# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1507895'
_audit_update_record             
;
2016-10-03 deposited with the CCDC.
2018-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H29 N3 Ni O2'
_chemical_formula_sum            'C27 H29 N3 Ni O2'
_chemical_formula_weight         486.24

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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.7052(6)
_cell_length_b                   18.0704(11)
_cell_length_c                   14.1301(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.8527(15)
_cell_angle_gamma                90
_cell_volume                     2358.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8847
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      28.46

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.852
_shelx_estimated_absorpt_T_min   0.822
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5929
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-Duo CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37576
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.887
_diffrn_reflns_theta_max         28.760
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6121
_reflns_number_gt                4530
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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-2014/7 (Sheldrick, 2014)'
_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     
'w=1/[σ²(Fo²)+(0.0808P)²+0.5189P] 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         6121
_refine_ls_number_parameters     304
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1353
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.022
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.34294(3) 0.04158(2) 0.31815(2) 0.03969(11) Uani 1 1 d . . . . .
N1 N 0.2198(2) -0.03034(9) 0.33828(14) 0.0420(4) Uani 1 1 d . . . . .
O1 O 0.30555(16) 0.00365(8) 0.19209(11) 0.0439(3) Uani 1 1 d . . . . .
C1 C 0.4652(3) 0.13553(13) 0.19909(19) 0.0528(5) Uani 1 1 d . U . . .
H1 H 0.4175 0.1066 0.1444 0.063 Uiso 1 1 calc R U . . .
C2 C 0.5442(3) 0.19588(14) 0.1860(2) 0.0613(6) Uani 1 1 d . U . . .
H2 H 0.5459 0.2088 0.1227 0.074 Uiso 1 1 calc R U . . .
O2 O 0.5727(3) 0.16640(14) 0.53917(17) 0.0911(7) Uani 1 1 d . . . . .
N2 N 0.4556(2) 0.11768(10) 0.28806(14) 0.0442(4) Uani 1 1 d . . . . .
C3 C 0.6207(3) 0.23701(15) 0.2672(2) 0.0657(7) Uani 1 1 d . U . . .
H3 H 0.6758 0.2774 0.2598 0.079 Uiso 1 1 calc R U . . .
N3 N 0.3978(2) 0.08145(10) 0.44785(14) 0.0452(4) Uani 1 1 d . . . . .
C5 C 0.5282(2) 0.15760(12) 0.36789(18) 0.0492(5) Uani 1 1 d . U . . .
C6 C 0.5026(3) 0.13546(13) 0.46248(18) 0.0544(6) Uani 1 1 d . . . . .
C7 C 0.3455(3) 0.05935(14) 0.52490(17) 0.0524(6) Uani 1 1 d . . . . .
C8 C 0.3887(4) 0.09202(19) 0.6201(2) 0.0726(8) Uani 1 1 d . . . . .
H8 H 0.4586 0.1291 0.6342 0.087 Uiso 1 1 calc R U . . .
C9 C 0.3300(5) 0.0704(2) 0.6924(2) 0.0876(11) Uani 1 1 d . . . . .
H9 H 0.3613 0.0934 0.7542 0.105 Uiso 1 1 calc R U . . .
C10 C 0.2261(5) 0.0155(2) 0.6769(2) 0.0896(11) Uani 1 1 d . . . . .
H10 H 0.1865 0.0023 0.7266 0.108 Uiso 1 1 calc R U . . .
C11 C 0.1832(4) -0.0187(2) 0.5861(2) 0.0777(9) Uani 1 1 d . . . . .
H11 H 0.1151 -0.0565 0.5746 0.093 Uiso 1 1 calc R U . . .
C12 C 0.2410(3) 0.00249(15) 0.50870(18) 0.0563(6) Uani 1 1 d . . . . .
C13 C 0.1860(3) -0.03927(13) 0.4188(2) 0.0556(6) Uani 1 1 d . . . . .
H13 H 0.1196 -0.0764 0.4186 0.067 Uiso 1 1 calc R U . . .
C14 C 0.1631(2) -0.07523(11) 0.25293(16) 0.0417(4) Uani 1 1 d . . . . .
C15 C 0.0645(3) -0.13371(12) 0.24237(19) 0.0493(5) Uani 1 1 d . . . . .
H15 H 0.0297 -0.1462 0.2947 0.059 Uiso 1 1 calc R U . . .
C16 C 0.0196(2) -0.17247(11) 0.15476(19) 0.0490(5) Uani 1 1 d . . . . .
C17 C 0.0764(2) -0.15197(12) 0.07862(17) 0.0468(5) Uani 1 1 d . . . . .
H17 H 0.0471 -0.1789 0.0197 0.056 Uiso 1 1 calc R U . . .
C19 C 0.2165(2) -0.05438(11) 0.17564(16) 0.0392(4) Uani 1 1 d . . . . .
C21 C -0.1370(4) -0.2517(2) 0.2314(3) 0.0955(12) Uani 1 1 d . . . . .
H21A H -0.1867 -0.2092 0.2456 0.143 Uiso 1 1 calc R U . . .
H21B H -0.0527 -0.2615 0.2869 0.143 Uiso 1 1 calc R U . . .
H21C H -0.2002 -0.2938 0.2198 0.143 Uiso 1 1 calc R U . . .
C20 C -0.0904(3) -0.23639(14) 0.1371(2) 0.0643(7) Uani 1 1 d . . . . .
C22 C -0.0231(4) -0.30697(17) 0.1154(4) 0.1034(14) Uani 1 1 d . . . . .
H22A H -0.0850 -0.3480 0.1175 0.155 Uiso 1 1 calc R U . . .
H22B H 0.0695 -0.3139 0.1644 0.155 Uiso 1 1 calc R U . . .
H22C H -0.0111 -0.3040 0.0506 0.155 Uiso 1 1 calc R U . . .
C23 C -0.2240(4) -0.2164(2) 0.0544(3) 0.1115(16) Uani 1 1 d . . . . .
H23A H -0.2014 -0.2142 -0.0071 0.167 Uiso 1 1 calc R U . . .
H23B H -0.2588 -0.1690 0.0678 0.167 Uiso 1 1 calc R U . . .
H23C H -0.2972 -0.2532 0.0495 0.167 Uiso 1 1 calc R U . . .
C24 C 0.2324(3) -0.07404(12) -0.00025(16) 0.0455(5) Uani 1 1 d . . . . .
C25 C 0.1696(3) -0.12308(17) -0.09142(19) 0.0671(7) Uani 1 1 d . . . . .
H25A H 0.0666 -0.1164 -0.1159 0.101 Uiso 1 1 calc R U . . .
H25B H 0.1911 -0.1740 -0.0734 0.101 Uiso 1 1 calc R U . . .
H25C H 0.2117 -0.1097 -0.1423 0.101 Uiso 1 1 calc R U . . .
C26 C 0.3978(3) -0.08221(15) 0.03420(19) 0.0545(6) Uani 1 1 d . . . . .
H26A H 0.4231 -0.1327 0.0530 0.082 Uiso 1 1 calc R U . . .
H26B H 0.4389 -0.0504 0.0902 0.082 Uiso 1 1 calc R U . . .
H26C H 0.4349 -0.0687 -0.0191 0.082 Uiso 1 1 calc R U . . .
C27 C 0.1921(3) 0.00613(14) -0.03357(19) 0.0583(6) Uani 1 1 d . . . . .
H27A H 0.2380 0.0199 -0.0822 0.087 Uiso 1 1 calc R U . . .
H27B H 0.2241 0.0385 0.0228 0.087 Uiso 1 1 calc R U . . .
H27C H 0.0890 0.0101 -0.0621 0.087 Uiso 1 1 calc R U . . .
C18 C 0.1737(2) -0.09409(11) 0.08505(16) 0.0401(4) Uani 1 1 d . . . . .
C4 C 0.6137(3) 0.21679(14) 0.3597(2) 0.0638(7) Uani 1 1 d . U . . .
H4 H 0.6660 0.2428 0.4161 0.077 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.8379(14) . ?
Ni1 N1 1.8454(18) . ?
Ni1 N2 1.8845(18) . ?
Ni1 N3 1.8876(18) . ?
N1 C13 1.287(3) . ?
N1 C14 1.417(3) . ?
O1 C19 1.333(2) . ?
C1 N2 1.329(3) . ?
C1 C2 1.378(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(4) . ?
C2 H2 0.9300 . ?
O2 C6 1.224(3) . ?
N2 C5 1.343(3) . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
N3 C6 1.379(3) . ?
N3 C7 1.394(3) . ?
C5 C4 1.379(4) . ?
C5 C6 1.487(4) . ?
C7 C8 1.410(3) . ?
C7 C12 1.412(4) . ?
C8 C9 1.370(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.425(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.433(4) . ?
C13 H13 0.9300 . ?
C14 C19 1.397(3) . ?
C14 C15 1.402(3) . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.401(3) . ?
C16 C20 1.540(3) . ?
C17 C18 1.393(3) . ?
C17 H17 0.9300 . ?
C19 C18 1.414(3) . ?
C21 C20 1.557(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C20 C23 1.499(4) . ?
C20 C22 1.506(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C18 1.527(3) . ?
C24 C25 1.528(3) . ?
C24 C26 1.535(3) . ?
C24 C27 1.536(3) . ?
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 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 N1 86.67(7) . . ?
O1 Ni1 N2 90.53(7) . . ?
N1 Ni1 N2 175.09(8) . . ?
O1 Ni1 N3 175.14(7) . . ?
N1 Ni1 N3 97.04(8) . . ?
N2 Ni1 N3 85.98(8) . . ?
C13 N1 C14 122.9(2) . . ?
C13 N1 Ni1 125.23(18) . . ?
C14 N1 Ni1 111.89(14) . . ?
C19 O1 Ni1 112.78(13) . . ?
N2 C1 C2 121.5(2) . . ?
N2 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C1 N2 C5 119.5(2) . . ?
C1 N2 Ni1 127.20(16) . . ?
C5 N2 Ni1 113.22(16) . . ?
C2 C3 C4 118.4(2) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C6 N3 C7 121.0(2) . . ?
C6 N3 Ni1 113.04(15) . . ?
C7 N3 Ni1 125.95(17) . . ?
N2 C5 C4 121.4(2) . . ?
N2 C5 C6 114.9(2) . . ?
C4 C5 C6 123.6(2) . . ?
O2 C6 N3 129.8(3) . . ?
O2 C6 C5 118.2(3) . . ?
N3 C6 C5 112.00(19) . . ?
N3 C7 C8 123.5(3) . . ?
N3 C7 C12 119.8(2) . . ?
C8 C7 C12 116.6(3) . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 122.4(3) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C11 C10 C9 118.0(3) . . ?
C11 C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
C10 C11 C12 121.3(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C7 C12 C11 120.2(3) . . ?
C7 C12 C13 125.5(2) . . ?
C11 C12 C13 114.3(3) . . ?
N1 C13 C12 126.2(2) . . ?
N1 C13 H13 116.9 . . ?
C12 C13 H13 116.9 . . ?
C19 C14 C15 121.6(2) . . ?
C19 C14 N1 111.75(18) . . ?
C15 C14 N1 126.6(2) . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 117.8(2) . . ?
C15 C16 C20 122.8(2) . . ?
C17 C16 C20 119.3(2) . . ?
C18 C17 C16 124.5(2) . . ?
C18 C17 H17 117.7 . . ?
C16 C17 H17 117.7 . . ?
O1 C19 C14 116.87(18) . . ?
O1 C19 C18 123.50(19) . . ?
C14 C19 C18 119.62(18) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C20 C22 111.8(3) . . ?
C23 C20 C16 109.6(2) . . ?
C22 C20 C16 110.2(2) . . ?
C23 C20 C21 107.5(3) . . ?
C22 C20 C21 106.3(3) . . ?
C16 C20 C21 111.3(2) . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 C24 C25 112.3(2) . . ?
C18 C24 C26 109.52(18) . . ?
C25 C24 C26 108.6(2) . . ?
C18 C24 C27 110.11(18) . . ?
C25 C24 C27 106.9(2) . . ?
C26 C24 C27 109.4(2) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C17 C18 C19 116.45(19) . . ?
C17 C18 C24 122.43(19) . . ?
C19 C18 C24 121.12(18) . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Ni1 N1 C13 -179.0(2) . . . . ?
N3 Ni1 N1 C13 4.2(2) . . . . ?
O1 Ni1 N1 C14 0.11(14) . . . . ?
N3 Ni1 N1 C14 -176.74(14) . . . . ?
N1 Ni1 O1 C19 -1.19(14) . . . . ?
N2 Ni1 O1 C19 -177.15(14) . . . . ?
N2 C1 C2 C3 3.0(4) . . . . ?
C2 C1 N2 C5 -2.3(4) . . . . ?
C2 C1 N2 Ni1 175.49(19) . . . . ?
O1 Ni1 N2 C1 11.0(2) . . . . ?
N3 Ni1 N2 C1 -172.4(2) . . . . ?
O1 Ni1 N2 C5 -171.04(15) . . . . ?
N3 Ni1 N2 C5 5.58(15) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
N1 Ni1 N3 C6 175.26(15) . . . . ?
N2 Ni1 N3 C6 -8.63(15) . . . . ?
N1 Ni1 N3 C7 -2.76(19) . . . . ?
N2 Ni1 N3 C7 173.35(19) . . . . ?
C1 N2 C5 C4 -0.3(3) . . . . ?
Ni1 N2 C5 C4 -178.44(18) . . . . ?
C1 N2 C5 C6 176.5(2) . . . . ?
Ni1 N2 C5 C6 -1.6(2) . . . . ?
C7 N3 C6 O2 7.0(4) . . . . ?
Ni1 N3 C6 O2 -171.1(2) . . . . ?
C7 N3 C6 C5 -172.27(19) . . . . ?
Ni1 N3 C6 C5 9.6(2) . . . . ?
N2 C5 C6 O2 175.3(2) . . . . ?
C4 C5 C6 O2 -7.9(4) . . . . ?
N2 C5 C6 N3 -5.3(3) . . . . ?
C4 C5 C6 N3 171.5(2) . . . . ?
C6 N3 C7 C8 3.2(3) . . . . ?
Ni1 N3 C7 C8 -178.93(19) . . . . ?
C6 N3 C7 C12 -178.3(2) . . . . ?
Ni1 N3 C7 C12 -0.4(3) . . . . ?
N3 C7 C8 C9 177.4(3) . . . . ?
C12 C7 C8 C9 -1.2(4) . . . . ?
C7 C8 C9 C10 0.2(5) . . . . ?
C8 C9 C10 C11 1.1(6) . . . . ?
C9 C10 C11 C12 -1.5(5) . . . . ?
N3 C7 C12 C11 -177.8(2) . . . . ?
C8 C7 C12 C11 0.8(4) . . . . ?
N3 C7 C12 C13 3.5(4) . . . . ?
C8 C7 C12 C13 -177.9(2) . . . . ?
C10 C11 C12 C7 0.5(5) . . . . ?
C10 C11 C12 C13 179.4(3) . . . . ?
C14 N1 C13 C12 178.5(2) . . . . ?
Ni1 N1 C13 C12 -2.6(4) . . . . ?
C7 C12 C13 N1 -2.0(4) . . . . ?
C11 C12 C13 N1 179.2(3) . . . . ?
C13 N1 C14 C19 -180.0(2) . . . . ?
Ni1 N1 C14 C19 0.9(2) . . . . ?
C13 N1 C14 C15 0.5(4) . . . . ?
Ni1 N1 C14 C15 -178.61(18) . . . . ?
C19 C14 C15 C16 0.7(3) . . . . ?
N1 C14 C15 C16 -179.8(2) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C14 C15 C16 C20 -178.9(2) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C20 C16 C17 C18 178.4(2) . . . . ?
Ni1 O1 C19 C14 2.1(2) . . . . ?
Ni1 O1 C19 C18 -178.73(16) . . . . ?
C15 C14 C19 O1 177.59(19) . . . . ?
N1 C14 C19 O1 -2.0(3) . . . . ?
C15 C14 C19 C18 -1.6(3) . . . . ?
N1 C14 C19 C18 178.80(18) . . . . ?
C15 C16 C20 C23 116.9(3) . . . . ?
C17 C16 C20 C23 -62.6(4) . . . . ?
C15 C16 C20 C22 -119.7(3) . . . . ?
C17 C16 C20 C22 60.8(4) . . . . ?
C15 C16 C20 C21 -2.0(3) . . . . ?
C17 C16 C20 C21 178.5(2) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C16 C17 C18 C24 180.0(2) . . . . ?
O1 C19 C18 C17 -178.03(19) . . . . ?
C14 C19 C18 C17 1.2(3) . . . . ?
O1 C19 C18 C24 2.2(3) . . . . ?
C14 C19 C18 C24 -178.6(2) . . . . ?
C25 C24 C18 C17 1.3(3) . . . . ?
C26 C24 C18 C17 -119.4(2) . . . . ?
C27 C24 C18 C17 120.3(2) . . . . ?
C25 C24 C18 C19 -178.9(2) . . . . ?
C26 C24 C18 C19 60.3(3) . . . . ?
C27 C24 C18 C19 -60.0(3) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
N2 C5 C4 C3 2.3(4) . . . . ?
C6 C5 C4 C3 -174.3(2) . . . . ?

_refine_diff_density_max         0.514
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1507896'
_audit_update_record             
;
2016-10-03 deposited with the CCDC.
2018-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H33 Cu N3 O2'
_chemical_formula_sum            'C28 H33 Cu N3 O2'
_chemical_formula_weight         507.11

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   15.8660(8)
_cell_length_b                   14.5267(7)
_cell_length_c                   22.0264(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5076.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8709
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      24.28

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark brown'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2136
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9322
_exptl_absorpt_correction_T_max  0.9653
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 Kappa APEX-Duo CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53953
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         28.32
_reflns_number_total             6308
_reflns_number_gt                4194
_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)+(0.0631P)²+1.9933P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6308
_refine_ls_number_parameters     393
_refine_ls_number_restraints     46
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.020
_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
Cu1 Cu 0.058550(19) 0.64935(2) 0.425196(14) 0.03658(11) Uani 1 1 d . . .
N1 N 0.13227(13) 0.69799(15) 0.48917(10) 0.0401(5) Uani 1 1 d . . .
N2 N 0.09465(14) 0.53165(14) 0.45389(10) 0.0402(5) Uani 1 1 d . . .
N3 N -0.01642(12) 0.60321(14) 0.36400(9) 0.0366(5) Uani 1 1 d . . .
O1 O 0.02696(12) 0.76779(12) 0.39621(9) 0.0439(4) Uani 1 1 d . . .
C4 C 0.2192(2) 0.6540(2) 0.57137(14) 0.0524(7) Uani 1 1 d . . .
C5 C 0.16727(16) 0.63252(18) 0.52323(12) 0.0401(6) Uani 1 1 d . . .
C6 C 0.14877(17) 0.53423(18) 0.50572(13) 0.0434(6) Uani 1 1 d D . .
H6 H 0.1531(18) 0.4818(16) 0.5413(11) 0.052 Uiso 1 1 d D . .
C1 C 0.1477(2) 0.7863(2) 0.50249(14) 0.0499(7) Uani 1 1 d . . .
C2 C 0.1995(2) 0.8114(2) 0.54928(15) 0.0570(8) Uani 1 1 d . . .
C3 C 0.2361(2) 0.7443(3) 0.58381(15) 0.0573(8) Uani 1 1 d . . .
C19 C -0.03283(16) 0.76325(18) 0.35467(12) 0.0375(6) Uani 1 1 d . . .
C14 C -0.05946(15) 0.67629(18) 0.33415(11) 0.0364(5) Uani 1 1 d . . .
C18 C -0.07201(16) 0.84251(18) 0.32989(12) 0.0398(6) Uani 1 1 d . . .
C16 C -0.16230(16) 0.7430(2) 0.26702(12) 0.0431(6) Uani 1 1 d . A .
C13 C -0.02589(18) 0.51687(19) 0.35139(13) 0.0425(6) Uani 1 1 d . . .
C15 C -0.12307(17) 0.6667(2) 0.29115(12) 0.0429(6) Uani 1 1 d . . .
C12 C 0.01136(16) 0.44099(18) 0.38317(13) 0.0424(6) Uani 1 1 d . . .
C7 C 0.06593(16) 0.44791(18) 0.43442(12) 0.0403(6) Uani 1 1 d . . .
C11 C -0.0124(2) 0.3529(2) 0.36258(18) 0.0559(8) Uani 1 1 d . . .
C17 C -0.13494(17) 0.8289(2) 0.28748(13) 0.0452(7) Uani 1 1 d . . .
C9 C 0.0609(2) 0.2808(2) 0.44300(19) 0.0621(9) Uani 1 1 d . . .
C8 C 0.0880(2) 0.36397(19) 0.46328(17) 0.0522(7) Uani 1 1 d . . .
H8 H 0.1244(19) 0.3651(19) 0.4955(14) 0.052(9) Uiso 1 1 d . . .
C10 C 0.0109(2) 0.2739(2) 0.3913(2) 0.0679(10) Uani 1 1 d . . .
O2 O 0.22984(13) 0.48984(15) 0.49708(10) 0.0637(6) Uani 1 1 d . . .
C20 C -0.04349(19) 0.93900(19) 0.34994(15) 0.0505(7) Uani 1 1 d . . .
C22 C -0.0544(2) 0.9507(3) 0.41853(18) 0.0646(9) Uani 1 1 d D . .
H22C H -0.034(3) 1.009(3) 0.4291(19) 0.097 Uiso 1 1 d . . .
H22B H -0.024(3) 0.903(3) 0.4429(19) 0.097 Uiso 1 1 d . . .
H22A H -0.1115(14) 0.949(3) 0.4326(17) 0.097 Uiso 1 1 d D . .
C23 C 0.0494(2) 0.9522(3) 0.3329(2) 0.0646(9) Uani 1 1 d . . .
H23A H 0.088(3) 0.910(3) 0.3544(19) 0.097 Uiso 1 1 d . . .
H23B H 0.055(3) 0.943(3) 0.290(2) 0.097 Uiso 1 1 d . . .
H23C H 0.066(3) 1.011(3) 0.345(2) 0.097 Uiso 1 1 d . . .
C21 C -0.0940(3) 1.0144(3) 0.3179(2) 0.0808(13) Uani 1 1 d . . .
H21B H -0.152(3) 1.011(3) 0.326(2) 0.121 Uiso 1 1 d . . .
H21C H -0.079(3) 1.070(3) 0.333(2) 0.121 Uiso 1 1 d . . .
H21A H -0.092(3) 1.006(3) 0.271(2) 0.121 Uiso 1 1 d . . .
C24 C -0.23725(17) 0.7357(2) 0.22305(13) 0.0531(7) Uani 1 1 d DU . .
C25 C -0.31854(19) 0.7541(3) 0.25646(16) 0.0749(11) Uani 1 1 d . A .
H25C H -0.3671 0.7511 0.2294 0.112 Uiso 1 1 d R . .
H25B H -0.3175 0.8193 0.2753 0.112 Uiso 1 1 d R . .
H25A H -0.3316 0.7105 0.2900 0.112 Uiso 1 1 d R . .
C26A C -0.2274(13) 0.7979(8) 0.1664(5) 0.086(3) Uani 0.608(13) 1 d PDU A 1
H26A H -0.2791 0.7980 0.1437 0.130 Uiso 0.608(13) 1 calc PR A 1
H26B H -0.1827 0.7747 0.1413 0.130 Uiso 0.608(13) 1 calc PR A 1
H26C H -0.2143 0.8595 0.1790 0.130 Uiso 0.608(13) 1 calc PR A 1
C27A C -0.2540(6) 0.6344(4) 0.2036(5) 0.081(2) Uani 0.608(13) 1 d PDU A 1
H27A H -0.2692 0.5987 0.2386 0.121 Uiso 0.608(13) 1 calc PR A 1
H27B H -0.2040 0.6092 0.1856 0.121 Uiso 0.608(13) 1 calc PR A 1
H27C H -0.2993 0.6328 0.1747 0.121 Uiso 0.608(13) 1 calc PR A 1
C26B C -0.235(2) 0.8212(11) 0.1811(8) 0.086(3) Uani 0.392(13) 1 d PDU A 2
H26D H -0.2721 0.8120 0.1473 0.130 Uiso 0.392(13) 1 calc PR A 2
H26E H -0.1783 0.8301 0.1664 0.130 Uiso 0.392(13) 1 calc PR A 2
H26F H -0.2522 0.8746 0.2035 0.130 Uiso 0.392(13) 1 calc PR A 2
C27B C -0.2241(10) 0.6536(9) 0.1788(7) 0.081(2) Uani 0.392(13) 1 d PDU A 2
H27D H -0.2312 0.5967 0.2004 0.121 Uiso 0.392(13) 1 calc PR A 2
H27E H -0.1683 0.6562 0.1621 0.121 Uiso 0.392(13) 1 calc PR A 2
H27F H -0.2647 0.6570 0.1466 0.121 Uiso 0.392(13) 1 calc PR A 2
C28 C 0.2761(2) 0.5200(3) 0.44519(18) 0.0790(11) Uani 1 1 d . . .
H28A H 0.2451 0.5054 0.4090 0.118 Uiso 1 1 calc R . .
H28B H 0.3297 0.4895 0.4442 0.118 Uiso 1 1 calc R . .
H28C H 0.2846 0.5853 0.4475 0.118 Uiso 1 1 calc R . .
H15 H -0.1392(14) 0.6092(17) 0.2827(10) 0.026(6) Uiso 1 1 d . . .
H11 H -0.049(2) 0.347(2) 0.3320(16) 0.058(10) Uiso 1 1 d . . .
H13 H -0.0617(17) 0.5032(19) 0.3199(14) 0.046(8) Uiso 1 1 d . . .
H1 H 0.1198(18) 0.8277(19) 0.4791(13) 0.048(8) Uiso 1 1 d . . .
H17 H -0.1612(18) 0.8798(19) 0.2702(13) 0.048(8) Uiso 1 1 d . . .
H9 H 0.0797(19) 0.227(2) 0.4670(15) 0.059(9) Uiso 1 1 d . . .
H3 H 0.2711(19) 0.760(2) 0.6115(14) 0.056(9) Uiso 1 1 d . . .
H2 H 0.210(2) 0.869(2) 0.5499(16) 0.074(11) Uiso 1 1 d . . .
H10 H -0.003(2) 0.218(3) 0.3768(17) 0.082(12) Uiso 1 1 d . . .
H4 H 0.243(2) 0.607(2) 0.5898(15) 0.064(10) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9024(17) . ?
Cu1 N2 1.911(2) . ?
Cu1 N3 1.919(2) . ?
Cu1 N1 1.963(2) . ?
N1 C5 1.333(3) . ?
N1 C1 1.338(3) . ?
N2 C7 1.368(3) . ?
N2 C6 1.429(3) . ?
N3 C13 1.293(3) . ?
N3 C14 1.423(3) . ?
O1 C19 1.319(3) . ?
C4 C3 1.366(5) . ?
C4 C5 1.379(4) . ?
C4 H4 0.87(3) . ?
C5 C6 1.508(4) . ?
C6 O2 1.451(3) . ?
C6 H6 1.094(17) . ?
C1 C2 1.368(4) . ?
C1 H1 0.91(3) . ?
C2 C3 1.366(5) . ?
C2 H2 0.86(3) . ?
C3 H3 0.86(3) . ?
C19 C14 1.407(4) . ?
C19 C18 1.418(3) . ?
C14 C15 1.391(4) . ?
C18 C17 1.382(4) . ?
C18 C20 1.538(4) . ?
C16 C15 1.378(4) . ?
C16 C17 1.395(4) . ?
C16 C24 1.537(4) . ?
C13 C12 1.433(4) . ?
C13 H13 0.92(3) . ?
C15 H15 0.89(2) . ?
C12 C11 1.409(4) . ?
C12 C7 1.426(4) . ?
C7 C8 1.419(4) . ?
C11 C10 1.362(5) . ?
C11 H11 0.90(3) . ?
C17 H17 0.93(3) . ?
C9 C8 1.358(4) . ?
C9 C10 1.392(6) . ?
C9 H9 0.99(3) . ?
C8 H8 0.92(3) . ?
C10 H10 0.90(4) . ?
O2 C28 1.427(4) . ?
C20 C21 1.530(4) . ?
C20 C22 1.530(5) . ?
C20 C23 1.533(5) . ?
C22 H22C 0.93(4) . ?
C22 H22B 1.00(4) . ?
C22 H22A 0.957(19) . ?
C23 H23A 0.99(4) . ?
C23 H23B 0.96(5) . ?
C23 H23C 0.93(4) . ?
C21 H21B 0.94(5) . ?
C21 H21C 0.91(5) . ?
C21 H21A 1.05(5) . ?
C24 C25 1.509(4) . ?
C24 C26A 1.548(6) . ?
C24 C26B 1.549(6) . ?
C24 C27B 1.554(5) . ?
C24 C27A 1.555(5) . ?
C25 H25C 0.9749 . ?
C25 H25B 1.0345 . ?
C25 H25A 0.9947 . ?
C26A H26A 0.9600 . ?
C26A H26B 0.9600 . ?
C26A H26C 0.9600 . ?
C27A H27A 0.9600 . ?
C27A H27B 0.9600 . ?
C27A H27C 0.9600 . ?
C26B H26D 0.9600 . ?
C26B H26E 0.9600 . ?
C26B H26F 0.9600 . ?
C27B H27D 0.9600 . ?
C27B H27E 0.9600 . ?
C27B H27F 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

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 Cu1 N2 177.83(9) . . ?
O1 Cu1 N3 85.23(8) . . ?
N2 Cu1 N3 96.06(9) . . ?
O1 Cu1 N1 94.15(8) . . ?
N2 Cu1 N1 84.61(9) . . ?
N3 Cu1 N1 178.25(9) . . ?
C5 N1 C1 119.0(2) . . ?
C5 N1 Cu1 113.30(17) . . ?
C1 N1 Cu1 127.70(19) . . ?
C7 N2 C6 118.3(2) . . ?
C7 N2 Cu1 126.30(18) . . ?
C6 N2 Cu1 114.90(16) . . ?
C13 N3 C14 124.6(2) . . ?
C13 N3 Cu1 124.17(19) . . ?
C14 N3 Cu1 111.19(16) . . ?
C19 O1 Cu1 112.14(15) . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4 125(2) . . ?
C5 C4 H4 116(2) . . ?
N1 C5 C4 121.4(3) . . ?
N1 C5 C6 116.8(2) . . ?
C4 C5 C6 121.8(2) . . ?
N2 C6 O2 114.6(2) . . ?
N2 C6 C5 110.2(2) . . ?
O2 C6 C5 106.4(2) . . ?
N2 C6 H6 126.3(15) . . ?
O2 C6 H6 74.3(15) . . ?
C5 C6 H6 117.6(15) . . ?
N1 C1 C2 122.1(3) . . ?
N1 C1 H1 114.9(18) . . ?
C2 C1 H1 123.0(18) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 127(3) . . ?
C1 C2 H2 113(3) . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 119(2) . . ?
C4 C3 H3 122(2) . . ?
O1 C19 C14 118.9(2) . . ?
O1 C19 C18 122.8(2) . . ?
C14 C19 C18 118.3(2) . . ?
C15 C14 C19 121.8(2) . . ?
C15 C14 N3 126.0(2) . . ?
C19 C14 N3 112.2(2) . . ?
C17 C18 C19 117.4(2) . . ?
C17 C18 C20 122.5(2) . . ?
C19 C18 C20 120.0(2) . . ?
C15 C16 C17 117.0(2) . . ?
C15 C16 C24 122.5(3) . . ?
C17 C16 C24 120.4(2) . . ?
N3 C13 C12 126.4(3) . . ?
N3 C13 H13 116.3(18) . . ?
C12 C13 H13 117.2(18) . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 122.9(15) . . ?
C14 C15 H15 116.3(15) . . ?
C11 C12 C7 118.8(3) . . ?
C11 C12 C13 115.5(3) . . ?
C7 C12 C13 125.6(2) . . ?
N2 C7 C8 122.8(3) . . ?
N2 C7 C12 120.9(2) . . ?
C8 C7 C12 116.4(3) . . ?
C10 C11 C12 122.9(3) . . ?
C10 C11 H11 116(2) . . ?
C12 C11 H11 120(2) . . ?
C18 C17 C16 124.9(3) . . ?
C18 C17 H17 119.0(18) . . ?
C16 C17 H17 116.1(18) . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9 115.3(19) . . ?
C10 C9 H9 123.7(19) . . ?
C9 C8 C7 122.6(3) . . ?
C9 C8 H8 118.1(18) . . ?
C7 C8 H8 119.3(19) . . ?
C11 C10 C9 118.2(3) . . ?
C11 C10 H10 122(2) . . ?
C9 C10 H10 120(2) . . ?
C28 O2 C6 115.1(2) . . ?
C21 C20 C22 108.4(3) . . ?
C21 C20 C23 107.6(3) . . ?
C22 C20 C23 109.6(3) . . ?
C21 C20 C18 111.5(3) . . ?
C22 C20 C18 110.6(3) . . ?
C23 C20 C18 109.1(3) . . ?
C20 C22 H22C 108(3) . . ?
C20 C22 H22B 113(2) . . ?
H22C C22 H22B 109(4) . . ?
C20 C22 H22A 115(2) . . ?
H22C C22 H22A 106(3) . . ?
H22B C22 H22A 105(3) . . ?
C20 C23 H23A 114(2) . . ?
C20 C23 H23B 108(2) . . ?
H23A C23 H23B 109(3) . . ?
C20 C23 H23C 108(3) . . ?
H23A C23 H23C 105(3) . . ?
H23B C23 H23C 113(4) . . ?
C20 C21 H21B 113(3) . . ?
C20 C21 H21C 110(3) . . ?
H21B C21 H21C 104(4) . . ?
C20 C21 H21A 111(3) . . ?
H21B C21 H21A 102(4) . . ?
H21C C21 H21A 117(4) . . ?
C25 C24 C16 110.0(2) . . ?
C25 C24 C26A 112.1(7) . . ?
C16 C24 C26A 112.9(8) . . ?
C25 C24 C26B 99.9(12) . . ?
C16 C24 C26B 107.5(12) . . ?
C25 C24 C27B 123.8(7) . . ?
C16 C24 C27B 110.1(5) . . ?
C26A C24 C27B 85.9(7) . . ?
C26B C24 C27B 103.8(10) . . ?
C25 C24 C27A 98.9(5) . . ?
C16 C24 C27A 111.8(4) . . ?
C26A C24 C27A 110.4(6) . . ?
C26B C24 C27A 126.8(9) . . ?
C24 C25 H25C 111.7 . . ?
C24 C25 H25B 110.1 . . ?
H25C C25 H25B 107.4 . . ?
C24 C25 H25A 115.3 . . ?
H25C C25 H25A 105.2 . . ?
H25B C25 H25A 106.8 . . ?
C24 C26A H26A 109.5 . . ?
C24 C26A H26B 109.5 . . ?
C24 C26A H26C 109.5 . . ?
C24 C27A H27A 109.5 . . ?
C24 C27A H27B 109.5 . . ?
C24 C27A H27C 109.5 . . ?
C24 C26B H26D 109.5 . . ?
C24 C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C24 C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
C24 C27B H27D 109.5 . . ?
C24 C27B H27E 109.5 . . ?
H27D C27B H27E 109.5 . . ?
C24 C27B H27F 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 109.5 . . ?
O2 C28 H28A 109.5 . . ?
O2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 N1 C5 178.25(18) . . . . ?
N2 Cu1 N1 C5 -3.54(19) . . . . ?
O1 Cu1 N1 C1 0.6(3) . . . . ?
N2 Cu1 N1 C1 178.8(3) . . . . ?
N3 Cu1 N2 C7 -3.3(2) . . . . ?
N1 Cu1 N2 C7 175.1(2) . . . . ?
N3 Cu1 N2 C6 -174.94(18) . . . . ?
N1 Cu1 N2 C6 3.44(19) . . . . ?
O1 Cu1 N3 C13 174.8(2) . . . . ?
N2 Cu1 N3 C13 -3.5(2) . . . . ?
O1 Cu1 N3 C14 -4.74(16) . . . . ?
N2 Cu1 N3 C14 177.01(17) . . . . ?
N3 Cu1 O1 C19 5.43(18) . . . . ?
N1 Cu1 O1 C19 -172.93(18) . . . . ?
C1 N1 C5 C4 -0.4(4) . . . . ?
Cu1 N1 C5 C4 -178.3(2) . . . . ?
C1 N1 C5 C6 -179.2(3) . . . . ?
Cu1 N1 C5 C6 3.0(3) . . . . ?
C3 C4 C5 N1 -0.9(5) . . . . ?
C3 C4 C5 C6 177.7(3) . . . . ?
C7 N2 C6 O2 65.0(3) . . . . ?
Cu1 N2 C6 O2 -122.6(2) . . . . ?
C7 N2 C6 C5 -175.1(2) . . . . ?
Cu1 N2 C6 C5 -2.7(3) . . . . ?
N1 C5 C6 N2 -0.2(3) . . . . ?
C4 C5 C6 N2 -179.0(3) . . . . ?
N1 C5 C6 O2 124.5(2) . . . . ?
C4 C5 C6 O2 -54.2(3) . . . . ?
C5 N1 C1 C2 1.2(4) . . . . ?
Cu1 N1 C1 C2 178.7(2) . . . . ?
N1 C1 C2 C3 -0.5(5) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C5 C4 C3 C2 1.6(5) . . . . ?
Cu1 O1 C19 C14 -5.1(3) . . . . ?
Cu1 O1 C19 C18 174.5(2) . . . . ?
O1 C19 C14 C15 179.0(2) . . . . ?
C18 C19 C14 C15 -0.6(4) . . . . ?
O1 C19 C14 N3 1.2(3) . . . . ?
C18 C19 C14 N3 -178.4(2) . . . . ?
C13 N3 C14 C15 6.1(4) . . . . ?
Cu1 N3 C14 C15 -174.4(2) . . . . ?
C13 N3 C14 C19 -176.3(2) . . . . ?
Cu1 N3 C14 C19 3.3(3) . . . . ?
O1 C19 C18 C17 -178.8(2) . . . . ?
C14 C19 C18 C17 0.8(4) . . . . ?
O1 C19 C18 C20 1.7(4) . . . . ?
C14 C19 C18 C20 -178.6(2) . . . . ?
C14 N3 C13 C12 -175.1(2) . . . . ?
Cu1 N3 C13 C12 5.5(4) . . . . ?
C17 C16 C15 C14 0.3(4) . . . . ?
C24 C16 C15 C14 -175.3(2) . . . . ?
C19 C14 C15 C16 0.1(4) . . . . ?
N3 C14 C15 C16 177.5(2) . . . . ?
N3 C13 C12 C11 176.7(3) . . . . ?
N3 C13 C12 C7 -0.3(5) . . . . ?
C6 N2 C7 C8 -0.4(4) . . . . ?
Cu1 N2 C7 C8 -171.8(2) . . . . ?
C6 N2 C7 C12 179.6(2) . . . . ?
Cu1 N2 C7 C12 8.2(4) . . . . ?
C11 C12 C7 N2 176.2(3) . . . . ?
C13 C12 C7 N2 -7.0(4) . . . . ?
C11 C12 C7 C8 -3.8(4) . . . . ?
C13 C12 C7 C8 173.0(3) . . . . ?
C7 C12 C11 C10 3.4(5) . . . . ?
C13 C12 C11 C10 -173.7(3) . . . . ?
C19 C18 C17 C16 -0.4(4) . . . . ?
C20 C18 C17 C16 179.0(3) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C24 C16 C17 C18 175.6(3) . . . . ?
C10 C9 C8 C7 1.6(5) . . . . ?
N2 C7 C8 C9 -178.5(3) . . . . ?
C12 C7 C8 C9 1.5(4) . . . . ?
C12 C11 C10 C9 -0.4(5) . . . . ?
C8 C9 C10 C11 -2.2(5) . . . . ?
N2 C6 O2 C28 52.6(3) . . . . ?
C5 C6 O2 C28 -69.4(3) . . . . ?
C17 C18 C20 C21 0.8(4) . . . . ?
C19 C18 C20 C21 -179.8(3) . . . . ?
C17 C18 C20 C22 121.5(3) . . . . ?
C19 C18 C20 C22 -59.1(4) . . . . ?
C17 C18 C20 C23 -117.8(3) . . . . ?
C19 C18 C20 C23 61.6(4) . . . . ?
C15 C16 C24 C25 101.4(3) . . . . ?
C17 C16 C24 C25 -74.0(4) . . . . ?
C15 C16 C24 C26A -132.6(6) . . . . ?
C17 C16 C24 C26A 52.0(7) . . . . ?
C15 C16 C24 C26B -150.8(10) . . . . ?
C17 C16 C24 C26B 33.7(11) . . . . ?
C15 C16 C24 C27B -38.4(9) . . . . ?
C17 C16 C24 C27B 146.2(9) . . . . ?
C15 C16 C24 C27A -7.4(6) . . . . ?
C17 C16 C24 C27A 177.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_e712a
_database_code_depnum_ccdc_archive 'CCDC 1825564'
_audit_update_record             
;
2018-02-24 deposited with the CCDC.
2018-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H33 N3 Ni O2'
_chemical_formula_sum            'C28 H33 N3 Ni O2'
_chemical_formula_weight         502.28

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3643(8)
_cell_length_b                   9.9780(8)
_cell_length_c                   14.3688(12)
_cell_angle_alpha                101.276(7)
_cell_angle_beta                 95.203(7)
_cell_angle_gamma                99.728(7)
_cell_volume                     1287.04(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4254
_cell_measurement_theta_min      2.1051
_cell_measurement_theta_max      28.1153

_exptl_crystal_description       Plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.544
_exptl_crystal_size_mid          0.318
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.783
_shelx_estimated_absorpt_T_min   0.676
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            8310
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.225
_diffrn_reflns_theta_max         28.096
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5514
_reflns_number_gt                4173
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB-2016 (Sheldrick, 2016)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0872P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     patterson
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5514
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1377
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.53502(3) -0.30081(3) 0.12129(2) 0.03601(13) Uani 1 1 d . . . . .
O1 O 0.4759(2) -0.3058(2) 0.23967(13) 0.0444(4) Uani 1 1 d . . . . .
C1 C 0.3714(3) -0.2331(3) 0.25887(17) 0.0377(6) Uani 1 1 d . . . . .
C2 C 0.3065(3) -0.2214(3) 0.34445(18) 0.0453(6) Uani 1 1 d . . . . .
C3 C 0.2031(3) -0.1371(3) 0.35484(18) 0.0450(7) Uani 1 1 d . . . . .
H3A H 0.159411 -0.128945 0.410760 0.054 Uiso 1 1 calc R U . . .
C4 C 0.1593(3) -0.0629(3) 0.28683(18) 0.0388(6) Uani 1 1 d . . . . .
C5 C 0.2220(3) -0.0781(3) 0.20262(17) 0.0377(6) Uani 1 1 d . . . . .
H5A H 0.196156 -0.030898 0.155843 0.045 Uiso 1 1 calc R U . . .
C6 C 0.3241(3) -0.1646(3) 0.18833(17) 0.0358(5) Uani 1 1 d . . . . .
N1 N 0.3958(2) -0.1939(2) 0.10542(14) 0.0345(4) Uani 1 1 d . . . . .
C7 C 0.3642(3) -0.1465(3) 0.02898(18) 0.0398(6) Uani 1 1 d . . . . .
H7A H 0.294726 -0.089806 0.031402 0.048 Uiso 1 1 calc R U . . .
C8 C 0.4271(3) -0.1742(3) -0.05749(18) 0.0391(6) Uani 1 1 d . . . . .
C9 C 0.3730(3) -0.1171(3) -0.13338(19) 0.0476(7) Uani 1 1 d . . . . .
H9A H 0.302695 -0.062156 -0.122841 0.057 Uiso 1 1 calc R U . . .
C10 C 0.4198(3) -0.1395(3) -0.22098(19) 0.0512(7) Uani 1 1 d . . . . .
H10A H 0.383831 -0.099685 -0.269310 0.061 Uiso 1 1 calc R U . . .
C11 C 0.5239(4) -0.2246(4) -0.2362(2) 0.0554(8) Uani 1 1 d . . . . .
H11A H 0.555176 -0.243211 -0.296154 0.066 Uiso 1 1 calc R U . . .
C12 C 0.5810(3) -0.2812(3) -0.16457(19) 0.0479(7) Uani 1 1 d . . . . .
H12A H 0.650940 -0.336075 -0.177150 0.058 Uiso 1 1 calc R U . . .
C13 C 0.5360(3) -0.2580(3) -0.07206(18) 0.0381(6) Uani 1 1 d . . . . .
N2 N 0.5947(2) -0.3091(2) 0.00117(15) 0.0381(5) Uani 1 1 d . . . . .
C14 C 0.7046(3) -0.3927(3) -0.01988(19) 0.0411(6) Uani 1 1 d . . . . .
H14A H 0.660929 -0.471930 -0.072254 0.049 Uiso 1 1 calc R U . . .
C15 C 0.7452(3) -0.4491(3) 0.0666(2) 0.0442(6) Uani 1 1 d . . . . .
C16 C 0.8497(3) -0.5311(3) 0.0702(3) 0.0574(8) Uani 1 1 d . . . . .
H16A H 0.892569 -0.561114 0.015976 0.069 Uiso 1 1 calc R U . . .
C17 C 0.8898(4) -0.5679(4) 0.1550(3) 0.0689(10) Uani 1 1 d . . . . .
H17A H 0.961893 -0.620783 0.159405 0.083 Uiso 1 1 calc R U . . .
C18 C 0.8204(4) -0.5244(4) 0.2338(3) 0.0626(9) Uani 1 1 d . . . . .
H18A H 0.845617 -0.547509 0.291983 0.075 Uiso 1 1 calc R U . . .
C19 C 0.7145(3) -0.4473(3) 0.2248(2) 0.0512(7) Uani 1 1 d . . . . .
H19A H 0.665989 -0.421279 0.277113 0.061 Uiso 1 1 calc R U . . .
N3 N 0.6775(2) -0.4073(2) 0.14285(16) 0.0407(5) Uani 1 1 d . . . . .
C20 C 0.3516(4) -0.2991(4) 0.4214(2) 0.0560(8) Uani 1 1 d . . . . .
C21 C 0.2630(5) -0.2788(5) 0.5057(2) 0.0925(15) Uani 1 1 d . . . . .
H21A H 0.276057 -0.181290 0.533884 0.111 Uiso 1 1 calc R U . . .
H21B H 0.161393 -0.315139 0.483440 0.111 Uiso 1 1 calc R U . . .
H21C H 0.295869 -0.327062 0.552609 0.111 Uiso 1 1 calc R U . . .
C22 C 0.5136(5) -0.2438(5) 0.4592(3) 0.0836(12) Uani 1 1 d . . . . .
H22A H 0.528461 -0.145860 0.486223 0.125 Uiso 1 1 calc R U . . .
H22B H 0.542622 -0.291555 0.507595 0.125 Uiso 1 1 calc R U . . .
H22C H 0.571255 -0.259551 0.407625 0.125 Uiso 1 1 calc R U . . .
C23 C 0.3282(5) -0.4543(4) 0.3787(3) 0.0782(12) Uani 1 1 d . . . . .
H23A H 0.382890 -0.469661 0.325510 0.117 Uiso 1 1 calc R U . . .
H23B H 0.360695 -0.501511 0.426385 0.117 Uiso 1 1 calc R U . . .
H23C H 0.226218 -0.489587 0.357216 0.117 Uiso 1 1 calc R U . . .
C24 C 0.0467(3) 0.0310(3) 0.30912(19) 0.0443(6) Uani 1 1 d . . . . .
C25 C 0.0217(4) 0.1132(3) 0.2317(2) 0.0573(8) Uani 1 1 d . . . . .
H25A H 0.112479 0.170005 0.225624 0.069 Uiso 1 1 calc R U . . .
H25B H -0.015483 0.049688 0.171822 0.069 Uiso 1 1 calc R U . . .
H25C H -0.047545 0.171475 0.249168 0.069 Uiso 1 1 calc R U . . .
C26 C 0.1021(4) 0.1358(4) 0.4030(2) 0.0689(10) Uani 1 1 d . . . . .
H26A H 0.193742 0.191639 0.397493 0.103 Uiso 1 1 calc R U . . .
H26B H 0.032257 0.194658 0.417208 0.103 Uiso 1 1 calc R U . . .
H26C H 0.115199 0.087046 0.453612 0.103 Uiso 1 1 calc R U . . .
C27 C -0.0985(4) -0.0579(4) 0.3173(3) 0.0638(9) Uani 1 1 d . . . . .
H27A H -0.132873 -0.123730 0.257978 0.077 Uiso 1 1 calc R U . . .
H27B H -0.085629 -0.106906 0.367774 0.077 Uiso 1 1 calc R U . . .
H27C H -0.168571 0.000706 0.331370 0.077 Uiso 1 1 calc R U . . .
O2 O 0.8348(2) -0.3216(2) -0.04814(13) 0.0474(5) Uani 1 1 d . . . . .
C28 C 0.9032(3) -0.1986(3) 0.0173(2) 0.0588(8) Uani 1 1 d . . . . .
H28A H 0.988814 -0.157061 -0.006261 0.071 Uiso 1 1 calc R U . . .
H28B H 0.836867 -0.134789 0.024880 0.071 Uiso 1 1 calc R U . . .
H28C H 0.930517 -0.219996 0.077950 0.071 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.8431(18) . ?
Ni1 N1 1.844(2) . ?
Ni1 N2 1.853(2) . ?
Ni1 N3 1.881(2) . ?
O1 C1 1.330(3) . ?
C1 C6 1.408(3) . ?
C1 C2 1.413(3) . ?
C2 C3 1.386(4) . ?
C2 C20 1.537(4) . ?
C3 C4 1.409(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(3) . ?
C4 C24 1.539(3) . ?
C5 C6 1.395(3) . ?
C5 H5A 0.9300 . ?
C6 N1 1.425(3) . ?
N1 C7 1.308(3) . ?
C7 C8 1.422(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.418(4) . ?
C8 C13 1.429(4) . ?
C9 C10 1.360(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.401(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.376(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.418(3) . ?
C12 H12A 0.9300 . ?
C13 N2 1.367(3) . ?
N2 C14 1.448(3) . ?
C14 O2 1.437(3) . ?
C14 C15 1.505(4) . ?
C14 H14A 0.9800 . ?
C15 N3 1.346(3) . ?
C15 C16 1.381(4) . ?
C16 C17 1.378(5) . ?
C16 H16A 0.9300 . ?
C17 C18 1.389(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.366(4) . ?
C18 H18A 0.9300 . ?
C19 N3 1.349(4) . ?
C19 H19A 0.9300 . ?
C20 C23 1.520(5) . ?
C20 C21 1.530(4) . ?
C20 C22 1.534(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C27 1.521(4) . ?
C24 C26 1.524(4) . ?
C24 C25 1.529(4) . ?
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 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
O2 C28 1.405(4) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 N1 86.58(8) . . ?
O1 Ni1 N2 175.97(9) . . ?
N1 Ni1 N2 96.36(9) . . ?
O1 Ni1 N3 91.35(9) . . ?
N1 Ni1 N3 177.69(9) . . ?
N2 Ni1 N3 85.77(9) . . ?
C1 O1 Ni1 113.08(16) . . ?
O1 C1 C6 116.8(2) . . ?
O1 C1 C2 124.2(2) . . ?
C6 C1 C2 119.0(2) . . ?
C3 C2 C1 116.9(2) . . ?
C3 C2 C20 122.7(2) . . ?
C1 C2 C20 120.4(2) . . ?
C2 C3 C4 124.7(2) . . ?
C2 C3 H3A 117.6 . . ?
C4 C3 H3A 117.6 . . ?
C5 C4 C3 117.4(2) . . ?
C5 C4 C24 123.3(2) . . ?
C3 C4 C24 119.3(2) . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
C5 C6 C1 122.1(2) . . ?
C5 C6 N1 126.7(2) . . ?
C1 C6 N1 111.2(2) . . ?
C7 N1 C6 121.9(2) . . ?
C7 N1 Ni1 125.88(18) . . ?
C6 N1 Ni1 112.19(16) . . ?
N1 C7 C8 125.5(2) . . ?
N1 C7 H7A 117.2 . . ?
C8 C7 H7A 117.2 . . ?
C9 C8 C7 116.5(2) . . ?
C9 C8 C13 119.5(2) . . ?
C7 C8 C13 123.9(2) . . ?
C10 C9 C8 122.6(3) . . ?
C10 C9 H9A 118.7 . . ?
C8 C9 H9A 118.7 . . ?
C9 C10 C11 117.9(3) . . ?
C9 C10 H10A 121.0 . . ?
C11 C10 H10A 121.0 . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 H11A 119.2 . . ?
C10 C11 H11A 119.2 . . ?
C11 C12 C13 121.7(3) . . ?
C11 C12 H12A 119.2 . . ?
C13 C12 H12A 119.2 . . ?
N2 C13 C12 122.8(2) . . ?
N2 C13 C8 120.7(2) . . ?
C12 C13 C8 116.5(2) . . ?
C13 N2 C14 117.0(2) . . ?
C13 N2 Ni1 127.27(18) . . ?
C14 N2 Ni1 115.36(18) . . ?
O2 C14 N2 115.0(2) . . ?
O2 C14 C15 109.2(2) . . ?
N2 C14 C15 108.8(2) . . ?
O2 C14 H14A 107.9 . . ?
N2 C14 H14A 107.9 . . ?
C15 C14 H14A 107.9 . . ?
N3 C15 C16 121.9(3) . . ?
N3 C15 C14 114.9(2) . . ?
C16 C15 C14 123.1(3) . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16A 120.3 . . ?
C15 C16 H16A 120.3 . . ?
C16 C17 C18 118.7(3) . . ?
C16 C17 H17A 120.6 . . ?
C18 C17 H17A 120.6 . . ?
C19 C18 C17 119.1(3) . . ?
C19 C18 H18A 120.5 . . ?
C17 C18 H18A 120.5 . . ?
N3 C19 C18 122.6(3) . . ?
N3 C19 H19A 118.7 . . ?
C18 C19 H19A 118.7 . . ?
C15 N3 C19 118.3(3) . . ?
C15 N3 Ni1 114.97(19) . . ?
C19 N3 Ni1 126.8(2) . . ?
C23 C20 C21 107.9(3) . . ?
C23 C20 C22 109.4(3) . . ?
C21 C20 C22 108.4(3) . . ?
C23 C20 C2 110.0(3) . . ?
C21 C20 C2 112.1(2) . . ?
C22 C20 C2 108.9(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C27 C24 C26 109.8(3) . . ?
C27 C24 C25 108.4(3) . . ?
C26 C24 C25 107.6(3) . . ?
C27 C24 C4 109.5(2) . . ?
C26 C24 C4 109.2(2) . . ?
C25 C24 C4 112.4(2) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C28 O2 C14 114.2(2) . . ?
O2 C28 H28A 109.5 . . ?
O2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Ni1 O1 C1 -1.51(18) . . . . ?
N3 Ni1 O1 C1 177.46(19) . . . . ?
Ni1 O1 C1 C6 -0.5(3) . . . . ?
Ni1 O1 C1 C2 179.4(2) . . . . ?
O1 C1 C2 C3 177.5(3) . . . . ?
C6 C1 C2 C3 -2.6(4) . . . . ?
O1 C1 C2 C20 -2.2(4) . . . . ?
C6 C1 C2 C20 177.8(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C20 C2 C3 C4 179.4(3) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C2 C3 C4 C24 -178.0(3) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C24 C4 C5 C6 179.5(2) . . . . ?
C4 C5 C6 C1 -2.9(4) . . . . ?
C4 C5 C6 N1 178.5(2) . . . . ?
O1 C1 C6 C5 -175.8(2) . . . . ?
C2 C1 C6 C5 4.2(4) . . . . ?
O1 C1 C6 N1 3.0(3) . . . . ?
C2 C1 C6 N1 -177.0(2) . . . . ?
C5 C6 N1 C7 -4.4(4) . . . . ?
C1 C6 N1 C7 176.9(2) . . . . ?
C5 C6 N1 Ni1 174.7(2) . . . . ?
C1 C6 N1 Ni1 -4.1(3) . . . . ?
O1 Ni1 N1 C7 -177.8(2) . . . . ?
N2 Ni1 N1 C7 -0.6(2) . . . . ?
O1 Ni1 N1 C6 3.14(17) . . . . ?
N2 Ni1 N1 C6 -179.64(17) . . . . ?
C6 N1 C7 C8 -178.0(2) . . . . ?
Ni1 N1 C7 C8 3.1(4) . . . . ?
N1 C7 C8 C9 177.4(3) . . . . ?
N1 C7 C8 C13 -0.6(4) . . . . ?
C7 C8 C9 C10 -177.6(3) . . . . ?
C13 C8 C9 C10 0.5(4) . . . . ?
C8 C9 C10 C11 1.1(5) . . . . ?
C9 C10 C11 C12 -1.8(5) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
C11 C12 C13 N2 -177.7(3) . . . . ?
C11 C12 C13 C8 0.7(4) . . . . ?
C9 C8 C13 N2 177.1(2) . . . . ?
C7 C8 C13 N2 -5.0(4) . . . . ?
C9 C8 C13 C12 -1.4(4) . . . . ?
C7 C8 C13 C12 176.6(2) . . . . ?
C12 C13 N2 C14 -1.5(4) . . . . ?
C8 C13 N2 C14 -179.9(2) . . . . ?
C12 C13 N2 Ni1 -173.9(2) . . . . ?
C8 C13 N2 Ni1 7.8(4) . . . . ?
N1 Ni1 N2 C13 -4.8(2) . . . . ?
N3 Ni1 N2 C13 176.1(2) . . . . ?
N1 Ni1 N2 C14 -177.29(18) . . . . ?
N3 Ni1 N2 C14 3.64(18) . . . . ?
C13 N2 C14 O2 62.2(3) . . . . ?
Ni1 N2 C14 O2 -124.5(2) . . . . ?
C13 N2 C14 C15 -175.0(2) . . . . ?
Ni1 N2 C14 C15 -1.7(3) . . . . ?
O2 C14 C15 N3 124.0(2) . . . . ?
N2 C14 C15 N3 -2.3(3) . . . . ?
O2 C14 C15 C16 -52.5(4) . . . . ?
N2 C14 C15 C16 -178.7(3) . . . . ?
N3 C15 C16 C17 -2.1(5) . . . . ?
C14 C15 C16 C17 174.1(3) . . . . ?
C15 C16 C17 C18 1.8(5) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C17 C18 C19 N3 -2.3(5) . . . . ?
C16 C15 N3 C19 0.2(4) . . . . ?
C14 C15 N3 C19 -176.3(2) . . . . ?
C16 C15 N3 Ni1 -178.3(2) . . . . ?
C14 C15 N3 Ni1 5.2(3) . . . . ?
C18 C19 N3 C15 2.1(5) . . . . ?
C18 C19 N3 Ni1 -179.7(2) . . . . ?
O1 Ni1 N3 C15 172.16(19) . . . . ?
N2 Ni1 N3 C15 -5.02(19) . . . . ?
O1 Ni1 N3 C19 -6.1(3) . . . . ?
N2 Ni1 N3 C19 176.7(3) . . . . ?
C3 C2 C20 C23 123.5(3) . . . . ?
C1 C2 C20 C23 -56.9(4) . . . . ?
C3 C2 C20 C21 3.4(5) . . . . ?
C1 C2 C20 C21 -177.0(3) . . . . ?
C3 C2 C20 C22 -116.6(3) . . . . ?
C1 C2 C20 C22 63.1(4) . . . . ?
C5 C4 C24 C27 116.0(3) . . . . ?
C3 C4 C24 C27 -64.5(3) . . . . ?
C5 C4 C24 C26 -123.7(3) . . . . ?
C3 C4 C24 C26 55.8(4) . . . . ?
C5 C4 C24 C25 -4.5(4) . . . . ?
C3 C4 C24 C25 175.0(3) . . . . ?
N2 C14 O2 C28 54.8(3) . . . . ?
C15 C14 O2 C28 -67.8(3) . . . . ?

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.087


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
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# Please retain this information to preserve the provenance of 
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data_e714a
_database_code_depnum_ccdc_archive 'CCDC 1825563'
_audit_update_record             
;
2018-02-24 deposited with the CCDC.
2018-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H33 N3 Ni O2'
_chemical_formula_sum            'C28 H33 N3 Ni O2'
_chemical_formula_weight         502.28

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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.5267(8)
_cell_length_b                   16.6156(10)
_cell_length_c                   13.6845(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.524(7)
_cell_angle_gamma                90
_cell_volume                     2537.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9381
_cell_measurement_theta_min      2.1914
_cell_measurement_theta_max      28.0309

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.225
_exptl_crystal_size_mid          0.678
_exptl_crystal_size_min          0.238
_exptl_absorpt_coefficient_mu    0.794
_shelx_estimated_absorpt_T_min   0.443
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.546
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            16146
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.199
_diffrn_reflns_theta_max         28.088
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5500
_reflns_number_gt                4538
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB-2016 (Sheldrick, 2016)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.8716P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5500
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.02891(2) 0.14192(2) 0.95220(2) 0.02926(8) Uani 1 1 d . . . . .
O1 O -0.11067(11) 0.16352(7) 0.85345(10) 0.0363(3) Uani 1 1 d . . . . .
C1 C -0.15695(15) 0.23590(10) 0.86488(13) 0.0301(4) Uani 1 1 d . . . . .
C2 C -0.26628(16) 0.26582(11) 0.80317(13) 0.0322(4) Uani 1 1 d . . . . .
C3 C -0.29747(16) 0.34444(11) 0.82126(14) 0.0334(4) Uani 1 1 d . . . . .
H3A H -0.368688 0.364869 0.781110 0.040 Uiso 1 1 calc R U . . .
C4 C -0.22812(15) 0.39528(10) 0.89657(14) 0.0305(4) Uani 1 1 d . . . . .
C5 C -0.12606(16) 0.36263(10) 0.95951(14) 0.0318(4) Uani 1 1 d . . . . .
H5A H -0.079401 0.393478 1.011423 0.038 Uiso 1 1 calc R U . . .
C6 C -0.09274(15) 0.28337(10) 0.94537(13) 0.0293(4) Uani 1 1 d . . . . .
N1 N 0.00499(13) 0.24011(8) 1.00788(11) 0.0304(3) Uani 1 1 d . . . . .
C7 C 0.05918(16) 0.26447(11) 1.09858(14) 0.0361(4) Uani 1 1 d . . . . .
H7A H 0.035286 0.313724 1.119273 0.043 Uiso 1 1 calc R U . . .
C8 C 0.15174(17) 0.22237(11) 1.16883(14) 0.0370(4) Uani 1 1 d . . . . .
C9 C 0.1860(2) 0.25421(13) 1.26772(16) 0.0511(5) Uani 1 1 d . . . . .
H9A H 0.151600 0.302099 1.281638 0.061 Uiso 1 1 calc R U . . .
C10 C 0.2686(2) 0.21658(15) 1.34378(18) 0.0606(6) Uani 1 1 d . . . . .
H10A H 0.288009 0.237393 1.408948 0.073 Uiso 1 1 calc R U . . .
C11 C 0.3225(2) 0.14637(14) 1.32091(18) 0.0530(6) Uani 1 1 d . . . . .
H11A H 0.380020 0.121063 1.371467 0.064 Uiso 1 1 calc R U . . .
C12 C 0.29297(18) 0.11343(14) 1.22544(16) 0.0445(5) Uani 1 1 d . . . . .
H12A H 0.332602 0.067361 1.212715 0.053 Uiso 1 1 calc R U . . .
C13 C 0.20294(16) 0.14839(11) 1.14559(14) 0.0346(4) Uani 1 1 d . . . . .
N2 N 0.16345(13) 0.11287(10) 1.05276(11) 0.0338(3) Uani 1 1 d . . . . .
C14 C 0.21369(16) 0.03417(12) 1.03978(15) 0.0374(4) Uani 1 1 d . . . . .
H14A H 0.202224 -0.000144 1.094848 0.045 Uiso 1 1 calc R U . . .
C15 C 0.14184(16) -0.00228(11) 0.94280(15) 0.0349(4) Uani 1 1 d . . . . .
C16 C 0.16573(18) -0.07804(12) 0.90899(17) 0.0438(5) Uani 1 1 d . . . . .
H16A H 0.229013 -0.108621 0.946379 0.053 Uiso 1 1 calc R U . . .
C17 C 0.09474(19) -0.10731(12) 0.81961(17) 0.0445(5) Uani 1 1 d . . . . .
H17A H 0.109476 -0.157820 0.796032 0.053 Uiso 1 1 calc R U . . .
C18 C 0.00119(19) -0.06047(12) 0.76539(16) 0.0430(5) Uani 1 1 d . . . . .
H18A H -0.047259 -0.078895 0.704590 0.052 Uiso 1 1 calc R U . . .
C19 C -0.01920(18) 0.01383(12) 0.80273(15) 0.0391(4) Uani 1 1 d . . . . .
H19A H -0.082437 0.045037 0.766473 0.047 Uiso 1 1 calc R U . . .
N3 N 0.05004(13) 0.04269(9) 0.89050(12) 0.0333(3) Uani 1 1 d . . . . .
C20 C -0.34565(18) 0.21268(12) 0.72066(16) 0.0445(5) Uani 1 1 d . . . . .
C21 C -0.3806(3) 0.13740(16) 0.7695(3) 0.0777(9) Uani 1 1 d . . . . .
H21A H -0.309620 0.109559 0.805073 0.093 Uiso 1 1 calc R U . . .
H21B H -0.427068 0.152214 0.815899 0.093 Uiso 1 1 calc R U . . .
H21C H -0.427342 0.102851 0.718213 0.093 Uiso 1 1 calc R U . . .
C22 C -0.4605(2) 0.25588(17) 0.6644(2) 0.0783(9) Uani 1 1 d . . . . .
H22A H -0.439995 0.303685 0.633068 0.094 Uiso 1 1 calc R U . . .
H22B H -0.506872 0.220827 0.613618 0.094 Uiso 1 1 calc R U . . .
H22C H -0.506598 0.270190 0.711304 0.094 Uiso 1 1 calc R U . . .
C23 C -0.2758(3) 0.19012(18) 0.64177(19) 0.0703(8) Uani 1 1 d . . . . .
H23A H -0.254301 0.238244 0.611640 0.084 Uiso 1 1 calc R U . . .
H23B H -0.204427 0.161186 0.674287 0.084 Uiso 1 1 calc R U . . .
H23C H -0.325136 0.156929 0.590401 0.084 Uiso 1 1 calc R U . . .
C24 C -0.26749(17) 0.48295(11) 0.90602(15) 0.0360(4) Uani 1 1 d . . . . .
C25 C -0.3922(2) 0.48591(14) 0.9243(2) 0.0591(6) Uani 1 1 d . . . . .
H25A H -0.392355 0.456983 0.984986 0.071 Uiso 1 1 calc R U . . .
H25B H -0.414399 0.540907 0.931167 0.071 Uiso 1 1 calc R U . . .
H25C H -0.448526 0.461703 0.868273 0.071 Uiso 1 1 calc R U . . .
C26 C -0.2709(4) 0.52923(16) 0.8096(2) 0.0951(12) Uani 1 1 d . . . . .
H26A H -0.192933 0.528237 0.796438 0.114 Uiso 1 1 calc R U . . .
H26B H -0.327985 0.504754 0.754343 0.114 Uiso 1 1 calc R U . . .
H26C H -0.293858 0.583958 0.817237 0.114 Uiso 1 1 calc R U . . .
C27 C -0.1848(2) 0.52620(16) 0.9953(3) 0.0928(12) Uani 1 1 d . . . . .
H27A H -0.182549 0.497030 1.056308 0.111 Uiso 1 1 calc R U . . .
H27B H -0.105502 0.529150 0.985085 0.111 Uiso 1 1 calc R U . . .
H27C H -0.214390 0.579611 1.000638 0.111 Uiso 1 1 calc R U . . .
O2 O 0.33854(12) 0.03295(9) 1.04348(12) 0.0491(4) Uani 1 1 d . . . . .
C28 C 0.3725(2) 0.08577(16) 0.9736(2) 0.0602(6) Uani 1 1 d . . . . .
H28A H 0.457215 0.081615 0.980562 0.072 Uiso 1 1 calc R U . . .
H28B H 0.330384 0.071227 0.906135 0.072 Uiso 1 1 calc R U . . .
H28C H 0.352671 0.140106 0.986994 0.072 Uiso 1 1 calc R U . . .


_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 N1 1.8504(15) . ?
Ni1 O1 1.8581(13) . ?
Ni1 N2 1.8604(15) . ?
Ni1 N3 1.8958(15) . ?
O1 C1 1.341(2) . ?
C1 C6 1.405(2) . ?
C1 C2 1.419(2) . ?
C2 C3 1.393(2) . ?
C2 C20 1.541(3) . ?
C3 C4 1.415(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.383(2) . ?
C4 C24 1.541(2) . ?
C5 C6 1.399(2) . ?
C5 H5A 0.9300 . ?
C6 N1 1.426(2) . ?
N1 C7 1.306(2) . ?
C7 C8 1.427(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.414(3) . ?
C8 C13 1.434(3) . ?
C9 C10 1.372(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.394(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.378(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.428(3) . ?
C12 H12A 0.9300 . ?
C13 N2 1.371(2) . ?
N2 C14 1.459(2) . ?
C14 O2 1.427(2) . ?
C14 C15 1.504(3) . ?
C14 H14A 0.9800 . ?
C15 N3 1.345(2) . ?
C15 C16 1.392(3) . ?
C16 C17 1.379(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.385(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.379(3) . ?
C18 H18A 0.9300 . ?
C19 N3 1.352(2) . ?
C19 H19A 0.9300 . ?
C20 C21 1.519(3) . ?
C20 C22 1.533(3) . ?
C20 C23 1.546(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C26 1.519(3) . ?
C24 C25 1.520(3) . ?
C24 C27 1.528(3) . ?
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 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
O2 C28 1.423(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 O1 86.44(6) . . ?
N1 Ni1 N2 96.13(7) . . ?
O1 Ni1 N2 175.63(6) . . ?
N1 Ni1 N3 177.90(6) . . ?
O1 Ni1 N3 91.64(6) . . ?
N2 Ni1 N3 85.83(7) . . ?
C1 O1 Ni1 112.69(11) . . ?
O1 C1 C6 116.63(15) . . ?
O1 C1 C2 124.39(16) . . ?
C6 C1 C2 118.96(15) . . ?
C3 C2 C1 116.92(16) . . ?
C3 C2 C20 122.36(16) . . ?
C1 C2 C20 120.71(16) . . ?
C2 C3 C4 124.43(16) . . ?
C2 C3 H3A 117.8 . . ?
C4 C3 H3A 117.8 . . ?
C5 C4 C3 117.16(16) . . ?
C5 C4 C24 122.75(16) . . ?
C3 C4 C24 120.08(16) . . ?
C4 C5 C6 120.22(16) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C5 C6 C1 121.87(16) . . ?
C5 C6 N1 126.48(16) . . ?
C1 C6 N1 111.64(14) . . ?
C7 N1 C6 122.10(15) . . ?
C7 N1 Ni1 125.41(12) . . ?
C6 N1 Ni1 111.98(11) . . ?
N1 C7 C8 125.93(17) . . ?
N1 C7 H7A 117.0 . . ?
C8 C7 H7A 117.0 . . ?
C9 C8 C7 116.34(18) . . ?
C9 C8 C13 120.09(18) . . ?
C7 C8 C13 123.41(17) . . ?
C10 C9 C8 122.0(2) . . ?
C10 C9 H9A 119.0 . . ?
C8 C9 H9A 119.0 . . ?
C9 C10 C11 118.3(2) . . ?
C9 C10 H10A 120.8 . . ?
C11 C10 H10A 120.8 . . ?
C12 C11 C10 121.8(2) . . ?
C12 C11 H11A 119.1 . . ?
C10 C11 H11A 119.1 . . ?
C11 C12 C13 121.5(2) . . ?
C11 C12 H12A 119.2 . . ?
C13 C12 H12A 119.2 . . ?
N2 C13 C12 122.87(17) . . ?
N2 C13 C8 121.01(16) . . ?
C12 C13 C8 116.08(18) . . ?
C13 N2 C14 116.67(15) . . ?
C13 N2 Ni1 126.53(12) . . ?
C14 N2 Ni1 115.17(12) . . ?
O2 C14 N2 115.84(16) . . ?
O2 C14 C15 110.66(15) . . ?
N2 C14 C15 108.70(14) . . ?
O2 C14 H14A 107.1 . . ?
N2 C14 H14A 107.1 . . ?
C15 C14 H14A 107.1 . . ?
N3 C15 C16 121.33(19) . . ?
N3 C15 C14 115.55(16) . . ?
C16 C15 C14 123.10(17) . . ?
C17 C16 C15 119.40(19) . . ?
C17 C16 H16A 120.3 . . ?
C15 C16 H16A 120.3 . . ?
C16 C17 C18 119.10(19) . . ?
C16 C17 H17A 120.5 . . ?
C18 C17 H17A 120.5 . . ?
C19 C18 C17 119.1(2) . . ?
C19 C18 H18A 120.4 . . ?
C17 C18 H18A 120.4 . . ?
N3 C19 C18 121.95(18) . . ?
N3 C19 H19A 119.0 . . ?
C18 C19 H19A 119.0 . . ?
C15 N3 C19 119.07(16) . . ?
C15 N3 Ni1 114.70(13) . . ?
C19 N3 Ni1 126.21(13) . . ?
C21 C20 C22 108.4(2) . . ?
C21 C20 C2 108.91(18) . . ?
C22 C20 C2 112.28(17) . . ?
C21 C20 C23 110.5(2) . . ?
C22 C20 C23 107.4(2) . . ?
C2 C20 C23 109.45(18) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C26 C24 C25 107.9(2) . . ?
C26 C24 C27 109.4(2) . . ?
C25 C24 C27 106.2(2) . . ?
C26 C24 C4 110.47(17) . . ?
C25 C24 C4 110.78(16) . . ?
C27 C24 C4 111.97(16) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C28 O2 C14 114.32(16) . . ?
O2 C28 H28A 109.5 . . ?
O2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Ni1 O1 C1 2.68(12) . . . . ?
N3 Ni1 O1 C1 -176.46(12) . . . . ?
Ni1 O1 C1 C6 1.75(19) . . . . ?
Ni1 O1 C1 C2 -176.64(14) . . . . ?
O1 C1 C2 C3 -175.92(16) . . . . ?
C6 C1 C2 C3 5.7(3) . . . . ?
O1 C1 C2 C20 4.3(3) . . . . ?
C6 C1 C2 C20 -174.08(17) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C20 C2 C3 C4 179.47(18) . . . . ?
C2 C3 C4 C5 -3.6(3) . . . . ?
C2 C3 C4 C24 176.48(17) . . . . ?
C3 C4 C5 C6 2.1(3) . . . . ?
C24 C4 C5 C6 -178.02(16) . . . . ?
C4 C5 C6 C1 3.3(3) . . . . ?
C4 C5 C6 N1 -175.59(16) . . . . ?
O1 C1 C6 C5 174.13(16) . . . . ?
C2 C1 C6 C5 -7.4(3) . . . . ?
O1 C1 C6 N1 -6.8(2) . . . . ?
C2 C1 C6 N1 171.67(15) . . . . ?
C5 C6 N1 C7 15.4(3) . . . . ?
C1 C6 N1 C7 -163.60(16) . . . . ?
C5 C6 N1 Ni1 -172.37(14) . . . . ?
C1 C6 N1 Ni1 8.62(18) . . . . ?
O1 Ni1 N1 C7 165.57(16) . . . . ?
N2 Ni1 N1 C7 -10.89(16) . . . . ?
O1 Ni1 N1 C6 -6.34(12) . . . . ?
N2 Ni1 N1 C6 177.20(12) . . . . ?
C6 N1 C7 C8 175.34(17) . . . . ?
Ni1 N1 C7 C8 4.2(3) . . . . ?
N1 C7 C8 C9 -171.4(2) . . . . ?
N1 C7 C8 C13 3.9(3) . . . . ?
C7 C8 C9 C10 175.9(2) . . . . ?
C13 C8 C9 C10 0.4(3) . . . . ?
C8 C9 C10 C11 2.2(4) . . . . ?
C9 C10 C11 C12 -1.6(4) . . . . ?
C10 C11 C12 C13 -1.8(4) . . . . ?
C11 C12 C13 N2 -173.5(2) . . . . ?
C11 C12 C13 C8 4.2(3) . . . . ?
C9 C8 C13 N2 174.27(19) . . . . ?
C7 C8 C13 N2 -0.9(3) . . . . ?
C9 C8 C13 C12 -3.5(3) . . . . ?
C7 C8 C13 C12 -178.70(18) . . . . ?
C12 C13 N2 C14 3.0(3) . . . . ?
C8 C13 N2 C14 -174.62(16) . . . . ?
C12 C13 N2 Ni1 167.69(15) . . . . ?
C8 C13 N2 Ni1 -10.0(3) . . . . ?
N1 Ni1 N2 C13 13.88(16) . . . . ?
N3 Ni1 N2 C13 -166.86(16) . . . . ?
N1 Ni1 N2 C14 178.74(13) . . . . ?
N3 Ni1 N2 C14 -2.00(13) . . . . ?
C13 N2 C14 O2 -66.6(2) . . . . ?
Ni1 N2 C14 O2 127.03(15) . . . . ?
C13 N2 C14 C15 168.15(15) . . . . ?
Ni1 N2 C14 C15 1.73(19) . . . . ?
O2 C14 C15 N3 -128.54(17) . . . . ?
N2 C14 C15 N3 -0.3(2) . . . . ?
O2 C14 C15 C16 52.7(2) . . . . ?
N2 C14 C15 C16 -179.06(17) . . . . ?
N3 C15 C16 C17 0.7(3) . . . . ?
C14 C15 C16 C17 179.41(18) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 N3 0.5(3) . . . . ?
C16 C15 N3 C19 -0.8(3) . . . . ?
C14 C15 N3 C19 -179.66(16) . . . . ?
C16 C15 N3 Ni1 177.54(14) . . . . ?
C14 C15 N3 Ni1 -1.3(2) . . . . ?
C18 C19 N3 C15 0.3(3) . . . . ?
C18 C19 N3 Ni1 -177.91(14) . . . . ?
O1 Ni1 N3 C15 -174.59(13) . . . . ?
N2 Ni1 N3 C15 1.84(13) . . . . ?
O1 Ni1 N3 C19 3.64(16) . . . . ?
N2 Ni1 N3 C19 -179.92(16) . . . . ?
C3 C2 C20 C21 -121.0(2) . . . . ?
C1 C2 C20 C21 58.8(3) . . . . ?
C3 C2 C20 C22 -1.0(3) . . . . ?
C1 C2 C20 C22 178.8(2) . . . . ?
C3 C2 C20 C23 118.2(2) . . . . ?
C1 C2 C20 C23 -62.1(2) . . . . ?
C5 C4 C24 C26 119.1(2) . . . . ?
C3 C4 C24 C26 -61.1(3) . . . . ?
C5 C4 C24 C25 -121.4(2) . . . . ?
C3 C4 C24 C25 58.4(2) . . . . ?
C5 C4 C24 C27 -3.1(3) . . . . ?
C3 C4 C24 C27 176.8(2) . . . . ?
N2 C14 O2 C28 -55.4(2) . . . . ?
C15 C14 O2 C28 68.9(2) . . . . ?

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
C12 H12A O2 0.93 2.40 2.987(3) 120.7 .
C19 H19A O1 0.93 2.36 2.854(2) 112.6 .

_refine_diff_density_max         0.384
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_z_sq
_database_code_depnum_ccdc_archive 'CCDC 1507897'
_audit_update_record             
;
2016-10-03 deposited with the CCDC.
2018-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H33 Cu N4 O'
_chemical_formula_weight         517.13

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   24.983(3)
_cell_length_b                   6.9452(7)
_cell_length_c                   16.3797(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2842.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5083
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      25.59

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.794
_shelx_estimated_absorpt_T_min   0.897
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6319
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-Duo CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20727
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.487
_diffrn_reflns_theta_max         28.695
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3878
_reflns_number_gt                2797
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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-2014/7 (Sheldrick, 2014)'
_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., SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0853P)²+1.6858P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3878
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1637
_refine_ls_wR_factor_gt          0.1476
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.95876(2) 0.2500 0.04124(3) 0.03884(17) Uani 1 2 d S T P . .
H1 H 1.001(2) 0.2500 0.216(3) 0.064(15) Uiso 1 2 d S . P . .
N1 N 1.02757(14) 0.2500 0.0994(2) 0.0425(7) Uani 1 2 d S T P . .
O1 O 0.91628(10) 0.2500 0.13832(16) 0.0459(7) Uani 1 2 d S T P . .
C1 C 1.03397(18) 0.2500 0.1808(3) 0.0508(10) Uani 1 2 d S T P . .
C2 C 1.0840(2) 0.2500 0.2153(3) 0.0650(13) Uani 1 2 d S T P . .
H2 H 1.0857 0.2500 0.2653 0.078 Uiso 1 2 d R U P . .
N2 N 1.00211(13) 0.2500 -0.05427(18) 0.0379(7) Uani 1 2 d S T P . .
C3 C 1.1281(2) 0.2500 0.1656(4) 0.0739(16) Uani 1 2 d S T P . .
H3 H 1.160(2) 0.2500 0.183(4) 0.079(18) Uiso 1 2 d S . P . .
N3 N 0.89102(12) 0.2500 -0.0152(2) 0.0388(7) Uani 1 2 d S T P . .
C4 C 1.12173(19) 0.2500 0.0816(4) 0.0652(13) Uani 1 2 d S T P . .
H4 H 1.1522 0.2500 0.0425 0.078 Uiso 1 2 d R U P . .
N4 N 0.7347(2) -0.2500 0.2619(4) 0.0998(18) Uani 1 2 d S T P . .
C5 C 1.06963(16) 0.2500 0.0504(3) 0.0440(9) Uani 1 2 d S T P . .
C13 C 0.88568(16) 0.2500 -0.0940(2) 0.0445(9) Uani 1 2 d S T P . .
H13 H 0.8568 0.2500 -0.1215 0.053 Uiso 1 2 d R U P . .
C14 C 0.84761(15) 0.2500 0.0405(2) 0.0383(8) Uani 1 2 d S T P . .
C15 C 0.79406(15) 0.2500 0.0184(2) 0.0405(8) Uani 1 2 d S T P . .
H15 H 0.7850 0.2500 -0.0339 0.049 Uiso 1 2 d R U P . .
C16 C 0.75449(15) 0.2500 0.0775(2) 0.0397(8) Uani 1 2 d S T P . .
C17 C 0.77166(16) 0.2500 0.1590(2) 0.0412(8) Uani 1 2 d S T P . .
H17 H 0.747(2) 0.2500 0.200(3) 0.073(16) Uiso 1 2 d S . P . .
C18 C 0.82409(15) 0.2500 0.1846(2) 0.0372(8) Uani 1 2 d S T P . .
C19 C 0.86409(15) 0.2500 0.1221(2) 0.0395(8) Uani 1 2 d S T P . .
C22 C 0.87369(13) 0.0697(5) 0.2937(2) 0.0587(8) Uani 1 1 d . . . . .
H22C H 0.8841 0.0704 0.3501 0.088 Uiso 1 1 calc R U . . .
H22B H 0.9051 0.0679 0.2599 0.088 Uiso 1 1 calc R U . . .
H22A H 0.8525 -0.0425 0.2827 0.088 Uiso 1 1 calc R U . . .
C21 C 0.79175(18) 0.2500 0.3317(3) 0.0563(11) Uani 1 2 d S T P . .
H21B H 0.8026 0.2500 0.3785 0.084 Uiso 1 2 d R U P . .
H21A H 0.7705 0.1470 0.3269 0.084 Uiso 1 1 d R U . . .
C20 C 0.84097(16) 0.2500 0.2751(2) 0.0444(9) Uani 1 2 d S T P . .
C25 C 0.66797(14) 0.0725(7) 0.0933(3) 0.0808(12) Uani 1 1 d . . . . .
H25A H 0.6300 0.0780 0.0842 0.121 Uiso 1 1 calc R U . . .
H25B H 0.6749 0.0677 0.1509 0.121 Uiso 1 1 calc R U . . .
H25C H 0.6823 -0.0406 0.0677 0.121 Uiso 1 1 calc R U . . .
C24 C 0.6839(2) 0.2500 -0.0345(3) 0.086(2) Uani 1 2 d S T P . .
H24A H 0.6461 0.2500 -0.0448 0.129 Uiso 1 2 d R U P . .
H24B H 0.6997 0.3629 -0.0582 0.129 Uiso 1 1 d R U . . .
C23 C 0.69420(16) 0.2500 0.0572(3) 0.0499(10) Uani 1 2 d S T P . .
C26 C 0.7942(3) -0.2500 0.1326(4) 0.0805(17) Uani 1 2 d S T P . .
H26A H 0.8313 -0.2500 0.1478 0.121 Uiso 1 2 d R U P . .
H26B H 0.7866 -0.3629 0.1009 0.121 Uiso 1 1 d R U . . .
C27 C 0.7612(2) -0.2500 0.2069(5) 0.0732(15) Uani 1 2 d S T P . .
C12 C 0.92870(16) 0.2500 -0.1527(2) 0.0430(9) Uani 1 2 d S T P . .
C11 C 0.9120(2) 0.2500 -0.2352(3) 0.0573(12) Uani 1 2 d S T P . .
H11 H 0.8795 0.2500 -0.2540 0.069 Uiso 1 2 d R U P . .
C10 C 0.9475(2) 0.2500 -0.2989(3) 0.0619(13) Uani 1 2 d S T P . .
H10 H 0.9367 0.2500 -0.3619 0.074 Uiso 1 2 d R U P . .
C9 C 1.0019(2) 0.2500 -0.2805(3) 0.0614(12) Uani 1 2 d S T P . .
H9 H 1.0356 0.2500 -0.3276 0.074 Uiso 1 2 d R U P . .
C8 C 1.01969(18) 0.2500 -0.2011(3) 0.0515(10) Uani 1 2 d S T P . .
H8 H 1.060(2) 0.2500 -0.194(3) 0.051(13) Uiso 1 2 d S . P . .
C7 C 0.98430(16) 0.2500 -0.1331(2) 0.0420(9) Uani 1 2 d S T P . .
C6 C 1.05901(18) 0.2500 -0.0401(3) 0.0457(9) Uani 1 2 d S T P . .
H6 H 1.089(2) 0.2500 -0.079(3) 0.055 Uiso 1 2 d S U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.903(3) . ?
Cu1 O1 1.912(3) . ?
Cu1 N3 1.929(3) . ?
Cu1 N1 1.965(3) . ?
N1 C5 1.323(5) . ?
N1 C1 1.343(6) . ?
O1 C19 1.331(5) . ?
C1 C2 1.372(6) . ?
C1 H1 1.01(5) . ?
C2 C3 1.370(8) . ?
C2 H2 0.8197 . ?
N2 C7 1.366(5) . ?
N2 C6 1.440(5) . ?
C3 C4 1.384(8) . ?
C3 H3 0.85(6) . ?
N3 C13 1.297(5) . ?
N3 C14 1.418(5) . ?
C4 C5 1.399(6) . ?
C4 H4 0.9940 . ?
N4 C27 1.117(8) . ?
C5 C6 1.505(6) . ?
C13 C12 1.442(5) . ?
C13 H13 0.8501 . ?
C14 C15 1.386(5) . ?
C14 C19 1.399(5) . ?
C15 C16 1.384(5) . ?
C15 H15 0.8855 . ?
C16 C17 1.402(6) . ?
C16 C23 1.543(5) . ?
C17 C18 1.375(5) . ?
C17 H17 0.92(6) . ?
C18 C19 1.431(5) . ?
C18 C20 1.541(5) . ?
C22 C20 1.526(4) . ?
C22 H22C 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22A 0.9600 . ?
C21 C20 1.540(6) . ?
C21 H21B 0.8136 . ?
C21 H21A 0.8941 . ?
C20 C22 1.526(4) 7_565 ?
C25 C23 1.516(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C24 C23 1.524(6) . ?
C24 H24A 0.9599 . ?
C24 H24B 0.9600 . ?
C23 C25 1.516(5) 7_565 ?
C26 C27 1.471(9) . ?
C26 H26A 0.9599 . ?
C26 H26B 0.9600 . ?
C12 C11 1.414(6) . ?
C12 C7 1.426(6) . ?
C11 C10 1.369(6) . ?
C11 H11 0.8680 . ?
C10 C9 1.392(7) . ?
C10 H10 1.0676 . ?
C9 C8 1.374(7) . ?
C9 H9 1.1414 . ?
C8 C7 1.421(6) . ?
C8 H8 1.00(5) . ?
C6 H6 0.98(5) . ?

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
N2 Cu1 O1 179.03(13) . . ?
N2 Cu1 N3 96.03(13) . . ?
O1 Cu1 N3 84.94(12) . . ?
N2 Cu1 N1 84.31(14) . . ?
O1 Cu1 N1 94.72(13) . . ?
N3 Cu1 N1 179.66(14) . . ?
C5 N1 C1 120.6(4) . . ?
C5 N1 Cu1 113.6(3) . . ?
C1 N1 Cu1 125.8(3) . . ?
C19 O1 Cu1 112.2(2) . . ?
N1 C1 C2 121.1(5) . . ?
N1 C1 H1 118(3) . . ?
C2 C1 H1 121(3) . . ?
C3 C2 C1 119.2(5) . . ?
C3 C2 H2 123.6 . . ?
C1 C2 H2 117.2 . . ?
C7 N2 C6 118.3(3) . . ?
C7 N2 Cu1 126.3(3) . . ?
C6 N2 Cu1 115.4(3) . . ?
C2 C3 C4 119.9(5) . . ?
C2 C3 H3 124(4) . . ?
C4 C3 H3 116(4) . . ?
C13 N3 C14 124.2(3) . . ?
C13 N3 Cu1 124.6(3) . . ?
C14 N3 Cu1 111.2(2) . . ?
C3 C4 C5 118.1(5) . . ?
C3 C4 H4 123.5 . . ?
C5 C4 H4 118.4 . . ?
N1 C5 C4 121.1(4) . . ?
N1 C5 C6 117.3(4) . . ?
C4 C5 C6 121.6(4) . . ?
N3 C13 C12 125.9(4) . . ?
N3 C13 H13 127.9 . . ?
C12 C13 H13 106.2 . . ?
C15 C14 C19 122.3(3) . . ?
C15 C14 N3 124.7(3) . . ?
C19 C14 N3 113.0(3) . . ?
C16 C15 C14 120.4(4) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 116.6(4) . . ?
C15 C16 C23 123.2(4) . . ?
C17 C16 C23 120.2(3) . . ?
C18 C17 C16 125.6(4) . . ?
C18 C17 H17 115(3) . . ?
C16 C17 H17 120(3) . . ?
C17 C18 C19 116.5(3) . . ?
C17 C18 C20 123.7(3) . . ?
C19 C18 C20 119.8(3) . . ?
O1 C19 C14 118.6(3) . . ?
O1 C19 C18 122.8(3) . . ?
C14 C19 C18 118.6(3) . . ?
C20 C22 H22C 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22C C22 H22B 109.5 . . ?
C20 C22 H22A 109.5 . . ?
H22C C22 H22A 109.5 . . ?
H22B C22 H22A 109.5 . . ?
C20 C21 H21B 107.5 . . ?
C20 C21 H21A 114.9 . . ?
H21B C21 H21A 106.3 . . ?
C22 C20 C22 110.3(4) 7_565 . ?
C22 C20 C21 107.9(2) 7_565 . ?
C22 C20 C21 107.9(2) . . ?
C22 C20 C18 109.8(2) 7_565 . ?
C22 C20 C18 109.8(2) . . ?
C21 C20 C18 111.1(3) . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C24 H24A 109.8 . . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 109.5 . . ?
C25 C23 C25 108.8(4) . 7_565 ?
C25 C23 C24 108.2(3) . . ?
C25 C23 C24 108.2(3) 7_565 . ?
C25 C23 C16 109.8(2) . . ?
C25 C23 C16 109.8(2) 7_565 . ?
C24 C23 C16 112.1(4) . . ?
C27 C26 H26A 109.1 . . ?
C27 C26 H26B 109.7 . . ?
H26A C26 H26B 109.5 . . ?
N4 C27 C26 177.9(7) . . ?
C11 C12 C7 120.1(4) . . ?
C11 C12 C13 114.7(4) . . ?
C7 C12 C13 125.2(4) . . ?
C10 C11 C12 122.5(5) . . ?
C10 C11 H11 109.6 . . ?
C12 C11 H11 127.9 . . ?
C11 C10 C9 117.9(5) . . ?
C11 C10 H10 125.0 . . ?
C9 C10 H10 117.1 . . ?
C8 C9 C10 121.4(4) . . ?
C8 C9 H9 113.7 . . ?
C10 C9 H9 124.9 . . ?
C9 C8 C7 122.7(4) . . ?
C9 C8 H8 116(3) . . ?
C7 C8 H8 122(3) . . ?
N2 C7 C8 122.5(4) . . ?
N2 C7 C12 122.0(3) . . ?
C8 C7 C12 115.5(4) . . ?
N2 C6 C5 109.4(3) . . ?
N2 C6 H6 131(3) . . ?
C5 C6 H6 120(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.000(0) . . . . ?
Cu1 N1 C1 C2 180.000(0) . . . . ?
N1 C1 C2 C3 0.000(0) . . . . ?
C1 C2 C3 C4 0.000(0) . . . . ?
C2 C3 C4 C5 0.000(0) . . . . ?
C1 N1 C5 C4 0.000(0) . . . . ?
Cu1 N1 C5 C4 180.0 . . . . ?
C1 N1 C5 C6 180.000(0) . . . . ?
Cu1 N1 C5 C6 0.000(0) . . . . ?
C3 C4 C5 N1 0.000(0) . . . . ?
C3 C4 C5 C6 180.000(0) . . . . ?
C14 N3 C13 C12 180.000(0) . . . . ?
Cu1 N3 C13 C12 0.000(0) . . . . ?
C13 N3 C14 C15 0.0 . . . . ?
Cu1 N3 C14 C15 180.0 . . . . ?
C13 N3 C14 C19 180.000(0) . . . . ?
Cu1 N3 C14 C19 0.0 . . . . ?
C19 C14 C15 C16 0.000(0) . . . . ?
N3 C14 C15 C16 180.0 . . . . ?
C14 C15 C16 C17 0.000(0) . . . . ?
C14 C15 C16 C23 180.0 . . . . ?
C15 C16 C17 C18 0.000(0) . . . . ?
C23 C16 C17 C18 180.000(0) . . . . ?
C16 C17 C18 C19 0.000(0) . . . . ?
C16 C17 C18 C20 180.000(0) . . . . ?
Cu1 O1 C19 C14 0.000(0) . . . . ?
Cu1 O1 C19 C18 180.000(0) . . . . ?
C15 C14 C19 O1 180.0 . . . . ?
N3 C14 C19 O1 0.000(0) . . . . ?
C15 C14 C19 C18 0.000(0) . . . . ?
N3 C14 C19 C18 180.000(0) . . . . ?
C17 C18 C19 O1 180.000(0) . . . . ?
C20 C18 C19 O1 0.000(0) . . . . ?
C17 C18 C19 C14 0.000(0) . . . . ?
C20 C18 C19 C14 180.000(0) . . . . ?
C17 C18 C20 C22 -119.3(2) . . . 7_565 ?
C19 C18 C20 C22 60.7(2) . . . 7_565 ?
C17 C18 C20 C22 119.3(2) . . . . ?
C19 C18 C20 C22 -60.7(2) . . . . ?
C17 C18 C20 C21 0.000(0) . . . . ?
C19 C18 C20 C21 180.000(0) . . . . ?
C15 C16 C23 C25 120.2(3) . . . . ?
C17 C16 C23 C25 -59.8(3) . . . . ?
C15 C16 C23 C25 -120.2(3) . . . 7_565 ?
C17 C16 C23 C25 59.8(3) . . . 7_565 ?
C15 C16 C23 C24 0.000(0) . . . . ?
C17 C16 C23 C24 180.000(0) . . . . ?
N3 C13 C12 C11 180.000(0) . . . . ?
N3 C13 C12 C7 0.000(0) . . . . ?
C7 C12 C11 C10 0.000(0) . . . . ?
C13 C12 C11 C10 180.000(0) . . . . ?
C12 C11 C10 C9 0.000(0) . . . . ?
C11 C10 C9 C8 0.000(0) . . . . ?
C10 C9 C8 C7 0.000(0) . . . . ?
C6 N2 C7 C8 0.000(0) . . . . ?
Cu1 N2 C7 C8 180.000(0) . . . . ?
C6 N2 C7 C12 180.000(0) . . . . ?
Cu1 N2 C7 C12 0.000(0) . . . . ?
C9 C8 C7 N2 180.000(0) . . . . ?
C9 C8 C7 C12 0.000(0) . . . . ?
C11 C12 C7 N2 180.000(0) . . . . ?
C13 C12 C7 N2 0.000(0) . . . . ?
C11 C12 C7 C8 0.000(0) . . . . ?
C13 C12 C7 C8 180.000(0) . . . . ?
C7 N2 C6 C5 180.0 . . . . ?
Cu1 N2 C6 C5 0.000(0) . . . . ?
N1 C5 C6 N2 0.0 . . . . ?
C4 C5 C6 N2 180.0 . . . . ?

_refine_diff_density_max         1.610
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.092

# start Validation Reply Form
_vrf_PLAT094_z_sq                
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       6.57 Report

RESPONSE: The largest peak in the difference electron density map (1.61
e/Ang**3) could be interpreted as an additional site for a partial occupied O2,
but this explanation is rejected not only because of its low occupancy (0.13)
but also because the Cu-O2 bond is too short (1.132 Angs) to be credible.
Therefore this peak is ascribed to a partial structure transformation of
 the crystal surface during data collection.
;
# end Validation Reply Form


