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

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

data_121123e
_database_code_depnum_ccdc_archive 'CCDC 971571'
_audit_update_record             
;
2013-11-12 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H24 N2 O10 Zn2'
_chemical_formula_weight         799.33

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)/n

loop_
_symmetry_equiv_pos_as_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                   8.3355(7)
_cell_length_b                   10.7168(9)
_cell_length_c                   19.0538(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.0940(10)
_cell_angle_gamma                90.00
_cell_volume                     1695.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             812
_exptl_absorpt_coefficient_mu    1.479
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8086
_exptl_absorpt_correction_T_max  0.8909
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            7671
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_sigmaI/netI    0.0885
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2967
_reflns_number_gt                1747
_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)+(0.0243P)²+0.0000P] 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         2967
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0729
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_restrained_S_all      0.879
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.46755(5) -0.14097(4) 0.04881(3) 0.04676(18) Uani 1 1 d . . .
N1 N 0.3052(3) -0.2792(3) 0.04036(16) 0.0420(8) Uani 1 1 d . . .
O1 O 0.3037(3) -0.0076(3) 0.04309(15) 0.0596(8) Uani 1 1 d . . .
O2 O 0.4274(3) 0.1724(3) 0.03689(14) 0.0571(8) Uani 1 1 d . . .
O3 O 0.6064(3) -0.0944(3) 0.13117(14) 0.0584(8) Uani 1 1 d . . .
O4 O 0.6777(3) -0.2866(3) 0.11123(15) 0.0657(9) Uani 1 1 d . . .
O5 O 0.3296(4) 0.3508(3) 0.12722(14) 0.0593(8) Uani 1 1 d . . .
C1 C 0.3152(4) 0.1076(4) 0.0549(2) 0.0443(11) Uani 1 1 d . . .
C2 C 0.1812(4) 0.1651(4) 0.0899(2) 0.0433(11) Uani 1 1 d . . .
C3 C 0.1931(5) 0.2775(4) 0.1249(2) 0.0507(11) Uani 1 1 d . . .
C4 C 0.0634(7) 0.3250(5) 0.1553(2) 0.0812(17) Uani 1 1 d . . .
H4 H 0.0726 0.4000 0.1799 0.097 Uiso 1 1 calc R . .
C5 C -0.0813(7) 0.2611(7) 0.1493(3) 0.0910(19) Uani 1 1 d . . .
H5 H -0.1698 0.2944 0.1692 0.109 Uiso 1 1 calc R . .
C6 C -0.0957(5) 0.1506(6) 0.1147(3) 0.0716(15) Uani 1 1 d . . .
H6 H -0.1932 0.1079 0.1105 0.086 Uiso 1 1 calc R . .
C7 C 0.0354(4) 0.1036(4) 0.0863(2) 0.0561(12) Uani 1 1 d . . .
H7 H 0.0264 0.0269 0.0634 0.067 Uiso 1 1 calc R . .
C8 C 0.6947(5) -0.1895(5) 0.1458(2) 0.0504(12) Uani 1 1 d . . .
C9 C 0.6775(5) 0.3209(4) 0.2949(2) 0.0440(10) Uani 1 1 d . . .
C10 C 0.5799(5) 0.2219(4) 0.2774(2) 0.0534(11) Uani 1 1 d . . .
H10 H 0.5936 0.1483 0.3030 0.064 Uiso 1 1 calc R . .
C11 C 0.4613(5) 0.2283(4) 0.2224(2) 0.0547(11) Uani 1 1 d . . .
H11 H 0.3947 0.1602 0.2113 0.066 Uiso 1 1 calc R . .
C12 C 0.4430(5) 0.3368(4) 0.1842(2) 0.0473(11) Uani 1 1 d . . .
C13 C 0.5412(5) 0.4371(4) 0.2004(2) 0.0525(11) Uani 1 1 d . . .
H13 H 0.5292 0.5101 0.1740 0.063 Uiso 1 1 calc R . .
C14 C 0.6577(5) 0.4289(4) 0.2560(2) 0.0516(11) Uani 1 1 d . . .
H14 H 0.7238 0.4972 0.2675 0.062 Uiso 1 1 calc R . .
C15 C 0.1616(4) -0.2671(4) 0.0638(2) 0.0515(11) Uani 1 1 d . . .
H15 H 0.1425 -0.1985 0.0917 0.062 Uiso 1 1 calc R . .
C16 C 0.0396(4) -0.3512(4) 0.0487(2) 0.0473(11) Uani 1 1 d . . .
H16 H -0.0606 -0.3382 0.0654 0.057 Uiso 1 1 calc R . .
C17 C 0.0657(4) -0.4549(4) 0.0089(2) 0.0396(10) Uani 1 1 d . . .
C18 C 0.2172(4) -0.4690(4) -0.0122(2) 0.0514(11) Uani 1 1 d . . .
H18 H 0.2425 -0.5392 -0.0377 0.062 Uiso 1 1 calc R . .
C19 C 0.3311(4) -0.3799(4) 0.0041(2) 0.0508(12) Uani 1 1 d . . .
H19 H 0.4329 -0.3912 -0.0113 0.061 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 O3 1.931(3) . ?
Zn1 O2 1.950(3) 3_655 ?
Zn1 O1 1.974(3) . ?
Zn1 N1 2.004(3) . ?
Zn1 O4 2.559(3) . ?
N1 C19 1.309(5) . ?
N1 C15 1.320(4) . ?
O1 C1 1.256(4) . ?
O2 C1 1.238(4) . ?
O2 Zn1 1.950(3) 3_655 ?
O3 C8 1.274(5) . ?
O4 C8 1.233(5) . ?
O5 C3 1.380(5) . ?
O5 C12 1.383(4) . ?
C1 C2 1.485(5) . ?
C2 C3 1.377(5) . ?
C2 C7 1.379(5) . ?
C3 C4 1.369(6) . ?
C4 C5 1.383(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.356(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.358(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.486(5) 2_645 ?
C9 C10 1.361(5) . ?
C9 C14 1.377(5) . ?
C9 C8 1.486(5) 2_655 ?
C10 C11 1.376(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(5) . ?
C13 C14 1.375(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.370(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.367(5) . ?
C17 C17 1.478(7) 3_545 ?
C18 C19 1.363(5) . ?
C18 H18 0.9300 . ?
C19 H19 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
O3 Zn1 O2 116.36(11) . 3_655 ?
O3 Zn1 O1 102.68(12) . . ?
O2 Zn1 O1 116.05(12) 3_655 . ?
O3 Zn1 N1 127.48(12) . . ?
O2 Zn1 N1 98.93(12) 3_655 . ?
O1 Zn1 N1 94.13(12) . . ?
O3 Zn1 O4 56.22(11) . . ?
O2 Zn1 O4 86.79(11) 3_655 . ?
O1 Zn1 O4 155.41(11) . . ?
N1 Zn1 O4 90.92(11) . . ?
C19 N1 C15 117.1(3) . . ?
C19 N1 Zn1 120.7(2) . . ?
C15 N1 Zn1 121.8(3) . . ?
C1 O1 Zn1 131.3(3) . . ?
C1 O2 Zn1 122.8(3) . 3_655 ?
C8 O3 Zn1 105.3(3) . . ?
C8 O4 Zn1 77.0(3) . . ?
C3 O5 C12 117.8(3) . . ?
O2 C1 O1 123.4(4) . . ?
O2 C1 C2 120.6(4) . . ?
O1 C1 C2 116.0(4) . . ?
C3 C2 C7 117.9(4) . . ?
C3 C2 C1 123.8(4) . . ?
C7 C2 C1 118.3(4) . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 O5 117.1(5) . . ?
C2 C3 O5 122.5(4) . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.8(5) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 118.6(5) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C6 C7 C2 122.7(5) . . ?
C6 C7 H7 118.7 . . ?
C2 C7 H7 118.7 . . ?
O4 C8 O3 121.4(4) . . ?
O4 C8 C9 120.7(4) . 2_645 ?
O3 C8 C9 117.9(4) . 2_645 ?
C10 C9 C14 118.9(4) . . ?
C10 C9 C8 120.1(4) . 2_655 ?
C14 C9 C8 121.0(4) . 2_655 ?
C9 C10 C11 121.4(4) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C12 118.9(4) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 O5 116.4(4) . . ?
C11 C12 O5 122.9(4) . . ?
C12 C13 C14 119.3(4) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C9 C14 C13 120.8(4) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
N1 C15 C16 122.9(4) . . ?
N1 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 116.6(3) . . ?
C18 C17 C17 123.0(4) . 3_545 ?
C16 C17 C17 120.4(4) . 3_545 ?
C19 C18 C17 119.9(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
N1 C19 C18 123.6(3) . . ?
N1 C19 H19 118.2 . . ?
C18 C19 H19 118.2 . . ?

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
O3 Zn1 N1 C19 -108.5(3) . . . . ?
O2 Zn1 N1 C19 24.9(3) 3_655 . . . ?
O1 Zn1 N1 C19 142.1(3) . . . . ?
O4 Zn1 N1 C19 -62.0(3) . . . . ?
O3 Zn1 N1 C15 79.4(3) . . . . ?
O2 Zn1 N1 C15 -147.2(3) 3_655 . . . ?
O1 Zn1 N1 C15 -30.0(3) . . . . ?
O4 Zn1 N1 C15 125.9(3) . . . . ?
O3 Zn1 O1 C1 38.4(4) . . . . ?
O2 Zn1 O1 C1 -89.7(4) 3_655 . . . ?
N1 Zn1 O1 C1 168.3(4) . . . . ?
O4 Zn1 O1 C1 66.9(5) . . . . ?
O2 Zn1 O3 C8 -65.0(3) 3_655 . . . ?
O1 Zn1 O3 C8 167.2(2) . . . . ?
N1 Zn1 O3 C8 61.8(3) . . . . ?
O4 Zn1 O3 C8 1.0(2) . . . . ?
O3 Zn1 O4 C8 -1.0(2) . . . . ?
O2 Zn1 O4 C8 123.9(2) 3_655 . . . ?
O1 Zn1 O4 C8 -35.2(4) . . . . ?
N1 Zn1 O4 C8 -137.2(2) . . . . ?
Zn1 O2 C1 O1 33.7(6) 3_655 . . . ?
Zn1 O2 C1 C2 -143.9(3) 3_655 . . . ?
Zn1 O1 C1 O2 40.5(6) . . . . ?
Zn1 O1 C1 C2 -141.8(3) . . . . ?
O2 C1 C2 C3 -21.9(6) . . . . ?
O1 C1 C2 C3 160.3(4) . . . . ?
O2 C1 C2 C7 156.9(4) . . . . ?
O1 C1 C2 C7 -20.8(5) . . . . ?
C7 C2 C3 C4 0.5(6) . . . . ?
C1 C2 C3 C4 179.3(4) . . . . ?
C7 C2 C3 O5 -175.2(3) . . . . ?
C1 C2 C3 O5 3.7(6) . . . . ?
C12 O5 C3 C4 90.4(5) . . . . ?
C12 O5 C3 C2 -93.8(5) . . . . ?
C2 C3 C4 C5 -1.6(7) . . . . ?
O5 C3 C4 C5 174.3(4) . . . . ?
C3 C4 C5 C6 1.2(8) . . . . ?
C4 C5 C6 C7 0.3(8) . . . . ?
C5 C6 C7 C2 -1.4(7) . . . . ?
C3 C2 C7 C6 1.1(6) . . . . ?
C1 C2 C7 C6 -177.8(4) . . . . ?
Zn1 O4 C8 O3 1.5(3) . . . . ?
Zn1 O4 C8 C9 -176.8(4) . . . 2_645 ?
Zn1 O3 C8 O4 -2.1(5) . . . . ?
Zn1 O3 C8 C9 176.4(3) . . . 2_645 ?
C14 C9 C10 C11 -0.8(6) . . . . ?
C8 C9 C10 C11 -179.5(3) 2_655 . . . ?
C9 C10 C11 C12 0.7(6) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C10 C11 C12 O5 178.5(3) . . . . ?
C3 O5 C12 C13 -155.5(4) . . . . ?
C3 O5 C12 C11 26.1(6) . . . . ?
C11 C12 C13 C14 -0.9(6) . . . . ?
O5 C12 C13 C14 -179.3(3) . . . . ?
C10 C9 C14 C13 0.1(6) . . . . ?
C8 C9 C14 C13 178.7(3) 2_655 . . . ?
C12 C13 C14 C9 0.8(6) . . . . ?
C19 N1 C15 C16 -3.3(6) . . . . ?
Zn1 N1 C15 C16 169.1(3) . . . . ?
N1 C15 C16 C17 1.5(6) . . . . ?
C15 C16 C17 C18 1.5(6) . . . . ?
C15 C16 C17 C17 -178.7(4) . . . 3_545 ?
C16 C17 C18 C19 -2.5(6) . . . . ?
C17 C17 C18 C19 177.7(4) 3_545 . . . ?
C15 N1 C19 C18 2.2(6) . . . . ?
Zn1 N1 C19 C18 -170.3(3) . . . . ?
C17 C18 C19 N1 0.7(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.064
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_121208a
_database_code_depnum_ccdc_archive 'CCDC 971575'
_audit_update_record             
;
2013-11-12 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H34 N2 Ni O14'
_chemical_formula_weight         801.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Ni Ni 0.3393 1.1124 '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/n

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

_cell_length_a                   12.4477(10)
_cell_length_b                   11.2748(7)
_cell_length_c                   13.6629(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.632(2)
_cell_angle_gamma                90.00
_cell_volume                     1827.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    833
_cell_measurement_theta_min      2.6446
_cell_measurement_theta_max      27.4588

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7602
_exptl_absorpt_correction_T_max  0.9310
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6088
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0899
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3235
_reflns_number_gt                2042
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0289P)²+0.5124P] 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         3235
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.7500 0.65047(6) 0.7500 0.0271(2) Uani 1 2 d S . .
N1 N 0.7500 0.4633(4) 0.7500 0.0268(11) Uani 1 2 d S . .
N2 N 0.7500 -0.1648(4) 0.7500 0.0317(12) Uani 1 2 d S . .
O1 O 0.7906(2) 0.6502(2) 0.90962(19) 0.0280(6) Uani 1 1 d . . .
O2 O 0.9749(2) 0.6805(3) 0.9551(2) 0.0610(10) Uani 1 1 d . . .
O3 O 0.6644(3) 1.3600(3) 1.0628(3) 0.0690(11) Uani 1 1 d . . .
O4 O 0.5271(3) 1.2341(3) 1.0617(3) 0.0642(10) Uani 1 1 d . . .
H4 H 0.4901 1.2955 1.0538 0.096 Uiso 1 1 calc R . .
O5 O 0.9277(3) 0.8716(2) 1.1038(3) 0.0532(9) Uani 1 1 d . . .
O6 O 0.5829(2) 0.6589(2) 0.7448(2) 0.0364(7) Uani 1 1 d . . .
H6B H 0.5689 0.6155 0.7904 0.044 Uiso 1 1 d R . .
H6C H 0.5385 0.6414 0.6859 0.044 Uiso 1 1 d R . .
O7 O 0.9012(2) 0.5745(2) 0.5495(2) 0.0493(9) Uani 1 1 d . . .
H7C H 0.8428 0.6000 0.5628 0.059 Uiso 1 1 d R . .
H7D H 0.8841 0.5105 0.5155 0.059 Uiso 1 1 d R . .
C1 C 0.8853(3) 0.6665(3) 0.9756(3) 0.0310(10) Uani 1 1 d . . .
C2 C 0.8888(3) 0.6632(3) 1.0865(3) 0.0284(9) Uani 1 1 d . . .
C3 C 0.9099(3) 0.7646(4) 1.1473(3) 0.0361(11) Uani 1 1 d . . .
C4 C 0.9194(4) 0.7594(5) 1.2506(4) 0.0568(14) Uani 1 1 d . . .
H4A H 0.9351 0.8275 1.2908 0.068 Uiso 1 1 calc R . .
C5 C 0.9054(4) 0.6525(5) 1.2933(4) 0.0596(14) Uani 1 1 d . . .
H5 H 0.9119 0.6484 1.3628 0.072 Uiso 1 1 calc R . .
C6 C 0.8820(4) 0.5517(4) 1.2346(4) 0.0501(13) Uani 1 1 d . . .
H6 H 0.8720 0.4796 1.2639 0.060 Uiso 1 1 calc R . .
C7 C 0.8732(4) 0.5581(4) 1.1315(4) 0.0432(12) Uani 1 1 d . . .
H7 H 0.8564 0.4898 1.0916 0.052 Uiso 1 1 calc R . .
C8 C 0.6335(4) 1.2599(4) 1.0691(3) 0.0432(12) Uani 1 1 d . . .
C9 C 0.7069(4) 1.1546(4) 1.0824(3) 0.0402(11) Uani 1 1 d . . .
C10 C 0.6701(4) 1.0395(4) 1.0887(4) 0.0484(13) Uani 1 1 d . . .
H10 H 0.5958 1.0268 1.0872 0.058 Uiso 1 1 calc R . .
C11 C 0.7416(4) 0.9429(4) 1.0973(4) 0.0499(13) Uani 1 1 d . . .
H11 H 0.7156 0.8662 1.1009 0.060 Uiso 1 1 calc R . .
C12 C 0.8525(4) 0.9629(4) 1.1005(3) 0.0414(12) Uani 1 1 d . . .
C13 C 0.8912(4) 1.0757(4) 1.0944(4) 0.0487(13) Uani 1 1 d . . .
H13 H 0.9655 1.0880 1.0957 0.058 Uiso 1 1 calc R . .
C14 C 0.8192(4) 1.1707(4) 1.0863(4) 0.0492(13) Uani 1 1 d . . .
H14 H 0.8462 1.2472 1.0834 0.059 Uiso 1 1 calc R . .
C15 C 0.6851(3) 0.4016(3) 0.6702(3) 0.0348(10) Uani 1 1 d . . .
H15 H 0.6386 0.4429 0.6145 0.042 Uiso 1 1 calc R . .
C16 C 0.6843(3) 0.2787(3) 0.6671(3) 0.0348(11) Uani 1 1 d . . .
H16 H 0.6397 0.2389 0.6095 0.042 Uiso 1 1 calc R . .
C17 C 0.7500 0.2162(5) 0.7500 0.0290(14) Uani 1 2 d S . .
C18 C 0.7885(4) -0.1026(3) 0.6846(3) 0.0450(12) Uani 1 1 d . . .
H18 H 0.8170 -0.1439 0.6389 0.054 Uiso 1 1 calc R . .
C19 C 0.7883(4) 0.0191(3) 0.6811(3) 0.0446(12) Uani 1 1 d . . .
H19 H 0.8138 0.0585 0.6326 0.053 Uiso 1 1 calc R . .
C20 C 0.7500 0.0824(5) 0.7500 0.0269(13) Uani 1 2 d S . .


_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
Ni1 O6 2.062(2) 2_656 ?
Ni1 O6 2.062(2) . ?
Ni1 N2 2.083(4) 1_565 ?
Ni1 O1 2.084(2) 2_656 ?
Ni1 O1 2.084(2) . ?
Ni1 N1 2.110(4) . ?
N1 C15 1.339(4) . ?
N1 C15 1.339(4) 2_656 ?
N2 C18 1.334(4) 2_656 ?
N2 C18 1.334(4) . ?
N2 Ni1 2.083(4) 1_545 ?
O1 C1 1.262(4) . ?
O2 C1 1.240(4) . ?
O3 C8 1.203(5) . ?
O4 C8 1.329(5) . ?
O5 C12 1.383(5) . ?
O5 C3 1.392(5) . ?
C1 C2 1.503(5) . ?
C2 C7 1.376(5) . ?
C2 C3 1.390(5) . ?
C3 C4 1.382(6) . ?
C4 C5 1.372(6) . ?
C5 C6 1.370(6) . ?
C6 C7 1.382(6) . ?
C8 C9 1.476(6) . ?
C9 C10 1.387(5) . ?
C9 C14 1.395(5) . ?
C10 C11 1.389(5) . ?
C11 C12 1.386(6) . ?
C12 C13 1.372(5) . ?
C13 C14 1.379(5) . ?
C15 C16 1.386(5) . ?
C16 C17 1.373(4) . ?
C17 C16 1.373(4) 2_656 ?
C17 C20 1.508(7) . ?
C18 C19 1.374(5) . ?
C19 C20 1.376(5) . ?
C20 C19 1.376(5) 2_656 ?

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
O6 Ni1 O6 174.74(14) 2_656 . ?
O6 Ni1 N2 87.37(7) 2_656 1_565 ?
O6 Ni1 N2 87.37(7) . 1_565 ?
O6 Ni1 O1 87.61(10) 2_656 2_656 ?
O6 Ni1 O1 92.40(10) . 2_656 ?
N2 Ni1 O1 90.08(7) 1_565 2_656 ?
O6 Ni1 O1 92.40(10) 2_656 . ?
O6 Ni1 O1 87.61(10) . . ?
N2 Ni1 O1 90.08(7) 1_565 . ?
O1 Ni1 O1 179.85(13) 2_656 . ?
O6 Ni1 N1 92.63(7) 2_656 . ?
O6 Ni1 N1 92.63(7) . . ?
N2 Ni1 N1 180.000(1) 1_565 . ?
O1 Ni1 N1 89.92(7) 2_656 . ?
O1 Ni1 N1 89.92(7) . . ?
C15 N1 C15 117.3(5) . 2_656 ?
C15 N1 Ni1 121.3(2) . . ?
C15 N1 Ni1 121.3(2) 2_656 . ?
C18 N2 C18 116.6(5) 2_656 . ?
C18 N2 Ni1 121.7(2) 2_656 1_545 ?
C18 N2 Ni1 121.7(2) . 1_545 ?
C1 O1 Ni1 128.7(3) . . ?
C12 O5 C3 117.7(3) . . ?
O2 C1 O1 124.6(4) . . ?
O2 C1 C2 118.5(4) . . ?
O1 C1 C2 116.9(3) . . ?
C7 C2 C3 117.9(4) . . ?
C7 C2 C1 120.4(4) . . ?
C3 C2 C1 121.7(4) . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 O5 119.9(4) . . ?
C2 C3 O5 118.9(4) . . ?
C5 C4 C3 119.2(4) . . ?
C6 C5 C4 120.8(5) . . ?
C5 C6 C7 119.4(4) . . ?
C2 C7 C6 121.5(4) . . ?
O3 C8 O4 122.2(4) . . ?
O3 C8 C9 124.3(4) . . ?
O4 C8 C9 113.5(4) . . ?
C10 C9 C14 117.8(4) . . ?
C10 C9 C8 123.8(4) . . ?
C14 C9 C8 118.4(4) . . ?
C9 C10 C11 121.6(4) . . ?
C12 C11 C10 118.8(4) . . ?
C13 C12 O5 116.4(4) . . ?
C13 C12 C11 120.9(4) . . ?
O5 C12 C11 122.5(4) . . ?
C12 C13 C14 119.6(4) . . ?
C13 C14 C9 121.4(4) . . ?
N1 C15 C16 122.8(4) . . ?
C17 C16 C15 119.4(4) . . ?
C16 C17 C16 118.3(5) 2_656 . ?
C16 C17 C20 120.9(2) 2_656 . ?
C16 C17 C20 120.9(2) . . ?
N2 C18 C19 123.4(4) . . ?
C18 C19 C20 119.5(4) . . ?
C19 C20 C19 117.5(5) . 2_656 ?
C19 C20 C17 121.2(3) . . ?
C19 C20 C17 121.2(3) 2_656 . ?

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
O6 Ni1 N1 C15 -116.6(2) 2_656 . . . ?
O6 Ni1 N1 C15 63.4(2) . . . . ?
N2 Ni1 N1 C15 -115(100) 1_565 . . . ?
O1 Ni1 N1 C15 -29.0(2) 2_656 . . . ?
O1 Ni1 N1 C15 151.0(2) . . . . ?
O6 Ni1 N1 C15 63.4(2) 2_656 . . 2_656 ?
O6 Ni1 N1 C15 -116.6(2) . . . 2_656 ?
N2 Ni1 N1 C15 65(100) 1_565 . . 2_656 ?
O1 Ni1 N1 C15 151.0(2) 2_656 . . 2_656 ?
O1 Ni1 N1 C15 -29.0(2) . . . 2_656 ?
O6 Ni1 O1 C1 8.1(3) 2_656 . . . ?
O6 Ni1 O1 C1 -166.6(3) . . . . ?
N2 Ni1 O1 C1 -79.2(3) 1_565 . . . ?
O1 Ni1 O1 C1 101(5) 2_656 . . . ?
N1 Ni1 O1 C1 100.8(3) . . . . ?
Ni1 O1 C1 O2 -3.7(6) . . . . ?
Ni1 O1 C1 C2 179.0(2) . . . . ?
O2 C1 C2 C7 -107.5(5) . . . . ?
O1 C1 C2 C7 70.0(5) . . . . ?
O2 C1 C2 C3 71.3(5) . . . . ?
O1 C1 C2 C3 -111.2(4) . . . . ?
C7 C2 C3 C4 2.6(6) . . . . ?
C1 C2 C3 C4 -176.2(4) . . . . ?
C7 C2 C3 O5 179.0(3) . . . . ?
C1 C2 C3 O5 0.2(6) . . . . ?
C12 O5 C3 C4 -65.4(5) . . . . ?
C12 O5 C3 C2 118.1(4) . . . . ?
C2 C3 C4 C5 -1.4(7) . . . . ?
O5 C3 C4 C5 -177.8(4) . . . . ?
C3 C4 C5 C6 -0.2(8) . . . . ?
C4 C5 C6 C7 0.5(7) . . . . ?
C3 C2 C7 C6 -2.3(6) . . . . ?
C1 C2 C7 C6 176.5(4) . . . . ?
C5 C6 C7 C2 0.8(7) . . . . ?
O3 C8 C9 C10 -179.5(5) . . . . ?
O4 C8 C9 C10 -1.3(7) . . . . ?
O3 C8 C9 C14 -1.1(7) . . . . ?
O4 C8 C9 C14 177.1(4) . . . . ?
C14 C9 C10 C11 -0.9(7) . . . . ?
C8 C9 C10 C11 177.6(4) . . . . ?
C9 C10 C11 C12 0.6(7) . . . . ?
C3 O5 C12 C13 156.5(4) . . . . ?
C3 O5 C12 C11 -27.3(6) . . . . ?
C10 C11 C12 C13 -0.6(7) . . . . ?
C10 C11 C12 O5 -176.6(4) . . . . ?
O5 C12 C13 C14 177.2(4) . . . . ?
C11 C12 C13 C14 0.9(7) . . . . ?
C12 C13 C14 C9 -1.2(7) . . . . ?
C10 C9 C14 C13 1.1(7) . . . . ?
C8 C9 C14 C13 -177.4(4) . . . . ?
C15 N1 C15 C16 -1.0(3) 2_656 . . . ?
Ni1 N1 C15 C16 179.0(3) . . . . ?
N1 C15 C16 C17 1.9(6) . . . . ?
C15 C16 C17 C16 -0.9(3) . . . 2_656 ?
C15 C16 C17 C20 179.1(3) . . . . ?
C18 N2 C18 C19 -1.1(3) 2_656 . . . ?
Ni1 N2 C18 C19 178.9(3) 1_545 . . . ?
N2 C18 C19 C20 2.1(7) . . . . ?
C18 C19 C20 C19 -1.0(3) . . . 2_656 ?
C18 C19 C20 C17 179.0(3) . . . . ?
C16 C17 C20 C19 -115.9(3) 2_656 . . . ?
C16 C17 C20 C19 64.1(3) . . . . ?
C16 C17 C20 C19 64.1(3) 2_656 . . 2_656 ?
C16 C17 C20 C19 -115.9(3) . . . 2_656 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.072
