# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1412834'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2016-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H26 Cu2 N6 O12'
_chemical_formula_sum            'C26 H26 Cu2 N6 O12'
_chemical_formula_weight         741.61

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.5555(2)
_cell_length_b                   9.9153(3)
_cell_length_c                   11.7151(3)
_cell_angle_alpha                102.312(2)
_cell_angle_beta                 108.492(3)
_cell_angle_gamma                102.900(3)
_cell_volume                     772.07(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9672
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.90

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_F_000             378
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.448
_shelx_estimated_absorpt_T_min   0.732
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18719
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.214
_diffrn_reflns_theta_max         25.975
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3008
_reflns_number_gt                2539
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0492P)²+0.4383P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3008
_refine_ls_number_parameters     214
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.99055(4) 0.01760(4) 0.62738(3) 0.02969(13) Uani 1 1 d . . . . .
O1 O 0.8378(3) -0.0945(2) 0.45320(16) 0.0349(5) Uani 1 1 d . . . . .
O2 O 1.1301(3) 0.1391(2) 0.79893(16) 0.0323(4) Uani 1 1 d . . . . .
O3 O 1.1686(3) 0.2199(2) 1.00030(16) 0.0334(4) Uani 1 1 d . . . . .
O4 O 0.2321(3) -0.4075(2) 0.07866(17) 0.0401(5) Uani 1 1 d . . . . .
O5 O -0.0024(3) -0.4490(3) 0.15557(19) 0.0455(5) Uani 1 1 d D . . . .
O6 O 1.1059(3) -0.1689(3) 0.68158(19) 0.0454(5) Uani 1 1 d D . . . .
N1 N 0.7475(3) -0.0437(2) 0.64973(19) 0.0259(5) Uani 1 1 d . . . . .
N2 N 0.7112(3) -0.0155(2) 0.75068(19) 0.0259(5) Uani 1 1 d . . . . .
N3 N 0.7594(4) 0.1129(3) 1.0522(2) 0.0466(7) Uani 1 1 d . . . . .
C1 C 0.6478(4) -0.1563(3) 0.4311(2) 0.0261(5) Uani 1 1 d . . . . .
C2 C 0.5110(4) -0.2401(3) 0.3128(2) 0.0287(6) Uani 1 1 d . . . . .
H2 H 0.5478 -0.2545 0.2437 0.034 Uiso 1 1 calc R U . . .
C3 C 0.3181(4) -0.3030(3) 0.2972(2) 0.0277(5) Uani 1 1 d . . . . .
C4 C 0.2609(4) -0.2805(3) 0.4000(2) 0.0315(6) Uani 1 1 d . . . . .
H4 H 0.1309 -0.3225 0.3884 0.038 Uiso 1 1 calc R U . . .
C5 C 0.3976(4) -0.1956(3) 0.5198(2) 0.0311(6) Uani 1 1 d . . . . .
H5 H 0.3599 -0.1805 0.5886 0.037 Uiso 1 1 calc R U . . .
C6 C 0.5905(4) -0.1338(3) 0.5354(2) 0.0253(5) Uani 1 1 d . . . . .
C7 C 0.1761(4) -0.3919(3) 0.1679(2) 0.0289(6) Uani 1 1 d . . . . .
C8 C 0.8572(4) 0.0719(3) 0.8597(2) 0.0263(5) Uani 1 1 d . . . . .
C9 C 0.8012(4) 0.0944(3) 0.9668(2) 0.0317(6) Uani 1 1 d . . . . .
C10 C 1.0575(4) 0.1437(3) 0.8809(2) 0.0279(6) Uani 1 1 d . . . . .
C11 C 1.3763(4) 0.2890(4) 1.0292(3) 0.0425(7) Uani 1 1 d . . . . .
H11A H 1.3919 0.3682 0.9931 0.051 Uiso 1 1 calc R U . . .
H11B H 1.4314 0.2190 0.9939 0.051 Uiso 1 1 calc R U . . .
C12 C 1.4792(5) 0.3454(4) 1.1702(3) 0.0546(9) Uani 1 1 d . . . . .
H12A H 1.6166 0.3916 1.1922 0.082 Uiso 1 1 calc R U . . .
H12B H 1.4237 0.4146 1.2041 0.082 Uiso 1 1 calc R U . . .
H12C H 1.4631 0.2661 1.2048 0.082 Uiso 1 1 calc R U . . .
C13 C 0.9771(7) -0.3129(4) 0.6372(4) 0.0749(12) Uani 1 1 d . . . . .
H13A H 1.0480 -0.3754 0.6681 0.112 Uiso 1 1 calc R U . . .
H13B H 0.8721 -0.3158 0.6670 0.112 Uiso 1 1 calc R U . . .
H13C H 0.9238 -0.3454 0.5464 0.112 Uiso 1 1 calc R U . . .
H5O H -0.067(7) -0.506(5) 0.078(2) 0.112 Uiso 1 1 d D U . . .
H6O H 1.175(7) -0.141(6) 0.762(2) 0.112 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 O2 1.9125(18) . ?
Cu1 N1 1.920(2) . ?
Cu1 O1 1.9228(17) . ?
Cu1 O1 1.9486(17) 2_756 ?
Cu1 O6 2.335(2) . ?
Cu1 Cu1 2.9830(6) 2_756 ?
O1 C1 1.344(3) . ?
O1 Cu1 1.9487(17) 2_756 ?
O2 C10 1.245(3) . ?
O3 C10 1.324(3) . ?
O3 C11 1.460(3) . ?
O4 C7 1.240(3) . ?
O5 C7 1.288(3) . ?
O5 H5O 0.869(19) . ?
O6 C13 1.413(5) . ?
O6 H6O 0.866(19) . ?
N1 N2 1.285(3) . ?
N1 C6 1.417(3) . ?
N2 C8 1.344(3) . ?
N3 C9 1.132(4) . ?
C1 C2 1.377(3) . ?
C1 C6 1.412(3) . ?
C2 C3 1.387(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(4) . ?
C3 C7 1.483(3) . ?
C4 C5 1.391(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9300 . ?
C8 C10 1.437(4) . ?
C8 C9 1.437(4) . ?
C11 C12 1.499(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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 N1 93.57(8) . . ?
O2 Cu1 O1 175.46(9) . . ?
N1 Cu1 O1 84.50(8) . . ?
O2 Cu1 O1 101.38(8) . 2_756 ?
N1 Cu1 O1 156.37(9) . 2_756 ?
O1 Cu1 O1 79.21(8) . 2_756 ?
O2 Cu1 O6 89.62(8) . . ?
N1 Cu1 O6 95.97(9) . . ?
O1 Cu1 O6 94.66(8) . . ?
O1 Cu1 O6 102.26(9) 2_756 . ?
O2 Cu1 Cu1 140.49(6) . 2_756 ?
N1 Cu1 Cu1 122.46(6) . 2_756 ?
O1 Cu1 Cu1 39.92(5) . 2_756 ?
O1 Cu1 Cu1 39.29(5) 2_756 2_756 ?
O6 Cu1 Cu1 101.02(5) . 2_756 ?
C1 O1 Cu1 112.77(15) . . ?
C1 O1 Cu1 142.15(16) . 2_756 ?
Cu1 O1 Cu1 100.79(8) . 2_756 ?
C10 O2 Cu1 123.26(17) . . ?
C10 O3 C11 116.8(2) . . ?
C7 O5 H5O 108(3) . . ?
C13 O6 Cu1 120.3(2) . . ?
C13 O6 H6O 113(4) . . ?
Cu1 O6 H6O 109(4) . . ?
N2 N1 C6 118.0(2) . . ?
N2 N1 Cu1 129.53(17) . . ?
C6 N1 Cu1 112.45(16) . . ?
N1 N2 C8 119.0(2) . . ?
O1 C1 C2 122.7(2) . . ?
O1 C1 C6 117.4(2) . . ?
C2 C1 C6 119.8(2) . . ?
C1 C2 C3 119.7(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 C7 117.7(2) . . ?
C4 C3 C7 121.7(2) . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 N1 126.6(2) . . ?
C1 C6 N1 112.8(2) . . ?
O4 C7 O5 123.6(2) . . ?
O4 C7 C3 119.8(2) . . ?
O5 C7 C3 116.6(2) . . ?
N2 C8 C10 128.3(2) . . ?
N2 C8 C9 114.4(2) . . ?
C10 C8 C9 117.4(2) . . ?
N3 C9 C8 179.2(3) . . ?
O2 C10 O3 119.8(2) . . ?
O2 C10 C8 126.0(2) . . ?
O3 C10 C8 114.1(2) . . ?
O3 C11 C12 107.5(3) . . ?
O3 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O3 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 C13 H13A 109.5 . . ?
O6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
C5 H5 O6 0.93 2.50 3.348(4) 151.6 1_455
C5 H5 O6 0.93 2.50 3.348(4) 151.6 1_455
O5 H5O O4 0.869(19) 1.75(2) 2.603(3) 167(5) 2_545
O6 H6O N3 0.866(19) 2.01(3) 2.840(3) 159(5) 2_757

_refine_diff_density_max         0.588
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.108

####################################################################### 
# 
# 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_Compound2
_database_code_depnum_ccdc_archive 'CCDC 1412835'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2016-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 Cu N4 O6'
_chemical_formula_sum            'C15 H16 Cu N4 O6'
_chemical_formula_weight         411.86

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.3116(5)
_cell_length_b                   10.4327(8)
_cell_length_c                   10.7676(8)
_cell_angle_alpha                105.623(4)
_cell_angle_beta                 92.203(4)
_cell_angle_gamma                109.315(3)
_cell_volume                     840.18(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2481
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      25.36

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_F_000             422
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.342
_shelx_estimated_absorpt_T_min   0.814
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12529
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.462
_diffrn_reflns_theta_max         25.544
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             3021
_reflns_number_gt                2190
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0515P)²+0.4551P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3021
_refine_ls_number_parameters     240
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.147
_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
Cu1 Cu 0.11796(6) 0.13562(5) 0.59227(5) 0.0397(2) Uani 1 1 d . . . . .
O1 O -0.1051(3) 0.0575(3) 0.4913(3) 0.0443(8) Uani 1 1 d . . . . .
O2 O 0.3380(3) 0.2162(3) 0.6955(3) 0.0339(7) Uani 1 1 d . . . . .
O3 O 0.5609(3) 0.3956(3) 0.8194(3) 0.0369(7) Uani 1 1 d . . . . .
O4 O -0.6564(3) 0.0607(3) 0.3013(3) 0.0501(8) Uani 1 1 d D . . . .
O5 O -0.6752(4) 0.2637(4) 0.4200(3) 0.0549(9) Uani 1 1 d . . . . .
O6 O -0.0080(4) 0.0546(4) 0.7898(4) 0.0623(10) Uani 1 1 d . . . . .
N1 N 0.0796(4) 0.3117(3) 0.6276(3) 0.0299(7) Uani 1 1 d . . . . .
N2 N 0.1782(4) 0.4364(3) 0.6964(3) 0.0309(8) Uani 1 1 d . . . . .
N3 N 0.5165(5) 0.7088(4) 0.8883(4) 0.0591(12) Uani 1 1 d . . . . .
N4 N 0.1229(5) -0.0724(4) 0.8691(4) 0.0473(10) Uani 1 1 d . . . . .
C1 C -0.1779(4) 0.1541(4) 0.4937(4) 0.0301(9) Uani 1 1 d . . . . .
C2 C -0.3415(5) 0.1210(4) 0.4315(4) 0.0337(10) Uani 1 1 d . . . . .
H2 H -0.4051 0.0280 0.3823 0.040 Uiso 1 1 calc R U . . .
C3 C -0.4102(5) 0.2269(4) 0.4426(4) 0.0308(9) Uani 1 1 d . . . . .
C4 C -0.3149(5) 0.3669(4) 0.5128(4) 0.0349(10) Uani 1 1 d . . . . .
H4 H -0.3621 0.4374 0.5190 0.042 Uiso 1 1 calc R U . . .
C5 C -0.1502(5) 0.4018(4) 0.5734(4) 0.0308(9) Uani 1 1 d . . . . .
H5 H -0.0855 0.4960 0.6189 0.037 Uiso 1 1 calc R U . . .
C6 C -0.0818(4) 0.2964(4) 0.5663(4) 0.0278(9) Uani 1 1 d . . . . .
C7 C -0.5922(5) 0.1887(5) 0.3871(4) 0.0377(10) Uani 1 1 d . . . . .
C8 C 0.3322(4) 0.4515(4) 0.7542(4) 0.0310(9) Uani 1 1 d . . . . .
C9 C 0.4347(5) 0.5962(4) 0.8281(4) 0.0395(10) Uani 1 1 d . . . . .
C10 C 0.4064(5) 0.3454(4) 0.7525(4) 0.0313(9) Uani 1 1 d . . . . .
C11 C 0.6441(5) 0.2935(4) 0.8213(4) 0.0384(10) Uani 1 1 d . . . . .
H11A H 0.6500 0.2414 0.7333 0.046 Uiso 1 1 calc R U . . .
H11B H 0.5801 0.2260 0.8644 0.046 Uiso 1 1 calc R U . . .
C12 C 0.8222(5) 0.3771(5) 0.8946(5) 0.0495(12) Uani 1 1 d . . . . .
H12A H 0.8818 0.3132 0.8982 0.074 Uiso 1 1 calc R U . . .
H12B H 0.8840 0.4433 0.8510 0.074 Uiso 1 1 calc R U . . .
H12C H 0.8144 0.4281 0.9815 0.074 Uiso 1 1 calc R U . . .
C13 C 0.1091(5) 0.0435(5) 0.8554(5) 0.0481(12) Uani 1 1 d . . . . .
H13 H 0.1975 0.1280 0.9002 0.058 Uiso 1 1 calc R U . . .
C14 C -0.0044(8) -0.2109(6) 0.8060(6) 0.088(2) Uani 1 1 d . . . . .
H14A H 0.0520 -0.2777 0.7745 0.132 Uiso 1 1 calc R U . . .
H14B H -0.0721 -0.2062 0.7342 0.132 Uiso 1 1 calc R U . . .
H14C H -0.0779 -0.2411 0.8672 0.132 Uiso 1 1 calc R U . . .
C15 C 0.2701(7) -0.0690(6) 0.9470(6) 0.0735(17) Uani 1 1 d . . . . .
H15A H 0.2320 -0.1140 1.0129 0.110 Uiso 1 1 calc R U . . .
H15B H 0.3437 0.0281 0.9876 0.110 Uiso 1 1 calc R U . . .
H15C H 0.3325 -0.1187 0.8925 0.110 Uiso 1 1 calc R U . . .
H4O H -0.767(3) 0.043(7) 0.276(6) 0.110 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 O2 1.900(2) . ?
Cu1 O1 1.911(2) . ?
Cu1 N1 1.908(3) . ?
Cu1 O1 1.938(3) 2_556 ?
Cu1 Cu1 2.9669(9) 2_556 ?
O1 C1 1.331(4) . ?
O1 Cu1 1.938(3) 2_556 ?
O2 C10 1.241(4) . ?
O3 C10 1.313(4) . ?
O3 C11 1.454(5) . ?
O4 C7 1.322(5) . ?
O4 H4O 0.89(2) . ?
O5 C7 1.200(5) . ?
O6 C13 1.235(5) . ?
N1 N2 1.282(4) . ?
N1 C6 1.412(4) . ?
N2 C8 1.343(5) . ?
N3 C9 1.136(5) . ?
N4 C13 1.298(6) . ?
N4 C14 1.439(6) . ?
N4 C15 1.441(6) . ?
C1 C2 1.383(5) . ?
C1 C6 1.413(5) . ?
C2 C3 1.382(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(5) . ?
C3 C7 1.486(5) . ?
C4 C5 1.380(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(5) . ?
C5 H5 0.9300 . ?
C8 C10 1.431(6) . ?
C8 C9 1.445(5) . ?
C11 C12 1.503(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 O1 178.71(12) . . ?
O2 Cu1 N1 94.56(12) . . ?
O1 Cu1 N1 84.40(12) . . ?
O2 Cu1 O1 101.99(11) . 2_556 ?
O1 Cu1 O1 79.14(12) . 2_556 ?
N1 Cu1 O1 161.94(13) . 2_556 ?
O2 Cu1 Cu1 141.23(8) . 2_556 ?
O1 Cu1 Cu1 39.89(8) . 2_556 ?
N1 Cu1 Cu1 123.92(9) . 2_556 ?
O1 Cu1 Cu1 39.24(7) 2_556 2_556 ?
C1 O1 Cu1 113.3(2) . . ?
C1 O1 Cu1 145.2(2) . 2_556 ?
Cu1 O1 Cu1 100.86(11) . 2_556 ?
C10 O2 Cu1 122.6(2) . . ?
C10 O3 C11 116.8(3) . . ?
C7 O4 H4O 109(4) . . ?
N2 N1 C6 118.1(3) . . ?
N2 N1 Cu1 129.3(3) . . ?
C6 N1 Cu1 112.6(2) . . ?
N1 N2 C8 118.3(3) . . ?
C13 N4 C14 122.4(4) . . ?
C13 N4 C15 121.2(4) . . ?
C14 N4 C15 116.3(4) . . ?
O1 C1 C2 123.4(3) . . ?
O1 C1 C6 117.2(3) . . ?
C2 C1 C6 119.5(3) . . ?
C1 C2 C3 119.8(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 C7 119.6(3) . . ?
C4 C3 C7 119.6(4) . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 N1 127.3(3) . . ?
C1 C6 N1 112.6(3) . . ?
O5 C7 O4 123.1(4) . . ?
O5 C7 C3 123.7(4) . . ?
O4 C7 C3 113.2(4) . . ?
N2 C8 C10 129.1(3) . . ?
N2 C8 C9 114.1(3) . . ?
C10 C8 C9 116.7(3) . . ?
N3 C9 C8 178.4(5) . . ?
O2 C10 O3 119.9(4) . . ?
O2 C10 C8 126.1(3) . . ?
O3 C10 C8 114.0(3) . . ?
O3 C11 C12 106.8(3) . . ?
O3 C11 H11A 110.4 . . ?
C12 C11 H11A 110.4 . . ?
O3 C11 H11B 110.4 . . ?
C12 C11 H11B 110.4 . . ?
H11A C11 H11B 108.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 C13 N4 127.5(4) . . ?
O6 C13 H13 116.3 . . ?
N4 C13 H13 116.3 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
C14 H14B O5 0.96 2.43 3.336(6) 157.8 2_456
C15 H15B N3 0.96 2.54 3.488(7) 168.4 2_667
O4 H4O O6 0.89(2) 1.81(3) 2.668(4) 161(6) 2_456

_refine_diff_density_max         0.613
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_Compound3
_database_code_depnum_ccdc_archive 'CCDC 1412836'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2016-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H25 Cu N7 O5, C H4 O, H2 O'
_chemical_formula_sum            'C17 H31 Cu N7 O7'
_chemical_formula_weight         509.03

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, 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                   30.610(3)
_cell_length_b                   6.9300(6)
_cell_length_c                   23.4642(19)
_cell_angle_alpha                90
_cell_angle_beta                 103.391(3)
_cell_angle_gamma                90
_cell_volume                     4842.1(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7752
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      26.36

_exptl_crystal_description       block
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             2136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.952
_shelx_estimated_absorpt_T_min   0.739
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28277
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.018
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4953
_reflns_number_gt                3681
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4953
_refine_ls_number_parameters     327
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.036 0.250 65 15 ' '
2 0.000 -0.037 0.750 65 15 ' '
3 0.500 0.463 0.750 65 15 ' '
4 0.500 0.536 0.250 65 15 ' '
_platon_squeeze_details          
;
;

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
C1 C 0.70839(8) 0.4780(3) 0.98329(10) 0.0172(5) Uani 1 1 d . . . . .
C2 C 0.75462(8) 0.4959(3) 1.01068(10) 0.0152(5) Uani 1 1 d . . . . .
C3 C 0.81458(8) 0.4082(3) 0.90210(10) 0.0155(5) Uani 1 1 d . . . . .
C4 C 0.85980(8) 0.4313(3) 0.93345(10) 0.0167(5) Uani 1 1 d . . . . .
C5 C 0.89398(8) 0.4165(4) 0.90434(11) 0.0196(6) Uani 1 1 d . . . . .
H5 H 0.9235 0.4315 0.9253 0.024 Uiso 1 1 calc R U . . .
C6 C 0.88552(8) 0.3799(4) 0.84471(11) 0.0184(5) Uani 1 1 d . . . . .
C7 C 0.84119(8) 0.3552(3) 0.81364(11) 0.0200(6) Uani 1 1 d . . . . .
H7 H 0.8349 0.3296 0.7737 0.024 Uiso 1 1 calc R U . . .
C8 C 0.80660(8) 0.3689(4) 0.84244(10) 0.0204(6) Uani 1 1 d . . . . .
H8 H 0.7772 0.3512 0.8213 0.024 Uiso 1 1 calc R U . . .
C9 C 0.92352(9) 0.3716(4) 0.81389(11) 0.0220(6) Uani 1 1 d . . . . .
C10 C 0.76881(8) 0.5464(3) 1.07142(11) 0.0192(5) Uani 1 1 d . . . . .
C11 C 0.74350(10) 0.6347(5) 1.15619(11) 0.0359(7) Uani 1 1 d . . . . .
H11A H 0.7582 0.7595 1.1604 0.043 Uiso 1 1 calc R U . . .
H11B H 0.7632 0.5422 1.1805 0.043 Uiso 1 1 calc R U . . .
C12 C 0.70023(13) 0.6464(5) 1.17396(15) 0.0587(11) Uani 1 1 d . . . . .
H12A H 0.7056 0.6864 1.2142 0.088 Uiso 1 1 calc R U . . .
H12B H 0.6810 0.7384 1.1496 0.088 Uiso 1 1 calc R U . . .
H12C H 0.6860 0.5221 1.1696 0.088 Uiso 1 1 calc R U . . .
C20 C 0.93721(12) 0.8838(5) 0.87073(15) 0.0523(9) Uani 1 1 d . . . . .
H20A H 0.9434 1.0160 0.8820 0.079 Uiso 1 1 calc R U . . .
H20B H 0.9097 0.8447 0.8803 0.079 Uiso 1 1 calc R U . . .
H20C H 0.9344 0.8708 0.8293 0.079 Uiso 1 1 calc R U . . .
C21 C 0.56310(10) 0.4843(4) 0.98292(12) 0.0340(7) Uani 1 1 d . . . . .
H21A H 0.5908 0.4988 1.0126 0.041 Uiso 1 1 calc R U . . .
H21B H 0.5398 0.4412 1.0018 0.041 Uiso 1 1 calc R U . . .
C22 C 0.55005(10) 0.6734(4) 0.95259(12) 0.0346(7) Uani 1 1 d . . . . .
H22A H 0.5202 0.6644 0.9272 0.042 Uiso 1 1 calc R U . . .
H22B H 0.5499 0.7743 0.9812 0.042 Uiso 1 1 calc R U . . .
C31 C 0.63684(10) 0.2760(4) 0.79867(11) 0.0307(7) Uani 1 1 d . . . . .
H31A H 0.6122 0.3024 0.7653 0.037 Uiso 1 1 calc R U . . .
H31B H 0.6543 0.1698 0.7887 0.037 Uiso 1 1 calc R U . . .
C32 C 0.66603(9) 0.4533(4) 0.81413(12) 0.0271(6) Uani 1 1 d . . . . .
H32A H 0.6926 0.4223 0.8442 0.032 Uiso 1 1 calc R U . . .
H32B H 0.6754 0.4999 0.7799 0.032 Uiso 1 1 calc R U . . .
N1 N 0.67109(7) 0.4611(3) 0.96097(9) 0.0258(5) Uani 1 1 d . . . . .
N2 N 0.78714(6) 0.4705(3) 0.98131(8) 0.0156(4) Uani 1 1 d . . . . .
N3 N 0.77627(6) 0.4275(3) 0.92596(8) 0.0169(5) Uani 1 1 d . . . . .
N21 N 0.56923(8) 0.3421(4) 0.93878(11) 0.0261(5) Uani 1 1 d . . . . .
N22 N 0.58340(8) 0.7179(3) 0.91782(10) 0.0263(5) Uani 1 1 d D . . . .
N31 N 0.61944(8) 0.2264(3) 0.85018(10) 0.0239(5) Uani 1 1 d D . . . .
N32 N 0.63936(8) 0.6025(3) 0.83563(10) 0.0219(5) Uani 1 1 d . . . . .
O1 O 0.91563(6) 0.3124(3) 0.76223(8) 0.0319(5) Uani 1 1 d . . . . .
O2 O 0.96174(6) 0.4259(3) 0.84266(8) 0.0333(5) Uani 1 1 d . . . . .
O1W O 0.54226(6) 0.9677(3) 0.81762(8) 0.0312(5) Uani 1 1 d D . . . .
O3 O 0.87040(6) 0.4698(3) 0.99211(7) 0.0222(4) Uani 1 1 d D . . . .
O4 O 0.73371(6) 0.5743(3) 1.09587(7) 0.0243(4) Uani 1 1 d . . . . .
O5 O 0.80803(6) 0.5647(3) 1.09887(7) 0.0254(4) Uani 1 1 d . . . . .
O20 O 0.97254(7) 0.7666(3) 0.90089(9) 0.0373(5) Uani 1 1 d D . . . .
Cu1 Cu 0.60498(2) 0.47118(4) 0.88804(2) 0.02033(11) Uani 1 1 d . . . . .
H1W1 H 0.5483(9) 0.919(4) 0.7861(9) 0.030 Uiso 1 1 d D U . . .
H1W2 H 0.5131(6) 0.952(4) 0.8156(11) 0.030 Uiso 1 1 d D U . . .
H3O H 0.8441(7) 0.483(4) 0.9999(12) 0.030 Uiso 1 1 d D U . . .
H20O H 0.9686(9) 0.652(3) 0.8864(12) 0.030 Uiso 1 1 d D U . . .
H21C H 0.5459(10) 0.299(4) 0.9202(13) 0.030 Uiso 1 1 d . U . . .
H21D H 0.5830(9) 0.232(4) 0.9552(12) 0.030 Uiso 1 1 d . U . . .
H22C H 0.6063(10) 0.774(4) 0.9391(12) 0.030 Uiso 1 1 d . U . . .
H22D H 0.5731(9) 0.804(3) 0.8916(10) 0.030 Uiso 1 1 d D U . . .
H31C H 0.6393(8) 0.162(4) 0.8745(10) 0.030 Uiso 1 1 d D U . . .
H31D H 0.5962(9) 0.164(4) 0.8414(12) 0.030 Uiso 1 1 d . U . . .
H32C H 0.6219(9) 0.662(4) 0.8107(13) 0.030 Uiso 1 1 d . U . . .
H32D H 0.6542(9) 0.698(4) 0.8511(12) 0.030 Uiso 1 1 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
C1 N1 1.146(3) . ?
C1 C2 1.418(3) . ?
C2 N2 1.347(3) . ?
C2 C10 1.434(3) . ?
C3 C8 1.391(3) . ?
C3 N3 1.418(3) . ?
C3 C4 1.418(3) . ?
C4 O3 1.365(3) . ?
C4 C5 1.379(3) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(3) . ?
C6 C9 1.506(3) . ?
C7 C8 1.385(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 O1 1.249(3) . ?
C9 O2 1.265(3) . ?
C10 O5 1.230(3) . ?
C10 O4 1.344(3) . ?
C11 O4 1.439(3) . ?
C11 C12 1.480(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C20 O20 1.406(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N21 1.473(4) . ?
C21 C22 1.500(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N22 1.479(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C31 N31 1.470(3) . ?
C31 C32 1.513(4) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 N32 1.477(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
N1 Cu1 2.329(2) . ?
N2 N3 1.298(3) . ?
N21 Cu1 2.005(2) . ?
N21 H21C 0.80(3) . ?
N21 H21D 0.91(3) . ?
N22 Cu1 2.015(2) . ?
N22 H22C 0.85(3) . ?
N22 H22D 0.863(17) . ?
N31 Cu1 2.011(2) . ?
N31 H31C 0.857(17) . ?
N31 H31D 0.82(3) . ?
N32 Cu1 2.012(2) . ?
N32 H32C 0.81(3) . ?
N32 H32D 0.84(3) . ?
O1W H1W1 0.871(16) . ?
O1W H1W2 0.890(16) . ?
O3 H3O 0.872(17) . ?
O20 H20O 0.862(17) . ?

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 C1 C2 179.1(3) . . ?
N2 C2 C1 122.3(2) . . ?
N2 C2 C10 116.8(2) . . ?
C1 C2 C10 120.9(2) . . ?
C8 C3 N3 116.6(2) . . ?
C8 C3 C4 117.8(2) . . ?
N3 C3 C4 125.6(2) . . ?
O3 C4 C5 118.9(2) . . ?
O3 C4 C3 121.4(2) . . ?
C5 C4 C3 119.7(2) . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C7 118.8(2) . . ?
C5 C6 C9 120.5(2) . . ?
C7 C6 C9 120.7(2) . . ?
C8 C7 C6 119.9(2) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C3 121.9(2) . . ?
C7 C8 H8 119.0 . . ?
C3 C8 H8 119.0 . . ?
O1 C9 O2 124.3(2) . . ?
O1 C9 C6 118.7(2) . . ?
O2 C9 C6 117.0(2) . . ?
O5 C10 O4 122.8(2) . . ?
O5 C10 C2 125.4(2) . . ?
O4 C10 C2 111.8(2) . . ?
O4 C11 C12 107.3(3) . . ?
O4 C11 H11A 110.3 . . ?
C12 C11 H11A 110.3 . . ?
O4 C11 H11B 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O20 C20 H20A 109.5 . . ?
O20 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O20 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N21 C21 C22 108.3(2) . . ?
N21 C21 H21A 110.0 . . ?
C22 C21 H21A 110.0 . . ?
N21 C21 H21B 110.0 . . ?
C22 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
N22 C22 C21 107.6(2) . . ?
N22 C22 H22A 110.2 . . ?
C21 C22 H22A 110.2 . . ?
N22 C22 H22B 110.2 . . ?
C21 C22 H22B 110.2 . . ?
H22A C22 H22B 108.5 . . ?
N31 C31 C32 107.4(2) . . ?
N31 C31 H31A 110.2 . . ?
C32 C31 H31A 110.2 . . ?
N31 C31 H31B 110.2 . . ?
C32 C31 H31B 110.2 . . ?
H31A C31 H31B 108.5 . . ?
N32 C32 C31 107.9(2) . . ?
N32 C32 H32A 110.1 . . ?
C31 C32 H32A 110.1 . . ?
N32 C32 H32B 110.1 . . ?
C31 C32 H32B 110.1 . . ?
H32A C32 H32B 108.4 . . ?
C1 N1 Cu1 159.46(19) . . ?
N3 N2 C2 119.54(19) . . ?
N2 N3 C3 111.89(19) . . ?
C21 N21 Cu1 107.16(17) . . ?
C21 N21 H21C 113(2) . . ?
Cu1 N21 H21C 113(2) . . ?
C21 N21 H21D 112.7(17) . . ?
Cu1 N21 H21D 111.2(17) . . ?
H21C N21 H21D 100(3) . . ?
C22 N22 Cu1 109.75(18) . . ?
C22 N22 H22C 110.5(19) . . ?
Cu1 N22 H22C 107.4(19) . . ?
C22 N22 H22D 110.8(18) . . ?
Cu1 N22 H22D 115.7(18) . . ?
H22C N22 H22D 102(3) . . ?
C31 N31 Cu1 108.92(17) . . ?
C31 N31 H31C 109.5(19) . . ?
Cu1 N31 H31C 110.0(19) . . ?
C31 N31 H31D 112(2) . . ?
Cu1 N31 H31D 107(2) . . ?
H31C N31 H31D 109(3) . . ?
C32 N32 Cu1 107.52(16) . . ?
C32 N32 H32C 116(2) . . ?
Cu1 N32 H32C 109(2) . . ?
C32 N32 H32D 115(2) . . ?
Cu1 N32 H32D 113.7(19) . . ?
H32C N32 H32D 96(3) . . ?
H1W1 O1W H1W2 108(2) . . ?
C4 O3 H3O 102.5(18) . . ?
C10 O4 C11 117.2(2) . . ?
C20 O20 H20O 108.2(19) . . ?
N21 Cu1 N31 95.29(10) . . ?
N21 Cu1 N32 178.52(10) . . ?
N31 Cu1 N32 84.94(9) . . ?
N21 Cu1 N22 84.53(10) . . ?
N31 Cu1 N22 172.78(10) . . ?
N32 Cu1 N22 95.06(9) . . ?
N21 Cu1 N1 92.93(9) . . ?
N31 Cu1 N1 93.25(9) . . ?
N32 Cu1 N1 88.52(9) . . ?
N22 Cu1 N1 93.97(9) . . ?

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
N21 H21C O20 0.80(3) 2.20(3) 2.933(3) 153(3) 3_445
N21 H21D O3 0.91(3) 2.17(3) 3.054(3) 163(2) 7_657
N22 H22C O3 0.85(3) 2.39(3) 3.125(3) 144(2) 7_667
N22 H22D O1W 0.863(17) 2.105(18) 2.956(3) 169(3) .
N31 H31C O5 0.857(17) 2.233(19) 3.033(3) 155(3) 7_657
N31 H31D O1W 0.82(3) 2.11(3) 2.923(3) 172(3) 1_545
N32 H32C O1 0.81(3) 2.10(3) 2.904(3) 171(3) 4_656
N32 H32D O5 0.84(3) 2.19(3) 3.021(3) 173(3) 7_667
O3 H3O N2 0.872(17) 1.70(2) 2.502(2) 152(3) .
O3 H3O N3 0.872(17) 2.41(3) 2.954(3) 121(2) .
O20 H20O O2 0.862(17) 1.857(18) 2.710(3) 169(3) .
O1W H1W2 O2 0.890(16) 1.835(18) 2.679(2) 157(2) 3_455
O1W H1W1 O1 0.871(16) 1.905(18) 2.729(2) 157(3) 4_656
N21 H21C O20 0.80(3) 2.20(3) 2.933(3) 153(3) 3_445
N21 H21D O3 0.91(3) 2.17(3) 3.054(3) 163(2) 7_657
N22 H22C O3 0.85(3) 2.39(3) 3.125(3) 144(2) 7_667
N22 H22D O1W 0.863(17) 2.105(18) 2.956(3) 169(3) .
N31 H31C O5 0.857(17) 2.233(19) 3.033(3) 155(3) 7_657
N31 H31D O1W 0.82(3) 2.11(3) 2.923(3) 172(3) 1_545
N32 H32C O1 0.81(3) 2.10(3) 2.904(3) 171(3) 4_656
N32 H32D O5 0.84(3) 2.19(3) 3.021(3) 173(3) 7_667
O3 H3O N2 0.872(17) 1.70(2) 2.502(2) 152(3) .
O3 H3O N3 0.872(17) 2.41(3) 2.954(3) 121(2) .
O20 H20O O2 0.862(17) 1.857(18) 2.710(3) 169(3) .
O1W H1W1 O1 0.871(16) 1.905(18) 2.729(2) 157(3) 4_656
O1W H1W2 O2 0.890(16) 1.835(18) 2.679(2) 157(2) 3_455

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_Compound4
_database_code_depnum_ccdc_archive 'CCDC 1412837'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2016-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 Fe N22'
_chemical_formula_sum            'C12 H7 Fe N22'
_chemical_formula_weight         515.25

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   13.9488(13)
_cell_length_b                   9.8504(10)
_cell_length_c                   15.1432(15)
_cell_angle_alpha                90
_cell_angle_beta                 112.754(3)
_cell_angle_gamma                90
_cell_volume                     1918.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4980
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      23.95

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_F_000             1036
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    0.847
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21975
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.530
_diffrn_reflns_theta_max         25.360
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3515
_reflns_number_gt                2223
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0883P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3515
_refine_ls_number_parameters     325
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1555
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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_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
C1 C 0.6949(4) 0.1999(4) 0.9594(3) 0.0360(11) Uani 1 1 d . . . . .
C2 C 0.5459(4) 0.2750(5) 0.8736(4) 0.0438(12) Uani 1 1 d . . . . .
H2 H 0.4899 0.3306 0.8397 0.053 Uiso 1 1 calc R U . . .
C3 C 0.9253(3) 0.3653(4) 1.0788(3) 0.0349(10) Uani 1 1 d . . . . .
C4 C 1.0047(4) 0.2718(5) 1.1305(3) 0.0426(12) Uani 1 1 d . . . . .
C5 C 0.8893(4) 0.7102(4) 1.0403(3) 0.0345(11) Uani 1 1 d . . . . .
C6 C 0.9704(4) 0.8911(5) 1.0739(4) 0.0505(14) Uani 1 1 d . . . . .
H6 H 1.0225 0.9562 1.0972 0.061 Uiso 1 1 calc R U . . .
C7 C 0.7055(3) 0.5671(5) 0.7840(3) 0.0345(11) Uani 1 1 d . . . . .
C8 C 0.8162(3) 0.4125(4) 0.8018(3) 0.0345(11) Uani 1 1 d . . . . .
H8 H 0.8634 0.3417 0.8256 0.041 Uiso 1 1 calc R U . . .
C9 C 0.5919(3) 0.6720(4) 0.9391(4) 0.0411(12) Uani 1 1 d . . . . .
C10 C 0.5194(4) 0.7776(5) 0.8951(4) 0.0484(13) Uani 1 1 d . . . . .
C11 C 0.7028(4) 0.4860(5) 1.1481(3) 0.0444(12) Uani 1 1 d . . . . .
C12 C 0.7182(6) 0.4694(10) 1.2885(5) 0.104(3) Uani 1 1 d . . . . .
H12 H 0.7137 0.4847 1.3473 0.125 Uiso 1 1 calc R U . . .
N1 N 0.8262(3) 0.3292(3) 1.0258(2) 0.0304(8) Uani 1 1 d . . . . .
N2 N 0.7991(3) 0.2015(4) 1.0155(3) 0.0370(9) Uani 1 1 d . . . . .
N3 N 0.8665(3) 0.5715(4) 1.0340(2) 0.0329(9) Uani 1 1 d . . . . .
N4 N 0.9482(3) 0.4974(4) 1.0844(3) 0.0371(9) Uani 1 1 d . . . . .
N5 N 0.9861(3) 0.7599(4) 1.0841(3) 0.0503(11) Uani 1 1 d . . . . .
N6 N 0.8155(3) 0.8027(4) 1.0026(3) 0.0460(11) Uani 1 1 d . . . . .
N7 N 0.8722(4) 0.9187(4) 1.0268(3) 0.0532(12) Uani 1 1 d D . . . .
N8 N 0.6414(3) 0.3159(4) 0.9226(3) 0.0388(9) Uani 1 1 d . . . . .
N9 N 0.5427(3) 0.1406(4) 0.8805(3) 0.0545(12) Uani 1 1 d D . . . .
N10 N 0.6380(3) 0.0885(4) 0.9350(3) 0.0477(10) Uani 1 1 d . . . . .
N11 N 1.0669(4) 0.1958(5) 1.1711(3) 0.0653(14) Uani 1 1 d . . . . .
N12 N 0.6489(3) 0.6128(3) 0.8939(3) 0.0319(9) Uani 1 1 d . . . . .
N13 N 0.6377(3) 0.6482(4) 0.8080(3) 0.0403(10) Uani 1 1 d . . . . .
N14 N 0.6787(3) 0.5322(4) 1.0551(3) 0.0413(10) Uani 1 1 d . . . . .
N15 N 0.6105(3) 0.6301(4) 1.0286(3) 0.0452(10) Uani 1 1 d . . . . .
N16 N 0.7187(3) 0.5709(4) 0.7028(3) 0.0465(10) Uani 1 1 d . . . . .
N17 N 0.7901(3) 0.4702(4) 0.7163(3) 0.0426(10) Uani 1 1 d D . . . .
N18 N 0.7641(3) 0.4725(3) 0.8468(2) 0.0287(8) Uani 1 1 d . . . . .
N19 N 0.6800(4) 0.5548(7) 1.2153(4) 0.0894(19) Uani 1 1 d . . . . .
N20 N 0.7632(4) 0.3606(6) 1.2703(4) 0.0774(15) Uani 1 1 d . . . . .
N21 N 0.7542(4) 0.3727(5) 1.1789(3) 0.0657(13) Uani 1 1 d . . . . .
N22 N 0.4606(4) 0.8612(5) 0.8587(4) 0.0825(17) Uani 1 1 d . . . . .
Fe1 Fe 0.73837(5) 0.47416(6) 0.96527(4) 0.0324(2) Uani 1 1 d . . . . .
H9N H 0.488(3) 0.085(4) 0.862(3) 0.049 Uiso 1 1 d D U . . .
H17N H 0.813(3) 0.457(5) 0.669(2) 0.049 Uiso 1 1 d D U . . .
H7N H 0.840(3) 0.999(3) 1.008(3) 0.049 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
C1 N10 1.320(6) . ?
C1 N8 1.360(5) . ?
C1 N2 1.372(6) . ?
C2 N8 1.313(6) . ?
C2 N9 1.330(6) . ?
C3 N4 1.334(6) . ?
C3 N1 1.350(5) . ?
C3 C4 1.421(6) . ?
C4 N11 1.130(6) . ?
C5 N6 1.327(5) . ?
C5 N5 1.346(6) . ?
C5 N3 1.398(6) . ?
C6 N7 1.305(6) . ?
C6 N5 1.310(6) . ?
C7 N16 1.312(6) . ?
C7 N18 1.356(5) . ?
C7 N13 1.390(6) . ?
C8 N18 1.314(5) . ?
C8 N17 1.329(6) . ?
C9 N15 1.343(6) . ?
C9 N12 1.365(6) . ?
C9 C10 1.423(7) . ?
C10 N22 1.142(6) . ?
C11 N21 1.311(7) . ?
C11 N19 1.359(7) . ?
C11 N14 1.392(6) . ?
C12 N20 1.324(9) . ?
C12 N19 1.328(8) . ?
N1 N2 1.305(5) . ?
N1 Fe1 1.874(3) . ?
N3 N4 1.320(5) . ?
N3 Fe1 1.939(4) . ?
N6 N7 1.356(5) . ?
N8 Fe1 2.000(4) . ?
N9 N10 1.365(5) . ?
N12 N13 1.296(5) . ?
N12 Fe1 1.883(3) . ?
N14 N15 1.304(5) . ?
N14 Fe1 1.936(4) . ?
N16 N17 1.363(5) . ?
N18 Fe1 1.961(3) . ?
N20 N21 1.346(6) . ?

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
N10 C1 N8 114.1(4) . . ?
N10 C1 N2 124.1(4) . . ?
N8 C1 N2 121.7(4) . . ?
N8 C2 N9 108.6(4) . . ?
N4 C3 N1 117.4(4) . . ?
N4 C3 C4 118.7(4) . . ?
N1 C3 C4 123.9(4) . . ?
N11 C4 C3 178.9(6) . . ?
N6 C5 N5 115.2(4) . . ?
N6 C5 N3 121.6(4) . . ?
N5 C5 N3 123.2(4) . . ?
N7 C6 N5 111.2(4) . . ?
N16 C7 N18 114.3(4) . . ?
N16 C7 N13 125.9(4) . . ?
N18 C7 N13 119.9(4) . . ?
N18 C8 N17 108.3(4) . . ?
N15 C9 N12 116.8(4) . . ?
N15 C9 C10 121.5(4) . . ?
N12 C9 C10 121.6(5) . . ?
N22 C10 C9 179.0(6) . . ?
N21 C11 N19 114.4(5) . . ?
N21 C11 N14 121.5(5) . . ?
N19 C11 N14 124.0(5) . . ?
N20 C12 N19 114.1(6) . . ?
N2 N1 C3 120.5(3) . . ?
N2 N1 Fe1 124.9(3) . . ?
C3 N1 Fe1 114.5(3) . . ?
N1 N2 C1 105.9(3) . . ?
N4 N3 C5 112.2(4) . . ?
N4 N3 Fe1 116.6(3) . . ?
C5 N3 Fe1 131.2(3) . . ?
N3 N4 C3 111.7(4) . . ?
C6 N5 C5 102.2(4) . . ?
C5 N6 N7 100.8(4) . . ?
C6 N7 N6 110.6(4) . . ?
C2 N8 C1 104.4(4) . . ?
C2 N8 Fe1 146.5(3) . . ?
C1 N8 Fe1 109.1(3) . . ?
C2 N9 N10 111.5(4) . . ?
C1 N10 N9 101.3(4) . . ?
N13 N12 C9 121.3(4) . . ?
N13 N12 Fe1 124.6(3) . . ?
C9 N12 Fe1 114.0(3) . . ?
N12 N13 C7 106.1(3) . . ?
N15 N14 C11 114.6(4) . . ?
N15 N14 Fe1 117.5(3) . . ?
C11 N14 Fe1 127.8(3) . . ?
N14 N15 C9 111.9(4) . . ?
C7 N16 N17 101.4(4) . . ?
C8 N17 N16 111.5(4) . . ?
C8 N18 C7 104.5(4) . . ?
C8 N18 Fe1 144.3(3) . . ?
C7 N18 Fe1 111.2(3) . . ?
C12 N19 C11 100.0(6) . . ?
C12 N20 N21 106.2(5) . . ?
C11 N21 N20 105.1(5) . . ?
N1 Fe1 N12 174.85(15) . . ?
N1 Fe1 N14 105.00(16) . . ?
N12 Fe1 N14 79.62(16) . . ?
N1 Fe1 N3 79.73(15) . . ?
N12 Fe1 N3 102.59(15) . . ?
N14 Fe1 N3 91.97(16) . . ?
N1 Fe1 N18 97.18(14) . . ?
N12 Fe1 N18 78.21(15) . . ?
N14 Fe1 N18 157.81(16) . . ?
N3 Fe1 N18 92.19(14) . . ?
N1 Fe1 N8 78.25(15) . . ?
N12 Fe1 N8 99.50(15) . . ?
N14 Fe1 N8 92.09(16) . . ?
N3 Fe1 N8 157.91(15) . . ?
N18 Fe1 N8 92.20(15) . . ?

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
C2 H2 N19 0.93 2.46 3.357(7) 162.0 3_667
C6 H6 N11 0.93 2.58 3.384(7) 144.6 1_565
C6 H6 N16 0.93 2.59 3.273(6) 130.2 4_676
C8 H8 N5 0.93 2.25 3.128(6) 157.4 3_767
N17 H17N N10 0.899(19) 2.34(4) 3.065(6) 138(4) 2_656
C2 H2 N19 0.93 2.46 3.357(7) 162.0 3_667
C6 H6 N11 0.93 2.58 3.384(7) 144.6 1_565
C6 H6 N16 0.93 2.59 3.273(6) 130.2 4_676
C8 H8 N5 0.93 2.25 3.128(6) 157.4 3_767
N17 H17N N10 0.899(19) 2.34(4) 3.065(6) 138(4) 2_656
N9 H9N N22 0.888(19) 2.23(4) 2.951(6) 137(4) 1_545

_refine_diff_density_max         0.764
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.128

