# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_rad2_0m
_database_code_depnum_ccdc_archive 'CCDC 1446335'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;
_audit_creation_date             2015-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C34 H39 F14 N3 Zn'
_chemical_formula_sum            'C34 H39 F14 N3 Zn'
_chemical_formula_weight         821.05
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2646(6)
_cell_length_b                   12.3503(7)
_cell_length_c                   15.2654(8)
_cell_angle_alpha                71.6280(10)
_cell_angle_beta                 86.7850(10)
_cell_angle_gamma                87.1630(10)
_cell_volume                     1832.65(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.79
_cell_measurement_theta_min      3.24
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0396 before and 0.0340 after correction.
The Ratio of minimum to maximum transmission is 0.9257.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20859
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         2.815
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6808
_reflns_number_total             7560
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         7560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+1.1044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0740
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C18(H18), C27(H27), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C), C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Zn Zn 0.81288(2) 0.65541(2) 0.75116(2) 0.01419(6) Uani 1 1 d . . . . .
F1 F 0.46461(10) 0.68346(9) 0.55213(7) 0.0234(2) Uani 1 1 d . . . . .
F2 F 0.33528(9) 0.65042(8) 0.67421(7) 0.0234(2) Uani 1 1 d . . . . .
F3 F 0.47168(10) 0.91513(8) 0.57659(7) 0.0245(2) Uani 1 1 d . . . . .
F4 F 0.28421(10) 0.86228(9) 0.64850(7) 0.0248(2) Uani 1 1 d . . . . .
F5 F 0.22098(9) 0.79446(8) 0.49868(7) 0.0247(2) Uani 1 1 d . . . . .
F6 F 0.39435(11) 0.87456(10) 0.42586(7) 0.0300(2) Uani 1 1 d . . . . .
F7 F 0.24863(12) 0.97278(9) 0.47656(8) 0.0347(3) Uani 1 1 d . . . . .
F8 F 0.47321(14) 0.74364(10) 0.95621(8) 0.0479(4) Uani 1 1 d . . . . .
F9 F 0.59359(11) 0.89127(12) 0.91129(9) 0.0447(4) Uani 1 1 d . . . . .
F10 F 0.43173(12) 0.97687(9) 0.75834(7) 0.0329(3) Uani 1 1 d . . . . .
F11 F 0.29817(10) 0.84327(11) 0.83559(8) 0.0362(3) Uani 1 1 d . . . . .
F12 F 0.32140(12) 0.92053(11) 0.98731(8) 0.0411(3) Uani 1 1 d . . . . .
F13 F 0.42802(13) 1.06138(10) 0.89894(9) 0.0411(3) Uani 1 1 d . . . . .
F14 F 0.23385(13) 1.03312(13) 0.86645(9) 0.0498(4) Uani 1 1 d . . . . .
N1 N 0.65876(12) 0.65737(11) 0.67680(8) 0.0126(2) Uani 1 1 d . . . . .
N2 N 0.51341(13) 0.75949(11) 0.75188(9) 0.0141(3) Uani 1 1 d . . . . .
N3 N 0.71414(13) 0.73889(11) 0.82687(8) 0.0133(3) Uani 1 1 d . . . . .
C1 C 0.54799(15) 0.70805(13) 0.68840(10) 0.0132(3) Uani 1 1 d . . . . .
C2 C 0.59152(15) 0.77099(13) 0.81513(10) 0.0138(3) Uani 1 1 d . . . . .
C3 C 0.43166(15) 0.71788(13) 0.62643(11) 0.0146(3) Uani 1 1 d . . . . .
C4 C 0.37470(15) 0.84201(13) 0.58872(11) 0.0160(3) Uani 1 1 d . . . . .
C5 C 0.30921(17) 0.87103(14) 0.49503(12) 0.0205(3) Uani 1 1 d . . . . .
C6 C 0.51581(16) 0.82737(14) 0.88111(11) 0.0188(3) Uani 1 1 d . . . . .
C7 C 0.39790(16) 0.90620(15) 0.84163(11) 0.0204(3) Uani 1 1 d . . . . .
C8 C 0.34591(19) 0.98224(17) 0.90067(13) 0.0307(4) Uani 1 1 d . . . . .
C9 C 0.68803(14) 0.59384(13) 0.61225(10) 0.0127(3) Uani 1 1 d . . . . .
C10 C 0.75930(15) 0.64672(13) 0.53001(10) 0.0139(3) Uani 1 1 d . . . . .
C11 C 0.80723(16) 0.57895(14) 0.47691(11) 0.0180(3) Uani 1 1 d . . . . .
H11 H 0.8568 0.6125 0.4213 0.022 Uiso 1 1 calc R . . . .
C12 C 0.78373(17) 0.46354(14) 0.50396(11) 0.0212(3) Uani 1 1 d . . . . .
H12 H 0.8185 0.4181 0.4677 0.025 Uiso 1 1 calc R . . . .
C13 C 0.70954(17) 0.41442(14) 0.58377(11) 0.0198(3) Uani 1 1 d . . . . .
H13 H 0.6920 0.3355 0.6008 0.024 Uiso 1 1 calc R . . . .
C14 C 0.65986(15) 0.47776(13) 0.63979(11) 0.0153(3) Uani 1 1 d . . . . .
C15 C 0.78448(15) 0.77367(13) 0.49738(11) 0.0161(3) Uani 1 1 d . . . . .
H15 H 0.7342 0.8091 0.5400 0.019 Uiso 1 1 calc R . . . .
C16 C 0.92889(17) 0.79494(15) 0.50119(13) 0.0251(4) Uani 1 1 d . . . . .
H16A H 0.9575 0.7588 0.5643 0.038 Uiso 1 1 calc GR . . . .
H16B H 0.9419 0.8773 0.4830 0.038 Uiso 1 1 calc GR . . . .
H16C H 0.9800 0.7624 0.4588 0.038 Uiso 1 1 calc GR . . . .
C17 C 0.73777(18) 0.83143(14) 0.39943(12) 0.0231(4) Uani 1 1 d . . . . .
H17A H 0.7875 0.7994 0.3562 0.035 Uiso 1 1 calc GR . . . .
H17B H 0.7512 0.9137 0.3817 0.035 Uiso 1 1 calc GR . . . .
H17C H 0.6447 0.8182 0.3978 0.035 Uiso 1 1 calc GR . . . .
C18 C 0.58000(17) 0.42077(14) 0.72775(11) 0.0194(3) Uani 1 1 d . . . . .
H18 H 0.5355 0.4824 0.7491 0.023 Uiso 1 1 calc R . . . .
C19 C 0.6681(2) 0.35097(19) 0.80356(13) 0.0377(5) Uani 1 1 d . . . . .
H19A H 0.7160 0.2919 0.7833 0.057 Uiso 1 1 calc GR . . . .
H19B H 0.6148 0.3149 0.8596 0.057 Uiso 1 1 calc GR . . . .
H19C H 0.7301 0.4011 0.8167 0.057 Uiso 1 1 calc GR . . . .
C20 C 0.4745(2) 0.3474(2) 0.71128(16) 0.0436(6) Uani 1 1 d . . . . .
H20A H 0.4215 0.3932 0.6603 0.065 Uiso 1 1 calc GR . . . .
H20B H 0.4187 0.3196 0.7675 0.065 Uiso 1 1 calc GR . . . .
H20C H 0.5156 0.2823 0.6955 0.065 Uiso 1 1 calc GR . . . .
C21 C 0.79021(15) 0.75226(13) 0.89979(10) 0.0147(3) Uani 1 1 d . . . . .
C22 C 0.86697(16) 0.84867(14) 0.88085(11) 0.0180(3) Uani 1 1 d . . . . .
C23 C 0.94640(17) 0.85510(15) 0.94981(13) 0.0244(4) Uani 1 1 d . . . . .
H23 H 0.9991 0.9195 0.9390 0.029 Uiso 1 1 calc R . . . .
C24 C 0.95004(19) 0.76940(16) 1.03370(13) 0.0273(4) Uani 1 1 d . . . . .
H24 H 1.0044 0.7757 1.0801 0.033 Uiso 1 1 calc R . . . .
C25 C 0.87506(17) 0.67480(15) 1.05037(12) 0.0233(4) Uani 1 1 d . . . . .
H25 H 0.8785 0.6166 1.1084 0.028 Uiso 1 1 calc R . . . .
C26 C 0.79426(16) 0.66300(14) 0.98362(11) 0.0168(3) Uani 1 1 d . . . . .
C27 C 0.86503(17) 0.94198(14) 0.78810(12) 0.0224(4) Uani 1 1 d . . . . .
H27 H 0.7845 0.9338 0.7570 0.027 Uiso 1 1 calc R . . . .
C28 C 0.9829(2) 0.92737(18) 0.72661(14) 0.0362(5) Uani 1 1 d . . . . .
H28A H 1.0632 0.9367 0.7548 0.054 Uiso 1 1 calc GR . . . .
H28B H 0.9771 0.9850 0.6657 0.054 Uiso 1 1 calc GR . . . .
H28C H 0.9838 0.8510 0.7199 0.054 Uiso 1 1 calc GR . . . .
C29 C 0.8604(3) 1.06172(17) 0.79701(16) 0.0462(6) Uani 1 1 d . . . . .
H29A H 0.7868 1.0693 0.8387 0.069 Uiso 1 1 calc GR . . . .
H29B H 0.8494 1.1182 0.7360 0.069 Uiso 1 1 calc GR . . . .
H29C H 0.9420 1.0746 0.8221 0.069 Uiso 1 1 calc GR . . . .
C30 C 0.71899(16) 0.55431(14) 1.00163(11) 0.0197(3) Uani 1 1 d . . . . .
H30 H 0.6542 0.5682 0.9524 0.024 Uiso 1 1 calc R . . . .
C31 C 0.81188(18) 0.45559(15) 0.99525(13) 0.0251(4) Uani 1 1 d . . . . .
H31A H 0.8579 0.4768 0.9346 0.038 Uiso 1 1 calc GR . . . .
H31B H 0.7616 0.3874 1.0034 0.038 Uiso 1 1 calc GR . . . .
H31C H 0.8754 0.4395 1.0437 0.038 Uiso 1 1 calc GR . . . .
C32 C 0.6440(2) 0.52169(17) 1.09506(13) 0.0318(4) Uani 1 1 d . . . . .
H32A H 0.7059 0.5041 1.1447 0.048 Uiso 1 1 calc GR . . . .
H32B H 0.5926 0.4545 1.1019 0.048 Uiso 1 1 calc GR . . . .
H32C H 0.5855 0.5855 1.0985 0.048 Uiso 1 1 calc GR . . . .
C33 C 0.99210(16) 0.59527(15) 0.74939(11) 0.0198(3) Uani 1 1 d . . . . .
H33A H 1.0469 0.6570 0.7095 0.024 Uiso 1 1 calc R . . . .
H33B H 1.0241 0.5747 0.8127 0.024 Uiso 1 1 calc R . . . .
C34 C 1.01244(17) 0.49116(16) 0.71556(12) 0.0254(4) Uani 1 1 d . . . . .
H34A H 0.9638 0.4273 0.7570 0.038 Uiso 1 1 calc GR . . . .
H34B H 1.1056 0.4696 0.7151 0.038 Uiso 1 1 calc GR . . . .
H34C H 0.9810 0.5099 0.6529 0.038 Uiso 1 1 calc GR . . . .


_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
Zn N1 1.9931(13) . ?
Zn N3 1.9855(13) . ?
Zn C33 1.9515(16) . ?
F1 C3 1.3521(17) . ?
F2 C3 1.3500(18) . ?
F3 C4 1.3430(18) . ?
F4 C4 1.3358(18) . ?
F5 C5 1.3280(19) . ?
F6 C5 1.323(2) . ?
F7 C5 1.3283(19) . ?
F8 C6 1.348(2) . ?
F9 C6 1.344(2) . ?
F10 C7 1.334(2) . ?
F11 C7 1.340(2) . ?
F12 C8 1.319(2) . ?
F13 C8 1.315(2) . ?
F14 C8 1.334(2) . ?
N1 C1 1.301(2) . ?
N1 C9 1.4518(18) . ?
N2 C1 1.340(2) . ?
N2 C2 1.334(2) . ?
N3 C2 1.306(2) . ?
N3 C21 1.4499(19) . ?
C1 C3 1.541(2) . ?
C2 C6 1.551(2) . ?
C3 C4 1.554(2) . ?
C4 C5 1.545(2) . ?
C6 C7 1.540(2) . ?
C7 C8 1.552(2) . ?
C9 C10 1.402(2) . ?
C9 C14 1.401(2) . ?
C10 C11 1.394(2) . ?
C10 C15 1.519(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(2) . ?
C14 C18 1.519(2) . ?
C15 H15 1.0000 . ?
C15 C16 1.526(2) . ?
C15 C17 1.533(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 1.0000 . ?
C18 C19 1.520(3) . ?
C18 C20 1.526(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.404(2) . ?
C21 C26 1.402(2) . ?
C22 C23 1.391(2) . ?
C22 C27 1.518(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.381(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.379(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.396(2) . ?
C26 C30 1.523(2) . ?
C27 H27 1.0000 . ?
C27 C28 1.528(3) . ?
C27 C29 1.525(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30 1.0000 . ?
C30 C31 1.534(2) . ?
C30 C32 1.528(2) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.531(2) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
N3 Zn N1 92.37(5) . . ?
C33 Zn N1 133.69(6) . . ?
C33 Zn N3 133.94(6) . . ?
C1 N1 Zn 122.59(10) . . ?
C1 N1 C9 126.60(13) . . ?
C9 N1 Zn 110.80(9) . . ?
C2 N2 C1 124.99(13) . . ?
C2 N3 Zn 122.90(10) . . ?
C2 N3 C21 124.36(13) . . ?
C21 N3 Zn 112.60(9) . . ?
N1 C1 N2 128.59(14) . . ?
N1 C1 C3 122.96(13) . . ?
N2 C1 C3 108.46(13) . . ?
N2 C2 C6 110.69(13) . . ?
N3 C2 N2 128.42(14) . . ?
N3 C2 C6 120.86(13) . . ?
F1 C3 C1 112.16(12) . . ?
F1 C3 C4 106.67(12) . . ?
F2 C3 F1 106.68(12) . . ?
F2 C3 C1 110.06(12) . . ?
F2 C3 C4 108.27(12) . . ?
C1 C3 C4 112.72(12) . . ?
F3 C4 C3 108.98(13) . . ?
F3 C4 C5 106.63(13) . . ?
F4 C4 F3 109.23(13) . . ?
F4 C4 C3 110.27(13) . . ?
F4 C4 C5 106.49(13) . . ?
C5 C4 C3 115.06(13) . . ?
F5 C5 F7 108.15(14) . . ?
F5 C5 C4 110.21(13) . . ?
F6 C5 F5 108.67(13) . . ?
F6 C5 F7 107.79(14) . . ?
F6 C5 C4 112.52(14) . . ?
F7 C5 C4 109.38(13) . . ?
F8 C6 C2 108.06(13) . . ?
F8 C6 C7 108.03(14) . . ?
F9 C6 F8 106.69(14) . . ?
F9 C6 C2 111.60(13) . . ?
F9 C6 C7 105.45(13) . . ?
C7 C6 C2 116.54(13) . . ?
F10 C7 F11 110.19(14) . . ?
F10 C7 C6 109.29(14) . . ?
F10 C7 C8 106.59(14) . . ?
F11 C7 C6 109.70(14) . . ?
F11 C7 C8 106.51(14) . . ?
C6 C7 C8 114.47(14) . . ?
F12 C8 F14 107.72(17) . . ?
F12 C8 C7 111.24(16) . . ?
F13 C8 F12 108.81(16) . . ?
F13 C8 F14 108.61(17) . . ?
F13 C8 C7 112.19(16) . . ?
F14 C8 C7 108.14(15) . . ?
C10 C9 N1 118.52(13) . . ?
C14 C9 N1 118.74(13) . . ?
C14 C9 C10 122.16(14) . . ?
C9 C10 C15 122.44(14) . . ?
C11 C10 C9 117.86(14) . . ?
C11 C10 C15 119.70(14) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.00(15) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.89(15) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.60(15) . . ?
C14 C13 H13 119.2 . . ?
C9 C14 C18 122.31(14) . . ?
C13 C14 C9 117.43(14) . . ?
C13 C14 C18 120.26(14) . . ?
C10 C15 H15 108.1 . . ?
C10 C15 C16 111.03(13) . . ?
C10 C15 C17 111.48(13) . . ?
C16 C15 H15 108.1 . . ?
C16 C15 C17 110.03(14) . . ?
C17 C15 H15 108.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18 107.7 . . ?
C14 C18 C19 110.70(14) . . ?
C14 C18 C20 111.90(14) . . ?
C19 C18 H18 107.7 . . ?
C19 C18 C20 110.92(17) . . ?
C20 C18 H18 107.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 N3 118.83(14) . . ?
C26 C21 N3 118.53(14) . . ?
C26 C21 C22 122.34(15) . . ?
C21 C22 C27 121.39(15) . . ?
C23 C22 C21 117.60(15) . . ?
C23 C22 C27 121.01(15) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.14(17) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.29(16) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 119.4 . . ?
C24 C25 C26 121.25(16) . . ?
C26 C25 H25 119.4 . . ?
C21 C26 C30 122.48(14) . . ?
C25 C26 C21 117.36(15) . . ?
C25 C26 C30 120.12(15) . . ?
C22 C27 H27 107.8 . . ?
C22 C27 C28 110.45(15) . . ?
C22 C27 C29 112.90(15) . . ?
C28 C27 H27 107.8 . . ?
C29 C27 H27 107.8 . . ?
C29 C27 C28 109.99(17) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 C30 H30 108.0 . . ?
C26 C30 C31 110.31(14) . . ?
C26 C30 C32 112.27(15) . . ?
C31 C30 H30 108.0 . . ?
C32 C30 H30 108.0 . . ?
C32 C30 C31 110.19(14) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
Zn C33 H33A 108.3 . . ?
Zn C33 H33B 108.3 . . ?
H33A C33 H33B 107.4 . . ?
C34 C33 Zn 115.93(12) . . ?
C34 C33 H33A 108.3 . . ?
C34 C33 H33B 108.3 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
Zn N1 C1 N2 -4.5(2) . . . . ?
Zn N1 C1 C3 175.24(10) . . . . ?
Zn N1 C9 C10 -79.49(14) . . . . ?
Zn N1 C9 C14 91.95(14) . . . . ?
Zn N3 C2 N2 -2.8(2) . . . . ?
Zn N3 C2 C6 175.07(11) . . . . ?
Zn N3 C21 C22 89.14(15) . . . . ?
Zn N3 C21 C26 -84.69(15) . . . . ?
F1 C3 C4 F3 -91.34(14) . . . . ?
F1 C3 C4 F4 148.77(12) . . . . ?
F1 C3 C4 C5 28.33(18) . . . . ?
F2 C3 C4 F3 154.17(12) . . . . ?
F2 C3 C4 F4 34.28(16) . . . . ?
F2 C3 C4 C5 -86.16(16) . . . . ?
F3 C4 C5 F5 173.40(13) . . . . ?
F3 C4 C5 F6 51.94(17) . . . . ?
F3 C4 C5 F7 -67.82(17) . . . . ?
F4 C4 C5 F5 -70.05(16) . . . . ?
F4 C4 C5 F6 168.49(13) . . . . ?
F4 C4 C5 F7 48.73(17) . . . . ?
F8 C6 C7 F10 -168.56(13) . . . . ?
F8 C6 C7 F11 -47.65(18) . . . . ?
F8 C6 C7 C8 71.99(19) . . . . ?
F9 C6 C7 F10 77.66(16) . . . . ?
F9 C6 C7 F11 -161.43(13) . . . . ?
F9 C6 C7 C8 -41.8(2) . . . . ?
F10 C7 C8 F12 -173.97(15) . . . . ?
F10 C7 C8 F13 -51.82(19) . . . . ?
F10 C7 C8 F14 67.9(2) . . . . ?
F11 C7 C8 F12 68.39(19) . . . . ?
F11 C7 C8 F13 -169.46(15) . . . . ?
F11 C7 C8 F14 -49.7(2) . . . . ?
N1 C1 C3 F1 -9.1(2) . . . . ?
N1 C1 C3 F2 109.50(16) . . . . ?
N1 C1 C3 C4 -129.52(15) . . . . ?
N1 C9 C10 C11 168.48(14) . . . . ?
N1 C9 C10 C15 -12.0(2) . . . . ?
N1 C9 C14 C13 -168.84(14) . . . . ?
N1 C9 C14 C18 10.3(2) . . . . ?
N2 C1 C3 F1 170.67(12) . . . . ?
N2 C1 C3 F2 -70.73(15) . . . . ?
N2 C1 C3 C4 50.25(16) . . . . ?
N2 C2 C6 F8 94.76(16) . . . . ?
N2 C2 C6 F9 -148.24(14) . . . . ?
N2 C2 C6 C7 -27.0(2) . . . . ?
N3 C2 C6 F8 -83.44(18) . . . . ?
N3 C2 C6 F9 33.6(2) . . . . ?
N3 C2 C6 C7 154.76(15) . . . . ?
N3 C21 C22 C23 -175.30(14) . . . . ?
N3 C21 C22 C27 3.9(2) . . . . ?
N3 C21 C26 C25 175.83(14) . . . . ?
N3 C21 C26 C30 -1.7(2) . . . . ?
C1 N1 C9 C10 101.85(18) . . . . ?
C1 N1 C9 C14 -86.72(19) . . . . ?
C1 N2 C2 N3 2.0(3) . . . . ?
C1 N2 C2 C6 -176.07(14) . . . . ?
C1 C3 C4 F3 32.18(17) . . . . ?
C1 C3 C4 F4 -87.71(15) . . . . ?
C1 C3 C4 C5 151.85(13) . . . . ?
C2 N2 C1 N1 2.2(3) . . . . ?
C2 N2 C1 C3 -177.53(14) . . . . ?
C2 N3 C21 C22 -95.12(18) . . . . ?
C2 N3 C21 C26 91.05(19) . . . . ?
C2 C6 C7 F10 -46.75(19) . . . . ?
C2 C6 C7 F11 74.16(18) . . . . ?
C2 C6 C7 C8 -166.20(15) . . . . ?
C3 C4 C5 F5 52.44(18) . . . . ?
C3 C4 C5 F6 -69.01(18) . . . . ?
C3 C4 C5 F7 171.22(13) . . . . ?
C6 C7 C8 F12 -53.0(2) . . . . ?
C6 C7 C8 F13 69.1(2) . . . . ?
C6 C7 C8 F14 -171.11(16) . . . . ?
C9 N1 C1 N2 174.04(14) . . . . ?
C9 N1 C1 C3 -6.2(2) . . . . ?
C9 C10 C11 C12 0.8(2) . . . . ?
C9 C10 C15 C16 112.13(17) . . . . ?
C9 C10 C15 C17 -124.80(16) . . . . ?
C9 C14 C18 C19 -102.77(19) . . . . ?
C9 C14 C18 C20 132.95(18) . . . . ?
C10 C9 C14 C13 2.3(2) . . . . ?
C10 C9 C14 C18 -178.56(14) . . . . ?
C10 C11 C12 C13 1.3(3) . . . . ?
C11 C10 C15 C16 -68.32(19) . . . . ?
C11 C10 C15 C17 54.7(2) . . . . ?
C11 C12 C13 C14 -1.7(3) . . . . ?
C12 C13 C14 C9 -0.1(2) . . . . ?
C12 C13 C14 C18 -179.25(16) . . . . ?
C13 C14 C18 C19 76.4(2) . . . . ?
C13 C14 C18 C20 -47.9(2) . . . . ?
C14 C9 C10 C11 -2.6(2) . . . . ?
C14 C9 C10 C15 176.92(14) . . . . ?
C15 C10 C11 C12 -178.75(15) . . . . ?
C21 N3 C2 N2 -178.10(15) . . . . ?
C21 N3 C2 C6 -0.2(2) . . . . ?
C21 C22 C23 C24 0.3(3) . . . . ?
C21 C22 C27 C28 -99.60(19) . . . . ?
C21 C22 C27 C29 136.79(18) . . . . ?
C21 C26 C30 C31 104.06(18) . . . . ?
C21 C26 C30 C32 -132.63(16) . . . . ?
C22 C21 C26 C25 2.2(2) . . . . ?
C22 C21 C26 C30 -175.27(14) . . . . ?
C22 C23 C24 C25 0.5(3) . . . . ?
C23 C22 C27 C28 79.6(2) . . . . ?
C23 C22 C27 C29 -44.0(2) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C24 C25 C26 C21 -1.4(2) . . . . ?
C24 C25 C26 C30 176.19(16) . . . . ?
C25 C26 C30 C31 -73.36(19) . . . . ?
C25 C26 C30 C32 49.9(2) . . . . ?
C26 C21 C22 C23 -1.7(2) . . . . ?
C26 C21 C22 C27 177.49(15) . . . . ?
C27 C22 C23 C24 -178.89(16) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_rad156_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1446336'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;
_audit_creation_date             2015-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C36 H18 Br12 F12 N6 O2 Zn2, 2(C6 H6)'
_chemical_formula_sum            'C48 H30 Br12 F12 N6 O2 Zn2'
_chemical_formula_weight         2040.44
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.462(2)
_cell_length_b                   11.6254(19)
_cell_length_c                   14.089(2)
_cell_angle_alpha                67.401(3)
_cell_angle_beta                 89.479(4)
_cell_angle_gamma                63.532(3)
_cell_volume                     1521.4(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7601
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      39.81
_cell_measurement_theta_min      2.97
_shelx_estimated_absorpt_T_max   0.669
_shelx_estimated_absorpt_T_min   0.089
_exptl_absorpt_coefficient_mu    8.748
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5420
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1109 before and 0.0690 after correction.
The Ratio of minimum to maximum transmission is 0.5420.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platy
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.538
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13064
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_min         3.002
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4815
_reflns_number_total             6386
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.921
_refine_diff_density_min         -1.990
_refine_diff_density_rms         0.253
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         6386
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0970P)²+5.6114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1591
_refine_ls_wR_factor_ref         0.1772
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C20) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C13(H13), C15(H15), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25)
3.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Zn Zn 0.42384(8) 0.15032(8) 0.47740(6) 0.0155(2) Uani 1 1 d . . . . .
Br1 Br 0.06251(8) 0.38104(9) 0.31442(6) 0.0272(2) Uani 1 1 d . . . . .
Br2 Br 0.18203(9) 0.32385(9) -0.06159(7) 0.0310(2) Uani 1 1 d . . . . .
Br3 Br 0.56916(8) 0.28673(10) 0.20516(7) 0.0329(2) Uani 1 1 d . . . . .
Br4 Br 0.07885(8) 0.29978(9) 0.59580(6) 0.0264(2) Uani 1 1 d . . . . .
Br5 Br 0.32430(9) -0.10402(10) 1.01575(6) 0.0303(2) Uani 1 1 d . . . . .
Br6 Br 0.63696(8) 0.05608(9) 0.73977(6) 0.0271(2) Uani 1 1 d . . . . .
F1 F 0.3273(8) 0.3826(6) 0.7127(5) 0.0560(19) Uani 1 1 d . . . . .
F2 F 0.1982(5) 0.5716(6) 0.5794(5) 0.0458(15) Uani 1 1 d . . . . .
F3 F 0.4068(6) 0.5049(6) 0.6057(5) 0.0389(13) Uani 1 1 d . . . . .
F4 F 0.3402(6) 0.5875(6) 0.1851(5) 0.0469(16) Uani 1 1 d . . . . .
F5 F 0.2605(7) 0.6986(5) 0.2797(4) 0.0530(19) Uani 1 1 d . . . . .
F6 F 0.1425(5) 0.6395(5) 0.2125(4) 0.0391(14) Uani 1 1 d . . . . .
O O 0.3904(5) -0.0063(5) 0.5015(4) 0.0185(11) Uani 1 1 d . . . . .
N1 N 0.3682(6) 0.2477(6) 0.5759(5) 0.0180(13) Uani 1 1 d . . . . .
N2 N 0.3283(6) 0.4710(6) 0.4429(5) 0.0193(14) Uani 1 1 d . . . . .
N3 N 0.3484(6) 0.3354(6) 0.3457(5) 0.0174(13) Uani 1 1 d . . . . .
C1 C 0.3183(7) 0.4515(7) 0.3564(6) 0.0165(15) Uani 1 1 d . . . . .
C2 C 0.3408(7) 0.3794(7) 0.5407(6) 0.0177(16) Uani 1 1 d . . . . .
C3 C 0.3082(7) 0.3383(7) 0.2479(5) 0.0164(15) Uani 1 1 d . . . . .
C4 C 0.1829(8) 0.3544(8) 0.2216(6) 0.0210(17) Uani 1 1 d . . . . .
C5 C 0.1432(8) 0.3493(9) 0.1311(6) 0.0235(17) Uani 1 1 d . . . . .
H5 H 0.0587 0.3569 0.1165 0.028 Uiso 1 1 calc R . . . .
C6 C 0.2303(8) 0.3329(7) 0.0628(6) 0.0202(17) Uani 1 1 d . . . . .
C7 C 0.3547(8) 0.3207(8) 0.0835(6) 0.0222(17) Uani 1 1 d . . . . .
H7 H 0.4119 0.3129 0.0345 0.027 Uiso 1 1 calc R . . . .
C8 C 0.3946(8) 0.3202(8) 0.1767(6) 0.0209(17) Uani 1 1 d . . . . .
C9 C 0.2663(9) 0.5958(9) 0.2575(7) 0.0278(19) Uani 1 1 d . . . . .
C10 C 0.3203(9) 0.4585(8) 0.6134(6) 0.0242(18) Uani 1 1 d . . . . .
C11 C 0.3555(8) 0.1684(7) 0.6800(6) 0.0161(15) Uani 1 1 d . . . . .
C12 C 0.2342(8) 0.1756(8) 0.7031(6) 0.0203(16) Uani 1 1 d . . . . .
C13 C 0.2222(8) 0.0957(8) 0.8004(6) 0.0208(16) Uani 1 1 d . . . . .
H13 H 0.1390 0.1000 0.8127 0.025 Uiso 1 1 calc R . . . .
C14 C 0.3361(8) 0.0071(8) 0.8816(6) 0.0194(16) Uani 1 1 d . . . . .
C15 C 0.4563(8) 0.0013(8) 0.8625(6) 0.0194(16) Uani 1 1 d . . . . .
H15 H 0.5316 -0.0546 0.9182 0.023 Uiso 1 1 calc R . . . .
C16 C 0.4679(7) 0.0765(8) 0.7628(6) 0.0183(16) Uani 1 1 d . . . . .
C18 C 0.2690(9) -0.0133(10) 0.5011(9) 0.040(2) Uani 1 1 d . . . . .
H18A H 0.2087 0.0574 0.4327 0.048 Uiso 1 1 calc R . . . .
H18B H 0.2257 0.0130 0.5561 0.048 Uiso 1 1 calc R . . . .
C19 C 0.2869(10) -0.1577(10) 0.5197(7) 0.032(2) Uani 1 1 d . . . . .
H19A H 0.3348 -0.1875 0.4684 0.048 Uiso 1 1 calc GR . . . .
H19B H 0.1997 -0.1526 0.5122 0.048 Uiso 1 1 calc GR . . . .
H19C H 0.3380 -0.2266 0.5907 0.048 Uiso 1 1 calc GR . . . .
C20 C 0.9430(16) 0.1395(18) 0.2733(13) 0.073(4) Uani 1 1 d . U . . .
H20 H 0.9412 0.1325 0.3427 0.088 Uiso 1 1 calc R . . . .
C21 C 1.0229(12) 0.0220(15) 0.2567(10) 0.055(3) Uani 1 1 d . . . . .
H21 H 1.0740 -0.0678 0.3143 0.066 Uiso 1 1 calc R . . . .
C22 C 1.0276(9) 0.0366(10) 0.1540(8) 0.036(2) Uani 1 1 d . . . . .
H22 H 1.0858 -0.0429 0.1416 0.044 Uiso 1 1 calc R . . . .
C23 C 0.9491(12) 0.1648(13) 0.0704(10) 0.056(3) Uani 1 1 d . . . . .
H23 H 0.9525 0.1738 0.0006 0.067 Uiso 1 1 calc R . . . .
C24 C 0.8650(14) 0.2807(15) 0.0891(14) 0.076(4) Uani 1 1 d . U . . .
H24 H 0.8077 0.3681 0.0316 0.091 Uiso 1 1 calc R . . . .
C25 C 0.8631(14) 0.2716(16) 0.1863(15) 0.073(4) Uani 1 1 d . U . . .
H25 H 0.8084 0.3534 0.1974 0.087 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
Zn Zn 2.9222(16) 2_656 ?
Zn O 1.929(5) . ?
Zn O 1.969(5) 2_656 ?
Zn N1 2.041(6) . ?
Zn N3 2.030(6) . ?
Br1 C4 1.899(8) . ?
Br2 C6 1.898(7) . ?
Br3 C8 1.875(8) . ?
Br4 C12 1.903(8) . ?
Br5 C14 1.880(8) . ?
Br6 C16 1.885(8) . ?
F1 C10 1.317(10) . ?
F2 C10 1.343(10) . ?
F3 C10 1.309(10) . ?
F4 C9 1.325(11) . ?
F5 C9 1.321(10) . ?
F6 C9 1.342(10) . ?
O Zn 1.969(5) 2_656 ?
O C18 1.430(11) . ?
N1 C2 1.297(10) . ?
N1 C11 1.448(10) . ?
N2 C1 1.337(10) . ?
N2 C2 1.339(10) . ?
N3 C1 1.305(9) . ?
N3 C3 1.441(9) . ?
C1 C9 1.562(11) . ?
C2 C10 1.573(10) . ?
C3 C4 1.397(11) . ?
C3 C8 1.410(11) . ?
C4 C5 1.389(11) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(12) . ?
C6 C7 1.391(12) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(11) . ?
C11 C12 1.398(11) . ?
C11 C16 1.416(10) . ?
C12 C13 1.376(11) . ?
C13 H13 0.9500 . ?
C13 C14 1.413(11) . ?
C14 C15 1.379(12) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(11) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.511(13) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20 0.9500 . ?
C20 C21 1.373(19) . ?
C20 C25 1.42(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.395(15) . ?
C22 H22 0.9500 . ?
C22 C23 1.376(15) . ?
C23 H23 0.9500 . ?
C23 C24 1.39(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.33(2) . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O Zn Zn 40.91(15) 2_656 2_656 ?
O Zn Zn 41.94(15) . 2_656 ?
O Zn O 82.9(2) . 2_656 ?
O Zn N1 118.1(3) . . ?
O Zn N1 120.3(2) 2_656 . ?
O Zn N3 118.5(2) 2_656 . ?
O Zn N3 125.9(2) . . ?
N1 Zn Zn 130.60(18) . 2_656 ?
N3 Zn Zn 135.15(17) . 2_656 ?
N3 Zn N1 94.1(2) . . ?
Zn O Zn 97.1(2) . 2_656 ?
C18 O Zn 131.1(5) . . ?
C18 O Zn 131.8(5) . 2_656 ?
C2 N1 Zn 118.2(5) . . ?
C2 N1 C11 123.2(6) . . ?
C11 N1 Zn 118.5(5) . . ?
C1 N2 C2 125.5(7) . . ?
C1 N3 Zn 117.9(5) . . ?
C1 N3 C3 121.9(6) . . ?
C3 N3 Zn 119.3(5) . . ?
N2 C1 C9 109.7(6) . . ?
N3 C1 N2 130.2(7) . . ?
N3 C1 C9 120.0(7) . . ?
N1 C2 N2 129.4(7) . . ?
N1 C2 C10 123.0(7) . . ?
N2 C2 C10 107.6(6) . . ?
C4 C3 N3 120.9(7) . . ?
C4 C3 C8 117.3(7) . . ?
C8 C3 N3 121.7(7) . . ?
C3 C4 Br1 118.8(6) . . ?
C5 C4 Br1 118.4(6) . . ?
C5 C4 C3 122.7(7) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 C4 118.1(7) . . ?
C6 C5 H5 120.9 . . ?
C5 C6 Br2 120.0(6) . . ?
C5 C6 C7 121.6(7) . . ?
C7 C6 Br2 118.4(6) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(7) . . ?
C8 C7 H7 120.3 . . ?
C3 C8 Br3 122.1(6) . . ?
C7 C8 Br3 117.1(6) . . ?
C7 C8 C3 120.8(8) . . ?
F4 C9 F6 107.0(7) . . ?
F4 C9 C1 112.9(7) . . ?
F5 C9 F4 107.0(8) . . ?
F5 C9 F6 106.4(7) . . ?
F5 C9 C1 112.9(7) . . ?
F6 C9 C1 110.3(7) . . ?
F1 C10 F2 106.2(7) . . ?
F1 C10 C2 115.0(6) . . ?
F2 C10 C2 108.6(7) . . ?
F3 C10 F1 109.7(8) . . ?
F3 C10 F2 107.8(7) . . ?
F3 C10 C2 109.4(7) . . ?
C12 C11 N1 122.2(7) . . ?
C12 C11 C16 117.0(7) . . ?
C16 C11 N1 120.7(7) . . ?
C11 C12 Br4 119.0(6) . . ?
C13 C12 Br4 118.2(6) . . ?
C13 C12 C11 122.8(7) . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 118.6(8) . . ?
C14 C13 H13 120.7 . . ?
C13 C14 Br5 120.1(6) . . ?
C15 C14 Br5 119.8(6) . . ?
C15 C14 C13 120.1(7) . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(7) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 Br6 120.6(6) . . ?
C15 C16 Br6 118.4(5) . . ?
C15 C16 C11 121.0(7) . . ?
O C18 H18A 108.8 . . ?
O C18 H18B 108.8 . . ?
O C18 C19 113.9(7) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 H20 120.1 . . ?
C21 C20 C25 119.8(14) . . ?
C25 C20 H20 120.1 . . ?
C20 C21 H21 120.6 . . ?
C20 C21 C22 118.9(13) . . ?
C22 C21 H21 120.6 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.8(11) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.4 . . ?
C22 C23 C24 119.3(13) . . ?
C24 C23 H23 120.4 . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.2(14) . . ?
C25 C24 H24 119.4 . . ?
C20 C25 H25 120.0 . . ?
C24 C25 C20 119.9(14) . . ?
C24 C25 H25 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn O C18 C19 -0.4(13) 2_656 . . . ?
Zn O C18 C19 177.6(6) . . . . ?
Zn N1 C2 N2 8.6(11) . . . . ?
Zn N1 C2 C10 -169.5(6) . . . . ?
Zn N1 C11 C12 -94.0(7) . . . . ?
Zn N1 C11 C16 84.3(8) . . . . ?
Zn N3 C1 N2 -0.4(11) . . . . ?
Zn N3 C1 C9 177.1(6) . . . . ?
Zn N3 C3 C4 83.5(8) . . . . ?
Zn N3 C3 C8 -94.3(8) . . . . ?
Br1 C4 C5 C6 178.7(6) . . . . ?
Br2 C6 C7 C8 -176.9(6) . . . . ?
Br4 C12 C13 C14 -177.7(6) . . . . ?
Br5 C14 C15 C16 176.4(6) . . . . ?
N1 C2 C10 F1 -2.8(12) . . . . ?
N1 C2 C10 F2 -121.5(8) . . . . ?
N1 C2 C10 F3 121.1(8) . . . . ?
N1 C11 C12 Br4 -2.8(9) . . . . ?
N1 C11 C12 C13 176.8(7) . . . . ?
N1 C11 C16 Br6 0.5(9) . . . . ?
N1 C11 C16 C15 179.5(7) . . . . ?
N2 C1 C9 F4 129.6(8) . . . . ?
N2 C1 C9 F5 8.1(10) . . . . ?
N2 C1 C9 F6 -110.7(8) . . . . ?
N2 C2 C10 F1 178.8(8) . . . . ?
N2 C2 C10 F2 60.0(9) . . . . ?
N2 C2 C10 F3 -57.4(8) . . . . ?
N3 C1 C9 F4 -48.3(11) . . . . ?
N3 C1 C9 F5 -169.8(8) . . . . ?
N3 C1 C9 F6 71.3(9) . . . . ?
N3 C3 C4 Br1 2.8(10) . . . . ?
N3 C3 C4 C5 -176.0(7) . . . . ?
N3 C3 C8 Br3 1.5(10) . . . . ?
N3 C3 C8 C7 178.8(7) . . . . ?
C1 N2 C2 N1 12.9(13) . . . . ?
C1 N2 C2 C10 -168.9(7) . . . . ?
C1 N3 C3 C4 -85.2(10) . . . . ?
C1 N3 C3 C8 97.1(9) . . . . ?
C2 N1 C11 C12 83.2(10) . . . . ?
C2 N1 C11 C16 -98.5(9) . . . . ?
C2 N2 C1 N3 -18.0(13) . . . . ?
C2 N2 C1 C9 164.3(7) . . . . ?
C3 N3 C1 N2 168.4(8) . . . . ?
C3 N3 C1 C9 -14.2(11) . . . . ?
C3 C4 C5 C6 -2.5(12) . . . . ?
C4 C3 C8 Br3 -176.3(6) . . . . ?
C4 C3 C8 C7 1.0(11) . . . . ?
C4 C5 C6 Br2 179.5(6) . . . . ?
C4 C5 C6 C7 0.4(12) . . . . ?
C5 C6 C7 C8 2.2(12) . . . . ?
C6 C7 C8 Br3 174.5(6) . . . . ?
C6 C7 C8 C3 -2.9(12) . . . . ?
C8 C3 C4 Br1 -179.4(5) . . . . ?
C8 C3 C4 C5 1.8(12) . . . . ?
C11 N1 C2 N2 -168.6(7) . . . . ?
C11 N1 C2 C10 13.3(12) . . . . ?
C11 C12 C13 C14 2.7(12) . . . . ?
C12 C11 C16 Br6 178.8(5) . . . . ?
C12 C11 C16 C15 -2.1(11) . . . . ?
C12 C13 C14 Br5 -180.0(6) . . . . ?
C12 C13 C14 C15 -0.3(11) . . . . ?
C13 C14 C15 C16 -3.2(11) . . . . ?
C14 C15 C16 Br6 -176.5(6) . . . . ?
C14 C15 C16 C11 4.5(11) . . . . ?
C16 C11 C12 Br4 178.9(5) . . . . ?
C16 C11 C12 C13 -1.5(11) . . . . ?
C20 C21 C22 C23 -3.1(17) . . . . ?
C21 C20 C25 C24 1(2) . . . . ?
C21 C22 C23 C24 0.4(17) . . . . ?
C22 C23 C24 C25 3(2) . . . . ?
C23 C24 C25 C20 -3(2) . . . . ?
C25 C20 C21 C22 2.6(19) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_rad205_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1446337'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;
_audit_creation_date             2015-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H11 Cl4 F14 N3 O Zn, C6 H6'
_chemical_formula_sum            'C28 H17 Cl4 F14 N3 O Zn'
_chemical_formula_weight         884.61
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.3583(10)
_cell_length_b                   12.0545(11)
_cell_length_c                   12.6061(11)
_cell_angle_alpha                88.972(2)
_cell_angle_beta                 79.294(2)
_cell_angle_gamma                87.809(2)
_cell_volume                     1694.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7498
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      31.88
_cell_measurement_theta_min      3.14
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.682
_exptl_absorpt_coefficient_mu    1.147
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0734 before and 0.0518 after correction.
The Ratio of minimum to maximum transmission is 0.7407.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platy
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.042
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16822
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.999
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.139
_diffrn_ambient_temperature      101.58
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5168
_reflns_number_total             6634
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         2.415
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         6634
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0898P)²+2.5736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1528
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C34) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C31)
\\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C25) \\sim Ueq,
Uanis(C24) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C27)
\\sim Ueq, Uanis(C26) \\sim Ueq: with sigma of 0.005 and sigma for terminal
atoms of 0.005
3. Rigid body (RIGU) restrains
 C34, C33, C32, C31, C30, C29, C25, C24, C23, C28, C27, C26
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Fixed Sof: C23(0.5) H23(0.5) C24(0.5) H24(0.5) C25(0.5) H25(0.5) C26(0.5)
 H26(0.5) C27(0.5) H27(0.5) C28(0.5) H28(0.5) C29(0.5) H29(0.5) C34(0.5)
 H34(0.5) C33(0.5) H33(0.5) C32(0.5) H32(0.5) C31(0.5) H31(0.5) C30(0.5)
 H30(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C23(H23), C24(H24),
 C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C34(H34), C33(H33), C32(H32),
  C31(H31), C30(H30)
5.c Fitted hexagon refined as free rotating group:
 C23(C24,C25,C26,C27,C28), C29(C34,C33,C32,C31,C30)
5.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Zn Zn 0.53490(4) 0.89528(4) 0.54807(4) 0.01722(15) Uani 1 1 d . . . . .
Cl1 Cl 0.33082(9) 0.61305(8) 0.64222(10) 0.0289(3) Uani 1 1 d . . . . .
Cl2 Cl 0.33482(9) 1.03832(8) 0.76407(9) 0.0259(2) Uani 1 1 d . . . . .
Cl3 Cl 0.54984(9) 0.64862(9) 0.39675(9) 0.0276(2) Uani 1 1 d . . . . .
Cl4 Cl 0.92128(9) 0.87983(9) 0.47603(9) 0.0269(2) Uani 1 1 d . . . . .
F1 F 0.4623(3) 0.6147(2) 0.8648(2) 0.0377(7) Uani 1 1 d . . . . .
F2 F 0.3455(2) 0.7620(3) 0.8935(2) 0.0361(7) Uani 1 1 d . . . . .
F3 F 0.6365(3) 0.7148(4) 0.9366(2) 0.0671(12) Uani 1 1 d . . . . .
F4 F 0.5443(5) 0.8753(3) 0.9302(3) 0.0775(13) Uani 1 1 d . . . . .
F5 F 0.3708(5) 0.8086(6) 1.0887(3) 0.139(3) Uani 1 1 d . . . . .
F6 F 0.5399(3) 0.7775(3) 1.1298(3) 0.0612(10) Uani 1 1 d . . . . .
F7 F 0.4438(6) 0.6458(4) 1.0828(3) 0.112(2) Uani 1 1 d . . . . .
F8 F 0.8687(2) 0.6247(2) 0.5305(2) 0.0395(7) Uani 1 1 d . . . . .
F9 F 0.8594(2) 0.6742(2) 0.6951(2) 0.0380(7) Uani 1 1 d . . . . .
F10 F 0.7072(3) 0.5213(2) 0.7681(2) 0.0493(9) Uani 1 1 d . . . . .
F11 F 0.6561(3) 0.5040(2) 0.6102(3) 0.0526(9) Uani 1 1 d . . . . .
F12 F 0.8660(3) 0.4045(3) 0.5338(3) 0.0559(9) Uani 1 1 d . . . . .
F13 F 0.9408(3) 0.4517(2) 0.6686(3) 0.0426(7) Uani 1 1 d . . . . .
F14 F 0.7987(3) 0.3368(2) 0.6903(3) 0.0650(11) Uani 1 1 d . . . . .
O O 0.4249(2) 0.9481(2) 0.4572(2) 0.0221(6) Uani 1 1 d . . . . .
N1 N 0.4476(3) 0.8217(3) 0.6839(3) 0.0164(7) Uani 1 1 d . . . . .
N2 N 0.6260(3) 0.7329(3) 0.7197(3) 0.0187(7) Uani 1 1 d . . . . .
N3 N 0.6737(3) 0.7819(3) 0.5328(3) 0.0158(7) Uani 1 1 d . . . . .
C1 C 0.5106(3) 0.7669(3) 0.7450(3) 0.0174(8) Uani 1 1 d . . . . .
C2 C 0.6899(3) 0.7273(3) 0.6197(3) 0.0181(8) Uani 1 1 d . . . . .
C3 C 0.3203(3) 0.8272(3) 0.7025(3) 0.0157(8) Uani 1 1 d . . . . .
C4 C 0.2554(4) 0.7382(3) 0.6799(3) 0.0196(8) Uani 1 1 d . . . . .
C5 C 0.1319(4) 0.7462(3) 0.6872(3) 0.0227(9) Uani 1 1 d . . . . .
H5 H 0.0894 0.6843 0.6709 0.027 Uiso 1 1 calc R . . . .
C6 C 0.0714(4) 0.8453(4) 0.7185(3) 0.0237(9) Uani 1 1 d . . . . .
H6 H -0.0131 0.8515 0.7233 0.028 Uiso 1 1 calc R . . . .
C7 C 0.1329(4) 0.9358(3) 0.7430(3) 0.0226(9) Uani 1 1 d . . . . .
H7 H 0.0910 1.0034 0.7658 0.027 Uiso 1 1 calc R . . . .
C8 C 0.2566(3) 0.9262(3) 0.7338(3) 0.0180(8) Uani 1 1 d . . . . .
C9 C 0.7427(3) 0.7586(3) 0.4278(3) 0.0175(8) Uani 1 1 d . . . . .
C10 C 0.6938(3) 0.6959(3) 0.3555(3) 0.0200(8) Uani 1 1 d . . . . .
C11 C 0.7569(4) 0.6698(3) 0.2542(4) 0.0258(9) Uani 1 1 d . . . . .
H11 H 0.7225 0.6249 0.2077 0.031 Uiso 1 1 calc R . . . .
C12 C 0.8706(4) 0.7093(3) 0.2209(4) 0.0266(10) Uani 1 1 d . . . . .
H12 H 0.9148 0.6912 0.1514 0.032 Uiso 1 1 calc R . . . .
C13 C 0.9204(4) 0.7751(3) 0.2886(3) 0.0243(9) Uani 1 1 d . . . . .
H13 H 0.9981 0.8031 0.2654 0.029 Uiso 1 1 calc R . . . .
C14 C 0.8562(3) 0.7999(3) 0.3907(3) 0.0195(8) Uani 1 1 d . . . . .
C15 C 0.4612(4) 0.7272(3) 0.8604(3) 0.0233(9) Uani 1 1 d . . . . .
C16 C 0.5296(4) 0.7671(4) 0.9453(4) 0.0332(11) Uani 1 1 d . . . . .
C17 C 0.4696(5) 0.7482(6) 1.0639(4) 0.0488(15) Uani 1 1 d . . . . .
C18 C 0.7933(3) 0.6393(3) 0.6242(3) 0.0208(9) Uani 1 1 d . . . . .
C19 C 0.7467(4) 0.5240(3) 0.6615(4) 0.0253(9) Uani 1 1 d . . . . .
C20 C 0.8396(4) 0.4270(4) 0.6370(4) 0.0335(11) Uani 1 1 d . . . . .
C21 C 0.3245(4) 0.8979(4) 0.4262(5) 0.0361(12) Uani 1 1 d . . . . .
H21A H 0.2533 0.9081 0.4842 0.043 Uiso 1 1 calc R . . . .
H21B H 0.3417 0.8172 0.4166 0.043 Uiso 1 1 calc R . . . .
C22 C 0.2980(5) 0.9485(4) 0.3224(4) 0.0378(12) Uani 1 1 d . . . . .
H22A H 0.3689 0.9392 0.2652 0.057 Uiso 1 1 calc GR . . . .
H22B H 0.2776 1.0278 0.3328 0.057 Uiso 1 1 calc GR . . . .
H22C H 0.2305 0.9114 0.3019 0.057 Uiso 1 1 calc GR . . . .
C23 C 0.9773(6) 1.0967(6) 0.9902(7) 0.042(2) Uani 0.5 1 d . U P A -1
H23 H 0.9371 1.1642 0.9754 0.051 Uiso 0.5 1 calc R . P A -1
C24 C 0.9243(5) 0.9959(8) 0.9822(7) 0.052(2) Uani 0.5 1 d G U P A -1
H24 H 0.8478 0.9945 0.9620 0.062 Uiso 0.5 1 calc R . P A -1
C25 C 0.9831(8) 0.8972(6) 1.0039(7) 0.058(3) Uani 0.5 1 d G U P A -1
H25 H 0.9468 0.8283 0.9985 0.070 Uiso 0.5 1 calc R . P A -1
C26 C 1.0949(7) 0.8993(6) 1.0334(7) 0.062(3) Uani 0.5 1 d G U P A -1
H26 H 1.1351 0.8318 1.0482 0.074 Uiso 0.5 1 calc R . P A -1
C27 C 1.1480(5) 1.0001(7) 1.0414(6) 0.056(2) Uani 0.5 1 d G U P A -1
H27 H 1.2244 1.0015 1.0616 0.067 Uiso 0.5 1 calc R . P A -1
C28 C 1.0892(6) 1.0988(6) 1.0197(6) 0.046(2) Uani 0.5 1 d G U P A -1
H28 H 1.1254 1.1677 1.0251 0.055 Uiso 0.5 1 calc R . P A -1
C29 C 0.8906(6) 0.4210(5) 1.0669(5) 0.044(2) Uani 0.5 1 d . U P B -1
H29 H 0.8460 0.3667 1.1111 0.053 Uiso 0.5 1 calc R . P B -1
C34 C 0.8352(4) 0.4892(6) 0.9994(6) 0.044(2) Uani 0.5 1 d G U P B -1
H34 H 0.7527 0.4815 0.9973 0.052 Uiso 0.5 1 calc R . P B -1
C33 C 0.9004(6) 0.5687(6) 0.9348(5) 0.051(2) Uani 0.5 1 d G U P B -1
H33 H 0.8625 0.6154 0.8887 0.061 Uiso 0.5 1 calc R . P B -1
C32 C 1.0211(6) 0.5801(6) 0.9379(6) 0.043(2) Uani 0.5 1 d G U P B -1
H32 H 1.0656 0.6344 0.8938 0.051 Uiso 0.5 1 calc R . P B -1
C31 C 1.0765(4) 0.5119(6) 1.0054(6) 0.0360(19) Uani 0.5 1 d G U P B -1
H31 H 1.1589 0.5196 1.0075 0.043 Uiso 0.5 1 calc R . P B -1
C30 C 1.0112(6) 0.4323(6) 1.0700(6) 0.038(2) Uani 0.5 1 d G U P B -1
H30 H 1.0491 0.3857 1.1162 0.046 Uiso 0.5 1 calc R . P B -1


_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
Zn Zn 2.9267(8) 2_676 ?
Zn O 1.929(3) . ?
Zn O 1.956(3) 2_676 ?
Zn N1 2.021(3) . ?
Zn N3 2.030(3) . ?
Cl1 C4 1.735(4) . ?
Cl2 C8 1.730(4) . ?
Cl3 C10 1.736(4) . ?
Cl4 C14 1.738(4) . ?
F1 C15 1.355(5) . ?
F2 C15 1.356(5) . ?
F3 C16 1.333(5) . ?
F4 C16 1.327(6) . ?
F5 C17 1.305(7) . ?
F6 C17 1.316(6) . ?
F7 C17 1.288(8) . ?
F8 C18 1.335(5) . ?
F9 C18 1.351(5) . ?
F10 C19 1.335(5) . ?
F11 C19 1.344(5) . ?
F12 C20 1.310(6) . ?
F13 C20 1.330(6) . ?
F14 C20 1.321(6) . ?
O Zn 1.956(3) 2_676 ?
O C21 1.431(5) . ?
N1 C1 1.301(5) . ?
N1 C3 1.420(5) . ?
N2 C1 1.340(5) . ?
N2 C2 1.334(5) . ?
N3 C2 1.307(5) . ?
N3 C9 1.434(5) . ?
C1 C15 1.534(6) . ?
C2 C18 1.560(5) . ?
C3 C4 1.388(6) . ?
C3 C8 1.397(5) . ?
C4 C5 1.388(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.387(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.389(6) . ?
C9 C10 1.398(6) . ?
C9 C14 1.395(6) . ?
C10 C11 1.378(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(6) . ?
C15 C16 1.529(6) . ?
C16 C17 1.541(7) . ?
C18 C19 1.541(6) . ?
C19 C20 1.540(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.509(7) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23 0.9500 . ?
C23 C24 1.3900 . ?
C23 C28 1.3900 . ?
C24 H24 0.9500 . ?
C24 C25 1.3900 . ?
C25 H25 0.9500 . ?
C25 C26 1.3900 . ?
C26 H26 0.9500 . ?
C26 C27 1.3900 . ?
C27 H27 0.9500 . ?
C27 C28 1.3900 . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C29 C34 1.3900 . ?
C29 C30 1.3900 . ?
C34 H34 0.9500 . ?
C34 C33 1.3900 . ?
C33 H33 0.9500 . ?
C33 C32 1.3900 . ?
C32 H32 0.9500 . ?
C32 C31 1.3900 . ?
C31 H31 0.9500 . ?
C31 C30 1.3900 . ?
C30 H30 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O Zn Zn 41.47(8) . 2_676 ?
O Zn Zn 40.78(8) 2_676 2_676 ?
O Zn O 82.25(12) . 2_676 ?
O Zn N1 122.29(13) 2_676 . ?
O Zn N1 111.32(13) . . ?
O Zn N3 135.22(13) . . ?
O Zn N3 116.93(12) 2_676 . ?
N1 Zn Zn 126.64(9) . 2_676 ?
N1 Zn N3 92.58(12) . . ?
N3 Zn Zn 140.40(9) . 2_676 ?
Zn O Zn 97.75(12) . 2_676 ?
C21 O Zn 131.5(2) . . ?
C21 O Zn 129.0(2) . 2_676 ?
C1 N1 Zn 118.3(3) . . ?
C1 N1 C3 124.2(3) . . ?
C3 N1 Zn 117.3(2) . . ?
C2 N2 C1 125.0(3) . . ?
C2 N3 Zn 117.4(3) . . ?
C2 N3 C9 122.9(3) . . ?
C9 N3 Zn 119.5(2) . . ?
N1 C1 N2 127.6(4) . . ?
N1 C1 C15 124.3(3) . . ?
N2 C1 C15 108.1(3) . . ?
N2 C2 C18 106.0(3) . . ?
N3 C2 N2 129.3(3) . . ?
N3 C2 C18 124.7(4) . . ?
C4 C3 N1 121.4(3) . . ?
C4 C3 C8 117.4(3) . . ?
C8 C3 N1 120.9(3) . . ?
C3 C4 Cl1 118.9(3) . . ?
C3 C4 C5 121.9(4) . . ?
C5 C4 Cl1 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.3(4) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.5(4) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.2(4) . . ?
C8 C7 H7 120.4 . . ?
C3 C8 Cl2 118.6(3) . . ?
C7 C8 Cl2 119.8(3) . . ?
C7 C8 C3 121.6(4) . . ?
C10 C9 N3 119.7(3) . . ?
C14 C9 N3 123.3(4) . . ?
C14 C9 C10 116.9(4) . . ?
C9 C10 Cl3 118.2(3) . . ?
C11 C10 Cl3 119.7(3) . . ?
C11 C10 C9 122.1(4) . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.5(4) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.2(4) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.6(4) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 Cl4 119.3(3) . . ?
C13 C14 Cl4 119.1(3) . . ?
C13 C14 C9 121.6(4) . . ?
F1 C15 F2 106.3(3) . . ?
F1 C15 C1 110.0(3) . . ?
F1 C15 C16 108.0(3) . . ?
F2 C15 C1 111.6(3) . . ?
F2 C15 C16 106.1(3) . . ?
C16 C15 C1 114.3(4) . . ?
F3 C16 C15 111.2(4) . . ?
F3 C16 C17 104.3(4) . . ?
F4 C16 F3 109.5(5) . . ?
F4 C16 C15 107.9(4) . . ?
F4 C16 C17 107.8(4) . . ?
C15 C16 C17 115.9(4) . . ?
F5 C17 F6 106.5(5) . . ?
F5 C17 C16 111.1(5) . . ?
F6 C17 C16 110.9(5) . . ?
F7 C17 F5 108.1(7) . . ?
F7 C17 F6 108.6(5) . . ?
F7 C17 C16 111.5(5) . . ?
F8 C18 F9 106.5(3) . . ?
F8 C18 C2 114.3(3) . . ?
F8 C18 C19 106.6(3) . . ?
F9 C18 C2 108.3(3) . . ?
F9 C18 C19 108.2(3) . . ?
C19 C18 C2 112.7(3) . . ?
F10 C19 F11 109.6(4) . . ?
F10 C19 C18 110.9(4) . . ?
F10 C19 C20 106.1(4) . . ?
F11 C19 C18 107.5(3) . . ?
F11 C19 C20 107.5(4) . . ?
C20 C19 C18 115.2(4) . . ?
F12 C20 F13 107.6(4) . . ?
F12 C20 F14 108.7(4) . . ?
F12 C20 C19 112.4(4) . . ?
F13 C20 C19 110.1(4) . . ?
F14 C20 F13 107.8(4) . . ?
F14 C20 C19 110.2(4) . . ?
O C21 H21A 109.4 . . ?
O C21 H21B 109.4 . . ?
O C21 C22 111.0(4) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 H23 120.0 . . ?
C24 C23 C28 120.0 . . ?
C28 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 120.0 . . ?
C28 C27 H27 120.0 . . ?
C23 C28 H28 120.0 . . ?
C27 C28 C23 120.0 . . ?
C27 C28 H28 120.0 . . ?
C34 C29 H29 120.0 . . ?
C34 C29 C30 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C34 H34 120.0 . . ?
C29 C34 C33 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 C33 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C31 H31 120.0 . . ?
C32 C31 C30 120.0 . . ?
C30 C31 H31 120.0 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn O C21 C22 41.5(6) 2_676 . . . ?
Zn O C21 C22 -157.0(3) . . . . ?
Zn N1 C1 N2 -14.8(5) . . . . ?
Zn N1 C1 C15 167.0(3) . . . . ?
Zn N1 C3 C4 100.3(4) . . . . ?
Zn N1 C3 C8 -73.2(4) . . . . ?
Zn N3 C2 N2 1.6(6) . . . . ?
Zn N3 C2 C18 -178.5(3) . . . . ?
Zn N3 C9 C10 -73.8(4) . . . . ?
Zn N3 C9 C14 103.1(4) . . . . ?
Cl1 C4 C5 C6 179.2(3) . . . . ?
Cl3 C10 C11 C12 178.8(3) . . . . ?
F1 C15 C16 F3 50.6(5) . . . . ?
F1 C15 C16 F4 170.7(4) . . . . ?
F1 C15 C16 C17 -68.3(5) . . . . ?
F2 C15 C16 F3 164.2(4) . . . . ?
F2 C15 C16 F4 -75.6(5) . . . . ?
F2 C15 C16 C17 45.3(5) . . . . ?
F3 C16 C17 F5 170.7(6) . . . . ?
F3 C16 C17 F6 52.5(6) . . . . ?
F3 C16 C17 F7 -68.7(6) . . . . ?
F4 C16 C17 F5 54.3(7) . . . . ?
F4 C16 C17 F6 -63.9(6) . . . . ?
F4 C16 C17 F7 175.0(5) . . . . ?
F8 C18 C19 F10 157.5(3) . . . . ?
F8 C18 C19 F11 -82.7(4) . . . . ?
F8 C18 C19 C20 37.0(5) . . . . ?
F9 C18 C19 F10 43.3(4) . . . . ?
F9 C18 C19 F11 163.1(3) . . . . ?
F9 C18 C19 C20 -77.2(5) . . . . ?
F10 C19 C20 F12 165.8(4) . . . . ?
F10 C19 C20 F13 -74.3(5) . . . . ?
F10 C19 C20 F14 44.5(5) . . . . ?
F11 C19 C20 F12 48.6(5) . . . . ?
F11 C19 C20 F13 168.5(4) . . . . ?
F11 C19 C20 F14 -72.7(5) . . . . ?
N1 C1 C15 F1 114.1(4) . . . . ?
N1 C1 C15 F2 -3.8(6) . . . . ?
N1 C1 C15 C16 -124.2(4) . . . . ?
N1 C3 C4 Cl1 7.0(5) . . . . ?
N1 C3 C4 C5 -173.3(4) . . . . ?
N1 C3 C8 Cl2 -7.0(5) . . . . ?
N1 C3 C8 C7 174.2(4) . . . . ?
N2 C1 C15 F1 -64.4(4) . . . . ?
N2 C1 C15 F2 177.7(3) . . . . ?
N2 C1 C15 C16 57.3(4) . . . . ?
N2 C2 C18 F8 -178.5(3) . . . . ?
N2 C2 C18 F9 -60.0(4) . . . . ?
N2 C2 C18 C19 59.7(4) . . . . ?
N3 C2 C18 F8 1.5(6) . . . . ?
N3 C2 C18 F9 120.0(4) . . . . ?
N3 C2 C18 C19 -120.3(4) . . . . ?
N3 C9 C10 Cl3 0.1(5) . . . . ?
N3 C9 C10 C11 -179.0(3) . . . . ?
N3 C9 C14 Cl4 2.3(5) . . . . ?
N3 C9 C14 C13 179.7(3) . . . . ?
C1 N1 C3 C4 -75.3(5) . . . . ?
C1 N1 C3 C8 111.2(4) . . . . ?
C1 N2 C2 N3 24.0(7) . . . . ?
C1 N2 C2 C18 -155.9(4) . . . . ?
C1 C15 C16 F3 -72.3(5) . . . . ?
C1 C15 C16 F4 47.9(5) . . . . ?
C1 C15 C16 C17 168.8(4) . . . . ?
C2 N2 C1 N1 -15.9(7) . . . . ?
C2 N2 C1 C15 162.5(4) . . . . ?
C2 N3 C9 C10 100.8(4) . . . . ?
C2 N3 C9 C14 -82.2(5) . . . . ?
C2 C18 C19 F10 -76.4(4) . . . . ?
C2 C18 C19 F11 43.4(5) . . . . ?
C2 C18 C19 C20 163.1(4) . . . . ?
C3 N1 C1 N2 160.8(4) . . . . ?
C3 N1 C1 C15 -17.5(6) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C4 C3 C8 Cl2 179.2(3) . . . . ?
C4 C3 C8 C7 0.4(6) . . . . ?
C4 C5 C6 C7 -0.3(6) . . . . ?
C5 C6 C7 C8 1.2(6) . . . . ?
C6 C7 C8 Cl2 180.0(3) . . . . ?
C6 C7 C8 C3 -1.2(6) . . . . ?
C8 C3 C4 Cl1 -179.3(3) . . . . ?
C8 C3 C4 C5 0.4(6) . . . . ?
C9 N3 C2 N2 -173.2(4) . . . . ?
C9 N3 C2 C18 6.7(6) . . . . ?
C9 C10 C11 C12 -2.1(6) . . . . ?
C10 C9 C14 Cl4 179.3(3) . . . . ?
C10 C9 C14 C13 -3.3(5) . . . . ?
C10 C11 C12 C13 -0.4(6) . . . . ?
C11 C12 C13 C14 0.9(6) . . . . ?
C12 C13 C14 Cl4 178.4(3) . . . . ?
C12 C13 C14 C9 1.0(6) . . . . ?
C14 C9 C10 Cl3 -177.0(3) . . . . ?
C14 C9 C10 C11 3.8(5) . . . . ?
C15 C16 C17 F5 -66.7(7) . . . . ?
C15 C16 C17 F6 175.1(4) . . . . ?
C15 C16 C17 F7 54.0(6) . . . . ?
C18 C19 C20 F12 -71.1(5) . . . . ?
C18 C19 C20 F13 48.8(5) . . . . ?
C18 C19 C20 F14 167.5(4) . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C23 C28 C27 0.0 . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C26 C27 C28 C23 0.0 . . . . ?
C28 C23 C24 C25 0.0 . . . . ?
C29 C34 C33 C32 0.0 . . . . ?
C34 C29 C30 C31 0.0 . . . . ?
C34 C33 C32 C31 0.0 . . . . ?
C33 C32 C31 C30 0.0 . . . . ?
C32 C31 C30 C29 0.0 . . . . ?
C30 C29 C34 C33 0.0 . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_rad157_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1446338'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;
_audit_creation_date             2015-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C44 H54 F28 N6 O4 Zn2'
_chemical_formula_sum            'C44 H54 F28 N6 O4 Zn2'
_chemical_formula_weight         1393.67
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8323(17)
_cell_length_b                   11.4141(18)
_cell_length_c                   12.2715(19)
_cell_angle_alpha                108.695(3)
_cell_angle_beta                 96.956(3)
_cell_angle_gamma                96.245(3)
_cell_volume                     1408.9(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6786
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.65
_cell_measurement_theta_min      3.02
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.746
_exptl_absorpt_coefficient_mu    0.990
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7773
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0696 before and 0.0478 after correction.
The Ratio of minimum to maximum transmission is 0.7773.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platy
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.062
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16540
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         2.857
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5360
_reflns_number_total             6994
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.181
_refine_diff_density_min         -0.810
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         6994
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0705P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1207
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C16(H16A,
 H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B),
 C21(H21A,H21B)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Zn Zn 0.49938(3) 0.51687(3) 0.12823(3) 0.01479(9) Uani 1 1 d . . . . .
F1 F 0.39994(15) 0.23415(14) 0.35348(14) 0.0252(3) Uani 1 1 d . . . . .
F2 F 0.34183(14) 0.14600(13) 0.16350(13) 0.0215(3) Uani 1 1 d . . . . .
F3 F 0.11388(14) 0.26086(14) 0.19920(15) 0.0260(4) Uani 1 1 d . . . . .
F4 F 0.17708(16) 0.28616(15) 0.38395(14) 0.0287(4) Uani 1 1 d . . . . .
F5 F 0.11022(16) 0.02056(15) 0.13291(15) 0.0328(4) Uani 1 1 d . . . . .
F6 F 0.21338(17) 0.02528(16) 0.29666(17) 0.0370(4) Uani 1 1 d . . . . .
F7 F 0.02648(17) 0.07578(16) 0.28838(18) 0.0405(5) Uani 1 1 d . . . . .
F8 F 0.25434(16) 0.76993(14) 0.35311(16) 0.0320(4) Uani 1 1 d . . . . .
F9 F 0.30749(15) 0.69122(16) 0.49048(14) 0.0306(4) Uani 1 1 d . . . . .
F10 F 0.07580(16) 0.54254(17) 0.24059(15) 0.0363(4) Uani 1 1 d . . . . .
F11 F 0.10834(16) 0.51326(15) 0.40962(17) 0.0337(4) Uani 1 1 d . . . . .
F12 F 0.01198(19) 0.76741(19) 0.34195(18) 0.0474(5) Uani 1 1 d . . . . .
F13 F -0.08542(16) 0.62496(18) 0.39466(18) 0.0436(5) Uani 1 1 d . . . . .
F14 F 0.06718(17) 0.75933(17) 0.51386(15) 0.0384(4) Uani 1 1 d . . . . .
O1 O 0.62159(16) 0.53281(15) 0.02671(15) 0.0171(4) Uani 1 1 d . . . . .
O2 O 0.69607(17) 0.65967(16) 0.06081(17) 0.0236(4) Uani 1 1 d . . . . .
N1 N 0.48176(19) 0.37891(18) 0.19583(18) 0.0147(4) Uani 1 1 d . . . . .
N2 N 0.30454(19) 0.45721(19) 0.27717(19) 0.0176(4) Uani 1 1 d . . . . .
N3 N 0.44076(19) 0.63232(18) 0.26555(18) 0.0156(4) Uani 1 1 d . . . . .
C1 C 0.3792(2) 0.3692(2) 0.2406(2) 0.0156(5) Uani 1 1 d . . . . .
C2 C 0.3448(2) 0.5800(2) 0.2990(2) 0.0164(5) Uani 1 1 d . . . . .
C3 C 0.5746(2) 0.2912(2) 0.1852(2) 0.0151(5) Uani 1 1 d . . . . .
H3 H 0.5512 0.2297 0.2246 0.018 Uiso 1 1 calc R . . . .
C4 C 0.7046(2) 0.3687(2) 0.2459(2) 0.0200(5) Uani 1 1 d . . . . .
H4A H 0.7249 0.4339 0.2109 0.024 Uiso 1 1 calc R . . . .
H4B H 0.7026 0.4109 0.3297 0.024 Uiso 1 1 calc R . . . .
C5 C 0.8064(2) 0.2841(3) 0.2329(2) 0.0250(6) Uani 1 1 d . . . . .
H5A H 0.7905 0.2243 0.2748 0.030 Uiso 1 1 calc R . . . .
H5B H 0.8897 0.3359 0.2689 0.030 Uiso 1 1 calc R . . . .
C6 C 0.8079(3) 0.2111(3) 0.1040(3) 0.0285(6) Uani 1 1 d . . . . .
H6A H 0.8337 0.2705 0.0642 0.034 Uiso 1 1 calc R . . . .
H6B H 0.8705 0.1533 0.0987 0.034 Uiso 1 1 calc R . . . .
C7 C 0.6786(3) 0.1365(2) 0.0429(2) 0.0237(6) Uani 1 1 d . . . . .
H7A H 0.6574 0.0702 0.0765 0.028 Uiso 1 1 calc R . . . .
H7B H 0.6809 0.0955 -0.0410 0.028 Uiso 1 1 calc R . . . .
C8 C 0.5767(2) 0.2213(2) 0.0565(2) 0.0178(5) Uani 1 1 d . . . . .
H8A H 0.5934 0.2826 0.0162 0.021 Uiso 1 1 calc R . . . .
H8B H 0.4934 0.1699 0.0194 0.021 Uiso 1 1 calc R . . . .
C9 C 0.3285(2) 0.2449(2) 0.2576(2) 0.0172(5) Uani 1 1 d . . . . .
C10 C 0.1891(2) 0.2232(2) 0.2734(2) 0.0210(5) Uani 1 1 d . . . . .
C11 C 0.1341(3) 0.0822(3) 0.2466(3) 0.0274(6) Uani 1 1 d . . . . .
C12 C 0.2592(2) 0.6600(2) 0.3751(2) 0.0211(5) Uani 1 1 d . . . . .
C13 C 0.1195(3) 0.5981(2) 0.3558(2) 0.0232(6) Uani 1 1 d . . . . .
C14 C 0.0273(3) 0.6915(3) 0.4031(3) 0.0273(6) Uani 1 1 d . . . . .
C15 C 0.5026(2) 0.7649(2) 0.3238(2) 0.0166(5) Uani 1 1 d . . . . .
H15 H 0.4660 0.8031 0.3957 0.020 Uiso 1 1 calc R . . . .
C16 C 0.4828(3) 0.8400(2) 0.2421(2) 0.0219(5) Uani 1 1 d . . . . .
H16A H 0.3917 0.8418 0.2231 0.026 Uiso 1 1 calc R . . . .
H16B H 0.5131 0.7985 0.1685 0.026 Uiso 1 1 calc R . . . .
C17 C 0.5527(3) 0.9739(3) 0.2972(3) 0.0317(7) Uani 1 1 d . . . . .
H17A H 0.5166 1.0182 0.3665 0.038 Uiso 1 1 calc R . . . .
H17B H 0.5417 1.0188 0.2406 0.038 Uiso 1 1 calc R . . . .
C18 C 0.6936(3) 0.9749(3) 0.3335(3) 0.0356(7) Uani 1 1 d . . . . .
H18A H 0.7317 0.9394 0.2631 0.043 Uiso 1 1 calc R . . . .
H18B H 0.7359 1.0624 0.3738 0.043 Uiso 1 1 calc R . . . .
C19 C 0.7144(3) 0.8991(3) 0.4142(3) 0.0326(7) Uani 1 1 d . . . . .
H19A H 0.6850 0.9402 0.4885 0.039 Uiso 1 1 calc R . . . .
H19B H 0.8056 0.8970 0.4322 0.039 Uiso 1 1 calc R . . . .
C20 C 0.6434(2) 0.7646(2) 0.3582(2) 0.0226(6) Uani 1 1 d . . . . .
H20A H 0.6785 0.7207 0.2881 0.027 Uiso 1 1 calc R . . . .
H20B H 0.6550 0.7189 0.4140 0.027 Uiso 1 1 calc R . . . .
C21 C 0.8220(3) 0.6423(3) 0.0473(3) 0.0352(7) Uani 1 1 d . . . . .
H21A H 0.8259 0.5932 -0.0345 0.042 Uiso 1 1 calc R . . . .
H21B H 0.8555 0.5973 0.0984 0.042 Uiso 1 1 calc R . . . .
C22 C 0.8973(3) 0.7725(3) 0.0816(3) 0.0472(9) Uani 1 1 d . . . . .
H22A H 0.8609 0.8169 0.0323 0.071 Uiso 1 1 calc GR . . . .
H22B H 0.9848 0.7659 0.0711 0.071 Uiso 1 1 calc GR . . . .
H22C H 0.8948 0.8189 0.1636 0.071 Uiso 1 1 calc GR . . . .


_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
Zn Zn 3.0474(7) 2_665 ?
Zn O1 2.0487(18) 2_665 ?
Zn O1 1.9570(17) . ?
Zn N1 2.004(2) . ?
Zn N3 1.999(2) . ?
F1 C9 1.375(3) . ?
F2 C9 1.367(3) . ?
F3 C10 1.351(3) . ?
F4 C10 1.346(3) . ?
F5 C11 1.323(3) . ?
F6 C11 1.336(3) . ?
F7 C11 1.334(3) . ?
F8 C12 1.370(3) . ?
F9 C12 1.365(3) . ?
F10 C13 1.350(3) . ?
F11 C13 1.339(3) . ?
F12 C14 1.326(3) . ?
F13 C14 1.340(3) . ?
F14 C14 1.321(3) . ?
O1 Zn 2.0487(18) 2_665 ?
O1 O2 1.483(2) . ?
O2 C21 1.421(3) . ?
N1 C1 1.307(3) . ?
N1 C3 1.483(3) . ?
N2 C1 1.357(3) . ?
N2 C2 1.351(3) . ?
N3 C2 1.316(3) . ?
N3 C15 1.490(3) . ?
C1 C9 1.550(3) . ?
C2 C12 1.553(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.540(3) . ?
C3 C8 1.529(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.532(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.537(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.525(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.536(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.550(3) . ?
C10 C11 1.568(4) . ?
C12 C13 1.555(4) . ?
C13 C14 1.565(4) . ?
C15 H15 1.0000 . ?
C15 C16 1.526(3) . ?
C15 C20 1.533(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.526(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.535(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.523(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.536(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.518(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
O1 Zn Zn 41.60(5) . 2_665 ?
O1 Zn Zn 39.36(5) 2_665 2_665 ?
O1 Zn O1 80.96(7) . 2_665 ?
O1 Zn N1 123.80(8) . . ?
O1 Zn N3 136.02(8) . . ?
N1 Zn Zn 125.81(6) . 2_665 ?
N1 Zn O1 109.82(8) . 2_665 ?
N3 Zn Zn 138.39(6) . 2_665 ?
N3 Zn O1 115.14(8) . 2_665 ?
N3 Zn N1 90.49(8) . . ?
Zn O1 Zn 99.04(7) . 2_665 ?
O2 O1 Zn 113.42(12) . 2_665 ?
O2 O1 Zn 114.30(12) . . ?
C21 O2 O1 106.47(18) . . ?
C1 N1 Zn 114.38(16) . . ?
C1 N1 C3 124.6(2) . . ?
C3 N1 Zn 120.87(15) . . ?
C2 N2 C1 121.9(2) . . ?
C2 N3 Zn 113.91(16) . . ?
C2 N3 C15 124.0(2) . . ?
C15 N3 Zn 122.06(15) . . ?
N1 C1 N2 128.3(2) . . ?
N1 C1 C9 120.4(2) . . ?
N2 C1 C9 111.4(2) . . ?
N2 C2 C12 109.7(2) . . ?
N3 C2 N2 128.8(2) . . ?
N3 C2 C12 121.5(2) . . ?
N1 C3 H3 109.6 . . ?
N1 C3 C4 107.79(19) . . ?
N1 C3 C8 109.84(19) . . ?
C4 C3 H3 109.6 . . ?
C8 C3 H3 109.6 . . ?
C8 C3 C4 110.5(2) . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.5(2) . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C4 C5 C6 111.3(2) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 C5 111.2(2) . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C6 C7 C8 111.2(2) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C3 C8 C7 110.9(2) . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
F1 C9 C1 109.4(2) . . ?
F1 C9 C10 106.6(2) . . ?
F2 C9 F1 106.80(19) . . ?
F2 C9 C1 109.49(19) . . ?
F2 C9 C10 105.87(19) . . ?
C10 C9 C1 118.0(2) . . ?
F3 C10 C9 110.9(2) . . ?
F3 C10 C11 104.9(2) . . ?
F4 C10 F3 109.6(2) . . ?
F4 C10 C9 109.9(2) . . ?
F4 C10 C11 107.5(2) . . ?
C9 C10 C11 113.8(2) . . ?
F5 C11 F6 108.6(2) . . ?
F5 C11 F7 108.2(2) . . ?
F5 C11 C10 111.2(2) . . ?
F6 C11 C10 111.5(2) . . ?
F7 C11 F6 108.3(2) . . ?
F7 C11 C10 109.0(2) . . ?
F8 C12 C2 110.8(2) . . ?
F8 C12 C13 105.2(2) . . ?
F9 C12 F8 106.9(2) . . ?
F9 C12 C2 110.0(2) . . ?
F9 C12 C13 108.0(2) . . ?
C2 C12 C13 115.5(2) . . ?
F10 C13 C12 110.0(2) . . ?
F10 C13 C14 105.7(2) . . ?
F11 C13 F10 109.7(2) . . ?
F11 C13 C12 110.8(2) . . ?
F11 C13 C14 106.0(2) . . ?
C12 C13 C14 114.5(2) . . ?
F12 C14 F13 107.8(2) . . ?
F12 C14 C13 112.2(2) . . ?
F13 C14 C13 108.4(2) . . ?
F14 C14 F12 109.0(2) . . ?
F14 C14 F13 108.3(2) . . ?
F14 C14 C13 111.0(2) . . ?
N3 C15 H15 109.3 . . ?
N3 C15 C16 110.6(2) . . ?
N3 C15 C20 107.80(19) . . ?
C16 C15 H15 109.3 . . ?
C16 C15 C20 110.4(2) . . ?
C20 C15 H15 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C15 C16 C17 111.4(2) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 C18 110.9(2) . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 C17 111.2(2) . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C18 C19 C20 111.2(3) . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
C15 C20 C19 110.7(2) . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
O2 C21 H21A 110.5 . . ?
O2 C21 H21B 110.5 . . ?
O2 C21 C22 106.1(3) . . ?
H21A C21 H21B 108.7 . . ?
C22 C21 H21A 110.5 . . ?
C22 C21 H21B 110.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
Zn O1 O2 C21 138.32(19) . . . . ?
Zn O1 O2 C21 -109.1(2) 2_665 . . . ?
Zn N1 C1 N2 -20.8(3) . . . . ?
Zn N1 C1 C9 159.16(18) . . . . ?
Zn N1 C3 C4 60.3(2) . . . . ?
Zn N1 C3 C8 -60.2(2) . . . . ?
Zn N3 C2 N2 20.3(3) . . . . ?
Zn N3 C2 C12 -160.17(19) . . . . ?
Zn N3 C15 C16 66.2(2) . . . . ?
Zn N3 C15 C20 -54.6(2) . . . . ?
F1 C9 C10 F3 165.32(19) . . . . ?
F1 C9 C10 F4 44.0(3) . . . . ?
F1 C9 C10 C11 -76.6(3) . . . . ?
F2 C9 C10 F3 -81.2(2) . . . . ?
F2 C9 C10 F4 157.49(19) . . . . ?
F2 C9 C10 C11 36.8(3) . . . . ?
F3 C10 C11 F5 46.2(3) . . . . ?
F3 C10 C11 F6 167.5(2) . . . . ?
F3 C10 C11 F7 -73.1(3) . . . . ?
F4 C10 C11 F5 162.7(2) . . . . ?
F4 C10 C11 F6 -76.0(3) . . . . ?
F4 C10 C11 F7 43.5(3) . . . . ?
F8 C12 C13 F10 78.8(2) . . . . ?
F8 C12 C13 F11 -159.9(2) . . . . ?
F8 C12 C13 C14 -40.1(3) . . . . ?
F9 C12 C13 F10 -167.29(19) . . . . ?
F9 C12 C13 F11 -45.9(3) . . . . ?
F9 C12 C13 C14 73.8(3) . . . . ?
F10 C13 C14 F12 -52.3(3) . . . . ?
F10 C13 C14 F13 66.6(3) . . . . ?
F10 C13 C14 F14 -174.7(2) . . . . ?
F11 C13 C14 F12 -168.7(2) . . . . ?
F11 C13 C14 F13 -49.8(3) . . . . ?
F11 C13 C14 F14 69.0(3) . . . . ?
O1 O2 C21 C22 179.6(2) . . . . ?
N1 C1 C9 F1 76.7(3) . . . . ?
N1 C1 C9 F2 -40.1(3) . . . . ?
N1 C1 C9 C10 -161.2(2) . . . . ?
N1 C3 C4 C5 -177.3(2) . . . . ?
N1 C3 C8 C7 176.1(2) . . . . ?
N2 C1 C9 F1 -103.3(2) . . . . ?
N2 C1 C9 F2 139.9(2) . . . . ?
N2 C1 C9 C10 18.8(3) . . . . ?
N2 C2 C12 F8 -150.6(2) . . . . ?
N2 C2 C12 F9 91.3(3) . . . . ?
N2 C2 C12 C13 -31.2(3) . . . . ?
N3 C2 C12 F8 29.8(3) . . . . ?
N3 C2 C12 F9 -88.2(3) . . . . ?
N3 C2 C12 C13 149.2(2) . . . . ?
N3 C15 C16 C17 -176.2(2) . . . . ?
N3 C15 C20 C19 177.5(2) . . . . ?
C1 N1 C3 C4 -124.9(2) . . . . ?
C1 N1 C3 C8 114.6(3) . . . . ?
C1 N2 C2 N3 17.5(4) . . . . ?
C1 N2 C2 C12 -162.0(2) . . . . ?
C1 C9 C10 F3 41.8(3) . . . . ?
C1 C9 C10 F4 -79.5(3) . . . . ?
C1 C9 C10 C11 159.8(2) . . . . ?
C2 N2 C1 N1 -17.2(4) . . . . ?
C2 N2 C1 C9 162.8(2) . . . . ?
C2 N3 C15 C16 -114.4(3) . . . . ?
C2 N3 C15 C20 124.8(3) . . . . ?
C2 C12 C13 F10 -43.7(3) . . . . ?
C2 C12 C13 F11 77.7(3) . . . . ?
C2 C12 C13 C14 -162.6(2) . . . . ?
C3 N1 C1 N2 164.1(2) . . . . ?
C3 N1 C1 C9 -16.0(4) . . . . ?
C3 C4 C5 C6 56.2(3) . . . . ?
C4 C3 C8 C7 57.3(3) . . . . ?
C4 C5 C6 C7 -55.3(3) . . . . ?
C5 C6 C7 C8 55.0(3) . . . . ?
C6 C7 C8 C3 -56.4(3) . . . . ?
C8 C3 C4 C5 -57.2(3) . . . . ?
C9 C10 C11 F5 -75.3(3) . . . . ?
C9 C10 C11 F6 46.0(3) . . . . ?
C9 C10 C11 F7 165.5(2) . . . . ?
C12 C13 C14 F12 68.9(3) . . . . ?
C12 C13 C14 F13 -172.2(2) . . . . ?
C12 C13 C14 F14 -53.4(3) . . . . ?
C15 N3 C2 N2 -159.1(2) . . . . ?
C15 N3 C2 C12 20.4(4) . . . . ?
C15 C16 C17 C18 56.2(3) . . . . ?
C16 C15 C20 C19 56.6(3) . . . . ?
C16 C17 C18 C19 -55.3(3) . . . . ?
C17 C18 C19 C20 55.5(3) . . . . ?
C18 C19 C20 C15 -56.3(3) . . . . ?
C20 C15 C16 C17 -57.0(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
