# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2016

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

data_binw2
_database_code_depnum_ccdc_archive 'CCDC 1495219'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 F10 N4 Zn'
_chemical_formula_weight         643.83

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'
F F 0.0171 0.0103 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2/C

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

_cell_length_a                   12.2298(13)
_cell_length_b                   7.6667(8)
_cell_length_c                   17.9898(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.106(5)
_cell_angle_gamma                90.00
_cell_volume                     1379.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    185(2)
_cell_measurement_reflns_used    2705
_cell_measurement_theta_min      2.306
_cell_measurement_theta_max      24.461

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7253
_exptl_absorpt_correction_T_max  0.8669
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      185(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 Smart Apex CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8307
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         26.02
_reflns_number_total             2726
_reflns_number_gt                2298
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0414P)²+0.5031P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2726
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0900
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.0000 0.42629(5) 0.2500 0.03502(14) Uani 1 2 d S . .
F1 F 0.20740(14) 0.6580(2) 0.24425(10) 0.0574(4) Uani 1 1 d . . .
F2 F 0.19626(16) 0.8364(2) 0.11172(12) 0.0662(5) Uani 1 1 d . . .
F3 F -0.03129(18) 0.8382(2) -0.05944(11) 0.0631(5) Uani 1 1 d . . .
F4 F -0.24837(16) 0.6556(3) -0.09669(9) 0.0666(5) Uani 1 1 d . . .
F5 F -0.23782(14) 0.4714(2) 0.03328(10) 0.0547(4) Uani 1 1 d . . .
N1 N 0.15082(19) 0.2416(3) 0.29906(13) 0.0379(5) Uani 1 1 d . . .
N2 N 0.4503(2) -0.1385(3) 0.40305(14) 0.0446(5) Uani 1 1 d . . .
C1 C -0.0145(2) 0.5572(3) 0.14564(14) 0.0332(5) Uani 1 1 d . . .
C2 C 0.0907(2) 0.6539(3) 0.15978(15) 0.0378(5) Uani 1 1 d . . .
C3 C 0.0882(3) 0.7476(3) 0.09339(18) 0.0421(6) Uani 1 1 d . . .
C4 C -0.0264(3) 0.7481(3) 0.00695(17) 0.0426(6) Uani 1 1 d . . .
C5 C -0.1349(2) 0.6561(3) -0.01148(15) 0.0416(6) Uani 1 1 d . . .
C6 C -0.1263(2) 0.5627(3) 0.05739(15) 0.0367(5) Uani 1 1 d . . .
C13 C 0.2396(2) 0.2370(3) 0.27785(15) 0.0399(6) Uani 1 1 d . . .
H13A H 0.2335 0.3248 0.2384 0.048 Uiso 1 1 calc R . .
C14 C 0.3378(3) 0.1149(4) 0.30914(16) 0.0433(6) Uani 1 1 d . . .
H14A H 0.3972 0.1199 0.2912 0.052 Uiso 1 1 calc R . .
C15 C 0.3518(2) -0.0189(3) 0.36800(15) 0.0371(5) Uani 1 1 d . . .
C16 C 0.2569(2) -0.0158(3) 0.38845(16) 0.0422(6) Uani 1 1 d . . .
H16A H 0.2584 -0.1034 0.4264 0.051 Uiso 1 1 calc R . .
C17 C 0.1627(3) 0.1125(3) 0.35398(18) 0.0451(6) Uani 1 1 d . . .
H17A H 0.1009 0.1107 0.3699 0.054 Uiso 1 1 calc R . .
C23 C 0.5376(3) -0.1487(5) 0.3734(2) 0.0724(10) Uani 1 1 d . . .
H23A H 0.5787 -0.0346 0.3807 0.109 Uiso 1 1 calc R . .
H23B H 0.4856 -0.1830 0.3093 0.109 Uiso 1 1 calc R . .
H23C H 0.6075 -0.2355 0.4100 0.109 Uiso 1 1 calc R . .
C24 C 0.4527(3) -0.2872(4) 0.45467(18) 0.0533(7) Uani 1 1 d . . .
H24A H 0.4396 -0.2462 0.5006 0.080 Uiso 1 1 calc R . .
H24B H 0.5391 -0.3466 0.4846 0.080 Uiso 1 1 calc R . .
H24C H 0.3809 -0.3685 0.4134 0.080 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
Zn1 C1 2.044(2) 2 ?
Zn1 C1 2.044(2) . ?
Zn1 N1 2.077(2) 2 ?
Zn1 N1 2.0770(19) . ?
F1 C2 1.361(3) . ?
F2 C3 1.348(3) . ?
F3 C4 1.351(3) . ?
F4 C5 1.352(3) . ?
F5 C6 1.363(3) . ?
N1 C13 1.342(3) . ?
N1 C17 1.346(3) . ?
N2 C15 1.348(3) . ?
N2 C23 1.444(4) . ?
N2 C24 1.460(3) . ?
C1 C2 1.376(3) . ?
C1 C6 1.377(3) . ?
C2 C3 1.379(3) . ?
C3 C4 1.369(4) . ?
C4 C5 1.365(4) . ?
C5 C6 1.382(3) . ?
C13 C14 1.364(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.412(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.405(3) . ?
C16 C17 1.364(4) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C1 Zn1 C1 121.21(12) 2 . ?
C1 Zn1 N1 108.17(8) 2 2 ?
C1 Zn1 N1 110.94(8) . 2 ?
C1 Zn1 N1 110.94(8) 2 . ?
C1 Zn1 N1 108.17(8) . . ?
N1 Zn1 N1 94.03(11) 2 . ?
C13 N1 C17 115.2(2) . . ?
C13 N1 Zn1 124.24(16) . . ?
C17 N1 Zn1 120.50(16) . . ?
C15 N2 C23 121.0(2) . . ?
C15 N2 C24 121.0(2) . . ?
C23 N2 C24 116.4(2) . . ?
C2 C1 C6 113.5(2) . . ?
C2 C1 Zn1 121.10(16) . . ?
C6 C1 Zn1 125.35(17) . . ?
F1 C2 C1 119.2(2) . . ?
F1 C2 C3 116.2(2) . . ?
C1 C2 C3 124.6(2) . . ?
F2 C3 C4 119.7(2) . . ?
F2 C3 C2 121.4(2) . . ?
C4 C3 C2 118.9(2) . . ?
F3 C4 C5 120.4(2) . . ?
F3 C4 C3 120.1(2) . . ?
C5 C4 C3 119.4(2) . . ?
F4 C5 C4 119.8(2) . . ?
F4 C5 C6 120.9(2) . . ?
C4 C5 C6 119.2(2) . . ?
F5 C6 C1 120.0(2) . . ?
F5 C6 C5 115.8(2) . . ?
C1 C6 C5 124.3(2) . . ?
N1 C13 C14 124.4(2) . . ?
N1 C13 H13A 117.8 . . ?
C14 C13 H13A 117.8 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
N2 C15 C16 122.6(2) . . ?
N2 C15 C14 122.4(2) . . ?
C16 C15 C14 115.0(2) . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
N1 C17 C16 124.8(2) . . ?
N1 C17 H17A 117.6 . . ?
C16 C17 H17A 117.6 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
C1 Zn1 N1 C13 -122.55(19) 2 . . . ?
C1 Zn1 N1 C13 12.6(2) . . . . ?
N1 Zn1 N1 C13 126.2(2) 2 . . . ?
C1 Zn1 N1 C17 59.3(2) 2 . . . ?
C1 Zn1 N1 C17 -165.47(19) . . . . ?
N1 Zn1 N1 C17 -51.88(17) 2 . . . ?
C1 Zn1 C1 C2 67.51(18) 2 . . . ?
N1 Zn1 C1 C2 -164.01(18) 2 . . . ?
N1 Zn1 C1 C2 -62.2(2) . . . . ?
C1 Zn1 C1 C6 -110.9(2) 2 . . . ?
N1 Zn1 C1 C6 17.6(2) 2 . . . ?
N1 Zn1 C1 C6 119.4(2) . . . . ?
C6 C1 C2 F1 -179.6(2) . . . . ?
Zn1 C1 C2 F1 1.9(3) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
Zn1 C1 C2 C3 -179.09(19) . . . . ?
F1 C2 C3 F2 0.6(3) . . . . ?
C1 C2 C3 F2 -178.5(2) . . . . ?
F1 C2 C3 C4 179.8(2) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
F2 C3 C4 F3 -0.5(4) . . . . ?
C2 C3 C4 F3 -179.7(2) . . . . ?
F2 C3 C4 C5 179.1(2) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
F3 C4 C5 F4 -0.3(4) . . . . ?
C3 C4 C5 F4 -179.9(2) . . . . ?
F3 C4 C5 C6 178.9(2) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C2 C1 C6 F5 179.3(2) . . . . ?
Zn1 C1 C6 F5 -2.2(3) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
Zn1 C1 C6 C5 178.14(19) . . . . ?
F4 C5 C6 F5 0.5(3) . . . . ?
C4 C5 C6 F5 -178.7(2) . . . . ?
F4 C5 C6 C1 -179.9(2) . . . . ?
C4 C5 C6 C1 1.0(4) . . . . ?
C17 N1 C13 C14 -1.1(4) . . . . ?
Zn1 N1 C13 C14 -179.27(19) . . . . ?
N1 C13 C14 C15 0.0(4) . . . . ?
C23 N2 C15 C16 173.6(3) . . . . ?
C24 N2 C15 C16 8.6(4) . . . . ?
C23 N2 C15 C14 -7.6(4) . . . . ?
C24 N2 C15 C14 -172.5(2) . . . . ?
C13 C14 C15 N2 -177.6(2) . . . . ?
C13 C14 C15 C16 1.3(4) . . . . ?
N2 C15 C16 C17 177.3(2) . . . . ?
C14 C15 C16 C17 -1.6(4) . . . . ?
C13 N1 C17 C16 0.7(4) . . . . ?
Zn1 N1 C17 C16 179.0(2) . . . . ?
C15 C16 C17 N1 0.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.057
