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

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

data_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1061236'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H32 Cl2 N2 O2 Zn'
_chemical_formula_sum            'C32 H32 Cl2 N2 O2 Zn'
_chemical_formula_weight         612.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   18.3252(3)
_cell_length_b                   11.6963(2)
_cell_length_c                   26.7400(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.0670(10)
_cell_angle_gamma                90
_cell_volume                     5687.83(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14848
_cell_measurement_theta_min      4.1070
_cell_measurement_theta_max      75.9690

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             2544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    3.182
_exptl_absorpt_correction_T_min  0.49341
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray source'
_diffrn_measurement_device_type  'Agilent SuperNova with AtlasS2 detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27764
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.331
_diffrn_reflns_theta_max         76.260
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5871
_reflns_number_gt                5447
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_cell_refinement       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction        
'CrysAlisPro V 1.171.37.31, Agilent Technologies'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+8.8434P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5871
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.73031(9) 0.51682(14) 0.75766(6) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.76361(10) 0.60722(15) 0.79137(7) 0.0185(3) Uani 1 1 d . . . . .
C3 C 0.74455(10) 0.66203(16) 0.83358(7) 0.0214(4) Uani 1 1 d . . . . .
H3 H 0.7033 0.6394 0.8482 0.026 Uiso 1 1 calc R U . . .
C4 C 0.78919(11) 0.75347(16) 0.85417(7) 0.0252(4) Uani 1 1 d . . . . .
H4 H 0.7767 0.7904 0.8827 0.030 Uiso 1 1 calc R U . . .
C5 C 0.85017(11) 0.78972(16) 0.83359(7) 0.0255(4) Uani 1 1 d . . . . .
H5 H 0.8785 0.8493 0.8486 0.031 Uiso 1 1 calc R U . . .
C6 C 0.87033(10) 0.73680(15) 0.78950(7) 0.0222(4) Uani 1 1 d . . . . .
C7 C 0.82577(10) 0.64605(15) 0.76949(7) 0.0195(4) Uani 1 1 d . . . . .
C8 C 0.92909(11) 0.76893(16) 0.76260(8) 0.0255(4) Uani 1 1 d . . . . .
H8 H 0.9607 0.8274 0.7749 0.031 Uiso 1 1 calc R U . . .
C9 C 0.93991(10) 0.71459(16) 0.71841(8) 0.0250(4) Uani 1 1 d . . . . .
H9 H 0.9781 0.7386 0.7011 0.030 Uiso 1 1 calc R U . . .
C10 C 0.89452(10) 0.62325(15) 0.69865(7) 0.0216(4) Uani 1 1 d . . . . .
H10 H 0.9027 0.5877 0.6687 0.026 Uiso 1 1 calc R U . . .
C11 C 0.83781(10) 0.58792(15) 0.72457(7) 0.0192(3) Uani 1 1 d . . . . .
C12 C 0.77730(9) 0.50506(14) 0.71510(6) 0.0172(3) Uani 1 1 d . . . . .
C13 C 0.62922(10) 0.45273(15) 0.79677(6) 0.0179(3) Uani 1 1 d . . . . .
C14 C 0.55407(10) 0.47069(15) 0.78696(7) 0.0190(3) Uani 1 1 d . . . . .
H14 H 0.5322 0.4784 0.7538 0.023 Uiso 1 1 calc R U . . .
C15 C 0.51100(10) 0.47731(15) 0.82627(7) 0.0199(3) Uani 1 1 d . . . . .
H15 H 0.4609 0.4927 0.8198 0.024 Uiso 1 1 calc R U . . .
C16 C 0.54399(10) 0.46061(16) 0.87549(7) 0.0210(4) Uani 1 1 d . . . . .
C17 C 0.61872(10) 0.43413(16) 0.88494(7) 0.0221(4) Uani 1 1 d . . . . .
H17 H 0.6398 0.4189 0.9177 0.027 Uiso 1 1 calc R U . . .
C18 C 0.66149(10) 0.43041(16) 0.84586(7) 0.0210(4) Uani 1 1 d . . . . .
H18 H 0.7113 0.4132 0.8522 0.025 Uiso 1 1 calc R U . . .
C19 C 0.43270(10) 0.50456(18) 0.90996(7) 0.0242(4) Uani 1 1 d . . . . .
H19A H 0.4020 0.4503 0.8896 0.029 Uiso 1 1 calc R U . . .
H19B H 0.4290 0.5783 0.8932 0.029 Uiso 1 1 calc R U . . .
C20 C 0.40848(11) 0.51392(19) 0.96192(7) 0.0269(4) Uani 1 1 d . . . . .
H20A H 0.4379 0.5716 0.9811 0.032 Uiso 1 1 calc R U . . .
H20B H 0.4171 0.4415 0.9793 0.032 Uiso 1 1 calc R U . . .
C21 C 0.32718(11) 0.54541(19) 0.95985(7) 0.0280(4) Uani 1 1 d . . . . .
H21A H 0.2985 0.4949 0.9363 0.034 Uiso 1 1 calc R U . . .
H21B H 0.3117 0.5330 0.9928 0.034 Uiso 1 1 calc R U . . .
C22 C 0.31071(12) 0.6682(2) 0.94411(9) 0.0333(5) Uani 1 1 d . . . . .
H22A H 0.3403 0.7188 0.9664 0.050 Uiso 1 1 calc R U . . .
H22B H 0.2596 0.6841 0.9456 0.050 Uiso 1 1 calc R U . . .
H22C H 0.3218 0.6794 0.9103 0.050 Uiso 1 1 calc R U . . .
C23 C 0.80311(10) 0.41235(15) 0.64134(7) 0.0188(3) Uani 1 1 d . . . . .
C24 C 0.77687(11) 0.43154(18) 0.59120(7) 0.0269(4) Uani 1 1 d . . . . .
H24 H 0.7287 0.4557 0.5822 0.032 Uiso 1 1 calc R U . . .
C25 C 0.82319(11) 0.4144(2) 0.55467(7) 0.0311(5) Uani 1 1 d . . . . .
H25 H 0.8062 0.4292 0.5211 0.037 Uiso 1 1 calc R U . . .
C26 C 0.89475(10) 0.37522(16) 0.56748(7) 0.0226(4) Uani 1 1 d . . . . .
C27 C 0.91973(10) 0.35162(16) 0.61759(7) 0.0221(4) Uani 1 1 d . . . . .
H27 H 0.9671 0.3237 0.6265 0.027 Uiso 1 1 calc R U . . .
C28 C 0.87358(11) 0.37002(16) 0.65424(7) 0.0229(4) Uani 1 1 d . . . . .
H28 H 0.8901 0.3538 0.6878 0.027 Uiso 1 1 calc R U . . .
C29 C 1.01093(10) 0.33113(17) 0.53952(7) 0.0246(4) Uani 1 1 d . . . . .
H29A H 1.0159 0.2600 0.5583 0.030 Uiso 1 1 calc R U . . .
H29B H 1.0372 0.3904 0.5597 0.030 Uiso 1 1 calc R U . . .
C30 C 1.04196(11) 0.31816(19) 0.49012(7) 0.0279(4) Uani 1 1 d . . . . .
H30A H 1.0322 0.3872 0.4703 0.034 Uiso 1 1 calc R U . . .
H30B H 1.0177 0.2550 0.4713 0.034 Uiso 1 1 calc R U . . .
C31 C 1.12470(12) 0.2962(2) 0.49839(8) 0.0333(5) Uani 1 1 d . . . . .
H31A H 1.1352 0.2381 0.5242 0.040 Uiso 1 1 calc R U . . .
H31B H 1.1497 0.3658 0.5105 0.040 Uiso 1 1 calc R U . . .
C32 C 1.15449(14) 0.2572(3) 0.45028(9) 0.0470(6) Uani 1 1 d . . . . .
H32A H 1.1300 0.1882 0.4382 0.070 Uiso 1 1 calc R U . . .
H32B H 1.2063 0.2431 0.4573 0.070 Uiso 1 1 calc R U . . .
H32C H 1.1459 0.3157 0.4251 0.070 Uiso 1 1 calc R U . . .
Cl1 Cl 0.65103(2) 0.17457(4) 0.70314(2) 0.02345(11) Uani 1 1 d . . . . .
Cl2 Cl 0.56427(2) 0.43045(4) 0.63677(2) 0.02649(11) Uani 1 1 d . . . . .
N1 N 0.67245(8) 0.45458(12) 0.75611(5) 0.0168(3) Uani 1 1 d . . . . .
N2 N 0.75667(8) 0.43381(12) 0.67965(5) 0.0171(3) Uani 1 1 d . . . . .
Zn1 Zn 0.65553(2) 0.36016(2) 0.68949(2) 0.01688(8) Uani 1 1 d . . . . .
O1 O 0.50775(7) 0.46617(12) 0.91692(5) 0.0253(3) Uani 1 1 d . . . . .
O2 O 0.93480(8) 0.36114(13) 0.52825(5) 0.0285(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.283(2) . ?
C1 C2 1.472(2) . ?
C1 C12 1.516(2) . ?
C2 C3 1.380(3) . ?
C2 C7 1.418(3) . ?
C3 C4 1.416(3) . ?
C4 C5 1.372(3) . ?
C5 C6 1.420(3) . ?
C6 C7 1.404(2) . ?
C6 C8 1.417(3) . ?
C7 C11 1.421(3) . ?
C8 C9 1.378(3) . ?
C9 C10 1.416(3) . ?
C10 C11 1.381(3) . ?
C11 C12 1.471(2) . ?
C12 N2 1.284(2) . ?
C13 C14 1.386(2) . ?
C13 C18 1.396(2) . ?
C13 N1 1.422(2) . ?
C14 C15 1.392(2) . ?
C15 C16 1.393(3) . ?
C16 O1 1.361(2) . ?
C16 C17 1.397(3) . ?
C17 C18 1.382(3) . ?
C19 O1 1.437(2) . ?
C19 C20 1.514(3) . ?
C20 C21 1.529(3) . ?
C21 C22 1.516(3) . ?
C23 C24 1.386(3) . ?
C23 C28 1.386(3) . ?
C23 N2 1.432(2) . ?
C24 C25 1.385(3) . ?
C25 C26 1.391(3) . ?
C26 O2 1.362(2) . ?
C26 C27 1.389(3) . ?
C27 C28 1.388(3) . ?
C29 O2 1.434(2) . ?
C29 C30 1.509(3) . ?
C30 C31 1.527(3) . ?
C31 C32 1.528(3) . ?
Cl1 Zn1 2.2044(5) . ?
Cl2 Zn1 2.2090(5) . ?
N1 Zn1 2.0865(14) . ?
N2 Zn1 2.0896(14) . ?

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
N1 C1 C2 134.92(16) . . ?
N1 C1 C12 117.91(15) . . ?
C2 C1 C12 107.09(14) . . ?
C3 C2 C7 119.07(17) . . ?
C3 C2 C1 134.98(17) . . ?
C7 C2 C1 105.72(15) . . ?
C2 C3 C4 118.46(18) . . ?
C5 C4 C3 122.52(18) . . ?
C4 C5 C6 120.41(17) . . ?
C7 C6 C8 116.70(18) . . ?
C7 C6 C5 116.57(18) . . ?
C8 C6 C5 126.68(18) . . ?
C6 C7 C2 122.94(17) . . ?
C6 C7 C11 122.71(17) . . ?
C2 C7 C11 114.32(16) . . ?
C9 C8 C6 120.78(17) . . ?
C8 C9 C10 121.89(18) . . ?
C11 C10 C9 118.82(18) . . ?
C10 C11 C7 119.06(17) . . ?
C10 C11 C12 135.09(17) . . ?
C7 C11 C12 105.59(15) . . ?
N2 C12 C11 134.61(17) . . ?
N2 C12 C1 118.06(15) . . ?
C11 C12 C1 107.27(14) . . ?
C14 C13 C18 120.15(16) . . ?
C14 C13 N1 119.15(15) . . ?
C18 C13 N1 120.68(16) . . ?
C13 C14 C15 120.53(16) . . ?
C14 C15 C16 119.02(16) . . ?
O1 C16 C15 124.32(17) . . ?
O1 C16 C17 115.40(16) . . ?
C15 C16 C17 120.27(17) . . ?
C18 C17 C16 120.32(17) . . ?
C17 C18 C13 119.41(17) . . ?
O1 C19 C20 106.73(15) . . ?
C19 C20 C21 112.25(16) . . ?
C22 C21 C20 113.45(17) . . ?
C24 C23 C28 120.01(17) . . ?
C24 C23 N2 119.85(16) . . ?
C28 C23 N2 120.13(16) . . ?
C25 C24 C23 119.27(18) . . ?
C24 C25 C26 120.98(18) . . ?
O2 C26 C27 125.02(18) . . ?
O2 C26 C25 115.52(17) . . ?
C27 C26 C25 119.45(17) . . ?
C28 C27 C26 119.55(18) . . ?
C23 C28 C27 120.63(17) . . ?
O2 C29 C30 107.60(15) . . ?
C29 C30 C31 111.39(17) . . ?
C30 C31 C32 112.31(19) . . ?
C1 N1 C13 121.33(15) . . ?
C1 N1 Zn1 111.31(11) . . ?
C13 N1 Zn1 127.33(11) . . ?
C12 N2 C23 119.67(15) . . ?
C12 N2 Zn1 111.10(12) . . ?
C23 N2 Zn1 129.20(11) . . ?
N1 Zn1 N2 81.27(6) . . ?
N1 Zn1 Cl1 112.61(4) . . ?
N2 Zn1 Cl1 118.60(4) . . ?
N1 Zn1 Cl2 111.66(4) . . ?
N2 Zn1 Cl2 112.32(4) . . ?
Cl1 Zn1 Cl2 115.555(19) . . ?
C16 O1 C19 117.67(14) . . ?
C26 O2 C29 118.04(15) . . ?

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
N1 C1 C2 C3 -2.0(4) . . . . ?
C12 C1 C2 C3 174.60(19) . . . . ?
N1 C1 C2 C7 -176.22(19) . . . . ?
C12 C1 C2 C7 0.40(18) . . . . ?
C7 C2 C3 C4 -1.6(3) . . . . ?
C1 C2 C3 C4 -175.19(18) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
C4 C5 C6 C8 176.30(18) . . . . ?
C8 C6 C7 C2 -177.82(16) . . . . ?
C5 C6 C7 C2 -0.1(3) . . . . ?
C8 C6 C7 C11 0.0(3) . . . . ?
C5 C6 C7 C11 177.70(16) . . . . ?
C3 C2 C7 C6 1.5(3) . . . . ?
C1 C2 C7 C6 176.80(16) . . . . ?
C3 C2 C7 C11 -176.49(16) . . . . ?
C1 C2 C7 C11 -1.2(2) . . . . ?
C7 C6 C8 C9 1.5(3) . . . . ?
C5 C6 C8 C9 -175.90(18) . . . . ?
C6 C8 C9 C10 -1.6(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C7 1.5(3) . . . . ?
C9 C10 C11 C12 174.67(18) . . . . ?
C6 C7 C11 C10 -1.5(3) . . . . ?
C2 C7 C11 C10 176.45(16) . . . . ?
C6 C7 C11 C12 -176.53(16) . . . . ?
C2 C7 C11 C12 1.5(2) . . . . ?
C10 C11 C12 N2 2.0(4) . . . . ?
C7 C11 C12 N2 175.81(19) . . . . ?
C10 C11 C12 C1 -174.90(19) . . . . ?
C7 C11 C12 C1 -1.10(18) . . . . ?
N1 C1 C12 N2 0.2(2) . . . . ?
C2 C1 C12 N2 -177.06(15) . . . . ?
N1 C1 C12 C11 177.74(15) . . . . ?
C2 C1 C12 C11 0.44(18) . . . . ?
C18 C13 C14 C15 6.0(3) . . . . ?
N1 C13 C14 C15 -175.52(16) . . . . ?
C13 C14 C15 C16 -2.8(3) . . . . ?
C14 C15 C16 O1 179.29(17) . . . . ?
C14 C15 C16 C17 -2.0(3) . . . . ?
O1 C16 C17 C18 -177.60(17) . . . . ?
C15 C16 C17 C18 3.5(3) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C14 C13 C18 C17 -4.4(3) . . . . ?
N1 C13 C18 C17 177.16(16) . . . . ?
O1 C19 C20 C21 -175.59(17) . . . . ?
C19 C20 C21 C22 -71.7(2) . . . . ?
C28 C23 C24 C25 -3.8(3) . . . . ?
N2 C23 C24 C25 177.71(18) . . . . ?
C23 C24 C25 C26 1.8(3) . . . . ?
C24 C25 C26 O2 179.68(19) . . . . ?
C24 C25 C26 C27 0.8(3) . . . . ?
O2 C26 C27 C28 179.75(18) . . . . ?
C25 C26 C27 C28 -1.5(3) . . . . ?
C24 C23 C28 C27 3.1(3) . . . . ?
N2 C23 C28 C27 -178.37(16) . . . . ?
C26 C27 C28 C23 -0.4(3) . . . . ?
O2 C29 C30 C31 175.09(17) . . . . ?
C29 C30 C31 C32 167.5(2) . . . . ?
C2 C1 N1 C13 -9.5(3) . . . . ?
C12 C1 N1 C13 174.13(14) . . . . ?
C2 C1 N1 Zn1 171.92(16) . . . . ?
C12 C1 N1 Zn1 -4.42(18) . . . . ?
C14 C13 N1 C1 128.57(18) . . . . ?
C18 C13 N1 C1 -53.0(2) . . . . ?
C14 C13 N1 Zn1 -53.1(2) . . . . ?
C18 C13 N1 Zn1 125.33(16) . . . . ?
C11 C12 N2 C23 9.2(3) . . . . ?
C1 C12 N2 C23 -174.12(14) . . . . ?
C11 C12 N2 Zn1 -172.57(16) . . . . ?
C1 C12 N2 Zn1 4.08(18) . . . . ?
C24 C23 N2 C12 -121.92(19) . . . . ?
C28 C23 N2 C12 59.5(2) . . . . ?
C24 C23 N2 Zn1 60.2(2) . . . . ?
C28 C23 N2 Zn1 -118.29(17) . . . . ?
C15 C16 O1 C19 -7.5(3) . . . . ?
C17 C16 O1 C19 173.73(16) . . . . ?
C20 C19 O1 C16 -174.46(16) . . . . ?
C27 C26 O2 C29 -6.9(3) . . . . ?
C25 C26 O2 C29 174.37(18) . . . . ?
C30 C29 O2 C26 178.74(16) . . . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1061237'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H32 Cl2 N2 O2 Zn, C H2 Cl2'
_chemical_formula_sum            'C33 H34 Cl4 N2 O2 Zn'
_chemical_formula_weight         697.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   17.490(3)
_cell_length_b                   11.6120(17)
_cell_length_c                   17.926(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.505(3)
_cell_angle_gamma                90
_cell_volume                     3229.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    24575
_cell_measurement_theta_min      6.21
_cell_measurement_theta_max      55.01

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.124
_shelx_estimated_absorpt_T_min   0.572
_shelx_estimated_absorpt_T_max   0.806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
Abscor. T. Higashi. (2001). Rigaku Corp. Tokyo, Japan
;



_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku SCX-Mini Mercury CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27165
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.105
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5671
_reflns_number_gt                5065
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_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     
'w=1/[σ²(Fo²)+(0.0944P)²+26.5826P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5671
_refine_ls_number_parameters     409
_refine_ls_number_restraints     93
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0761
_refine_ls_wR_factor_ref         0.2013
_refine_ls_wR_factor_gt          0.1944
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4843(3) 0.2662(4) 0.9546(3) 0.0170(10) Uani 1 1 d . . . . .
C2 C 0.5426(3) 0.3565(4) 0.9511(3) 0.0178(10) Uani 1 1 d . . . . .
C3 C 0.5552(3) 0.4066(4) 0.8878(3) 0.0211(11) Uani 1 1 d . . . . .
H3 H 0.5253 0.3807 0.8326 0.025 Uiso 1 1 calc R U . . .
C4 C 0.6151(3) 0.4989(5) 0.9091(3) 0.0242(11) Uani 1 1 d . . . . .
H4 H 0.6241 0.5327 0.8668 0.029 Uiso 1 1 calc R U . . .
C5 C 0.6604(3) 0.5402(5) 0.9899(4) 0.0241(11) Uani 1 1 d . . . . .
H5 H 0.6997 0.5998 1.0013 0.029 Uiso 1 1 calc R U . . .
C6 C 0.6472(3) 0.4921(4) 1.0559(3) 0.0192(10) Uani 1 1 d . . . . .
C7 C 0.5879(3) 0.4001(4) 1.0346(3) 0.0168(10) Uani 1 1 d . . . . .
C8 C 0.6864(3) 0.5285(4) 1.1413(3) 0.0216(11) Uani 1 1 d . . . . .
H8 H 0.7266 0.5879 1.1588 0.026 Uiso 1 1 calc R U . . .
C9 C 0.6651(3) 0.4761(4) 1.1985(3) 0.0219(11) Uani 1 1 d . . . . .
H9 H 0.6911 0.5019 1.2539 0.026 Uiso 1 1 calc R U . . .
C10 C 0.6051(3) 0.3846(4) 1.1755(3) 0.0199(10) Uani 1 1 d . . . . .
H10 H 0.5919 0.3510 1.2153 0.024 Uiso 1 1 calc R U . . .
C11 C 0.5665(3) 0.3456(4) 1.0936(3) 0.0178(10) Uani 1 1 d . . . . .
C12 C 0.4984(3) 0.2607(4) 1.0445(3) 0.0173(10) Uani 1 1 d . . . . .
C13 C 0.4111(3) 0.1978(4) 0.8137(3) 0.0208(11) Uani 1 1 d . . . . .
C14 C 0.3298(3) 0.2223(5) 0.7497(3) 0.0222(11) Uani 1 1 d . . . . .
H14 H 0.2852 0.2384 0.7626 0.027 Uiso 1 1 calc R U . . .
C15 C 0.3142(4) 0.2229(5) 0.6660(3) 0.0252(11) Uani 1 1 d . . . . .
H15 H 0.2601 0.2425 0.6232 0.030 Uiso 1 1 calc R U . . .
C16 C 0.3808(4) 0.1938(5) 0.6476(3) 0.0254(12) Uani 1 1 d . . . . .
C17 C 0.4618(4) 0.1633(5) 0.7122(3) 0.0270(12) Uani 1 1 d . . . . .
H17 H 0.5055 0.1413 0.6993 0.032 Uiso 1 1 calc R U . . .
C18 C 0.4772(4) 0.1658(5) 0.7950(3) 0.0244(11) Uani 1 1 d . . . . .
H18 H 0.5312 0.1463 0.8379 0.029 Uiso 1 1 calc R U . . .
C19 C 0.2933(4) 0.2366(6) 0.5011(4) 0.0391(15) Uani 1 1 d . . . . .
H19A H 0.2819 0.3135 0.5147 0.047 Uiso 1 1 calc R U . . .
H19B H 0.2455 0.1871 0.4933 0.047 Uiso 1 1 calc R U . . .
C20 C 0.3038(6) 0.2391(9) 0.4221(4) 0.063(2) Uani 1 1 d . . . . .
H20A H 0.3501 0.2919 0.4307 0.075 Uiso 1 1 calc R U . . .
H20B H 0.3211 0.1630 0.4133 0.075 Uiso 1 1 calc R U . . .
C21 C 0.2266(8) 0.2733(12) 0.3458(6) 0.092(4) Uani 1 1 d . . . . .
H21A H 0.2360 0.2608 0.2972 0.111 Uiso 1 1 calc R U . . .
H21B H 0.1783 0.2259 0.3395 0.111 Uiso 1 1 calc R U . . .
C22 C 0.2059(7) 0.3952(11) 0.3495(7) 0.084(3) Uani 1 1 d . . . . .
H22A H 0.1806 0.4038 0.3867 0.126 Uiso 1 1 calc R U . . .
H22B H 0.1658 0.4211 0.2942 0.126 Uiso 1 1 calc R U . . .
H22C H 0.2576 0.4403 0.3699 0.126 Uiso 1 1 calc R U . . .
C23 C 0.4601(3) 0.1754(4) 1.1429(3) 0.0197(10) Uani 1 1 d . . . . .
C24 C 0.3885(4) 0.1867(5) 1.1577(4) 0.0303(13) Uani 1 1 d . . . . .
H24 H 0.3344 0.2029 1.1137 0.036 Uiso 1 1 calc R U . . .
C25 C 0.3995(4) 0.1733(6) 1.2390(4) 0.0399(16) Uani 1 1 d . . . . .
H25 H 0.3528 0.1831 1.2498 0.048 Uiso 1 1 calc R U . . .
C26 C 0.4806(4) 0.1453(6) 1.3049(4) 0.0331(14) Uani 1 1 d . . . . .
C27 C 0.5504(4) 0.1266(5) 1.2888(3) 0.0260(12) Uani 1 1 d . . . . .
H27 H 0.6035 0.1038 1.3318 0.031 Uiso 1 1 calc R U . . .
C28 C 0.5398(3) 0.1425(4) 1.2075(3) 0.0214(11) Uani 1 1 d . . . . .
H28 H 0.5861 0.1310 1.1964 0.026 Uiso 1 1 calc R U . . .
C29 C 0.5698(5) 0.1272(7) 1.4539(4) 0.0491(19) Uani 1 1 d . . . . .
H29A H 0.6099 0.1802 1.4486 0.059 Uiso 1 1 calc R U . . .
H29B H 0.5913 0.0494 1.4571 0.059 Uiso 1 1 calc R U . . .
C30 C 0.5595(7) 0.1555(10) 1.5329(5) 0.074(3) Uani 1 1 d . . . . .
H30A H 0.5209 0.2208 1.5202 0.089 Uiso 1 1 calc R U . . .
H30B H 0.5322 0.0904 1.5448 0.089 Uiso 1 1 calc R U . . .
C31 C 0.6374(10) 0.1813(17) 1.6069(8) 0.130(6) Uani 1 1 d . . . . .
H31A H 0.6672 0.2443 1.5959 0.156 Uiso 1 1 calc R U . . .
H31B H 0.6243 0.2047 1.6518 0.156 Uiso 1 1 calc R U . . .
C32 C 0.6898(8) 0.0833(16) 1.6313(10) 0.136(7) Uani 1 1 d . . . . .
H32A H 0.6565 0.0186 1.5995 0.205 Uiso 1 1 d R U . . .
H32B H 0.7099 0.0692 1.6902 0.205 Uiso 1 1 d R U . . .
H32C H 0.7383 0.0941 1.6206 0.205 Uiso 1 1 d R U . . .
N1 N 0.4257(3) 0.2015(4) 0.8995(3) 0.0180(9) Uani 1 1 d . . . . .
N2 N 0.4486(3) 0.1936(4) 1.0599(3) 0.0185(9) Uani 1 1 d . . . . .
O1 O 0.3731(3) 0.1927(4) 0.5678(2) 0.0364(10) Uani 1 1 d . . . . .
O2 O 0.4851(3) 0.1386(5) 1.3831(3) 0.0461(12) Uani 1 1 d . . . . .
Cl2 Cl 0.36346(8) -0.07617(11) 0.95097(9) 0.0290(3) Uani 1 1 d . . . . .
Cl1 Cl 0.22678(8) 0.19081(12) 0.90379(9) 0.0276(3) Uani 1 1 d . . . . .
Zn1 Zn 0.35733(3) 0.11329(5) 0.95070(3) 0.0172(2) Uani 1 1 d . . . . .
Cl3 Cl 0.4156(5) 0.5258(5) 0.5167(3) 0.105(2) Uani 0.5 1 d D U P A 1
C34 C 0.4553(14) 0.521(2) 0.6191(11) 0.095(4) Uani 0.5 1 d D U P A 1
H34A H 0.4138 0.4792 0.6303 0.114 Uiso 0.5 1 calc R U P A 1
H34B H 0.4550 0.5997 0.6372 0.114 Uiso 0.5 1 calc R U P A 1
Cl5 Cl 0.5578(7) 0.4639(10) 0.6884(5) 0.152(3) Uani 0.5 1 d D U P A 1
Cl4 Cl 0.4339(4) 0.4707(8) 0.6503(4) 0.111(2) Uani 0.5 1 d D U P B 2
C33 C 0.5113(9) 0.5622(13) 0.6783(9) 0.048(3) Uani 0.5 1 d D U P B 2
H33A H 0.5206 0.5963 0.7312 0.057 Uiso 0.5 1 calc R U P B 2
H33B H 0.4929 0.6233 0.6367 0.057 Uiso 0.5 1 calc R U P B 2
Cl6 Cl 0.6108(5) 0.5088(12) 0.6905(6) 0.172(4) Uani 0.5 1 d D U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.287(7) . ?
C1 C2 1.483(7) . ?
C1 C12 1.516(7) . ?
C2 C3 1.380(7) . ?
C2 C7 1.425(7) . ?
C3 C4 1.422(8) . ?
C4 C5 1.376(8) . ?
C5 C6 1.421(7) . ?
C6 C7 1.413(7) . ?
C6 C8 1.423(7) . ?
C7 C11 1.423(7) . ?
C8 C9 1.383(8) . ?
C9 C10 1.414(7) . ?
C10 C11 1.379(7) . ?
C11 C12 1.482(7) . ?
C12 N2 1.290(7) . ?
C13 C14 1.382(7) . ?
C13 C18 1.395(7) . ?
C13 N1 1.438(6) . ?
C14 C15 1.396(7) . ?
C15 C16 1.391(8) . ?
C16 O1 1.374(6) . ?
C16 C17 1.400(8) . ?
C17 C18 1.381(8) . ?
C19 O1 1.448(7) . ?
C19 C20 1.510(9) . ?
C20 C21 1.465(12) . ?
C21 C22 1.470(16) . ?
C23 C28 1.392(7) . ?
C23 C24 1.401(8) . ?
C23 N2 1.423(6) . ?
C24 C25 1.387(8) . ?
C25 C26 1.401(9) . ?
C26 O2 1.369(7) . ?
C26 C27 1.396(9) . ?
C27 C28 1.393(7) . ?
C29 O2 1.444(9) . ?
C29 C30 1.543(10) . ?
C30 C31 1.427(16) . ?
C31 C32 1.40(2) . ?
N1 Zn1 2.083(4) . ?
N2 Zn1 2.088(4) . ?
Cl2 Zn1 2.2026(15) . ?
Cl1 Zn1 2.2265(14) . ?
Cl3 C34 1.636(18) . ?
C34 Cl5 1.772(16) . ?
Cl4 C33 1.608(16) . ?
C33 Cl6 1.763(14) . ?

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
N1 C1 C2 134.4(5) . . ?
N1 C1 C12 118.2(4) . . ?
C2 C1 C12 107.3(4) . . ?
C3 C2 C7 119.4(5) . . ?
C3 C2 C1 134.9(5) . . ?
C7 C2 C1 105.4(4) . . ?
C2 C3 C4 118.3(5) . . ?
C5 C4 C3 122.6(5) . . ?
C4 C5 C6 120.3(5) . . ?
C7 C6 C5 116.9(5) . . ?
C7 C6 C8 116.4(5) . . ?
C5 C6 C8 126.6(5) . . ?
C6 C7 C11 123.2(5) . . ?
C6 C7 C2 122.4(5) . . ?
C11 C7 C2 114.5(4) . . ?
C9 C8 C6 120.3(5) . . ?
C8 C9 C10 122.2(5) . . ?
C11 C10 C9 119.3(5) . . ?
C10 C11 C7 118.6(5) . . ?
C10 C11 C12 135.6(5) . . ?
C7 C11 C12 105.6(4) . . ?
N2 C12 C11 135.4(5) . . ?
N2 C12 C1 117.3(4) . . ?
C11 C12 C1 107.1(4) . . ?
C14 C13 C18 120.3(5) . . ?
C14 C13 N1 119.2(5) . . ?
C18 C13 N1 120.5(5) . . ?
C13 C14 C15 120.6(5) . . ?
C16 C15 C14 118.9(5) . . ?
O1 C16 C15 124.0(5) . . ?
O1 C16 C17 115.7(5) . . ?
C15 C16 C17 120.3(5) . . ?
C18 C17 C16 120.2(5) . . ?
C17 C18 C13 119.5(5) . . ?
O1 C19 C20 107.0(6) . . ?
C21 C20 C19 114.9(8) . . ?
C22 C21 C20 111.1(10) . . ?
C28 C23 C24 120.4(5) . . ?
C28 C23 N2 121.0(5) . . ?
C24 C23 N2 118.5(5) . . ?
C25 C24 C23 119.1(5) . . ?
C24 C25 C26 120.5(6) . . ?
O2 C26 C27 124.1(6) . . ?
O2 C26 C25 115.7(5) . . ?
C27 C26 C25 120.2(5) . . ?
C28 C27 C26 119.3(5) . . ?
C27 C28 C23 120.4(5) . . ?
O2 C29 C30 106.3(7) . . ?
C31 C30 C29 115.7(9) . . ?
C32 C31 C30 109.0(15) . . ?
C1 N1 C13 121.6(4) . . ?
C1 N1 Zn1 111.4(3) . . ?
C13 N1 Zn1 127.0(3) . . ?
C12 N2 C23 122.0(4) . . ?
C12 N2 Zn1 111.6(3) . . ?
C23 N2 Zn1 126.3(3) . . ?
C16 O1 C19 116.8(5) . . ?
C26 O2 C29 117.1(5) . . ?
N1 Zn1 N2 81.24(16) . . ?
N1 Zn1 Cl2 117.04(12) . . ?
N2 Zn1 Cl2 115.36(12) . . ?
N1 Zn1 Cl1 109.42(12) . . ?
N2 Zn1 Cl1 112.35(12) . . ?
Cl2 Zn1 Cl1 116.43(5) . . ?
Cl3 C34 Cl5 124.6(13) . . ?
Cl4 C33 Cl6 116.6(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 1.3(10) . . . . ?
C12 C1 C2 C3 -174.6(5) . . . . ?
N1 C1 C2 C7 176.1(5) . . . . ?
C12 C1 C2 C7 0.2(5) . . . . ?
C7 C2 C3 C4 1.5(7) . . . . ?
C1 C2 C3 C4 175.7(5) . . . . ?
C2 C3 C4 C5 -0.3(8) . . . . ?
C3 C4 C5 C6 -1.2(8) . . . . ?
C4 C5 C6 C7 1.4(7) . . . . ?
C4 C5 C6 C8 -177.3(5) . . . . ?
C5 C6 C7 C11 -178.3(5) . . . . ?
C8 C6 C7 C11 0.6(7) . . . . ?
C5 C6 C7 C2 -0.2(7) . . . . ?
C8 C6 C7 C2 178.7(4) . . . . ?
C3 C2 C7 C6 -1.3(7) . . . . ?
C1 C2 C7 C6 -177.0(4) . . . . ?
C3 C2 C7 C11 177.0(4) . . . . ?
C1 C2 C7 C11 1.2(6) . . . . ?
C7 C6 C8 C9 -1.0(7) . . . . ?
C5 C6 C8 C9 177.7(5) . . . . ?
C6 C8 C9 C10 0.7(8) . . . . ?
C8 C9 C10 C11 0.2(7) . . . . ?
C9 C10 C11 C7 -0.6(7) . . . . ?
C9 C10 C11 C12 -174.9(5) . . . . ?
C6 C7 C11 C10 0.3(7) . . . . ?
C2 C7 C11 C10 -178.0(4) . . . . ?
C6 C7 C11 C12 176.1(4) . . . . ?
C2 C7 C11 C12 -2.1(6) . . . . ?
C10 C11 C12 N2 2.0(10) . . . . ?
C7 C11 C12 N2 -172.8(5) . . . . ?
C10 C11 C12 C1 176.9(5) . . . . ?
C7 C11 C12 C1 2.1(5) . . . . ?
N1 C1 C12 N2 -2.1(7) . . . . ?
C2 C1 C12 N2 174.5(4) . . . . ?
N1 C1 C12 C11 -178.1(4) . . . . ?
C2 C1 C12 C11 -1.5(5) . . . . ?
C18 C13 C14 C15 -4.4(8) . . . . ?
N1 C13 C14 C15 178.0(5) . . . . ?
C13 C14 C15 C16 2.7(8) . . . . ?
C14 C15 C16 O1 -179.3(5) . . . . ?
C14 C15 C16 C17 0.6(8) . . . . ?
O1 C16 C17 C18 177.7(5) . . . . ?
C15 C16 C17 C18 -2.3(8) . . . . ?
C16 C17 C18 C13 0.6(8) . . . . ?
C14 C13 C18 C17 2.7(8) . . . . ?
N1 C13 C18 C17 -179.7(5) . . . . ?
O1 C19 C20 C21 175.6(9) . . . . ?
C19 C20 C21 C22 68.2(12) . . . . ?
C28 C23 C24 C25 4.9(9) . . . . ?
N2 C23 C24 C25 -177.7(5) . . . . ?
C23 C24 C25 C26 -2.1(10) . . . . ?
C24 C25 C26 O2 177.5(6) . . . . ?
C24 C25 C26 C27 -2.2(10) . . . . ?
O2 C26 C27 C28 -176.1(5) . . . . ?
C25 C26 C27 C28 3.6(9) . . . . ?
C26 C27 C28 C23 -0.7(8) . . . . ?
C24 C23 C28 C27 -3.6(8) . . . . ?
N2 C23 C28 C27 179.1(5) . . . . ?
O2 C29 C30 C31 -163.0(11) . . . . ?
C29 C30 C31 C32 -64.7(16) . . . . ?
C2 C1 N1 C13 7.4(8) . . . . ?
C12 C1 N1 C13 -177.1(4) . . . . ?
C2 C1 N1 Zn1 -170.7(5) . . . . ?
C12 C1 N1 Zn1 4.8(5) . . . . ?
C14 C13 N1 C1 -123.5(5) . . . . ?
C18 C13 N1 C1 58.9(7) . . . . ?
C14 C13 N1 Zn1 54.3(6) . . . . ?
C18 C13 N1 Zn1 -123.4(5) . . . . ?
C11 C12 N2 C23 -10.2(9) . . . . ?
C1 C12 N2 C23 175.4(4) . . . . ?
C11 C12 N2 Zn1 172.7(5) . . . . ?
C1 C12 N2 Zn1 -1.8(5) . . . . ?
C28 C23 N2 C12 -52.3(7) . . . . ?
C24 C23 N2 C12 130.3(5) . . . . ?
C28 C23 N2 Zn1 124.4(4) . . . . ?
C24 C23 N2 Zn1 -53.0(6) . . . . ?
C15 C16 O1 C19 6.9(8) . . . . ?
C17 C16 O1 C19 -173.0(5) . . . . ?
C20 C19 O1 C16 173.8(6) . . . . ?
C27 C26 O2 C29 8.8(9) . . . . ?
C25 C26 O2 C29 -170.9(6) . . . . ?
C30 C29 O2 C26 164.6(6) . . . . ?

_refine_diff_density_max         2.068
_refine_diff_density_min         -2.158
_refine_diff_density_rms         0.139

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1061238'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 Cl2 N2 O2 Zn, C2 H4 O2'
_chemical_formula_sum            'C28 H24 Cl2 N2 O4 Zn'
_chemical_formula_weight         588.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   12.4510(3)
_cell_length_b                   11.7454(3)
_cell_length_c                   17.4508(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.969(2)
_cell_angle_gamma                90
_cell_volume                     2538.20(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5211
_cell_measurement_theta_min      4.5450
_cell_measurement_theta_max      74.0860

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    3.603
_shelx_estimated_absorpt_T_min   0.632
_shelx_estimated_absorpt_T_max   0.787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74906
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray source'
_diffrn_measurement_device_type  'Agilent SuperNova with AtlasS2 detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9920
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.569
_diffrn_reflns_theta_max         74.329
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5030
_reflns_number_gt                4504
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_cell_refinement       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction        
'CrysAlisPro V 1.171.37.31, Agilent Technologies'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²+0.8230P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5030
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0871
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.93278(14) 0.23747(15) 0.51823(10) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.94838(15) 0.14960(16) 0.57845(10) 0.0179(3) Uani 1 1 d . . . . .
C3 C 0.88630(15) 0.10605(16) 0.63256(11) 0.0202(4) Uani 1 1 d . . . . .
H3 H 0.8169 0.1365 0.6382 0.024 Uiso 1 1 calc R U . . .
C4 C 0.92873(16) 0.01447(16) 0.67976(11) 0.0216(4) Uani 1 1 d . . . . .
H4 H 0.8864 -0.0161 0.7171 0.026 Uiso 1 1 calc R U . . .
C5 C 1.02904(16) -0.03125(16) 0.67316(11) 0.0217(4) Uani 1 1 d . . . . .
H5 H 1.0551 -0.0915 0.7063 0.026 Uiso 1 1 calc R U . . .
C6 C 1.09391(15) 0.01079(16) 0.61732(11) 0.0197(4) Uani 1 1 d . . . . .
C7 C 1.05136(15) 0.10106(16) 0.57092(10) 0.0176(4) Uani 1 1 d . . . . .
C8 C 1.19788(16) -0.02920(16) 0.60375(11) 0.0229(4) Uani 1 1 d . . . . .
H8 H 1.2304 -0.0897 0.6339 0.027 Uiso 1 1 calc R U . . .
C9 C 1.25158(16) 0.01943(17) 0.54702(12) 0.0241(4) Uani 1 1 d . . . . .
H9 H 1.3212 -0.0085 0.5391 0.029 Uiso 1 1 calc R U . . .
C10 C 1.20701(16) 0.10981(16) 0.49988(11) 0.0219(4) Uani 1 1 d . . . . .
H10 H 1.2457 0.1414 0.4608 0.026 Uiso 1 1 calc R U . . .
C11 C 1.10635(14) 0.15077(15) 0.51209(10) 0.0177(3) Uani 1 1 d . . . . .
C12 C 1.03182(14) 0.23589(15) 0.47450(10) 0.0170(3) Uani 1 1 d . . . . .
C13 C 0.76256(15) 0.32337(15) 0.53405(10) 0.0187(4) Uani 1 1 d . . . . .
C14 C 0.66140(15) 0.31993(17) 0.49192(11) 0.0214(4) Uani 1 1 d . . . . .
H14 H 0.6556 0.3040 0.4383 0.026 Uiso 1 1 calc R U . . .
C15 C 0.56864(15) 0.33966(17) 0.52800(11) 0.0225(4) Uani 1 1 d . . . . .
H15 H 0.4996 0.3359 0.4993 0.027 Uiso 1 1 calc R U . . .
C16 C 0.57763(15) 0.36497(16) 0.60635(11) 0.0199(4) Uani 1 1 d . . . . .
C17 C 0.67921(15) 0.37079(16) 0.64806(11) 0.0210(4) Uani 1 1 d . . . . .
H17 H 0.6852 0.3892 0.7014 0.025 Uiso 1 1 calc R U . . .
C18 C 0.77139(15) 0.34996(16) 0.61227(11) 0.0205(4) Uani 1 1 d . . . . .
H18 H 0.8405 0.3538 0.6410 0.025 Uiso 1 1 calc R U . . .
C19 C 0.38603(16) 0.3774(2) 0.60768(13) 0.0290(4) Uani 1 1 d . . . . .
H19A H 0.3784 0.4310 0.5644 0.044 Uiso 1 1 calc R U . . .
H19B H 0.3325 0.3952 0.6433 0.044 Uiso 1 1 calc R U . . .
H19C H 0.3744 0.2996 0.5882 0.044 Uiso 1 1 calc R U . . .
C20 C 1.12198(15) 0.30872(15) 0.37147(11) 0.0184(4) Uani 1 1 d . . . . .
C21 C 1.10822(15) 0.29014(16) 0.29204(11) 0.0198(4) Uani 1 1 d . . . . .
H21 H 1.0386 0.2735 0.2669 0.024 Uiso 1 1 calc R U . . .
C22 C 1.19655(15) 0.29609(16) 0.25012(11) 0.0210(4) Uani 1 1 d . . . . .
H22 H 1.1880 0.2805 0.1964 0.025 Uiso 1 1 calc R U . . .
C23 C 1.29798(15) 0.32489(16) 0.28631(11) 0.0215(4) Uani 1 1 d . . . . .
C24 C 1.31007(15) 0.35020(17) 0.36490(11) 0.0222(4) Uani 1 1 d . . . . .
H24 H 1.3784 0.3730 0.3894 0.027 Uiso 1 1 calc R U . . .
C25 C 1.22179(15) 0.34195(16) 0.40714(11) 0.0212(4) Uani 1 1 d . . . . .
H25 H 1.2298 0.3591 0.4606 0.025 Uiso 1 1 calc R U . . .
C26 C 1.48846(16) 0.3311(2) 0.27764(14) 0.0311(5) Uani 1 1 d . . . . .
H26A H 1.5005 0.4059 0.3018 0.047 Uiso 1 1 calc R U . . .
H26B H 1.5398 0.3198 0.2394 0.047 Uiso 1 1 calc R U . . .
H26C H 1.4990 0.2716 0.3171 0.047 Uiso 1 1 calc R U . . .
C27 C 0.43245(15) 0.02524(17) 0.39630(11) 0.0225(4) Uani 1 1 d . . . . .
C28 C 0.37580(18) 0.04541(19) 0.31783(12) 0.0283(4) Uani 1 1 d . . . . .
H28A H 0.3203 0.1039 0.3207 0.042 Uiso 1 1 calc R U . . .
H28B H 0.3419 -0.0255 0.2981 0.042 Uiso 1 1 calc R U . . .
H28C H 0.4281 0.0710 0.2832 0.042 Uiso 1 1 calc R U . . .
Cl1 Cl 0.77656(4) 0.30919(4) 0.29921(2) 0.02220(11) Uani 1 1 d . . . . .
Cl2 Cl 0.90528(4) 0.57361(4) 0.39206(3) 0.02370(11) Uani 1 1 d . . . . .
N1 N 0.85598(12) 0.30634(13) 0.49482(8) 0.0173(3) Uani 1 1 d . . . . .
N2 N 1.03060(12) 0.29876(13) 0.41419(9) 0.0172(3) Uani 1 1 d . . . . .
O1 O 0.49243(11) 0.38665(12) 0.64733(8) 0.0249(3) Uani 1 1 d . . . . .
O2 O 1.38029(11) 0.32494(13) 0.24048(8) 0.0272(3) Uani 1 1 d . . . . .
O3 O 0.44189(14) -0.08210(13) 0.41618(10) 0.0327(3) Uani 1 1 d . . . . .
O4 O 0.46596(12) 0.10376(13) 0.43874(9) 0.0295(3) Uani 1 1 d . . . . .
Zn1 Zn 0.88650(2) 0.38725(2) 0.39305(2) 0.01727(9) Uani 1 1 d . . . . .
H1O H 0.471(3) -0.089(3) 0.460(2) 0.059(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.286(2) . ?
C1 C2 1.471(3) . ?
C1 C12 1.516(2) . ?
C2 C3 1.379(3) . ?
C2 C7 1.422(3) . ?
C3 C4 1.423(3) . ?
C4 C5 1.375(3) . ?
C5 C6 1.417(3) . ?
C6 C7 1.404(3) . ?
C6 C8 1.420(3) . ?
C7 C11 1.418(3) . ?
C8 C9 1.375(3) . ?
C9 C10 1.420(3) . ?
C10 C11 1.380(3) . ?
C11 C12 1.471(2) . ?
C12 N2 1.284(2) . ?
C13 C14 1.391(3) . ?
C13 C18 1.394(3) . ?
C13 N1 1.424(2) . ?
C14 C15 1.391(3) . ?
C15 C16 1.392(3) . ?
C16 O1 1.364(2) . ?
C16 C17 1.394(3) . ?
C17 C18 1.384(3) . ?
C19 O1 1.434(2) . ?
C20 C25 1.387(3) . ?
C20 C21 1.396(3) . ?
C20 N2 1.428(2) . ?
C21 C22 1.385(3) . ?
C22 C23 1.394(3) . ?
C23 O2 1.364(2) . ?
C23 C24 1.396(3) . ?
C24 C25 1.389(3) . ?
C26 O2 1.435(2) . ?
C27 O4 1.228(2) . ?
C27 O3 1.310(3) . ?
C27 C28 1.493(3) . ?
Cl1 Zn1 2.2203(5) . ?
Cl2 Zn1 2.2016(5) . ?
N1 Zn1 2.0838(15) . ?
N2 Zn1 2.0730(15) . ?

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
N1 C1 C2 134.95(17) . . ?
N1 C1 C12 117.68(16) . . ?
C2 C1 C12 107.28(15) . . ?
C3 C2 C7 119.31(17) . . ?
C3 C2 C1 135.02(17) . . ?
C7 C2 C1 105.58(15) . . ?
C2 C3 C4 118.41(17) . . ?
C5 C4 C3 122.18(18) . . ?
C4 C5 C6 120.59(18) . . ?
C7 C6 C5 116.85(17) . . ?
C7 C6 C8 116.71(18) . . ?
C5 C6 C8 126.44(18) . . ?
C6 C7 C11 123.16(17) . . ?
C6 C7 C2 122.64(17) . . ?
C11 C7 C2 114.20(16) . . ?
C9 C8 C6 120.17(18) . . ?
C8 C9 C10 122.52(18) . . ?
C11 C10 C9 118.54(18) . . ?
C10 C11 C7 118.89(17) . . ?
C10 C11 C12 135.17(17) . . ?
C7 C11 C12 105.84(15) . . ?
N2 C12 C11 135.17(17) . . ?
N2 C12 C1 117.67(16) . . ?
C11 C12 C1 106.99(15) . . ?
C14 C13 C18 119.93(17) . . ?
C14 C13 N1 118.81(16) . . ?
C18 C13 N1 121.15(16) . . ?
C15 C14 C13 120.31(17) . . ?
C14 C15 C16 119.62(18) . . ?
O1 C16 C15 124.57(17) . . ?
O1 C16 C17 115.47(17) . . ?
C15 C16 C17 119.95(17) . . ?
C18 C17 C16 120.37(17) . . ?
C17 C18 C13 119.80(17) . . ?
C25 C20 C21 120.09(17) . . ?
C25 C20 N2 120.93(17) . . ?
C21 C20 N2 118.90(16) . . ?
C22 C21 C20 119.64(18) . . ?
C21 C22 C23 120.33(18) . . ?
O2 C23 C22 115.79(17) . . ?
O2 C23 C24 124.41(18) . . ?
C22 C23 C24 119.80(17) . . ?
C25 C24 C23 119.73(18) . . ?
C20 C25 C24 120.21(18) . . ?
O4 C27 O3 123.20(19) . . ?
O4 C27 C28 122.17(19) . . ?
O3 C27 C28 114.62(18) . . ?
C1 N1 C13 123.59(16) . . ?
C1 N1 Zn1 111.22(12) . . ?
C13 N1 Zn1 125.19(12) . . ?
C12 N2 C20 122.17(15) . . ?
C12 N2 Zn1 111.74(12) . . ?
C20 N2 Zn1 125.99(12) . . ?
C16 O1 C19 117.58(15) . . ?
C23 O2 C26 117.54(16) . . ?
N2 Zn1 N1 81.42(6) . . ?
N2 Zn1 Cl2 114.15(4) . . ?
N1 Zn1 Cl2 119.28(4) . . ?
N2 Zn1 Cl1 112.33(4) . . ?
N1 Zn1 Cl1 106.69(4) . . ?
Cl2 Zn1 Cl1 117.554(19) . . ?

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1061239'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 Cl2 N2 O2 Zn, C H2 Cl2'
_chemical_formula_sum            'C27 H22 Cl4 N2 O2 Zn'
_chemical_formula_weight         613.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.840(5)
_cell_length_b                   11.647(4)
_cell_length_c                   17.844(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.446(4)
_cell_angle_gamma                90
_cell_volume                     2677.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3112
_cell_measurement_theta_min      2.3581
_cell_measurement_theta_max      31.8787

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.345
_shelx_estimated_absorpt_T_min   0.834
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5110
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
Abscor. T. Higashi. (2001). Rigaku Corp. Tokyo, Japan
;



_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku SCX-Mini Mercury CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20087
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.136
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6116
_reflns_number_gt                5430
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_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     
'w=1/[σ²(Fo²)+(0.0434P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6116
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.44986(13) 0.26018(16) 0.51104(10) 0.0142(4) Uani 1 1 d . . . . .
C2 C 0.47001(13) 0.34644(16) 0.57522(10) 0.0139(4) Uani 1 1 d . . . . .
C3 C 0.41692(14) 0.38574(16) 0.62228(11) 0.0162(4) Uani 1 1 d . . . . .
H3 H 0.3538 0.3503 0.6194 0.019 Uiso 1 1 calc R U . . .
C4 C 0.45777(15) 0.47964(16) 0.67487(11) 0.0175(4) Uani 1 1 d . . . . .
H4 H 0.4215 0.5063 0.7075 0.021 Uiso 1 1 calc R U . . .
C5 C 0.54882(15) 0.53350(16) 0.67996(11) 0.0175(4) Uani 1 1 d . . . . .
H5 H 0.5744 0.5957 0.7163 0.021 Uiso 1 1 calc R U . . .
C6 C 0.60467(14) 0.49693(17) 0.63151(11) 0.0158(4) Uani 1 1 d . . . . .
C7 C 0.56325(14) 0.40269(16) 0.58039(10) 0.0142(4) Uani 1 1 d . . . . .
C8 C 0.69633(14) 0.54730(17) 0.62798(11) 0.0180(4) Uani 1 1 d . . . . .
H8 H 0.7282 0.6097 0.6625 0.022 Uiso 1 1 calc R U . . .
C9 C 0.73928(15) 0.50591(17) 0.57457(11) 0.0189(4) Uani 1 1 d . . . . .
H9 H 0.7997 0.5420 0.5724 0.023 Uiso 1 1 calc R U . . .
C10 C 0.69672(14) 0.41207(17) 0.52318(11) 0.0171(4) Uani 1 1 d . . . . .
H10 H 0.7277 0.3856 0.4869 0.021 Uiso 1 1 calc R U . . .
C11 C 0.60890(14) 0.35927(16) 0.52665(10) 0.0140(3) Uani 1 1 d . . . . .
C12 C 0.53894(13) 0.26729(15) 0.48084(10) 0.0133(4) Uani 1 1 d . . . . .
C13 C 0.29236(14) 0.16639(16) 0.50060(11) 0.0149(4) Uani 1 1 d . . . . .
C14 C 0.19189(14) 0.16257(18) 0.44340(11) 0.0189(4) Uani 1 1 d . . . . .
H14 H 0.1802 0.1748 0.3881 0.023 Uiso 1 1 calc R U . . .
C15 C 0.10914(14) 0.14087(19) 0.46738(12) 0.0225(4) Uani 1 1 d . . . . .
H15 H 0.0403 0.1408 0.4288 0.027 Uiso 1 1 calc R U . . .
C16 C 0.12687(15) 0.11918(16) 0.54814(12) 0.0187(4) Uani 1 1 d . . . . .
C17 C 0.22747(15) 0.11573(16) 0.60452(11) 0.0172(4) Uani 1 1 d . . . . .
H17 H 0.2397 0.0972 0.6591 0.021 Uiso 1 1 calc R U . . .
C18 C 0.31011(14) 0.13971(16) 0.58042(11) 0.0164(4) Uani 1 1 d . . . . .
H18 H 0.3791 0.1378 0.6187 0.020 Uiso 1 1 calc R U . . .
C19 C 0.05311(17) 0.0957(2) 0.64956(13) 0.0279(5) Uani 1 1 d . . . . .
H19A H 0.0945 0.0278 0.6740 0.042 Uiso 1 1 calc R U . . .
H19B H -0.0150 0.0904 0.6545 0.042 Uiso 1 1 calc R U . . .
H19C H 0.0890 0.1649 0.6773 0.042 Uiso 1 1 calc R U . . .
C20 C 0.62162(13) 0.19844(16) 0.39495(11) 0.0144(4) Uani 1 1 d . . . . .
C21 C 0.60286(14) 0.22020(16) 0.31442(11) 0.0163(4) Uani 1 1 d . . . . .
H21 H 0.5340 0.2336 0.2780 0.020 Uiso 1 1 calc R U . . .
C22 C 0.68520(14) 0.22248(17) 0.28693(11) 0.0178(4) Uani 1 1 d . . . . .
H22 H 0.6730 0.2392 0.2321 0.021 Uiso 1 1 calc R U . . .
C23 C 0.78519(14) 0.20002(16) 0.34054(11) 0.0173(4) Uani 1 1 d . . . . .
C24 C 0.80322(14) 0.17262(17) 0.42066(11) 0.0184(4) Uani 1 1 d . . . . .
H24 H 0.8714 0.1546 0.4565 0.022 Uiso 1 1 calc R U . . .
C25 C 0.72149(14) 0.17171(16) 0.44789(11) 0.0171(4) Uani 1 1 d . . . . .
H25 H 0.7334 0.1530 0.5024 0.020 Uiso 1 1 calc R U . . .
C26 C 0.85623(17) 0.2298(2) 0.23784(13) 0.0277(5) Uani 1 1 d . . . . .
H26A H 0.8120 0.1711 0.2022 0.041 Uiso 1 1 calc R U . . .
H26B H 0.9235 0.2317 0.2312 0.041 Uiso 1 1 calc R U . . .
H26C H 0.8226 0.3050 0.2240 0.041 Uiso 1 1 calc R U . . .
C27 C 0.11384(18) -0.0115(2) 0.13258(15) 0.0319(5) Uani 1 1 d . . . . .
H27A H 0.0985 -0.0879 0.1065 0.038 Uiso 1 1 calc R U . . .
H27B H 0.1848 -0.0141 0.1740 0.038 Uiso 1 1 calc R U . . .
N1 N 0.37599(11) 0.19020(13) 0.47446(9) 0.0134(3) Uani 1 1 d . . . . .
N2 N 0.53647(11) 0.20147(13) 0.42237(9) 0.0145(3) Uani 1 1 d . . . . .
O1 O 0.03975(11) 0.10166(13) 0.56593(9) 0.0253(3) Uani 1 1 d . . . . .
O2 O 0.87172(10) 0.20269(13) 0.31991(8) 0.0237(3) Uani 1 1 d . . . . .
Cl1 Cl 0.39624(4) -0.07665(5) 0.37659(3) 0.02424(12) Uani 1 1 d . . . . .
Cl2 Cl 0.29396(4) 0.18813(4) 0.26101(3) 0.01944(11) Uani 1 1 d . . . . .
Cl3 Cl 0.02433(5) 0.01757(7) 0.17930(5) 0.05146(19) Uani 1 1 d . . . . .
Cl4 Cl 0.10930(5) 0.09283(5) 0.05991(4) 0.03995(16) Uani 1 1 d . . . . .
Zn1 Zn 0.39682(2) 0.11224(2) 0.37705(2) 0.01364(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.284(2) . ?
C1 C2 1.471(2) . ?
C1 C12 1.518(2) . ?
C2 C3 1.380(2) . ?
C2 C7 1.420(3) . ?
C3 C4 1.417(3) . ?
C4 C5 1.381(3) . ?
C5 C6 1.419(3) . ?
C6 C7 1.408(3) . ?
C6 C8 1.420(3) . ?
C7 C11 1.421(2) . ?
C8 C9 1.381(3) . ?
C9 C10 1.410(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.475(3) . ?
C12 N2 1.285(2) . ?
C13 C18 1.389(3) . ?
C13 C14 1.393(2) . ?
C13 N1 1.424(2) . ?
C14 C15 1.384(3) . ?
C15 C16 1.394(3) . ?
C16 O1 1.370(2) . ?
C16 C17 1.388(3) . ?
C17 C18 1.389(3) . ?
C19 O1 1.437(2) . ?
C20 C21 1.387(3) . ?
C20 C25 1.395(3) . ?
C20 N2 1.432(2) . ?
C21 C22 1.396(2) . ?
C22 C23 1.390(3) . ?
C23 O2 1.376(2) . ?
C23 C24 1.395(3) . ?
C24 C25 1.385(3) . ?
C26 O2 1.435(2) . ?
C27 Cl3 1.761(2) . ?
C27 Cl4 1.762(2) . ?
N1 Zn1 2.0725(16) . ?
N2 Zn1 2.0800(16) . ?
Cl1 Zn1 2.2000(9) . ?
Cl2 Zn1 2.2225(7) . ?

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
N1 C1 C2 135.93(16) . . ?
N1 C1 C12 116.96(16) . . ?
C2 C1 C12 106.96(15) . . ?
C3 C2 C7 118.74(17) . . ?
C3 C2 C1 135.09(17) . . ?
C7 C2 C1 105.95(15) . . ?
C2 C3 C4 119.11(17) . . ?
C5 C4 C3 121.85(17) . . ?
C4 C5 C6 120.72(18) . . ?
C7 C6 C5 116.42(17) . . ?
C7 C6 C8 116.87(17) . . ?
C5 C6 C8 126.69(18) . . ?
C6 C7 C2 123.14(17) . . ?
C6 C7 C11 122.59(17) . . ?
C2 C7 C11 114.20(16) . . ?
C9 C8 C6 120.22(18) . . ?
C8 C9 C10 122.44(18) . . ?
C11 C10 C9 118.72(17) . . ?
C10 C11 C7 119.13(17) . . ?
C10 C11 C12 135.05(17) . . ?
C7 C11 C12 105.60(15) . . ?
N2 C12 C11 134.47(16) . . ?
N2 C12 C1 118.16(16) . . ?
C11 C12 C1 107.27(15) . . ?
C18 C13 C14 119.94(16) . . ?
C18 C13 N1 121.27(16) . . ?
C14 C13 N1 118.65(16) . . ?
C15 C14 C13 119.77(17) . . ?
C14 C15 C16 119.99(17) . . ?
O1 C16 C17 124.22(18) . . ?
O1 C16 C15 115.44(17) . . ?
C17 C16 C15 120.34(17) . . ?
C16 C17 C18 119.40(17) . . ?
C13 C18 C17 120.34(17) . . ?
C21 C20 C25 120.41(16) . . ?
C21 C20 N2 118.93(15) . . ?
C25 C20 N2 120.65(16) . . ?
C20 C21 C22 120.00(17) . . ?
C23 C22 C21 119.35(17) . . ?
O2 C23 C22 123.84(17) . . ?
O2 C23 C24 115.61(16) . . ?
C22 C23 C24 120.55(16) . . ?
C25 C24 C23 119.88(17) . . ?
C24 C25 C20 119.68(17) . . ?
Cl3 C27 Cl4 111.94(13) . . ?
C1 N1 C13 123.27(15) . . ?
C1 N1 Zn1 112.06(12) . . ?
C13 N1 Zn1 124.62(12) . . ?
C12 N2 C20 120.74(15) . . ?
C12 N2 Zn1 111.03(12) . . ?
C20 N2 Zn1 128.21(12) . . ?
C16 O1 C19 117.26(16) . . ?
C23 O2 C26 117.26(15) . . ?
N1 Zn1 N2 81.34(6) . . ?
N1 Zn1 Cl1 116.09(5) . . ?
N2 Zn1 Cl1 120.18(5) . . ?
N1 Zn1 Cl2 111.65(5) . . ?
N2 Zn1 Cl2 110.55(5) . . ?
Cl1 Zn1 Cl2 113.20(2) . . ?

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
N1 C1 C2 C3 0.6(4) . . . . ?
C12 C1 C2 C3 175.8(2) . . . . ?
N1 C1 C2 C7 -173.6(2) . . . . ?
C12 C1 C2 C7 1.65(19) . . . . ?
C7 C2 C3 C4 -0.9(3) . . . . ?
C1 C2 C3 C4 -174.49(19) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C7 -1.3(3) . . . . ?
C4 C5 C6 C8 177.06(18) . . . . ?
C5 C6 C7 C2 0.9(3) . . . . ?
C8 C6 C7 C2 -177.60(16) . . . . ?
C5 C6 C7 C11 177.85(17) . . . . ?
C8 C6 C7 C11 -0.7(3) . . . . ?
C3 C2 C7 C6 0.1(3) . . . . ?
C1 C2 C7 C6 175.47(16) . . . . ?
C3 C2 C7 C11 -177.01(16) . . . . ?
C1 C2 C7 C11 -1.7(2) . . . . ?
C7 C6 C8 C9 1.8(3) . . . . ?
C5 C6 C8 C9 -176.55(19) . . . . ?
C6 C8 C9 C10 -1.4(3) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C7 1.4(3) . . . . ?
C9 C10 C11 C12 174.95(19) . . . . ?
C6 C7 C11 C10 -0.9(3) . . . . ?
C2 C7 C11 C10 176.26(16) . . . . ?
C6 C7 C11 C12 -176.21(16) . . . . ?
C2 C7 C11 C12 1.0(2) . . . . ?
C10 C11 C12 N2 2.1(4) . . . . ?
C7 C11 C12 N2 176.2(2) . . . . ?
C10 C11 C12 C1 -174.0(2) . . . . ?
C7 C11 C12 C1 0.15(19) . . . . ?
N1 C1 C12 N2 -1.7(2) . . . . ?
C2 C1 C12 N2 -177.97(16) . . . . ?
N1 C1 C12 C11 175.14(15) . . . . ?
C2 C1 C12 C11 -1.13(19) . . . . ?
C18 C13 C14 C15 5.0(3) . . . . ?
N1 C13 C14 C15 -179.28(18) . . . . ?
C13 C14 C15 C16 -2.1(3) . . . . ?
C14 C15 C16 O1 178.39(18) . . . . ?
C14 C15 C16 C17 -2.0(3) . . . . ?
O1 C16 C17 C18 -177.23(18) . . . . ?
C15 C16 C17 C18 3.2(3) . . . . ?
C14 C13 C18 C17 -3.8(3) . . . . ?
N1 C13 C18 C17 -179.41(17) . . . . ?
C16 C17 C18 C13 -0.3(3) . . . . ?
C25 C20 C21 C22 -4.0(3) . . . . ?
N2 C20 C21 C22 177.33(17) . . . . ?
C20 C21 C22 C23 1.6(3) . . . . ?
C21 C22 C23 O2 -178.48(18) . . . . ?
C21 C22 C23 C24 1.6(3) . . . . ?
O2 C23 C24 C25 177.76(17) . . . . ?
C22 C23 C24 C25 -2.3(3) . . . . ?
C23 C24 C25 C20 -0.1(3) . . . . ?
C21 C20 C25 C24 3.3(3) . . . . ?
N2 C20 C25 C24 -178.07(17) . . . . ?
C2 C1 N1 C13 -11.2(3) . . . . ?
C12 C1 N1 C13 173.95(15) . . . . ?
C2 C1 N1 Zn1 171.25(18) . . . . ?
C12 C1 N1 Zn1 -3.62(19) . . . . ?
C18 C13 N1 C1 -48.5(3) . . . . ?
C14 C13 N1 C1 135.81(19) . . . . ?
C18 C13 N1 Zn1 128.76(16) . . . . ?
C14 C13 N1 Zn1 -46.9(2) . . . . ?
C11 C12 N2 C20 8.6(3) . . . . ?
C1 C12 N2 C20 -175.61(15) . . . . ?
C11 C12 N2 Zn1 -169.82(17) . . . . ?
C1 C12 N2 Zn1 6.0(2) . . . . ?
C21 C20 N2 C12 -124.33(19) . . . . ?
C25 C20 N2 C12 57.0(3) . . . . ?
C21 C20 N2 Zn1 53.8(2) . . . . ?
C25 C20 N2 Zn1 -124.86(16) . . . . ?
C17 C16 O1 C19 9.2(3) . . . . ?
C15 C16 O1 C19 -171.16(18) . . . . ?
C22 C23 O2 C26 -0.4(3) . . . . ?
C24 C23 O2 C26 179.57(18) . . . . ?

_refine_diff_density_max         0.688
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1061240'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 Cl2 N2 S2 Zn, C2 H4 O2'
_chemical_formula_sum            'C28 H24 Cl2 N2 O2 S2 Zn'
_chemical_formula_weight         620.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.036(3)
_cell_length_b                   11.7210(15)
_cell_length_c                   17.716(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.657(16)
_cell_angle_gamma                90
_cell_volume                     2676.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    511
_cell_measurement_theta_min      5.0390
_cell_measurement_theta_max      41.4700

_exptl_crystal_description       chip
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    4.813
_shelx_estimated_absorpt_T_min   0.729
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray source'
_diffrn_measurement_device_type  'Agilent SuperNova with AtlasS2 detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16148
_diffrn_reflns_av_unetI/netI     0.8214
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.429
_diffrn_reflns_theta_max         67.484
_diffrn_reflns_theta_full        67.484
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             16148
_reflns_number_gt                2476
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_cell_refinement       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction        
'CrysAlisPro V 1.171.37.31, Agilent Technologies'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         16148
_refine_ls_number_parameters     338
_refine_ls_number_restraints     528
_refine_ls_R_factor_all          0.3689
_refine_ls_R_factor_gt           0.1556
_refine_ls_wR_factor_ref         0.3854
_refine_ls_wR_factor_gt          0.3454
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.075
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.546(3) 0.269(3) 0.4714(19) 0.034(6) Uani 1 1 d . U . . .
C2 C 0.614(3) 0.353(3) 0.5098(18) 0.036(7) Uani 1 1 d . U . . .
C3 C 0.707(3) 0.400(3) 0.4971(19) 0.044(8) Uani 1 1 d . U . . .
H3 H 0.7399 0.3727 0.4563 0.052 Uiso 1 1 calc R U . . .
C4 C 0.753(2) 0.489(3) 0.5466(17) 0.035(7) Uani 1 1 d . U . . .
H4 H 0.8175 0.5217 0.5388 0.042 Uiso 1 1 calc R U . . .
C5 C 0.707(3) 0.525(3) 0.6016(18) 0.043(8) Uani 1 1 d . U . . .
H5 H 0.7430 0.5786 0.6364 0.051 Uiso 1 1 calc R U . . .
C6 C 0.608(3) 0.492(2) 0.6135(19) 0.039(7) Uani 1 1 d . U . . .
C7 C 0.564(2) 0.393(3) 0.5665(18) 0.036(7) Uani 1 1 d . U . . .
C8 C 0.547(2) 0.526(3) 0.6690(17) 0.033(7) Uani 1 1 d . U . . .
H8 H 0.5744 0.5828 0.7048 0.039 Uiso 1 1 calc R U . . .
C9 C 0.452(2) 0.483(3) 0.6740(18) 0.042(8) Uani 1 1 d . U . . .
H9 H 0.4125 0.5141 0.7100 0.050 Uiso 1 1 calc R U . . .
C10 C 0.410(3) 0.391(3) 0.6270(18) 0.042(8) Uani 1 1 d . U . . .
H10 H 0.3458 0.3565 0.6331 0.050 Uiso 1 1 calc R U . . .
C11 C 0.465(3) 0.357(3) 0.5730(19) 0.040(7) Uani 1 1 d . U . . .
C12 C 0.449(3) 0.264(3) 0.5108(19) 0.037(7) Uani 1 1 d . U . . .
C13 C 0.629(3) 0.195(3) 0.3664(19) 0.032(6) Uani 1 1 d . U . . .
C14 C 0.607(3) 0.218(2) 0.2893(18) 0.034(7) Uani 1 1 d . U . . .
H14 H 0.5396 0.2365 0.2647 0.040 Uiso 1 1 calc R U . . .
C15 C 0.690(2) 0.211(2) 0.2508(18) 0.028(7) Uani 1 1 d . U . . .
H15 H 0.6806 0.2282 0.1978 0.033 Uiso 1 1 calc R U . . .
C16 C 0.787(3) 0.179(3) 0.2863(19) 0.035(7) Uani 1 1 d . U . . .
C17 C 0.802(2) 0.154(2) 0.3635(17) 0.030(7) Uani 1 1 d . U . . .
H17 H 0.8682 0.1289 0.3879 0.037 Uiso 1 1 calc R U . . .
C18 C 0.721(2) 0.164(2) 0.4052(18) 0.028(6) Uani 1 1 d . U . . .
H18 H 0.7294 0.1497 0.4585 0.033 Uiso 1 1 calc R U . . .
C19 C 1.010(2) 0.191(3) 0.2947(17) 0.045(9) Uani 1 1 d . U . . .
H19A H 1.0064 0.2652 0.3203 0.068 Uiso 1 1 calc R U . . .
H19B H 1.0685 0.1910 0.2663 0.068 Uiso 1 1 calc R U . . .
H19C H 1.0180 0.1304 0.3329 0.068 Uiso 1 1 calc R U . . .
C20 C 0.284(3) 0.177(2) 0.5224(18) 0.031(6) Uani 1 1 d . U . . .
C21 C 0.188(2) 0.184(2) 0.4767(18) 0.032(7) Uani 1 1 d . U . . .
H21 H 0.1821 0.2032 0.4241 0.039 Uiso 1 1 calc R U . . .
C22 C 0.098(3) 0.162(2) 0.5118(18) 0.042(8) Uani 1 1 d . U . . .
H22 H 0.0299 0.1673 0.4841 0.050 Uiso 1 1 calc R U . . .
C23 C 0.116(3) 0.131(3) 0.5885(17) 0.037(7) Uani 1 1 d . U . . .
C24 C 0.213(2) 0.127(2) 0.6313(18) 0.033(7) Uani 1 1 d . U . . .
H24 H 0.2202 0.1092 0.6841 0.040 Uiso 1 1 calc R U . . .
C25 C 0.298(3) 0.149(2) 0.5986(18) 0.032(7) Uani 1 1 d . U . . .
H25 H 0.3652 0.1452 0.6276 0.039 Uiso 1 1 calc R U . . .
C26 C -0.107(2) 0.130(3) 0.5733(18) 0.052(10) Uani 1 1 d . U . . .
H26A H -0.1005 0.2039 0.5483 0.077 Uiso 1 1 calc R U . . .
H26B H -0.1669 0.1323 0.6008 0.077 Uiso 1 1 calc R U . . .
H26C H -0.1169 0.0697 0.5348 0.077 Uiso 1 1 calc R U . . .
C27 C 0.925(3) 0.484(3) 0.395(2) 0.043(8) Uani 1 1 d . U . . .
C28 C 0.871(2) 0.474(3) 0.3162(17) 0.042(8) Uani 1 1 d . U . . .
H28A H 0.9207 0.4849 0.2805 0.063 Uiso 1 1 calc R U . . .
H28B H 0.8163 0.5313 0.3069 0.063 Uiso 1 1 calc R U . . .
H28C H 0.8403 0.3973 0.3087 0.063 Uiso 1 1 calc R U . . .
N1 N 0.539(2) 0.206(2) 0.4064(16) 0.041(6) Uani 1 1 d . U . . .
N2 N 0.3712(19) 0.1989(19) 0.4835(13) 0.024(5) Uani 1 1 d . U . . .
S1 S 0.8875(7) 0.1686(8) 0.2275(5) 0.046(3) Uani 1 1 d . U . . .
S2 S 0.0084(7) 0.1026(8) 0.6393(5) 0.046(3) Uani 1 1 d . U . . .
Cl1 Cl 0.2984(7) 0.1995(7) 0.2863(5) 0.040(2) Uani 1 1 d . U . . .
Cl2 Cl 0.4061(8) -0.0679(6) 0.3901(5) 0.046(3) Uani 1 1 d . U . . .
Zn1 Zn 0.3994(4) 0.1182(4) 0.3847(3) 0.0362(13) Uani 1 1 d . U . . .
O1 O 0.953(2) 0.5916(17) 0.4188(12) 0.046(6) Uani 1 1 d . U . . .
H1 H 0.9687 0.5922 0.4665 0.070 Uiso 1 1 calc R U . . .
O2 O 0.953(2) 0.4027(18) 0.4392(14) 0.055(7) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.36(4) . ?
C1 C2 1.43(4) . ?
C1 C12 1.53(4) . ?
C2 C7 1.36(4) . ?
C2 C3 1.38(4) . ?
C3 C4 1.44(4) . ?
C4 C5 1.29(4) . ?
C5 C6 1.40(4) . ?
C6 C8 1.41(4) . ?
C6 C7 1.49(4) . ?
C7 C11 1.37(4) . ?
C8 C9 1.36(4) . ?
C9 C10 1.41(4) . ?
C10 C11 1.35(4) . ?
C11 C12 1.54(4) . ?
C12 N2 1.30(4) . ?
C13 C18 1.34(4) . ?
C13 C14 1.38(4) . ?
C13 N1 1.46(4) . ?
C14 C15 1.36(4) . ?
C15 C16 1.37(4) . ?
C16 C17 1.39(4) . ?
C16 S1 1.80(3) . ?
C17 C18 1.39(4) . ?
C19 S1 1.86(3) . ?
C20 C25 1.37(4) . ?
C20 C21 1.39(4) . ?
C20 N2 1.44(4) . ?
C21 C22 1.43(4) . ?
C22 C23 1.39(4) . ?
C23 C24 1.37(4) . ?
C23 S2 1.81(3) . ?
C24 C25 1.35(4) . ?
C26 S2 1.79(3) . ?
C27 O2 1.25(4) . ?
C27 O1 1.36(3) . ?
C27 C28 1.47(4) . ?
N1 Zn1 2.08(3) . ?
N2 Zn1 2.07(2) . ?
Cl1 Zn1 2.232(9) . ?
Cl2 Zn1 2.185(8) . ?

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
N1 C1 C2 137(3) . . ?
N1 C1 C12 114(3) . . ?
C2 C1 C12 108(3) . . ?
C7 C2 C3 121(3) . . ?
C7 C2 C1 105(3) . . ?
C3 C2 C1 134(3) . . ?
C2 C3 C4 119(3) . . ?
C5 C4 C3 120(3) . . ?
C4 C5 C6 125(3) . . ?
C5 C6 C8 131(3) . . ?
C5 C6 C7 115(3) . . ?
C8 C6 C7 114(3) . . ?
C2 C7 C11 121(3) . . ?
C2 C7 C6 120(3) . . ?
C11 C7 C6 119(3) . . ?
C9 C8 C6 124(3) . . ?
C8 C9 C10 121(3) . . ?
C11 C10 C9 116(3) . . ?
C10 C11 C7 125(3) . . ?
C10 C11 C12 133(3) . . ?
C7 C11 C12 101(3) . . ?
N2 C12 C1 120(3) . . ?
N2 C12 C11 134(3) . . ?
C1 C12 C11 105(3) . . ?
C18 C13 C14 126(3) . . ?
C18 C13 N1 120(3) . . ?
C14 C13 N1 114(3) . . ?
C15 C14 C13 115(3) . . ?
C14 C15 C16 122(3) . . ?
C15 C16 C17 120(3) . . ?
C15 C16 S1 117(3) . . ?
C17 C16 S1 123(3) . . ?
C18 C17 C16 120(3) . . ?
C13 C18 C17 117(3) . . ?
C25 C20 C21 124(3) . . ?
C25 C20 N2 121(3) . . ?
C21 C20 N2 115(3) . . ?
C20 C21 C22 118(3) . . ?
C23 C22 C21 116(3) . . ?
C24 C23 C22 124(3) . . ?
C24 C23 S2 116(2) . . ?
C22 C23 S2 120(3) . . ?
C25 C24 C23 120(3) . . ?
C24 C25 C20 118(3) . . ?
O2 C27 O1 118(3) . . ?
O2 C27 C28 126(3) . . ?
O1 C27 C28 116(3) . . ?
C1 N1 C13 120(3) . . ?
C1 N1 Zn1 112(2) . . ?
C13 N1 Zn1 128(2) . . ?
C12 N2 C20 123(3) . . ?
C12 N2 Zn1 111(2) . . ?
C20 N2 Zn1 125(2) . . ?
C16 S1 C19 104.4(15) . . ?
C26 S2 C23 106.3(15) . . ?
N2 Zn1 N1 83.0(10) . . ?
N2 Zn1 Cl2 115.5(7) . . ?
N1 Zn1 Cl2 117.3(8) . . ?
N2 Zn1 Cl1 107.8(7) . . ?
N1 Zn1 Cl1 109.3(8) . . ?
Cl2 Zn1 Cl1 118.4(4) . . ?

_refine_diff_density_max         0.690
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.160

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1061241'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 Cl2 N2 S2 Zn, C H2 Cl2'
_chemical_formula_sum            'C27 H22 Cl4 N2 S2 Zn'
_chemical_formula_weight         645.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.2610(2)
_cell_length_b                   12.02200(10)
_cell_length_c                   18.1350(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.1270(10)
_cell_angle_gamma                90
_cell_volume                     2731.54(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11647
_cell_measurement_theta_min      3.6390
_cell_measurement_theta_max      75.7340

_exptl_crystal_description       chunk
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.464
_shelx_estimated_absorpt_T_min   0.779
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray source'
_diffrn_measurement_device_type  'Agilent SuperNova with AtlasS2 detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16166
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.625
_diffrn_reflns_theta_max         26.554
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5505
_reflns_number_gt                5409
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_cell_refinement       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction        
'CrysAlisPro V 1.171.37.31, Agilent Technologies'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+31.7236P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5505
_refine_ls_number_parameters     356
_refine_ls_number_restraints     294
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0711
_refine_ls_wR_factor_ref         0.1750
_refine_ls_wR_factor_gt          0.1747
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_restrained_S_all      1.207
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0461(4) 0.2611(5) 1.0353(3) 0.0136(11) Uani 1 1 d . U . . .
C2 C 0.0253(4) 0.3438(5) 1.0883(3) 0.0149(11) Uani 1 1 d . U . . .
C3 C 0.0785(5) 0.3798(5) 1.1634(3) 0.0163(11) Uani 1 1 d . U . . .
H3 H 0.1417 0.3436 1.1946 0.020 Uiso 1 1 calc R U . . .
C4 C 0.0369(5) 0.4719(5) 1.1930(3) 0.0186(12) Uani 1 1 d . U . . .
H4 H 0.0738 0.4971 1.2445 0.022 Uiso 1 1 calc R U . . .
C5 C -0.0550(5) 0.5261(5) 1.1499(3) 0.0178(11) Uani 1 1 d . U . . .
H5 H -0.0811 0.5866 1.1722 0.021 Uiso 1 1 calc R U . . .
C6 C -0.1109(4) 0.4920(5) 1.0725(3) 0.0164(11) Uani 1 1 d . U . . .
C7 C -0.0691(4) 0.4009(5) 1.0439(3) 0.0134(11) Uani 1 1 d . U . . .
C8 C -0.2034(5) 0.5429(5) 1.0199(3) 0.0180(12) Uani 1 1 d . U . . .
H8 H -0.2346 0.6051 1.0365 0.022 Uiso 1 1 calc R U . . .
C9 C -0.2481(4) 0.5028(5) 0.9447(3) 0.0185(12) Uani 1 1 d . U . . .
H9 H -0.3094 0.5388 0.9106 0.022 Uiso 1 1 calc R U . . .
C10 C -0.2060(4) 0.4102(5) 0.9171(3) 0.0167(11) Uani 1 1 d . U . . .
H10 H -0.2389 0.3835 0.8654 0.020 Uiso 1 1 calc R U . . .
C11 C -0.1158(4) 0.3589(5) 0.9665(3) 0.0150(11) Uani 1 1 d . U . . .
C12 C -0.0459(4) 0.2677(5) 0.9589(3) 0.0133(10) Uani 1 1 d . U . . .
C13 C 0.2081(4) 0.1711(5) 1.1086(3) 0.0153(11) Uani 1 1 d . U . . .
C14 C 0.3126(5) 0.1751(5) 1.1066(3) 0.0203(12) Uani 1 1 d . U . . .
H14 H 0.3259 0.1935 1.0597 0.024 Uiso 1 1 calc R U . . .
C15 C 0.3962(5) 0.1518(6) 1.1740(4) 0.0223(13) Uani 1 1 d . U . . .
H15 H 0.4676 0.1567 1.1736 0.027 Uiso 1 1 calc R U . . .
C16 C 0.3770(4) 0.1210(5) 1.2426(3) 0.0168(11) Uani 1 1 d . U . . .
C17 C 0.2719(4) 0.1136(5) 1.2426(3) 0.0169(11) Uani 1 1 d . U . . .
H17 H 0.2581 0.0917 1.2887 0.020 Uiso 1 1 calc R U . . .
C18 C 0.1877(4) 0.1380(5) 1.1756(3) 0.0154(11) Uani 1 1 d . U . . .
H18 H 0.1163 0.1321 1.1756 0.019 Uiso 1 1 calc R U . . .
C19 C 0.4358(5) 0.0959(6) 1.4041(4) 0.0270(14) Uani 1 1 d . U . . .
H19A H 0.4035 0.1689 1.4053 0.041 Uiso 1 1 calc R U . . .
H19B H 0.4934 0.0833 1.4535 0.041 Uiso 1 1 calc R U . . .
H19C H 0.3814 0.0379 1.3967 0.041 Uiso 1 1 calc R U . . .
C20 C -0.1293(4) 0.2020(5) 0.8305(3) 0.0147(11) Uani 1 1 d . U . . .
C21 C -0.1067(4) 0.2271(5) 0.7619(3) 0.0173(11) Uani 1 1 d . U . . .
H21 H -0.0356 0.2431 0.7643 0.021 Uiso 1 1 calc R U . . .
C22 C -0.1879(5) 0.2286(5) 0.6912(3) 0.0193(12) Uani 1 1 d . U . . .
H22 H -0.1727 0.2471 0.6451 0.023 Uiso 1 1 calc R U . . .
C23 C -0.2924(4) 0.2032(5) 0.6869(3) 0.0154(11) Uani 1 1 d . U . . .
C24 C -0.3134(5) 0.1730(5) 0.7549(4) 0.0197(12) Uani 1 1 d . U . . .
H24 H -0.3837 0.1521 0.7519 0.024 Uiso 1 1 calc R U . . .
C25 C -0.2334(5) 0.1732(5) 0.8263(3) 0.0177(12) Uani 1 1 d . U . . .
H25 H -0.2488 0.1539 0.8723 0.021 Uiso 1 1 calc R U . . .
C26 C -0.3427(6) 0.2590(8) 0.5303(4) 0.0379(18) Uani 1 1 d . U . . .
H26A H -0.3158 0.3344 0.5453 0.057 Uiso 1 1 calc R U . . .
H26B H -0.3966 0.2606 0.4782 0.057 Uiso 1 1 calc R U . . .
H26C H -0.2835 0.2106 0.5296 0.057 Uiso 1 1 calc R U . . .
N1 N 0.1224(4) 0.1943(4) 1.0381(3) 0.0138(9) Uani 1 1 d . U . . .
N2 N -0.0444(4) 0.2032(4) 0.9029(3) 0.0144(9) Uani 1 1 d . U . . .
S1 S 0.48905(12) 0.09144(15) 1.32483(9) 0.0252(4) Uani 1 1 d . U . . .
S2 S -0.40145(11) 0.20642(14) 0.59935(8) 0.0207(3) Uani 1 1 d . U . . .
Cl1 Cl 0.19687(12) 0.20348(12) 0.86856(8) 0.0199(3) Uani 1 1 d . . . . .
Cl2 Cl 0.09951(12) -0.06469(12) 0.92862(9) 0.0229(3) Uani 1 1 d . . . . .
Zn1 Zn 0.10010(6) 0.11775(6) 0.93119(4) 0.0218(2) Uani 1 1 d . . . . .
Cl3 Cl 0.6166(4) -0.0902(4) 1.2195(3) 0.0382(9) Uani 0.55 1 d . U P A 1
C27 C 0.6418(13) -0.0012(13) 1.1524(10) 0.047(4) Uani 0.55 1 d . U P A 1
H27A H 0.7158 -0.0129 1.1526 0.056 Uiso 0.55 1 calc R U P A 1
H27B H 0.6357 0.0767 1.1682 0.056 Uiso 0.55 1 calc R U P A 1
Cl4 Cl 0.5519(4) -0.0229(4) 1.0565(3) 0.0643(12) Uani 0.55 1 d . U P A 1
Cl5 Cl 0.6833(2) 0.0309(3) 1.21292(18) 0.0171(6) Uani 0.45 1 d . U P B 2
C27A C 0.587(3) -0.096(4) 1.202(3) 0.086(13) Uani 0.45 1 d . U P B 2
H27C H 0.6291 -0.1642 1.2039 0.103 Uiso 0.45 1 calc R U P B 2
H27D H 0.5627 -0.0964 1.2478 0.103 Uiso 0.45 1 calc R U P B 2
Cl6 Cl 0.4957(3) -0.1027(3) 1.1351(2) 0.0348(9) Uani 0.45 1 d . U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.280(7) . ?
C1 C2 1.472(8) . ?
C1 C12 1.518(7) . ?
C2 C3 1.382(8) . ?
C2 C7 1.424(8) . ?
C3 C4 1.418(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.417(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(8) . ?
C6 C8 1.423(8) . ?
C7 C11 1.427(8) . ?
C8 C9 1.383(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.410(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.472(8) . ?
C12 N2 1.281(7) . ?
C13 C18 1.387(8) . ?
C13 C14 1.399(8) . ?
C13 N1 1.432(7) . ?
C14 C15 1.383(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.397(8) . ?
C16 S1 1.762(6) . ?
C17 C18 1.385(8) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 S1 1.798(7) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.401(8) . ?
C20 C21 1.404(8) . ?
C20 N2 1.422(7) . ?
C21 C22 1.378(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.396(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.398(8) . ?
C23 S2 1.763(6) . ?
C24 C25 1.379(8) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 S2 1.793(7) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N1 Zn1 2.077(5) . ?
N2 Zn1 2.085(5) . ?
Cl1 Zn1 2.2257(15) . ?
Cl2 Zn1 2.1936(16) . ?
Cl3 C27 1.732(17) . ?
C27 Cl4 1.776(18) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
Cl4 Cl4 2.134(9) 3_657 ?
Cl5 C27A 1.95(4) . ?
C27A Cl6 1.40(4) . ?
C27A H27C 0.9900 . ?
C27A H27D 0.9900 . ?

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
N1 C1 C2 135.5(5) . . ?
N1 C1 C12 117.2(5) . . ?
C2 C1 C12 107.2(5) . . ?
C3 C2 C7 118.5(5) . . ?
C3 C2 C1 135.3(5) . . ?
C7 C2 C1 105.9(5) . . ?
C2 C3 C4 118.7(5) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 122.5(5) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 120.2(5) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 116.9(5) . . ?
C7 C6 C8 116.5(5) . . ?
C5 C6 C8 126.6(5) . . ?
C6 C7 C2 123.2(5) . . ?
C6 C7 C11 123.0(5) . . ?
C2 C7 C11 113.8(5) . . ?
C9 C8 C6 120.5(5) . . ?
C9 C8 H8 119.7 . . ?
C6 C8 H8 119.7 . . ?
C8 C9 C10 122.3(5) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C11 C10 C9 118.7(5) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C7 118.9(5) . . ?
C10 C11 C12 135.1(5) . . ?
C7 C11 C12 105.8(5) . . ?
N2 C12 C11 134.3(5) . . ?
N2 C12 C1 118.3(5) . . ?
C11 C12 C1 107.2(4) . . ?
C18 C13 C14 120.8(5) . . ?
C18 C13 N1 120.9(5) . . ?
C14 C13 N1 118.2(5) . . ?
C15 C14 C13 119.0(5) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 120.8(5) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 119.3(5) . . ?
C17 C16 S1 123.5(5) . . ?
C15 C16 S1 117.2(4) . . ?
C18 C17 C16 120.3(5) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 119.8(5) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
S1 C19 H19A 109.5 . . ?
S1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
S1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 119.8(5) . . ?
C25 C20 N2 121.4(5) . . ?
C21 C20 N2 118.8(5) . . ?
C22 C21 C20 119.9(5) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.5(5) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 119.2(5) . . ?
C22 C23 S2 123.5(4) . . ?
C24 C23 S2 117.3(4) . . ?
C25 C24 C23 120.9(5) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C20 119.5(5) . . ?
C24 C25 H25 120.2 . . ?
C20 C25 H25 120.2 . . ?
S2 C26 H26A 109.5 . . ?
S2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
S2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 N1 C13 122.9(5) . . ?
C1 N1 Zn1 111.8(4) . . ?
C13 N1 Zn1 125.2(4) . . ?
C12 N2 C20 121.6(5) . . ?
C12 N2 Zn1 110.8(4) . . ?
C20 N2 Zn1 127.4(4) . . ?
C16 S1 C19 103.2(3) . . ?
C23 S2 C26 102.8(3) . . ?
N1 Zn1 N2 81.34(18) . . ?
N1 Zn1 Cl2 117.44(14) . . ?
N2 Zn1 Cl2 119.41(14) . . ?
N1 Zn1 Cl1 109.97(14) . . ?
N2 Zn1 Cl1 106.47(14) . . ?
Cl2 Zn1 Cl1 116.80(6) . . ?
Cl3 C27 Cl4 112.0(9) . . ?
Cl3 C27 H27A 109.2 . . ?
Cl4 C27 H27A 109.2 . . ?
Cl3 C27 H27B 109.2 . . ?
Cl4 C27 H27B 109.2 . . ?
H27A C27 H27B 107.9 . . ?
C27 Cl4 Cl4 156.6(7) . 3_657 ?
Cl6 C27A Cl5 119(3) . . ?
Cl6 C27A H27C 107.5 . . ?
Cl5 C27A H27C 107.5 . . ?
Cl6 C27A H27D 107.5 . . ?
Cl5 C27A H27D 107.5 . . ?
H27C C27A H27D 107.0 . . ?

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
N1 C1 C2 C3 -2.5(12) . . . . ?
C12 C1 C2 C3 -178.0(6) . . . . ?
N1 C1 C2 C7 171.6(6) . . . . ?
C12 C1 C2 C7 -3.8(6) . . . . ?
C7 C2 C3 C4 0.0(8) . . . . ?
C1 C2 C3 C4 173.6(6) . . . . ?
C2 C3 C4 C5 0.6(9) . . . . ?
C3 C4 C5 C6 -1.2(9) . . . . ?
C4 C5 C6 C7 1.2(8) . . . . ?
C4 C5 C6 C8 -176.7(6) . . . . ?
C5 C6 C7 C2 -0.6(8) . . . . ?
C8 C6 C7 C2 177.5(5) . . . . ?
C5 C6 C7 C11 -178.7(5) . . . . ?
C8 C6 C7 C11 -0.6(8) . . . . ?
C3 C2 C7 C6 0.0(8) . . . . ?
C1 C2 C7 C6 -175.3(5) . . . . ?
C3 C2 C7 C11 178.3(5) . . . . ?
C1 C2 C7 C11 3.0(6) . . . . ?
C7 C6 C8 C9 0.1(8) . . . . ?
C5 C6 C8 C9 178.0(6) . . . . ?
C6 C8 C9 C10 0.7(9) . . . . ?
C8 C9 C10 C11 -1.0(9) . . . . ?
C9 C10 C11 C7 0.5(8) . . . . ?
C9 C10 C11 C12 -175.7(6) . . . . ?
C6 C7 C11 C10 0.2(8) . . . . ?
C2 C7 C11 C10 -178.0(5) . . . . ?
C6 C7 C11 C12 177.5(5) . . . . ?
C2 C7 C11 C12 -0.7(6) . . . . ?
C10 C11 C12 N2 0.0(12) . . . . ?
C7 C11 C12 N2 -176.6(6) . . . . ?
C10 C11 C12 C1 174.9(6) . . . . ?
C7 C11 C12 C1 -1.7(6) . . . . ?
N1 C1 C12 N2 2.9(8) . . . . ?
C2 C1 C12 N2 179.3(5) . . . . ?
N1 C1 C12 C11 -172.9(5) . . . . ?
C2 C1 C12 C11 3.5(6) . . . . ?
C18 C13 C14 C15 -3.8(9) . . . . ?
N1 C13 C14 C15 -179.3(6) . . . . ?
C13 C14 C15 C16 2.1(10) . . . . ?
C14 C15 C16 C17 0.2(9) . . . . ?
C14 C15 C16 S1 179.3(5) . . . . ?
C15 C16 C17 C18 -0.9(9) . . . . ?
S1 C16 C17 C18 -179.9(5) . . . . ?
C16 C17 C18 C13 -0.7(9) . . . . ?
C14 C13 C18 C17 3.1(9) . . . . ?
N1 C13 C18 C17 178.5(5) . . . . ?
C25 C20 C21 C22 3.2(9) . . . . ?
N2 C20 C21 C22 -178.7(5) . . . . ?
C20 C21 C22 C23 -1.3(9) . . . . ?
C21 C22 C23 C24 -1.8(9) . . . . ?
C21 C22 C23 S2 178.4(5) . . . . ?
C22 C23 C24 C25 3.1(9) . . . . ?
S2 C23 C24 C25 -177.1(5) . . . . ?
C23 C24 C25 C20 -1.2(9) . . . . ?
C21 C20 C25 C24 -1.9(9) . . . . ?
N2 C20 C25 C24 -180.0(5) . . . . ?
C2 C1 N1 C13 11.8(10) . . . . ?
C12 C1 N1 C13 -173.1(5) . . . . ?
C2 C1 N1 Zn1 -172.1(5) . . . . ?
C12 C1 N1 Zn1 3.0(6) . . . . ?
C18 C13 N1 C1 52.2(8) . . . . ?
C14 C13 N1 C1 -132.3(6) . . . . ?
C18 C13 N1 Zn1 -123.4(5) . . . . ?
C14 C13 N1 Zn1 52.1(7) . . . . ?
C11 C12 N2 C20 -7.7(10) . . . . ?
C1 C12 N2 C20 177.9(5) . . . . ?
C11 C12 N2 Zn1 167.4(5) . . . . ?
C1 C12 N2 Zn1 -7.0(6) . . . . ?
C25 C20 N2 C12 -61.2(8) . . . . ?
C21 C20 N2 C12 120.7(6) . . . . ?
C25 C20 N2 Zn1 124.6(5) . . . . ?
C21 C20 N2 Zn1 -53.5(7) . . . . ?
C17 C16 S1 C19 -16.9(6) . . . . ?
C15 C16 S1 C19 164.1(5) . . . . ?
C22 C23 S2 C26 -4.8(6) . . . . ?
C24 C23 S2 C26 175.4(5) . . . . ?
Cl3 C27 Cl4 Cl4 138.9(14) . . . 3_657 ?

_refine_diff_density_max         0.543
_refine_diff_density_min         -0.945
_refine_diff_density_rms         0.139

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1061242'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H24 Cl2 N2 O2 Zn'
_chemical_formula_sum            'C36 H24 Cl2 N2 O2 Zn'
_chemical_formula_weight         652.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   14.0015(9)
_cell_length_b                   11.7228(9)
_cell_length_c                   17.9471(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.996(6)
_cell_angle_gamma                90
_cell_volume                     2944.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2439
_cell_measurement_theta_min      4.4880
_cell_measurement_theta_max      71.6610

_exptl_crystal_description       chip
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    3.122
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89282
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray source'
_diffrn_measurement_device_type  'Agilent SuperNova with AtlasS2 detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33186
_diffrn_reflns_av_unetI/netI     0.2099
_diffrn_reflns_av_R_equivalents  0.1948
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.506
_diffrn_reflns_theta_max         76.612
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6070
_reflns_number_gt                3220
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_cell_refinement       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction        
'CrysAlisPro V 1.171.37.31, Agilent Technologies'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0900P)²+6.3083P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6070
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2048
_refine_ls_R_factor_gt           0.1160
_refine_ls_wR_factor_ref         0.3473
_refine_ls_wR_factor_gt          0.3155
_refine_ls_goodness_of_fit_ref   1.409
_refine_ls_restrained_S_all      1.409
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4642(7) 0.2256(8) 0.4661(6) 0.027(2) Uani 1 1 d . . . . .
C2 C 0.3972(7) 0.1387(8) 0.4927(6) 0.028(2) Uani 1 1 d . . . . .
C3 C 0.3143(8) 0.0900(9) 0.4649(6) 0.033(3) Uani 1 1 d . . . . .
H3 H 0.2865 0.1141 0.4185 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2716(8) 0.0038(8) 0.5065(6) 0.033(3) Uani 1 1 d . . . . .
H4 H 0.2139 -0.0294 0.4873 0.039 Uiso 1 1 calc R U . . .
C5 C 0.3097(8) -0.0353(8) 0.5744(7) 0.037(3) Uani 1 1 d . . . . .
H5 H 0.2774 -0.0923 0.6015 0.045 Uiso 1 1 calc R U . . .
C6 C 0.3973(8) 0.0111(8) 0.6028(6) 0.031(3) Uani 1 1 d . . . . .
C7 C 0.4386(8) 0.0984(8) 0.5614(6) 0.027(2) Uani 1 1 d . . . . .
C8 C 0.4465(8) -0.0220(9) 0.6702(6) 0.034(3) Uani 1 1 d . . . . .
H8 H 0.4199 -0.0783 0.7013 0.041 Uiso 1 1 calc R U . . .
C9 C 0.5330(8) 0.0280(8) 0.6902(6) 0.032(3) Uani 1 1 d . . . . .
H9 H 0.5660 0.0027 0.7343 0.038 Uiso 1 1 calc R U . . .
C10 C 0.5742(8) 0.1153(8) 0.6476(6) 0.030(2) Uani 1 1 d . . . . .
H10 H 0.6333 0.1490 0.6631 0.036 Uiso 1 1 calc R U . . .
C11 C 0.5269(7) 0.1504(8) 0.5832(6) 0.028(2) Uani 1 1 d . . . . .
C12 C 0.5469(7) 0.2313(7) 0.5229(5) 0.023(2) Uani 1 1 d . . . . .
C13 C 0.3894(8) 0.2901(8) 0.3544(6) 0.032(3) Uani 1 1 d . . . . .
C14 C 0.4037(8) 0.2609(8) 0.2805(6) 0.028(2) Uani 1 1 d . . . . .
H14 H 0.4659 0.2418 0.2650 0.034 Uiso 1 1 calc R U . . .
C15 C 0.3266(8) 0.2596(9) 0.2295(6) 0.034(3) Uani 1 1 d . . . . .
H15 H 0.3354 0.2380 0.1792 0.040 Uiso 1 1 calc R U . . .
C16 C 0.2364(8) 0.2904(8) 0.2529(6) 0.031(3) Uani 1 1 d . . . . .
C17 C 0.2241(8) 0.3271(8) 0.3252(6) 0.032(3) Uani 1 1 d . . . . .
H17 H 0.1632 0.3528 0.3397 0.038 Uiso 1 1 calc R U . . .
C18 C 0.3007(8) 0.3266(8) 0.3769(6) 0.031(3) Uani 1 1 d . . . . .
H18 H 0.2923 0.3508 0.4267 0.037 Uiso 1 1 calc R U . . .
C19 C 0.1537(8) 0.2223(9) 0.1443(6) 0.031(3) Uani 1 1 d . . . . .
C20 C 0.1334(8) 0.2719(9) 0.0761(6) 0.036(3) Uani 1 1 d . . . . .
H20 H 0.1271 0.3523 0.0718 0.043 Uiso 1 1 calc R U . . .
C21 C 0.1222(8) 0.2023(10) 0.0130(6) 0.037(3) Uani 1 1 d . . . . .
H21 H 0.1072 0.2354 -0.0343 0.045 Uiso 1 1 calc R U . . .
C22 C 0.1330(8) 0.0851(10) 0.0194(7) 0.042(3) Uani 1 1 d . . . . .
H22 H 0.1260 0.0379 -0.0234 0.050 Uiso 1 1 calc R U . . .
C23 C 0.1539(9) 0.0375(10) 0.0886(7) 0.043(3) Uani 1 1 d . . . . .
H23 H 0.1608 -0.0429 0.0933 0.052 Uiso 1 1 calc R U . . .
C24 C 0.1648(9) 0.1058(9) 0.1507(6) 0.039(3) Uani 1 1 d . . . . .
H24 H 0.1800 0.0727 0.1979 0.047 Uiso 1 1 calc R U . . .
C25 C 0.6978(7) 0.3151(8) 0.5573(6) 0.028(2) Uani 1 1 d . . . . .
C26 C 0.7889(8) 0.2950(9) 0.5299(7) 0.038(3) Uani 1 1 d . . . . .
H26 H 0.7962 0.2634 0.4816 0.045 Uiso 1 1 calc R U . . .
C27 C 0.8679(8) 0.3224(9) 0.5748(6) 0.036(3) Uani 1 1 d . . . . .
H27 H 0.9303 0.3081 0.5579 0.044 Uiso 1 1 calc R U . . .
C28 C 0.8559(8) 0.3706(9) 0.6445(6) 0.036(3) Uani 1 1 d . . . . .
C29 C 0.7674(8) 0.3870(9) 0.6715(6) 0.032(3) Uani 1 1 d . . . . .
H29 H 0.7606 0.4172 0.7202 0.038 Uiso 1 1 calc R U . . .
C30 C 0.6870(8) 0.3596(9) 0.6279(6) 0.033(3) Uani 1 1 d . . . . .
H30 H 0.6250 0.3712 0.6464 0.040 Uiso 1 1 calc R U . . .
C31 C 0.9521(8) 0.4108(10) 0.7557(6) 0.036(3) Uani 1 1 d . . . . .
C32 C 1.0033(9) 0.5024(11) 0.7867(8) 0.049(4) Uani 1 1 d . . . . .
H32 H 1.0228 0.5638 0.7562 0.059 Uiso 1 1 calc R U . . .
C33 C 1.0252(10) 0.5026(11) 0.8619(8) 0.055(4) Uani 1 1 d . . . . .
H33 H 1.0609 0.5639 0.8835 0.066 Uiso 1 1 calc R U . . .
C34 C 0.9954(10) 0.4135(12) 0.9063(8) 0.058(4) Uani 1 1 d . . . . .
H34 H 1.0098 0.4143 0.9584 0.070 Uiso 1 1 calc R U . . .
C35 C 0.9455(9) 0.3252(12) 0.8752(7) 0.048(3) Uani 1 1 d . . . . .
H35 H 0.9250 0.2646 0.9059 0.058 Uiso 1 1 calc R U . . .
C36 C 0.9243(8) 0.3225(10) 0.7996(7) 0.039(3) Uani 1 1 d . . . . .
H36 H 0.8906 0.2596 0.7782 0.047 Uiso 1 1 calc R U . . .
Cl1 Cl 0.69215(19) 0.3073(2) 0.32131(15) 0.0330(7) Uani 1 1 d . . . . .
Cl2 Cl 0.5741(2) 0.5647(2) 0.40697(16) 0.0365(7) Uani 1 1 d . . . . .
N1 N 0.4685(6) 0.2868(6) 0.4077(5) 0.026(2) Uani 1 1 d . . . . .
N2 N 0.6172(6) 0.2963(7) 0.5071(5) 0.027(2) Uani 1 1 d . . . . .
O1 O 0.1560(5) 0.2928(6) 0.2061(4) 0.041(2) Uani 1 1 d . . . . .
O2 O 0.9401(6) 0.4118(8) 0.6789(5) 0.051(2) Uani 1 1 d . . . . .
Zn1 Zn 0.59541(10) 0.37871(11) 0.40469(8) 0.0291(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.273(12) . ?
C1 C2 1.475(14) . ?
C1 C12 1.517(12) . ?
C2 C3 1.371(14) . ?
C2 C7 1.425(13) . ?
C3 C4 1.403(15) . ?
C4 C5 1.392(14) . ?
C5 C6 1.420(14) . ?
C6 C7 1.402(14) . ?
C6 C8 1.425(14) . ?
C7 C11 1.421(14) . ?
C8 C9 1.382(14) . ?
C9 C10 1.412(14) . ?
C10 C11 1.375(13) . ?
C11 C12 1.474(14) . ?
C12 N2 1.284(13) . ?
C13 C18 1.385(15) . ?
C13 C14 1.391(15) . ?
C13 N1 1.439(12) . ?
C14 C15 1.391(13) . ?
C15 C16 1.392(15) . ?
C16 O1 1.381(11) . ?
C16 C17 1.385(15) . ?
C17 C18 1.393(13) . ?
C19 C20 1.376(14) . ?
C19 C24 1.378(14) . ?
C19 O1 1.382(12) . ?
C20 C21 1.400(14) . ?
C21 C22 1.386(15) . ?
C22 C23 1.384(16) . ?
C23 C24 1.377(15) . ?
C25 C30 1.384(14) . ?
C25 C26 1.404(16) . ?
C25 N2 1.436(11) . ?
C26 C27 1.383(14) . ?
C27 C28 1.388(16) . ?
C28 C29 1.361(16) . ?
C28 O2 1.398(12) . ?
C29 C30 1.386(13) . ?
C31 C36 1.366(15) . ?
C31 O2 1.383(13) . ?
C31 C32 1.396(16) . ?
C32 C33 1.373(17) . ?
C33 C34 1.39(2) . ?
C34 C35 1.357(18) . ?
C35 C36 1.379(15) . ?
Cl1 Zn1 2.217(3) . ?
Cl2 Zn1 2.201(3) . ?
N1 Zn1 2.080(8) . ?
N2 Zn1 2.089(8) . ?

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
N1 C1 C2 134.8(9) . . ?
N1 C1 C12 118.1(9) . . ?
C2 C1 C12 107.0(8) . . ?
C3 C2 C7 119.4(10) . . ?
C3 C2 C1 135.2(10) . . ?
C7 C2 C1 105.3(8) . . ?
C2 C3 C4 118.6(10) . . ?
C5 C4 C3 123.1(10) . . ?
C4 C5 C6 119.2(10) . . ?
C7 C6 C5 117.2(9) . . ?
C7 C6 C8 116.9(10) . . ?
C5 C6 C8 125.9(10) . . ?
C6 C7 C11 122.5(9) . . ?
C6 C7 C2 122.5(9) . . ?
C11 C7 C2 114.9(10) . . ?
C9 C8 C6 120.0(10) . . ?
C8 C9 C10 122.4(9) . . ?
C11 C10 C9 118.6(10) . . ?
C10 C11 C7 119.5(10) . . ?
C10 C11 C12 135.4(10) . . ?
C7 C11 C12 105.0(9) . . ?
N2 C12 C11 135.3(9) . . ?
N2 C12 C1 116.8(9) . . ?
C11 C12 C1 107.8(8) . . ?
C18 C13 C14 120.9(9) . . ?
C18 C13 N1 119.5(10) . . ?
C14 C13 N1 119.5(10) . . ?
C15 C14 C13 119.7(11) . . ?
C14 C15 C16 119.4(11) . . ?
O1 C16 C17 116.0(10) . . ?
O1 C16 C15 123.4(10) . . ?
C17 C16 C15 120.5(9) . . ?
C16 C17 C18 120.3(11) . . ?
C13 C18 C17 119.0(10) . . ?
C20 C19 C24 120.7(10) . . ?
C20 C19 O1 117.3(9) . . ?
C24 C19 O1 121.8(10) . . ?
C19 C20 C21 119.2(10) . . ?
C22 C21 C20 120.1(11) . . ?
C23 C22 C21 119.6(11) . . ?
C24 C23 C22 120.3(11) . . ?
C23 C24 C19 120.1(10) . . ?
C30 C25 C26 120.9(9) . . ?
C30 C25 N2 121.7(10) . . ?
C26 C25 N2 117.3(9) . . ?
C27 C26 C25 118.4(11) . . ?
C26 C27 C28 120.0(11) . . ?
C29 C28 C27 121.3(10) . . ?
C29 C28 O2 123.9(11) . . ?
C27 C28 O2 114.4(11) . . ?
C28 C29 C30 119.8(11) . . ?
C25 C30 C29 119.5(11) . . ?
C36 C31 O2 123.7(10) . . ?
C36 C31 C32 120.3(11) . . ?
O2 C31 C32 115.7(11) . . ?
C33 C32 C31 119.1(12) . . ?
C32 C33 C34 120.2(12) . . ?
C35 C34 C33 119.9(13) . . ?
C34 C35 C36 120.8(13) . . ?
C31 C36 C35 119.6(12) . . ?
C1 N1 C13 120.3(9) . . ?
C1 N1 Zn1 112.2(6) . . ?
C13 N1 Zn1 127.4(7) . . ?
C12 N2 C25 122.9(9) . . ?
C12 N2 Zn1 112.3(6) . . ?
C25 N2 Zn1 124.6(7) . . ?
C16 O1 C19 118.1(8) . . ?
C31 O2 C28 120.6(9) . . ?
N1 Zn1 N2 80.6(3) . . ?
N1 Zn1 Cl2 113.3(2) . . ?
N2 Zn1 Cl2 117.2(2) . . ?
N1 Zn1 Cl1 111.4(2) . . ?
N2 Zn1 Cl1 110.2(2) . . ?
Cl2 Zn1 Cl1 118.23(12) . . ?

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
N1 C1 C2 C3 0(2) . . . . ?
C12 C1 C2 C3 -175.1(12) . . . . ?
N1 C1 C2 C7 176.4(12) . . . . ?
C12 C1 C2 C7 0.8(11) . . . . ?
C7 C2 C3 C4 1.8(16) . . . . ?
C1 C2 C3 C4 177.3(11) . . . . ?
C2 C3 C4 C5 -0.5(17) . . . . ?
C3 C4 C5 C6 -1.9(17) . . . . ?
C4 C5 C6 C7 2.8(16) . . . . ?
C4 C5 C6 C8 -178.3(11) . . . . ?
C5 C6 C7 C11 -179.0(10) . . . . ?
C8 C6 C7 C11 2.0(16) . . . . ?
C5 C6 C7 C2 -1.5(16) . . . . ?
C8 C6 C7 C2 179.4(10) . . . . ?
C3 C2 C7 C6 -0.8(16) . . . . ?
C1 C2 C7 C6 -177.5(10) . . . . ?
C3 C2 C7 C11 176.8(10) . . . . ?
C1 C2 C7 C11 0.2(12) . . . . ?
C7 C6 C8 C9 -2.9(16) . . . . ?
C5 C6 C8 C9 178.1(11) . . . . ?
C6 C8 C9 C10 2.5(17) . . . . ?
C8 C9 C10 C11 -1.0(17) . . . . ?
C9 C10 C11 C7 0.0(16) . . . . ?
C9 C10 C11 C12 -176.1(11) . . . . ?
C6 C7 C11 C10 -0.5(17) . . . . ?
C2 C7 C11 C10 -178.2(9) . . . . ?
C6 C7 C11 C12 176.6(10) . . . . ?
C2 C7 C11 C12 -1.0(12) . . . . ?
C10 C11 C12 N2 3(2) . . . . ?
C7 C11 C12 N2 -173.8(11) . . . . ?
C10 C11 C12 C1 177.9(12) . . . . ?
C7 C11 C12 C1 1.5(11) . . . . ?
N1 C1 C12 N2 -1.6(14) . . . . ?
C2 C1 C12 N2 174.8(9) . . . . ?
N1 C1 C12 C11 -177.9(9) . . . . ?
C2 C1 C12 C11 -1.4(11) . . . . ?
C18 C13 C14 C15 -5.0(15) . . . . ?
N1 C13 C14 C15 177.5(9) . . . . ?
C13 C14 C15 C16 1.5(15) . . . . ?
C14 C15 C16 O1 179.3(9) . . . . ?
C14 C15 C16 C17 3.1(15) . . . . ?
O1 C16 C17 C18 179.2(9) . . . . ?
C15 C16 C17 C18 -4.3(15) . . . . ?
C14 C13 C18 C17 3.8(15) . . . . ?
N1 C13 C18 C17 -178.6(9) . . . . ?
C16 C17 C18 C13 0.8(15) . . . . ?
C24 C19 C20 C21 1.2(17) . . . . ?
O1 C19 C20 C21 -174.5(10) . . . . ?
C19 C20 C21 C22 -1.0(17) . . . . ?
C20 C21 C22 C23 0.6(18) . . . . ?
C21 C22 C23 C24 -0.5(19) . . . . ?
C22 C23 C24 C19 0.8(19) . . . . ?
C20 C19 C24 C23 -1.1(18) . . . . ?
O1 C19 C24 C23 174.4(11) . . . . ?
C30 C25 C26 C27 -0.9(15) . . . . ?
N2 C25 C26 C27 174.2(9) . . . . ?
C25 C26 C27 C28 -1.3(15) . . . . ?
C26 C27 C28 C29 3.1(16) . . . . ?
C26 C27 C28 O2 -169.7(9) . . . . ?
C27 C28 C29 C30 -2.6(16) . . . . ?
O2 C28 C29 C30 169.5(10) . . . . ?
C26 C25 C30 C29 1.4(15) . . . . ?
N2 C25 C30 C29 -173.5(9) . . . . ?
C28 C29 C30 C25 0.3(15) . . . . ?
C36 C31 C32 C33 -0.1(19) . . . . ?
O2 C31 C32 C33 -174.6(11) . . . . ?
C31 C32 C33 C34 -1(2) . . . . ?
C32 C33 C34 C35 1(2) . . . . ?
C33 C34 C35 C36 0(2) . . . . ?
O2 C31 C36 C35 175.2(11) . . . . ?
C32 C31 C36 C35 1.2(18) . . . . ?
C34 C35 C36 C31 -1.3(19) . . . . ?
C2 C1 N1 C13 8.8(18) . . . . ?
C12 C1 N1 C13 -176.0(9) . . . . ?
C2 C1 N1 Zn1 -173.5(10) . . . . ?
C12 C1 N1 Zn1 1.7(11) . . . . ?
C18 C13 N1 C1 59.4(13) . . . . ?
C14 C13 N1 C1 -123.0(11) . . . . ?
C18 C13 N1 Zn1 -117.9(10) . . . . ?
C14 C13 N1 Zn1 59.7(11) . . . . ?
C11 C12 N2 C25 -8.6(18) . . . . ?
C1 C12 N2 C25 176.4(8) . . . . ?
C11 C12 N2 Zn1 175.5(10) . . . . ?
C1 C12 N2 Zn1 0.6(11) . . . . ?
C30 C25 N2 C12 -58.5(14) . . . . ?
C26 C25 N2 C12 126.4(11) . . . . ?
C30 C25 N2 Zn1 116.8(10) . . . . ?
C26 C25 N2 Zn1 -58.3(11) . . . . ?
C17 C16 O1 C19 -157.3(9) . . . . ?
C15 C16 O1 C19 26.3(15) . . . . ?
C20 C19 O1 C16 -127.1(11) . . . . ?
C24 C19 O1 C16 57.2(15) . . . . ?
C36 C31 O2 C28 40.8(17) . . . . ?
C32 C31 O2 C28 -144.9(11) . . . . ?
C29 C28 O2 C31 38.7(16) . . . . ?
C27 C28 O2 C31 -148.7(10) . . . . ?

_refine_diff_density_max         0.512
_refine_diff_density_min         -0.877
_refine_diff_density_rms         0.110

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1061243'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C72 H48 Cl4 N4 O4 Zn2, 0.742(C H2 Cl2)'
_chemical_formula_sum            'C72.74 H49.48 Cl5.48 N4 O4 Zn2'
_chemical_formula_weight         1369.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   17.442(7)
_cell_length_b                   11.790(5)
_cell_length_c                   31.054(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.238(7)
_cell_angle_gamma                90
_cell_volume                     6190(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11595
_cell_measurement_theta_min      1.5197
_cell_measurement_theta_max      31.1401

_exptl_crystal_description       chip
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             2798
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.068
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7810
_exptl_absorpt_process_details   
;
Abscor. T. Higashi. (2001). Rigaku Corp. Tokyo, Japan
;


_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku AFC-12 with Saturn 724+ CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47397
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.855
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7097
_reflns_number_gt                6447
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_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     
'w=1/[σ²(Fo²)+(0.0897P)²+14.4254P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7097
_refine_ls_number_parameters     527
_refine_ls_number_restraints     879
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0730
_refine_ls_wR_factor_ref         0.1962
_refine_ls_wR_factor_gt          0.1896
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_restrained_S_all      1.236
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2777(2) 0.0163(3) 0.75977(14) 0.0394(8) Uani 1 1 d . U . . .
C2 C 1.2610(3) 0.1042(3) 0.79004(15) 0.0431(9) Uani 1 1 d . U . . .
C3 C 1.3012(3) 0.1502(4) 0.83008(17) 0.0522(11) Uani 1 1 d . U . . .
H3 H 1.3503 0.1222 0.8453 0.063 Uiso 1 1 calc R U . . .
C4 C 1.2649(4) 0.2418(4) 0.84726(19) 0.0629(13) Uani 1 1 d . U . . .
H4 H 1.2912 0.2725 0.8745 0.075 Uiso 1 1 calc R U . . .
C5 C 1.1943(3) 0.2868(4) 0.82630(19) 0.0606(12) Uani 1 1 d . U . . .
H5 H 1.1736 0.3468 0.8393 0.073 Uiso 1 1 calc R U . . .
C6 C 1.1516(3) 0.2435(4) 0.78484(18) 0.0545(11) Uani 1 1 d . U . . .
C7 C 1.1865(3) 0.1506(3) 0.76749(16) 0.0465(9) Uani 1 1 d . U . . .
C8 C 1.0788(3) 0.2817(4) 0.7585(2) 0.0593(12) Uani 1 1 d . U . . .
H8 H 1.0532 0.3414 0.7687 0.071 Uiso 1 1 calc R U . . .
C9 C 1.0444(3) 0.2338(4) 0.7183(2) 0.0584(12) Uani 1 1 d . U . . .
H9 H 0.9969 0.2631 0.7016 0.070 Uiso 1 1 calc R U . . .
C10 C 1.0796(3) 0.1397(4) 0.70112(19) 0.0526(11) Uani 1 1 d . U . . .
H10 H 1.0552 0.1074 0.6739 0.063 Uiso 1 1 calc R U . . .
C11 C 1.1507(2) 0.0984(3) 0.72601(15) 0.0441(9) Uani 1 1 d . U . . .
C12 C 1.2074(2) 0.0094(3) 0.72007(14) 0.0395(8) Uani 1 1 d . U . . .
C13 C 1.4026(3) -0.0569(3) 0.79799(14) 0.0405(8) Uani 1 1 d . U . . .
C14 C 1.4795(2) -0.0450(3) 0.79314(14) 0.0426(9) Uani 1 1 d . U . . .
H14 H 1.4881 -0.0331 0.7651 0.051 Uiso 1 1 calc R U . . .
C15 C 1.5432(3) -0.0509(4) 0.82984(15) 0.0480(10) Uani 1 1 d . U . . .
H15 H 1.5944 -0.0399 0.8268 0.058 Uiso 1 1 calc R U . . .
C16 C 1.5298(3) -0.0733(4) 0.87087(16) 0.0551(11) Uani 1 1 d . U . . .
C17 C 1.4533(3) -0.0909(4) 0.87569(16) 0.0604(12) Uani 1 1 d . U . . .
H17 H 1.4452 -0.1077 0.9035 0.072 Uiso 1 1 calc R U . . .
C18 C 1.3897(3) -0.0834(4) 0.83935(15) 0.0505(10) Uani 1 1 d . U . . .
H18 H 1.3386 -0.0959 0.8424 0.061 Uiso 1 1 calc R U . . .
C19 C 1.1449(2) -0.0853(4) 0.65219(14) 0.0437(9) Uani 1 1 d . U . . .
C20 C 1.0695(2) -0.1096(4) 0.65759(15) 0.0446(9) Uani 1 1 d . U . . .
H20 H 1.0602 -0.1086 0.6858 0.054 Uiso 1 1 calc R U . . .
C21 C 1.0086(3) -0.1353(4) 0.62109(16) 0.0500(10) Uani 1 1 d . U . . .
H21 H 0.9581 -0.1500 0.6247 0.060 Uiso 1 1 calc R U . . .
C22 C 1.0228(3) -0.1390(5) 0.57962(17) 0.0629(13) Uani 1 1 d . U . . .
C23 C 1.0980(4) -0.1186(7) 0.57381(19) 0.0829(19) Uani 1 1 d . U . . .
H23 H 1.1073 -0.1229 0.5456 0.099 Uiso 1 1 calc R U . . .
C24 C 1.1594(3) -0.0918(6) 0.61032(17) 0.0679(14) Uani 1 1 d . U . . .
H24 H 1.2099 -0.0783 0.6067 0.081 Uiso 1 1 calc R U . . .
C25 C 1.6590(3) -0.0207(5) 0.91524(17) 0.0547(16) Uani 0.773 1 d D U P A 1
C26 C 1.6595(3) 0.0906(5) 0.90145(16) 0.0551(14) Uani 0.773 1 d D U P A 1
H26 H 1.6137 0.1222 0.8837 0.066 Uiso 0.773 1 calc R U P A 1
C27 C 1.7272(3) 0.1556(5) 0.91377(18) 0.0674(17) Uani 0.773 1 d D U P A 1
H27 H 1.7270 0.2304 0.9042 0.081 Uiso 0.773 1 calc R U P A 1
C28 C 1.7955(3) 0.1092(6) 0.9404(2) 0.077(2) Uani 0.773 1 d D U P A 1
H28 H 1.8411 0.1529 0.9492 0.092 Uiso 0.773 1 calc R U P A 1
C29 C 1.7956(4) -0.0020(6) 0.9540(2) 0.095(3) Uani 0.773 1 d D U P A 1
H29 H 1.8416 -0.0338 0.9715 0.114 Uiso 0.773 1 calc R U P A 1
C36 C 1.7280(4) -0.0662(5) 0.9417(2) 0.085(2) Uani 0.773 1 d D U P A 1
H36 H 1.7284 -0.1410 0.9513 0.102 Uiso 0.773 1 calc R U P A 1
C25A C 1.6672(5) -0.0625(17) 0.9207(7) 0.068(5) Uani 0.227 1 d D U P B 2
C26A C 1.6860(9) 0.0450(15) 0.9104(6) 0.070(5) Uani 0.227 1 d D U P B 2
H26A H 1.6466 0.0959 0.8970 0.084 Uiso 0.227 1 calc R U P B 2
C27A C 1.7650(11) 0.0766(14) 0.9202(7) 0.081(6) Uani 0.227 1 d D U P B 2
H27A H 1.7790 0.1493 0.9133 0.097 Uiso 0.227 1 calc R U P B 2
C28A C 1.8227(7) 0.0000(18) 0.9400(7) 0.078(6) Uani 0.227 1 d D U P B 2
H28A H 1.8757 0.0212 0.9467 0.094 Uiso 0.227 1 calc R U P B 2
C29A C 1.8020(8) -0.1080(16) 0.9501(7) 0.088(6) Uani 0.227 1 d D U P B 2
H29A H 1.8410 -0.1596 0.9634 0.106 Uiso 0.227 1 calc R U P B 2
C36A C 1.7232(10) -0.1397(14) 0.9403(7) 0.077(5) Uani 0.227 1 d D U P B 2
H36A H 1.7087 -0.2123 0.9470 0.092 Uiso 0.227 1 calc R U P B 2
C30 C 0.9698(4) -0.2077(5) 0.50457(17) 0.0529(17) Uani 0.629 1 d D U P C 1
C31 C 0.9963(4) -0.3131(5) 0.4975(2) 0.0561(18) Uani 0.629 1 d D U P C 1
H31 H 1.0080 -0.3654 0.5206 0.067 Uiso 0.629 1 calc R U P C 1
C32 C 1.0060(5) -0.3427(6) 0.4556(2) 0.065(2) Uani 0.629 1 d D U P C 1
H32 H 1.0241 -0.4146 0.4507 0.077 Uiso 0.629 1 calc R U P C 1
C33 C 0.9889(7) -0.2659(8) 0.4221(2) 0.088(5) Uani 0.629 1 d D U P C 1
H33 H 0.9950 -0.2853 0.3941 0.105 Uiso 0.629 1 calc R U P C 1
C34 C 0.9621(7) -0.1582(7) 0.4295(3) 0.112(4) Uani 0.629 1 d D U P C 1
H34 H 0.9511 -0.1053 0.4065 0.135 Uiso 0.629 1 calc R U P C 1
C35 C 0.9518(6) -0.1298(6) 0.4708(3) 0.098(3) Uani 0.629 1 d D U P C 1
H35 H 0.9329 -0.0584 0.4757 0.118 Uiso 0.629 1 calc R U P C 1
C30A C 0.8940(4) -0.0958(7) 0.5275(3) 0.048(2) Uani 0.371 1 d D U P D 2
C31A C 0.8770(5) 0.0082(7) 0.5440(3) 0.049(2) Uani 0.371 1 d D U P D 2
H31A H 0.9164 0.0453 0.5667 0.058 Uiso 0.371 1 d R U P D 2
C32A C 0.8044(5) 0.0585(7) 0.5281(3) 0.057(3) Uani 0.371 1 d D U P D 2
H32A H 0.7932 0.1303 0.5398 0.068 Uiso 0.371 1 d R U P D 2
C33A C 0.7478(5) 0.0055(8) 0.4955(4) 0.071(3) Uani 0.371 1 d D U P D 2
H33A H 0.6970 0.0405 0.4846 0.085 Uiso 0.371 1 d R U P D 2
C34A C 0.7633(5) -0.0969(8) 0.4788(3) 0.059(3) Uani 0.371 1 d D U P D 2
H34A H 0.7237 -0.1334 0.4560 0.071 Uiso 0.371 1 d R U P D 2
C35A C 0.8361(6) -0.1480(7) 0.4946(3) 0.059(3) Uani 0.371 1 d D U P D 2
H35A H 0.8470 -0.2198 0.4829 0.071 Uiso 0.371 1 d R U P D 2
Cl1A Cl 0.9904(3) -0.3953(5) 0.48283(18) 0.0911(13) Uani 0.371 1 d . U P E 2
Cl2A Cl 0.9740(4) -0.2478(5) 0.4084(2) 0.0873(15) Uani 0.371 1 d . U P E 2
C1AA C 1.0329(10) -0.2780(16) 0.4622(5) 0.071(4) Uani 0.371 1 d . U P E 2
H1AA H 1.0859 -0.2955 0.4607 0.086 Uiso 0.371 1 d R U P E 2
H1AB H 1.0343 -0.2135 0.4812 0.086 Uiso 0.371 1 d R U P E 2
N1 N 1.33780(19) -0.0478(3) 0.75999(11) 0.0374(7) Uani 1 1 d . U . F 2
N2 N 1.20995(19) -0.0626(3) 0.68946(11) 0.0395(7) Uani 1 1 d . U . F 2
O1 O 1.5895(3) -0.0878(4) 0.90912(13) 0.0795(12) Uani 1 1 d D U . B 2
O2 O 0.9604(2) -0.1673(4) 0.54435(12) 0.0766(12) Uani 1 1 d D U . D 2
Cl1 Cl 1.33521(6) -0.32577(8) 0.71297(4) 0.0408(2) Uani 1 1 d . U . F 2
Cl2 Cl 1.38232(6) -0.06924(9) 0.65254(4) 0.0489(3) Uani 1 1 d . U . F 2
Zn1 Zn 1.32115(2) -0.14156(4) 0.70140(2) 0.03657(16) Uani 1 1 d . U . F 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.291(5) . ?
C1 C2 1.476(5) . ?
C1 C12 1.513(6) . ?
C2 C3 1.379(7) . ?
C2 C7 1.424(7) . ?
C3 C4 1.421(6) . ?
C4 C5 1.352(8) . ?
C5 C6 1.414(8) . ?
C6 C8 1.406(8) . ?
C6 C7 1.422(6) . ?
C7 C11 1.426(7) . ?
C8 C9 1.367(8) . ?
C9 C10 1.432(6) . ?
C10 C11 1.378(7) . ?
C11 C12 1.484(5) . ?
C12 N2 1.284(5) . ?
C13 C14 1.394(6) . ?
C13 C18 1.393(6) . ?
C13 N1 1.423(6) . ?
C14 C15 1.384(6) . ?
C15 C16 1.376(6) . ?
C16 O1 1.384(6) . ?
C16 C17 1.396(7) . ?
C17 C18 1.377(7) . ?
C19 C24 1.386(6) . ?
C19 C20 1.396(6) . ?
C19 N2 1.433(6) . ?
C20 C21 1.383(6) . ?
C21 C22 1.371(7) . ?
C22 O2 1.382(6) . ?
C22 C23 1.387(8) . ?
C23 C24 1.391(8) . ?
C25 C26 1.381(6) . ?
C25 C36 1.388(6) . ?
C26 C27 1.381(6) . ?
C27 C28 1.386(7) . ?
C28 C29 1.376(7) . ?
C29 C36 1.375(7) . ?
C25A O1 1.348(8) . ?
C25A C36A 1.363(8) . ?
C25A C26A 1.367(8) . ?
C26A C27A 1.386(8) . ?
C27A C28A 1.380(8) . ?
C28A C29A 1.380(8) . ?
C29A C36A 1.384(8) . ?
C30 C31 1.362(7) . ?
C30 C35 1.372(7) . ?
C31 C32 1.398(7) . ?
C32 C33 1.355(7) . ?
C33 C34 1.391(8) . ?
C34 C35 1.380(7) . ?
C30A C31A 1.388(7) . ?
C30A C35A 1.391(8) . ?
C30A O2 1.423(6) . ?
C31A C32A 1.376(8) . ?
C32A C33A 1.194(14) 2_656 ?
C32A C33A 1.378(8) . ?
C33A C33A 0.27(2) 2_656 ?
C33A C32A 1.194(14) 2_656 ?
C33A C34A 1.367(8) . ?
C33A C34A 1.487(14) 2_656 ?
C34A C35A 1.381(8) . ?
C34A C33A 1.487(14) 2_656 ?
C34A C34A 1.50(2) 2_656 ?
Cl1A C1AA 1.762(19) . ?
Cl2A C1AA 1.768(18) . ?
N1 Zn1 2.087(3) . ?
N2 Zn1 2.100(3) . ?
Cl1 Zn1 2.2052(14) . ?
Cl2 Zn1 2.2278(12) . ?

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
N1 C1 C2 134.1(4) . . ?
N1 C1 C12 117.9(3) . . ?
C2 C1 C12 108.0(3) . . ?
C3 C2 C7 119.5(4) . . ?
C3 C2 C1 135.5(4) . . ?
C7 C2 C1 104.8(4) . . ?
C2 C3 C4 117.5(5) . . ?
C5 C4 C3 123.7(5) . . ?
C4 C5 C6 120.7(4) . . ?
C8 C6 C5 127.8(4) . . ?
C8 C6 C7 115.8(5) . . ?
C5 C6 C7 116.4(5) . . ?
C2 C7 C6 122.2(5) . . ?
C2 C7 C11 115.0(4) . . ?
C6 C7 C11 122.8(5) . . ?
C9 C8 C6 122.0(4) . . ?
C8 C9 C10 121.9(5) . . ?
C11 C10 C9 118.3(5) . . ?
C10 C11 C7 119.2(4) . . ?
C10 C11 C12 135.7(5) . . ?
C7 C11 C12 105.1(4) . . ?
N2 C12 C11 134.9(4) . . ?
N2 C12 C1 118.0(3) . . ?
C11 C12 C1 107.0(3) . . ?
C14 C13 C18 120.0(4) . . ?
C14 C13 N1 119.5(4) . . ?
C18 C13 N1 120.4(4) . . ?
C15 C14 C13 120.3(4) . . ?
C16 C15 C14 119.2(4) . . ?
C15 C16 O1 123.8(5) . . ?
C15 C16 C17 120.8(5) . . ?
O1 C16 C17 115.3(4) . . ?
C18 C17 C16 120.1(4) . . ?
C17 C18 C13 119.4(4) . . ?
C24 C19 C20 119.7(4) . . ?
C24 C19 N2 118.5(4) . . ?
C20 C19 N2 121.6(4) . . ?
C21 C20 C19 120.2(4) . . ?
C22 C21 C20 119.8(4) . . ?
C21 C22 O2 117.6(5) . . ?
C21 C22 C23 120.8(5) . . ?
O2 C22 C23 121.6(5) . . ?
C22 C23 C24 119.7(5) . . ?
C19 C24 C23 119.7(5) . . ?
C26 C25 C36 118.7(4) . . ?
C27 C26 C25 120.8(4) . . ?
C26 C27 C28 119.9(5) . . ?
C29 C28 C27 119.6(5) . . ?
C36 C29 C28 120.3(5) . . ?
C29 C36 C25 120.7(5) . . ?
O1 C25A C36A 122.3(14) . . ?
O1 C25A C26A 115.2(14) . . ?
C36A C25A C26A 122.5(5) . . ?
C25A C26A C27A 118.7(5) . . ?
C28A C27A C26A 119.9(6) . . ?
C27A C28A C29A 120.1(6) . . ?
C28A C29A C36A 120.1(5) . . ?
C25A C36A C29A 118.7(5) . . ?
C31 C30 C35 120.7(4) . . ?
C30 C31 C32 120.1(4) . . ?
C33 C32 C31 119.6(5) . . ?
C32 C33 C34 120.2(5) . . ?
C35 C34 C33 120.0(5) . . ?
C30 C35 C34 119.4(5) . . ?
C31A C30A C35A 118.6(5) . . ?
C31A C30A O2 128.0(7) . . ?
C35A C30A O2 112.7(7) . . ?
C32A C31A C30A 120.6(5) . . ?
C33A C32A C31A 119.3(7) 2_656 . ?
C33A C32A C33A 9.0(11) 2_656 . ?
C31A C32A C33A 119.9(5) . . ?
C33A C33A C32A 128(4) 2_656 2_656 ?
C33A C33A C34A 111.0(14) 2_656 . ?
C32A C33A C34A 115.0(11) 2_656 . ?
C33A C33A C32A 43(3) 2_656 . ?
C32A C33A C32A 120.8(10) 2_656 . ?
C34A C33A C32A 120.4(5) . . ?
C33A C33A C34A 59.1(16) 2_656 2_656 ?
C32A C33A C34A 125.0(11) 2_656 2_656 ?
C34A C33A C34A 63.4(8) . 2_656 ?
C32A C33A C34A 97.9(8) . 2_656 ?
C33A C34A C35A 120.0(5) . . ?
C33A C34A C33A 9.9(8) . 2_656 ?
C35A C34A C33A 113.1(7) . 2_656 ?
C33A C34A C34A 62.2(5) . 2_656 ?
C35A C34A C34A 98.2(7) . 2_656 ?
C33A C34A C34A 54.4(7) 2_656 2_656 ?
C34A C35A C30A 120.4(5) . . ?
Cl1A C1AA Cl2A 107.7(10) . . ?
C1 N1 C13 121.8(3) . . ?
C1 N1 Zn1 111.5(3) . . ?
C13 N1 Zn1 126.5(2) . . ?
C12 N2 C19 123.9(3) . . ?
C12 N2 Zn1 111.2(3) . . ?
C19 N2 Zn1 125.0(3) . . ?
C25A O1 C16 134.2(10) . . ?
C22 O2 C30A 124.0(5) . . ?
N1 Zn1 N2 81.01(13) . . ?
N1 Zn1 Cl1 113.17(10) . . ?
N2 Zn1 Cl1 121.74(10) . . ?
N1 Zn1 Cl2 113.81(9) . . ?
N2 Zn1 Cl2 106.63(10) . . ?
Cl1 Zn1 Cl2 115.80(4) . . ?

_refine_diff_density_max         1.564
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.092

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1061244'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14 Cl2 F2 N2 Zn'
_chemical_formula_sum            'C24 H14 Cl2 F2 N2 Zn'
_chemical_formula_weight         504.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.984(3)
_cell_length_b                   11.965(4)
_cell_length_c                   17.609(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.504(5)
_cell_angle_gamma                90
_cell_volume                     2061.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7303
_cell_measurement_theta_min      2.0713
_cell_measurement_theta_max      31.0197

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.483
_shelx_estimated_absorpt_T_min   0.854
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7659
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
Abscor. T. Higashi. (2001). Rigaku Corp. Tokyo, Japan
;


_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku AFC-12 with Saturn 724+ CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21742
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.071
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3627
_reflns_number_gt                3503
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_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     
'w=1/[σ²(Fo²)+(0.0107P)²+4.0396P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3627
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.0881
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   1.245
_refine_ls_restrained_S_all      1.245
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4271(3) 0.2639(3) 0.4678(2) 0.0145(8) Uani 1 1 d . . . . .
C2 C 0.4465(4) 0.3521(3) 0.4125(2) 0.0149(7) Uani 1 1 d . . . . .
C3 C 0.3691(4) 0.3954(3) 0.3451(2) 0.0177(8) Uani 1 1 d . . . . .
H3 H 0.2825 0.3641 0.3232 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4214(4) 0.4878(3) 0.3093(2) 0.0181(8) Uani 1 1 d . . . . .
H4 H 0.3689 0.5171 0.2625 0.022 Uiso 1 1 calc R U . . .
C5 C 0.5453(4) 0.5362(3) 0.3399(2) 0.0185(8) Uani 1 1 d . . . . .
H5 H 0.5772 0.5971 0.3138 0.022 Uiso 1 1 calc R U . . .
C6 C 0.6258(4) 0.4960(3) 0.4102(2) 0.0162(8) Uani 1 1 d . . . . .
C7 C 0.5734(4) 0.4039(3) 0.4448(2) 0.0150(8) Uani 1 1 d . . . . .
C8 C 0.7533(4) 0.5396(3) 0.4497(2) 0.0205(8) Uani 1 1 d . . . . .
H8 H 0.7937 0.6007 0.4281 0.025 Uiso 1 1 calc R U . . .
C9 C 0.8187(4) 0.4937(3) 0.5190(2) 0.0179(8) Uani 1 1 d . . . . .
H9 H 0.9036 0.5245 0.5443 0.022 Uiso 1 1 calc R U . . .
C10 C 0.7639(4) 0.4027(3) 0.5538(2) 0.0180(8) Uani 1 1 d . . . . .
H10 H 0.8103 0.3735 0.6021 0.022 Uiso 1 1 calc R U . . .
C11 C 0.6411(4) 0.3566(3) 0.5161(2) 0.0155(8) Uani 1 1 d . . . . .
C12 C 0.5499(3) 0.2688(3) 0.5345(2) 0.0142(7) Uani 1 1 d . . . . .
C13 C 0.2212(4) 0.1629(3) 0.4131(2) 0.0153(8) Uani 1 1 d . . . . .
C14 C 0.0975(4) 0.1359(3) 0.4345(2) 0.0194(8) Uani 1 1 d . . . . .
H14 H 0.0901 0.1395 0.4874 0.023 Uiso 1 1 calc R U . . .
C15 C -0.0146(4) 0.1038(3) 0.3784(2) 0.0202(8) Uani 1 1 d . . . . .
H15 H -0.0999 0.0869 0.3918 0.024 Uiso 1 1 calc R U . . .
C16 C 0.0019(4) 0.0973(3) 0.3027(2) 0.0202(8) Uani 1 1 d . . . . .
C17 C 0.1237(4) 0.1194(3) 0.2800(2) 0.0190(8) Uani 1 1 d . . . . .
H17 H 0.1314 0.1126 0.2273 0.023 Uiso 1 1 calc R U . . .
C18 C 0.2349(4) 0.1518(3) 0.3364(2) 0.0176(8) Uani 1 1 d . . . . .
H18 H 0.3204 0.1664 0.3225 0.021 Uiso 1 1 calc R U . . .
C19 C 0.6667(4) 0.1921(3) 0.6549(2) 0.0166(8) Uani 1 1 d . . . . .
C20 C 0.6454(4) 0.2006(3) 0.7301(2) 0.0196(8) Uani 1 1 d . . . . .
H20 H 0.5567 0.2166 0.7393 0.023 Uiso 1 1 calc R U . . .
C21 C 0.7554(4) 0.1856(3) 0.7925(2) 0.0228(9) Uani 1 1 d . . . . .
H21 H 0.7438 0.1933 0.8445 0.027 Uiso 1 1 calc R U . . .
C22 C 0.8806(4) 0.1594(3) 0.7761(2) 0.0225(9) Uani 1 1 d . . . . .
C23 C 0.9045(4) 0.1512(3) 0.7022(2) 0.0214(8) Uani 1 1 d . . . . .
H23 H 0.9935 0.1354 0.6934 0.026 Uiso 1 1 calc R U . . .
C24 C 0.7956(4) 0.1667(3) 0.6405(2) 0.0178(8) Uani 1 1 d . . . . .
H24 H 0.8088 0.1600 0.5887 0.021 Uiso 1 1 calc R U . . .
N1 N 0.3347(3) 0.1901(2) 0.47317(17) 0.0148(6) Uani 1 1 d . . . . .
N2 N 0.5516(3) 0.2024(2) 0.59254(17) 0.0157(7) Uani 1 1 d . . . . .
F1 F -0.1071(2) 0.06524(19) 0.24726(13) 0.0272(5) Uani 1 1 d . . . . .
F2 F 0.9868(2) 0.13970(19) 0.83675(13) 0.0310(6) Uani 1 1 d . . . . .
Cl1 Cl 0.23790(10) 0.19176(8) 0.65290(5) 0.0210(2) Uani 1 1 d . . . . .
Cl2 Cl 0.37859(10) -0.07247(7) 0.58545(6) 0.0235(2) Uani 1 1 d . . . . .
Zn1 Zn 0.37163(4) 0.11159(3) 0.58109(2) 0.01530(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.293(4) . ?
C1 C2 1.475(5) . ?
C1 C12 1.521(5) . ?
C2 C3 1.381(5) . ?
C2 C7 1.424(5) . ?
C3 C4 1.424(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.419(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.409(5) . ?
C6 C8 1.423(5) . ?
C7 C11 1.419(5) . ?
C8 C9 1.378(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.412(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.468(5) . ?
C12 N2 1.292(5) . ?
C13 C18 1.391(5) . ?
C13 C14 1.399(5) . ?
C13 N1 1.425(5) . ?
C14 C15 1.392(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(5) . ?
C15 H15 0.9500 . ?
C16 F1 1.364(4) . ?
C16 C17 1.380(5) . ?
C17 C18 1.388(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.387(5) . ?
C19 C24 1.395(5) . ?
C19 N2 1.428(5) . ?
C20 C21 1.401(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.375(6) . ?
C21 H21 0.9500 . ?
C22 F2 1.367(4) . ?
C22 C23 1.373(5) . ?
C23 C24 1.388(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
N1 Zn1 2.086(3) . ?
N2 Zn1 2.075(3) . ?
Cl1 Zn1 2.2305(11) . ?
Cl2 Zn1 2.2042(12) . ?

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
N1 C1 C2 136.6(3) . . ?
N1 C1 C12 116.6(3) . . ?
C2 C1 C12 106.9(3) . . ?
C3 C2 C7 118.8(3) . . ?
C3 C2 C1 135.3(3) . . ?
C7 C2 C1 105.7(3) . . ?
C2 C3 C4 118.7(3) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 122.3(3) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 116.6(3) . . ?
C7 C6 C8 116.6(3) . . ?
C5 C6 C8 126.7(3) . . ?
C6 C7 C11 122.8(3) . . ?
C6 C7 C2 123.0(3) . . ?
C11 C7 C2 114.1(3) . . ?
C9 C8 C6 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C6 C8 H8 119.8 . . ?
C8 C9 C10 122.4(3) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C11 C10 C9 118.7(3) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C10 C11 C7 119.0(3) . . ?
C10 C11 C12 134.9(3) . . ?
C7 C11 C12 105.9(3) . . ?
N2 C12 C11 134.7(3) . . ?
N2 C12 C1 117.9(3) . . ?
C11 C12 C1 107.3(3) . . ?
C18 C13 C14 120.1(3) . . ?
C18 C13 N1 121.7(3) . . ?
C14 C13 N1 117.8(3) . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 117.9(3) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
F1 C16 C15 118.5(3) . . ?
F1 C16 C17 118.0(3) . . ?
C15 C16 C17 123.5(3) . . ?
C16 C17 C18 118.1(3) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C17 C18 C13 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C20 C19 C24 120.9(3) . . ?
C20 C19 N2 118.4(3) . . ?
C24 C19 N2 120.6(3) . . ?
C19 C20 C21 119.6(4) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 117.9(4) . . ?
C22 C21 H21 121.0 . . ?
C20 C21 H21 121.0 . . ?
F2 C22 C23 118.3(4) . . ?
F2 C22 C21 118.1(4) . . ?
C23 C22 C21 123.6(4) . . ?
C22 C23 C24 118.4(4) . . ?
C22 C23 H23 120.8 . . ?
C24 C23 H23 120.8 . . ?
C23 C24 C19 119.6(4) . . ?
C23 C24 H24 120.2 . . ?
C19 C24 H24 120.2 . . ?
C1 N1 C13 125.1(3) . . ?
C1 N1 Zn1 112.0(2) . . ?
C13 N1 Zn1 122.9(2) . . ?
C12 N2 C19 122.9(3) . . ?
C12 N2 Zn1 111.8(2) . . ?
C19 N2 Zn1 125.3(2) . . ?
N2 Zn1 N1 81.06(11) . . ?
N2 Zn1 Cl2 119.96(9) . . ?
N1 Zn1 Cl2 118.72(9) . . ?
N2 Zn1 Cl1 108.91(9) . . ?
N1 Zn1 Cl1 107.81(8) . . ?
Cl2 Zn1 Cl1 115.35(4) . . ?

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
N1 C1 C2 C3 4.2(7) . . . . ?
C12 C1 C2 C3 -174.1(4) . . . . ?
N1 C1 C2 C7 178.8(4) . . . . ?
C12 C1 C2 C7 0.5(4) . . . . ?
C7 C2 C3 C4 2.2(5) . . . . ?
C1 C2 C3 C4 176.2(4) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C4 C5 C6 C7 1.3(5) . . . . ?
C4 C5 C6 C8 -178.0(3) . . . . ?
C5 C6 C7 C11 -178.4(3) . . . . ?
C8 C6 C7 C11 1.0(5) . . . . ?
C5 C6 C7 C2 0.0(5) . . . . ?
C8 C6 C7 C2 179.4(3) . . . . ?
C3 C2 C7 C6 -1.8(5) . . . . ?
C1 C2 C7 C6 -177.4(3) . . . . ?
C3 C2 C7 C11 176.8(3) . . . . ?
C1 C2 C7 C11 1.1(4) . . . . ?
C7 C6 C8 C9 -1.2(5) . . . . ?
C5 C6 C8 C9 178.2(3) . . . . ?
C6 C8 C9 C10 0.2(6) . . . . ?
C8 C9 C10 C11 1.2(5) . . . . ?
C9 C10 C11 C7 -1.3(5) . . . . ?
C9 C10 C11 C12 -175.9(4) . . . . ?
C6 C7 C11 C10 0.3(5) . . . . ?
C2 C7 C11 C10 -178.3(3) . . . . ?
C6 C7 C11 C12 176.3(3) . . . . ?
C2 C7 C11 C12 -2.3(4) . . . . ?
C10 C11 C12 N2 -0.2(7) . . . . ?
C7 C11 C12 N2 -175.3(4) . . . . ?
C10 C11 C12 C1 177.5(4) . . . . ?
C7 C11 C12 C1 2.4(4) . . . . ?
N1 C1 C12 N2 -2.4(5) . . . . ?
C2 C1 C12 N2 176.3(3) . . . . ?
N1 C1 C12 C11 179.5(3) . . . . ?
C2 C1 C12 C11 -1.8(4) . . . . ?
C18 C13 C14 C15 -3.6(5) . . . . ?
N1 C13 C14 C15 -177.1(3) . . . . ?
C13 C14 C15 C16 1.5(5) . . . . ?
C14 C15 C16 F1 179.6(3) . . . . ?
C14 C15 C16 C17 0.9(6) . . . . ?
F1 C16 C17 C18 -179.8(3) . . . . ?
C15 C16 C17 C18 -1.2(6) . . . . ?
C16 C17 C18 C13 -1.0(5) . . . . ?
C14 C13 C18 C17 3.3(5) . . . . ?
N1 C13 C18 C17 176.6(3) . . . . ?
C24 C19 C20 C21 1.2(5) . . . . ?
N2 C19 C20 C21 177.0(3) . . . . ?
C19 C20 C21 C22 -1.9(5) . . . . ?
C20 C21 C22 F2 -177.1(3) . . . . ?
C20 C21 C22 C23 2.5(6) . . . . ?
F2 C22 C23 C24 177.4(3) . . . . ?
C21 C22 C23 C24 -2.1(6) . . . . ?
C22 C23 C24 C19 1.3(5) . . . . ?
C20 C19 C24 C23 -0.9(5) . . . . ?
N2 C19 C24 C23 -176.6(3) . . . . ?
C2 C1 N1 C13 10.0(6) . . . . ?
C12 C1 N1 C13 -171.8(3) . . . . ?
C2 C1 N1 Zn1 -170.8(3) . . . . ?
C12 C1 N1 Zn1 7.4(4) . . . . ?
C18 C13 N1 C1 42.1(5) . . . . ?
C14 C13 N1 C1 -144.5(3) . . . . ?
C18 C13 N1 Zn1 -137.0(3) . . . . ?
C14 C13 N1 Zn1 36.4(4) . . . . ?
C11 C12 N2 C19 -8.5(6) . . . . ?
C1 C12 N2 C19 174.0(3) . . . . ?
C11 C12 N2 Zn1 173.4(3) . . . . ?
C1 C12 N2 Zn1 -4.1(4) . . . . ?
C20 C19 N2 C12 129.8(4) . . . . ?
C24 C19 N2 C12 -54.4(5) . . . . ?
C20 C19 N2 Zn1 -52.4(4) . . . . ?
C24 C19 N2 Zn1 123.4(3) . . . . ?

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1061245'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H14 Cl2 F2 N2 Zn), 3(C4 H8 O)'
_chemical_formula_sum            'C60 H52 Cl4 F4 N4 O3 Zn2'
_chemical_formula_weight         1225.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Zn Zn 0.2839 1.4301 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   14.3180(15)
_cell_length_b                   11.7050(8)
_cell_length_c                   17.7720(18)
_cell_angle_alpha                90
_cell_angle_beta                 112.958(4)
_cell_angle_gamma                90
_cell_volume                     2742.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5573
_cell_measurement_theta_min      2.1393
_cell_measurement_theta_max      31.7731

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.133
_shelx_estimated_absorpt_T_min   0.781
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7994
_exptl_absorpt_process_details   
;
Abscor. T. Higashi. (2001). Rigaku Corp. Tokyo, Japan
;



_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku SCX-Mini Mercury CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28653
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.139
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6289
_reflns_number_gt                4787
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_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     
'w=1/[σ²(Fo²)+(0.0405P)²+3.4748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6289
_refine_ls_number_parameters     417
_refine_ls_number_restraints     672
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4466(2) 0.2702(3) 0.50068(18) 0.0272(6) Uani 1 1 d . U . . .
C2 C 0.4671(2) 0.3532(3) 0.56749(18) 0.0271(6) Uani 1 1 d . U . . .
C3 C 0.4151(3) 0.3923(3) 0.61317(19) 0.0316(7) Uani 1 1 d . U . . .
H3 H 0.3507 0.3615 0.6055 0.038 Uiso 1 1 calc R U . . .
C4 C 0.4594(3) 0.4791(3) 0.6718(2) 0.0350(7) Uani 1 1 d . U . . .
H4 H 0.4231 0.5072 0.7027 0.042 Uiso 1 1 calc R U . . .
C5 C 0.5530(3) 0.5239(3) 0.6852(2) 0.0348(7) Uani 1 1 d . U . . .
H5 H 0.5809 0.5809 0.7259 0.042 Uiso 1 1 calc R U . . .
C6 C 0.6087(2) 0.4860(3) 0.63903(18) 0.0307(7) Uani 1 1 d . U . . .
C7 C 0.5640(2) 0.4008(3) 0.58104(18) 0.0280(6) Uani 1 1 d . U . . .
C8 C 0.7054(3) 0.5256(3) 0.6460(2) 0.0376(8) Uani 1 1 d . U . . .
H8 H 0.7398 0.5822 0.6855 0.045 Uiso 1 1 calc R U . . .
C9 C 0.7497(3) 0.4823(3) 0.5957(2) 0.0382(8) Uani 1 1 d . U . . .
H9 H 0.8141 0.5108 0.6011 0.046 Uiso 1 1 calc R U . . .
C10 C 0.7031(2) 0.3974(3) 0.5365(2) 0.0353(7) Uani 1 1 d . U . . .
H10 H 0.7352 0.3695 0.5024 0.042 Uiso 1 1 calc R U . . .
C11 C 0.6097(2) 0.3558(3) 0.52929(19) 0.0273(6) Uani 1 1 d . U . . .
C12 C 0.5366(2) 0.2727(3) 0.47561(18) 0.0255(6) Uani 1 1 d . U . . .
C13 C 0.2871(2) 0.1897(3) 0.4826(2) 0.0303(7) Uani 1 1 d . U . . .
C14 C 0.1919(3) 0.2151(4) 0.4250(2) 0.0470(9) Uani 1 1 d . U . . .
H14 H 0.1840 0.2433 0.3727 0.056 Uiso 1 1 calc R U . . .
C15 C 0.1074(3) 0.1987(4) 0.4446(3) 0.0616(12) Uani 1 1 d . U . . .
H15 H 0.0412 0.2170 0.4065 0.074 Uiso 1 1 calc R U . . .
C16 C 0.1225(3) 0.1558(4) 0.5201(3) 0.0523(10) Uani 1 1 d . U . . .
C17 C 0.2155(3) 0.1302(3) 0.5780(2) 0.0425(8) Uani 1 1 d . U . . .
H17 H 0.2226 0.1014 0.6299 0.051 Uiso 1 1 calc R U . . .
C18 C 0.2999(3) 0.1473(3) 0.5590(2) 0.0353(7) Uani 1 1 d . U . . .
H18 H 0.3659 0.1302 0.5980 0.042 Uiso 1 1 calc R U . . .
C19 C 0.6167(2) 0.2028(3) 0.39058(19) 0.0284(6) Uani 1 1 d . U . . .
C20 C 0.6036(2) 0.2330(3) 0.31184(19) 0.0318(7) Uani 1 1 d . U . . .
H20 H 0.5392 0.2582 0.2743 0.038 Uiso 1 1 calc R U . . .
C21 C 0.6853(3) 0.2264(3) 0.2877(2) 0.0386(8) Uani 1 1 d . U . . .
H21 H 0.6786 0.2496 0.2347 0.046 Uiso 1 1 calc R U . . .
C22 C 0.7751(3) 0.1853(3) 0.3431(2) 0.0418(8) Uani 1 1 d . U . . .
C23 C 0.7899(3) 0.1517(3) 0.4210(2) 0.0415(8) Uani 1 1 d . U . . .
H23 H 0.8536 0.1231 0.4574 0.050 Uiso 1 1 calc R U . . .
C24 C 0.7086(2) 0.1608(3) 0.4449(2) 0.0360(7) Uani 1 1 d . U . . .
H24 H 0.7161 0.1383 0.4983 0.043 Uiso 1 1 calc R U . . .
O1 O 0.0403(6) 0.3707(6) 0.2714(4) 0.088(2) Uani 0.623 1 d D U P A 1
C25 C -0.0051(8) 0.4694(8) 0.2215(7) 0.108(3) Uani 0.623 1 d D U P A 1
H25A H 0.0374 0.4961 0.1925 0.130 Uiso 0.623 1 calc R U P A 1
H25B H -0.0126 0.5326 0.2558 0.130 Uiso 0.623 1 calc R U P A 1
C26 C -0.1065(7) 0.4311(8) 0.1621(6) 0.088(3) Uani 0.623 1 d D U P A 1
H26A H -0.1214 0.4639 0.1073 0.106 Uiso 0.623 1 calc R U P A 1
H26B H -0.1608 0.4540 0.1805 0.106 Uiso 0.623 1 calc R U P A 1
C27 C -0.0980(8) 0.3037(8) 0.1605(7) 0.061(3) Uani 0.623 1 d D U P A 1
H27A H -0.1060 0.2767 0.1055 0.074 Uiso 0.623 1 calc R U P A 1
H27B H -0.1499 0.2664 0.1760 0.074 Uiso 0.623 1 calc R U P A 1
C28 C 0.0066(5) 0.2792(7) 0.2221(4) 0.0592(18) Uani 0.623 1 d D U P A 1
H28A H 0.0053 0.2112 0.2548 0.071 Uiso 0.623 1 calc R U P A 1
H28B H 0.0527 0.2631 0.1939 0.071 Uiso 0.623 1 calc R U P A 1
O1A O 0.0100(8) 0.4046(13) 0.2824(7) 0.090(4) Uani 0.377 1 d D U P B 2
C25A C 0.0272(11) 0.3537(18) 0.2145(10) 0.094(5) Uani 0.377 1 d D U P B 2
H25C H 0.0789 0.2926 0.2338 0.113 Uiso 0.377 1 calc R U P B 2
H25D H 0.0499 0.4119 0.1849 0.113 Uiso 0.377 1 calc R U P B 2
C26A C -0.0754(14) 0.305(2) 0.1601(15) 0.091(7) Uani 0.377 1 d D U P B 2
H26C H -0.0852 0.3066 0.1018 0.109 Uiso 0.377 1 calc R U P B 2
H26D H -0.0839 0.2258 0.1759 0.109 Uiso 0.377 1 calc R U P B 2
C27A C -0.1461(10) 0.3853(17) 0.1768(10) 0.099(5) Uani 0.377 1 d D U P B 2
H27C H -0.2057 0.3437 0.1781 0.119 Uiso 0.377 1 calc R U P B 2
H27D H -0.1701 0.4450 0.1340 0.119 Uiso 0.377 1 calc R U P B 2
C28A C -0.0868(10) 0.4368(14) 0.2574(9) 0.093(4) Uani 0.377 1 d D U P B 2
H28C H -0.0915 0.5211 0.2532 0.112 Uiso 0.377 1 calc R U P B 2
H28D H -0.1149 0.4119 0.2976 0.112 Uiso 0.377 1 calc R U P B 2
N2 N 0.53199(19) 0.2110(2) 0.41471(15) 0.0272(5) Uani 1 1 d . U . . .
N1 N 0.37253(18) 0.2038(2) 0.46066(15) 0.0276(5) Uani 1 1 d . U . . .
F1 F 0.03952(19) 0.1376(3) 0.53895(18) 0.0837(9) Uani 1 1 d . U . . .
F2 F 0.85544(17) 0.1758(2) 0.31961(15) 0.0637(7) Uani 1 1 d . U . . .
Cl2 Cl 0.29097(7) 0.18980(8) 0.24739(5) 0.0410(2) Uani 1 1 d . U . . .
Cl1 Cl 0.41855(7) -0.06622(8) 0.37854(6) 0.0459(2) Uani 1 1 d . U . . .
Zn1 Zn 0.39554(3) 0.11988(3) 0.36557(2) 0.02861(12) Uani 1 1 d . U . . .
O2 O 0.9865(13) 0.5617(18) 0.4491(9) 0.197(7) Uani 0.5 1 d D U P C -1
C30 C 0.9393(12) 0.4842(18) 0.4877(11) 0.149(6) Uani 0.5 1 d D U P C -1
H30A H 0.9256 0.4093 0.4596 0.179 Uiso 0.5 1 calc R U P C -1
H30B H 0.8745 0.5162 0.4859 0.179 Uiso 0.5 1 calc R U P C -1
C31 C 1.0143(15) 0.471(3) 0.5752(12) 0.190(8) Uani 0.5 1 d D U P C -1
H31A H 0.9967 0.5218 0.6124 0.228 Uiso 0.5 1 calc R U P C -1
H31B H 1.0174 0.3912 0.5940 0.228 Uiso 0.5 1 calc R U P C -1
C32 C 1.1128(11) 0.5068(16) 0.5699(10) 0.151(6) Uani 0.5 1 d D U P C -1
H32A H 1.1579 0.5451 0.6208 0.182 Uiso 0.5 1 calc R U P C -1
H32B H 1.1487 0.4403 0.5594 0.182 Uiso 0.5 1 calc R U P C -1
C33 C 1.0795(12) 0.5868(13) 0.5002(10) 0.121(5) Uani 0.5 1 d D U P C -1
H33A H 1.0814 0.6660 0.5204 0.146 Uiso 0.5 1 calc R U P C -1
H33B H 1.1262 0.5821 0.4714 0.146 Uiso 0.5 1 calc R U P C -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
C1 N1 1.282(4) . ?
C1 C2 1.472(4) . ?
C1 C12 1.520(4) . ?
C2 C3 1.376(4) . ?
C2 C7 1.425(4) . ?
C3 C4 1.416(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.421(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.398(4) . ?
C6 C8 1.419(5) . ?
C7 C11 1.422(4) . ?
C8 C9 1.378(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.412(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.473(4) . ?
C12 N2 1.281(4) . ?
C13 C14 1.380(5) . ?
C13 C18 1.390(5) . ?
C13 N1 1.431(4) . ?
C14 C15 1.396(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.369(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.362(6) . ?
C16 F1 1.371(4) . ?
C17 C18 1.389(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.383(4) . ?
C19 C20 1.383(4) . ?
C19 N2 1.439(4) . ?
C20 C21 1.395(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.366(5) . ?
C21 H21 0.9500 . ?
C22 F2 1.372(4) . ?
C22 C23 1.374(5) . ?
C23 C24 1.391(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
O1 C28 1.348(8) . ?
O1 C25 1.447(10) . ?
C25 C26 1.493(11) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.497(10) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.498(10) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
O1A C28A 1.335(10) . ?
O1A C25A 1.449(11) . ?
C25A C26A 1.520(13) . ?
C25A H25C 0.9900 . ?
C25A H25D 0.9900 . ?
C26A C27A 1.493(12) . ?
C26A H26C 0.9900 . ?
C26A H26D 0.9900 . ?
C27A C28A 1.479(12) . ?
C27A H27C 0.9900 . ?
C27A H27D 0.9900 . ?
C28A H28C 0.9900 . ?
C28A H28D 0.9900 . ?
N2 Zn1 2.094(3) . ?
N1 Zn1 2.089(3) . ?
Cl2 Zn1 2.2067(9) . ?
Cl1 Zn1 2.2017(10) . ?
O2 C33 1.318(11) . ?
O2 C30 1.454(11) . ?
C30 C31 1.513(13) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.509(13) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.476(12) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

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
N1 C1 C2 135.2(3) . . ?
N1 C1 C12 117.5(3) . . ?
C2 C1 C12 107.3(3) . . ?
C3 C2 C7 119.0(3) . . ?
C3 C2 C1 135.3(3) . . ?
C7 C2 C1 105.6(3) . . ?
C2 C3 C4 118.9(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C8 116.7(3) . . ?
C7 C6 C5 116.7(3) . . ?
C8 C6 C5 126.6(3) . . ?
C6 C7 C11 123.2(3) . . ?
C6 C7 C2 122.7(3) . . ?
C11 C7 C2 114.1(3) . . ?
C9 C8 C6 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C6 C8 H8 119.9 . . ?
C8 C9 C10 122.6(3) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
C11 C10 C9 118.5(3) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C10 C11 C7 118.8(3) . . ?
C10 C11 C12 135.2(3) . . ?
C7 C11 C12 105.9(3) . . ?
N2 C12 C11 135.1(3) . . ?
N2 C12 C1 117.8(3) . . ?
C11 C12 C1 107.0(3) . . ?
C14 C13 C18 121.2(3) . . ?
C14 C13 N1 118.4(3) . . ?
C18 C13 N1 120.4(3) . . ?
C13 C14 C15 119.1(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 118.3(4) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C17 C16 C15 123.7(4) . . ?
C17 C16 F1 117.9(4) . . ?
C15 C16 F1 118.5(4) . . ?
C16 C17 C18 118.2(3) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C17 C18 C13 119.5(3) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
C24 C19 C20 120.9(3) . . ?
C24 C19 N2 119.9(3) . . ?
C20 C19 N2 119.2(3) . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 117.7(3) . . ?
C22 C21 H21 121.1 . . ?
C20 C21 H21 121.1 . . ?
C21 C22 F2 118.4(3) . . ?
C21 C22 C23 123.9(3) . . ?
F2 C22 C23 117.7(3) . . ?
C22 C23 C24 117.9(3) . . ?
C22 C23 H23 121.1 . . ?
C24 C23 H23 121.1 . . ?
C19 C24 C23 119.7(3) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C28 O1 C25 106.0(6) . . ?
O1 C25 C26 105.9(7) . . ?
O1 C25 H25A 110.6 . . ?
C26 C25 H25A 110.6 . . ?
O1 C25 H25B 110.6 . . ?
C26 C25 H25B 110.6 . . ?
H25A C25 H25B 108.7 . . ?
C25 C26 C27 104.4(8) . . ?
C25 C26 H26A 110.9 . . ?
C27 C26 H26A 110.9 . . ?
C25 C26 H26B 110.9 . . ?
C27 C26 H26B 110.9 . . ?
H26A C26 H26B 108.9 . . ?
C26 C27 C28 104.0(8) . . ?
C26 C27 H27A 110.9 . . ?
C28 C27 H27A 110.9 . . ?
C26 C27 H27B 110.9 . . ?
C28 C27 H27B 110.9 . . ?
H27A C27 H27B 109.0 . . ?
O1 C28 C27 108.9(6) . . ?
O1 C28 H28A 109.9 . . ?
C27 C28 H28A 109.9 . . ?
O1 C28 H28B 109.9 . . ?
C27 C28 H28B 109.9 . . ?
H28A C28 H28B 108.3 . . ?
C28A O1A C25A 109.3(8) . . ?
O1A C25A C26A 104.3(10) . . ?
O1A C25A H25C 110.9 . . ?
C26A C25A H25C 110.9 . . ?
O1A C25A H25D 110.9 . . ?
C26A C25A H25D 110.9 . . ?
H25C C25A H25D 108.9 . . ?
C27A C26A C25A 101.6(10) . . ?
C27A C26A H26C 111.5 . . ?
C25A C26A H26C 111.5 . . ?
C27A C26A H26D 111.5 . . ?
C25A C26A H26D 111.5 . . ?
H26C C26A H26D 109.3 . . ?
C26A C27A C28A 105.7(11) . . ?
C26A C27A H27C 110.6 . . ?
C28A C27A H27C 110.6 . . ?
C26A C27A H27D 110.6 . . ?
C28A C27A H27D 110.6 . . ?
H27C C27A H27D 108.7 . . ?
O1A C28A C27A 109.7(9) . . ?
O1A C28A H28C 109.7 . . ?
C27A C28A H28C 109.7 . . ?
O1A C28A H28D 109.7 . . ?
C27A C28A H28D 109.7 . . ?
H28C C28A H28D 108.2 . . ?
C12 N2 C19 121.2(3) . . ?
C12 N2 Zn1 111.8(2) . . ?
C19 N2 Zn1 126.82(19) . . ?
C1 N1 C13 121.9(3) . . ?
C1 N1 Zn1 112.1(2) . . ?
C13 N1 Zn1 125.9(2) . . ?
N1 Zn1 N2 80.73(10) . . ?
N1 Zn1 Cl1 116.43(8) . . ?
N2 Zn1 Cl1 112.52(7) . . ?
N1 Zn1 Cl2 109.45(7) . . ?
N2 Zn1 Cl2 112.60(7) . . ?
Cl1 Zn1 Cl2 119.00(4) . . ?
C33 O2 C30 110.2(9) . . ?
O2 C30 C31 105.8(10) . . ?
O2 C30 H30A 110.6 . . ?
C31 C30 H30A 110.6 . . ?
O2 C30 H30B 110.6 . . ?
C31 C30 H30B 110.6 . . ?
H30A C30 H30B 108.7 . . ?
C32 C31 C30 102.4(11) . . ?
C32 C31 H31A 111.3 . . ?
C30 C31 H31A 111.3 . . ?
C32 C31 H31B 111.3 . . ?
C30 C31 H31B 111.3 . . ?
H31A C31 H31B 109.2 . . ?
C33 C32 C31 102.9(11) . . ?
C33 C32 H32A 111.2 . . ?
C31 C32 H32A 111.2 . . ?
C33 C32 H32B 111.2 . . ?
C31 C32 H32B 111.2 . . ?
H32A C32 H32B 109.1 . . ?
O2 C33 C32 110.2(10) . . ?
O2 C33 H33A 109.6 . . ?
C32 C33 H33A 109.6 . . ?
O2 C33 H33B 109.6 . . ?
C32 C33 H33B 109.6 . . ?
H33A C33 H33B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.1(6) . . . . ?
C12 C1 C2 C3 177.5(3) . . . . ?
N1 C1 C2 C7 -178.0(3) . . . . ?
C12 C1 C2 C7 -0.4(3) . . . . ?
C7 C2 C3 C4 0.4(5) . . . . ?
C1 C2 C3 C4 -177.2(3) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C3 C4 C5 C6 1.4(5) . . . . ?
C4 C5 C6 C7 -0.9(5) . . . . ?
C4 C5 C6 C8 179.3(3) . . . . ?
C8 C6 C7 C11 -1.4(5) . . . . ?
C5 C6 C7 C11 178.9(3) . . . . ?
C8 C6 C7 C2 -180.0(3) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
C3 C2 C7 C6 0.0(5) . . . . ?
C1 C2 C7 C6 178.2(3) . . . . ?
C3 C2 C7 C11 -178.7(3) . . . . ?
C1 C2 C7 C11 -0.4(4) . . . . ?
C7 C6 C8 C9 1.6(5) . . . . ?
C5 C6 C8 C9 -178.7(3) . . . . ?
C6 C8 C9 C10 -0.7(5) . . . . ?
C8 C9 C10 C11 -0.5(5) . . . . ?
C9 C10 C11 C7 0.6(5) . . . . ?
C9 C10 C11 C12 177.7(3) . . . . ?
C6 C7 C11 C10 0.3(5) . . . . ?
C2 C7 C11 C10 179.0(3) . . . . ?
C6 C7 C11 C12 -177.6(3) . . . . ?
C2 C7 C11 C12 1.1(4) . . . . ?
C10 C11 C12 N2 -2.1(6) . . . . ?
C7 C11 C12 N2 175.2(3) . . . . ?
C10 C11 C12 C1 -178.7(4) . . . . ?
C7 C11 C12 C1 -1.3(3) . . . . ?
N1 C1 C12 N2 1.9(4) . . . . ?
C2 C1 C12 N2 -176.2(3) . . . . ?
N1 C1 C12 C11 179.1(3) . . . . ?
C2 C1 C12 C11 1.1(3) . . . . ?
C18 C13 C14 C15 0.6(6) . . . . ?
N1 C13 C14 C15 178.3(4) . . . . ?
C13 C14 C15 C16 -1.3(7) . . . . ?
C14 C15 C16 C17 1.4(7) . . . . ?
C14 C15 C16 F1 -178.8(4) . . . . ?
C15 C16 C17 C18 -0.8(7) . . . . ?
F1 C16 C17 C18 179.4(3) . . . . ?
C16 C17 C18 C13 0.1(5) . . . . ?
C14 C13 C18 C17 0.0(5) . . . . ?
N1 C13 C18 C17 -177.6(3) . . . . ?
C24 C19 C20 C21 -3.1(5) . . . . ?
N2 C19 C20 C21 179.5(3) . . . . ?
C19 C20 C21 C22 2.6(5) . . . . ?
C20 C21 C22 F2 178.5(3) . . . . ?
C20 C21 C22 C23 -0.8(6) . . . . ?
C21 C22 C23 C24 -0.4(6) . . . . ?
F2 C22 C23 C24 -179.8(3) . . . . ?
C20 C19 C24 C23 1.8(5) . . . . ?
N2 C19 C24 C23 179.2(3) . . . . ?
C22 C23 C24 C19 0.0(5) . . . . ?
C28 O1 C25 C26 32.9(13) . . . . ?
O1 C25 C26 C27 -20.5(14) . . . . ?
C25 C26 C27 C28 2.3(13) . . . . ?
C25 O1 C28 C27 -31.9(12) . . . . ?
C26 C27 C28 O1 18.3(12) . . . . ?
C28A O1A C25A C26A -28(2) . . . . ?
O1A C25A C26A C27A 30(2) . . . . ?
C25A C26A C27A C28A -23(3) . . . . ?
C25A O1A C28A C27A 13(2) . . . . ?
C26A C27A C28A O1A 7(3) . . . . ?
C11 C12 N2 C19 7.9(5) . . . . ?
C1 C12 N2 C19 -175.8(3) . . . . ?
C11 C12 N2 Zn1 -176.5(3) . . . . ?
C1 C12 N2 Zn1 -0.2(3) . . . . ?
C24 C19 N2 C12 60.2(4) . . . . ?
C20 C19 N2 C12 -122.4(3) . . . . ?
C24 C19 N2 Zn1 -114.7(3) . . . . ?
C20 C19 N2 Zn1 62.8(4) . . . . ?
C2 C1 N1 C13 -6.6(5) . . . . ?
C12 C1 N1 C13 176.0(3) . . . . ?
C2 C1 N1 Zn1 175.0(3) . . . . ?
C12 C1 N1 Zn1 -2.4(3) . . . . ?
C14 C13 N1 C1 121.7(4) . . . . ?
C18 C13 N1 C1 -60.6(4) . . . . ?
C14 C13 N1 Zn1 -60.1(4) . . . . ?
C18 C13 N1 Zn1 117.6(3) . . . . ?
C33 O2 C30 C31 5(3) . . . . ?
O2 C30 C31 C32 -21(3) . . . . ?
C30 C31 C32 C33 28(2) . . . . ?
C30 O2 C33 C32 14(3) . . . . ?
C31 C32 C33 O2 -27(2) . . . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.079

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

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1061246'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14 Br2 Cl2 N2 Zn, C H2 Cl2'
_chemical_formula_sum            'C25 H16 Br2 Cl4 N2 Zn'
_chemical_formula_weight         711.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.10500(10)
_cell_length_b                   11.84230(10)
_cell_length_c                   17.5235(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.0250(10)
_cell_angle_gamma                90
_cell_volume                     2555.12(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15594
_cell_measurement_theta_min      4.5560
_cell_measurement_theta_max      76.0160

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    8.994
_shelx_estimated_absorpt_T_min   0.366
_shelx_estimated_absorpt_T_max   0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray source'
_diffrn_measurement_device_type  'Agilent SuperNova with AtlasS2 detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25415
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.590
_diffrn_reflns_theta_max         76.359
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5292
_reflns_number_gt                5075
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_cell_refinement       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction        
'CrysAlisPro V 1.171.37.31, Agilent Technologies'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+1.8084P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5292
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0691
_refine_ls_wR_factor_gt          0.0682
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.55063(14) 0.23516(15) 0.53509(10) 0.0150(3) Uani 1 1 d . . . . .
C2 C 0.53175(14) 0.14939(15) 0.58931(11) 0.0158(3) Uani 1 1 d . . . . .
C3 C 0.59067(15) 0.11019(16) 0.66600(11) 0.0177(3) Uani 1 1 d . . . . .
H3 H 0.6582 0.1435 0.6967 0.021 Uiso 1 1 calc R U . . .
C4 C 0.54755(16) 0.01885(16) 0.69760(11) 0.0195(4) Uani 1 1 d . . . . .
H4 H 0.5873 -0.0086 0.7504 0.023 Uiso 1 1 calc R U . . .
C5 C 0.45013(15) -0.03147(16) 0.65445(11) 0.0186(4) Uani 1 1 d . . . . .
H5 H 0.4238 -0.0922 0.6780 0.022 Uiso 1 1 calc R U . . .
C6 C 0.38852(14) 0.00658(16) 0.57500(11) 0.0166(3) Uani 1 1 d . . . . .
C7 C 0.43189(14) 0.09698(15) 0.54451(11) 0.0153(3) Uani 1 1 d . . . . .
C8 C 0.28834(15) -0.03850(16) 0.52277(12) 0.0189(4) Uani 1 1 d . . . . .
H8 H 0.2548 -0.0989 0.5409 0.023 Uiso 1 1 calc R U . . .
C9 C 0.23978(15) 0.00515(16) 0.44597(12) 0.0200(4) Uani 1 1 d . . . . .
H9 H 0.1733 -0.0269 0.4120 0.024 Uiso 1 1 calc R U . . .
C10 C 0.28514(15) 0.09594(16) 0.41570(11) 0.0180(3) Uani 1 1 d . . . . .
H10 H 0.2500 0.1241 0.3623 0.022 Uiso 1 1 calc R U . . .
C11 C 0.38126(14) 0.14239(15) 0.46532(11) 0.0158(3) Uani 1 1 d . . . . .
C12 C 0.45504(14) 0.23054(15) 0.45590(10) 0.0149(3) Uani 1 1 d . . . . .
C13 C 0.71395(14) 0.31986(15) 0.61534(11) 0.0157(3) Uani 1 1 d . . . . .
C14 C 0.81900(15) 0.29156(16) 0.62109(11) 0.0188(4) Uani 1 1 d . . . . .
H14 H 0.8338 0.2649 0.5748 0.023 Uiso 1 1 calc R U . . .
C15 C 0.90242(15) 0.30271(17) 0.69529(12) 0.0213(4) Uani 1 1 d . . . . .
H15 H 0.9746 0.2821 0.7007 0.026 Uiso 1 1 calc R U . . .
C16 C 0.87884(15) 0.34430(16) 0.76110(11) 0.0199(4) Uani 1 1 d . . . . .
C17 C 0.77541(16) 0.37887(16) 0.75477(11) 0.0194(4) Uani 1 1 d . . . . .
H17 H 0.7619 0.4108 0.8001 0.023 Uiso 1 1 calc R U . . .
C18 C 0.69172(15) 0.36614(16) 0.68097(11) 0.0185(4) Uani 1 1 d . . . . .
H18 H 0.6200 0.3888 0.6753 0.022 Uiso 1 1 calc R U . . .
C19 C 0.36618(14) 0.30235(15) 0.32406(11) 0.0154(3) Uani 1 1 d . . . . .
C20 C 0.38084(15) 0.27541(16) 0.25120(11) 0.0184(4) Uani 1 1 d . . . . .
H20 H 0.4505 0.2535 0.2509 0.022 Uiso 1 1 calc R U . . .
C21 C 0.29325(16) 0.28067(17) 0.17878(11) 0.0203(4) Uani 1 1 d . . . . .
H21 H 0.3015 0.2597 0.1289 0.024 Uiso 1 1 calc R U . . .
C22 C 0.19342(15) 0.31720(16) 0.18084(11) 0.0192(4) Uani 1 1 d . . . . .
C23 C 0.17850(15) 0.34805(16) 0.25252(12) 0.0188(4) Uani 1 1 d . . . . .
H23 H 0.1099 0.3742 0.2523 0.023 Uiso 1 1 calc R U . . .
C24 C 0.26613(15) 0.34000(15) 0.32504(11) 0.0172(3) Uani 1 1 d . . . . .
H24 H 0.2575 0.3602 0.3750 0.021 Uiso 1 1 calc R U . . .
C26 C 0.9385(2) 0.4775(2) 0.38213(14) 0.0374(5) Uani 1 1 d . . . . .
H26A H 0.9190 0.5513 0.3997 0.045 Uiso 1 1 calc R U . . .
H26B H 0.8976 0.4182 0.3992 0.045 Uiso 1 1 calc R U . . .
Br1 Br 0.99087(2) 0.35186(2) 0.86398(2) 0.03033(7) Uani 1 1 d . . . . .
Br2 Br 0.07493(2) 0.32642(2) 0.08103(2) 0.02860(7) Uani 1 1 d . . . . .
Cl1 Cl 0.60349(4) 0.57148(4) 0.43200(3) 0.02317(10) Uani 1 1 d . . . . .
Cl2 Cl 0.71079(4) 0.30573(4) 0.37189(3) 0.02136(10) Uani 1 1 d . . . . .
Cl3 Cl 0.90023(5) 0.47629(5) 0.27503(3) 0.03715(13) Uani 1 1 d . . . . .
Cl4 Cl 1.07880(5) 0.45414(5) 0.43031(3) 0.03399(12) Uani 1 1 d . . . . .
N1 N 0.62714(12) 0.30472(13) 0.54001(9) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.45683(12) 0.29646(13) 0.39821(9) 0.0157(3) Uani 1 1 d . . . . .
Zn1 Zn 0.60462(2) 0.38595(2) 0.43072(2) 0.01520(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.278(2) . ?
C1 C2 1.469(2) . ?
C1 C12 1.519(2) . ?
C2 C3 1.381(3) . ?
C2 C7 1.418(2) . ?
C3 C4 1.418(3) . ?
C4 C5 1.377(3) . ?
C5 C6 1.422(3) . ?
C6 C7 1.401(3) . ?
C6 C8 1.422(3) . ?
C7 C11 1.423(2) . ?
C8 C9 1.377(3) . ?
C9 C10 1.417(3) . ?
C10 C11 1.377(3) . ?
C11 C12 1.470(2) . ?
C12 N2 1.284(2) . ?
C13 C14 1.387(3) . ?
C13 C18 1.392(3) . ?
C13 N1 1.428(2) . ?
C14 C15 1.389(3) . ?
C15 C16 1.383(3) . ?
C16 C17 1.384(3) . ?
C16 Br1 1.8977(18) . ?
C17 C18 1.388(3) . ?
C19 C24 1.391(3) . ?
C19 C20 1.392(3) . ?
C19 N2 1.431(2) . ?
C20 C21 1.391(3) . ?
C21 C22 1.390(3) . ?
C22 C23 1.385(3) . ?
C22 Br2 1.9031(18) . ?
C23 C24 1.394(3) . ?
C26 Cl4 1.762(3) . ?
C26 Cl3 1.769(2) . ?
Cl1 Zn1 2.1974(5) . ?
Cl2 Zn1 2.2098(5) . ?
N1 Zn1 2.0720(15) . ?
N2 Zn1 2.1079(15) . ?

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
N1 C1 C2 134.78(16) . . ?
N1 C1 C12 117.88(16) . . ?
C2 C1 C12 107.29(15) . . ?
C3 C2 C7 119.61(17) . . ?
C3 C2 C1 134.45(17) . . ?
C7 C2 C1 105.81(15) . . ?
C2 C3 C4 118.15(17) . . ?
C5 C4 C3 122.29(17) . . ?
C4 C5 C6 120.62(17) . . ?
C7 C6 C8 116.55(17) . . ?
C7 C6 C5 116.55(17) . . ?
C8 C6 C5 126.89(17) . . ?
C6 C7 C2 122.78(17) . . ?
C6 C7 C11 123.10(16) . . ?
C2 C7 C11 114.10(16) . . ?
C9 C8 C6 120.25(17) . . ?
C8 C9 C10 122.55(17) . . ?
C11 C10 C9 118.51(17) . . ?
C10 C11 C7 119.03(17) . . ?
C10 C11 C12 135.04(17) . . ?
C7 C11 C12 105.84(15) . . ?
N2 C12 C11 135.25(16) . . ?
N2 C12 C1 117.76(16) . . ?
C11 C12 C1 106.94(15) . . ?
C14 C13 C18 121.23(17) . . ?
C14 C13 N1 119.58(16) . . ?
C18 C13 N1 119.15(16) . . ?
C13 C14 C15 119.26(17) . . ?
C16 C15 C14 119.03(18) . . ?
C15 C16 C17 122.09(18) . . ?
C15 C16 Br1 119.20(15) . . ?
C17 C16 Br1 118.69(15) . . ?
C16 C17 C18 118.84(18) . . ?
C17 C18 C13 119.37(17) . . ?
C24 C19 C20 120.78(16) . . ?
C24 C19 N2 119.84(16) . . ?
C20 C19 N2 119.30(16) . . ?
C21 C20 C19 119.78(17) . . ?
C22 C21 C20 118.71(17) . . ?
C23 C22 C21 122.14(17) . . ?
C23 C22 Br2 119.62(14) . . ?
C21 C22 Br2 118.23(14) . . ?
C22 C23 C24 118.74(17) . . ?
C19 C24 C23 119.77(17) . . ?
Cl4 C26 Cl3 112.18(13) . . ?
C1 N1 C13 120.11(15) . . ?
C1 N1 Zn1 112.14(12) . . ?
C13 N1 Zn1 127.75(12) . . ?
C12 N2 C19 120.76(15) . . ?
C12 N2 Zn1 110.84(12) . . ?
C19 N2 Zn1 128.41(12) . . ?
N1 Zn1 N2 80.98(6) . . ?
N1 Zn1 Cl1 117.01(5) . . ?
N2 Zn1 Cl1 119.78(4) . . ?
N1 Zn1 Cl2 108.57(4) . . ?
N2 Zn1 Cl2 108.95(4) . . ?
Cl1 Zn1 Cl2 116.240(19) . . ?

_refine_diff_density_max         0.511
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1061247'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H14 Cl2 F6 N2 O2 Zn'
_chemical_formula_sum            'C26 H14 Cl2 F6 N2 O2 Zn'
_chemical_formula_weight         636.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.1932(8)
_cell_length_b                   12.0306(16)
_cell_length_c                   14.760(2)
_cell_angle_alpha                112.425(13)
_cell_angle_beta                 91.392(9)
_cell_angle_gamma                109.799(10)
_cell_volume                     1245.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2695
_cell_measurement_theta_min      4.2000
_cell_measurement_theta_max      71.3130

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_F_000             636
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    4.024
_shelx_estimated_absorpt_T_min   0.739
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90542
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray source'
_diffrn_measurement_device_type  'Agilent SuperNova with AtlasS2 detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9457
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.189
_diffrn_reflns_theta_max         76.579
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4945
_reflns_number_gt                3931
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_cell_refinement       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction        
'CrysAlisPro V 1.171.37.31, Agilent Technologies'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+0.1534P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4945
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0259(4) 0.2095(3) -0.0468(2) 0.0160(7) Uani 1 1 d . . . . .
C2 C -0.1752(4) 0.0899(3) -0.0603(2) 0.0185(7) Uani 1 1 d . . . . .
C3 C -0.3086(4) -0.0049(3) -0.1384(3) 0.0218(7) Uani 1 1 d . . . . .
H3 H -0.3221 0.0020 -0.1999 0.026 Uiso 1 1 calc R U . . .
C4 C -0.4246(5) -0.1124(3) -0.1240(3) 0.0266(8) Uani 1 1 d . . . . .
H4 H -0.5172 -0.1774 -0.1770 0.032 Uiso 1 1 calc R U . . .
C5 C -0.4088(5) -0.1265(3) -0.0367(3) 0.0240(8) Uani 1 1 d . . . . .
H5 H -0.4902 -0.1998 -0.0302 0.029 Uiso 1 1 calc R U . . .
C6 C -0.2709(4) -0.0317(3) 0.0441(3) 0.0218(7) Uani 1 1 d . . . . .
C7 C -0.1583(4) 0.0750(3) 0.0291(2) 0.0181(7) Uani 1 1 d . . . . .
C8 C -0.2336(5) -0.0336(3) 0.1380(3) 0.0243(8) Uani 1 1 d . . . . .
H8 H -0.3072 -0.1029 0.1522 0.029 Uiso 1 1 calc R U . . .
C9 C -0.0914(5) 0.0645(3) 0.2087(3) 0.0236(8) Uani 1 1 d . . . . .
H9 H -0.0679 0.0595 0.2700 0.028 Uiso 1 1 calc R U . . .
C10 C 0.0197(5) 0.1713(3) 0.1932(3) 0.0230(8) Uani 1 1 d . . . . .
H10 H 0.1161 0.2377 0.2433 0.028 Uiso 1 1 calc R U . . .
C11 C -0.0141(4) 0.1775(3) 0.1039(2) 0.0182(7) Uani 1 1 d . . . . .
C12 C 0.0721(4) 0.2667(3) 0.0593(2) 0.0170(7) Uani 1 1 d . . . . .
C13 C -0.0569(4) 0.2308(3) -0.1975(2) 0.0180(7) Uani 1 1 d . . . . .
C14 C 0.0235(5) 0.2002(3) -0.2802(3) 0.0244(8) Uani 1 1 d . . . . .
H14 H 0.1406 0.2032 -0.2728 0.029 Uiso 1 1 calc R U . . .
C15 C -0.0672(5) 0.1650(4) -0.3743(3) 0.0282(8) Uani 1 1 d . . . . .
H15 H -0.0144 0.1413 -0.4317 0.034 Uiso 1 1 calc R U . . .
C16 C -0.2352(5) 0.1652(3) -0.3823(3) 0.0236(8) Uani 1 1 d . . . . .
C17 C -0.3147(5) 0.2005(3) -0.2998(3) 0.0226(8) Uani 1 1 d . . . . .
H17 H -0.4291 0.2026 -0.3068 0.027 Uiso 1 1 calc R U . . .
C18 C -0.2253(4) 0.2326(3) -0.2071(3) 0.0207(7) Uani 1 1 d . . . . .
H18 H -0.2788 0.2559 -0.1500 0.025 Uiso 1 1 calc R U . . .
C19 C -0.2789(5) 0.1108(4) -0.5572(3) 0.0280(8) Uani 1 1 d . . . . .
C20 C 0.2781(4) 0.4392(3) 0.1954(2) 0.0175(7) Uani 1 1 d . . . . .
C21 C 0.4501(4) 0.4568(3) 0.2257(3) 0.0206(7) Uani 1 1 d . . . . .
H21 H 0.5182 0.4261 0.1780 0.025 Uiso 1 1 calc R U . . .
C22 C 0.5225(5) 0.5201(3) 0.3273(3) 0.0237(8) Uani 1 1 d . . . . .
H22 H 0.6394 0.5318 0.3496 0.028 Uiso 1 1 calc R U . . .
C23 C 0.4212(5) 0.5652(3) 0.3946(3) 0.0229(8) Uani 1 1 d . . . . .
C24 C 0.2492(5) 0.5472(3) 0.3654(3) 0.0215(7) Uani 1 1 d . . . . .
H24 H 0.1813 0.5775 0.4134 0.026 Uiso 1 1 calc R U . . .
C25 C 0.1777(4) 0.4838(3) 0.2644(3) 0.0202(7) Uani 1 1 d . . . . .
H25 H 0.0601 0.4710 0.2427 0.024 Uiso 1 1 calc R U . . .
C26 C 0.6461(5) 0.7153(4) 0.5345(3) 0.0303(9) Uani 1 1 d . . . . .
Cl1 Cl 0.46533(10) 0.36234(7) -0.10279(6) 0.01848(17) Uani 1 1 d . . . . .
Cl2 Cl 0.18814(10) 0.57122(8) -0.07741(6) 0.02060(18) Uani 1 1 d . . . . .
N1 N 0.0363(3) 0.2688(3) -0.1010(2) 0.0168(6) Uani 1 1 d . . . . .
N2 N 0.2023(3) 0.3768(3) 0.09114(19) 0.0154(6) Uani 1 1 d . . . . .
O1 O -0.3421(3) 0.1334(3) -0.47222(18) 0.0288(6) Uani 1 1 d . . . . .
O2 O 0.4809(3) 0.6278(2) 0.49933(18) 0.0275(6) Uani 1 1 d . . . . .
Zn1 Zn 0.26944(6) 0.44672(4) -0.01999(3) 0.01702(12) Uani 1 1 d . . . . .
F1 F -0.4047(3) 0.0909(2) -0.62715(16) 0.0350(6) Uani 1 1 d . . . . .
F2 F -0.1354(3) 0.2106(2) -0.55203(16) 0.0345(5) Uani 1 1 d . . . . .
F3 F -0.2357(3) 0.0064(2) -0.58756(16) 0.0355(5) Uani 1 1 d . . . . .
F4 F 0.6904(3) 0.8001(2) 0.49400(18) 0.0421(6) Uani 1 1 d . . . . .
F5 F 0.7669(3) 0.6621(2) 0.52321(18) 0.0406(6) Uani 1 1 d . . . . .
F6 F 0.6582(3) 0.7802(2) 0.63251(16) 0.0397(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.273(4) . ?
C1 C2 1.477(4) . ?
C1 C12 1.520(4) . ?
C2 C3 1.384(4) . ?
C2 C7 1.407(5) . ?
C3 C4 1.417(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.370(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.422(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.405(5) . ?
C6 C8 1.421(5) . ?
C7 C11 1.431(4) . ?
C8 C9 1.381(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.405(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.460(5) . ?
C12 N2 1.288(4) . ?
C13 C14 1.385(5) . ?
C13 C18 1.392(5) . ?
C13 N1 1.427(4) . ?
C14 C15 1.396(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(5) . ?
C16 O1 1.416(4) . ?
C17 C18 1.383(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 F1 1.333(4) . ?
C19 O1 1.335(4) . ?
C19 F3 1.336(4) . ?
C19 F2 1.341(4) . ?
C20 C25 1.388(5) . ?
C20 C21 1.388(4) . ?
C20 N2 1.439(4) . ?
C21 C22 1.400(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(5) . ?
C23 O2 1.422(4) . ?
C24 C25 1.392(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 F4 1.325(5) . ?
C26 F5 1.332(4) . ?
C26 F6 1.338(4) . ?
C26 O2 1.339(4) . ?
Cl1 Zn1 2.3135(9) . ?
Cl1 Zn1 2.5562(10) 2_665 ?
Cl2 Zn1 2.2411(9) . ?
N1 Zn1 2.197(3) . ?
N2 Zn1 2.117(3) . ?
Zn1 Cl1 2.5562(10) 2_665 ?

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
N1 C1 C2 136.0(3) . . ?
N1 C1 C12 117.2(3) . . ?
C2 C1 C12 106.7(3) . . ?
C3 C2 C7 119.1(3) . . ?
C3 C2 C1 134.9(3) . . ?
C7 C2 C1 105.9(3) . . ?
C2 C3 C4 118.2(3) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 122.7(3) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C8 116.5(3) . . ?
C7 C6 C5 116.3(3) . . ?
C8 C6 C5 127.3(3) . . ?
C6 C7 C2 123.4(3) . . ?
C6 C7 C11 122.3(3) . . ?
C2 C7 C11 114.2(3) . . ?
C9 C8 C6 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C6 C8 H8 119.7 . . ?
C8 C9 C10 122.4(3) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C11 C10 C9 118.6(3) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C10 C11 C7 119.5(3) . . ?
C10 C11 C12 134.7(3) . . ?
C7 C11 C12 105.7(3) . . ?
N2 C12 C11 134.2(3) . . ?
N2 C12 C1 118.4(3) . . ?
C11 C12 C1 107.4(3) . . ?
C14 C13 C18 120.2(3) . . ?
C14 C13 N1 120.3(3) . . ?
C18 C13 N1 119.4(3) . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 118.6(4) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C17 121.9(3) . . ?
C15 C16 O1 125.0(3) . . ?
C17 C16 O1 113.1(3) . . ?
C18 C17 C16 119.1(3) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C13 120.0(3) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
F1 C19 O1 107.5(3) . . ?
F1 C19 F3 108.0(3) . . ?
O1 C19 F3 113.4(3) . . ?
F1 C19 F2 108.0(3) . . ?
O1 C19 F2 113.1(3) . . ?
F3 C19 F2 106.7(3) . . ?
C25 C20 C21 120.8(3) . . ?
C25 C20 N2 118.9(3) . . ?
C21 C20 N2 120.3(3) . . ?
C20 C21 C22 119.4(3) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 118.9(3) . . ?
C23 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C22 C23 C24 122.3(3) . . ?
C22 C23 O2 123.2(3) . . ?
C24 C23 O2 114.4(3) . . ?
C23 C24 C25 118.5(3) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
C20 C25 C24 120.0(3) . . ?
C20 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
F4 C26 F5 107.3(3) . . ?
F4 C26 F6 108.4(3) . . ?
F5 C26 F6 106.8(3) . . ?
F4 C26 O2 113.6(3) . . ?
F5 C26 O2 113.3(3) . . ?
F6 C26 O2 107.2(3) . . ?
Zn1 Cl1 Zn1 92.00(3) . 2_665 ?
C1 N1 C13 121.2(3) . . ?
C1 N1 Zn1 112.3(2) . . ?
C13 N1 Zn1 125.8(2) . . ?
C12 N2 C20 118.1(3) . . ?
C12 N2 Zn1 113.6(2) . . ?
C20 N2 Zn1 128.3(2) . . ?
C19 O1 C16 120.9(3) . . ?
C26 O2 C23 118.6(3) . . ?
N2 Zn1 N1 78.07(10) . . ?
N2 Zn1 Cl2 135.57(8) . . ?
N1 Zn1 Cl2 95.83(7) . . ?
N2 Zn1 Cl1 109.09(8) . . ?
N1 Zn1 Cl1 94.47(8) . . ?
Cl2 Zn1 Cl1 115.27(4) . . ?
N2 Zn1 Cl1 90.27(7) . 2_665 ?
N1 Zn1 Cl1 168.26(8) . 2_665 ?
Cl2 Zn1 Cl1 93.46(3) . 2_665 ?
Cl1 Zn1 Cl1 88.00(3) . 2_665 ?

_refine_diff_density_max         0.597
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1061248'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H14 Cl2 F6 N2 O2 Zn, C H2 Cl2'
_chemical_formula_sum            'C54 H32 Cl8 F12 N4 O4 Zn2'
_chemical_formula_weight         1443.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.8689(6)
_cell_length_b                   14.1948(11)
_cell_length_c                   17.6232(16)
_cell_angle_alpha                107.262(7)
_cell_angle_beta                 92.978(5)
_cell_angle_gamma                94.504(5)
_cell_volume                     2817.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8416
_cell_measurement_theta_min      3.7410
_cell_measurement_theta_max      76.0230

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    5.342
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.45025
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray source'
_diffrn_measurement_device_type  'Agilent SuperNova with AtlasS2 detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17297
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.530
_diffrn_reflns_theta_max         76.980
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             17297
_reflns_number_gt                13336
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_cell_refinement       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction        
'CrysAlisPro V 1.171.37.31, Agilent Technologies'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1204P)²+14.1177P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         17297
_refine_ls_number_parameters     758
_refine_ls_number_restraints     702
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0877
_refine_ls_wR_factor_ref         0.2449
_refine_ls_wR_factor_gt          0.2289
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7317(6) 0.4485(4) 0.4669(4) 0.0209(12) Uani 1 1 d . U . . .
C2 C 0.6465(6) 0.4673(5) 0.4103(4) 0.0229(12) Uani 1 1 d . U . . .
C3 C 0.6034(6) 0.4159(5) 0.3341(4) 0.0250(13) Uani 1 1 d . U . . .
H3 H 0.6309 0.3569 0.3061 0.030 Uiso 1 1 calc R U . . .
C4 C 0.5154(6) 0.4558(5) 0.2993(4) 0.0271(14) Uani 1 1 d . U . . .
H4 H 0.4859 0.4221 0.2475 0.033 Uiso 1 1 calc R U . . .
C5 C 0.4717(6) 0.5433(5) 0.3397(4) 0.0264(14) Uani 1 1 d . U . . .
H5 H 0.4145 0.5675 0.3149 0.032 Uiso 1 1 calc R U . . .
C6 C 0.5144(6) 0.5954(5) 0.4186(4) 0.0226(12) Uani 1 1 d . U . . .
C7 C 0.6036(6) 0.5570(4) 0.4513(4) 0.0209(12) Uani 1 1 d . U . . .
C8 C 0.4751(6) 0.6833(5) 0.4691(4) 0.0268(14) Uani 1 1 d . U . . .
H8 H 0.4174 0.7128 0.4499 0.032 Uiso 1 1 calc R U . . .
C9 C 0.5221(6) 0.7241(5) 0.5457(4) 0.0280(14) Uani 1 1 d . U . . .
H9 H 0.4933 0.7800 0.5780 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6130(6) 0.6845(5) 0.5778(4) 0.0251(13) Uani 1 1 d . U . . .
H10 H 0.6444 0.7143 0.6297 0.030 Uiso 1 1 calc R U . . .
C11 C 0.6529(6) 0.6012(5) 0.5298(4) 0.0226(12) Uani 1 1 d . U . . .
C12 C 0.7380(6) 0.5361(5) 0.5429(4) 0.0227(12) Uani 1 1 d . U . . .
C13 C 0.7938(6) 0.2916(5) 0.4016(4) 0.0231(13) Uani 1 1 d . U . . .
C14 C 0.7643(6) 0.2001(5) 0.4098(4) 0.0275(14) Uani 1 1 d . U . . .
H14 H 0.7420 0.1948 0.4583 0.033 Uiso 1 1 calc R U . . .
C15 C 0.7674(7) 0.1153(5) 0.3459(4) 0.0328(16) Uani 1 1 d . U . . .
H15 H 0.7441 0.0531 0.3502 0.039 Uiso 1 1 calc R U . . .
C16 C 0.8060(7) 0.1254(5) 0.2756(4) 0.0301(15) Uani 1 1 d . U . . .
C17 C 0.8376(6) 0.2167(5) 0.2664(4) 0.0304(15) Uani 1 1 d . U . . .
H17 H 0.8622 0.2217 0.2184 0.036 Uiso 1 1 calc R U . . .
C18 C 0.8319(6) 0.3010(5) 0.3302(4) 0.0261(14) Uani 1 1 d . U . . .
H18 H 0.8532 0.3634 0.3256 0.031 Uiso 1 1 calc R U . . .
C19 C 0.7509(9) 0.0142(6) 0.1480(5) 0.0451(19) Uani 1 1 d . U . . .
C20 C 0.8211(6) 0.6204(5) 0.6717(4) 0.0252(13) Uani 1 1 d . U . . .
C21 C 0.7952(7) 0.6080(6) 0.7448(4) 0.0304(15) Uani 1 1 d . U . . .
H21 H 0.7716 0.5453 0.7480 0.037 Uiso 1 1 calc R U . . .
C22 C 0.8047(7) 0.6892(6) 0.8124(5) 0.0336(16) Uani 1 1 d . U . . .
H22 H 0.7836 0.6823 0.8607 0.040 Uiso 1 1 calc R U . . .
C23 C 0.8456(7) 0.7807(6) 0.8075(5) 0.0373(16) Uani 1 1 d . U . . .
C24 C 0.8757(7) 0.7941(5) 0.7362(5) 0.0328(15) Uani 1 1 d . U . . .
H24 H 0.9035 0.8562 0.7337 0.039 Uiso 1 1 calc R U . . .
C25 C 0.8631(6) 0.7118(5) 0.6683(4) 0.0299(15) Uani 1 1 d . U . . .
H25 H 0.8835 0.7189 0.6199 0.036 Uiso 1 1 calc R U . . .
C26 C 0.8837(14) 0.9454(10) 0.8904(8) 0.085(3) Uani 1 1 d . U . . .
C27 C 0.7600(6) 0.4554(5) -0.0321(4) 0.0216(12) Uani 1 1 d . U . . .
C28 C 0.8453(6) 0.4696(5) -0.0854(4) 0.0232(12) Uani 1 1 d . U . . .
C29 C 0.8786(6) 0.4132(5) -0.1564(4) 0.0262(13) Uani 1 1 d . U . . .
H29 H 0.8406 0.3513 -0.1827 0.031 Uiso 1 1 calc R U . . .
C30 C 0.9722(6) 0.4510(5) -0.1891(4) 0.0275(14) Uani 1 1 d . U . . .
H30 H 0.9955 0.4125 -0.2371 0.033 Uiso 1 1 calc R U . . .
C31 C 1.0291(6) 0.5415(5) -0.1525(4) 0.0267(14) Uani 1 1 d . U . . .
H31 H 1.0892 0.5640 -0.1765 0.032 Uiso 1 1 calc R U . . .
C32 C 0.9979(6) 0.6022(5) -0.0781(4) 0.0240(13) Uani 1 1 d . U . . .
C33 C 0.9054(6) 0.5626(5) -0.0461(4) 0.0227(12) Uani 1 1 d . U . . .
C34 C 1.0493(6) 0.6964(5) -0.0324(4) 0.0288(14) Uani 1 1 d . U . . .
H34 H 1.1098 0.7260 -0.0514 0.035 Uiso 1 1 calc R U . . .
C35 C 1.0111(6) 0.7450(5) 0.0397(4) 0.0302(15) Uani 1 1 d . U . . .
H35 H 1.0469 0.8070 0.0684 0.036 Uiso 1 1 calc R U . . .
C36 C 0.9196(6) 0.7045(5) 0.0720(4) 0.0286(14) Uani 1 1 d . U . . .
H36 H 0.8953 0.7390 0.1210 0.034 Uiso 1 1 calc R U . . .
C37 C 0.8670(6) 0.6121(5) 0.0288(4) 0.0225(12) Uani 1 1 d . U . . .
C38 C 0.7744(6) 0.5457(5) 0.0416(4) 0.0225(12) Uani 1 1 d . U . . .
C39 C 0.6492(6) 0.3045(5) -0.1025(4) 0.0241(13) Uani 1 1 d . U . . .
C40 C 0.6388(7) 0.2090(5) -0.0965(4) 0.0306(15) Uani 1 1 d . U . . .
H40 H 0.6578 0.1979 -0.0483 0.037 Uiso 1 1 calc R U . . .
C41 C 0.5996(7) 0.1297(5) -0.1636(5) 0.0358(17) Uani 1 1 d . U . . .
H41 H 0.5948 0.0650 -0.1611 0.043 Uiso 1 1 calc R U . . .
C42 C 0.5679(7) 0.1491(5) -0.2337(4) 0.0319(15) Uani 1 1 d . U . . .
C43 C 0.5748(6) 0.2446(5) -0.2395(4) 0.0284(14) Uani 1 1 d . U . . .
H43 H 0.5521 0.2559 -0.2871 0.034 Uiso 1 1 calc R U . . .
C44 C 0.6160(6) 0.3228(5) -0.1736(4) 0.0264(14) Uani 1 1 d . U . . .
H44 H 0.6215 0.3873 -0.1765 0.032 Uiso 1 1 calc R U . . .
C45 C 0.5797(9) 0.0310(6) -0.3588(5) 0.049(2) Uani 1 1 d . U . . .
C46 C 0.7182(6) 0.6284(5) 0.1691(4) 0.0227(13) Uani 1 1 d . U . . .
C47 C 0.7450(6) 0.6144(5) 0.2420(4) 0.0277(14) Uani 1 1 d . U . . .
H47 H 0.7553 0.5512 0.2449 0.033 Uiso 1 1 calc R U . . .
C48 C 0.7565(7) 0.6949(5) 0.3111(4) 0.0311(15) Uani 1 1 d . U . . .
H48 H 0.7764 0.6868 0.3604 0.037 Uiso 1 1 calc R U . . .
C49 C 0.7378(6) 0.7866(5) 0.3046(4) 0.0271(14) Uani 1 1 d . U . . .
C50 C 0.7054(7) 0.8015(5) 0.2328(4) 0.0292(15) Uani 1 1 d . U . . .
H50 H 0.6909 0.8641 0.2307 0.035 Uiso 1 1 calc R U . . .
C51 C 0.6950(6) 0.7215(5) 0.1644(4) 0.0281(14) Uani 1 1 d . U . . .
H51 H 0.6728 0.7296 0.1155 0.034 Uiso 1 1 calc R U . . .
C52 C 0.7250(12) 0.8798(7) 0.4379(6) 0.060(2) Uani 1 1 d . U . . .
C53 C 0.5507(13) 0.8252(11) 0.8681(9) 0.089(4) Uani 1 1 d . U . . .
H53A H 0.4758 0.7972 0.8744 0.107 Uiso 1 1 calc R U . . .
H53B H 0.6038 0.7777 0.8714 0.107 Uiso 1 1 calc R U . . .
C54 C 0.9390(11) 1.0957(8) 0.6393(8) 0.072(3) Uani 1 1 d . U . . .
H54A H 0.9916 1.1369 0.6194 0.087 Uiso 1 1 calc R U . . .
H54B H 0.8635 1.0975 0.6162 0.087 Uiso 1 1 calc R U . . .
Cl1 Cl 0.79527(15) 0.30695(12) 0.64097(10) 0.0285(4) Uani 1 1 d . U . . .
Cl2 Cl 1.06639(15) 0.41793(14) 0.58004(12) 0.0355(4) Uani 1 1 d . U . . .
Cl3 Cl 0.42586(15) 0.40671(12) 0.07483(10) 0.0279(3) Uani 1 1 d . U . . .
Cl4 Cl 0.69528(15) 0.32214(13) 0.14282(10) 0.0293(4) Uani 1 1 d . U . . .
Cl5 Cl 0.5512(3) 0.8421(2) 0.77464(19) 0.0779(9) Uani 1 1 d . U . . .
Cl6 Cl 0.5852(5) 0.9301(4) 0.9435(2) 0.1252(18) Uani 1 1 d . U . . .
Cl7 Cl 0.9757(3) 0.9725(2) 0.6102(3) 0.0899(11) Uani 1 1 d . U . . .
Cl8 Cl 0.9425(5) 1.1425(3) 0.7427(2) 0.1228(18) Uani 1 1 d . U . . .
F1 F 0.6403(6) 0.0029(5) 0.1643(4) 0.0684(17) Uani 1 1 d . U . . .
F2 F 0.7559(6) 0.0787(4) 0.1086(3) 0.0541(14) Uani 1 1 d . U . . .
F3 F 0.7740(6) -0.0723(3) 0.1015(3) 0.0542(14) Uani 1 1 d . U . . .
F4 F 0.8145(9) 0.9824(6) 0.8401(5) 0.105(3) Uani 1 1 d . U . . .
F5 F 0.8759(8) 1.0015(5) 0.9619(4) 0.102(3) Uani 1 1 d . U . . .
F6 F 0.9856(9) 0.9651(8) 0.8684(5) 0.142(4) Uani 1 1 d . U . . .
F7 F 0.6256(6) 0.0981(4) -0.3892(3) 0.0631(17) Uani 1 1 d . U . . .
F8 F 0.5136(6) -0.0352(3) -0.4143(3) 0.0561(15) Uani 1 1 d . U . . .
F9 F 0.6645(6) -0.0133(5) -0.3369(4) 0.0747(18) Uani 1 1 d . U . . .
F10 F 0.7356(6) 0.9726(4) 0.4836(3) 0.0636(18) Uani 1 1 d . U . . .
F11 F 0.6020(6) 0.8519(5) 0.4226(4) 0.0739(18) Uani 1 1 d . U . . .
F12 F 0.7490(7) 0.8222(4) 0.4776(3) 0.072(2) Uani 1 1 d . U . . .
N1 N 0.7912(5) 0.3780(4) 0.4685(3) 0.0226(11) Uani 1 1 d . U . . .
N2 N 0.8067(5) 0.5366(4) 0.6022(3) 0.0245(11) Uani 1 1 d . U . . .
N3 N 0.6829(5) 0.3858(4) -0.0337(3) 0.0233(11) Uani 1 1 d . U . . .
N4 N 0.7110(5) 0.5452(4) 0.0992(3) 0.0218(11) Uani 1 1 d . U . . .
O1 O 0.8171(6) 0.0373(4) 0.2149(3) 0.0427(14) Uani 1 1 d . U . . .
O2 O 0.8505(7) 0.8566(5) 0.8800(4) 0.0565(17) Uani 1 1 d . U . . .
O3 O 0.5161(5) 0.0703(4) -0.2980(3) 0.0379(13) Uani 1 1 d . U . . .
O4 O 0.7569(6) 0.8744(4) 0.3694(3) 0.0418(14) Uani 1 1 d . U . . .
Zn1 Zn 0.88097(8) 0.40347(6) 0.57909(5) 0.0230(2) Uani 1 1 d . U . . .
Zn2 Zn 0.61197(8) 0.41095(6) 0.07560(5) 0.0230(2) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.275(8) . ?
C1 C2 1.478(9) . ?
C1 C12 1.527(9) . ?
C2 C3 1.374(9) . ?
C2 C7 1.413(9) . ?
C3 C4 1.422(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(9) . ?
C6 C8 1.429(10) . ?
C7 C11 1.412(9) . ?
C8 C9 1.369(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.422(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.475(9) . ?
C12 N2 1.290(9) . ?
C13 C14 1.370(9) . ?
C13 C18 1.398(10) . ?
C13 N1 1.430(8) . ?
C14 C15 1.387(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(10) . ?
C16 O1 1.404(8) . ?
C17 C18 1.387(10) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 F2 1.303(10) . ?
C19 F3 1.316(10) . ?
C19 O1 1.322(11) . ?
C19 F1 1.366(12) . ?
C20 C25 1.372(10) . ?
C20 C21 1.397(10) . ?
C20 N2 1.423(8) . ?
C21 C22 1.383(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(11) . ?
C22 H22 0.9300 . ?
C23 C24 1.387(12) . ?
C23 O2 1.401(9) . ?
C24 C25 1.394(10) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 O2 1.248(14) . ?
C26 F5 1.288(13) . ?
C26 F6 1.323(16) . ?
C26 F4 1.416(19) . ?
C27 N3 1.286(9) . ?
C27 C28 1.458(10) . ?
C27 C38 1.521(9) . ?
C28 C29 1.367(9) . ?
C28 C33 1.411(9) . ?
C29 C30 1.417(10) . ?
C29 H29 0.9300 . ?
C30 C31 1.360(10) . ?
C30 H30 0.9300 . ?
C31 C32 1.426(9) . ?
C31 H31 0.9300 . ?
C32 C33 1.412(10) . ?
C32 C34 1.410(10) . ?
C33 C37 1.416(9) . ?
C34 C35 1.373(10) . ?
C34 H34 0.9300 . ?
C35 C36 1.412(10) . ?
C35 H35 0.9300 . ?
C36 C37 1.386(9) . ?
C36 H36 0.9300 . ?
C37 C38 1.462(9) . ?
C38 N4 1.297(9) . ?
C39 C40 1.387(9) . ?
C39 C44 1.396(10) . ?
C39 N3 1.418(8) . ?
C40 C41 1.397(10) . ?
C40 H40 0.9300 . ?
C41 C42 1.383(11) . ?
C41 H41 0.9300 . ?
C42 C43 1.386(10) . ?
C42 O3 1.408(9) . ?
C43 C44 1.383(9) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?
C45 F8 1.309(10) . ?
C45 F7 1.319(10) . ?
C45 F9 1.327(13) . ?
C45 O3 1.350(10) . ?
C46 C47 1.382(9) . ?
C46 C51 1.396(9) . ?
C46 N4 1.425(8) . ?
C47 C48 1.393(10) . ?
C47 H47 0.9300 . ?
C48 C49 1.375(10) . ?
C48 H48 0.9300 . ?
C49 C50 1.383(10) . ?
C49 O4 1.412(8) . ?
C50 C51 1.382(9) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?
C52 F12 1.262(12) . ?
C52 O4 1.267(11) . ?
C52 F10 1.317(10) . ?
C52 F11 1.471(15) . ?
C53 Cl6 1.680(16) . ?
C53 Cl5 1.734(14) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C54 Cl8 1.741(13) . ?
C54 Cl7 1.768(11) . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?
Cl1 Zn1 2.2101(18) . ?
Cl2 Zn1 2.1929(19) . ?
Cl3 Zn2 2.2042(18) . ?
Cl4 Zn2 2.2206(18) . ?
N1 Zn1 2.091(5) . ?
N2 Zn1 2.087(6) . ?
N3 Zn2 2.087(6) . ?
N4 Zn2 2.077(5) . ?

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
N1 C1 C2 136.3(6) . . ?
N1 C1 C12 116.9(6) . . ?
C2 C1 C12 106.6(5) . . ?
C3 C2 C7 120.0(6) . . ?
C3 C2 C1 133.9(6) . . ?
C7 C2 C1 106.0(6) . . ?
C2 C3 C4 117.8(6) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C5 C4 C3 122.5(6) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 119.8(6) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 117.1(6) . . ?
C7 C6 C8 116.3(6) . . ?
C5 C6 C8 126.5(6) . . ?
C6 C7 C11 122.7(6) . . ?
C6 C7 C2 122.7(6) . . ?
C11 C7 C2 114.4(6) . . ?
C9 C8 C6 120.3(6) . . ?
C9 C8 H8 119.9 . . ?
C6 C8 H8 119.9 . . ?
C8 C9 C10 122.6(7) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
C11 C10 C9 117.8(6) . . ?
C11 C10 H10 121.1 . . ?
C9 C10 H10 121.1 . . ?
C10 C11 C7 120.1(6) . . ?
C10 C11 C12 133.5(6) . . ?
C7 C11 C12 106.2(6) . . ?
N2 C12 C11 134.7(6) . . ?
N2 C12 C1 118.5(6) . . ?
C11 C12 C1 106.7(5) . . ?
C14 C13 C18 120.8(6) . . ?
C14 C13 N1 119.3(6) . . ?
C18 C13 N1 119.9(6) . . ?
C13 C14 C15 120.2(7) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 118.5(7) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C17 C16 C15 122.2(7) . . ?
C17 C16 O1 121.1(7) . . ?
C15 C16 O1 116.6(6) . . ?
C16 C17 C18 118.6(7) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C17 C18 C13 119.6(6) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
F2 C19 F3 109.4(7) . . ?
F2 C19 O1 116.1(7) . . ?
F3 C19 O1 108.7(8) . . ?
F2 C19 F1 105.9(9) . . ?
F3 C19 F1 106.7(7) . . ?
O1 C19 F1 109.6(7) . . ?
C25 C20 C21 119.8(6) . . ?
C25 C20 N2 121.1(6) . . ?
C21 C20 N2 119.0(6) . . ?
C22 C21 C20 119.8(7) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C23 C22 C21 119.4(7) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 121.8(7) . . ?
C22 C23 O2 113.6(7) . . ?
C24 C23 O2 124.6(8) . . ?
C23 C24 C25 117.9(7) . . ?
C23 C24 H24 121.0 . . ?
C25 C24 H24 121.0 . . ?
C20 C25 C24 121.1(7) . . ?
C20 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
O2 C26 F5 113.5(13) . . ?
O2 C26 F6 117.3(13) . . ?
F5 C26 F6 108.7(11) . . ?
O2 C26 F4 108.8(12) . . ?
F5 C26 F4 106.1(12) . . ?
F6 C26 F4 101.1(13) . . ?
N3 C27 C28 134.9(6) . . ?
N3 C27 C38 117.4(6) . . ?
C28 C27 C38 107.6(5) . . ?
C29 C28 C33 119.5(6) . . ?
C29 C28 C27 134.9(6) . . ?
C33 C28 C27 105.4(6) . . ?
C28 C29 C30 118.7(6) . . ?
C28 C29 H29 120.6 . . ?
C30 C29 H29 120.6 . . ?
C31 C30 C29 122.2(7) . . ?
C31 C30 H30 118.9 . . ?
C29 C30 H30 118.9 . . ?
C30 C31 C32 120.9(7) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C33 C32 C34 116.4(6) . . ?
C33 C32 C31 115.9(6) . . ?
C34 C32 C31 127.7(7) . . ?
C28 C33 C32 122.7(6) . . ?
C28 C33 C37 114.5(6) . . ?
C32 C33 C37 122.7(6) . . ?
C35 C34 C32 120.9(7) . . ?
C35 C34 H34 119.6 . . ?
C32 C34 H34 119.6 . . ?
C34 C35 C36 122.5(6) . . ?
C34 C35 H35 118.7 . . ?
C36 C35 H35 118.7 . . ?
C37 C36 C35 118.2(6) . . ?
C37 C36 H36 120.9 . . ?
C35 C36 H36 120.9 . . ?
C36 C37 C33 119.2(6) . . ?
C36 C37 C38 134.9(6) . . ?
C33 C37 C38 105.9(6) . . ?
N4 C38 C37 135.8(6) . . ?
N4 C38 C27 117.7(6) . . ?
C37 C38 C27 106.5(5) . . ?
C40 C39 C44 120.9(6) . . ?
C40 C39 N3 119.7(6) . . ?
C44 C39 N3 119.1(6) . . ?
C39 C40 C41 119.5(7) . . ?
C39 C40 H40 120.3 . . ?
C41 C40 H40 120.3 . . ?
C42 C41 C40 118.9(7) . . ?
C42 C41 H41 120.6 . . ?
C40 C41 H41 120.6 . . ?
C41 C42 C43 122.0(7) . . ?
C41 C42 O3 118.4(6) . . ?
C43 C42 O3 119.3(7) . . ?
C44 C43 C42 119.0(7) . . ?
C44 C43 H43 120.5 . . ?
C42 C43 H43 120.5 . . ?
C43 C44 C39 119.7(6) . . ?
C43 C44 H44 120.2 . . ?
C39 C44 H44 120.2 . . ?
F8 C45 F7 109.1(8) . . ?
F8 C45 F9 108.4(7) . . ?
F7 C45 F9 106.5(9) . . ?
F8 C45 O3 107.6(8) . . ?
F7 C45 O3 112.7(7) . . ?
F9 C45 O3 112.4(8) . . ?
C47 C46 C51 120.7(6) . . ?
C47 C46 N4 118.6(6) . . ?
C51 C46 N4 120.6(6) . . ?
C46 C47 C48 119.9(6) . . ?
C46 C47 H47 120.0 . . ?
C48 C47 H47 120.0 . . ?
C49 C48 C47 118.2(7) . . ?
C49 C48 H48 120.9 . . ?
C47 C48 H48 120.9 . . ?
C48 C49 C50 122.7(6) . . ?
C48 C49 O4 122.9(7) . . ?
C50 C49 O4 114.3(6) . . ?
C51 C50 C49 118.7(6) . . ?
C51 C50 H50 120.6 . . ?
C49 C50 H50 120.6 . . ?
C50 C51 C46 119.5(6) . . ?
C50 C51 H51 120.3 . . ?
C46 C51 H51 120.3 . . ?
F12 C52 O4 125.2(10) . . ?
F12 C52 F10 110.9(8) . . ?
O4 C52 F10 110.3(8) . . ?
F12 C52 F11 99.1(8) . . ?
O4 C52 F11 103.3(9) . . ?
F10 C52 F11 105.1(9) . . ?
Cl6 C53 Cl5 113.6(8) . . ?
Cl6 C53 H53A 108.8 . . ?
Cl5 C53 H53A 108.8 . . ?
Cl6 C53 H53B 108.8 . . ?
Cl5 C53 H53B 108.8 . . ?
H53A C53 H53B 107.7 . . ?
Cl8 C54 Cl7 110.7(7) . . ?
Cl8 C54 H54A 109.5 . . ?
Cl7 C54 H54A 109.5 . . ?
Cl8 C54 H54B 109.5 . . ?
Cl7 C54 H54B 109.5 . . ?
H54A C54 H54B 108.1 . . ?
C1 N1 C13 122.9(6) . . ?
C1 N1 Zn1 112.3(4) . . ?
C13 N1 Zn1 124.8(4) . . ?
C12 N2 C20 120.0(6) . . ?
C12 N2 Zn1 110.8(4) . . ?
C20 N2 Zn1 129.1(4) . . ?
C27 N3 C39 123.4(6) . . ?
C27 N3 Zn2 111.5(4) . . ?
C39 N3 Zn2 125.1(4) . . ?
C38 N4 C46 120.6(6) . . ?
C38 N4 Zn2 111.4(4) . . ?
C46 N4 Zn2 128.0(4) . . ?
C19 O1 C16 119.6(7) . . ?
C26 O2 C23 125.4(9) . . ?
C45 O3 C42 117.6(7) . . ?
C52 O4 C49 122.5(7) . . ?
N2 Zn1 N1 81.2(2) . . ?
N2 Zn1 Cl2 115.04(17) . . ?
N1 Zn1 Cl2 116.25(17) . . ?
N2 Zn1 Cl1 109.85(17) . . ?
N1 Zn1 Cl1 107.74(16) . . ?
Cl2 Zn1 Cl1 120.12(7) . . ?
N4 Zn2 N3 81.4(2) . . ?
N4 Zn2 Cl3 120.39(16) . . ?
N3 Zn2 Cl3 117.55(17) . . ?
N4 Zn2 Cl4 107.52(16) . . ?
N3 Zn2 Cl4 108.04(16) . . ?
Cl3 Zn2 Cl4 116.52(7) . . ?

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
N1 C1 C2 C3 -4.5(14) . . . . ?
C12 C1 C2 C3 -179.1(7) . . . . ?
N1 C1 C2 C7 172.6(7) . . . . ?
C12 C1 C2 C7 -1.9(7) . . . . ?
C7 C2 C3 C4 -0.3(10) . . . . ?
C1 C2 C3 C4 176.5(7) . . . . ?
C2 C3 C4 C5 -0.6(10) . . . . ?
C3 C4 C5 C6 -0.5(11) . . . . ?
C4 C5 C6 C7 2.5(10) . . . . ?
C4 C5 C6 C8 -176.9(7) . . . . ?
C5 C6 C7 C11 -179.1(6) . . . . ?
C8 C6 C7 C11 0.3(9) . . . . ?
C5 C6 C7 C2 -3.5(10) . . . . ?
C8 C6 C7 C2 175.9(6) . . . . ?
C3 C2 C7 C6 2.5(10) . . . . ?
C1 C2 C7 C6 -175.2(6) . . . . ?
C3 C2 C7 C11 178.4(6) . . . . ?
C1 C2 C7 C11 0.8(8) . . . . ?
C7 C6 C8 C9 -1.7(10) . . . . ?
C5 C6 C8 C9 177.7(7) . . . . ?
C6 C8 C9 C10 2.1(11) . . . . ?
C8 C9 C10 C11 -1.1(11) . . . . ?
C9 C10 C11 C7 -0.3(10) . . . . ?
C9 C10 C11 C12 -175.0(7) . . . . ?
C6 C7 C11 C10 0.6(10) . . . . ?
C2 C7 C11 C10 -175.3(6) . . . . ?
C6 C7 C11 C12 176.7(6) . . . . ?
C2 C7 C11 C12 0.8(8) . . . . ?
C10 C11 C12 N2 -3.0(13) . . . . ?
C7 C11 C12 N2 -178.3(7) . . . . ?
C10 C11 C12 C1 173.4(7) . . . . ?
C7 C11 C12 C1 -1.9(7) . . . . ?
N1 C1 C12 N2 3.7(9) . . . . ?
C2 C1 C12 N2 179.5(6) . . . . ?
N1 C1 C12 C11 -173.4(6) . . . . ?
C2 C1 C12 C11 2.4(7) . . . . ?
C18 C13 C14 C15 -2.6(11) . . . . ?
N1 C13 C14 C15 -179.3(7) . . . . ?
C13 C14 C15 C16 3.0(11) . . . . ?
C14 C15 C16 C17 -2.2(12) . . . . ?
C14 C15 C16 O1 174.6(7) . . . . ?
C15 C16 C17 C18 0.9(12) . . . . ?
O1 C16 C17 C18 -175.8(7) . . . . ?
C16 C17 C18 C13 -0.4(11) . . . . ?
C14 C13 C18 C17 1.3(11) . . . . ?
N1 C13 C18 C17 178.0(6) . . . . ?
C25 C20 C21 C22 4.4(11) . . . . ?
N2 C20 C21 C22 -177.6(7) . . . . ?
C20 C21 C22 C23 -3.5(12) . . . . ?
C21 C22 C23 C24 1.2(13) . . . . ?
C21 C22 C23 O2 179.8(7) . . . . ?
C22 C23 C24 C25 0.2(12) . . . . ?
O2 C23 C24 C25 -178.2(8) . . . . ?
C21 C20 C25 C24 -3.0(11) . . . . ?
N2 C20 C25 C24 179.1(7) . . . . ?
C23 C24 C25 C20 0.7(12) . . . . ?
N3 C27 C28 C29 -2.5(14) . . . . ?
C38 C27 C28 C29 175.1(7) . . . . ?
N3 C27 C28 C33 -178.1(7) . . . . ?
C38 C27 C28 C33 -0.5(7) . . . . ?
C33 C28 C29 C30 -1.0(10) . . . . ?
C27 C28 C29 C30 -176.2(7) . . . . ?
C28 C29 C30 C31 -0.5(11) . . . . ?
C29 C30 C31 C32 1.2(11) . . . . ?
C30 C31 C32 C33 -0.3(10) . . . . ?
C30 C31 C32 C34 178.9(7) . . . . ?
C29 C28 C33 C32 1.9(10) . . . . ?
C27 C28 C33 C32 178.3(6) . . . . ?
C29 C28 C33 C37 -176.8(6) . . . . ?
C27 C28 C33 C37 -0.4(8) . . . . ?
C34 C32 C33 C28 179.5(6) . . . . ?
C31 C32 C33 C28 -1.2(10) . . . . ?
C34 C32 C33 C37 -1.9(10) . . . . ?
C31 C32 C33 C37 177.4(6) . . . . ?
C33 C32 C34 C35 1.0(10) . . . . ?
C31 C32 C34 C35 -178.3(7) . . . . ?
C32 C34 C35 C36 -0.1(12) . . . . ?
C34 C35 C36 C37 0.1(11) . . . . ?
C35 C36 C37 C33 -0.9(10) . . . . ?
C35 C36 C37 C38 178.4(7) . . . . ?
C28 C33 C37 C36 -179.4(6) . . . . ?
C32 C33 C37 C36 1.9(10) . . . . ?
C28 C33 C37 C38 1.1(8) . . . . ?
C32 C33 C37 C38 -177.6(6) . . . . ?
C36 C37 C38 N4 -4.6(14) . . . . ?
C33 C37 C38 N4 174.8(7) . . . . ?
C36 C37 C38 C27 179.2(8) . . . . ?
C33 C37 C38 C27 -1.4(7) . . . . ?
N3 C27 C38 N4 2.3(9) . . . . ?
C28 C27 C38 N4 -175.8(6) . . . . ?
N3 C27 C38 C37 179.3(6) . . . . ?
C28 C27 C38 C37 1.2(7) . . . . ?
C44 C39 C40 C41 3.1(11) . . . . ?
N3 C39 C40 C41 176.5(7) . . . . ?
C39 C40 C41 C42 -2.5(12) . . . . ?
C40 C41 C42 C43 0.5(12) . . . . ?
C40 C41 C42 O3 -172.7(7) . . . . ?
C41 C42 C43 C44 0.8(12) . . . . ?
O3 C42 C43 C44 174.0(7) . . . . ?
C42 C43 C44 C39 -0.3(11) . . . . ?
C40 C39 C44 C43 -1.7(11) . . . . ?
N3 C39 C44 C43 -175.1(6) . . . . ?
C51 C46 C47 C48 -4.3(11) . . . . ?
N4 C46 C47 C48 177.8(7) . . . . ?
C46 C47 C48 C49 1.6(11) . . . . ?
C47 C48 C49 C50 1.6(12) . . . . ?
C47 C48 C49 O4 -174.1(7) . . . . ?
C48 C49 C50 C51 -2.2(12) . . . . ?
O4 C49 C50 C51 173.9(7) . . . . ?
C49 C50 C51 C46 -0.5(11) . . . . ?
C47 C46 C51 C50 3.7(11) . . . . ?
N4 C46 C51 C50 -178.4(7) . . . . ?
C2 C1 N1 C13 6.0(12) . . . . ?
C12 C1 N1 C13 -179.8(6) . . . . ?
C2 C1 N1 Zn1 -173.4(6) . . . . ?
C12 C1 N1 Zn1 0.8(7) . . . . ?
C14 C13 N1 C1 -122.4(7) . . . . ?
C18 C13 N1 C1 60.8(9) . . . . ?
C14 C13 N1 Zn1 56.9(8) . . . . ?
C18 C13 N1 Zn1 -119.8(6) . . . . ?
C11 C12 N2 C20 -8.7(12) . . . . ?
C1 C12 N2 C20 175.3(6) . . . . ?
C11 C12 N2 Zn1 170.1(6) . . . . ?
C1 C12 N2 Zn1 -5.9(7) . . . . ?
C25 C20 N2 C12 -62.1(9) . . . . ?
C21 C20 N2 C12 120.0(7) . . . . ?
C25 C20 N2 Zn1 119.4(7) . . . . ?
C21 C20 N2 Zn1 -58.6(9) . . . . ?
C28 C27 N3 C39 -11.9(12) . . . . ?
C38 C27 N3 C39 170.7(6) . . . . ?
C28 C27 N3 Zn2 170.1(6) . . . . ?
C38 C27 N3 Zn2 -7.4(7) . . . . ?
C40 C39 N3 C27 133.0(7) . . . . ?
C44 C39 N3 C27 -53.5(10) . . . . ?
C40 C39 N3 Zn2 -49.2(9) . . . . ?
C44 C39 N3 Zn2 124.3(6) . . . . ?
C37 C38 N4 C46 5.7(12) . . . . ?
C27 C38 N4 C46 -178.5(5) . . . . ?
C37 C38 N4 Zn2 -171.7(7) . . . . ?
C27 C38 N4 Zn2 4.1(7) . . . . ?
C47 C46 N4 C38 -121.8(7) . . . . ?
C51 C46 N4 C38 60.3(9) . . . . ?
C47 C46 N4 Zn2 55.1(8) . . . . ?
C51 C46 N4 Zn2 -122.8(6) . . . . ?
F2 C19 O1 C16 58.2(12) . . . . ?
F3 C19 O1 C16 -178.0(7) . . . . ?
F1 C19 O1 C16 -61.7(10) . . . . ?
C17 C16 O1 C19 -69.3(11) . . . . ?
C15 C16 O1 C19 113.8(9) . . . . ?
F5 C26 O2 C23 177.3(10) . . . . ?
F6 C26 O2 C23 -54(2) . . . . ?
F4 C26 O2 C23 59.5(15) . . . . ?
C22 C23 O2 C26 -179.5(13) . . . . ?
C24 C23 O2 C26 -1.0(17) . . . . ?
F8 C45 O3 C42 -175.3(7) . . . . ?
F7 C45 O3 C42 -54.9(12) . . . . ?
F9 C45 O3 C42 65.5(10) . . . . ?
C41 C42 O3 C45 -104.0(9) . . . . ?
C43 C42 O3 C45 82.6(10) . . . . ?
F12 C52 O4 C49 53.9(17) . . . . ?
F10 C52 O4 C49 -169.4(8) . . . . ?
F11 C52 O4 C49 -57.5(11) . . . . ?
C48 C49 O4 C52 -44.8(13) . . . . ?
C50 C49 O4 C52 139.1(10) . . . . ?

_refine_diff_density_max         2.192
_refine_diff_density_min         -1.217
_refine_diff_density_rms         0.164

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1061249'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H28 Cl4 F12 N4 Zn2'
_chemical_formula_sum            'C52 H28 Cl4 F12 N4 Zn2'
_chemical_formula_weight         1209.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.9861(17)
_cell_length_b                   14.4270(17)
_cell_length_c                   16.0295(14)
_cell_angle_alpha                99.188(9)
_cell_angle_beta                 102.008(11)
_cell_angle_gamma                114.266(13)
_cell_volume                     2376.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1100
_cell_measurement_theta_min      3.5030
_cell_measurement_theta_max      64.8140

_exptl_crystal_description       chip
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    4.116
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.44297
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray source'
_diffrn_measurement_device_type  'Agilent SuperNova with AtlasS2 detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17656
_diffrn_reflns_av_unetI/netI     0.1825
_diffrn_reflns_av_R_equivalents  0.1294
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.931
_diffrn_reflns_theta_max         67.498
_diffrn_reflns_theta_full        67.498
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8564
_reflns_number_gt                4159
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_cell_refinement       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction        
'CrysAlisPro V 1.171.37.31, Agilent Technologies'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1008P)²+21.7325P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8564
_refine_ls_number_parameters     667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1975
_refine_ls_R_factor_gt           0.1127
_refine_ls_wR_factor_ref         0.3387
_refine_ls_wR_factor_gt          0.2856
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2452(12) 0.0557(10) 0.6055(9) 0.030(3) Uani 1 1 d . . . . .
C2 C -0.3405(13) 0.0944(11) 0.6082(8) 0.032(3) Uani 1 1 d . . . . .
C3 C -0.3513(17) 0.1833(13) 0.5966(10) 0.050(4) Uani 1 1 d . . . . .
H3 H -0.2844 0.2384 0.5869 0.060 Uiso 1 1 calc R U . . .
C4 C -0.4625(17) 0.1899(14) 0.5993(11) 0.058(5) Uani 1 1 d . . . . .
H4 H -0.4715 0.2478 0.5872 0.069 Uiso 1 1 calc R U . . .
C5 C -0.5596(15) 0.1144(12) 0.6191(11) 0.047(4) Uani 1 1 d . . . . .
H5 H -0.6299 0.1245 0.6243 0.057 Uiso 1 1 calc R U . . .
C6 C -0.5554(15) 0.0205(12) 0.6319(10) 0.044(4) Uani 1 1 d . . . . .
C7 C -0.4458(14) 0.0100(11) 0.6231(10) 0.039(3) Uani 1 1 d . . . . .
C8 C -0.6504(16) -0.0698(15) 0.6484(11) 0.058(5) Uani 1 1 d . . . . .
H8 H -0.7249 -0.0687 0.6557 0.070 Uiso 1 1 calc R U . . .
C9 C -0.6339(15) -0.1560(13) 0.6534(11) 0.049(4) Uani 1 1 d . . . . .
H9 H -0.6984 -0.2133 0.6627 0.058 Uiso 1 1 calc R U . . .
C10 C -0.5233(15) -0.1620(12) 0.6452(9) 0.044(4) Uani 1 1 d . . . . .
H10 H -0.5144 -0.2223 0.6492 0.053 Uiso 1 1 calc R U . . .
C11 C -0.4262(13) -0.0768(11) 0.6311(10) 0.036(3) Uani 1 1 d . . . . .
C12 C -0.3020(14) -0.0551(10) 0.6189(9) 0.034(3) Uani 1 1 d . . . . .
C13 C -0.0679(13) 0.2024(9) 0.5941(10) 0.033(3) Uani 1 1 d . . . . .
C14 C -0.0478(14) 0.2212(10) 0.5145(10) 0.036(3) Uani 1 1 d . . . . .
H14 H -0.0823 0.1653 0.4634 0.043 Uiso 1 1 calc R U . . .
C15 C 0.0230(15) 0.3226(12) 0.5119(11) 0.046(4) Uani 1 1 d . . . . .
H15 H 0.0381 0.3359 0.4594 0.055 Uiso 1 1 calc R U . . .
C16 C 0.0716(15) 0.4043(11) 0.5875(10) 0.041(3) Uani 1 1 d . . . . .
C17 C 0.0492(14) 0.3850(11) 0.6669(10) 0.042(4) Uani 1 1 d . . . . .
H17 H 0.0826 0.4408 0.7179 0.051 Uiso 1 1 calc R U . . .
C18 C -0.0208(15) 0.2851(10) 0.6691(10) 0.039(3) Uani 1 1 d . . . . .
H18 H -0.0374 0.2720 0.7214 0.047 Uiso 1 1 calc R U . . .
C19 C 0.1606(17) 0.5173(11) 0.5886(12) 0.049(4) Uani 1 1 d . . . . .
C20 C -0.2768(15) -0.2077(12) 0.6285(10) 0.044(4) Uani 1 1 d . . . . .
C21 C -0.3064(15) -0.2944(11) 0.5605(11) 0.047(4) Uani 1 1 d . . . . .
H21 H -0.3059 -0.2883 0.5037 0.056 Uiso 1 1 calc R U . . .
C22 C -0.3367(16) -0.3903(11) 0.5795(10) 0.047(4) Uani 1 1 d . . . . .
H22 H -0.3552 -0.4494 0.5353 0.057 Uiso 1 1 calc R U . . .
C23 C -0.3399(15) -0.3995(11) 0.6664(11) 0.044(4) Uani 1 1 d . . . . .
C24 C -0.3065(16) -0.3114(11) 0.7315(10) 0.046(4) Uani 1 1 d . . . . .
H24 H -0.3042 -0.3159 0.7890 0.055 Uiso 1 1 calc R U . . .
C25 C -0.2759(14) -0.2146(10) 0.7127(9) 0.037(3) Uani 1 1 d . . . . .
H25 H -0.2549 -0.1549 0.7572 0.044 Uiso 1 1 calc R U . . .
C26 C -0.3776(18) -0.5045(13) 0.6844(14) 0.060(5) Uani 1 1 d . . . . .
C27 C 0.3036(12) 0.0983(9) 0.8785(9) 0.028(3) Uani 1 1 d . . . . .
C28 C 0.4288(13) 0.1309(10) 0.8647(9) 0.031(3) Uani 1 1 d . . . . .
C29 C 0.5170(12) 0.2211(10) 0.8522(9) 0.033(3) Uani 1 1 d . . . . .
H29 H 0.5009 0.2788 0.8510 0.040 Uiso 1 1 calc R U . . .
C30 C 0.6332(14) 0.2245(11) 0.8411(10) 0.040(3) Uani 1 1 d . . . . .
H30 H 0.6897 0.2830 0.8278 0.049 Uiso 1 1 calc R U . . .
C31 C 0.6649(14) 0.1442(10) 0.8493(10) 0.038(3) Uani 1 1 d . . . . .
H31 H 0.7446 0.1517 0.8460 0.046 Uiso 1 1 calc R U . . .
C32 C 0.5773(13) 0.0504(11) 0.8627(9) 0.035(3) Uani 1 1 d . . . . .
C33 C 0.4611(13) 0.0471(9) 0.8700(9) 0.032(3) Uani 1 1 d . . . . .
C34 C 0.5951(14) -0.0365(11) 0.8740(9) 0.038(3) Uani 1 1 d . . . . .
H34 H 0.6717 -0.0370 0.8714 0.045 Uiso 1 1 calc R U . . .
C35 C 0.5021(15) -0.1224(12) 0.8891(10) 0.042(4) Uani 1 1 d . . . . .
H35 H 0.5181 -0.1788 0.8970 0.050 Uiso 1 1 calc R U . . .
C36 C 0.3842(15) -0.1267(11) 0.8929(10) 0.040(3) Uani 1 1 d . . . . .
H36 H 0.3229 -0.1855 0.9028 0.047 Uiso 1 1 calc R U . . .
C37 C 0.3596(13) -0.0437(9) 0.8817(8) 0.027(3) Uani 1 1 d . . . . .
C38 C 0.2561(14) -0.0152(10) 0.8843(9) 0.033(3) Uani 1 1 d . . . . .
C39 C 0.2651(13) 0.2471(10) 0.8838(10) 0.034(3) Uani 1 1 d . . . . .
C40 C 0.2783(15) 0.3202(11) 0.9567(10) 0.042(4) Uani 1 1 d . . . . .
H40 H 0.2624 0.2997 1.0069 0.051 Uiso 1 1 calc R U . . .
C41 C 0.3151(15) 0.4237(10) 0.9554(10) 0.041(3) Uani 1 1 d . . . . .
H41 H 0.3306 0.4742 1.0062 0.049 Uiso 1 1 calc R U . . .
C42 C 0.3290(15) 0.4525(10) 0.8789(10) 0.043(4) Uani 1 1 d . . . . .
C43 C 0.3087(15) 0.3784(10) 0.8037(10) 0.041(3) Uani 1 1 d . . . . .
H43 H 0.3184 0.3981 0.7522 0.049 Uiso 1 1 calc R U . . .
C44 C 0.2732(14) 0.2728(10) 0.8052(9) 0.037(3) Uani 1 1 d . . . . .
H44 H 0.2555 0.2215 0.7543 0.045 Uiso 1 1 calc R U . . .
C45 C 0.3699(17) 0.5634(12) 0.8762(12) 0.053(4) Uani 1 1 d . . . . .
C46 C 0.0912(13) -0.1764(9) 0.8841(10) 0.033(3) Uani 1 1 d . . . . .
C47 C 0.0785(13) -0.2089(9) 0.9594(9) 0.030(3) Uani 1 1 d . . . . .
H47 H 0.1032 -0.1600 1.0135 0.037 Uiso 1 1 calc R U . . .
C48 C 0.0277(14) -0.3170(11) 0.9525(9) 0.038(3) Uani 1 1 d . . . . .
H48 H 0.0170 -0.3412 1.0021 0.046 Uiso 1 1 calc R U . . .
C49 C -0.0069(15) -0.3882(11) 0.8706(10) 0.039(3) Uani 1 1 d . . . . .
C50 C 0.0035(15) -0.3543(11) 0.7971(10) 0.042(3) Uani 1 1 d . . . . .
H50 H -0.0244 -0.4029 0.7422 0.050 Uiso 1 1 calc R U . . .
C51 C 0.0562(14) -0.2463(10) 0.8043(10) 0.039(3) Uani 1 1 d . . . . .
H51 H 0.0674 -0.2222 0.7547 0.047 Uiso 1 1 calc R U . . .
C52 C -0.0572(17) -0.5051(12) 0.8647(11) 0.051(4) Uani 1 1 d . . . . .
Cl1 Cl -0.1355(3) -0.1139(3) 0.4408(2) 0.0368(8) Uani 1 1 d . . . . .
Cl2 Cl 0.0590(4) -0.0593(3) 0.6876(2) 0.0405(8) Uani 1 1 d . . . . .
Cl3 Cl -0.0721(3) 0.0850(3) 0.8228(2) 0.0340(7) Uani 1 1 d . . . . .
Cl4 Cl 0.1316(3) 0.1111(2) 1.0619(2) 0.0334(7) Uani 1 1 d . . . . .
F1 F 0.2854(10) 0.5442(8) 0.6224(8) 0.073(3) Uani 1 1 d . . . . .
F2 F 0.1383(11) 0.5888(7) 0.6371(7) 0.067(3) Uani 1 1 d . . . . .
F3 F 0.1459(10) 0.5312(7) 0.5067(7) 0.059(3) Uani 1 1 d . . . . .
F4 F -0.3456(11) -0.4998(7) 0.7685(7) 0.065(3) Uani 1 1 d . . . . .
F5 F -0.3211(11) -0.5571(7) 0.6441(8) 0.069(3) Uani 1 1 d . . . . .
F6 F -0.5024(10) -0.5704(7) 0.6480(7) 0.064(3) Uani 1 1 d . . . . .
F7 F 0.2838(10) 0.5822(7) 0.8278(8) 0.079(4) Uani 1 1 d . . . . .
F8 F 0.4721(12) 0.6008(8) 0.8437(9) 0.089(4) Uani 1 1 d . . . . .
F9 F 0.4127(12) 0.6323(7) 0.9558(7) 0.076(4) Uani 1 1 d . . . . .
F10 F -0.1291(10) -0.5664(6) 0.7823(6) 0.055(2) Uani 1 1 d . . . . .
F11 F -0.1243(11) -0.5331(7) 0.9221(7) 0.063(3) Uani 1 1 d . . . . .
F12 F 0.0412(10) -0.5308(7) 0.8881(7) 0.064(3) Uani 1 1 d . . . . .
N1 N -0.1355(11) 0.0929(8) 0.5973(8) 0.035(3) Uani 1 1 d . . . . .
N2 N -0.2366(12) -0.1041(9) 0.6126(8) 0.037(3) Uani 1 1 d . . . . .
N3 N 0.2319(11) 0.1414(8) 0.8902(7) 0.030(2) Uani 1 1 d . . . . .
N4 N 0.1419(10) -0.0649(8) 0.8891(7) 0.028(2) Uani 1 1 d . . . . .
Zn1 Zn -0.05627(18) -0.01425(14) 0.58895(12) 0.0341(5) Uani 1 1 d . . . . .
Zn2 Zn 0.05080(18) 0.03168(14) 0.90809(12) 0.0326(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.245(16) . ?
C1 C2 1.468(18) . ?
C1 C12 1.529(17) . ?
C2 C3 1.378(19) . ?
C2 C7 1.445(19) . ?
C3 C4 1.38(2) . ?
C4 C5 1.37(2) . ?
C5 C6 1.42(2) . ?
C6 C7 1.42(2) . ?
C6 C8 1.44(2) . ?
C7 C11 1.385(19) . ?
C8 C9 1.35(2) . ?
C9 C10 1.40(2) . ?
C10 C11 1.39(2) . ?
C11 C12 1.453(19) . ?
C12 N2 1.261(17) . ?
C13 C18 1.377(19) . ?
C13 C14 1.395(18) . ?
C13 N1 1.465(15) . ?
C14 C15 1.368(18) . ?
C15 C16 1.37(2) . ?
C16 C17 1.40(2) . ?
C16 C19 1.53(2) . ?
C17 C18 1.348(19) . ?
C19 F1 1.342(19) . ?
C19 F2 1.340(18) . ?
C19 F3 1.345(19) . ?
C20 C25 1.368(19) . ?
C20 C21 1.38(2) . ?
C20 N2 1.452(17) . ?
C21 C22 1.381(19) . ?
C22 C23 1.43(2) . ?
C23 C24 1.36(2) . ?
C23 C26 1.49(2) . ?
C24 C25 1.391(18) . ?
C26 F4 1.31(2) . ?
C26 F6 1.33(2) . ?
C26 F5 1.38(2) . ?
C27 N3 1.278(16) . ?
C27 C28 1.453(18) . ?
C27 C38 1.523(17) . ?
C28 C29 1.376(17) . ?
C28 C33 1.422(18) . ?
C29 C30 1.423(19) . ?
C30 C31 1.376(19) . ?
C31 C32 1.414(19) . ?
C32 C34 1.388(19) . ?
C32 C33 1.403(19) . ?
C33 C37 1.448(17) . ?
C34 C35 1.38(2) . ?
C35 C36 1.40(2) . ?
C36 C37 1.375(17) . ?
C37 C38 1.464(18) . ?
C38 N4 1.283(17) . ?
C39 C44 1.380(18) . ?
C39 C40 1.376(19) . ?
C39 N3 1.437(15) . ?
C40 C41 1.377(18) . ?
C41 C42 1.38(2) . ?
C42 C43 1.38(2) . ?
C42 C45 1.480(18) . ?
C43 C44 1.409(18) . ?
C45 F7 1.30(2) . ?
C45 F9 1.335(19) . ?
C45 F8 1.37(2) . ?
C46 C47 1.378(18) . ?
C46 C51 1.36(2) . ?
C46 N4 1.448(15) . ?
C47 C48 1.397(17) . ?
C48 C49 1.39(2) . ?
C49 C50 1.355(18) . ?
C49 C52 1.519(19) . ?
C50 C51 1.394(18) . ?
C52 F10 1.340(19) . ?
C52 F11 1.347(17) . ?
C52 F12 1.37(2) . ?
Cl1 Zn1 2.337(4) . ?
Cl1 Zn1 2.484(4) 2_556 ?
Cl2 Zn1 2.234(4) . ?
Cl3 Zn2 2.249(4) . ?
Cl4 Zn2 2.350(4) . ?
Cl4 Zn2 2.512(4) 2_557 ?
N1 Zn1 2.121(11) . ?
N2 Zn1 2.166(12) . ?
N3 Zn2 2.209(10) . ?
N4 Zn2 2.117(10) . ?
Zn1 Cl1 2.484(4) 2_556 ?
Zn2 Cl4 2.512(4) 2_557 ?

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
N1 C1 C2 135.1(12) . . ?
N1 C1 C12 118.1(12) . . ?
C2 C1 C12 106.8(11) . . ?
C3 C2 C7 119.2(14) . . ?
C3 C2 C1 135.8(14) . . ?
C7 C2 C1 104.9(11) . . ?
C2 C3 C4 119.4(16) . . ?
C5 C4 C3 122.4(16) . . ?
C4 C5 C6 121.3(14) . . ?
C7 C6 C5 116.5(15) . . ?
C7 C6 C8 114.0(14) . . ?
C5 C6 C8 129.4(14) . . ?
C11 C7 C6 124.8(13) . . ?
C11 C7 C2 114.2(13) . . ?
C6 C7 C2 120.9(14) . . ?
C9 C8 C6 121.6(15) . . ?
C8 C9 C10 122.2(15) . . ?
C11 C10 C9 119.4(15) . . ?
C10 C11 C7 118.0(13) . . ?
C10 C11 C12 134.9(13) . . ?
C7 C11 C12 107.1(12) . . ?
N2 C12 C11 137.1(13) . . ?
N2 C12 C1 115.9(12) . . ?
C11 C12 C1 106.9(11) . . ?
C18 C13 C14 120.5(12) . . ?
C18 C13 N1 120.6(12) . . ?
C14 C13 N1 118.8(12) . . ?
C15 C14 C13 119.6(14) . . ?
C14 C15 C16 119.5(14) . . ?
C17 C16 C15 120.7(14) . . ?
C17 C16 C19 118.6(14) . . ?
C15 C16 C19 120.6(14) . . ?
C18 C17 C16 119.7(14) . . ?
C17 C18 C13 120.0(14) . . ?
F1 C19 F2 106.7(14) . . ?
F1 C19 F3 106.1(14) . . ?
F2 C19 F3 106.8(12) . . ?
F1 C19 C16 112.9(12) . . ?
F2 C19 C16 111.7(13) . . ?
F3 C19 C16 112.2(13) . . ?
C25 C20 C21 122.0(14) . . ?
C25 C20 N2 118.1(14) . . ?
C21 C20 N2 119.8(14) . . ?
C22 C21 C20 118.1(15) . . ?
C21 C22 C23 120.6(14) . . ?
C24 C23 C22 119.1(13) . . ?
C24 C23 C26 121.3(15) . . ?
C22 C23 C26 119.6(15) . . ?
C23 C24 C25 120.4(14) . . ?
C20 C25 C24 119.7(14) . . ?
F4 C26 F6 108.6(15) . . ?
F4 C26 F5 107.1(14) . . ?
F6 C26 F5 102.7(15) . . ?
F4 C26 C23 114.1(16) . . ?
F6 C26 C23 113.1(15) . . ?
F5 C26 C23 110.4(14) . . ?
N3 C27 C28 136.5(11) . . ?
N3 C27 C38 116.4(11) . . ?
C28 C27 C38 107.0(11) . . ?
C29 C28 C33 118.1(12) . . ?
C29 C28 C27 134.8(12) . . ?
C33 C28 C27 107.1(11) . . ?
C28 C29 C30 118.7(12) . . ?
C31 C30 C29 122.4(12) . . ?
C30 C31 C32 120.5(13) . . ?
C34 C32 C33 116.1(13) . . ?
C34 C32 C31 127.7(13) . . ?
C33 C32 C31 116.1(12) . . ?
C32 C33 C28 124.1(12) . . ?
C32 C33 C37 123.3(12) . . ?
C28 C33 C37 112.6(12) . . ?
C35 C34 C32 121.7(13) . . ?
C34 C35 C36 121.7(13) . . ?
C37 C36 C35 119.8(13) . . ?
C36 C37 C33 117.2(12) . . ?
C36 C37 C38 136.9(13) . . ?
C33 C37 C38 105.7(11) . . ?
N4 C38 C37 133.9(12) . . ?
N4 C38 C27 118.7(11) . . ?
C37 C38 C27 107.4(12) . . ?
C44 C39 C40 120.8(12) . . ?
C44 C39 N3 121.3(12) . . ?
C40 C39 N3 117.7(12) . . ?
C41 C40 C39 120.1(14) . . ?
C40 C41 C42 120.0(14) . . ?
C41 C42 C43 120.3(12) . . ?
C41 C42 C45 121.0(14) . . ?
C43 C42 C45 118.6(14) . . ?
C42 C43 C44 119.8(14) . . ?
C39 C44 C43 118.6(13) . . ?
F7 C45 F9 105.3(14) . . ?
F7 C45 F8 104.5(14) . . ?
F9 C45 F8 103.0(14) . . ?
F7 C45 C42 116.3(15) . . ?
F9 C45 C42 114.0(14) . . ?
F8 C45 C42 112.4(14) . . ?
C47 C46 C51 121.8(11) . . ?
C47 C46 N4 119.6(12) . . ?
C51 C46 N4 118.6(12) . . ?
C46 C47 C48 118.5(12) . . ?
C49 C48 C47 119.4(12) . . ?
C50 C49 C48 120.9(13) . . ?
C50 C49 C52 120.2(14) . . ?
C48 C49 C52 118.9(12) . . ?
C49 C50 C51 119.6(14) . . ?
C46 C51 C50 119.8(13) . . ?
F10 C52 F11 109.8(13) . . ?
F10 C52 F12 106.5(13) . . ?
F11 C52 F12 104.6(13) . . ?
F10 C52 C49 112.1(13) . . ?
F11 C52 C49 111.9(13) . . ?
F12 C52 C49 111.6(14) . . ?
Zn1 Cl1 Zn1 90.04(13) . 2_556 ?
Zn2 Cl4 Zn2 92.94(13) . 2_557 ?
C1 N1 C13 121.8(11) . . ?
C1 N1 Zn1 114.8(9) . . ?
C13 N1 Zn1 123.4(8) . . ?
C12 N2 C20 121.2(12) . . ?
C12 N2 Zn1 114.0(9) . . ?
C20 N2 Zn1 124.6(9) . . ?
C27 N3 C39 121.4(11) . . ?
C27 N3 Zn2 112.6(8) . . ?
C39 N3 Zn2 125.8(9) . . ?
C38 N4 C46 118.7(11) . . ?
C38 N4 Zn2 113.9(8) . . ?
C46 N4 Zn2 127.3(8) . . ?
N1 Zn1 N2 77.0(4) . . ?
N1 Zn1 Cl2 134.8(3) . . ?
N2 Zn1 Cl2 94.9(3) . . ?
N1 Zn1 Cl1 106.7(3) . . ?
N2 Zn1 Cl1 91.9(3) . . ?
Cl2 Zn1 Cl1 118.11(14) . . ?
N1 Zn1 Cl1 92.3(3) . 2_556 ?
N2 Zn1 Cl1 169.2(3) . 2_556 ?
Cl2 Zn1 Cl1 93.60(14) . 2_556 ?
Cl1 Zn1 Cl1 89.96(13) . 2_556 ?
N4 Zn2 N3 77.7(4) . . ?
N4 Zn2 Cl3 137.4(3) . . ?
N3 Zn2 Cl3 94.7(3) . . ?
N4 Zn2 Cl4 103.3(3) . . ?
N3 Zn2 Cl4 90.8(3) . . ?
Cl3 Zn2 Cl4 118.84(13) . . ?
N4 Zn2 Cl4 92.5(3) . 2_557 ?
N3 Zn2 Cl4 169.2(3) . 2_557 ?
Cl3 Zn2 Cl4 95.68(13) . 2_557 ?
Cl4 Zn2 Cl4 87.06(13) . 2_557 ?

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
N1 C1 C2 C3 6(3) . . . . ?
C12 C1 C2 C3 -176.1(16) . . . . ?
N1 C1 C2 C7 -177.7(16) . . . . ?
C12 C1 C2 C7 0.4(14) . . . . ?
C7 C2 C3 C4 0(2) . . . . ?
C1 C2 C3 C4 176.1(16) . . . . ?
C2 C3 C4 C5 4(3) . . . . ?
C3 C4 C5 C6 -5(3) . . . . ?
C4 C5 C6 C7 0(2) . . . . ?
C4 C5 C6 C8 -176.3(16) . . . . ?
C5 C6 C7 C11 -178.4(14) . . . . ?
C8 C6 C7 C11 -1(2) . . . . ?
C5 C6 C7 C2 4(2) . . . . ?
C8 C6 C7 C2 -178.7(13) . . . . ?
C3 C2 C7 C11 178.0(13) . . . . ?
C1 C2 C7 C11 0.8(17) . . . . ?
C3 C2 C7 C6 -4(2) . . . . ?
C1 C2 C7 C6 178.4(13) . . . . ?
C7 C6 C8 C9 -1(2) . . . . ?
C5 C6 C8 C9 175.7(16) . . . . ?
C6 C8 C9 C10 2(3) . . . . ?
C8 C9 C10 C11 0(2) . . . . ?
C9 C10 C11 C7 -2(2) . . . . ?
C9 C10 C11 C12 -179.3(16) . . . . ?
C6 C7 C11 C10 3(2) . . . . ?
C2 C7 C11 C10 -179.8(13) . . . . ?
C6 C7 C11 C12 -179.1(14) . . . . ?
C2 C7 C11 C12 -1.7(17) . . . . ?
C10 C11 C12 N2 4(3) . . . . ?
C7 C11 C12 N2 -174.1(17) . . . . ?
C10 C11 C12 C1 179.4(16) . . . . ?
C7 C11 C12 C1 1.8(15) . . . . ?
N1 C1 C12 N2 -6(2) . . . . ?
C2 C1 C12 N2 175.5(12) . . . . ?
N1 C1 C12 C11 177.1(13) . . . . ?
C2 C1 C12 C11 -1.4(15) . . . . ?
C18 C13 C14 C15 2(2) . . . . ?
N1 C13 C14 C15 -175.4(12) . . . . ?
C13 C14 C15 C16 -1(2) . . . . ?
C14 C15 C16 C17 0(2) . . . . ?
C14 C15 C16 C19 174.8(14) . . . . ?
C15 C16 C17 C18 0(2) . . . . ?
C19 C16 C17 C18 -175.1(14) . . . . ?
C16 C17 C18 C13 1(2) . . . . ?
C14 C13 C18 C17 -2(2) . . . . ?
N1 C13 C18 C17 175.2(13) . . . . ?
C17 C16 C19 F1 77.7(18) . . . . ?
C15 C16 C19 F1 -97.3(18) . . . . ?
C17 C16 C19 F2 -43(2) . . . . ?
C15 C16 C19 F2 142.4(15) . . . . ?
C17 C16 C19 F3 -162.5(13) . . . . ?
C15 C16 C19 F3 22(2) . . . . ?
C25 C20 C21 C22 0(2) . . . . ?
N2 C20 C21 C22 176.2(14) . . . . ?
C20 C21 C22 C23 1(3) . . . . ?
C21 C22 C23 C24 -3(3) . . . . ?
C21 C22 C23 C26 177.7(16) . . . . ?
C22 C23 C24 C25 3(3) . . . . ?
C26 C23 C24 C25 -177.7(15) . . . . ?
C21 C20 C25 C24 -1(2) . . . . ?
N2 C20 C25 C24 -176.3(14) . . . . ?
C23 C24 C25 C20 -1(2) . . . . ?
C24 C23 C26 F4 -16(2) . . . . ?
C22 C23 C26 F4 163.0(16) . . . . ?
C24 C23 C26 F6 109(2) . . . . ?
C22 C23 C26 F6 -72(2) . . . . ?
C24 C23 C26 F5 -136.8(17) . . . . ?
C22 C23 C26 F5 42(2) . . . . ?
N3 C27 C28 C29 -6(3) . . . . ?
C38 C27 C28 C29 177.9(16) . . . . ?
N3 C27 C28 C33 171.2(16) . . . . ?
C38 C27 C28 C33 -4.9(15) . . . . ?
C33 C28 C29 C30 3(2) . . . . ?
C27 C28 C29 C30 179.7(15) . . . . ?
C28 C29 C30 C31 -5(2) . . . . ?
C29 C30 C31 C32 5(2) . . . . ?
C30 C31 C32 C34 -178.6(15) . . . . ?
C30 C31 C32 C33 -2(2) . . . . ?
C34 C32 C33 C28 176.8(13) . . . . ?
C31 C32 C33 C28 0(2) . . . . ?
C34 C32 C33 C37 -5(2) . . . . ?
C31 C32 C33 C37 178.5(13) . . . . ?
C29 C28 C33 C32 0(2) . . . . ?
C27 C28 C33 C32 -177.9(13) . . . . ?
C29 C28 C33 C37 -179.0(12) . . . . ?
C27 C28 C33 C37 3.3(16) . . . . ?
C33 C32 C34 C35 2(2) . . . . ?
C31 C32 C34 C35 178.2(15) . . . . ?
C32 C34 C35 C36 1(2) . . . . ?
C34 C35 C36 C37 0(2) . . . . ?
C35 C36 C37 C33 -2(2) . . . . ?
C35 C36 C37 C38 -176.9(15) . . . . ?
C32 C33 C37 C36 5(2) . . . . ?
C28 C33 C37 C36 -176.2(13) . . . . ?
C32 C33 C37 C38 -178.9(13) . . . . ?
C28 C33 C37 C38 -0.1(15) . . . . ?
C36 C37 C38 N4 -9(3) . . . . ?
C33 C37 C38 N4 176.1(15) . . . . ?
C36 C37 C38 C27 172.0(16) . . . . ?
C33 C37 C38 C27 -2.9(14) . . . . ?
N3 C27 C38 N4 8.7(19) . . . . ?
C28 C27 C38 N4 -174.2(12) . . . . ?
N3 C27 C38 C37 -172.1(12) . . . . ?
C28 C27 C38 C37 4.9(15) . . . . ?
C44 C39 C40 C41 -8(2) . . . . ?
N3 C39 C40 C41 177.4(13) . . . . ?
C39 C40 C41 C42 5(2) . . . . ?
C40 C41 C42 C43 -1(3) . . . . ?
C40 C41 C42 C45 -179.3(15) . . . . ?
C41 C42 C43 C44 0(2) . . . . ?
C45 C42 C43 C44 178.2(15) . . . . ?
C40 C39 C44 C43 7(2) . . . . ?
N3 C39 C44 C43 -178.8(13) . . . . ?
C42 C43 C44 C39 -3(2) . . . . ?
C41 C42 C45 F7 -111.6(19) . . . . ?
C43 C42 C45 F7 70(2) . . . . ?
C41 C42 C45 F9 11(2) . . . . ?
C43 C42 C45 F9 -166.7(16) . . . . ?
C41 C42 C45 F8 128.0(17) . . . . ?
C43 C42 C45 F8 -50(2) . . . . ?
C51 C46 C47 C48 0(2) . . . . ?
N4 C46 C47 C48 179.1(12) . . . . ?
C46 C47 C48 C49 1(2) . . . . ?
C47 C48 C49 C50 -3(2) . . . . ?
C47 C48 C49 C52 177.7(14) . . . . ?
C48 C49 C50 C51 4(2) . . . . ?
C52 C49 C50 C51 -176.6(14) . . . . ?
C47 C46 C51 C50 1(2) . . . . ?
N4 C46 C51 C50 -178.1(13) . . . . ?
C49 C50 C51 C46 -3(2) . . . . ?
C50 C49 C52 F10 -23(2) . . . . ?
C48 C49 C52 F10 156.8(14) . . . . ?
C50 C49 C52 F11 -146.7(15) . . . . ?
C48 C49 C52 F11 33(2) . . . . ?
C50 C49 C52 F12 96.5(18) . . . . ?
C48 C49 C52 F12 -83.8(17) . . . . ?
C2 C1 N1 C13 5(3) . . . . ?
C12 C1 N1 C13 -173.1(12) . . . . ?
C2 C1 N1 Zn1 -175.4(13) . . . . ?
C12 C1 N1 Zn1 6.7(16) . . . . ?
C18 C13 N1 C1 71.5(19) . . . . ?
C14 C13 N1 C1 -110.8(16) . . . . ?
C18 C13 N1 Zn1 -108.3(13) . . . . ?
C14 C13 N1 Zn1 69.4(15) . . . . ?
C11 C12 N2 C20 -8(3) . . . . ?
C1 C12 N2 C20 176.8(12) . . . . ?
C11 C12 N2 Zn1 177.6(15) . . . . ?
C1 C12 N2 Zn1 2.1(16) . . . . ?
C25 C20 N2 C12 -66.9(19) . . . . ?
C21 C20 N2 C12 117.2(17) . . . . ?
C25 C20 N2 Zn1 107.2(14) . . . . ?
C21 C20 N2 Zn1 -68.6(18) . . . . ?
C28 C27 N3 C39 6(2) . . . . ?
C38 C27 N3 C39 -178.3(12) . . . . ?
C28 C27 N3 Zn2 -179.3(14) . . . . ?
C38 C27 N3 Zn2 -3.4(15) . . . . ?
C44 C39 N3 C27 63.4(19) . . . . ?
C40 C39 N3 C27 -121.8(15) . . . . ?
C44 C39 N3 Zn2 -110.8(13) . . . . ?
C40 C39 N3 Zn2 64.0(17) . . . . ?
C37 C38 N4 C46 -6(2) . . . . ?
C27 C38 N4 C46 172.8(11) . . . . ?
C37 C38 N4 Zn2 172.0(13) . . . . ?
C27 C38 N4 Zn2 -9.1(16) . . . . ?
C47 C46 N4 C38 107.2(15) . . . . ?
C51 C46 N4 C38 -73.5(18) . . . . ?
C47 C46 N4 Zn2 -70.6(16) . . . . ?
C51 C46 N4 Zn2 108.8(13) . . . . ?

_refine_diff_density_max         0.851
_refine_diff_density_min         -1.056
_refine_diff_density_rms         0.147

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1061250'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H16 Cl4 F6 N2 Zn'
_chemical_formula_sum            'C27 H16 Cl4 F6 N2 Zn'
_chemical_formula_weight         689.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.7395(5)
_cell_length_b                   11.9489(3)
_cell_length_c                   17.6137(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.023(4)
_cell_angle_gamma                90
_cell_volume                     2699.19(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4837
_cell_measurement_theta_min      4.5650
_cell_measurement_theta_max      75.7620

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    5.486
_shelx_estimated_absorpt_T_min   0.207
_shelx_estimated_absorpt_T_max   0.668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray source'
_diffrn_measurement_device_type  'Agilent SuperNova with AtlasS2 detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10491
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.575
_diffrn_reflns_theta_max         76.256
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5421
_reflns_number_gt                4837
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_cell_refinement       
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction        
'CrysAlisPro V 1.171.37.31, Agilent Technologies'

_computing_structure_solution    
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'

_refine_special_details          
;
 ?
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0706P)²+2.1343P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5421
_refine_ls_number_parameters     390
_refine_ls_number_restraints     366
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.965
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.55217(17) 0.23489(18) 0.53834(13) 0.0177(4) Uani 1 1 d . U . . .
C2 C 0.53386(17) 0.14960(18) 0.59181(13) 0.0181(4) Uani 1 1 d . U . . .
C3 C 0.58932(18) 0.11113(19) 0.66920(14) 0.0202(4) Uani 1 1 d . U . . .
H3 H 0.6538 0.1445 0.7011 0.024 Uiso 1 1 calc R U . . .
C4 C 0.54775(19) 0.02053(19) 0.69998(14) 0.0219(5) Uani 1 1 d . U . . .
H4 H 0.5854 -0.0065 0.7532 0.026 Uiso 1 1 calc R U . . .
C5 C 0.45451(19) -0.02946(18) 0.65509(14) 0.0204(4) Uani 1 1 d . U . . .
H5 H 0.4288 -0.0895 0.6779 0.025 Uiso 1 1 calc R U . . .
C6 C 0.39642(17) 0.0080(2) 0.57498(14) 0.0192(4) Uani 1 1 d . U . . .
C7 C 0.43823(17) 0.09763(18) 0.54534(13) 0.0178(4) Uani 1 1 d . U . . .
C8 C 0.30115(18) -0.03764(19) 0.52124(15) 0.0217(4) Uani 1 1 d . U . . .
H8 H 0.2693 -0.0982 0.5385 0.026 Uiso 1 1 calc R U . . .
C9 C 0.25478(18) 0.0059(2) 0.44404(15) 0.0226(5) Uani 1 1 d . U . . .
H9 H 0.1913 -0.0262 0.4090 0.027 Uiso 1 1 calc R U . . .
C10 C 0.29802(18) 0.0961(2) 0.41519(14) 0.0216(4) Uani 1 1 d . U . . .
H10 H 0.2645 0.1242 0.3617 0.026 Uiso 1 1 calc R U . . .
C11 C 0.38982(17) 0.14239(19) 0.46624(13) 0.0181(4) Uani 1 1 d . U . . .
C12 C 0.46018(16) 0.23064(18) 0.45818(13) 0.0172(4) Uani 1 1 d . U . . .
C13 C 0.71246(18) 0.31707(19) 0.61803(14) 0.0203(4) Uani 1 1 d . U . . .
C14 C 0.81155(19) 0.2907(2) 0.62040(15) 0.0268(5) Uani 1 1 d . U . . .
H14 H 0.8218 0.2637 0.5731 0.032 Uiso 1 1 calc R U . . .
C15 C 0.8961(2) 0.3040(3) 0.69283(17) 0.0329(6) Uani 1 1 d . U . . .
H15 H 0.9643 0.2847 0.6955 0.039 Uiso 1 1 calc R U . . .
C16 C 0.88039(19) 0.3454(2) 0.76101(15) 0.0268(5) Uani 1 1 d . U . . .
C17 C 0.78131(19) 0.3753(2) 0.75760(14) 0.0240(5) Uani 1 1 d . U . . .
H17 H 0.7715 0.4054 0.8043 0.029 Uiso 1 1 calc R U . . .
C18 C 0.69652(18) 0.3610(2) 0.68582(14) 0.0219(4) Uani 1 1 d . U . . .
H18 H 0.6284 0.3810 0.6830 0.026 Uiso 1 1 calc R U . . .
C19 C 0.9708(2) 0.3631(3) 0.83853(17) 0.0370(6) Uani 1 1 d . U . . .
C20 C 0.37678(17) 0.30081(18) 0.32507(13) 0.0193(4) Uani 1 1 d . U . . .
C21 C 0.39621(19) 0.2748(2) 0.25460(14) 0.0227(5) Uani 1 1 d . U . . .
H21 H 0.4645 0.2552 0.2577 0.027 Uiso 1 1 calc R U . . .
C22 C 0.3149(2) 0.2780(2) 0.17979(14) 0.0256(5) Uani 1 1 d . U . . .
H22 H 0.3268 0.2581 0.1316 0.031 Uiso 1 1 calc R U . . .
C23 C 0.2165(2) 0.3103(2) 0.17586(15) 0.0271(5) Uani 1 1 d . U . . .
C24 C 0.19763(19) 0.3400(2) 0.24617(15) 0.0260(5) Uani 1 1 d . U . . .
H24 H 0.1301 0.3633 0.2426 0.031 Uiso 1 1 calc R U . . .
C25 C 0.27833(18) 0.3351(2) 0.32106(14) 0.0224(5) Uani 1 1 d . U . . .
H25 H 0.2664 0.3549 0.3692 0.027 Uiso 1 1 calc R U . . .
C26 C 0.1299(2) 0.3172(2) 0.09364(16) 0.0340(6) Uani 1 1 d . U . . .
Cl1 Cl 0.59357(5) 0.56824(5) 0.43218(4) 0.02864(15) Uani 1 1 d . U . . .
Cl2 Cl 0.70180(4) 0.30371(5) 0.37535(3) 0.02496(14) Uani 1 1 d . U . . .
F1 F 1.00057(14) 0.47156(17) 0.84890(12) 0.0486(5) Uani 1 1 d . U . . .
F2 F 1.05547(13) 0.30536(18) 0.84107(12) 0.0491(5) Uani 1 1 d . U . . .
F3 F 0.94882(15) 0.3349(2) 0.90386(10) 0.0570(6) Uani 1 1 d . U . . .
F4 F 0.1486(2) 0.2545(2) 0.03871(13) 0.0800(9) Uani 1 1 d . U . . .
F5 F 0.11870(14) 0.42086(17) 0.06366(10) 0.0446(4) Uani 1 1 d . U . . .
F6 F 0.03749(16) 0.2904(2) 0.09657(12) 0.0711(8) Uani 1 1 d . U . . .
N1 N 0.62601(15) 0.30339(16) 0.54383(11) 0.0179(4) Uani 1 1 d . U . . .
N2 N 0.46131(14) 0.29620(16) 0.40110(11) 0.0182(4) Uani 1 1 d . U . . .
Zn1 Zn 0.60226(2) 0.38500(2) 0.43402(2) 0.01825(11) Uani 1 1 d . U . . .
C27 C 1.0771(8) 0.5327(10) 0.6166(5) 0.056(2) Uani 0.72 1 d . U P A 1
H27C H 1.0982 0.4722 0.5873 0.067 Uiso 0.72 1 calc R U P A 1
H27D H 1.1016 0.6047 0.6021 0.067 Uiso 0.72 1 calc R U P A 1
Cl3 Cl 0.9384(3) 0.5351(2) 0.58563(16) 0.0610(6) Uani 0.72 1 d . U P A 1
Cl4 Cl 1.1355(3) 0.5107(3) 0.72191(17) 0.0723(10) Uani 0.72 1 d . U P A 1
C27' C 1.086(2) 0.558(3) 0.623(2) 0.099(14) Uani 0.28 1 d . U P A -1
H27E H 1.0958 0.6381 0.6382 0.119 Uiso 0.28 1 calc R U P A -1
H27F H 1.1167 0.5449 0.5803 0.119 Uiso 0.28 1 calc R U P A -1
Cl4' Cl 1.1465(7) 0.4773(9) 0.7044(6) 0.095(3) Uani 0.28 1 d . U P A -1
Cl3' Cl 0.9549(8) 0.5263(11) 0.5845(9) 0.139(6) Uani 0.28 1 d . U P A -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
C1 N1 1.280(3) . ?
C1 C2 1.469(3) . ?
C1 C12 1.521(3) . ?
C2 C3 1.380(3) . ?
C2 C7 1.418(3) . ?
C3 C4 1.419(3) . ?
C4 C5 1.377(3) . ?
C5 C6 1.421(3) . ?
C6 C7 1.402(3) . ?
C6 C8 1.420(3) . ?
C7 C11 1.416(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.411(3) . ?
C10 C11 1.375(3) . ?
C11 C12 1.471(3) . ?
C12 N2 1.279(3) . ?
C13 C14 1.384(3) . ?
C13 C18 1.392(3) . ?
C13 N1 1.425(3) . ?
C14 C15 1.393(3) . ?
C15 C16 1.386(4) . ?
C16 C17 1.387(4) . ?
C16 C19 1.495(3) . ?
C17 C18 1.389(3) . ?
C19 F3 1.333(4) . ?
C19 F2 1.339(4) . ?
C19 F1 1.352(4) . ?
C20 C25 1.391(3) . ?
C20 C21 1.395(3) . ?
C20 N2 1.425(3) . ?
C21 C22 1.389(3) . ?
C22 C23 1.384(4) . ?
C23 C24 1.399(4) . ?
C23 C26 1.511(3) . ?
C24 C25 1.387(3) . ?
C26 F4 1.320(4) . ?
C26 F6 1.328(4) . ?
C26 F5 1.333(3) . ?
Cl1 Zn1 2.1924(6) . ?
Cl2 Zn1 2.2127(6) . ?
N1 Zn1 2.0845(18) . ?
N2 Zn1 2.0992(19) . ?
C27 Cl3' 1.569(15) . ?
C27 Cl4' 1.637(12) . ?
C27 Cl4 1.757(9) . ?
C27 Cl3 1.784(12) . ?
Cl3 C27' 1.92(3) . ?
Cl4 Cl4' 0.558(13) . ?
Cl4 C27' 1.73(3) . ?
C27' Cl3' 1.72(3) . ?
C27' Cl4' 1.69(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 135.1(2) . . ?
N1 C1 C12 117.62(19) . . ?
C2 C1 C12 107.19(18) . . ?
C3 C2 C7 119.6(2) . . ?
C3 C2 C1 134.7(2) . . ?
C7 C2 C1 105.66(19) . . ?
C2 C3 C4 118.4(2) . . ?
C5 C4 C3 122.0(2) . . ?
C4 C5 C6 120.6(2) . . ?
C7 C6 C8 116.6(2) . . ?
C7 C6 C5 116.8(2) . . ?
C8 C6 C5 126.6(2) . . ?
C6 C7 C11 123.0(2) . . ?
C6 C7 C2 122.6(2) . . ?
C11 C7 C2 114.4(2) . . ?
C9 C8 C6 120.1(2) . . ?
C8 C9 C10 122.5(2) . . ?
C11 C10 C9 118.5(2) . . ?
C10 C11 C7 119.2(2) . . ?
C10 C11 C12 134.9(2) . . ?
C7 C11 C12 105.83(19) . . ?
N2 C12 C11 135.1(2) . . ?
N2 C12 C1 117.96(19) . . ?
C11 C12 C1 106.87(18) . . ?
C14 C13 C18 121.1(2) . . ?
C14 C13 N1 119.3(2) . . ?
C18 C13 N1 119.6(2) . . ?
C13 C14 C15 119.3(2) . . ?
C16 C15 C14 119.8(2) . . ?
C15 C16 C17 120.7(2) . . ?
C15 C16 C19 120.3(2) . . ?
C17 C16 C19 119.0(2) . . ?
C16 C17 C18 119.8(2) . . ?
C17 C18 C13 119.2(2) . . ?
F3 C19 F2 107.7(3) . . ?
F3 C19 F1 106.0(3) . . ?
F2 C19 F1 105.8(2) . . ?
F3 C19 C16 112.4(2) . . ?
F2 C19 C16 112.7(2) . . ?
F1 C19 C16 111.7(2) . . ?
C25 C20 C21 120.9(2) . . ?
C25 C20 N2 120.6(2) . . ?
C21 C20 N2 118.4(2) . . ?
C22 C21 C20 119.5(2) . . ?
C23 C22 C21 119.6(2) . . ?
C22 C23 C24 121.0(2) . . ?
C22 C23 C26 118.9(2) . . ?
C24 C23 C26 120.1(2) . . ?
C25 C24 C23 119.5(2) . . ?
C24 C25 C20 119.5(2) . . ?
F4 C26 F6 109.4(3) . . ?
F4 C26 F5 105.2(2) . . ?
F6 C26 F5 105.3(3) . . ?
F4 C26 C23 112.2(2) . . ?
F6 C26 C23 112.6(2) . . ?
F5 C26 C23 111.7(2) . . ?
C1 N1 C13 121.31(19) . . ?
C1 N1 Zn1 111.91(15) . . ?
C13 N1 Zn1 126.78(15) . . ?
C12 N2 C20 121.80(19) . . ?
C12 N2 Zn1 111.26(15) . . ?
C20 N2 Zn1 126.89(14) . . ?
N1 Zn1 N2 80.89(7) . . ?
N1 Zn1 Cl1 118.06(5) . . ?
N2 Zn1 Cl1 117.44(6) . . ?
N1 Zn1 Cl2 108.11(5) . . ?
N2 Zn1 Cl2 108.22(5) . . ?
Cl1 Zn1 Cl2 118.10(2) . . ?
Cl3' C27 Cl4' 120.4(8) . . ?
Cl3' C27 Cl4 113.4(8) . . ?
Cl4' C27 Cl4 18.5(5) . . ?
Cl3' C27 Cl3 4.8(6) . . ?
Cl4' C27 Cl3 119.4(7) . . ?
Cl4 C27 Cl3 111.0(6) . . ?
C27 Cl3 C27' 9.4(14) . . ?
Cl4' Cl4 C27' 76.1(19) . . ?
Cl4' Cl4 C27 68.6(12) . . ?
C27' Cl4 C27 10.9(14) . . ?
Cl3' C27' Cl4' 109.3(19) . . ?
Cl3' C27' Cl4 107.3(19) . . ?
Cl4' C27' Cl4 18.8(6) . . ?
Cl3' C27' Cl3 5.5(6) . . ?
Cl4' C27' Cl3 110.1(18) . . ?
Cl4 C27' Cl3 106.2(18) . . ?
Cl4 Cl4' C27 92.9(14) . . ?
Cl4 Cl4' C27' 85(2) . . ?
C27 Cl4' C27' 11.3(14) . . ?
C27 Cl3' C27' 10.2(16) . . ?

_refine_diff_density_max         0.434
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.084

