# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_Ni-1
_database_code_depnum_ccdc_archive 'CCDC 1502000'
_audit_update_record             
;
2016-09-01 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H8 Ni0.75 O6.75'
_chemical_formula_weight         340.25

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'
Ni Ni 0.3393 1.1124 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pmna  '

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'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x, y, z'
'x-1/2, -y, z-1/2'

_cell_length_a                   27.2662(6)
_cell_length_b                   11.5396(3)
_cell_length_c                   13.9678(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4394.84(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    14771
_cell_measurement_theta_min      2.289
_cell_measurement_theta_max      27.492

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.028
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1384
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      220(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            27339
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3973
_reflns_number_gt                3518
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.1830P)²+19.4926P] 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         3973
_refine_ls_number_parameters     257
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0921
_refine_ls_wR_factor_ref         0.2963
_refine_ls_wR_factor_gt          0.2896
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0.001

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 0.0000 -0.14970(7) 1.28137(6) 0.0189(2) Uani 1 2 d S . .
Ni2 Ni 0.0000 0.0000 1.5000 0.0138(3) Uani 1 4 d S . .
O1 O 0.0000 -0.1558(3) 1.4295(3) 0.0184(10) Uani 1 2 d S . .
O4 O 0.05617(14) -0.0326(3) 1.2782(3) 0.0361(10) Uani 1 1 d . . .
O2 O 0.0000 -0.1501(5) 1.1346(4) 0.0435(15) Uani 1 2 d S . .
O3 O 0.0525(2) 0.0623(5) 1.4157(4) 0.1056(19) Uani 1 1 d U . .
C1 C 0.0722(2) 0.0371(5) 1.3387(4) 0.0389(14) Uani 1 1 d . . .
C5 C 0.20504(18) 0.2223(4) 1.2747(4) 0.0314(13) Uani 1 1 d . . .
C10 C 0.29486(18) 0.4768(4) 1.2272(4) 0.0301(12) Uani 1 1 d . . .
C8 C 0.2500 0.2895(6) 1.2500 0.0309(17) Uani 1 2 d S . .
C9 C 0.2500 0.4066(6) 1.2500 0.0303(17) Uani 1 2 d S . .
C2 C 0.1197(2) 0.0988(5) 1.3165(4) 0.0388(14) Uani 1 1 d . . .
C4 C 0.1841(2) 0.2262(5) 1.3646(4) 0.0437(15) Uani 1 1 d . . .
H4A H 0.1994 0.2716 1.4138 0.052 Uiso 1 1 d R . .
C3 C 0.1420(2) 0.1666(6) 1.3849(5) 0.0478(16) Uani 1 1 d . . .
H3A H 0.1278 0.1722 1.4476 0.057 Uiso 1 1 d R . .
C6 C 0.1824(3) 0.1543(7) 1.2057(5) 0.068(2) Uani 1 1 d . . .
H6A H 0.1962 0.1496 1.1426 0.081 Uiso 1 1 d R . .
C7 C 0.1402(3) 0.0932(7) 1.2270(5) 0.075(2) Uani 1 1 d . . .
H7A H 0.1251 0.0463 1.1785 0.089 Uiso 1 1 d R . .
C11 C 0.3319(3) 0.4934(8) 1.2910(6) 0.069(2) Uani 1 1 d . . .
H11A H 0.3306 0.4552 1.3520 0.083 Uiso 1 1 d R . .
C15 C 0.2990(3) 0.5290(8) 1.1397(6) 0.068(2) Uani 1 1 d . . .
H15A H 0.2736 0.5191 1.0928 0.081 Uiso 1 1 d R . .
C14 C 0.3398(3) 0.5964(8) 1.1181(5) 0.067(2) Uani 1 1 d . . .
H14A H 0.3424 0.6311 1.0558 0.081 Uiso 1 1 d R . .
C13 C 0.37619(18) 0.6142(5) 1.1836(4) 0.0327(12) Uani 1 1 d . . .
C16 C 0.41947(19) 0.6902(5) 1.1586(4) 0.0334(12) Uani 1 1 d . . .
C12 C 0.3708(3) 0.5628(8) 1.2705(5) 0.068(2) Uani 1 1 d . . .
H12A H 0.3951 0.5761 1.3190 0.081 Uiso 1 1 d R . .
O5 O 0.44657(13) 0.7217(3) 1.2258(2) 0.0323(9) Uani 1 1 d . . .
O6 O 0.42521(17) 0.7147(5) 1.0725(3) 0.0612(14) Uani 1 1 d . . .
O1W O 0.0000 0.5446(10) 0.1478(9) 0.116(4) Uani 1 2 d S . .
O2W O -0.0281(7) -0.3269(13) 1.6484(15) 0.164(9) Uani 0.50 1 d P . .
O3W O 0.0000 0.142(2) 1.133(5) 0.27(3) Uani 0.50 2 d SP . .
O4W O -0.036(2) -0.5000 1.5000 0.056(15) Uani 0.13 2 d SP . .
O5W O 0.065(2) 0.545(5) -0.003(4) 0.036(17) Uani 0.06 1 d P . .
O6W O 0.0656(17) 0.789(4) 0.001(2) 0.069(12) Uani 0.13 1 d PU . .
O7W O 0.2496(14) 0.110(4) 1.593(4) 0.091(16) Uani 0.13 1 d P . .
O8W O 0.339(3) 0.160(3) 1.639(4) 0.16(3) Uani 0.13 1 d P . .


_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 O4 2.043(4) 7 ?
Ni1 O4 2.043(4) . ?
Ni1 O2 2.050(6) . ?
Ni1 O1 2.070(5) . ?
Ni1 O5 2.082(4) 6_548 ?
Ni1 O5 2.082(4) 4_547 ?
Ni2 O3 1.988(5) 7 ?
Ni2 O3 1.988(5) 5_558 ?
Ni2 O3 1.988(5) . ?
Ni2 O3 1.988(5) 3_558 ?
Ni2 O1 2.050(4) . ?
Ni2 O1 2.050(4) 5_558 ?
O4 C1 1.246(7) . ?
O3 C1 1.236(7) . ?
C1 C2 1.511(7) . ?
C5 C4 1.380(8) . ?
C5 C6 1.387(9) . ?
C5 C8 1.491(6) . ?
C10 C11 1.361(9) . ?
C10 C15 1.368(10) . ?
C10 C9 1.502(6) . ?
C8 C9 1.351(10) . ?
C8 C5 1.491(6) 4_557 ?
C9 C10 1.502(6) 4_557 ?
C2 C7 1.372(9) . ?
C2 C3 1.376(9) . ?
C4 C3 1.369(8) . ?
C4 H4A 0.9599 . ?
C3 H3A 0.9601 . ?
C6 C7 1.381(10) . ?
C6 H6A 0.9600 . ?
C7 H7A 0.9601 . ?
C11 C12 1.358(10) . ?
C11 H11A 0.9599 . ?
C15 C14 1.390(9) . ?
C15 H15A 0.9600 . ?
C14 C13 1.366(9) . ?
C14 H14A 0.9600 . ?
C13 C12 1.359(9) . ?
C13 C16 1.511(7) . ?
C16 O6 1.246(7) . ?
C16 O5 1.248(6) . ?
C12 H12A 0.9601 . ?
O5 Ni1 2.082(4) 6_668 ?
O2W O2W 1.53(4) 7 ?
O5W O5W 1.04(13) 3_565 ?

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
O4 Ni1 O4 97.1(2) 7 . ?
O4 Ni1 O2 88.84(15) 7 . ?
O4 Ni1 O2 88.84(15) . . ?
O4 Ni1 O1 92.54(13) 7 . ?
O4 Ni1 O1 92.54(13) . . ?
O2 Ni1 O1 177.9(2) . . ?
O4 Ni1 O5 86.90(16) 7 6_548 ?
O4 Ni1 O5 174.26(15) . 6_548 ?
O2 Ni1 O5 87.15(15) . 6_548 ?
O1 Ni1 O5 91.36(13) . 6_548 ?
O4 Ni1 O5 174.27(15) 7 4_547 ?
O4 Ni1 O5 86.90(16) . 4_547 ?
O2 Ni1 O5 87.15(15) . 4_547 ?
O1 Ni1 O5 91.36(13) . 4_547 ?
O5 Ni1 O5 88.8(2) 6_548 4_547 ?
O3 Ni2 O3 87.9(4) 7 5_558 ?
O3 Ni2 O3 92.1(4) 7 . ?
O3 Ni2 O3 180.000(1) 5_558 . ?
O3 Ni2 O3 180.000(2) 7 3_558 ?
O3 Ni2 O3 92.1(4) 5_558 3_558 ?
O3 Ni2 O3 87.9(4) . 3_558 ?
O3 Ni2 O1 91.86(16) 7 . ?
O3 Ni2 O1 88.14(16) 5_558 . ?
O3 Ni2 O1 91.86(16) . . ?
O3 Ni2 O1 88.14(16) 3_558 . ?
O3 Ni2 O1 88.14(16) 7 5_558 ?
O3 Ni2 O1 91.86(16) 5_558 5_558 ?
O3 Ni2 O1 88.14(16) . 5_558 ?
O3 Ni2 O1 91.86(16) 3_558 5_558 ?
O1 Ni2 O1 180.000(1) . 5_558 ?
Ni2 O1 Ni1 116.8(2) . . ?
C1 O4 Ni1 132.4(3) . . ?
C1 O3 Ni2 138.0(4) . . ?
O3 C1 O4 126.2(5) . . ?
O3 C1 C2 116.1(5) . . ?
O4 C1 C2 117.7(5) . . ?
C4 C5 C6 117.8(5) . . ?
C4 C5 C8 122.2(5) . . ?
C6 C5 C8 120.0(5) . . ?
C11 C10 C15 117.5(5) . . ?
C11 C10 C9 122.8(5) . . ?
C15 C10 C9 119.6(5) . . ?
C9 C8 C5 121.3(3) . . ?
C9 C8 C5 121.3(3) . 4_557 ?
C5 C8 C5 117.3(6) . 4_557 ?
C8 C9 C10 122.7(3) . 4_557 ?
C8 C9 C10 122.7(3) . . ?
C10 C9 C10 114.6(6) 4_557 . ?
C7 C2 C3 118.7(5) . . ?
C7 C2 C1 121.0(6) . . ?
C3 C2 C1 120.3(5) . . ?
C3 C4 C5 121.3(6) . . ?
C3 C4 H4A 119.3 . . ?
C5 C4 H4A 119.4 . . ?
C4 C3 C2 120.8(6) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C7 C6 C5 120.6(6) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C2 C7 C6 120.8(7) . . ?
C2 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C12 C11 C10 121.6(7) . . ?
C12 C11 H11A 119.2 . . ?
C10 C11 H11A 119.2 . . ?
C10 C15 C14 120.4(6) . . ?
C10 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C13 C14 C15 121.4(6) . . ?
C13 C14 H14A 119.3 . . ?
C15 C14 H14A 119.3 . . ?
C12 C13 C14 117.0(5) . . ?
C12 C13 C16 123.0(5) . . ?
C14 C13 C16 120.0(5) . . ?
O6 C16 O5 125.8(5) . . ?
O6 C16 C13 116.9(5) . . ?
O5 C16 C13 117.2(5) . . ?
C11 C12 C13 122.0(7) . . ?
C11 C12 H12A 119.0 . . ?
C13 C12 H12A 119.0 . . ?
C16 O5 Ni1 125.8(3) . 6_668 ?

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 Ni2 O1 Ni1 46.1(2) 7 . . . ?
O3 Ni2 O1 Ni1 133.9(2) 5_558 . . . ?
O3 Ni2 O1 Ni1 -46.1(2) . . . . ?
O3 Ni2 O1 Ni1 -133.9(2) 3_558 . . . ?
O1 Ni2 O1 Ni1 -90.0(10) 5_558 . . . ?
O4 Ni1 O1 Ni2 -48.62(12) 7 . . . ?
O4 Ni1 O1 Ni2 48.62(12) . . . . ?
O2 Ni1 O1 Ni2 180.00(2) . . . . ?
O5 Ni1 O1 Ni2 -135.58(11) 6_548 . . . ?
O5 Ni1 O1 Ni2 135.58(11) 4_547 . . . ?
O4 Ni1 O4 C1 71.4(6) 7 . . . ?
O2 Ni1 O4 C1 160.1(6) . . . . ?
O1 Ni1 O4 C1 -21.4(6) . . . . ?
O5 Ni1 O4 C1 -154.3(14) 6_548 . . . ?
O5 Ni1 O4 C1 -112.7(6) 4_547 . . . ?
O3 Ni2 O3 C1 -77.5(10) 7 . . . ?
O3 Ni2 O3 C1 115(100) 5_558 . . . ?
O3 Ni2 O3 C1 102.5(10) 3_558 . . . ?
O1 Ni2 O3 C1 14.4(9) . . . . ?
O1 Ni2 O3 C1 -165.6(9) 5_558 . . . ?
Ni2 O3 C1 O4 15.3(14) . . . . ?
Ni2 O3 C1 C2 -165.7(6) . . . . ?
Ni1 O4 C1 O3 -10.0(11) . . . . ?
Ni1 O4 C1 C2 171.0(4) . . . . ?
C4 C5 C8 C9 -64.6(6) . . . . ?
C6 C5 C8 C9 114.4(6) . . . . ?
C4 C5 C8 C5 115.4(6) . . . 4_557 ?
C6 C5 C8 C5 -65.6(6) . . . 4_557 ?
C5 C8 C9 C10 -1.1(4) . . . 4_557 ?
C5 C8 C9 C10 178.9(4) 4_557 . . 4_557 ?
C5 C8 C9 C10 178.9(4) . . . . ?
C5 C8 C9 C10 -1.1(4) 4_557 . . . ?
C11 C10 C9 C8 -77.6(7) . . . . ?
C15 C10 C9 C8 103.7(6) . . . . ?
C11 C10 C9 C10 102.4(7) . . . 4_557 ?
C15 C10 C9 C10 -76.3(6) . . . 4_557 ?
O3 C1 C2 C7 -168.5(8) . . . . ?
O4 C1 C2 C7 10.6(10) . . . . ?
O3 C1 C2 C3 8.2(10) . . . . ?
O4 C1 C2 C3 -172.7(6) . . . . ?
C6 C5 C4 C3 -1.1(10) . . . . ?
C8 C5 C4 C3 178.0(6) . . . . ?
C5 C4 C3 C2 1.4(10) . . . . ?
C7 C2 C3 C4 -0.9(11) . . . . ?
C1 C2 C3 C4 -177.7(6) . . . . ?
C4 C5 C6 C7 0.3(11) . . . . ?
C8 C5 C6 C7 -178.8(7) . . . . ?
C3 C2 C7 C6 0.1(13) . . . . ?
C1 C2 C7 C6 176.8(7) . . . . ?
C5 C6 C7 C2 0.2(14) . . . . ?
C15 C10 C11 C12 2.6(13) . . . . ?
C9 C10 C11 C12 -176.1(8) . . . . ?
C11 C10 C15 C14 -0.1(12) . . . . ?
C9 C10 C15 C14 178.6(7) . . . . ?
C10 C15 C14 C13 -1.3(14) . . . . ?
C15 C14 C13 C12 0.2(12) . . . . ?
C15 C14 C13 C16 -178.6(7) . . . . ?
C12 C13 C16 O6 167.0(7) . . . . ?
C14 C13 C16 O6 -14.2(9) . . . . ?
C12 C13 C16 O5 -12.2(9) . . . . ?
C14 C13 C16 O5 166.6(6) . . . . ?
C10 C11 C12 C13 -3.8(15) . . . . ?
C14 C13 C12 C11 2.3(13) . . . . ?
C16 C13 C12 C11 -179.0(8) . . . . ?
O6 C16 O5 Ni1 13.6(9) . . . 6_668 ?
C13 C16 O5 Ni1 -167.3(4) . . . 6_668 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.319
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.228
####################################################################### 
# 
# 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_Ni-2
_database_code_depnum_ccdc_archive 'CCDC 1502001'
_audit_update_record             
;
2016-09-19 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            Ni-2
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.75 H2.25 Ni0.25 O1.34'
_chemical_formula_weight         83.45

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'
Ni Ni 0.3393 1.1124 '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'

_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_H-M   'P6/mmm '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x-y, x, z'
'-y, x-y, z'
'-x, -y, z'
'-x+y, -x, z'
'y, -x+y, z'
'-y, -x, -z'
'x-y, -y, -z'
'x, x-y, -z'
'y, x, -z'
'-x+y, y, -z'
'-x, -x+y, -z'
'-x, -y, -z'
'-x+y, -x, -z'
'y, -x+y, -z'
'x, y, -z'
'x-y, x, -z'
'-y, x-y, -z'
'y, x, z'
'-x+y, y, z'
'-x, -x+y, z'
'-y, -x, z'
'x-y, -y, z'
'x, x-y, z'

_cell_length_a                   26.2500(4)
_cell_length_b                   26.2500(4)
_cell_length_c                   11.2436(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     6709.6(3)
_cell_formula_units_Z            24
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    43427
_cell_measurement_theta_min      2.366
_cell_measurement_theta_max      27.482

_exptl_crystal_description       Stick
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1020
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      220(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            99704
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2312
_reflns_number_gt                1935
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.1930P)²+32.0065P] 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         2312
_refine_ls_number_parameters     80
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0983
_refine_ls_wR_factor_ref         0.3359
_refine_ls_wR_factor_gt          0.3269
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.005
_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 0.28992(2) 0.57984(5) 0.0000 0.0314(5) Uani 1 4 d S . .
O1 O 0.3333 0.6667 0.0000 0.043(3) Uani 1 12 d S . .
O3 O 0.34155(19) 0.57370(19) 0.1287(4) 0.0635(13) Uani 1 1 d . . .
O2 O 0.2435(2) 0.4870(4) 0.0000 0.083(3) Uani 1 4 d S . .
H2A H 0.2158 0.4746 -0.0506 0.125 Uiso 0.25 1 d PR . .
C1 C 0.39380(15) 0.60620(15) 0.1562(6) 0.0408(17) Uani 1 2 d S A .
C2 C 0.42126(15) 0.57874(15) 0.2323(6) 0.0421(18) Uani 1 2 d S . .
C5 C 0.47226(15) 0.52774(15) 0.3686(6) 0.048(2) Uani 1 2 d S . .
C6 C 0.5000 0.5000 0.4405(9) 0.048(3) Uani 1 4 d S . .
C3' C 0.4035(7) 0.5216(6) 0.2247(11) 0.060(3) Uani 0.50 1 d P A 1
H3A H 0.3898 0.4957 0.1573 0.072 Uiso 0.50 1 d PR A 1
C3 C 0.3860(6) 0.5317(6) 0.3073(11) 0.058(3) Uani 0.50 1 d P A 2
H3'A H 0.3511 0.5216 0.3523 0.070 Uiso 0.50 1 d PR A 2
C4 C 0.4128(6) 0.5067(7) 0.3774(12) 0.063(4) Uani 0.50 1 d P A 1
H4A H 0.3856 0.4898 0.4423 0.076 Uiso 0.50 1 d PR A 1
C4' C 0.4299(7) 0.4965(6) 0.2886(11) 0.064(4) Uani 0.50 1 d P A 2
H4'A H 0.4245 0.4650 0.2370 0.077 Uiso 0.50 1 d PR A 2
O1W O 0.3333 0.6667 0.5000 0.037(12) Uani 0.10 12 d SPU . .


_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 O1 1.9737(11) . ?
Ni1 O3 2.043(4) 11 ?
Ni1 O3 2.043(4) . ?
Ni1 O3 2.043(4) 20 ?
Ni1 O3 2.043(4) 16 ?
Ni1 O2 2.110(9) . ?
O1 Ni1 1.9737(11) 14_565 ?
O1 Ni1 1.9737(11) 3_665 ?
O3 C1 1.239(5) . ?
O2 H2A 0.8502 . ?
C1 O3 1.239(5) 22_665 ?
C1 C2 1.513(9) . ?
C2 C3' 1.333(13) . ?
C2 C3' 1.333(13) 22_665 ?
C2 C3 1.397(13) 22_665 ?
C2 C3 1.397(13) . ?
C5 C4' 1.344(14) . ?
C5 C4' 1.344(14) 22_665 ?
C5 C4 1.374(14) 22_665 ?
C5 C4 1.374(14) . ?
C5 C6 1.498(9) . ?
C6 C6 1.34(2) 13_666 ?
C6 C5 1.498(9) 4_665 ?
C3' C4 1.804(17) . ?
C3' C3' 1.97(3) 22_665 ?
C3' H3A 0.9600 . ?
C3 C4' 1.815(17) . ?
C3 H3'A 0.9601 . ?
C4 H4A 0.9599 . ?
C4' C4' 1.93(3) 22_665 ?
C4' H4'A 0.9602 . ?

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 Ni1 O3 93.92(13) . 11 ?
O1 Ni1 O3 93.92(13) . . ?
O3 Ni1 O3 172.2(3) 11 . ?
O1 Ni1 O3 93.92(13) . 20 ?
O3 Ni1 O3 90.2(3) 11 20 ?
O3 Ni1 O3 89.3(3) . 20 ?
O1 Ni1 O3 93.92(13) . 16 ?
O3 Ni1 O3 89.3(3) 11 16 ?
O3 Ni1 O3 90.2(3) . 16 ?
O3 Ni1 O3 172.2(3) 20 16 ?
O1 Ni1 O2 180.00(7) . . ?
O3 Ni1 O2 86.08(13) 11 . ?
O3 Ni1 O2 86.08(13) . . ?
O3 Ni1 O2 86.08(13) 20 . ?
O3 Ni1 O2 86.08(13) 16 . ?
Ni1 O1 Ni1 120.0 14_565 . ?
Ni1 O1 Ni1 120.000(1) 14_565 3_665 ?
Ni1 O1 Ni1 120.0 . 3_665 ?
C1 O3 Ni1 132.3(4) . . ?
Ni1 O2 H2A 109.5 . . ?
O3 C1 O3 127.7(7) . 22_665 ?
O3 C1 C2 116.1(3) . . ?
O3 C1 C2 116.1(3) 22_665 . ?
C3' C2 C3' 95.0(13) . 22_665 ?
C3' C2 C3 118.7(9) . 22_665 ?
C3' C2 C3 48.7(8) 22_665 22_665 ?
C3' C2 C3 48.7(8) . . ?
C3' C2 C3 118.7(9) 22_665 . ?
C3 C2 C3 101.4(12) 22_665 . ?
C3' C2 C1 121.3(6) . . ?
C3' C2 C1 121.3(6) 22_665 . ?
C3 C2 C1 119.9(6) 22_665 . ?
C3 C2 C1 119.9(6) . . ?
C4' C5 C4' 91.9(13) . 22_665 ?
C4' C5 C4 118.8(9) . 22_665 ?
C4' C5 C4 51.4(8) 22_665 22_665 ?
C4' C5 C4 51.4(8) . . ?
C4' C5 C4 118.8(9) 22_665 . ?
C4 C5 C4 100.5(13) 22_665 . ?
C4' C5 C6 121.3(6) . . ?
C4' C5 C6 121.3(6) 22_665 . ?
C4 C5 C6 119.7(6) 22_665 . ?
C4 C5 C6 119.7(6) . . ?
C6 C6 C5 122.7(4) 13_666 . ?
C6 C6 C5 122.7(4) 13_666 4_665 ?
C5 C6 C5 114.7(8) . 4_665 ?
C2 C3' C4 100.0(9) . . ?
C2 C3' C3' 42.5(7) . 22_665 ?
C4 C3' C3' 92.4(7) . 22_665 ?
C2 C3' H3A 130.0 . . ?
C4 C3' H3A 130.0 . . ?
C3' C3' H3A 122.8 22_665 . ?
C2 C3 C4' 94.0(9) . . ?
C2 C3 H3'A 133.0 . . ?
C4' C3 H3'A 133.0 . . ?
C5 C4 C3' 95.4(9) . . ?
C5 C4 H4A 132.3 . . ?
C3' C4 H4A 132.3 . . ?
C5 C4' C3 98.9(9) . . ?
C5 C4' C4' 44.1(7) . 22_665 ?
C3 C4' C4' 93.6(6) . 22_665 ?
C5 C4' H4'A 130.5 . . ?
C3 C4' H4'A 130.6 . . ?
C4' C4' H4'A 120.2 22_665 . ?

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 Ni1 O1 Ni1 45.22(15) 11 . . 14_565 ?
O3 Ni1 O1 Ni1 -134.78(15) . . . 14_565 ?
O3 Ni1 O1 Ni1 -45.22(15) 20 . . 14_565 ?
O3 Ni1 O1 Ni1 134.78(15) 16 . . 14_565 ?
O2 Ni1 O1 Ni1 0(100) . . . 14_565 ?
O3 Ni1 O1 Ni1 -134.78(15) 11 . . 3_665 ?
O3 Ni1 O1 Ni1 45.22(15) . . . 3_665 ?
O3 Ni1 O1 Ni1 134.78(15) 20 . . 3_665 ?
O3 Ni1 O1 Ni1 -45.22(15) 16 . . 3_665 ?
O2 Ni1 O1 Ni1 0(100) . . . 3_665 ?
O1 Ni1 O3 C1 -29.6(7) . . . . ?
O3 Ni1 O3 C1 150.4(6) 11 . . . ?
O3 Ni1 O3 C1 -123.4(6) 20 . . . ?
O3 Ni1 O3 C1 64.4(7) 16 . . . ?
O2 Ni1 O3 C1 150.4(7) . . . . ?
Ni1 O3 C1 O3 17.1(13) . . . 22_665 ?
Ni1 O3 C1 C2 -162.7(5) . . . . ?
O3 C1 C2 C3' 30.3(12) . . . . ?
O3 C1 C2 C3' -149.5(10) 22_665 . . . ?
O3 C1 C2 C3' 149.5(10) . . . 22_665 ?
O3 C1 C2 C3' -30.3(12) 22_665 . . 22_665 ?
O3 C1 C2 C3 -153.4(9) . . . 22_665 ?
O3 C1 C2 C3 26.9(11) 22_665 . . 22_665 ?
O3 C1 C2 C3 -26.9(11) . . . . ?
O3 C1 C2 C3 153.4(9) 22_665 . . . ?
C4' C5 C6 C6 -122.8(9) . . . 13_666 ?
C4' C5 C6 C6 122.8(9) 22_665 . . 13_666 ?
C4 C5 C6 C6 62.3(9) 22_665 . . 13_666 ?
C4 C5 C6 C6 -62.3(9) . . . 13_666 ?
C4' C5 C6 C5 57.2(9) . . . 4_665 ?
C4' C5 C6 C5 -57.2(9) 22_665 . . 4_665 ?
C4 C5 C6 C5 -117.7(9) 22_665 . . 4_665 ?
C4 C5 C6 C5 117.7(9) . . . 4_665 ?
C3' C2 C3' C4 82.4(11) 22_665 . . . ?
C3 C2 C3' C4 37.5(14) 22_665 . . . ?
C3 C2 C3' C4 -42.0(9) . . . . ?
C1 C2 C3' C4 -146.1(7) . . . . ?
C3 C2 C3' C3' -44.9(8) 22_665 . . 22_665 ?
C3 C2 C3' C3' -124.4(10) . . . 22_665 ?
C1 C2 C3' C3' 131.5(12) . . . 22_665 ?
C3' C2 C3 C4' 39.1(9) . . . . ?
C3' C2 C3 C4' -30.4(13) 22_665 . . . ?
C3 C2 C3 C4' -79.2(11) 22_665 . . . ?
C1 C2 C3 C4' 146.1(7) . . . . ?
C4' C5 C4 C3' -38.8(8) . . . . ?
C4' C5 C4 C3' 28.2(14) 22_665 . . . ?
C4 C5 C4 C3' 79.8(11) 22_665 . . . ?
C6 C5 C4 C3' -146.8(7) . . . . ?
C2 C3' C4 C5 -81.1(10) . . . . ?
C3' C3' C4 C5 -39.0(7) 22_665 . . . ?
C4' C5 C4' C3 -86.0(10) 22_665 . . . ?
C4 C5 C4' C3 -40.0(14) 22_665 . . . ?
C4 C5 C4' C3 40.1(9) . . . . ?
C6 C5 C4' C3 145.0(7) . . . . ?
C4 C5 C4' C4' 46.0(9) 22_665 . . 22_665 ?
C4 C5 C4' C4' 126.2(10) . . . 22_665 ?
C6 C5 C4' C4' -128.9(11) . . . 22_665 ?
C2 C3 C4' C5 82.6(10) . . . . ?
C2 C3 C4' C4' 38.6(7) . . . 22_665 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.041
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.155

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.004 -0.003 -0.015 4562 662 ' '
2 0.333 0.667 0.250 7 1 ' '
3 0.333 0.667 0.750 7 1 ' '
4 0.667 0.333 0.250 7 1 ' '
5 0.667 0.333 0.750 7 1 ' '
_platon_squeeze_details          
;
;
