# Electronic Supplementary Material (ESI) for ChemComm.
# 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_13yuj22
_database_code_depnum_ccdc_archive 'CCDC 1052385'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H24 Cl2 N Ni O3 P'
_chemical_formula_weight         607.08

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'
P P 0.1023 0.0942 '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                   10.2518(6)
_cell_length_b                   11.9007(7)
_cell_length_c                   13.0245(7)
_cell_angle_alpha                111.4380(10)
_cell_angle_beta                 97.5860(10)
_cell_angle_gamma                98.5930(10)
_cell_volume                     1432.11(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5078
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.79

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7900
_exptl_absorpt_correction_T_max  0.8550
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18730
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5629
_reflns_number_gt                4659
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0228P)²+0.8868P] 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         5629
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0708
_refine_ls_wR_factor_gt          0.0650
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Ni1 Ni 0.23868(3) 0.89322(2) 0.07060(2) 0.01836(8) Uani 1 1 d . . .
O1 O 0.02559(17) 0.69069(15) -0.09439(14) 0.0349(4) Uani 1 1 d . . .
O2 O 0.1850(2) 1.13260(16) 0.08217(15) 0.0412(5) Uani 1 1 d . . .
O3 O 0.49102(17) 0.85813(18) -0.00791(14) 0.0402(5) Uani 1 1 d . . .
N1 N 0.28346(18) 0.89346(16) 0.31030(15) 0.0215(4) Uani 1 1 d . . .
C1 C 0.2649(2) 0.89211(18) 0.22062(18) 0.0179(4) Uani 1 1 d . . .
C2 C 0.1056(2) 0.7687(2) -0.02583(18) 0.0235(5) Uani 1 1 d . . .
C3 C 0.2055(2) 1.0403(2) 0.08037(18) 0.0252(5) Uani 1 1 d . . .
C4 C 0.3939(2) 0.8727(2) 0.02412(17) 0.0261(5) Uani 1 1 d . . .
P1 P 0.42911(5) 0.26373(5) 0.54932(4) 0.01368(12) Uani 1 1 d . . .
C5 C 0.3909(2) 0.11914(17) 0.56672(16) 0.0150(4) Uani 1 1 d . . .
H5A H 0.3528 0.0522 0.4916 0.018 Uiso 1 1 calc R . .
H5B H 0.4761 0.1020 0.5968 0.018 Uiso 1 1 calc R . .
C6 C 0.2932(2) 0.11493(17) 0.64383(16) 0.0150(4) Uani 1 1 d . . .
C7 C 0.3404(2) 0.12030(18) 0.75110(17) 0.0181(4) Uani 1 1 d . . .
H7 H 0.4342 0.1304 0.7770 0.022 Uiso 1 1 calc R . .
C8 C 0.2511(2) 0.11102(19) 0.82035(18) 0.0228(5) Uani 1 1 d . . .
H8 H 0.2838 0.1133 0.8930 0.027 Uiso 1 1 calc R . .
C9 C 0.1141(2) 0.09834(19) 0.78400(18) 0.0229(5) Uani 1 1 d . . .
H9 H 0.0532 0.0926 0.8318 0.027 Uiso 1 1 calc R . .
C10 C 0.0665(2) 0.09414(18) 0.67789(18) 0.0217(5) Uani 1 1 d . . .
H10 H -0.0271 0.0859 0.6529 0.026 Uiso 1 1 calc R . .
C11 C 0.1555(2) 0.10192(18) 0.60788(17) 0.0181(4) Uani 1 1 d . . .
H11 H 0.1222 0.0983 0.5349 0.022 Uiso 1 1 calc R . .
C12 C 0.5454(2) 0.24833(18) 0.45536(16) 0.0153(4) Uani 1 1 d . . .
C13 C 0.5167(2) 0.27468(19) 0.36003(17) 0.0190(4) Uani 1 1 d . . .
H13 H 0.4379 0.3043 0.3463 0.023 Uiso 1 1 calc R . .
C14 C 0.6033(2) 0.25757(19) 0.28543(17) 0.0218(5) Uani 1 1 d . . .
H14 H 0.5837 0.2751 0.2202 0.026 Uiso 1 1 calc R . .
C15 C 0.7184(2) 0.21503(19) 0.30531(17) 0.0207(5) Uani 1 1 d . . .
H15 H 0.7768 0.2022 0.2531 0.025 Uiso 1 1 calc R . .
C16 C 0.7489(2) 0.19101(18) 0.40140(18) 0.0203(5) Uani 1 1 d . . .
H16 H 0.8295 0.1640 0.4157 0.024 Uiso 1 1 calc R . .
C17 C 0.6624(2) 0.20635(18) 0.47656(17) 0.0172(4) Uani 1 1 d . . .
H17 H 0.6824 0.1886 0.5416 0.021 Uiso 1 1 calc R . .
C18 C 0.5000(2) 0.38996(18) 0.68277(16) 0.0150(4) Uani 1 1 d . . .
C19 C 0.6303(2) 0.45834(18) 0.70268(17) 0.0179(4) Uani 1 1 d . . .
H19 H 0.6832 0.4372 0.6466 0.022 Uiso 1 1 calc R . .
C20 C 0.6820(2) 0.55734(19) 0.80472(18) 0.0233(5) Uani 1 1 d . . .
H20 H 0.7709 0.6041 0.8188 0.028 Uiso 1 1 calc R . .
C21 C 0.6046(2) 0.58824(19) 0.88620(17) 0.0236(5) Uani 1 1 d . . .
H21 H 0.6406 0.6563 0.9560 0.028 Uiso 1 1 calc R . .
C22 C 0.4751(2) 0.52075(19) 0.86670(17) 0.0216(5) Uani 1 1 d . . .
H22 H 0.4228 0.5426 0.9232 0.026 Uiso 1 1 calc R . .
C23 C 0.4214(2) 0.42138(19) 0.76508(17) 0.0198(5) Uani 1 1 d . . .
H23 H 0.3324 0.3752 0.7514 0.024 Uiso 1 1 calc R . .
C24 C 0.28107(19) 0.29602(18) 0.48525(16) 0.0150(4) Uani 1 1 d . . .
C25 C 0.1972(2) 0.20365(18) 0.38860(16) 0.0168(4) Uani 1 1 d . . .
H25 H 0.2131 0.1222 0.3619 0.020 Uiso 1 1 calc R . .
C26 C 0.0908(2) 0.23149(19) 0.33192(16) 0.0179(4) Uani 1 1 d . . .
H26 H 0.0326 0.1687 0.2668 0.021 Uiso 1 1 calc R . .
C27 C 0.0690(2) 0.35101(19) 0.37015(17) 0.0180(4) Uani 1 1 d . . .
H27 H -0.0032 0.3700 0.3303 0.022 Uiso 1 1 calc R . .
C28 C 0.1516(2) 0.44238(18) 0.46578(17) 0.0176(4) Uani 1 1 d . . .
H28 H 0.1355 0.5238 0.4919 0.021 Uiso 1 1 calc R . .
C29 C 0.2579(2) 0.41553(18) 0.52375(16) 0.0156(4) Uani 1 1 d . . .
H29 H 0.3148 0.4784 0.5895 0.019 Uiso 1 1 calc R . .
Cl1 Cl -0.00493(7) 0.61527(5) 0.31228(5) 0.03357(15) Uani 1 1 d . . .
Cl2 Cl -0.13137(6) 0.57049(5) 0.08229(5) 0.02957(14) Uani 1 1 d . . .
C30 C 0.0223(2) 0.6153(2) 0.18067(18) 0.0246(5) Uani 1 1 d . . .
H30A H 0.0687 0.6991 0.1912 0.029 Uiso 1 1 calc R . .
H30B H 0.0814 0.5575 0.1510 0.029 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 C2 1.794(2) . ?
Ni1 C4 1.795(2) . ?
Ni1 C3 1.795(2) . ?
Ni1 C1 1.942(2) . ?
O1 C2 1.143(3) . ?
O2 C3 1.141(3) . ?
O3 C4 1.142(3) . ?
N1 C1 1.152(3) . ?
P1 C24 1.795(2) . ?
P1 C18 1.799(2) . ?
P1 C12 1.800(2) . ?
P1 C5 1.809(2) . ?
C5 C6 1.517(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.392(3) . ?
C6 C11 1.394(3) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.394(3) . ?
C12 C17 1.399(3) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.394(3) . ?
C18 C23 1.401(3) . ?
C19 C20 1.385(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C29 1.393(3) . ?
C24 C25 1.397(3) . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.388(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.381(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.387(3) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
Cl1 C30 1.773(2) . ?
Cl2 C30 1.768(2) . ?
C30 H30A 0.9900 . ?
C30 H30B 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
C2 Ni1 C4 108.70(10) . . ?
C2 Ni1 C3 111.26(10) . . ?
C4 Ni1 C3 110.53(10) . . ?
C2 Ni1 C1 111.84(9) . . ?
C4 Ni1 C1 105.95(9) . . ?
C3 Ni1 C1 108.44(9) . . ?
N1 C1 Ni1 178.28(19) . . ?
O1 C2 Ni1 174.2(2) . . ?
O2 C3 Ni1 177.22(19) . . ?
O3 C4 Ni1 178.4(2) . . ?
C24 P1 C18 108.69(9) . . ?
C24 P1 C12 107.40(9) . . ?
C18 P1 C12 110.83(9) . . ?
C24 P1 C5 111.26(9) . . ?
C18 P1 C5 110.96(9) . . ?
C12 P1 C5 107.65(9) . . ?
C6 C5 P1 115.09(13) . . ?
C6 C5 H5A 108.5 . . ?
P1 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
P1 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C7 C6 C11 119.07(18) . . ?
C7 C6 C5 119.84(17) . . ?
C11 C6 C5 121.06(18) . . ?
C8 C7 C6 120.26(19) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C6 120.53(19) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
C13 C12 C17 120.20(18) . . ?
C13 C12 P1 119.98(15) . . ?
C17 C12 P1 119.79(15) . . ?
C14 C13 C12 119.83(19) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.20(19) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 120.32(19) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 119.18(19) . . ?
C16 C17 H17 120.4 . . ?
C12 C17 H17 120.4 . . ?
C19 C18 C23 120.33(18) . . ?
C19 C18 P1 120.29(15) . . ?
C23 C18 P1 119.35(15) . . ?
C20 C19 C18 119.58(19) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C21 C20 C19 120.1(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 120.48(19) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.3(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 119.19(19) . . ?
C22 C23 H23 120.4 . . ?
C18 C23 H23 120.4 . . ?
C29 C24 C25 120.02(18) . . ?
C29 C24 P1 120.30(15) . . ?
C25 C24 P1 119.29(15) . . ?
C26 C25 C24 119.62(19) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 120.08(19) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C28 C27 C26 120.37(19) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 120.12(19) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C28 C29 C24 119.78(18) . . ?
C28 C29 H29 120.1 . . ?
C24 C29 H29 120.1 . . ?
Cl2 C30 Cl1 111.24(12) . . ?
Cl2 C30 H30A 109.4 . . ?
Cl1 C30 H30A 109.4 . . ?
Cl2 C30 H30B 109.4 . . ?
Cl1 C30 H30B 109.4 . . ?
H30A C30 H30B 108.0 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_14yuj35
_database_code_depnum_ccdc_archive 'CCDC 1052386'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H40 N4 Ni O2'
_chemical_formula_weight         427.27

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   'C 2/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                   14.857(3)
_cell_length_b                   10.303(2)
_cell_length_c                   15.562(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.009(2)
_cell_angle_gamma                90.00
_cell_volume                     2352.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2962
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8230
_exptl_absorpt_correction_T_max  0.9203
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13307
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         26.42
_reflns_number_total             2418
_reflns_number_gt                1973
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0440P)²+0.9971P] 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         2418
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.17157(3) 0.2500 0.02723(13) Uani 1 2 d S . .
O1 O 0.37227(13) 0.00159(19) 0.14253(12) 0.0599(5) Uani 1 1 d . . .
N1 N 0.41137(12) 0.35187(17) 0.37376(12) 0.0354(4) Uani 1 1 d . . .
C1 C 0.44405(13) 0.28692(19) 0.32628(13) 0.0280(4) Uani 1 1 d . . .
C2 C 0.42018(14) 0.0737(2) 0.18406(14) 0.0339(5) Uani 1 1 d . . .
N2 N 0.30761(11) 0.44445(15) 0.61680(10) 0.0261(4) Uani 1 1 d . . .
C3 C 0.36223(15) 0.33966(19) 0.58013(14) 0.0333(5) Uani 1 1 d . . .
H3A H 0.3357 0.2543 0.5913 0.040 Uiso 1 1 calc R . .
H3B H 0.3552 0.3511 0.5163 0.040 Uiso 1 1 calc R . .
C4 C 0.46266(16) 0.3367(2) 0.61586(18) 0.0493(6) Uani 1 1 d . . .
H4A H 0.4926 0.2702 0.5852 0.074 Uiso 1 1 calc R . .
H4B H 0.4710 0.3161 0.6781 0.074 Uiso 1 1 calc R . .
H4C H 0.4896 0.4217 0.6075 0.074 Uiso 1 1 calc R . .
C5 C 0.34217(15) 0.57838(19) 0.59713(15) 0.0356(5) Uani 1 1 d . . .
H5A H 0.3077 0.6442 0.6250 0.043 Uiso 1 1 calc R . .
H5B H 0.4070 0.5854 0.6239 0.043 Uiso 1 1 calc R . .
C6 C 0.33439(17) 0.6100(2) 0.50183(16) 0.0444(6) Uani 1 1 d . . .
H6A H 0.3643 0.6933 0.4948 0.067 Uiso 1 1 calc R . .
H6B H 0.2699 0.6157 0.4762 0.067 Uiso 1 1 calc R . .
H6C H 0.3639 0.5416 0.4724 0.067 Uiso 1 1 calc R . .
C7 C 0.31775(15) 0.4362(2) 0.71526(13) 0.0334(5) Uani 1 1 d . . .
H7A H 0.3812 0.4592 0.7400 0.040 Uiso 1 1 calc R . .
H7B H 0.2773 0.5019 0.7357 0.040 Uiso 1 1 calc R . .
C8 C 0.29608(16) 0.3057(2) 0.75082(14) 0.0400(5) Uani 1 1 d . . .
H8A H 0.3031 0.3102 0.8144 0.060 Uiso 1 1 calc R . .
H8B H 0.3378 0.2403 0.7338 0.060 Uiso 1 1 calc R . .
H8C H 0.2332 0.2818 0.7273 0.060 Uiso 1 1 calc R . .
C9 C 0.20962(13) 0.4246(2) 0.57455(13) 0.0320(5) Uani 1 1 d . . .
H9A H 0.2074 0.4250 0.5106 0.038 Uiso 1 1 calc R . .
H9B H 0.1899 0.3374 0.5910 0.038 Uiso 1 1 calc R . .
C10 C 0.14186(15) 0.5229(2) 0.59717(16) 0.0429(6) Uani 1 1 d . . .
H10A H 0.0809 0.5009 0.5669 0.064 Uiso 1 1 calc R . .
H10B H 0.1589 0.6095 0.5792 0.064 Uiso 1 1 calc R . .
H10C H 0.1418 0.5221 0.6601 0.064 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 C2 1.759(2) 2_655 ?
Ni1 C2 1.759(2) . ?
Ni1 C1 1.955(2) . ?
Ni1 C1 1.955(2) 2_655 ?
O1 C2 1.154(3) . ?
N1 C1 1.158(3) . ?
N2 C9 1.515(2) . ?
N2 C3 1.515(2) . ?
N2 C7 1.518(2) . ?
N2 C5 1.520(2) . ?
C3 C4 1.509(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.505(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.507(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.508(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Ni1 C2 110.08(14) 2_655 . ?
C2 Ni1 C1 107.82(9) 2_655 . ?
C2 Ni1 C1 112.99(9) . . ?
C2 Ni1 C1 112.99(9) 2_655 2_655 ?
C2 Ni1 C1 107.82(9) . 2_655 ?
C1 Ni1 C1 105.12(11) . 2_655 ?
N1 C1 Ni1 177.55(18) . . ?
O1 C2 Ni1 174.7(2) . . ?
C9 N2 C3 105.98(15) . . ?
C9 N2 C7 111.55(15) . . ?
C3 N2 C7 111.45(15) . . ?
C9 N2 C5 111.56(15) . . ?
C3 N2 C5 110.69(15) . . ?
C7 N2 C5 105.72(15) . . ?
C4 C3 N2 115.66(17) . . ?
C4 C3 H3A 108.4 . . ?
N2 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
N2 C3 H3B 108.4 . . ?
H3A C3 H3B 107.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N2 114.75(17) . . ?
C6 C5 H5A 108.6 . . ?
N2 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
N2 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N2 115.30(16) . . ?
C8 C7 H7A 108.5 . . ?
N2 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
N2 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N2 116.06(17) . . ?
C10 C9 H9A 108.3 . . ?
N2 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
N2 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.053

