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

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#
#                 Cambridge Crystallographic Data Centre
#                                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.
#
#  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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
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data_pj024_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H72 N4 O4 Zn2'
_chemical_formula_weight         755.72

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   10.6599(9)
_cell_length_b                   12.5644(10)
_cell_length_c                   15.3343(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.876(3)
_cell_angle_gamma                90.00
_cell_volume                     1943.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9251
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.35

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    1.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6393
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21215
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         27.43
_reflns_number_total             4418
_reflns_number_gt                3357
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0287P)²+0.3245P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4418
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0909
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.37824(2) 0.93841(2) 0.919781(17) 0.01517(10) Uani 1 1 d . . .
O1 O 0.62568(14) 0.91413(13) 1.06492(10) 0.0193(4) Uani 1 1 d . . .
O2 O 0.24118(14) 0.86925(12) 0.83125(11) 0.0196(4) Uani 1 1 d . . .
N1 N 0.53506(16) 0.84739(15) 0.99672(12) 0.0151(4) Uani 1 1 d . . .
C2 C 0.4841(2) 0.76363(18) 1.04933(16) 0.0189(5) Uani 1 1 d . . .
C3 C 0.3988(2) 0.68460(19) 0.97893(17) 0.0248(6) Uani 1 1 d . . .
H3A H 0.3702 0.6269 1.0123 0.030 Uiso 1 1 calc R . .
H3B H 0.3181 0.7216 0.9400 0.030 Uiso 1 1 calc R . .
C4 C 0.4693(2) 0.6356(2) 0.91710(18) 0.0274(6) Uani 1 1 d . . .
H4A H 0.4077 0.5883 0.8712 0.033 Uiso 1 1 calc R . .
H4B H 0.5453 0.5923 0.9545 0.033 Uiso 1 1 calc R . .
C5 C 0.5182(2) 0.72344(19) 0.86799(16) 0.0240(6) Uani 1 1 d . . .
H5A H 0.4407 0.7619 0.8265 0.029 Uiso 1 1 calc R . .
H5B H 0.5667 0.6910 0.8295 0.029 Uiso 1 1 calc R . .
C6 C 0.6097(2) 0.80361(18) 0.93468(15) 0.0186(5) Uani 1 1 d . . .
C7 C 0.6354(2) 0.8974(2) 0.87953(17) 0.0235(6) Uani 1 1 d . . .
H7A H 0.6937 0.9488 0.9216 0.035 Uiso 1 1 calc R . .
H7B H 0.5511 0.9318 0.8459 0.035 Uiso 1 1 calc R . .
H7C H 0.6780 0.8717 0.8356 0.035 Uiso 1 1 calc R . .
C8 C 0.7451(2) 0.7542(2) 0.98801(18) 0.0266(6) Uani 1 1 d . . .
H8A H 0.7875 0.7963 1.0435 0.040 Uiso 1 1 calc R . .
H8B H 0.8016 0.7538 0.9488 0.040 Uiso 1 1 calc R . .
H8C H 0.7321 0.6811 1.0056 0.040 Uiso 1 1 calc R . .
C9 C 0.3974(2) 0.8218(2) 1.09604(17) 0.0255(6) Uani 1 1 d . . .
H9A H 0.3258 0.8590 1.0494 0.038 Uiso 1 1 calc R . .
H9B H 0.4514 0.8735 1.1403 0.038 Uiso 1 1 calc R . .
H9C H 0.3594 0.7702 1.1284 0.038 Uiso 1 1 calc R . .
C10 C 0.5942(2) 0.7071(2) 1.12547(17) 0.0276(6) Uani 1 1 d . . .
H10A H 0.5560 0.6732 1.1687 0.041 Uiso 1 1 calc R . .
H10B H 0.6611 0.7593 1.1585 0.041 Uiso 1 1 calc R . .
H10C H 0.6357 0.6529 1.0978 0.041 Uiso 1 1 calc R . .
N2 N 0.15002(17) 0.95313(14) 0.78284(13) 0.0162(4) Uani 1 1 d . . .
C12 C 0.0223(2) 0.93655(18) 0.80009(17) 0.0204(5) Uani 1 1 d . . .
C13 C -0.0389(2) 0.8249(2) 0.77710(18) 0.0276(6) Uani 1 1 d . . .
H13A H 0.0307 0.7711 0.7991 0.041 Uiso 1 1 calc R . .
H13B H -0.0802 0.8181 0.7102 0.041 Uiso 1 1 calc R . .
H13C H -0.1061 0.8145 0.8073 0.041 Uiso 1 1 calc R . .
C14 C 0.0489(3) 0.9553(2) 0.90315(18) 0.0318(6) Uani 1 1 d . . .
H14A H 0.0882 1.0259 0.9201 0.048 Uiso 1 1 calc R . .
H14B H 0.1102 0.9008 0.9386 0.048 Uiso 1 1 calc R . .
H14C H -0.0348 0.9510 0.9167 0.048 Uiso 1 1 calc R . .
C15 C -0.0734(2) 1.0236(2) 0.74673(19) 0.0308(6) Uani 1 1 d . . .
H15A H -0.1623 1.0102 0.7518 0.037 Uiso 1 1 calc R . .
H15B H -0.0424 1.0934 0.7756 0.037 Uiso 1 1 calc R . .
C16 C -0.0848(2) 1.0286(2) 0.64539(19) 0.0328(7) Uani 1 1 d . . .
H16A H -0.1417 1.0894 0.6156 0.039 Uiso 1 1 calc R . .
H16B H -0.1262 0.9625 0.6140 0.039 Uiso 1 1 calc R . .
C17 C 0.0525(2) 1.0419(2) 0.63645(18) 0.0275(6) Uani 1 1 d . . .
H17A H 0.0895 1.1114 0.6629 0.033 Uiso 1 1 calc R . .
H17B H 0.0446 1.0422 0.5703 0.033 Uiso 1 1 calc R . .
C18 C 0.1484(2) 0.95331(18) 0.68534(16) 0.0190(5) Uani 1 1 d . . .
C19 C 0.2882(2) 0.9862(2) 0.68759(18) 0.0271(6) Uani 1 1 d . . .
H19A H 0.3121 1.0538 0.7206 0.041 Uiso 1 1 calc R . .
H19B H 0.2897 0.9945 0.6244 0.041 Uiso 1 1 calc R . .
H19C H 0.3518 0.9311 0.7192 0.041 Uiso 1 1 calc R . .
C20 C 0.1145(2) 0.8471(2) 0.63319(17) 0.0261(6) Uani 1 1 d . . .
H20A H 0.0187 0.8349 0.6148 0.039 Uiso 1 1 calc R . .
H20B H 0.1611 0.7890 0.6734 0.039 Uiso 1 1 calc R . .
H20C H 0.1422 0.8497 0.5782 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 O2 1.8572(15) . ?
Zn1 O1 1.8696(16) 3_677 ?
Zn1 N1 2.0539(17) . ?
O1 N1 1.441(2) . ?
O1 Zn1 1.8696(16) 3_677 ?
O2 N2 1.463(2) . ?
N1 C6 1.527(3) . ?
N1 C2 1.529(3) . ?
C2 C9 1.526(3) . ?
C2 C3 1.531(3) . ?
C2 C10 1.535(3) . ?
C3 C4 1.518(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.520(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.538(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.526(3) . ?
C6 C8 1.540(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N2 C12 1.483(3) . ?
N2 C18 1.490(3) . ?
C12 C14 1.531(4) . ?
C12 C15 1.538(3) . ?
C12 C13 1.539(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.520(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.522(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.533(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.535(3) . ?
C18 C20 1.538(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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 120.74(6) . 3_677 ?
O2 Zn1 N1 117.45(7) . . ?
O1 Zn1 N1 121.78(7) 3_677 . ?
N1 O1 Zn1 129.11(12) . 3_677 ?
N2 O2 Zn1 105.68(11) . . ?
O1 N1 C6 107.45(15) . . ?
O1 N1 C2 106.68(15) . . ?
C6 N1 C2 115.26(17) . . ?
O1 N1 Zn1 108.83(12) . . ?
C6 N1 Zn1 109.52(13) . . ?
C2 N1 Zn1 108.91(12) . . ?
C9 C2 N1 106.90(18) . . ?
C9 C2 C3 109.26(19) . . ?
N1 C2 C3 107.81(18) . . ?
C9 C2 C10 107.11(19) . . ?
N1 C2 C10 113.87(18) . . ?
C3 C2 C10 111.71(19) . . ?
C4 C3 C2 113.72(19) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C5 109.5(2) . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
C4 C5 C6 113.0(2) . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 N1 106.89(18) . . ?
C7 C6 C5 109.04(19) . . ?
N1 C6 C5 107.69(17) . . ?
C7 C6 C8 107.45(19) . . ?
N1 C6 C8 113.70(18) . . ?
C5 C6 C8 111.88(19) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 N2 C12 107.81(16) . . ?
O2 N2 C18 107.49(16) . . ?
C12 N2 C18 117.77(17) . . ?
N2 C12 C14 106.77(18) . . ?
N2 C12 C15 107.10(19) . . ?
C14 C12 C15 108.0(2) . . ?
N2 C12 C13 115.61(19) . . ?
C14 C12 C13 107.4(2) . . ?
C15 C12 C13 111.6(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C12 113.2(2) . . ?
C16 C15 H15A 108.9 . . ?
C12 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C12 C15 H15B 108.9 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 109.6(2) . . ?
C15 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C16 C17 C18 112.6(2) . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
N2 C18 C17 106.34(19) . . ?
N2 C18 C19 106.37(18) . . ?
C17 C18 C19 107.7(2) . . ?
N2 C18 C20 116.43(19) . . ?
C17 C18 C20 111.6(2) . . ?
C19 C18 C20 107.94(19) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1 Zn1 O2 N2 2.72(14) 3_677 . . . ?
N1 Zn1 O2 N2 -175.57(11) . . . . ?
Zn1 O1 N1 C6 112.51(17) 3_677 . . . ?
Zn1 O1 N1 C2 -123.36(16) 3_677 . . . ?
Zn1 O1 N1 Zn1 -5.99(19) 3_677 . . . ?
O2 Zn1 N1 O1 -176.25(11) . . . . ?
O1 Zn1 N1 O1 5.47(18) 3_677 . . . ?
O2 Zn1 N1 C6 66.55(15) . . . . ?
O1 Zn1 N1 C6 -111.73(14) 3_677 . . . ?
O2 Zn1 N1 C2 -60.32(15) . . . . ?
O1 Zn1 N1 C2 121.40(13) 3_677 . . . ?
O1 N1 C2 C9 68.4(2) . . . . ?
C6 N1 C2 C9 -172.41(17) . . . . ?
Zn1 N1 C2 C9 -48.90(19) . . . . ?
O1 N1 C2 C3 -174.22(16) . . . . ?
C6 N1 C2 C3 -55.0(2) . . . . ?
Zn1 N1 C2 C3 68.47(18) . . . . ?
O1 N1 C2 C10 -49.7(2) . . . . ?
C6 N1 C2 C10 69.5(2) . . . . ?
Zn1 N1 C2 C10 -166.98(16) . . . . ?
C9 C2 C3 C4 170.4(2) . . . . ?
N1 C2 C3 C4 54.5(2) . . . . ?
C10 C2 C3 C4 -71.3(3) . . . . ?
C2 C3 C4 C5 -56.5(3) . . . . ?
C3 C4 C5 C6 56.8(2) . . . . ?
O1 N1 C6 C7 -68.62(19) . . . . ?
C2 N1 C6 C7 172.64(17) . . . . ?
Zn1 N1 C6 C7 49.44(18) . . . . ?
O1 N1 C6 C5 174.33(16) . . . . ?
C2 N1 C6 C5 55.6(2) . . . . ?
Zn1 N1 C6 C5 -67.61(19) . . . . ?
O1 N1 C6 C8 49.8(2) . . . . ?
C2 N1 C6 C8 -69.0(2) . . . . ?
Zn1 N1 C6 C8 167.84(15) . . . . ?
C4 C5 C6 C7 -171.10(19) . . . . ?
C4 C5 C6 N1 -55.5(2) . . . . ?
C4 C5 C6 C8 70.2(3) . . . . ?
Zn1 O2 N2 C12 -116.09(15) . . . . ?
Zn1 O2 N2 C18 116.00(14) . . . . ?
O2 N2 C12 C14 65.9(2) . . . . ?
C18 N2 C12 C14 -172.37(19) . . . . ?
O2 N2 C12 C15 -178.57(18) . . . . ?
C18 N2 C12 C15 -56.8(3) . . . . ?
O2 N2 C12 C13 -53.5(2) . . . . ?
C18 N2 C12 C13 68.2(3) . . . . ?
N2 C12 C15 C16 53.0(3) . . . . ?
C14 C12 C15 C16 167.6(2) . . . . ?
C13 C12 C15 C16 -74.5(3) . . . . ?
C12 C15 C16 C17 -55.0(3) . . . . ?
C15 C16 C17 C18 56.5(3) . . . . ?
O2 N2 C18 C17 -179.91(17) . . . . ?
C12 N2 C18 C17 58.2(2) . . . . ?
O2 N2 C18 C19 -65.3(2) . . . . ?
C12 N2 C18 C19 172.84(19) . . . . ?
O2 N2 C18 C20 55.0(2) . . . . ?
C12 N2 C18 C20 -66.9(3) . . . . ?
C16 C17 C18 N2 -55.7(3) . . . . ?
C16 C17 C18 C19 -169.4(2) . . . . ?
C16 C17 C18 C20 72.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.085
_database_code_depnum_ccdc_archive 'CCDC 1000444'
#######################################################################
#
#                 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_t1_twin

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7.50 H15 N0.75 O0.75 Zn0.75'
_chemical_formula_weight         176.73

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'

_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   R-3

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   19.8098(6)
_cell_length_b                   19.8098(6)
_cell_length_c                   14.6920(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4993.1(3)
_cell_formula_units_Z            24
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2250
_exptl_absorpt_coefficient_mu    2.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6136
_exptl_absorpt_correction_T_max  0.7333
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1944
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1944
_reflns_number_gt                1837
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0422P)²+4.4934P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1944
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.84711(2) 0.97321(2) 0.00705(3) 0.01833(13) Uani 1 1 d . . .
O1 O 0.81261(13) 1.03405(13) -0.06260(16) 0.0203(5) Uani 1 1 d . . .
N1 N 0.76725(17) 0.87658(17) 0.08665(19) 0.0184(6) Uani 1 1 d . . .
C9 C 0.8688(3) 0.9151(3) 0.2056(3) 0.0309(9) Uani 1 1 d . . .
H9A H 0.8754 0.8694 0.1991 0.046 Uiso 1 1 calc R . .
H9B H 0.8838 0.9362 0.2673 0.046 Uiso 1 1 calc R . .
H9C H 0.9019 0.9549 0.1612 0.046 Uiso 1 1 calc R . .
C8 C 0.6828(2) 0.8502(2) -0.0469(3) 0.0285(9) Uani 1 1 d . . .
H8A H 0.6320 0.8408 -0.0684 0.043 Uiso 1 1 calc R . .
H8B H 0.6903 0.8069 -0.0659 0.043 Uiso 1 1 calc R . .
H8C H 0.7242 0.8990 -0.0730 0.043 Uiso 1 1 calc R . .
C7 C 0.7707(3) 0.9587(2) 0.2143(3) 0.0301(9) Uani 1 1 d . . .
H7A H 0.7775 0.9676 0.2808 0.036 Uiso 1 1 calc R . .
H7B H 0.8104 1.0068 0.1837 0.036 Uiso 1 1 calc R . .
C6 C 0.6859(2) 0.8561(2) 0.0568(3) 0.0232(8) Uani 1 1 d . . .
C5 C 0.7840(2) 0.8912(2) 0.1889(2) 0.0233(8) Uani 1 1 d . . .
C4 C 0.6902(3) 0.9433(3) 0.1877(3) 0.0387(10) Uani 1 1 d . . .
H4A H 0.6858 0.9899 0.2018 0.046 Uiso 1 1 calc R . .
H4B H 0.6504 0.8992 0.2241 0.046 Uiso 1 1 calc R . .
C3 C 0.6740(2) 0.9240(2) 0.0860(3) 0.0295(9) Uani 1 1 d . . .
H3A H 0.6197 0.9104 0.0724 0.035 Uiso 1 1 calc R . .
H3B H 0.7092 0.9708 0.0500 0.035 Uiso 1 1 calc R . .
C2 C 0.7361(3) 0.8186(3) 0.2480(3) 0.0398(10) Uani 1 1 d . . .
H2A H 0.7383 0.7743 0.2217 0.060 Uiso 1 1 calc R . .
H2B H 0.6818 0.8068 0.2502 0.060 Uiso 1 1 calc R . .
H2C H 0.7577 0.8285 0.3097 0.060 Uiso 1 1 calc R . .
C1 C 0.6208(2) 0.7781(2) 0.0926(3) 0.0337(10) Uani 1 1 d . . .
H1F H 0.5724 0.7637 0.0598 0.051 Uiso 1 1 calc R . .
H1G H 0.6133 0.7827 0.1577 0.051 Uiso 1 1 calc R . .
H1H H 0.6351 0.7379 0.0832 0.051 Uiso 1 1 calc R . .
C100 C 0.4062(3) 0.7319(3) 0.1676(5) 0.0696(18) Uani 1 1 d . . .
H10A H 0.4566 0.7770 0.1700 0.083 Uiso 1 1 calc R . .
H1 H 0.895(3) 1.045(3) -0.001(3) 0.050 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 1.947(2) . ?
Zn1 N1 2.123(3) . ?
Zn1 Zn1 2.8090(4) 11_565 ?
Zn1 Zn1 2.8090(4) 12_655 ?
Zn1 H1 1.26(5) . ?
O1 N1 1.437(4) 11_565 ?
N1 O1 1.437(4) 12_655 ?
N1 C6 1.518(5) . ?
N1 C5 1.535(4) . ?
C9 C5 1.521(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 C6 1.527(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 C4 1.518(6) . ?
C7 C5 1.533(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C6 C1 1.528(5) . ?
C6 C3 1.537(5) . ?
C5 C2 1.534(6) . ?
C4 C3 1.536(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C1 H1F 0.9800 . ?
C1 H1G 0.9800 . ?
C1 H1H 0.9800 . ?
C100 C100 1.375(5) 14_455 ?
C100 C100 1.375(5) 15 ?
C100 H10A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 N1 120.92(11) . . ?
O1 Zn1 Zn1 72.05(7) . 11_565 ?
N1 Zn1 Zn1 150.80(8) . 11_565 ?
O1 Zn1 Zn1 142.43(8) . 12_655 ?
N1 Zn1 Zn1 68.02(8) . 12_655 ?
Zn1 Zn1 Zn1 119.462(5) 11_565 12_655 ?
O1 Zn1 H1 63(2) . . ?
N1 Zn1 H1 150(2) . . ?
Zn1 Zn1 H1 10(2) 11_565 . ?
Zn1 Zn1 H1 129(2) 12_655 . ?
N1 O1 Zn1 111.80(18) 11_565 . ?
O1 N1 C6 107.8(3) 12_655 . ?
O1 N1 C5 107.0(3) 12_655 . ?
C6 N1 C5 115.7(3) . . ?
O1 N1 Zn1 106.58(17) 12_655 . ?
C6 N1 Zn1 107.1(2) . . ?
C5 N1 Zn1 112.1(2) . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C7 C5 112.5(3) . . ?
C4 C7 H7A 109.1 . . ?
C5 C7 H7A 109.1 . . ?
C4 C7 H7B 109.1 . . ?
C5 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N1 C6 C1 114.6(3) . . ?
N1 C6 C8 107.8(3) . . ?
C1 C6 C8 106.6(3) . . ?
N1 C6 C3 106.9(3) . . ?
C1 C6 C3 111.6(3) . . ?
C8 C6 C3 109.2(3) . . ?
C9 C5 C7 109.5(3) . . ?
C9 C5 C2 105.6(3) . . ?
C7 C5 C2 112.6(3) . . ?
C9 C5 N1 108.5(3) . . ?
C7 C5 N1 106.8(3) . . ?
C2 C5 N1 113.8(3) . . ?
C7 C4 C3 111.6(3) . . ?
C7 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C7 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C6 C3 C4 112.7(3) . . ?
C6 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C6 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C2 H2A 109.5 . . ?
C5 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C5 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C6 C1 H1F 109.5 . . ?
C6 C1 H1G 109.5 . . ?
H1F C1 H1G 109.5 . . ?
C6 C1 H1H 109.5 . . ?
H1F C1 H1H 109.5 . . ?
H1G C1 H1H 109.5 . . ?
C100 C100 C100 119.96(5) 14_455 15 ?
C100 C100 H10A 120.0 14_455 . ?
C100 C100 H10A 120.0 15 . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.143
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.082
#===end
_database_code_depnum_ccdc_archive 'CCDC 1000445'
