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

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

data_pbcn
_database_code_depnum_ccdc_archive 'CCDC 1030268'
_audit_update_record             
;
2014-10-22 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 Co F2 N6 O4'
_chemical_formula_weight         473.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   7.8197(4)
_cell_length_b                   17.8112(9)
_cell_length_c                   26.5942(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3704.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1912
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7559
_exptl_absorpt_correction_T_max  0.7974
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17808
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3307
_reflns_number_gt                2795
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0328P)²+1.8561P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3307
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0649
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co -0.01709(3) 0.040753(15) 0.381106(10) 0.02316(9) Uani 1 1 d . . .
O1 O 0.25868(18) 0.03325(9) 0.37203(5) 0.0344(4) Uani 1 1 d . . .
O2 O 0.15100(17) 0.06417(9) 0.44511(5) 0.0341(4) Uani 1 1 d . . .
O3 O 0.0980(3) -0.30953(10) 0.30960(7) 0.0588(5) Uani 1 1 d . . .
O4 O 0.2014(2) -0.20405(9) 0.27530(6) 0.0482(4) Uani 1 1 d . . .
N1 N 0.7561(2) 0.05594(9) 0.42647(6) 0.0258(4) Uani 1 1 d . . .
N2 N -0.0122(2) -0.07839(10) 0.39025(6) 0.0257(4) Uani 1 1 d . . .
N3 N -0.1402(2) 0.02982(9) 0.31189(6) 0.0276(4) Uani 1 1 d . . .
N4 N -0.2682(2) 0.08802(11) 0.24934(7) 0.0329(4) Uani 1 1 d . . .
N5 N -0.0360(2) 0.15556(10) 0.35980(7) 0.0314(4) Uani 1 1 d . . .
F1 F 0.66809(17) 0.13930(10) 0.54559(5) 0.0602(5) Uani 1 1 d . . .
F2 F -0.1660(3) -0.22383(8) 0.47001(6) 0.0788(6) Uani 1 1 d . . .
C1 C 0.2766(2) 0.05338(11) 0.41666(7) 0.0256(4) Uani 1 1 d . . .
C2 C 0.4535(2) 0.06554(11) 0.43702(7) 0.0236(4) Uani 1 1 d . . .
C3 C 0.5965(2) 0.04544(11) 0.40971(7) 0.0262(4) Uani 1 1 d . . .
H3 H 0.5812 0.0236 0.3783 0.031 Uiso 1 1 calc R . .
C4 C 0.7767(3) 0.08733(12) 0.47167(8) 0.0319(5) Uani 1 1 d . . .
H4 H 0.8866 0.0951 0.4840 0.038 Uiso 1 1 calc R . .
C5 C 0.6395(3) 0.10818(13) 0.50014(8) 0.0325(5) Uani 1 1 d . . .
C6 C 0.4763(2) 0.09836(12) 0.48361(8) 0.0302(5) Uani 1 1 d . . .
H6 H 0.3833 0.1132 0.5030 0.036 Uiso 1 1 calc R . .
C7 C 0.1234(3) -0.24035(14) 0.30809(9) 0.0389(6) Uani 1 1 d . . .
C8 C 0.0489(3) -0.19699(12) 0.35173(8) 0.0310(5) Uani 1 1 d . . .
C9 C 0.0549(2) -0.11969(12) 0.35306(8) 0.0282(5) Uani 1 1 d . . .
H9 H 0.1085 -0.0948 0.3267 0.034 Uiso 1 1 calc R . .
C10 C -0.0832(3) -0.11421(12) 0.42870(8) 0.0306(5) Uani 1 1 d . . .
H10 H -0.1285 -0.0867 0.4553 0.037 Uiso 1 1 calc R . .
C11 C -0.0910(3) -0.19075(13) 0.42983(8) 0.0409(6) Uani 1 1 d . . .
C12 C -0.0279(3) -0.23361(13) 0.39149(9) 0.0430(6) Uani 1 1 d . . .
H12 H -0.0363 -0.2857 0.3922 0.052 Uiso 1 1 calc R . .
C13 C -0.2105(3) -0.02260(12) 0.28005(8) 0.0309(5) Uani 1 1 d . . .
H13 H -0.2048 -0.0744 0.2843 0.037 Uiso 1 1 calc R . .
C14 C -0.2889(3) 0.01291(13) 0.24173(8) 0.0333(5) Uani 1 1 d . . .
H14 H -0.3464 -0.0096 0.2151 0.040 Uiso 1 1 calc R . .
C15 C -0.1786(2) 0.09594(12) 0.29173(7) 0.0276(5) Uani 1 1 d . . .
C16 C -0.1208(3) 0.16314(12) 0.31696(8) 0.0298(5) Uani 1 1 d . . .
C17 C -0.0584(3) 0.27646(13) 0.34034(9) 0.0447(6) Uani 1 1 d . . .
H17 H -0.0486 0.3285 0.3415 0.054 Uiso 1 1 calc R . .
C18 C 0.0030(3) 0.22715(13) 0.37470(9) 0.0391(5) Uani 1 1 d . . .
H18 H 0.0623 0.2399 0.4038 0.047 Uiso 1 1 calc R . .
H1 H -0.306(3) 0.1244(16) 0.2302(10) 0.055(8) Uiso 1 1 d . . .
H2 H -0.199(4) 0.2555(17) 0.2751(11) 0.076(9) Uiso 1 1 d . . .
N6 N -0.1378(2) 0.23532(11) 0.30359(7) 0.0378(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N3 2.0863(16) . ?
Co1 N5 2.1271(18) . ?
Co1 N2 2.1363(17) . ?
Co1 N1 2.1620(16) 1_455 ?
Co1 O1 2.1740(14) . ?
Co1 O2 2.1907(14) . ?
O1 C1 1.248(2) . ?
O2 C1 1.255(2) . ?
O3 C7 1.249(3) . ?
O4 C7 1.245(3) . ?
N1 C4 1.335(2) . ?
N1 C3 1.339(2) . ?
N1 Co1 2.1620(16) 1_655 ?
N2 C10 1.327(3) . ?
N2 C9 1.340(3) . ?
N3 C15 1.328(3) . ?
N3 C13 1.375(3) . ?
N4 C15 1.335(3) . ?
N4 C14 1.363(3) . ?
N4 H1 0.87(3) . ?
N5 C16 1.325(3) . ?
N5 C18 1.370(3) . ?
F1 C5 1.348(2) . ?
F2 C11 1.354(3) . ?
C1 C2 1.501(3) . ?
C2 C3 1.380(3) . ?
C2 C6 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.511(3) . ?
C8 C9 1.378(3) . ?
C8 C12 1.380(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.347(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.445(3) . ?
C16 N6 1.341(3) . ?
C17 C18 1.355(3) . ?
C17 N6 1.370(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
N6 H2 0.97(3) . ?

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
N3 Co1 N5 79.79(7) . . ?
N3 Co1 N2 90.92(6) . . ?
N5 Co1 N2 170.58(6) . . ?
N3 Co1 N1 97.22(6) . 1_455 ?
N5 Co1 N1 88.36(6) . 1_455 ?
N2 Co1 N1 94.33(6) . 1_455 ?
N3 Co1 O1 110.72(6) . . ?
N5 Co1 O1 95.64(6) . . ?
N2 Co1 O1 86.20(6) . . ?
N1 Co1 O1 152.05(6) 1_455 . ?
N3 Co1 O2 168.56(6) . . ?
N5 Co1 O2 93.76(6) . . ?
N2 Co1 O2 95.16(6) . . ?
N1 Co1 O2 91.99(5) 1_455 . ?
O1 Co1 O2 60.19(5) . . ?
C1 O1 Co1 89.33(12) . . ?
C1 O2 Co1 88.39(11) . . ?
C4 N1 C3 118.09(17) . . ?
C4 N1 Co1 117.11(13) . 1_655 ?
C3 N1 Co1 124.17(13) . 1_655 ?
C10 N2 C9 117.96(18) . . ?
C10 N2 Co1 123.89(14) . . ?
C9 N2 Co1 117.93(14) . . ?
C15 N3 C13 105.25(16) . . ?
C15 N3 Co1 112.19(13) . . ?
C13 N3 Co1 142.29(14) . . ?
C15 N4 C14 106.95(18) . . ?
C15 N4 H1 126.2(18) . . ?
C14 N4 H1 126.8(18) . . ?
C16 N5 C18 105.38(18) . . ?
C16 N5 Co1 111.21(14) . . ?
C18 N5 Co1 143.37(15) . . ?
O1 C1 O2 121.98(18) . . ?
O1 C1 C2 119.22(17) . . ?
O2 C1 C2 118.80(17) . . ?
C3 C2 C6 118.50(18) . . ?
C3 C2 C1 121.28(17) . . ?
C6 C2 C1 120.22(17) . . ?
N1 C3 C2 122.94(18) . . ?
N1 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
N1 C4 C5 121.21(18) . . ?
N1 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
F1 C5 C6 119.87(18) . . ?
F1 C5 C4 118.59(18) . . ?
C6 C5 C4 121.54(19) . . ?
C5 C6 C2 117.70(18) . . ?
C5 C6 H6 121.1 . . ?
C2 C6 H6 121.1 . . ?
O4 C7 O3 127.8(2) . . ?
O4 C7 C8 117.5(2) . . ?
O3 C7 C8 114.7(2) . . ?
C9 C8 C12 117.88(19) . . ?
C9 C8 C7 121.1(2) . . ?
C12 C8 C7 121.0(2) . . ?
N2 C9 C8 123.6(2) . . ?
N2 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
N2 C10 C11 121.04(19) . . ?
N2 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
F2 C11 C10 118.1(2) . . ?
F2 C11 C12 120.2(2) . . ?
C10 C11 C12 121.7(2) . . ?
C11 C12 C8 117.7(2) . . ?
C11 C12 H12 121.1 . . ?
C8 C12 H12 121.1 . . ?
C14 C13 N3 109.22(19) . . ?
C14 C13 H13 125.4 . . ?
N3 C13 H13 125.4 . . ?
C13 C14 N4 107.11(19) . . ?
C13 C14 H14 126.4 . . ?
N4 C14 H14 126.4 . . ?
N3 C15 N4 111.46(18) . . ?
N3 C15 C16 118.45(18) . . ?
N4 C15 C16 130.09(19) . . ?
N5 C16 N6 112.06(19) . . ?
N5 C16 C15 118.12(19) . . ?
N6 C16 C15 129.82(19) . . ?
C18 C17 N6 107.2(2) . . ?
C18 C17 H17 126.4 . . ?
N6 C17 H17 126.4 . . ?
C17 C18 N5 109.2(2) . . ?
C17 C18 H18 125.4 . . ?
N5 C18 H18 125.4 . . ?
C16 N6 C17 106.18(19) . . ?
C16 N6 H2 127.9(18) . . ?
C17 N6 H2 125.8(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Co1 O1 C1 170.39(12) . . . . ?
N5 Co1 O1 C1 89.20(12) . . . . ?
N2 Co1 O1 C1 -100.07(12) . . . . ?
N1 Co1 O1 C1 -8.0(2) 1_455 . . . ?
O2 Co1 O1 C1 -1.91(11) . . . . ?
N3 Co1 O2 C1 -37.3(4) . . . . ?
N5 Co1 O2 C1 -92.45(13) . . . . ?
N2 Co1 O2 C1 84.52(12) . . . . ?
N1 Co1 O2 C1 179.06(12) 1_455 . . . ?
O1 Co1 O2 C1 1.90(11) . . . . ?
N3 Co1 N2 C10 -121.43(16) . . . . ?
N5 Co1 N2 C10 -130.5(4) . . . . ?
N1 Co1 N2 C10 -24.12(16) 1_455 . . . ?
O1 Co1 N2 C10 127.86(16) . . . . ?
O2 Co1 N2 C10 68.27(16) . . . . ?
N3 Co1 N2 C9 53.17(15) . . . . ?
N5 Co1 N2 C9 44.1(5) . . . . ?
N1 Co1 N2 C9 150.48(14) 1_455 . . . ?
O1 Co1 N2 C9 -57.54(14) . . . . ?
O2 Co1 N2 C9 -117.13(14) . . . . ?
N5 Co1 N3 C15 -4.45(13) . . . . ?
N2 Co1 N3 C15 177.05(14) . . . . ?
N1 Co1 N3 C15 82.57(14) 1_455 . . . ?
O1 Co1 N3 C15 -96.66(14) . . . . ?
O2 Co1 N3 C15 -60.8(4) . . . . ?
N5 Co1 N3 C13 -177.1(2) . . . . ?
N2 Co1 N3 C13 4.4(2) . . . . ?
N1 Co1 N3 C13 -90.1(2) 1_455 . . . ?
O1 Co1 N3 C13 90.7(2) . . . . ?
O2 Co1 N3 C13 126.6(3) . . . . ?
N3 Co1 N5 C16 3.54(14) . . . . ?
N2 Co1 N5 C16 12.7(5) . . . . ?
N1 Co1 N5 C16 -94.10(14) 1_455 . . . ?
O1 Co1 N5 C16 113.62(14) . . . . ?
O2 Co1 N5 C16 174.01(14) . . . . ?
N3 Co1 N5 C18 -179.4(3) . . . . ?
N2 Co1 N5 C18 -170.1(3) . . . . ?
N1 Co1 N5 C18 83.0(3) 1_455 . . . ?
O1 Co1 N5 C18 -69.3(3) . . . . ?
O2 Co1 N5 C18 -8.9(3) . . . . ?
Co1 O1 C1 O2 3.4(2) . . . . ?
Co1 O1 C1 C2 -176.25(16) . . . . ?
Co1 O2 C1 O1 -3.4(2) . . . . ?
Co1 O2 C1 C2 176.27(16) . . . . ?
O1 C1 C2 C3 -8.7(3) . . . . ?
O2 C1 C2 C3 171.60(19) . . . . ?
O1 C1 C2 C6 170.35(19) . . . . ?
O2 C1 C2 C6 -9.3(3) . . . . ?
C4 N1 C3 C2 0.0(3) . . . . ?
Co1 N1 C3 C2 -170.59(15) 1_655 . . . ?
C6 C2 C3 N1 0.4(3) . . . . ?
C1 C2 C3 N1 179.48(18) . . . . ?
C3 N1 C4 C5 0.0(3) . . . . ?
Co1 N1 C4 C5 171.28(17) 1_655 . . . ?
N1 C4 C5 F1 179.7(2) . . . . ?
N1 C4 C5 C6 -0.4(4) . . . . ?
F1 C5 C6 C2 -179.4(2) . . . . ?
C4 C5 C6 C2 0.8(3) . . . . ?
C3 C2 C6 C5 -0.7(3) . . . . ?
C1 C2 C6 C5 -179.85(19) . . . . ?
O4 C7 C8 C9 5.2(3) . . . . ?
O3 C7 C8 C9 -174.7(2) . . . . ?
O4 C7 C8 C12 -175.0(2) . . . . ?
O3 C7 C8 C12 5.1(3) . . . . ?
C10 N2 C9 C8 2.3(3) . . . . ?
Co1 N2 C9 C8 -172.60(16) . . . . ?
C12 C8 C9 N2 -1.3(3) . . . . ?
C7 C8 C9 N2 178.57(19) . . . . ?
C9 N2 C10 C11 -1.4(3) . . . . ?
Co1 N2 C10 C11 173.25(17) . . . . ?
N2 C10 C11 F2 -179.6(2) . . . . ?
N2 C10 C11 C12 -0.6(4) . . . . ?
F2 C11 C12 C8 -179.3(2) . . . . ?
C10 C11 C12 C8 1.7(4) . . . . ?
C9 C8 C12 C11 -0.7(3) . . . . ?
C7 C8 C12 C11 179.4(2) . . . . ?
C15 N3 C13 C14 0.1(2) . . . . ?
Co1 N3 C13 C14 173.02(17) . . . . ?
N3 C13 C14 N4 0.0(2) . . . . ?
C15 N4 C14 C13 0.0(2) . . . . ?
C13 N3 C15 N4 -0.1(2) . . . . ?
Co1 N3 C15 N4 -175.44(13) . . . . ?
C13 N3 C15 C16 -179.85(18) . . . . ?
Co1 N3 C15 C16 4.8(2) . . . . ?
C14 N4 C15 N3 0.1(2) . . . . ?
C14 N4 C15 C16 179.8(2) . . . . ?
C18 N5 C16 N6 0.2(2) . . . . ?
Co1 N5 C16 N6 178.38(14) . . . . ?
C18 N5 C16 C15 179.61(18) . . . . ?
Co1 N5 C16 C15 -2.2(2) . . . . ?
N3 C15 C16 N5 -1.8(3) . . . . ?
N4 C15 C16 N5 178.5(2) . . . . ?
N3 C15 C16 N6 177.6(2) . . . . ?
N4 C15 C16 N6 -2.2(4) . . . . ?
N6 C17 C18 N5 0.4(3) . . . . ?
C16 N5 C18 C17 -0.3(3) . . . . ?
Co1 N5 C18 C17 -177.53(19) . . . . ?
N5 C16 N6 C17 0.1(3) . . . . ?
C15 C16 N6 C17 -179.3(2) . . . . ?
C18 C17 N6 C16 -0.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H2 O4 0.97(3) 1.71(3) 2.673(2) 176(3) 6_566
N4 H1 O3 0.87(3) 1.75(3) 2.623(2) 173(3) 6_566

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_p1
_database_code_depnum_ccdc_archive 'CCDC 1030269'
_audit_update_record             
;
2014-10-22 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Cd F2 N10 O4'
_chemical_formula_weight         660.88

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'
Cd Cd -0.8075 1.2024 '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'
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                   7.3743(4)
_cell_length_b                   8.4333(5)
_cell_length_c                   10.3961(5)
_cell_angle_alpha                92.632(2)
_cell_angle_beta                 94.015(2)
_cell_angle_gamma                94.544(2)
_cell_volume                     642.05(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             330
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7831
_exptl_absorpt_correction_T_max  0.8097
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3262
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2243
_reflns_number_gt                2190
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0347P)²+0.2837P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2243
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0636
_refine_ls_wR_factor_gt          0.0622
_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
Cd1 Cd 1.0000 0.5000 0.0000 0.03661(10) Uani 1 2 d S . .
O1 O 1.1832(2) 0.7090(2) 0.13395(16) 0.0443(4) Uani 1 1 d . . .
O2 O 1.2861(3) 0.6884(3) 0.33829(19) 0.0679(6) Uani 1 1 d . . .
N1 N 0.7780(3) 0.9854(3) 0.2539(2) 0.0542(6) Uani 1 1 d . . .
N2 N 0.8190(2) 0.4615(2) 0.16949(17) 0.0327(4) Uani 1 1 d . . .
N3 N 0.5814(3) 0.5362(2) 0.26704(18) 0.0359(4) Uani 1 1 d . . .
N4 N 0.7711(2) 0.6656(2) -0.03263(17) 0.0343(4) Uani 1 1 d . . .
N5 N 0.5099(3) 0.7394(2) 0.02973(18) 0.0331(4) Uani 1 1 d . . .
F1 F 0.7256(3) 0.8308(3) 0.56394(19) 0.0918(7) Uani 1 1 d . . .
C1 C 1.1738(3) 0.7285(3) 0.2546(2) 0.0396(5) Uani 1 1 d . . .
C2 C 1.0118(3) 0.8087(3) 0.2990(2) 0.0352(5) Uani 1 1 d . . .
C3 C 0.9227(3) 0.9113(3) 0.2210(2) 0.0422(5) Uani 1 1 d . . .
H3 H 0.9663 0.9298 0.1408 0.051 Uiso 1 1 calc R . .
C4 C 0.7164(4) 0.9562(3) 0.3683(3) 0.0570(7) Uani 1 1 d . . .
H4 H 0.6148 1.0051 0.3933 0.068 Uiso 1 1 calc R . .
C5 C 0.7973(4) 0.8570(3) 0.4497(3) 0.0522(6) Uani 1 1 d . . .
C6 C 0.9475(4) 0.7813(3) 0.4180(2) 0.0453(6) Uani 1 1 d . . .
H6 H 1.0034 0.7144 0.4743 0.054 Uiso 1 1 calc R . .
C7 C 0.8108(3) 0.3875(3) 0.2834(2) 0.0403(5) Uani 1 1 d . . .
H7 H 0.8926 0.3173 0.3143 0.048 Uiso 1 1 calc R . .
C8 C 0.6651(3) 0.4321(3) 0.3445(2) 0.0425(5) Uani 1 1 d . . .
H8 H 0.6289 0.3988 0.4235 0.051 Uiso 1 1 calc R . .
C9 C 0.6788(3) 0.5504(2) 0.16341(19) 0.0288(4) Uani 1 1 d . . .
C10 C 0.6492(3) 0.6508(2) 0.05476(19) 0.0284(4) Uani 1 1 d . . .
C11 C 0.5420(3) 0.8155(3) -0.0811(2) 0.0393(5) Uani 1 1 d . . .
H11 H 0.4680 0.8847 -0.1225 0.047 Uiso 1 1 calc R . .
C12 C 0.7033(3) 0.7694(3) -0.1183(2) 0.0399(5) Uani 1 1 d . . .
H12 H 0.7595 0.8031 -0.1907 0.048 Uiso 1 1 calc R . .
H1 H 0.480(4) 0.591(3) 0.281(3) 0.054(8) Uiso 1 1 d . . .
H2 H 0.413(4) 0.729(3) 0.068(3) 0.050(8) Uiso 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
Cd1 N4 2.2915(18) . ?
Cd1 N4 2.2915(18) 2_765 ?
Cd1 N2 2.3031(18) . ?
Cd1 N2 2.3031(18) 2_765 ?
Cd1 O1 2.4503(16) 2_765 ?
Cd1 O1 2.4503(16) . ?
O1 C1 1.265(3) . ?
O2 C1 1.236(3) . ?
N1 C4 1.328(4) . ?
N1 C3 1.335(3) . ?
N2 C9 1.324(3) . ?
N2 C7 1.367(3) . ?
N3 C9 1.341(3) . ?
N3 C8 1.371(3) . ?
N3 H1 0.92(3) . ?
N4 C10 1.325(3) . ?
N4 C12 1.374(3) . ?
N5 C10 1.336(3) . ?
N5 C11 1.370(3) . ?
N5 H2 0.85(3) . ?
F1 C5 1.353(3) . ?
C1 C2 1.508(3) . ?
C2 C6 1.378(3) . ?
C2 C3 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.355(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.457(3) . ?
C11 C12 1.356(3) . ?
C11 H11 0.9300 . ?
C12 H12 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
N4 Cd1 N4 180.0 . 2_765 ?
N4 Cd1 N2 75.02(6) . . ?
N4 Cd1 N2 104.98(6) 2_765 . ?
N4 Cd1 N2 104.98(6) . 2_765 ?
N4 Cd1 N2 75.02(6) 2_765 2_765 ?
N2 Cd1 N2 180.0 . 2_765 ?
N4 Cd1 O1 89.29(6) . 2_765 ?
N4 Cd1 O1 90.71(6) 2_765 2_765 ?
N2 Cd1 O1 91.44(6) . 2_765 ?
N2 Cd1 O1 88.56(6) 2_765 2_765 ?
N4 Cd1 O1 90.71(6) . . ?
N4 Cd1 O1 89.29(6) 2_765 . ?
N2 Cd1 O1 88.56(6) . . ?
N2 Cd1 O1 91.44(6) 2_765 . ?
O1 Cd1 O1 180.0 2_765 . ?
C1 O1 Cd1 123.52(15) . . ?
C4 N1 C3 117.2(2) . . ?
C9 N2 C7 105.51(18) . . ?
C9 N2 Cd1 111.92(13) . . ?
C7 N2 Cd1 142.27(15) . . ?
C9 N3 C8 106.69(19) . . ?
C9 N3 H1 124.3(18) . . ?
C8 N3 H1 129.0(19) . . ?
C10 N4 C12 105.17(18) . . ?
C10 N4 Cd1 112.12(13) . . ?
C12 N4 Cd1 142.42(15) . . ?
C10 N5 C11 107.23(19) . . ?
C10 N5 H2 122(2) . . ?
C11 N5 H2 129(2) . . ?
O2 C1 O1 125.6(2) . . ?
O2 C1 C2 117.7(2) . . ?
O1 C1 C2 116.7(2) . . ?
C6 C2 C3 118.1(2) . . ?
C6 C2 C1 120.9(2) . . ?
C3 C2 C1 121.0(2) . . ?
N1 C3 C2 124.0(2) . . ?
N1 C3 H3 118.0 . . ?
C2 C3 H3 118.0 . . ?
N1 C4 C5 122.0(3) . . ?
N1 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
F1 C5 C4 118.8(3) . . ?
F1 C5 C6 119.5(3) . . ?
C4 C5 C6 121.6(3) . . ?
C5 C6 C2 117.1(2) . . ?
C5 C6 H6 121.4 . . ?
C2 C6 H6 121.4 . . ?
C8 C7 N2 109.6(2) . . ?
C8 C7 H7 125.2 . . ?
N2 C7 H7 125.2 . . ?
C7 C8 N3 106.6(2) . . ?
C7 C8 H8 126.7 . . ?
N3 C8 H8 126.7 . . ?
N2 C9 N3 111.66(18) . . ?
N2 C9 C10 120.26(18) . . ?
N3 C9 C10 128.06(19) . . ?
N4 C10 N5 111.68(18) . . ?
N4 C10 C9 120.38(18) . . ?
N5 C10 C9 127.91(19) . . ?
C12 C11 N5 106.20(19) . . ?
C12 C11 H11 126.9 . . ?
N5 C11 H11 126.9 . . ?
C11 C12 N4 109.7(2) . . ?
C11 C12 H12 125.1 . . ?
N4 C12 H12 125.1 . . ?

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
N4 Cd1 O1 C1 89.09(18) . . . . ?
N4 Cd1 O1 C1 -90.91(18) 2_765 . . . ?
N2 Cd1 O1 C1 14.10(18) . . . . ?
N2 Cd1 O1 C1 -165.90(18) 2_765 . . . ?
O1 Cd1 O1 C1 -180(41) 2_765 . . . ?
N4 Cd1 N2 C9 0.15(13) . . . . ?
N4 Cd1 N2 C9 -179.85(13) 2_765 . . . ?
N2 Cd1 N2 C9 -11(20) 2_765 . . . ?
O1 Cd1 N2 C9 -88.74(14) 2_765 . . . ?
O1 Cd1 N2 C9 91.26(14) . . . . ?
N4 Cd1 N2 C7 -172.3(3) . . . . ?
N4 Cd1 N2 C7 7.7(3) 2_765 . . . ?
N2 Cd1 N2 C7 176(20) 2_765 . . . ?
O1 Cd1 N2 C7 98.8(2) 2_765 . . . ?
O1 Cd1 N2 C7 -81.2(2) . . . . ?
N4 Cd1 N4 C10 3(14) 2_765 . . . ?
N2 Cd1 N4 C10 -3.17(13) . . . . ?
N2 Cd1 N4 C10 176.83(13) 2_765 . . . ?
O1 Cd1 N4 C10 88.51(14) 2_765 . . . ?
O1 Cd1 N4 C10 -91.49(14) . . . . ?
N4 Cd1 N4 C12 -169(14) 2_765 . . . ?
N2 Cd1 N4 C12 -175.7(3) . . . . ?
N2 Cd1 N4 C12 4.3(3) 2_765 . . . ?
O1 Cd1 N4 C12 -84.0(2) 2_765 . . . ?
O1 Cd1 N4 C12 96.0(2) . . . . ?
Cd1 O1 C1 O2 103.2(3) . . . . ?
Cd1 O1 C1 C2 -77.2(2) . . . . ?
O2 C1 C2 C6 -26.4(3) . . . . ?
O1 C1 C2 C6 154.0(2) . . . . ?
O2 C1 C2 C3 153.9(2) . . . . ?
O1 C1 C2 C3 -25.7(3) . . . . ?
C4 N1 C3 C2 -0.8(4) . . . . ?
C6 C2 C3 N1 -0.1(4) . . . . ?
C1 C2 C3 N1 179.6(2) . . . . ?
C3 N1 C4 C5 0.8(4) . . . . ?
N1 C4 C5 F1 -179.0(3) . . . . ?
N1 C4 C5 C6 -0.1(5) . . . . ?
F1 C5 C6 C2 178.2(2) . . . . ?
C4 C5 C6 C2 -0.8(4) . . . . ?
C3 C2 C6 C5 0.8(3) . . . . ?
C1 C2 C6 C5 -178.9(2) . . . . ?
C9 N2 C7 C8 0.2(3) . . . . ?
Cd1 N2 C7 C8 172.98(18) . . . . ?
N2 C7 C8 N3 -0.1(3) . . . . ?
C9 N3 C8 C7 -0.1(3) . . . . ?
C7 N2 C9 N3 -0.3(2) . . . . ?
Cd1 N2 C9 N3 -175.53(13) . . . . ?
C7 N2 C9 C10 178.04(18) . . . . ?
Cd1 N2 C9 C10 2.8(2) . . . . ?
C8 N3 C9 N2 0.3(2) . . . . ?
C8 N3 C9 C10 -177.9(2) . . . . ?
C12 N4 C10 N5 -0.3(2) . . . . ?
Cd1 N4 C10 N5 -175.60(13) . . . . ?
C12 N4 C10 C9 -178.83(18) . . . . ?
Cd1 N4 C10 C9 5.9(2) . . . . ?
C11 N5 C10 N4 0.5(2) . . . . ?
C11 N5 C10 C9 178.86(19) . . . . ?
N2 C9 C10 N4 -6.2(3) . . . . ?
N3 C9 C10 N4 171.8(2) . . . . ?
N2 C9 C10 N5 175.51(19) . . . . ?
N3 C9 C10 N5 -6.4(3) . . . . ?
C10 N5 C11 C12 -0.4(2) . . . . ?
N5 C11 C12 N4 0.3(3) . . . . ?
C10 N4 C12 C11 0.0(3) . . . . ?
Cd1 N4 C12 C11 172.85(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H1 O2 0.92(3) 1.83(3) 2.743(3) 170(3) 1_455
N5 H2 O1 0.85(3) 1.87(3) 2.709(3) 173(3) 1_455

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.103
####################################################################### 
# 
# 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_203_9co
_database_code_depnum_ccdc_archive 'CCDC 1030270'
_audit_update_record             
;
2014-10-22 deposited with the CCDC.
2015-01-05 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 H14 Co F2 N2 O8'
_chemical_formula_weight         411.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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           Monoclinic
_symmetry_space_group_name_H-M   I2/m

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

_cell_length_a                   8.4112(5)
_cell_length_b                   6.8339(5)
_cell_length_c                   13.2136(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.514(6)
_cell_angle_gamma                90.00
_cell_volume                     754.63(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             418
_exptl_absorpt_coefficient_mu    1.208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7362
_exptl_absorpt_correction_T_max  0.7685
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1376
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         25.04
_reflns_number_total             722
_reflns_number_gt                653
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0596P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         722
_refine_ls_number_parameters     80
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1009
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 0.5000 0.5000 0.0223(3) Uani 1 4 d S . .
O1 O 1.0714(4) 0.5000 0.1840(2) 0.0390(8) Uani 1 2 d S . .
O2 O 1.0904(4) 0.5000 0.3537(2) 0.0464(9) Uani 1 2 d S . .
O3 O 0.6632(3) 0.7191(4) 0.55429(16) 0.0327(6) Uani 1 1 d . . .
H1W H 0.6229 0.7883 0.5952 0.049 Uiso 1 1 calc R . .
N1 N 0.6053(4) 0.5000 0.3585(2) 0.0255(8) Uani 1 2 d S . .
F1 F 0.4667(3) 0.5000 0.09378(18) 0.0600(10) Uani 1 2 d S . .
C1 C 1.0125(5) 0.5000 0.2676(3) 0.0292(10) Uani 1 2 d S . .
C2 C 0.8326(5) 0.5000 0.2634(3) 0.0236(9) Uani 1 2 d S . .
C3 C 0.7620(5) 0.5000 0.3541(3) 0.0261(9) Uani 1 2 d S . .
H1 H 0.8290 0.5000 0.4152 0.031 Uiso 1 2 calc SR . .
C4 C 0.5077(5) 0.5000 0.2694(3) 0.0297(10) Uani 1 2 d S . .
H4 H 0.3973 0.5000 0.2700 0.036 Uiso 1 2 calc SR . .
C5 C 0.5720(5) 0.5000 0.1784(3) 0.0318(10) Uani 1 2 d S . .
C6 C 0.7331(5) 0.5000 0.1727(3) 0.0307(10) Uani 1 2 d S . .
H6 H 0.7742 0.5000 0.1102 0.037 Uiso 1 2 calc SR . .
H2W H 0.744(5) 0.688(7) 0.587(3) 0.061(14) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O3 2.102(2) . ?
Co1 O3 2.102(2) 5_666 ?
Co1 O3 2.102(2) 6_565 ?
Co1 O3 2.102(2) 2_656 ?
Co1 N1 2.157(3) 5_666 ?
Co1 N1 2.157(3) . ?
O1 C1 1.261(5) . ?
O2 C1 1.247(5) . ?
O3 H1W 0.8200 . ?
O3 H2W 0.79(4) . ?
N1 C3 1.326(5) . ?
N1 C4 1.357(5) . ?
F1 C5 1.345(4) . ?
C1 C2 1.508(5) . ?
C2 C6 1.382(5) . ?
C2 C3 1.397(5) . ?
C3 H1 0.9300 . ?
C4 C5 1.373(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(6) . ?
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
O3 Co1 O3 180.0 . 5_666 ?
O3 Co1 O3 90.86(14) . 6_565 ?
O3 Co1 O3 89.14(14) 5_666 6_565 ?
O3 Co1 O3 89.14(14) . 2_656 ?
O3 Co1 O3 90.86(14) 5_666 2_656 ?
O3 Co1 O3 180.00(11) 6_565 2_656 ?
O3 Co1 N1 91.18(8) . 5_666 ?
O3 Co1 N1 88.82(8) 5_666 5_666 ?
O3 Co1 N1 91.18(8) 6_565 5_666 ?
O3 Co1 N1 88.82(8) 2_656 5_666 ?
O3 Co1 N1 88.82(8) . . ?
O3 Co1 N1 91.18(8) 5_666 . ?
O3 Co1 N1 88.82(8) 6_565 . ?
O3 Co1 N1 91.18(8) 2_656 . ?
N1 Co1 N1 180.0 5_666 . ?
Co1 O3 H1W 109.5 . . ?
Co1 O3 H2W 119(3) . . ?
H1W O3 H2W 100.9 . . ?
C3 N1 C4 117.9(3) . . ?
C3 N1 Co1 123.1(2) . . ?
C4 N1 Co1 119.0(3) . . ?
O2 C1 O1 125.6(4) . . ?
O2 C1 C2 117.0(4) . . ?
O1 C1 C2 117.4(3) . . ?
C6 C2 C3 118.0(4) . . ?
C6 C2 C1 122.6(3) . . ?
C3 C2 C1 119.4(3) . . ?
N1 C3 C2 124.0(3) . . ?
N1 C3 H1 118.0 . . ?
C2 C3 H1 118.0 . . ?
N1 C4 C5 120.1(4) . . ?
N1 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
F1 C5 C6 121.2(3) . . ?
F1 C5 C4 116.1(4) . . ?
C6 C5 C4 122.7(4) . . ?
C5 C6 C2 117.3(4) . . ?
C5 C6 H6 121.3 . . ?
C2 C6 H6 121.3 . . ?

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
O3 Co1 N1 C3 45.44(7) . . . . ?
O3 Co1 N1 C3 -134.56(7) 5_666 . . . ?
O3 Co1 N1 C3 -45.44(7) 6_565 . . . ?
O3 Co1 N1 C3 134.56(7) 2_656 . . . ?
N1 Co1 N1 C3 0(100) 5_666 . . . ?
O3 Co1 N1 C4 -134.56(7) . . . . ?
O3 Co1 N1 C4 45.44(7) 5_666 . . . ?
O3 Co1 N1 C4 134.56(7) 6_565 . . . ?
O3 Co1 N1 C4 -45.44(7) 2_656 . . . ?
N1 Co1 N1 C4 180.0(16) 5_666 . . . ?
O2 C1 C2 C6 180.0 . . . . ?
O1 C1 C2 C6 0.0 . . . . ?
O2 C1 C2 C3 0.0 . . . . ?
O1 C1 C2 C3 180.0 . . . . ?
C4 N1 C3 C2 0.0 . . . . ?
Co1 N1 C3 C2 180.0 . . . . ?
C6 C2 C3 N1 0.0 . . . . ?
C1 C2 C3 N1 180.0 . . . . ?
C3 N1 C4 C5 0.0 . . . . ?
Co1 N1 C4 C5 180.0 . . . . ?
N1 C4 C5 F1 180.0 . . . . ?
N1 C4 C5 C6 0.0 . . . . ?
F1 C5 C6 C2 180.0 . . . . ?
C4 C5 C6 C2 0.0 . . . . ?
C3 C2 C6 C5 0.0 . . . . ?
C1 C2 C6 C5 180.0 . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H1W O1 0.82 1.94 2.742(3) 164.8 3_455
O3 H2W O2 0.79(4) 1.99(4) 2.728(4) 155(5) 5_766

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_202_10ni
_database_code_depnum_ccdc_archive 'CCDC 1030271'
_audit_update_record             
;
2014-10-22 deposited with the CCDC.
2015-01-05 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 H7 F2 N2 Ni O4.50'
_chemical_formula_weight         347.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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           Tetragonal
_symmetry_space_group_name_H-M   P4/ncc

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

_cell_length_a                   20.5004(7)
_cell_length_b                   20.5004(7)
_cell_length_c                   13.9201(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5850.2(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2800
_exptl_absorpt_coefficient_mu    1.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_T_max  0.7716
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14382
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2611
_reflns_number_gt                2151
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0419P)²+3.5132P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2611
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.382486(17) 0.536016(17) 0.34268(2) 0.02046(14) Uani 1 1 d . . .
O1 O 0.51639(10) 0.46488(9) 0.65165(13) 0.0261(5) Uani 1 1 d . . .
O2 O 0.47685(10) 0.37537(9) 0.72505(13) 0.0263(5) Uani 1 1 d . . .
O3 O 0.19501(11) 0.60321(14) 0.60637(15) 0.0458(6) Uani 1 1 d . . .
O4 O 0.09636(10) 0.60685(10) 0.53823(14) 0.0289(5) Uani 1 1 d . . .
O5 O 0.38316(9) 0.61684(9) 0.2500 0.0229(6) Uani 1 2 d S . .
H1W H 0.3524 0.6165 0.2066 0.028 Uiso 1 1 d R . .
N1 N 0.38726(11) 0.45434(11) 0.43215(16) 0.0233(5) Uani 1 1 d . . .
N2 N 0.28002(12) 0.54061(12) 0.35404(16) 0.0259(6) Uani 1 1 d . . .
F1 F 0.34591(12) 0.28514(9) 0.44093(18) 0.0680(8) Uani 1 1 d . . .
F2 F 0.13870(10) 0.51007(15) 0.21133(15) 0.0742(8) Uani 1 1 d . . .
C1 C 0.47890(13) 0.41719(14) 0.65825(18) 0.0212(6) Uani 1 1 d . . .
C2 C 0.43315(13) 0.40725(14) 0.57457(19) 0.0226(6) Uani 1 1 d . . .
C3 C 0.42250(13) 0.45878(14) 0.51288(19) 0.0237(6) Uani 1 1 d . . .
H3 H 0.4408 0.4989 0.5282 0.028 Uiso 1 1 calc R . .
C4 C 0.36210(16) 0.39586(15) 0.4095(2) 0.0332(7) Uani 1 1 d . . .
H4 H 0.3379 0.3912 0.3534 0.040 Uiso 1 1 calc R . .
C5 C 0.37162(17) 0.34324(15) 0.4678(2) 0.0381(8) Uani 1 1 d . . .
C6 C 0.40619(16) 0.34736(15) 0.5520(2) 0.0332(7) Uani 1 1 d . . .
H6 H 0.4113 0.3114 0.5920 0.040 Uiso 1 1 calc R . .
C7 C 0.15676(14) 0.59596(14) 0.5376(2) 0.0260(7) Uani 1 1 d . . .
C8 C 0.18478(14) 0.56946(14) 0.4447(2) 0.0265(7) Uani 1 1 d . . .
C9 C 0.25174(15) 0.56279(14) 0.4345(2) 0.0281(7) Uani 1 1 d . . .
H9 H 0.2783 0.5742 0.4860 0.034 Uiso 1 1 calc R . .
C10 C 0.24160(15) 0.52350(16) 0.2808(2) 0.0340(8) Uani 1 1 d . . .
H10 H 0.2602 0.5079 0.2244 0.041 Uiso 1 1 calc R . .
C11 C 0.17500(15) 0.52866(18) 0.2876(2) 0.0394(9) Uani 1 1 d . . .
C12 C 0.14487(15) 0.55162(17) 0.3692(2) 0.0363(8) Uani 1 1 d . . .
H12 H 0.0997 0.5550 0.3733 0.044 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
Ni1 O2 2.0429(19) 13 ?
Ni1 O1 2.075(2) 9_666 ?
Ni1 O4 2.0800(19) 15_666 ?
Ni1 N1 2.089(2) . ?
Ni1 O5 2.1001(15) . ?
Ni1 N2 2.109(2) . ?
O1 C1 1.247(3) . ?
O1 Ni1 2.075(2) 9_666 ?
O2 C1 1.265(3) . ?
O2 Ni1 2.0429(19) 13_556 ?
O3 C7 1.247(4) . ?
O4 C7 1.258(4) . ?
O4 Ni1 2.0801(19) 10_566 ?
O5 Ni1 2.1001(15) 5_665 ?
O5 H1W 0.8731 . ?
N1 C3 1.339(3) . ?
N1 C4 1.343(4) . ?
N2 C10 1.335(4) . ?
N2 C9 1.341(4) . ?
F1 C5 1.355(3) . ?
F2 C11 1.352(3) . ?
C1 C2 1.509(4) . ?
C2 C3 1.379(4) . ?
C2 C6 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.516(4) . ?
C8 C12 1.381(4) . ?
C8 C9 1.387(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(4) . ?
C12 H12 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
O2 Ni1 O1 95.54(7) 13 9_666 ?
O2 Ni1 O4 178.05(8) 13 15_666 ?
O1 Ni1 O4 82.53(8) 9_666 15_666 ?
O2 Ni1 N1 90.31(8) 13 . ?
O1 Ni1 N1 85.61(8) 9_666 . ?
O4 Ni1 N1 89.81(8) 15_666 . ?
O2 Ni1 O5 88.65(6) 13 . ?
O1 Ni1 O5 91.36(7) 9_666 . ?
O4 Ni1 O5 91.13(6) 15_666 . ?
N1 Ni1 O5 176.69(9) . . ?
O2 Ni1 N2 90.89(8) 13 . ?
O1 Ni1 N2 173.20(8) 9_666 . ?
O4 Ni1 N2 91.05(9) 15_666 . ?
N1 Ni1 N2 92.16(9) . . ?
O5 Ni1 N2 90.99(9) . . ?
C1 O1 Ni1 127.32(18) . 9_666 ?
C1 O2 Ni1 121.40(18) . 13_556 ?
C7 O4 Ni1 127.58(19) . 10_566 ?
Ni1 O5 Ni1 112.81(12) . 5_665 ?
Ni1 O5 H1W 114.4 . . ?
Ni1 O5 H1W 98.4 5_665 . ?
C3 N1 C4 117.7(2) . . ?
C3 N1 Ni1 118.10(19) . . ?
C4 N1 Ni1 123.89(19) . . ?
C10 N2 C9 118.2(3) . . ?
C10 N2 Ni1 121.24(19) . . ?
C9 N2 Ni1 120.6(2) . . ?
O1 C1 O2 127.3(2) . . ?
O1 C1 C2 115.6(2) . . ?
O2 C1 C2 117.1(2) . . ?
C3 C2 C6 118.4(3) . . ?
C3 C2 C1 118.4(2) . . ?
C6 C2 C1 123.0(3) . . ?
N1 C3 C2 123.8(3) . . ?
N1 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
N1 C4 C5 120.7(3) . . ?
N1 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
F1 C5 C4 118.4(3) . . ?
F1 C5 C6 119.4(3) . . ?
C4 C5 C6 122.2(3) . . ?
C5 C6 C2 117.1(3) . . ?
C5 C6 H6 121.4 . . ?
C2 C6 H6 121.4 . . ?
O3 C7 O4 126.3(3) . . ?
O3 C7 C8 117.4(3) . . ?
O4 C7 C8 116.3(3) . . ?
C12 C8 C9 118.9(3) . . ?
C12 C8 C7 121.3(3) . . ?
C9 C8 C7 119.8(3) . . ?
N2 C9 C8 123.1(3) . . ?
N2 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
N2 C10 C11 120.9(3) . . ?
N2 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
F2 C11 C10 118.1(3) . . ?
F2 C11 C12 119.9(3) . . ?
C10 C11 C12 122.0(3) . . ?
C11 C12 C8 116.9(3) . . ?
C11 C12 H12 121.5 . . ?
C8 C12 H12 121.5 . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 0.750 -0.008 270 31 ' '
2 0.750 0.250 -0.013 270 31 ' '
3 0.250 0.250 0.203 144 6 ' '
4 0.750 0.750 0.297 144 6 ' '
5 0.250 0.250 0.703 144 6 ' '
6 0.750 0.750 0.797 144 6 ' '

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Ni1 O5 Ni1 -62.67(5) 13 . . 5_665 ?
O1 Ni1 O5 Ni1 32.84(5) 9_666 . . 5_665 ?
O4 Ni1 O5 Ni1 115.39(6) 15_666 . . 5_665 ?
N1 Ni1 O5 Ni1 9.0(11) . . . 5_665 ?
N2 Ni1 O5 Ni1 -153.54(6) . . . 5_665 ?
O2 Ni1 N1 C3 148.1(2) 13 . . . ?
O1 Ni1 N1 C3 52.6(2) 9_666 . . . ?
O4 Ni1 N1 C3 -29.9(2) 15_666 . . . ?
O5 Ni1 N1 C3 76.5(12) . . . . ?
N2 Ni1 N1 C3 -121.0(2) . . . . ?
O2 Ni1 N1 C4 -25.6(2) 13 . . . ?
O1 Ni1 N1 C4 -121.1(2) 9_666 . . . ?
O4 Ni1 N1 C4 156.4(2) 15_666 . . . ?
O5 Ni1 N1 C4 -97.2(11) . . . . ?
N2 Ni1 N1 C4 65.3(3) . . . . ?
O2 Ni1 N2 C10 -16.9(2) 13 . . . ?
O1 Ni1 N2 C10 -178(25) 9_666 . . . ?
O4 Ni1 N2 C10 162.9(2) 15_666 . . . ?
N1 Ni1 N2 C10 -107.2(2) . . . . ?
O5 Ni1 N2 C10 71.8(2) . . . . ?
O2 Ni1 N2 C9 165.2(2) 13 . . . ?
O1 Ni1 N2 C9 4.1(9) 9_666 . . . ?
O4 Ni1 N2 C9 -15.0(2) 15_666 . . . ?
N1 Ni1 N2 C9 74.8(2) . . . . ?
O5 Ni1 N2 C9 -106.2(2) . . . . ?
Ni1 O1 C1 O2 54.4(4) 9_666 . . . ?
Ni1 O1 C1 C2 -122.7(2) 9_666 . . . ?
Ni1 O2 C1 O1 2.8(4) 13_556 . . . ?
Ni1 O2 C1 C2 179.92(18) 13_556 . . . ?
O1 C1 C2 C3 -18.0(4) . . . . ?
O2 C1 C2 C3 164.6(2) . . . . ?
O1 C1 C2 C6 155.9(3) . . . . ?
O2 C1 C2 C6 -21.5(4) . . . . ?
C4 N1 C3 C2 -1.4(4) . . . . ?
Ni1 N1 C3 C2 -175.5(2) . . . . ?
C6 C2 C3 N1 0.2(4) . . . . ?
C1 C2 C3 N1 174.4(2) . . . . ?
C3 N1 C4 C5 0.9(4) . . . . ?
Ni1 N1 C4 C5 174.6(2) . . . . ?
N1 C4 C5 F1 -179.1(3) . . . . ?
N1 C4 C5 C6 0.8(5) . . . . ?
F1 C5 C6 C2 178.0(3) . . . . ?
C4 C5 C6 C2 -1.9(5) . . . . ?
C3 C2 C6 C5 1.4(5) . . . . ?
C1 C2 C6 C5 -172.5(3) . . . . ?
Ni1 O4 C7 O3 -16.7(5) 10_566 . . . ?
Ni1 O4 C7 C8 161.29(19) 10_566 . . . ?
O3 C7 C8 C12 171.2(3) . . . . ?
O4 C7 C8 C12 -6.9(4) . . . . ?
O3 C7 C8 C9 -8.8(4) . . . . ?
O4 C7 C8 C9 173.1(3) . . . . ?
C10 N2 C9 C8 -0.8(4) . . . . ?
Ni1 N2 C9 C8 177.2(2) . . . . ?
C12 C8 C9 N2 1.0(5) . . . . ?
C7 C8 C9 N2 -179.0(3) . . . . ?
C9 N2 C10 C11 0.2(5) . . . . ?
Ni1 N2 C10 C11 -177.8(3) . . . . ?
N2 C10 C11 F2 -179.5(3) . . . . ?
N2 C10 C11 C12 0.2(6) . . . . ?
F2 C11 C12 C8 179.7(3) . . . . ?
C10 C11 C12 C8 0.0(5) . . . . ?
C9 C8 C12 C11 -0.6(5) . . . . ?
C7 C8 C12 C11 179.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.066
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_201_4cd
_database_code_depnum_ccdc_archive 'CCDC 1030272'
_audit_update_record             
;
2014-10-22 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Cd F2 N4 O6'
_chemical_formula_weight         608.82

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'
Cd Cd -0.8075 1.2024 '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           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   14.6749(10)
_cell_length_b                   8.0043(4)
_cell_length_c                   21.4102(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.405(7)
_cell_angle_gamma                90.00
_cell_volume                     2399.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7654
_exptl_absorpt_correction_T_max  0.7999
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9817
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_sigmaI/netI    0.0896
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         25.05
_reflns_number_total             4250
_reflns_number_gt                2886
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0530P)²+2.2008P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4250
_refine_ls_number_parameters     329
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1595
_refine_ls_wR_factor_gt          0.1333
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.072
_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
Cd1 Cd 0.20398(3) 1.02687(6) 0.48296(3) 0.0475(2) Uani 1 1 d . . .
O1 O 0.2044(3) 0.7352(6) 0.4807(3) 0.0603(14) Uani 1 1 d . . .
O2 O 0.1315(3) 0.8469(6) 0.5467(3) 0.0595(14) Uani 1 1 d . . .
O3 O 0.0675(4) 1.0737(8) 0.4029(3) 0.0865(19) Uani 1 1 d . . .
O4 O 0.1527(5) 0.9860(9) 0.3430(4) 0.101(2) Uani 1 1 d . . .
O5 O 0.1828(6) 0.6119(18) 0.3358(6) 0.249(7) Uani 1 1 d . . .
H1W H 0.1741 0.7165 0.3579 0.299 Uiso 1 1 d R . .
H2W H 0.2089 0.5632 0.3103 0.299 Uiso 1 1 d R . .
O6 O 0.2622(12) 0.4559(19) 0.2592(9) 0.319(9) Uiso 1 1 d D . .
H3W H 0.2879 0.4623 0.2285 0.383 Uiso 1 1 d R . .
H4W H 0.2517 0.5705 0.2326 0.383 Uiso 1 1 d RD . .
N1 N 0.1472(4) 0.2563(6) 0.5301(3) 0.0434(14) Uani 1 1 d . . .
N2 N -0.0790(8) 1.0310(13) 0.1745(5) 0.115(3) Uani 1 1 d . . .
N3 N 0.3408(5) 1.0184(8) 0.5798(3) 0.0602(18) Uani 1 1 d . . .
N4 N 0.3310(5) 1.1665(8) 0.4637(4) 0.0664(19) Uani 1 1 d . . .
F1 F 0.0045(3) 0.3430(6) 0.6356(3) 0.0845(15) Uani 1 1 d . . .
F2 F -0.2540(5) 1.1727(13) 0.2424(4) 0.187(4) Uani 1 1 d . . .
C1 C 0.1581(4) 0.7238(8) 0.5212(4) 0.0458(17) Uani 1 1 d . . .
C2 C 0.1337(4) 0.5516(7) 0.5392(3) 0.0408(16) Uani 1 1 d . . .
C3 C 0.1669(5) 0.4133(8) 0.5158(3) 0.0456(16) Uani 1 1 d . . .
H3 H 0.2051 0.4283 0.4885 0.055 Uiso 1 1 calc R . .
C4 C 0.0914(5) 0.2343(9) 0.5690(4) 0.0526(19) Uani 1 1 d . . .
H4 H 0.0749 0.1270 0.5784 0.063 Uiso 1 1 calc R . .
C5 C 0.0586(5) 0.3712(9) 0.5952(4) 0.0557(19) Uani 1 1 d . . .
C6 C 0.0783(5) 0.5300(8) 0.5804(4) 0.0476(18) Uani 1 1 d . . .
H6 H 0.0549 0.6214 0.5976 0.057 Uiso 1 1 calc R . .
C7 C 0.0774(6) 1.0364(11) 0.3494(5) 0.063(2) Uani 1 1 d . . .
C8 C -0.0103(6) 1.0549(9) 0.2910(4) 0.057(2) Uani 1 1 d . . .
C9 C -0.0066(8) 1.0206(13) 0.2300(5) 0.092(3) Uani 1 1 d . . .
H9 H 0.0521 0.9864 0.2262 0.110 Uiso 1 1 calc R . .
C10 C -0.1586(9) 1.0815(16) 0.1824(6) 0.107(4) Uani 1 1 d . . .
H10 H -0.2112 1.0914 0.1454 0.128 Uiso 1 1 calc R . .
C11 C -0.1705(6) 1.1212(14) 0.2412(6) 0.092(3) Uani 1 1 d . . .
C12 C -0.0955(6) 1.1046(10) 0.2974(4) 0.067(2) Uani 1 1 d . . .
H12 H -0.1027 1.1266 0.3383 0.081 Uiso 1 1 calc R . .
C13 C 0.3450(6) 0.9494(12) 0.6361(5) 0.080(3) Uani 1 1 d . . .
H13 H 0.2907 0.8976 0.6409 0.096 Uiso 1 1 calc R . .
C14 C 0.4282(9) 0.9510(15) 0.6891(6) 0.111(4) Uani 1 1 d . . .
H14 H 0.4281 0.9011 0.7283 0.133 Uiso 1 1 calc R . .
C15 C 0.5072(9) 1.0222(16) 0.6844(7) 0.122(5) Uani 1 1 d . . .
H15 H 0.5624 1.0223 0.7199 0.146 Uiso 1 1 calc R . .
C16 C 0.5064(6) 1.0980(12) 0.6251(6) 0.083(3) Uani 1 1 d . . .
C17 C 0.4180(5) 1.0925(11) 0.5731(5) 0.069(2) Uani 1 1 d . . .
C18 C 0.5884(9) 1.1739(17) 0.6148(9) 0.139(7) Uani 1 1 d . . .
H18 H 0.6460 1.1734 0.6483 0.167 Uiso 1 1 calc R . .
C19 C 0.5838(9) 1.2467(16) 0.5570(9) 0.137(7) Uani 1 1 d . . .
H19 H 0.6381 1.2976 0.5519 0.165 Uiso 1 1 calc R . .
C20 C 0.4978(7) 1.2475(12) 0.5035(7) 0.097(4) Uani 1 1 d . . .
C21 C 0.4147(6) 1.1703(10) 0.5124(5) 0.069(3) Uani 1 1 d . . .
C22 C 0.4871(10) 1.3234(14) 0.4431(9) 0.124(6) Uani 1 1 d . . .
H22 H 0.5389 1.3778 0.4358 0.149 Uiso 1 1 calc R . .
C23 C 0.4034(10) 1.3198(14) 0.3952(7) 0.127(5) Uani 1 1 d . . .
H23 H 0.3972 1.3694 0.3549 0.152 Uiso 1 1 calc R . .
C24 C 0.3262(7) 1.2400(12) 0.4075(6) 0.092(3) Uani 1 1 d . . .
H24 H 0.2683 1.2382 0.3744 0.110 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
Cd1 O3 2.243(5) . ?
Cd1 N4 2.313(7) . ?
Cd1 O1 2.335(5) . ?
Cd1 N1 2.364(5) 1_565 ?
Cd1 N3 2.417(6) . ?
Cd1 O2 2.437(5) . ?
O1 C1 1.254(8) . ?
O2 C1 1.245(8) . ?
O3 C7 1.234(10) . ?
O4 C7 1.221(11) . ?
O5 H1W 0.9889 . ?
O5 H2W 0.8496 . ?
O6 H3W 0.8509 . ?
O6 H4W 1.0665 . ?
N1 C4 1.344(9) . ?
N1 C3 1.345(8) . ?
N1 Cd1 2.364(5) 1_545 ?
N2 C10 1.294(14) . ?
N2 C9 1.338(12) . ?
N3 C13 1.310(11) . ?
N3 C17 1.324(10) . ?
N4 C24 1.322(11) . ?
N4 C21 1.354(10) . ?
F1 C5 1.356(8) . ?
F2 C11 1.300(10) . ?
C1 C2 1.503(9) . ?
C2 C3 1.364(9) . ?
C2 C6 1.378(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.509(11) . ?
C8 C9 1.353(12) . ?
C8 C12 1.357(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.360(15) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.397(12) . ?
C13 H13 0.9300 . ?
C14 C15 1.322(18) . ?
C14 H14 0.9300 . ?
C15 C16 1.405(17) . ?
C15 H15 0.9300 . ?
C16 C18 1.424(17) . ?
C16 C17 1.435(12) . ?
C17 C21 1.428(12) . ?
C18 C19 1.35(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.427(16) . ?
C19 H19 0.9300 . ?
C20 C22 1.395(17) . ?
C20 C21 1.430(12) . ?
C22 C23 1.344(17) . ?
C22 H22 0.9300 . ?
C23 C24 1.392(13) . ?
C23 H23 0.9300 . ?
C24 H24 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
O3 Cd1 N4 111.4(3) . . ?
O3 Cd1 O1 99.2(2) . . ?
N4 Cd1 O1 118.2(2) . . ?
O3 Cd1 N1 81.3(2) . 1_565 ?
N4 Cd1 N1 96.1(2) . 1_565 ?
O1 Cd1 N1 142.09(19) . 1_565 ?
O3 Cd1 N3 169.2(2) . . ?
N4 Cd1 N3 70.1(3) . . ?
O1 Cd1 N3 89.01(19) . . ?
N1 Cd1 N3 88.0(2) 1_565 . ?
O3 Cd1 O2 95.0(2) . . ?
N4 Cd1 O2 153.6(2) . . ?
O1 Cd1 O2 54.89(17) . . ?
N1 Cd1 O2 87.22(18) 1_565 . ?
N3 Cd1 O2 83.9(2) . . ?
C1 O1 Cd1 93.0(4) . . ?
C1 O2 Cd1 88.6(4) . . ?
C7 O3 Cd1 110.0(6) . . ?
H1W O5 H2W 147.6 . . ?
H3W O6 H4W 64.0 . . ?
C4 N1 C3 118.4(6) . . ?
C4 N1 Cd1 121.4(4) . 1_545 ?
C3 N1 Cd1 120.1(5) . 1_545 ?
C10 N2 C9 114.3(11) . . ?
C13 N3 C17 118.9(8) . . ?
C13 N3 Cd1 126.8(6) . . ?
C17 N3 Cd1 114.4(6) . . ?
C24 N4 C21 118.6(8) . . ?
C24 N4 Cd1 123.5(6) . . ?
C21 N4 Cd1 117.9(6) . . ?
O2 C1 O1 123.5(6) . . ?
O2 C1 C2 118.9(7) . . ?
O1 C1 C2 117.6(7) . . ?
C3 C2 C6 118.5(6) . . ?
C3 C2 C1 120.8(7) . . ?
C6 C2 C1 120.7(6) . . ?
N1 C3 C2 123.4(7) . . ?
N1 C3 H3 118.3 . . ?
C2 C3 H3 118.3 . . ?
N1 C4 C5 119.9(6) . . ?
N1 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
F1 C5 C6 120.6(7) . . ?
F1 C5 C4 117.9(7) . . ?
C6 C5 C4 121.5(7) . . ?
C5 C6 C2 118.2(7) . . ?
C5 C6 H6 120.9 . . ?
C2 C6 H6 120.9 . . ?
O4 C7 O3 123.1(9) . . ?
O4 C7 C8 121.0(9) . . ?
O3 C7 C8 115.9(8) . . ?
C9 C8 C12 117.4(8) . . ?
C9 C8 C7 120.6(8) . . ?
C12 C8 C7 121.9(8) . . ?
N2 C9 C8 126.4(10) . . ?
N2 C9 H9 116.8 . . ?
C8 C9 H9 116.8 . . ?
N2 C10 C11 124.4(10) . . ?
N2 C10 H10 117.8 . . ?
C11 C10 H10 117.8 . . ?
F2 C11 C10 118.3(11) . . ?
F2 C11 C12 121.9(11) . . ?
C10 C11 C12 119.8(9) . . ?
C8 C12 C11 117.6(9) . . ?
C8 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
N3 C13 C14 122.2(10) . . ?
N3 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C15 C14 C13 121.0(13) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 118.9(11) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C15 C16 C18 123.0(12) . . ?
C15 C16 C17 116.8(9) . . ?
C18 C16 C17 120.2(12) . . ?
N3 C17 C21 119.8(7) . . ?
N3 C17 C16 122.2(10) . . ?
C21 C17 C16 118.0(9) . . ?
C19 C18 C16 120.8(14) . . ?
C19 C18 H18 119.6 . . ?
C16 C18 H18 119.6 . . ?
C18 C19 C20 121.8(14) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C22 C20 C19 125.0(12) . . ?
C22 C20 C21 116.6(11) . . ?
C19 C20 C21 118.4(13) . . ?
N4 C21 C17 117.8(7) . . ?
N4 C21 C20 121.4(11) . . ?
C17 C21 C20 120.8(10) . . ?
C23 C22 C20 121.4(11) . . ?
C23 C22 H22 119.3 . . ?
C20 C22 H22 119.3 . . ?
C22 C23 C24 118.4(13) . . ?
C22 C23 H23 120.8 . . ?
C24 C23 H23 120.8 . . ?
N4 C24 C23 123.5(12) . . ?
N4 C24 H24 118.3 . . ?
C23 C24 H24 118.3 . . ?

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
O3 Cd1 O1 C1 -89.2(4) . . . . ?
N4 Cd1 O1 C1 150.4(4) . . . . ?
N1 Cd1 O1 C1 -1.7(5) 1_565 . . . ?
N3 Cd1 O1 C1 83.7(4) . . . . ?
O2 Cd1 O1 C1 0.5(4) . . . . ?
O3 Cd1 O2 C1 97.2(4) . . . . ?
N4 Cd1 O2 C1 -83.7(6) . . . . ?
O1 Cd1 O2 C1 -0.5(4) . . . . ?
N1 Cd1 O2 C1 178.2(4) 1_565 . . . ?
N3 Cd1 O2 C1 -93.6(4) . . . . ?
N4 Cd1 O3 C7 55.2(7) . . . . ?
O1 Cd1 O3 C7 -70.0(6) . . . . ?
N1 Cd1 O3 C7 148.4(6) 1_565 . . . ?
N3 Cd1 O3 C7 151.3(11) . . . . ?
O2 Cd1 O3 C7 -125.2(6) . . . . ?
O3 Cd1 N3 C13 78.6(15) . . . . ?
N4 Cd1 N3 C13 178.8(8) . . . . ?
O1 Cd1 N3 C13 -60.7(8) . . . . ?
N1 Cd1 N3 C13 81.5(8) 1_565 . . . ?
O2 Cd1 N3 C13 -5.9(7) . . . . ?
O3 Cd1 N3 C17 -101.5(14) . . . . ?
N4 Cd1 N3 C17 -1.3(5) . . . . ?
O1 Cd1 N3 C17 119.2(6) . . . . ?
N1 Cd1 N3 C17 -98.6(6) 1_565 . . . ?
O2 Cd1 N3 C17 174.0(6) . . . . ?
O3 Cd1 N4 C24 -10.8(8) . . . . ?
O1 Cd1 N4 C24 103.0(7) . . . . ?
N1 Cd1 N4 C24 -93.8(7) 1_565 . . . ?
N3 Cd1 N4 C24 -179.4(8) . . . . ?
O2 Cd1 N4 C24 170.2(6) . . . . ?
O3 Cd1 N4 C21 170.3(5) . . . . ?
O1 Cd1 N4 C21 -75.9(6) . . . . ?
N1 Cd1 N4 C21 87.3(5) 1_565 . . . ?
N3 Cd1 N4 C21 1.7(5) . . . . ?
O2 Cd1 N4 C21 -8.7(8) . . . . ?
Cd1 O2 C1 O1 0.9(7) . . . . ?
Cd1 O2 C1 C2 -179.0(5) . . . . ?
Cd1 O1 C1 O2 -0.9(7) . . . . ?
Cd1 O1 C1 C2 179.0(5) . . . . ?
O2 C1 C2 C3 -175.6(6) . . . . ?
O1 C1 C2 C3 4.5(9) . . . . ?
O2 C1 C2 C6 3.7(10) . . . . ?
O1 C1 C2 C6 -176.2(6) . . . . ?
C4 N1 C3 C2 0.5(10) . . . . ?
Cd1 N1 C3 C2 177.6(5) 1_545 . . . ?
C6 C2 C3 N1 0.9(10) . . . . ?
C1 C2 C3 N1 -179.8(6) . . . . ?
C3 N1 C4 C5 -2.3(10) . . . . ?
Cd1 N1 C4 C5 -179.3(5) 1_545 . . . ?
N1 C4 C5 F1 -178.3(6) . . . . ?
N1 C4 C5 C6 2.7(11) . . . . ?
F1 C5 C6 C2 179.9(6) . . . . ?
C4 C5 C6 C2 -1.2(11) . . . . ?
C3 C2 C6 C5 -0.6(10) . . . . ?
C1 C2 C6 C5 -179.9(6) . . . . ?
Cd1 O3 C7 O4 -1.8(11) . . . . ?
Cd1 O3 C7 C8 177.6(5) . . . . ?
O4 C7 C8 C9 -2.0(13) . . . . ?
O3 C7 C8 C9 178.6(9) . . . . ?
O4 C7 C8 C12 177.5(8) . . . . ?
O3 C7 C8 C12 -1.9(12) . . . . ?
C10 N2 C9 C8 1.0(18) . . . . ?
C12 C8 C9 N2 0.1(16) . . . . ?
C7 C8 C9 N2 179.6(10) . . . . ?
C9 N2 C10 C11 0(2) . . . . ?
N2 C10 C11 F2 179.1(12) . . . . ?
N2 C10 C11 C12 -2(2) . . . . ?
C9 C8 C12 C11 -1.9(13) . . . . ?
C7 C8 C12 C11 178.6(8) . . . . ?
F2 C11 C12 C8 -178.0(10) . . . . ?
C10 C11 C12 C8 2.7(16) . . . . ?
C17 N3 C13 C14 -0.2(14) . . . . ?
Cd1 N3 C13 C14 179.7(7) . . . . ?
N3 C13 C14 C15 -0.4(17) . . . . ?
C13 C14 C15 C16 0.3(18) . . . . ?
C14 C15 C16 C18 -178.3(11) . . . . ?
C14 C15 C16 C17 0.2(17) . . . . ?
C13 N3 C17 C21 -179.3(8) . . . . ?
Cd1 N3 C17 C21 0.8(10) . . . . ?
C13 N3 C17 C16 0.8(12) . . . . ?
Cd1 N3 C17 C16 -179.1(6) . . . . ?
C15 C16 C17 N3 -0.8(14) . . . . ?
C18 C16 C17 N3 177.8(9) . . . . ?
C15 C16 C17 C21 179.3(9) . . . . ?
C18 C16 C17 C21 -2.2(13) . . . . ?
C15 C16 C18 C19 -179.3(13) . . . . ?
C17 C16 C18 C19 2(2) . . . . ?
C16 C18 C19 C20 -1(2) . . . . ?
C18 C19 C20 C22 178.4(13) . . . . ?
C18 C19 C20 C21 0.7(19) . . . . ?
C24 N4 C21 C17 179.0(8) . . . . ?
Cd1 N4 C21 C17 -2.0(9) . . . . ?
C24 N4 C21 C20 -1.7(12) . . . . ?
Cd1 N4 C21 C20 177.2(6) . . . . ?
N3 C17 C21 N4 0.8(11) . . . . ?
C16 C17 C21 N4 -179.3(7) . . . . ?
N3 C17 C21 C20 -178.5(7) . . . . ?
C16 C17 C21 C20 1.5(12) . . . . ?
C22 C20 C21 N4 2.2(13) . . . . ?
C19 C20 C21 N4 -179.9(8) . . . . ?
C22 C20 C21 C17 -178.6(8) . . . . ?
C19 C20 C21 C17 -0.7(13) . . . . ?
C19 C20 C22 C23 -179.5(11) . . . . ?
C21 C20 C22 C23 -1.8(16) . . . . ?
C20 C22 C23 C24 0.9(18) . . . . ?
C21 N4 C24 C23 0.8(14) . . . . ?
Cd1 N4 C24 C23 -178.1(8) . . . . ?
C22 C23 C24 N4 -0.4(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H3W O4 0.85 1.98 2.84(2) 178.0 2_545
O5 H2W O6 0.85 1.75 2.60(2) 177.8 .
O5 H1W O4 0.99 2.19 3.038(15) 142.9 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.108
