# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_NorCor_CN
_database_code_depnum_ccdc_archive 'CCDC 1446038'
_audit_update_record             
;
2016-01-08 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C37 H33 N5 Ni'
_chemical_formula_moiety         'C37 H33 N5 Ni'
_chemical_formula_weight         606.40
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/a 1'
_space_group_name_Hall           '-P 2yab'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.08430(10)
_cell_length_b                   25.1223(2)
_cell_length_c                   8.23270(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.8436(4)
_cell_angle_gamma                90.0000
_cell_volume                     1422.65(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    18840
_cell_measurement_theta_min      3.802
_cell_measurement_theta_max      28.739
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636.00
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           synchrotron
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
'1.00 degrees, -1.0 sec, detector distance 74.98 mm'
_diffrn_radiation_wavelength     0.80000
_diffrn_measurement_device_type  'CCD (MX225HE Rayonix)'
_diffrn_reflns_number            18840
_diffrn_reflns_av_R_equivalents  0.073
_diffrn_reflns_theta_max         28.739
_diffrn_reflns_theta_min         3.802
_diffrn_reflns_theta_full        28.685
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             2532
_reflns_number_gt                2522
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1381
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2532
_refine_ls_number_parameters     208
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0253P)²+6.4079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.56
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Ni Ni 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.5000 0.5000 0.5000 0.0133(2) Uani 1 2 d S . P . .
N1 N 0.7005(4) 0.47825(11) 0.6592(4) 0.0154(6) Uani 1 1 d . . . . .
N2 N 0.3430(4) 0.44633(11) 0.5279(4) 0.0136(6) Uani 1 1 d . . . . .
N3 N 1.0887(9) 0.3725(2) 1.0801(8) 0.0217(13) Uani 0.5 1 d . . P A 1
C1 C 0.8688(5) 0.50768(13) 0.6800(4) 0.0139(7) Uani 1 1 d . . . . .
C2 C 1.0089(5) 0.48215(13) 0.8060(4) 0.0150(7) Uani 1 1 d . . . . .
H2 H 1.1371 0.4928 0.8477 0.018 Uiso 1 1 calc R U . . .
C3 C 0.9184(5) 0.43740(13) 0.8569(4) 0.0153(7) Uani 1 1 d . . . . .
H3 H 0.9762 0.4129 0.9384 0.018 Uiso 0.5 1 calc R U P B 2
C4 C 0.7225(5) 0.43634(12) 0.7614(4) 0.0139(7) Uani 1 1 d . . . . .
C5 C 0.5570(5) 0.39965(12) 0.7576(4) 0.0124(7) Uani 1 1 d . . . . .
C6 C 0.3817(5) 0.40475(12) 0.6440(4) 0.0129(7) Uani 1 1 d . . . . .
C7 C 0.1986(5) 0.37102(13) 0.6137(4) 0.0157(7) Uani 1 1 d . . . . .
H7A H 0.1511 0.3683 0.7145 0.019 Uiso 1 1 calc R U . . .
H7B H 0.2229 0.3355 0.5771 0.019 Uiso 1 1 calc R U . . .
C8 C 0.0492(5) 0.40127(13) 0.4731(4) 0.0145(7) Uani 1 1 d . . . . .
H8A H 0.0036 0.3788 0.3759 0.017 Uiso 1 1 calc R U . . .
H8B H -0.0616 0.4134 0.5132 0.017 Uiso 1 1 calc R U . . .
C9 C 0.1641(5) 0.44739(13) 0.4329(4) 0.0131(7) Uani 1 1 d . . . . .
C10 C 1.0083(10) 0.4014(3) 0.9786(8) 0.0160(14) Uani 0.5 1 d . . P A 1
C11 C 0.5881(5) 0.35643(13) 0.8862(4) 0.0133(7) Uani 1 1 d . . . . .
C12 C 0.5708(5) 0.36867(14) 1.0490(4) 0.0184(7) Uani 1 1 d . . . . .
C13 C 0.6034(5) 0.32809(16) 1.1684(4) 0.0223(8) Uani 1 1 d . . . . .
H13 H 0.5928 0.3358 1.2763 0.027 Uiso 1 1 calc R U . . .
C14 C 0.6509(5) 0.27700(16) 1.1319(5) 0.0255(9) Uani 1 1 d . . . . .
C15 C 0.6697(5) 0.26576(15) 0.9710(5) 0.0237(8) Uani 1 1 d . . . . .
H15 H 0.7013 0.2314 0.9449 0.028 Uiso 1 1 calc R U . . .
C16 C 0.6420(5) 0.30508(14) 0.8482(4) 0.0166(7) Uani 1 1 d . . . . .
C17 C 0.5168(7) 0.42347(16) 1.0953(5) 0.0286(9) Uani 1 1 d . . . . .
H17A H 0.3791 0.4285 1.0556 0.034 Uiso 1 1 calc R U . . .
H17B H 0.5841 0.4495 1.0451 0.034 Uiso 1 1 calc R U . . .
H17C H 0.5527 0.4274 1.2147 0.034 Uiso 1 1 calc R U . . .
C18 C 0.6791(7) 0.2343(2) 1.2635(7) 0.0452(14) Uani 1 1 d . . . . .
H18A H 0.5546 0.2220 1.2749 0.054 Uiso 1 1 calc R U . . .
H18B H 0.7508 0.2485 1.3684 0.054 Uiso 1 1 calc R U . . .
H18C H 0.7497 0.2051 1.2313 0.054 Uiso 1 1 calc R U . . .
C19 C 0.6734(6) 0.29230(14) 0.6788(5) 0.0237(8) Uani 1 1 d . . . . .
H19A H 0.7231 0.2567 0.6791 0.028 Uiso 1 1 calc R U . . .
H19B H 0.7649 0.3170 0.6522 0.028 Uiso 1 1 calc R U . . .
H19C H 0.5521 0.2950 0.5967 0.028 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       DENZO
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.1.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.773(3) 3_666 ?
Ni1 N1 1.773(3) . ?
Ni1 N2 1.797(3) . ?
Ni1 N2 1.797(3) 3_666 ?
N1 C4 1.333(4) . ?
N1 C1 1.378(4) . ?
N2 C9 1.321(5) . ?
N2 C6 1.398(4) . ?
N3 C10 1.150(9) . ?
C1 C2 1.407(5) . ?
C1 C9 1.446(5) 3_666 ?
C2 C3 1.407(5) . ?
C2 H2 0.9300 . ?
C3 C10 1.387(8) . ?
C3 C4 1.422(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.486(5) . ?
C5 C6 1.370(5) . ?
C5 C11 1.496(4) . ?
C6 C7 1.519(5) . ?
C7 C8 1.565(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.498(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C1 1.446(5) 3_666 ?
C11 C16 1.402(5) . ?
C11 C12 1.409(5) . ?
C12 C13 1.396(5) . ?
C12 C17 1.502(5) . ?
C13 C14 1.378(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.392(6) . ?
C14 C18 1.504(5) . ?
C15 C16 1.393(5) . ?
C15 H15 0.9300 . ?
C16 C19 1.498(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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 N1 180.00(16) 3_666 . ?
N1 Ni1 N2 85.11(13) 3_666 . ?
N1 Ni1 N2 94.89(13) . . ?
N1 Ni1 N2 94.89(13) 3_666 3_666 ?
N1 Ni1 N2 85.11(13) . 3_666 ?
N2 Ni1 N2 180.00(11) . 3_666 ?
C4 N1 C1 112.2(3) . . ?
C4 N1 Ni1 131.4(2) . . ?
C1 N1 Ni1 116.3(2) . . ?
C9 N2 C6 115.0(3) . . ?
C9 N2 Ni1 116.4(2) . . ?
C6 N2 Ni1 128.4(2) . . ?
N1 C1 C2 106.5(3) . . ?
N1 C1 C9 109.7(3) . 3_666 ?
C2 C1 C9 143.8(3) . 3_666 ?
C1 C2 C3 107.0(3) . . ?
C1 C2 H2 126.5 . . ?
C3 C2 H2 126.5 . . ?
C10 C3 C2 125.0(4) . . ?
C10 C3 C4 127.3(4) . . ?
C2 C3 C4 107.7(3) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
N1 C4 C3 106.6(3) . . ?
N1 C4 C5 120.3(3) . . ?
C3 C4 C5 133.1(3) . . ?
C6 C5 C4 122.6(3) . . ?
C6 C5 C11 120.4(3) . . ?
C4 C5 C11 117.0(3) . . ?
C5 C6 N2 122.3(3) . . ?
C5 C6 C7 131.2(3) . . ?
N2 C6 C7 106.5(3) . . ?
C6 C7 C8 104.5(3) . . ?
C6 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C9 C8 C7 103.4(3) . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.0 . . ?
N2 C9 C1 112.4(3) . 3_666 ?
N2 C9 C8 110.4(3) . . ?
C1 C9 C8 137.2(3) 3_666 . ?
N3 C10 C3 177.6(7) . . ?
C16 C11 C12 120.2(3) . . ?
C16 C11 C5 120.8(3) . . ?
C12 C11 C5 118.9(3) . . ?
C13 C12 C11 118.2(3) . . ?
C13 C12 C17 120.0(3) . . ?
C11 C12 C17 121.8(3) . . ?
C14 C13 C12 122.3(3) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
C13 C14 C15 118.7(3) . . ?
C13 C14 C18 120.3(4) . . ?
C15 C14 C18 121.0(4) . . ?
C14 C15 C16 121.2(4) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 119.3(3) . . ?
C15 C16 C19 119.8(3) . . ?
C11 C16 C19 120.9(3) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
N2 Ni1 N1 C4 0.2(3) . . . . ?
N2 Ni1 N1 C4 -179.8(3) 3_666 . . . ?
N2 Ni1 N1 C1 177.1(2) . . . . ?
N2 Ni1 N1 C1 -2.9(2) 3_666 . . . ?
N1 Ni1 N2 C9 -2.3(2) 3_666 . . . ?
N1 Ni1 N2 C9 177.7(2) . . . . ?
N1 Ni1 N2 C6 -178.4(3) 3_666 . . . ?
N1 Ni1 N2 C6 1.6(3) . . . . ?
C4 N1 C1 C2 0.0(4) . . . . ?
Ni1 N1 C1 C2 -177.4(2) . . . . ?
C4 N1 C1 C9 -179.7(3) . . . 3_666 ?
Ni1 N1 C1 C9 2.9(4) . . . 3_666 ?
N1 C1 C2 C3 0.2(4) . . . . ?
C9 C1 C2 C3 179.7(4) 3_666 . . . ?
C1 C2 C3 C10 179.5(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C1 N1 C4 C3 -0.2(4) . . . . ?
Ni1 N1 C4 C3 176.7(2) . . . . ?
C1 N1 C4 C5 -179.9(3) . . . . ?
Ni1 N1 C4 C5 -3.0(5) . . . . ?
C10 C3 C4 N1 -179.4(5) . . . . ?
C2 C3 C4 N1 0.3(4) . . . . ?
C10 C3 C4 C5 0.2(7) . . . . ?
C2 C3 C4 C5 180.0(3) . . . . ?
N1 C4 C5 C6 4.5(5) . . . . ?
C3 C4 C5 C6 -175.2(3) . . . . ?
N1 C4 C5 C11 -174.7(3) . . . . ?
C3 C4 C5 C11 5.6(5) . . . . ?
C4 C5 C6 N2 -2.8(5) . . . . ?
C11 C5 C6 N2 176.3(3) . . . . ?
C4 C5 C6 C7 177.3(3) . . . . ?
C11 C5 C6 C7 -3.6(5) . . . . ?
C9 N2 C6 C5 -176.6(3) . . . . ?
Ni1 N2 C6 C5 -0.4(5) . . . . ?
C9 N2 C6 C7 3.4(4) . . . . ?
Ni1 N2 C6 C7 179.5(2) . . . . ?
C5 C6 C7 C8 176.5(3) . . . . ?
N2 C6 C7 C8 -3.4(3) . . . . ?
C6 C7 C8 C9 2.4(3) . . . . ?
C6 N2 C9 C1 177.9(3) . . . 3_666 ?
Ni1 N2 C9 C1 1.2(4) . . . 3_666 ?
C6 N2 C9 C8 -1.8(4) . . . . ?
Ni1 N2 C9 C8 -178.5(2) . . . . ?
C7 C8 C9 N2 -0.5(4) . . . . ?
C7 C8 C9 C1 179.9(4) . . . 3_666 ?
C6 C5 C11 C16 84.2(4) . . . . ?
C4 C5 C11 C16 -96.6(4) . . . . ?
C6 C5 C11 C12 -98.6(4) . . . . ?
C4 C5 C11 C12 80.6(4) . . . . ?
C16 C11 C12 C13 -1.7(5) . . . . ?
C5 C11 C12 C13 -178.9(3) . . . . ?
C16 C11 C12 C17 178.9(3) . . . . ?
C5 C11 C12 C17 1.7(5) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C17 C12 C13 C14 179.2(4) . . . . ?
C12 C13 C14 C15 1.0(6) . . . . ?
C12 C13 C14 C18 -178.2(4) . . . . ?
C13 C14 C15 C16 0.2(6) . . . . ?
C18 C14 C15 C16 179.4(4) . . . . ?
C14 C15 C16 C11 -2.1(5) . . . . ?
C14 C15 C16 C19 176.9(3) . . . . ?
C12 C11 C16 C15 2.8(5) . . . . ?
C5 C11 C16 C15 -180.0(3) . . . . ?
C12 C11 C16 C19 -176.1(3) . . . . ?
C5 C11 C16 C19 1.1(5) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
