665 yes
N1 Zn1 O1 93.88(5) 2_665 2_665 yes
O2 Zn1 O1 94.47(4) . 2_665 yes
O2 Zn1 O1 61.70(4) 2_665 2_665 ?
N1 Zn1 O1 93.88(5) . . ?
N1 Zn1 O1 163.82(5) 2_665 . ?
O2 Zn1 O1 61.70(4) . . yes
O2 Zn1 O1 94.47(4) 2_665 . ?
O1 Zn1 O1 86.29(6) 2_665 . ?
N1 Zn1 O1 93.88(5) . 1 ?
N1 Zn1 O1 163.82(5) 2_665 1 ?
O2 Zn1 O1 61.70(4) . 1 ?
O2 Zn1 O1 94.47(4) 2_665 1 ?
O1 Zn1 O1 86.29(6) 2_665 1 ?
O1 Zn1 O1 0.00(8) . 1 ?
N1 Zn1 C11 132.98(5) . 2_665 ?
N1 Zn1 C11 100.37(5) 2_665 2_665 ?
O2 Zn1 C11 121.65(5) . 2_665 ?
O2 Zn1 C11 31.03(5) 2_665 2_665 ?
O1 Zn1 C11 30.83(5) 2_665 2_665 ?
O1 Zn1 C11 88.05(4) . 2_665 ?
O1 Zn1 C11 88.05(4) 1 2_665 ?
N1 Zn1 C11 100.37(5) . . ?
N1 Zn1 C11 132.99(5) 2_665 . ?
O2 Zn1 C11 31.03(5) . . ?
O2 Zn1 C11 121.65(5) 2_665 . ?
O1 Zn1 C11 88.05(4) 2_665 . ?
O1 Zn1 C11 30.83(5) . . ?
O1 Zn1 C11 30.83(5) 1 . ?
C11 Zn1 C11 104.57(7) 2_665 . ?
C6 Fe1 C6 180.00(9) . 5_666 ?
C6 Fe1 C7 41.00(7) . . ?
C6 Fe1 C7 139.00(7) 5_666 . ?
C6 Fe1 C7 139.00(7) . 5_666 ?
C6 Fe1 C7 41.00(7) 5_666 5_666 ?
C7 Fe1 C7 180.00(8) . 5_666 ?
C6 Fe1 C10 139.08(6) . 5_666 ?
C6 Fe1 C10 40.91(6) 5_666 5_666 ?
C7 Fe1 C10 111.28(7) . 5_666 ?
C7 Fe1 C10 68.72(7) 5_666 5_666 ?
C6 Fe1 C10 40.92(6) . . ?
C6 Fe1 C10 139.08(6) 5_666 . ?
C7 Fe1 C10 68.72(7) . . ?
C7 Fe1 C10 111.28(7) 5_666 . ?
C10 Fe1 C10 180.0 5_666 . ?
C6 Fe1 C8 111.58(7) . 5_666 ?
C6 Fe1 C8 68.42(7) 5_666 5_666 ?
C7 Fe1 C8 139.33(7) . 5_666 ?
C7 Fe1 C8 40.67(7) 5_666 5_666 ?
C10 Fe1 C8 68.01(7) 5_666 5_666 ?
C10 Fe1 C8 111.99(7) . 5_666 ?
C6 Fe1 C8 68.42(7) . . ?
C6 Fe1 C8 111.58(7) 5_666 . ?
C7 Fe1 C8 40.67(7) . . ?
C7 Fe1 C8 139.33(7) 5_666 . ?
C10 Fe1 C8 111.99(7) 5_666 . ?
C10 Fe1 C8 68.01(7) . . ?
C8 Fe1 C8 180.0 5_666 . ?
C6 Fe1 C9 68.48(7) . . ?
C6 Fe1 C9 111.52(7) 5_666 . ?
C7 Fe1 C9 68.41(7) . . ?
C7 Fe1 C9 111.59(7) 5_666 . ?
C10 Fe1 C9 139.54(8) 5_666 . ?
C10 Fe1 C9 40.46(8) . . ?
C8 Fe1 C9 139.75(7) 5_666 . ?
C8 Fe1 C9 40.25(7) . . ?
C6 Fe1 C9 111.52(7) . 5_666 ?
C6 Fe1 C9 68.48(7) 5_666 5_666 ?
C7 Fe1 C9 111.59(7) . 5_666 ?
C7 Fe1 C9 68.40(7) 5_666 5_666 ?
C10 Fe1 C9 40.46(8) 5_666 5_666 ?
C10 Fe1 C9 139.54(8) . 5_666 ?
C8 Fe1 C9 40.25(7) 5_666 5_666 ?
C8 Fe1 C9 139.75(7) . 5_666 ?
C9 Fe1 C9 180.0 . 5_666 ?
C1 N1 C5 118.39(15) . . ?
C1 N1 Zn1 123.01(11) . . ?
C5 N1 Zn1 118.44(12) . . ?
N1 C1 C2 122.57(15) . . ?
C1 C2 C3 119.28(16) . . ?
C2 C3 C4 118.15(16) . . ?
C2 C3 C3 120.04(11) . 3_554 ?
C4 C3 C3 121.82(11) . 3_554 ?
C5 C4 C3 118.99(16) . . ?
N1 C5 C4 122.57(16) . . ?
C7 C6 C10 108.02(15) . . ?
C7 C6 C11 127.37(15) . . ?
C10 C6 C11 124.27(15) . . ?
C7 C6 Fe1 69.77(9) . . ?
C10 C6 Fe1 70.24(9) . . ?
C11 C6 Fe1 120.44(11) . . ?
C8 C7 C6 107.48(15) . . ?
C8 C7 Fe1 70.14(9) . . ?
C6 C7 Fe1 69.23(9) . . ?
C9 C8 C7 108.57(15) . . ?
C9 C8 Fe1 70.03(10) . . ?
C7 C8 Fe1 69.19(9) . . ?
C8 C9 C10 108.14(16) . . ?
C8 C9 Fe1 69.72(10) . . ?
C10 C9 Fe1 69.56(8) . . ?
C9 C10 C6 107.79(16) . . ?
C9 C10 Fe1 69.97(8) . . ?
C6 C10 Fe1 68.85(9) . . ?
O1 C11 O1 0.00(13) 1 . ?
O1 C11 O2 121.04(14) 1 . yes
O1 C11 O2 121.04(14) . . ?
O1 C11 C6 118.27(14) 1 . ?
O1 C11 C6 118.27(14) . . ?
O2 C11 C6 120.65(15) . . ?
O1 C11 Zn1 61.20(8) 1 . ?
O1 C11 Zn1 61.20(8) . . ?
O2 C11 Zn1 60.34(9) . . ?
C6 C11 Zn1 170.74(11) . . ?
O1 O1 C11 0(10) 1 . ?
O1 O1 Zn1 0(7) 1 . ?
C11 O1 Zn1 87.97(9) . . ?
C11 O2 Zn1 88.63(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
O2 Zn1 O1 C11 -4.68(8) . . . . no
N1 Zn1 O1 C11 -103.81(9) . . . . no
O1 Zn1 O1 C11 92.41(9) 2_665 . . . no
O2 Zn1 O1 C11 153.62(9) 2_665 . . . no
C11 Zn1 O1 C11 123.24(9) 2_665 . . . no
O1 Zn1 O2 C11 4.66(8) . . . . no
N1 Zn1 O2 C11 93.76(10) . . . . no
O1 Zn1 O2 C11 -78.70(9) 2_665 . . . no
O2 Zn1 O2 C11 -40.18(11) 2_665 . . . no
N1 Zn1 O2 C11 -173.65(9) 2_665 . . . no
C11 Zn1 O2 C11 -63.18(10) 2_665 . . . no
O1 Zn1 N1 C1 -88.56(14) . . . . no
O1 Zn1 N1 C5 96.14(13) . . . . no
O2 Zn1 N1 C1 -150.49(14) . . . . no
O2 Zn1 N1 C5 34.21(14) . . . . no
C11 Zn1 N1 C1 -118.96(14) . . . . no
C11 Zn1 N1 C5 65.74(14) . . . . no
O2 Zn1 N1 C1 6.86(15) 2_665 . . . no
O2 Zn1 N1 C5 -168.44(13) 2_665 . . . no
N1 Zn1 N1 C1 107.05(14) 2_665 . . . no
N1 Zn1 N1 C5 -68.25(13) 2_665 . . . no
C11 Zn1 N1 C1 2.39(18) 2_665 . . . no
C11 Zn1 N1 C5 -172.91(11) 2_665 . . . no
O1 Zn1 C11 O2 -171.98(14) . . . . no
O2 Zn1 C11 O1 171.98(14) . . . . no
N1 Zn1 C11 O1 80.06(9) . . . . no
N1 Zn1 C11 O2 -91.92(9) . . . . no
O1 Zn1 C11 O1 -86.03(8) 2_665 . . . no
O1 Zn1 C11 O2 101.99(9) 2_665 . . . no
O2 Zn1 C11 O1 -31.35(10) 2_665 . . . no
O2 Zn1 C11 O2 156.66(8) 2_665 . . . no
N1 Zn1 C11 O1 -179.51(9) 2_665 . . . no
N1 Zn1 C11 O2 8.50(12) 2_665 . . . no
C11 Zn1 C11 O1 -59.74(9) 2_665 . . . no
C11 Zn1 C11 O2 128.28(9) 2_665 . . . no
C7 Fe1 C6 C10 -118.87(13) . . . . no
C7 Fe1 C6 C11 122.27(16) . . . . no
C8 Fe1 C6 C7 37.98(9) . . . . no
C8 Fe1 C6 C10 -80.89(10) . . . . no
C8 Fe1 C6 C11 160.24(14) . . . . no
C9 Fe1 C6 C7 81.41(10) . . . . no
C9 Fe1 C6 C10 -37.46(10) . . . . no
C9 Fe1 C6 C11 -156.33(15) . . . . no
C10 Fe1 C6 C7 118.87(13) . . . . no
C10 Fe1 C6 C11 -118.87(17) . . . . no
C7 Fe1 C6 C7 -179.98(10) 5_666 . . . no
C7 Fe1 C6 C10 61.13(13) 5_666 . . . no
C7 Fe1 C6 C11 -57.74(16) 5_666 . . . no
C8 Fe1 C6 C7 -142.02(9) 5_666 . . . no
C8 Fe1 C6 C10 99.11(10) 5_666 . . . no
C8 Fe1 C6 C11 -19.76(14) 5_666 . . . no
C9 Fe1 C6 C7 -98.60(10) 5_666 . . . no
C9 Fe1 C6 C10 142.54(10) 5_666 . . . no
C9 Fe1 C6 C11 23.67(15) 5_666 . . . no
C10 Fe1 C6 C7 -61.13(13) 5_666 . . . no
C10 Fe1 C6 C10 -180.00(11) 5_666 . . . no
C10 Fe1 C6 C11 61.13(17) 5_666 . . . no
C6 Fe1 C7 C8 118.60(13) . . . . no
C8 Fe1 C7 C6 -118.60(13) . . . . no
C9 Fe1 C7 C6 -81.61(10) . . . . no
C9 Fe1 C7 C8 36.99(10) . . . . no
C10 Fe1 C7 C6 -37.99(9) . . . . no
C10 Fe1 C7 C8 80.61(10) . . . . no
C6 Fe1 C7 C6 -179.98(12) 5_666 . . . no
C6 Fe1 C7 C8 -61.40(13) 5_666 . . . no
C8 Fe1 C7 C6 61.40(13) 5_666 . . . no
C8 Fe1 C7 C8 -179.98(11) 5_666 . . . no
C9 Fe1 C7 C6 98.39(10) 5_666 . . . no
C9 Fe1 C7 C8 -143.01(10) 5_666 . . . no
C10 Fe1 C7 C6 142.01(9) 5_666 . . . no
C10 Fe1 C7 C8 -99.39(10) 5_666 . . . no
C6 Fe1 C8 C7 -38.27(9) . . . . no
C6 Fe1 C8 C9 81.76(11) . . . . no
C7 Fe1 C8 C9 120.03(14) . . . . no
C9 Fe1 C8 C7 -120.03(14) . . . . no
C10 Fe1 C8 C7 -82.49(10) . . . . no
C10 Fe1 C8 C9 37.54(10) . . . . no
C6 Fe1 C8 C7 141.73(9) 5_666 . . . no
C6 Fe1 C8 C9 -98.24(11) 5_666 . . . no
C7 Fe1 C8 C7 179.98(11) 5_666 . . . no
C7 Fe1 C8 C9 -59.97(14) 5_666 . . . no
C9 Fe1 C8 C7 59.97(14) 5_666 . . . no
C9 Fe1 C8 C9 180.00(11) 5_666 . . . no
C10 Fe1 C8 C7 97.51(10) 5_666 . . . no
C10 Fe1 C8 C9 -142.46(10) 5_666 . . . no
C6 Fe1 C9 C8 -81.60(11) . . . . no
C6 Fe1 C9 C10 37.87(10) . . . . no
C7 Fe1 C9 C8 -37.36(10) . . . . no
C7 Fe1 C9 C10 82.11(11) . . . . no
C8 Fe1 C9 C10 119.47(15) . . . . no
C10 Fe1 C9 C8 -119.47(15) . . . . no
C6 Fe1 C9 C8 98.40(11) 5_666 . . . no
C6 Fe1 C9 C10 -142.13(10) 5_666 . . . no
C7 Fe1 C9 C8 142.64(10) 5_666 . . . no
C7 Fe1 C9 C10 -97.89(11) 5_666 . . . no
C8 Fe1 C9 C8 180.00(10) 5_666 . . . no
C8 Fe1 C9 C10 -60.53(15) 5_666 . . . no
C10 Fe1 C9 C8 60.53(15) 5_666 . . . no
C10 Fe1 C9 C10 180.00(10) 5_666 . . . no
C6 Fe1 C10 C9 -119.32(14) . . . . no
C7 Fe1 C10 C6 38.07(10) . . . . no
C7 Fe1 C10 C9 -81.25(11) . . . . no
C8 Fe1 C10 C6 81.97(10) . . . . no
C8 Fe1 C10 C9 -37.35(10) . . . . no
C9 Fe1 C10 C6 119.32(14) . . . . no
C6 Fe1 C10 C6 180.00(9) 5_666 . . . no
C6 Fe1 C10 C9 60.68(14) 5_666 . . . no
C7 Fe1 C10 C6 -141.94(10) 5_666 . . . no
C7 Fe1 C10 C9 98.75(11) 5_666 . . . no
C8 Fe1 C10 C6 -98.03(10) 5_666 . . . no
C8 Fe1 C10 C9 142.65(10) 5_666 . . . no
C9 Fe1 C10 C6 -60.68(14) 5_666 . . . no
C9 Fe1 C10 C9 -180.00(10) 5_666 . . . no
Zn1 O1 C11 O2 8.13(14) . . . . no
Zn1 O1 C11 C6 -169.48(13) . . . . no
Zn1 O2 C11 O1 -8.20(14) . . . . no
Zn1 O2 C11 C6 169.36(13) . . . . no
Zn1 N1 C1 C2 -174.04(13) . . . . no
C5 N1 C1 C2 1.3(3) . . . . no
Zn1 N1 C5 C4 176.47(13) . . . . no
C1 N1 C5 C4 1.0(3) . . . . no
N1 C1 C2 C3 -2.0(3) . . . . no
C1 C2 C3 C3 -179.87(15) . . . 3_554 no
C1 C2 C3 C4 0.6(2) . . . . no
C2 C3 C4 C5 1.5(2) . . . . no
C4 C3 C3 C4 -38.5(2) . . 3_554 3_554 yes
C4 C3 C3 C2 141.97(17) . . 3_554 3_554 no
C3 C3 C4 C5 -178.07(16) 3_554 . . . no
C2 C3 C3 C2 -37.6(2) . . 3_554 3_554 no
C2 C3 C3 C4 141.97(17) . . 3_554 3_554 no
C3 C4 C5 N1 -2.3(3) . . . . no
C10 C6 C7 Fe1 60.08(11) . . . . no
C10 C6 C7 C8 0.10(18) . . . . no
Fe1 C6 C7 C8 -59.97(11) . . . . no
C7 C6 C10 C9 -0.43(18) . . . . no
C11 C6 C10 Fe1 113.99(15) . . . . no
C11 C6 C10 C9 173.34(15) . . . . no
C11 C6 C7 Fe1 -113.45(16) . . . . no
C11 C6 C7 C8 -173.42(15) . . . . no
Fe1 C6 C10 C9 59.35(12) . . . . no
C7 C6 C10 Fe1 -59.78(11) . . . . no
C10 C6 C11 O1 7.4(2) . . . . no
C10 C6 C11 O2 -170.18(15) . . . . no
Fe1 C6 C11 O2 -84.44(17) . . . . no
C7 C6 C11 O1 179.98(14) . . . . no
Fe1 C6 C11 O1 93.18(15) . . . . no
C7 C6 C11 O2 2.4(2) . . . . no
Fe1 C7 C8 C9 -59.13(12) . . . . no
C6 C7 C8 Fe1 59.40(11) . . . . no
C6 C7 C8 C9 0.27(19) . . . . no
Fe1 C8 C9 C10 -59.15(12) . . . . no
C7 C8 C9 Fe1 58.61(12) . . . . no
C7 C8 C9 C10 -0.53(19) . . . . no
C8 C9 C10 Fe1 59.24(12) . . . . no
C8 C9 C10 C6 0.59(19) . . . . no
Fe1 C9 C10 C6 -58.65(11) . . . . no

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
_geom_hbond_publ_flag
O1W H1W O1 0.902(16) 1.979(17) 2.8671(15) 167(2) 1 yes
C5 H5 O2 0.9500 2.5700 3.342(2) 139.00 . yes
C9 H9 O1W 1.0000 2.4400 3.3211(19) 147.00 . yes

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-3


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
####################################################################### 
# 
# 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_Cu_struct
_database_code_depnum_ccdc_archive 'CCDC 1411033'

_audit_update_record             
;
2015-07-06 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
_publcif_datablock.id            {4187f1bd-782a-4a73-8ef5-88758b338c63}
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 Cu Fe N2 O4, H2O'
_chemical_formula_sum            'C11 H9 Cu0.50 Fe0.50 N O2.50'
_chemical_formula_weight         254.89

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'
Fe Fe 0.3463 0.8444 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.016(2)
_cell_length_b                   14.441(2)
_cell_length_c                   11.1347(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1932.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3232
_cell_measurement_theta_min      2.8155
_cell_measurement_theta_max      29.9213


_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_F_000             1036
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.891
_shelx_estimated_absorpt_T_min   0.752
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_T_min  0.90791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_reflns_number            11779
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.821
_diffrn_reflns_theta_max         29.987
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2476
_reflns_number_gt                1810
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'Superflip (Palatinus L., Chapuis G. (2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+2.0649P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0003(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2476
_refine_ls_number_parameters     147
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1416
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.7500 0.5000 0.12505(4) 0.01179(19) Uani 1 2 d S T P . .
Fe1 Fe 0.5000 0.5000 0.5000 0.0149(2) Uani 1 2 d S . P . .
N1 N 0.7390(2) 0.40283(19) -0.0023(2) 0.0156(6) Uani 1 1 d . . . . .
C1 C 0.8290(3) 0.35400(19) -0.0327(3) 0.0178(6) Uani 1 1 d . . . . .
H1 H 0.8948 0.3606 0.0138 0.021 Uiso 1 1 calc R U . . .
C2 C 0.8299(3) 0.2944(2) -0.1294(3) 0.0184(6) Uani 1 1 d . . . . .
H2 H 0.8959 0.2615 -0.1491 0.022 Uiso 1 1 calc R U . . .
C3 C 0.7346(2) 0.2822(2) -0.1980(3) 0.0155(6) Uani 1 1 d . . . . .
C4 C 0.6399(2) 0.3317(2) -0.1646(3) 0.0193(6) Uani 1 1 d . . . . .
H4 H 0.5719 0.3243 -0.2071 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6469(2) 0.3921(2) -0.0679(3) 0.0190(6) Uani 1 1 d . . . . .
H5 H 0.5831 0.4276 -0.0474 0.023 Uiso 1 1 calc R U . . .
C6 C 0.5140(3) 0.4198(2) 0.3505(3) 0.0172(6) Uani 1 1 d . . . . .
C7 C 0.4016(3) 0.4495(2) 0.3661(3) 0.0190(6) Uani 1 1 d . . . . .
H7 H 0.3570 0.4870 0.3080 0.023 Uiso 1 1 calc R U . . .
C8 C 0.3644(3) 0.4156(2) 0.4795(3) 0.0217(7) Uani 1 1 d . . . . .
H8 H 0.2891 0.4262 0.5153 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4528(3) 0.3657(2) 0.5340(3) 0.0215(7) Uani 1 1 d . . . . .
H9 H 0.4507 0.3351 0.6145 0.026 Uiso 1 1 calc R U . . .
C10 C 0.5451(3) 0.3673(2) 0.4541(3) 0.0181(6) Uani 1 1 d . . . . .
H10 H 0.6194 0.3381 0.4687 0.022 Uiso 1 1 calc R U . . .
C11 C 0.5887(2) 0.44927(19) 0.2522(2) 0.0148(6) Uani 1 1 d . . . . .
O1 O 0.68812(17) 0.41795(13) 0.25245(17) 0.0169(5) Uani 1 1 d . . . . .
O2 O 0.5553(2) 0.50467(13) 0.1737(2) 0.0210(5) Uani 1 1 d . . . . .
O1W O 0.8193(3) 0.2500 0.2500 0.0289(8) Uani 1 2 d DS T P . .
H1W H 0.769(3) 0.297(2) 0.254(4) 0.043 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.992(2) 2_665 ?
Cu1 O1 1.9923(19) 1 ?
Cu1 O1 1.9923(19) . yes
Cu1 N1 1.999(3) . yes
Cu1 N1 1.999(3) 2_665 ?
Cu1 O2 2.402(2) 2_665 ?
Cu1 O2 2.402(2) . yes
Cu1 C11 2.509(3) 2_665 ?
Cu1 C11 2.509(3) . ?
Fe1 C6 2.035(3) . ?
Fe1 C6 2.035(3) 5_666 ?
Fe1 C7 2.038(3) 5_666 ?
Fe1 C7 2.038(3) . ?
Fe1 C8 2.047(3) . ?
Fe1 C8 2.047(3) 5_666 ?
Fe1 C9 2.056(3) . ?
Fe1 C9 2.056(3) 5_666 ?
Fe1 C10 2.056(3) . ?
Fe1 C10 2.056(3) 5_666 ?
N1 C1 1.335(4) . yes
N1 C5 1.336(4) . yes
C1 C2 1.379(4) . ?
C2 C3 1.388(4) . ?
C3 C4 1.395(4) . ?
C3 C3 1.484(6) 3_554 ?
C4 C5 1.388(4) . ?
C6 C7 1.428(4) . ?
C6 C10 1.430(4) . ?
C6 C11 1.478(4) . ?
C7 C8 1.426(4) . ?
C8 C9 1.420(5) . ?
C9 C10 1.422(5) . ?
C11 O2 1.251(3) . yes
C11 O1 1.277(4) 1 ?
C11 O1 1.277(4) . yes
O1 O1 0.000(6) 1 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag

O1 Cu1 O1 89.20(12) 2_665 1 ?
O1 Cu1 O1 89.20(12) 2_665 . yes
O1 Cu1 O1 0.00(14) . . ?
O1 Cu1 N1 161.27(9) 2_665 . yes
O1 Cu1 N1 93.60(9) 1 . yes
O1 Cu1 N1 93.60(9) . . yes
O1 Cu1 N1 93.60(9) 2_665 2_665 ?
O1 Cu1 N1 161.27(9) 1 2_665 ?
O1 Cu1 N1 161.27(9) . 2_665 ?
N1 Cu1 N1 89.67(16) . 2_665 yes
O1 Cu1 O2 59.51(8) 2_665 2_665 ?
O1 Cu1 O2 100.73(8) 1 2_665 yes
O1 Cu1 O2 100.73(8) . 2_665 ?
N1 Cu1 O2 101.80(8) . 2_665 ?
N1 Cu1 O2 96.63(9) 2_665 2_665 ?
O1 Cu1 O2 100.73(8) 2_665 . ?
O1 Cu1 O2 59.51(8) 1 . yes
O1 Cu1 O2 59.51(8) . . yes
N1 Cu1 O2 96.63(9) . . yes
N1 Cu1 O2 101.80(8) 2_665 . ?
O2 Cu1 O2 153.92(11) 2_665 . yes
O1 Cu1 C11 30.28(9) 2_665 2_665 ?
O1 Cu1 C11 93.45(8) 1 2_665 ?
O1 Cu1 C11 93.45(8) . 2_665 ?
N1 Cu1 C11 130.99(9) . 2_665 ?
N1 Cu1 C11 98.29(9) 2_665 2_665 ?
O2 Cu1 C11 29.40(8) 2_665 2_665 ?
O2 Cu1 C11 128.07(9) . 2_665 ?
O1 Cu1 C11 93.45(8) 2_665 . ?
O1 Cu1 C11 30.28(9) 1 . ?
O1 Cu1 C11 30.28(9) . . ?
N1 Cu1 C11 98.29(9) . . ?
N1 Cu1 C11 130.99(9) 2_665 . ?
O2 Cu1 C11 128.07(9) 2_665 . ?
O2 Cu1 C11 29.40(8) . . ?
C11 Cu1 C11 111.31(13) 2_665 . ?
C6 Fe1 C6 180.0 . 5_666 ?
C6 Fe1 C7 138.96(12) . 5_666 ?
C6 Fe1 C7 41.04(12) 5_666 5_666 ?
C6 Fe1 C7 41.04(12) . . ?
C6 Fe1 C7 138.96(12) 5_666 . ?
C7 Fe1 C7 180.00(14) 5_666 . ?
C6 Fe1 C8 68.65(12) . . ?
C6 Fe1 C8 111.35(12) 5_666 . ?
C7 Fe1 C8 139.15(12) 5_666 . ?
C7 Fe1 C8 40.85(12) . . ?
C6 Fe1 C8 111.35(12) . 5_666 ?
C6 Fe1 C8 68.65(12) 5_666 5_666 ?
C7 Fe1 C8 40.85(12) 5_666 5_666 ?
C7 Fe1 C8 139.15(12) . 5_666 ?
C8 Fe1 C8 180.0 . 5_666 ?
C6 Fe1 C9 68.68(12) . . ?
C6 Fe1 C9 111.32(12) 5_666 . ?
C7 Fe1 C9 111.30(12) 5_666 . ?
C7 Fe1 C9 68.70(12) . . ?
C8 Fe1 C9 40.49(13) . . ?
C8 Fe1 C9 139.51(13) 5_666 . ?
C6 Fe1 C9 111.32(12) . 5_666 ?
C6 Fe1 C9 68.68(12) 5_666 5_666 ?
C7 Fe1 C9 68.70(12) 5_666 5_666 ?
C7 Fe1 C9 111.30(12) . 5_666 ?
C8 Fe1 C9 139.51(13) . 5_666 ?
C8 Fe1 C9 40.49(13) 5_666 5_666 ?
C9 Fe1 C9 180.0 . 5_666 ?
C6 Fe1 C10 40.91(12) . . ?
C6 Fe1 C10 139.09(12) 5_666 . ?
C7 Fe1 C10 111.28(12) 5_666 . ?
C7 Fe1 C10 68.72(12) . . ?
C8 Fe1 C10 68.11(12) . . ?
C8 Fe1 C10 111.89(12) 5_666 . ?
C9 Fe1 C10 40.46(13) . . ?
C9 Fe1 C10 139.54(13) 5_666 . ?
C6 Fe1 C10 139.09(12) . 5_666 ?
C6 Fe1 C10 40.91(12) 5_666 5_666 ?
C7 Fe1 C10 68.72(12) 5_666 5_666 ?
C7 Fe1 C10 111.28(12) . 5_666 ?
C8 Fe1 C10 111.89(12) . 5_666 ?
C8 Fe1 C10 68.11(12) 5_666 5_666 ?
C9 Fe1 C10 139.54(13) . 5_666 ?
C9 Fe1 C10 40.46(13) 5_666 5_666 ?
C10 Fe1 C10 180.0 . 5_666 ?
C1 N1 C5 118.1(3) . . ?
C1 N1 Cu1 119.9(2) . . ?
C5 N1 Cu1 121.6(2) . . ?
N1 C1 C2 122.3(3) . . ?
C1 C2 C3 120.2(3) . . ?
C2 C3 C4 117.4(3) . . ?
C2 C3 C3 120.60(19) . 3_554 ?
C4 C3 C3 121.97(19) . 3_554 ?
C5 C4 C3 118.7(3) . . ?
N1 C5 C4 123.2(3) . . ?
C7 C6 C10 107.9(3) . . ?
C7 C6 C11 125.3(3) . . ?
C10 C6 C11 126.3(3) . . ?
C7 C6 Fe1 69.57(17) . . ?
C10 C6 Fe1 70.32(16) . . ?
C11 C6 Fe1 119.5(2) . . ?
C8 C7 C6 107.6(3) . . ?
C8 C7 Fe1 69.94(17) . . ?
C6 C7 Fe1 69.39(17) . . ?
C9 C8 C7 108.5(3) . . ?
C9 C8 Fe1 70.07(17) . . ?
C7 C8 Fe1 69.21(17) . . ?
C8 C9 C10 107.9(3) . . ?
C8 C9 Fe1 69.44(17) . . ?
C10 C9 Fe1 69.78(15) . . ?
C9 C10 C6 108.1(3) . . ?
C9 C10 Fe1 69.77(16) . . ?
C6 C10 Fe1 68.77(16) . . ?
O2 C11 O1 121.9(3) . 1 ?
O2 C11 O1 121.9(3) . . yes
O1 C11 O1 0.0(2) 1 . ?
O2 C11 C6 120.5(3) . . ?
O1 C11 C6 117.7(2) 1 . ?
O1 C11 C6 117.7(2) . . ?
O2 C11 Cu1 70.54(16) . . ?
O1 C11 Cu1 51.86(13) 1 . ?
O1 C11 Cu1 51.86(13) . . ?
C6 C11 Cu1 166.1(2) . . ?
O1 O1 C11 0(10) 1 . ?
O1 O1 Cu1 0(10) 1 . ?
C11 O1 Cu1 97.86(17) . . ?
C11 O2 Cu1 80.05(18) . . ?





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 C11 -4.73(14) . . . . no
N1 Cu1 O1 C11 -100.29(16) . . . . no
O1 Cu1 O1 C11 98.24(16) 2_665 . . . no
O2 Cu1 O1 C11 156.97(15) 2_665 . . . no
C11 Cu1 O1 C11 128.23(16) 2_665 . . . no
O1 Cu1 O2 C11 4.85(15) . . . . no
N1 Cu1 O2 C11 95.15(16) . . . . no
O1 Cu1 O2 C11 -77.79(16) 2_665 . . . no
O2 Cu1 O2 C11 -39.8(2) 2_665 . . . no
N1 Cu1 O2 C11 -173.82(16) 2_665 . . . no
C11 Cu1 O2 C11 -63.28(18) 2_665 . . . no
O1 Cu1 N1 C1 -99.1(2) . . . . no
O1 Cu1 N1 C5 88.5(2) . . . . no
O2 Cu1 N1 C1 -158.8(2) . . . . no
O2 Cu1 N1 C5 28.8(2) . . . . no
C11 Cu1 N1 C1 -129.2(2) . . . . no
C11 Cu1 N1 C5 58.4(2) . . . . no
O2 Cu1 N1 C1 2.6(2) 2_665 . . . no
O2 Cu1 N1 C5 -169.7(2) 2_665 . . . no
N1 Cu1 N1 C1 99.3(2) 2_665 . . . no
N1 Cu1 N1 C5 -73.0(2) 2_665 . . . no
C11 Cu1 N1 C1 -1.4(3) 2_665 . . . no
C11 Cu1 N1 C5 -173.7(2) 2_665 . . . no
O1 Cu1 C11 O2 -171.7(2) . . . . no
O2 Cu1 C11 O1 171.7(2) . . . . no
N1 Cu1 C11 O1 82.91(16) . . . . no
N1 Cu1 C11 O2 -88.78(16) . . . . no
O1 Cu1 C11 O1 -82.47(16) 2_665 . . . no
O1 Cu1 C11 O2 105.84(15) 2_665 . . . no
O2 Cu1 C11 O1 -29.23(19) 2_665 . . . no
O2 Cu1 C11 O2 159.08(13) 2_665 . . . no
N1 Cu1 C11 O1 179.72(15) 2_665 . . . no
N1 Cu1 C11 O2 8.0(2) 2_665 . . . no
C11 Cu1 C11 O1 -57.31(17) 2_665 . . . no
C11 Cu1 C11 O2 131.00(15) 2_665 . . . no
C7 Fe1 C6 C10 -118.8(3) . . . . no
C7 Fe1 C6 C11 119.9(3) . . . . no
C8 Fe1 C6 C7 38.04(18) . . . . no
C8 Fe1 C6 C10 -80.8(2) . . . . no
C8 Fe1 C6 C11 157.9(3) . . . . no
C9 Fe1 C6 C7 81.7(2) . . . . no
C9 Fe1 C6 C10 -37.2(2) . . . . no
C9 Fe1 C6 C11 -158.5(3) . . . . no
C10 Fe1 C6 C7 118.8(3) . . . . no
C10 Fe1 C6 C11 -121.3(3) . . . . no
C7 Fe1 C6 C7 180.0(2) 5_666 . . . no
C7 Fe1 C6 C10 61.2(3) 5_666 . . . no
C7 Fe1 C6 C11 -60.1(3) 5_666 . . . no
C8 Fe1 C6 C7 -141.96(18) 5_666 . . . no
C8 Fe1 C6 C10 99.2(2) 5_666 . . . no
C8 Fe1 C6 C11 -22.1(3) 5_666 . . . no
C9 Fe1 C6 C7 -98.4(2) 5_666 . . . no
C9 Fe1 C6 C10 142.8(2) 5_666 . . . no
C9 Fe1 C6 C11 21.5(3) 5_666 . . . no
C10 Fe1 C6 C7 -61.2(3) 5_666 . . . no
C10 Fe1 C6 C10 -180.0(2) 5_666 . . . no
C10 Fe1 C6 C11 58.7(3) 5_666 . . . no
C6 Fe1 C7 C8 118.7(3) . . . . no
C8 Fe1 C7 C6 -118.7(3) . . . . no
C9 Fe1 C7 C6 -81.57(19) . . . . no
C9 Fe1 C7 C8 37.12(19) . . . . no
C10 Fe1 C7 C6 -38.00(18) . . . . no
C10 Fe1 C7 C8 80.7(2) . . . . no
C6 Fe1 C7 C6 179.97(19) 5_666 . . . no
C6 Fe1 C7 C8 -61.3(3) 5_666 . . . no
C8 Fe1 C7 C6 61.3(3) 5_666 . . . no
C8 Fe1 C7 C8 -180.00(19) 5_666 . . . no
C9 Fe1 C7 C6 98.43(19) 5_666 . . . no
C9 Fe1 C7 C8 -142.88(19) 5_666 . . . no
C10 Fe1 C7 C6 142.00(18) 5_666 . . . no
C10 Fe1 C7 C8 -99.3(2) 5_666 . . . no
C6 Fe1 C8 C7 -38.21(18) . . . . no
C6 Fe1 C8 C9 81.8(2) . . . . no
C7 Fe1 C8 C9 120.0(3) . . . . no
C9 Fe1 C8 C7 -120.0(3) . . . . no
C10 Fe1 C8 C7 -82.4(2) . . . . no
C10 Fe1 C8 C9 37.61(19) . . . . no
C6 Fe1 C8 C7 141.80(18) 5_666 . . . no
C6 Fe1 C8 C9 -98.2(2) 5_666 . . . no
C7 Fe1 C8 C7 -180.00(19) 5_666 . . . no
C7 Fe1 C8 C9 -60.0(3) 5_666 . . . no
C9 Fe1 C8 C7 60.0(3) 5_666 . . . no
C9 Fe1 C8 C9 180.0(2) 5_666 . . . no
C10 Fe1 C8 C7 97.6(2) 5_666 . . . no
C10 Fe1 C8 C9 -142.39(19) 5_666 . . . no
C6 Fe1 C9 C8 -81.7(2) . . . . no
C6 Fe1 C9 C10 37.6(2) . . . . no
C7 Fe1 C9 C8 -37.5(2) . . . . no
C7 Fe1 C9 C10 81.8(2) . . . . no
C8 Fe1 C9 C10 119.3(3) . . . . no
C10 Fe1 C9 C8 -119.3(3) . . . . no
C6 Fe1 C9 C8 98.3(2) 5_666 . . . no
C6 Fe1 C9 C10 -142.4(2) 5_666 . . . no
C7 Fe1 C9 C8 142.5(2) 5_666 . . . no
C7 Fe1 C9 C10 -98.2(2) 5_666 . . . no
C8 Fe1 C9 C8 179.98(19) 5_666 . . . no
C8 Fe1 C9 C10 -60.8(3) 5_666 . . . no
C10 Fe1 C9 C8 60.8(3) 5_666 . . . no
C10 Fe1 C9 C10 180.0(3) 5_666 . . . no
C6 Fe1 C10 C9 -119.8(3) . . . . no
C7 Fe1 C10 C6 38.1(2) . . . . no
C7 Fe1 C10 C9 -81.7(2) . . . . no
C8 Fe1 C10 C6 82.2(2) . . . . no
C8 Fe1 C10 C9 -37.6(2) . . . . no
C9 Fe1 C10 C6 119.8(3) . . . . no
C6 Fe1 C10 C6 -180.0(2) 5_666 . . . no
C6 Fe1 C10 C9 60.2(3) 5_666 . . . no
C7 Fe1 C10 C6 -141.9(2) 5_666 . . . no
C7 Fe1 C10 C9 98.3(2) 5_666 . . . no
C8 Fe1 C10 C6 -97.8(2) 5_666 . . . no
C8 Fe1 C10 C9 142.4(2) 5_666 . . . no
C9 Fe1 C10 C6 -60.2(3) 5_666 . . . no
C9 Fe1 C10 C9 -180.0(2) 5_666 . . . no
Cu1 O1 C11 O2 9.2(3) . . . . no
Cu1 O1 C11 C6 -169.1(2) . . . . no
Cu1 O2 C11 O1 -7.7(2) . . . . no
Cu1 O2 C11 C6 170.6(2) . . . . no
Cu1 N1 C1 C2 -171.9(2) . . . . no
C5 N1 C1 C2 0.7(4) . . . . no
Cu1 N1 C5 C4 173.5(2) . . . . no
C1 N1 C5 C4 1.1(4) . . . . no
N1 C1 C2 C3 -1.1(5) . . . . no
C1 C2 C3 C3 -179.7(3) . . . 3_554 no
C1 C2 C3 C4 -0.3(5) . . . . no
C2 C3 C4 C5 2.0(4) . . . . no
C4 C3 C3 C4 -31.8(5) . . 3_554 3_554 yes
C4 C3 C3 C2 147.5(3) . . 3_554 3_554 no
C3 C3 C4 C5 -178.7(3) 3_554 . . . no
C2 C3 C3 C2 -33.2(4) . . 3_554 3_554 no
C2 C3 C3 C4 147.5(3) . . 3_554 3_554 no
C3 C4 C5 N1 -2.5(5) . . . . no
C10 C6 C7 Fe1 60.1(2) . . . . no
C10 C6 C7 C8 0.4(3) . . . . no
Fe1 C6 C7 C8 -59.8(2) . . . . no
C7 C6 C10 C9 -0.8(3) . . . . no
C11 C6 C10 Fe1 112.7(3) . . . . no
C11 C6 C10 C9 171.6(3) . . . . no
C11 C6 C7 Fe1 -112.3(3) . . . . no
C11 C6 C7 C8 -172.1(3) . . . . no
Fe1 C6 C10 C9 58.9(2) . . . . no
C7 C6 C10 Fe1 -59.7(2) . . . . no
C10 C6 C11 O1 7.3(4) . . . . no
C10 C6 C11 O2 -171.1(3) . . . . no
Fe1 C6 C11 O2 -84.8(3) . . . . no
C7 C6 C11 O1 178.4(3) . . . . no
Fe1 C6 C11 O1 93.6(3) . . . . no
C7 C6 C11 O2 0.0(5) . . . . no
Fe1 C7 C8 C9 -59.2(2) . . . . no
C6 C7 C8 Fe1 59.4(2) . . . . no
C6 C7 C8 C9 0.2(3) . . . . no
Fe1 C8 C9 C10 -59.4(2) . . . . no
C7 C8 C9 Fe1 58.7(2) . . . . no
C7 C8 C9 C10 -0.7(4) . . . . no
C8 C9 C10 Fe1 59.2(2) . . . . no
C8 C9 C10 C6 0.9(3) . . . . no
Fe1 C9 C10 C6 -58.2(2) . . . . no

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
_geom_hbond_publ_flag
O1W H1W O1 0.915(18) 1.99(2) 2.893(3) 167(4) 1 yes
C5 H5 O2 0.9500 2.3900 3.084(4) 130.00 . yes
C9 H9 O1W 1.0000 2.5100 3.339(4) 141.00 . yes

_refine_diff_density_max         0.903
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.151

_shelxl_version_number           2013-3


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
