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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1047940'
_audit_update_record             
;
2015-04-08 deposited with the CCDC.
2015-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H45 N3 Ni O2'
_chemical_formula_weight         550.41

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'

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

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                   13.6320(10)
_cell_length_b                   17.9180(10)
_cell_length_c                   12.6470(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.475(7)
_cell_angle_gamma                90.00
_cell_volume                     3047.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    20454
_cell_measurement_theta_min      4.105
_cell_measurement_theta_max      29.322

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7316
_exptl_absorpt_correction_T_max  0.9611
_exptl_absorpt_process_details   
;
 CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
face-indexed (CrysAlis RED; Oxford Diffraction, 2006)
;

_diffrn_ambient_temperature      303(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  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19184
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.17
_diffrn_reflns_theta_max         24.99
_reflns_number_total             5330
_reflns_number_gt                3315
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  ' enCIFer (Allen et al., 2004)'

_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)+(0.0534P)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         5330
_refine_ls_number_parameters     338
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.990
_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 1.0456(2) 0.13297(16) 0.7825(2) 0.0401(8) Uani 1 1 d . B .
C2 C 1.1383(2) 0.16352(16) 0.7619(2) 0.0408(8) Uani 1 1 d . . .
C3 C 1.1846(2) 0.12846(19) 0.6870(3) 0.0529(9) Uani 1 1 d . . .
H3 H 1.2437 0.1491 0.6729 0.063 Uiso 1 1 calc R . .
C4 C 1.1497(2) 0.06416(19) 0.6304(3) 0.0522(9) Uani 1 1 d . . .
C5 C 1.0646(2) 0.03385(17) 0.6537(3) 0.0505(9) Uani 1 1 d . . .
H5 H 1.0407 -0.0101 0.6197 0.061 Uiso 1 1 calc R . .
C6 C 1.0117(2) 0.06673(16) 0.7276(2) 0.0406(8) Uani 1 1 d . . .
C7 C 0.9248(2) 0.02716(17) 0.7499(3) 0.0468(8) Uani 1 1 d . . .
H7 H 0.9160 -0.0214 0.7239 0.056 Uiso 1 1 calc R . .
C8 C 0.7825(2) 0.00205(18) 0.8292(3) 0.0609(10) Uani 1 1 d D . .
H8A H 0.7810 -0.0432 0.7870 0.073 Uiso 1 1 calc R A 1
H8B H 0.7179 0.0259 0.8126 0.073 Uiso 1 1 calc R A 1
C9A C 0.8038(7) -0.0170(4) 0.9460(5) 0.0752(15) Uani 0.763(3) 1 d PD B 1
H9A1 H 0.7410 -0.0247 0.9709 0.090 Uiso 0.763(3) 1 calc PR B 1
H9A2 H 0.8398 -0.0639 0.9541 0.090 Uiso 0.763(3) 1 calc PR B 1
C10A C 0.8623(4) 0.0396(3) 1.0169(4) 0.0774(11) Uani 0.763(3) 1 d PD B 1
H10A H 0.9312 0.0345 1.0077 0.093 Uiso 0.763(3) 1 calc PR B 1
H10B H 0.8589 0.0257 1.0903 0.093 Uiso 0.763(3) 1 calc PR B 1
C11A C 0.8987(4) 0.1617(3) 1.0880(4) 0.0774(11) Uani 0.763(3) 1 d PD B 1
H11A H 0.9673 0.1499 1.0833 0.093 Uiso 0.763(3) 1 calc PR B 1
H11B H 0.8859 0.1433 1.1566 0.093 Uiso 0.763(3) 1 calc PR B 1
C12A C 0.8880(7) 0.2448(3) 1.0876(5) 0.0752(15) Uani 0.763(3) 1 d PD B 1
H12A H 0.9309 0.2641 1.1505 0.090 Uiso 0.763(3) 1 calc PR B 1
H12B H 0.8201 0.2564 1.0957 0.090 Uiso 0.763(3) 1 calc PR B 1
C13 C 0.9113(3) 0.2876(2) 0.9899(3) 0.0709(11) Uani 1 1 d D . .
H13A H 0.9060 0.3409 1.0012 0.085 Uiso 1 1 calc R B 1
H13B H 0.9785 0.2766 0.9788 0.085 Uiso 1 1 calc R B 1
C14 C 0.7697(3) 0.30971(19) 0.8584(3) 0.0550(9) Uani 1 1 d . . .
H14 H 0.7749 0.3579 0.8860 0.066 Uiso 1 1 calc R B .
C15 C 0.6843(2) 0.29494(18) 0.7792(3) 0.0483(8) Uani 1 1 d . B .
C16 C 0.6608(2) 0.22229(18) 0.7372(2) 0.0442(8) Uani 1 1 d . . .
C17 C 0.5744(2) 0.21389(19) 0.6564(3) 0.0507(9) Uani 1 1 d . B .
C18 C 0.5188(3) 0.2767(2) 0.6261(3) 0.0703(11) Uani 1 1 d . . .
H18 H 0.4633 0.2712 0.5730 0.084 Uiso 1 1 calc R B .
C19 C 0.5390(3) 0.3474(2) 0.6684(3) 0.0778(12) Uani 1 1 d . B .
C20 C 0.6210(3) 0.35517(19) 0.7448(3) 0.0673(11) Uani 1 1 d . . .
H20 H 0.6357 0.4019 0.7752 0.081 Uiso 1 1 calc R B .
C21 C 1.2064(3) 0.0316(2) 0.5476(3) 0.0768(12) Uani 1 1 d . . .
H21A H 1.2641 0.0616 0.5438 0.092 Uiso 1 1 calc R . .
H21B H 1.1643 0.0310 0.4788 0.092 Uiso 1 1 calc R . .
H21C H 1.2267 -0.0185 0.5677 0.092 Uiso 1 1 calc R . .
C22 C 1.1834(2) 0.23322(17) 0.8224(3) 0.0504(9) Uani 1 1 d . . .
C23 C 1.2020(3) 0.2185(2) 0.9429(3) 0.0670(10) Uani 1 1 d . . .
H23A H 1.1409 0.2041 0.9655 0.080 Uiso 1 1 calc R . .
H23B H 1.2270 0.2630 0.9802 0.080 Uiso 1 1 calc R . .
H23C H 1.2499 0.1791 0.9589 0.080 Uiso 1 1 calc R . .
C24 C 1.2827(3) 0.2561(2) 0.7898(3) 0.0822(12) Uani 1 1 d . . .
H24A H 1.2730 0.2657 0.7142 0.099 Uiso 1 1 calc R . .
H24B H 1.3301 0.2165 0.8069 0.099 Uiso 1 1 calc R . .
H24C H 1.3071 0.3004 0.8281 0.099 Uiso 1 1 calc R . .
C25 C 1.1127(3) 0.30025(18) 0.7968(3) 0.0725(11) Uani 1 1 d . . .
H25A H 1.1013 0.3092 0.7210 0.087 Uiso 1 1 calc R . .
H25B H 1.1422 0.3437 0.8335 0.087 Uiso 1 1 calc R . .
H25C H 1.0506 0.2896 0.8201 0.087 Uiso 1 1 calc R . .
C26 C 0.4704(4) 0.4129(3) 0.6298(4) 0.143(2) Uani 1 1 d . . .
H26A H 0.4171 0.3959 0.5760 0.172 Uiso 1 1 calc R B .
H26B H 0.5076 0.4508 0.6000 0.172 Uiso 1 1 calc R . .
H26C H 0.4435 0.4332 0.6892 0.172 Uiso 1 1 calc R . .
C27 C 0.5445(2) 0.13720(19) 0.6084(3) 0.0528(9) Uani 1 1 d . . .
C28 C 0.6299(2) 0.1018(2) 0.5622(3) 0.0682(11) Uani 1 1 d . B .
H28A H 0.6486 0.1339 0.5080 0.082 Uiso 1 1 calc R . .
H28B H 0.6092 0.0543 0.5312 0.082 Uiso 1 1 calc R . .
H28C H 0.6858 0.0950 0.6184 0.082 Uiso 1 1 calc R . .
C29 C 0.4561(3) 0.1422(2) 0.5151(3) 0.0865(13) Uani 1 1 d . B .
H29A H 0.4001 0.1643 0.5404 0.104 Uiso 1 1 calc R . .
H29B H 0.4387 0.0931 0.4882 0.104 Uiso 1 1 calc R . .
H29C H 0.4744 0.1724 0.4588 0.104 Uiso 1 1 calc R . .
C30 C 0.5127(2) 0.0877(2) 0.6949(3) 0.0769(12) Uani 1 1 d . B .
H30A H 0.4589 0.1111 0.7227 0.092 Uiso 1 1 calc R . .
H30B H 0.5679 0.0808 0.7519 0.092 Uiso 1 1 calc R . .
H30C H 0.4913 0.0402 0.6647 0.092 Uiso 1 1 calc R . .
C31A C 0.7277(3) 0.1266(3) 1.0201(4) 0.0787(16) Uani 0.763(3) 1 d PD B 1
H31A H 0.6871 0.0993 0.9638 0.118 Uiso 0.763(3) 1 calc PR B 1
H31B H 0.7073 0.1779 1.0174 0.118 Uiso 0.763(3) 1 calc PR B 1
H31C H 0.7204 0.1056 1.0882 0.118 Uiso 0.763(3) 1 calc PR B 1
N1 N 0.85925(18) 0.05237(13) 0.8017(2) 0.0460(7) Uani 1 1 d . B .
N2 N 0.8363(2) 0.12157(18) 1.0053(2) 0.0664(9) Uani 1 1 d D . .
N3 N 0.84014(19) 0.26455(15) 0.8960(2) 0.0525(7) Uani 1 1 d . B .
O1 O 0.99630(14) 0.16613(11) 0.84912(18) 0.0501(6) Uani 1 1 d . . .
O2 O 0.71507(14) 0.16415(11) 0.76961(17) 0.0484(6) Uani 1 1 d . B .
Ni1 Ni 0.85057(3) 0.15793(2) 0.85183(3) 0.04431(17) Uani 1 1 d . B .
C9B C 0.786(3) -0.0014(14) 0.9512(12) 0.0752(15) Uani 0.237(3) 1 d PD B 2
H9B1 H 0.7388 -0.0392 0.9645 0.090 Uiso 0.237(3) 1 calc PR B 2
H9B2 H 0.8516 -0.0201 0.9816 0.090 Uiso 0.237(3) 1 calc PR B 2
C31B C 0.9482(9) 0.1052(11) 1.0615(12) 0.0787(16) Uani 0.237(3) 1 d PD B 2
H31D H 0.9893 0.1473 1.0518 0.118 Uiso 0.237(3) 1 calc PR B 2
H31E H 0.9726 0.0618 1.0297 0.118 Uiso 0.237(3) 1 calc PR B 2
H31F H 0.9498 0.0967 1.1367 0.118 Uiso 0.237(3) 1 calc PR B 2
C11B C 0.8215(13) 0.1931(8) 1.0708(13) 0.0774(11) Uani 0.237(3) 1 d PD B 2
H11C H 0.7536 0.2083 1.0442 0.093 Uiso 0.237(3) 1 calc PR B 2
H11D H 0.8212 0.1750 1.1430 0.093 Uiso 0.237(3) 1 calc PR B 2
C10B C 0.7681(12) 0.0643(9) 1.0145(13) 0.0774(11) Uani 0.237(3) 1 d PD B 2
H10C H 0.7012 0.0824 0.9901 0.093 Uiso 0.237(3) 1 calc PR B 2
H10D H 0.7731 0.0501 1.0892 0.093 Uiso 0.237(3) 1 calc PR B 2
C12B C 0.878(3) 0.2650(12) 1.0865(16) 0.0752(15) Uani 0.237(3) 1 d PD B 2
H12C H 0.8357 0.3036 1.1086 0.090 Uiso 0.237(3) 1 calc PR B 2
H12D H 0.9350 0.2590 1.1429 0.090 Uiso 0.237(3) 1 calc PR B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.305(3) . ?
C1 C6 1.414(4) . ?
C1 C2 1.439(4) . ?
C2 C3 1.373(4) . ?
C2 C22 1.539(4) . ?
C3 C4 1.398(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(4) . ?
C4 C21 1.517(4) . ?
C5 C6 1.401(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.447(4) . ?
C7 N1 1.275(3) . ?
C7 H7 0.9300 . ?
C8 N1 1.466(4) . ?
C8 C9A 1.497(6) . ?
C8 C9B 1.537(15) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9A C10A 1.494(9) . ?
C9A H9A1 0.9700 . ?
C9A H9A2 0.9700 . ?
C10A N2 1.512(5) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C11A N2 1.429(5) . ?
C11A C12A 1.497(7) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C12A C13 1.531(7) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C13 C12B 1.430(15) . ?
C13 N3 1.463(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N3 1.286(4) . ?
C14 C15 1.429(4) . ?
C14 H14 0.9300 . ?
C15 C20 1.405(4) . ?
C15 C16 1.423(4) . ?
C16 O2 1.304(3) . ?
C16 C17 1.434(4) . ?
C17 C18 1.375(4) . ?
C17 C27 1.530(4) . ?
C18 C19 1.385(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.359(5) . ?
C19 C26 1.530(5) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.526(4) . ?
C22 C24 1.534(4) . ?
C22 C25 1.541(4) . ?
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 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.524(4) . ?
C27 C30 1.526(4) . ?
C27 C29 1.544(4) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31A N2 1.524(5) . ?
C31A H31A 0.9600 . ?
C31A H31B 0.9600 . ?
C31A H31C 0.9600 . ?
N1 Ni1 2.005(2) . ?
N2 C10B 1.402(11) . ?
N2 C11B 1.558(12) . ?
N2 C31B 1.600(12) . ?
N2 Ni1 2.087(3) . ?
N3 Ni1 2.002(3) . ?
O1 Ni1 1.998(2) . ?
O2 Ni1 1.9680(19) . ?
C9B C10B 1.466(15) . ?
C9B H9B1 0.9700 . ?
C9B H9B2 0.9700 . ?
C31B H31D 0.9600 . ?
C31B H31E 0.9600 . ?
C31B H31F 0.9600 . ?
C11B C12B 1.497(16) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 122.5(3) . . ?
O1 C1 C2 120.3(3) . . ?
C6 C1 C2 117.1(3) . . ?
C3 C2 C1 117.9(3) . . ?
C3 C2 C22 121.5(3) . . ?
C1 C2 C22 120.6(3) . . ?
C2 C3 C4 125.0(3) . . ?
C2 C3 H3 117.5 . . ?
C4 C3 H3 117.5 . . ?
C5 C4 C3 116.7(3) . . ?
C5 C4 C21 123.2(3) . . ?
C3 C4 C21 120.1(3) . . ?
C4 C5 C6 122.0(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 C7 116.9(3) . . ?
C1 C6 C7 121.8(3) . . ?
N1 C7 C6 126.3(3) . . ?
N1 C7 H7 116.8 . . ?
C6 C7 H7 116.8 . . ?
N1 C8 C9A 110.2(4) . . ?
N1 C8 C9B 110.9(13) . . ?
C9A C8 C9B 14.3(12) . . ?
N1 C8 H8A 109.6 . . ?
C9A C8 H8A 109.6 . . ?
C9B C8 H8A 120.9 . . ?
N1 C8 H8B 109.6 . . ?
C9A C8 H8B 109.6 . . ?
C9B C8 H8B 96.6 . . ?
H8A C8 H8B 108.1 . . ?
C10A C9A C8 115.8(6) . . ?
C10A C9A H9A1 108.3 . . ?
C8 C9A H9A1 108.3 . . ?
C10A C9A H9A2 108.3 . . ?
C8 C9A H9A2 108.3 . . ?
H9A1 C9A H9A2 107.4 . . ?
C9A C10A N2 120.5(4) . . ?
C9A C10A H10A 107.2 . . ?
N2 C10A H10A 107.2 . . ?
C9A C10A H10B 107.2 . . ?
N2 C10A H10B 107.2 . . ?
H10A C10A H10B 106.8 . . ?
N2 C11A C12A 116.9(5) . . ?
N2 C11A H11A 108.1 . . ?
C12A C11A H11A 108.1 . . ?
N2 C11A H11B 108.1 . . ?
C12A C11A H11B 108.1 . . ?
H11A C11A H11B 107.3 . . ?
C11A C12A C13 117.9(5) . . ?
C11A C12A H12A 107.8 . . ?
C13 C12A H12A 107.8 . . ?
C11A C12A H12B 107.8 . . ?
C13 C12A H12B 107.8 . . ?
H12A C12A H12B 107.2 . . ?
C12B C13 N3 110.7(12) . . ?
C12B C13 C12A 14.5(13) . . ?
N3 C13 C12A 108.4(4) . . ?
C12B C13 H13A 96.3 . . ?
N3 C13 H13A 110.0 . . ?
C12A C13 H13A 110.0 . . ?
C12B C13 H13B 120.4 . . ?
N3 C13 H13B 110.0 . . ?
C12A C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
N3 C14 C15 128.0(3) . . ?
N3 C14 H14 116.0 . . ?
C15 C14 H14 116.0 . . ?
C20 C15 C16 119.8(3) . . ?
C20 C15 C14 117.6(3) . . ?
C16 C15 C14 122.6(3) . . ?
O2 C16 C15 122.1(3) . . ?
O2 C16 C17 119.8(3) . . ?
C15 C16 C17 118.1(3) . . ?
C18 C17 C16 117.6(3) . . ?
C18 C17 C27 121.7(3) . . ?
C16 C17 C27 120.7(3) . . ?
C17 C18 C19 125.1(3) . . ?
C17 C18 H18 117.5 . . ?
C19 C18 H18 117.5 . . ?
C20 C19 C18 117.2(3) . . ?
C20 C19 C26 122.4(4) . . ?
C18 C19 C26 120.4(4) . . ?
C19 C20 C15 122.2(3) . . ?
C19 C20 H20 118.9 . . ?
C15 C20 H20 118.9 . . ?
C4 C21 H21A 109.5 . . ?
C4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C24 107.8(3) . . ?
C23 C22 C2 110.1(3) . . ?
C24 C22 C2 112.4(3) . . ?
C23 C22 C25 109.9(3) . . ?
C24 C22 C25 106.5(3) . . ?
C2 C22 C25 110.1(2) . . ?
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 . . ?
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 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C19 C26 H26A 109.5 . . ?
C19 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C19 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C30 111.0(3) . . ?
C28 C27 C17 110.8(3) . . ?
C30 C27 C17 109.0(3) . . ?
C28 C27 C29 106.4(3) . . ?
C30 C27 C29 107.7(3) . . ?
C17 C27 C29 112.0(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 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N2 C31A H31A 109.5 . . ?
N2 C31A H31B 109.5 . . ?
H31A C31A H31B 109.5 . . ?
N2 C31A H31C 109.5 . . ?
H31A C31A H31C 109.5 . . ?
H31B C31A H31C 109.5 . . ?
C7 N1 C8 119.5(3) . . ?
C7 N1 Ni1 125.4(2) . . ?
C8 N1 Ni1 115.1(2) . . ?
C10B N2 C11A 129.1(7) . . ?
C10B N2 C10A 55.1(8) . . ?
C11A N2 C10A 108.4(3) . . ?
C10B N2 C31A 50.4(7) . . ?
C11A N2 C31A 110.7(4) . . ?
C10A N2 C31A 105.2(3) . . ?
C10B N2 C11B 114.4(10) . . ?
C11A N2 C11B 46.4(6) . . ?
C10A N2 C11B 142.8(7) . . ?
C31A N2 C11B 71.0(7) . . ?
C10B N2 C31B 115.2(10) . . ?
C11A N2 C31B 50.1(7) . . ?
C10A N2 C31B 65.7(7) . . ?
C31A N2 C31B 146.1(6) . . ?
C11B N2 C31B 96.4(10) . . ?
C10B N2 Ni1 118.0(7) . . ?
C11A N2 Ni1 112.8(3) . . ?
C10A N2 Ni1 109.7(3) . . ?
C31A N2 Ni1 109.7(2) . . ?
C11B N2 Ni1 106.1(6) . . ?
C31B N2 Ni1 104.0(6) . . ?
C14 N3 C13 118.6(3) . . ?
C14 N3 Ni1 125.5(2) . . ?
C13 N3 Ni1 115.3(2) . . ?
C1 O1 Ni1 126.68(18) . . ?
C16 O2 Ni1 130.2(2) . . ?
O2 Ni1 O1 146.74(9) . . ?
O2 Ni1 N3 89.42(9) . . ?
O1 Ni1 N3 92.93(9) . . ?
O2 Ni1 N1 89.16(9) . . ?
O1 Ni1 N1 87.32(9) . . ?
N3 Ni1 N1 177.78(11) . . ?
O2 Ni1 N2 106.62(10) . . ?
O1 Ni1 N2 106.51(10) . . ?
N3 Ni1 N2 90.94(12) . . ?
N1 Ni1 N2 91.10(12) . . ?
C10B C9B C8 122.3(17) . . ?
C10B C9B H9B1 106.7 . . ?
C8 C9B H9B1 106.7 . . ?
C10B C9B H9B2 106.7 . . ?
C8 C9B H9B2 106.7 . . ?
H9B1 C9B H9B2 106.6 . . ?
N2 C31B H31D 109.5 . . ?
N2 C31B H31E 109.5 . . ?
H31D C31B H31E 109.5 . . ?
N2 C31B H31F 109.5 . . ?
H31D C31B H31F 109.5 . . ?
H31E C31B H31F 109.5 . . ?
C12B C11B N2 132.1(15) . . ?
C12B C11B H11C 104.2 . . ?
N2 C11B H11C 104.2 . . ?
C12B C11B H11D 104.2 . . ?
N2 C11B H11D 104.2 . . ?
H11C C11B H11D 105.5 . . ?
N2 C10B C9B 111.7(18) . . ?
N2 C10B H10C 109.3 . . ?
C9B C10B H10C 109.3 . . ?
N2 C10B H10D 109.3 . . ?
C9B C10B H10D 109.3 . . ?
H10C C10B H10D 108.0 . . ?
C13 C12B C11B 111.0(15) . . ?
C13 C12B H12C 109.4 . . ?
C11B C12B H12C 109.4 . . ?
C13 C12B H12D 109.4 . . ?
C11B C12B H12D 109.4 . . ?
H12C C12B H12D 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -176.8(3) . . . . ?
C6 C1 C2 C3 3.0(4) . . . . ?
O1 C1 C2 C22 3.3(4) . . . . ?
C6 C1 C2 C22 -176.9(3) . . . . ?
C1 C2 C3 C4 -1.4(5) . . . . ?
C22 C2 C3 C4 178.6(3) . . . . ?
C2 C3 C4 C5 -1.5(5) . . . . ?
C2 C3 C4 C21 178.6(3) . . . . ?
C3 C4 C5 C6 2.6(5) . . . . ?
C21 C4 C5 C6 -177.5(3) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
C4 C5 C6 C7 -176.9(3) . . . . ?
O1 C1 C6 C5 177.8(3) . . . . ?
C2 C1 C6 C5 -2.0(4) . . . . ?
O1 C1 C6 C7 -6.4(4) . . . . ?
C2 C1 C6 C7 173.8(3) . . . . ?
C5 C6 C7 N1 -169.1(3) . . . . ?
C1 C6 C7 N1 14.9(5) . . . . ?
N1 C8 C9A C10A 26.6(7) . . . . ?
C9B C8 C9A C10A -69(6) . . . . ?
C8 C9A C10A N2 45.6(8) . . . . ?
N2 C11A C12A C13 -61.7(9) . . . . ?
C11A C12A C13 C12B 165(7) . . . . ?
C11A C12A C13 N3 63.5(8) . . . . ?
N3 C14 C15 C20 -175.2(3) . . . . ?
N3 C14 C15 C16 6.3(5) . . . . ?
C20 C15 C16 O2 -177.3(3) . . . . ?
C14 C15 C16 O2 1.1(5) . . . . ?
C20 C15 C16 C17 2.9(5) . . . . ?
C14 C15 C16 C17 -178.7(3) . . . . ?
O2 C16 C17 C18 179.0(3) . . . . ?
C15 C16 C17 C18 -1.2(4) . . . . ?
O2 C16 C17 C27 0.6(4) . . . . ?
C15 C16 C17 C27 -179.6(3) . . . . ?
C16 C17 C18 C19 -0.8(6) . . . . ?
C27 C17 C18 C19 177.6(4) . . . . ?
C17 C18 C19 C20 0.9(6) . . . . ?
C17 C18 C19 C26 -178.8(4) . . . . ?
C18 C19 C20 C15 0.9(6) . . . . ?
C26 C19 C20 C15 -179.4(4) . . . . ?
C16 C15 C20 C19 -2.8(6) . . . . ?
C14 C15 C20 C19 178.7(4) . . . . ?
C3 C2 C22 C23 -120.8(3) . . . . ?
C1 C2 C22 C23 59.1(4) . . . . ?
C3 C2 C22 C24 -0.6(4) . . . . ?
C1 C2 C22 C24 179.3(3) . . . . ?
C3 C2 C22 C25 117.9(3) . . . . ?
C1 C2 C22 C25 -62.2(4) . . . . ?
C18 C17 C27 C28 126.1(3) . . . . ?
C16 C17 C27 C28 -55.6(4) . . . . ?
C18 C17 C27 C30 -111.5(4) . . . . ?
C16 C17 C27 C30 66.8(4) . . . . ?
C18 C17 C27 C29 7.5(5) . . . . ?
C16 C17 C27 C29 -174.2(3) . . . . ?
C6 C7 N1 C8 -172.2(3) . . . . ?
C6 C7 N1 Ni1 7.4(4) . . . . ?
C9A C8 N1 C7 105.5(4) . . . . ?
C9B C8 N1 C7 120.8(11) . . . . ?
C9A C8 N1 Ni1 -74.2(4) . . . . ?
C9B C8 N1 Ni1 -58.9(11) . . . . ?
C12A C11A N2 C10B -123.1(11) . . . . ?
C12A C11A N2 C10A 177.2(5) . . . . ?
C12A C11A N2 C31A -67.9(6) . . . . ?
C12A C11A N2 C11B -35.3(9) . . . . ?
C12A C11A N2 C31B 144.9(10) . . . . ?
C12A C11A N2 Ni1 55.5(6) . . . . ?
C9A C10A N2 C10B 50.2(9) . . . . ?
C9A C10A N2 C11A 175.6(5) . . . . ?
C9A C10A N2 C31A 57.1(6) . . . . ?
C9A C10A N2 C11B 135.4(11) . . . . ?
C9A C10A N2 C31B -157.7(8) . . . . ?
C9A C10A N2 Ni1 -60.8(5) . . . . ?
C15 C14 N3 C13 -169.5(3) . . . . ?
C15 C14 N3 Ni1 0.6(5) . . . . ?
C12B C13 N3 C14 90.2(13) . . . . ?
C12A C13 N3 C14 105.4(4) . . . . ?
C12B C13 N3 Ni1 -80.8(13) . . . . ?
C12A C13 N3 Ni1 -65.7(4) . . . . ?
C6 C1 O1 Ni1 -23.4(4) . . . . ?
C2 C1 O1 Ni1 156.4(2) . . . . ?
C15 C16 O2 Ni1 -15.2(4) . . . . ?
C17 C16 O2 Ni1 164.5(2) . . . . ?
C16 O2 Ni1 O1 -77.6(3) . . . . ?
C16 O2 Ni1 N3 16.9(3) . . . . ?
C16 O2 Ni1 N1 -161.4(3) . . . . ?
C16 O2 Ni1 N2 107.7(3) . . . . ?
C1 O1 Ni1 O2 -51.1(3) . . . . ?
C1 O1 Ni1 N3 -144.5(2) . . . . ?
C1 O1 Ni1 N1 33.3(2) . . . . ?
C1 O1 Ni1 N2 123.6(2) . . . . ?
C14 N3 Ni1 O2 -9.1(3) . . . . ?
C13 N3 Ni1 O2 161.3(2) . . . . ?
C14 N3 Ni1 O1 137.7(3) . . . . ?
C13 N3 Ni1 O1 -51.9(2) . . . . ?
C14 N3 Ni1 N1 41(3) . . . . ?
C13 N3 Ni1 N1 -148(3) . . . . ?
C14 N3 Ni1 N2 -115.7(3) . . . . ?
C13 N3 Ni1 N2 54.7(3) . . . . ?
C7 N1 Ni1 O2 122.2(3) . . . . ?
C8 N1 Ni1 O2 -58.2(2) . . . . ?
C7 N1 Ni1 O1 -24.7(3) . . . . ?
C8 N1 Ni1 O1 154.9(2) . . . . ?
C7 N1 Ni1 N3 72(3) . . . . ?
C8 N1 Ni1 N3 -108(3) . . . . ?
C7 N1 Ni1 N2 -131.2(3) . . . . ?
C8 N1 Ni1 N2 48.4(2) . . . . ?
C10B N2 Ni1 O2 42.2(9) . . . . ?
C11A N2 Ni1 O2 -136.6(3) . . . . ?
C10A N2 Ni1 O2 102.4(3) . . . . ?
C31A N2 Ni1 O2 -12.6(3) . . . . ?
C11B N2 Ni1 O2 -87.7(7) . . . . ?
C31B N2 Ni1 O2 171.2(7) . . . . ?
C10B N2 Ni1 O1 -134.7(9) . . . . ?
C11A N2 Ni1 O1 46.5(3) . . . . ?
C10A N2 Ni1 O1 -74.6(3) . . . . ?
C31A N2 Ni1 O1 170.4(3) . . . . ?
C11B N2 Ni1 O1 95.3(7) . . . . ?
C31B N2 Ni1 O1 -5.7(8) . . . . ?
C10B N2 Ni1 N3 131.9(9) . . . . ?
C11A N2 Ni1 N3 -46.9(3) . . . . ?
C10A N2 Ni1 N3 -167.9(3) . . . . ?
C31A N2 Ni1 N3 77.1(3) . . . . ?
C11B N2 Ni1 N3 2.0(7) . . . . ?
C31B N2 Ni1 N3 -99.1(8) . . . . ?
C10B N2 Ni1 N1 -47.2(9) . . . . ?
C11A N2 Ni1 N1 134.0(3) . . . . ?
C10A N2 Ni1 N1 13.0(3) . . . . ?
C31A N2 Ni1 N1 -102.1(3) . . . . ?
C11B N2 Ni1 N1 -177.1(7) . . . . ?
C31B N2 Ni1 N1 81.8(8) . . . . ?
N1 C8 C9B C10B 63(3) . . . . ?
C9A C8 C9B C10B 152(9) . . . . ?
C10B N2 C11B C12B 178(2) . . . . ?
C11A N2 C11B C12B 56(2) . . . . ?
C10A N2 C11B C12B 114(2) . . . . ?
C31A N2 C11B C12B -156(2) . . . . ?
C31B N2 C11B C12B 56(2) . . . . ?
Ni1 N2 C11B C12B -50(2) . . . . ?
C11A N2 C10B C9B -127.2(14) . . . . ?
C10A N2 C10B C9B -41.2(13) . . . . ?
C31A N2 C10B C9B 147.3(19) . . . . ?
C11B N2 C10B C9B -179.8(15) . . . . ?
C31B N2 C10B C9B -69.4(17) . . . . ?
Ni1 N2 C10B C9B 54.2(17) . . . . ?
C8 C9B C10B N2 -60(3) . . . . ?
N3 C13 C12B C11B 33(3) . . . . ?
C12A C13 C12B C11B -51(5) . . . . ?
N2 C11B C12B C13 38(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.047

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1047941'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 Br2 N3 Ni O2'
_chemical_formula_weight         567.95

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

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                   10.1636(7)
_cell_length_b                   26.5733(13)
_cell_length_c                   8.5995(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.486(9)
_cell_angle_gamma                90.00
_cell_volume                     2130.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    15524
_cell_measurement_theta_min      3.001
_cell_measurement_theta_max      32.154

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    4.685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2833
_exptl_absorpt_correction_T_max  0.4255
_exptl_absorpt_process_details   
;
 CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
face-indexed (CrysAlis RED; Oxford Diffraction, 2006)
;

_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  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16408
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3736
_reflns_number_gt                2747
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  ' enCIFer (Allen et al., 2004)'

_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)+(0.0307P)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         3736
_refine_ls_number_parameters     286
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0577
_refine_ls_wR_factor_gt          0.0553
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_restrained_S_all      0.910
_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
Br1 Br 1.05885(4) 0.383282(14) 0.65248(5) 0.05437(13) Uani 1 1 d . . .
Br2 Br 0.14553(3) 0.016209(12) 0.89316(4) 0.03460(10) Uani 1 1 d . . .
C1 C 0.8520(3) 0.22413(11) 0.6454(4) 0.0250(7) Uani 1 1 d . B .
C2 C 0.9928(3) 0.23593(11) 0.7611(4) 0.0286(8) Uani 1 1 d . . .
H2 H 1.0478 0.2108 0.8383 0.034 Uiso 1 1 calc R . .
C3 C 1.0523(3) 0.28254(12) 0.7655(4) 0.0325(8) Uani 1 1 d . . .
H3 H 1.1466 0.2895 0.8456 0.039 Uiso 1 1 calc R . .
C4 C 0.9738(4) 0.31935(12) 0.6522(4) 0.0325(8) Uani 1 1 d . . .
C5 C 0.8396(3) 0.30986(11) 0.5388(4) 0.0297(8) Uani 1 1 d . . .
H5 H 0.7881 0.3354 0.4609 0.036 Uiso 1 1 calc R . .
C6 C 0.7746(3) 0.26307(11) 0.5335(4) 0.0256(7) Uani 1 1 d . . .
C7 C 0.6314(3) 0.25620(12) 0.4065(4) 0.0289(7) Uani 1 1 d . . .
H7 H 0.5934 0.2822 0.3250 0.035 Uiso 1 1 calc R . .
C8 C 0.4158(3) 0.21429(14) 0.2459(4) 0.0416(9) Uani 1 1 d . . .
H8A H 0.3878 0.2479 0.1932 0.050 Uiso 1 1 calc R A 1
H8B H 0.3395 0.2024 0.2811 0.050 Uiso 1 1 calc R A 1
C9 C 0.4308(4) 0.17791(15) 0.1177(4) 0.0526(11) Uani 0.802(4) 1 d P B 1
H9A H 0.3456 0.1557 0.0768 0.063 Uiso 0.802(4) 1 calc PR B 1
H9B H 0.4291 0.1976 0.0193 0.063 Uiso 0.802(4) 1 calc PR B 1
C10 C 0.5610(6) 0.14566(19) 0.1777(5) 0.0460(14) Uani 0.802(4) 1 d PU B 1
H10C H 0.6453 0.1678 0.2023 0.055 Uiso 0.802(4) 1 calc PR B 1
H10D H 0.5551 0.1234 0.0829 0.055 Uiso 0.802(4) 1 calc PR B 1
C11 C 0.4604(4) 0.07788(16) 0.2807(5) 0.0360(11) Uani 0.802(4) 1 d PD B 1
H11D H 0.3726 0.0975 0.2555 0.054 Uiso 0.802(4) 1 calc PR B 1
H11E H 0.4743 0.0548 0.3749 0.054 Uiso 0.802(4) 1 calc PR B 1
H11F H 0.4520 0.0585 0.1802 0.054 Uiso 0.802(4) 1 calc PR B 1
C12 C 0.7200(5) 0.08601(18) 0.3666(5) 0.0426(13) Uani 0.802(4) 1 d PU B 1
H12C H 0.7993 0.1106 0.3935 0.051 Uiso 0.802(4) 1 calc PR B 1
H12D H 0.7120 0.0679 0.2627 0.051 Uiso 0.802(4) 1 calc PR B 1
C13 C 0.7620(4) 0.04740(13) 0.5139(5) 0.0442(9) Uani 0.802(4) 1 d P B 1
H13C H 0.6862 0.0214 0.4833 0.053 Uiso 0.802(4) 1 calc PR B 1
H13D H 0.8517 0.0305 0.5235 0.053 Uiso 0.802(4) 1 calc PR B 1
C14 C 0.7842(3) 0.06842(12) 0.6864(4) 0.0329(8) Uani 1 1 d . . .
H14A H 0.8101 0.0408 0.7707 0.040 Uiso 1 1 calc R B 1
H14B H 0.8640 0.0930 0.7228 0.040 Uiso 1 1 calc R B 1
C15 C 0.5748(3) 0.06978(11) 0.7405(4) 0.0236(7) Uani 1 1 d . . .
H15 H 0.6125 0.0393 0.7990 0.028 Uiso 1 1 calc R B .
C16 C 0.4364(3) 0.08480(10) 0.7307(3) 0.0183(6) Uani 1 1 d . B .
C17 C 0.3682(3) 0.05272(11) 0.8048(3) 0.0231(7) Uani 1 1 d . . .
H17 H 0.4155 0.0228 0.8594 0.028 Uiso 1 1 calc R B .
C18 C 0.2354(3) 0.06345(11) 0.8003(4) 0.0223(7) Uani 1 1 d . B .
C19 C 0.1667(3) 0.10748(11) 0.7265(4) 0.0257(7) Uani 1 1 d . . .
H19 H 0.0761 0.1157 0.7277 0.031 Uiso 1 1 calc R B .
C20 C 0.2298(3) 0.13916(11) 0.6518(4) 0.0258(7) Uani 1 1 d . B .
H20 H 0.1809 0.1692 0.6012 0.031 Uiso 1 1 calc R . .
C21 C 0.3652(3) 0.12930(10) 0.6462(4) 0.0213(7) Uani 1 1 d . . .
N1 N 0.5513(3) 0.21816(10) 0.3943(3) 0.0283(6) Uani 1 1 d . B .
N2 N 0.5889(3) 0.11354(11) 0.3296(4) 0.0390(7) Uani 1 1 d D . .
N3 N 0.6528(2) 0.09310(9) 0.6788(3) 0.0234(6) Uani 1 1 d . B .
Ni1 Ni 0.60203(4) 0.156389(14) 0.53866(5) 0.02299(11) Uani 1 1 d . B .
O1 O 0.8024(2) 0.17910(7) 0.6460(3) 0.0303(5) Uani 1 1 d . . .
O2 O 0.4166(2) 0.15972(7) 0.5665(2) 0.0252(5) Uani 1 1 d . B .
C9B C 0.4308(4) 0.17791(15) 0.1177(4) 0.0526(11) Uani 0.198(4) 1 d P B 2
H9B1 H 0.5013 0.1915 0.0757 0.063 Uiso 0.198(4) 1 calc PR B 2
H9B2 H 0.3373 0.1749 0.0198 0.063 Uiso 0.198(4) 1 calc PR B 2
C10B C 0.483(3) 0.1222(9) 0.200(3) 0.065(7) Uani 0.198(4) 1 d PU B 2
H10A H 0.4005 0.1075 0.2172 0.078 Uiso 0.198(4) 1 calc PR B 2
H10B H 0.4949 0.1020 0.1094 0.078 Uiso 0.198(4) 1 calc PR B 2
C11B C 0.7332(16) 0.1336(7) 0.303(2) 0.0360(11) Uani 0.198(4) 1 d PD B 2
H11A H 0.7513 0.1117 0.2222 0.054 Uiso 0.198(4) 1 calc PR B 2
H11B H 0.8162 0.1328 0.4123 0.054 Uiso 0.198(4) 1 calc PR B 2
H11C H 0.7173 0.1681 0.2598 0.054 Uiso 0.198(4) 1 calc PR B 2
C12B C 0.637(2) 0.0593(7) 0.384(2) 0.046(5) Uani 0.198(4) 1 d PU B 2
H12A H 0.5601 0.0433 0.4090 0.056 Uiso 0.198(4) 1 calc PR B 2
H12B H 0.6387 0.0420 0.2825 0.056 Uiso 0.198(4) 1 calc PR B 2
C13B C 0.7620(4) 0.04740(13) 0.5139(5) 0.0442(9) Uani 0.198(4) 1 d P B 2
H13A H 0.8420 0.0592 0.4851 0.053 Uiso 0.198(4) 1 calc PR B 2
H13B H 0.7688 0.0103 0.5230 0.053 Uiso 0.198(4) 1 calc PR B 2


_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
Br1 C4 1.906(3) . ?
Br2 C18 1.904(3) . ?
C1 O1 1.299(3) . ?
C1 C2 1.414(4) . ?
C1 C6 1.419(4) . ?
C2 C3 1.372(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.348(4) . ?
C5 C6 1.400(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.441(4) . ?
C7 N1 1.276(4) . ?
C7 H7 0.9500 . ?
C8 N1 1.461(4) . ?
C8 C9 1.519(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.486(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.490(5) . ?
C10 H10C 0.9900 . ?
C10 H10D 0.9900 . ?
C11 N2 1.531(5) . ?
C11 H11D 0.9800 . ?
C11 H11E 0.9800 . ?
C11 H11F 0.9800 . ?
C12 N2 1.440(5) . ?
C12 C13 1.552(6) . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C13 C14 1.516(5) . ?
C13 H13C 0.9900 . ?
C13 H13D 0.9900 . ?
C14 N3 1.466(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N3 1.277(3) . ?
C15 C16 1.432(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.402(4) . ?
C16 C21 1.425(4) . ?
C17 C18 1.366(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(4) . ?
C19 C20 1.364(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.420(4) . ?
C20 H20 0.9500 . ?
C21 O2 1.297(3) . ?
N1 Ni1 1.998(3) . ?
N2 C10B 1.23(2) . ?
N2 C12B 1.53(2) . ?
N2 C11B 1.659(13) . ?
N2 Ni1 2.087(3) . ?
N3 Ni1 2.013(2) . ?
Ni1 O1 1.966(2) . ?
Ni1 O2 1.9936(19) . ?
C10B H10A 0.9900 . ?
C10B H10B 0.9900 . ?
C11B H11A 0.9800 . ?
C11B H11B 0.9800 . ?
C11B H11C 0.9800 . ?
C12B H12A 0.9900 . ?
C12B H12B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 119.1(3) . . ?
O1 C1 C6 124.3(3) . . ?
C2 C1 C6 116.6(3) . . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 Br1 119.7(2) . . ?
C3 C4 Br1 119.6(3) . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 C7 117.3(3) . . ?
C1 C6 C7 122.8(3) . . ?
N1 C7 C6 125.5(3) . . ?
N1 C7 H7 117.2 . . ?
C6 C7 H7 117.2 . . ?
N1 C8 C9 110.3(3) . . ?
N1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 116.6(3) . . ?
C10 C9 H9A 108.1 . . ?
C8 C9 H9A 108.1 . . ?
C10 C9 H9B 108.1 . . ?
C8 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?
C9 C10 N2 117.8(4) . . ?
C9 C10 H10C 107.9 . . ?
N2 C10 H10C 107.9 . . ?
C9 C10 H10D 107.9 . . ?
N2 C10 H10D 107.9 . . ?
H10C C10 H10D 107.2 . . ?
N2 C11 H11D 109.5 . . ?
N2 C11 H11E 109.5 . . ?
N2 C11 H11F 109.5 . . ?
N2 C12 C13 116.5(3) . . ?
N2 C12 H12C 108.2 . . ?
C13 C12 H12C 108.2 . . ?
N2 C12 H12D 108.2 . . ?
C13 C12 H12D 108.2 . . ?
H12C C12 H12D 107.3 . . ?
C14 C13 C12 116.1(3) . . ?
C14 C13 H13C 108.3 . . ?
C12 C13 H13C 108.3 . . ?
C14 C13 H13D 108.3 . . ?
C12 C13 H13D 108.3 . . ?
H13C C13 H13D 107.4 . . ?
N3 C14 C13 110.1(3) . . ?
N3 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
N3 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.2 . . ?
N3 C15 C16 126.7(3) . . ?
N3 C15 H15 116.6 . . ?
C16 C15 H15 116.6 . . ?
C17 C16 C21 119.6(3) . . ?
C17 C16 C15 117.1(3) . . ?
C21 C16 C15 123.3(2) . . ?
C18 C17 C16 121.5(3) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 Br2 119.0(2) . . ?
C19 C18 Br2 120.8(2) . . ?
C20 C19 C18 119.5(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 123.1(3) . . ?
C19 C20 H20 118.5 . . ?
C21 C20 H20 118.5 . . ?
O2 C21 C20 120.2(3) . . ?
O2 C21 C16 123.8(3) . . ?
C20 C21 C16 116.0(3) . . ?
C7 N1 C8 118.4(3) . . ?
C7 N1 Ni1 127.0(2) . . ?
C8 N1 Ni1 113.9(2) . . ?
C10B N2 C12 134.1(10) . . ?
C10B N2 C10 45.7(11) . . ?
C12 N2 C10 108.7(3) . . ?
C10B N2 C11 61.5(11) . . ?
C12 N2 C11 111.1(3) . . ?
C10 N2 C11 105.7(3) . . ?
C10B N2 C12B 120.8(13) . . ?
C12 N2 C12B 45.5(7) . . ?
C10 N2 C12B 136.9(7) . . ?
C11 N2 C12B 68.7(7) . . ?
C10B N2 C11B 108.5(13) . . ?
C12 N2 C11B 53.3(7) . . ?
C10 N2 C11B 64.3(7) . . ?
C11 N2 C11B 149.9(6) . . ?
C12B N2 C11B 98.6(10) . . ?
C10B N2 Ni1 114.5(10) . . ?
C12 N2 Ni1 110.6(3) . . ?
C10 N2 Ni1 111.5(2) . . ?
C11 N2 Ni1 109.2(2) . . ?
C12B N2 Ni1 110.4(7) . . ?
C11B N2 Ni1 100.7(6) . . ?
C15 N3 C14 118.0(2) . . ?
C15 N3 Ni1 126.9(2) . . ?
C14 N3 Ni1 114.36(18) . . ?
O1 Ni1 O2 141.42(8) . . ?
O1 Ni1 N1 90.11(9) . . ?
O2 Ni1 N1 90.91(9) . . ?
O1 Ni1 N3 90.29(9) . . ?
O2 Ni1 N3 89.67(9) . . ?
N1 Ni1 N3 178.50(10) . . ?
O1 Ni1 N2 105.69(11) . . ?
O2 Ni1 N2 112.87(10) . . ?
N1 Ni1 N2 90.06(11) . . ?
N3 Ni1 N2 88.44(11) . . ?
C1 O1 Ni1 127.75(19) . . ?
C21 O2 Ni1 129.43(18) . . ?
N2 C10B H10A 106.0 . . ?
N2 C10B H10B 106.0 . . ?
H10A C10B H10B 106.3 . . ?
N2 C11B H11A 109.5 . . ?
N2 C11B H11B 109.5 . . ?
H11A C11B H11B 109.5 . . ?
N2 C11B H11C 109.5 . . ?
H11A C11B H11C 109.5 . . ?
H11B C11B H11C 109.5 . . ?
N2 C12B H12A 106.4 . . ?
N2 C12B H12B 106.4 . . ?
H12A C12B H12B 106.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.070
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1047942'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 I2 N3 Ni O2'
_chemical_formula_weight         661.93

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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                   10.3149(6)
_cell_length_b                   27.6223(12)
_cell_length_c                   8.4460(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.807(7)
_cell_angle_gamma                90.00
_cell_volume                     2201.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    15211
_cell_measurement_theta_min      3.022
_cell_measurement_theta_max      32.432

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.997
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    3.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3487
_exptl_absorpt_correction_T_max  0.6062
_exptl_absorpt_process_details   
;
 CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
face-indexed (CrysAlis RED; Oxford Diffraction, 2006)
;


_diffrn_ambient_temperature      130(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  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14177
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3863
_reflns_number_gt                3305
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  ' enCIFer (Allen et al., 2004)'

_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)+(0.0320P)²+4.0732P] 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         3863
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0634
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.3629(4) 0.12940(13) 0.6349(5) 0.0169(8) Uani 1 1 d . B .
C2 C 0.2312(4) 0.13851(14) 0.6429(5) 0.0194(8) Uani 1 1 d . . .
H2 H 0.1841 0.1681 0.5972 0.023 Uiso 1 1 calc R . .
C3 C 0.1682(4) 0.10653(14) 0.7139(5) 0.0206(8) Uani 1 1 d . . .
H3 H 0.0784 0.1137 0.7147 0.025 Uiso 1 1 calc R . .
C4 C 0.2371(4) 0.06327(14) 0.7851(5) 0.0196(8) Uani 1 1 d . . .
C5 C 0.3671(4) 0.05364(14) 0.7860(5) 0.0177(8) Uani 1 1 d . . .
H5 H 0.4136 0.0243 0.8361 0.021 Uiso 1 1 calc R . .
C6 C 0.4338(4) 0.08603(13) 0.7149(5) 0.0167(8) Uani 1 1 d . . .
C7 C 0.5697(4) 0.07199(14) 0.7216(5) 0.0195(8) Uani 1 1 d . . .
H7 H 0.6066 0.0419 0.7753 0.023 Uiso 1 1 calc R . .
C8 C 0.7748(4) 0.07324(15) 0.6662(5) 0.0231(9) Uani 1 1 d . . .
H8A H 0.8021 0.0462 0.7504 0.028 Uiso 1 1 calc R A 1
H8B H 0.8530 0.0971 0.7042 0.028 Uiso 1 1 calc R A 1
C9A C 0.7512(5) 0.05410(16) 0.4874(6) 0.0317(10) Uani 0.791(5) 1 d P B 1
H9A1 H 0.6754 0.0294 0.4534 0.038 Uiso 0.791(5) 1 calc PR B 1
H9A2 H 0.8391 0.0378 0.4950 0.038 Uiso 0.791(5) 1 calc PR B 1
C9B C 0.7512(5) 0.05410(16) 0.4874(6) 0.0317(10) Uani 0.209(5) 1 d P B 2
H9B1 H 0.7547 0.0183 0.4918 0.038 Uiso 0.209(5) 1 calc PR B 2
H9B2 H 0.8300 0.0653 0.4581 0.038 Uiso 0.209(5) 1 calc PR B 2
C10A C 0.7107(6) 0.0925(2) 0.3447(7) 0.0318(13) Uani 0.791(5) 1 d P B 1
H10A H 0.7881 0.1167 0.3775 0.038 Uiso 0.791(5) 1 calc PR B 1
H10B H 0.7048 0.0767 0.2369 0.038 Uiso 0.791(5) 1 calc PR B 1
C11A C 0.4560(6) 0.08200(19) 0.2603(7) 0.0274(12) Uani 0.791(5) 1 d P B 1
H11A H 0.4503 0.0632 0.1593 0.041 Uiso 0.791(5) 1 calc PR B 1
H11B H 0.3665 0.0992 0.2332 0.041 Uiso 0.791(5) 1 calc PR B 1
H11C H 0.4739 0.0602 0.3583 0.041 Uiso 0.791(5) 1 calc PR B 1
C12A C 0.5463(6) 0.1496(2) 0.1557(7) 0.0302(13) Uani 0.791(5) 1 d P B 1
H12A H 0.5382 0.1287 0.0569 0.036 Uiso 0.791(5) 1 calc PR B 1
H12B H 0.6289 0.1711 0.1800 0.036 Uiso 0.791(5) 1 calc PR B 1
C13A C 0.4147(5) 0.18089(17) 0.0999(6) 0.0327(11) Uani 0.791(5) 1 d P B 1
H13A H 0.3310 0.1593 0.0602 0.039 Uiso 0.791(5) 1 calc PR B 1
H13B H 0.4092 0.2004 -0.0010 0.039 Uiso 0.791(5) 1 calc PR B 1
C13B C 0.4147(5) 0.18089(17) 0.0999(6) 0.0327(11) Uani 0.209(5) 1 d P B 2
H13C H 0.3227 0.1801 -0.0018 0.039 Uiso 0.209(5) 1 calc PR B 2
H13D H 0.4870 0.1933 0.0611 0.039 Uiso 0.209(5) 1 calc PR B 2
C14 C 0.4032(4) 0.21541(16) 0.2353(5) 0.0273(10) Uani 1 1 d . . .
H14A H 0.3749 0.2480 0.1842 0.033 Uiso 1 1 calc R B 1
H14B H 0.3299 0.2036 0.2736 0.033 Uiso 1 1 calc R B 1
C15 C 0.6192(4) 0.25476(14) 0.3956(5) 0.0214(9) Uani 1 1 d . . .
H15 H 0.5809 0.2802 0.3144 0.026 Uiso 1 1 calc R B .
C16 C 0.7615(4) 0.26048(14) 0.5225(5) 0.0198(8) Uani 1 1 d . B .
C17 C 0.8256(4) 0.30571(14) 0.5281(5) 0.0226(9) Uani 1 1 d . . .
H17 H 0.7739 0.3306 0.4510 0.027 Uiso 1 1 calc R B .
C18 C 0.9612(4) 0.31414(14) 0.6431(5) 0.0214(9) Uani 1 1 d . B .
C19 C 1.0403(4) 0.27811(15) 0.7544(5) 0.0220(9) Uani 1 1 d . . .
H19 H 1.1349 0.2843 0.8339 0.026 Uiso 1 1 calc R B .
C20 C 0.9806(4) 0.23330(14) 0.7486(5) 0.0215(9) Uani 1 1 d . B .
H20 H 1.0355 0.2087 0.8249 0.026 Uiso 1 1 calc R . .
C21 C 0.8413(4) 0.22276(14) 0.6335(5) 0.0194(8) Uani 1 1 d . . .
N1 N 0.6459(3) 0.09608(12) 0.6623(4) 0.0182(7) Uani 1 1 d . B .
N2 N 0.5764(4) 0.11850(13) 0.3070(4) 0.0256(8) Uani 1 1 d . . .
N3 N 0.5398(3) 0.21816(12) 0.3831(4) 0.0199(7) Uani 1 1 d . B .
O1 O 0.4134(3) 0.16026(9) 0.5581(4) 0.0213(6) Uani 1 1 d . . .
O2 O 0.7912(3) 0.17952(10) 0.6322(4) 0.0232(6) Uani 1 1 d . B .
Ni1 Ni 0.59315(5) 0.157718(18) 0.52538(6) 0.01694(12) Uani 1 1 d . B .
I1 I 0.14026(3) 0.011097(9) 0.88055(4) 0.02560(9) Uani 1 1 d . . .
I2 I 1.05139(3) 0.382150(10) 0.64033(4) 0.03102(9) Uani 1 1 d . . .
C11B C 0.710(2) 0.1394(7) 0.268(3) 0.0274(12) Uani 0.209(5) 1 d P B 2
H11D H 0.7983 0.1354 0.3719 0.041 Uiso 0.209(5) 1 calc PR B 2
H11E H 0.6951 0.1738 0.2382 0.041 Uiso 0.209(5) 1 calc PR B 2
H11F H 0.7170 0.1214 0.1720 0.041 Uiso 0.209(5) 1 calc PR B 2
C12B C 0.454(2) 0.1308(8) 0.168(3) 0.0302(13) Uani 0.209(5) 1 d P B 2
H12C H 0.3745 0.1189 0.1950 0.036 Uiso 0.209(5) 1 calc PR B 2
H12D H 0.4523 0.1111 0.0691 0.036 Uiso 0.209(5) 1 calc PR B 2
C10B C 0.606(2) 0.0702(8) 0.338(3) 0.0318(13) Uani 0.209(5) 1 d P B 2
H10C H 0.6018 0.0555 0.2293 0.038 Uiso 0.209(5) 1 calc PR B 2
H10D H 0.5290 0.0556 0.3633 0.038 Uiso 0.209(5) 1 calc PR B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.300(5) . ?
C1 C2 1.410(5) . ?
C1 C6 1.424(5) . ?
C2 C3 1.370(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.364(5) . ?
C4 I1 2.092(4) . ?
C5 C6 1.402(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.434(5) . ?
C7 N1 1.276(5) . ?
C7 H7 0.9500 . ?
C8 N1 1.459(5) . ?
C8 C9A 1.525(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9A C10A 1.532(7) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A N2 1.476(7) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A N2 1.523(6) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A N2 1.465(6) . ?
C12A C13A 1.515(8) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A C14 1.530(6) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C14 N3 1.459(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N3 1.279(5) . ?
C15 C16 1.434(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.405(5) . ?
C16 C21 1.421(6) . ?
C17 C18 1.363(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(6) . ?
C18 I2 2.101(4) . ?
C19 C20 1.374(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.402(6) . ?
C20 H20 0.9500 . ?
C21 O2 1.300(5) . ?
N1 Ni1 2.006(3) . ?
N2 C10B 1.37(2) . ?
N2 C12B 1.38(2) . ?
N2 C11B 1.65(2) . ?
N2 Ni1 2.085(3) . ?
N3 Ni1 2.000(3) . ?
O1 Ni1 1.983(3) . ?
O2 Ni1 1.965(3) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 119.7(3) . . ?
O1 C1 C6 123.8(3) . . ?
C2 C1 C6 116.6(3) . . ?
C3 C2 C1 122.8(4) . . ?
C3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C2 C3 C4 119.4(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 I1 119.0(3) . . ?
C3 C4 I1 121.1(3) . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 C7 116.8(3) . . ?
C1 C6 C7 123.5(3) . . ?
N1 C7 C6 126.2(4) . . ?
N1 C7 H7 116.9 . . ?
C6 C7 H7 116.9 . . ?
N1 C8 C9A 110.4(3) . . ?
N1 C8 H8A 109.6 . . ?
C9A C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C9A C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9A C10A 115.0(4) . . ?
C8 C9A H9A1 108.5 . . ?
C10A C9A H9A1 108.5 . . ?
C8 C9A H9A2 108.5 . . ?
C10A C9A H9A2 108.5 . . ?
H9A1 C9A H9A2 107.5 . . ?
N2 C10A C9A 116.1(4) . . ?
N2 C10A H10A 108.3 . . ?
C9A C10A H10A 108.3 . . ?
N2 C10A H10B 108.3 . . ?
C9A C10A H10B 108.3 . . ?
H10A C10A H10B 107.4 . . ?
N2 C11A H11A 109.5 . . ?
N2 C11A H11B 109.5 . . ?
N2 C11A H11C 109.5 . . ?
N2 C12A C13A 117.0(4) . . ?
N2 C12A H12A 108.1 . . ?
C13A C12A H12A 108.1 . . ?
N2 C12A H12B 108.1 . . ?
C13A C12A H12B 108.1 . . ?
H12A C12A H12B 107.3 . . ?
C12A C13A C14 116.9(4) . . ?
C12A C13A H13A 108.1 . . ?
C14 C13A H13A 108.1 . . ?
C12A C13A H13B 108.1 . . ?
C14 C13A H13B 108.1 . . ?
H13A C13A H13B 107.3 . . ?
N3 C14 C13A 109.4(4) . . ?
N3 C14 H14A 109.8 . . ?
C13A C14 H14A 109.8 . . ?
N3 C14 H14B 109.8 . . ?
C13A C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
N3 C15 C16 125.2(4) . . ?
N3 C15 H15 117.4 . . ?
C16 C15 H15 117.4 . . ?
C17 C16 C21 119.3(4) . . ?
C17 C16 C15 116.7(4) . . ?
C21 C16 C15 123.9(4) . . ?
C18 C17 C16 120.6(4) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 121.0(4) . . ?
C17 C18 I2 118.5(3) . . ?
C19 C18 I2 120.5(3) . . ?
C20 C19 C18 119.3(4) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 122.0(4) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
O2 C21 C20 119.3(4) . . ?
O2 C21 C16 123.0(4) . . ?
C20 C21 C16 117.6(4) . . ?
C7 N1 C8 117.7(3) . . ?
C7 N1 Ni1 127.0(3) . . ?
C8 N1 Ni1 114.4(3) . . ?
C10B N2 C12B 117.5(13) . . ?
C10B N2 C12A 133.7(9) . . ?
C12B N2 C12A 46.6(9) . . ?
C10B N2 C10A 50.7(10) . . ?
C12B N2 C10A 139.7(9) . . ?
C12A N2 C10A 108.9(4) . . ?
C10B N2 C11A 60.1(10) . . ?
C12B N2 C11A 64.5(9) . . ?
C12A N2 C11A 107.4(4) . . ?
C10A N2 C11A 109.3(4) . . ?
C10B N2 C11B 103.7(12) . . ?
C12B N2 C11B 107.4(12) . . ?
C12A N2 C11B 61.4(8) . . ?
C10A N2 C11B 54.8(8) . . ?
C11A N2 C11B 147.4(8) . . ?
C10B N2 Ni1 113.8(9) . . ?
C12B N2 Ni1 110.3(9) . . ?
C12A N2 Ni1 112.3(3) . . ?
C10A N2 Ni1 109.1(3) . . ?
C11A N2 Ni1 109.9(3) . . ?
C11B N2 Ni1 102.5(7) . . ?
C15 N3 C14 118.5(3) . . ?
C15 N3 Ni1 126.8(3) . . ?
C14 N3 Ni1 114.0(3) . . ?
C1 O1 Ni1 129.2(2) . . ?
C21 O2 Ni1 128.5(3) . . ?
O2 Ni1 O1 141.47(12) . . ?
O2 Ni1 N3 90.16(12) . . ?
O1 Ni1 N3 90.48(12) . . ?
O2 Ni1 N1 90.33(12) . . ?
O1 Ni1 N1 90.05(12) . . ?
N3 Ni1 N1 178.45(13) . . ?
O2 Ni1 N2 105.35(13) . . ?
O1 Ni1 N2 113.18(13) . . ?
N3 Ni1 N2 89.87(13) . . ?
N1 Ni1 N2 88.58(13) . . ?
N2 C11B H11D 109.5 . . ?
N2 C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N2 C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
N2 C12B H12C 106.2 . . ?
N2 C12B H12D 106.2 . . ?
H12C C12B H12D 106.4 . . ?
N2 C10B H10C 107.4 . . ?
N2 C10B H10D 107.4 . . ?
H10C C10B H10D 106.9 . . ?

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
C8 H8B O2 0.99 2.38 2.961(5) 117.1 .
C11A H11B I2 0.98 3.06 4.002(6) 160.7 4_465
C11A H11C N1 0.98 2.65 3.185(6) 114.3 .
C14 H14B O1 0.99 2.51 3.088(5) 117.3 .
C11B H11D O2 0.98 2.54 3.05(2) 112.2 .
C11B H11E N3 0.98 2.67 3.18(2) 112.8 .
C12B H12C I2 0.99 3.17 4.08(2) 152.2 4_465

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.896
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.101
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1047943'
_audit_update_record             
;
2015-04-08 deposited with the CCDC.
2015-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H25 N3 Ni O2'
_chemical_formula_weight         410.15

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'

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

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                   6.9490(8)
_cell_length_b                   14.037(2)
_cell_length_c                   20.113(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.008(13)
_cell_angle_gamma                90.00
_cell_volume                     1960.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8223
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      32.41

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    1.010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7188
_exptl_absorpt_correction_T_max  0.7652
_exptl_absorpt_process_details   
;
 CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
face-indexed (CrysAlis RED; Oxford Diffraction, 2006)
;


_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7791
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3411
_reflns_number_gt                1865
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  ' enCIFer (Allen et al., 2004)'

_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)+(0.0746P)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         3411
_refine_ls_number_parameters     274
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1378
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_restrained_S_all      0.881
_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 0.3105(7) 0.3675(4) 0.3655(3) 0.0552(13) Uani 1 1 d . B .
C2 C 0.1416(7) 0.3109(4) 0.3646(3) 0.0652(15) Uani 1 1 d . . .
H2 H 0.0351 0.3299 0.3386 0.078 Uiso 1 1 calc R . .
C3 C 0.1316(9) 0.2291(4) 0.4010(3) 0.0782(18) Uani 1 1 d . . .
H3 H 0.0199 0.1927 0.3975 0.094 Uiso 1 1 calc R . .
C4 C 0.2796(10) 0.1985(4) 0.4424(3) 0.0796(18) Uani 1 1 d . . .
H4 H 0.2691 0.1427 0.4669 0.096 Uiso 1 1 calc R . .
C5 C 0.4442(9) 0.2528(4) 0.4467(3) 0.0749(17) Uani 1 1 d . . .
H5 H 0.5447 0.2336 0.4754 0.090 Uiso 1 1 calc R . .
C6 C 0.4653(7) 0.3363(4) 0.4092(2) 0.0539(13) Uani 1 1 d . . .
C7 C 0.6424(7) 0.3909(4) 0.4171(2) 0.0570(13) Uani 1 1 d . . .
H7 H 0.7267 0.3740 0.4520 0.068 Uiso 1 1 calc R . .
C8 C 0.8682(6) 0.5145(4) 0.3981(3) 0.0668(16) Uani 1 1 d D . .
H8A H 0.9484 0.5194 0.3597 0.080 Uiso 1 1 calc R A 1
H8B H 0.9415 0.4824 0.4334 0.080 Uiso 1 1 calc R A 1
C9A C 0.810(5) 0.6135(14) 0.4209(16) 0.072(4) Uani 0.460(8) 1 d PD B 1
H9A1 H 0.9074 0.6583 0.4070 0.086 Uiso 0.460(8) 1 calc PR B 1
H9A2 H 0.8128 0.6139 0.4692 0.086 Uiso 0.460(8) 1 calc PR B 1
C10A C 0.6137(15) 0.6500(9) 0.3959(5) 0.063(4) Uani 0.460(8) 1 d PD B 1
H10A H 0.5177 0.6173 0.4214 0.076 Uiso 0.460(8) 1 calc PR B 1
H10B H 0.6071 0.7168 0.4078 0.076 Uiso 0.460(8) 1 calc PR B 1
C9B C 0.826(4) 0.6202(11) 0.4105(14) 0.072(4) Uani 0.540(8) 1 d PD B 2
H9B1 H 0.7388 0.6249 0.4469 0.086 Uiso 0.540(8) 1 calc PR B 2
H9B2 H 0.9458 0.6511 0.4248 0.086 Uiso 0.540(8) 1 calc PR B 2
C10B C 0.7398(14) 0.6752(9) 0.3509(7) 0.101(5) Uani 0.540(8) 1 d PD B 2
H10C H 0.7279 0.7416 0.3635 0.121 Uiso 0.540(8) 1 calc PR B 2
H10D H 0.8297 0.6723 0.3151 0.121 Uiso 0.540(8) 1 calc PR B 2
C11A C 0.7014(17) 0.6949(9) 0.2817(6) 0.073(4) Uani 0.460(8) 1 d P B 1
H11A H 0.6679 0.6855 0.2355 0.110 Uiso 0.460(8) 1 calc PR B 1
H11B H 0.8278 0.6697 0.2913 0.110 Uiso 0.460(8) 1 calc PR B 1
H11C H 0.7002 0.7617 0.2918 0.110 Uiso 0.460(8) 1 calc PR B 1
C11B C 0.3909(14) 0.6572(8) 0.3770(6) 0.081(4) Uani 0.540(8) 1 d P B 2
H11D H 0.3797 0.7238 0.3870 0.122 Uiso 0.540(8) 1 calc PR B 2
H11E H 0.4240 0.6228 0.4170 0.122 Uiso 0.540(8) 1 calc PR B 2
H11F H 0.2703 0.6342 0.3586 0.122 Uiso 0.540(8) 1 calc PR B 2
C12A C 0.3657(14) 0.6838(8) 0.3136(6) 0.060(4) Uani 0.460(8) 1 d PD B 1
H12A H 0.3717 0.7485 0.3306 0.072 Uiso 0.460(8) 1 calc PR B 1
H12B H 0.2768 0.6492 0.3409 0.072 Uiso 0.460(8) 1 calc PR B 1
C13A C 0.275(5) 0.6884(11) 0.2433(16) 0.072(4) Uani 0.460(8) 1 d PD B 1
H13A H 0.1547 0.7231 0.2441 0.086 Uiso 0.460(8) 1 calc PR B 1
H13B H 0.3608 0.7225 0.2145 0.086 Uiso 0.460(8) 1 calc PR B 1
C12B C 0.4985(13) 0.7074(8) 0.2683(5) 0.081(4) Uani 0.540(8) 1 d PD B 2
H12C H 0.5949 0.7011 0.2348 0.098 Uiso 0.540(8) 1 calc PR B 2
H12D H 0.5040 0.7725 0.2844 0.098 Uiso 0.540(8) 1 calc PR B 2
C13B C 0.299(4) 0.6910(9) 0.2344(14) 0.072(4) Uani 0.540(8) 1 d PD B 2
H13C H 0.2032 0.7163 0.2636 0.086 Uiso 0.540(8) 1 calc PR B 2
H13D H 0.2923 0.7290 0.1940 0.086 Uiso 0.540(8) 1 calc PR B 2
C14 C 0.2387(6) 0.5890(4) 0.2157(3) 0.0657(15) Uani 1 1 d D . .
H14A H 0.1536 0.5555 0.2449 0.079 Uiso 1 1 calc R B 1
H14B H 0.1730 0.5944 0.1725 0.079 Uiso 1 1 calc R B 1
C15 C 0.4680(6) 0.5078(3) 0.1511(2) 0.0538(12) Uani 1 1 d . . .
H15 H 0.3844 0.5229 0.1155 0.065 Uiso 1 1 calc R B .
C16 C 0.6444(6) 0.4596(4) 0.1353(2) 0.0506(12) Uani 1 1 d . B .
C17 C 0.6728(8) 0.4341(4) 0.0694(3) 0.0704(15) Uani 1 1 d . . .
H17 H 0.5732 0.4444 0.0381 0.084 Uiso 1 1 calc R B .
C18 C 0.8420(9) 0.3943(4) 0.0483(3) 0.0797(18) Uani 1 1 d . B .
H18 H 0.8569 0.3788 0.0038 0.096 Uiso 1 1 calc R . .
C19 C 0.9899(8) 0.3778(4) 0.0956(3) 0.0745(17) Uani 1 1 d . . .
H19 H 1.1049 0.3506 0.0829 0.089 Uiso 1 1 calc R B .
C20 C 0.9664(7) 0.4014(4) 0.1603(3) 0.0625(14) Uani 1 1 d . B .
H20 H 1.0675 0.3901 0.1908 0.075 Uiso 1 1 calc R . .
C21 C 0.7935(6) 0.4430(3) 0.1838(2) 0.0498(12) Uani 1 1 d . . .
N1 N 0.6922(5) 0.4596(3) 0.38053(19) 0.0534(10) Uani 1 1 d . B .
N2 N 0.5523(5) 0.6423(3) 0.3251(2) 0.0588(11) Uani 1 1 d D . .
N3 N 0.4155(5) 0.5317(3) 0.20849(19) 0.0505(10) Uani 1 1 d . B .
O1 O 0.3157(4) 0.4430(3) 0.32852(17) 0.0673(10) Uani 1 1 d . . .
O2 O 0.7846(4) 0.4641(3) 0.24652(16) 0.0672(10) Uani 1 1 d . B .
Ni1 Ni 0.55394(7) 0.49944(5) 0.29518(3) 0.0451(2) Uani 1 1 d . B .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.296(6) . ?
C1 C2 1.417(6) . ?
C1 C6 1.434(7) . ?
C2 C3 1.364(7) . ?
C3 C4 1.370(8) . ?
C4 C5 1.374(8) . ?
C5 C6 1.405(7) . ?
C6 C7 1.454(7) . ?
C7 N1 1.267(6) . ?
C8 N1 1.478(6) . ?
C8 C9A 1.522(13) . ?
C8 C9B 1.534(11) . ?
C9A C10A 1.527(19) . ?
C10A N2 1.476(9) . ?
C9B C10B 1.533(18) . ?
C10B N2 1.460(9) . ?
C11A N2 1.563(11) . ?
C11B N2 1.572(9) . ?
C12A N2 1.433(9) . ?
C12A C13A 1.53(2) . ?
C13A C14 1.521(13) . ?
C12B N2 1.501(10) . ?
C12B C13B 1.541(17) . ?
C13B C14 1.535(12) . ?
C14 N3 1.480(5) . ?
C15 N3 1.267(5) . ?
C15 C16 1.445(6) . ?
C16 C17 1.395(6) . ?
C16 C21 1.416(6) . ?
C17 C18 1.382(7) . ?
C18 C19 1.396(8) . ?
C19 C20 1.357(7) . ?
C20 C21 1.430(6) . ?
C21 O2 1.300(5) . ?
N1 Ni1 2.017(4) . ?
N2 Ni1 2.094(4) . ?
N3 Ni1 2.013(4) . ?
O1 Ni1 1.974(3) . ?
O2 Ni1 1.971(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
O1 C1 C2 119.4(5) . . ?
O1 C1 C6 124.5(4) . . ?
C2 C1 C6 116.1(5) . . ?
C3 C2 C1 121.5(5) . . ?
C2 C3 C4 122.6(6) . . ?
C3 C4 C5 118.1(6) . . ?
C4 C5 C6 122.1(6) . . ?
C5 C6 C1 119.6(5) . . ?
C5 C6 C7 119.1(5) . . ?
C1 C6 C7 121.3(5) . . ?
N1 C7 C6 125.8(5) . . ?
N1 C8 C9A 108.9(13) . . ?
N1 C8 C9B 112.6(11) . . ?
C9A C8 C9B 10(3) . . ?
C8 C9A C10A 116.7(14) . . ?
N2 C10A C9A 121.2(15) . . ?
C10B C9B C8 115.5(13) . . ?
N2 C10B C9B 116.1(15) . . ?
N2 C12A C13A 120.4(16) . . ?
C14 C13A C12A 110.9(14) . . ?
N2 C12B C13B 116.3(13) . . ?
C14 C13B C12B 118.7(11) . . ?
N3 C14 C13A 113.9(13) . . ?
N3 C14 C13B 108.1(10) . . ?
C13A C14 C13B 9(3) . . ?
N3 C15 C16 126.7(4) . . ?
C17 C16 C21 119.2(4) . . ?
C17 C16 C15 118.6(4) . . ?
C21 C16 C15 122.1(4) . . ?
C18 C17 C16 123.1(5) . . ?
C17 C18 C19 118.1(5) . . ?
C20 C19 C18 120.2(5) . . ?
C19 C20 C21 123.1(5) . . ?
O2 C21 C16 124.9(4) . . ?
O2 C21 C20 118.8(4) . . ?
C16 C21 C20 116.3(4) . . ?
C7 N1 C8 119.9(4) . . ?
C7 N1 Ni1 125.0(3) . . ?
C8 N1 Ni1 115.1(3) . . ?
C12A N2 C10B 136.1(7) . . ?
C12A N2 C10A 110.8(7) . . ?
C10B N2 C10A 53.9(7) . . ?
C12A N2 C12B 55.2(6) . . ?
C10B N2 C12B 105.8(7) . . ?
C10A N2 C12B 138.3(7) . . ?
C12A N2 C11A 109.4(8) . . ?
C10B N2 C11A 56.5(7) . . ?
C10A N2 C11A 109.2(8) . . ?
C12B N2 C11A 55.9(6) . . ?
C12A N2 C11B 52.4(6) . . ?
C10B N2 C11B 111.8(8) . . ?
C10A N2 C11B 62.6(6) . . ?
C12B N2 C11B 105.1(7) . . ?
C11A N2 C11B 144.1(7) . . ?
C12A N2 Ni1 110.9(5) . . ?
C10B N2 Ni1 113.0(5) . . ?
C10A N2 Ni1 110.1(5) . . ?
C12B N2 Ni1 111.6(5) . . ?
C11A N2 Ni1 106.3(5) . . ?
C11B N2 Ni1 109.2(5) . . ?
C15 N3 C14 119.9(4) . . ?
C15 N3 Ni1 125.8(3) . . ?
C14 N3 Ni1 114.3(3) . . ?
C1 O1 Ni1 124.3(3) . . ?
C21 O2 Ni1 127.4(3) . . ?
O2 Ni1 O1 140.73(18) . . ?
O2 Ni1 N3 89.93(14) . . ?
O1 Ni1 N3 90.20(14) . . ?
O2 Ni1 N1 88.93(14) . . ?
O1 Ni1 N1 88.84(15) . . ?
N3 Ni1 N1 176.86(17) . . ?
O2 Ni1 N2 113.39(16) . . ?
O1 Ni1 N2 105.86(16) . . ?
N3 Ni1 N2 91.52(17) . . ?
N1 Ni1 N2 91.62(18) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.096
