# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_znclorg
_audit_creation_date             2013-09-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C3 H6 Cl N2 Zn0.5)'
_chemical_formula_sum            'C6 H12 Cl2 N4 Zn'
_chemical_formula_weight         276.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn Cl2 N4 C6'
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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 '-x, -y, -z'
4 'x, -y, z-1/2'

_cell_length_a                   14.6053(6)
_cell_length_b                   5.98157(17)
_cell_length_c                   15.2271(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.214(5)
_cell_angle_gamma                90.00
_cell_volume                     1172.23(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3115
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.1756
_cell_measurement_theta_min      3.2910
_exptl_absorpt_coefficient_mu    6.828
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lamina
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4799
_diffrn_reflns_theta_full        69.98
_diffrn_reflns_theta_max         69.98
_diffrn_reflns_theta_min         3.43
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0747679000
_diffrn_orient_matrix_UB_12      -0.2011237000
_diffrn_orient_matrix_UB_13      -0.0321000000
_diffrn_orient_matrix_UB_21      0.0406930000
_diffrn_orient_matrix_UB_22      -0.0647915000
_diffrn_orient_matrix_UB_23      0.1101535000
_diffrn_orient_matrix_UB_31      -0.0840666000
_diffrn_orient_matrix_UB_32      0.1473248000
_diffrn_orient_matrix_UB_33      0.0046703000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_number_gt                1961
_reflns_number_total             2118
_reflns_odcompleteness_completeness 91.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0256
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0409P)²+0.1563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0682
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.0000 0.38940(6) 0.2500 0.01504(11) Uani 1 2 d S . .
Cl1 Cl 0.12894(4) 0.58403(9) 0.36574(4) 0.02705(14) Uani 1 1 d . . .
N1 N 0.04762(12) 0.1803(3) 0.17497(14) 0.0222(4) Uani 1 1 d . . .
C1 C 0.08404(13) 0.0610(3) 0.14081(15) 0.0172(4) Uani 1 1 d . . .
N2 N 0.12349(12) -0.0730(3) 0.10034(14) 0.0198(4) Uani 1 1 d . . .
C2 C 0.10296(15) -0.3128(3) 0.09403(16) 0.0209(4) Uani 1 1 d . . .
H2A H 0.1562 -0.3857 0.1518 0.031 Uiso 1 1 calc R . .
H2B H 0.1025 -0.3718 0.0352 0.031 Uiso 1 1 calc R . .
H2C H 0.0366 -0.3388 0.0910 0.031 Uiso 1 1 calc R . .
C3 C 0.20294(15) 0.0086(4) 0.07851(17) 0.0249(5) Uani 1 1 d . . .
H3A H 0.2107 0.1670 0.0898 0.037 Uiso 1 1 calc R . .
H3B H 0.1838 -0.0222 0.0101 0.037 Uiso 1 1 calc R . .
H3C H 0.2675 -0.0644 0.1210 0.037 Uiso 1 1 calc R . .
Zn2 Zn 0.5000 0.35311(6) 0.2500 0.01475(11) Uani 1 2 d S . .
Cl2 Cl 0.37150(4) 0.54785(9) 0.23997(4) 0.02633(14) Uani 1 1 d . . .
N3 N 0.45176(13) 0.1481(3) 0.12699(13) 0.0221(4) Uani 1 1 d . . .
C4 C 0.41615(13) 0.0306(3) 0.05626(15) 0.0178(4) Uani 1 1 d . . .
N4 N 0.37860(12) -0.1036(3) -0.02333(12) 0.0184(4) Uani 1 1 d . . .
C5 C 0.30636(17) -0.0222(4) -0.12631(16) 0.0279(5) Uani 1 1 d . . .
H5A H 0.2370 -0.0712 -0.1450 0.042 Uiso 1 1 calc R . .
H5B H 0.3277 -0.0816 -0.1724 0.042 Uiso 1 1 calc R . .
H5C H 0.3081 0.1381 -0.1276 0.042 Uiso 1 1 calc R . .
C6 C 0.38946(18) -0.3452(3) -0.00661(17) 0.0262(4) Uani 1 1 d . . .
H6A H 0.4489 -0.3756 0.0565 0.039 Uiso 1 1 calc R . .
H6B H 0.3984 -0.4153 -0.0588 0.039 Uiso 1 1 calc R . .
H6C H 0.3282 -0.4033 -0.0066 0.039 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 Cl1 2.2068(5) . ?
Zn1 Cl1 2.2067(5) 2 ?
Zn1 N1 2.0259(17) . ?
Zn1 N1 2.0259(17) 2 ?
N1 C1 1.151(3) . ?
C1 N2 1.300(3) . ?
N2 C2 1.459(3) . ?
N2 C3 1.435(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
Zn2 Cl2 2.1522(5) 2_655 ?
Zn2 Cl2 2.1521(5) . ?
Zn2 N3 2.0642(17) . ?
Zn2 N3 2.0641(17) 2_655 ?
N3 C4 1.181(3) . ?
C4 N4 1.336(3) . ?
N4 C5 1.498(3) . ?
N4 C6 1.463(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

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
Cl1 Zn1 Cl1 116.32(3) 2 . ?
N1 Zn1 Cl1 105.43(5) 2 . ?
N1 Zn1 Cl1 112.66(5) . . ?
N1 Zn1 Cl1 112.66(5) 2 2 ?
N1 Zn1 Cl1 105.43(5) . 2 ?
N1 Zn1 N1 103.76(10) 2 . ?
C1 N1 Zn1 173.19(17) . . ?
N1 C1 N2 178.8(2) . . ?
C1 N2 C2 120.94(16) . . ?
C1 N2 C3 119.21(17) . . ?
C3 N2 C2 118.85(16) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
Cl2 Zn2 Cl2 114.46(3) . 2_655 ?
N3 Zn2 Cl2 107.34(5) . 2_655 ?
N3 Zn2 Cl2 110.18(5) 2_655 2_655 ?
N3 Zn2 Cl2 110.18(5) . . ?
N3 Zn2 Cl2 107.34(5) 2_655 . ?
N3 Zn2 N3 107.10(10) 2_655 . ?
C4 N3 Zn2 174.45(15) . . ?
N3 C4 N4 178.36(19) . . ?
C4 N4 C5 122.55(17) . . ?
C4 N4 C6 118.14(17) . . ?
C6 N4 C5 117.88(17) . . ?
N4 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
N4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 N1 C1 N2 -168(9) . . . . ?
Cl1 Zn1 N1 C1 27.9(14) . . . . ?
Cl1 Zn1 N1 C1 155.8(14) 2 . . . ?
N1 Zn1 N1 C1 -85.6(14) 2 . . . ?
N1 C1 N2 C2 -92(10) . . . . ?
N1 C1 N2 C3 99(10) . . . . ?
Zn2 N3 C4 N4 -166(6) . . . . ?
Cl2 Zn2 N3 C4 -154.3(17) 2_655 . . . ?
Cl2 Zn2 N3 C4 -29.1(18) . . . . ?
N3 Zn2 N3 C4 87.4(17) 2_655 . . . ?
N3 C4 N4 C5 -120(7) . . . . ?
N3 C4 N4 C6 74(8) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1002740'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sas_38
_audit_creation_date             2013-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C3 H6 Br N2 Zn0.5)'
_chemical_formula_sum            'C6 H12 Br2 N4 Zn'
_chemical_formula_weight         365.39
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 '-x, -y, -z'
4 'x, -y, z-1/2'

_cell_length_a                   14.8739(10)
_cell_length_b                   6.1147(3)
_cell_length_c                   15.5444(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.993(8)
_cell_angle_gamma                90.00
_cell_volume                     1248.35(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4322
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.6799
_cell_measurement_theta_min      2.5962
_exptl_absorpt_coefficient_mu    8.336
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent white'
_exptl_crystal_density_diffrn    1.944
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10011
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.97
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9987
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0308742000
_diffrn_orient_matrix_UB_12      0.0938128000
_diffrn_orient_matrix_UB_13      0.0201706000
_diffrn_orient_matrix_UB_21      0.0436438000
_diffrn_orient_matrix_UB_22      -0.0676967000
_diffrn_orient_matrix_UB_23      0.0232571000
_diffrn_orient_matrix_UB_31      0.0078607000
_diffrn_orient_matrix_UB_32      0.0075718000
_diffrn_orient_matrix_UB_33      -0.0415151000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_number_gt                2503
_reflns_number_total             2857
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         1.286
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.331
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.331
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0061P)²+12.3802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1081
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.36584(5) 0.04434(13) 0.73755(5) 0.02675(18) Uani 1 1 d . . .
Br2 Br 0.13435(5) -1.07794(13) 0.36786(5) 0.02656(18) Uani 1 1 d . . .
Zn1 Zn 0.5000 -0.15814(17) 0.7500 0.0158(2) Uani 1 2 d S . .
Zn2 Zn 0.0000 -0.87429(17) 0.2500 0.0158(2) Uani 1 2 d S . .
N1 N 0.4521(4) -0.3572(10) 0.6293(5) 0.0257(13) Uani 1 1 d . . .
N2 N 0.3818(4) -0.6040(9) 0.4826(4) 0.0213(12) Uani 1 1 d . . .
N3 N 0.0468(4) -0.6708(9) 0.1764(5) 0.0244(13) Uani 1 1 d . . .
N4 N 0.1204(4) -0.4273(9) 0.1010(4) 0.0207(12) Uani 1 1 d . . .
C1 C 0.4172(5) -0.4722(11) 0.5598(5) 0.0194(13) Uani 1 1 d . . .
C2 C 0.3094(6) -0.5258(13) 0.3807(5) 0.0292(16) Uani 1 1 d . . .
H2A H 0.3058 -0.3690 0.3802 0.044 Uiso 1 1 calc R . .
H2B H 0.2429 -0.5857 0.3610 0.044 Uiso 1 1 calc R . .
H2C H 0.3336 -0.5731 0.3363 0.044 Uiso 1 1 calc R . .
C3 C 0.3968(6) -0.8392(12) 0.4982(5) 0.0277(16) Uani 1 1 d . . .
H3A H 0.3384 -0.9028 0.4993 0.042 Uiso 1 1 calc R . .
H3B H 0.4562 -0.8664 0.5592 0.042 Uiso 1 1 calc R . .
H3C H 0.4057 -0.9033 0.4463 0.042 Uiso 1 1 calc R . .
C4 C 0.0825(5) -0.5557(11) 0.1423(5) 0.0173(13) Uani 1 1 d . . .
C5 C 0.1976(5) -0.5071(12) 0.0792(6) 0.0273(16) Uani 1 1 d . . .
H5A H 0.2608 -0.4350 0.1200 0.041 Uiso 1 1 calc R . .
H5B H 0.1784 -0.4781 0.0120 0.041 Uiso 1 1 calc R . .
H5C H 0.2054 -0.6618 0.0907 0.041 Uiso 1 1 calc R . .
C6 C 0.0976(5) -0.1922(12) 0.0912(5) 0.0245(15) Uani 1 1 d . . .
H6A H 0.0379 -0.1659 0.0985 0.037 Uiso 1 1 calc R . .
H6B H 0.0857 -0.1433 0.0280 0.037 Uiso 1 1 calc R . .
H6C H 0.1542 -0.1137 0.1406 0.037 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Zn1 2.2781(9) . ?
Br2 Zn2 2.3374(9) . ?
Zn1 Br1 2.2782(9) 2_656 ?
Zn1 N1 2.063(6) 2_656 ?
Zn1 N1 2.063(6) . ?
Zn2 Br2 2.3375(9) 2 ?
Zn2 N3 2.022(6) . ?
Zn2 N3 2.022(6) 2 ?
N1 C1 1.185(9) . ?
N2 C1 1.332(9) . ?
N2 C2 1.515(9) . ?
N2 C3 1.458(9) . ?
N3 C4 1.151(8) . ?
N4 C4 1.298(8) . ?
N4 C5 1.427(8) . ?
N4 C6 1.469(9) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

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
Br1 Zn1 Br1 114.16(6) . 2_656 ?
N1 Zn1 Br1 108.21(17) . 2_656 ?
N1 Zn1 Br1 109.20(17) 2_656 2_656 ?
N1 Zn1 Br1 108.21(17) 2_656 . ?
N1 Zn1 Br1 109.20(17) . . ?
N1 Zn1 N1 107.7(4) . 2_656 ?
Br2 Zn2 Br2 115.62(6) . 2 ?
N3 Zn2 Br2 112.12(17) 2 2 ?
N3 Zn2 Br2 106.20(18) . 2 ?
N3 Zn2 Br2 112.12(17) . . ?
N3 Zn2 Br2 106.20(18) 2 . ?
N3 Zn2 N3 104.0(3) 2 . ?
C1 N1 Zn1 174.7(5) . . ?
C1 N2 C2 122.5(6) . . ?
C1 N2 C3 118.8(6) . . ?
C3 N2 C2 117.6(6) . . ?
C4 N3 Zn2 173.4(6) . . ?
C4 N4 C5 119.7(6) . . ?
C4 N4 C6 120.7(5) . . ?
C5 N4 C6 118.8(5) . . ?
N1 C1 N2 177.6(7) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N3 C4 N4 178.1(8) . . ?
N4 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
N4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 Zn1 N1 C1 -156(6) 2_656 . . . ?
Br1 Zn1 N1 C1 -32(6) . . . . ?
Br2 Zn2 N3 C4 -152(5) 2 . . . ?
Br2 Zn2 N3 C4 -25(5) . . . . ?
Zn1 N1 C1 N2 -158(14) . . . . ?
Zn2 N3 C4 N4 161(18) . . . . ?
N1 Zn1 N1 C1 86(6) 2_656 . . . ?
N3 Zn2 N3 C4 90(5) 2 . . . ?
C2 N2 C1 N1 -127(18) . . . . ?
C3 N2 C1 N1 65(18) . . . . ?
C5 N4 C4 N3 -97(22) . . . . ?
C6 N4 C4 N3 94(22) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1002739'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sas_61
_audit_creation_date             2013-11-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 H12 I2 N4 Zn'
_chemical_formula_sum            'C6 H12 I2 N4 Zn'
_chemical_formula_weight         459.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn1 I2 N2 C5 H10'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z+1/2'
4 '-x, y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z-1/2'
8 'x, -y-1/2, z'

_cell_length_a                   13.8920(3)
_cell_length_b                   13.3250(4)
_cell_length_c                   7.5335(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1394.53(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.7590
_cell_measurement_theta_min      2.9240
_exptl_absorpt_coefficient_mu    6.160
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    2.188
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11091
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0393489000
_diffrn_orient_matrix_UB_12      0.0568989000
_diffrn_orient_matrix_UB_13      0.0107416000
_diffrn_orient_matrix_UB_21      -0.0179258000
_diffrn_orient_matrix_UB_22      -0.0130527000
_diffrn_orient_matrix_UB_23      -0.0493074000
_diffrn_orient_matrix_UB_31      -0.0271528000
_diffrn_orient_matrix_UB_32      -0.0738617000
_diffrn_orient_matrix_UB_33      0.0169512000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_number_gt                1554
_reflns_number_total             1655
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     66
_refine_ls_number_reflns         1655
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0143
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0133P)²+0.6638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0309
_refine_ls_wR_factor_ref         0.0317
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
I1 I -0.646410(13) 0.2500 0.89613(2) 0.01829(5) Uani 1 2 d . . S T
I2 I -0.370607(13) 0.2500 1.17688(2) 0.01937(6) Uani 1 2 d . . S T
Zn1 Zn -0.46227(2) 0.2500 0.88262(4) 0.01462(8) Uani 1 2 d . . S T
N1 N -0.41947(12) 0.13439(13) 0.7301(2) 0.0213(4) Uani 1 1 d . . . .
N2 N -0.36639(12) -0.01297(12) 0.5627(2) 0.0204(4) Uani 1 1 d . . . .
C1 C -0.39345(14) 0.06589(15) 0.6519(3) 0.0175(4) Uani 1 1 d . . . .
C2 C -0.40131(15) -0.11227(15) 0.6161(3) 0.0234(5) Uani 1 1 d . . . .
H2A H -0.4563 -0.1048 0.6921 0.035 Uiso 1 1 calc . . GR .
H2B H -0.3513 -0.1472 0.6788 0.035 Uiso 1 1 calc . . GR .
H2C H -0.4191 -0.1499 0.5125 0.035 Uiso 1 1 calc . . GR .
C3 C -0.28701(16) -0.00707(15) 0.4346(3) 0.0247(5) Uani 1 1 d . . . .
H3A H -0.2310 -0.0389 0.4835 0.037 Uiso 1 1 calc . . GR .
H3B H -0.2729 0.0620 0.4098 0.037 Uiso 1 1 calc . . GR .
H3C H -0.3052 -0.0405 0.3268 0.037 Uiso 1 1 calc . . GR .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Zn1 2.5601(4) . ?
I2 Zn1 2.5565(4) . ?
Zn1 N1 2.0119(16) . ?
Zn1 N1 2.0119(17) 8_565 ?
N1 C1 1.145(3) . ?
N2 C1 1.303(3) . ?
N2 C2 1.466(2) . ?
N2 C3 1.467(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?

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
I2 Zn1 I1 117.594(13) . . ?
N1 Zn1 I1 108.54(5) . . ?
N1 Zn1 I1 108.54(5) 8_565 . ?
N1 Zn1 I2 110.37(5) . . ?
N1 Zn1 I2 110.38(5) 8_565 . ?
N1 Zn1 N1 99.94(10) 8_565 . ?
C1 N1 Zn1 176.09(17) . . ?
C1 N2 C2 119.41(16) . . ?
C1 N2 C3 120.85(17) . . ?
C2 N2 C3 118.54(16) . . ?
N1 C1 N2 178.4(2) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 Zn1 N1 C1 -107(3) . . . . ?
I2 Zn1 N1 C1 23(3) . . . . ?
Zn1 N1 C1 N2 100(8) . . . . ?
N1 Zn1 N1 C1 140(2) 8_565 . . . ?
C2 N2 C1 N1 -48(7) . . . . ?
C3 N2 C1 N1 145(7) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1002738'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sasn55
_audit_creation_date             2013-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H20 Br2 N4 Zn'
_chemical_formula_sum            'C26 H20 Br2 N4 Zn'
_chemical_formula_weight         613.65
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.6653(9)
_cell_length_b                   18.1538(16)
_cell_length_c                   14.5506(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.564(8)
_cell_angle_gamma                90
_cell_volume                     2550.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4541
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.7187
_cell_measurement_theta_min      2.5789
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13595
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.722
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0708486000
_diffrn_orient_matrix_UB_12      -0.0103692000
_diffrn_orient_matrix_UB_13      -0.0047309000
_diffrn_orient_matrix_UB_21      -0.0193205000
_diffrn_orient_matrix_UB_22      0.0345005000
_diffrn_orient_matrix_UB_23      0.0184308000
_diffrn_orient_matrix_UB_31      -0.0040545000
_diffrn_orient_matrix_UB_32      0.0152060000
_diffrn_orient_matrix_UB_33      -0.0448280000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4519
_reflns_number_total             5860
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5860
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      0.980
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0165P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0551
_refine_ls_wR_factor_ref         0.0605
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.73331(3) 0.74972(2) 0.27923(2) 0.02075(7) Uani 1 1 d . . . . .
Br2 Br 0.51467(3) 0.83793(2) 0.48889(2) 0.02797(8) Uani 1 1 d . . . . .
Zn1 Zn 0.68573(3) 0.75870(2) 0.43565(2) 0.01639(8) Uani 1 1 d . . . . .
N1 N 0.8591(3) 0.78809(12) 0.51159(15) 0.0244(6) Uani 1 1 d . . . . .
N2 N 1.0120(2) 0.85872(11) 0.62043(14) 0.0181(5) Uani 1 1 d . . . . .
N3 N 0.6657(2) 0.65420(12) 0.48558(14) 0.0214(5) Uani 1 1 d . . . . .
N4 N 0.6885(2) 0.52733(11) 0.54655(14) 0.0161(5) Uani 1 1 d . . . . .
C1 C 0.9302(3) 0.82080(14) 0.56276(18) 0.0197(6) Uani 1 1 d . . . . .
C2 C 0.9964(3) 0.93805(14) 0.62572(17) 0.0164(6) Uani 1 1 d . . . . .
C3 C 0.8738(3) 0.97025(15) 0.59230(17) 0.0198(6) Uani 1 1 d . . . . .
H3 H 0.8011 0.9411 0.5692 0.024 Uiso 1 1 calc R . . . .
C4 C 0.8609(3) 1.04691(15) 0.59373(18) 0.0242(7) Uani 1 1 d . . . . .
H4 H 0.7795 1.0691 0.5713 0.029 Uiso 1 1 calc R . . . .
C5 C 0.9691(3) 1.08953(15) 0.62849(18) 0.0257(7) Uani 1 1 d . . . . .
H5 H 0.9603 1.1405 0.6292 0.031 Uiso 1 1 calc R . . . .
C6 C 1.0906(3) 1.05726(15) 0.66227(17) 0.0228(7) Uani 1 1 d . . . . .
H6 H 1.1626 1.0866 0.6859 0.027 Uiso 1 1 calc R . . . .
C7 C 1.1057(3) 0.98058(14) 0.66096(17) 0.0193(6) Uani 1 1 d . . . . .
H7 H 1.1873 0.9586 0.6833 0.023 Uiso 1 1 calc R . . . .
C8 C 1.1181(3) 0.81781(14) 0.67332(17) 0.0172(6) Uani 1 1 d . . . . .
C9 C 1.2293(3) 0.78897(15) 0.62912(19) 0.0238(7) Uani 1 1 d . . . . .
H9 H 1.2379 0.7967 0.5664 0.029 Uiso 1 1 calc R . . . .
C10 C 1.3277(3) 0.74852(16) 0.6790(2) 0.0316(7) Uani 1 1 d . . . . .
H10 H 1.4026 0.7284 0.6499 0.038 Uiso 1 1 calc R . . . .
C11 C 1.3148(3) 0.73804(15) 0.7724(2) 0.0310(8) Uani 1 1 d . . . . .
H11 H 1.3808 0.7105 0.8058 0.037 Uiso 1 1 calc R . . . .
C12 C 1.2049(3) 0.76814(15) 0.8159(2) 0.0275(7) Uani 1 1 d . . . . .
H12 H 1.1984 0.7620 0.8790 0.033 Uiso 1 1 calc R . . . .
C13 C 1.1032(3) 0.80773(14) 0.76654(18) 0.0218(6) Uani 1 1 d . . . . .
H13 H 1.0273 0.8269 0.7955 0.026 Uiso 1 1 calc R . . . .
C14 C 0.6762(3) 0.59543(14) 0.51435(17) 0.0163(6) Uani 1 1 d . . . . .
C15 C 0.6228(3) 0.50812(14) 0.63065(16) 0.0145(6) Uani 1 1 d . . . . .
C16 C 0.5931(3) 0.56333(14) 0.69288(17) 0.0192(6) Uani 1 1 d . . . . .
H16 H 0.6163 0.6121 0.6812 0.023 Uiso 1 1 calc R . . . .
C17 C 0.5282(3) 0.54456(15) 0.77295(18) 0.0255(7) Uani 1 1 d . . . . .
H17 H 0.5079 0.5810 0.8152 0.031 Uiso 1 1 calc R . . . .
C18 C 0.4936(3) 0.47217(16) 0.79017(19) 0.0245(7) Uani 1 1 d . . . . .
H18 H 0.4506 0.4601 0.8441 0.029 Uiso 1 1 calc R . . . .
C19 C 0.5228(3) 0.41718(15) 0.72738(18) 0.0206(6) Uani 1 1 d . . . . .
H19 H 0.4992 0.3685 0.7392 0.025 Uiso 1 1 calc R . . . .
C20 C 0.5875(3) 0.43509(14) 0.64677(17) 0.0158(6) Uani 1 1 d . . . . .
H20 H 0.6068 0.3987 0.6042 0.019 Uiso 1 1 calc R . . . .
C21 C 0.7790(3) 0.47660(14) 0.49882(17) 0.0163(6) Uani 1 1 d . . . . .
C22 C 0.8772(3) 0.43630(14) 0.54837(18) 0.0188(6) Uani 1 1 d . . . . .
H22 H 0.8860 0.4406 0.6121 0.023 Uiso 1 1 calc R . . . .
C23 C 0.9629(3) 0.38918(15) 0.50198(19) 0.0247(7) Uani 1 1 d . . . . .
H23 H 1.0274 0.3603 0.5349 0.030 Uiso 1 1 calc R . . . .
C24 C 0.9528(3) 0.38491(15) 0.4071(2) 0.0274(7) Uani 1 1 d . . . . .
H24 H 1.0118 0.3540 0.3761 0.033 Uiso 1 1 calc R . . . .
C25 C 0.8552(3) 0.42649(16) 0.3584(2) 0.0302(8) Uani 1 1 d . . . . .
H25 H 0.8492 0.4236 0.2945 0.036 Uiso 1 1 calc R . . . .
C26 C 0.7657(3) 0.47260(15) 0.40359(18) 0.0228(6) Uani 1 1 d . . . . .
H26 H 0.6987 0.5000 0.3709 0.027 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Zn1 2.3478(4) . ?
Br2 Zn1 2.3488(4) . ?
Zn1 N1 2.037(2) . ?
Zn1 N3 2.044(2) . ?
N1 C1 1.155(3) . ?
N2 C1 1.321(3) . ?
N2 C2 1.451(3) . ?
N2 C8 1.457(3) . ?
N3 C14 1.149(3) . ?
N4 C14 1.326(3) . ?
N4 C15 1.446(3) . ?
N4 C21 1.466(3) . ?
C2 C3 1.390(4) . ?
C2 C7 1.388(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.397(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.400(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(4) . ?
C8 C13 1.382(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.391(4) . ?
C13 H13 0.9300 . ?
C15 C16 1.389(3) . ?
C15 C20 1.392(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.390(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.391(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.377(4) . ?
C21 C26 1.388(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.387(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.380(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.390(4) . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 Zn1 Br2 122.245(17) . . ?
N1 Zn1 Br1 110.61(7) . . ?
N1 Zn1 Br2 103.59(7) . . ?
N1 Zn1 N3 97.99(9) . . ?
N3 Zn1 Br1 107.81(6) . . ?
N3 Zn1 Br2 111.84(6) . . ?
C1 N1 Zn1 159.4(2) . . ?
C1 N2 C2 119.4(2) . . ?
C1 N2 C8 117.2(2) . . ?
C2 N2 C8 123.4(2) . . ?
C14 N3 Zn1 169.6(2) . . ?
C14 N4 C15 119.2(2) . . ?
C14 N4 C21 117.7(2) . . ?
C15 N4 C21 122.9(2) . . ?
N1 C1 N2 179.3(3) . . ?
C3 C2 N2 119.2(2) . . ?
C7 C2 N2 119.5(2) . . ?
C7 C2 C3 121.2(2) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.3(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 118.7(3) . . ?
C2 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C9 C8 N2 119.4(2) . . ?
C9 C8 C13 121.6(3) . . ?
C13 C8 N2 119.0(2) . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.3(3) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.9(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.7(3) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 118.2(3) . . ?
C8 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
N3 C14 N4 179.3(3) . . ?
C16 C15 N4 119.3(2) . . ?
C16 C15 C20 121.2(2) . . ?
C20 C15 N4 119.5(2) . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 118.9(2) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.9(2) . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 119.2(2) . . ?
C15 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C22 C21 N4 119.9(2) . . ?
C22 C21 C26 121.7(3) . . ?
C26 C21 N4 118.4(2) . . ?
C21 C22 H22 120.5 . . ?
C21 C22 C23 119.1(3) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.3(3) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 119.9(3) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.8(3) . . ?
C26 C25 H25 119.6 . . ?
C21 C26 C25 118.2(3) . . ?
C21 C26 H26 120.9 . . ?
C25 C26 H26 120.9 . . ?

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
N2 C2 C3 C4 -177.3(2) . . . . ?
N2 C2 C7 C6 177.6(2) . . . . ?
N2 C8 C9 C10 -178.3(2) . . . . ?
N2 C8 C13 C12 179.6(2) . . . . ?
N4 C15 C16 C17 179.1(2) . . . . ?
N4 C15 C20 C19 -179.2(2) . . . . ?
N4 C21 C22 C23 -179.3(2) . . . . ?
N4 C21 C26 C25 177.6(2) . . . . ?
C1 N2 C2 C3 18.9(4) . . . . ?
C1 N2 C2 C7 -158.9(2) . . . . ?
C1 N2 C8 C9 70.3(3) . . . . ?
C1 N2 C8 C13 -108.5(3) . . . . ?
C2 N2 C8 C9 -107.3(3) . . . . ?
C2 N2 C8 C13 73.9(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C2 C7 C6 -0.1(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C5 C6 C7 C2 -0.3(4) . . . . ?
C7 C2 C3 C4 0.4(4) . . . . ?
C8 N2 C2 C3 -163.6(2) . . . . ?
C8 N2 C2 C7 18.7(4) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C9 C8 C13 C12 0.8(4) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 C13 1.8(4) . . . . ?
C11 C12 C13 C8 -1.9(4) . . . . ?
C13 C8 C9 C10 0.5(4) . . . . ?
C14 N4 C15 C16 -23.3(4) . . . . ?
C14 N4 C15 C20 155.1(3) . . . . ?
C14 N4 C21 C22 130.4(3) . . . . ?
C14 N4 C21 C26 -47.4(4) . . . . ?
C15 N4 C21 C22 -44.1(4) . . . . ?
C15 N4 C21 C26 138.1(3) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C15 C20 C19 -0.9(4) . . . . ?
C16 C17 C18 C19 -0.3(5) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C15 0.4(4) . . . . ?
C20 C15 C16 C17 0.7(4) . . . . ?
C21 N4 C15 C16 151.1(3) . . . . ?
C21 N4 C15 C20 -30.5(4) . . . . ?
C21 C22 C23 C24 2.3(4) . . . . ?
C22 C21 C26 C25 -0.1(4) . . . . ?
C22 C23 C24 C25 -1.4(4) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C24 C25 C26 C21 1.1(4) . . . . ?
C26 C21 C22 C23 -1.6(4) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1002743'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_but101
_audit_creation_date             2014-06-10
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H20 I2 N4 Zn'
_chemical_formula_sum            'C26 H20 I2 N4 Zn'
_chemical_formula_weight         707.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c26 h20 n4 zn1 i2'
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.93005(20)
_cell_length_b                   18.0924(4)
_cell_length_c                   14.7012(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.9238(18)
_cell_angle_gamma                90.00
_cell_volume                     2634.99(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6188
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.9840
_cell_measurement_theta_min      3.2810
_exptl_absorpt_coefficient_mu    3.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13063
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.65
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9987
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00    0.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -31.00   42.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777   57.0000 -180.0000 73

#__ type_ start__ end____ width___ exp.time_
  3 omega  -14.00   24.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega  -34.00   12.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -57.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
  5 omega  -45.00   23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -57.0000    0.0000 68
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0344814000
_diffrn_orient_matrix_UB_12      -0.0317572000
_diffrn_orient_matrix_UB_13      0.0177587000
_diffrn_orient_matrix_UB_21      -0.0591920000
_diffrn_orient_matrix_UB_22      -0.0214240000
_diffrn_orient_matrix_UB_23      -0.0090824000
_diffrn_orient_matrix_UB_31      0.0206760000
_diffrn_orient_matrix_UB_32      -0.0083673000
_diffrn_orient_matrix_UB_33      -0.0440799000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5025
_reflns_number_total             5869
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5869
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0134P)²+0.4415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0504
_refine_ls_wR_factor_ref         0.0535
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.242582(19) 0.243442(11) 0.764709(12) 0.01983(6) Uani 1 1 d . . .
I2 I 0.02429(2) 0.345417(13) 0.989684(13) 0.02975(7) Uani 1 1 d . . .
Zn1 Zn 0.19972(3) 0.258521(18) 0.93240(2) 0.01687(8) Uani 1 1 d . . .
C13 C 0.0922(3) 0.06260(17) 1.18137(19) 0.0233(7) Uani 1 1 d . . .
H13 H 0.1133 0.1117 1.1699 0.028 Uiso 1 1 calc R . .
N2 N 0.1941(2) 0.02714(13) 1.04135(15) 0.0187(5) Uani 1 1 d . . .
C12 C 0.0270(3) 0.0432(2) 1.2585(2) 0.0315(8) Uani 1 1 d . . .
H12 H 0.0042 0.0797 1.2993 0.038 Uiso 1 1 calc R . .
C2 C 0.1253(3) 0.00711(16) 1.12179(18) 0.0160(6) Uani 1 1 d . . .
C1 C 0.1865(3) 0.09522(18) 1.01108(19) 0.0196(6) Uani 1 1 d . . .
N1 N 0.1811(2) 0.15458(14) 0.98403(16) 0.0233(6) Uani 1 1 d . . .
C4 C 0.2729(3) -0.02833(19) 0.9037(2) 0.0288(8) Uani 1 1 d . . .
H4 H 0.2084 -0.0011 0.8693 0.035 Uiso 1 1 calc R . .
C3 C 0.2832(3) -0.02364(16) 0.99744(19) 0.0194(6) Uani 1 1 d . . .
C9 C 0.0930(3) -0.06592(16) 1.13701(19) 0.0191(6) Uani 1 1 d . . .
H9 H 0.1143 -0.1024 1.0958 0.023 Uiso 1 1 calc R . .
C11 C -0.0045(3) -0.02986(19) 1.2753(2) 0.0290(8) Uani 1 1 d . . .
H11 H -0.0476 -0.0425 1.3273 0.035 Uiso 1 1 calc R . .
C10 C 0.0284(3) -0.08381(18) 1.2144(2) 0.0257(7) Uani 1 1 d . . .
H10 H 0.0069 -0.1329 1.2255 0.031 Uiso 1 1 calc R . .
N1A N 0.3721(2) 0.28833(14) 1.00663(16) 0.0212(5) Uani 1 1 d . . .
C8 C 0.3783(3) -0.06307(16) 1.0502(2) 0.0217(7) Uani 1 1 d . . .
H8 H 0.3848 -0.0583 1.1133 0.026 Uiso 1 1 calc R . .
C7 C 0.4640(3) -0.10978(18) 1.0071(2) 0.0283(8) Uani 1 1 d . . .
H7 H 0.5271 -0.1378 1.0417 0.034 Uiso 1 1 calc R . .
C5 C 0.3622(3) -0.0751(2) 0.8616(2) 0.0371(9) Uani 1 1 d . . .
H5 H 0.3576 -0.0790 0.7984 0.045 Uiso 1 1 calc R . .
C6 C 0.4567(3) -0.11523(19) 0.9135(2) 0.0333(8) Uani 1 1 d . . .
H6 H 0.5159 -0.1462 0.8853 0.040 Uiso 1 1 calc R . .
C1A C 0.4418(3) 0.32029(16) 1.05785(19) 0.0181(6) Uani 1 1 d . . .
N2A N 0.5229(2) 0.35762(14) 1.11596(15) 0.0197(5) Uani 1 1 d . . .
C2A C 0.5061(3) 0.43656(16) 1.12461(18) 0.0181(6) Uani 1 1 d . . .
C3A C 0.6267(3) 0.31628(16) 1.16874(19) 0.0190(6) Uani 1 1 d . . .
C8A C 0.6179(3) 0.30758(18) 1.2617(2) 0.0261(7) Uani 1 1 d . . .
H8A H 0.5475 0.3290 1.2909 0.031 Uiso 1 1 calc R . .
C9A C 0.6134(3) 0.47899(17) 1.15995(19) 0.0216(7) Uani 1 1 d . . .
H9A H 0.6946 0.4570 1.1802 0.026 Uiso 1 1 calc R . .
C4A C 0.7304(3) 0.28537(18) 1.1243(2) 0.0271(7) Uani 1 1 d . . .
H4A H 0.7352 0.2921 1.0619 0.033 Uiso 1 1 calc R . .
C13A C 0.3848(3) 0.46857(17) 1.09508(19) 0.0227(7) Uani 1 1 d . . .
H13A H 0.3134 0.4394 1.0719 0.027 Uiso 1 1 calc R . .
C10A C 0.5973(3) 0.55478(17) 1.16458(19) 0.0252(7) Uani 1 1 d . . .
H10A H 0.6686 0.5839 1.1880 0.030 Uiso 1 1 calc R . .
C12A C 0.3705(3) 0.54477(18) 1.1004(2) 0.0270(7) Uani 1 1 d . . .
H12A H 0.2892 0.5669 1.0805 0.032 Uiso 1 1 calc R . .
C11A C 0.4768(3) 0.58773(18) 1.13501(19) 0.0260(7) Uani 1 1 d . . .
H11A H 0.4673 0.6388 1.1384 0.031 Uiso 1 1 calc R . .
C7A C 0.7152(3) 0.26671(19) 1.3101(2) 0.0335(8) Uani 1 1 d . . .
H7A H 0.7109 0.2607 1.3727 0.040 Uiso 1 1 calc R . .
C6A C 0.8195(3) 0.23447(19) 1.2664(2) 0.0371(9) Uani 1 1 d . . .
H6A H 0.8841 0.2063 1.2995 0.045 Uiso 1 1 calc R . .
C5A C 0.8276(3) 0.24410(19) 1.1737(3) 0.0374(9) Uani 1 1 d . . .
H5A H 0.8983 0.2229 1.1444 0.045 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Zn1 2.5449(4) . ?
I2 Zn1 2.5331(4) . ?
Zn1 N1 2.041(2) . ?
Zn1 N1A 2.038(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.389(4) . ?
C13 C2 1.387(4) . ?
N2 C2 1.451(3) . ?
N2 C1 1.310(4) . ?
N2 C3 1.456(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.385(5) . ?
C2 C9 1.381(4) . ?
C1 N1 1.145(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.377(4) . ?
C4 C5 1.399(4) . ?
C3 C8 1.379(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.379(4) . ?
C10 H10 0.9300 . ?
N1A C1A 1.144(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.383(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(5) . ?
C6 H6 0.9300 . ?
C1A N2A 1.319(4) . ?
N2A C2A 1.445(4) . ?
N2A C3A 1.454(4) . ?
C2A C9A 1.385(4) . ?
C2A C13A 1.379(4) . ?
C3A C8A 1.385(4) . ?
C3A C4A 1.375(4) . ?
C8A H8A 0.9300 . ?
C8A C7A 1.376(4) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.383(4) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.386(4) . ?
C13A H13A 0.9300 . ?
C13A C12A 1.389(4) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.380(4) . ?
C12A H12A 0.9300 . ?
C12A C11A 1.380(4) . ?
C11A H11A 0.9300 . ?
C7A H7A 0.9300 . ?
C7A C6A 1.383(5) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.383(5) . ?
C5A H5A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I2 Zn1 I1 123.573(14) . . ?
N1 Zn1 I1 106.68(7) . . ?
N1 Zn1 I2 111.48(7) . . ?
N1A Zn1 I1 110.92(7) . . ?
N1A Zn1 I2 103.24(7) . . ?
N1A Zn1 N1 97.99(10) . . ?
C12 C13 H13 120.7 . . ?
C2 C13 H13 120.7 . . ?
C2 C13 C12 118.5(3) . . ?
C2 N2 C3 122.5(2) . . ?
C1 N2 C2 119.5(2) . . ?
C1 N2 C3 117.7(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C2 N2 118.6(3) . . ?
C9 C2 C13 121.5(3) . . ?
C9 C2 N2 119.9(2) . . ?
N1 C1 N2 179.2(3) . . ?
C1 N1 Zn1 171.8(2) . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.3(3) . . ?
C5 C4 H4 120.8 . . ?
C4 C3 N2 118.5(3) . . ?
C4 C3 C8 122.1(3) . . ?
C8 C3 N2 119.4(2) . . ?
C2 C9 H9 120.5 . . ?
C10 C9 C2 118.9(3) . . ?
C10 C9 H9 120.5 . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11 120.2 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C1A N1A Zn1 159.1(2) . . ?
C3 C8 H8 120.7 . . ?
C3 C8 C7 118.6(3) . . ?
C7 C8 H8 120.7 . . ?
C8 C7 H7 119.7 . . ?
C6 C7 C8 120.6(3) . . ?
C6 C7 H7 119.7 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N1A C1A N2A 179.2(3) . . ?
C1A N2A C2A 119.6(2) . . ?
C1A N2A C3A 117.5(2) . . ?
C2A N2A C3A 122.9(2) . . ?
C9A C2A N2A 119.4(3) . . ?
C13A C2A N2A 119.4(3) . . ?
C13A C2A C9A 121.2(3) . . ?
C8A C3A N2A 119.7(3) . . ?
C4A C3A N2A 118.8(3) . . ?
C4A C3A C8A 121.5(3) . . ?
C3A C8A H8A 120.6 . . ?
C7A C8A C3A 118.8(3) . . ?
C7A C8A H8A 120.6 . . ?
C2A C9A H9A 120.7 . . ?
C10A C9A C2A 118.6(3) . . ?
C10A C9A H9A 120.7 . . ?
C3A C4A H4A 120.4 . . ?
C3A C4A C5A 119.2(3) . . ?
C5A C4A H4A 120.4 . . ?
C2A C13A H13A 120.3 . . ?
C2A C13A C12A 119.3(3) . . ?
C12A C13A H13A 120.3 . . ?
C9A C10A H10A 119.5 . . ?
C11A C10A C9A 120.9(3) . . ?
C11A C10A H10A 119.5 . . ?
C13A C12A H12A 120.0 . . ?
C11A C12A C13A 120.1(3) . . ?
C11A C12A H12A 120.0 . . ?
C10A C11A C12A 119.8(3) . . ?
C10A C11A H11A 120.1 . . ?
C12A C11A H11A 120.1 . . ?
C8A C7A H7A 119.7 . . ?
C8A C7A C6A 120.5(3) . . ?
C6A C7A H7A 119.7 . . ?
C7A C6A H6A 120.0 . . ?
C5A C6A C7A 120.0(3) . . ?
C5A C6A H6A 120.0 . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A C4A 119.9(3) . . ?
C6A C5A H5A 120.1 . . ?

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
I1 Zn1 N1 C1 66.1(18) . . . . ?
I1 Zn1 N1A C1A 132.3(7) . . . . ?
I2 Zn1 N1 C1 -156.3(17) . . . . ?
I2 Zn1 N1A C1A -2.0(7) . . . . ?
Zn1 N1A C1A N2A -103(27) . . . . ?
C13 C12 C11 C10 -0.5(5) . . . . ?
C13 C2 C9 C10 -1.2(4) . . . . ?
N2 C2 C9 C10 179.5(2) . . . . ?
N2 C1 N1 Zn1 -24(31) . . . . ?
N2 C3 C8 C7 -178.6(3) . . . . ?
C12 C13 C2 N2 -179.7(3) . . . . ?
C12 C13 C2 C9 1.0(4) . . . . ?
C12 C11 C10 C9 0.3(5) . . . . ?
C2 C13 C12 C11 -0.1(5) . . . . ?
C2 N2 C1 N1 164(30) . . . . ?
C2 N2 C3 C4 136.4(3) . . . . ?
C2 N2 C3 C8 -46.2(4) . . . . ?
C2 C9 C10 C11 0.6(4) . . . . ?
C1 N2 C2 C13 -21.2(4) . . . . ?
C1 N2 C2 C9 158.1(3) . . . . ?
C1 N2 C3 C4 -49.8(4) . . . . ?
C1 N2 C3 C8 127.6(3) . . . . ?
N1 Zn1 N1A C1A -116.4(7) . . . . ?
C4 C3 C8 C7 -1.3(4) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C3 N2 C2 C13 152.5(3) . . . . ?
C3 N2 C2 C9 -28.2(4) . . . . ?
C3 N2 C1 N1 -10(30) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C3 C8 C7 C6 1.7(4) . . . . ?
N1A Zn1 N1 C1 -48.6(18) . . . . ?
N1A C1A N2A C2A 65(27) . . . . ?
N1A C1A N2A C3A -115(27) . . . . ?
C8 C7 C6 C5 -1.1(5) . . . . ?
C5 C4 C3 N2 177.6(3) . . . . ?
C5 C4 C3 C8 0.3(5) . . . . ?
C1A N2A C2A C9A -158.3(3) . . . . ?
C1A N2A C2A C13A 19.8(4) . . . . ?
C1A N2A C3A C8A -111.0(3) . . . . ?
C1A N2A C3A C4A 67.7(3) . . . . ?
N2A C2A C9A C10A 177.6(2) . . . . ?
N2A C2A C13A C12A -177.6(2) . . . . ?
N2A C3A C8A C7A 178.4(3) . . . . ?
N2A C3A C4A C5A -178.2(3) . . . . ?
C2A N2A C3A C8A 69.2(4) . . . . ?
C2A N2A C3A C4A -112.1(3) . . . . ?
C2A C9A C10A C11A 0.2(4) . . . . ?
C2A C13A C12A C11A -0.1(4) . . . . ?
C3A N2A C2A C9A 21.5(4) . . . . ?
C3A N2A C2A C13A -160.4(2) . . . . ?
C3A C8A C7A C6A -0.4(5) . . . . ?
C3A C4A C5A C6A 0.0(5) . . . . ?
C8A C3A C4A C5A 0.5(5) . . . . ?
C8A C7A C6A C5A 1.0(5) . . . . ?
C9A C2A C13A C12A 0.4(4) . . . . ?
C9A C10A C11A C12A 0.1(4) . . . . ?
C4A C3A C8A C7A -0.3(5) . . . . ?
C13A C2A C9A C10A -0.5(4) . . . . ?
C13A C12A C11A C10A -0.2(4) . . . . ?
C7A C6A C5A C4A -0.8(5) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1007640'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sas_44
_audit_creation_date             2014-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C52 H44 N8 O2 Zn, Cl6 Zn2'
_chemical_formula_sum            'C52 H44 Cl6 N8 O2 Zn3'
_chemical_formula_weight         1221.82
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.9007(3)
_cell_length_b                   25.2926(8)
_cell_length_c                   10.9442(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.116(3)
_cell_angle_gamma                90
_cell_volume                     2724.99(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5216
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.6980
_cell_measurement_theta_min      2.6220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16137
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         2.622
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0687431000
_diffrn_orient_matrix_UB_12      0.0049409000
_diffrn_orient_matrix_UB_13      0.0222634000
_diffrn_orient_matrix_UB_21      -0.0216063000
_diffrn_orient_matrix_UB_22      0.0159909000
_diffrn_orient_matrix_UB_23      0.0475793000
_diffrn_orient_matrix_UB_31      -0.0001625000
_diffrn_orient_matrix_UB_32      -0.0225238000
_diffrn_orient_matrix_UB_33      0.0385001000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4976
_reflns_number_total             6107
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         6107
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0213P)²+1.9045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0706
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C23(H23), C9(H9), C22(H22), C11(H11), C13(H13), C25(H25), C19(H19),
 C5(H5), C10(H10), C12(H12), C4(H4), C17(H17), C6(H6), C18(H18), C24(H24),
 C3(H3), C20(H20), C16(H16), C26(H26)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.5000 0.5000 1.0000 0.01102(8) Uani 1 2 d S T P . .
Zn2 Zn 0.49292(2) 0.56380(2) 0.49901(2) 0.01404(7) Uani 1 1 d . . . . .
Cl1 Cl 0.51521(5) 0.60473(2) 0.32325(5) 0.01613(11) Uani 1 1 d . . . . .
Cl2 Cl 0.67235(5) 0.50329(2) 0.53423(5) 0.01788(11) Uani 1 1 d . . . . .
N4 N 0.77375(16) 0.62781(7) 0.87029(17) 0.0144(4) Uani 1 1 d . . . . .
N1 N 0.63921(17) 0.43960(7) 0.96263(17) 0.0165(4) Uani 1 1 d . . . . .
C7 C 0.8303(2) 0.27303(9) 0.9312(2) 0.0220(5) Uani 1 1 d . . . . .
H7 H 0.8467 0.2719 0.8492 0.026 Uiso 1 1 calc R . . . .
N2 N 0.79749(16) 0.36880(7) 0.91467(17) 0.0152(4) Uani 1 1 d . . . . .
C15 C 0.8860(2) 0.60883(8) 0.8077(2) 0.0154(4) Uani 1 1 d . . . . .
N3 N 0.63953(17) 0.55940(7) 0.96325(18) 0.0187(4) Uani 1 1 d . . . . .
C1 C 0.7119(2) 0.40662(8) 0.94008(19) 0.0146(4) Uani 1 1 d . . . . .
C2 C 0.79898(19) 0.32055(8) 0.9854(2) 0.0156(4) Uani 1 1 d . . . . .
C23 C 0.8115(2) 0.77350(9) 0.8952(2) 0.0216(5) Uani 1 1 d . . . . .
H23 H 0.8775 0.7992 0.8887 0.026 Uiso 1 1 calc R . . . .
C9 C 1.0298(2) 0.36093(9) 0.8582(2) 0.0186(5) Uani 1 1 d . . . . .
H9 H 1.0493 0.3360 0.9200 0.022 Uiso 1 1 calc R . . . .
C22 C 0.8416(2) 0.72090(8) 0.8765(2) 0.0166(4) Uani 1 1 d . . . . .
H22 H 0.9277 0.7111 0.8582 0.020 Uiso 1 1 calc R . . . .
C11 C 1.1014(2) 0.41391(9) 0.6938(2) 0.0222(5) Uani 1 1 d . . . . .
H11 H 1.1687 0.4243 0.6458 0.027 Uiso 1 1 calc R . . . .
C13 C 0.8705(2) 0.41967(8) 0.7444(2) 0.0166(4) Uani 1 1 d . . . . .
H13 H 0.7838 0.4340 0.7305 0.020 Uiso 1 1 calc R . . . .
C8 C 0.9008(2) 0.38249(8) 0.83664(19) 0.0143(4) Uani 1 1 d . . . . .
C25 C 0.5856(2) 0.75010(10) 0.9319(3) 0.0288(6) Uani 1 1 d . . . . .
H25 H 0.4998 0.7599 0.9510 0.035 Uiso 1 1 calc R . . . .
C19 C 1.0114(3) 0.60911(11) 0.6346(3) 0.0336(6) Uani 1 1 d . . . . .
H19 H 1.0265 0.6225 0.5581 0.040 Uiso 1 1 calc R . . . .
C5 C 0.8083(2) 0.22899(10) 1.1223(3) 0.0316(6) Uani 1 1 d . . . . .
H5 H 0.8124 0.1982 1.1689 0.038 Uiso 1 1 calc R . . . .
C14 C 0.7004(2) 0.59163(8) 0.9194(2) 0.0155(4) Uani 1 1 d . . . . .
C10 C 1.1294(2) 0.37713(9) 0.7866(2) 0.0221(5) Uani 1 1 d . . . . .
H10 H 1.2164 0.3630 0.8011 0.027 Uiso 1 1 calc R . . . .
C12 C 0.9715(2) 0.43510(9) 0.6733(2) 0.0201(5) Uani 1 1 d . . . . .
H12 H 0.9520 0.4599 0.6112 0.024 Uiso 1 1 calc R . . . .
C4 C 0.7736(2) 0.27619(10) 1.1742(2) 0.0281(6) Uani 1 1 d . . . . .
H4 H 0.7524 0.2769 1.2549 0.034 Uiso 1 1 calc R . . . .
C17 C 1.0744(2) 0.54991(10) 0.8014(3) 0.0289(6) Uani 1 1 d . . . . .
H17 H 1.1302 0.5232 0.8367 0.035 Uiso 1 1 calc R . . . .
C21 C 0.7424(2) 0.68300(8) 0.8851(2) 0.0147(4) Uani 1 1 d . . . . .
C6 C 0.8366(2) 0.22728(9) 1.0019(3) 0.0275(6) Uani 1 1 d . . . . .
H6 H 0.8601 0.1954 0.9677 0.033 Uiso 1 1 calc R . . . .
C18 C 1.0957(2) 0.56994(10) 0.6879(3) 0.0339(7) Uani 1 1 d . . . . .
H18 H 1.1667 0.5571 0.6472 0.041 Uiso 1 1 calc R . . . .
C24 C 0.6838(2) 0.78822(9) 0.9237(2) 0.0260(5) Uani 1 1 d . . . . .
H24 H 0.6644 0.8236 0.9371 0.031 Uiso 1 1 calc R . . . .
C3 C 0.7704(2) 0.32262(9) 1.1062(2) 0.0192(5) Uani 1 1 d . . . . .
H3 H 0.7492 0.3546 1.1414 0.023 Uiso 1 1 calc R . . . .
C20 C 0.9050(2) 0.62855(9) 0.6935(2) 0.0232(5) Uani 1 1 d . . . . .
H20 H 0.8475 0.6544 0.6567 0.028 Uiso 1 1 calc R . . . .
C16 C 0.9694(2) 0.56967(8) 0.8629(2) 0.0198(5) Uani 1 1 d . . . . .
H16 H 0.9553 0.5568 0.9401 0.024 Uiso 1 1 calc R . . . .
C26 C 0.6135(2) 0.69710(9) 0.9119(2) 0.0237(5) Uani 1 1 d . . . . .
H26 H 0.5467 0.6715 0.9163 0.028 Uiso 1 1 calc R . . . .
O1 O 0.58377(16) 0.49863(7) 1.18426(15) 0.0172(3) Uani 1 1 d . . . . .
Cl3 Cl 0.46308(6) 0.60963(2) 0.66571(5) 0.02193(12) Uani 1 1 d . . . . .
H1A H 0.569(3) 0.5239(12) 1.223(3) 0.039(9) Uiso 1 1 d . . . . .
H1B H 0.566(3) 0.4735(12) 1.221(3) 0.044(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
Zn1 N1 2.1261(17) 3_667 ?
Zn1 N1 2.1262(17) . ?
Zn1 N3 2.1086(18) 3_667 ?
Zn1 N3 2.1086(18) . ?
Zn1 O1 2.0974(16) 3_667 ?
Zn1 O1 2.0974(16) . ?
Zn2 Cl1 2.2160(6) . ?
Zn2 Cl2 2.3585(5) 3_666 ?
Zn2 Cl2 2.3454(5) . ?
Zn2 Cl3 2.2078(6) . ?
Cl2 Zn2 2.3585(5) 3_666 ?
N4 C15 1.448(3) . ?
N4 C14 1.318(3) . ?
N4 C21 1.443(3) . ?
N1 C1 1.146(3) . ?
C7 H7 0.9300 . ?
C7 C2 1.390(3) . ?
C7 C6 1.389(3) . ?
N2 C1 1.327(3) . ?
N2 C2 1.444(3) . ?
N2 C8 1.443(3) . ?
C15 C20 1.377(3) . ?
C15 C16 1.386(3) . ?
N3 C14 1.149(3) . ?
C2 C3 1.382(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.384(3) . ?
C23 C24 1.384(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.386(3) . ?
C9 C10 1.386(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.383(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.383(3) . ?
C11 C12 1.389(3) . ?
C13 H13 0.9300 . ?
C13 C8 1.389(3) . ?
C13 C12 1.386(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.379(3) . ?
C25 C26 1.391(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.384(4) . ?
C19 C20 1.382(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.381(4) . ?
C5 C6 1.377(4) . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.389(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(4) . ?
C17 C16 1.391(3) . ?
C21 C26 1.386(3) . ?
C6 H6 0.9300 . ?
C18 H18 0.9300 . ?
C24 H24 0.9300 . ?
C3 H3 0.9300 . ?
C20 H20 0.9300 . ?
C16 H16 0.9300 . ?
C26 H26 0.9300 . ?
O1 H1A 0.79(3) . ?
O1 H1B 0.79(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 Zn1 N1 180.00(9) 3_667 . ?
N3 Zn1 N1 91.37(7) 3_667 3_667 ?
N3 Zn1 N1 88.63(7) . 3_667 ?
N3 Zn1 N1 91.37(7) . . ?
N3 Zn1 N1 88.63(7) 3_667 . ?
N3 Zn1 N3 180.0 . 3_667 ?
O1 Zn1 N1 91.44(7) 3_667 . ?
O1 Zn1 N1 88.57(7) . . ?
O1 Zn1 N1 88.56(7) 3_667 3_667 ?
O1 Zn1 N1 91.43(7) . 3_667 ?
O1 Zn1 N3 89.72(7) . . ?
O1 Zn1 N3 90.27(7) 3_667 . ?
O1 Zn1 N3 89.73(7) 3_667 3_667 ?
O1 Zn1 N3 90.28(7) . 3_667 ?
O1 Zn1 O1 180.00(8) 3_667 . ?
Cl1 Zn2 Cl2 109.50(2) . 3_666 ?
Cl1 Zn2 Cl2 107.68(2) . . ?
Cl2 Zn2 Cl2 93.253(18) . 3_666 ?
Cl3 Zn2 Cl1 120.43(2) . . ?
Cl3 Zn2 Cl2 111.87(2) . . ?
Cl3 Zn2 Cl2 110.70(2) . 3_666 ?
Zn2 Cl2 Zn2 86.747(18) . 3_666 ?
C14 N4 C15 116.55(17) . . ?
C14 N4 C21 119.42(17) . . ?
C21 N4 C15 123.99(17) . . ?
C1 N1 Zn1 178.25(18) . . ?
C2 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C2 118.8(2) . . ?
C1 N2 C2 117.86(18) . . ?
C1 N2 C8 117.36(17) . . ?
C8 N2 C2 123.55(16) . . ?
C20 C15 N4 119.68(19) . . ?
C20 C15 C16 121.5(2) . . ?
C16 C15 N4 118.8(2) . . ?
C14 N3 Zn1 165.65(18) . . ?
N1 C1 N2 179.2(2) . . ?
C7 C2 N2 119.5(2) . . ?
C3 C2 C7 121.2(2) . . ?
C3 C2 N2 119.27(19) . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.5(2) . . ?
C24 C23 H23 119.7 . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C10 C9 C8 119.1(2) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 C23 119.4(2) . . ?
C21 C22 H22 120.3 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.2(2) . . ?
C12 C11 H11 120.4 . . ?
C8 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C8 119.09(19) . . ?
C9 C8 N2 120.21(19) . . ?
C9 C8 C13 120.9(2) . . ?
C13 C8 N2 118.78(18) . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.7(2) . . ?
C26 C25 H25 119.7 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C20 C19 C18 120.9(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.4(2) . . ?
N3 C14 N4 178.2(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C18 C17 H17 120.1 . . ?
C18 C17 C16 119.9(2) . . ?
C16 C17 H17 120.1 . . ?
C22 C21 N4 120.01(18) . . ?
C22 C21 C26 120.83(19) . . ?
C26 C21 N4 119.13(18) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.3(2) . . ?
C5 C6 H6 119.8 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 120.0(2) . . ?
C17 C18 H18 120.0 . . ?
C23 C24 H24 120.2 . . ?
C25 C24 C23 119.6(2) . . ?
C25 C24 H24 120.2 . . ?
C2 C3 C4 119.0(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C15 C20 C19 118.6(2) . . ?
C15 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C15 C16 C17 119.1(2) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C25 C26 H26 120.5 . . ?
C21 C26 C25 119.0(2) . . ?
C21 C26 H26 120.5 . . ?
Zn1 O1 H1A 115(2) . . ?
Zn1 O1 H1B 115(2) . . ?
H1A O1 H1B 109(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C15 C20 C19 -178.8(2) . . . . ?
N4 C15 C16 C17 177.70(19) . . . . ?
N4 C21 C26 C25 177.0(2) . . . . ?
C7 C2 C3 C4 0.2(3) . . . . ?
N2 C2 C3 C4 -179.20(18) . . . . ?
C15 N4 C21 C22 -21.4(3) . . . . ?
C15 N4 C21 C26 160.7(2) . . . . ?
C1 N2 C2 C7 148.96(19) . . . . ?
C1 N2 C2 C3 -31.6(3) . . . . ?
C1 N2 C8 C9 143.2(2) . . . . ?
C1 N2 C8 C13 -33.4(3) . . . . ?
C2 C7 C6 C5 1.9(3) . . . . ?
C2 N2 C8 C9 -23.9(3) . . . . ?
C2 N2 C8 C13 159.60(19) . . . . ?
C23 C22 C21 N4 -177.7(2) . . . . ?
C23 C22 C21 C26 0.2(3) . . . . ?
C22 C23 C24 C25 -0.8(4) . . . . ?
C22 C21 C26 C25 -1.0(4) . . . . ?
C8 N2 C2 C7 -44.1(3) . . . . ?
C8 N2 C2 C3 135.4(2) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C8 C13 C12 C11 -0.2(3) . . . . ?
C5 C4 C3 C2 1.6(3) . . . . ?
C14 N4 C15 C20 133.5(2) . . . . ?
C14 N4 C15 C16 -44.3(3) . . . . ?
C14 N4 C21 C22 156.2(2) . . . . ?
C14 N4 C21 C26 -21.8(3) . . . . ?
C10 C9 C8 N2 -176.19(19) . . . . ?
C10 C9 C8 C13 0.3(3) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C12 C11 C10 C9 0.5(3) . . . . ?
C12 C13 C8 N2 176.59(19) . . . . ?
C12 C13 C8 C9 0.1(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C21 N4 C15 C20 -48.9(3) . . . . ?
C21 N4 C15 C16 133.3(2) . . . . ?
C6 C7 C2 N2 177.46(18) . . . . ?
C6 C7 C2 C3 -2.0(3) . . . . ?
C6 C5 C4 C3 -1.6(3) . . . . ?
C18 C19 C20 C15 1.2(4) . . . . ?
C18 C17 C16 C15 1.1(3) . . . . ?
C24 C23 C22 C21 0.7(3) . . . . ?
C24 C25 C26 C21 0.9(4) . . . . ?
C20 C15 C16 C17 0.0(3) . . . . ?
C20 C19 C18 C17 -0.2(4) . . . . ?
C16 C15 C20 C19 -1.1(3) . . . . ?
C16 C17 C18 C19 -1.0(4) . . . . ?
C26 C25 C24 C23 0.0(4) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 1002745'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sas_n55
_audit_creation_date             2013-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C52 H44 N8 O2 Zn, Br6 Zn2'
_chemical_formula_sum            'C52 H44 Br6 N8 O2 Zn3'
_chemical_formula_weight         1488.52
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.9094(4)
_cell_length_b                   25.7218(12)
_cell_length_c                   14.0861(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 128.053(3)
_cell_angle_gamma                90.00
_cell_volume                     2827.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2875
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8554
_cell_measurement_theta_min      2.5995
_exptl_absorpt_coefficient_mu    5.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9183
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.60
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0355175000
_diffrn_orient_matrix_UB_12      -0.0017694000
_diffrn_orient_matrix_UB_13      -0.0517360000
_diffrn_orient_matrix_UB_21      0.0108034000
_diffrn_orient_matrix_UB_22      -0.0269130000
_diffrn_orient_matrix_UB_23      0.0110591000
_diffrn_orient_matrix_UB_31      -0.0616764000
_diffrn_orient_matrix_UB_32      -0.0057056000
_diffrn_orient_matrix_UB_33      -0.0359842000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_number_gt                3878
_reflns_number_total             4844
_reflns_odcompleteness_completeness 94.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         1.277
_refine_diff_density_min         -1.093
_refine_diff_density_rms         0.146
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4844
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0305P)²+6.5325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1120
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1-H1A
 0.9 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Zn1 Zn 1.0000 0.0000 0.5000 0.0124(2) Uani 1 2 d . . S T
O1 O 0.9023(6) 0.0010(2) 0.3181(4) 0.0175(10) Uani 1 1 d . . D .
N1 N 0.8177(7) -0.0574(2) 0.4649(5) 0.0166(12) Uani 1 1 d . . . .
N2 N 0.6189(7) -0.1287(2) 0.4204(5) 0.0148(12) Uani 1 1 d . . . .
N3 N 1.1678(7) -0.0600(2) 0.5339(5) 0.0190(13) Uani 1 1 d . . . .
N4 N 1.3938(6) -0.1280(2) 0.6266(5) 0.0135(12) Uani 1 1 d . . . .
C1 C 0.7253(9) -0.0901(3) 0.4440(5) 0.0149(15) Uani 1 1 d . . . .
C2 C 0.6879(8) -0.1758(3) 0.4892(6) 0.0152(14) Uani 1 1 d . . . .
C3 C 0.8343(8) -0.1732(3) 0.6095(6) 0.0163(15) Uani 1 1 d . . . .
H3 H 0.8865 -0.1414 0.6443 0.020 Uiso 1 1 calc . . R .
C4 C 0.9005(9) -0.2183(3) 0.6762(7) 0.0264(17) Uani 1 1 d . . . .
H4 H 1.0006 -0.2171 0.7554 0.032 Uiso 1 1 calc . . R .
C5 C 0.8200(10) -0.2650(3) 0.6267(7) 0.0299(19) Uani 1 1 d . . . .
H5 H 0.8633 -0.2951 0.6731 0.036 Uiso 1 1 calc . . R .
C6 C 0.6722(10) -0.2674(3) 0.5062(7) 0.0255(18) Uani 1 1 d . . . .
H6 H 0.6166 -0.2989 0.4726 0.031 Uiso 1 1 calc . . R .
C7 C 0.6098(9) -0.2225(3) 0.4378(6) 0.0212(16) Uani 1 1 d . . . .
H7 H 0.5149 -0.2241 0.3568 0.025 Uiso 1 1 calc . . R .
C8 C 0.4367(8) -0.1166(3) 0.3427(6) 0.0177(15) Uani 1 1 d . . . .
C9 C 0.3713(8) -0.0816(3) 0.2498(5) 0.0147(14) Uani 1 1 d . . . .
H9 H 0.4423 -0.0670 0.2348 0.018 Uiso 1 1 calc . . R .
C10 C 0.1986(9) -0.0682(3) 0.1786(6) 0.0205(16) Uani 1 1 d . . . .
H10 H 0.1550 -0.0440 0.1170 0.025 Uiso 1 1 calc . . R .
C11 C 0.0905(9) -0.0907(3) 0.1988(6) 0.0233(17) Uani 1 1 d . . . .
H11 H -0.0251 -0.0820 0.1509 0.028 Uiso 1 1 calc . . R .
C12 C 0.1587(8) -0.1265(3) 0.2918(6) 0.0218(16) Uani 1 1 d . . . .
H12 H 0.0878 -0.1415 0.3064 0.026 Uiso 1 1 calc . . R .
C13 C 0.3292(8) -0.1401(3) 0.3629(6) 0.0180(15) Uani 1 1 d . . . .
H13 H 0.3724 -0.1647 0.4237 0.022 Uiso 1 1 calc . . R .
C14 C 1.2719(8) -0.0920(3) 0.5777(6) 0.0148(15) Uani 1 1 d . . . .
C15 C 1.5677(8) -0.1095(3) 0.6926(6) 0.0175(15) Uani 1 1 d . . . .
C16 C 1.6020(9) -0.0701(3) 0.6421(7) 0.0241(17) Uani 1 1 d . . . .
H16 H 1.5153 -0.0567 0.5665 0.029 Uiso 1 1 calc . . R .
C17 C 1.7689(11) -0.0514(3) 0.7074(8) 0.036(2) Uani 1 1 d . . . .
H17 H 1.7936 -0.0253 0.6745 0.044 Uiso 1 1 calc . . R .
C18 C 1.8965(10) -0.0704(4) 0.8186(8) 0.041(2) Uani 1 1 d . . . .
H18 H 2.0071 -0.0572 0.8616 0.050 Uiso 1 1 calc . . R .
C19 C 1.8599(10) -0.1103(4) 0.8678(7) 0.041(2) Uani 1 1 d . . . .
H19 H 1.9474 -0.1241 0.9429 0.049 Uiso 1 1 calc . . R .
C20 C 1.6951(9) -0.1293(3) 0.8056(6) 0.0266(17) Uani 1 1 d . . . .
H20 H 1.6703 -0.1550 0.8392 0.032 Uiso 1 1 calc . . R .
C21 C 1.3468(8) -0.1822(3) 0.6107(6) 0.0160(15) Uani 1 1 d . . . .
C22 C 1.4555(9) -0.2199(3) 0.6220(6) 0.0195(16) Uani 1 1 d . . . .
H22 H 1.5616 -0.2108 0.6430 0.023 Uiso 1 1 calc . . R .
C23 C 1.4051(10) -0.2710(3) 0.6017(6) 0.0250(17) Uani 1 1 d . . . .
H23 H 1.4785 -0.2963 0.6097 0.030 Uiso 1 1 calc . . R .
C24 C 1.2485(10) -0.2857(3) 0.5699(7) 0.0304(18) Uani 1 1 d . . . .
H24 H 1.2153 -0.3204 0.5560 0.036 Uiso 1 1 calc . . R .
C25 C 1.1414(10) -0.2472(3) 0.5592(8) 0.035(2) Uani 1 1 d . . . .
H25 H 1.0356 -0.2566 0.5385 0.042 Uiso 1 1 calc . . R .
C26 C 1.1871(9) -0.1963(3) 0.5782(7) 0.0261(18) Uani 1 1 d . . . .
H26 H 1.1130 -0.1711 0.5697 0.031 Uiso 1 1 calc . . R .
Br1 Br 0.30479(8) 0.10921(3) -0.18592(5) 0.01555(17) Uani 1 1 d . . . .
Br2 Br 0.35423(8) 0.00623(3) 0.03867(6) 0.01794(17) Uani 1 1 d . . . .
Br3 Br 0.71558(9) 0.11495(3) 0.16587(6) 0.02103(18) Uani 1 1 d . . . .
Zn2 Zn 0.51020(10) 0.06503(3) -0.00386(7) 0.01460(19) Uani 1 1 d . . . .
H1A H 0.841(7) 0.0294(16) 0.281(5) 0.014(18) Uiso 1 1 d . . D .
H1B H 0.865(12) -0.032(4) 0.284(8) 0.06(3) 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
Zn1 O1 2.108(4) . ?
Zn1 O1 2.108(4) 3_756 ?
Zn1 N1 2.142(5) 3_756 ?
Zn1 N1 2.142(5) . ?
Zn1 N3 2.096(6) . ?
Zn1 N3 2.096(6) 3_756 ?
O1 H1A 0.89(2) . ?
O1 H1B 0.93(9) . ?
N1 C1 1.140(8) . ?
N2 C1 1.333(8) . ?
N2 C2 1.435(8) . ?
N2 C8 1.455(8) . ?
N3 C14 1.157(8) . ?
N4 C14 1.328(8) . ?
N4 C15 1.444(8) . ?
N4 C21 1.443(8) . ?
C2 C3 1.396(9) . ?
C2 C7 1.370(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(11) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(9) . ?
C8 C13 1.398(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.392(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(9) . ?
C13 H13 0.9300 . ?
C15 C16 1.394(9) . ?
C15 C20 1.382(10) . ?
C16 H16 0.9300 . ?
C16 C17 1.392(10) . ?
C17 H17 0.9300 . ?
C17 C18 1.360(12) . ?
C18 H18 0.9300 . ?
C18 C19 1.406(12) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(9) . ?
C21 C26 1.397(9) . ?
C22 H22 0.9300 . ?
C22 C23 1.370(10) . ?
C23 H23 0.9300 . ?
C23 C24 1.377(10) . ?
C24 H24 0.9300 . ?
C24 C25 1.390(10) . ?
C25 H25 0.9300 . ?
C25 C26 1.356(10) . ?
C26 H26 0.9300 . ?
Br1 Zn2 2.3613(10) . ?
Br2 Zn2 2.4934(10) 3_655 ?
Br2 Zn2 2.4852(9) . ?
Br3 Zn2 2.3470(10) . ?
Zn2 Br2 2.4935(10) 3_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 180.0 3_756 . ?
O1 Zn1 N1 87.83(19) 3_756 . ?
O1 Zn1 N1 92.17(19) . . ?
O1 Zn1 N1 92.17(19) 3_756 3_756 ?
O1 Zn1 N1 87.83(19) . 3_756 ?
N1 Zn1 N1 179.999(1) . 3_756 ?
N3 Zn1 O1 90.5(2) . 3_756 ?
N3 Zn1 O1 89.5(2) 3_756 3_756 ?
N3 Zn1 O1 90.5(2) 3_756 . ?
N3 Zn1 O1 89.5(2) . . ?
N3 Zn1 N1 91.0(2) 3_756 . ?
N3 Zn1 N1 91.0(2) . 3_756 ?
N3 Zn1 N1 89.0(2) 3_756 3_756 ?
N3 Zn1 N1 89.0(2) . . ?
N3 Zn1 N3 180.000(1) 3_756 . ?
Zn1 O1 H1A 111(4) . . ?
Zn1 O1 H1B 111(5) . . ?
H1A O1 H1B 122(7) . . ?
C1 N1 Zn1 175.6(5) . . ?
C1 N2 C2 119.1(5) . . ?
C1 N2 C8 116.9(6) . . ?
C2 N2 C8 122.9(5) . . ?
C14 N3 Zn1 165.2(5) . . ?
C14 N4 C15 116.5(5) . . ?
C14 N4 C21 119.3(5) . . ?
C21 N4 C15 124.1(5) . . ?
N1 C1 N2 179.2(8) . . ?
C3 C2 N2 119.0(6) . . ?
C7 C2 N2 120.3(6) . . ?
C7 C2 C3 120.7(6) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(7) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.5(7) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(7) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.5(7) . . ?
C7 C6 H6 120.2 . . ?
C2 C7 C6 119.9(7) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 N2 119.6(6) . . ?
C9 C8 C13 120.3(6) . . ?
C13 C8 N2 120.1(6) . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.8(6) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.5(6) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.7 . . ?
C12 C11 C10 118.7(6) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.4(6) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 H13 120.3 . . ?
C12 C13 C8 119.3(6) . . ?
C12 C13 H13 120.3 . . ?
N3 C14 N4 178.2(7) . . ?
C16 C15 N4 118.7(6) . . ?
C20 C15 N4 120.0(6) . . ?
C20 C15 C16 121.2(6) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.6(7) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.2(8) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.4(7) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(8) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 H20 120.5 . . ?
C19 C20 C15 118.9(7) . . ?
C19 C20 H20 120.5 . . ?
C22 C21 N4 120.4(6) . . ?
C22 C21 C26 119.9(6) . . ?
C26 C21 N4 119.6(6) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.3(6) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 H23 119.2 . . ?
C22 C23 C24 121.7(7) . . ?
C24 C23 H23 119.2 . . ?
C23 C24 H24 121.0 . . ?
C23 C24 C25 118.0(7) . . ?
C25 C24 H24 121.0 . . ?
C24 C25 H25 119.1 . . ?
C26 C25 C24 121.8(7) . . ?
C26 C25 H25 119.1 . . ?
C21 C26 H26 120.4 . . ?
C25 C26 C21 119.2(7) . . ?
C25 C26 H26 120.4 . . ?
Zn2 Br2 Zn2 84.81(3) . 3_655 ?
Br1 Zn2 Br2 110.39(3) . 3_655 ?
Br1 Zn2 Br2 107.87(4) . . ?
Br2 Zn2 Br2 95.19(3) . 3_655 ?
Br3 Zn2 Br1 117.96(4) . . ?
Br3 Zn2 Br2 111.62(4) . 3_655 ?
Br3 Zn2 Br2 111.41(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 N1 C1 N2 48(51) . . . . ?
Zn1 N3 C14 N4 -124(23) . . . . ?
O1 Zn1 N1 C1 61(7) . . . . ?
O1 Zn1 N1 C1 -119(7) 3_756 . . . ?
O1 Zn1 N3 C14 -1(2) 3_756 . . . ?
O1 Zn1 N3 C14 179(2) . . . . ?
N1 Zn1 N1 C1 147(19) 3_756 . . . ?
N1 Zn1 N3 C14 91(2) 3_756 . . . ?
N1 Zn1 N3 C14 -89(2) . . . . ?
N2 C2 C3 C4 179.6(5) . . . . ?
N2 C2 C7 C6 -176.9(6) . . . . ?
N2 C8 C9 C10 -177.1(6) . . . . ?
N2 C8 C13 C12 177.1(6) . . . . ?
N3 Zn1 N1 C1 -28(7) . . . . ?
N3 Zn1 N1 C1 152(7) 3_756 . . . ?
N3 Zn1 N3 C14 -146(100) 3_756 . . . ?
N4 C15 C16 C17 178.2(6) . . . . ?
N4 C15 C20 C19 -178.9(6) . . . . ?
N4 C21 C22 C23 -177.4(6) . . . . ?
N4 C21 C26 C25 177.7(6) . . . . ?
C1 N2 C2 C3 32.4(8) . . . . ?
C1 N2 C2 C7 -148.4(6) . . . . ?
C1 N2 C8 C9 34.8(8) . . . . ?
C1 N2 C8 C13 -144.6(6) . . . . ?
C2 N2 C1 N1 16(48) . . . . ?
C2 N2 C8 C9 -157.6(6) . . . . ?
C2 N2 C8 C13 23.0(9) . . . . ?
C2 C3 C4 C5 -2.6(10) . . . . ?
C3 C2 C7 C6 2.3(9) . . . . ?
C3 C4 C5 C6 2.1(10) . . . . ?
C4 C5 C6 C7 0.6(10) . . . . ?
C5 C6 C7 C2 -2.9(10) . . . . ?
C7 C2 C3 C4 0.4(9) . . . . ?
C8 N2 C1 N1 -176(100) . . . . ?
C8 N2 C2 C3 -134.9(6) . . . . ?
C8 N2 C2 C7 44.3(8) . . . . ?
C8 C9 C10 C11 -1.4(10) . . . . ?
C9 C8 C13 C12 -2.3(10) . . . . ?
C9 C10 C11 C12 0.5(10) . . . . ?
C10 C11 C12 C13 -0.5(11) . . . . ?
C11 C12 C13 C8 1.4(10) . . . . ?
C13 C8 C9 C10 2.3(10) . . . . ?
C14 N4 C15 C16 -44.9(8) . . . . ?
C14 N4 C15 C20 132.6(7) . . . . ?
C14 N4 C21 C22 157.4(6) . . . . ?
C14 N4 C21 C26 -19.6(9) . . . . ?
C15 N4 C14 N3 46(24) . . . . ?
C15 N4 C21 C22 -22.0(9) . . . . ?
C15 N4 C21 C26 161.0(6) . . . . ?
C15 C16 C17 C18 -0.5(11) . . . . ?
C16 C15 C20 C19 -1.4(10) . . . . ?
C16 C17 C18 C19 0.9(12) . . . . ?
C17 C18 C19 C20 -1.6(12) . . . . ?
C18 C19 C20 C15 1.8(11) . . . . ?
C20 C15 C16 C17 0.8(10) . . . . ?
C21 N4 C14 N3 -134(24) . . . . ?
C21 N4 C15 C16 134.5(6) . . . . ?
C21 N4 C15 C20 -47.9(9) . . . . ?
C21 C22 C23 C24 0.3(10) . . . . ?
C22 C21 C26 C25 0.7(11) . . . . ?
C22 C23 C24 C25 -0.3(11) . . . . ?
C23 C24 C25 C26 0.6(12) . . . . ?
C24 C25 C26 C21 -0.7(12) . . . . ?
C26 C21 C22 C23 -0.4(10) . . . . ?
Zn2 Br2 Zn2 Br1 113.38(4) 3_655 . . . ?
Zn2 Br2 Zn2 Br2 0.0 3_655 . . 3_655 ?
Zn2 Br2 Zn2 Br3 -115.66(5) 3_655 . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1002744'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sas_triflate
_audit_creation_date             2013-10-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H22 N6 O2 Zn, 2(C F3 O3 S)'
_chemical_formula_sum            'C11 H22 F6 N6 O8 S2 Zn'
_chemical_formula_weight         609.84
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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'
S S 0.3331 0.5567 '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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   14.7059(7)
_cell_length_b                   9.2052(4)
_cell_length_c                   18.8942(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.429(5)
_cell_angle_gamma                90.00
_cell_volume                     2487.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2985
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.6270
_cell_measurement_theta_min      5.0600
_exptl_absorpt_coefficient_mu    3.809
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13153
_diffrn_reflns_theta_full        69.95
_diffrn_reflns_theta_max         69.95
_diffrn_reflns_theta_min         3.09
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9950
_diffrn_measured_fraction_theta_max 0.9950
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0644367000
_diffrn_orient_matrix_UB_12      -0.0273504000
_diffrn_orient_matrix_UB_13      0.0755434000
_diffrn_orient_matrix_UB_21      0.0248995000
_diffrn_orient_matrix_UB_22      -0.1508822000
_diffrn_orient_matrix_UB_23      -0.0252871000
_diffrn_orient_matrix_UB_31      0.0826440000
_diffrn_orient_matrix_UB_32      0.0669658000
_diffrn_orient_matrix_UB_33      -0.0260424000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_number_gt                3502
_reflns_number_total             4668
_reflns_odcompleteness_completeness 99.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4668
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0624P)²+1.4974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1209
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C2(H2C,H2D,H2E), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C8(H8A,
 H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.22879(3) 0.22278(5) 0.27946(2) 0.02615(14) Uani 1 1 d . . .
S1 S 0.15216(6) 0.72935(9) 0.11761(5) 0.0307(2) Uani 1 1 d . . .
S2 S 0.41080(6) -0.28613(9) 0.38067(4) 0.02939(19) Uani 1 1 d . . .
F1 F -0.02313(16) 0.7241(2) 0.04671(14) 0.0542(6) Uani 1 1 d . . .
F2 F 0.03216(17) 0.5157(2) 0.08605(16) 0.0602(7) Uani 1 1 d . . .
F3 F -0.00123(19) 0.6746(3) 0.16025(16) 0.0683(8) Uani 1 1 d . . .
F4 F 0.40108(17) -0.1712(3) 0.50473(12) 0.0476(6) Uani 1 1 d . . .
F5 F 0.53257(16) -0.1385(2) 0.47583(13) 0.0464(6) Uani 1 1 d . . .
F6 F 0.49988(17) -0.3463(2) 0.51426(12) 0.0491(6) Uani 1 1 d . . .
O1 O 0.22036(19) 0.4502(3) 0.28737(16) 0.0343(6) Uani 1 1 d . . .
H1A H 0.266(3) 0.490(5) 0.323(3) 0.056(13) Uiso 1 1 d . . .
H1B H 0.214(3) 0.501(5) 0.256(2) 0.048(15) Uiso 1 1 d . . .
O2 O 0.22153(19) -0.0028(3) 0.27073(15) 0.0324(5) Uani 1 1 d . . .
H2A H 0.200(3) -0.045(5) 0.234(3) 0.053(14) Uiso 1 1 d . . .
H2B H 0.269(4) -0.052(6) 0.297(3) 0.075(17) Uiso 1 1 d . . .
O3 O 0.1785(2) 0.7055(3) 0.05057(15) 0.0476(7) Uani 1 1 d . . .
O4 O 0.2026(2) 0.6455(3) 0.17786(16) 0.0523(8) Uani 1 1 d . . .
O5 O 0.14088(18) 0.8799(3) 0.13459(14) 0.0403(6) Uani 1 1 d . . .
O6 O 0.37218(18) -0.1520(3) 0.34739(14) 0.0416(6) Uani 1 1 d . . .
O7 O 0.48711(19) -0.3419(3) 0.35351(14) 0.0450(7) Uani 1 1 d . . .
O8 O 0.34159(19) -0.3923(3) 0.38972(15) 0.0455(7) Uani 1 1 d . . .
N1 N 0.11078(19) 0.2294(3) 0.20090(16) 0.0317(6) Uani 1 1 d . . .
N2 N -0.04751(19) 0.1937(3) 0.12674(17) 0.0329(7) Uani 1 1 d . . .
N3 N 0.2394(2) 0.2176(3) 0.38701(16) 0.0350(7) Uani 1 1 d . . .
N4 N 0.2568(2) 0.2706(3) 0.51633(16) 0.0334(6) Uani 1 1 d . . .
N5 N 0.35721(19) 0.2264(3) 0.25855(16) 0.0324(6) Uani 1 1 d . . .
N6 N 0.52388(19) 0.2016(3) 0.31675(15) 0.0287(6) Uani 1 1 d . . .
C1 C 0.0366(2) 0.2107(3) 0.16722(18) 0.0298(7) Uani 1 1 d . . .
C2 C -0.0721(3) 0.0580(4) 0.0858(2) 0.0379(8) Uani 1 1 d . . .
H2C H -0.0160 0.0083 0.0821 0.057 Uiso 1 1 calc R . .
H2D H -0.1087 0.0798 0.0380 0.057 Uiso 1 1 calc R . .
H2E H -0.1076 -0.0028 0.1107 0.057 Uiso 1 1 calc R . .
C3 C -0.1234(2) 0.2913(4) 0.1344(2) 0.0419(9) Uani 1 1 d . . .
H3A H -0.1657 0.2403 0.1574 0.063 Uiso 1 1 calc R . .
H3B H -0.1565 0.3241 0.0872 0.063 Uiso 1 1 calc R . .
H3C H -0.0978 0.3734 0.1637 0.063 Uiso 1 1 calc R . .
C4 C 0.2478(2) 0.2422(3) 0.44768(19) 0.0293(7) Uani 1 1 d . . .
C5 C 0.2340(3) 0.1611(5) 0.5656(2) 0.0480(10) Uani 1 1 d . . .
H5A H 0.1775 0.1883 0.5793 0.072 Uiso 1 1 calc R . .
H5B H 0.2841 0.1545 0.6083 0.072 Uiso 1 1 calc R . .
H5C H 0.2254 0.0686 0.5415 0.072 Uiso 1 1 calc R . .
C6 C 0.2906(3) 0.4137(4) 0.5455(2) 0.0405(9) Uani 1 1 d . . .
H6A H 0.3477 0.4022 0.5820 0.061 Uiso 1 1 calc R . .
H6B H 0.2444 0.4587 0.5668 0.061 Uiso 1 1 calc R . .
H6C H 0.3017 0.4738 0.5069 0.061 Uiso 1 1 calc R . .
C7 C 0.4358(2) 0.2145(3) 0.28565(18) 0.0284(7) Uani 1 1 d . . .
C8 C 0.5687(3) 0.0583(4) 0.3213(2) 0.0343(8) Uani 1 1 d . . .
H8A H 0.5220 -0.0161 0.3176 0.052 Uiso 1 1 calc R . .
H8B H 0.6134 0.0494 0.3671 0.052 Uiso 1 1 calc R . .
H8C H 0.5999 0.0477 0.2823 0.052 Uiso 1 1 calc R . .
C9 C 0.5841(2) 0.3306(4) 0.33039(19) 0.0323(7) Uani 1 1 d . . .
H9A H 0.6160 0.3416 0.2918 0.049 Uiso 1 1 calc R . .
H9B H 0.6291 0.3195 0.3758 0.049 Uiso 1 1 calc R . .
H9C H 0.5465 0.4151 0.3325 0.049 Uiso 1 1 calc R . .
C10 C 0.0334(3) 0.6574(4) 0.1022(2) 0.0420(9) Uani 1 1 d . . .
C11 C 0.4637(3) -0.2336(4) 0.47402(19) 0.0325(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
Zn1 O1 2.104(3) . ?
Zn1 O2 2.084(2) . ?
Zn1 N1 2.006(3) . ?
Zn1 N3 2.002(3) . ?
Zn1 N5 2.017(3) . ?
S1 O3 1.425(3) . ?
S1 O4 1.431(3) . ?
S1 O5 1.440(3) . ?
S1 C10 1.827(4) . ?
S2 O6 1.441(3) . ?
S2 O7 1.433(3) . ?
S2 O8 1.449(3) . ?
S2 C11 1.820(4) . ?
F1 C10 1.327(4) . ?
F2 C10 1.339(4) . ?
F3 C10 1.321(5) . ?
F4 C11 1.328(4) . ?
F5 C11 1.333(4) . ?
F6 C11 1.323(4) . ?
O1 H1A 0.92(5) . ?
O1 H1B 0.75(5) . ?
O2 H2A 0.80(5) . ?
O2 H2B 0.88(5) . ?
N1 C1 1.141(4) . ?
N2 C1 1.304(4) . ?
N2 C2 1.469(4) . ?
N2 C3 1.466(4) . ?
N3 C4 1.147(4) . ?
N4 C4 1.299(5) . ?
N4 C5 1.463(5) . ?
N4 C6 1.470(4) . ?
N5 C7 1.156(4) . ?
N6 C7 1.297(4) . ?
N6 C8 1.469(4) . ?
N6 C9 1.468(4) . ?
C2 H2C 0.9600 . ?
C2 H2D 0.9600 . ?
C2 H2E 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Zn1 O1 173.77(10) . . ?
N1 Zn1 O1 88.13(11) . . ?
N1 Zn1 O2 87.24(11) . . ?
N1 Zn1 N5 122.89(12) . . ?
N3 Zn1 O1 86.77(12) . . ?
N3 Zn1 O2 92.69(11) . . ?
N3 Zn1 N1 126.99(13) . . ?
N3 Zn1 N5 110.10(12) . . ?
N5 Zn1 O1 94.05(11) . . ?
N5 Zn1 O2 91.96(11) . . ?
O3 S1 O4 115.23(19) . . ?
O3 S1 O5 114.53(17) . . ?
O3 S1 C10 104.49(19) . . ?
O4 S1 O5 113.98(17) . . ?
O4 S1 C10 103.35(18) . . ?
O5 S1 C10 103.22(17) . . ?
O6 S2 O8 114.37(17) . . ?
O6 S2 C11 103.40(16) . . ?
O7 S2 O6 114.37(17) . . ?
O7 S2 O8 115.50(18) . . ?
O7 S2 C11 104.37(16) . . ?
O8 S2 C11 102.63(16) . . ?
Zn1 O1 H1A 114(3) . . ?
Zn1 O1 H1B 124(4) . . ?
H1A O1 H1B 106(4) . . ?
Zn1 O2 H2A 124(3) . . ?
Zn1 O2 H2B 117(3) . . ?
H2A O2 H2B 111(5) . . ?
C1 N1 Zn1 163.5(3) . . ?
C1 N2 C2 119.6(3) . . ?
C1 N2 C3 120.6(3) . . ?
C3 N2 C2 118.2(3) . . ?
C4 N3 Zn1 167.1(3) . . ?
C4 N4 C5 120.8(3) . . ?
C4 N4 C6 120.1(3) . . ?
C5 N4 C6 119.1(3) . . ?
C7 N5 Zn1 142.9(3) . . ?
C7 N6 C8 119.7(3) . . ?
C7 N6 C9 120.3(3) . . ?
C9 N6 C8 118.2(3) . . ?
N1 C1 N2 177.5(4) . . ?
N2 C2 H2C 109.5 . . ?
N2 C2 H2D 109.5 . . ?
N2 C2 H2E 109.5 . . ?
H2C C2 H2D 109.5 . . ?
H2C C2 H2E 109.5 . . ?
H2D C2 H2E 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N3 C4 N4 179.6(4) . . ?
N4 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
N4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N5 C7 N6 179.4(4) . . ?
N6 C8 H8A 109.5 . . ?
N6 C8 H8B 109.5 . . ?
N6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N6 C9 H9A 109.5 . . ?
N6 C9 H9B 109.5 . . ?
N6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
F1 C10 S1 111.0(3) . . ?
F1 C10 F2 107.3(3) . . ?
F2 C10 S1 110.5(3) . . ?
F3 C10 S1 111.3(3) . . ?
F3 C10 F1 108.0(3) . . ?
F3 C10 F2 108.6(3) . . ?
F4 C11 S2 110.8(2) . . ?
F4 C11 F5 107.7(3) . . ?
F5 C11 S2 110.5(2) . . ?
F6 C11 S2 111.9(2) . . ?
F6 C11 F4 108.4(3) . . ?
F6 C11 F5 107.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 N1 C1 N2 174(8) . . . . ?
Zn1 N3 C4 N4 74(66) . . . . ?
Zn1 N5 C7 N6 -31(40) . . . . ?
O1 Zn1 N1 C1 -123.5(10) . . . . ?
O1 Zn1 N3 C4 -11.8(13) . . . . ?
O1 Zn1 N5 C7 97.3(4) . . . . ?
O2 Zn1 N1 C1 52.4(10) . . . . ?
O2 Zn1 N3 C4 174.4(13) . . . . ?
O2 Zn1 N5 C7 -84.3(4) . . . . ?
O3 S1 C10 F1 -58.6(3) . . . . ?
O3 S1 C10 F2 60.4(3) . . . . ?
O3 S1 C10 F3 -178.9(3) . . . . ?
O4 S1 C10 F1 -179.5(3) . . . . ?
O4 S1 C10 F2 -60.6(3) . . . . ?
O4 S1 C10 F3 60.1(3) . . . . ?
O5 S1 C10 F1 61.5(3) . . . . ?
O5 S1 C10 F2 -179.6(3) . . . . ?
O5 S1 C10 F3 -58.9(3) . . . . ?
O6 S2 C11 F4 56.2(3) . . . . ?
O6 S2 C11 F5 -63.1(3) . . . . ?
O6 S2 C11 F6 177.3(3) . . . . ?
O7 S2 C11 F4 176.2(2) . . . . ?
O7 S2 C11 F5 56.9(3) . . . . ?
O7 S2 C11 F6 -62.7(3) . . . . ?
O8 S2 C11 F4 -63.0(3) . . . . ?
O8 S2 C11 F5 177.7(2) . . . . ?
O8 S2 C11 F6 58.1(3) . . . . ?
N1 Zn1 N3 C4 -97.1(13) . . . . ?
N1 Zn1 N5 C7 -172.3(4) . . . . ?
N3 Zn1 N1 C1 -38.9(10) . . . . ?
N3 Zn1 N5 C7 9.2(5) . . . . ?
N5 Zn1 N1 C1 142.9(10) . . . . ?
N5 Zn1 N3 C4 81.3(13) . . . . ?
C2 N2 C1 N1 111(9) . . . . ?
C3 N2 C1 N1 -83(9) . . . . ?
C5 N4 C4 N3 94(65) . . . . ?
C6 N4 C4 N3 -86(66) . . . . ?
C8 N6 C7 N5 122(40) . . . . ?
C9 N6 C7 N5 -74(40) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 967882'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sas_but_107
_audit_creation_date             2014-01-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H12 F6 N4 O6 S2 Zn'
_chemical_formula_sum            'C8 H12 F6 N4 O6 S2 Zn'
_chemical_formula_weight         503.71
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3213(6)
_cell_length_b                   9.5366(7)
_cell_length_c                   11.0391(10)
_cell_angle_alpha                98.656(7)
_cell_angle_beta                 113.153(7)
_cell_angle_gamma                92.342(6)
_cell_volume                     886.56(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2874
_cell_measurement_temperature    99.99(16)
_cell_measurement_theta_max      27.9440
_cell_measurement_theta_min      3.3200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8380
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.695
_diffrn_ambient_temperature      99.99(16)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0134996000
_diffrn_orient_matrix_UB_12      0.0675238000
_diffrn_orient_matrix_UB_13      -0.0193652000
_diffrn_orient_matrix_UB_21      -0.0241555000
_diffrn_orient_matrix_UB_22      -0.0325811000
_diffrn_orient_matrix_UB_23      -0.0680898000
_diffrn_orient_matrix_UB_31      -0.0785337000
_diffrn_orient_matrix_UB_32      -0.0104191000
_diffrn_orient_matrix_UB_33      -0.0061870000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3152
_reflns_number_total             3941
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+0.1280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0907
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C2A(H2AA,H2AB,H2AC), C3(H3A,H3B,H3C), C3A(H3AA,H3AB,H3AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.5000 0.5000 0.5000 0.01224(12) Uani 1 2 d S T P . .
Zn1A Zn 0.5000 0.0000 0.5000 0.01356(13) Uani 1 2 d S T P . .
S1 S 0.45087(8) 0.71119(8) 0.26836(7) 0.01404(17) Uani 1 1 d . . . . .
S1A S 0.23186(8) 0.21402(8) 0.34868(7) 0.01355(16) Uani 1 1 d . . . . .
F1 F 0.1714(2) 0.5661(2) 0.16792(19) 0.0302(5) Uani 1 1 d . . . . .
F1A F 0.26656(19) 0.0662(2) 0.14329(18) 0.0257(4) Uani 1 1 d . . . . .
F2 F 0.2035(2) 0.7147(2) 0.04990(19) 0.0324(5) Uani 1 1 d . . . . .
F2A F 0.0431(2) 0.0204(2) 0.15022(19) 0.0293(5) Uani 1 1 d . . . . .
F3 F 0.3079(2) 0.5183(2) 0.05256(19) 0.0315(5) Uani 1 1 d . . . . .
F3A F 0.0954(2) 0.2154(2) 0.09300(19) 0.0338(5) Uani 1 1 d . . . . .
O1 O 0.5132(2) 0.5962(2) 0.3397(2) 0.0158(4) Uani 1 1 d . . . . .
O1A O 0.3553(2) 0.3176(2) 0.3556(2) 0.0148(4) Uani 1 1 d . . . . .
O2 O 0.3898(2) 0.8158(2) 0.3397(2) 0.0157(4) Uani 1 1 d . . . . .
O2A O 0.2894(2) 0.1003(2) 0.4228(2) 0.0161(4) Uani 1 1 d . . . . .
O3 O 0.5455(2) 0.7656(2) 0.2071(2) 0.0211(5) Uani 1 1 d . . . . .
O3A O 0.0992(2) 0.2706(2) 0.3644(2) 0.0203(5) Uani 1 1 d . . . . .
N1 N 0.3017(3) 0.5868(3) 0.4896(3) 0.0152(5) Uani 1 1 d . . . . .
N1A N 0.5926(3) 0.0831(3) 0.3867(3) 0.0155(5) Uani 1 1 d . . . . .
N2 N 0.0394(3) 0.6657(3) 0.3937(3) 0.0190(6) Uani 1 1 d . . . . .
N2A N 0.6088(3) 0.1518(3) 0.1872(3) 0.0208(6) Uani 1 1 d . . . . .
C1 C 0.1799(3) 0.6245(3) 0.4432(3) 0.0139(6) Uani 1 1 d . . . . .
C1A C 0.6005(3) 0.1149(3) 0.2939(3) 0.0154(6) Uani 1 1 d . . . . .
C2 C 0.0180(4) 0.8149(4) 0.3836(4) 0.0329(9) Uani 1 1 d . . . . .
H2A H 0.1172 0.8724 0.4310 0.049 Uiso 1 1 calc GR . . . .
H2B H -0.0540 0.8460 0.4221 0.049 Uiso 1 1 calc GR . . . .
H2C H -0.0232 0.8245 0.2911 0.049 Uiso 1 1 calc GR . . . .
C2A C 0.7016(4) 0.0764(4) 0.1254(4) 0.0380(10) Uani 1 1 d . . . . .
H2AA H 0.8016 0.1311 0.1532 0.057 Uiso 1 1 calc GR . . . .
H2AB H 0.6476 0.0631 0.0297 0.057 Uiso 1 1 calc GR . . . .
H2AC H 0.7172 -0.0149 0.1524 0.057 Uiso 1 1 calc GR . . . .
C3 C -0.0981(3) 0.5600(3) 0.3258(3) 0.0233(7) Uani 1 1 d . . . . .
H3A H -0.1382 0.5581 0.2310 0.035 Uiso 1 1 calc GR . . . .
H3B H -0.1776 0.5850 0.3576 0.035 Uiso 1 1 calc GR . . . .
H3C H -0.0691 0.4676 0.3441 0.035 Uiso 1 1 calc GR . . . .
C3A C 0.5524(4) 0.2854(3) 0.1458(3) 0.0240(7) Uani 1 1 d . . . . .
H3AA H 0.4950 0.3240 0.1963 0.036 Uiso 1 1 calc GR . . . .
H3AB H 0.4850 0.2671 0.0521 0.036 Uiso 1 1 calc GR . . . .
H3AC H 0.6403 0.3526 0.1620 0.036 Uiso 1 1 calc GR . . . .
C4 C 0.2726(4) 0.6227(3) 0.1280(3) 0.0210(7) Uani 1 1 d . . . . .
C14 C 0.1551(3) 0.1238(3) 0.1744(3) 0.0178(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
Zn1 O1 2.1542(19) . ?
Zn1 O1 2.1542(19) 2_666 ?
Zn1 O1A 2.161(2) 2_666 ?
Zn1 O1A 2.161(2) . ?
Zn1 N1 2.026(2) . ?
Zn1 N1 2.026(2) 2_666 ?
Zn1A O2 2.181(2) 2_666 ?
Zn1A O2 2.181(2) 1_545 ?
Zn1A O2A 2.1395(19) . ?
Zn1A O2A 2.1395(19) 2_656 ?
Zn1A N1A 2.007(2) 2_656 ?
Zn1A N1A 2.007(2) . ?
S1 O1 1.453(2) . ?
S1 O2 1.450(2) . ?
S1 O3 1.429(2) . ?
S1 C4 1.828(3) . ?
S1A O1A 1.4557(19) . ?
S1A O2A 1.450(2) . ?
S1A O3A 1.430(2) . ?
S1A C14 1.823(3) . ?
F1 C4 1.317(3) . ?
F1A C14 1.330(3) . ?
F2 C4 1.328(3) . ?
F2A C14 1.324(3) . ?
F3 C4 1.336(4) . ?
F3A C14 1.328(3) . ?
O2 Zn1A 2.181(2) 1_565 ?
N1 C1 1.146(4) . ?
N1A C1A 1.140(4) . ?
N2 C1 1.308(4) . ?
N2 C2 1.460(4) . ?
N2 C3 1.460(4) . ?
N2A C1A 1.308(4) . ?
N2A C2A 1.449(4) . ?
N2A C3A 1.466(4) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3A H3AA 0.9600 . ?
C3A H3AB 0.9600 . ?
C3A H3AC 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 180.0 2_666 . ?
O1 Zn1 O1A 90.15(7) . 2_666 ?
O1 Zn1 O1A 89.85(7) 2_666 2_666 ?
O1 Zn1 O1A 90.15(7) 2_666 . ?
O1 Zn1 O1A 89.85(7) . . ?
O1A Zn1 O1A 180.00(11) . 2_666 ?
N1 Zn1 O1 93.23(8) 2_666 2_666 ?
N1 Zn1 O1 86.77(8) . 2_666 ?
N1 Zn1 O1 93.23(8) . . ?
N1 Zn1 O1 86.77(8) 2_666 . ?
N1 Zn1 O1A 91.32(9) . 2_666 ?
N1 Zn1 O1A 91.32(9) 2_666 . ?
N1 Zn1 O1A 88.68(9) . . ?
N1 Zn1 O1A 88.68(9) 2_666 2_666 ?
N1 Zn1 N1 180.0 2_666 . ?
O2 Zn1A O2 180.0 2_666 1_545 ?
O2A Zn1A O2 90.77(8) . 2_666 ?
O2A Zn1A O2 89.22(8) 2_656 2_666 ?
O2A Zn1A O2 89.23(8) . 1_545 ?
O2A Zn1A O2 90.78(8) 2_656 1_545 ?
O2A Zn1A O2A 180.0 2_656 . ?
N1A Zn1A O2 90.06(9) 2_656 1_545 ?
N1A Zn1A O2 89.94(9) . 1_545 ?
N1A Zn1A O2 89.94(9) 2_656 2_666 ?
N1A Zn1A O2 90.06(9) . 2_666 ?
N1A Zn1A O2A 86.87(8) . 2_656 ?
N1A Zn1A O2A 93.13(8) 2_656 2_656 ?
N1A Zn1A O2A 86.87(8) 2_656 . ?
N1A Zn1A O2A 93.13(8) . . ?
N1A Zn1A N1A 180.0 2_656 . ?
O1 S1 C4 103.12(14) . . ?
O2 S1 O1 113.67(12) . . ?
O2 S1 C4 102.36(13) . . ?
O3 S1 O1 114.26(12) . . ?
O3 S1 O2 116.54(12) . . ?
O3 S1 C4 104.60(14) . . ?
O1A S1A C14 102.25(13) . . ?
O2A S1A O1A 113.96(12) . . ?
O2A S1A C14 103.36(13) . . ?
O3A S1A O1A 116.37(13) . . ?
O3A S1A O2A 114.19(12) . . ?
O3A S1A C14 104.41(13) . . ?
S1 O1 Zn1 139.45(12) . . ?
S1A O1A Zn1 135.34(12) . . ?
S1 O2 Zn1A 133.16(12) . 1_565 ?
S1A O2A Zn1A 138.99(12) . . ?
C1 N1 Zn1 159.1(2) . . ?
C1A N1A Zn1A 159.1(2) . . ?
C1 N2 C2 121.0(3) . . ?
C1 N2 C3 120.2(3) . . ?
C2 N2 C3 118.0(2) . . ?
C1A N2A C2A 119.7(3) . . ?
C1A N2A C3A 120.4(3) . . ?
C2A N2A C3A 118.8(3) . . ?
N1 C1 N2 177.8(3) . . ?
N1A C1A N2A 179.6(3) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2A C2A H2AA 109.5 . . ?
N2A C2A H2AB 109.5 . . ?
N2A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2A C3A H3AA 109.5 . . ?
N2A C3A H3AB 109.5 . . ?
N2A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
F1 C4 S1 112.3(2) . . ?
F1 C4 F2 108.8(3) . . ?
F1 C4 F3 107.8(3) . . ?
F2 C4 S1 110.3(2) . . ?
F2 C4 F3 107.2(3) . . ?
F3 C4 S1 110.3(2) . . ?
F1A C14 S1A 111.7(2) . . ?
F2A C14 S1A 110.8(2) . . ?
F2A C14 F1A 107.8(3) . . ?
F2A C14 F3A 108.3(2) . . ?
F3A C14 S1A 110.4(2) . . ?
F3A C14 F1A 107.7(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
O1 S1 O2 Zn1A 81.84(18) . . . 1_565 ?
O1 S1 C4 F1 60.3(2) . . . . ?
O1 S1 C4 F2 -178.2(2) . . . . ?
O1 S1 C4 F3 -60.0(2) . . . . ?
O1A S1A O2A Zn1A -21.5(2) . . . . ?
O1A S1A C14 F1A 57.6(2) . . . . ?
O1A S1A C14 F2A 177.78(19) . . . . ?
O1A S1A C14 F3A -62.2(2) . . . . ?
O2 S1 O1 Zn1 18.6(2) . . . . ?
O2 S1 C4 F1 -58.0(2) . . . . ?
O2 S1 C4 F2 63.6(2) . . . . ?
O2 S1 C4 F3 -178.19(19) . . . . ?
O2A S1A O1A Zn1 -80.16(19) . . . . ?
O2A S1A C14 F1A -61.0(2) . . . . ?
O2A S1A C14 F2A 59.2(2) . . . . ?
O2A S1A C14 F3A 179.17(19) . . . . ?
O3 S1 O1 Zn1 155.74(17) . . . . ?
O3 S1 O2 Zn1A -54.2(2) . . . 1_565 ?
O3 S1 C4 F1 -180.0(2) . . . . ?
O3 S1 C4 F2 -58.4(2) . . . . ?
O3 S1 C4 F3 59.8(2) . . . . ?
O3A S1A O1A Zn1 56.0(2) . . . . ?
O3A S1A O2A Zn1A -158.57(18) . . . . ?
O3A S1A C14 F1A 179.2(2) . . . . ?
O3A S1A C14 F2A -60.5(2) . . . . ?
O3A S1A C14 F3A 59.4(2) . . . . ?
C4 S1 O1 Zn1 -91.4(2) . . . . ?
C4 S1 O2 Zn1A -167.69(16) . . . 1_565 ?
C14 S1A O1A Zn1 169.04(16) . . . . ?
C14 S1A O2A Zn1A 88.7(2) . . . . ?


_database_code_depnum_ccdc_archive 'CCDC 1006350'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sas_trifl_3
_audit_creation_date             2013-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H34 N6 O2 Zn, 2(C F3 O3 S)'
_chemical_formula_sum            'C20 H34 F6 N6 O8 S2 Zn'
_chemical_formula_weight         730.02
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
S S 0.3331 0.5567 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y+1/2, z'
3 'x+1/2, -y, -z+1/2'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y-1/2, -z'
7 '-x-1/2, y, z-1/2'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   7.5157(2)
_cell_length_b                   17.6633(6)
_cell_length_c                   23.4601(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3114.37(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5380
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.5750
_cell_measurement_theta_min      3.7600
_exptl_absorpt_coefficient_mu    3.148
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19816
_diffrn_reflns_theta_full        72.50
_diffrn_reflns_theta_max         72.50
_diffrn_reflns_theta_min         3.77
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9925
_diffrn_measured_fraction_theta_max 0.9925
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0905962000
_diffrn_orient_matrix_UB_12      0.0161991000
_diffrn_orient_matrix_UB_13      0.0576423000
_diffrn_orient_matrix_UB_21      -0.0303527000
_diffrn_orient_matrix_UB_22      0.0828316000
_diffrn_orient_matrix_UB_23      -0.0181168000
_diffrn_orient_matrix_UB_31      -0.1813281000
_diffrn_orient_matrix_UB_32      -0.0218571000
_diffrn_orient_matrix_UB_33      -0.0257960000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_number_gt                2488
_reflns_number_total             3097
_reflns_odcompleteness_completeness 94.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0520P)²+4.1567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1196
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 C10-H10A
 0.96 with sigma of 0.02
3. Others
 Fixed Sof: C8(0.5) H8A(0.5) H8B(0.5) C9(0.5) H9A(0.5) H9B(0.5) C10(0.5)
 H10A(0.5) H10B(0.5) C11(0.5) H11A(0.5) H11B(0.5) C12(0.5) H12A(0.5) H12B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B),
 C9(H9A,H9B), C12(H12A,H12B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.2500 0.2500 0.26934(2) 0.02520(16) Uani 1 2 d S . .
S1 S 0.22156(9) 0.58388(4) 0.61922(3) 0.02923(18) Uani 1 1 d . . .
F1 F 0.2756(3) 0.65674(14) 0.52386(9) 0.0608(6) Uani 1 1 d . . .
F2 F 0.4061(4) 0.54856(18) 0.52958(9) 0.0980(12) Uani 1 1 d . . .
F3 F 0.1248(4) 0.55536(14) 0.51476(10) 0.0859(9) Uani 1 1 d . . .
O1 O 0.4848(3) 0.25146(14) 0.31099(9) 0.0321(4) Uani 1 1 d . . .
H1A H 0.521(6) 0.286(3) 0.3265(18) 0.067(15) Uiso 1 1 d . . .
H1B H 0.515(6) 0.215(3) 0.333(2) 0.080(16) Uiso 1 1 d . . .
O2 O 0.0612(3) 0.62827(12) 0.62579(9) 0.0393(5) Uani 1 1 d . . .
O3 O 0.3802(3) 0.61823(12) 0.64177(10) 0.0409(5) Uani 1 1 d . . .
O4 O 0.2028(3) 0.50495(12) 0.63164(11) 0.0478(6) Uani 1 1 d . . .
N1 N 0.2481(3) 0.36759(13) 0.27507(10) 0.0306(5) Uani 1 1 d . . .
N2 N 0.2356(3) 0.49683(12) 0.31253(10) 0.0307(5) Uani 1 1 d . . .
N3 N 0.2500 0.2500 0.18339(14) 0.0348(8) Uani 1 2 d S . .
N4 N 0.2500 0.2500 0.07861(16) 0.0536(12) Uani 1 2 d S . .
C1 C 0.2379(4) 0.42778(15) 0.29303(11) 0.0275(6) Uani 1 1 d . . .
C2 C 0.1380(4) 0.55739(16) 0.28235(14) 0.0353(7) Uani 1 1 d . . .
H2A H 0.0223 0.5649 0.2998 0.042 Uiso 1 1 calc R . .
H2B H 0.1203 0.5434 0.2428 0.042 Uiso 1 1 calc R . .
C3 C 0.2466(4) 0.62996(16) 0.28601(15) 0.0385(7) Uani 1 1 d . . .
H3A H 0.3554 0.6241 0.2642 0.046 Uiso 1 1 calc R . .
H3B H 0.1793 0.6713 0.2695 0.046 Uiso 1 1 calc R . .
C4 C 0.2926(4) 0.64895(16) 0.34743(15) 0.0385(7) Uani 1 1 d . . .
H4A H 0.1843 0.6601 0.3683 0.046 Uiso 1 1 calc R . .
H4B H 0.3674 0.6937 0.3483 0.046 Uiso 1 1 calc R . .
C5 C 0.3898(4) 0.58318(16) 0.37615(13) 0.0361(7) Uani 1 1 d . . .
H5A H 0.5033 0.5750 0.3575 0.043 Uiso 1 1 calc R . .
H5B H 0.4126 0.5956 0.4158 0.043 Uiso 1 1 calc R . .
C6 C 0.2791(4) 0.51147(16) 0.37282(12) 0.0339(6) Uani 1 1 d . . .
H6A H 0.3453 0.4692 0.3885 0.041 Uiso 1 1 calc R . .
H6B H 0.1706 0.5175 0.3948 0.041 Uiso 1 1 calc R . .
C7 C 0.2500 0.2500 0.13418(18) 0.0358(9) Uani 0.50 1 d P A .
C8 C 0.3434(11) 0.3293(4) 0.0528(3) 0.0381(14) Uani 0.50 1 d P A 1
H8A H 0.3231 0.3713 0.0785 0.046 Uiso 0.50 1 calc PR A 1
H8B H 0.4706 0.3224 0.0482 0.046 Uiso 0.50 1 calc PR A 1
C9 C 0.2558(9) 0.3445(4) -0.0049(3) 0.0396(14) Uani 0.50 1 d P A 1
H9A H 0.1335 0.3602 0.0011 0.048 Uiso 0.50 1 calc PR A 1
H9B H 0.3179 0.3855 -0.0239 0.048 Uiso 0.50 1 calc PR A 1
C10 C 0.2591(12) 0.2748(4) -0.0425(3) 0.0412(17) Uani 0.50 1 d PD . 1
H10A H 0.204(9) 0.285(4) -0.0789(16) 0.05(2) Uiso 0.50 1 d PD B 1
H10B H 0.396(10) 0.260(4) -0.051(3) 0.036(17) Uiso 0.50 1 d P C 1
C11 C 0.3274(13) 0.2919(5) -0.0132(4) 0.0499(18) Uani 0.50 1 d P . 2
H11A H 0.445(11) 0.281(4) -0.004(3) 0.05(2) Uiso 0.50 1 d P D 2
H11B H 0.321(11) 0.340(5) -0.035(3) 0.05(2) Uiso 0.50 1 d P E 2
C12 C 0.2438(11) 0.3088(4) 0.0438(3) 0.0403(15) Uani 0.50 1 d P A 2
H12A H 0.3053 0.3512 0.0613 0.048 Uiso 0.50 1 calc PR A 2
H12B H 0.1207 0.3235 0.0381 0.048 Uiso 0.50 1 calc PR A 2
C13 C 0.2585(5) 0.5866(2) 0.54290(14) 0.0501(9) 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
Zn1 O1 2.017(2) 2 ?
Zn1 O1 2.017(2) . ?
Zn1 N1 2.081(2) . ?
Zn1 N1 2.081(2) 2 ?
Zn1 N3 2.016(3) . ?
S1 O2 1.446(2) . ?
S1 O3 1.438(2) . ?
S1 O4 1.431(2) . ?
S1 C13 1.812(3) . ?
F1 C13 1.323(5) . ?
F2 C13 1.334(4) . ?
F3 C13 1.323(5) . ?
O1 H1A 0.76(5) . ?
O1 H1B 0.85(5) . ?
N1 C1 1.146(4) . ?
N2 C1 1.303(3) . ?
N2 C2 1.478(3) . ?
N2 C6 1.475(4) . ?
N3 C7 1.155(5) . ?
N4 C7 1.304(6) . ?
N4 C8 1.679(7) . ?
N4 C8 1.679(7) 2 ?
N4 C12 1.322(7) 2 ?
N4 C12 1.322(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.522(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.519(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.529(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.518(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.528(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.515(10) . ?
C9 H11B 0.87(8) . ?
C10 C10 0.886(14) 2 ?
C10 H10A 0.97(2) . ?
C10 H10B 1.08(7) . ?
C10 H11B 1.25(8) . ?
C11 H10B 1.17(7) . ?
C11 C11 1.883(17) 2 ?
C11 H11A 0.93(8) . ?
C11 H11B 0.99(8) . ?
C11 C12 1.509(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 122.06(12) . 2 ?
O1 Zn1 N1 87.82(9) 2 2 ?
O1 Zn1 N1 87.82(9) . . ?
O1 Zn1 N1 88.59(10) 2 . ?
O1 Zn1 N1 88.60(10) . 2 ?
N1 Zn1 N1 172.60(13) 2 . ?
N3 Zn1 O1 118.97(6) . . ?
N3 Zn1 O1 118.97(6) . 2 ?
N3 Zn1 N1 93.70(6) . 2 ?
N3 Zn1 N1 93.70(6) . . ?
O2 S1 C13 102.62(14) . . ?
O3 S1 O2 115.01(13) . . ?
O3 S1 C13 103.02(17) . . ?
O4 S1 O2 115.10(14) . . ?
O4 S1 O3 114.69(14) . . ?
O4 S1 C13 104.02(17) . . ?
Zn1 O1 H1A 124(3) . . ?
Zn1 O1 H1B 121(3) . . ?
H1A O1 H1B 103(4) . . ?
C1 N1 Zn1 161.8(2) . . ?
C1 N2 C2 121.1(2) . . ?
C1 N2 C6 119.9(2) . . ?
C6 N2 C2 116.3(2) . . ?
C7 N3 Zn1 180.0 . . ?
C7 N4 C8 111.2(3) . 2 ?
C7 N4 C8 111.2(3) . . ?
C7 N4 C12 128.1(3) . 2 ?
C7 N4 C12 128.1(3) . . ?
C8 N4 C8 137.7(5) . 2 ?
C12 N4 C8 30.3(4) 2 2 ?
C12 N4 C8 114.7(5) . 2 ?
C12 N4 C8 30.3(4) . . ?
C12 N4 C8 114.7(5) 2 . ?
C12 N4 C12 103.7(6) 2 . ?
N1 C1 N2 176.8(3) . . ?
N2 C2 H2A 110.0 . . ?
N2 C2 H2B 110.0 . . ?
N2 C2 C3 108.4(2) . . ?
H2A C2 H2B 108.4 . . ?
C3 C2 H2A 110.0 . . ?
C3 C2 H2B 110.0 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.2(3) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C3 C4 C5 111.0(2) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C4 110.5(2) . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
N2 C6 C5 108.5(2) . . ?
N2 C6 H6A 110.0 . . ?
N2 C6 H6B 110.0 . . ?
C5 C6 H6A 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
N3 C7 N4 180.0 . . ?
N4 C8 H8A 110.4 . . ?
N4 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C9 C8 N4 106.7(5) . . ?
C9 C8 H8A 110.4 . . ?
C9 C8 H8B 110.4 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C8 C9 H11B 118(6) . . ?
H9A C9 H9B 108.0 . . ?
H9A C9 H11B 132.9 . . ?
H9B C9 H11B 54.7 . . ?
C10 C9 C8 111.4(6) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C10 C9 H11B 56(5) . . ?
C9 C10 H10A 110(4) . . ?
C9 C10 H10B 109(4) . . ?
C9 C10 H11B 35(4) . . ?
C10 C10 C9 143.2(5) 2 . ?
C10 C10 H10A 97(4) 2 . ?
C10 C10 H10B 85(4) 2 . ?
C10 C10 H11B 165(4) 2 . ?
H10A C10 H10B 107(6) . . ?
H10A C10 H11B 96(6) . . ?
H10B C10 H11B 84(5) . . ?
H10B C11 H11A 71(6) . . ?
H10B C11 H11B 93(6) . . ?
C11 C11 H10B 84(3) 2 . ?
C11 C11 H11A 115(5) 2 . ?
C11 C11 H11B 130(5) 2 . ?
H11A C11 H11B 110(7) . . ?
C12 C11 H10B 162(3) . . ?
C12 C11 C11 84.2(5) . 2 ?
C12 C11 H11A 103(5) . . ?
C12 C11 H11B 106(5) . . ?
N4 C12 C11 112.2(6) . . ?
N4 C12 H12A 109.2 . . ?
N4 C12 H12B 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
F1 C13 S1 111.9(2) . . ?
F1 C13 F2 108.2(3) . . ?
F2 C13 S1 110.2(2) . . ?
F3 C13 S1 111.5(3) . . ?
F3 C13 F1 107.2(3) . . ?
F3 C13 F2 107.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 N1 C1 N2 120(5) . . . . ?
Zn1 N3 C7 N4 0(100) . . . . ?
O1 Zn1 N1 C1 -72.2(7) . . . . ?
O1 Zn1 N1 C1 50.0(7) 2 . . . ?
O1 Zn1 N3 C7 -80(100) 2 . . . ?
O1 Zn1 N3 C7 100(96) . . . . ?
O2 S1 C13 F1 58.6(3) . . . . ?
O2 S1 C13 F2 179.0(3) . . . . ?
O2 S1 C13 F3 -61.5(3) . . . . ?
O3 S1 C13 F1 -61.2(3) . . . . ?
O3 S1 C13 F2 59.2(3) . . . . ?
O3 S1 C13 F3 178.7(2) . . . . ?
O4 S1 C13 F1 178.8(3) . . . . ?
O4 S1 C13 F2 -60.8(3) . . . . ?
O4 S1 C13 F3 58.8(3) . . . . ?
N1 Zn1 N1 C1 -11.1(7) 2 . . . ?
N1 Zn1 N3 C7 10(96) 2 . . . ?
N1 Zn1 N3 C7 -170(100) . . . . ?
N2 C2 C3 C4 -53.8(3) . . . . ?
N3 Zn1 N1 C1 168.9(7) . . . . ?
N4 C8 C9 C10 -50.7(7) . . . . ?
C1 N2 C2 C3 -141.7(3) . . . . ?
C1 N2 C6 C5 140.5(3) . . . . ?
C2 N2 C1 N1 106(5) . . . . ?
C2 N2 C6 C5 -58.2(3) . . . . ?
C2 C3 C4 C5 55.8(4) . . . . ?
C3 C4 C5 C6 -56.4(3) . . . . ?
C4 C5 C6 N2 55.3(3) . . . . ?
C6 N2 C1 N1 -94(5) . . . . ?
C6 N2 C2 C3 57.2(3) . . . . ?
C7 N4 C8 C9 -151.0(4) . . . . ?
C7 N4 C12 C11 153.9(5) . . . . ?
C8 N4 C7 N3 -157(100) 2 . . . ?
C8 N4 C7 N3 23(84) . . . . ?
C8 N4 C8 C9 29.0(4) 2 . . . ?
C8 N4 C12 C11 89.6(10) . . . . ?
C8 N4 C12 C11 -56.1(7) 2 . . . ?
C8 C9 C10 C10 44(3) . . . 2 ?
C11 C11 C12 N4 52.7(8) 2 . . . ?
C12 N4 C7 N3 174(100) 2 . . . ?
C12 N4 C7 N3 -6(84) . . . . ?
C12 N4 C8 C9 53.9(7) 2 . . . ?
C12 N4 C8 C9 -20.5(7) . . . . ?
C12 N4 C12 C11 -26.1(5) 2 . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1002742'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_but139
_audit_creation_date             2014-05-20
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 H16 Cl2 N4 O2 Zn'
_chemical_formula_sum            'C6 H16 Cl2 N4 O2 Zn'
_chemical_formula_weight         312.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H16 o2 zn1 cl2'
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'
O O 0.0492 0.0322 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   13.2455(7)
_cell_length_b                   10.3779(9)
_cell_length_c                   18.5884(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2555.2(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2631
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.9070
_cell_measurement_theta_min      4.7570
_exptl_absorpt_coefficient_mu    6.456
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8196
_diffrn_reflns_theta_full        72.49
_diffrn_reflns_theta_max         72.49
_diffrn_reflns_theta_min         4.76
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9565
_diffrn_measured_fraction_theta_max 0.9565
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -105.00  -79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -131.0000   12.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega -114.00  -67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -140.0000 -161.0000 47

#__ type_ start__ end____ width___ exp.time_
  3 omega  -44.00    0.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
  4 omega  -48.00   31.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -150.0000 79

#__ type_ start__ end____ width___ exp.time_
  5 omega   35.00   61.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   49.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
  8 omega   43.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   74.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 35

#__ type_ start__ end____ width___ exp.time_
 10 omega  108.00  146.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
 11 omega   35.00   63.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 12 omega   98.00  143.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
 13 omega  109.00  138.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega   45.00   89.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -150.0000 44

#__ type_ start__ end____ width___ exp.time_
 15 omega   42.00   67.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega   54.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
 17 omega  148.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  -90.0000 29
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0624290000
_diffrn_orient_matrix_UB_12      0.0992596000
_diffrn_orient_matrix_UB_13      -0.0425331000
_diffrn_orient_matrix_UB_21      0.0593150000
_diffrn_orient_matrix_UB_22      0.1102852000
_diffrn_orient_matrix_UB_23      0.0358021000
_diffrn_orient_matrix_UB_31      0.0780780000
_diffrn_orient_matrix_UB_32      -0.0044129000
_diffrn_orient_matrix_UB_33      -0.0615356000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1967
_reflns_number_total             2447
_reflns_odcompleteness_completeness 91.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0632P)²+0.5055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1095
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.53482(3) 0.80852(4) 0.34598(2) 0.01828(15) Uani 1 1 d . . .
Cl1 Cl 0.59883(6) 0.63857(8) 0.40307(4) 0.02377(19) Uani 1 1 d . . .
Cl1A Cl 0.36532(5) 0.81409(8) 0.33915(4) 0.02114(19) Uani 1 1 d . . .
O1A O 0.58816(16) 0.8187(2) 0.24550(11) 0.0212(5) Uani 1 1 d . . .
O1 O 0.58686(16) 0.9696(2) 0.38779(11) 0.0218(5) Uani 1 1 d . . .
N2 N 0.6285(2) 1.1802(3) 0.39612(14) 0.0214(6) Uani 1 1 d . . .
N1A N 0.63135(19) 0.6102(3) 0.22495(14) 0.0231(6) Uani 1 1 d . . .
H1AA H 0.6299 0.5937 0.2703 0.028 Uiso 1 1 calc R . .
H1AB H 0.6463 0.5504 0.1948 0.028 Uiso 1 1 calc R . .
N1 N 0.6270(2) 1.0793(3) 0.28512(14) 0.0253(6) Uani 1 1 d . . .
H1A H 0.6003 1.0125 0.2653 0.030 Uiso 1 1 d R . .
H1B H 0.5985 1.1478 0.2686 0.030 Uiso 1 1 d R . .
N2A N 0.61407(19) 0.7544(3) 0.13103(13) 0.0193(6) Uani 1 1 d . . .
C1A C 0.6105(2) 0.7284(3) 0.20155(17) 0.0197(6) Uani 1 1 d . . .
C1 C 0.6136(2) 1.0738(3) 0.35685(17) 0.0204(6) Uani 1 1 d . . .
C2A C 0.6037(2) 0.8863(4) 0.10579(17) 0.0258(7) Uani 1 1 d . . .
H2AA H 0.5603 0.9332 0.1378 0.039 Uiso 1 1 calc R . .
H2AB H 0.5750 0.8863 0.0584 0.039 Uiso 1 1 calc R . .
H2AC H 0.6689 0.9266 0.1045 0.039 Uiso 1 1 calc R . .
C2 C 0.6223(3) 1.1735(4) 0.47429(17) 0.0276(7) Uani 1 1 d . . .
H2A H 0.5792 1.1033 0.4879 0.041 Uiso 1 1 calc R . .
H2B H 0.5950 1.2528 0.4926 0.041 Uiso 1 1 calc R . .
H2C H 0.6885 1.1601 0.4939 0.041 Uiso 1 1 calc R . .
C3A C 0.6476(2) 0.6562(4) 0.07931(16) 0.0243(7) Uani 1 1 d . . .
H3AA H 0.7175 0.6369 0.0875 0.036 Uiso 1 1 calc R . .
H3AB H 0.6391 0.6883 0.0312 0.036 Uiso 1 1 calc R . .
H3AC H 0.6081 0.5794 0.0854 0.036 Uiso 1 1 calc R . .
C3 C 0.6638(3) 1.2996(3) 0.36323(19) 0.0274(7) Uani 1 1 d . . .
H3A H 0.7264 1.2841 0.3387 0.041 Uiso 1 1 calc R . .
H3B H 0.6738 1.3635 0.3999 0.041 Uiso 1 1 calc R . .
H3C H 0.6143 1.3297 0.3294 0.041 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 Cl1 2.2262(9) . ?
Zn1 Cl1A 2.2493(8) . ?
Zn1 O1A 2.000(2) . ?
Zn1 O1 1.968(2) . ?
O1A C1A 1.278(4) . ?
O1 C1 1.275(4) . ?
N2 C1 1.338(4) . ?
N2 C2 1.457(4) . ?
N2 C3 1.458(4) . ?
N1A H1AA 0.8600 . ?
N1A H1AB 0.8600 . ?
N1A C1A 1.330(4) . ?
N1 H1A 0.8617 . ?
N1 H1B 0.8616 . ?
N1 C1 1.347(4) . ?
N2A C1A 1.339(4) . ?
N2A C2A 1.454(4) . ?
N2A C3A 1.469(4) . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3A H3AA 0.9600 . ?
C3A H3AB 0.9600 . ?
C3A H3AC 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?

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
Cl1 Zn1 Cl1A 115.30(3) . . ?
O1A Zn1 Cl1 110.65(7) . . ?
O1A Zn1 Cl1A 107.37(7) . . ?
O1 Zn1 Cl1 110.57(7) . . ?
O1 Zn1 Cl1A 110.48(7) . . ?
O1 Zn1 O1A 101.54(9) . . ?
C1A O1A Zn1 129.8(2) . . ?
C1 O1 Zn1 129.8(2) . . ?
C1 N2 C2 119.7(3) . . ?
C1 N2 C3 121.3(3) . . ?
C2 N2 C3 118.5(3) . . ?
H1AA N1A H1AB 120.0 . . ?
C1A N1A H1AA 120.0 . . ?
C1A N1A H1AB 120.0 . . ?
H1A N1 H1B 109.3 . . ?
C1 N1 H1A 109.6 . . ?
C1 N1 H1B 109.2 . . ?
C1A N2A C2A 120.1(3) . . ?
C1A N2A C3A 120.8(3) . . ?
C2A N2A C3A 118.0(3) . . ?
O1A C1A N1A 121.0(3) . . ?
O1A C1A N2A 119.1(3) . . ?
N1A C1A N2A 119.9(3) . . ?
O1 C1 N2 119.7(3) . . ?
O1 C1 N1 121.3(3) . . ?
N2 C1 N1 119.0(3) . . ?
N2A C2A H2AA 109.5 . . ?
N2A C2A H2AB 109.5 . . ?
N2A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2A C3A H3AA 109.5 . . ?
N2A C3A H3AB 109.5 . . ?
N2A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1A C1A N1A -22.0(4) . . . . ?
Zn1 O1A C1A N2A 158.9(2) . . . . ?
Zn1 O1 C1 N2 167.2(2) . . . . ?
Zn1 O1 C1 N1 -12.7(4) . . . . ?
Cl1 Zn1 O1A C1A 34.8(3) . . . . ?
Cl1 Zn1 O1 C1 140.7(2) . . . . ?
Cl1A Zn1 O1A C1A -91.8(2) . . . . ?
Cl1A Zn1 O1 C1 -90.5(2) . . . . ?
O1A Zn1 O1 C1 23.2(3) . . . . ?
O1 Zn1 O1A C1A 152.2(2) . . . . ?
C2A N2A C1A O1A 6.8(4) . . . . ?
C2A N2A C1A N1A -172.4(3) . . . . ?
C2 N2 C1 O1 5.0(4) . . . . ?
C2 N2 C1 N1 -175.1(3) . . . . ?
C3A N2A C1A O1A 174.9(3) . . . . ?
C3A N2A C1A N1A -4.3(4) . . . . ?
C3 N2 C1 O1 177.0(3) . . . . ?
C3 N2 C1 N1 -3.0(4) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1004423'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_643
_audit_creation_date             2014-06-11
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 H16 Br2 N4 O2 Zn'
_chemical_formula_sum            'C6 H16 Br2 N4 O2 Zn'
_chemical_formula_weight         401.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N7 C6 H14 zn1 br2'
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'
Zn Zn -1.5491 0.6778 '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'
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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.5270(5)
_cell_length_b                   12.6536(9)
_cell_length_c                   14.1711(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 89.364(6)
_cell_angle_gamma                90.00
_cell_volume                     1349.62(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3490
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.2630
_cell_measurement_theta_min      4.6750
_exptl_absorpt_coefficient_mu    9.407
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.976
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7946
_diffrn_reflns_theta_full        72.50
_diffrn_reflns_theta_max         72.50
_diffrn_reflns_theta_min         4.69
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9526
_diffrn_measured_fraction_theta_max 0.9526
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -126.00  -40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -178.0000  -60.0000 86

#__ type_ start__ end____ width___ exp.time_
  2 omega -113.00  -71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  120.0000 42

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega   87.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
  5 omega   40.00   80.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
  6 omega   58.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 56

#__ type_ start__ end____ width___ exp.time_
  8 omega  119.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega   57.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   30.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 65

#__ type_ start__ end____ width___ exp.time_
 11 omega   56.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
 12 omega   34.00   72.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
 13 omega  150.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   86.00  120.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 34

#__ type_ start__ end____ width___ exp.time_
 15 omega  -84.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   19.0000  -90.0000 123

#__ type_ start__ end____ width___ exp.time_
 16 omega  -44.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  150.0000 70

#__ type_ start__ end____ width___ exp.time_
 17 omega    4.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
 18 omega   36.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000 -150.0000 43

#__ type_ start__ end____ width___ exp.time_
 19 omega  129.00  155.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   82.00  115.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 21 omega  127.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
 22 omega   41.00   67.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   40.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   30.0000 69

#__ type_ start__ end____ width___ exp.time_
 24 omega  148.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  120.0000 29
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1942693000
_diffrn_orient_matrix_UB_12      -0.0099644000
_diffrn_orient_matrix_UB_13      0.0342972000
_diffrn_orient_matrix_UB_21      -0.0128760000
_diffrn_orient_matrix_UB_22      0.1213811000
_diffrn_orient_matrix_UB_23      0.0059549000
_diffrn_orient_matrix_UB_31      -0.0629997000
_diffrn_orient_matrix_UB_32      0.0040152000
_diffrn_orient_matrix_UB_33      -0.1029241000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2228
_reflns_number_total             2578
_reflns_odcompleteness_completeness 90.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2578
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0379P)²+1.1749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0815
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1A Br 0.14490(6) 0.52535(3) 0.88732(3) 0.02355(12) Uani 1 1 d . . .
Br1 Br 0.39808(5) 0.50191(3) 0.63630(3) 0.02217(12) Uani 1 1 d . . .
Zn1 Zn 0.12585(7) 0.50251(4) 0.72310(3) 0.01786(13) Uani 1 1 d . . .
N1A N -0.1525(4) 0.4359(3) 0.5635(2) 0.0238(7) Uani 1 1 d . . .
H1AA H -0.2559 0.4248 0.5394 0.029 Uiso 1 1 d R . .
H1AB H -0.1553 0.4953 0.5938 0.029 Uiso 1 1 d R . .
O1A O -0.0106(4) 0.3752(2) 0.69303(19) 0.0242(6) Uani 1 1 d . . .
N2 N -0.1295(4) 0.7761(3) 0.6278(2) 0.0234(7) Uani 1 1 d . . .
C3A C -0.1109(6) 0.1716(3) 0.6647(3) 0.0300(9) Uani 1 1 d . . .
H3AA H -0.0245 0.1317 0.6294 0.045 Uiso 1 1 calc R . .
H3AB H -0.2100 0.1271 0.6806 0.045 Uiso 1 1 calc R . .
H3AC H -0.0580 0.1978 0.7214 0.045 Uiso 1 1 calc R . .
N2A N -0.1721(4) 0.2606(3) 0.6077(2) 0.0231(7) Uani 1 1 d . . .
C1A C -0.1109(5) 0.3579(3) 0.6232(2) 0.0196(8) Uani 1 1 d . . .
N1 N 0.0694(5) 0.7587(3) 0.7504(2) 0.0266(7) Uani 1 1 d . . .
H1A H 0.1180 0.7092 0.7830 0.032 Uiso 1 1 d R . .
H1B H 0.1516 0.7975 0.7256 0.032 Uiso 1 1 d R . .
O1 O -0.0271(4) 0.6154(2) 0.66771(19) 0.0227(6) Uani 1 1 d . . .
C1 C -0.0289(5) 0.7142(3) 0.6820(3) 0.0196(7) Uani 1 1 d . . .
C2 C -0.1351(6) 0.8910(3) 0.6408(3) 0.0275(9) Uani 1 1 d . . .
H2A H -0.1877 0.9071 0.7012 0.041 Uiso 1 1 calc R . .
H2B H -0.2047 0.9223 0.5919 0.041 Uiso 1 1 calc R . .
H2C H -0.0165 0.9189 0.6380 0.041 Uiso 1 1 calc R . .
C2A C -0.2877(6) 0.2377(4) 0.5280(3) 0.0310(10) Uani 1 1 d . . .
H2AA H -0.2215 0.2451 0.4701 0.047 Uiso 1 1 calc R . .
H2AB H -0.3857 0.2863 0.5283 0.047 Uiso 1 1 calc R . .
H2AC H -0.3318 0.1667 0.5332 0.047 Uiso 1 1 calc R . .
C3 C -0.2419(6) 0.7276(3) 0.5558(3) 0.0353(11) Uani 1 1 d . . .
H3A H -0.1686 0.6902 0.5111 0.053 Uiso 1 1 calc R . .
H3B H -0.3073 0.7817 0.5238 0.053 Uiso 1 1 calc R . .
H3C H -0.3233 0.6791 0.5854 0.053 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1A Zn1 2.3510(6) . ?
Br1 Zn1 2.3782(7) . ?
Zn1 O1A 1.960(3) . ?
Zn1 O1 2.001(3) . ?
N1A H1AA 0.8646 . ?
N1A H1AB 0.8654 . ?
N1A C1A 1.340(5) . ?
O1A C1A 1.270(4) . ?
N2 C1 1.337(5) . ?
N2 C2 1.467(5) . ?
N2 C3 1.467(5) . ?
C3A H3AA 0.9600 . ?
C3A H3AB 0.9600 . ?
C3A H3AC 0.9600 . ?
C3A N2A 1.462(5) . ?
N2A C1A 1.334(5) . ?
N2A C2A 1.463(5) . ?
N1 H1A 0.8620 . ?
N1 H1B 0.8623 . ?
N1 C1 1.349(5) . ?
O1 C1 1.266(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?

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
Br1A Zn1 Br1 116.79(3) . . ?
O1A Zn1 Br1A 110.74(8) . . ?
O1A Zn1 Br1 109.61(9) . . ?
O1A Zn1 O1 101.33(11) . . ?
O1 Zn1 Br1A 110.01(8) . . ?
O1 Zn1 Br1 107.19(9) . . ?
H1AA N1A H1AB 108.7 . . ?
C1A N1A H1AA 110.2 . . ?
C1A N1A H1AB 109.3 . . ?
C1A O1A Zn1 129.0(3) . . ?
C1 N2 C2 121.6(3) . . ?
C1 N2 C3 119.2(3) . . ?
C2 N2 C3 119.1(3) . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
N2A C3A H3AA 109.5 . . ?
N2A C3A H3AB 109.5 . . ?
N2A C3A H3AC 109.5 . . ?
C3A N2A C2A 117.9(3) . . ?
C1A N2A C3A 120.6(3) . . ?
C1A N2A C2A 121.3(3) . . ?
O1A C1A N1A 120.7(4) . . ?
O1A C1A N2A 119.8(4) . . ?
N2A C1A N1A 119.5(3) . . ?
H1A N1 H1B 109.0 . . ?
C1 N1 H1A 108.7 . . ?
C1 N1 H1B 110.0 . . ?
C1 O1 Zn1 130.3(2) . . ?
N2 C1 N1 119.1(3) . . ?
O1 C1 N2 119.4(3) . . ?
O1 C1 N1 121.5(4) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2A C2A H2AA 109.5 . . ?
N2A C2A H2AB 109.5 . . ?
N2A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1A Zn1 O1A C1A 147.4(3) . . . . ?
Br1A Zn1 O1 C1 45.6(4) . . . . ?
Br1 Zn1 O1A C1A -82.3(3) . . . . ?
Br1 Zn1 O1 C1 -82.3(3) . . . . ?
Zn1 O1A C1A N1A -8.2(5) . . . . ?
Zn1 O1A C1A N2A 170.2(3) . . . . ?
Zn1 O1 C1 N2 171.9(3) . . . . ?
Zn1 O1 C1 N1 -7.7(6) . . . . ?
O1A Zn1 O1 C1 162.8(3) . . . . ?
C3A N2A C1A N1A 172.3(4) . . . . ?
C3A N2A C1A O1A -6.1(6) . . . . ?
O1 Zn1 O1A C1A 30.7(4) . . . . ?
C2 N2 C1 N1 0.2(6) . . . . ?
C2 N2 C1 O1 -179.4(4) . . . . ?
C2A N2A C1A N1A -1.6(6) . . . . ?
C2A N2A C1A O1A -179.9(4) . . . . ?
C3 N2 C1 N1 -177.6(4) . . . . ?
C3 N2 C1 O1 2.8(6) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1007855'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_but140
_audit_creation_date             2014-05-20
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H24 Cl2 N4 O2 Zn'
_chemical_formula_sum            'C12 H24 Cl2 N4 O2 Zn'
_chemical_formula_weight         392.62
_chemical_melting_point          ?
_chemical_oxdiff_formula         'zn1 cl2 c6 n3 o2 h12'
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'
O O 0.0492 0.0322 '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'

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

_cell_length_a                   9.6999(11)
_cell_length_b                   9.9427(11)
_cell_length_c                   10.1598(7)
_cell_angle_alpha                88.738(7)
_cell_angle_beta                 88.449(7)
_cell_angle_gamma                61.132(11)
_cell_volume                     857.73(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2272
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9870
_cell_measurement_theta_min      4.3540
_exptl_absorpt_coefficient_mu    4.935
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8757
_diffrn_reflns_theta_full        71.50
_diffrn_reflns_theta_max         71.50
_diffrn_reflns_theta_min         4.35
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9011
_diffrn_measured_fraction_theta_max 0.9485
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -42.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1287   38.0000 -180.0000 71

#__ type_ start__ end____ width___ exp.time_
  2 omega -126.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1287    0.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
  3 omega   66.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1287 -178.0000  -60.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega   39.00   90.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 51

#__ type_ start__ end____ width___ exp.time_
  5 omega   37.00  147.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  150.0000 110

#__ type_ start__ end____ width___ exp.time_
  6 omega  122.00  147.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00   84.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
  8 omega   29.00   68.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 39

#__ type_ start__ end____ width___ exp.time_
  9 omega  142.00  172.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
 10 omega  101.00  128.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega  146.00  171.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   55.00   90.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
 13 omega   46.00   89.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 43

#__ type_ start__ end____ width___ exp.time_
 14 omega   88.00  122.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 34

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  108.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega  115.00  174.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   99.0000 -124.0000 59

#__ type_ start__ end____ width___ exp.time_
 17 omega   70.00  128.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
 18 omega  141.00  170.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
 19 omega  131.00  158.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega   65.00  115.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
 21 omega -114.00  -25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1287  -38.0000 -180.0000 89

#__ type_ start__ end____ width___ exp.time_
 22 omega  -67.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1287  -19.0000   60.0000 62

#__ type_ start__ end____ width___ exp.time_
 23 omega  103.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1287  178.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   39.00   66.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -53.0000  102.3406 27

#__ type_ start__ end____ width___ exp.time_
 25 omega   40.00   67.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 26 omega   90.00  115.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega   57.00   83.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   85.00  110.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 29 omega   84.00  112.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
 30 omega  121.00  148.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 31 omega   38.00   65.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 32 omega   88.00  115.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 33 omega   55.00   80.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 34 omega   35.00   61.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 35 omega   52.00   86.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 36 omega   80.00  107.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -53.0000  102.3406 27

#__ type_ start__ end____ width___ exp.time_
 37 omega   75.00  102.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 38 omega   37.00   69.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
 39 omega   54.00   90.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -37.0000  130.8288 36

#__ type_ start__ end____ width___ exp.time_
 40 omega  122.00  174.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   60.0000 52

#__ type_ start__ end____ width___ exp.time_
 41 omega   73.00   98.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 42 omega   58.00   84.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 43 omega   99.00  164.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000    0.0000 65

#__ type_ start__ end____ width___ exp.time_
 44 omega  102.00  129.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 45 omega   55.00   82.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 46 omega   76.00  119.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -119.0000  114.4801 43

#__ type_ start__ end____ width___ exp.time_
 47 omega  -69.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1287  178.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 48 omega -128.00 -103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1287  178.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 49 omega   30.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1287  -57.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 50 omega  -31.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1287  -57.0000 -180.0000 20
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0903059000
_diffrn_orient_matrix_UB_12      0.1667790000
_diffrn_orient_matrix_UB_13      0.0487412000
_diffrn_orient_matrix_UB_21      0.1545046000
_diffrn_orient_matrix_UB_22      0.0084484000
_diffrn_orient_matrix_UB_23      -0.0022379000
_diffrn_orient_matrix_UB_31      -0.0294600000
_diffrn_orient_matrix_UB_32      0.0583938000
_diffrn_orient_matrix_UB_33      -0.1436507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2453
_reflns_number_total             3206
_reflns_odcompleteness_completeness 90.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.867
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0830P)²+0.4240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1601
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.66486(7) 0.06467(7) 0.25980(6) 0.0231(2) Uani 1 1 d . . .
Cl1A Cl 0.79508(12) -0.18915(12) 0.22111(11) 0.0256(3) Uani 1 1 d . . .
Cl1 Cl 0.73016(14) 0.14624(14) 0.43609(11) 0.0304(3) Uani 1 1 d . . .
O1A O 0.6683(4) 0.1789(4) 0.1010(3) 0.0271(7) Uani 1 1 d . . .
O1 O 0.4400(4) 0.1128(4) 0.2696(3) 0.0258(7) Uani 1 1 d . . .
C1A C 0.5902(5) 0.2053(5) -0.0035(5) 0.0238(9) Uani 1 1 d . . .
N2A N 0.6371(5) 0.2499(5) -0.1136(4) 0.0275(8) Uani 1 1 d . . .
N2 N 0.1933(5) 0.1718(4) 0.3368(4) 0.0257(8) Uani 1 1 d . . .
N1 N 0.3651(5) 0.1927(5) 0.4798(4) 0.0269(8) Uani 1 1 d D . .
C1 C 0.3343(5) 0.1583(5) 0.3602(5) 0.0233(9) Uani 1 1 d . . .
N1A N 0.4594(5) 0.1901(5) -0.0049(4) 0.0271(8) Uani 1 1 d . . .
H1AA H 0.4664 0.1311 -0.0690 0.033 Uiso 1 1 d R . .
H1AB H 0.4496 0.1492 0.0685 0.033 Uiso 1 1 d R . .
C2 C 0.1564(5) 0.1447(5) 0.2034(5) 0.0282(10) Uani 1 1 d . . .
H2A H 0.1014 0.0851 0.2091 0.034 Uiso 1 1 calc R . .
H2B H 0.2532 0.0866 0.1531 0.034 Uiso 1 1 calc R . .
C2A C 0.7872(6) 0.2535(6) -0.1171(5) 0.0316(10) Uani 1 1 d . . .
H2AA H 0.8609 0.1757 -0.1769 0.038 Uiso 1 1 calc R . .
H2AB H 0.8322 0.2308 -0.0301 0.038 Uiso 1 1 calc R . .
C6A C 0.5562(6) 0.2870(6) -0.2385(5) 0.0299(10) Uani 1 1 d . . .
H6AA H 0.4566 0.2869 -0.2273 0.036 Uiso 1 1 calc R . .
H6AB H 0.6196 0.2096 -0.3029 0.036 Uiso 1 1 calc R . .
C3 C 0.0540(6) 0.2970(6) 0.1341(5) 0.0284(10) Uani 1 1 d . . .
H3A H 0.0272 0.2786 0.0475 0.034 Uiso 1 1 calc R . .
H3B H 0.1112 0.3542 0.1233 0.034 Uiso 1 1 calc R . .
C6 C 0.0526(6) 0.2540(6) 0.4208(5) 0.0299(10) Uani 1 1 d . . .
H6A H 0.0829 0.2694 0.5070 0.036 Uiso 1 1 calc R . .
H6B H -0.0011 0.1936 0.4317 0.036 Uiso 1 1 calc R . .
C5 C -0.0566(6) 0.4079(6) 0.3582(5) 0.0331(11) Uani 1 1 d . . .
H5A H -0.0070 0.4724 0.3577 0.040 Uiso 1 1 calc R . .
H5B H -0.1531 0.4584 0.4105 0.040 Uiso 1 1 calc R . .
C3A C 0.7604(6) 0.4115(6) -0.1628(5) 0.0343(11) Uani 1 1 d . . .
H3AA H 0.6952 0.4878 -0.0983 0.041 Uiso 1 1 calc R . .
H3AB H 0.8606 0.4109 -0.1701 0.041 Uiso 1 1 calc R . .
C4A C 0.6802(7) 0.4534(7) -0.2956(7) 0.0445(14) Uani 1 1 d . . .
H4AA H 0.7502 0.3832 -0.3620 0.053 Uiso 1 1 calc R . .
H4AB H 0.6578 0.5565 -0.3208 0.053 Uiso 1 1 calc R . .
C4 C -0.0965(6) 0.3900(6) 0.2165(5) 0.0315(10) Uani 1 1 d . . .
H4A H -0.1597 0.3384 0.2179 0.038 Uiso 1 1 calc R . .
H4B H -0.1579 0.4907 0.1766 0.038 Uiso 1 1 calc R . .
C5A C 0.5265(7) 0.4448(7) -0.2885(6) 0.0401(12) Uani 1 1 d . . .
H5AA H 0.4520 0.5235 -0.2298 0.048 Uiso 1 1 calc R . .
H5AB H 0.4810 0.4642 -0.3752 0.048 Uiso 1 1 calc R . .
H1A H 0.457(3) 0.182(6) 0.494(5) 0.020(12) Uiso 1 1 d D . .
H1B H 0.305(6) 0.208(7) 0.548(3) 0.028(15) Uiso 1 1 d 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
Zn1 Cl1A 2.2489(12) . ?
Zn1 Cl1 2.2110(12) . ?
Zn1 O1A 1.962(3) . ?
Zn1 O1 1.995(3) . ?
O1A C1A 1.268(6) . ?
O1 C1 1.274(5) . ?
C1A N2A 1.342(6) . ?
C1A N1A 1.349(6) . ?
N2A C2A 1.472(6) . ?
N2A C6A 1.455(6) . ?
N2 C1 1.336(6) . ?
N2 C2 1.474(6) . ?
N2 C6 1.466(6) . ?
N1 C1 1.348(6) . ?
N1 H1A 0.860(5) . ?
N1 H1B 0.860(5) . ?
N1A H1AA 0.8659 . ?
N1A H1AB 0.8659 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.521(7) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A C3A 1.527(7) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C6A C5A 1.530(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.534(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.516(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.537(7) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C3A C4A 1.522(9) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C5A 1.533(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?

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
Cl1 Zn1 Cl1A 117.29(5) . . ?
O1A Zn1 Cl1A 110.07(10) . . ?
O1A Zn1 Cl1 111.61(9) . . ?
O1A Zn1 O1 101.74(14) . . ?
O1 Zn1 Cl1A 103.34(10) . . ?
O1 Zn1 Cl1 111.37(10) . . ?
C1A O1A Zn1 129.1(3) . . ?
C1 O1 Zn1 134.6(3) . . ?
O1A C1A N2A 119.9(4) . . ?
O1A C1A N1A 120.6(4) . . ?
N2A C1A N1A 119.5(4) . . ?
C1A N2A C2A 120.2(4) . . ?
C1A N2A C6A 125.2(4) . . ?
C6A N2A C2A 114.5(4) . . ?
C1 N2 C2 119.9(4) . . ?
C1 N2 C6 124.9(4) . . ?
C6 N2 C2 112.8(4) . . ?
C1 N1 H1A 119(3) . . ?
C1 N1 H1B 123(4) . . ?
H1A N1 H1B 116(5) . . ?
O1 C1 N2 120.0(4) . . ?
O1 C1 N1 119.9(4) . . ?
N2 C1 N1 120.1(4) . . ?
C1A N1A H1AA 109.6 . . ?
C1A N1A H1AB 110.0 . . ?
H1AA N1A H1AB 108.7 . . ?
N2 C2 H2A 109.6 . . ?
N2 C2 H2B 109.6 . . ?
N2 C2 C3 110.1(4) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
N2A C2A H2AA 109.6 . . ?
N2A C2A H2AB 109.6 . . ?
N2A C2A C3A 110.1(4) . . ?
H2AA C2A H2AB 108.1 . . ?
C3A C2A H2AA 109.6 . . ?
C3A C2A H2AB 109.6 . . ?
N2A C6A H6AA 109.6 . . ?
N2A C6A H6AB 109.6 . . ?
N2A C6A C5A 110.4(4) . . ?
H6AA C6A H6AB 108.1 . . ?
C5A C6A H6AA 109.6 . . ?
C5A C6A H6AB 109.6 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C2 C3 C4 109.2(4) . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
N2 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
N2 C6 C5 109.6(4) . . ?
H6A C6 H6B 108.2 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C6 C5 C4 111.6(4) . . ?
H5A C5 H5B 108.0 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C2A C3A H3AA 109.6 . . ?
C2A C3A H3AB 109.6 . . ?
H3AA C3A H3AB 108.1 . . ?
C4A C3A C2A 110.4(4) . . ?
C4A C3A H3AA 109.6 . . ?
C4A C3A H3AB 109.6 . . ?
C3A C4A H4AA 109.6 . . ?
C3A C4A H4AB 109.6 . . ?
C3A C4A C5A 110.4(5) . . ?
H4AA C4A H4AB 108.1 . . ?
C5A C4A H4AA 109.6 . . ?
C5A C4A H4AB 109.6 . . ?
C3 C4 C5 110.8(4) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C6A C5A C4A 110.9(4) . . ?
C6A C5A H5AA 109.5 . . ?
C6A C5A H5AB 109.5 . . ?
C4A C5A H5AA 109.5 . . ?
C4A C5A H5AB 109.5 . . ?
H5AA C5A H5AB 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
Zn1 O1A C1A N2A -162.5(3) . . . . ?
Zn1 O1A C1A N1A 18.0(6) . . . . ?
Zn1 O1 C1 N2 -176.0(3) . . . . ?
Zn1 O1 C1 N1 4.0(6) . . . . ?
Cl1A Zn1 O1A C1A 75.3(4) . . . . ?
Cl1A Zn1 O1 C1 114.4(4) . . . . ?
Cl1 Zn1 O1A C1A -152.7(4) . . . . ?
Cl1 Zn1 O1 C1 -12.3(4) . . . . ?
O1A Zn1 O1 C1 -131.4(4) . . . . ?
O1A C1A N2A C2A 6.0(7) . . . . ?
O1A C1A N2A C6A -178.5(4) . . . . ?
O1 Zn1 O1A C1A -33.8(4) . . . . ?
C1A N2A C2A C3A -126.6(5) . . . . ?
C1A N2A C6A C5A 127.7(5) . . . . ?
N2A C2A C3A C4A -55.7(6) . . . . ?
N2A C6A C5A C4A 54.2(6) . . . . ?
N2 C2 C3 C4 -57.6(5) . . . . ?
N2 C6 C5 C4 54.5(5) . . . . ?
C1 N2 C2 C3 -101.8(5) . . . . ?
C1 N2 C6 C5 103.3(5) . . . . ?
N1A C1A N2A C2A -174.4(4) . . . . ?
N1A C1A N2A C6A 1.0(7) . . . . ?
C2 N2 C1 O1 -4.3(6) . . . . ?
C2 N2 C1 N1 175.7(4) . . . . ?
C2 N2 C6 C5 -59.1(5) . . . . ?
C2 C3 C4 C5 54.3(5) . . . . ?
C2A N2A C6A C5A -56.6(6) . . . . ?
C2A C3A C4A C5A 55.6(6) . . . . ?
C6A N2A C2A C3A 57.5(6) . . . . ?
C6 N2 C1 O1 -165.6(4) . . . . ?
C6 N2 C1 N1 14.4(7) . . . . ?
C6 N2 C2 C3 61.6(5) . . . . ?
C6 C5 C4 C3 -53.6(5) . . . . ?
C3A C4A C5A C6A -54.9(7) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1004425'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sas_68
_audit_creation_date             2013-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H24 Br2 N4 O2 Zn'
_chemical_formula_sum            'C12 H24 Br2 N4 O2 Zn'
_chemical_formula_weight         481.54
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.6266(2)
_cell_length_b                   17.3401(5)
_cell_length_c                   9.7944(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.340(2)
_cell_angle_gamma                90
_cell_volume                     1801.71(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3988
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.7230
_cell_measurement_theta_min      2.9800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10704
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        27.496
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.990
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0386722000
_diffrn_orient_matrix_UB_12      -0.0300249000
_diffrn_orient_matrix_UB_13      -0.0280655000
_diffrn_orient_matrix_UB_21      0.0520642000
_diffrn_orient_matrix_UB_22      -0.0257332000
_diffrn_orient_matrix_UB_23      0.0054017000
_diffrn_orient_matrix_UB_31      -0.0162428000
_diffrn_orient_matrix_UB_32      -0.0105368000
_diffrn_orient_matrix_UB_33      0.0666450000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3291
_reflns_number_total             4014
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4014
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0201P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0561
_refine_ls_wR_factor_ref         0.0609
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C1(H1A,H1B), C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B),
 C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C7(H7A,H7B)
2.b X=CH2 refined with riding coordinates:
 N11(H11A,H11B), N2(H2A,H2B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.78093(3) 0.10516(2) 0.15451(3) 0.02006(9) Uani 1 1 d . . . . .
Zn2 Zn 0.74737(3) -0.02822(2) 0.19873(3) 0.01529(9) Uani 1 1 d . . . . .
Br3 Br 0.57370(3) -0.05464(2) 0.32652(3) 0.02325(9) Uani 1 1 d . . . . .
O2 O 0.89830(17) -0.07700(12) 0.2824(2) 0.0216(5) Uani 1 1 d . . . . .
N4 N 1.1095(2) -0.08834(16) 0.3107(3) 0.0241(6) Uani 1 1 d . . . . .
C8 C 1.0047(3) -0.08232(18) 0.2304(3) 0.0203(7) Uani 1 1 d . . . . .
N11 N 1.0103(2) -0.08055(16) 0.0943(3) 0.0321(7) Uani 1 1 d . . . . .
H11A H 0.9422 -0.0759 0.0430 0.038 Uiso 1 1 calc R . . . .
H11B H 1.0819 -0.0841 0.0581 0.038 Uiso 1 1 calc R . . . .
C6 C 1.2371(3) -0.09778(19) 0.2623(3) 0.0271(8) Uani 1 1 d . . . . .
H6A H 1.2926 -0.0591 0.3047 0.033 Uiso 1 1 calc R . . . .
H6B H 1.2348 -0.0902 0.1641 0.033 Uiso 1 1 calc R . . . .
C1 C 1.1036(3) -0.10074(19) 0.4574(3) 0.0285(8) Uani 1 1 d . . . . .
H1A H 1.0175 -0.0944 0.4833 0.034 Uiso 1 1 calc R . . . .
H1B H 1.1557 -0.0628 0.5068 0.034 Uiso 1 1 calc R . . . .
C9 C 1.1494(3) -0.18078(19) 0.4951(3) 0.0277(8) Uani 1 1 d . . . . .
H9A H 1.0935 -0.2187 0.4512 0.033 Uiso 1 1 calc R . . . .
H9B H 1.1483 -0.1878 0.5932 0.033 Uiso 1 1 calc R . . . .
C10 C 1.2831(3) -0.19270(18) 0.4498(3) 0.0272(8) Uani 1 1 d . . . . .
H10A H 1.3403 -0.1580 0.5002 0.033 Uiso 1 1 calc R . . . .
H10B H 1.3099 -0.2452 0.4699 0.033 Uiso 1 1 calc R . . . .
C13 C 1.2881(3) -0.17751(18) 0.2971(3) 0.0270(8) Uani 1 1 d . . . . .
H13A H 1.3745 -0.1814 0.2709 0.032 Uiso 1 1 calc R . . . .
H13B H 1.2384 -0.2160 0.2463 0.032 Uiso 1 1 calc R . . . .
O3 O 0.74283(17) -0.07367(12) 0.01146(19) 0.0182(5) Uani 1 1 d . . . . .
N2 N 0.5346(2) -0.09816(13) -0.0273(2) 0.0214(6) Uani 1 1 d . . . . .
H2A H 0.5211 -0.0872 0.0563 0.026 Uiso 1 1 calc R . . . .
H2B H 0.4729 -0.1118 -0.0828 0.026 Uiso 1 1 calc R . . . .
C5 C 0.6520(3) -0.09389(16) -0.0711(3) 0.0173(7) Uani 1 1 d . . . . .
N7 N 0.6724(2) -0.11095(15) -0.2004(2) 0.0218(6) Uani 1 1 d . . . . .
C12 C 0.5807(3) -0.14475(18) -0.3006(3) 0.0243(7) Uani 1 1 d . . . . .
H12A H 0.5748 -0.1131 -0.3824 0.029 Uiso 1 1 calc R . . . .
H12B H 0.4983 -0.1462 -0.2630 0.029 Uiso 1 1 calc R . . . .
C14 C 0.8005(3) -0.10756(18) -0.2503(3) 0.0257(8) Uani 1 1 d . . . . .
H14A H 0.8574 -0.0841 -0.1813 0.031 Uiso 1 1 calc R . . . .
H14B H 0.8000 -0.0760 -0.3321 0.031 Uiso 1 1 calc R . . . .
C15 C 0.8457(3) -0.18780(19) -0.2820(3) 0.0295(8) Uani 1 1 d . . . . .
H15A H 0.8514 -0.2184 -0.1989 0.035 Uiso 1 1 calc R . . . .
H15B H 0.9290 -0.1851 -0.3173 0.035 Uiso 1 1 calc R . . . .
C16 C 0.6204(3) -0.2257(2) -0.3371(4) 0.0346(9) Uani 1 1 d . . . . .
H16A H 0.5625 -0.2461 -0.4084 0.042 Uiso 1 1 calc R . . . .
H16B H 0.6169 -0.2587 -0.2575 0.042 Uiso 1 1 calc R . . . .
C7 C 0.7550(3) -0.2258(2) -0.3869(4) 0.0375(9) Uani 1 1 d . . . . .
H7A H 0.7815 -0.2784 -0.4023 0.045 Uiso 1 1 calc R . . . .
H7B H 0.7562 -0.1981 -0.4729 0.045 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Zn2 2.3836(5) . ?
Zn2 Br3 2.3348(4) . ?
Zn2 O2 1.951(2) . ?
Zn2 O3 1.9944(19) . ?
O2 C8 1.270(3) . ?
N4 C8 1.329(4) . ?
N4 C6 1.471(3) . ?
N4 C1 1.458(4) . ?
C8 N11 1.339(4) . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C13 1.516(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C9 1.509(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.527(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C13 1.523(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
O3 C5 1.272(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C5 1.345(3) . ?
C5 N7 1.330(3) . ?
N7 C12 1.465(4) . ?
N7 C14 1.474(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C16 1.514(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.510(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C7 1.518(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C7 1.538(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

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
Br3 Zn2 Br1 114.777(17) . . ?
O2 Zn2 Br1 111.66(6) . . ?
O2 Zn2 Br3 110.24(5) . . ?
O2 Zn2 O3 100.97(8) . . ?
O3 Zn2 Br1 102.25(6) . . ?
O3 Zn2 Br3 115.97(5) . . ?
C8 O2 Zn2 126.34(19) . . ?
C8 N4 C6 125.0(3) . . ?
C8 N4 C1 120.8(2) . . ?
C1 N4 C6 113.2(2) . . ?
O2 C8 N4 120.2(3) . . ?
O2 C8 N11 119.3(3) . . ?
N4 C8 N11 120.5(3) . . ?
C8 N11 H11A 120.0 . . ?
C8 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
N4 C6 C13 110.7(2) . . ?
H6A C6 H6B 108.1 . . ?
C13 C6 H6A 109.5 . . ?
C13 C6 H6B 109.5 . . ?
N4 C1 H1A 109.6 . . ?
N4 C1 H1B 109.6 . . ?
N4 C1 C9 110.2(2) . . ?
H1A C1 H1B 108.1 . . ?
C9 C1 H1A 109.6 . . ?
C9 C1 H1B 109.6 . . ?
C1 C9 H9A 109.6 . . ?
C1 C9 H9B 109.6 . . ?
C1 C9 C10 110.2(3) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C13 C10 C9 110.4(3) . . ?
C13 C10 H10A 109.6 . . ?
C13 C10 H10B 109.6 . . ?
C6 C13 C10 110.2(2) . . ?
C6 C13 H13A 109.6 . . ?
C6 C13 H13B 109.6 . . ?
C10 C13 H13A 109.6 . . ?
C10 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C5 O3 Zn2 132.10(17) . . ?
H2A N2 H2B 120.0 . . ?
C5 N2 H2A 120.0 . . ?
C5 N2 H2B 120.0 . . ?
O3 C5 N2 119.8(3) . . ?
O3 C5 N7 120.5(3) . . ?
N7 C5 N2 119.8(3) . . ?
C5 N7 C12 126.0(2) . . ?
C5 N7 C14 120.8(3) . . ?
C12 N7 C14 112.6(2) . . ?
N7 C12 H12A 109.6 . . ?
N7 C12 H12B 109.6 . . ?
N7 C12 C16 110.2(3) . . ?
H12A C12 H12B 108.1 . . ?
C16 C12 H12A 109.6 . . ?
C16 C12 H12B 109.6 . . ?
N7 C14 H14A 109.7 . . ?
N7 C14 H14B 109.7 . . ?
N7 C14 C15 110.0(2) . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C14 C15 C7 110.0(3) . . ?
H15A C15 H15B 108.2 . . ?
C7 C15 H15A 109.7 . . ?
C7 C15 H15B 109.7 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 C7 110.6(3) . . ?
H16A C16 H16B 108.1 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
C15 C7 C16 110.5(3) . . ?
C15 C7 H7A 109.5 . . ?
C15 C7 H7B 109.5 . . ?
C16 C7 H7A 109.5 . . ?
C16 C7 H7B 109.5 . . ?
H7A C7 H7B 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
Zn2 O2 C8 N4 153.7(2) . . . . ?
Zn2 O2 C8 N11 -25.2(4) . . . . ?
Zn2 O3 C5 N2 -11.5(4) . . . . ?
Zn2 O3 C5 N7 168.6(2) . . . . ?
N4 C6 C13 C10 -54.9(3) . . . . ?
N4 C1 C9 C10 57.1(3) . . . . ?
C8 N4 C6 C13 -111.3(3) . . . . ?
C8 N4 C1 C9 110.8(3) . . . . ?
C6 N4 C8 O2 177.6(3) . . . . ?
C6 N4 C8 N11 -3.5(5) . . . . ?
C6 N4 C1 C9 -58.6(4) . . . . ?
C1 N4 C8 O2 9.4(5) . . . . ?
C1 N4 C8 N11 -171.7(3) . . . . ?
C1 N4 C6 C13 57.7(4) . . . . ?
C1 C9 C10 C13 -56.1(3) . . . . ?
C9 C10 C13 C6 55.0(3) . . . . ?
O3 C5 N7 C12 171.2(3) . . . . ?
O3 C5 N7 C14 0.6(4) . . . . ?
N2 C5 N7 C12 -8.7(5) . . . . ?
N2 C5 N7 C14 -179.3(3) . . . . ?
C5 N7 C12 C16 -112.5(3) . . . . ?
C5 N7 C14 C15 111.5(3) . . . . ?
N7 C12 C16 C7 -55.0(4) . . . . ?
N7 C14 C15 C7 57.7(3) . . . . ?
C12 N7 C14 C15 -60.2(3) . . . . ?
C12 C16 C7 C15 54.4(4) . . . . ?
C14 N7 C12 C16 58.8(3) . . . . ?
C14 C15 C7 C16 -55.5(4) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1002741'
