# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ha49

_audit_creation_date             2013-10-17T15:44:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H20 N4 Ni2 O4'
_chemical_formula_sum            'C16 H20 N4 Ni2 O4'
_chemical_formula_weight         449.78
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0898(2)
_cell_length_b                   12.8028(2)
_cell_length_c                   14.4904(2)
_cell_angle_alpha                90
_cell_angle_beta                 120.131(1)
_cell_angle_gamma                90
_cell_volume                     1779.36(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14243
_cell_measurement_theta_min      2.493
_cell_measurement_theta_max      29.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.565
_exptl_absorpt_correction_T_max  0.847


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_number            13854
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.493
_diffrn_reflns_theta_max         29.48
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.98
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.98
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.98
_reflns_number_total             4860
_reflns_number_gt                3640
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0506P)²+0.5574P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4860
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.51
_refine_diff_density_rms         0.073

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3355(2) 0.03610(15) -0.09749(16) 0.0299(4) Uani 1 d . .
C2 C 0.3754(2) 0.11229(17) -0.02027(17) 0.0330(4) Uani 1 d . .
H2 H 0.342(3) 0.1090(19) 0.028(2) 0.04 Uiso 1 d . .
C3 C 0.4624(2) 0.19234(16) -0.01565(17) 0.0317(4) Uani 1 d . .
C4 C 0.5082(2) 0.19776(15) -0.09647(17) 0.0315(4) Uani 1 d . .
C5 C 0.4676(2) 0.12098(16) -0.17473(18) 0.0327(4) Uani 1 d . .
H5 H 0.492(3) 0.1224(17) -0.223(2) 0.039 Uiso 1 d . .
C6 C 0.3826(2) 0.03931(15) -0.17786(16) 0.0292(4) Uani 1 d . .
C7 C -0.0301(3) -0.3513(2) -0.1869(2) 0.0480(6) Uani 1 d . .
H7A H 0.0277 -0.3549 -0.1107 0.072 Uiso 1 calc . .
H7B H -0.056 -0.4207 -0.2153 0.072 Uiso 1 calc . .
H7C H -0.1126 -0.3117 -0.2049 0.072 Uiso 1 calc . .
C8 C 0.0484(2) -0.29961(16) -0.23307(17) 0.0348(5) Uani 1 d . .
C9 C 0.0489(3) -0.34302(18) -0.3209(2) 0.0392(5) Uani 1 d . .
H9 H -0.001(3) -0.398(2) -0.347(2) 0.047 Uiso 1 d . .
C10 C 0.1236(2) -0.30245(16) -0.36556(17) 0.0347(5) Uani 1 d . .
C11 C 0.1211(3) -0.3571(2) -0.4582(2) 0.0536(7) Uani 1 d . .
H11A H 0.0933 -0.3088 -0.516 0.08 Uiso 1 calc . .
H11B H 0.0559 -0.414 -0.4809 0.08 Uiso 1 calc . .
H11C H 0.2124 -0.3836 -0.4368 0.08 Uiso 1 calc . .
C12 C 0.7013(3) 0.5822(2) 0.2713(2) 0.0550(7) Uani 1 d . .
H12A H 0.6296 0.5512 0.2811 0.083 Uiso 1 calc . .
H12B H 0.685 0.6559 0.2599 0.083 Uiso 1 calc . .
H12C H 0.7905 0.5703 0.3337 0.083 Uiso 1 calc . .
C13 C 0.6992(3) 0.53356(18) 0.17560(19) 0.0415(5) Uani 1 d . .
C14 C 0.7664(3) 0.5832(2) 0.1293(2) 0.0502(6) Uani 1 d . .
H14 H 0.806(3) 0.644(2) 0.161(3) 0.06 Uiso 1 d . .
C15 C 0.7664(3) 0.54792(19) 0.0391(2) 0.0458(6) Uani 1 d . .
C16 C 0.8371(4) 0.6101(2) -0.0074(3) 0.0697(9) Uani 1 d . .
H16A H 0.9259 0.5793 0.0128 0.105 Uiso 1 calc . .
H16B H 0.8506 0.6805 0.019 0.105 Uiso 1 calc . .
H16C H 0.7803 0.6106 -0.0837 0.105 Uiso 1 calc . .
N1 N 0.2536(2) -0.04493(14) -0.11457(15) 0.0362(4) Uani 1 d . .
H1 H 0.229(3) -0.055(2) -0.070(2) 0.043 Uiso 1 d . .
N2 N 0.3315(2) -0.04025(14) -0.24459(15) 0.0338(4) Uani 1 d . .
H2A H 0.347(3) -0.042(2) -0.291(2) 0.041 Uiso 1 d . .
N3 N 0.5149(2) 0.26972(15) 0.05316(16) 0.0390(4) Uani 1 d . .
H3 H 0.492(3) 0.268(2) 0.100(2) 0.047 Uiso 1 d . .
N4 N 0.5872(2) 0.28062(14) -0.08022(16) 0.0368(4) Uani 1 d . .
H4 H 0.620(3) 0.286(2) -0.117(2) 0.044 Uiso 1 d . .
O1 O 0.11149(16) -0.21552(12) -0.18720(12) 0.0391(4) Uani 1 d . .
O2 O 0.19935(17) -0.22020(12) -0.33391(12) 0.0375(3) Uani 1 d . .
O3 O 0.63224(17) 0.44762(12) 0.14333(13) 0.0421(4) Uani 1 d . .
O4 O 0.70908(18) 0.46307(12) -0.01037(14) 0.0445(4) Uani 1 d . .
Ni1 Ni 0.22092(3) -0.13582(2) -0.22299(2) 0.03086(10) Uani 1 d . .
Ni2 Ni 0.61598(3) 0.37052(2) 0.02960(2) 0.03437(10) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C1 N1 1.318(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.498(3) . ?
C2 C3 1.386(3) . ?
C2 H2 0.94(3) . ?
C3 N3 1.316(3) . ?
C3 C4 1.494(3) . ?
C4 N4 1.319(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.393(3) . ?
C5 H5 0.87(3) . ?
C6 N2 1.320(3) . ?
C7 C8 1.494(3) . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
C8 O1 1.274(2) . ?
C8 C9 1.391(3) . ?
C9 C10 1.383(3) . ?
C9 H9 0.85(3) . ?
C10 O2 1.280(3) . ?
C10 C11 1.501(3) . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C12 C13 1.509(3) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 O3 1.277(3) . ?
C13 C14 1.382(4) . ?
C14 C15 1.383(4) . ?
C14 H14 0.90(3) . ?
C15 O4 1.281(3) . ?
C15 C16 1.494(4) . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
N1 Ni1 1.8389(19) . ?
N1 H1 0.83(3) . ?
N2 Ni1 1.8664(18) . ?
N2 H2A 0.78(3) . ?
N3 Ni2 1.8503(19) . ?
N3 H3 0.84(3) . ?
N4 Ni2 1.857(2) . ?
N4 H4 0.78(3) . ?
O1 Ni1 1.8479(15) . ?
O2 Ni1 1.8499(15) . ?
O3 Ni2 1.8504(16) . ?
O4 Ni2 1.8455(16) . ?

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 C1 C2 128.27(19) . . ?
N1 C1 C6 110.62(18) . . ?
C2 C1 C6 121.10(18) . . ?
C1 C2 C3 119.61(19) . . ?
C1 C2 H2 119.1(15) . . ?
C3 C2 H2 121.3(15) . . ?
N3 C3 C2 128.7(2) . . ?
N3 C3 C4 111.32(18) . . ?
C2 C3 C4 119.94(19) . . ?
N4 C4 C5 128.8(2) . . ?
N4 C4 C3 110.73(19) . . ?
C5 C4 C3 120.44(18) . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 117.9(16) . . ?
C4 C5 H5 122.5(16) . . ?
N2 C6 C5 129.65(19) . . ?
N2 C6 C1 111.02(17) . . ?
C5 C6 C1 119.32(18) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 C9 124.2(2) . . ?
O1 C8 C7 115.6(2) . . ?
C9 C8 C7 120.2(2) . . ?
C10 C9 C8 123.8(2) . . ?
C10 C9 H9 120.1(18) . . ?
C8 C9 H9 116.1(18) . . ?
O2 C10 C9 125.5(2) . . ?
O2 C10 C11 114.7(2) . . ?
C9 C10 C11 119.8(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 C14 125.0(2) . . ?
O3 C13 C12 115.4(2) . . ?
C14 C13 C12 119.5(2) . . ?
C13 C14 C15 124.4(2) . . ?
C13 C14 H14 113(2) . . ?
C15 C14 H14 123(2) . . ?
O4 C15 C14 124.8(2) . . ?
O4 C15 C16 115.2(2) . . ?
C14 C15 C16 120.1(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 N1 Ni1 118.71(15) . . ?
C1 N1 H1 116.0(18) . . ?
Ni1 N1 H1 124.7(18) . . ?
C6 N2 Ni1 117.39(14) . . ?
C6 N2 H2A 117.1(19) . . ?
Ni1 N2 H2A 125.5(19) . . ?
C3 N3 Ni2 117.64(15) . . ?
C3 N3 H3 113.6(18) . . ?
Ni2 N3 H3 128.6(18) . . ?
C4 N4 Ni2 117.69(16) . . ?
C4 N4 H4 117(2) . . ?
Ni2 N4 H4 126(2) . . ?
C8 O1 Ni1 125.86(14) . . ?
C10 O2 Ni1 124.56(14) . . ?
C13 O3 Ni2 124.36(16) . . ?
C15 O4 Ni2 124.59(17) . . ?
N1 Ni1 O1 89.16(7) . . ?
N1 Ni1 O2 174.81(7) . . ?
O1 Ni1 O2 96.01(7) . . ?
N1 Ni1 N2 82.19(8) . . ?
O1 Ni1 N2 171.22(7) . . ?
O2 Ni1 N2 92.66(7) . . ?
O4 Ni2 O3 96.73(7) . . ?
O4 Ni2 N3 172.76(8) . . ?
O3 Ni2 N3 90.28(8) . . ?
O4 Ni2 N4 90.67(8) . . ?
O3 Ni2 N4 172.60(7) . . ?
N3 Ni2 N4 82.32(8) . . ?

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 1011676'
