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

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

data_7
_database_code_depnum_ccdc_archive 'CCDC 1031676'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 B2 Cu F8 N24'
_chemical_formula_weight         729.62

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.3592(7)
_cell_length_b                   8.5498(7)
_cell_length_c                   11.5516(9)
_cell_angle_alpha                111.219(2)
_cell_angle_beta                 106.8930(10)
_cell_angle_gamma                92.670(2)
_cell_volume                     725.67(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1851
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      26.49

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             363
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8610
_exptl_absorpt_correction_T_max  0.8750
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4175
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2522
_reflns_number_gt                2336
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1077P)²+1.9998P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2522
_refine_ls_number_parameters     230
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.1809
_refine_ls_wR_factor_gt          0.1771
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.0000 0.0000 0.0165(3) Uani 1 2 d S . .
N1 N 0.1058(5) 0.0335(6) -0.3411(4) 0.0354(10) Uani 1 1 d . . .
N2 N 0.2577(5) 0.0526(6) -0.1485(4) 0.0331(9) Uani 1 1 d . . .
N3 N 0.0869(5) 0.0115(6) -0.1640(4) 0.0398(11) Uani 1 1 d . . .
N4 N 0.0755(6) 0.0271(6) -0.4682(4) 0.0419(11) Uani 1 1 d . . .
N5 N 0.6499(4) 0.1918(4) -0.0006(3) 0.0209(8) Uani 1 1 d . . .
N6 N 0.5844(5) 0.3404(5) 0.0034(4) 0.0310(9) Uani 1 1 d . . .
N7 N 0.8425(4) 0.3676(4) -0.0009(4) 0.0217(8) Uani 1 1 d . . .
N8 N 0.9984(4) 0.4265(5) -0.0014(4) 0.0242(8) Uani 1 1 d . . .
N9 N 0.4532(5) 0.1674(5) 0.1577(3) 0.0239(8) Uani 1 1 d . . .
N10 N 0.2907(5) 0.1786(6) 0.1621(4) 0.0366(10) Uani 1 1 d . . .
N11 N 0.4720(5) 0.3593(5) 0.3450(4) 0.0320(9) Uani 1 1 d . . .
N12 N 0.5533(6) 0.4779(6) 0.4726(4) 0.0398(11) Uani 1 1 d . . .
B1 B 0.0160(8) 0.4335(7) 0.6188(6) 0.077(4) Uani 0.544(4) 1 d PD A 1
F1 F -0.0674(12) 0.3326(10) 0.4914(7) 0.123(3) Uani 0.544(4) 1 d PD A 1
F2 F 0.0258(10) 0.5982(7) 0.6340(9) 0.102(2) Uani 0.544(4) 1 d PD A 1
F3 F -0.0685(14) 0.4057(14) 0.6948(10) 0.166(5) Uani 0.544(4) 1 d PD A 1
F4 F 0.1739(9) 0.3974(12) 0.6547(11) 0.142(4) Uani 0.544(4) 1 d PD A 1
B2 B -0.3870(9) 0.1896(9) 0.6215(8) 0.077(4) Uani 0.456(4) 1 d PD A 2
F5 F -0.4924(13) 0.2910(11) 0.6678(11) 0.123(3) Uani 0.456(4) 1 d PD A 2
F6 F -0.4042(12) 0.0455(10) 0.6427(12) 0.102(2) Uani 0.456(4) 1 d PD A 2
F7 F -0.2252(10) 0.2720(15) 0.6843(13) 0.166(5) Uani 0.456(4) 1 d PD A 2
F8 F -0.4260(17) 0.1501(15) 0.4912(8) 0.142(4) Uani 0.456(4) 1 d PD A 2
C1 C 0.2632(6) 0.0680(8) -0.2543(5) 0.0393(12) Uani 1 1 d . . .
H1 H 0.3618 0.0986 -0.2686 0.047 Uiso 1 1 calc R . .
C2 C -0.0003(7) -0.0006(8) -0.2803(5) 0.0421(13) Uani 1 1 d . . .
H2 H -0.1178 -0.0284 -0.3169 0.051 Uiso 1 1 calc R . .
C3 C 0.7023(6) 0.4437(6) 0.0031(5) 0.0309(11) Uani 1 1 d . . .
H3 H 0.6934 0.5527 0.0052 0.037 Uiso 1 1 calc R . .
C4 C 0.8031(5) 0.2106(5) -0.0028(4) 0.0215(9) Uani 1 1 d . . .
H4 H 0.8745 0.1301 -0.0054 0.026 Uiso 1 1 calc R . .
C5 C 0.3055(7) 0.2940(7) 0.2757(5) 0.0410(13) Uani 1 1 d . . .
H5 H 0.2157 0.3275 0.3056 0.049 Uiso 1 1 calc R . .
C6 C 0.5599(6) 0.2775(7) 0.2673(5) 0.0336(11) Uani 1 1 d . . .
H6 H 0.6773 0.2965 0.2885 0.040 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N5 2.020(3) 2_655 ?
Cu1 N5 2.020(3) . ?
Cu1 N9 2.024(3) 2_655 ?
Cu1 N9 2.024(3) . ?
Cu1 N2 2.423(4) 2_655 ?
Cu1 N2 2.423(4) . ?
N1 C1 1.344(6) . ?
N1 C2 1.360(7) . ?
N1 N4 1.395(5) . ?
N2 C1 1.289(6) . ?
N2 N3 1.397(6) . ?
N3 C2 1.293(6) . ?
N4 N4 1.228(9) 2_554 ?
N5 C4 1.293(6) . ?
N5 N6 1.397(5) . ?
N6 C3 1.294(6) . ?
N7 C4 1.357(5) . ?
N7 C3 1.371(6) . ?
N7 N8 1.378(5) . ?
N8 N8 1.245(7) 2_765 ?
N9 C6 1.299(6) . ?
N9 N10 1.381(5) . ?
N10 C5 1.292(6) . ?
N11 C6 1.346(6) . ?
N11 C5 1.359(7) . ?
N11 N12 1.391(5) . ?
N12 N12 1.234(9) 2_666 ?
B1 F2 1.3497(10) . ?
B1 F4 1.3500(10) . ?
B1 F3 1.3500(10) . ?
B1 F1 1.3503(10) . ?
B2 F6 1.3497(10) . ?
B2 F5 1.3497(10) . ?
B2 F7 1.3499(11) . ?
B2 F8 1.3501(10) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Cu1 N5 180.0 2_655 . ?
N5 Cu1 N9 89.30(14) 2_655 2_655 ?
N5 Cu1 N9 90.70(14) . 2_655 ?
N5 Cu1 N9 90.70(14) 2_655 . ?
N5 Cu1 N9 89.30(14) . . ?
N9 Cu1 N9 180.0 2_655 . ?
N5 Cu1 N2 90.23(14) 2_655 2_655 ?
N5 Cu1 N2 89.77(14) . 2_655 ?
N9 Cu1 N2 90.89(15) 2_655 2_655 ?
N9 Cu1 N2 89.11(15) . 2_655 ?
N5 Cu1 N2 89.77(14) 2_655 . ?
N5 Cu1 N2 90.23(14) . . ?
N9 Cu1 N2 89.11(15) 2_655 . ?
N9 Cu1 N2 90.89(15) . . ?
N2 Cu1 N2 180.0(2) 2_655 . ?
C1 N1 C2 105.8(4) . . ?
C1 N1 N4 122.3(4) . . ?
C2 N1 N4 131.7(4) . . ?
C1 N2 N3 107.3(4) . . ?
C1 N2 Cu1 122.1(3) . . ?
N3 N2 Cu1 126.9(3) . . ?
C2 N3 N2 107.0(4) . . ?
N4 N4 N1 109.2(5) 2_554 . ?
C4 N5 N6 108.8(3) . . ?
C4 N5 Cu1 133.3(3) . . ?
N6 N5 Cu1 118.0(3) . . ?
C3 N6 N5 106.7(3) . . ?
C4 N7 C3 106.5(3) . . ?
C4 N7 N8 122.5(4) . . ?
C3 N7 N8 130.9(4) . . ?
N8 N8 N7 109.6(4) 2_765 . ?
C6 N9 N10 108.7(4) . . ?
C6 N9 Cu1 129.1(3) . . ?
N10 N9 Cu1 122.2(3) . . ?
C5 N10 N9 106.5(4) . . ?
C6 N11 C5 106.4(4) . . ?
C6 N11 N12 121.6(4) . . ?
C5 N11 N12 131.9(4) . . ?
N12 N12 N11 109.2(5) 2_666 . ?
F2 B1 F4 109.50(8) . . ?
F2 B1 F3 109.48(8) . . ?
F4 B1 F3 109.47(8) . . ?
F2 B1 F1 109.47(8) . . ?
F4 B1 F1 109.46(8) . . ?
F3 B1 F1 109.46(8) . . ?
F6 B2 F5 109.49(8) . . ?
F6 B2 F7 109.48(8) . . ?
F5 B2 F7 109.48(8) . . ?
F6 B2 F8 109.47(8) . . ?
F5 B2 F8 109.47(8) . . ?
F7 B2 F8 109.45(8) . . ?
N2 C1 N1 110.2(5) . . ?
N2 C1 H1 124.9 . . ?
N1 C1 H1 124.9 . . ?
N3 C2 N1 109.7(4) . . ?
N3 C2 H2 125.1 . . ?
N1 C2 H2 125.1 . . ?
N6 C3 N7 109.4(4) . . ?
N6 C3 H3 125.3 . . ?
N7 C3 H3 125.3 . . ?
N5 C4 N7 108.6(4) . . ?
N5 C4 H4 125.7 . . ?
N7 C4 H4 125.7 . . ?
N10 C5 N11 109.9(4) . . ?
N10 C5 H5 125.1 . . ?
N11 C5 H5 125.1 . . ?
N9 C6 N11 108.5(4) . . ?
N9 C6 H6 125.8 . . ?
N11 C6 H6 125.8 . . ?

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
N5 Cu1 N2 C1 -131.0(4) 2_655 . . . ?
N5 Cu1 N2 C1 49.0(4) . . . . ?
N9 Cu1 N2 C1 -41.7(4) 2_655 . . . ?
N9 Cu1 N2 C1 138.3(4) . . . . ?
N2 Cu1 N2 C1 -31(36) 2_655 . . . ?
N5 Cu1 N2 N3 24.2(4) 2_655 . . . ?
N5 Cu1 N2 N3 -155.8(4) . . . . ?
N9 Cu1 N2 N3 113.5(4) 2_655 . . . ?
N9 Cu1 N2 N3 -66.5(4) . . . . ?
N2 Cu1 N2 N3 125(36) 2_655 . . . ?
C1 N2 N3 C2 1.9(6) . . . . ?
Cu1 N2 N3 C2 -156.2(4) . . . . ?
C1 N1 N4 N4 171.7(6) . . . 2_554 ?
C2 N1 N4 N4 -3.6(10) . . . 2_554 ?
N5 Cu1 N5 C4 115(7) 2_655 . . . ?
N9 Cu1 N5 C4 -51.1(4) 2_655 . . . ?
N9 Cu1 N5 C4 128.9(4) . . . . ?
N2 Cu1 N5 C4 39.8(4) 2_655 . . . ?
N2 Cu1 N5 C4 -140.2(4) . . . . ?
N5 Cu1 N5 N6 -65(7) 2_655 . . . ?
N9 Cu1 N5 N6 129.6(3) 2_655 . . . ?
N9 Cu1 N5 N6 -50.4(3) . . . . ?
N2 Cu1 N5 N6 -139.5(3) 2_655 . . . ?
N2 Cu1 N5 N6 40.5(3) . . . . ?
C4 N5 N6 C3 0.1(5) . . . . ?
Cu1 N5 N6 C3 179.6(3) . . . . ?
C4 N7 N8 N8 -179.7(4) . . . 2_765 ?
C3 N7 N8 N8 -0.6(8) . . . 2_765 ?
N5 Cu1 N9 C6 129.7(4) 2_655 . . . ?
N5 Cu1 N9 C6 -50.3(4) . . . . ?
N9 Cu1 N9 C6 -154(23) 2_655 . . . ?
N2 Cu1 N9 C6 39.5(4) 2_655 . . . ?
N2 Cu1 N9 C6 -140.5(4) . . . . ?
N5 Cu1 N9 N10 -50.0(4) 2_655 . . . ?
N5 Cu1 N9 N10 130.0(4) . . . . ?
N9 Cu1 N9 N10 26(23) 2_655 . . . ?
N2 Cu1 N9 N10 -140.2(4) 2_655 . . . ?
N2 Cu1 N9 N10 39.8(4) . . . . ?
C6 N9 N10 C5 -0.9(6) . . . . ?
Cu1 N9 N10 C5 178.9(4) . . . . ?
C6 N11 N12 N12 -173.5(6) . . . 2_666 ?
C5 N11 N12 N12 2.2(10) . . . 2_666 ?
N3 N2 C1 N1 -2.2(6) . . . . ?
Cu1 N2 C1 N1 157.3(4) . . . . ?
C2 N1 C1 N2 1.6(7) . . . . ?
N4 N1 C1 N2 -174.8(5) . . . . ?
N2 N3 C2 N1 -1.0(7) . . . . ?
C1 N1 C2 N3 -0.3(7) . . . . ?
N4 N1 C2 N3 175.6(5) . . . . ?
N5 N6 C3 N7 0.0(6) . . . . ?
C4 N7 C3 N6 -0.1(6) . . . . ?
N8 N7 C3 N6 -179.3(4) . . . . ?
N6 N5 C4 N7 -0.2(5) . . . . ?
Cu1 N5 C4 N7 -179.5(3) . . . . ?
C3 N7 C4 N5 0.1(5) . . . . ?
N8 N7 C4 N5 179.4(4) . . . . ?
N9 N10 C5 N11 0.5(6) . . . . ?
C6 N11 C5 N10 0.1(7) . . . . ?
N12 N11 C5 N10 -176.0(5) . . . . ?
N10 N9 C6 N11 1.0(6) . . . . ?
Cu1 N9 C6 N11 -178.7(3) . . . . ?
C5 N11 C6 N9 -0.7(6) . . . . ?
N12 N11 C6 N9 176.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.433
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.125
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8
_database_code_depnum_ccdc_archive 'CCDC 1031678'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H21.50 Cu2 N8 O13.75 S'
_chemical_formula_weight         560.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Pc

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

_cell_length_a                   6.9597(11)
_cell_length_b                   6.8943(11)
_cell_length_c                   18.317(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.213(4)
_cell_angle_gamma                90.00
_cell_volume                     873.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2137
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      28.30

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    2.132
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             571
_exptl_absorpt_coefficient_mu    2.645
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7779
_exptl_absorpt_correction_T_max  0.8163
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4820
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0596
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2168
_reflns_number_gt                1967
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0315P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.90(3)
_refine_ls_number_reflns         2168
_refine_ls_number_parameters     263
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0734
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.00411(6) 1.04749(8) 0.27074(3) 0.00590(19) Uani 1 1 d . . .
Cu2 Cu 0.01651(6) 0.54676(8) 0.26537(3) 0.0066(2) Uani 1 1 d . . .
S1 S -0.0167(2) 0.79750(16) 0.50896(9) 0.0100(3) Uani 1 1 d . . .
O1 O -0.1139(5) 0.9855(5) 0.4930(2) 0.0148(9) Uani 1 1 d . . .
O2 O -0.1578(5) 0.6379(5) 0.4905(2) 0.0155(9) Uani 1 1 d . . .
O3 O 0.0565(6) 0.7839(5) 0.5869(2) 0.0182(10) Uani 1 1 d . . .
O4 O 0.1445(5) 0.7767(5) 0.4637(2) 0.0157(9) Uani 1 1 d . . .
O5 O 0.7728(6) 0.4996(6) 0.3507(3) 0.0131(10) Uani 1 1 d . . .
H5A H 0.6668 0.5553 0.3358 0.020 Uiso 1 1 d R . .
H5B H 0.8188 0.5561 0.3900 0.020 Uiso 1 1 d R . .
O6 O 0.2579(6) 0.6071(6) 0.1791(3) 0.0131(10) Uani 1 1 d . . .
H6A H 0.2268 0.5829 0.1339 0.020 Uiso 1 1 d R . .
H6B H 0.3279 0.5137 0.1968 0.020 Uiso 1 1 d R . .
O7 O 0.0898(5) 0.7972(5) 0.3103(2) 0.0062(9) Uani 1 1 d . . .
H7 H 0.0844 0.7970 0.3564 0.009 Uiso 1 1 d R . .
O8 O -0.2457(6) 1.0961(6) 0.3524(3) 0.0142(11) Uani 1 1 d . . .
H8A H -0.1846 1.0822 0.3949 0.021 Uiso 1 1 d R . .
H8B H -0.2722 1.2159 0.3469 0.021 Uiso 1 1 d R . .
O9 O 0.2795(6) 1.0096(6) 0.1889(3) 0.0111(10) Uani 1 1 d . . .
H9A H 0.2854 0.8888 0.1802 0.017 Uiso 1 1 d R . .
H9B H 0.2322 1.0645 0.1494 0.017 Uiso 1 1 d R . .
O10 O -0.0707(6) 1.2961(5) 0.2240(2) 0.0095(10) Uani 1 1 d . . .
H10 H -0.0397 1.2754 0.1810 0.014 Uiso 1 1 d R . .
O11 O 0.5055(6) 0.7897(5) 0.3204(3) 0.0226(11) Uani 1 1 d . . .
H11A H 0.3845 0.8091 0.3120 0.034 Uiso 1 1 d R . .
H11B H 0.5597 0.8999 0.3261 0.034 Uiso 1 1 d R . .
O12 O 0.5160(7) 0.3253(5) 0.2268(3) 0.0320(13) Uani 1 1 d U . .
H12A H 0.6386 0.3172 0.2300 0.048 Uiso 1 1 d R . .
H12B H 0.4706 0.2365 0.1976 0.048 Uiso 1 1 d R . .
O13 O 0.5079(9) 0.7131(7) 0.5583(4) 0.0240(14) Uani 0.75 1 d P . .
H13A H 0.4223 0.7902 0.5385 0.036 Uiso 0.75 1 d PR . .
H13B H 0.6087 0.7281 0.5365 0.036 Uiso 0.75 1 d PR . .
O14 O 0.0866(6) 0.3222(5) 0.5370(2) 0.0181(10) Uani 1 1 d . . .
H14A H 0.0230 0.4210 0.5204 0.027 Uiso 1 1 d R . .
H14B H 0.0245 0.2223 0.5207 0.027 Uiso 1 1 d R . .
N1 N 0.3868(7) 0.3027(6) 0.4343(3) 0.0059(11) Uani 1 1 d U . .
N2 N 0.1808(7) 0.1978(6) 0.3465(3) 0.0081(11) Uani 1 1 d . . .
N3 N 0.1997(7) 0.3984(7) 0.3384(3) 0.0097(12) Uani 1 1 d . . .
N4 N 0.5121(7) 0.3232(7) 0.4980(3) 0.0127(13) Uani 1 1 d . . .
N5 N 0.5225(7) 0.1709(7) 0.5334(3) 0.0084(11) Uani 1 1 d U . .
N6 N 0.6453(7) 0.1961(6) 0.5977(3) 0.0084(11) Uani 1 1 d . . .
N7 N 0.8284(7) 0.1015(6) 0.6936(3) 0.0057(10) Uani 1 1 d U . .
N8 N 0.8363(7) 0.3024(6) 0.6903(3) 0.0084(11) Uani 1 1 d U . .
C1 C 0.3273(9) 0.4568(8) 0.3927(4) 0.0106(15) Uani 1 1 d . . .
H1 H 0.3691 0.5838 0.4009 0.013 Uiso 1 1 calc R . .
C2 C 0.2910(8) 0.1402(9) 0.4041(4) 0.0093(14) Uani 1 1 d . . .
H2 H 0.3033 0.0139 0.4218 0.011 Uiso 1 1 calc R . .
C3 C 0.7146(9) 0.0403(8) 0.6386(4) 0.0102(15) Uani 1 1 d . . .
H3 H 0.6843 -0.0889 0.6282 0.012 Uiso 1 1 calc R . .
C4 C 0.7247(9) 0.3569(9) 0.6314(4) 0.0106(14) Uani 1 1 d . . .
H4 H 0.7038 0.4840 0.6155 0.013 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O7 1.940(4) . ?
Cu1 O10 1.961(4) . ?
Cu1 N2 2.035(5) 1_565 ?
Cu1 N7 2.042(5) 2_464 ?
Cu1 O8 2.437(5) . ?
Cu1 O9 2.571(5) . ?
Cu2 O10 1.957(4) 1_545 ?
Cu2 O7 1.956(4) . ?
Cu2 N3 2.023(5) . ?
Cu2 N8 2.042(5) 2_464 ?
Cu2 O6 2.463(5) . ?
S1 O3 1.466(4) . ?
S1 O4 1.472(4) . ?
S1 O1 1.477(4) . ?
S1 O2 1.489(4) . ?
O5 H5A 0.8500 . ?
O5 H5B 0.8501 . ?
O6 H6A 0.8499 . ?
O6 H6B 0.8504 . ?
O7 H7 0.8499 . ?
O8 H8A 0.8500 . ?
O8 H8B 0.8500 . ?
O9 H9A 0.8500 . ?
O9 H9B 0.8501 . ?
O10 Cu2 1.957(4) 1_565 ?
O10 H10 0.8500 . ?
O11 H11A 0.8500 . ?
O11 H11B 0.8500 . ?
O12 H12A 0.8504 . ?
O12 H12B 0.8509 . ?
O13 H13A 0.8498 . ?
O13 H13B 0.8504 . ?
O14 H14A 0.8500 . ?
O14 H14B 0.8500 . ?
N1 C1 1.346(7) . ?
N1 N4 1.387(7) . ?
N1 C2 1.388(8) . ?
N2 C2 1.298(8) . ?
N2 N3 1.398(6) . ?
N2 Cu1 2.035(5) 1_545 ?
N3 C1 1.323(8) . ?
N4 N5 1.232(5) . ?
N5 N6 1.389(7) . ?
N6 C4 1.357(8) . ?
N6 C3 1.367(8) . ?
N7 C3 1.285(8) . ?
N7 N8 1.388(6) . ?
N7 Cu1 2.042(5) 2_665 ?
N8 C4 1.314(8) . ?
N8 Cu2 2.042(5) 2_665 ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 Cu1 O10 175.4(2) . . ?
O7 Cu1 N2 93.43(18) . 1_565 ?
O10 Cu1 N2 87.99(18) . 1_565 ?
O7 Cu1 N7 87.01(17) . 2_464 ?
O10 Cu1 N7 91.53(17) . 2_464 ?
N2 Cu1 N7 179.2(2) 1_565 2_464 ?
O7 Cu1 O8 95.95(17) . . ?
O10 Cu1 O8 88.55(17) . . ?
N2 Cu1 O8 85.97(18) 1_565 . ?
N7 Cu1 O8 94.61(18) 2_464 . ?
O7 Cu1 O9 84.80(16) . . ?
O10 Cu1 O9 90.77(16) . . ?
N2 Cu1 O9 90.91(18) 1_565 . ?
N7 Cu1 O9 88.50(18) 2_464 . ?
O8 Cu1 O9 176.83(15) . . ?
O10 Cu2 O7 176.4(2) 1_545 . ?
O10 Cu2 N3 87.50(18) 1_545 . ?
O7 Cu2 N3 92.94(18) . . ?
O10 Cu2 N8 92.67(17) 1_545 2_464 ?
O7 Cu2 N8 86.96(17) . 2_464 ?
N3 Cu2 N8 178.8(2) . 2_464 ?
O10 Cu2 O6 96.03(16) 1_545 . ?
O7 Cu2 O6 87.49(16) . . ?
N3 Cu2 O6 94.85(19) . . ?
N8 Cu2 O6 83.92(18) 2_464 . ?
O3 S1 O4 109.7(2) . . ?
O3 S1 O1 110.6(2) . . ?
O4 S1 O1 109.6(2) . . ?
O3 S1 O2 109.0(2) . . ?
O4 S1 O2 108.9(2) . . ?
O1 S1 O2 109.1(2) . . ?
H5A O5 H5B 107.4 . . ?
Cu2 O6 H6A 118.2 . . ?
Cu2 O6 H6B 91.7 . . ?
H6A O6 H6B 107.4 . . ?
Cu1 O7 Cu2 124.9(2) . . ?
Cu1 O7 H7 109.1 . . ?
Cu2 O7 H7 112.3 . . ?
Cu1 O8 H8A 103.1 . . ?
Cu1 O8 H8B 102.7 . . ?
H8A O8 H8B 107.4 . . ?
Cu1 O9 H9A 105.2 . . ?
Cu1 O9 H9B 101.9 . . ?
H9A O9 H9B 107.4 . . ?
Cu2 O10 Cu1 123.1(2) 1_565 . ?
Cu2 O10 H10 114.1 1_565 . ?
Cu1 O10 H10 100.1 . . ?
H11A O11 H11B 107.4 . . ?
H12A O12 H12B 107.3 . . ?
H13A O13 H13B 107.4 . . ?
H14A O14 H14B 107.4 . . ?
C1 N1 N4 121.5(4) . . ?
C1 N1 C2 107.8(5) . . ?
N4 N1 C2 130.5(5) . . ?
C2 N2 N3 109.5(5) . . ?
C2 N2 Cu1 131.2(4) . 1_545 ?
N3 N2 Cu1 119.2(4) . 1_545 ?
C1 N3 N2 106.5(5) . . ?
C1 N3 Cu2 131.8(4) . . ?
N2 N3 Cu2 120.7(3) . . ?
N5 N4 N1 110.6(4) . . ?
N4 N5 N6 109.6(4) . . ?
C4 N6 C3 106.9(5) . . ?
C4 N6 N5 132.1(5) . . ?
C3 N6 N5 120.9(5) . . ?
C3 N7 N8 108.5(5) . . ?
C3 N7 Cu1 130.6(4) . 2_665 ?
N8 N7 Cu1 120.6(3) . 2_665 ?
C4 N8 N7 107.4(5) . . ?
C4 N8 Cu2 132.3(4) . 2_665 ?
N7 N8 Cu2 120.2(3) . 2_665 ?
N3 C1 N1 109.0(5) . . ?
N3 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
N2 C2 N1 107.1(5) . . ?
N2 C2 H2 126.5 . . ?
N1 C2 H2 126.5 . . ?
N7 C3 N6 108.8(5) . . ?
N7 C3 H3 125.6 . . ?
N6 C3 H3 125.6 . . ?
N8 C4 N6 108.4(5) . . ?
N8 C4 H4 125.8 . . ?
N6 C4 H4 125.8 . . ?

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
O10 Cu1 O7 Cu2 -65(2) . . . . ?
N2 Cu1 O7 Cu2 -173.1(3) 1_565 . . . ?
N7 Cu1 O7 Cu2 6.3(3) 2_464 . . . ?
O8 Cu1 O7 Cu2 100.6(3) . . . . ?
O9 Cu1 O7 Cu2 -82.5(3) . . . . ?
O10 Cu2 O7 Cu1 -90(3) 1_545 . . . ?
N3 Cu2 O7 Cu1 173.4(3) . . . . ?
N8 Cu2 O7 Cu1 -5.4(3) 2_464 . . . ?
O6 Cu2 O7 Cu1 78.6(3) . . . . ?
O7 Cu1 O10 Cu2 -113(2) . . . 1_565 ?
N2 Cu1 O10 Cu2 -5.2(3) 1_565 . . 1_565 ?
N7 Cu1 O10 Cu2 175.4(3) 2_464 . . 1_565 ?
O8 Cu1 O10 Cu2 80.8(3) . . . 1_565 ?
O9 Cu1 O10 Cu2 -96.1(3) . . . 1_565 ?
C2 N2 N3 C1 0.9(8) . . . . ?
Cu1 N2 N3 C1 -177.5(5) 1_545 . . . ?
C2 N2 N3 Cu2 -169.3(4) . . . . ?
Cu1 N2 N3 Cu2 12.3(6) 1_545 . . . ?
O10 Cu2 N3 C1 -179.8(7) 1_545 . . . ?
O7 Cu2 N3 C1 -3.4(7) . . . . ?
N8 Cu2 N3 C1 82(9) 2_464 . . . ?
O6 Cu2 N3 C1 84.3(7) . . . . ?
O10 Cu2 N3 N2 -12.6(4) 1_545 . . . ?
O7 Cu2 N3 N2 163.9(5) . . . . ?
N8 Cu2 N3 N2 -111(9) 2_464 . . . ?
O6 Cu2 N3 N2 -108.4(4) . . . . ?
C1 N1 N4 N5 169.0(6) . . . . ?
C2 N1 N4 N5 -5.9(9) . . . . ?
N1 N4 N5 N6 -178.7(6) . . . . ?
N4 N5 N6 C4 11.9(9) . . . . ?
N4 N5 N6 C3 -165.5(6) . . . . ?
C3 N7 N8 C4 -0.4(8) . . . . ?
Cu1 N7 N8 C4 173.3(4) 2_665 . . . ?
C3 N7 N8 Cu2 -176.2(5) . . . 2_665 ?
Cu1 N7 N8 Cu2 -2.5(6) 2_665 . . 2_665 ?
N2 N3 C1 N1 -0.5(8) . . . . ?
Cu2 N3 C1 N1 168.1(4) . . . . ?
N4 N1 C1 N3 -175.9(6) . . . . ?
C2 N1 C1 N3 0.0(8) . . . . ?
N3 N2 C2 N1 -0.9(7) . . . . ?
Cu1 N2 C2 N1 177.3(4) 1_545 . . . ?
C1 N1 C2 N2 0.6(7) . . . . ?
N4 N1 C2 N2 176.0(6) . . . . ?
N8 N7 C3 N6 0.2(8) . . . . ?
Cu1 N7 C3 N6 -172.7(4) 2_665 . . . ?
C4 N6 C3 N7 0.2(8) . . . . ?
N5 N6 C3 N7 178.1(6) . . . . ?
N7 N8 C4 N6 0.5(8) . . . . ?
Cu2 N8 C4 N6 175.5(4) 2_665 . . . ?
C3 N6 C4 N8 -0.4(8) . . . . ?
N5 N6 C4 N8 -178.1(6) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.096
####################################################################### 
# 
# 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_n130710b
_database_code_depnum_ccdc_archive 'CCDC 1031679'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H10 Cl2 Fe N8 O3'
_chemical_formula_weight         344.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.0475(5)
_cell_length_b                   11.7191(7)
_cell_length_c                   12.4796(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.9300(10)
_cell_angle_gamma                90.00
_cell_volume                     1174.18(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3757
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      28.30

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.951
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    1.755
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7429
_exptl_absorpt_correction_T_max  0.8170
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5910
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2067
_reflns_number_gt                1928
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0146P)²+1.1748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2067
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0485
_refine_ls_wR_factor_gt          0.0473
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 1.0000 1.0000 0.0000 0.00766(10) Uani 1 2 d S . .
Fe2 Fe 0.5000 1.0000 0.0000 0.00784(10) Uani 1 2 d S . .
Cl1 Cl 0.76100(5) 0.93123(4) 0.09847(3) 0.01015(11) Uani 1 1 d . . .
Cl2 Cl 0.25892(6) 0.34174(4) 0.08252(4) 0.01819(12) Uani 1 1 d . . .
O1 O 0.98064(16) 1.15839(11) 0.07316(10) 0.0115(3) Uani 1 1 d . . .
H1A H 0.9492 1.1555 0.1359 0.017 Uiso 1 1 d R . .
H1B H 1.0619 1.2032 0.0717 0.017 Uiso 1 1 d R . .
O2 O 0.53802(16) 1.16019(11) 0.07050(10) 0.0120(3) Uani 1 1 d . . .
H2A H 0.4615 1.2090 0.0656 0.018 Uiso 1 1 d R . .
H2B H 0.5803 1.1588 0.1339 0.018 Uiso 1 1 d R . .
O3 O 0.28404(19) 0.17882(13) 0.29716(13) 0.0258(4) Uani 1 1 d . . .
H3A H 0.2795 0.2152 0.2390 0.039 Uiso 1 1 d R . .
H3B H 0.2717 0.2317 0.3413 0.039 Uiso 1 1 d R . .
N1 N 0.28380(19) 0.91942(13) 0.29710(12) 0.0085(3) Uani 1 1 d . . .
N2 N 0.35212(19) 0.95067(13) 0.13452(13) 0.0099(3) Uani 1 1 d . . .
N3 N 0.17772(19) 0.94837(13) 0.13480(13) 0.0100(3) Uani 1 1 d . . .
N4 N 0.3119(2) 0.90135(14) 0.40717(13) 0.0123(3) Uani 1 1 d . . .
N5 N 0.1767(2) 0.89446(14) 0.44862(13) 0.0129(4) Uani 1 1 d . . .
N6 N 0.2030(2) 0.87304(14) 0.55715(13) 0.0124(3) Uani 1 1 d . . .
N7 N 0.3076(2) 0.84165(14) 0.72006(13) 0.0157(4) Uani 1 1 d . . .
N8 N 0.1336(2) 0.84440(14) 0.72071(13) 0.0161(4) Uani 1 1 d . . .
C1 C 0.4117(2) 0.93275(15) 0.23286(15) 0.0101(4) Uani 1 1 d . . .
H1 H 0.5266 0.9295 0.2559 0.012 Uiso 1 1 calc R . .
C2 C 0.1403(2) 0.92916(15) 0.23291(15) 0.0103(4) Uani 1 1 d . . .
H2 H 0.0306 0.9229 0.2561 0.012 Uiso 1 1 calc R . .
C3 C 0.3466(2) 0.85931(17) 0.62148(16) 0.0148(4) Uani 1 1 d . . .
H3 H 0.4565 0.8622 0.5982 0.018 Uiso 1 1 calc R . .
C4 C 0.0745(2) 0.86357(17) 0.62212(16) 0.0150(4) Uani 1 1 d . . .
H4 H -0.0403 0.8699 0.5994 0.018 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O1 2.0791(13) . ?
Fe1 O1 2.0791(13) 3_775 ?
Fe1 N3 2.2162(15) 1_655 ?
Fe1 N3 2.2162(15) 3_675 ?
Fe1 Cl1 2.4865(4) 3_775 ?
Fe1 Cl1 2.4865(4) . ?
Fe2 O2 2.0869(13) . ?
Fe2 O2 2.0869(13) 3_675 ?
Fe2 N2 2.2006(15) . ?
Fe2 N2 2.2006(15) 3_675 ?
Fe2 Cl1 2.4934(4) . ?
Fe2 Cl1 2.4934(4) 3_675 ?
O1 H1A 0.8400 . ?
O1 H1B 0.8400 . ?
O2 H2A 0.8400 . ?
O2 H2B 0.8400 . ?
O3 H3A 0.8401 . ?
O3 H3B 0.8401 . ?
N1 C1 1.357(2) . ?
N1 C2 1.365(2) . ?
N1 N4 1.393(2) . ?
N2 C1 1.304(2) . ?
N2 N3 1.404(2) . ?
N3 C2 1.300(2) . ?
N3 Fe1 2.2163(15) 1_455 ?
N4 N5 1.239(2) . ?
N5 N6 1.379(2) . ?
N6 C4 1.362(3) . ?
N6 C3 1.370(3) . ?
N7 C3 1.307(3) . ?
N7 N8 1.401(2) . ?
N8 C4 1.308(3) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 O1 179.999(1) . 3_775 ?
O1 Fe1 N3 88.52(5) . 1_655 ?
O1 Fe1 N3 91.47(5) 3_775 1_655 ?
O1 Fe1 N3 91.48(5) . 3_675 ?
O1 Fe1 N3 88.53(5) 3_775 3_675 ?
N3 Fe1 N3 180.0 1_655 3_675 ?
O1 Fe1 Cl1 90.65(4) . 3_775 ?
O1 Fe1 Cl1 89.35(4) 3_775 3_775 ?
N3 Fe1 Cl1 89.02(4) 1_655 3_775 ?
N3 Fe1 Cl1 90.99(4) 3_675 3_775 ?
O1 Fe1 Cl1 89.34(4) . . ?
O1 Fe1 Cl1 90.66(4) 3_775 . ?
N3 Fe1 Cl1 90.98(4) 1_655 . ?
N3 Fe1 Cl1 89.01(4) 3_675 . ?
Cl1 Fe1 Cl1 180.0 3_775 . ?
O2 Fe2 O2 180.0 . 3_675 ?
O2 Fe2 N2 89.20(5) . . ?
O2 Fe2 N2 90.80(5) 3_675 . ?
O2 Fe2 N2 90.80(5) . 3_675 ?
O2 Fe2 N2 89.20(5) 3_675 3_675 ?
N2 Fe2 N2 180.0 . 3_675 ?
O2 Fe2 Cl1 89.36(4) . . ?
O2 Fe2 Cl1 90.64(4) 3_675 . ?
N2 Fe2 Cl1 91.17(4) . . ?
N2 Fe2 Cl1 88.83(4) 3_675 . ?
O2 Fe2 Cl1 90.64(4) . 3_675 ?
O2 Fe2 Cl1 89.36(4) 3_675 3_675 ?
N2 Fe2 Cl1 88.83(4) . 3_675 ?
N2 Fe2 Cl1 91.17(4) 3_675 3_675 ?
Cl1 Fe2 Cl1 180.0 . 3_675 ?
Fe1 Cl1 Fe2 107.800(17) . . ?
Fe1 O1 H1A 114.2 . . ?
Fe1 O1 H1B 117.8 . . ?
H1A O1 H1B 109.3 . . ?
Fe2 O2 H2A 119.8 . . ?
Fe2 O2 H2B 114.7 . . ?
H2A O2 H2B 109.3 . . ?
H3A O3 H3B 101.1 . . ?
C1 N1 C2 106.84(15) . . ?
C1 N1 N4 121.46(15) . . ?
C2 N1 N4 131.70(15) . . ?
C1 N2 N3 107.34(15) . . ?
C1 N2 Fe2 125.24(13) . . ?
N3 N2 Fe2 126.87(11) . . ?
C2 N3 N2 107.58(15) . . ?
C2 N3 Fe1 125.64(12) . 1_455 ?
N2 N3 Fe1 125.88(11) . 1_455 ?
N5 N4 N1 109.51(15) . . ?
N4 N5 N6 109.97(15) . . ?
C4 N6 C3 106.61(16) . . ?
C4 N6 N5 121.84(16) . . ?
C3 N6 N5 131.54(16) . . ?
C3 N7 N8 107.83(16) . . ?
C4 N8 N7 107.34(16) . . ?
N2 C1 N1 109.24(16) . . ?
N2 C1 H1 125.4 . . ?
N1 C1 H1 125.4 . . ?
N3 C2 N1 109.00(16) . . ?
N3 C2 H2 125.5 . . ?
N1 C2 H2 125.5 . . ?
N7 C3 N6 108.85(17) . . ?
N7 C3 H3 125.6 . . ?
N6 C3 H3 125.6 . . ?
N8 C4 N6 109.37(18) . . ?
N8 C4 H4 125.3 . . ?
N6 C4 H4 125.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Fe1 Cl1 Fe2 80.66(4) . . . . ?
O1 Fe1 Cl1 Fe2 -99.35(4) 3_775 . . . ?
N3 Fe1 Cl1 Fe2 169.17(4) 1_655 . . . ?
N3 Fe1 Cl1 Fe2 -10.83(4) 3_675 . . . ?
Cl1 Fe1 Cl1 Fe2 85(8) 3_775 . . . ?
O2 Fe2 Cl1 Fe1 -79.36(4) . . . . ?
O2 Fe2 Cl1 Fe1 100.64(4) 3_675 . . . ?
N2 Fe2 Cl1 Fe1 -168.55(4) . . . . ?
N2 Fe2 Cl1 Fe1 11.45(4) 3_675 . . . ?
Cl1 Fe2 Cl1 Fe1 -92(11) 3_675 . . . ?
O2 Fe2 N2 C1 -70.12(15) . . . . ?
O2 Fe2 N2 C1 109.88(15) 3_675 . . . ?
N2 Fe2 N2 C1 -55(8) 3_675 . . . ?
Cl1 Fe2 N2 C1 19.22(15) . . . . ?
Cl1 Fe2 N2 C1 -160.78(15) 3_675 . . . ?
O2 Fe2 N2 N3 100.24(14) . . . . ?
O2 Fe2 N2 N3 -79.76(14) 3_675 . . . ?
N2 Fe2 N2 N3 115(8) 3_675 . . . ?
Cl1 Fe2 N2 N3 -170.42(13) . . . . ?
Cl1 Fe2 N2 N3 9.58(13) 3_675 . . . ?
C1 N2 N3 C2 0.0(2) . . . . ?
Fe2 N2 N3 C2 -171.81(12) . . . . ?
C1 N2 N3 Fe1 169.53(12) . . . 1_455 ?
Fe2 N2 N3 Fe1 -2.2(2) . . . 1_455 ?
C1 N1 N4 N5 178.46(16) . . . . ?
C2 N1 N4 N5 -0.5(3) . . . . ?
N1 N4 N5 N6 178.16(14) . . . . ?
N4 N5 N6 C4 178.82(17) . . . . ?
N4 N5 N6 C3 0.1(3) . . . . ?
C3 N7 N8 C4 0.1(2) . . . . ?
N3 N2 C1 N1 -0.3(2) . . . . ?
Fe2 N2 C1 N1 171.66(11) . . . . ?
C2 N1 C1 N2 0.5(2) . . . . ?
N4 N1 C1 N2 -178.68(15) . . . . ?
N2 N3 C2 N1 0.3(2) . . . . ?
Fe1 N3 C2 N1 -169.26(11) 1_455 . . . ?
C1 N1 C2 N3 -0.5(2) . . . . ?
N4 N1 C2 N3 178.54(17) . . . . ?
N8 N7 C3 N6 -0.3(2) . . . . ?
C4 N6 C3 N7 0.4(2) . . . . ?
N5 N6 C3 N7 179.31(18) . . . . ?
N7 N8 C4 N6 0.2(2) . . . . ?
C3 N6 C4 N8 -0.4(2) . . . . ?
N5 N6 C4 N8 -179.41(16) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.054
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1031680'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 Fe N10 O2 S2'
_chemical_formula_weight         372.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.046(3)
_cell_length_b                   6.820(3)
_cell_length_c                   9.086(4)
_cell_angle_alpha                83.370(7)
_cell_angle_beta                 81.332(7)
_cell_angle_gamma                68.356(6)
_cell_volume                     343.5(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1777
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      28.37

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             188
_exptl_absorpt_coefficient_mu    1.423
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7837
_exptl_absorpt_correction_T_max  0.8366
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1760
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1192
_reflns_number_gt                1165
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0305P)²+0.2956P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1192
_refine_ls_number_parameters     97
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0632
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 1.0000 0.5000 0.5000 0.00720(14) Uani 1 2 d S . .
S1 S 1.53990(9) 0.72009(8) 0.12058(5) 0.01365(15) Uani 1 1 d . . .
O1 O 0.6717(2) 0.7290(2) 0.44765(14) 0.0115(3) Uani 1 1 d . . .
H1A H 0.6573 0.7202 0.3584 0.017 Uiso 1 1 d R . .
H1B H 0.5441 0.7340 0.5013 0.017 Uiso 1 1 d R . .
N1 N 0.9429(3) 0.2974(2) 0.34861(17) 0.0098(3) Uani 1 1 d . . .
N2 N 0.7593(3) 0.2155(2) 0.36962(17) 0.0110(3) Uani 1 1 d . . .
N3 N 0.9623(3) 0.1355(2) 0.15247(16) 0.0084(3) Uani 1 1 d . . .
N4 N 1.0507(3) 0.0600(2) 0.01239(17) 0.0089(3) Uani 1 1 d . . .
N5 N 1.1841(3) 0.6147(3) 0.31049(17) 0.0121(3) Uani 1 1 d . . .
C1 C 0.7757(3) 0.1190(3) 0.2514(2) 0.0106(4) Uani 1 1 d . . .
H1 H 0.6734 0.0476 0.2360 0.013 Uiso 1 1 calc R . .
C2 C 1.0594(3) 0.2487(3) 0.2177(2) 0.0100(4) Uani 1 1 d . . .
H2 H 1.1923 0.2865 0.1743 0.012 Uiso 1 1 calc R . .
C3 C 1.3311(3) 0.6558(3) 0.2300(2) 0.0096(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O1 2.1049(15) . ?
Fe1 O1 2.1049(15) 2_766 ?
Fe1 N5 2.1375(17) 2_766 ?
Fe1 N5 2.1375(17) . ?
Fe1 N1 2.2030(17) 2_766 ?
Fe1 N1 2.2031(17) . ?
S1 C3 1.644(2) . ?
O1 H1A 0.8400 . ?
O1 H1B 0.8400 . ?
N1 C2 1.299(3) . ?
N1 N2 1.396(2) . ?
N2 C1 1.296(3) . ?
N3 C2 1.355(2) . ?
N3 C1 1.363(2) . ?
N3 N4 1.384(2) . ?
N4 N4 1.245(3) 2_755 ?
N5 C3 1.159(3) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 O1 180.0 . 2_766 ?
O1 Fe1 N5 89.76(6) . 2_766 ?
O1 Fe1 N5 90.23(6) 2_766 2_766 ?
O1 Fe1 N5 90.23(6) . . ?
O1 Fe1 N5 89.77(6) 2_766 . ?
N5 Fe1 N5 179.999(1) 2_766 . ?
O1 Fe1 N1 93.20(6) . 2_766 ?
O1 Fe1 N1 86.80(6) 2_766 2_766 ?
N5 Fe1 N1 87.00(7) 2_766 2_766 ?
N5 Fe1 N1 93.00(7) . 2_766 ?
O1 Fe1 N1 86.80(6) . . ?
O1 Fe1 N1 93.20(6) 2_766 . ?
N5 Fe1 N1 93.00(7) 2_766 . ?
N5 Fe1 N1 87.00(7) . . ?
N1 Fe1 N1 180.00(8) 2_766 . ?
Fe1 O1 H1A 108.7 . . ?
Fe1 O1 H1B 119.8 . . ?
H1A O1 H1B 109.3 . . ?
C2 N1 N2 107.43(15) . . ?
C2 N1 Fe1 126.30(13) . . ?
N2 N1 Fe1 125.99(12) . . ?
C1 N2 N1 107.32(15) . . ?
C2 N3 C1 106.06(15) . . ?
C2 N3 N4 122.64(16) . . ?
C1 N3 N4 131.29(15) . . ?
N4 N4 N3 109.29(19) 2_755 . ?
C3 N5 Fe1 162.59(15) . . ?
N2 C1 N3 109.58(16) . . ?
N2 C1 H1 125.2 . . ?
N3 C1 H1 125.2 . . ?
N1 C2 N3 109.61(17) . . ?
N1 C2 H2 125.2 . . ?
N3 C2 H2 125.2 . . ?
N5 C3 S1 177.77(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Fe1 N1 C2 108.10(16) . . . . ?
O1 Fe1 N1 C2 -71.90(16) 2_766 . . . ?
N5 Fe1 N1 C2 -162.30(16) 2_766 . . . ?
N5 Fe1 N1 C2 17.70(16) . . . . ?
N1 Fe1 N1 C2 130(35) 2_766 . . . ?
O1 Fe1 N1 N2 -65.07(14) . . . . ?
O1 Fe1 N1 N2 114.93(14) 2_766 . . . ?
N5 Fe1 N1 N2 24.52(14) 2_766 . . . ?
N5 Fe1 N1 N2 -155.48(14) . . . . ?
N1 Fe1 N1 N2 -43(35) 2_766 . . . ?
C2 N1 N2 C1 0.8(2) . . . . ?
Fe1 N1 N2 C1 175.07(12) . . . . ?
C2 N3 N4 N4 171.64(18) . . . 2_755 ?
C1 N3 N4 N4 -8.4(3) . . . 2_755 ?
O1 Fe1 N5 C3 153.5(5) . . . . ?
O1 Fe1 N5 C3 -26.5(5) 2_766 . . . ?
N5 Fe1 N5 C3 175(53) 2_766 . . . ?
N1 Fe1 N5 C3 60.3(5) 2_766 . . . ?
N1 Fe1 N5 C3 -119.7(5) . . . . ?
N1 N2 C1 N3 -0.5(2) . . . . ?
C2 N3 C1 N2 0.0(2) . . . . ?
N4 N3 C1 N2 180.00(17) . . . . ?
N2 N1 C2 N3 -0.9(2) . . . . ?
Fe1 N1 C2 N3 -175.07(12) . . . . ?
C1 N3 C2 N1 0.6(2) . . . . ?
N4 N3 C2 N1 -179.46(15) . . . . ?
Fe1 N5 C3 S1 -63(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.079
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1031681'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 Fe N10 O2 S2'
_chemical_formula_weight         372.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   22.145(7)
_cell_length_b                   5.6942(18)
_cell_length_c                   11.621(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.190(6)
_cell_angle_gamma                90.00
_cell_volume                     1450.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2247
_cell_measurement_theta_min      3.54
_cell_measurement_theta_max      28.21

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    1.348
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7934
_exptl_absorpt_correction_T_max  0.8132
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3597
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1281
_reflns_number_gt                1201
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0323P)²+4.7750P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1281
_refine_ls_number_parameters     97
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0747
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.2500 1.2500 0.5000 0.02045(18) Uani 1 2 d S . .
S1 S 0.08030(4) 0.82352(17) 0.29966(7) 0.0440(3) Uani 1 1 d U . .
O1W O 0.25197(9) 1.0228(4) 0.64377(16) 0.0336(5) Uani 1 1 d . . .
H1A H 0.2731 1.0361 0.7105 0.050 Uiso 1 1 d R . .
H1B H 0.2304 0.9003 0.6481 0.050 Uiso 1 1 d R . .
N1 N 0.19196(10) 1.0119(4) 0.3974(2) 0.0312(5) Uani 1 1 d U . .
N2 N 0.48804(9) 0.9316(4) 0.46221(19) 0.0253(5) Uani 1 1 d . . .
N3 N 0.42541(9) 0.9643(4) 0.44414(19) 0.0232(5) Uani 1 1 d . . .
N4 N 0.33275(10) 1.0782(4) 0.45075(19) 0.0254(5) Uani 1 1 d . . .
N5 N 0.33137(10) 0.8931(5) 0.3719(2) 0.0347(6) Uani 1 1 d . . .
C1 C 0.38922(11) 1.1170(5) 0.4929(2) 0.0258(6) Uani 1 1 d . . .
H1 H 0.4028 1.2311 0.5478 0.031 Uiso 1 1 calc R . .
C3 C 0.14639(13) 0.9271(5) 0.3564(2) 0.0294(5) Uani 1 1 d U . .
C2 C 0.38750(13) 0.8298(6) 0.3700(3) 0.0343(7) Uani 1 1 d . . .
H9 H 0.3998 0.7096 0.3244 0.041 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O1W 2.108(2) . ?
Fe1 O1W 2.108(2) 7_576 ?
Fe1 N1 2.115(2) 7_576 ?
Fe1 N1 2.115(2) . ?
Fe1 N4 2.223(2) 7_576 ?
Fe1 N4 2.223(2) . ?
S1 C3 1.628(3) . ?
O1W H1A 0.8499 . ?
O1W H1B 0.8513 . ?
N1 C3 1.158(4) . ?
N2 N2 1.235(5) 5_676 ?
N2 N3 1.385(3) . ?
N3 C2 1.351(4) . ?
N3 C1 1.360(3) . ?
N4 C1 1.295(3) . ?
N4 N5 1.394(3) . ?
N5 C2 1.297(4) . ?
C1 H1 0.9300 . ?
C2 H9 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1W Fe1 O1W 180.0 . 7_576 ?
O1W Fe1 N1 90.23(9) . 7_576 ?
O1W Fe1 N1 89.77(9) 7_576 7_576 ?
O1W Fe1 N1 89.77(9) . . ?
O1W Fe1 N1 90.23(9) 7_576 . ?
N1 Fe1 N1 180.00(11) 7_576 . ?
O1W Fe1 N4 89.47(8) . 7_576 ?
O1W Fe1 N4 90.53(8) 7_576 7_576 ?
N1 Fe1 N4 91.71(9) 7_576 7_576 ?
N1 Fe1 N4 88.29(9) . 7_576 ?
O1W Fe1 N4 90.53(8) . . ?
O1W Fe1 N4 89.47(8) 7_576 . ?
N1 Fe1 N4 88.29(9) 7_576 . ?
N1 Fe1 N4 91.71(9) . . ?
N4 Fe1 N4 180.0 7_576 . ?
Fe1 O1W H1A 128.0 . . ?
Fe1 O1W H1B 126.9 . . ?
H1A O1W H1B 105.1 . . ?
C3 N1 Fe1 157.3(2) . . ?
N2 N2 N3 110.0(3) 5_676 . ?
C2 N3 C1 106.2(2) . . ?
C2 N3 N2 122.5(2) . . ?
C1 N3 N2 131.3(2) . . ?
C1 N4 N5 107.9(2) . . ?
C1 N4 Fe1 127.90(19) . . ?
N5 N4 Fe1 124.07(16) . . ?
C2 N5 N4 106.8(2) . . ?
N4 C1 N3 109.1(2) . . ?
N4 C1 H1 125.4 . . ?
N3 C1 H1 125.4 . . ?
N1 C3 S1 176.4(3) . . ?
N5 C2 N3 110.0(3) . . ?
N5 C2 H9 125.0 . . ?
N3 C2 H9 125.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1W Fe1 N1 C3 88.9(6) . . . . ?
O1W Fe1 N1 C3 -91.1(6) 7_576 . . . ?
N1 Fe1 N1 C3 -57(18) 7_576 . . . ?
N4 Fe1 N1 C3 -0.6(6) 7_576 . . . ?
N4 Fe1 N1 C3 179.4(6) . . . . ?
N2 N2 N3 C2 -176.7(3) 5_676 . . . ?
N2 N2 N3 C1 1.1(5) 5_676 . . . ?
O1W Fe1 N4 C1 -81.9(2) . . . . ?
O1W Fe1 N4 C1 98.1(2) 7_576 . . . ?
N1 Fe1 N4 C1 8.3(2) 7_576 . . . ?
N1 Fe1 N4 C1 -171.7(2) . . . . ?
N4 Fe1 N4 C1 5(5) 7_576 . . . ?
O1W Fe1 N4 N5 93.3(2) . . . . ?
O1W Fe1 N4 N5 -86.7(2) 7_576 . . . ?
N1 Fe1 N4 N5 -176.5(2) 7_576 . . . ?
N1 Fe1 N4 N5 3.5(2) . . . . ?
N4 Fe1 N4 N5 180(5) 7_576 . . . ?
C1 N4 N5 C2 -0.3(3) . . . . ?
Fe1 N4 N5 C2 -176.4(2) . . . . ?
N5 N4 C1 N3 0.3(3) . . . . ?
Fe1 N4 C1 N3 176.16(17) . . . . ?
C2 N3 C1 N4 -0.2(3) . . . . ?
N2 N3 C1 N4 -178.3(3) . . . . ?
Fe1 N1 C3 S1 25(5) . . . . ?
N4 N5 C2 N3 0.2(4) . . . . ?
C1 N3 C2 N5 0.0(4) . . . . ?
N2 N3 C2 N5 178.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.060
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1031682'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H12 Br Fe0.50 N12 O3'
_chemical_formula_weight         408.11

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.3937(8)
_cell_length_b                   8.1980(9)
_cell_length_c                   12.7674(14)
_cell_angle_alpha                76.242(2)
_cell_angle_beta                 74.662(2)
_cell_angle_gamma                86.512(2)
_cell_volume                     724.90(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2465
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      28.33

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.870
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    3.353
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5836
_exptl_absorpt_correction_T_max  0.6160
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4184
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2556
_reflns_number_gt                2284
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0498P)²+0.3127P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2556
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.0000 0.0000 0.5000 0.00715(16) Uani 1 2 d S . .
Br1 Br 0.73881(5) 0.27096(4) 0.07029(3) 0.01929(13) Uani 1 1 d . . .
O1 O -0.1459(3) 0.2189(2) 0.50718(16) 0.0114(4) Uani 1 1 d . . .
H1A H -0.2251 0.2383 0.5646 0.017 Uiso 1 1 d R . .
H1B H -0.1043 0.3149 0.4684 0.017 Uiso 1 1 d R . .
O2 O 0.9268(4) 0.5537(3) 0.15208(19) 0.0261(6) Uani 1 1 d . . .
H2A H 0.8798 0.4756 0.1343 0.039 Uiso 1 1 d R . .
H2B H 1.0126 0.5964 0.0946 0.039 Uiso 1 1 d R . .
O3 O 1.0029(3) 0.5059(3) 0.64329(18) 0.0150(5) Uani 1 1 d . . .
H3A H 1.0382 0.4840 0.7033 0.023 Uiso 1 1 d R . .
H3B H 0.8858 0.4855 0.6637 0.023 Uiso 1 1 d R . .
N1 N -0.2606(3) -0.1378(3) 0.53131(19) 0.0092(5) Uani 1 1 d . . .
N2 N -0.4248(4) -0.1156(3) 0.6125(2) 0.0122(5) Uani 1 1 d . . .
N3 N -0.4614(3) -0.3271(3) 0.5433(2) 0.0091(5) Uani 1 1 d . . .
N4 N -0.5510(3) -0.4660(3) 0.5359(2) 0.0106(5) Uani 1 1 d . . .
N5 N 0.0363(3) 0.0501(3) 0.3180(2) 0.0106(5) Uani 1 1 d . . .
N6 N -0.0109(4) -0.0726(3) 0.2687(2) 0.0136(6) Uani 1 1 d . . .
N7 N 0.1678(4) 0.1191(3) 0.1403(2) 0.0100(5) Uani 1 1 d . . .
N8 N 0.2827(4) 0.2126(3) 0.0425(2) 0.0117(5) Uani 1 1 d . . .
N9 N 0.3023(4) 0.1346(3) -0.0318(2) 0.0149(6) Uani 1 1 d . . .
N10 N 0.4239(4) 0.2192(3) -0.1296(2) 0.0121(5) Uani 1 1 d . . .
N11 N 0.6226(4) 0.3914(3) -0.2574(2) 0.0141(6) Uani 1 1 d . . .
N12 N 0.5969(4) 0.2530(3) -0.2993(2) 0.0142(6) Uani 1 1 d . . .
C1 C -0.5408(4) -0.2310(4) 0.6175(2) 0.0121(6) Uani 1 1 d . . .
H1 H -0.6610 -0.2463 0.6649 0.014 Uiso 1 1 calc R . .
C2 C -0.2854(4) -0.2645(4) 0.4915(2) 0.0103(6) Uani 1 1 d . . .
H2 H -0.1978 -0.3055 0.4369 0.012 Uiso 1 1 calc R . .
C3 C 0.1405(4) 0.1617(4) 0.2396(2) 0.0116(6) Uani 1 1 d . . .
H3 H 0.1893 0.2569 0.2499 0.014 Uiso 1 1 calc R . .
C4 C 0.0704(4) -0.0283(4) 0.1627(3) 0.0141(7) Uani 1 1 d . . .
H4 H 0.0637 -0.0872 0.1099 0.017 Uiso 1 1 calc R . .
C5 C 0.5185(4) 0.3678(4) -0.1558(3) 0.0140(7) Uani 1 1 d . . .
H5 H 0.5096 0.4400 -0.1085 0.017 Uiso 1 1 calc R . .
C6 C 0.4779(5) 0.1531(4) -0.2214(2) 0.0151(7) Uani 1 1 d . . .
H6 H 0.4357 0.0518 -0.2272 0.018 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O1 2.0455(19) 2_556 ?
Fe1 O1 2.0455(19) . ?
Fe1 N1 2.189(2) . ?
Fe1 N1 2.189(2) 2_556 ?
Fe1 N5 2.207(2) . ?
Fe1 N5 2.207(2) 2_556 ?
O1 H1A 0.8499 . ?
O1 H1B 0.8499 . ?
O2 H2A 0.8485 . ?
O2 H2B 0.8500 . ?
O3 H3A 0.8500 . ?
O3 H3B 0.8500 . ?
N1 C2 1.302(4) . ?
N1 N2 1.407(3) . ?
N2 C1 1.295(4) . ?
N3 C2 1.363(4) . ?
N3 C1 1.367(4) . ?
N3 N4 1.386(3) . ?
N4 N4 1.243(5) 2_446 ?
N5 C3 1.294(4) . ?
N5 N6 1.410(3) . ?
N6 C4 1.299(4) . ?
N7 C3 1.355(4) . ?
N7 C4 1.376(4) . ?
N7 N8 1.390(3) . ?
N8 N9 1.238(4) . ?
N9 N10 1.385(4) . ?
N10 C6 1.362(4) . ?
N10 C5 1.368(4) . ?
N11 C5 1.297(4) . ?
N11 N12 1.407(4) . ?
N12 C6 1.293(4) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 O1 180.0 2_556 . ?
O1 Fe1 N1 89.17(9) 2_556 . ?
O1 Fe1 N1 90.83(9) . . ?
O1 Fe1 N1 90.83(9) 2_556 2_556 ?
O1 Fe1 N1 89.17(9) . 2_556 ?
N1 Fe1 N1 180.0 . 2_556 ?
O1 Fe1 N5 89.03(8) 2_556 . ?
O1 Fe1 N5 90.97(8) . . ?
N1 Fe1 N5 91.20(9) . . ?
N1 Fe1 N5 88.80(9) 2_556 . ?
O1 Fe1 N5 90.97(8) 2_556 2_556 ?
O1 Fe1 N5 89.03(8) . 2_556 ?
N1 Fe1 N5 88.80(9) . 2_556 ?
N1 Fe1 N5 91.20(9) 2_556 2_556 ?
N5 Fe1 N5 179.999(1) . 2_556 ?
Fe1 O1 H1A 125.2 . . ?
Fe1 O1 H1B 124.0 . . ?
H1A O1 H1B 105.2 . . ?
H2A O2 H2B 105.1 . . ?
H3A O3 H3B 105.2 . . ?
C2 N1 N2 108.6(2) . . ?
C2 N1 Fe1 127.6(2) . . ?
N2 N1 Fe1 123.32(17) . . ?
C1 N2 N1 106.2(2) . . ?
C2 N3 C1 106.3(2) . . ?
C2 N3 N4 131.2(2) . . ?
C1 N3 N4 122.4(2) . . ?
N4 N4 N3 110.1(3) 2_446 . ?
C3 N5 N6 107.9(2) . . ?
C3 N5 Fe1 128.9(2) . . ?
N6 N5 Fe1 120.81(17) . . ?
C4 N6 N5 106.7(2) . . ?
C3 N7 C4 106.0(2) . . ?
C3 N7 N8 122.1(2) . . ?
C4 N7 N8 131.9(2) . . ?
N9 N8 N7 108.6(2) . . ?
N8 N9 N10 110.5(2) . . ?
C6 N10 C5 106.6(3) . . ?
C6 N10 N9 121.7(3) . . ?
C5 N10 N9 131.7(2) . . ?
C5 N11 N12 107.7(2) . . ?
C6 N12 N11 107.4(3) . . ?
N2 C1 N3 110.3(3) . . ?
N2 C1 H1 124.8 . . ?
N3 C1 H1 124.8 . . ?
N1 C2 N3 108.6(3) . . ?
N1 C2 H2 125.7 . . ?
N3 C2 H2 125.7 . . ?
N5 C3 N7 109.8(3) . . ?
N5 C3 H3 125.1 . . ?
N7 C3 H3 125.1 . . ?
N6 C4 N7 109.6(3) . . ?
N6 C4 H4 125.2 . . ?
N7 C4 H4 125.2 . . ?
N11 C5 N10 108.9(3) . . ?
N11 C5 H5 125.6 . . ?
N10 C5 H5 125.6 . . ?
N12 C6 N10 109.4(3) . . ?
N12 C6 H6 125.3 . . ?
N10 C6 H6 125.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Fe1 N1 C2 -34.5(2) 2_556 . . . ?
O1 Fe1 N1 C2 145.5(2) . . . . ?
N1 Fe1 N1 C2 -143(8) 2_556 . . . ?
N5 Fe1 N1 C2 54.5(2) . . . . ?
N5 Fe1 N1 C2 -125.5(2) 2_556 . . . ?
O1 Fe1 N1 N2 136.1(2) 2_556 . . . ?
O1 Fe1 N1 N2 -43.9(2) . . . . ?
N1 Fe1 N1 N2 28(8) 2_556 . . . ?
N5 Fe1 N1 N2 -134.9(2) . . . . ?
N5 Fe1 N1 N2 45.1(2) 2_556 . . . ?
C2 N1 N2 C1 0.1(3) . . . . ?
Fe1 N1 N2 C1 -172.03(19) . . . . ?
C2 N3 N4 N4 -4.2(5) . . . 2_446 ?
C1 N3 N4 N4 -178.6(3) . . . 2_446 ?
O1 Fe1 N5 C3 -109.0(3) 2_556 . . . ?
O1 Fe1 N5 C3 71.0(3) . . . . ?
N1 Fe1 N5 C3 161.9(3) . . . . ?
N1 Fe1 N5 C3 -18.1(3) 2_556 . . . ?
N5 Fe1 N5 C3 76(9) 2_556 . . . ?
O1 Fe1 N5 N6 51.2(2) 2_556 . . . ?
O1 Fe1 N5 N6 -128.8(2) . . . . ?
N1 Fe1 N5 N6 -38.0(2) . . . . ?
N1 Fe1 N5 N6 142.0(2) 2_556 . . . ?
N5 Fe1 N5 N6 -124(9) 2_556 . . . ?
C3 N5 N6 C4 0.8(3) . . . . ?
Fe1 N5 N6 C4 -163.1(2) . . . . ?
C3 N7 N8 N9 171.3(3) . . . . ?
C4 N7 N8 N9 -5.0(4) . . . . ?
N7 N8 N9 N10 -176.9(2) . . . . ?
N8 N9 N10 C6 175.5(3) . . . . ?
N8 N9 N10 C5 -0.9(4) . . . . ?
C5 N11 N12 C6 0.4(3) . . . . ?
N1 N2 C1 N3 -0.4(3) . . . . ?
C2 N3 C1 N2 0.5(3) . . . . ?
N4 N3 C1 N2 176.2(2) . . . . ?
N2 N1 C2 N3 0.2(3) . . . . ?
Fe1 N1 C2 N3 171.92(17) . . . . ?
C1 N3 C2 N1 -0.5(3) . . . . ?
N4 N3 C2 N1 -175.6(3) . . . . ?
N6 N5 C3 N7 -0.8(3) . . . . ?
Fe1 N5 C3 N7 161.34(19) . . . . ?
C4 N7 C3 N5 0.5(3) . . . . ?
N8 N7 C3 N5 -176.6(2) . . . . ?
N5 N6 C4 N7 -0.5(3) . . . . ?
C3 N7 C4 N6 0.0(3) . . . . ?
N8 N7 C4 N6 176.7(3) . . . . ?
N12 N11 C5 N10 -0.5(3) . . . . ?
C6 N10 C5 N11 0.4(3) . . . . ?
N9 N10 C5 N11 177.2(3) . . . . ?
N11 N12 C6 N10 -0.1(3) . . . . ?
C5 N10 C6 N12 -0.2(3) . . . . ?
N9 N10 C6 N12 -177.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.851
_refine_diff_density_min         -1.084
_refine_diff_density_rms         0.102
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_10
_database_code_depnum_ccdc_archive 'CCDC 1045134'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H4 N10 S2 Zn'
_chemical_formula_weight         345.68

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   12.2481(13)
_cell_length_b                   5.6785(6)
_cell_length_c                   17.9506(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.572(2)
_cell_angle_gamma                90.00
_cell_volume                     1196.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2802
_cell_measurement_theta_min      3.47
_cell_measurement_theta_max      28.26

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            Pale
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.404
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6715
_exptl_absorpt_correction_T_max  0.7144
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3164
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1034
_reflns_number_gt                1010
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0210P)²+2.1870P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1034
_refine_ls_number_parameters     87
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0201
_refine_ls_wR_factor_ref         0.0511
_refine_ls_wR_factor_gt          0.0503
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.5000 0.23981(4) 0.2500 0.00783(12) Uani 1 2 d S . .
S1 S 0.42279(5) -0.26399(8) 0.43605(3) 0.01657(14) Uani 1 1 d . . .
N1 N 0.62197(12) 0.4621(3) 0.31085(8) 0.0094(3) Uani 1 1 d . . .
N2 N 0.67415(12) 0.6368(3) 0.27760(8) 0.0110(3) Uani 1 1 d . . .
N3 N 0.71306(12) 0.6927(3) 0.40289(8) 0.0081(3) Uani 1 1 d . . .
N4 N 0.75979(12) 0.8072(3) 0.47320(9) 0.0098(3) Uani 1 1 d . . .
N5 N 0.47429(13) 0.0619(3) 0.33515(9) 0.0147(3) Uani 1 1 d . . .
C1 C 0.64655(14) 0.4971(3) 0.38550(10) 0.0092(4) Uani 1 1 d . . .
H1 H 0.6223 0.4027 0.4215 0.011 Uiso 1 1 calc R . .
C2 C 0.72763(16) 0.7730(3) 0.33419(10) 0.0106(4) Uani 1 1 d . . .
H2 H 0.7705 0.9083 0.3289 0.013 Uiso 1 1 calc R . .
C3 C 0.45239(14) -0.0734(3) 0.37765(10) 0.0106(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N5 1.9314(15) . ?
Zn1 N5 1.9314(15) 2_655 ?
Zn1 N1 2.0218(14) . ?
Zn1 N1 2.0218(14) 2_655 ?
S1 C3 1.6184(19) . ?
N1 C1 1.302(2) . ?
N1 N2 1.402(2) . ?
N2 C2 1.296(2) . ?
N3 C1 1.360(2) . ?
N3 C2 1.373(2) . ?
N3 N4 1.390(2) . ?
N4 N4 1.240(3) 7_666 ?
N5 C3 1.167(2) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Zn1 N5 116.94(9) . 2_655 ?
N5 Zn1 N1 99.27(6) . . ?
N5 Zn1 N1 119.47(6) 2_655 . ?
N5 Zn1 N1 119.47(6) . 2_655 ?
N5 Zn1 N1 99.27(6) 2_655 2_655 ?
N1 Zn1 N1 102.73(8) . 2_655 ?
C1 N1 N2 109.29(14) . . ?
C1 N1 Zn1 124.72(12) . . ?
N2 N1 Zn1 124.61(11) . . ?
C2 N2 N1 106.17(14) . . ?
C1 N3 C2 106.73(14) . . ?
C1 N3 N4 130.94(15) . . ?
C2 N3 N4 122.31(15) . . ?
N4 N4 N3 109.79(18) 7_666 . ?
C3 N5 Zn1 169.03(14) . . ?
N1 C1 N3 107.97(15) . . ?
N1 C1 H1 126.0 . . ?
N3 C1 H1 126.0 . . ?
N2 C2 N3 109.84(16) . . ?
N2 C2 H2 125.1 . . ?
N3 C2 H2 125.1 . . ?
N5 C3 S1 179.19(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N5 Zn1 N1 C1 -14.79(15) . . . . ?
N5 Zn1 N1 C1 -143.07(14) 2_655 . . . ?
N1 Zn1 N1 C1 108.43(15) 2_655 . . . ?
N5 Zn1 N1 N2 -179.95(13) . . . . ?
N5 Zn1 N1 N2 51.77(15) 2_655 . . . ?
N1 Zn1 N1 N2 -56.73(11) 2_655 . . . ?
C1 N1 N2 C2 -0.71(19) . . . . ?
Zn1 N1 N2 C2 166.40(12) . . . . ?
C1 N3 N4 N4 5.4(3) . . . 7_666 ?
C2 N3 N4 N4 -176.04(18) . . . 7_666 ?
N5 Zn1 N5 C3 -26.4(8) 2_655 . . . ?
N1 Zn1 N5 C3 -156.4(8) . . . . ?
N1 Zn1 N5 C3 93.2(8) 2_655 . . . ?
N2 N1 C1 N3 0.61(18) . . . . ?
Zn1 N1 C1 N3 -166.48(11) . . . . ?
C2 N3 C1 N1 -0.30(19) . . . . ?
N4 N3 C1 N1 178.45(16) . . . . ?
N1 N2 C2 N3 0.51(19) . . . . ?
C1 N3 C2 N2 -0.2(2) . . . . ?
N4 N3 C2 N2 -179.03(15) . . . . ?
Zn1 N5 C3 S1 43(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.055
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9
_database_code_depnum_ccdc_archive 'CCDC 1045135'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H5 N10 O0.50 S2 Zn'
_chemical_formula_weight         354.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.4935(6)
_cell_length_b                   7.8714(6)
_cell_length_c                   12.2388(10)
_cell_angle_alpha                72.3250(10)
_cell_angle_beta                 83.1640(10)
_cell_angle_gamma                82.9130(10)
_cell_volume                     680.02(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2272
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      28.60

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            RED
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             354
_exptl_absorpt_coefficient_mu    2.120
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5882
_exptl_absorpt_correction_T_max  0.6765
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3836
_diffrn_reflns_av_R_equivalents  0.0122
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2655
_reflns_number_gt                2390
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0394P)²+0.3493P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2655
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.25857(4) 0.72981(4) 0.15751(2) 0.03870(12) Uani 1 1 d . . .
S1 S 0.14952(12) 1.09043(13) -0.21489(7) 0.0703(3) Uani 1 1 d . . .
S2 S 0.02953(16) 0.24243(14) 0.43623(11) 0.1010(4) Uani 1 1 d . . .
N1 N 0.3226(3) 0.8699(3) 0.25703(17) 0.0346(4) Uani 1 1 d . . .
N2 N 0.3559(3) 1.0490(3) 0.21283(17) 0.0378(5) Uani 1 1 d . . .
N3 N 0.4190(3) 0.9492(3) 0.39115(16) 0.0335(4) Uani 1 1 d . . .
N4 N 0.4731(3) 0.9292(3) 0.49931(17) 0.0361(4) Uani 1 1 d . . .
N5 N 0.5202(3) 0.6149(3) 0.12518(18) 0.0393(5) Uani 1 1 d . . .
N6 N 0.5941(3) 0.4652(3) 0.20753(19) 0.0464(5) Uani 1 1 d . . .
N7 N 0.7916(3) 0.5478(3) 0.06062(17) 0.0374(5) Uani 1 1 d . . .
N8 N 0.9427(3) 0.5628(3) -0.01776(18) 0.0400(5) Uani 1 1 d . . .
N9 N 0.2138(3) 0.8648(3) 0.00205(19) 0.0495(6) Uani 1 1 d . . .
N10 N 0.1463(3) 0.5209(3) 0.2535(2) 0.0514(6) Uani 1 1 d . . .
C1 C 0.4133(4) 1.0927(3) 0.2948(2) 0.0374(5) Uani 1 1 d . . .
H1 H 0.4461 1.2054 0.2892 0.045 Uiso 1 1 calc R . .
C2 C 0.3605(4) 0.8132(3) 0.3632(2) 0.0379(5) Uani 1 1 d . . .
H2 H 0.3494 0.6980 0.4122 0.046 Uiso 1 1 calc R . .
C3 C 0.7561(4) 0.4280(3) 0.1669(2) 0.0458(6) Uani 1 1 d . . .
H3 H 0.8366 0.3344 0.2039 0.055 Uiso 1 1 calc R . .
C4 C 0.6414(4) 0.6616(3) 0.0395(2) 0.0398(6) Uani 1 1 d . . .
H4 H 0.6269 0.7583 -0.0261 0.048 Uiso 1 1 calc R . .
C5 C 0.1866(3) 0.9599(4) -0.0879(2) 0.0419(6) Uani 1 1 d . . .
C6 C 0.0984(4) 0.4076(4) 0.3312(3) 0.0517(7) Uani 1 1 d . . .
O1 O 0.6671(11) 0.5642(9) 0.4531(6) 0.120(2) Uani 0.50 1 d P . .


_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 N9 1.923(2) . ?
Zn1 N10 1.930(2) . ?
Zn1 N1 2.0037(19) . ?
Zn1 N5 2.101(2) . ?
S1 C5 1.616(3) . ?
S2 C6 1.613(3) . ?
N1 C2 1.293(3) . ?
N1 N2 1.391(3) . ?
N2 C1 1.288(3) . ?
N3 C2 1.352(3) . ?
N3 C1 1.363(3) . ?
N3 N4 1.388(3) . ?
N4 N4 1.236(4) 2_676 ?
N5 C4 1.296(3) . ?
N5 N6 1.400(3) . ?
N6 C3 1.290(4) . ?
N7 C4 1.348(3) . ?
N7 C3 1.373(3) . ?
N7 N8 1.386(3) . ?
N8 N8 1.235(4) 2_765 ?
N9 C5 1.153(3) . ?
N10 C6 1.145(4) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N9 Zn1 N10 127.71(11) . . ?
N9 Zn1 N1 116.03(9) . . ?
N10 Zn1 N1 109.13(10) . . ?
N9 Zn1 N5 98.61(9) . . ?
N10 Zn1 N5 100.54(9) . . ?
N1 Zn1 N5 97.25(8) . . ?
C2 N1 N2 108.68(19) . . ?
C2 N1 Zn1 128.81(17) . . ?
N2 N1 Zn1 122.04(14) . . ?
C1 N2 N1 106.52(18) . . ?
C2 N3 C1 106.18(19) . . ?
C2 N3 N4 122.44(19) . . ?
C1 N3 N4 131.4(2) . . ?
N4 N4 N3 109.4(2) 2_676 . ?
C4 N5 N6 108.2(2) . . ?
C4 N5 Zn1 131.54(17) . . ?
N6 N5 Zn1 120.20(16) . . ?
C3 N6 N5 106.7(2) . . ?
C4 N7 C3 106.2(2) . . ?
C4 N7 N8 121.9(2) . . ?
C3 N7 N8 131.8(2) . . ?
N8 N8 N7 109.7(3) 2_765 . ?
C5 N9 Zn1 173.6(2) . . ?
C6 N10 Zn1 162.9(3) . . ?
N2 C1 N3 110.0(2) . . ?
N2 C1 H1 125.0 . . ?
N3 C1 H1 125.0 . . ?
N1 C2 N3 108.7(2) . . ?
N1 C2 H2 125.7 . . ?
N3 C2 H2 125.7 . . ?
N6 C3 N7 109.6(2) . . ?
N6 C3 H3 125.2 . . ?
N7 C3 H3 125.2 . . ?
N5 C4 N7 109.2(2) . . ?
N5 C4 H4 125.4 . . ?
N7 C4 H4 125.4 . . ?
N9 C5 S1 179.0(3) . . ?
N10 C6 S2 177.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N9 Zn1 N1 C2 -179.3(2) . . . . ?
N10 Zn1 N1 C2 27.8(3) . . . . ?
N5 Zn1 N1 C2 -76.0(2) . . . . ?
N9 Zn1 N1 N2 -8.1(2) . . . . ?
N10 Zn1 N1 N2 -160.93(18) . . . . ?
N5 Zn1 N1 N2 95.22(18) . . . . ?
C2 N1 N2 C1 0.2(3) . . . . ?
Zn1 N1 N2 C1 -172.59(17) . . . . ?
C2 N3 N4 N4 177.3(3) . . . 2_676 ?
C1 N3 N4 N4 -1.6(4) . . . 2_676 ?
N9 Zn1 N5 C4 21.4(3) . . . . ?
N10 Zn1 N5 C4 152.5(2) . . . . ?
N1 Zn1 N5 C4 -96.4(2) . . . . ?
N9 Zn1 N5 N6 -162.20(19) . . . . ?
N10 Zn1 N5 N6 -31.1(2) . . . . ?
N1 Zn1 N5 N6 79.98(18) . . . . ?
C4 N5 N6 C3 -0.6(3) . . . . ?
Zn1 N5 N6 C3 -177.76(18) . . . . ?
C4 N7 N8 N8 -175.7(3) . . . 2_765 ?
C3 N7 N8 N8 3.6(4) . . . 2_765 ?
N10 Zn1 N9 C5 135(2) . . . . ?
N1 Zn1 N9 C5 -12(2) . . . . ?
N5 Zn1 N9 C5 -115(2) . . . . ?
N9 Zn1 N10 C6 -165.1(8) . . . . ?
N1 Zn1 N10 C6 -16.3(8) . . . . ?
N5 Zn1 N10 C6 85.3(8) . . . . ?
N1 N2 C1 N3 -0.1(3) . . . . ?
C2 N3 C1 N2 -0.1(3) . . . . ?
N4 N3 C1 N2 178.9(2) . . . . ?
N2 N1 C2 N3 -0.3(3) . . . . ?
Zn1 N1 C2 N3 171.89(16) . . . . ?
C1 N3 C2 N1 0.2(3) . . . . ?
N4 N3 C2 N1 -178.9(2) . . . . ?
N5 N6 C3 N7 0.0(3) . . . . ?
C4 N7 C3 N6 0.6(3) . . . . ?
N8 N7 C3 N6 -178.8(2) . . . . ?
N6 N5 C4 N7 0.9(3) . . . . ?
Zn1 N5 C4 N7 177.69(16) . . . . ?
C3 N7 C4 N5 -0.9(3) . . . . ?
N8 N7 C4 N5 178.5(2) . . . . ?
Zn1 N9 C5 S1 163(14) . . . . ?
Zn1 N10 C6 S2 -160(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.057
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1045136'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H20 B2 F8 Fe N24 O4'
_chemical_formula_weight         793.99

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.940(4)
_cell_length_b                   8.039(4)
_cell_length_c                   12.890(7)
_cell_angle_alpha                100.729(7)
_cell_angle_beta                 107.661(7)
_cell_angle_gamma                91.364(8)
_cell_volume                     767.4(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1292
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      28.38

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            RED
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8984
_exptl_absorpt_correction_T_max  0.9143
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3914
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0863
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2677
_reflns_number_gt                1830
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1230P)²+0.0551P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2677
_refine_ls_number_parameters     248
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2141
_refine_ls_wR_factor_gt          0.1919
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.5000 0.5000 0.5000 0.0269(4) Uani 1 2 d S . .
B1 B 0.8694(10) 0.1797(10) 0.0898(6) 0.074(3) Uani 0.894(6) 1 d PD A 1
F1 F 0.7798(7) 0.2945(7) 0.1401(4) 0.124(3) Uani 0.894(6) 1 d PD A 1
F2 F 0.7571(7) 0.0395(6) 0.0309(5) 0.118(2) Uani 0.894(6) 1 d PD A 1
F3 F 0.9319(8) 0.2517(7) 0.0191(5) 0.118(2) Uani 0.894(6) 1 d PD A 1
F4 F 1.0080(7) 0.1338(7) 0.1684(4) 0.143(3) Uani 0.894(6) 1 d PD A 1
B1' B 0.869(3) 0.168(3) 0.115(3) 0.074(3) Uani 0.106(6) 1 d PD A 2
F1' F 0.952(3) 0.327(3) 0.158(3) 0.124(3) Uani 0.106(6) 1 d PD A 2
F2' F 0.724(4) 0.155(5) 0.149(4) 0.118(2) Uani 0.106(6) 1 d PD A 2
F3' F 0.818(7) 0.139(6) 0.002(2) 0.118(2) Uani 0.106(6) 1 d PD A 2
F4' F 0.982(5) 0.052(4) 0.152(5) 0.143(3) Uani 0.106(6) 1 d PD A 2
O1W O 0.3791(5) 0.2704(4) 0.5023(3) 0.0380(10) Uani 1 1 d . . .
H1A H 0.3437 0.2369 0.5515 0.057 Uiso 1 1 d R . .
H1B H 0.3397 0.1956 0.4427 0.057 Uiso 1 1 d R . .
O2W O 0.2932(6) 0.0141(5) 0.3235(4) 0.0601(13) Uani 1 1 d . . .
H2A H 0.3840 -0.0198 0.3066 0.090 Uiso 1 1 d R . .
H2B H 0.2115 0.0146 0.2631 0.090 Uiso 1 1 d R . .
N1 N 0.3787(6) 0.4626(5) 0.3181(4) 0.0355(11) Uani 1 1 d . . .
N2 N 0.2443(8) 0.5598(7) 0.2675(4) 0.0594(17) Uani 1 1 d . . .
N3 N 0.3312(6) 0.4020(6) 0.1399(4) 0.0391(12) Uani 1 1 d . . .
N4 N 0.3633(7) 0.3203(7) 0.0428(4) 0.0459(13) Uani 1 1 d . . .
N5 N 0.2664(8) 0.3632(6) -0.0385(4) 0.0503(14) Uani 1 1 d . . .
N6 N 0.3071(7) 0.2816(6) -0.1321(4) 0.0435(13) Uani 1 1 d . . .
N7 N 0.3035(7) 0.2250(7) -0.3048(4) 0.0518(14) Uani 1 1 d . . .
N8 N 0.4241(8) 0.1283(8) -0.2451(5) 0.0627(17) Uani 1 1 d . . .
N9 N 0.7245(5) 0.3654(5) 0.4733(3) 0.0307(11) Uani 1 1 d . . .
N10 N 0.8147(6) 0.4075(6) 0.4016(4) 0.0412(13) Uani 1 1 d . . .
N11 N 0.9158(5) 0.1813(5) 0.4612(4) 0.0302(11) Uani 1 1 d . . .
N12 N 1.0179(5) 0.0422(5) 0.4688(4) 0.0316(11) Uani 1 1 d . . .
C1 C 0.4251(8) 0.3718(8) 0.2394(5) 0.0433(16) Uani 1 1 d . . .
H1 H 0.5120 0.2955 0.2501 0.052 Uiso 1 1 calc R . .
C2 C 0.2210(10) 0.5214(9) 0.1618(5) 0.061(2) Uani 1 1 d . . .
H2 H 0.1406 0.5685 0.1085 0.073 Uiso 1 1 calc R . .
C3 C 0.2372(10) 0.3156(9) -0.2346(5) 0.0579(19) Uani 1 1 d . . .
H3 H 0.1533 0.3930 -0.2525 0.070 Uiso 1 1 calc R . .
C4 C 0.4251(9) 0.1629(10) -0.1432(5) 0.062(2) Uani 1 1 d . . .
H4 H 0.4948 0.1150 -0.0861 0.074 Uiso 1 1 calc R . .
C5 C 0.7878(7) 0.2306(7) 0.5082(4) 0.0321(13) Uani 1 1 d . . .
H5 H 0.7518 0.1771 0.5570 0.039 Uiso 1 1 calc R . .
C6 C 0.9268(7) 0.2923(7) 0.3962(5) 0.0421(15) Uani 1 1 d . . .
H6 H 1.0033 0.2874 0.3537 0.051 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O1W 2.069(4) . ?
Fe1 O1W 2.069(4) 2_666 ?
Fe1 N9 2.189(4) 2_666 ?
Fe1 N9 2.189(4) . ?
Fe1 N1 2.206(4) . ?
Fe1 N1 2.206(4) 2_666 ?
B1 F4 1.362(7) . ?
B1 F2 1.366(8) . ?
B1 F1 1.366(7) . ?
B1 F3 1.367(8) . ?
B1' F2' 1.361(10) . ?
B1' F4' 1.361(10) . ?
B1' F3' 1.362(10) . ?
B1' F1' 1.362(10) . ?
O1W H1A 0.8500 . ?
O1W H1B 0.8500 . ?
O2W H2A 0.8502 . ?
O2W H2B 0.8494 . ?
N1 C1 1.289(7) . ?
N1 N2 1.408(6) . ?
N2 C2 1.293(8) . ?
N3 C1 1.344(7) . ?
N3 C2 1.363(7) . ?
N3 N4 1.399(6) . ?
N4 N5 1.210(6) . ?
N5 N6 1.393(6) . ?
N6 C3 1.352(8) . ?
N6 C4 1.371(8) . ?
N7 C3 1.298(8) . ?
N7 N8 1.387(7) . ?
N8 C4 1.289(8) . ?
N9 C5 1.304(6) . ?
N9 N10 1.409(6) . ?
N10 C6 1.307(6) . ?
N11 C6 1.351(7) . ?
N11 C5 1.364(6) . ?
N11 N12 1.397(5) . ?
N12 N12 1.233(8) 2_756 ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1W Fe1 O1W 179.999(1) . 2_666 ?
O1W Fe1 N9 91.26(15) . 2_666 ?
O1W Fe1 N9 88.74(15) 2_666 2_666 ?
O1W Fe1 N9 88.74(15) . . ?
O1W Fe1 N9 91.26(15) 2_666 . ?
N9 Fe1 N9 179.999(1) 2_666 . ?
O1W Fe1 N1 91.46(16) . . ?
O1W Fe1 N1 88.54(16) 2_666 . ?
N9 Fe1 N1 90.96(15) 2_666 . ?
N9 Fe1 N1 89.04(15) . . ?
O1W Fe1 N1 88.54(16) . 2_666 ?
O1W Fe1 N1 91.46(16) 2_666 2_666 ?
N9 Fe1 N1 89.04(15) 2_666 2_666 ?
N9 Fe1 N1 90.96(15) . 2_666 ?
N1 Fe1 N1 180.00(10) . 2_666 ?
F4 B1 F2 109.6(5) . . ?
F4 B1 F1 109.6(5) . . ?
F2 B1 F1 109.4(5) . . ?
F4 B1 F3 109.6(5) . . ?
F2 B1 F3 109.3(5) . . ?
F1 B1 F3 109.3(5) . . ?
F2' B1' F4' 109.5(6) . . ?
F2' B1' F3' 109.5(6) . . ?
F4' B1' F3' 109.5(6) . . ?
F2' B1' F1' 109.5(6) . . ?
F4' B1' F1' 109.5(6) . . ?
F3' B1' F1' 109.4(6) . . ?
Fe1 O1W H1A 131.9 . . ?
Fe1 O1W H1B 120.0 . . ?
H1A O1W H1B 107.4 . . ?
H2A O2W H2B 107.4 . . ?
C1 N1 N2 106.7(4) . . ?
C1 N1 Fe1 129.8(4) . . ?
N2 N1 Fe1 122.9(3) . . ?
C2 N2 N1 106.7(5) . . ?
C1 N3 C2 105.3(5) . . ?
C1 N3 N4 120.7(5) . . ?
C2 N3 N4 134.0(5) . . ?
N5 N4 N3 111.3(5) . . ?
N4 N5 N6 108.9(5) . . ?
C3 N6 C4 105.2(5) . . ?
C3 N6 N5 124.0(5) . . ?
C4 N6 N5 130.8(5) . . ?
C3 N7 N8 106.6(5) . . ?
C4 N8 N7 108.3(5) . . ?
C5 N9 N10 108.4(4) . . ?
C5 N9 Fe1 129.1(4) . . ?
N10 N9 Fe1 122.2(3) . . ?
C6 N10 N9 106.0(4) . . ?
C6 N11 C5 106.9(4) . . ?
C6 N11 N12 122.4(4) . . ?
C5 N11 N12 130.7(4) . . ?
N12 N12 N11 110.5(5) 2_756 . ?
N1 C1 N3 111.0(5) . . ?
N1 C1 H1 124.5 . . ?
N3 C1 H1 124.5 . . ?
N2 C2 N3 110.2(5) . . ?
N2 C2 H2 124.9 . . ?
N3 C2 H2 124.9 . . ?
N7 C3 N6 110.6(6) . . ?
N7 C3 H3 124.7 . . ?
N6 C3 H3 124.7 . . ?
N8 C4 N6 109.3(6) . . ?
N8 C4 H4 125.3 . . ?
N6 C4 H4 125.3 . . ?
N9 C5 N11 108.4(5) . . ?
N9 C5 H5 125.8 . . ?
N11 C5 H5 125.8 . . ?
N10 C6 N11 110.3(5) . . ?
N10 C6 H6 124.9 . . ?
N11 C6 H6 124.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1W Fe1 N1 C1 -79.8(6) . . . . ?
O1W Fe1 N1 C1 100.2(6) 2_666 . . . ?
N9 Fe1 N1 C1 -171.1(6) 2_666 . . . ?
N9 Fe1 N1 C1 8.9(6) . . . . ?
N1 Fe1 N1 C1 -176(30) 2_666 . . . ?
O1W Fe1 N1 N2 110.0(5) . . . . ?
O1W Fe1 N1 N2 -70.0(5) 2_666 . . . ?
N9 Fe1 N1 N2 18.7(5) 2_666 . . . ?
N9 Fe1 N1 N2 -161.3(5) . . . . ?
N1 Fe1 N1 N2 13(30) 2_666 . . . ?
C1 N1 N2 C2 -0.6(8) . . . . ?
Fe1 N1 N2 C2 171.6(5) . . . . ?
C1 N3 N4 N5 180.0(6) . . . . ?
C2 N3 N4 N5 -2.8(10) . . . . ?
N3 N4 N5 N6 178.5(5) . . . . ?
N4 N5 N6 C3 -172.4(6) . . . . ?
N4 N5 N6 C4 3.8(9) . . . . ?
C3 N7 N8 C4 0.4(8) . . . . ?
O1W Fe1 N9 C5 -31.8(5) . . . . ?
O1W Fe1 N9 C5 148.2(5) 2_666 . . . ?
N9 Fe1 N9 C5 65(15) 2_666 . . . ?
N1 Fe1 N9 C5 -123.3(5) . . . . ?
N1 Fe1 N9 C5 56.7(5) 2_666 . . . ?
O1W Fe1 N9 N10 141.4(4) . . . . ?
O1W Fe1 N9 N10 -38.6(4) 2_666 . . . ?
N9 Fe1 N9 N10 -121(15) 2_666 . . . ?
N1 Fe1 N9 N10 49.9(4) . . . . ?
N1 Fe1 N9 N10 -130.1(4) 2_666 . . . ?
C5 N9 N10 C6 1.0(6) . . . . ?
Fe1 N9 N10 C6 -173.5(4) . . . . ?
C6 N11 N12 N12 -178.6(6) . . . 2_756 ?
C5 N11 N12 N12 -1.6(9) . . . 2_756 ?
N2 N1 C1 N3 0.1(7) . . . . ?
Fe1 N1 C1 N3 -171.3(4) . . . . ?
C2 N3 C1 N1 0.4(7) . . . . ?
N4 N3 C1 N1 178.3(5) . . . . ?
N1 N2 C2 N3 0.9(8) . . . . ?
C1 N3 C2 N2 -0.8(8) . . . . ?
N4 N3 C2 N2 -178.3(6) . . . . ?
N8 N7 C3 N6 -0.7(8) . . . . ?
C4 N6 C3 N7 0.7(8) . . . . ?
N5 N6 C3 N7 177.7(6) . . . . ?
N7 N8 C4 N6 0.0(8) . . . . ?
C3 N6 C4 N8 -0.4(8) . . . . ?
N5 N6 C4 N8 -177.2(6) . . . . ?
N10 N9 C5 N11 -0.5(6) . . . . ?
Fe1 N9 C5 N11 173.4(3) . . . . ?
C6 N11 C5 N9 -0.1(6) . . . . ?
N12 N11 C5 N9 -177.4(5) . . . . ?
N9 N10 C6 N11 -1.0(6) . . . . ?
C5 N11 C6 N10 0.7(7) . . . . ?
N12 N11 C6 N10 178.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         1.269
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.118
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6
_database_code_depnum_ccdc_archive 'CCDC 1055570'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 B2 Cu F8 N24 O2'
_chemical_formula_weight         765.65

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   8.2723(12)
_cell_length_b                   20.345(3)
_cell_length_c                   8.6343(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.360(2)
_cell_angle_gamma                90.00
_cell_volume                     1451.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3782
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      28.22

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             766
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8597
_exptl_absorpt_correction_T_max  0.8810
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8281
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2556
_reflns_number_gt                2322
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0316P)²+1.1813P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2556
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0764
_refine_ls_wR_factor_gt          0.0744
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 0.0000 0.0000 0.00730(12) Uani 1 2 d S . .
F1 F 0.23760(16) 0.31643(8) 0.26078(15) 0.0335(4) Uani 1 1 d . . .
F2 F 0.18154(19) 0.25129(7) 0.05190(17) 0.0381(4) Uani 1 1 d . . .
F3 F 0.32541(19) 0.34565(8) 0.02468(18) 0.0429(4) Uani 1 1 d . . .
F4 F 0.05672(18) 0.35004(8) 0.07064(17) 0.0369(4) Uani 1 1 d . . .
O1 O 0.3346(2) 0.16594(9) 0.3056(2) 0.0368(5) Uani 1 1 d . . .
H1A H 0.3896 0.1660 0.3909 0.055 Uiso 1 1 d R . .
H1B H 0.2936 0.2040 0.2939 0.055 Uiso 1 1 d R . .
N1 N 0.8244(2) 0.17370(8) 0.17497(19) 0.0122(4) Uani 1 1 d . . .
N2 N 0.88513(19) 0.07828(8) 0.08636(18) 0.0105(4) Uani 1 1 d . . .
N3 N 0.71693(19) 0.08132(8) 0.09159(19) 0.0133(4) Uani 1 1 d . . .
N4 N 0.8513(2) 0.23687(8) 0.2320(2) 0.0141(4) Uani 1 1 d . . .
N5 N 0.7233(2) 0.26875(9) 0.2216(2) 0.0149(4) Uani 1 1 d . . .
N6 N 0.7468(2) 0.33094(8) 0.28326(19) 0.0125(4) Uani 1 1 d . . .
N7 N 0.8400(2) 0.41647(9) 0.4115(2) 0.0149(4) Uani 1 1 d . . .
N8 N 0.67476(19) 0.42627(8) 0.37118(19) 0.0134(4) Uani 1 1 d . . .
N9 N 1.34348(19) 0.00047(8) 0.36659(19) 0.0102(4) Uani 1 1 d . . .
N10 N 1.1507(2) 0.00079(8) 0.19038(18) 0.0100(4) Uani 1 1 d . . .
N11 N 1.0804(2) 0.00360(8) 0.33536(19) 0.0143(4) Uani 1 1 d . . .
N12 N 1.5005(2) -0.00060(8) 0.4279(2) 0.0115(4) Uani 1 1 d . . .
B1 B 0.2011(3) 0.31588(13) 0.1011(3) 0.0233(6) Uani 1 1 d . . .
C1 C 0.9466(2) 0.13332(10) 0.1379(2) 0.0136(4) Uani 1 1 d . . .
H1 H 1.0586 0.1434 0.1479 0.016 Uiso 1 1 calc R . .
C2 C 0.6833(2) 0.13911(10) 0.1454(2) 0.0148(4) Uani 1 1 d . . .
H2 H 0.5775 0.1551 0.1619 0.018 Uiso 1 1 calc R . .
C3 C 0.8791(2) 0.35924(10) 0.3586(2) 0.0150(4) Uani 1 1 d . . .
H3 H 0.9833 0.3398 0.3701 0.018 Uiso 1 1 calc R . .
C4 C 0.6236(2) 0.37465(10) 0.2952(2) 0.0153(4) Uani 1 1 d . . .
H4 H 0.5164 0.3684 0.2543 0.018 Uiso 1 1 calc R . .
C5 C 1.3077(2) -0.00071(9) 0.2117(2) 0.0103(4) Uani 1 1 d . . .
H5 H 1.3840 -0.0023 0.1324 0.012 Uiso 1 1 calc R . .
C6 C 1.1982(2) 0.00305(10) 0.4389(2) 0.0137(4) Uani 1 1 d . . .
H6 H 1.1862 0.0042 0.5478 0.016 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 2.0134(16) 3_755 ?
Cu1 N2 2.0134(16) . ?
Cu1 N10 2.0216(17) 3_755 ?
Cu1 N10 2.0216(17) . ?
Cu1 N8 2.3896(16) 2_645 ?
Cu1 N8 2.3896(16) 4_665 ?
F1 B1 1.400(3) . ?
F2 B1 1.388(3) . ?
F3 B1 1.384(3) . ?
F4 B1 1.398(3) . ?
O1 H1A 0.8500 . ?
O1 H1B 0.8500 . ?
N1 C1 1.351(3) . ?
N1 C2 1.377(3) . ?
N1 N4 1.391(2) . ?
N2 C1 1.301(3) . ?
N2 N3 1.395(2) . ?
N3 C2 1.299(3) . ?
N4 N5 1.241(2) . ?
N5 N6 1.383(2) . ?
N6 C4 1.360(3) . ?
N6 C3 1.376(3) . ?
N7 C3 1.296(3) . ?
N7 N8 1.411(2) . ?
N8 C4 1.300(3) . ?
N8 Cu1 2.3896(16) 2_655 ?
N9 C5 1.358(3) . ?
N9 C6 1.378(3) . ?
N9 N12 1.383(2) . ?
N10 C5 1.305(3) . ?
N10 N11 1.403(2) . ?
N11 C6 1.295(3) . ?
N12 N12 1.245(3) 3_856 ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N2 180.00(8) 3_755 . ?
N2 Cu1 N10 88.69(6) 3_755 3_755 ?
N2 Cu1 N10 91.31(6) . 3_755 ?
N2 Cu1 N10 91.31(6) 3_755 . ?
N2 Cu1 N10 88.69(6) . . ?
N10 Cu1 N10 180.0 3_755 . ?
N2 Cu1 N8 88.83(6) 3_755 2_645 ?
N2 Cu1 N8 91.17(6) . 2_645 ?
N10 Cu1 N8 90.52(6) 3_755 2_645 ?
N10 Cu1 N8 89.48(6) . 2_645 ?
N2 Cu1 N8 91.17(6) 3_755 4_665 ?
N2 Cu1 N8 88.83(6) . 4_665 ?
N10 Cu1 N8 89.49(6) 3_755 4_665 ?
N10 Cu1 N8 90.51(6) . 4_665 ?
N8 Cu1 N8 180.0 2_645 4_665 ?
H1A O1 H1B 107.4 . . ?
C1 N1 C2 106.37(16) . . ?
C1 N1 N4 122.37(16) . . ?
C2 N1 N4 131.25(16) . . ?
C1 N2 N3 109.07(16) . . ?
C1 N2 Cu1 128.62(14) . . ?
N3 N2 Cu1 122.24(12) . . ?
C2 N3 N2 106.27(16) . . ?
N5 N4 N1 109.50(16) . . ?
N4 N5 N6 110.13(16) . . ?
C4 N6 C3 105.92(16) . . ?
C4 N6 N5 122.25(17) . . ?
C3 N6 N5 131.38(17) . . ?
C3 N7 N8 107.07(16) . . ?
C4 N8 N7 107.60(16) . . ?
C4 N8 Cu1 123.47(13) . 2_655 ?
N7 N8 Cu1 124.93(12) . 2_655 ?
C5 N9 C6 106.76(17) . . ?
C5 N9 N12 122.68(17) . . ?
C6 N9 N12 130.56(17) . . ?
C5 N10 N11 108.77(16) . . ?
C5 N10 Cu1 133.73(14) . . ?
N11 N10 Cu1 117.51(12) . . ?
C6 N11 N10 106.77(16) . . ?
N12 N12 N9 109.7(2) 3_856 . ?
F3 B1 F2 110.4(2) . . ?
F3 B1 F1 109.4(2) . . ?
F2 B1 F1 109.1(2) . . ?
F3 B1 F4 109.8(2) . . ?
F2 B1 F4 109.0(2) . . ?
F1 B1 F4 109.2(2) . . ?
N2 C1 N1 108.60(17) . . ?
N2 C1 H1 125.7 . . ?
N1 C1 H1 125.7 . . ?
N3 C2 N1 109.67(17) . . ?
N3 C2 H2 125.2 . . ?
N1 C2 H2 125.2 . . ?
N7 C3 N6 109.69(18) . . ?
N7 C3 H3 125.2 . . ?
N6 C3 H3 125.2 . . ?
N8 C4 N6 109.72(18) . . ?
N8 C4 H4 125.1 . . ?
N6 C4 H4 125.1 . . ?
N10 C5 N9 108.27(17) . . ?
N10 C5 H5 125.9 . . ?
N9 C5 H5 125.9 . . ?
N11 C6 N9 109.43(18) . . ?
N11 C6 H6 125.3 . . ?
N9 C6 H6 125.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Cu1 N2 C1 91(30) 3_755 . . . ?
N10 Cu1 N2 C1 -128.86(17) 3_755 . . . ?
N10 Cu1 N2 C1 51.14(17) . . . . ?
N8 Cu1 N2 C1 140.60(17) 2_645 . . . ?
N8 Cu1 N2 C1 -39.40(17) 4_665 . . . ?
N2 Cu1 N2 N3 -92(30) 3_755 . . . ?
N10 Cu1 N2 N3 47.83(14) 3_755 . . . ?
N10 Cu1 N2 N3 -132.17(14) . . . . ?
N8 Cu1 N2 N3 -42.72(14) 2_645 . . . ?
N8 Cu1 N2 N3 137.29(14) 4_665 . . . ?
C1 N2 N3 C2 0.6(2) . . . . ?
Cu1 N2 N3 C2 -176.64(13) . . . . ?
C1 N1 N4 N5 164.09(18) . . . . ?
C2 N1 N4 N5 -16.4(3) . . . . ?
N1 N4 N5 N6 177.77(15) . . . . ?
N4 N5 N6 C4 -175.85(18) . . . . ?
N4 N5 N6 C3 -4.7(3) . . . . ?
C3 N7 N8 C4 -0.5(2) . . . . ?
C3 N7 N8 Cu1 157.52(14) . . . 2_655 ?
N2 Cu1 N10 C5 50.00(19) 3_755 . . . ?
N2 Cu1 N10 C5 -130.00(19) . . . . ?
N10 Cu1 N10 C5 -165(4) 3_755 . . . ?
N8 Cu1 N10 C5 138.82(18) 2_645 . . . ?
N8 Cu1 N10 C5 -41.18(18) 4_665 . . . ?
N2 Cu1 N10 N11 -130.12(13) 3_755 . . . ?
N2 Cu1 N10 N11 49.88(13) . . . . ?
N10 Cu1 N10 N11 15(4) 3_755 . . . ?
N8 Cu1 N10 N11 -41.30(13) 2_645 . . . ?
N8 Cu1 N10 N11 138.70(13) 4_665 . . . ?
C5 N10 N11 C6 -0.6(2) . . . . ?
Cu1 N10 N11 C6 179.48(13) . . . . ?
C5 N9 N12 N12 -179.74(19) . . . 3_856 ?
C6 N9 N12 N12 0.6(3) . . . 3_856 ?
N3 N2 C1 N1 -1.1(2) . . . . ?
Cu1 N2 C1 N1 175.91(13) . . . . ?
C2 N1 C1 N2 1.2(2) . . . . ?
N4 N1 C1 N2 -179.24(17) . . . . ?
N2 N3 C2 N1 0.1(2) . . . . ?
C1 N1 C2 N3 -0.8(2) . . . . ?
N4 N1 C2 N3 179.67(18) . . . . ?
N8 N7 C3 N6 0.7(2) . . . . ?
C4 N6 C3 N7 -0.6(2) . . . . ?
N5 N6 C3 N7 -172.87(18) . . . . ?
N7 N8 C4 N6 0.1(2) . . . . ?
Cu1 N8 C4 N6 -158.30(13) 2_655 . . . ?
C3 N6 C4 N8 0.3(2) . . . . ?
N5 N6 C4 N8 173.44(17) . . . . ?
N11 N10 C5 N9 0.5(2) . . . . ?
Cu1 N10 C5 N9 -179.60(13) . . . . ?
C6 N9 C5 N10 -0.2(2) . . . . ?
N12 N9 C5 N10 -179.98(16) . . . . ?
N10 N11 C6 N9 0.5(2) . . . . ?
C5 N9 C6 N11 -0.2(2) . . . . ?
N12 N9 C6 N11 179.56(18) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.059
