# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 1835306'
_audit_update_record             
;
2018-04-06 deposited with the CCDC.
2018-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H15 F4 N5 O4 Zn'
_chemical_formula_weight         602.80

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8391(8)
_cell_length_b                   11.1144(9)
_cell_length_c                   11.6293(9)
_cell_angle_alpha                116.6100(10)
_cell_angle_beta                 91.5160(10)
_cell_angle_gamma                103.2240(10)
_cell_volume                     1205.92(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5489
_cell_measurement_theta_min      1.952
_cell_measurement_theta_max      27.559

_exptl_crystal_description       bulk
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      1.660
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    1.095
_shelx_estimated_absorpt_T_min   0.761
_shelx_estimated_absorpt_T_max   0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_T_max  0.812
_exptl_absorpt_process_details   SADABS;Bruck,2000
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11076
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.952
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             5576
_reflns_number_gt                4754
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+0.5205P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5576
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0833
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5171(2) 0.3912(2) 0.5745(2) 0.0278(5) Uani 1 1 d . . . . .
H1 H 0.4666 0.4474 0.6230 0.033 Uiso 1 1 calc R U . . .
C2 C 0.4780(2) 0.2510(2) 0.5025(2) 0.0283(5) Uani 1 1 d . . . . .
H2 H 0.3969 0.1934 0.4921 0.034 Uiso 1 1 calc R U . . .
C3 C 0.67939(19) 0.3259(2) 0.4865(2) 0.0213(4) Uani 1 1 d . . . . .
H3 H 0.7603 0.3269 0.4617 0.026 Uiso 1 1 calc R U . . .
C4 C 0.58533(19) 0.0693(2) 0.36167(19) 0.0201(4) Uani 1 1 d . . . . .
C5 C 0.47568(19) -0.0277(2) 0.2787(2) 0.0233(4) Uani 1 1 d . . . . .
H5 H 0.3989 -0.0035 0.2803 0.028 Uiso 1 1 calc R U . . .
C6 C 0.48218(19) -0.1619(2) 0.1929(2) 0.0232(4) Uani 1 1 d . . . . .
H6 H 0.4087 -0.2273 0.1377 0.028 Uiso 1 1 calc R U . . .
C7 C 0.59642(19) -0.1998(2) 0.18838(19) 0.0196(4) Uani 1 1 d . . . . .
C8 C 0.7046(2) -0.1008(2) 0.2733(2) 0.0274(5) Uani 1 1 d . . . . .
H8 H 0.7817 -0.1246 0.2722 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6991(2) 0.0324(2) 0.3594(2) 0.0272(5) Uani 1 1 d . . . . .
H9 H 0.7721 0.0973 0.4159 0.033 Uiso 1 1 calc R U . . .
C10 C 0.68988(18) -0.4019(2) 0.10088(19) 0.0191(4) Uani 1 1 d . . . . .
C11 C 0.73654(19) -0.4834(2) -0.0111(2) 0.0214(4) Uani 1 1 d . . . . .
H11 H 0.7097 -0.4882 -0.0901 0.026 Uiso 1 1 calc R U . . .
C12 C 0.82245(18) -0.5572(2) -0.00591(19) 0.0208(4) Uani 1 1 d . . . . .
H12 H 0.8535 -0.6104 -0.0806 0.025 Uiso 1 1 calc R U . . .
C13 C 0.86128(18) -0.5506(2) 0.11168(19) 0.0191(4) Uani 1 1 d . . . . .
C14 C 0.81315(19) -0.4733(2) 0.22295(19) 0.0209(4) Uani 1 1 d . . . . .
H14 H 0.8366 -0.4728 0.3007 0.025 Uiso 1 1 calc R U . . .
C15 C 0.73061(19) -0.3974(2) 0.21818(19) 0.0209(4) Uani 1 1 d . . . . .
H15 H 0.7017 -0.3427 0.2938 0.025 Uiso 1 1 calc R U . . .
C16 C 0.9732(2) -0.7437(2) 0.0293(2) 0.0250(4) Uani 1 1 d . . . . .
H16 H 0.9288 -0.7986 -0.0547 0.030 Uiso 1 1 calc R U . . .
C17 C 1.0702(2) -0.7683(2) 0.0839(2) 0.0252(4) Uani 1 1 d . . . . .
H17 H 1.1041 -0.8443 0.0433 0.030 Uiso 1 1 calc R U . . .
C18 C 1.03827(19) -0.5762(2) 0.2295(2) 0.0221(4) Uani 1 1 d . . . . .
H18 H 1.0451 -0.4952 0.3068 0.027 Uiso 1 1 calc R U . . .
C19 C 0.93402(19) 0.7451(2) 0.53118(18) 0.0195(4) Uani 1 1 d . . . . .
C20 C 0.96766(18) 0.8765(2) 0.51462(19) 0.0189(4) Uani 1 1 d . . . . .
C21 C 1.03610(18) 0.8844(2) 0.41711(19) 0.0207(4) Uani 1 1 d . . . . .
C22 C 0.93304(18) 0.9956(2) 0.59634(19) 0.0209(4) Uani 1 1 d . . . . .
C23 C 0.58973(19) 0.7587(2) 0.83217(19) 0.0220(4) Uani 1 1 d . . . . .
C24 C 0.54285(19) 0.8830(2) 0.91915(19) 0.0202(4) Uani 1 1 d . . . . .
C25 C 0.62650(19) 1.0047(2) 1.0136(2) 0.0222(4) Uani 1 1 d . . . . .
C26 C 0.58538(19) 1.1190(2) 1.09260(19) 0.0216(4) Uani 1 1 d . . . . .
F1 F 0.86911(13) 0.99854(13) 0.69536(12) 0.0312(3) Uani 1 1 d . . . . .
F2 F 0.67065(12) 1.23268(13) 1.18563(12) 0.0303(3) Uani 1 1 d . . . . .
F3 F 0.75204(11) 1.01101(14) 1.03091(13) 0.0321(3) Uani 1 1 d . . . . .
F4 F 1.07320(12) 0.77320(13) 0.33294(12) 0.0293(3) Uani 1 1 d . . . . .
H3A H 0.570(2) -0.352(3) 0.025(2) 0.021(6) Uiso 1 1 d . . . . .
N1 N 0.64450(16) 0.43833(18) 0.56495(16) 0.0205(4) Uani 1 1 d . . . . .
N2 N 0.58174(16) 0.20962(17) 0.44729(16) 0.0202(3) Uani 1 1 d . . . . .
N3 N 0.59942(17) -0.33333(19) 0.09392(18) 0.0227(4) Uani 1 1 d . . . . .
N4 N 0.95308(16) -0.62128(18) 0.12242(16) 0.0199(3) Uani 1 1 d . . . . .
N5 N 1.11053(16) -0.66231(18) 0.20984(16) 0.0215(4) Uani 1 1 d . . . . .
O1 O 0.81580(13) 0.70823(15) 0.54164(13) 0.0221(3) Uani 1 1 d . . . . .
O2 O 1.01734(14) 0.68768(16) 0.53176(15) 0.0285(3) Uani 1 1 d . . . . .
O3 O 0.66285(15) 0.78095(16) 0.75568(15) 0.0272(3) Uani 1 1 d . . . . .
O4 O 0.55731(16) 0.65065(16) 0.84126(15) 0.0305(4) Uani 1 1 d . . . . .
Zn1 Zn 0.74863(2) 0.63634(2) 0.65928(2) 0.01739(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.349(3) . ?
C1 N1 1.387(3) . ?
C1 H1 0.9300 . ?
C2 N2 1.377(3) . ?
C2 H2 0.9300 . ?
C3 N1 1.323(3) . ?
C3 N2 1.349(3) . ?
C3 H3 0.9300 . ?
C4 C9 1.383(3) . ?
C4 C5 1.388(3) . ?
C4 N2 1.437(3) . ?
C5 C6 1.393(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.391(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.392(3) . ?
C7 N3 1.405(3) . ?
C8 C9 1.383(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 N3 1.393(3) . ?
C10 C15 1.398(3) . ?
C10 C11 1.400(3) . ?
C11 C12 1.391(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(3) . ?
C13 N4 1.436(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.356(3) . ?
C16 N4 1.378(3) . ?
C16 H16 0.9300 . ?
C17 N5 1.381(3) . ?
C17 H17 0.9300 . ?
C18 N5 1.318(3) . ?
C18 N4 1.350(3) . ?
C18 H18 0.9300 . ?
C19 O2 1.221(3) . ?
C19 O1 1.280(2) . ?
C19 C20 1.521(3) . ?
C20 C22 1.384(3) . ?
C20 C21 1.396(3) . ?
C21 F4 1.346(2) . ?
C21 C22 1.379(3) 2_776 ?
C22 F1 1.351(2) . ?
C22 C21 1.379(3) 2_776 ?
C23 O4 1.225(3) . ?
C23 O3 1.275(2) . ?
C23 C24 1.512(3) . ?
C24 C25 1.383(3) . ?
C24 C26 1.387(3) 2_677 ?
C25 F3 1.351(2) . ?
C25 C26 1.375(3) . ?
C26 F2 1.345(2) . ?
C26 C24 1.387(3) 2_677 ?
N1 Zn1 1.9889(17) . ?
N3 H3A 0.77(2) . ?
N5 Zn1 2.0030(17) 2_756 ?
O1 Zn1 1.9509(14) . ?
O3 Zn1 1.9568(15) . ?
Zn1 N5 2.0030(17) 2_756 ?

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
C2 C1 N1 109.24(19) . . ?
C2 C1 H1 125.4 . . ?
N1 C1 H1 125.4 . . ?
C1 C2 N2 106.61(18) . . ?
C1 C2 H2 126.7 . . ?
N2 C2 H2 126.7 . . ?
N1 C3 N2 110.88(18) . . ?
N1 C3 H3 124.6 . . ?
N2 C3 H3 124.6 . . ?
C9 C4 C5 120.14(19) . . ?
C9 C4 N2 119.85(18) . . ?
C5 C4 N2 119.98(18) . . ?
C4 C5 C6 119.16(19) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 121.28(18) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 118.36(19) . . ?
C6 C7 N3 118.78(18) . . ?
C8 C7 N3 122.77(19) . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C4 120.20(19) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?
N3 C10 C15 120.84(19) . . ?
N3 C10 C11 120.59(19) . . ?
C15 C10 C11 118.47(19) . . ?
C12 C11 C10 120.91(19) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 119.34(19) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.45(19) . . ?
C12 C13 N4 121.22(18) . . ?
C14 C13 N4 118.32(18) . . ?
C15 C14 C13 120.03(19) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.74(19) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C17 C16 N4 106.64(18) . . ?
C17 C16 H16 126.7 . . ?
N4 C16 H16 126.7 . . ?
C16 C17 N5 108.93(19) . . ?
C16 C17 H17 125.5 . . ?
N5 C17 H17 125.5 . . ?
N5 C18 N4 110.96(18) . . ?
N5 C18 H18 124.5 . . ?
N4 C18 H18 124.5 . . ?
O2 C19 O1 128.10(19) . . ?
O2 C19 C20 119.24(17) . . ?
O1 C19 C20 112.65(17) . . ?
C22 C20 C21 116.17(18) . . ?
C22 C20 C19 121.80(17) . . ?
C21 C20 C19 122.02(18) . . ?
F4 C21 C22 118.31(17) . 2_776 ?
F4 C21 C20 120.16(18) . . ?
C22 C21 C20 121.53(19) 2_776 . ?
F1 C22 C21 117.42(18) . 2_776 ?
F1 C22 C20 120.26(18) . . ?
C21 C22 C20 122.30(18) 2_776 . ?
O4 C23 O3 126.7(2) . . ?
O4 C23 C24 119.51(18) . . ?
O3 C23 C24 113.80(18) . . ?
C25 C24 C26 116.88(18) . 2_677 ?
C25 C24 C23 121.34(18) . . ?
C26 C24 C23 121.78(18) 2_677 . ?
F3 C25 C26 118.78(18) . . ?
F3 C25 C24 119.24(18) . . ?
C26 C25 C24 121.97(19) . . ?
F2 C26 C25 119.19(18) . . ?
F2 C26 C24 119.62(18) . 2_677 ?
C25 C26 C24 121.15(18) . 2_677 ?
C3 N1 C1 105.98(17) . . ?
C3 N1 Zn1 129.18(14) . . ?
C1 N1 Zn1 124.80(14) . . ?
C3 N2 C2 107.28(17) . . ?
C3 N2 C4 126.05(18) . . ?
C2 N2 C4 126.67(17) . . ?
C10 N3 C7 124.90(18) . . ?
C10 N3 H3A 115.8(18) . . ?
C7 N3 H3A 113.6(19) . . ?
C18 N4 C16 107.05(17) . . ?
C18 N4 C13 124.82(17) . . ?
C16 N4 C13 128.12(17) . . ?
C18 N5 C17 106.41(17) . . ?
C18 N5 Zn1 124.99(14) . 2_756 ?
C17 N5 Zn1 128.59(15) . 2_756 ?
C19 O1 Zn1 126.02(13) . . ?
C23 O3 Zn1 116.29(14) . . ?
O1 Zn1 O3 97.46(6) . . ?
O1 Zn1 N1 112.46(6) . . ?
O3 Zn1 N1 118.71(7) . . ?
O1 Zn1 N5 111.14(6) . 2_756 ?
O3 Zn1 N5 104.75(7) . 2_756 ?
N1 Zn1 N5 111.39(7) . 2_756 ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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 1835307'
_audit_update_record             
;
2018-04-06 deposited with the CCDC.
2018-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H24 Cd F4 N6 O6'
_chemical_formula_weight         740.94

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'
F F 0.0171 0.0103 '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'

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

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

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

_cell_length_a                   17.7736(18)
_cell_length_b                   17.8696(18)
_cell_length_c                   18.3763(19)
_cell_angle_alpha                90
_cell_angle_beta                 98.7620(10)
_cell_angle_gamma                90
_cell_volume                     5768.3(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7520
_cell_measurement_theta_min      1.626
_cell_measurement_theta_max      28.247

_exptl_crystal_description       bulk
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      1.706
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_F_000             2976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    0.839
_shelx_estimated_absorpt_T_min   0.797
_shelx_estimated_absorpt_T_max   0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.797
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_process_details   SADABS;Bruck,2000
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26942
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.626
_diffrn_reflns_theta_max         28.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7143
_reflns_number_gt                5913
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0317P)²+19.3362P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7143
_refine_ls_number_parameters     427
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6083(2) 0.90441(19) 0.1762(2) 0.0407(9) Uani 1 1 d . . . . .
H1 H 0.6131 0.8871 0.1294 0.049 Uiso 1 1 calc R U . . .
C2 C 0.59735(19) 0.90647(17) 0.28938(18) 0.0268(7) Uani 1 1 d . . . . .
H2 H 0.5921 0.8912 0.3367 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6059(3) 0.9773(2) 0.1955(2) 0.0460(10) Uani 1 1 d . . . . .
H3 H 0.6077 1.0185 0.1649 0.055 Uiso 1 1 calc R U . . .
C4 C 0.59424(17) 1.04354(17) 0.31306(17) 0.0224(6) Uani 1 1 d . . . . .
C5 C 0.5752(2) 1.03796(19) 0.3831(2) 0.0379(9) Uani 1 1 d . . . . .
H5 H 0.5675 0.9911 0.4028 0.046 Uiso 1 1 calc R U . . .
C6 C 0.5676(2) 1.10195(19) 0.42409(19) 0.0343(8) Uani 1 1 d . . . . .
H6 H 0.5550 1.0974 0.4712 0.041 Uiso 1 1 calc R U . . .
C7 C 0.57829(17) 1.17228(16) 0.39619(17) 0.0231(6) Uani 1 1 d . . . . .
C8 C 0.60054(19) 1.17683(18) 0.32716(18) 0.0279(7) Uani 1 1 d . . . . .
H8 H 0.6107 1.2235 0.3085 0.033 Uiso 1 1 calc R U . . .
C9 C 0.60802(18) 1.11355(18) 0.28525(18) 0.0266(7) Uani 1 1 d . . . . .
H9 H 0.6222 1.1180 0.2388 0.032 Uiso 1 1 calc R U . . .
C10 C 0.53058(18) 1.30004(17) 0.40497(16) 0.0223(6) Uani 1 1 d . . . . .
C11 C 0.47790(19) 1.29485(17) 0.34099(17) 0.0268(7) Uani 1 1 d . . . . .
H11 H 0.4676 1.2484 0.3189 0.032 Uiso 1 1 calc R U . . .
C12 C 0.54138(19) 1.36987(18) 0.43905(18) 0.0290(7) Uani 1 1 d . . . . .
H12 H 0.5754 1.3745 0.4826 0.035 Uiso 1 1 calc R U . . .
C13 C 0.56002(17) 0.56123(16) 0.18954(17) 0.0220(6) Uani 1 1 d . . . . .
H13 H 0.5134 0.5766 0.1640 0.026 Uiso 1 1 calc R U . . .
C14 C 0.67015(19) 0.56164(18) 0.2559(2) 0.0344(8) Uani 1 1 d . . . . .
H14 H 0.7143 0.5783 0.2852 0.041 Uiso 1 1 calc R U . . .
C15 C 0.65688(19) 0.49052(19) 0.2338(2) 0.0352(8) Uani 1 1 d . . . . .
H15 H 0.6889 0.4497 0.2451 0.042 Uiso 1 1 calc R U . . .
C17 C 0.54683(17) 0.42599(16) 0.15687(17) 0.0226(6) Uani 1 1 d . . . . .
C18 C 0.55935(19) 0.35763(18) 0.19025(18) 0.0274(7) Uani 1 1 d . . . . .
H18 H 0.5930 0.3534 0.2341 0.033 Uiso 1 1 calc R U . . .
C19 C 0.49770(19) 0.43221(18) 0.09088(18) 0.0294(7) Uani 1 1 d . . . . .
H19 H 0.4911 0.4781 0.0669 0.035 Uiso 1 1 calc R U . . .
C20 C 0.48940(15) 0.73941(16) 0.10971(15) 0.0177(5) Uani 1 1 d . . . . .
C21 C 0.42302(15) 0.74269(16) 0.04700(15) 0.0162(5) Uani 1 1 d . . . . .
C22 C 0.40513(17) 0.80831(17) 0.00936(17) 0.0230(6) Uani 1 1 d . . . . .
C23 C 0.38335(16) 0.68008(17) 0.02055(16) 0.0206(6) Uani 1 1 d . . . . .
C24 C 0.7624(2) 0.7498(3) 0.34440(18) 0.0463(12) Uani 1 1 d D . . . .
C25 C 0.81362(17) 0.7518(2) 0.41878(17) 0.0273(7) Uani 1 1 d D . . . .
C26 C 0.83001(17) 0.81743(19) 0.45726(17) 0.0271(7) Uani 1 1 d . . . . .
C27 C 0.85204(18) 0.68847(19) 0.44686(18) 0.0278(7) Uani 1 1 d . . . . .
C28 C 0.7915(2) 0.9379(2) -0.0730(2) 0.0434(9) Uani 1 1 d . . . . .
H28A H 0.8011 0.8932 -0.0991 0.065 Uiso 1 1 calc R U . . .
H28B H 0.8378 0.9660 -0.0616 0.065 Uiso 1 1 calc R U . . .
H28C H 0.7540 0.9676 -0.1032 0.065 Uiso 1 1 calc R U . . .
C29 C 0.7491(4) 0.9790(3) 0.0421(3) 0.0764(18) Uani 1 1 d . . . . .
H29A H 0.7374 0.9591 0.0876 0.115 Uiso 1 1 calc R U . . .
H29B H 0.7068 1.0080 0.0186 0.115 Uiso 1 1 calc R U . . .
H29C H 0.7934 1.0104 0.0518 0.115 Uiso 1 1 calc R U . . .
C30 C 0.7456(2) 0.8489(2) 0.0060(2) 0.0468(10) Uani 1 1 d . . . . .
H30 H 0.7561 0.8125 -0.0273 0.056 Uiso 1 1 calc R U . . .
Cd1 Cd 0.60707(2) 0.73311(2) 0.23587(2) 0.01532(6) Uani 1 1 d . . . . .
F1 F 0.44124(13) 0.87221(11) 0.03387(12) 0.0399(5) Uani 1 1 d . . . . .
F2 F 0.39866(12) 0.61376(10) 0.05441(11) 0.0353(5) Uani 1 1 d . . . . .
F3 F 0.79424(13) 0.88080(13) 0.43298(12) 0.0500(6) Uani 1 1 d . . . . .
F4 F 0.83943(14) 0.62281(13) 0.41080(13) 0.0509(6) Uani 1 1 d . . . . .
N1 N 0.60271(14) 0.86017(15) 0.23506(14) 0.0231(5) Uani 1 1 d . . . . .
N2 N 0.60025(15) 0.97848(14) 0.26905(14) 0.0233(5) Uani 1 1 d . . . . .
N3 N 0.56916(16) 1.23766(14) 0.43687(14) 0.0256(6) Uani 1 1 d . . . . .
H3A H 0.5880 1.2390 0.4828 0.031 Uiso 1 1 calc R U . . .
N4 N 0.60928(14) 0.60630(14) 0.22929(14) 0.0220(5) Uani 1 1 d . . . . .
N5 N 0.58602(14) 0.49035(14) 0.19077(14) 0.0229(5) Uani 1 1 d . . . . .
N6 N 0.76377(18) 0.91812(17) -0.00578(18) 0.0382(7) Uani 1 1 d . . . . .
O1 O 0.55321(12) 0.75024(15) 0.09314(12) 0.0338(6) Uani 1 1 d . . . . .
O2 O 0.47704(11) 0.72571(12) 0.17347(11) 0.0222(4) Uani 1 1 d . . . . .
O3 O 0.69710(12) 0.73503(15) 0.34142(12) 0.0322(5) Uani 1 1 d . . . . .
O4 O 0.8005(3) 0.7271(7) 0.2942(3) 0.067(4) Uani 0.518(11) 1 d . U P A 1
O5 O 0.7153(2) 0.82895(19) 0.0590(2) 0.0707(10) Uani 1 1 d . . . . .
O4' O 0.7837(4) 0.8004(6) 0.2949(3) 0.055(3) Uani 0.482(11) 1 d . . P A 2
O1W O 0.70997(12) 0.73084(14) 0.17108(12) 0.0303(5) Uani 1 1 d . . . . .
H1WA H 0.7111 0.7608 0.1353 0.045 Uiso 1 1 d R U . . .
H1WB H 0.7326 0.7515 0.2100 0.045 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.352(5) . ?
C1 N1 1.355(4) . ?
C2 N1 1.311(4) . ?
C2 N2 1.343(4) . ?
C3 N2 1.371(4) . ?
C4 C5 1.383(5) . ?
C4 C9 1.387(4) . ?
C4 N2 1.429(4) . ?
C5 C6 1.388(5) . ?
C6 C7 1.381(4) . ?
C7 C8 1.387(4) . ?
C7 N3 1.410(4) . ?
C8 C9 1.386(4) . ?
C10 C11 1.390(4) . ?
C10 N3 1.391(4) . ?
C10 C12 1.396(4) . ?
C11 C18 1.382(4) 2_665 ?
C12 C19 1.382(4) 2_665 ?
C13 N4 1.324(4) . ?
C13 N5 1.347(4) . ?
C14 C15 1.345(5) . ?
C14 N4 1.373(4) . ?
C15 N5 1.381(4) . ?
C17 C18 1.370(4) . ?
C17 C19 1.387(4) . ?
C17 N5 1.437(4) . ?
C18 C11 1.382(4) 2_645 ?
C19 C12 1.382(4) 2_645 ?
C20 O1 1.234(4) . ?
C20 O2 1.249(3) . ?
C20 C21 1.520(4) . ?
C21 C23 1.371(4) . ?
C21 C22 1.374(4) . ?
C22 F1 1.353(3) . ?
C22 C27 1.372(4) 8_465 ?
C23 F2 1.347(3) . ?
C23 C26 1.385(4) 8_465 ?
C24 O3 1.183(4) . ?
C24 O4 1.290(6) . ?
C24 O4' 1.375(7) . ?
C24 C25 1.523(4) . ?
C25 C26 1.377(5) . ?
C25 C27 1.381(5) . ?
C26 F3 1.341(4) . ?
C26 C23 1.385(4) 8_566 ?
C27 F4 1.349(4) . ?
C27 C22 1.372(4) 8_566 ?
C28 N6 1.442(5) . ?
C29 N6 1.448(5) . ?
C30 O5 1.234(5) . ?
C30 N6 1.306(5) . ?
Cd1 N4 2.270(3) . ?
Cd1 N1 2.272(3) . ?
Cd1 O3 2.319(2) . ?
Cd1 O1W 2.330(2) . ?
Cd1 O2 2.406(2) 2_655 ?
Cd1 O2 2.422(2) . ?
O2 Cd1 2.405(2) 2_655 ?

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
C3 C1 N1 110.1(3) . . ?
N1 C2 N2 112.5(3) . . ?
C1 C3 N2 106.4(3) . . ?
C5 C4 C9 119.3(3) . . ?
C5 C4 N2 121.2(3) . . ?
C9 C4 N2 119.5(3) . . ?
C4 C5 C6 120.3(3) . . ?
C7 C6 C5 121.2(3) . . ?
C6 C7 C8 117.9(3) . . ?
C6 C7 N3 121.6(3) . . ?
C8 C7 N3 120.5(3) . . ?
C9 C8 C7 121.7(3) . . ?
C8 C9 C4 119.6(3) . . ?
C11 C10 N3 121.9(3) . . ?
C11 C10 C12 117.9(3) . . ?
N3 C10 C12 120.1(3) . . ?
C18 C11 C10 121.0(3) 2_665 . ?
C19 C12 C10 121.0(3) 2_665 . ?
N4 C13 N5 111.5(3) . . ?
C15 C14 N4 110.4(3) . . ?
C14 C15 N5 106.1(3) . . ?
C18 C17 C19 120.1(3) . . ?
C18 C17 N5 119.0(3) . . ?
C19 C17 N5 120.9(3) . . ?
C17 C18 C11 120.2(3) . 2_645 ?
C12 C19 C17 119.7(3) 2_645 . ?
O1 C20 O2 124.2(3) . . ?
O1 C20 C21 116.3(2) . . ?
O2 C20 C21 119.5(2) . . ?
C23 C21 C22 116.8(3) . . ?
C23 C21 C20 122.4(2) . . ?
C22 C21 C20 120.5(3) . . ?
F1 C22 C27 118.3(3) . 8_465 ?
F1 C22 C21 119.4(3) . . ?
C27 C22 C21 122.3(3) 8_465 . ?
F2 C23 C21 119.8(2) . . ?
F2 C23 C26 118.7(3) . 8_465 ?
C21 C23 C26 121.4(3) . 8_465 ?
O3 C24 O4 121.0(4) . . ?
O3 C24 O4' 118.8(4) . . ?
O3 C24 C25 119.7(3) . . ?
O4 C24 C25 110.1(4) . . ?
O4' C24 C25 113.0(3) . . ?
C26 C25 C27 116.9(3) . . ?
C26 C25 C24 122.1(3) . . ?
C27 C25 C24 120.7(3) . . ?
F3 C26 C25 119.7(3) . . ?
F3 C26 C23 118.8(3) . 8_566 ?
C25 C26 C23 121.5(3) . 8_566 ?
F4 C27 C22 119.3(3) . 8_566 ?
F4 C27 C25 119.6(3) . . ?
C22 C27 C25 121.1(3) 8_566 . ?
O5 C30 N6 123.6(4) . . ?
N4 Cd1 N1 176.58(9) . . ?
N4 Cd1 O3 92.52(9) . . ?
N1 Cd1 O3 90.53(9) . . ?
N4 Cd1 O1W 86.22(9) . . ?
N1 Cd1 O1W 92.44(9) . . ?
O3 Cd1 O1W 86.12(8) . . ?
N4 Cd1 O2 89.98(8) . 2_655 ?
N1 Cd1 O2 92.03(8) . 2_655 ?
O3 Cd1 O2 81.03(7) . 2_655 ?
O1W Cd1 O2 166.42(7) . 2_655 ?
N4 Cd1 O2 86.75(8) . . ?
N1 Cd1 O2 91.28(8) . . ?
O3 Cd1 O2 152.11(7) . . ?
O1W Cd1 O2 121.59(7) . . ?
O2 Cd1 O2 71.10(7) 2_655 . ?
C2 N1 C1 105.2(3) . . ?
C2 N1 Cd1 129.2(2) . . ?
C1 N1 Cd1 125.6(2) . . ?
C2 N2 C3 105.7(3) . . ?
C2 N2 C4 127.8(3) . . ?
C3 N2 C4 126.4(3) . . ?
C10 N3 C7 122.0(3) . . ?
C13 N4 C14 105.2(3) . . ?
C13 N4 Cd1 128.4(2) . . ?
C14 N4 Cd1 125.5(2) . . ?
C13 N5 C15 106.7(3) . . ?
C13 N5 C17 127.1(3) . . ?
C15 N5 C17 126.1(3) . . ?
C30 N6 C28 120.0(3) . . ?
C30 N6 C29 122.7(4) . . ?
C28 N6 C29 116.9(3) . . ?
C20 O2 Cd1 148.84(19) . 2_655 ?
C20 O2 Cd1 98.16(17) . . ?
Cd1 O2 Cd1 108.54(7) 2_655 . ?
C24 O3 Cd1 126.1(2) . . ?

_refine_diff_density_max         1.192
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.095

