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

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

data_HLMePh
_database_code_depnum_ccdc_archive 'CCDC 1045504'
_audit_update_record             
;
2015-01-26 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
  ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 N2 O'
_chemical_formula_sum            'C12 H16 N2 O'
_chemical_formula_weight         204.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   5.6189(10)
_cell_length_b                   10.2238(17)
_cell_length_c                   10.2350(16)
_cell_angle_alpha                84.128(4)
_cell_angle_beta                 77.868(4)
_cell_angle_gamma                86.846(5)
_cell_volume                     571.48(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3192
_cell_measurement_theta_min      3.71
_cell_measurement_theta_max      29.05

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             220
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9773
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
  Bruker-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8458
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2000
_reflns_number_gt                1573
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_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)+(0.0573P)²+0.0726P] 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         2000
_refine_ls_number_parameters     142
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.11116(17) 0.54834(9) 0.35299(9) 0.0358(3) Uani 1 1 d . . .
N1 N 0.7301(2) 0.69210(11) 0.47216(11) 0.0306(3) Uani 1 1 d D . .
H1N H 0.841(3) 0.6306(15) 0.4850(15) 0.046 Uiso 1 1 d D . .
N2 N 0.55305(19) 0.72772(10) 0.58226(11) 0.0292(3) Uani 1 1 d . . .
C1 C 1.2223(3) 0.55893(18) 0.11605(16) 0.0535(5) Uani 1 1 d . . .
H1A H 1.3888 0.5879 0.1071 0.080 Uiso 1 1 calc R . .
H1B H 1.1547 0.5991 0.0400 0.080 Uiso 1 1 calc R . .
H1C H 1.2243 0.4629 0.1171 0.080 Uiso 1 1 calc R . .
C2 C 1.0668(2) 0.60016(12) 0.24515(13) 0.0321(3) Uani 1 1 d . . .
C3 C 0.8763(3) 0.69584(13) 0.23704(13) 0.0332(3) Uani 1 1 d . . .
H3 H 0.8593 0.7334 0.1505 0.040 Uiso 1 1 calc R . .
C4 C 0.7144(2) 0.73768(12) 0.34681(13) 0.0306(3) Uani 1 1 d . . .
C5 C 0.5107(3) 0.83497(14) 0.33044(15) 0.0415(4) Uani 1 1 d . . .
H5A H 0.3562 0.7896 0.3505 0.062 Uiso 1 1 calc R . .
H5B H 0.5397 0.8759 0.2379 0.062 Uiso 1 1 calc R . .
H5C H 0.5031 0.9029 0.3923 0.062 Uiso 1 1 calc R . .
C6 C 0.3685(2) 0.62883(13) 0.62831(15) 0.0374(4) Uani 1 1 d . . .
H6A H 0.3186 0.5984 0.5507 0.056 Uiso 1 1 calc R . .
H6B H 0.2268 0.6675 0.6866 0.056 Uiso 1 1 calc R . .
H6C H 0.4361 0.5542 0.6785 0.056 Uiso 1 1 calc R . .
C7 C 0.6470(2) 0.78987(11) 0.67623(13) 0.0285(3) Uani 1 1 d . . .
C8 C 0.5207(3) 0.78917(13) 0.80867(14) 0.0407(4) Uani 1 1 d . . .
H8 H 0.3738 0.7430 0.8372 0.049 Uiso 1 1 calc R . .
C9 C 0.6086(4) 0.85571(16) 0.89901(17) 0.0564(5) Uani 1 1 d . . .
H9 H 0.5206 0.8549 0.9891 0.068 Uiso 1 1 calc R . .
C10 C 0.8204(4) 0.92261(17) 0.8606(2) 0.0637(6) Uani 1 1 d . . .
H10 H 0.8803 0.9671 0.9235 0.076 Uiso 1 1 calc R . .
C11 C 0.9448(3) 0.92447(16) 0.7298(2) 0.0571(5) Uani 1 1 d . . .
H11 H 1.0911 0.9712 0.7023 0.069 Uiso 1 1 calc R . .
C12 C 0.8606(3) 0.85937(13) 0.63714(16) 0.0392(4) Uani 1 1 d . . .
H12 H 0.9486 0.8621 0.5469 0.047 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2419(16) . ?
N1 C4 1.3386(17) . ?
N1 N2 1.4018(15) . ?
N1 H1N 0.879(13) . ?
N2 C7 1.4081(17) . ?
N2 C6 1.4603(17) . ?
C1 C2 1.508(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.4198(19) . ?
C3 C4 1.3780(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.4994(18) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.391(2) . ?
C7 C12 1.3927(19) . ?
C8 C9 1.386(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.370(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.372(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
C4 N1 N2 120.84(11) . . ?
C4 N1 H1N 119.5(10) . . ?
N2 N1 H1N 119.1(10) . . ?
N1 N2 C7 113.87(10) . . ?
N1 N2 C6 112.59(10) . . ?
C7 N2 C6 120.01(11) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 123.36(12) . . ?
O1 C2 C1 118.41(12) . . ?
C3 C2 C1 118.22(12) . . ?
C4 C3 C2 124.11(11) . . ?
C4 C3 H3 117.9 . . ?
C2 C3 H3 117.9 . . ?
N1 C4 C3 121.55(12) . . ?
N1 C4 C5 117.24(12) . . ?
C3 C4 C5 121.21(11) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 118.59(13) . . ?
C8 C7 N2 120.48(13) . . ?
C12 C7 N2 120.83(12) . . ?
C9 C8 C7 120.12(16) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 121.10(17) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 119.02(15) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C12 121.15(17) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C7 120.01(16) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 N2 C7 -121.84(13) . . . . ?
C4 N1 N2 C6 97.22(14) . . . . ?
O1 C2 C3 C4 -2.7(2) . . . . ?
C1 C2 C3 C4 176.92(14) . . . . ?
N2 N1 C4 C3 -174.98(11) . . . . ?
N2 N1 C4 C5 4.18(18) . . . . ?
C2 C3 C4 N1 1.8(2) . . . . ?
C2 C3 C4 C5 -177.34(13) . . . . ?
N1 N2 C7 C8 -157.03(11) . . . . ?
C6 N2 C7 C8 -19.24(17) . . . . ?
N1 N2 C7 C12 26.57(15) . . . . ?
C6 N2 C7 C12 164.36(11) . . . . ?
C12 C7 C8 C9 -0.53(19) . . . . ?
N2 C7 C8 C9 -177.01(12) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C8 C9 C10 C11 0.8(2) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C10 C11 C12 C7 -0.3(2) . . . . ?
C8 C7 C12 C11 0.82(19) . . . . ?
N2 C7 C12 C11 177.29(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.879(13) 2.384(14) 3.0936(14) 138.0(13) 2_766
N1 H1N O1 0.879(13) 2.018(15) 2.6749(14) 130.6(13) .

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_HLPhPh
_database_code_depnum_ccdc_archive 'CCDC 1045505'
_audit_update_record             
;
2015-01-26 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
  ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 N2 O'
_chemical_formula_sum            'C17 H18 N2 O'
_chemical_formula_weight         266.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.1428(4)
_cell_length_b                   9.2155(4)
_cell_length_c                   9.7631(4)
_cell_angle_alpha                75.8880(10)
_cell_angle_beta                 64.8270(10)
_cell_angle_gamma                74.5770(10)
_cell_volume                     709.56(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    8698
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      30.48

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;
_diffrn_ambient_temperature      213(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-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12160
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2538
_reflns_number_gt                2303
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_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)+(0.0677P)²+0.1598P] 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         2538
_refine_ls_number_parameters     186
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
O1 O 0.33339(11) 1.07515(11) 0.10242(10) 0.0405(3) Uani 1 1 d . . .
N1 N 0.50273(12) 0.84610(11) 0.24073(12) 0.0297(3) Uani 1 1 d D . .
H1N H 0.503(2) 0.8928(18) 0.1473(16) 0.045 Uiso 1 1 d D . .
N2 N 0.62627(12) 0.72074(11) 0.24815(12) 0.0304(3) Uani 1 1 d . . .
C1 C 0.10178(17) 1.23944(16) 0.25210(18) 0.0440(4) Uani 1 1 d . . .
H1A H 0.1200 1.3086 0.1564 0.066 Uiso 1 1 calc R . .
H1B H 0.0903 1.2933 0.3310 0.066 Uiso 1 1 calc R . .
H1C H 0.0023 1.2003 0.2818 0.066 Uiso 1 1 calc R . .
C2 C 0.24654(14) 1.10844(13) 0.23195(14) 0.0300(3) Uani 1 1 d . . .
C3 C 0.27255(15) 1.02764(14) 0.36598(14) 0.0310(3) Uani 1 1 d . . .
H3 H 0.2019 1.0624 0.4594 0.037 Uiso 1 1 calc R . .
C4 C 0.39362(14) 0.90228(13) 0.36893(13) 0.0285(3) Uani 1 1 d . . .
C5 C 0.40821(18) 0.82269(17) 0.51685(15) 0.0426(3) Uani 1 1 d . . .
H5A H 0.4082 0.7152 0.5278 0.064 Uiso 1 1 calc R . .
H5B H 0.3159 0.8662 0.6012 0.064 Uiso 1 1 calc R . .
H5C H 0.5100 0.8350 0.5175 0.064 Uiso 1 1 calc R . .
C6 C 0.61984(14) 0.58747(13) 0.20519(13) 0.0272(3) Uani 1 1 d . . .
C7 C 0.46902(17) 0.55099(16) 0.24018(17) 0.0406(3) Uani 1 1 d . . .
H7 H 0.3714 0.6140 0.2939 0.049 Uiso 1 1 calc R . .
C8 C 0.4618(2) 0.42217(17) 0.1963(2) 0.0522(4) Uani 1 1 d . . .
H8 H 0.3588 0.3987 0.2205 0.063 Uiso 1 1 calc R . .
C9 C 0.6026(2) 0.32765(16) 0.11776(19) 0.0485(4) Uani 1 1 d . . .
H9 H 0.5965 0.2408 0.0876 0.058 Uiso 1 1 calc R . .
C10 C 0.75233(19) 0.36258(15) 0.08433(16) 0.0414(3) Uani 1 1 d . . .
H10 H 0.8494 0.2982 0.0319 0.050 Uiso 1 1 calc R . .
C11 C 0.76242(16) 0.49132(14) 0.12678(14) 0.0330(3) Uani 1 1 d . . .
H11 H 0.8659 0.5138 0.1026 0.040 Uiso 1 1 calc R . .
C12 C 0.76949(14) 0.74983(13) 0.24990(13) 0.0269(3) Uani 1 1 d . . .
C13 C 0.85924(15) 0.63882(14) 0.32462(15) 0.0332(3) Uani 1 1 d . . .
H13 H 0.8256 0.5447 0.3711 0.040 Uiso 1 1 calc R . .
C14 C 0.99736(16) 0.66710(15) 0.33034(15) 0.0362(3) Uani 1 1 d . . .
H14 H 1.0586 0.5910 0.3788 0.043 Uiso 1 1 calc R . .
C15 C 1.04663(16) 0.80611(15) 0.26566(15) 0.0357(3) Uani 1 1 d . . .
H15 H 1.1403 0.8251 0.2704 0.043 Uiso 1 1 calc R . .
C16 C 0.95613(16) 0.91639(14) 0.19413(15) 0.0353(3) Uani 1 1 d . . .
H16 H 0.9881 1.0116 0.1509 0.042 Uiso 1 1 calc R . .
C17 C 0.81913(15) 0.88909(14) 0.18499(14) 0.0317(3) Uani 1 1 d . . .
H17 H 0.7596 0.9650 0.1347 0.038 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2366(16) . ?
N1 C4 1.3450(15) . ?
N1 N2 1.3965(13) . ?
N1 H1N 0.908(13) . ?
N2 C12 1.4124(16) . ?
N2 C6 1.4135(16) . ?
C1 C2 1.5140(16) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.4208(18) . ?
C3 C4 1.3753(17) . ?
C3 H3 0.9400 . ?
C4 C5 1.4955(17) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 C7 1.3860(18) . ?
C6 C11 1.3921(17) . ?
C7 C8 1.382(2) . ?
C7 H7 0.9400 . ?
C8 C9 1.376(2) . ?
C8 H8 0.9400 . ?
C9 C10 1.373(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.3851(19) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
C12 C17 1.3867(17) . ?
C12 C13 1.3967(17) . ?
C13 C14 1.3812(18) . ?
C13 H13 0.9400 . ?
C14 C15 1.3833(19) . ?
C14 H14 0.9400 . ?
C15 C16 1.3796(19) . ?
C15 H15 0.9400 . ?
C16 C17 1.3835(18) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?

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
C4 N1 N2 120.21(10) . . ?
C4 N1 H1N 121.1(10) . . ?
N2 N1 H1N 118.5(10) . . ?
N1 N2 C12 117.05(9) . . ?
N1 N2 C6 115.97(10) . . ?
C12 N2 C6 123.84(9) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 123.45(11) . . ?
O1 C2 C1 119.28(12) . . ?
C3 C2 C1 117.25(11) . . ?
C4 C3 C2 124.76(11) . . ?
C4 C3 H3 117.6 . . ?
C2 C3 H3 117.6 . . ?
N1 C4 C3 121.96(11) . . ?
N1 C4 C5 117.36(11) . . ?
C3 C4 C5 120.68(11) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 118.66(12) . . ?
C7 C6 N2 119.87(11) . . ?
C11 C6 N2 121.47(11) . . ?
C8 C7 C6 120.16(13) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 121.24(14) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 118.76(13) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 120.98(13) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C6 120.20(13) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C17 C12 C13 119.04(11) . . ?
C17 C12 N2 121.42(10) . . ?
C13 C12 N2 119.47(11) . . ?
C14 C13 C12 120.10(12) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.78(12) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 118.96(12) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 121.03(12) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C12 120.07(11) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 N2 C12 -83.26(14) . . . . ?
C4 N1 N2 C6 115.96(12) . . . . ?
O1 C2 C3 C4 -1.4(2) . . . . ?
C1 C2 C3 C4 177.17(12) . . . . ?
N2 N1 C4 C3 178.48(11) . . . . ?
N2 N1 C4 C5 -1.65(17) . . . . ?
C2 C3 C4 N1 1.4(2) . . . . ?
C2 C3 C4 C5 -178.44(12) . . . . ?
N1 N2 C6 C7 -35.77(15) . . . . ?
C12 N2 C6 C7 164.90(12) . . . . ?
N1 N2 C6 C11 143.72(11) . . . . ?
C12 N2 C6 C11 -15.61(17) . . . . ?
C11 C6 C7 C8 -0.6(2) . . . . ?
N2 C6 C7 C8 178.93(13) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C8 C9 C10 C11 -0.8(2) . . . . ?
C9 C10 C11 C6 0.3(2) . . . . ?
C7 C6 C11 C10 0.38(18) . . . . ?
N2 C6 C11 C10 -179.13(11) . . . . ?
N1 N2 C12 C17 -26.40(16) . . . . ?
C6 N2 C12 C17 132.73(12) . . . . ?
N1 N2 C12 C13 150.61(11) . . . . ?
C6 N2 C12 C13 -50.26(16) . . . . ?
C17 C12 C13 C14 -1.39(18) . . . . ?
N2 C12 C13 C14 -178.48(11) . . . . ?
C12 C13 C14 C15 1.5(2) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
C14 C15 C16 C17 -0.73(19) . . . . ?
C15 C16 C17 C12 0.80(19) . . . . ?
C13 C12 C17 C16 0.27(18) . . . . ?
N2 C12 C17 C16 177.29(10) . . . . ?



loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.908(13) 2.062(15) 2.7067(13) 126.9(13) .
N1 H1N O1 0.908(13) 2.247(15) 3.0196(14) 142.6(14) 2_675

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_Cu(LMePh)2
_database_code_depnum_ccdc_archive 'CCDC 1045506'
_audit_update_record             
;
2015-01-26 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
  ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H30 Cu N4 O2'
_chemical_formula_sum            'C24 H30 Cu N4 O2'
_chemical_formula_weight         470.06

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.0551(13)
_cell_length_b                   10.772(2)
_cell_length_c                   14.825(2)
_cell_angle_alpha                69.265(3)
_cell_angle_beta                 84.322(4)
_cell_angle_gamma                78.302(4)
_cell_volume                     1177.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    7277
_cell_measurement_theta_min      2.08
_cell_measurement_theta_max      28.96

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             494
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6574
_exptl_absorpt_correction_T_max  0.6834
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;
_diffrn_ambient_temperature      213(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-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21398
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4223
_reflns_number_gt                3909
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_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)+(0.0881P)²+0.8654P] 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         4223
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0653
_refine_ls_wR_factor_ref         0.2106
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.74456(11) 0.05086(9) 0.25010(6) 0.0340(4) Uani 1 1 d . . .
O1 O 0.6908(8) -0.0915(6) 0.2160(4) 0.0460(14) Uani 1 1 d . . .
O2 O 0.7203(8) 0.2078(6) 0.2854(4) 0.0443(14) Uani 1 1 d . . .
N1 N 0.7843(9) 0.1598(7) 0.1148(5) 0.0373(15) Uani 1 1 d . . .
N2 N 0.8369(9) 0.2852(7) 0.0898(5) 0.0410(15) Uani 1 1 d . . .
N3 N 0.7678(8) -0.0694(6) 0.3848(5) 0.0343(14) Uani 1 1 d . . .
N4 N 0.8095(9) -0.2105(7) 0.4081(5) 0.0400(15) Uani 1 1 d . . .
C1 C 0.6574(17) -0.2290(12) 0.1288(8) 0.066(3) Uani 1 1 d . . .
H1A H 0.7403 -0.3039 0.1659 0.099 Uiso 1 1 calc R . .
H1B H 0.6635 -0.2259 0.0624 0.099 Uiso 1 1 calc R . .
H1C H 0.5447 -0.2407 0.1560 0.099 Uiso 1 1 calc R . .
C2 C 0.6945(11) -0.0975(9) 0.1320(6) 0.0423(19) Uani 1 1 d . . .
C3 C 0.7280(13) 0.0000(10) 0.0471(7) 0.051(2) Uani 1 1 d . . .
H3 H 0.7165 -0.0154 -0.0103 0.061 Uiso 1 1 calc R . .
C4 C 0.7783(12) 0.1222(10) 0.0386(6) 0.047(2) Uani 1 1 d . . .
C5 C 0.8214(18) 0.2129(13) -0.0618(7) 0.069(3) Uani 1 1 d . . .
H5A H 0.7478 0.3003 -0.0761 0.104 Uiso 1 1 calc R . .
H5B H 0.8055 0.1724 -0.1085 0.104 Uiso 1 1 calc R . .
H5C H 0.9386 0.2240 -0.0649 0.104 Uiso 1 1 calc R . .
C6 C 0.9913(11) 0.2818(8) 0.1272(5) 0.0390(17) Uani 1 1 d . . .
C7 C 1.1143(11) 0.1635(9) 0.1492(6) 0.0447(19) Uani 1 1 d . . .
H7 H 1.0900 0.0855 0.1425 0.054 Uiso 1 1 calc R . .
C8 C 1.2713(13) 0.1615(12) 0.1807(7) 0.060(3) Uani 1 1 d . . .
H8 H 1.3532 0.0820 0.1954 0.072 Uiso 1 1 calc R . .
C9 C 1.3087(14) 0.2760(13) 0.1907(7) 0.064(3) Uani 1 1 d . . .
H9 H 1.4152 0.2745 0.2123 0.076 Uiso 1 1 calc R . .
C10 C 1.1894(16) 0.3904(12) 0.1688(7) 0.065(3) Uani 1 1 d . . .
H10 H 1.2153 0.4681 0.1752 0.077 Uiso 1 1 calc R . .
C11 C 1.0312(14) 0.3962(10) 0.1373(7) 0.053(2) Uani 1 1 d . . .
H11 H 0.9511 0.4767 0.1228 0.063 Uiso 1 1 calc R . .
C12 C 0.6995(13) 0.3996(9) 0.0790(8) 0.055(2) Uani 1 1 d . . .
H12A H 0.6698 0.4101 0.1413 0.083 Uiso 1 1 calc R . .
H12B H 0.6015 0.3843 0.0541 0.083 Uiso 1 1 calc R . .
H12C H 0.7354 0.4809 0.0345 0.083 Uiso 1 1 calc R . .
C13 C 0.7074(17) 0.3529(11) 0.3725(9) 0.068(3) Uani 1 1 d . . .
H13A H 0.8078 0.3889 0.3418 0.102 Uiso 1 1 calc R . .
H13B H 0.6978 0.3496 0.4390 0.102 Uiso 1 1 calc R . .
H13C H 0.6078 0.4105 0.3384 0.102 Uiso 1 1 calc R . .
C14 C 0.7211(10) 0.2134(9) 0.3698(7) 0.0417(18) Uani 1 1 d . . .
C15 C 0.7344(12) 0.1056(9) 0.4541(6) 0.046(2) Uani 1 1 d . . .
H15 H 0.7225 0.1246 0.5119 0.055 Uiso 1 1 calc R . .
C16 C 0.7644(11) -0.0310(9) 0.4621(6) 0.0411(18) Uani 1 1 d . . .
C17 C 0.7870(17) -0.1354(11) 0.5614(7) 0.063(3) Uani 1 1 d . . .
H17A H 0.6842 -0.1728 0.5824 0.094 Uiso 1 1 calc R . .
H17B H 0.8101 -0.0937 0.6060 0.094 Uiso 1 1 calc R . .
H17C H 0.8811 -0.2068 0.5599 0.094 Uiso 1 1 calc R . .
C18 C 0.9649(11) -0.2603(8) 0.3737(5) 0.0373(17) Uani 1 1 d . . .
C19 C 1.0036(14) -0.3926(9) 0.3743(7) 0.052(2) Uani 1 1 d . . .
H19 H 0.9206 -0.4477 0.3947 0.062 Uiso 1 1 calc R . .
C20 C 1.1609(16) -0.4431(10) 0.3455(8) 0.065(3) Uani 1 1 d . . .
H20 H 1.1838 -0.5319 0.3450 0.078 Uiso 1 1 calc R . .
C21 C 1.2913(14) -0.3639(11) 0.3161(8) 0.060(3) Uani 1 1 d . . .
H21 H 1.4012 -0.4003 0.2992 0.072 Uiso 1 1 calc R . .
C22 C 1.2513(12) -0.2350(11) 0.3133(7) 0.055(2) Uani 1 1 d . . .
H22 H 1.3337 -0.1797 0.2907 0.066 Uiso 1 1 calc R . .
C23 C 1.0927(11) -0.1809(8) 0.3426(6) 0.0399(17) Uani 1 1 d . . .
H23 H 1.0706 -0.0914 0.3417 0.048 Uiso 1 1 calc R . .
C24 C 0.6651(13) -0.2776(10) 0.4206(7) 0.053(2) Uani 1 1 d . . .
H24A H 0.6456 -0.2882 0.3604 0.080 Uiso 1 1 calc R . .
H24B H 0.5652 -0.2237 0.4393 0.080 Uiso 1 1 calc R . .
H24C H 0.6882 -0.3657 0.4705 0.080 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.909(6) . ?
Cu1 O1 1.912(6) . ?
Cu1 N3 1.960(7) . ?
Cu1 N1 1.965(7) . ?
O1 C2 1.267(10) . ?
O2 C14 1.273(11) . ?
N1 C4 1.336(12) . ?
N1 N2 1.411(9) . ?
N2 C6 1.400(11) . ?
N2 C12 1.453(12) . ?
N3 C16 1.346(11) . ?
N3 N4 1.410(9) . ?
N4 C18 1.382(11) . ?
N4 C24 1.453(11) . ?
C1 C2 1.524(12) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.368(13) . ?
C3 C4 1.414(14) . ?
C3 H3 0.9400 . ?
C4 C5 1.515(13) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 C11 1.394(13) . ?
C6 C7 1.404(13) . ?
C7 C8 1.385(13) . ?
C7 H7 0.9400 . ?
C8 C9 1.387(17) . ?
C8 H8 0.9400 . ?
C9 C10 1.359(18) . ?
C9 H9 0.9400 . ?
C10 C11 1.382(15) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 C14 1.499(12) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 C15 1.368(13) . ?
C15 C16 1.406(12) . ?
C15 H15 0.9400 . ?
C16 C17 1.504(12) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 C19 1.394(12) . ?
C18 C23 1.410(12) . ?
C19 C20 1.365(15) . ?
C19 H19 0.9400 . ?
C20 C21 1.424(17) . ?
C20 H20 0.9400 . ?
C21 C22 1.347(15) . ?
C21 H21 0.9400 . ?
C22 C23 1.388(13) . ?
C22 H22 0.9400 . ?
C23 H23 0.9400 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O1 161.4(3) . . ?
O2 Cu1 N3 92.1(3) . . ?
O1 Cu1 N3 89.9(3) . . ?
O2 Cu1 N1 89.9(3) . . ?
O1 Cu1 N1 92.7(3) . . ?
N3 Cu1 N1 165.5(3) . . ?
C2 O1 Cu1 126.8(6) . . ?
C14 O2 Cu1 127.8(6) . . ?
C4 N1 N2 112.8(7) . . ?
C4 N1 Cu1 125.7(6) . . ?
N2 N1 Cu1 121.4(5) . . ?
C6 N2 N1 115.7(6) . . ?
C6 N2 C12 120.3(8) . . ?
N1 N2 C12 114.6(7) . . ?
C16 N3 N4 112.7(7) . . ?
C16 N3 Cu1 126.1(5) . . ?
N4 N3 Cu1 120.8(5) . . ?
C18 N4 N3 116.6(6) . . ?
C18 N4 C24 121.3(7) . . ?
N3 N4 C24 114.8(7) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 126.9(8) . . ?
O1 C2 C1 114.5(8) . . ?
C3 C2 C1 118.7(8) . . ?
C2 C3 C4 125.4(8) . . ?
C2 C3 H3 117.3 . . ?
C4 C3 H3 117.3 . . ?
N1 C4 C3 122.3(8) . . ?
N1 C4 C5 120.3(9) . . ?
C3 C4 C5 117.4(9) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 N2 121.6(8) . . ?
C11 C6 C7 118.7(8) . . ?
N2 C6 C7 119.6(8) . . ?
C8 C7 C6 120.1(9) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.5(10) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 119.1(9) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 122.0(10) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C6 119.6(10) . . ?
C10 C11 H11 120.2 . . ?
C6 C11 H11 120.2 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C15 125.9(8) . . ?
O2 C14 C13 114.5(8) . . ?
C15 C14 C13 119.6(8) . . ?
C14 C15 C16 125.8(8) . . ?
C14 C15 H15 117.1 . . ?
C16 C15 H15 117.1 . . ?
N3 C16 C15 122.0(8) . . ?
N3 C16 C17 120.1(8) . . ?
C15 C16 C17 117.8(8) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C18 C19 121.1(8) . . ?
N4 C18 C23 120.7(7) . . ?
C19 C18 C23 118.0(8) . . ?
C20 C19 C18 120.6(10) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 121.4(10) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 117.5(10) . . ?
C22 C21 H21 121.3 . . ?
C20 C21 H21 121.3 . . ?
C21 C22 C23 122.4(10) . . ?
C21 C22 H22 118.8 . . ?
C23 C22 H22 118.8 . . ?
C22 C23 C18 120.0(8) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
N4 C24 H24A 109.5 . . ?
N4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O2 Cu1 O1 C2 100.5(10) . . . . ?
N3 Cu1 O1 C2 -163.0(8) . . . . ?
N1 Cu1 O1 C2 2.7(8) . . . . ?
O1 Cu1 O2 C14 95.8(10) . . . . ?
N3 Cu1 O2 C14 -0.3(7) . . . . ?
N1 Cu1 O2 C14 -165.9(7) . . . . ?
O2 Cu1 N1 C4 -165.0(7) . . . . ?
O1 Cu1 N1 C4 -3.3(7) . . . . ?
N3 Cu1 N1 C4 96.8(11) . . . . ?
O2 Cu1 N1 N2 20.4(6) . . . . ?
O1 Cu1 N1 N2 -178.0(6) . . . . ?
N3 Cu1 N1 N2 -77.8(12) . . . . ?
C4 N1 N2 C6 -115.4(8) . . . . ?
Cu1 N1 N2 C6 59.9(9) . . . . ?
C4 N1 N2 C12 97.7(9) . . . . ?
Cu1 N1 N2 C12 -86.9(8) . . . . ?
O2 Cu1 N3 C16 -0.3(7) . . . . ?
O1 Cu1 N3 C16 -161.8(7) . . . . ?
N1 Cu1 N3 C16 97.7(12) . . . . ?
O2 Cu1 N3 N4 -173.0(6) . . . . ?
O1 Cu1 N3 N4 25.4(6) . . . . ?
N1 Cu1 N3 N4 -75.1(12) . . . . ?
C16 N3 N4 C18 -111.4(8) . . . . ?
Cu1 N3 N4 C18 62.3(8) . . . . ?
C16 N3 N4 C24 98.0(9) . . . . ?
Cu1 N3 N4 C24 -88.3(8) . . . . ?
Cu1 O1 C2 C3 -4.2(14) . . . . ?
Cu1 O1 C2 C1 175.7(7) . . . . ?
O1 C2 C3 C4 5.4(16) . . . . ?
C1 C2 C3 C4 -174.5(10) . . . . ?
N2 N1 C4 C3 -179.7(8) . . . . ?
Cu1 N1 C4 C3 5.2(13) . . . . ?
N2 N1 C4 C5 -1.4(12) . . . . ?
Cu1 N1 C4 C5 -176.5(8) . . . . ?
C2 C3 C4 N1 -5.9(16) . . . . ?
C2 C3 C4 C5 175.8(10) . . . . ?
N1 N2 C6 C11 -157.7(8) . . . . ?
C12 N2 C6 C11 -12.9(12) . . . . ?
N1 N2 C6 C7 26.7(11) . . . . ?
C12 N2 C6 C7 171.5(8) . . . . ?
C11 C6 C7 C8 0.3(13) . . . . ?
N2 C6 C7 C8 176.1(8) . . . . ?
C6 C7 C8 C9 -0.1(14) . . . . ?
C7 C8 C9 C10 -0.3(15) . . . . ?
C8 C9 C10 C11 0.4(16) . . . . ?
C9 C10 C11 C6 -0.1(15) . . . . ?
N2 C6 C11 C10 -175.9(8) . . . . ?
C7 C6 C11 C10 -0.2(13) . . . . ?
Cu1 O2 C14 C15 -2.3(13) . .. . . ?
Cu1 O2 C14 C13 177.1(7) . . . . ?
O2 C14 C15 C16 5.9(15) . . . . ?
C13 C14 C15 C16 -173.5(10) . . . . ?
N4 N3 C16 C15 176.5(8) . . . . ?
Cu1 N3 C16 C15 3.3(12) . . . . ?
N4 N3 C16 C17 -5.7(12) . . . . ?
Cu1 N3 C16 C17 -178.9(7) . . . . ?
C14 C15 C16 N3 -6.3(15) . . . . ?
C14 C15 C16 C17 175.8(9) . . . . ?
N3 N4 C18 C19 -166.0(7) . . . . ?
C24 N4 C18 C19 -17.5(12) . . . . ?
N3 N4 C18 C23 17.9(10) . . . . ?
C24 N4 C18 C23 166.5(8) . . . . ?
N4 C18 C19 C20 -176.1(9) . . . . ?
C23 C18 C19 C20 0.0(13) . . . . ?
C18 C19 C20 C21 1.4(16) . . . . ?
C19 C20 C21 C22 -3.1(16) . . . . ?
C20 C21 C22 C23 3.5(16) . . . . ?
C21 C22 C23 C18 -2.2(14) . . . . ?
N4 C18 C23 C22 176.5(8) . . . . ?
C19 C18 C23 C22 0.3(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.912
_refine_diff_density_min         -0.898
_refine_diff_density_rms         0.254
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Ni(LMePh)2
_database_code_depnum_ccdc_archive 'CCDC 1045507'
_audit_update_record             
;
2015-01-26 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
  ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H30 N4 Ni O2'
_chemical_formula_sum            'C24 H30 N4 Ni O2'
_chemical_formula_weight         465.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   6.1698(4)
_cell_length_b                   9.4346(5)
_cell_length_c                   10.2894(5)
_cell_angle_alpha                81.887(2)
_cell_angle_beta                 77.659(2)
_cell_angle_gamma                81.547(2)
_cell_volume                     575.00(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    3849
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      24.86

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             246
_exptl_absorpt_coefficient_mu    0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8451
_exptl_absorpt_correction_T_max  0.9577
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;

_diffrn_ambient_temperature      213(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-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9359
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.61
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2036
_reflns_number_gt                1896
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_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)+(0.0744P)²+0.1669P] 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         2036
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.1044
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.0000 0.5000 0.5000 0.02565(18) Uani 1 2 d S . .
O1 O -0.1130(3) 0.4707(2) 0.67853(18) 0.0389(4) Uani 1 1 d . . .
N1 N 0.2386(3) 0.3445(2) 0.5113(2) 0.0268(4) Uani 1 1 d . . .
N2 N 0.3854(3) 0.2996(2) 0.3939(2) 0.0291(5) Uani 1 1 d . . .
C1 C -0.1705(6) 0.3960(4) 0.9088(3) 0.0626(10) Uani 1 1 d . . .
H1A H -0.1882 0.4942 0.9310 0.094 Uiso 1 1 calc R . .
H1B H -0.0973 0.3320 0.9731 0.094 Uiso 1 1 calc R . .
H1C H -0.3162 0.3673 0.9115 0.094 Uiso 1 1 calc R . .
C2 C -0.0314(5) 0.3877(3) 0.7715(3) 0.0354(6) Uani 1 1 d . . .
C3 C 0.1634(4) 0.2974(3) 0.7496(3) 0.0354(6) Uani 1 1 d . . .
H3 H 0.2144 0.2469 0.8250 0.043 Uiso 1 1 calc R . .
C4 C 0.2930(4) 0.2743(2) 0.6236(3) 0.0305(5) Uani 1 1 d . . .
C5 C 0.5005(5) 0.1676(3) 0.6187(3) 0.0488(7) Uani 1 1 d . . .
H5A H 0.5058 0.1028 0.5525 0.073 Uiso 1 1 calc R . .
H5B H 0.4982 0.1125 0.7059 0.073 Uiso 1 1 calc R . .
H5C H 0.6313 0.2188 0.5946 0.073 Uiso 1 1 calc R . .
C6 C 0.2969(4) 0.2270(2) 0.3146(2) 0.0282(5) Uani 1 1 d . . .
C7 C 0.1053(4) 0.1579(3) 0.3660(3) 0.0342(6) Uani 1 1 d . . .
H7 H 0.0301 0.1658 0.4549 0.041 Uiso 1 1 calc R . .
C8 C 0.0257(5) 0.0782(3) 0.2872(3) 0.0485(7) Uani 1 1 d . . .
H8 H -0.1032 0.0327 0.3230 0.058 Uiso 1 1 calc R . .
C9 C 0.1341(7) 0.0646(4) 0.1561(3) 0.0581(9) Uani 1 1 d . . .
H9 H 0.0803 0.0100 0.1029 0.070 Uiso 1 1 calc R . .
C10 C 0.3222(7) 0.1328(3) 0.1051(3) 0.0543(9) Uani 1 1 d . . .
H10 H 0.3958 0.1246 0.0161 0.065 Uiso 1 1 calc R . .
C11 C 0.4044(5) 0.2123(3) 0.1813(3) 0.0415(6) Uani 1 1 d . . .
H11 H 0.5335 0.2572 0.1441 0.050 Uiso 1 1 calc R . .
C12 C 0.5640(4) 0.3896(3) 0.3373(3) 0.0415(6) Uani 1 1 d . . .
H12A H 0.6941 0.3309 0.2933 0.062 Uiso 1 1 calc R . .
H12B H 0.6031 0.4322 0.4084 0.062 Uiso 1 1 calc R . .
H12C H 0.5135 0.4655 0.2727 0.062 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.8174(18) . ?
Ni1 O1 1.8174(18) 2_566 ?
Ni1 N1 1.9294(19) . ?
Ni1 N1 1.9294(19) 2_566 ?
O1 C2 1.288(3) . ?
N1 C4 1.331(3) . ?
N1 N2 1.423(3) . ?
N2 C6 1.376(3) . ?
N2 C12 1.461(3) . ?
C1 C2 1.494(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.363(4) . ?
C3 C4 1.397(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.504(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 C7 1.401(4) . ?
C6 C11 1.407(4) . ?
C7 C8 1.384(4) . ?
C7 H7 0.9400 . ?
C8 C9 1.386(5) . ?
C8 H8 0.9400 . ?
C9 C10 1.378(5) . ?
C9 H9 0.9400 . ?
C10 C11 1.372(4) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O1 180.000(1) . 2_566 ?
O1 Ni1 N1 92.29(8) . . ?
O1 Ni1 N1 87.71(8) 2_566 . ?
O1 Ni1 N1 87.71(8) . 2_566 ?
O1 Ni1 N1 92.29(8) 2_566 2_566 ?
N1 Ni1 N1 180.000(1) . 2_566 ?
C2 O1 Ni1 129.77(18) . . ?
C4 N1 N2 113.0(2) . . ?
C4 N1 Ni1 125.93(17) . . ?
N2 N1 Ni1 120.98(15) . . ?
C6 N2 N1 116.47(19) . . ?
C6 N2 C12 121.6(2) . . ?
N1 N2 C12 115.02(19) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.2(2) . . ?
O1 C2 C1 114.4(2) . . ?
C3 C2 C1 121.5(2) . . ?
C2 C3 C4 125.0(2) . . ?
C2 C3 H3 117.5 . . ?
C4 C3 H3 117.5 . . ?
N1 C4 C3 121.9(2) . . ?
N1 C4 C5 120.5(2) . . ?
C3 C4 C5 117.5(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 121.3(2) . . ?
N2 C6 C11 120.7(2) . . ?
C7 C6 C11 117.9(2) . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 118.8(3) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C11 C10 C9 121.5(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C6 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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 C2 8.4(2) . . . . ?
O1 Ni1 N1 C4 -10.3(2) . . . . ?
O1 Ni1 N1 C4 169.7(2) 2_566 . . . ?
O1 Ni1 N1 N2 173.60(17) . . . . ?
O1 Ni1 N1 N2 -6.40(17) 2_566 . . . ?
C4 N1 N2 C6 111.9(2) . . . . ?
Ni1 N1 N2 C6 -71.5(2) . . . . ?
C4 N1 N2 C12 -96.6(2) . . . . ?
Ni1 N1 N2 C12 80.0(2) . . . . ?
Ni1 O1 C2 C3 -2.7(4) . . . . ?
Ni1 O1 C2 C1 178.1(2) . . . . ?
O1 C2 C3 C4 -4.8(4) . . . . ?
C1 C2 C3 C4 174.3(3) . . . . ?
N2 N1 C4 C3 -176.8(2) . . . . ?
Ni1 N1 C4 C3 6.8(3) . . . . ?
N2 N1 C4 C5 4.1(3) . . . . ?
Ni1 N1 C4 C5 -172.33(19) . . . . ?
C2 C3 C4 N1 2.3(4) . . . . ?
C2 C3 C4 C5 -178.5(3) . . . . ?
N1 N2 C6 C7 -21.2(3) . . . . ?
C12 N2 C6 C7 -170.7(2) . . . . ?
N1 N2 C6 C11 162.7(2) . . . . ?
C12 N2 C6 C11 13.2(3) . . . . ?
N2 C6 C7 C8 -176.2(2) . . . . ?
C11 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C8 C9 C10 C11 0.5(5) . . . . ?
C9 C10 C11 C6 -0.4(4) . . . . ?
N2 C6 C11 C10 176.3(2) . . . . ?
C7 C6 C11 C10 0.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.062



###END





