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# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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#  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.
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#  fide research purposes only. It may contain copyright material
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data_1

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H27 Cl N3 Na Ni O8'
_chemical_formula_weight         602.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

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

_cell_length_a                   11.394(13)
_cell_length_b                   29.49(4)
_cell_length_c                   9.154(10)
_cell_angle_alpha                90
_cell_angle_beta                 123.07(4)
_cell_angle_gamma                90
_cell_volume                     2578(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15794
_cell_measurement_theta_min      2.428
_cell_measurement_theta_max      27.098

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.927
_shelx_estimated_absorpt_T_min   0.702
_shelx_estimated_absorpt_T_max   0.829
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15794
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.428
_diffrn_reflns_theta_max         27.098
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5637
_reflns_number_gt                5056
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.981
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.993

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

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_structure_solution    WINGX
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Diamond 3'
_computing_publication_material  'Microsoft word 2010'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+1.1093P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2283 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.013(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5637
_refine_ls_number_parameters     343
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6545(6) -0.03166(18) -0.1573(7) 0.0305(12) Uani 1 1 d . . . . .
H1 H 0.6115 -0.0372 -0.0885 0.037 Uiso 1 1 calc R U . . .
C2 C 0.8008(6) -0.05029(17) -0.0557(7) 0.0303(11) Uani 1 1 d . . . . .
H2 H 0.8400 -0.0467 -0.1297 0.036 Uiso 1 1 calc R U . . .
C3 C 0.8044(5) -0.10161(15) -0.0162(7) 0.0279(11) Uani 1 1 d . . . . .
H3A H 0.7673 -0.1069 0.0581 0.033 Uiso 1 1 calc R U . . .
H3B H 0.9016 -0.1132 0.0454 0.033 Uiso 1 1 calc R U . . .
C4 C 0.7117(6) -0.12590(18) -0.1944(8) 0.0428(14) Uani 1 1 d . . . . .
H4A H 0.7586 -0.1239 -0.2588 0.051 Uiso 1 1 calc R U . . .
H4B H 0.7051 -0.1584 -0.1728 0.051 Uiso 1 1 calc R U . . .
C5 C 0.5671(6) -0.10723(18) -0.3067(7) 0.0377(13) Uani 1 1 d . . . . .
H5A H 0.5136 -0.1144 -0.2533 0.045 Uiso 1 1 calc R U . . .
H5B H 0.5195 -0.1222 -0.4222 0.045 Uiso 1 1 calc R U . . .
C6 C 0.5661(5) -0.05620(16) -0.3313(6) 0.0257(10) Uani 1 1 d . . . . .
H6A H 0.4685 -0.0450 -0.3927 0.031 Uiso 1 1 calc R U . . .
H6B H 0.6029 -0.0494 -0.4050 0.031 Uiso 1 1 calc R U . . .
C11 C 0.5773(6) 0.04169(16) -0.2927(7) 0.0236(12) Uani 1 1 d . . . . .
H11 H 0.4993 0.0259 -0.3851 0.028 Uiso 1 1 calc R U . . .
C12 C 0.5792(5) 0.08997(16) -0.3088(6) 0.0230(9) Uani 1 1 d . . . . .
C13 C 0.4758(6) 0.11115(18) -0.4673(7) 0.0286(12) Uani 1 1 d . . . . .
H13 H 0.4030 0.0933 -0.5581 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4795(5) 0.15692(18) -0.4913(7) 0.0343(12) Uani 1 1 d . . . . .
H14 H 0.4109 0.1706 -0.5989 0.041 Uiso 1 1 calc R U . . .
C15 C 0.5849(5) 0.18343(16) -0.3562(7) 0.0312(11) Uani 1 1 d . . . . .
H15 H 0.5886 0.2150 -0.3737 0.037 Uiso 1 1 calc R U . . .
C16 C 0.6838(5) 0.16419(15) -0.1977(6) 0.0238(10) Uani 1 1 d . . . . .
C17 C 0.6855(5) 0.11650(15) -0.1725(6) 0.0215(9) Uani 1 1 d . . . . .
C18 C 0.7999(6) 0.23469(16) -0.0759(8) 0.0355(12) Uani 1 1 d . . . . .
H18A H 0.8773 0.2474 0.0339 0.053 Uiso 1 1 calc R U . . .
H18B H 0.7124 0.2499 -0.1083 0.053 Uiso 1 1 calc R U . . .
H18C H 0.8182 0.2393 -0.1678 0.053 Uiso 1 1 calc R U . . .
C21 C 0.9822(6) -0.03461(16) 0.2502(7) 0.0251(11) Uani 1 1 d . . . . .
H21 H 0.9937 -0.0665 0.2667 0.030 Uiso 1 1 calc R U . . .
C22 C 1.0767(5) -0.00599(16) 0.3957(6) 0.0224(9) Uani 1 1 d . . . . .
C23 C 1.1766(5) -0.02634(18) 0.5583(7) 0.0285(11) Uani 1 1 d . . . . .
H23 H 1.1804 -0.0584 0.5686 0.034 Uiso 1 1 calc R U . . .
C24 C 1.2663(5) -0.00080(19) 0.6985(6) 0.0317(11) Uani 1 1 d . . . . .
H24 H 1.3320 -0.0151 0.8061 0.038 Uiso 1 1 calc R U . . .
C25 C 1.2631(5) 0.04706(18) 0.6860(6) 0.0297(11) Uani 1 1 d . . . . .
H25 H 1.3258 0.0648 0.7853 0.036 Uiso 1 1 calc R U . . .
C26 C 1.1688(5) 0.06791(17) 0.5292(6) 0.0253(10) Uani 1 1 d . . . . .
C27 C 1.0740(6) 0.04199(16) 0.3807(7) 0.0213(11) Uani 1 1 d . . . . .
C28 C 1.2419(6) 0.14229(19) 0.6514(7) 0.0358(12) Uani 1 1 d . . . . .
H28A H 1.2243 0.1742 0.6165 0.054 Uiso 1 1 calc R U . . .
H28B H 1.3409 0.1353 0.7014 0.054 Uiso 1 1 calc R U . . .
H28C H 1.2190 0.1365 0.7385 0.054 Uiso 1 1 calc R U . . .
C31 C 0.9956(12) 0.2734(3) 0.5607(11) 0.089(3) Uani 1 1 d . . . . .
C32 C 0.9689(6) 0.2338(2) 0.4450(8) 0.0436(14) Uani 1 1 d . . . . .
N1 N 0.6722(4) 0.01775(13) -0.1637(5) 0.0240(8) Uani 1 1 d . . . . .
N2 N 0.8829(4) -0.02001(12) 0.0985(5) 0.0214(8) Uani 1 1 d . . . . .
N3 N 0.9595(5) 0.20551(16) 0.3592(6) 0.0396(11) Uani 1 1 d . . . . .
O1 O 0.7863(3) 0.09999(10) -0.0230(4) 0.0243(7) Uani 1 1 d . . . . .
O2 O 0.9846(3) 0.06415(10) 0.2353(4) 0.0215(7) Uani 1 1 d . . . . .
O3 O 0.7880(3) 0.18690(10) -0.0545(5) 0.0273(7) Uani 1 1 d . . . . .
O4 O 1.1560(4) 0.11401(12) 0.5010(4) 0.0282(8) Uani 1 1 d . . . . .
O5 O 1.0206(6) 0.1449(3) -0.1088(9) 0.119(3) Uani 1 1 d . . . . .
O6 O 1.1327(4) 0.18326(17) 0.1495(5) 0.0504(11) Uani 1 1 d . . . . .
O7 O 1.2606(4) 0.14827(16) 0.0475(6) 0.0511(11) Uani 1 1 d . . . . .
O8 O 1.1295(11) 0.2129(3) -0.0798(13) 0.154(5) Uani 1 1 d . . . . .
Ni1 Ni 0.83216(5) 0.03989(2) 0.03579(6) 0.01817(14) Uani 1 1 d . . . . .
Cl1 Cl 1.13546(13) 0.17195(4) -0.00009(15) 0.0305(3) Uani 1 1 d . . . . .
Na1 Na 0.97598(19) 0.14263(6) 0.1929(2) 0.0257(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.477(7) . ?
C1 C2 1.501(8) . ?
C1 C6 1.525(7) . ?
C1 H1 1.0000 . ?
C2 N2 1.491(6) . ?
C2 C3 1.551(7) . ?
C2 H2 1.0000 . ?
C3 C4 1.553(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.492(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.521(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C11 N1 1.291(7) . ?
C11 C12 1.433(7) . ?
C11 H11 0.9500 . ?
C12 C17 1.409(7) . ?
C12 C13 1.421(7) . ?
C13 C14 1.372(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.401(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(7) . ?
C15 H15 0.9500 . ?
C16 O3 1.370(6) . ?
C16 C17 1.424(6) . ?
C17 O1 1.309(6) . ?
C18 O3 1.439(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 N2 1.296(7) . ?
C21 C22 1.443(8) . ?
C21 H21 0.9500 . ?
C22 C27 1.420(7) . ?
C22 C23 1.422(7) . ?
C23 C24 1.352(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.415(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(7) . ?
C25 H25 0.9500 . ?
C26 O4 1.377(6) . ?
C26 C27 1.413(7) . ?
C27 O2 1.325(6) . ?
C28 O4 1.441(6) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C31 C32 1.492(9) . ?
C32 N3 1.111(7) . ?
N1 Ni1 1.858(4) . ?
N2 Ni1 1.850(4) . ?
N3 Na1 2.470(5) . ?
O1 Ni1 1.843(4) . ?
O1 Na1 2.345(4) . ?
O2 Ni1 1.844(3) . ?
O2 Na1 2.340(4) . ?
O3 Na1 2.476(4) . ?
O4 Na1 2.561(5) . ?
O5 Cl1 1.386(6) . ?
O6 Cl1 1.427(4) . ?
O6 Na1 2.357(5) . ?
O7 Cl1 1.426(5) . ?
O8 Cl1 1.394(6) . ?
Ni1 Na1 3.371(4) . ?
Cl1 Na1 3.268(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 104.8(4) . . ?
N1 C1 C6 117.0(4) . . ?
C2 C1 C6 110.5(5) . . ?
N1 C1 H1 108.1 . . ?
C2 C1 H1 108.1 . . ?
C6 C1 H1 108.1 . . ?
N2 C2 C1 106.2(4) . . ?
N2 C2 C3 116.1(4) . . ?
C1 C2 C3 112.4(4) . . ?
N2 C2 H2 107.2 . . ?
C1 C2 H2 107.2 . . ?
C3 C2 H2 107.2 . . ?
C2 C3 C4 106.8(4) . . ?
C2 C3 H3A 110.4 . . ?
C4 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
C4 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
C5 C4 C3 114.6(5) . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 112.6(5) . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 C1 111.6(4) . . ?
C5 C6 H6A 109.3 . . ?
C1 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C1 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N1 C11 C12 125.8(5) . . ?
N1 C11 H11 117.1 . . ?
C12 C11 H11 117.1 . . ?
C17 C12 C13 119.5(4) . . ?
C17 C12 C11 121.0(4) . . ?
C13 C12 C11 119.4(4) . . ?
C14 C13 C12 121.0(5) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.6(5) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.8(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
O3 C16 C15 126.0(4) . . ?
O3 C16 C17 113.6(4) . . ?
C15 C16 C17 120.4(4) . . ?
O1 C17 C12 124.0(4) . . ?
O1 C17 C16 117.6(4) . . ?
C12 C17 C16 118.4(4) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C21 C22 124.8(4) . . ?
N2 C21 H21 117.6 . . ?
C22 C21 H21 117.6 . . ?
C27 C22 C23 119.0(5) . . ?
C27 C22 C21 121.8(4) . . ?
C23 C22 C21 119.2(4) . . ?
C24 C23 C22 121.1(5) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 120.4(4) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C24 119.9(5) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
O4 C26 C25 125.2(4) . . ?
O4 C26 C27 114.0(4) . . ?
C25 C26 C27 120.8(5) . . ?
O2 C27 C26 117.7(4) . . ?
O2 C27 C22 123.6(5) . . ?
C26 C27 C22 118.8(5) . . ?
O4 C28 H28A 109.5 . . ?
O4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C32 C31 173.6(8) . . ?
C11 N1 C1 120.8(4) . . ?
C11 N1 Ni1 126.1(3) . . ?
C1 N1 Ni1 113.0(3) . . ?
C21 N2 C2 123.0(4) . . ?
C21 N2 Ni1 126.3(3) . . ?
C2 N2 Ni1 110.5(3) . . ?
C32 N3 Na1 171.7(5) . . ?
C17 O1 Ni1 127.6(3) . . ?
C17 O1 Na1 124.1(3) . . ?
Ni1 O1 Na1 106.59(16) . . ?
C27 O2 Ni1 126.6(3) . . ?
C27 O2 Na1 126.4(3) . . ?
Ni1 O2 Na1 106.72(14) . . ?
C16 O3 C18 116.5(4) . . ?
C16 O3 Na1 118.9(3) . . ?
C18 O3 Na1 122.8(3) . . ?
C26 O4 C28 116.4(4) . . ?
C26 O4 Na1 118.1(3) . . ?
C28 O4 Na1 125.4(3) . . ?
Cl1 O6 Na1 117.3(2) . . ?
O1 Ni1 O2 83.10(14) . . ?
O1 Ni1 N2 178.55(17) . . ?
O2 Ni1 N2 95.57(17) . . ?
O1 Ni1 N1 94.66(17) . . ?
O2 Ni1 N1 176.74(17) . . ?
N2 Ni1 N1 86.69(18) . . ?
O1 Ni1 Na1 41.81(12) . . ?
O2 Ni1 Na1 41.67(10) . . ?
N2 Ni1 Na1 136.80(14) . . ?
N1 Ni1 Na1 136.32(12) . . ?
O5 Cl1 O8 111.5(6) . . ?
O5 Cl1 O7 109.4(3) . . ?
O8 Cl1 O7 109.8(4) . . ?
O5 Cl1 O6 108.5(4) . . ?
O8 Cl1 O6 106.2(4) . . ?
O7 Cl1 O6 111.3(3) . . ?
O5 Cl1 Na1 69.5(4) . . ?
O8 Cl1 Na1 129.0(3) . . ?
O7 Cl1 Na1 117.6(2) . . ?
O6 Cl1 Na1 39.87(18) . . ?
O2 Na1 O1 62.95(12) . . ?
O2 Na1 O6 124.32(17) . . ?
O1 Na1 O6 124.42(17) . . ?
O2 Na1 N3 130.60(17) . . ?
O1 Na1 N3 125.23(17) . . ?
O6 Na1 N3 92.37(18) . . ?
O2 Na1 O3 127.62(13) . . ?
O1 Na1 O3 64.67(14) . . ?
O6 Na1 O3 86.23(17) . . ?
N3 Na1 O3 81.32(17) . . ?
O2 Na1 O4 63.61(12) . . ?
O1 Na1 O4 124.57(15) . . ?
O6 Na1 O4 97.36(17) . . ?
N3 Na1 O4 81.58(17) . . ?
O3 Na1 O4 162.65(14) . . ?
O2 Na1 Cl1 111.49(10) . . ?
O1 Na1 Cl1 102.42(14) . . ?
O6 Na1 Cl1 22.83(10) . . ?
N3 Na1 Cl1 112.70(14) . . ?
O3 Na1 Cl1 79.87(14) . . ?
O4 Na1 Cl1 109.59(14) . . ?
O2 Na1 Ni1 31.60(9) . . ?
O1 Na1 Ni1 31.61(8) . . ?
O6 Na1 Ni1 128.43(13) . . ?
N3 Na1 Ni1 139.04(14) . . ?
O3 Na1 Ni1 96.15(12) . . ?
O4 Na1 Ni1 94.85(11) . . ?
Cl1 Na1 Ni1 106.94(8) . . ?

_refine_diff_density_max         0.649
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 1026191'
#######################################################################
#
#                 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_2

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 N8 O4 Zn2'
_chemical_formula_weight         595.23

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.3070(2)
_cell_length_b                   17.3040(2)
_cell_length_c                   11.8370(2)
_cell_angle_alpha                90.000(2)
_cell_angle_beta                 103.407(2)
_cell_angle_gamma                90.000(2)
_cell_volume                     2252.87(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    35459
_cell_measurement_theta_min      2.535
_cell_measurement_theta_max      27.000

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    2.179
_shelx_estimated_absorpt_T_min   0.520
_shelx_estimated_absorpt_T_max   0.875
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35459
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.535
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             4773
_reflns_number_gt                4099
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_structure_solution    WINGX
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Diamond 3'
_computing_publication_material  'Microsoft word 2010'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0210P)²+50.5386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4773
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0895
_refine_ls_wR_factor_ref         0.1910
_refine_ls_wR_factor_gt          0.1856
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3010(7) 0.1140(4) 0.4208(7) 0.0213(17) Uani 1 1 d . . . . .
C2 C 0.2155(8) 0.0640(4) 0.3507(7) 0.0218(17) Uani 1 1 d . . . . .
C3 C 0.2099(10) -0.0135(5) 0.3877(9) 0.035(2) Uani 1 1 d . . . . .
H3 H 0.1515 -0.0476 0.3429 0.042 Uiso 1 1 calc R U . . .
C4 C 0.2870(10) -0.0403(5) 0.4868(8) 0.040(3) Uani 1 1 d . . . . .
H4 H 0.2812 -0.0925 0.5100 0.048 Uiso 1 1 calc R U . . .
C5 C 0.3748(9) 0.0089(5) 0.5547(8) 0.032(2) Uani 1 1 d . . . . .
H5 H 0.4291 -0.0109 0.6221 0.038 Uiso 1 1 calc R U . . .
C6 C 0.3829(8) 0.0859(5) 0.5243(8) 0.030(2) Uani 1 1 d . . . . .
C7 C 0.5296(9) 0.1177(7) 0.6933(8) 0.041(3) Uani 1 1 d . . . . .
H7A H 0.5832 0.1609 0.7248 0.061 Uiso 1 1 calc R U . . .
H7B H 0.5786 0.0716 0.6887 0.061 Uiso 1 1 calc R U . . .
H7C H 0.4744 0.1072 0.7443 0.061 Uiso 1 1 calc R U . . .
C8 C 0.1293(7) 0.0871(4) 0.2454(7) 0.0209(16) Uani 1 1 d . . . . .
H8 H 0.0684 0.0507 0.2119 0.025 Uiso 1 1 calc R U . . .
C9 C 0.0293(7) 0.1738(4) 0.0912(6) 0.0179(15) Uani 1 1 d . . . . .
H9 H -0.0418 0.1921 0.1209 0.021 Uiso 1 1 calc R U . . .
C10 C -0.0152(8) 0.1087(4) 0.0051(7) 0.0248(17) Uani 1 1 d . . . . .
H10A H 0.0536 0.0882 -0.0245 0.030 Uiso 1 1 calc R U . . .
H10B H -0.0482 0.0661 0.0444 0.030 Uiso 1 1 calc R U . . .
C11 C -0.1135(9) 0.1389(5) -0.0955(8) 0.033(2) Uani 1 1 d . . . . .
H11A H -0.1853 0.1544 -0.0664 0.040 Uiso 1 1 calc R U . . .
H11B H -0.1389 0.0971 -0.1531 0.040 Uiso 1 1 calc R U . . .
C12 C -0.0694(9) 0.2080(5) -0.1547(7) 0.032(2) Uani 1 1 d . . . . .
H12A H -0.0034 0.1912 -0.1914 0.039 Uiso 1 1 calc R U . . .
H12B H -0.1371 0.2277 -0.2167 0.039 Uiso 1 1 calc R U . . .
C13 C -0.0228(7) 0.2727(4) -0.0688(6) 0.0217(16) Uani 1 1 d . . . . .
H13A H 0.0107 0.3150 -0.1084 0.026 Uiso 1 1 calc R U . . .
H13B H -0.0906 0.2938 -0.0384 0.026 Uiso 1 1 calc R U . . .
C14 C 0.0739(8) 0.2423(4) 0.0292(7) 0.0216(16) Uani 1 1 d . . . . .
H14 H 0.1390 0.2212 -0.0067 0.026 Uiso 1 1 calc R U . . .
C15 C 0.1101(7) 0.3686(4) 0.1177(6) 0.0149(14) Uani 1 1 d . . . . .
H15 H 0.0518 0.3883 0.0530 0.018 Uiso 1 1 calc R U . . .
C16 C 0.1653(6) 0.4227(4) 0.2086(6) 0.0126(13) Uani 1 1 d . . . . .
C17 C 0.1378(7) 0.5015(4) 0.1860(7) 0.0181(15) Uani 1 1 d . . . . .
H17 H 0.0847 0.5157 0.1144 0.022 Uiso 1 1 calc R U . . .
C18 C 0.1854(7) 0.5583(4) 0.2644(7) 0.0214(16) Uani 1 1 d . . . . .
H18 H 0.1665 0.6110 0.2459 0.026 Uiso 1 1 calc R U . . .
C19 C 0.2614(7) 0.5388(4) 0.3708(7) 0.0186(15) Uani 1 1 d . . . . .
H19 H 0.2948 0.5778 0.4253 0.022 Uiso 1 1 calc R U . . .
C20 C 0.2877(6) 0.4612(4) 0.3961(6) 0.0149(14) Uani 1 1 d . . . . .
C21 C 0.2443(6) 0.4020(4) 0.3151(6) 0.0128(13) Uani 1 1 d . . . . .
C22 C 0.3899(8) 0.4885(5) 0.5928(7) 0.0257(17) Uani 1 1 d . . . . .
H22A H 0.4407 0.4628 0.6607 0.039 Uiso 1 1 calc R U . . .
H22B H 0.3155 0.5076 0.6121 0.039 Uiso 1 1 calc R U . . .
H22C H 0.4348 0.5319 0.5698 0.039 Uiso 1 1 calc R U . . .
N1 N 0.1275(6) 0.1519(4) 0.1935(5) 0.0178(13) Uani 1 1 d . . . . .
N2 N 0.1341(6) 0.2967(3) 0.1184(5) 0.0159(12) Uani 1 1 d . . . . .
N3 N 0.3871(6) 0.2901(4) 0.6605(7) 0.0273(15) Uani 1 1 d . . . . .
N4 N 0.4781(8) 0.3131(5) 0.7226(6) 0.0368(19) Uani 1 1 d . . . . .
N5 N 0.5648(8) 0.3341(5) 0.7819(7) 0.040(2) Uani 1 1 d . . . . .
N6 N 0.5574(7) 0.3051(5) 0.4762(7) 0.0340(17) Uani 1 1 d . . . . .
N7 N 0.6453(7) 0.2699(5) 0.5284(7) 0.0313(17) Uani 1 1 d . . . . .
N8 N 0.7306(8) 0.2388(6) 0.5768(8) 0.048(2) Uani 1 1 d . . . . .
O1 O 0.3106(5) 0.1881(3) 0.3987(4) 0.0202(11) Uani 1 1 d . . . . .
O2 O 0.2768(4) 0.3304(3) 0.3457(4) 0.0138(10) Uani 1 1 d . . . . .
O3 O 0.4610(6) 0.1370(4) 0.5812(5) 0.0317(14) Uani 1 1 d . . . . .
O4 O 0.3590(5) 0.4344(3) 0.4984(5) 0.0228(12) Uani 1 1 d . . . . .
Zn1 Zn 0.25349(8) 0.23722(5) 0.24193(7) 0.0138(2) Uani 1 1 d . . . . .
Zn2 Zn 0.39337(9) 0.28272(6) 0.49111(8) 0.0248(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.318(9) . ?
C1 C2 1.415(12) . ?
C1 C6 1.439(11) . ?
C2 C3 1.417(11) . ?
C2 C8 1.448(11) . ?
C3 C4 1.370(14) . ?
C4 C5 1.410(15) . ?
C5 C6 1.389(12) . ?
C6 O3 1.320(12) . ?
C7 O3 1.414(10) . ?
C8 N1 1.277(10) . ?
C9 N1 1.490(10) . ?
C9 C10 1.524(10) . ?
C9 C14 1.540(10) . ?
C10 C11 1.521(13) . ?
C11 C12 1.527(12) . ?
C12 C13 1.522(11) . ?
C13 C14 1.492(11) . ?
C14 N2 1.460(9) . ?
C15 N2 1.272(9) . ?
C15 C16 1.453(10) . ?
C16 C17 1.410(10) . ?
C16 C21 1.412(10) . ?
C17 C18 1.374(11) . ?
C18 C19 1.391(11) . ?
C19 C20 1.392(10) . ?
C20 O4 1.371(9) . ?
C20 C21 1.412(10) . ?
C21 O2 1.319(8) . ?
C22 O4 1.436(9) . ?
N1 Zn1 2.039(6) . ?
N2 Zn1 2.027(6) . ?
N3 N4 1.186(11) . ?
N3 Zn2 2.026(7) . ?
N3 Zn1 2.027(7) 4_566 ?
N4 N5 1.125(11) . ?
N6 N7 1.206(10) . ?
N6 Zn2 1.942(8) . ?
N7 N8 1.137(11) . ?
O1 Zn1 2.006(5) . ?
O1 Zn2 2.069(6) . ?
O2 Zn1 2.006(5) . ?
O2 Zn2 2.080(5) . ?
Zn1 N3 2.027(7) 4_565 ?
Zn1 Zn2 3.1077(13) . ?

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 C1 C2 123.8(7) . . ?
O1 C1 C6 115.6(8) . . ?
C2 C1 C6 120.6(7) . . ?
C1 C2 C3 118.1(8) . . ?
C1 C2 C8 124.5(7) . . ?
C3 C2 C8 117.3(8) . . ?
C4 C3 C2 121.3(10) . . ?
C3 C4 C5 120.6(8) . . ?
C6 C5 C4 120.7(8) . . ?
O3 C6 C5 126.0(8) . . ?
O3 C6 C1 115.4(7) . . ?
C5 C6 C1 118.6(9) . . ?
N1 C8 C2 126.1(7) . . ?
N1 C9 C10 115.1(6) . . ?
N1 C9 C14 108.5(6) . . ?
C10 C9 C14 110.1(6) . . ?
C11 C10 C9 109.7(7) . . ?
C10 C11 C12 111.8(8) . . ?
C13 C12 C11 111.6(7) . . ?
C14 C13 C12 109.7(7) . . ?
N2 C14 C13 118.0(6) . . ?
N2 C14 C9 107.6(6) . . ?
C13 C14 C9 112.3(6) . . ?
N2 C15 C16 124.8(7) . . ?
C17 C16 C21 118.7(6) . . ?
C17 C16 C15 116.4(6) . . ?
C21 C16 C15 124.9(6) . . ?
C18 C17 C16 122.0(7) . . ?
C17 C18 C19 120.0(7) . . ?
C18 C19 C20 119.0(7) . . ?
O4 C20 C19 124.7(7) . . ?
O4 C20 C21 113.3(6) . . ?
C19 C20 C21 122.0(7) . . ?
O2 C21 C16 124.2(6) . . ?
O2 C21 C20 117.7(6) . . ?
C16 C21 C20 118.1(6) . . ?
C8 N1 C9 122.7(7) . . ?
C8 N1 Zn1 124.6(6) . . ?
C9 N1 Zn1 112.7(4) . . ?
C15 N2 C14 124.3(7) . . ?
C15 N2 Zn1 127.3(5) . . ?
C14 N2 Zn1 108.4(5) . . ?
N4 N3 Zn2 114.2(6) . . ?
N4 N3 Zn1 114.7(6) . 4_566 ?
Zn2 N3 Zn1 131.1(4) . 4_566 ?
N5 N4 N3 179.2(11) . . ?
N7 N6 Zn2 122.9(6) . . ?
N8 N7 N6 177.6(10) . . ?
C1 O1 Zn1 124.9(5) . . ?
C1 O1 Zn2 135.5(5) . . ?
Zn1 O1 Zn2 99.4(2) . . ?
C21 O2 Zn1 126.7(4) . . ?
C21 O2 Zn2 133.0(4) . . ?
Zn1 O2 Zn2 99.0(2) . . ?
C6 O3 C7 118.5(8) . . ?
C20 O4 C22 117.0(6) . . ?
O2 Zn1 O1 78.8(2) . . ?
O2 Zn1 N2 90.3(2) . . ?
O1 Zn1 N2 154.2(2) . . ?
O2 Zn1 N3 118.1(3) . 4_565 ?
O1 Zn1 N3 103.0(3) . 4_565 ?
N2 Zn1 N3 102.7(3) . 4_565 ?
O2 Zn1 N1 137.5(2) . . ?
O1 Zn1 N1 90.4(2) . . ?
N2 Zn1 N1 81.9(2) . . ?
N3 Zn1 N1 104.3(3) 4_565 . ?
O2 Zn1 Zn2 41.39(14) . . ?
O1 Zn1 Zn2 41.05(16) . . ?
N2 Zn1 Zn2 131.57(17) . . ?
N3 Zn1 Zn2 103.8(2) 4_565 . ?
N1 Zn1 Zn2 128.24(17) . . ?
N6 Zn2 N3 109.3(3) . . ?
N6 Zn2 O1 115.7(3) . . ?
N3 Zn2 O1 117.2(2) . . ?
N6 Zn2 O2 106.3(3) . . ?
N3 Zn2 O2 129.3(3) . . ?
O1 Zn2 O2 75.75(19) . . ?
N6 Zn2 Zn1 104.5(2) . . ?
N3 Zn2 Zn1 145.9(2) . . ?
O1 Zn2 Zn1 39.57(14) . . ?
O2 Zn2 Zn1 39.62(13) . . ?

_refine_diff_density_max         1.238
_refine_diff_density_min         -1.579
_refine_diff_density_rms         0.177

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 1026192'
