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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H54 Cl6 N4 Ni2 O8'
_chemical_formula_weight         1169.09

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'
Cl Cl 0.1484 0.1585 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.747(2)
_cell_length_b                   11.215(2)
_cell_length_c                   12.347(3)
_cell_angle_alpha                103.63(3)
_cell_angle_beta                 109.84(3)
_cell_angle_gamma                91.01(3)
_cell_volume                     1352.5(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2202
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    1.047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8340
_exptl_absorpt_correction_T_max  0.9495
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9834
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.1060
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         27.94
_reflns_number_total             6418
_reflns_number_gt                3852
_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)+(0.1055P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6418
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.2028
_refine_ls_wR_factor_gt          0.1758
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
C1 C 0.8903(4) 0.9194(4) 0.9114(4) 0.0237(9) Uani 1 1 d . . .
C2 C 0.9544(4) 1.0220(4) 0.8851(4) 0.0245(9) Uani 1 1 d . . .
C3 C 1.0613(4) 1.0998(4) 0.9738(4) 0.0259(9) Uani 1 1 d . . .
H3 H 1.1005 1.1644 0.9571 0.031 Uiso 1 1 calc R . .
C4 C 0.7231(4) 0.7473(4) 0.8265(4) 0.0277(9) Uani 1 1 d . . .
C5 C 0.7901(4) 0.6452(4) 0.8447(4) 0.0339(10) Uani 1 1 d . . .
H5 H 0.8793 0.6465 0.8524 0.041 Uiso 1 1 calc R . .
C6 C 0.7246(5) 0.5410(4) 0.8516(4) 0.0356(11) Uani 1 1 d . . .
H6 H 0.7702 0.4731 0.8651 0.043 Uiso 1 1 calc R . .
C7 C 0.5913(4) 0.5382(4) 0.8382(4) 0.0312(10) Uani 1 1 d . . .
C8 C 0.5240(4) 0.6402(4) 0.8193(4) 0.0342(10) Uani 1 1 d . . .
H8 H 0.4343 0.6387 0.8100 0.041 Uiso 1 1 calc R . .
C9 C 0.5910(4) 0.7443(4) 0.8145(4) 0.0322(10) Uani 1 1 d . . .
H9 H 0.5462 0.8130 0.8030 0.039 Uiso 1 1 calc R . .
C10 C 0.4007(5) 0.4280(5) 0.8441(4) 0.0404(12) Uani 1 1 d . . .
H10A H 0.3411 0.4403 0.7694 0.049 Uiso 1 1 calc R . .
H10B H 0.3944 0.4931 0.9088 0.049 Uiso 1 1 calc R . .
C11 C 0.3635(5) 0.3037(5) 0.8579(5) 0.0493(14) Uani 1 1 d . . .
H11A H 0.3627 0.2405 0.7899 0.074 Uiso 1 1 calc R . .
H11B H 0.2768 0.3017 0.8640 0.074 Uiso 1 1 calc R . .
H11C H 0.4274 0.2897 0.9287 0.074 Uiso 1 1 calc R . .
C12 C 0.9506(4) 1.1182(4) 0.7318(4) 0.0268(9) Uani 1 1 d . . .
C13 C 0.9258(5) 1.2401(4) 0.7605(4) 0.0358(11) Uani 1 1 d . . .
H13 H 0.8777 1.2647 0.8104 0.043 Uiso 1 1 calc R . .
C14 C 0.9727(5) 1.3256(4) 0.7151(5) 0.0407(12) Uani 1 1 d . . .
H14 H 0.9567 1.4077 0.7351 0.049 Uiso 1 1 calc R . .
C15 C 1.0430(4) 1.2895(4) 0.6402(4) 0.0308(10) Uani 1 1 d . . .
C16 C 1.0668(4) 1.1686(4) 0.6106(4) 0.0315(10) Uani 1 1 d . . .
H16 H 1.1139 1.1439 0.5598 0.038 Uiso 1 1 calc R . .
C17 C 1.0202(4) 1.0831(4) 0.6568(4) 0.0310(10) Uani 1 1 d . . .
H17 H 1.0363 1.0011 0.6367 0.037 Uiso 1 1 calc R . .
C18 C 1.1562(5) 1.3466(5) 0.5201(5) 0.0387(11) Uani 1 1 d . . .
H18A H 1.0986 1.2891 0.4474 0.046 Uiso 1 1 calc R . .
H18B H 1.2337 1.3069 0.5555 0.046 Uiso 1 1 calc R . .
C19 C 1.1976(6) 1.4609(5) 0.4931(6) 0.0542(15) Uani 1 1 d . . .
H19A H 1.1202 1.4996 0.4584 0.081 Uiso 1 1 calc R . .
H19B H 1.2439 1.4397 0.4381 0.081 Uiso 1 1 calc R . .
H19C H 1.2553 1.5168 0.5654 0.081 Uiso 1 1 calc R . .
C20 C 0.5322(5) 0.7728(5) 0.4907(4) 0.0358(11) Uani 1 1 d . . .
C21 C 0.5351(4) 0.8472(4) 0.4169(4) 0.0347(11) Uani 1 1 d . . .
H21 H 0.4687 0.8317 0.3421 0.042 Uiso 1 1 calc R . .
C22 C 0.6343(4) 0.9454(4) 0.4504(4) 0.0304(10) Uani 1 1 d . . .
C23 C 0.4272(5) 0.6659(5) 0.4491(5) 0.0485(14) Uani 1 1 d . . .
H23A H 0.4563 0.5944 0.4083 0.073 Uiso 1 1 calc R . .
H23B H 0.3463 0.6854 0.3959 0.073 Uiso 1 1 calc R . .
H23C H 0.4115 0.6494 0.5166 0.073 Uiso 1 1 calc R . .
C24 C 0.6352(5) 1.0196(5) 0.3649(4) 0.0406(12) Uani 1 1 d . . .
H24A H 0.6592 1.1052 0.4070 0.061 Uiso 1 1 calc R . .
H24B H 0.5482 1.0096 0.3049 0.061 Uiso 1 1 calc R . .
H24C H 0.6986 0.9919 0.3280 0.061 Uiso 1 1 calc R . .
C25 C 0.7914(7) 0.1826(7) 0.0976(7) 0.076(2) Uani 1 1 d . . .
H25 H 0.8650 0.1399 0.0825 0.092 Uiso 1 1 calc R . .
Cl1 Cl 0.7259(3) 0.2595(3) -0.0098(3) 0.1431(12) Uani 1 1 d . . .
Cl2 Cl 0.8475(3) 0.2746(5) 0.2365(3) 0.235(3) Uani 1 1 d . . .
Cl3 Cl 0.6690(3) 0.0739(3) 0.0875(4) 0.1541(14) Uani 1 1 d . . .
N1 N 0.7906(3) 0.8537(3) 0.8178(3) 0.0270(8) Uani 1 1 d . . .
N2 N 0.8986(3) 1.0272(3) 0.7730(3) 0.0253(8) Uani 1 1 d . . .
Ni1 Ni 0.75297(5) 0.90864(5) 0.67783(5) 0.02686(19) Uani 1 1 d . . .
O1 O 0.5345(3) 0.4303(3) 0.8456(3) 0.0387(8) Uani 1 1 d . . .
O2 O 1.0873(3) 1.3818(3) 0.6010(3) 0.0395(8) Uani 1 1 d . . .
O3 O 0.6145(3) 0.7856(3) 0.5957(3) 0.0327(7) Uani 1 1 d . . .
O4 O 0.7278(3) 0.9768(3) 0.5507(3) 0.0310(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.325(5) . ?
C1 C3 1.405(6) 2_777 ?
C1 C2 1.484(6) . ?
C2 N2 1.325(5) . ?
C2 C3 1.393(6) . ?
C3 C1 1.405(6) 2_777 ?
C3 H3 0.9300 . ?
C4 C9 1.375(6) . ?
C4 C5 1.386(6) . ?
C4 N1 1.431(5) . ?
C5 C6 1.388(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(6) . ?
C6 H6 0.9300 . ?
C7 O1 1.382(5) . ?
C7 C8 1.388(6) . ?
C8 C9 1.384(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 O1 1.431(6) . ?
C10 C11 1.506(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.371(6) . ?
C12 C13 1.384(6) . ?
C12 N2 1.424(5) . ?
C13 C14 1.384(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(6) . ?
C15 O2 1.381(5) . ?
C16 C17 1.390(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O2 1.425(6) . ?
C18 C19 1.494(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 O3 1.270(5) . ?
C20 C21 1.380(6) . ?
C20 C23 1.498(7) . ?
C21 C22 1.401(6) . ?
C21 H21 0.9300 . ?
C22 O4 1.267(5) . ?
C22 C24 1.492(6) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 Cl2 1.677(9) . ?
C25 Cl1 1.710(7) . ?
C25 Cl3 1.729(8) . ?
C25 H25 0.9800 . ?
N1 Ni1 1.888(3) . ?
N2 Ni1 1.881(3) . ?
Ni1 O3 1.842(3) . ?
Ni1 O4 1.846(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 C3 127.3(4) . 2_777 ?
N1 C1 C2 113.1(4) . . ?
C3 C1 C2 119.6(4) 2_777 . ?
N2 C2 C3 127.1(4) . . ?
N2 C2 C1 112.5(4) . . ?
C3 C2 C1 120.4(4) . . ?
C2 C3 C1 119.9(4) . 2_777 ?
C2 C3 H3 120.0 . . ?
C1 C3 H3 120.0 2_777 . ?
C9 C4 C5 119.5(4) . . ?
C9 C4 N1 120.5(4) . . ?
C5 C4 N1 120.0(4) . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 119.9(4) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C6 115.7(4) . . ?
O1 C7 C8 124.4(4) . . ?
C6 C7 C8 119.9(4) . . ?
C9 C8 C7 119.6(4) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C4 C9 C8 120.8(4) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
O1 C10 C11 107.5(4) . . ?
O1 C10 H10A 110.2 . . ?
C11 C10 H10A 110.2 . . ?
O1 C10 H10B 110.2 . . ?
C11 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 119.2(4) . . ?
C17 C12 N2 119.4(4) . . ?
C13 C12 N2 121.3(4) . . ?
C14 C13 C12 120.1(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.2(4) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 O2 124.2(4) . . ?
C14 C15 O2 115.8(4) . . ?
C15 C16 C17 119.7(4) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C12 C17 C16 120.8(4) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
O2 C18 C19 107.7(4) . . ?
O2 C18 H18A 110.2 . . ?
C19 C18 H18A 110.2 . . ?
O2 C18 H18B 110.2 . . ?
C19 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
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 . . ?
O3 C20 C21 125.2(4) . . ?
O3 C20 C23 114.2(4) . . ?
C21 C20 C23 120.6(4) . . ?
C20 C21 C22 122.5(4) . . ?
C20 C21 H21 118.7 . . ?
C22 C21 H21 118.7 . . ?
O4 C22 C21 124.3(4) . . ?
O4 C22 C24 115.6(4) . . ?
C21 C22 C24 120.1(4) . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
Cl2 C25 Cl1 113.6(5) . . ?
Cl2 C25 Cl3 108.4(5) . . ?
Cl1 C25 Cl3 108.4(4) . . ?
Cl2 C25 H25 108.8 . . ?
Cl1 C25 H25 108.8 . . ?
Cl3 C25 H25 108.8 . . ?
C1 N1 C4 120.0(4) . . ?
C1 N1 Ni1 115.2(3) . . ?
C4 N1 Ni1 124.8(3) . . ?
C2 N2 C12 119.8(4) . . ?
C2 N2 Ni1 115.7(3) . . ?
C12 N2 Ni1 124.5(3) . . ?
O3 Ni1 O4 94.41(13) . . ?
O3 Ni1 N2 174.82(14) . . ?
O4 Ni1 N2 90.72(14) . . ?
O3 Ni1 N1 91.37(14) . . ?
O4 Ni1 N1 174.09(14) . . ?
N2 Ni1 N1 83.51(15) . . ?
C7 O1 C10 117.5(4) . . ?
C15 O2 C18 117.2(4) . . ?
C20 O3 Ni1 126.4(3) . . ?
C22 O4 Ni1 126.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.94
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.239
_refine_diff_density_min         -0.977
_refine_diff_density_rms         0.105
_database_code_depnum_ccdc_archive 'CCDC 1023068'
#######################################################################
#
#                 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_1c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H52 N4 Ni2 O8'
_chemical_formula_weight         930.36

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   13.7366(7)
_cell_length_b                   11.9450(6)
_cell_length_c                   14.3878(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.0800(10)
_cell_angle_gamma                90.00
_cell_volume                     2244.24(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7281
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.91

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8271
_exptl_absorpt_correction_T_max  0.8847
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16268
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         27.91
_reflns_number_total             10286
_reflns_number_gt                9456
_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)+(0.0514P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.273(8)
_refine_ls_number_reflns         10286
_refine_ls_number_parameters     567
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
C1 C 0.63470(18) 0.5121(2) 0.28617(16) 0.0200(5) Uani 1 1 d . . .
C2 C 0.57731(18) 0.6057(2) 0.22593(16) 0.0204(5) Uani 1 1 d . . .
C3 C 0.47043(18) 0.6059(2) 0.19642(17) 0.0199(5) Uani 1 1 d . . .
H3 H 0.4334 0.6643 0.1557 0.024 Uiso 1 1 calc R . .
C4 C 0.41831(18) 0.5209(2) 0.22656(16) 0.0189(5) Uani 1 1 d . . .
C5 C 0.47519(18) 0.4249(2) 0.28358(16) 0.0187(5) Uani 1 1 d . . .
C6 C 0.58249(17) 0.4248(2) 0.31434(17) 0.0194(5) Uani 1 1 d . . .
H6 H 0.6194 0.3658 0.3541 0.023 Uiso 1 1 calc R . .
C7 C 0.80167(18) 0.4366(2) 0.35824(18) 0.0254(5) Uani 1 1 d . . .
C8 C 0.80214(19) 0.3308(2) 0.31671(19) 0.0279(5) Uani 1 1 d . . .
C9 C 0.8694(2) 0.2482(3) 0.3676(2) 0.0381(7) Uani 1 1 d . . .
H9 H 0.8679 0.1754 0.3407 0.046 Uiso 1 1 calc R . .
C10 C 0.9388(2) 0.2739(3) 0.4584(2) 0.0443(8) Uani 1 1 d . . .
H10 H 0.9857 0.2183 0.4928 0.053 Uiso 1 1 calc R . .
C11 C 0.9408(2) 0.3784(3) 0.4995(2) 0.0430(7) Uani 1 1 d . . .
H11 H 0.9889 0.3950 0.5613 0.052 Uiso 1 1 calc R . .
C12 C 0.8713(2) 0.4594(3) 0.44933(19) 0.0337(6) Uani 1 1 d . . .
H12 H 0.8716 0.5312 0.4778 0.040 Uiso 1 1 calc R . .
C13 C 0.7364(2) 0.2131(2) 0.1754(2) 0.0361(6) Uani 1 1 d . . .
H13A H 0.7133 0.1514 0.2094 0.043 Uiso 1 1 calc R . .
H13B H 0.8068 0.1964 0.1749 0.043 Uiso 1 1 calc R . .
C14 C 0.6666(3) 0.2239(3) 0.0737(2) 0.0513(9) Uani 1 1 d . . .
H14A H 0.5982 0.2455 0.0750 0.077 Uiso 1 1 calc R . .
H14B H 0.6626 0.1520 0.0399 0.077 Uiso 1 1 calc R . .
H14C H 0.6931 0.2812 0.0391 0.077 Uiso 1 1 calc R . .
C15 C 0.59603(19) 0.7750(2) 0.14548(18) 0.0258(5) Uani 1 1 d . . .
C16 C 0.6145(2) 0.7845(2) 0.05513(18) 0.0281(5) Uani 1 1 d . . .
C17 C 0.5774(2) 0.8779(3) -0.00359(18) 0.0342(6) Uani 1 1 d . . .
H17 H 0.5906 0.8861 -0.0643 0.041 Uiso 1 1 calc R . .
C18 C 0.5214(2) 0.9583(3) 0.0266(2) 0.0397(7) Uani 1 1 d . . .
H18 H 0.4950 1.0207 -0.0144 0.048 Uiso 1 1 calc R . .
C19 C 0.5034(2) 0.9492(2) 0.1155(2) 0.0384(7) Uani 1 1 d . . .
H19 H 0.4654 1.0052 0.1360 0.046 Uiso 1 1 calc R . .
C20 C 0.5415(2) 0.8577(2) 0.17426(19) 0.0317(6) Uani 1 1 d . . .
H20 H 0.5299 0.8516 0.2358 0.038 Uiso 1 1 calc R . .
C21 C 0.7071(3) 0.7121(3) -0.0479(2) 0.0442(8) Uani 1 1 d . . .
H21A H 0.7429 0.7848 -0.0431 0.053 Uiso 1 1 calc R . .
H21B H 0.6510 0.7094 -0.1108 0.053 Uiso 1 1 calc R . .
C22 C 0.7801(4) 0.6174(4) -0.0414(3) 0.0745(14) Uani 1 1 d . . .
H22A H 0.8348 0.6208 0.0214 0.112 Uiso 1 1 calc R . .
H22B H 0.8100 0.6233 -0.0949 0.112 Uiso 1 1 calc R . .
H22C H 0.7435 0.5461 -0.0466 0.112 Uiso 1 1 calc R . .
C23 C 0.25455(18) 0.6055(2) 0.16515(17) 0.0235(5) Uani 1 1 d . . .
C24 C 0.26949(19) 0.7114(2) 0.21087(18) 0.0257(5) Uani 1 1 d . . .
C25 C 0.2078(2) 0.8010(3) 0.1650(2) 0.0346(6) Uani 1 1 d . . .
H25 H 0.2186 0.8732 0.1942 0.042 Uiso 1 1 calc R . .
C26 C 0.1314(2) 0.7851(3) 0.0777(2) 0.0401(7) Uani 1 1 d . . .
H26 H 0.0893 0.8465 0.0478 0.048 Uiso 1 1 calc R . .
C27 C 0.1149(2) 0.6816(3) 0.0331(2) 0.0376(7) Uani 1 1 d . . .
H27 H 0.0618 0.6714 -0.0270 0.045 Uiso 1 1 calc R . .
C28 C 0.1774(2) 0.5920(2) 0.07742(18) 0.0300(6) Uani 1 1 d . . .
H28 H 0.1668 0.5205 0.0469 0.036 Uiso 1 1 calc R . .
C29 C 0.3680(2) 0.8222(2) 0.34918(19) 0.0302(6) Uani 1 1 d . . .
H29A H 0.3525 0.8845 0.3015 0.036 Uiso 1 1 calc R . .
H29B H 0.4420 0.8251 0.3861 0.036 Uiso 1 1 calc R . .
C30 C 0.3065(2) 0.8361(3) 0.41880(19) 0.0354(6) Uani 1 1 d . . .
H30A H 0.2338 0.8431 0.3816 0.053 Uiso 1 1 calc R . .
H30B H 0.3292 0.9036 0.4583 0.053 Uiso 1 1 calc R . .
H30C H 0.3166 0.7706 0.4618 0.053 Uiso 1 1 calc R . .
C31 C 0.45442(18) 0.2486(2) 0.35254(17) 0.0217(5) Uani 1 1 d . . .
C32 C 0.43141(19) 0.2216(2) 0.43881(17) 0.0240(5) Uani 1 1 d . . .
C33 C 0.4722(2) 0.1252(2) 0.4903(2) 0.0316(6) Uani 1 1 d . . .
H33 H 0.4567 0.1069 0.5485 0.038 Uiso 1 1 calc R . .
C34 C 0.5350(2) 0.0556(2) 0.4575(2) 0.0374(7) Uani 1 1 d . . .
H34 H 0.5632 -0.0096 0.4936 0.045 Uiso 1 1 calc R . .
C35 C 0.5568(2) 0.0807(2) 0.3724(2) 0.0363(6) Uani 1 1 d . . .
H35 H 0.5993 0.0323 0.3495 0.044 Uiso 1 1 calc R . .
C36 C 0.51677(19) 0.1766(2) 0.32042(19) 0.0275(5) Uani 1 1 d . . .
H36 H 0.5321 0.1934 0.2619 0.033 Uiso 1 1 calc R . .
C37 C 0.3208(2) 0.2591(3) 0.5350(2) 0.0367(6) Uani 1 1 d . . .
H37A H 0.3703 0.2586 0.6018 0.044 Uiso 1 1 calc R . .
H37B H 0.2939 0.1823 0.5189 0.044 Uiso 1 1 calc R . .
C38 C 0.2347(2) 0.3384(3) 0.5302(2) 0.0467(8) Uani 1 1 d . . .
H38A H 0.2614 0.4149 0.5418 0.070 Uiso 1 1 calc R . .
H38B H 0.2031 0.3181 0.5803 0.070 Uiso 1 1 calc R . .
H38C H 0.1834 0.3339 0.4655 0.070 Uiso 1 1 calc R . .
C39 C 1.0940(2) 0.6122(3) 0.3500(2) 0.0367(7) Uani 1 1 d . . .
H39A H 1.0839 0.5413 0.3800 0.055 Uiso 1 1 calc R . .
H39B H 1.1374 0.6617 0.4002 0.055 Uiso 1 1 calc R . .
H39C H 1.1273 0.5977 0.2999 0.055 Uiso 1 1 calc R . .
C40 C 0.99168(19) 0.6673(2) 0.30338(18) 0.0285(6) Uani 1 1 d . . .
C41 C 0.9860(2) 0.7671(3) 0.25297(19) 0.0352(6) Uani 1 1 d . . .
H41 H 1.0471 0.7972 0.2454 0.042 Uiso 1 1 calc R . .
C42 C 0.8944(2) 0.8255(3) 0.21273(19) 0.0344(6) Uani 1 1 d . . .
C43 C 0.8927(3) 0.9377(3) 0.1658(3) 0.0592(10) Uani 1 1 d . . .
H43A H 0.8257 0.9497 0.1169 0.089 Uiso 1 1 calc R . .
H43B H 0.9463 0.9407 0.1341 0.089 Uiso 1 1 calc R . .
H43C H 0.9051 0.9963 0.2159 0.089 Uiso 1 1 calc R . .
C44 C 0.1543(2) 0.0763(2) 0.3076(2) 0.0389(7) Uani 1 1 d . . .
H44A H 0.1515 0.0243 0.2541 0.058 Uiso 1 1 calc R . .
H44B H 0.0945 0.0645 0.3299 0.058 Uiso 1 1 calc R . .
H44C H 0.2170 0.0630 0.3619 0.058 Uiso 1 1 calc R . .
C45 C 0.15401(19) 0.1947(2) 0.27201(18) 0.0255(5) Uani 1 1 d . . .
C46 C 0.06305(19) 0.2530(2) 0.23582(19) 0.0293(6) Uani 1 1 d . . .
H46 H 0.0011 0.2173 0.2352 0.035 Uiso 1 1 calc R . .
C47 C 0.05861(18) 0.3619(2) 0.20021(17) 0.0253(5) Uani 1 1 d . . .
C48 C -0.04344(19) 0.4202(3) 0.1630(2) 0.0319(6) Uani 1 1 d . . .
H48A H -0.0626 0.4500 0.2183 0.048 Uiso 1 1 calc R . .
H48B H -0.0955 0.3667 0.1267 0.048 Uiso 1 1 calc R . .
H48C H -0.0386 0.4817 0.1196 0.048 Uiso 1 1 calc R . .
N1 N 0.73555(15) 0.52329(18) 0.30706(14) 0.0223(4) Uani 1 1 d . . .
N2 N 0.63833(15) 0.68117(18) 0.20598(14) 0.0228(4) Uani 1 1 d . . .
N3 N 0.31724(15) 0.51363(18) 0.20979(14) 0.0205(4) Uani 1 1 d . . .
N4 N 0.41304(15) 0.34679(17) 0.30016(14) 0.0205(4) Uani 1 1 d . . .
Ni1 Ni 0.77916(2) 0.65505(2) 0.26006(2) 0.02269(8) Uani 1 1 d . . .
Ni2 Ni 0.27205(2) 0.37635(2) 0.24702(2) 0.01984(8) Uani 1 1 d . . .
O1 O 0.73491(14) 0.31637(16) 0.22467(13) 0.0316(4) Uani 1 1 d . . .
O2 O 0.36984(14) 0.29581(15) 0.46633(12) 0.0282(4) Uani 1 1 d . . .
O3 O 0.34478(15) 0.71764(16) 0.29807(13) 0.0319(4) Uani 1 1 d . . .
O4 O 0.66736(15) 0.69873(17) 0.03186(13) 0.0340(4) Uani 1 1 d . . .
O5 O 0.91508(13) 0.61597(16) 0.31475(14) 0.0295(4) Uani 1 1 d . . .
O6 O 0.80704(15) 0.79162(17) 0.21460(14) 0.0330(4) Uani 1 1 d . . .
O7 O 0.24240(13) 0.23264(15) 0.27718(13) 0.0258(4) Uani 1 1 d . . .
O8 O 0.13626(13) 0.41848(15) 0.19765(13) 0.0256(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 1.330(3) . ?
C1 C6 1.395(3) . ?
C1 C2 1.482(3) . ?
C2 N2 1.322(3) . ?
C2 C3 1.396(3) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 N3 1.336(3) . ?
C4 C5 1.484(3) . ?
C5 N4 1.335(3) . ?
C5 C6 1.401(3) . ?
C6 H6 0.9500 . ?
C7 C12 1.389(4) . ?
C7 C8 1.398(4) . ?
C7 N1 1.423(3) . ?
C8 O1 1.370(3) . ?
C8 C9 1.394(4) . ?
C9 C10 1.392(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 O1 1.425(3) . ?
C13 C14 1.485(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.379(4) . ?
C15 C16 1.404(3) . ?
C15 N2 1.427(3) . ?
C16 O4 1.356(3) . ?
C16 C17 1.397(4) . ?
C17 C18 1.382(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 O4 1.424(3) . ?
C21 C22 1.495(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C28 1.383(3) . ?
C23 C24 1.410(4) . ?
C23 N3 1.420(3) . ?
C24 O3 1.358(3) . ?
C24 C25 1.398(4) . ?
C25 C26 1.377(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.380(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.397(4) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 O3 1.434(3) . ?
C29 C30 1.507(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C36 1.390(3) . ?
C31 C32 1.410(3) . ?
C31 N4 1.415(3) . ?
C32 O2 1.366(3) . ?
C32 C33 1.390(4) . ?
C33 C34 1.382(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.385(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 O2 1.427(3) . ?
C37 C38 1.499(5) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.508(4) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 O5 1.272(3) . ?
C40 C41 1.384(4) . ?
C41 C42 1.397(4) . ?
C41 H41 0.9500 . ?
C42 O6 1.274(3) . ?
C42 C43 1.498(4) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 C45 1.503(4) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 O7 1.276(3) . ?
C45 C46 1.383(4) . ?
C46 C47 1.392(4) . ?
C46 H46 0.9500 . ?
C47 O8 1.273(3) . ?
C47 C48 1.507(4) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
N1 Ni1 1.883(2) . ?
N2 Ni1 1.874(2) . ?
N3 Ni2 1.889(2) . ?
N4 Ni2 1.882(2) . ?
Ni1 O6 1.8416(19) . ?
Ni1 O5 1.8469(18) . ?
Ni2 O7 1.8468(18) . ?
Ni2 O8 1.8479(17) . ?

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 C6 127.1(2) . . ?
N1 C1 C2 112.6(2) . . ?
C6 C1 C2 120.3(2) . . ?
N2 C2 C3 127.6(2) . . ?
N2 C2 C1 112.5(2) . . ?
C3 C2 C1 119.8(2) . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
N3 C4 C3 126.8(2) . . ?
N3 C4 C5 112.9(2) . . ?
C3 C4 C5 120.3(2) . . ?
N4 C5 C6 127.7(2) . . ?
N4 C5 C4 112.5(2) . . ?
C6 C5 C4 119.8(2) . . ?
C1 C6 C5 119.5(2) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C12 C7 C8 119.2(2) . . ?
C12 C7 N1 119.2(2) . . ?
C8 C7 N1 121.6(2) . . ?
O1 C8 C9 123.8(3) . . ?
O1 C8 C7 115.8(2) . . ?
C9 C8 C7 120.3(3) . . ?
C10 C9 C8 119.1(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.2(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C7 C12 C11 120.8(3) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
O1 C13 C14 108.1(2) . . ?
O1 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
O1 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 119.4(2) . . ?
C20 C15 N2 122.4(2) . . ?
C16 C15 N2 118.1(2) . . ?
O4 C16 C17 125.2(2) . . ?
O4 C16 C15 115.6(2) . . ?
C17 C16 C15 119.2(3) . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.9(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 119.1(3) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C15 C20 C19 121.4(2) . . ?
C15 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
O4 C21 C22 106.4(3) . . ?
O4 C21 H21A 110.4 . . ?
C22 C21 H21A 110.4 . . ?
O4 C21 H21B 110.4 . . ?
C22 C21 H21B 110.4 . . ?
H21A C21 H21B 108.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C23 C24 119.4(2) . . ?
C28 C23 N3 120.5(2) . . ?
C24 C23 N3 120.1(2) . . ?
O3 C24 C25 124.8(2) . . ?
O3 C24 C23 116.0(2) . . ?
C25 C24 C23 119.2(2) . . ?
C26 C25 C24 120.3(3) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 121.1(3) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C28 119.1(3) . . ?
C26 C27 H27 120.5 . . ?
C28 C27 H27 120.5 . . ?
C23 C28 C27 121.0(3) . . ?
C23 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
O3 C29 C30 110.8(2) . . ?
O3 C29 H29A 109.5 . . ?
C30 C29 H29A 109.5 . . ?
O3 C29 H29B 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C36 C31 C32 118.8(2) . . ?
C36 C31 N4 121.5(2) . . ?
C32 C31 N4 119.7(2) . . ?
O2 C32 C33 124.5(2) . . ?
O2 C32 C31 115.8(2) . . ?
C33 C32 C31 119.7(2) . . ?
C34 C33 C32 120.4(3) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C35 C34 C33 120.2(3) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C34 C35 C36 119.9(3) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 C31 121.0(2) . . ?
C35 C36 H36 119.5 . . ?
C31 C36 H36 119.5 . . ?
O2 C37 C38 108.0(2) . . ?
O2 C37 H37A 110.1 . . ?
C38 C37 H37A 110.1 . . ?
O2 C37 H37B 110.1 . . ?
C38 C37 H37B 110.1 . . ?
H37A C37 H37B 108.4 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 H39A 109.5 . . ?
C40 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C40 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O5 C40 C41 124.6(3) . . ?
O5 C40 C39 115.2(3) . . ?
C41 C40 C39 120.2(2) . . ?
C40 C41 C42 123.0(3) . . ?
C40 C41 H41 118.5 . . ?
C42 C41 H41 118.5 . . ?
O6 C42 C41 124.4(3) . . ?
O6 C42 C43 114.3(3) . . ?
C41 C42 C43 121.3(3) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C45 C44 H44A 109.5 . . ?
C45 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C45 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
O7 C45 C46 125.1(3) . . ?
O7 C45 C44 114.4(2) . . ?
C46 C45 C44 120.6(2) . . ?
C45 C46 C47 122.7(2) . . ?
C45 C46 H46 118.6 . . ?
C47 C46 H46 118.6 . . ?
O8 C47 C46 124.4(2) . . ?
O8 C47 C48 116.1(2) . . ?
C46 C47 C48 119.5(2) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C1 N1 C7 119.8(2) . . ?
C1 N1 Ni1 115.33(17) . . ?
C7 N1 Ni1 124.83(15) . . ?
C2 N2 C15 120.2(2) . . ?
C2 N2 Ni1 116.02(17) . . ?
C15 N2 Ni1 123.81(16) . . ?
C4 N3 C23 118.8(2) . . ?
C4 N3 Ni2 114.82(16) . . ?
C23 N3 Ni2 126.37(16) . . ?
C5 N4 C31 120.1(2) . . ?
C5 N4 Ni2 115.53(17) . . ?
C31 N4 Ni2 124.39(16) . . ?
O6 Ni1 O5 94.65(8) . . ?
O6 Ni1 N2 90.38(9) . . ?
O5 Ni1 N2 174.82(9) . . ?
O6 Ni1 N1 172.99(9) . . ?
O5 Ni1 N1 91.60(9) . . ?
N2 Ni1 N1 83.44(9) . . ?
O7 Ni2 O8 94.22(8) . . ?
O7 Ni2 N4 90.25(8) . . ?
O8 Ni2 N4 174.95(9) . . ?
O7 Ni2 N3 171.67(8) . . ?
O8 Ni2 N3 92.06(9) . . ?
N4 Ni2 N3 83.73(9) . . ?
C8 O1 C13 118.7(2) . . ?
C32 O2 C37 118.0(2) . . ?
C24 O3 C29 120.4(2) . . ?
C16 O4 C21 118.9(2) . . ?
C40 O5 Ni1 126.21(19) . . ?
C42 O6 Ni1 126.1(2) . . ?
C45 O7 Ni2 126.27(18) . . ?
C47 O8 Ni2 126.81(18) . . ?

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
N1 C1 C2 N2 -0.4(3) . . . . ?
C6 C1 C2 N2 179.9(2) . . . . ?
N1 C1 C2 C3 179.1(2) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
N2 C2 C3 C4 -178.2(2) . . . . ?
C1 C2 C3 C4 2.4(3) . . . . ?
C2 C3 C4 N3 175.3(2) . . . . ?
C2 C3 C4 C5 -4.8(3) . . . . ?
N3 C4 C5 N4 4.7(3) . . . . ?
C3 C4 C5 N4 -175.22(19) . . . . ?
N3 C4 C5 C6 -174.6(2) . . . . ?
C3 C4 C5 C6 5.5(3) . . . . ?
N1 C1 C6 C5 -178.3(2) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
N4 C5 C6 C1 177.2(2) . . . . ?
C4 C5 C6 C1 -3.7(3) . . . . ?
C12 C7 C8 O1 -176.8(2) . . . . ?
N1 C7 C8 O1 -0.4(3) . . . . ?
C12 C7 C8 C9 2.1(4) . . . . ?
N1 C7 C8 C9 178.5(2) . . . . ?
O1 C8 C9 C10 176.2(2) . . . . ?
C7 C8 C9 C10 -2.6(4) . . . . ?
C8 C9 C10 C11 1.3(4) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C8 C7 C12 C11 -0.3(4) . . . . ?
N1 C7 C12 C11 -176.7(2) . . . . ?
C10 C11 C12 C7 -1.1(4) . . . . ?
C20 C15 C16 O4 -179.1(2) . . . . ?
N2 C15 C16 O4 3.3(3) . . . . ?
C20 C15 C16 C17 0.1(4) . . . . ?
N2 C15 C16 C17 -177.5(2) . . . . ?
O4 C16 C17 C18 177.8(3) . . . . ?
C15 C16 C17 C18 -1.3(4) . . . . ?
C16 C17 C18 C19 1.5(4) . . . . ?
C17 C18 C19 C20 -0.5(5) . . . . ?
C16 C15 C20 C19 0.8(4) . . . . ?
N2 C15 C20 C19 178.4(3) . . . . ?
C18 C19 C20 C15 -0.7(4) . . . . ?
C28 C23 C24 O3 178.3(2) . . . . ?
N3 C23 C24 O3 -0.8(3) . . . . ?
C28 C23 C24 C25 -1.8(4) . . . . ?
N3 C23 C24 C25 179.2(2) . . . . ?
O3 C24 C25 C26 -178.1(2) . . . . ?
C23 C24 C25 C26 1.9(4) . . . . ?
C24 C25 C26 C27 -0.9(4) . . . . ?
C25 C26 C27 C28 -0.3(4) . . . . ?
C24 C23 C28 C27 0.6(4) . . . . ?
N3 C23 C28 C27 179.7(2) . . . . ?
C26 C27 C28 C23 0.4(4) . . . . ?
C36 C31 C32 O2 180.0(2) . . . . ?
N4 C31 C32 O2 -0.8(3) . . . . ?
C36 C31 C32 C33 0.8(4) . . . . ?
N4 C31 C32 C33 -179.9(2) . . . . ?
O2 C32 C33 C34 -179.1(2) . . . . ?
C31 C32 C33 C34 0.0(4) . . . . ?
C32 C33 C34 C35 -0.8(4) . . . . ?
C33 C34 C35 C36 0.8(4) . . . . ?
C34 C35 C36 C31 0.0(4) . . . . ?
C32 C31 C36 C35 -0.8(4) . . . . ?
N4 C31 C36 C35 180.0(2) . . . . ?
O5 C40 C41 C42 3.3(4) . . . . ?
C39 C40 C41 C42 -176.4(3) . . . . ?
C40 C41 C42 O6 -2.9(5) . . . . ?
C40 C41 C42 C43 174.9(3) . . . . ?
O7 C45 C46 C47 0.1(4) . . . . ?
C44 C45 C46 C47 -178.7(2) . . . . ?
C45 C46 C47 O8 -0.4(4) . . . . ?
C45 C46 C47 C48 -179.4(2) . . . . ?
C6 C1 N1 C7 4.3(4) . . . . ?
C2 C1 N1 C7 -175.4(2) . . . . ?
C6 C1 N1 Ni1 -178.04(19) . . . . ?
C2 C1 N1 Ni1 2.3(3) . . . . ?
C12 C7 N1 C1 -117.9(3) . . . . ?
C8 C7 N1 C1 65.7(3) . . . . ?
C12 C7 N1 Ni1 64.7(3) . . . . ?
C8 C7 N1 Ni1 -111.7(2) . . . . ?
C3 C2 N2 C15 -1.9(4) . . . . ?
C1 C2 N2 C15 177.6(2) . . . . ?
C3 C2 N2 Ni1 178.88(19) . . . . ?
C1 C2 N2 Ni1 -1.7(2) . . . . ?
C20 C15 N2 C2 67.0(3) . . . . ?
C16 C15 N2 C2 -115.5(3) . . . . ?
C20 C15 N2 Ni1 -113.8(2) . . . . ?
C16 C15 N2 Ni1 63.7(3) . . . . ?
C3 C4 N3 C23 -6.8(3) . . . . ?
C5 C4 N3 C23 173.3(2) . . . . ?
C3 C4 N3 Ni2 171.99(19) . . . . ?
C5 C4 N3 Ni2 -7.9(2) . . . . ?
C28 C23 N3 C4 120.8(2) . . . . ?
C24 C23 N3 C4 -60.2(3) . . . . ?
C28 C23 N3 Ni2 -57.8(3) . . . . ?
C24 C23 N3 Ni2 121.2(2) . . . . ?
C6 C5 N4 C31 -1.6(4) . . . . ?
C4 C5 N4 C31 179.2(2) . . . . ?
C6 C5 N4 Ni2 179.89(19) . . . . ?
C4 C5 N4 Ni2 0.7(2) . . . . ?
C36 C31 N4 C5 -58.7(3) . . . . ?
C32 C31 N4 C5 122.1(2) . . . . ?
C36 C31 N4 Ni2 119.7(2) . . . . ?
C32 C31 N4 Ni2 -59.6(3) . . . . ?
C2 N2 Ni1 O6 -174.37(17) . . . . ?
C15 N2 Ni1 O6 6.4(2) . . . . ?
C2 N2 Ni1 O5 19.2(10) . . . . ?
C15 N2 Ni1 O5 -160.0(8) . . . . ?
C2 N2 Ni1 N1 2.32(17) . . . . ?
C15 N2 Ni1 N1 -176.9(2) . . . . ?
C1 N1 Ni1 O6 25.7(8) . . . . ?
C7 N1 Ni1 O6 -156.8(7) . . . . ?
C1 N1 Ni1 O5 178.95(17) . . . . ?
C7 N1 Ni1 O5 -3.5(2) . . . . ?
C1 N1 Ni1 N2 -2.55(17) . . . . ?
C7 N1 Ni1 N2 175.0(2) . . . . ?
C5 N4 Ni2 O7 170.29(17) . . . . ?
C31 N4 Ni2 O7 -8.14(19) . . . . ?
C5 N4 Ni2 O8 -37.6(10) . . . . ?
C31 N4 Ni2 O8 144.0(9) . . . . ?
C5 N4 Ni2 N3 -3.95(16) . . . . ?
C31 N4 Ni2 N3 177.63(19) . . . . ?
C4 N3 Ni2 O7 -37.2(7) . . . . ?
C23 N3 Ni2 O7 141.5(5) . . . . ?
C4 N3 Ni2 O8 -176.08(16) . . . . ?
C23 N3 Ni2 O8 2.6(2) . . . . ?
C4 N3 Ni2 N4 6.72(16) . . . . ?
C23 N3 Ni2 N4 -174.6(2) . . . . ?
C9 C8 O1 C13 -3.1(4) . . . . ?
C7 C8 O1 C13 175.7(2) . . . . ?
C14 C13 O1 C8 -173.0(2) . . . . ?
C33 C32 O2 C37 -18.2(3) . . . . ?
C31 C32 O2 C37 162.6(2) . . . . ?
C38 C37 O2 C32 -162.7(2) . . . . ?
C25 C24 O3 C29 -1.7(4) . . . . ?
C23 C24 O3 C29 178.2(2) . . . . ?
C30 C29 O3 C24 91.2(3) . . . . ?
C17 C16 O4 C21 13.4(4) . . . . ?
C15 C16 O4 C21 -167.4(3) . . . . ?
C22 C21 O4 C16 167.3(3) . . . . ?
C41 C40 O5 Ni1 4.9(4) . . . . ?
C39 C40 O5 Ni1 -175.33(17) . . . . ?
O6 Ni1 O5 C40 -9.8(2) . . . . ?
N2 Ni1 O5 C40 156.6(8) . . . . ?
N1 Ni1 O5 C40 173.4(2) . . . . ?
C41 C42 O6 Ni1 -5.6(4) . . . . ?
C43 C42 O6 Ni1 176.4(2) . . . . ?
O5 Ni1 O6 C42 10.1(2) . . . . ?
N2 Ni1 O6 C42 -168.7(2) . . . . ?
N1 Ni1 O6 C42 163.3(6) . . . . ?
C46 C45 O7 Ni2 5.0(4) . . . . ?
C44 C45 O7 Ni2 -176.16(18) . . . . ?
O8 Ni2 O7 C45 -7.2(2) . . . . ?
N4 Ni2 O7 C45 170.4(2) . . . . ?
N3 Ni2 O7 C45 -146.0(5) . . . . ?
C46 C47 O8 Ni2 -4.6(4) . . . . ?
C48 C47 O8 Ni2 174.46(17) . . . . ?
O7 Ni2 O8 C47 7.1(2) . . . . ?
N4 Ni2 O8 C47 -144.9(9) . . . . ?
N3 Ni2 O8 C47 -178.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.91
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 1023069'
#######################################################################
#
#                 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_1e

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H68 N4 Ni2 O4'
_chemical_formula_weight         978.56

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.4280(8)
_cell_length_b                   11.7109(10)
_cell_length_c                   13.9731(13)
_cell_angle_alpha                113.575(2)
_cell_angle_beta                 91.422(2)
_cell_angle_gamma                93.090(2)
_cell_volume                     1260.6(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1312
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8967
_exptl_absorpt_correction_T_max  0.9391
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         42
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  160
_diffrn_standards_decay_%        2
_diffrn_reflns_number            9380
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0957
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         27.95
_reflns_number_total             6006
_reflns_number_gt                4369
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART-W2K/NT(Bruker, 2003)'
_computing_cell_refinement       'SAINT-W2K/NT(Bruker, 2003)'
_computing_data_reduction        SAINT-W2K/NT
_computing_structure_solution    'SHELXTL-NT(Bruker, 2003)'
_computing_structure_refinement  SHELXTL-NT
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXTL-NT

_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)+(0.0608P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6006
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_ref         0.1431
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
C1 C 0.5053(4) 0.8766(3) 0.9246(2) 0.0188(7) Uani 1 1 d . . .
C2 C 0.5712(3) 0.9854(3) 0.9054(2) 0.0188(7) Uani 1 1 d . . .
C3 C 0.5651(4) 1.1060(3) 0.9818(2) 0.0202(7) Uani 1 1 d . . .
H3 H 0.6084 1.1757 0.9702 0.024 Uiso 1 1 calc R . .
C4 C 0.4439(4) 0.6556(3) 0.8416(2) 0.0222(7) Uani 1 1 d . . .
C5 C 0.5298(4) 0.5768(3) 0.8725(3) 0.0261(8) Uani 1 1 d . . .
C6 C 0.6976(4) 0.6162(3) 0.9167(3) 0.0347(9) Uani 1 1 d . . .
H6A H 0.6938 0.6731 0.9913 0.042 Uiso 1 1 calc R . .
H6B H 0.7484 0.6646 0.8803 0.042 Uiso 1 1 calc R . .
C7 C 0.8027(5) 0.5127(4) 0.9095(4) 0.0501(12) Uani 1 1 d . . .
H7A H 0.7621 0.4707 0.9530 0.075 Uiso 1 1 calc R . .
H7B H 0.9115 0.5482 0.9342 0.075 Uiso 1 1 calc R . .
H7C H 0.8027 0.4523 0.8367 0.075 Uiso 1 1 calc R . .
C8 C 0.4526(4) 0.4636(3) 0.8627(3) 0.0325(8) Uani 1 1 d . . .
H8 H 0.5089 0.4069 0.8815 0.039 Uiso 1 1 calc R . .
C9 C 0.2971(5) 0.4335(3) 0.8264(3) 0.0368(9) Uani 1 1 d . . .
H9 H 0.2461 0.3570 0.8218 0.044 Uiso 1 1 calc R . .
C10 C 0.2139(4) 0.5124(3) 0.7965(3) 0.0335(9) Uani 1 1 d . . .
H10 H 0.1061 0.4900 0.7714 0.040 Uiso 1 1 calc R . .
C11 C 0.2860(4) 0.6251(3) 0.8025(3) 0.0258(7) Uani 1 1 d . . .
C12 C 0.2016(4) 0.7133(3) 0.7677(3) 0.0354(9) Uani 1 1 d . . .
H12A H 0.2666 0.7297 0.7160 0.042 Uiso 1 1 calc R . .
H12B H 0.1970 0.7937 0.8289 0.042 Uiso 1 1 calc R . .
C13 C 0.0341(5) 0.6700(4) 0.7199(4) 0.0499(12) Uani 1 1 d . . .
H13A H 0.0363 0.5908 0.6587 0.075 Uiso 1 1 calc R . .
H13B H -0.0083 0.7330 0.6986 0.075 Uiso 1 1 calc R . .
H13C H -0.0339 0.6581 0.7716 0.075 Uiso 1 1 calc R . .
C14 C 0.6869(4) 1.0442(3) 0.7757(2) 0.0212(7) Uani 1 1 d . . .
C15 C 0.5797(4) 1.0961(3) 0.7293(3) 0.0259(8) Uani 1 1 d . . .
C16 C 0.4025(4) 1.0656(3) 0.7230(3) 0.0321(8) Uani 1 1 d . . .
H16A H 0.3465 1.1393 0.7268 0.039 Uiso 1 1 calc R . .
H16B H 0.3735 1.0469 0.7837 0.039 Uiso 1 1 calc R . .
C17 C 0.3475(5) 0.9541(4) 0.6222(4) 0.0489(11) Uani 1 1 d . . .
H17A H 0.3803 0.9706 0.5619 0.073 Uiso 1 1 calc R . .
H17B H 0.2313 0.9409 0.6192 0.073 Uiso 1 1 calc R . .
H17C H 0.3956 0.8792 0.6210 0.073 Uiso 1 1 calc R . .
C18 C 0.6412(5) 1.1764(3) 0.6857(3) 0.0350(9) Uani 1 1 d . . .
H18 H 0.5707 1.2150 0.6556 0.042 Uiso 1 1 calc R . .
C19 C 0.8027(5) 1.2004(4) 0.6857(3) 0.0419(10) Uani 1 1 d . . .
H19 H 0.8428 1.2525 0.6531 0.050 Uiso 1 1 calc R . .
C20 C 0.9068(4) 1.1496(3) 0.7324(3) 0.0348(9) Uani 1 1 d . . .
H20 H 1.0180 1.1688 0.7334 0.042 Uiso 1 1 calc R . .
C21 C 0.8515(4) 1.0704(3) 0.7782(3) 0.0264(8) Uani 1 1 d . . .
C22 C 0.9674(4) 1.0184(4) 0.8305(3) 0.0365(9) Uani 1 1 d . . .
H22A H 1.0583 0.9895 0.7854 0.044 Uiso 1 1 calc R . .
H22B H 0.9149 0.9451 0.8383 0.044 Uiso 1 1 calc R . .
C23 C 1.0290(6) 1.1122(5) 0.9365(4) 0.0696(15) Uani 1 1 d . . .
H23A H 1.0778 1.1863 0.9298 0.104 Uiso 1 1 calc R . .
H23B H 1.1086 1.0751 0.9654 0.104 Uiso 1 1 calc R . .
H23C H 0.9407 1.1362 0.9833 0.104 Uiso 1 1 calc R . .
C24 C 0.6804(5) 0.4096(3) 0.5437(3) 0.0382(10) Uani 1 1 d . . .
H24A H 0.6071 0.3845 0.5862 0.057 Uiso 1 1 calc R . .
H24B H 0.7882 0.3885 0.5552 0.057 Uiso 1 1 calc R . .
H24C H 0.6468 0.3656 0.4696 0.057 Uiso 1 1 calc R . .
C25 C 0.6793(4) 0.5481(3) 0.5745(3) 0.0261(8) Uani 1 1 d . . .
C26 C 0.7386(4) 0.6010(3) 0.5091(3) 0.0296(8) Uani 1 1 d . . .
H26 H 0.7704 0.5472 0.4422 0.036 Uiso 1 1 calc R . .
C27 C 0.7539(4) 0.7289(3) 0.5366(3) 0.0271(8) Uani 1 1 d . . .
C28 C 0.8226(5) 0.7824(4) 0.4643(3) 0.0445(11) Uani 1 1 d . . .
H28A H 0.7509 0.8415 0.4563 0.067 Uiso 1 1 calc R . .
H28B H 0.8354 0.7148 0.3959 0.067 Uiso 1 1 calc R . .
H28C H 0.9265 0.8258 0.4935 0.067 Uiso 1 1 calc R . .
N1 N 0.5200(3) 0.7689(2) 0.8433(2) 0.0202(6) Uani 1 1 d . . .
N2 N 0.6275(3) 0.9522(2) 0.8114(2) 0.0204(6) Uani 1 1 d . . .
Ni1 Ni 0.62321(5) 0.77993(4) 0.72984(3) 0.01919(14) Uani 1 1 d . . .
O1 O 0.6248(3) 0.60850(19) 0.66387(17) 0.0243(5) Uani 1 1 d . . .
O2 O 0.7162(3) 0.8102(2) 0.62381(17) 0.0265(5) 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 1.332(4) . ?
C1 C3 1.394(4) 2_677 ?
C1 C2 1.486(4) . ?
C2 N2 1.322(4) . ?
C2 C3 1.394(4) . ?
C3 C1 1.394(4) 2_677 ?
C3 H3 0.9500 . ?
C4 C5 1.393(5) . ?
C4 C11 1.397(5) . ?
C4 N1 1.433(4) . ?
C5 C8 1.399(5) . ?
C5 C6 1.501(5) . ?
C6 C7 1.511(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.369(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.374(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.508(5) . ?
C12 C13 1.517(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.397(5) . ?
C14 C21 1.401(4) . ?
C14 N2 1.429(4) . ?
C15 C18 1.395(5) . ?
C15 C16 1.508(5) . ?
C16 C17 1.528(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.375(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.374(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.498(5) . ?
C22 C23 1.506(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.503(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 O1 1.276(4) . ?
C25 C26 1.382(5) . ?
C26 C27 1.388(5) . ?
C26 H26 0.9500 . ?
C27 O2 1.271(4) . ?
C27 C28 1.497(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N1 Ni1 1.873(3) . ?
N2 Ni1 1.876(3) . ?
Ni1 O2 1.839(2) . ?
Ni1 O1 1.845(2) . ?

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 C3 127.3(3) . 2_677 ?
N1 C1 C2 112.1(3) . . ?
C3 C1 C2 120.5(3) 2_677 . ?
N2 C2 C3 127.4(3) . . ?
N2 C2 C1 112.4(3) . . ?
C3 C2 C1 120.2(3) . . ?
C2 C3 C1 119.3(3) . 2_677 ?
C2 C3 H3 120.4 . . ?
C1 C3 H3 120.4 2_677 . ?
C5 C4 C11 122.2(3) . . ?
C5 C4 N1 120.0(3) . . ?
C11 C4 N1 117.7(3) . . ?
C4 C5 C8 117.6(3) . . ?
C4 C5 C6 119.8(3) . . ?
C8 C5 C6 122.6(3) . . ?
C5 C6 C7 116.4(3) . . ?
C5 C6 H6A 108.2 . . ?
C7 C6 H6A 108.2 . . ?
C5 C6 H6B 108.2 . . ?
C7 C6 H6B 108.2 . . ?
H6A C6 H6B 107.3 . . ?
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 . . ?
C9 C8 C5 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C5 C8 H8 119.6 . . ?
C8 C9 C10 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 120.7(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C4 117.8(3) . . ?
C10 C11 C12 122.8(3) . . ?
C4 C11 C12 119.4(3) . . ?
C11 C12 C13 116.3(3) . . ?
C11 C12 H12A 108.2 . . ?
C13 C12 H12A 108.2 . . ?
C11 C12 H12B 108.2 . . ?
C13 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
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 . . ?
C15 C14 C21 121.6(3) . . ?
C15 C14 N2 118.7(3) . . ?
C21 C14 N2 119.4(3) . . ?
C18 C15 C14 117.9(3) . . ?
C18 C15 C16 119.8(3) . . ?
C14 C15 C16 122.2(3) . . ?
C15 C16 C17 112.1(3) . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C15 120.8(4) . . ?
C19 C18 H18 119.6 . . ?
C15 C18 H18 119.6 . . ?
C20 C19 C18 120.6(4) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 120.8(4) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C14 118.2(3) . . ?
C20 C21 C22 119.7(3) . . ?
C14 C21 C22 122.1(3) . . ?
C21 C22 C23 112.8(3) . . ?
C21 C22 H22A 109.0 . . ?
C23 C22 H22A 109.0 . . ?
C21 C22 H22B 109.0 . . ?
C23 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O1 C25 C26 125.1(3) . . ?
O1 C25 C24 114.7(3) . . ?
C26 C25 C24 120.2(3) . . ?
C25 C26 C27 123.1(3) . . ?
C25 C26 H26 118.4 . . ?
C27 C26 H26 118.4 . . ?
O2 C27 C26 124.3(3) . . ?
O2 C27 C28 114.4(3) . . ?
C26 C27 C28 121.3(3) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C1 N1 C4 120.0(3) . . ?
C1 N1 Ni1 115.9(2) . . ?
C4 N1 Ni1 123.7(2) . . ?
C2 N2 C14 120.8(3) . . ?
C2 N2 Ni1 116.1(2) . . ?
C14 N2 Ni1 123.1(2) . . ?
O2 Ni1 O1 94.92(10) . . ?
O2 Ni1 N1 173.00(10) . . ?
O1 Ni1 N1 91.69(10) . . ?
O2 Ni1 N2 90.29(11) . . ?
O1 Ni1 N2 173.36(11) . . ?
N1 Ni1 N2 83.28(11) . . ?
C25 O1 Ni1 125.7(2) . . ?
C27 O2 Ni1 126.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 1.1(4) . . . . ?
C3 C1 C2 N2 -177.5(3) 2_677 . . . ?
N1 C1 C2 C3 179.5(3) . . . . ?
C3 C1 C2 C3 0.9(5) 2_677 . . . ?
N2 C2 C3 C1 177.2(3) . . . 2_677 ?
C1 C2 C3 C1 -0.9(5) . . . 2_677 ?
C11 C4 C5 C8 0.3(5) . . . . ?
N1 C4 C5 C8 -175.9(3) . . . . ?
C11 C4 C5 C6 -178.3(3) . . . . ?
N1 C4 C5 C6 5.6(5) . . . . ?
C4 C5 C6 C7 -157.1(3) . . . . ?
C8 C5 C6 C7 24.4(5) . . . . ?
C4 C5 C8 C9 -1.5(5) . . . . ?
C6 C5 C8 C9 177.0(3) . . . . ?
C5 C8 C9 C10 1.4(6) . . . . ?
C8 C9 C10 C11 0.0(6) . . . . ?
C9 C10 C11 C4 -1.1(5) . . . . ?
C9 C10 C11 C12 178.2(3) . . . . ?
C5 C4 C11 C10 1.0(5) . . . . ?
N1 C4 C11 C10 177.3(3) . . . . ?
C5 C4 C11 C12 -178.3(3) . . . . ?
N1 C4 C11 C12 -2.1(5) . . . . ?
C10 C11 C12 C13 -3.0(5) . . . . ?
C4 C11 C12 C13 176.3(3) . . . . ?
C21 C14 C15 C18 -0.5(5) . . . . ?
N2 C14 C15 C18 -173.8(3) . . . . ?
C21 C14 C15 C16 178.1(3) . . . . ?
N2 C14 C15 C16 4.7(5) . . . . ?
C18 C15 C16 C17 87.6(4) . . . . ?
C14 C15 C16 C17 -90.9(4) . . . . ?
C14 C15 C18 C19 2.0(5) . . . . ?
C16 C15 C18 C19 -176.6(3) . . . . ?
C15 C18 C19 C20 -2.6(6) . . . . ?
C18 C19 C20 C21 1.7(6) . . . . ?
C19 C20 C21 C14 -0.2(5) . . . . ?
C19 C20 C21 C22 -178.8(4) . . . . ?
C15 C14 C21 C20 -0.4(5) . . . . ?
N2 C14 C21 C20 172.9(3) . . . . ?
C15 C14 C21 C22 178.1(3) . . . . ?
N2 C14 C21 C22 -8.6(5) . . . . ?
C20 C21 C22 C23 76.8(5) . . . . ?
C14 C21 C22 C23 -101.8(4) . . . . ?
O1 C25 C26 C27 3.8(6) . . . . ?
C24 C25 C26 C27 -174.2(3) . . . . ?
C25 C26 C27 O2 0.3(6) . . . . ?
C25 C26 C27 C28 178.4(4) . . . . ?
C3 C1 N1 C4 7.2(5) 2_677 . . . ?
C2 C1 N1 C4 -171.3(3) . . . . ?
C3 C1 N1 Ni1 -179.6(3) 2_677 . . . ?
C2 C1 N1 Ni1 1.9(3) . . . . ?
C5 C4 N1 C1 -97.2(4) . . . . ?
C11 C4 N1 C1 86.4(4) . . . . ?
C5 C4 N1 Ni1 90.1(3) . . . . ?
C11 C4 N1 Ni1 -86.3(3) . . . . ?
C3 C2 N2 C14 -2.2(5) . . . . ?
C1 C2 N2 C14 176.1(3) . . . . ?
C3 C2 N2 Ni1 178.1(3) . . . . ?
C1 C2 N2 Ni1 -3.7(3) . . . . ?
C15 C14 N2 C2 -85.7(4) . . . . ?
C21 C14 N2 C2 100.8(4) . . . . ?
C15 C14 N2 Ni1 94.1(3) . . . . ?
C21 C14 N2 Ni1 -79.4(3) . . . . ?
C1 N1 Ni1 O2 -26.6(11) . . . . ?
C4 N1 Ni1 O2 146.4(8) . . . . ?
C1 N1 Ni1 O1 172.5(2) . . . . ?
C4 N1 Ni1 O1 -14.5(3) . . . . ?
C1 N1 Ni1 N2 -3.1(2) . . . . ?
C4 N1 Ni1 N2 169.9(3) . . . . ?
C2 N2 Ni1 O2 -178.9(2) . . . . ?
C14 N2 Ni1 O2 1.3(3) . . . . ?
C2 N2 Ni1 O1 -37.2(10) . . . . ?
C14 N2 Ni1 O1 143.1(8) . . . . ?
C2 N2 Ni1 N1 3.8(2) . . . . ?
C14 N2 Ni1 N1 -175.9(3) . . . . ?
C26 C25 O1 Ni1 -3.9(5) . . . . ?
C24 C25 O1 Ni1 174.3(2) . . . . ?
O2 Ni1 O1 C25 0.7(3) . . . . ?
N1 Ni1 O1 C25 178.4(3) . . . . ?
N2 Ni1 O1 C25 -140.9(9) . . . . ?
C26 C27 O2 Ni1 -3.9(5) . . . . ?
C28 C27 O2 Ni1 177.9(2) . . . . ?
O1 Ni1 O2 C27 3.1(3) . . . . ?
N1 Ni1 O2 C27 -157.7(8) . . . . ?
N2 Ni1 O2 C27 179.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.95
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.093
_database_code_depnum_ccdc_archive 'CCDC 1023070'
#######################################################################
#
#                 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_2c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C76 H80 Cl2 N8 Ni O16'
_chemical_formula_weight         1491.09

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'
Cl Cl 0.1484 0.1585 '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   C2/c

loop_
_symmetry_equiv_pos_as_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'
'-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                   27.029(6)
_cell_length_b                   13.321(3)
_cell_length_c                   25.424(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.358(3)
_cell_angle_gamma                90.00
_cell_volume                     8525(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3745
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      21.16

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3128
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9723
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_process_details   'SADABS-2008/1 - Bruker AXS 2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            44934
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         26.37
_reflns_number_total             8727
_reflns_number_gt                4792
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.1662P)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         8727
_refine_ls_number_parameters     477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1363
_refine_ls_R_factor_gt           0.0826
_refine_ls_wR_factor_ref         0.2701
_refine_ls_wR_factor_gt          0.2385
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.014
_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
C1 C 0.89609(15) 0.3836(3) 0.17511(17) 0.0374(9) Uani 1 1 d . . .
C2 C 0.90021(15) 0.3305(3) 0.22759(17) 0.0415(10) Uani 1 1 d . . .
C3 C 0.85477(16) 0.2814(4) 0.23005(18) 0.0486(11) Uani 1 1 d . . .
H1 H 0.8573 0.2471 0.2628 0.058 Uiso 1 1 calc R . .
C4 C 0.80740(16) 0.2829(4) 0.18604(18) 0.0476(11) Uani 1 1 d . . .
C5 C 0.80199(14) 0.3439(3) 0.13477(16) 0.0398(9) Uani 1 1 d . . .
C6 C 0.84579(15) 0.3886(3) 0.13089(16) 0.0390(9) Uani 1 1 d . . .
H2 H 0.8426 0.4235 0.0981 0.047 Uiso 1 1 calc R . .
C7 C 0.95023(16) 0.4686(4) 0.13093(19) 0.0463(10) Uani 1 1 d . . .
C8 C 0.99393(18) 0.5331(4) 0.14621(19) 0.0533(12) Uani 1 1 d . . .
C9 C 1.0083(2) 0.5789(5) 0.1057(3) 0.087(2) Uani 1 1 d . . .
H9 H 1.0368 0.6234 0.1161 0.105 Uiso 1 1 calc R . .
C10 C 0.9804(3) 0.5586(6) 0.0495(2) 0.101(3) Uani 1 1 d . . .
H10 H 0.9892 0.5914 0.0218 0.121 Uiso 1 1 calc R . .
C11 C 0.9398(2) 0.4905(5) 0.0345(2) 0.0844(19) Uani 1 1 d . . .
H11 H 0.9223 0.4746 -0.0034 0.101 Uiso 1 1 calc R . .
C12 C 0.92496(18) 0.4458(4) 0.07435(19) 0.0551(13) Uani 1 1 d . . .
H12 H 0.8974 0.3993 0.0635 0.066 Uiso 1 1 calc R . .
C13 C 1.0731(2) 0.5951(5) 0.2245(3) 0.0800(18) Uani 1 1 d . . .
H13A H 1.0936 0.5702 0.2619 0.096 Uiso 1 1 calc R . .
H13B H 1.0919 0.5785 0.1996 0.096 Uiso 1 1 calc R . .
C14 C 1.0673(3) 0.7037(6) 0.2264(4) 0.120(3) Uani 1 1 d . . .
H14A H 1.0448 0.7275 0.1899 0.179 Uiso 1 1 calc R . .
H14B H 1.1016 0.7348 0.2369 0.179 Uiso 1 1 calc R . .
H14C H 1.0517 0.7202 0.2537 0.179 Uiso 1 1 calc R . .
C15 C 0.95855(18) 0.2886(4) 0.3211(2) 0.0658(15) Uani 1 1 d . . .
C16 C 0.9340(2) 0.3169(5) 0.3571(2) 0.0772(19) Uani 1 1 d . . .
C17 C 0.9517(3) 0.2796(7) 0.4116(3) 0.116(3) Uani 1 1 d . . .
H17 H 0.9338 0.2966 0.4354 0.140 Uiso 1 1 calc R . .
C18 C 0.9928(4) 0.2214(10) 0.4299(4) 0.149(5) Uani 1 1 d . . .
H18 H 1.0053 0.2020 0.4676 0.179 Uiso 1 1 calc R . .
C19 C 1.0203(4) 0.1851(8) 0.3939(5) 0.164(6) Uani 1 1 d . . .
H19 H 1.0483 0.1400 0.4082 0.197 Uiso 1 1 calc R . .
C20 C 1.0046(2) 0.2180(5) 0.3377(3) 0.099(3) Uani 1 1 d . . .
H20 H 1.0213 0.1979 0.3132 0.119 Uiso 1 1 calc R . .
C21 C 0.8597(4) 0.3941(8) 0.3675(4) 0.130(3) Uani 1 1 d . . .
H21A H 0.8781 0.4309 0.4020 0.156 Uiso 1 1 calc R . .
H21B H 0.8489 0.3297 0.3776 0.156 Uiso 1 1 calc R . .
C22 C 0.8113(4) 0.4519(8) 0.3316(4) 0.147(4) Uani 1 1 d . . .
H22A H 0.8198 0.5220 0.3329 0.220 Uiso 1 1 calc R . .
H22B H 0.7832 0.4420 0.3458 0.220 Uiso 1 1 calc R . .
H22C H 0.8000 0.4285 0.2934 0.220 Uiso 1 1 calc R . .
C23 C 0.7604(2) 0.1828(5) 0.2338(2) 0.0683(16) Uani 1 1 d . . .
C24 C 0.7920(3) 0.0992(6) 0.2583(3) 0.091(2) Uani 1 1 d . . .
C25 C 0.7882(4) 0.0539(7) 0.3057(4) 0.131(4) Uani 1 1 d . . .
H25 H 0.8097 -0.0001 0.3229 0.157 Uiso 1 1 calc R . .
C26 C 0.7512(4) 0.0915(10) 0.3266(4) 0.150(5) Uani 1 1 d . . .
H26 H 0.7461 0.0587 0.3565 0.180 Uiso 1 1 calc R . .
C27 C 0.7245(4) 0.1685(10) 0.3063(4) 0.145(4) Uani 1 1 d . . .
H27 H 0.7023 0.1959 0.3232 0.174 Uiso 1 1 calc R . .
C28 C 0.7282(3) 0.2135(7) 0.2575(3) 0.115(3) Uani 1 1 d . . .
H28 H 0.7064 0.2680 0.2416 0.138 Uiso 1 1 calc R . .
C29 C 0.8661(6) -0.0048(9) 0.2611(6) 0.195(6) Uani 1 1 d . . .
H29A H 0.8517 -0.0705 0.2638 0.234 Uiso 1 1 calc R . .
H29B H 0.8856 0.0200 0.2989 0.234 Uiso 1 1 calc R . .
C30 C 0.9016(9) -0.0088(13) 0.2259(7) 0.307(12) Uani 1 1 d . . .
H30A H 0.8967 -0.0719 0.2064 0.460 Uiso 1 1 calc R . .
H30B H 0.9381 -0.0020 0.2503 0.460 Uiso 1 1 calc R . .
H30C H 0.8923 0.0449 0.1989 0.460 Uiso 1 1 calc R . .
C31 C 0.74368(15) 0.3918(3) 0.03871(17) 0.0447(10) Uani 1 1 d . . .
C32 C 0.7006(2) 0.4545(5) 0.0137(2) 0.0708(15) Uani 1 1 d . . .
C33 C 0.6871(3) 0.4864(6) -0.0412(3) 0.103(2) Uani 1 1 d . . .
H33 H 0.6574 0.5267 -0.0579 0.124 Uiso 1 1 calc R . .
C34 C 0.7183(3) 0.4577(7) -0.0715(3) 0.106(3) Uani 1 1 d . . .
H34 H 0.7096 0.4789 -0.1086 0.127 Uiso 1 1 calc R . .
C35 C 0.7610(2) 0.3995(5) -0.0474(2) 0.0743(16) Uani 1 1 d . . .
H35 H 0.7826 0.3832 -0.0674 0.089 Uiso 1 1 calc R . .
C36 C 0.77335(18) 0.3633(4) 0.00702(18) 0.0546(12) Uani 1 1 d . . .
H36 H 0.8018 0.3195 0.0223 0.065 Uiso 1 1 calc R . .
C37 C 0.6195(3) 0.5158(9) 0.0183(4) 0.162(5) Uani 1 1 d . . .
H37A H 0.6201 0.5789 -0.0005 0.194 Uiso 1 1 calc R . .
H37B H 0.5997 0.4672 -0.0099 0.194 Uiso 1 1 calc R . .
C38 C 0.5953(4) 0.5292(9) 0.0594(5) 0.181(5) Uani 1 1 d . . .
H38A H 0.5892 0.4648 0.0728 0.271 Uiso 1 1 calc R . .
H38B H 0.5621 0.5637 0.0424 0.271 Uiso 1 1 calc R . .
H38C H 0.6184 0.5680 0.0904 0.271 Uiso 1 1 calc R . .
Cl1 Cl 0.61902(5) 0.24549(12) 0.08136(6) 0.0733(4) Uani 1 1 d . . .
H3 H 0.734(2) 0.245(4) 0.162(2) 0.060(15) Uiso 1 1 d . . .
H4 H 0.7258(18) 0.348(3) 0.1025(18) 0.047(13) Uiso 1 1 d . . .
N1 N 0.94041(12) 0.4252(3) 0.17614(13) 0.0384(8) Uani 1 1 d . . .
N2 N 0.94744(13) 0.3314(3) 0.26718(15) 0.0487(9) Uani 1 1 d . . .
N3 N 0.76413(16) 0.2319(3) 0.18648(17) 0.0577(12) Uani 1 1 d . . .
N4 N 0.75301(14) 0.3535(3) 0.09319(15) 0.0443(9) Uani 1 1 d . . .
Ni1 Ni 1.0000 0.42075(6) 0.2500 0.0401(3) Uani 1 2 d S . .
O1 O 1.01987(12) 0.5467(3) 0.20351(13) 0.0575(9) Uani 1 1 d . . .
O2 O 0.89543(18) 0.3784(4) 0.33678(18) 0.0883(13) Uani 1 1 d . . .
O3 O 0.8244(2) 0.0641(4) 0.2302(2) 0.1072(16) Uani 1 1 d . . .
O4 O 0.67363(15) 0.4801(3) 0.04834(18) 0.0833(12) Uani 1 1 d . . .
O5 O 0.62877(18) 0.2579(4) 0.02940(18) 0.1001(15) Uani 1 1 d . . .
O6 O 0.56802(13) 0.2802(4) 0.07383(19) 0.0967(15) Uani 1 1 d . . .
O7 O 0.62473(19) 0.1437(4) 0.0987(3) 0.1218(19) Uani 1 1 d . . .
O8 O 0.65832(13) 0.3030(4) 0.12376(16) 0.0895(13) 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 1.311(5) . ?
C1 C6 1.415(5) . ?
C1 C2 1.478(6) . ?
C2 N2 1.306(5) . ?
C2 C3 1.413(6) . ?
C3 C4 1.359(6) . ?
C3 H1 0.9300 . ?
C4 N3 1.356(5) . ?
C4 C5 1.498(6) . ?
C5 C6 1.360(5) . ?
C5 N4 1.366(5) . ?
C6 H2 0.9300 . ?
C7 C12 1.383(6) . ?
C7 N1 1.396(5) . ?
C7 C8 1.397(6) . ?
C8 C9 1.369(7) . ?
C8 O1 1.379(5) . ?
C9 C10 1.377(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.356(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.457(10) . ?
C13 O1 1.486(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.364(8) . ?
C15 N2 1.413(6) . ?
C15 C20 1.493(8) . ?
C16 O2 1.277(7) . ?
C16 C17 1.383(8) . ?
C17 C18 1.295(14) . ?
C17 H17 0.9300 . ?
C18 C19 1.455(16) . ?
C18 H18 0.9300 . ?
C19 C20 1.405(11) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O2 1.462(8) . ?
C21 C22 1.505(11) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C28 1.292(9) . ?
C23 C24 1.405(9) . ?
C23 N3 1.405(6) . ?
C24 C25 1.383(10) . ?
C24 O3 1.396(8) . ?
C25 C26 1.384(14) . ?
C25 H25 0.9300 . ?
C26 C27 1.253(14) . ?
C26 H26 0.9300 . ?
C27 C28 1.414(10) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 O3 1.444(12) . ?
C29 C30 1.536(19) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C36 1.381(6) . ?
C31 C32 1.385(7) . ?
C31 N4 1.410(5) . ?
C32 O4 1.374(7) . ?
C32 C33 1.376(8) . ?
C33 C34 1.388(9) . ?
C33 H33 0.9300 . ?
C34 C35 1.337(9) . ?
C34 H34 0.9300 . ?
C35 C36 1.386(7) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 C38 1.431(12) . ?
C37 O4 1.461(8) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
Cl1 O6 1.399(4) . ?
Cl1 O7 1.417(5) . ?
Cl1 O8 1.429(4) . ?
Cl1 O5 1.447(4) . ?
N1 Ni1 1.980(3) . ?
N2 Ni1 2.019(4) . ?
N3 H3 0.85(5) . ?
N4 H4 0.85(5) . ?
Ni1 N1 1.980(3) 2_755 ?
Ni1 N2 2.019(4) 2_755 ?
Ni1 O1 2.228(3) 2_755 ?
Ni1 O1 2.228(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 C6 127.0(4) . . ?
N1 C1 C2 114.6(3) . . ?
C6 C1 C2 118.3(3) . . ?
N2 C2 C3 126.3(4) . . ?
N2 C2 C1 115.0(3) . . ?
C3 C2 C1 118.7(3) . . ?
C4 C3 C2 122.0(4) . . ?
C4 C3 H1 119.0 . . ?
C2 C3 H1 119.0 . . ?
N3 C4 C3 122.9(4) . . ?
N3 C4 C5 117.9(4) . . ?
C3 C4 C5 119.2(4) . . ?
C6 C5 N4 121.8(4) . . ?
C6 C5 C4 119.3(3) . . ?
N4 C5 C4 118.9(3) . . ?
C5 C6 C1 122.1(4) . . ?
C5 C6 H2 118.9 . . ?
C1 C6 H2 118.9 . . ?
C12 C7 N1 126.5(4) . . ?
C12 C7 C8 118.1(4) . . ?
N1 C7 C8 114.9(4) . . ?
C9 C8 O1 124.2(4) . . ?
C9 C8 C7 120.5(5) . . ?
O1 C8 C7 115.3(4) . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.0(5) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.6(5) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 120.8(5) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C14 C13 O1 110.0(6) . . ?
C14 C13 H13A 109.7 . . ?
O1 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
O1 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N2 123.7(5) . . ?
C16 C15 C20 123.0(5) . . ?
N2 C15 C20 112.9(5) . . ?
O2 C16 C15 115.6(5) . . ?
O2 C16 C17 124.6(7) . . ?
C15 C16 C17 119.8(7) . . ?
C18 C17 C16 120.9(9) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 122.8(8) . . ?
C17 C18 H18 118.6 . . ?
C19 C18 H18 118.6 . . ?
C20 C19 C18 120.1(9) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C15 113.3(9) . . ?
C19 C20 H20 123.4 . . ?
C15 C20 H20 123.4 . . ?
O2 C21 C22 110.4(7) . . ?
O2 C21 H21A 109.6 . . ?
C22 C21 H21A 109.6 . . ?
O2 C21 H21B 109.6 . . ?
C22 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C23 C24 116.6(6) . . ?
C28 C23 N3 121.5(6) . . ?
C24 C23 N3 121.8(6) . . ?
C25 C24 O3 124.0(8) . . ?
C25 C24 C23 120.3(8) . . ?
O3 C24 C23 115.6(6) . . ?
C24 C25 C26 118.1(9) . . ?
C24 C25 H25 121.0 . . ?
C26 C25 H25 121.0 . . ?
C27 C26 C25 121.8(8) . . ?
C27 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C26 C27 C28 119.5(10) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.2 . . ?
C23 C28 C27 123.4(9) . . ?
C23 C28 H28 118.3 . . ?
C27 C28 H28 118.3 . . ?
O3 C29 C30 103.5(11) . . ?
O3 C29 H29A 111.1 . . ?
C30 C29 H29A 111.0 . . ?
O3 C29 H29B 111.1 . . ?
C30 C29 H29B 111.1 . . ?
H29A C29 H29B 109.0 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C36 C31 C32 117.9(4) . . ?
C36 C31 N4 122.7(4) . . ?
C32 C31 N4 119.2(4) . . ?
O4 C32 C33 124.5(5) . . ?
O4 C32 C31 114.2(4) . . ?
C33 C32 C31 121.3(6) . . ?
C32 C33 C34 119.2(6) . . ?
C32 C33 H33 120.4 . . ?
C34 C33 H33 120.4 . . ?
C35 C34 C33 120.2(6) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C34 C35 C36 120.9(6) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C31 C36 C35 120.4(5) . . ?
C31 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C38 C37 O4 107.2(8) . . ?
C38 C37 H37A 110.3 . . ?
O4 C37 H37A 110.3 . . ?
C38 C37 H37B 110.3 . . ?
O4 C37 H37B 110.3 . . ?
H37A C37 H37B 108.5 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O6 Cl1 O7 110.4(3) . . ?
O6 Cl1 O8 110.5(3) . . ?
O7 Cl1 O8 108.1(3) . . ?
O6 Cl1 O5 109.6(3) . . ?
O7 Cl1 O5 111.0(4) . . ?
O8 Cl1 O5 107.1(3) . . ?
C1 N1 C7 127.2(3) . . ?
C1 N1 Ni1 115.3(3) . . ?
C7 N1 Ni1 117.4(2) . . ?
C2 N2 C15 123.1(4) . . ?
C2 N2 Ni1 114.0(3) . . ?
C15 N2 Ni1 122.0(3) . . ?
C4 N3 C23 124.8(4) . . ?
C4 N3 H3 119(3) . . ?
C23 N3 H3 113(3) . . ?
C5 N4 C31 124.7(4) . . ?
C5 N4 H4 118(3) . . ?
C31 N4 H4 116(3) . . ?
N1 Ni1 N1 176.6(2) . 2_755 ?
N1 Ni1 N2 101.88(14) . 2_755 ?
N1 Ni1 N2 80.17(13) 2_755 2_755 ?
N1 Ni1 N2 80.17(13) . . ?
N1 Ni1 N2 101.87(14) 2_755 . ?
N2 Ni1 N2 107.8(2) 2_755 . ?
N1 Ni1 O1 102.17(13) . 2_755 ?
N1 Ni1 O1 75.19(12) 2_755 2_755 ?
N2 Ni1 O1 152.02(13) 2_755 2_755 ?
N2 Ni1 O1 90.26(15) . 2_755 ?
N1 Ni1 O1 75.19(12) . . ?
N1 Ni1 O1 102.17(13) 2_755 . ?
N2 Ni1 O1 90.26(15) 2_755 . ?
N2 Ni1 O1 152.02(13) . . ?
O1 Ni1 O1 82.27(18) 2_755 . ?
C8 O1 C13 119.2(4) . . ?
C8 O1 Ni1 109.5(3) . . ?
C13 O1 Ni1 121.7(3) . . ?
C16 O2 C21 118.5(5) . . ?
C24 O3 C29 116.3(8) . . ?
C32 O4 C37 114.2(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
N1 C1 C2 N2 -0.8(6) . . . . ?
C6 C1 C2 N2 -178.1(4) . . . . ?
N1 C1 C2 C3 -178.7(4) . . . . ?
C6 C1 C2 C3 4.1(6) . . . . ?
N2 C2 C3 C4 -178.5(5) . . . . ?
C1 C2 C3 C4 -0.9(7) . . . . ?
C2 C3 C4 N3 176.4(5) . . . . ?
C2 C3 C4 C5 -4.2(7) . . . . ?
N3 C4 C5 C6 -174.2(4) . . . . ?
C3 C4 C5 C6 6.5(7) . . . . ?
N3 C4 C5 N4 6.1(7) . . . . ?
C3 C4 C5 N4 -173.3(4) . . . . ?
N4 C5 C6 C1 176.5(4) . . . . ?
C4 C5 C6 C1 -3.3(7) . . . . ?
N1 C1 C6 C5 -178.7(4) . . . . ?
C2 C1 C6 C5 -1.8(6) . . . . ?
C12 C7 C8 C9 5.4(8) . . . . ?
N1 C7 C8 C9 178.7(5) . . . . ?
C12 C7 C8 O1 -175.2(4) . . . . ?
N1 C7 C8 O1 -1.9(6) . . . . ?
O1 C8 C9 C10 178.6(6) . . . . ?
C7 C8 C9 C10 -2.0(10) . . . . ?
C8 C9 C10 C11 -2.3(12) . . . . ?
C9 C10 C11 C12 3.2(12) . . . . ?
C10 C11 C12 C7 0.4(10) . . . . ?
N1 C7 C12 C11 -177.0(5) . . . . ?
C8 C7 C12 C11 -4.6(8) . . . . ?
N2 C15 C16 O2 7.3(8) . . . . ?
C20 C15 C16 O2 179.5(5) . . . . ?
N2 C15 C16 C17 -172.4(5) . . . . ?
C20 C15 C16 C17 -0.2(9) . . . . ?
O2 C16 C17 C18 -176.5(8) . . . . ?
C15 C16 C17 C18 3.1(11) . . . . ?
C16 C17 C18 C19 -5.0(14) . . . . ?
C17 C18 C19 C20 4.1(14) . . . . ?
C18 C19 C20 C15 -1.1(10) . . . . ?
C16 C15 C20 C19 -0.7(8) . . . . ?
N2 C15 C20 C19 172.3(5) . . . . ?
C28 C23 C24 C25 -0.3(10) . . . . ?
N3 C23 C24 C25 178.6(6) . . . . ?
C28 C23 C24 O3 176.6(6) . . . . ?
N3 C23 C24 O3 -4.5(8) . . . . ?
O3 C24 C25 C26 -174.6(8) . . . . ?
C23 C24 C25 C26 2.1(11) . . . . ?
C24 C25 C26 C27 -5.1(16) . . . . ?
C25 C26 C27 C28 5.9(17) . . . . ?
C24 C23 C28 C27 1.2(12) . . . . ?
N3 C23 C28 C27 -177.8(7) . . . . ?
C26 C27 C28 C23 -4.1(15) . . . . ?
C36 C31 C32 O4 -179.3(4) . . . . ?
N4 C31 C32 O4 5.6(7) . . . . ?
C36 C31 C32 C33 1.1(9) . . . . ?
N4 C31 C32 C33 -174.0(6) . . . . ?
O4 C32 C33 C34 178.2(7) . . . . ?
C31 C32 C33 C34 -2.2(11) . . . . ?
C32 C33 C34 C35 0.2(12) . . . . ?
C33 C34 C35 C36 2.9(11) . . . . ?
C32 C31 C36 C35 2.0(7) . . . . ?
N4 C31 C36 C35 176.9(4) . . . . ?
C34 C35 C36 C31 -4.0(9) . . . . ?
C6 C1 N1 C7 -11.9(7) . . . . ?
C2 C1 N1 C7 171.2(4) . . . . ?
C6 C1 N1 Ni1 170.3(4) . . . . ?
C2 C1 N1 Ni1 -6.7(5) . . . . ?
C12 C7 N1 C1 -25.9(7) . . . . ?
C8 C7 N1 C1 161.4(4) . . . . ?
C12 C7 N1 Ni1 151.9(4) . . . . ?
C8 C7 N1 Ni1 -20.8(5) . . . . ?
C3 C2 N2 C15 -5.3(8) . . . . ?
C1 C2 N2 C15 177.1(5) . . . . ?
C3 C2 N2 Ni1 -174.7(4) . . . . ?
C1 C2 N2 Ni1 7.7(5) . . . . ?
C16 C15 N2 C2 -58.7(7) . . . . ?
C20 C15 N2 C2 128.4(5) . . . . ?
C16 C15 N2 Ni1 109.9(5) . . . . ?
C20 C15 N2 Ni1 -63.0(6) . . . . ?
C3 C4 N3 C23 8.5(8) . . . . ?
C5 C4 N3 C23 -170.8(5) . . . . ?
C28 C23 N3 C4 113.3(7) . . . . ?
C24 C23 N3 C4 -65.6(8) . . . . ?
C6 C5 N4 C31 12.9(7) . . . . ?
C4 C5 N4 C31 -167.3(4) . . . . ?
C36 C31 N4 C5 45.3(7) . . . . ?
C32 C31 N4 C5 -139.9(5) . . . . ?
C1 N1 Ni1 N1 -118.7(3) . . . 2_755 ?
C7 N1 Ni1 N1 63.2(3) . . . 2_755 ?
C1 N1 Ni1 N2 114.6(3) . . . 2_755 ?
C7 N1 Ni1 N2 -63.5(3) . . . 2_755 ?
C1 N1 Ni1 N2 8.3(3) . . . . ?
C7 N1 Ni1 N2 -169.7(3) . . . . ?
C1 N1 Ni1 O1 -79.8(3) . . . 2_755 ?
C7 N1 Ni1 O1 102.1(3) . . . 2_755 ?
C1 N1 Ni1 O1 -158.3(3) . . . . ?
C7 N1 Ni1 O1 23.6(3) . . . . ?
C2 N2 Ni1 N1 -8.7(3) . . . . ?
C15 N2 Ni1 N1 -178.2(4) . . . . ?
C2 N2 Ni1 N1 168.5(3) . . . 2_755 ?
C15 N2 Ni1 N1 -1.0(4) . . . 2_755 ?
C2 N2 Ni1 N2 -108.1(3) . . . 2_755 ?
C15 N2 Ni1 N2 82.4(4) . . . 2_755 ?
C2 N2 Ni1 O1 93.6(3) . . . 2_755 ?
C15 N2 Ni1 O1 -75.9(4) . . . 2_755 ?
C2 N2 Ni1 O1 19.8(5) . . . . ?
C15 N2 Ni1 O1 -149.8(4) . . . . ?
C9 C8 O1 C13 -14.0(8) . . . . ?
C7 C8 O1 C13 166.7(5) . . . . ?
C9 C8 O1 Ni1 -160.7(5) . . . . ?
C7 C8 O1 Ni1 19.9(5) . . . . ?
C14 C13 O1 C8 88.6(7) . . . . ?
C14 C13 O1 Ni1 -128.8(5) . . . . ?
N1 Ni1 O1 C8 -23.3(3) . . . . ?
N1 Ni1 O1 C8 159.0(3) 2_755 . . . ?
N2 Ni1 O1 C8 79.0(3) 2_755 . . . ?
N2 Ni1 O1 C8 -52.3(5) . . . . ?
O1 Ni1 O1 C8 -128.1(3) 2_755 . . . ?
N1 Ni1 O1 C13 -169.1(4) . . . . ?
N1 Ni1 O1 C13 13.1(4) 2_755 . . . ?
N2 Ni1 O1 C13 -66.9(4) 2_755 . . . ?
N2 Ni1 O1 C13 161.9(4) . . . . ?
O1 Ni1 O1 C13 86.1(4) 2_755 . . . ?
C15 C16 O2 C21 166.0(6) . . . . ?
C17 C16 O2 C21 -14.4(10) . . . . ?
C22 C21 O2 C16 -168.7(7) . . . . ?
C25 C24 O3 C29 -17.8(11) . . . . ?
C23 C24 O3 C29 165.4(8) . . . . ?
C30 C29 O3 C24 -166.9(10) . . . . ?
C33 C32 O4 C37 19.5(10) . . . . ?
C31 C32 O4 C37 -160.1(7) . . . . ?
C38 C37 O4 C32 174.2(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4 O8 0.85(5) 2.17(5) 3.009(5) 169(4) .
N3 H3 O8 0.85(5) 2.07(5) 2.880(6) 160(5) .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.082



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
1 0.250 -0.250 0.500 429 105
2 0.250 0.250 1.000 429 105
3 0.750 -0.250 0.000 429 105
4 0.750 0.250 0.500 429 105

_platon_squeeze_details          
;
The hexane solvent molecule could not be resolved due to extensive
disorder and their assumed presence was removed from the overall 
scattering by the PLATON SQUEEZE procedure [Spek (2009). Acta Cryst. 
D65, 148-155]. A total of 105 e was found in each cavity (estimated 
volume 429 Å³),corresponding to approximately two hexane molecules 
per cavity.
;
_database_code_depnum_ccdc_archive 'CCDC 1023071'
#######################################################################
#
#                 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-EtApH2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H40 N4'
_chemical_formula_weight         552.74

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'

_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                   10.5962(6)
_cell_length_b                   7.4665(4)
_cell_length_c                   19.8942(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.3650(10)
_cell_angle_gamma                90.00
_cell_volume                     1573.93(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3662
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      27.27

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.42
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9613
_exptl_absorpt_correction_T_max  0.9717
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11093
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         27.89
_reflns_number_total             3738
_reflns_number_gt                2894
_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)+(0.0791P)²+0.1667P] 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         3738
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1483
_refine_ls_wR_factor_gt          0.1385
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.62931(11) 0.51093(15) 1.02039(6) 0.0395(3) Uani 1 1 d . . .
C2 C 0.59197(11) 0.45446(16) 0.95087(6) 0.0402(3) Uani 1 1 d . . .
C3 C 0.46059(11) 0.44770(16) 0.93401(6) 0.0419(3) Uani 1 1 d . . .
H3 H 0.4358 0.4135 0.8899 0.050 Uiso 1 1 calc R . .
C4 C 0.82783(11) 0.55340(18) 1.08746(6) 0.0433(3) Uani 1 1 d . . .
C5 C 0.79794(13) 0.69766(18) 1.12810(6) 0.0509(3) Uani 1 1 d . . .
H5 H 0.7258 0.7686 1.1181 0.061 Uiso 1 1 calc R . .
C6 C 0.87256(15) 0.7391(2) 1.18323(7) 0.0622(4) Uani 1 1 d . . .
H6 H 0.8505 0.8365 1.2115 0.075 Uiso 1 1 calc R . .
C7 C 0.97837(15) 0.6395(3) 1.19710(8) 0.0707(5) Uani 1 1 d . . .
H7 H 1.0296 0.6675 1.2350 0.085 Uiso 1 1 calc R . .
C8 C 1.00975(14) 0.4990(2) 1.15574(8) 0.0651(4) Uani 1 1 d . . .
H8 H 1.0841 0.4325 1.1653 0.078 Uiso 1 1 calc R . .
C9 C 0.93642(12) 0.45094(19) 1.10046(7) 0.0500(3) Uani 1 1 d . . .
C10 C 0.97210(14) 0.2929(2) 1.05756(8) 0.0623(4) Uani 1 1 d . . .
H10A H 1.0622 0.2643 1.0654 0.075 Uiso 1 1 calc R . .
H10B H 0.9618 0.3257 1.0096 0.075 Uiso 1 1 calc R . .
C11 C 0.8937(2) 0.1283(3) 1.07190(10) 0.0921(6) Uani 1 1 d . . .
H11A H 0.9015 0.0970 1.1196 0.138 Uiso 1 1 calc R . .
H11B H 0.9238 0.0283 1.0444 0.138 Uiso 1 1 calc R . .
H11C H 0.8051 0.1528 1.0610 0.138 Uiso 1 1 calc R . .
C12 C 0.66662(11) 0.3643(2) 0.84430(6) 0.0524(3) Uani 1 1 d . . .
C13 C 0.61972(15) 0.4876(2) 0.79859(7) 0.0637(4) Uani 1 1 d . . .
H13 H 0.5930 0.6019 0.8139 0.076 Uiso 1 1 calc R . .
C14 C 0.61132(17) 0.4461(3) 0.73079(8) 0.0782(5) Uani 1 1 d . . .
H14 H 0.5783 0.5310 0.6998 0.094 Uiso 1 1 calc R . .
C15 C 0.65087(17) 0.2823(4) 0.70892(9) 0.0882(7) Uani 1 1 d . . .
H15 H 0.6454 0.2529 0.6625 0.106 Uiso 1 1 calc R . .
C16 C 0.69824(18) 0.1612(3) 0.75358(10) 0.0900(6) Uani 1 1 d . . .
H16 H 0.7254 0.0480 0.7374 0.108 Uiso 1 1 calc R . .
C17 C 0.70837(14) 0.1972(2) 0.82249(8) 0.0705(5) Uani 1 1 d . . .
C18 C 0.7615(2) 0.0643(3) 0.87081(12) 0.0985(7) Uani 1 1 d . . .
H18A H 0.8205 0.1264 0.9018 0.118 Uiso 1 1 calc R . .
H18B H 0.8106 -0.0260 0.8455 0.118 Uiso 1 1 calc R . .
C19 C 0.6616(3) -0.0312(3) 0.91191(15) 0.1271(10) Uani 1 1 d . . .
H19A H 0.6133 0.0571 0.9376 0.191 Uiso 1 1 calc R . .
H19B H 0.7025 -0.1154 0.9429 0.191 Uiso 1 1 calc R . .
H19C H 0.6047 -0.0968 0.8817 0.191 Uiso 1 1 calc R . .
N1 N 0.75629(10) 0.51163(17) 1.02981(6) 0.0491(3) Uani 1 1 d . . .
N2 N 0.68506(10) 0.41146(16) 0.91251(5) 0.0496(3) Uani 1 1 d . . .
H1 H 0.7943(15) 0.473(2) 0.9958(8) 0.057(4) 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
C1 C3 1.3553(17) 3_667 ?
C1 N1 1.3573(15) . ?
C1 C2 1.4968(16) . ?
C2 N2 1.2915(15) . ?
C2 C3 1.4307(16) . ?
C3 C1 1.3554(17) 3_667 ?
C3 H3 0.9500 . ?
C4 C5 1.3848(19) . ?
C4 C9 1.4043(18) . ?
C4 N1 1.4057(15) . ?
C5 C6 1.3830(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.372(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.375(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.506(2) . ?
C10 C11 1.512(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.384(2) . ?
C12 C17 1.394(2) . ?
C12 N2 1.4143(16) . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.365(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.362(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.401(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.490(3) . ?
C18 C19 1.519(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N1 H1 0.840(16) . ?

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
C3 C1 N1 127.38(11) 3_667 . ?
C3 C1 C2 119.99(10) 3_667 . ?
N1 C1 C2 112.63(10) . . ?
N2 C2 C3 126.75(11) . . ?
N2 C2 C1 114.68(10) . . ?
C3 C2 C1 118.54(10) . . ?
C1 C3 C2 121.46(10) 3_667 . ?
C1 C3 H3 119.3 3_667 . ?
C2 C3 H3 119.3 . . ?
C5 C4 C9 120.43(11) . . ?
C5 C4 N1 121.65(11) . . ?
C9 C4 N1 117.79(12) . . ?
C6 C5 C4 120.34(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.05(15) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 119.56(13) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 122.30(14) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C8 C9 C4 117.28(14) . . ?
C8 C9 C10 120.65(13) . . ?
C4 C9 C10 122.06(12) . . ?
C9 C10 C11 112.95(12) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 120.26(13) . . ?
C13 C12 N2 120.79(13) . . ?
C17 C12 N2 118.65(14) . . ?
C12 C13 C14 120.76(17) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 119.49(19) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C16 C15 C14 120.00(16) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 122.46(18) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C12 C17 C16 117.02(18) . . ?
C12 C17 C18 120.99(14) . . ?
C16 C17 C18 121.99(17) . . ?
C17 C18 C19 113.45(19) . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
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 . . ?
C1 N1 C4 129.98(11) . . ?
C1 N1 H1 111.6(10) . . ?
C4 N1 H1 118.3(10) . . ?
C2 N2 C12 121.83(10) . . ?

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
C3 C1 C2 N2 -177.37(11) 3_667 . . . ?
N1 C1 C2 N2 1.87(16) . . . . ?
C3 C1 C2 C3 0.75(19) 3_667 . . . ?
N1 C1 C2 C3 179.99(11) . . . . ?
N2 C2 C3 C1 177.11(12) . . . 3_667 ?
C1 C2 C3 C1 -0.76(19) . . . 3_667 ?
C9 C4 C5 C6 -2.03(19) . . . . ?
N1 C4 C5 C6 -177.82(12) . . . . ?
C4 C5 C6 C7 1.4(2) . . . . ?
C5 C6 C7 C8 0.2(2) . . . . ?
C6 C7 C8 C9 -1.3(2) . . . . ?
C7 C8 C9 C4 0.6(2) . . . . ?
C7 C8 C9 C10 -178.26(14) . . . . ?
C5 C4 C9 C8 1.00(19) . . . . ?
N1 C4 C9 C8 176.94(12) . . . . ?
C5 C4 C9 C10 179.88(12) . . . . ?
N1 C4 C9 C10 -4.17(18) . . . . ?
C8 C9 C10 C11 102.16(17) . . . . ?
C4 C9 C10 C11 -76.69(18) . . . . ?
C17 C12 C13 C14 1.2(2) . . . . ?
N2 C12 C13 C14 174.70(13) . . . . ?
C12 C13 C14 C15 -0.6(2) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C13 C12 C17 C16 -1.1(2) . . . . ?
N2 C12 C17 C16 -174.74(14) . . . . ?
C13 C12 C17 C18 178.76(17) . . . . ?
N2 C12 C17 C18 5.1(2) . . . . ?
C15 C16 C17 C12 0.5(3) . . . . ?
C15 C16 C17 C18 -179.4(2) . . . . ?
C12 C17 C18 C19 77.1(2) . . . . ?
C16 C17 C18 C19 -103.1(2) . . . . ?
C3 C1 N1 C4 0.2(2) 3_667 . . . ?
C2 C1 N1 C4 -178.97(12) . . . . ?
C5 C4 N1 C1 -42.1(2) . . . . ?
C9 C4 N1 C1 141.98(14) . . . . ?
C3 C2 N2 C12 5.5(2) . . . . ?
C1 C2 N2 C12 -176.57(12) . . . . ?
C13 C12 N2 C2 64.04(19) . . . . ?
C17 C12 N2 C2 -122.33(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.840(16) 2.068(15) 2.5597(14) 116.9(13) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.89
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 1023072'
#######################################################################
#
#                 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-OEtApH2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H40 N4 O4'
_chemical_formula_weight         616.74

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'

_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                   10.680(9)
_cell_length_b                   9.276(7)
_cell_length_c                   16.587(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.173(14)
_cell_angle_gamma                90.00
_cell_volume                     1622(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2095
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.37

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10836
_diffrn_reflns_av_R_equivalents  0.1054
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         27.86
_reflns_number_total             3814
_reflns_number_gt                1856
_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)+(0.0654P)²+0.5437P] 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         3814
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1476
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.1846
_refine_ls_wR_factor_gt          0.1499
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
C1 C 0.3801(2) 0.4906(3) 1.02698(15) 0.0413(7) Uani 1 1 d . . .
C2 C 0.4125(2) 0.6151(3) 0.97777(15) 0.0389(7) Uani 1 1 d . . .
C3 C 0.5350(2) 0.6153(3) 0.95210(15) 0.0438(7) Uani 1 1 d . . .
H3 H 0.5561 0.6910 0.9200 0.053 Uiso 1 1 calc R . .
C4 C 0.1820(2) 0.3885(3) 1.06602(15) 0.0419(7) Uani 1 1 d . . .
C5 C 0.0764(2) 0.4309(4) 1.10017(16) 0.0438(7) Uani 1 1 d . . .
C6 C -0.0095(3) 0.3303(4) 1.11646(18) 0.0568(9) Uani 1 1 d . . .
H6 H -0.0799 0.3590 1.1390 0.068 Uiso 1 1 calc R . .
C7 C 0.0070(3) 0.1878(4) 1.1000(2) 0.0653(10) Uani 1 1 d . . .
H7 H -0.0516 0.1200 1.1118 0.078 Uiso 1 1 calc R . .
C8 C 0.1101(3) 0.1445(4) 1.0659(2) 0.0625(9) Uani 1 1 d . . .
H8 H 0.1214 0.0478 1.0541 0.075 Uiso 1 1 calc R . .
C9 C 0.1965(3) 0.2464(4) 1.04942(18) 0.0527(8) Uani 1 1 d . . .
H9 H 0.2663 0.2173 1.0264 0.063 Uiso 1 1 calc R . .
C10 C -0.0322(3) 0.6254(4) 1.1528(2) 0.0640(10) Uani 1 1 d . . .
H10A H -0.0277 0.5803 1.2060 0.077 Uiso 1 1 calc R . .
H10B H -0.1138 0.6026 1.1206 0.077 Uiso 1 1 calc R . .
C11 C -0.0170(3) 0.7836(4) 1.1619(2) 0.0763(11) Uani 1 1 d . . .
H11A H 0.0637 0.8048 1.1942 0.115 Uiso 1 1 calc R . .
H11B H -0.0835 0.8216 1.1885 0.115 Uiso 1 1 calc R . .
H11C H -0.0215 0.8270 1.1090 0.115 Uiso 1 1 calc R . .
C12 C 0.3384(2) 0.8237(3) 0.90671(17) 0.0425(7) Uani 1 1 d . . .
C13 C 0.3197(2) 0.7946(4) 0.82343(18) 0.0489(8) Uani 1 1 d . . .
C14 C 0.3163(3) 0.9045(5) 0.7683(2) 0.0648(10) Uani 1 1 d . . .
H14 H 0.3025 0.8846 0.7126 0.078 Uiso 1 1 calc R . .
C15 C 0.3332(3) 1.0435(5) 0.7948(2) 0.0710(11) Uani 1 1 d . . .
H15 H 0.3309 1.1180 0.7571 0.085 Uiso 1 1 calc R . .
C16 C 0.3534(3) 1.0739(4) 0.8765(2) 0.0691(10) Uani 1 1 d . . .
H16 H 0.3667 1.1684 0.8945 0.083 Uiso 1 1 calc R . .
C17 C 0.3541(3) 0.9627(4) 0.9318(2) 0.0549(8) Uani 1 1 d . . .
H17 H 0.3655 0.9834 0.9874 0.066 Uiso 1 1 calc R . .
C18 C 0.3403(3) 0.6025(5) 0.7303(2) 0.0810(12) Uani 1 1 d . . .
H18A H 0.4226 0.6420 0.7248 0.097 Uiso 1 1 calc R . .
H18B H 0.2798 0.6325 0.6833 0.097 Uiso 1 1 calc R . .
C19 C 0.3469(4) 0.4437(5) 0.7342(3) 0.1031(15) Uani 1 1 d . . .
H19A H 0.4025 0.4149 0.7828 0.155 Uiso 1 1 calc R . .
H19B H 0.3788 0.4075 0.6872 0.155 Uiso 1 1 calc R . .
H19C H 0.2637 0.4052 0.7351 0.155 Uiso 1 1 calc R . .
N1 N 0.2611(2) 0.4987(3) 1.04571(15) 0.0480(7) Uani 1 1 d . . .
N2 N 0.32712(19) 0.7116(3) 0.96198(14) 0.0459(6) Uani 1 1 d . . .
O1 O 0.06799(16) 0.5741(3) 1.11292(12) 0.0534(6) Uani 1 1 d . . .
O2 O 0.3020(2) 0.6533(3) 0.80297(13) 0.0690(7) Uani 1 1 d . . .
H1 H 0.227(3) 0.583(4) 1.0362(19) 0.062(11) 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
C1 C3 1.344(4) 3_667 ?
C1 N1 1.358(3) . ?
C1 C2 1.486(4) . ?
C2 N2 1.275(3) . ?
C2 C3 1.439(3) . ?
C3 C1 1.344(4) 3_667 ?
C3 H3 0.9300 . ?
C4 C9 1.360(4) . ?
C4 C5 1.397(4) . ?
C4 N1 1.401(4) . ?
C5 O1 1.350(4) . ?
C5 C6 1.365(4) . ?
C6 C7 1.367(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.375(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.378(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 O1 1.427(3) . ?
C10 C11 1.481(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.358(4) . ?
C12 C13 1.390(4) . ?
C12 N2 1.404(4) . ?
C13 O2 1.360(4) . ?
C13 C14 1.366(5) . ?
C14 C15 1.366(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.366(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O2 1.414(4) . ?
C18 C19 1.476(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N1 H1 0.87(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
C3 C1 N1 126.8(3) 3_667 . ?
C3 C1 C2 120.2(2) 3_667 . ?
N1 C1 C2 113.0(2) . . ?
N2 C2 C3 126.3(3) . . ?
N2 C2 C1 115.9(2) . . ?
C3 C2 C1 117.7(2) . . ?
C1 C3 C2 122.0(3) 3_667 . ?
C1 C3 H3 119.0 3_667 . ?
C2 C3 H3 119.0 . . ?
C9 C4 C5 118.7(3) . . ?
C9 C4 N1 124.5(2) . . ?
C5 C4 N1 116.6(3) . . ?
O1 C5 C6 125.3(3) . . ?
O1 C5 C4 114.7(2) . . ?
C6 C5 C4 119.9(3) . . ?
C5 C6 C7 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 120.1(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C9 119.1(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C4 C9 C8 121.5(3) . . ?
C4 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
O1 C10 C11 107.5(3) . . ?
O1 C10 H10A 110.2 . . ?
C11 C10 H10A 110.2 . . ?
O1 C10 H10B 110.2 . . ?
C11 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 118.7(3) . . ?
C17 C12 N2 121.5(3) . . ?
C13 C12 N2 119.5(3) . . ?
O2 C13 C14 124.3(3) . . ?
O2 C13 C12 115.3(3) . . ?
C14 C13 C12 120.4(3) . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.3(4) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C12 C17 C16 121.2(3) . . ?
C12 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
O2 C18 C19 108.2(4) . . ?
O2 C18 H18A 110.1 . . ?
C19 C18 H18A 110.1 . . ?
O2 C18 H18B 110.1 . . ?
C19 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
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 . . ?
C1 N1 C4 129.5(3) . . ?
C1 N1 H1 113(2) . . ?
C4 N1 H1 117(2) . . ?
C2 N2 C12 121.4(2) . . ?
C5 O1 C10 118.3(2) . . ?
C13 O2 C18 119.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 N2 -178.8(3) 3_667 . . . ?
N1 C1 C2 N2 1.6(3) . . . . ?
C3 C1 C2 C3 1.7(4) 3_667 . . . ?
N1 C1 C2 C3 -178.0(2) . . . . ?
N2 C2 C3 C1 178.8(3) . . . 3_667 ?
C1 C2 C3 C1 -1.7(4) . . . 3_667 ?
C9 C4 C5 O1 -178.6(2) . . . . ?
N1 C4 C5 O1 -3.2(3) . . . . ?
C9 C4 C5 C6 0.2(4) . . . . ?
N1 C4 C5 C6 175.6(2) . . . . ?
O1 C5 C6 C7 178.9(3) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C6 C7 C8 C9 0.6(5) . . . . ?
C5 C4 C9 C8 -0.3(4) . . . . ?
N1 C4 C9 C8 -175.3(3) . . . . ?
C7 C8 C9 C4 -0.1(5) . . . . ?
C17 C12 C13 O2 -178.7(2) . . . . ?
N2 C12 C13 O2 -5.4(3) . . . . ?
C17 C12 C13 C14 -0.6(4) . . . . ?
N2 C12 C13 C14 172.7(2) . . . . ?
O2 C13 C14 C15 178.9(3) . . . . ?
C12 C13 C14 C15 1.0(4) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C14 C15 C16 C17 -1.3(5) . . . . ?
C13 C12 C17 C16 -0.8(4) . . . . ?
N2 C12 C17 C16 -174.0(3) . . . . ?
C15 C16 C17 C12 1.8(5) . . . . ?
C3 C1 N1 C4 -22.8(5) 3_667 . . . ?
C2 C1 N1 C4 156.7(3) . . . . ?
C9 C4 N1 C1 -19.0(5) . . . . ?
C5 C4 N1 C1 166.0(3) . . . . ?
C3 C2 N2 C12 8.7(4) . . . . ?
C1 C2 N2 C12 -170.8(2) . . . . ?
C17 C12 N2 C2 -112.8(3) . . . . ?
C13 C12 N2 C2 74.1(3) . . . . ?
C6 C5 O1 C10 5.6(4) . . . . ?
C4 C5 O1 C10 -175.7(2) . . . . ?
C11 C10 O1 C5 177.9(3) . . . . ?
C14 C13 O2 C18 31.3(4) . . . . ?
C12 C13 O2 C18 -150.7(3) . . . . ?
C19 C18 O2 C13 163.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.87(3) 2.28(3) 2.592(3) 101(2) .
N1 H1 N2 0.87(3) 2.12(3) 2.576(4) 112(3) .

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.86
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 1023073'
#######################################################################
#
#                 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_2,6-Et2ApH2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H56 N4'
_chemical_formula_weight         664.95

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.4801(6)
_cell_length_b                   10.2051(7)
_cell_length_c                   11.4803(8)
_cell_angle_alpha                83.630(2)
_cell_angle_beta                 85.344(2)
_cell_angle_gamma                80.261(2)
_cell_volume                     971.17(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2972
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.86

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9664
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 8.366
_diffrn_standards_number         116
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        2
_diffrn_reflns_number            7174
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         27.91
_reflns_number_total             4603
_reflns_number_gt                3823
_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)+(0.1015P)²+0.4073P] 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         4603
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.1922
_refine_ls_wR_factor_gt          0.1815
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
C1 C 0.56226(17) 0.11846(15) -0.04306(13) 0.0262(3) Uani 1 1 d . . .
C2 C 0.49685(17) 0.09724(15) 0.08142(12) 0.0253(3) Uani 1 1 d . . .
C3 C 0.43742(18) -0.02529(15) 0.11900(13) 0.0271(3) Uani 1 1 d . . .
H3 H 0.3982 -0.0411 0.1964 0.033 Uiso 1 1 calc R . .
C4 C 0.67570(19) 0.28429(15) -0.18330(13) 0.0297(3) Uani 1 1 d . . .
C5 C 0.8293(2) 0.23367(17) -0.22689(15) 0.0345(4) Uani 1 1 d . . .
C6 C 0.8818(2) 0.2880(2) -0.33693(16) 0.0444(5) Uani 1 1 d . . .
H6 H 0.9833 0.2550 -0.3686 0.053 Uiso 1 1 calc R . .
C7 C 0.7868(3) 0.3894(2) -0.39957(16) 0.0473(5) Uani 1 1 d . . .
H7 H 0.8250 0.4250 -0.4724 0.057 Uiso 1 1 calc R . .
C8 C 0.6350(3) 0.4387(2) -0.35500(17) 0.0453(5) Uani 1 1 d . . .
H8 H 0.5715 0.5073 -0.3982 0.054 Uiso 1 1 calc R . .
C9 C 0.5758(2) 0.38675(18) -0.24593(16) 0.0379(4) Uani 1 1 d . . .
C10 C 0.9402(2) 0.1283(2) -0.15677(19) 0.0465(5) Uani 1 1 d . . .
H10A H 0.8773 0.0834 -0.0954 0.056 Uiso 1 1 calc R . .
H10B H 0.9927 0.0622 -0.2079 0.056 Uiso 1 1 calc R . .
C11 C 1.0645(5) 0.1839(4) -0.1024(4) 0.1188(17) Uani 1 1 d . . .
H11A H 1.1174 0.2389 -0.1610 0.178 Uiso 1 1 calc R . .
H11B H 1.1416 0.1120 -0.0699 0.178 Uiso 1 1 calc R . .
H11C H 1.0148 0.2366 -0.0411 0.178 Uiso 1 1 calc R . .
C12 C 0.4123(3) 0.4424(3) -0.1919(2) 0.0625(6) Uani 1 1 d . . .
H12A H 0.3700 0.3701 -0.1443 0.075 Uiso 1 1 calc R . .
H12B H 0.4266 0.5073 -0.1396 0.075 Uiso 1 1 calc R . .
C13 C 0.2911(4) 0.5068(3) -0.2747(3) 0.0888(10) Uani 1 1 d . . .
H13A H 0.3282 0.5820 -0.3196 0.133 Uiso 1 1 calc R . .
H13B H 0.1921 0.5365 -0.2316 0.133 Uiso 1 1 calc R . .
H13C H 0.2743 0.4437 -0.3268 0.133 Uiso 1 1 calc R . .
C14 C 0.44023(18) 0.19177(15) 0.26276(13) 0.0269(3) Uani 1 1 d . . .
C15 C 0.5510(2) 0.15878(16) 0.34996(14) 0.0306(3) Uani 1 1 d . . .
C16 C 0.4960(2) 0.17213(18) 0.46639(15) 0.0377(4) Uani 1 1 d . . .
H16 H 0.5680 0.1515 0.5252 0.045 Uiso 1 1 calc R . .
C17 C 0.3366(2) 0.21542(19) 0.49554(15) 0.0410(4) Uani 1 1 d . . .
H17 H 0.3017 0.2244 0.5736 0.049 Uiso 1 1 calc R . .
C18 C 0.2282(2) 0.24551(18) 0.40931(16) 0.0383(4) Uani 1 1 d . . .
H18 H 0.1205 0.2738 0.4302 0.046 Uiso 1 1 calc R . .
C19 C 0.27712(19) 0.23423(16) 0.29140(14) 0.0305(3) Uani 1 1 d . . .
C20 C 0.7241(2) 0.1091(2) 0.31334(17) 0.0410(4) Uani 1 1 d . . .
H20A H 0.7585 0.1713 0.2501 0.049 Uiso 1 1 calc R . .
H20B H 0.7297 0.0239 0.2820 0.049 Uiso 1 1 calc R . .
C21 C 0.8417(2) 0.0914(2) 0.40835(19) 0.0497(5) Uani 1 1 d . . .
H21A H 0.8388 0.1752 0.4399 0.075 Uiso 1 1 calc R . .
H21B H 0.9478 0.0616 0.3756 0.075 Uiso 1 1 calc R . .
H21C H 0.8131 0.0263 0.4698 0.075 Uiso 1 1 calc R . .
C22 C 0.1586(2) 0.27175(19) 0.19751(16) 0.0375(4) Uani 1 1 d . . .
H22A H 0.0514 0.2693 0.2332 0.045 Uiso 1 1 calc R . .
H22B H 0.1801 0.2059 0.1410 0.045 Uiso 1 1 calc R . .
C23 C 0.1648(3) 0.4094(2) 0.13332(18) 0.0479(5) Uani 1 1 d . . .
H23A H 0.1341 0.4759 0.1874 0.072 Uiso 1 1 calc R . .
H23B H 0.0924 0.4254 0.0713 0.072 Uiso 1 1 calc R . .
H23C H 0.2719 0.4139 0.1007 0.072 Uiso 1 1 calc R . .
H1 H 0.598(3) 0.286(2) -0.012(2) 0.045(6) Uiso 1 1 d . . .
N1 N 0.62004(18) 0.23474(14) -0.06907(12) 0.0325(3) Uani 1 1 d . . .
N2 N 0.49918(15) 0.19469(13) 0.14345(11) 0.0275(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 N1 1.353(2) . ?
C1 C3 1.359(2) 2_655 ?
C1 C2 1.497(2) . ?
C2 N2 1.289(2) . ?
C2 C3 1.436(2) . ?
C3 C1 1.359(2) 2_655 ?
C3 H3 0.9300 . ?
C4 C5 1.392(2) . ?
C4 C9 1.400(2) . ?
C4 N1 1.425(2) . ?
C5 C6 1.392(2) . ?
C5 C10 1.509(3) . ?
C6 C7 1.372(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.394(3) . ?
C8 H8 0.9300 . ?
C9 C12 1.517(3) . ?
C10 C11 1.486(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.478(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.401(2) . ?
C14 C15 1.403(2) . ?
C14 N2 1.4184(19) . ?
C15 C16 1.393(2) . ?
C15 C20 1.511(2) . ?
C16 C17 1.376(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.395(2) . ?
C18 H18 0.9300 . ?
C19 C22 1.507(2) . ?
C20 C21 1.513(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.519(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N1 H1 0.87(2) . ?

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 C3 125.31(14) . 2_655 ?
N1 C1 C2 113.85(13) . . ?
C3 C1 C2 120.83(13) 2_655 . ?
N2 C2 C3 127.02(13) . . ?
N2 C2 C1 114.76(13) . . ?
C3 C2 C1 118.22(13) . . ?
C1 C3 C2 120.93(13) 2_655 . ?
C1 C3 H3 119.5 2_655 . ?
C2 C3 H3 119.5 . . ?
C5 C4 C9 122.18(15) . . ?
C5 C4 N1 119.24(15) . . ?
C9 C4 N1 118.52(14) . . ?
C4 C5 C6 117.63(16) . . ?
C4 C5 C10 122.19(15) . . ?
C6 C5 C10 120.12(16) . . ?
C7 C6 C5 121.33(17) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 120.33(17) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 120.69(18) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 117.83(16) . . ?
C8 C9 C12 122.12(18) . . ?
C4 C9 C12 119.97(17) . . ?
C11 C10 C5 113.0(2) . . ?
C11 C10 H10A 109.0 . . ?
C5 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C5 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C9 116.4(2) . . ?
C13 C12 H12A 108.2 . . ?
C9 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
C9 C12 H12B 108.2 . . ?
H12A C12 H12B 107.3 . . ?
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 . . ?
C19 C14 C15 121.25(14) . . ?
C19 C14 N2 120.10(14) . . ?
C15 C14 N2 118.33(13) . . ?
C16 C15 C14 118.44(15) . . ?
C16 C15 C20 123.07(15) . . ?
C14 C15 C20 118.49(14) . . ?
C17 C16 C15 120.89(16) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.19(15) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C19 121.19(16) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C14 118.02(15) . . ?
C18 C19 C22 120.75(15) . . ?
C14 C19 C22 121.20(14) . . ?
C15 C20 C21 116.19(16) . . ?
C15 C20 H20A 108.2 . . ?
C21 C20 H20A 108.2 . . ?
C15 C20 H20B 108.2 . . ?
C21 C20 H20B 108.2 . . ?
H20A C20 H20B 107.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 C23 113.15(15) . . ?
C19 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
C19 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 C4 125.00(13) . . ?
C1 N1 H1 111.8(15) . . ?
C4 N1 H1 121.7(15) . . ?
C2 N2 C14 122.17(13) . . ?

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
N1 C1 C2 N2 2.74(19) . . . . ?
C3 C1 C2 N2 -178.07(14) 2_655 . . . ?
N1 C1 C2 C3 -177.98(13) . . . . ?
C3 C1 C2 C3 1.2(2) 2_655 . . . ?
N2 C2 C3 C1 177.97(15) . . . 2_655 ?
C1 C2 C3 C1 -1.2(2) . . . 2_655 ?
C9 C4 C5 C6 -0.4(3) . . . . ?
N1 C4 C5 C6 -177.63(15) . . . . ?
C9 C4 C5 C10 176.75(17) . . . . ?
N1 C4 C5 C10 -0.5(2) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C10 C5 C6 C7 -176.17(18) . . . . ?
C5 C6 C7 C8 -0.9(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C4 0.5(3) . . . . ?
C7 C8 C9 C12 177.4(2) . . . . ?
C5 C4 C9 C8 -0.4(3) . . . . ?
N1 C4 C9 C8 176.87(16) . . . . ?
C5 C4 C9 C12 -177.25(19) . . . . ?
N1 C4 C9 C12 0.0(3) . . . . ?
C4 C5 C10 C11 -101.7(3) . . . . ?
C6 C5 C10 C11 75.4(3) . . . . ?
C8 C9 C12 C13 27.1(3) . . . . ?
C4 C9 C12 C13 -156.2(2) . . . . ?
C19 C14 C15 C16 -1.5(2) . . . . ?
N2 C14 C15 C16 172.02(14) . . . . ?
C19 C14 C15 C20 177.88(15) . . . . ?
N2 C14 C15 C20 -8.6(2) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C20 C15 C16 C17 -178.74(17) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 C14 -0.2(3) . . . . ?
C17 C18 C19 C22 -177.94(16) . . . . ?
C15 C14 C19 C18 1.3(2) . . . . ?
N2 C14 C19 C18 -172.10(14) . . . . ?
C15 C14 C19 C22 179.01(15) . . . . ?
N2 C14 C19 C22 5.6(2) . . . . ?
C16 C15 C20 C21 -8.0(3) . . . . ?
C14 C15 C20 C21 172.66(16) . . . . ?
C18 C19 C22 C23 100.2(2) . . . . ?
C14 C19 C22 C23 -77.4(2) . . . . ?
C3 C1 N1 C4 6.7(3) 2_655 . . . ?
C2 C1 N1 C4 -174.18(14) . . . . ?
C5 C4 N1 C1 -80.0(2) . . . . ?
C9 C4 N1 C1 102.72(19) . . . . ?
C3 C2 N2 C14 0.1(2) . . . . ?
C1 C2 N2 C14 179.33(13) . . . . ?
C19 C14 N2 C2 -86.32(19) . . . . ?
C15 C14 N2 C2 100.09(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.87(2) 2.10(2) 2.5854(19) 114.5(18) .

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.91
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 1023074'
