# 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_2Ni-80K
_database_code_depnum_ccdc_archive 'CCDC 1840714'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 Ni O8'
_chemical_formula_weight         356.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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 ccn'

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                   7.7921(1)
_cell_length_b                   22.0548(3)
_cell_length_c                   8.4600(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1453.88(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    80.0
_cell_measurement_reflns_used    9258
_cell_measurement_theta_min      3.9910
_cell_measurement_theta_max      76.1130

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.049
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.370
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      80.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20889
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0118
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.01
_diffrn_reflns_theta_max         76.35
_reflns_number_total             1529
_reflns_number_gt                1422
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0331P)²+1.0916P] 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     SHELXL
_refine_ls_extinction_coef       0.00050(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1529
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0635
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.0000 0.0000 0.00811(11) Uani 1 2 d S . .
O1 O 0.06900(11) -0.02600(4) 0.22454(10) 0.01093(19) Uani 1 1 d . . .
O2 O 0.25198(12) -0.01690(4) 0.42473(10) 0.01181(19) Uani 1 1 d . . .
O3 O 0.04778(12) 0.08831(4) 0.06760(11) 0.0132(2) Uani 1 1 d . . .
O4 O 0.08172(15) 0.18709(4) 0.02671(12) 0.0208(2) Uani 1 1 d . . .
C1 C 0.19942(16) -0.00338(5) 0.28813(15) 0.0103(2) Uani 1 1 d . . .
H1 H 0.2628 0.0258 0.2297 0.012 Uiso 1 1 calc R . .
C2 C 0.08724(18) 0.13312(6) -0.01647(15) 0.0140(3) Uani 1 1 d . . .
H2 H 0.1243 0.1252 -0.1215 0.017 Uiso 1 1 calc R . .
C3 C -0.05157(17) 0.15865(6) 0.44267(15) 0.0138(3) Uani 1 1 d . . .
C4 C -0.1076(2) 0.17118(6) 0.60829(16) 0.0215(3) Uani 1 1 d . . .
H4A H -0.2243 0.1878 0.6074 0.032 Uiso 1 1 calc R . .
H4B H -0.0294 0.2006 0.6568 0.032 Uiso 1 1 calc R . .
H4C H -0.1060 0.1334 0.6693 0.032 Uiso 1 1 calc R . .
N1 N -0.07883(15) 0.10474(5) 0.38306(13) 0.0146(2) Uani 1 1 d . . .
H1A H -0.0492 0.0969 0.2848 0.018 Uiso 1 1 calc R . .
H1B H -0.1268 0.0763 0.4412 0.018 Uiso 1 1 calc R . .
N2 N 0.01974(15) 0.20228(5) 0.35954(14) 0.0162(2) Uani 1 1 d . . .
H2A H 0.0506 0.1956 0.2610 0.019 Uiso 1 1 calc R . .
H2B H 0.0366 0.2381 0.4025 0.019 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.00926(18) 0.00900(17) 0.00608(17) -0.00015(10) 0.00014(10) 0.00007(10)
O1 0.0118(4) 0.0129(4) 0.0081(4) 0.0005(3) -0.0009(3) -0.0006(3)
O2 0.0113(4) 0.0158(4) 0.0083(4) 0.0013(3) -0.0013(3) -0.0008(4)
O3 0.0185(5) 0.0107(4) 0.0106(4) -0.0006(3) 0.0001(4) -0.0009(3)
O4 0.0345(6) 0.0110(4) 0.0167(5) 0.0002(4) 0.0052(4) -0.0004(4)
C1 0.0107(6) 0.0107(5) 0.0096(6) -0.0004(4) 0.0013(5) 0.0008(4)
C2 0.0168(6) 0.0131(6) 0.0119(6) 0.0004(4) 0.0010(5) 0.0002(5)
C3 0.0153(6) 0.0143(6) 0.0118(6) 0.0007(5) -0.0012(5) 0.0018(5)
C4 0.0367(8) 0.0159(6) 0.0120(6) -0.0021(5) 0.0050(6) -0.0013(6)
N1 0.0204(6) 0.0129(5) 0.0106(5) -0.0003(4) 0.0023(4) -0.0021(4)
N2 0.0247(6) 0.0112(5) 0.0128(5) -0.0015(4) 0.0023(5) -0.0025(4)

_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 2.0558(9) 5 ?
Ni1 O1 2.0558(9) . ?
Ni1 O3 2.0637(9) 5 ?
Ni1 O3 2.0637(9) . ?
Ni1 O2 2.0686(9) 8_655 ?
Ni1 O2 2.0686(9) 4_455 ?
O1 C1 1.2535(16) . ?
O2 C1 1.2618(15) . ?
O2 Ni1 2.0686(9) 4 ?
O3 C2 1.2559(16) . ?
O4 C2 1.2460(17) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 N1 1.3088(17) . ?
C3 N2 1.3151(18) . ?
C3 C4 1.4935(18) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?

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 180.00(7) 5 . ?
O1 Ni1 O3 87.71(4) 5 5 ?
O1 Ni1 O3 92.29(4) . 5 ?
O1 Ni1 O3 92.29(4) 5 . ?
O1 Ni1 O3 87.71(4) . . ?
O3 Ni1 O3 180.000(16) 5 . ?
O1 Ni1 O2 90.58(3) 5 8_655 ?
O1 Ni1 O2 89.42(3) . 8_655 ?
O3 Ni1 O2 85.02(4) 5 8_655 ?
O3 Ni1 O2 94.98(4) . 8_655 ?
O1 Ni1 O2 89.42(3) 5 4_455 ?
O1 Ni1 O2 90.58(3) . 4_455 ?
O3 Ni1 O2 94.98(4) 5 4_455 ?
O3 Ni1 O2 85.02(4) . 4_455 ?
O2 Ni1 O2 180.00(7) 8_655 4_455 ?
C1 O1 Ni1 119.84(8) . . ?
C1 O2 Ni1 122.86(8) . 4 ?
C2 O3 Ni1 129.04(8) . . ?
O1 C1 O2 124.21(11) . . ?
O1 C1 H1 117.9 . . ?
O2 C1 H1 117.9 . . ?
O4 C2 O3 125.26(12) . . ?
O4 C2 H2 117.4 . . ?
O3 C2 H2 117.4 . . ?
N1 C3 N2 121.82(12) . . ?
N1 C3 C4 118.83(12) . . ?
N2 C3 C4 119.33(12) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.95 2.42 2.9538(16) 115.5 4
C4 H4C O1 0.98 2.55 3.5131(17) 167.6 5_556
N1 H1A O3 0.88 2.00 2.8682(14) 171.0 .
N1 H1B O2 0.88 1.99 2.8667(14) 175.1 5_556
N2 H2A O4 0.88 2.01 2.8764(15) 170.1 .
N2 H2B O4 0.88 1.99 2.8612(15) 172.1 7_566

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        76.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_1Co-360K
_database_code_depnum_ccdc_archive 'CCDC 1840731'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 Co N4 O8'
_chemical_formula_weight         357.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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 ccn'

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                   7.9102(2)
_cell_length_b                   22.1031(7)
_cell_length_c                   8.6003(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1503.68(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    360.0
_cell_measurement_reflns_used    5338
_cell_measurement_theta_min      7.8590
_cell_measurement_theta_max      76.1260

_exptl_crystal_description       block
_exptl_crystal_colour            purple-red
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             740
_exptl_absorpt_coefficient_mu    9.378
_exptl_absorpt_correction_T_min  0.323
_exptl_absorpt_correction_T_max  0.565
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      360.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21208
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         76.61
_reflns_number_total             1563
_reflns_number_gt                1275
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0377P)²+0.8801P] 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     SHELXL
_refine_ls_extinction_coef       0.00039(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1563
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0781
_refine_ls_wR_factor_gt          0.0724
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
Co1 Co 0.0000 0.0000 0.0000 0.02448(14) Uani 1 2 d S . .
O1 O 0.07113(16) -0.02513(6) 0.22700(14) 0.0338(3) Uani 1 1 d . . .
O2 O 0.25105(17) -0.01703(6) 0.42328(15) 0.0381(3) Uani 1 1 d . . .
O3 O 0.0476(2) 0.09009(6) 0.06617(17) 0.0444(4) Uani 1 1 d . . .
O4 O 0.0790(4) 0.18751(8) 0.0268(2) 0.0782(7) Uani 1 1 d . . .
C1 C 0.1980(2) -0.00332(8) 0.2907(2) 0.0317(4) Uani 1 1 d . . .
H1 H 0.2587 0.0256 0.2354 0.038 Uiso 1 1 calc R . .
C2 C 0.0842(4) 0.13428(10) -0.0135(3) 0.0505(6) Uani 1 1 d . . .
H2 H 0.1194 0.1266 -0.1148 0.061 Uiso 1 1 calc R . .
C3 C -0.0481(3) 0.15882(10) 0.4388(3) 0.0453(5) Uani 1 1 d . . .
C4 C -0.0919(5) 0.17076(13) 0.6036(3) 0.0783(10) Uani 1 1 d . . .
H4A H -0.1994 0.1908 0.6088 0.117 Uiso 1 1 calc R . .
H4B H -0.0068 0.1961 0.6496 0.117 Uiso 1 1 calc R . .
H4C H -0.0978 0.1332 0.6592 0.117 Uiso 1 1 calc R . .
N1 N -0.0774(3) 0.10570(8) 0.3814(2) 0.0517(5) Uani 1 1 d . . .
H1A H -0.0529 0.0981 0.2859 0.062 Uiso 1 1 calc R . .
H1B H -0.1215 0.0780 0.4387 0.062 Uiso 1 1 calc R . .
N2 N 0.0186(3) 0.20206(9) 0.3557(3) 0.0596(6) Uani 1 1 d . . .
H2A H 0.0443 0.1957 0.2600 0.071 Uiso 1 1 calc R . .
H2B H 0.0368 0.2369 0.3967 0.071 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.0263(2) 0.0280(2) 0.0190(2) -0.00018(15) 0.00035(15) 0.00043(16)
O1 0.0316(6) 0.0445(8) 0.0252(6) 0.0035(5) -0.0054(5) -0.0037(6)
O2 0.0324(6) 0.0554(8) 0.0265(6) 0.0053(6) -0.0061(5) -0.0059(6)
O3 0.0667(10) 0.0314(7) 0.0352(7) -0.0006(6) 0.0017(7) -0.0038(7)
O4 0.142(2) 0.0306(9) 0.0618(11) 0.0013(8) 0.0235(13) -0.0028(11)
C1 0.0299(9) 0.0377(10) 0.0275(8) 0.0027(7) -0.0017(7) -0.0008(7)
C2 0.0766(18) 0.0364(13) 0.0387(11) 0.0022(9) 0.0064(11) -0.0011(11)
C3 0.0590(13) 0.0384(12) 0.0385(11) -0.0002(9) -0.0010(10) 0.0003(10)
C4 0.137(3) 0.0552(16) 0.0429(14) -0.0080(11) 0.0159(17) -0.0095(18)
N1 0.0739(14) 0.0409(10) 0.0403(10) -0.0038(8) 0.0082(10) -0.0105(10)
N2 0.0954(17) 0.0375(11) 0.0458(11) -0.0024(9) 0.0080(11) -0.0104(10)

_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
Co1 O3 2.1050(14) 5 ?
Co1 O3 2.1050(14) . ?
Co1 O1 2.1062(12) 5 ?
Co1 O1 2.1062(12) . ?
Co1 O2 2.1107(13) 4_455 ?
Co1 O2 2.1107(13) 8_655 ?
O1 C1 1.241(2) . ?
O2 C1 1.252(2) . ?
O2 Co1 2.1107(13) 4 ?
O3 C2 1.228(3) . ?
O4 C2 1.227(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 N1 1.295(3) . ?
C3 N2 1.304(3) . ?
C3 C4 1.483(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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
O3 Co1 O3 180.00(8) 5 . ?
O3 Co1 O1 87.19(6) 5 5 ?
O3 Co1 O1 92.81(6) . 5 ?
O3 Co1 O1 92.81(6) 5 . ?
O3 Co1 O1 87.19(6) . . ?
O1 Co1 O1 180.00(8) 5 . ?
O3 Co1 O2 94.95(6) 5 4_455 ?
O3 Co1 O2 85.05(6) . 4_455 ?
O1 Co1 O2 89.63(5) 5 4_455 ?
O1 Co1 O2 90.37(5) . 4_455 ?
O3 Co1 O2 85.05(6) 5 8_655 ?
O3 Co1 O2 94.95(6) . 8_655 ?
O1 Co1 O2 90.37(5) 5 8_655 ?
O1 Co1 O2 89.63(5) . 8_655 ?
O2 Co1 O2 180.00(7) 4_455 8_655 ?
C1 O1 Co1 121.53(12) . . ?
C1 O2 Co1 123.66(13) . 4 ?
C2 O3 Co1 130.07(15) . . ?
O1 C1 O2 125.40(18) . . ?
O1 C1 H1 117.3 . . ?
O2 C1 H1 117.3 . . ?
O4 C2 O3 126.6(2) . . ?
O4 C2 H2 116.7 . . ?
O3 C2 H2 116.7 . . ?
N1 C3 N2 121.9(2) . . ?
N1 C3 C4 118.9(2) . . ?
N2 C3 C4 119.2(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.93 2.49 3.022(2) 116.3 4
C4 H4C O1 0.96 2.59 3.537(3) 169.3 5_556
N1 H1A O3 0.86 2.06 2.906(2) 168.7 .
N1 H1B O2 0.86 2.07 2.924(2) 173.8 5_556
N2 H2A O4 0.86 2.03 2.887(3) 172.6 .
N2 H2B O4 0.86 2.04 2.890(3) 170.9 7_566

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        76.61
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_2Ni-140K
_database_code_depnum_ccdc_archive 'CCDC 1840715'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 Ni O8'
_chemical_formula_weight         356.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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 ccn'

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                   7.7962(1)
_cell_length_b                   22.0461(3)
_cell_length_c                   8.4718(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1456.10(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    140.0
_cell_measurement_reflns_used    9309
_cell_measurement_theta_min      3.9880
_cell_measurement_theta_max      76.3710

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.049
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.367
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20948
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.01
_diffrn_reflns_theta_max         76.49
_reflns_number_total             1532
_reflns_number_gt                1397
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0320P)²+0.9990P] 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     SHELXL
_refine_ls_extinction_coef       0.00062(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1532
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0633
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.0000 0.0000 0.01102(11) Uani 1 2 d S . .
O1 O 0.06959(11) -0.02586(4) 0.22435(10) 0.01454(19) Uani 1 1 d . . .
O2 O 0.25212(12) -0.01691(4) 0.42437(10) 0.01600(19) Uani 1 1 d . . .
O3 O 0.04730(13) 0.08843(4) 0.06734(11) 0.0183(2) Uani 1 1 d . . .
O4 O 0.08228(18) 0.18691(5) 0.02601(13) 0.0312(3) Uani 1 1 d . . .
C1 C 0.19972(17) -0.00343(5) 0.28793(15) 0.0136(3) Uani 1 1 d . . .
H1 H 0.2633 0.0257 0.2296 0.016 Uiso 1 1 calc R . .
C2 C 0.08759(19) 0.13295(6) -0.01627(16) 0.0201(3) Uani 1 1 d . . .
H2 H 0.1254 0.1249 -0.1208 0.024 Uiso 1 1 calc R . .
C3 C -0.05049(19) 0.15882(6) 0.44191(16) 0.0195(3) Uani 1 1 d . . .
C4 C -0.1033(3) 0.17125(7) 0.60778(18) 0.0329(4) Uani 1 1 d . . .
H4A H -0.2173 0.1900 0.6084 0.049 Uiso 1 1 calc R . .
H4B H -0.0206 0.1989 0.6570 0.049 Uiso 1 1 calc R . .
H4C H -0.1069 0.1331 0.6671 0.049 Uiso 1 1 calc R . .
N1 N -0.07822(16) 0.10499(5) 0.38293(14) 0.0209(3) Uani 1 1 d . . .
H1A H -0.0499 0.0971 0.2845 0.025 Uiso 1 1 calc R . .
H1B H -0.1252 0.0766 0.4416 0.025 Uiso 1 1 calc R . .
N2 N 0.01933(17) 0.20237(5) 0.35802(15) 0.0244(3) Uani 1 1 d . . .
H2A H 0.0488 0.1957 0.2593 0.029 Uiso 1 1 calc R . .
H2B H 0.0367 0.2383 0.4005 0.029 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.01228(18) 0.01237(17) 0.00841(17) -0.00006(10) 0.00008(11) 0.00006(10)
O1 0.0148(4) 0.0176(4) 0.0112(4) 0.0010(3) -0.0017(3) -0.0011(3)
O2 0.0150(4) 0.0221(4) 0.0109(4) 0.0018(3) -0.0024(3) -0.0017(4)
O3 0.0264(5) 0.0143(4) 0.0142(4) -0.0007(3) 0.0004(4) -0.0015(4)
O4 0.0544(7) 0.0148(5) 0.0243(5) 0.0010(4) 0.0090(5) -0.0009(5)
C1 0.0138(6) 0.0150(5) 0.0120(6) 0.0005(4) 0.0010(5) 0.0006(4)
C2 0.0264(7) 0.0170(6) 0.0168(6) 0.0004(5) 0.0025(5) 0.0004(5)
C3 0.0227(7) 0.0191(6) 0.0168(6) 0.0005(5) -0.0013(5) 0.0020(5)
C4 0.0579(11) 0.0226(7) 0.0181(7) -0.0030(5) 0.0077(7) -0.0025(7)
N1 0.0288(6) 0.0180(5) 0.0161(5) -0.0007(4) 0.0030(5) -0.0040(5)
N2 0.0382(7) 0.0158(5) 0.0192(6) -0.0013(4) 0.0034(5) -0.0033(5)

_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 2.0571(9) . ?
Ni1 O1 2.0571(9) 5 ?
Ni1 O3 2.0644(9) . ?
Ni1 O3 2.0644(9) 5 ?
Ni1 O2 2.0699(9) 4_455 ?
Ni1 O2 2.0699(9) 8_655 ?
O1 C1 1.2507(16) . ?
O2 C1 1.2614(16) . ?
O2 Ni1 2.0699(9) 4 ?
O3 C2 1.2505(17) . ?
O4 C2 1.2431(18) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 N1 1.3057(18) . ?
C3 N2 1.3127(19) . ?
C3 C4 1.4898(19) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?

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 180.00(5) . 5 ?
O1 Ni1 O3 87.67(4) . . ?
O1 Ni1 O3 92.33(4) 5 . ?
O1 Ni1 O3 92.33(4) . 5 ?
O1 Ni1 O3 87.67(4) 5 5 ?
O3 Ni1 O3 180.00(5) . 5 ?
O1 Ni1 O2 90.58(3) . 4_455 ?
O1 Ni1 O2 89.42(3) 5 4_455 ?
O3 Ni1 O2 84.90(4) . 4_455 ?
O3 Ni1 O2 95.10(4) 5 4_455 ?
O1 Ni1 O2 89.42(3) . 8_655 ?
O1 Ni1 O2 90.58(3) 5 8_655 ?
O3 Ni1 O2 95.10(4) . 8_655 ?
O3 Ni1 O2 84.90(4) 5 8_655 ?
O2 Ni1 O2 180.00(5) 4_455 8_655 ?
C1 O1 Ni1 120.15(8) . . ?
C1 O2 Ni1 122.92(8) . 4 ?
C2 O3 Ni1 129.02(9) . . ?
O1 C1 O2 124.34(12) . . ?
O1 C1 H1 117.8 . . ?
O2 C1 H1 117.8 . . ?
O4 C2 O3 125.42(13) . . ?
O4 C2 H2 117.3 . . ?
O3 C2 H2 117.3 . . ?
N1 C3 N2 121.75(13) . . ?
N1 C3 C4 118.84(13) . . ?
N2 C3 C4 119.39(13) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.95 2.42 2.9567(16) 115.6 4
C4 H4C O1 0.98 2.55 3.5165(18) 167.4 5_556
N1 H1A O3 0.88 2.00 2.8704(15) 170.5 .
N1 H1B O2 0.88 2.00 2.8763(15) 174.5 5_556
N2 H2A O4 0.88 2.00 2.8754(17) 171.2 .
N2 H2B O4 0.88 1.99 2.8677(16) 171.7 7_566

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        76.49
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_2Ni-290K
_database_code_depnum_ccdc_archive 'CCDC 1840719'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 Ni O8'
_chemical_formula_weight         356.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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 ccn'

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                   7.8376(2)
_cell_length_b                   22.0576(4)
_cell_length_c                   8.5034(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1470.06(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    290.0
_cell_measurement_reflns_used    7357
_cell_measurement_theta_min      3.9920
_cell_measurement_theta_max      76.2870

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.049
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.344
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21185
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.01
_diffrn_reflns_theta_max         76.53
_reflns_number_total             1545
_reflns_number_gt                1378
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0427P)²+0.8000P] 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     SHELXL
_refine_ls_extinction_coef       0.00073(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1545
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 0.0000 0.0000 0.01864(14) Uani 1 2 d S . .
O1 O 0.07160(13) -0.02527(5) 0.22393(12) 0.0247(2) Uani 1 1 d . . .
O2 O 0.25300(15) -0.01679(5) 0.42279(12) 0.0280(2) Uani 1 1 d . . .
O3 O 0.04656(17) 0.08877(5) 0.06603(14) 0.0328(3) Uani 1 1 d . . .
O4 O 0.0823(3) 0.18647(6) 0.02473(18) 0.0587(5) Uani 1 1 d . . .
C1 C 0.2008(2) -0.00331(6) 0.28746(17) 0.0230(3) Uani 1 1 d . . .
H1 H 0.2631 0.0251 0.2307 0.028 Uiso 1 1 calc R . .
C2 C 0.0868(3) 0.13275(8) -0.0158(2) 0.0373(4) Uani 1 1 d . . .
H2 H 0.1240 0.1246 -0.1175 0.045 Uiso 1 1 calc R . .
C3 C -0.0488(2) 0.15896(8) 0.4402(2) 0.0345(4) Uani 1 1 d . . .
C4 C -0.0969(4) 0.17131(10) 0.6061(2) 0.0605(7) Uani 1 1 d . . .
H4A H -0.2036 0.1927 0.6088 0.091 Uiso 1 1 calc R . .
H4B H -0.0101 0.1956 0.6550 0.091 Uiso 1 1 calc R . .
H4C H -0.1081 0.1337 0.6618 0.091 Uiso 1 1 calc R . .
N1 N -0.0776(2) 0.10541(6) 0.38278(18) 0.0388(4) Uani 1 1 d . . .
H1A H -0.0521 0.0976 0.2865 0.047 Uiso 1 1 calc R . .
H1B H -0.1223 0.0777 0.4410 0.047 Uiso 1 1 calc R . .
N2 N 0.0188(2) 0.20229(7) 0.3559(2) 0.0451(4) Uani 1 1 d . . .
H2A H 0.0456 0.1957 0.2593 0.054 Uiso 1 1 calc R . .
H2B H 0.0364 0.2374 0.3970 0.054 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.0204(2) 0.0214(2) 0.0141(2) -0.00008(11) 0.00016(12) 0.00011(12)
O1 0.0239(5) 0.0318(5) 0.0183(5) 0.0025(4) -0.0035(4) -0.0029(4)
O2 0.0249(5) 0.0404(6) 0.0188(5) 0.0038(4) -0.0043(4) -0.0040(5)
O3 0.0494(7) 0.0242(5) 0.0249(6) -0.0013(4) 0.0015(5) -0.0033(5)
O4 0.1046(14) 0.0251(6) 0.0464(8) 0.0020(6) 0.0172(9) -0.0023(8)
C1 0.0235(7) 0.0269(7) 0.0186(6) 0.0024(5) 0.0003(6) 0.0000(5)
C2 0.0546(12) 0.0278(8) 0.0294(8) 0.0009(6) 0.0053(8) -0.0004(8)
C3 0.0435(9) 0.0308(8) 0.0293(8) -0.0009(7) -0.0005(8) 0.0009(7)
C4 0.107(2) 0.0417(10) 0.0329(10) -0.0065(8) 0.0131(11) -0.0065(12)
N1 0.0551(10) 0.0317(7) 0.0295(7) -0.0024(6) 0.0061(7) -0.0082(6)
N2 0.0712(12) 0.0285(7) 0.0355(8) -0.0013(6) 0.0062(8) -0.0074(7)

_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 2.0619(10) 5 ?
Ni1 O1 2.0619(10) . ?
Ni1 O3 2.0694(11) . ?
Ni1 O3 2.0694(11) 5 ?
Ni1 O2 2.0775(11) 4_455 ?
Ni1 O2 2.0775(11) 8_655 ?
O1 C1 1.2455(19) . ?
O2 C1 1.2571(18) . ?
O2 Ni1 2.0775(11) 4 ?
O3 C2 1.235(2) . ?
O4 C2 1.235(2) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 N1 1.298(2) . ?
C3 N2 1.307(2) . ?
C3 C4 1.486(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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 180.00(8) 5 . ?
O1 Ni1 O3 92.45(4) 5 . ?
O1 Ni1 O3 87.55(4) . . ?
O1 Ni1 O3 87.55(4) 5 5 ?
O1 Ni1 O3 92.45(4) . 5 ?
O3 Ni1 O3 180.00(6) . 5 ?
O1 Ni1 O2 89.43(4) 5 4_455 ?
O1 Ni1 O2 90.57(4) . 4_455 ?
O3 Ni1 O2 84.83(5) . 4_455 ?
O3 Ni1 O2 95.17(5) 5 4_455 ?
O1 Ni1 O2 90.57(4) 5 8_655 ?
O1 Ni1 O2 89.43(4) . 8_655 ?
O3 Ni1 O2 95.17(5) . 8_655 ?
O3 Ni1 O2 84.83(5) 5 8_655 ?
O2 Ni1 O2 180.00(6) 4_455 8_655 ?
C1 O1 Ni1 121.10(9) . . ?
C1 O2 Ni1 123.41(10) . 4 ?
C2 O3 Ni1 129.46(11) . . ?
O1 C1 O2 124.74(14) . . ?
O1 C1 H1 117.6 . . ?
O2 C1 H1 117.6 . . ?
O4 C2 O3 126.13(17) . . ?
O4 C2 H2 116.9 . . ?
O3 C2 H2 116.9 . . ?
N1 C3 N2 121.97(17) . . ?
N1 C3 C4 118.69(17) . . ?
N2 C3 C4 119.34(17) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.93 2.45 2.9757(19) 115.9 4
C4 H4C O1 0.96 2.60 3.536(2) 166.2 5_556
N1 H1A O3 0.86 2.04 2.8874(19) 169.5 .
N1 H1B O2 0.86 2.05 2.9058(18) 173.8 5_556
N2 H2A O4 0.86 2.03 2.881(2) 172.8 .
N2 H2B O4 0.86 2.03 2.886(2) 171.5 7_566

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        76.53
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_2Ni-220K
_database_code_depnum_ccdc_archive 'CCDC 1840717'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 Ni O8'
_chemical_formula_weight         356.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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 ccn'

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                   7.8166(1)
_cell_length_b                   22.0478(3)
_cell_length_c                   8.4882(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1462.85(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    220.0
_cell_measurement_reflns_used    8108
_cell_measurement_theta_min      3.9920
_cell_measurement_theta_max      76.2970

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.049
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.356
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      220.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21056
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.01
_diffrn_reflns_theta_max         76.32
_reflns_number_total             1539
_reflns_number_gt                1374
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0388P)²+0.7941P] 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     SHELXL
_refine_ls_extinction_coef       0.00063(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1539
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0700
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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 0.0000 0.0000 0.01515(12) Uani 1 2 d S . .
O1 O 0.07043(12) -0.02557(4) 0.22421(11) 0.0199(2) Uani 1 1 d . . .
O2 O 0.25246(13) -0.01689(4) 0.42353(11) 0.0226(2) Uani 1 1 d . . .
O3 O 0.04697(15) 0.08860(4) 0.06676(12) 0.0261(2) Uani 1 1 d . . .
O4 O 0.0824(2) 0.18662(5) 0.02530(15) 0.0455(4) Uani 1 1 d . . .
C1 C 0.20029(18) -0.00336(6) 0.28767(15) 0.0185(3) Uani 1 1 d . . .
H1 H 0.2633 0.0254 0.2301 0.022 Uiso 1 1 calc R . .
C2 C 0.0874(2) 0.13288(7) -0.01605(18) 0.0291(3) Uani 1 1 d . . .
H2 H 0.1251 0.1248 -0.1191 0.035 Uiso 1 1 calc R . .
C3 C -0.0495(2) 0.15895(7) 0.44089(18) 0.0277(3) Uani 1 1 d . . .
C4 C -0.0993(3) 0.17132(8) 0.6070(2) 0.0480(5) Uani 1 1 d . . .
H4A H -0.2082 0.1924 0.6089 0.072 Uiso 1 1 calc R . .
H4B H -0.0126 0.1963 0.6567 0.072 Uiso 1 1 calc R . .
H4C H -0.1096 0.1333 0.6637 0.072 Uiso 1 1 calc R . .
N1 N -0.07775(19) 0.10523(6) 0.38282(15) 0.0304(3) Uani 1 1 d . . .
H1A H -0.0509 0.0974 0.2855 0.036 Uiso 1 1 calc R . .
H1B H -0.1235 0.0772 0.4414 0.036 Uiso 1 1 calc R . .
N2 N 0.0191(2) 0.20243(6) 0.35654(18) 0.0355(3) Uani 1 1 d . . .
H2A H 0.0472 0.1958 0.2589 0.043 Uiso 1 1 calc R . .
H2B H 0.0366 0.2379 0.3982 0.043 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.01674(19) 0.01710(19) 0.01162(18) -0.00007(10) 0.00024(11) 0.00002(11)
O1 0.0197(5) 0.0248(5) 0.0152(4) 0.0018(3) -0.0026(4) -0.0019(4)
O2 0.0200(4) 0.0323(5) 0.0154(4) 0.0029(4) -0.0037(4) -0.0030(4)
O3 0.0386(6) 0.0197(4) 0.0200(5) -0.0011(4) 0.0010(5) -0.0024(4)
O4 0.0807(10) 0.0203(5) 0.0355(6) 0.0016(5) 0.0130(7) -0.0016(6)
C1 0.0185(6) 0.0215(6) 0.0157(6) 0.0011(4) 0.0010(5) 0.0001(4)
C2 0.0412(9) 0.0224(7) 0.0238(7) 0.0008(5) 0.0043(6) -0.0004(6)
C3 0.0341(8) 0.0255(7) 0.0237(7) 0.0003(6) -0.0012(6) 0.0012(6)
C4 0.0845(15) 0.0330(8) 0.0265(8) -0.0047(6) 0.0112(9) -0.0044(9)
N1 0.0428(8) 0.0249(6) 0.0234(6) -0.0018(5) 0.0050(6) -0.0063(5)
N2 0.0551(9) 0.0224(6) 0.0289(7) -0.0014(5) 0.0046(6) -0.0058(6)

_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 2.0598(9) 5 ?
Ni1 O1 2.0598(9) . ?
Ni1 O3 2.0669(10) 5 ?
Ni1 O3 2.0669(10) . ?
Ni1 O2 2.0746(10) 8_655 ?
Ni1 O2 2.0746(10) 4_455 ?
O1 C1 1.2491(17) . ?
O2 C1 1.2590(17) . ?
O2 Ni1 2.0746(10) 4 ?
O3 C2 1.2438(18) . ?
O4 C2 1.237(2) . ?
C1 H1 0.9400 . ?
C2 H2 0.9400 . ?
C3 N1 1.3018(19) . ?
C3 N2 1.311(2) . ?
C3 C4 1.488(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
N1 H1A 0.8700 . ?
N1 H1B 0.8700 . ?
N2 H2A 0.8700 . ?
N2 H2B 0.8700 . ?

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 180.00(5) 5 . ?
O1 Ni1 O3 87.59(4) 5 5 ?
O1 Ni1 O3 92.41(4) . 5 ?
O1 Ni1 O3 92.41(4) 5 . ?
O1 Ni1 O3 87.59(4) . . ?
O3 Ni1 O3 180.00(6) 5 . ?
O1 Ni1 O2 90.54(4) 5 8_655 ?
O1 Ni1 O2 89.46(4) . 8_655 ?
O3 Ni1 O2 84.85(4) 5 8_655 ?
O3 Ni1 O2 95.15(4) . 8_655 ?
O1 Ni1 O2 89.46(4) 5 4_455 ?
O1 Ni1 O2 90.54(4) . 4_455 ?
O3 Ni1 O2 95.15(4) 5 4_455 ?
O3 Ni1 O2 84.85(4) . 4_455 ?
O2 Ni1 O2 180.00(7) 8_655 4_455 ?
C1 O1 Ni1 120.55(8) . . ?
C1 O2 Ni1 123.10(9) . 4 ?
C2 O3 Ni1 129.19(10) . . ?
O1 C1 O2 124.43(12) . . ?
O1 C1 H1 117.8 . . ?
O2 C1 H1 117.8 . . ?
O4 C2 O3 125.70(15) . . ?
O4 C2 H2 117.1 . . ?
O3 C2 H2 117.1 . . ?
N1 C3 N2 121.85(14) . . ?
N1 C3 C4 118.77(14) . . ?
N2 C3 C4 119.38(14) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.94 2.43 2.9645(17) 115.8 4
C4 H4C O1 0.97 2.58 3.526(2) 165.9 5_556
N1 H1A O3 0.87 2.02 2.8778(17) 170.0 .
N1 H1B O2 0.87 2.02 2.8915(16) 174.1 5_556
N2 H2A O4 0.87 2.01 2.8759(19) 172.1 .
N2 H2B O4 0.87 2.01 2.8776(18) 171.4 7_566

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        76.32
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_1Co-400K
_database_code_depnum_ccdc_archive 'CCDC 1840732'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 Co N4 O8'
_chemical_formula_weight         357.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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 ccn'

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                   7.9282(2)
_cell_length_b                   22.1074(8)
_cell_length_c                   8.6031(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1507.88(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    400.0
_cell_measurement_reflns_used    5105
_cell_measurement_theta_min      7.8480
_cell_measurement_theta_max      76.3940

_exptl_crystal_description       block
_exptl_crystal_colour            purple-red
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             740
_exptl_absorpt_coefficient_mu    9.352
_exptl_absorpt_correction_T_min  0.324
_exptl_absorpt_correction_T_max  0.566
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      400.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21273
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         76.89
_reflns_number_total             1566
_reflns_number_gt                1235
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0377P)²+0.8166P] 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     SHELXL
_refine_ls_extinction_coef       0.00039(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1566
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0795
_refine_ls_wR_factor_gt          0.0724
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
Co1 Co 0.0000 0.0000 0.0000 0.02729(14) Uani 1 2 d S . .
O1 O 0.07196(17) -0.02489(6) 0.22690(15) 0.0374(3) Uani 1 1 d . . .
O2 O 0.25156(18) -0.01691(7) 0.42267(16) 0.0423(3) Uani 1 1 d . . .
O3 O 0.0474(2) 0.09021(7) 0.06546(18) 0.0490(4) Uani 1 1 d . . .
O4 O 0.0788(4) 0.18743(8) 0.0269(2) 0.0865(7) Uani 1 1 d . . .
C1 C 0.1987(3) -0.00325(9) 0.2903(2) 0.0349(4) Uani 1 1 d . . .
H1 H 0.2595 0.0255 0.2348 0.042 Uiso 1 1 calc R . .
C2 C 0.0835(4) 0.13420(11) -0.0134(3) 0.0565(6) Uani 1 1 d . . .
H2 H 0.1183 0.1266 -0.1147 0.068 Uiso 1 1 calc R . .
C3 C -0.0474(3) 0.15872(11) 0.4386(3) 0.0504(5) Uani 1 1 d . . .
C4 C -0.0911(5) 0.17066(13) 0.6034(3) 0.0861(11) Uani 1 1 d . . .
H4A H -0.1945 0.1932 0.6082 0.129 Uiso 1 1 calc R . .
H4B H -0.0024 0.1936 0.6513 0.129 Uiso 1 1 calc R . .
H4C H -0.1048 0.1330 0.6573 0.129 Uiso 1 1 calc R . .
N1 N -0.0774(3) 0.10576(9) 0.3816(2) 0.0575(5) Uani 1 1 d . . .
H1A H -0.0538 0.0982 0.2860 0.069 Uiso 1 1 calc R . .
H1B H -0.1210 0.0781 0.4392 0.069 Uiso 1 1 calc R . .
N2 N 0.0185(3) 0.20197(10) 0.3556(3) 0.0662(7) Uani 1 1 d . . .
H2A H 0.0434 0.1957 0.2596 0.079 Uiso 1 1 calc R . .
H2B H 0.0370 0.2368 0.3967 0.079 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.0296(2) 0.0310(2) 0.0212(2) -0.00030(16) 0.00039(15) 0.00037(17)
O1 0.0354(7) 0.0491(8) 0.0277(6) 0.0038(6) -0.0068(6) -0.0041(6)
O2 0.0363(7) 0.0610(9) 0.0296(6) 0.0064(6) -0.0070(6) -0.0064(7)
O3 0.0742(10) 0.0342(8) 0.0387(8) -0.0010(6) 0.0019(8) -0.0050(7)
O4 0.157(2) 0.0345(10) 0.0679(12) 0.0017(8) 0.0258(14) -0.0028(12)
C1 0.0342(9) 0.0405(11) 0.0299(9) 0.0031(8) -0.0021(8) -0.0009(7)
C2 0.0854(19) 0.0411(14) 0.0429(12) 0.0020(9) 0.0071(12) -0.0003(13)
C3 0.0646(14) 0.0430(13) 0.0434(12) -0.0012(10) -0.0016(11) 0.0005(11)
C4 0.149(3) 0.0610(18) 0.0480(15) -0.0089(12) 0.0185(18) -0.013(2)
N1 0.0818(15) 0.0452(11) 0.0455(11) -0.0051(8) 0.0095(11) -0.0115(10)
N2 0.106(2) 0.0413(11) 0.0508(12) -0.0016(9) 0.0076(12) -0.0112(11)

_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
Co1 O3 2.1060(15) . ?
Co1 O3 2.1060(15) 5 ?
Co1 O1 2.1068(12) 5 ?
Co1 O1 2.1069(12) . ?
Co1 O2 2.1124(14) 4_455 ?
Co1 O2 2.1124(14) 8_655 ?
O1 C1 1.239(2) . ?
O2 C1 1.251(2) . ?
O2 Co1 2.1124(14) 4 ?
O3 C2 1.220(3) . ?
O4 C2 1.227(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 N1 1.292(3) . ?
C3 N2 1.303(3) . ?
C3 C4 1.483(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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
O3 Co1 O3 180.00(9) . 5 ?
O3 Co1 O1 92.79(6) . 5 ?
O3 Co1 O1 87.21(6) 5 5 ?
O3 Co1 O1 87.21(6) . . ?
O3 Co1 O1 92.79(6) 5 . ?
O1 Co1 O1 180.00(8) 5 . ?
O3 Co1 O2 85.09(6) . 4_455 ?
O3 Co1 O2 94.91(6) 5 4_455 ?
O1 Co1 O2 89.60(5) 5 4_455 ?
O1 Co1 O2 90.40(5) . 4_455 ?
O3 Co1 O2 94.91(6) . 8_655 ?
O3 Co1 O2 85.09(6) 5 8_655 ?
O1 Co1 O2 90.40(5) 5 8_655 ?
O1 Co1 O2 89.60(5) . 8_655 ?
O2 Co1 O2 180.00(8) 4_455 8_655 ?
C1 O1 Co1 121.76(13) . . ?
C1 O2 Co1 123.81(13) . 4 ?
C2 O3 Co1 130.41(16) . . ?
O1 C1 O2 125.39(19) . . ?
O1 C1 H1 117.3 . . ?
O2 C1 H1 117.3 . . ?
O3 C2 O4 126.9(2) . . ?
O3 C2 H2 116.5 . . ?
O4 C2 H2 116.5 . . ?
N1 C3 N2 122.1(2) . . ?
N1 C3 C4 118.8(2) . . ?
N2 C3 C4 119.1(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.93 2.50 3.028(2) 116.3 4
C4 H4C O1 0.96 2.60 3.541(3) 166.2 5_556
N1 H1A O3 0.86 2.07 2.914(3) 168.1 .
N1 H1B O2 0.86 2.08 2.933(2) 173.5 5_556
N2 H2A O4 0.86 2.03 2.886(3) 173.2 .
N2 H2B O4 0.86 2.04 2.895(3) 171.0 7_566

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        76.89
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_1Co-320K
_database_code_depnum_ccdc_archive 'CCDC 1840730'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 Co N4 O8'
_chemical_formula_weight         357.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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 ccn'

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                   7.8926(2)
_cell_length_b                   22.0966(7)
_cell_length_c                   8.5875(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1497.66(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    320.0
_cell_measurement_reflns_used    5647
_cell_measurement_theta_min      7.8710
_cell_measurement_theta_max      76.2870

_exptl_crystal_description       block
_exptl_crystal_colour            purple-red
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             740
_exptl_absorpt_coefficient_mu    9.416
_exptl_absorpt_correction_T_min  0.321
_exptl_absorpt_correction_T_max  0.563
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      320.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21119
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         76.47
_reflns_number_total             1556
_reflns_number_gt                1297
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0367P)²+0.8876P] 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     SHELXL
_refine_ls_extinction_coef       0.00035(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1556
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0754
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
Co1 Co 0.0000 0.0000 0.0000 0.02192(13) Uani 1 2 d S . .
O1 O 0.07012(15) -0.02534(6) 0.22726(13) 0.0303(3) Uani 1 1 d . . .
O2 O 0.25035(16) -0.01712(6) 0.42404(14) 0.0341(3) Uani 1 1 d . . .
O3 O 0.0479(2) 0.08997(6) 0.06643(16) 0.0393(3) Uani 1 1 d . . .
O4 O 0.0795(3) 0.18760(7) 0.0270(2) 0.0692(6) Uani 1 1 d . . .
C1 C 0.1976(2) -0.00341(8) 0.2909(2) 0.0285(4) Uani 1 1 d . . .
H1 H 0.2587 0.0254 0.2354 0.034 Uiso 1 1 calc R . .
C2 C 0.0849(3) 0.13425(10) -0.0138(2) 0.0444(5) Uani 1 1 d . . .
H2 H 0.1205 0.1266 -0.1151 0.053 Uiso 1 1 calc R . .
C3 C -0.0484(3) 0.15878(9) 0.4390(2) 0.0409(4) Uani 1 1 d . . .
C4 C -0.0937(5) 0.17076(12) 0.6039(3) 0.0692(8) Uani 1 1 d . . .
H4A H -0.2001 0.1917 0.6081 0.104 Uiso 1 1 calc R . .
H4B H -0.0074 0.1952 0.6512 0.104 Uiso 1 1 calc R . .
H4C H -0.1029 0.1331 0.6589 0.104 Uiso 1 1 calc R . .
N1 N -0.0776(3) 0.10567(8) 0.3815(2) 0.0454(4) Uani 1 1 d . . .
H1A H -0.0530 0.0981 0.2859 0.054 Uiso 1 1 calc R . .
H1B H -0.1217 0.0779 0.4389 0.054 Uiso 1 1 calc R . .
N2 N 0.0185(3) 0.20219(9) 0.3558(2) 0.0531(5) Uani 1 1 d . . .
H2A H 0.0444 0.1959 0.2599 0.064 Uiso 1 1 calc R . .
H2B H 0.0366 0.2371 0.3969 0.064 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.0238(2) 0.0247(2) 0.01721(19) -0.00031(14) 0.00037(14) 0.00026(15)
O1 0.0285(6) 0.0394(7) 0.0231(5) 0.0032(5) -0.0048(5) -0.0034(5)
O2 0.0291(6) 0.0492(7) 0.0239(6) 0.0045(5) -0.0053(5) -0.0055(6)
O3 0.0589(8) 0.0281(7) 0.0310(7) -0.0009(5) 0.0015(7) -0.0038(6)
O4 0.1258(18) 0.0281(9) 0.0538(10) 0.0015(7) 0.0209(11) -0.0017(10)
C1 0.0276(8) 0.0335(9) 0.0243(8) 0.0028(7) -0.0011(7) -0.0013(6)
C2 0.0665(15) 0.0325(11) 0.0342(10) 0.0013(8) 0.0051(10) -0.0003(10)
C3 0.0523(12) 0.0353(11) 0.0350(10) -0.0001(8) -0.0013(9) 0.0009(9)
C4 0.121(3) 0.0477(14) 0.0385(12) -0.0073(10) 0.0149(14) -0.0077(15)
N1 0.0646(12) 0.0360(10) 0.0355(9) -0.0034(7) 0.0067(9) -0.0090(8)
N2 0.0846(15) 0.0329(10) 0.0417(10) -0.0020(8) 0.0073(10) -0.0088(9)

_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
Co1 O3 2.1025(13) . ?
Co1 O3 2.1025(13) 5 ?
Co1 O1 2.1044(11) 5 ?
Co1 O1 2.1044(11) . ?
Co1 O2 2.1098(13) 4_455 ?
Co1 O2 2.1098(13) 8_655 ?
O1 C1 1.244(2) . ?
O2 C1 1.254(2) . ?
O2 Co1 2.1098(13) 4 ?
O3 C2 1.232(2) . ?
O4 C2 1.231(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 N1 1.294(3) . ?
C3 N2 1.307(3) . ?
C3 C4 1.484(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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
O3 Co1 O3 180.00(8) . 5 ?
O3 Co1 O1 92.71(5) . 5 ?
O3 Co1 O1 87.29(5) 5 5 ?
O3 Co1 O1 87.29(5) . . ?
O3 Co1 O1 92.71(5) 5 . ?
O1 Co1 O1 180.00(7) 5 . ?
O3 Co1 O2 85.09(6) . 4_455 ?
O3 Co1 O2 94.91(6) 5 4_455 ?
O1 Co1 O2 89.62(5) 5 4_455 ?
O1 Co1 O2 90.38(5) . 4_455 ?
O3 Co1 O2 94.91(6) . 8_655 ?
O3 Co1 O2 85.09(6) 5 8_655 ?
O1 Co1 O2 90.38(5) 5 8_655 ?
O1 Co1 O2 89.62(5) . 8_655 ?
O2 Co1 O2 180.00(7) 4_455 8_655 ?
C1 O1 Co1 121.11(11) . . ?
C1 O2 Co1 123.27(12) . 4 ?
C2 O3 Co1 129.94(13) . . ?
O1 C1 O2 125.11(17) . . ?
O1 C1 H1 117.4 . . ?
O2 C1 H1 117.4 . . ?
O4 C2 O3 126.4(2) . . ?
O4 C2 H2 116.8 . . ?
O3 C2 H2 116.8 . . ?
N1 C3 N2 121.9(2) . . ?
N1 C3 C4 118.8(2) . . ?
N2 C3 C4 119.2(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.93 2.48 3.012(2) 116.6 4
C4 H4C O1 0.96 2.59 3.530(3) 167.6 5_556
N1 H1A O3 0.86 2.05 2.902(2) 168.7 .
N1 H1B O2 0.86 2.05 2.911(2) 173.9 5_556
N2 H2A O4 0.86 2.03 2.882(3) 172.7 .
N2 H2B O4 0.86 2.03 2.885(3) 170.9 7_566

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        76.47
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_2Ni-320K
_database_code_depnum_ccdc_archive 'CCDC 1840720'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 Ni O8'
_chemical_formula_weight         356.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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 ccn'

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                   7.8494(2)
_cell_length_b                   22.0641(4)
_cell_length_c                   8.5078(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1473.47(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    320.0
_cell_measurement_reflns_used    7039
_cell_measurement_theta_min      3.9910
_cell_measurement_theta_max      76.0700

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.049
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.339
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      320.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21231
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.01
_diffrn_reflns_theta_max         76.61
_reflns_number_total             1550
_reflns_number_gt                1335
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0431P)²+0.8139P] 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     SHELXL
_refine_ls_extinction_coef       0.00068(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1550
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.0000 0.0000 0.02023(14) Uani 1 2 d S . .
O1 O 0.07201(14) -0.02508(5) 0.22400(12) 0.0266(2) Uani 1 1 d . . .
O2 O 0.25345(15) -0.01676(5) 0.42237(13) 0.0306(3) Uani 1 1 d . . .
O3 O 0.04645(18) 0.08882(5) 0.06579(14) 0.0357(3) Uani 1 1 d . . .
O4 O 0.0820(3) 0.18633(6) 0.02456(19) 0.0646(5) Uani 1 1 d . . .
C1 C 0.2010(2) -0.00330(6) 0.28731(18) 0.0247(3) Uani 1 1 d . . .
H1 H 0.2634 0.0251 0.2304 0.030 Uiso 1 1 calc R . .
C2 C 0.0865(3) 0.13270(8) -0.0157(2) 0.0411(4) Uani 1 1 d . . .
H2 H 0.1237 0.1246 -0.1174 0.049 Uiso 1 1 calc R . .
C3 C -0.0487(3) 0.15894(8) 0.4401(2) 0.0378(4) Uani 1 1 d . . .
C4 C -0.0956(4) 0.17136(10) 0.6059(3) 0.0669(8) Uani 1 1 d . . .
H4A H -0.1994 0.1944 0.6088 0.100 Uiso 1 1 calc R . .
H4B H -0.0062 0.1940 0.6556 0.100 Uiso 1 1 calc R . .
H4C H -0.1117 0.1337 0.6605 0.100 Uiso 1 1 calc R . .
N1 N -0.0774(2) 0.10549(7) 0.38283(19) 0.0430(4) Uani 1 1 d . . .
H1A H -0.0519 0.0977 0.2867 0.052 Uiso 1 1 calc R . .
H1B H -0.1220 0.0778 0.4410 0.052 Uiso 1 1 calc R . .
N2 N 0.0189(3) 0.20221(7) 0.3555(2) 0.0499(5) Uani 1 1 d . . .
H2A H 0.0457 0.1956 0.2590 0.060 Uiso 1 1 calc R . .
H2B H 0.0366 0.2373 0.3964 0.060 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.0224(2) 0.0233(2) 0.0151(2) -0.00001(12) 0.00034(13) 0.00012(12)
O1 0.0262(5) 0.0347(6) 0.0190(5) 0.0029(4) -0.0042(4) -0.0030(4)
O2 0.0274(5) 0.0444(6) 0.0200(5) 0.0044(4) -0.0048(4) -0.0044(5)
O3 0.0540(8) 0.0262(5) 0.0270(6) -0.0016(4) 0.0017(6) -0.0039(5)
O4 0.1173(16) 0.0267(7) 0.0499(8) 0.0020(6) 0.0191(10) -0.0024(8)
C1 0.0254(7) 0.0289(7) 0.0198(7) 0.0028(5) 0.0006(6) -0.0002(5)
C2 0.0611(13) 0.0299(9) 0.0322(9) 0.0010(7) 0.0064(8) -0.0015(8)
C3 0.0483(10) 0.0332(8) 0.0318(9) -0.0007(7) -0.0013(8) 0.0003(8)
C4 0.119(2) 0.0453(11) 0.0361(11) -0.0074(9) 0.0153(13) -0.0077(13)
N1 0.0620(11) 0.0346(7) 0.0324(8) -0.0030(6) 0.0068(8) -0.0089(7)
N2 0.0791(13) 0.0312(8) 0.0393(9) -0.0014(7) 0.0065(9) -0.0088(8)

_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 2.0634(10) . ?
Ni1 O1 2.0634(10) 5 ?
Ni1 O3 2.0704(11) . ?
Ni1 O3 2.0704(11) 5 ?
Ni1 O2 2.0780(12) 4_455 ?
Ni1 O2 2.0780(12) 8_655 ?
O1 C1 1.244(2) . ?
O2 C1 1.2561(19) . ?
O2 Ni1 2.0780(12) 4 ?
O3 C2 1.232(2) . ?
O4 C2 1.232(2) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 N1 1.296(2) . ?
C3 N2 1.308(3) . ?
C3 C4 1.483(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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 180.00(6) . 5 ?
O1 Ni1 O3 87.48(5) . . ?
O1 Ni1 O3 92.52(5) 5 . ?
O1 Ni1 O3 92.52(5) . 5 ?
O1 Ni1 O3 87.48(5) 5 5 ?
O3 Ni1 O3 180.00(2) . 5 ?
O1 Ni1 O2 90.53(4) . 4_455 ?
O1 Ni1 O2 89.47(4) 5 4_455 ?
O3 Ni1 O2 84.82(5) . 4_455 ?
O3 Ni1 O2 95.18(5) 5 4_455 ?
O1 Ni1 O2 89.47(4) . 8_655 ?
O1 Ni1 O2 90.53(4) 5 8_655 ?
O3 Ni1 O2 95.18(5) . 8_655 ?
O3 Ni1 O2 84.82(5) 5 8_655 ?
O2 Ni1 O2 180.00(6) 4_455 8_655 ?
C1 O1 Ni1 121.29(10) . . ?
C1 O2 Ni1 123.62(11) . 4 ?
C2 O3 Ni1 129.55(12) . . ?
O1 C1 O2 124.86(15) . . ?
O1 C1 H1 117.6 . . ?
O2 C1 H1 117.6 . . ?
O3 C2 O4 126.20(18) . . ?
O3 C2 H2 116.9 . . ?
O4 C2 H2 116.9 . . ?
N1 C3 N2 121.87(18) . . ?
N1 C3 C4 118.84(18) . . ?
N2 C3 C4 119.28(18) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.93 2.45 2.980(2) 115.9 4
C4 H4C O1 0.96 2.61 3.542(3) 164.0 5_556
N1 H1A O3 0.86 2.04 2.891(2) 169.6 .
N1 H1B O2 0.86 2.06 2.9134(19) 173.7 5_556
N2 H2A O4 0.86 2.03 2.880(2) 172.6 .
N2 H2B O4 0.86 2.04 2.892(2) 171.4 7_566

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        76.61
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_1Co-260K
_database_code_depnum_ccdc_archive 'CCDC 1840728'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 Co N4 O8'
_chemical_formula_weight         357.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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 ccn'

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                   7.8675(2)
_cell_length_b                   22.0901(6)
_cell_length_c                   8.5777(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1490.75(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    260.0
_cell_measurement_reflns_used    6104
_cell_measurement_theta_min      7.8800
_cell_measurement_theta_max      76.1730

_exptl_crystal_description       block
_exptl_crystal_colour            purple-red
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             740
_exptl_absorpt_coefficient_mu    9.460
_exptl_absorpt_correction_T_min  0.320
_exptl_absorpt_correction_T_max  0.561
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      260.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21004
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         76.41
_reflns_number_total             1547
_reflns_number_gt                1316
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0377P)²+0.8536P] 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     SHELXL
_refine_ls_extinction_coef       0.00042(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1547
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0726
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.004
_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
Co1 Co 0.0000 0.0000 0.0000 0.01800(13) Uani 1 2 d S . .
O1 O 0.06890(14) -0.02570(5) 0.22758(12) 0.0251(3) Uani 1 1 d . . .
O2 O 0.24985(15) -0.01716(6) 0.42495(13) 0.0283(3) Uani 1 1 d . . .
O3 O 0.04859(18) 0.08983(5) 0.06710(14) 0.0323(3) Uani 1 1 d . . .
O4 O 0.0793(3) 0.18776(7) 0.02711(18) 0.0566(5) Uani 1 1 d . . .
C1 C 0.1970(2) -0.00346(7) 0.29136(18) 0.0236(3) Uani 1 1 d . . .
H1 H 0.2579 0.0255 0.2358 0.028 Uiso 1 1 calc R . .
C2 C 0.0858(3) 0.13424(9) -0.0139(2) 0.0361(4) Uani 1 1 d . . .
H2 H 0.1221 0.1266 -0.1152 0.043 Uiso 1 1 calc R . .
C3 C -0.0489(3) 0.15885(8) 0.4393(2) 0.0333(4) Uani 1 1 d . . .
C4 C -0.0956(4) 0.17084(10) 0.6044(3) 0.0568(7) Uani 1 1 d . . .
H4A H -0.2047 0.1902 0.6082 0.085 Uiso 1 1 calc R . .
H4B H -0.0119 0.1967 0.6510 0.085 Uiso 1 1 calc R . .
H4C H -0.1004 0.1333 0.6605 0.085 Uiso 1 1 calc R . .
N1 N -0.0777(2) 0.10558(7) 0.38117(18) 0.0369(4) Uani 1 1 d . . .
H1A H -0.0525 0.0981 0.2855 0.044 Uiso 1 1 calc R . .
H1B H -0.1221 0.0778 0.4383 0.044 Uiso 1 1 calc R . .
N2 N 0.0185(2) 0.20234(8) 0.3562(2) 0.0431(4) Uani 1 1 d . . .
H2A H 0.0448 0.1960 0.2602 0.052 Uiso 1 1 calc R . .
H2B H 0.0363 0.2372 0.3974 0.052 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.01945(19) 0.0205(2) 0.01400(19) -0.00009(13) 0.00040(12) 0.00026(13)
O1 0.0235(5) 0.0326(6) 0.0192(5) 0.0027(4) -0.0039(4) -0.0027(5)
O2 0.0243(5) 0.0409(7) 0.0197(5) 0.0041(5) -0.0042(5) -0.0040(5)
O3 0.0482(7) 0.0236(6) 0.0251(6) -0.0008(5) 0.0012(6) -0.0028(5)
O4 0.1028(14) 0.0240(8) 0.0429(8) 0.0009(6) 0.0155(9) -0.0015(8)
C1 0.0225(7) 0.0278(8) 0.0206(7) 0.0024(6) -0.0008(6) -0.0001(6)
C2 0.0527(12) 0.0282(10) 0.0273(9) 0.0011(7) 0.0044(8) 0.0000(8)
C3 0.0418(9) 0.0300(9) 0.0282(9) -0.0007(7) -0.0010(8) 0.0017(8)
C4 0.098(2) 0.0401(12) 0.0319(11) -0.0064(8) 0.0125(12) -0.0044(12)
N1 0.0526(10) 0.0300(8) 0.0281(7) -0.0024(6) 0.0060(7) -0.0071(7)
N2 0.0679(12) 0.0272(9) 0.0342(9) -0.0017(7) 0.0063(8) -0.0067(7)

_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
Co1 O3 2.1012(12) . ?
Co1 O3 2.1012(12) 5 ?
Co1 O1 2.1040(11) 5 ?
Co1 O1 2.1040(11) . ?
Co1 O2 2.1051(11) 8_655 ?
Co1 O2 2.1051(11) 4_455 ?
O1 C1 1.247(2) . ?
O2 C1 1.256(2) . ?
O2 Co1 2.1051(11) 4 ?
O3 C2 1.237(2) . ?
O4 C2 1.235(2) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 N1 1.298(2) . ?
C3 N2 1.309(3) . ?
C3 C4 1.486(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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
O3 Co1 O3 180.00(2) . 5 ?
O3 Co1 O1 92.65(5) . 5 ?
O3 Co1 O1 87.35(5) 5 5 ?
O3 Co1 O1 87.35(5) . . ?
O3 Co1 O1 92.65(5) 5 . ?
O1 Co1 O1 180.00(6) 5 . ?
O3 Co1 O2 94.80(5) . 8_655 ?
O3 Co1 O2 85.20(5) 5 8_655 ?
O1 Co1 O2 90.33(4) 5 8_655 ?
O1 Co1 O2 89.67(4) . 8_655 ?
O3 Co1 O2 85.20(5) . 4_455 ?
O3 Co1 O2 94.80(5) 5 4_455 ?
O1 Co1 O2 89.67(4) 5 4_455 ?
O1 Co1 O2 90.33(4) . 4_455 ?
O2 Co1 O2 180.00(6) 8_655 4_455 ?
C1 O1 Co1 120.58(10) . . ?
C1 O2 Co1 123.05(11) . 4 ?
C2 O3 Co1 129.63(12) . . ?
O1 C1 O2 124.95(15) . . ?
O1 C1 H1 117.5 . . ?
O2 C1 H1 117.5 . . ?
O4 C2 O3 126.08(18) . . ?
O4 C2 H2 117.0 . . ?
O3 C2 H2 117.0 . . ?
N1 C3 N2 121.79(18) . . ?
N1 C3 C4 118.96(18) . . ?
N2 C3 C4 119.24(18) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.93 2.47 3.001(2) 116.6 4
C4 H4C O1 0.96 2.58 3.522(3) 168.8 5_556
N1 H1A O3 0.86 2.04 2.892(2) 169.0 .
N1 H1B O2 0.86 2.04 2.9007(19) 174.0 5_556
N2 H2A O4 0.86 2.03 2.881(2) 172.4 .
N2 H2B O4 0.86 2.02 2.876(2) 170.9 7_566

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        76.41
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_1Co-220K
_database_code_depnum_ccdc_archive 'CCDC 1840727'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 Co N4 O8'
_chemical_formula_weight         357.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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 ccn'

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                   7.8547(2)
_cell_length_b                   22.0887(6)
_cell_length_c                   8.5717(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1487.19(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    220.0
_cell_measurement_reflns_used    6398
_cell_measurement_theta_min      5.9880
_cell_measurement_theta_max      76.3160

_exptl_crystal_description       block
_exptl_crystal_colour            purple-red
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             740
_exptl_absorpt_coefficient_mu    9.482
_exptl_absorpt_correction_T_min  0.319
_exptl_absorpt_correction_T_max  0.561
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      220.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20949
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         76.45
_reflns_number_total             1544
_reflns_number_gt                1340
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0368P)²+0.9071P] 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     SHELXL
_refine_ls_extinction_coef       0.00041(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1544
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0704
_refine_ls_wR_factor_gt          0.0667
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
Co1 Co 0.0000 0.0000 0.0000 0.01534(12) Uani 1 2 d S . .
O1 O 0.06828(13) -0.02593(5) 0.22779(12) 0.0216(2) Uani 1 1 d . . .
O2 O 0.24955(14) -0.01722(5) 0.42550(13) 0.0243(2) Uani 1 1 d . . .
O3 O 0.04878(17) 0.08966(5) 0.06755(14) 0.0276(3) Uani 1 1 d . . .
O4 O 0.0794(3) 0.18782(6) 0.02738(17) 0.0484(4) Uani 1 1 d . . .
C1 C 0.1965(2) -0.00354(7) 0.29162(18) 0.0201(3) Uani 1 1 d . . .
H1 H 0.2580 0.0257 0.2354 0.024 Uiso 1 1 calc R . .
C2 C 0.0863(3) 0.13423(8) -0.0142(2) 0.0309(4) Uani 1 1 d . . .
H2 H 0.1231 0.1265 -0.1167 0.037 Uiso 1 1 calc R . .
C3 C -0.0491(2) 0.15884(8) 0.4395(2) 0.0286(4) Uani 1 1 d . . .
C4 C -0.0972(4) 0.17084(10) 0.6046(2) 0.0483(6) Uani 1 1 d . . .
H4A H -0.2078 0.1903 0.6078 0.072 Uiso 1 1 calc R . .
H4B H -0.0130 0.1971 0.6521 0.072 Uiso 1 1 calc R . .
H4C H -0.1020 0.1329 0.6614 0.072 Uiso 1 1 calc R . .
N1 N -0.0781(2) 0.10545(6) 0.38109(17) 0.0312(3) Uani 1 1 d . . .
H1A H -0.0524 0.0979 0.2843 0.037 Uiso 1 1 calc R . .
H1B H -0.1232 0.0773 0.4388 0.037 Uiso 1 1 calc R . .
N2 N 0.0186(2) 0.20241(7) 0.3564(2) 0.0371(4) Uani 1 1 d . . .
H2A H 0.0455 0.1960 0.2593 0.045 Uiso 1 1 calc R . .
H2B H 0.0367 0.2377 0.3983 0.045 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.01660(19) 0.0177(2) 0.01168(18) -0.00025(12) 0.00035(12) 0.00015(12)
O1 0.0202(5) 0.0285(6) 0.0160(5) 0.0021(4) -0.0033(4) -0.0016(4)
O2 0.0212(5) 0.0349(6) 0.0170(5) 0.0034(4) -0.0035(4) -0.0034(5)
O3 0.0408(6) 0.0206(6) 0.0215(6) -0.0006(4) 0.0014(5) -0.0024(5)
O4 0.0879(12) 0.0210(7) 0.0364(7) 0.0011(6) 0.0146(8) -0.0011(7)
C1 0.0190(7) 0.0234(8) 0.0179(7) 0.0016(6) -0.0007(6) -0.0005(5)
C2 0.0440(10) 0.0246(9) 0.0240(8) 0.0012(6) 0.0034(7) -0.0001(8)
C3 0.0352(9) 0.0264(9) 0.0243(8) 0.0000(7) -0.0014(7) 0.0016(7)
C4 0.0838(17) 0.0343(11) 0.0268(10) -0.0049(7) 0.0102(10) -0.0039(11)
N1 0.0440(9) 0.0251(8) 0.0244(7) -0.0021(6) 0.0050(6) -0.0055(6)
N2 0.0589(10) 0.0241(8) 0.0284(8) -0.0020(6) 0.0061(7) -0.0062(7)

_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
Co1 O3 2.0986(11) . ?
Co1 O3 2.0986(11) 5 ?
Co1 O2 2.1030(11) 4_455 ?
Co1 O2 2.1030(11) 8_655 ?
Co1 O1 2.1043(10) 5 ?
Co1 O1 2.1043(10) . ?
O1 C1 1.2485(19) . ?
O2 C1 1.2577(19) . ?
O2 Co1 2.1030(11) 4 ?
O3 C2 1.244(2) . ?
O4 C2 1.237(2) . ?
C1 H1 0.9400 . ?
C2 H2 0.9400 . ?
C3 N1 1.301(2) . ?
C3 N2 1.310(2) . ?
C3 C4 1.488(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
N1 H1A 0.8700 . ?
N1 H1B 0.8700 . ?
N2 H2A 0.8700 . ?
N2 H2B 0.8700 . ?

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
O3 Co1 O3 180.00(2) . 5 ?
O3 Co1 O2 85.20(5) . 4_455 ?
O3 Co1 O2 94.80(5) 5 4_455 ?
O3 Co1 O2 94.80(5) . 8_655 ?
O3 Co1 O2 85.20(5) 5 8_655 ?
O2 Co1 O2 180.00(9) 4_455 8_655 ?
O3 Co1 O1 92.62(4) . 5 ?
O3 Co1 O1 87.38(4) 5 5 ?
O2 Co1 O1 89.66(4) 4_455 5 ?
O2 Co1 O1 90.34(4) 8_655 5 ?
O3 Co1 O1 87.38(4) . . ?
O3 Co1 O1 92.62(4) 5 . ?
O2 Co1 O1 90.34(4) 4_455 . ?
O2 Co1 O1 89.66(4) 8_655 . ?
O1 Co1 O1 180.00(6) 5 . ?
C1 O1 Co1 120.29(10) . . ?
C1 O2 Co1 122.92(10) . 4 ?
C2 O3 Co1 129.39(11) . . ?
O1 C1 O2 124.88(15) . . ?
O1 C1 H1 117.6 . . ?
O2 C1 H1 117.6 . . ?
O4 C2 O3 125.74(17) . . ?
O4 C2 H2 117.1 . . ?
O3 C2 H2 117.1 . . ?
N1 C3 N2 121.84(17) . . ?
N1 C3 C4 118.88(17) . . ?
N2 C3 C4 119.27(17) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.94 2.46 2.9964(19) 116.4 4
C4 H4C O1 0.97 2.56 3.516(2) 168.4 5_556
N1 H1A O3 0.87 2.03 2.8875(19) 168.9 .
N1 H1B O2 0.87 2.02 2.8913(18) 174.2 5_556
N2 H2A O4 0.87 2.01 2.879(2) 172.2 .
N2 H2B O4 0.87 2.01 2.873(2) 170.9 7_566

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        76.45
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.317
_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_1Co-290K
_database_code_depnum_ccdc_archive 'CCDC 1840729'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 Co N4 O8'
_chemical_formula_weight         357.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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 ccn'

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                   7.8811(2)
_cell_length_b                   22.0928(6)
_cell_length_c                   8.5825(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1494.35(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    290.0
_cell_measurement_reflns_used    5864
_cell_measurement_theta_min      7.8940
_cell_measurement_theta_max      76.5200

_exptl_crystal_description       block
_exptl_crystal_colour            purple-red
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             740
_exptl_absorpt_coefficient_mu    9.437
_exptl_absorpt_correction_T_min  0.318
_exptl_absorpt_correction_T_max  0.562
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21070
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         76.51
_reflns_number_total             1552
_reflns_number_gt                1306
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0407P)²+0.8345P] 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     SHELXL
_refine_ls_extinction_coef       0.00042(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1552
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0720
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.006
_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
Co1 Co 0.0000 0.0000 0.0000 0.01971(13) Uani 1 2 d S . .
O1 O 0.06951(15) -0.02556(6) 0.22746(13) 0.0275(3) Uani 1 1 d . . .
O2 O 0.25016(16) -0.01713(6) 0.42446(14) 0.0310(3) Uani 1 1 d . . .
O3 O 0.04824(19) 0.08986(6) 0.06696(15) 0.0354(3) Uani 1 1 d . . .
O4 O 0.0793(3) 0.18763(7) 0.0270(2) 0.0626(5) Uani 1 1 d . . .
C1 C 0.1973(2) -0.00342(7) 0.29141(19) 0.0259(4) Uani 1 1 d . . .
H1 H 0.2582 0.0255 0.2360 0.031 Uiso 1 1 calc R . .
C2 C 0.0853(3) 0.13423(9) -0.0140(2) 0.0399(5) Uani 1 1 d . . .
H2 H 0.1211 0.1266 -0.1153 0.048 Uiso 1 1 calc R . .
C3 C -0.0487(3) 0.15879(9) 0.4390(2) 0.0368(4) Uani 1 1 d . . .
C4 C -0.0943(4) 0.17078(11) 0.6041(3) 0.0628(8) Uani 1 1 d . . .
H4A H -0.2005 0.1920 0.6082 0.094 Uiso 1 1 calc R . .
H4B H -0.0075 0.1950 0.6517 0.094 Uiso 1 1 calc R . .
H4C H -0.1042 0.1331 0.6590 0.094 Uiso 1 1 calc R . .
N1 N -0.0778(2) 0.10558(7) 0.3812(2) 0.0406(4) Uani 1 1 d . . .
H1A H -0.0528 0.0981 0.2856 0.049 Uiso 1 1 calc R . .
H1B H -0.1220 0.0778 0.4384 0.049 Uiso 1 1 calc R . .
N2 N 0.0183(3) 0.20225(8) 0.3560(2) 0.0480(5) Uani 1 1 d . . .
H2A H 0.0445 0.1960 0.2601 0.058 Uiso 1 1 calc R . .
H2B H 0.0363 0.2371 0.3973 0.058 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.0212(2) 0.0226(2) 0.01534(19) -0.00016(13) 0.00035(13) 0.00029(14)
O1 0.0262(6) 0.0353(7) 0.0208(5) 0.0028(5) -0.0047(5) -0.0029(5)
O2 0.0266(6) 0.0449(7) 0.0215(5) 0.0043(5) -0.0047(5) -0.0052(6)
O3 0.0531(8) 0.0249(6) 0.0282(6) -0.0014(5) 0.0014(6) -0.0030(6)
O4 0.1140(16) 0.0259(8) 0.0481(9) 0.0012(7) 0.0178(10) -0.0017(9)
C1 0.0242(8) 0.0305(9) 0.0230(8) 0.0024(6) -0.0009(7) -0.0006(6)
C2 0.0585(14) 0.0298(11) 0.0313(10) 0.0017(7) 0.0049(9) -0.0005(9)
C3 0.0463(10) 0.0329(10) 0.0311(9) 0.0002(8) -0.0010(9) 0.0014(8)
C4 0.109(2) 0.0433(13) 0.0357(12) -0.0061(9) 0.0137(13) -0.0068(14)
N1 0.0582(11) 0.0320(9) 0.0317(8) -0.0030(6) 0.0056(8) -0.0084(8)
N2 0.0765(14) 0.0301(9) 0.0374(10) -0.0020(7) 0.0072(9) -0.0072(8)

_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
Co1 O3 2.1014(13) 5 ?
Co1 O3 2.1014(13) . ?
Co1 O1 2.1047(11) . ?
Co1 O1 2.1047(11) 5 ?
Co1 O2 2.1073(12) 8_655 ?
Co1 O2 2.1073(12) 4_455 ?
O1 C1 1.247(2) . ?
O2 C1 1.253(2) . ?
O2 Co1 2.1073(12) 4 ?
O3 C2 1.236(2) . ?
O4 C2 1.232(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 N1 1.296(3) . ?
C3 N2 1.307(3) . ?
C3 C4 1.485(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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
O3 Co1 O3 180.00(7) 5 . ?
O3 Co1 O1 92.71(5) 5 . ?
O3 Co1 O1 87.29(5) . . ?
O3 Co1 O1 87.29(5) 5 5 ?
O3 Co1 O1 92.71(5) . 5 ?
O1 Co1 O1 180.00(7) . 5 ?
O3 Co1 O2 85.14(5) 5 8_655 ?
O3 Co1 O2 94.86(5) . 8_655 ?
O1 Co1 O2 89.65(5) . 8_655 ?
O1 Co1 O2 90.35(5) 5 8_655 ?
O3 Co1 O2 94.86(5) 5 4_455 ?
O3 Co1 O2 85.14(5) . 4_455 ?
O1 Co1 O2 90.35(5) . 4_455 ?
O1 Co1 O2 89.65(5) 5 4_455 ?
O2 Co1 O2 180.0 8_655 4_455 ?
C1 O1 Co1 120.88(11) . . ?
C1 O2 Co1 123.20(11) . 4 ?
C2 O3 Co1 129.66(13) . . ?
O1 C1 O2 125.09(16) . . ?
O1 C1 H1 117.5 . . ?
O2 C1 H1 117.5 . . ?
O4 C2 O3 126.14(19) . . ?
O4 C2 H2 116.9 . . ?
O3 C2 H2 116.9 . . ?
N1 C3 N2 121.92(19) . . ?
N1 C3 C4 118.97(19) . . ?
N2 C3 C4 119.11(19) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.93 2.47 3.007(2) 116.5 4
C4 H4C O1 0.96 2.58 3.525(3) 167.0 5_556
N1 H1A O3 0.86 2.05 2.895(2) 168.8 .
N1 H1B O2 0.86 2.05 2.906(2) 173.9 5_556
N2 H2A O4 0.86 2.03 2.882(3) 172.6 .
N2 H2B O4 0.86 2.03 2.882(3) 171.0 7_566

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        76.51
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.288
_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_1Co-180K
_database_code_depnum_ccdc_archive 'CCDC 1840726'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 Co N4 O8'
_chemical_formula_weight         357.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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 ccn'

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                   7.8422(2)
_cell_length_b                   22.0907(6)
_cell_length_c                   8.5634(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1483.52(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    180.0
_cell_measurement_reflns_used    6654
_cell_measurement_theta_min      5.9690
_cell_measurement_theta_max      76.3300

_exptl_crystal_description       block
_exptl_crystal_colour            purple-red
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             740
_exptl_absorpt_coefficient_mu    9.506
_exptl_absorpt_correction_T_min  0.314
_exptl_absorpt_correction_T_max  0.558
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20877
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         76.60
_reflns_number_total             1544
_reflns_number_gt                1366
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0372P)²+0.9773P] 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     SHELXL
_refine_ls_extinction_coef       0.00037(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1544
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0706
_refine_ls_wR_factor_gt          0.0677
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
Co1 Co 0.0000 0.0000 0.0000 0.01322(12) Uani 1 2 d S . .
O1 O 0.06755(13) -0.02610(5) 0.22802(12) 0.0187(2) Uani 1 1 d . . .
O2 O 0.24925(14) -0.01729(5) 0.42606(12) 0.0209(2) Uani 1 1 d . . .
O3 O 0.04913(16) 0.08959(5) 0.06782(13) 0.0235(3) Uani 1 1 d . . .
O4 O 0.0794(2) 0.18793(6) 0.02760(16) 0.0409(4) Uani 1 1 d . . .
C1 C 0.1962(2) -0.00359(7) 0.29184(18) 0.0178(3) Uani 1 1 d . . .
H1 H 0.2584 0.0260 0.2350 0.021 Uiso 1 1 calc R . .
C2 C 0.0865(2) 0.13431(8) -0.01448(19) 0.0260(4) Uani 1 1 d . . .
H2 H 0.1236 0.1266 -0.1182 0.031 Uiso 1 1 calc R . .
C3 C -0.0497(2) 0.15872(8) 0.43980(19) 0.0246(3) Uani 1 1 d . . .
C4 C -0.0987(3) 0.17081(9) 0.6052(2) 0.0410(5) Uani 1 1 d . . .
H4A H -0.2133 0.1885 0.6083 0.062 Uiso 1 1 calc R . .
H4B H -0.0171 0.1991 0.6520 0.062 Uiso 1 1 calc R . .
H4C H -0.0981 0.1328 0.6641 0.062 Uiso 1 1 calc R . .
N1 N -0.0782(2) 0.10530(6) 0.38114(16) 0.0262(3) Uani 1 1 d . . .
H1A H -0.0514 0.0977 0.2833 0.031 Uiso 1 1 calc R . .
H1B H -0.1242 0.0768 0.4393 0.031 Uiso 1 1 calc R . .
N2 N 0.0188(2) 0.20244(7) 0.35700(19) 0.0314(4) Uani 1 1 d . . .
H2A H 0.0468 0.1961 0.2589 0.038 Uiso 1 1 calc R . .
H2B H 0.0366 0.2381 0.3996 0.038 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.01410(19) 0.0157(2) 0.00983(18) -0.00018(12) 0.00034(12) 0.00016(12)
O1 0.0180(5) 0.0243(6) 0.0138(5) 0.0020(4) -0.0024(4) -0.0016(4)
O2 0.0178(5) 0.0306(6) 0.0143(5) 0.0023(4) -0.0026(4) -0.0029(5)
O3 0.0340(6) 0.0180(6) 0.0184(5) -0.0006(4) 0.0005(5) -0.0020(5)
O4 0.0734(11) 0.0190(7) 0.0302(6) 0.0008(5) 0.0122(7) -0.0011(7)
C1 0.0163(7) 0.0213(8) 0.0158(7) 0.0015(5) -0.0004(6) -0.0002(5)
C2 0.0367(10) 0.0209(9) 0.0204(8) 0.0009(6) 0.0035(7) 0.0001(7)
C3 0.0294(8) 0.0237(9) 0.0207(8) 0.0002(7) -0.0018(7) 0.0016(7)
C4 0.0707(14) 0.0296(10) 0.0228(9) -0.0040(7) 0.0091(9) -0.0017(10)
N1 0.0366(8) 0.0225(7) 0.0196(6) -0.0011(5) 0.0043(6) -0.0046(6)
N2 0.0491(9) 0.0209(8) 0.0243(8) -0.0017(6) 0.0051(7) -0.0047(6)

_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
Co1 O3 2.0982(11) 5 ?
Co1 O3 2.0982(11) . ?
Co1 O2 2.1009(11) 8_655 ?
Co1 O2 2.1009(11) 4_455 ?
Co1 O1 2.1038(10) . ?
Co1 O1 2.1038(10) 5 ?
O1 C1 1.2505(19) . ?
O2 C1 1.2592(19) . ?
O2 Co1 2.1009(11) 4 ?
O3 C2 1.248(2) . ?
O4 C2 1.239(2) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 N1 1.302(2) . ?
C3 N2 1.313(2) . ?
C3 C4 1.492(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?

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
O3 Co1 O3 180.00(6) 5 . ?
O3 Co1 O2 85.24(5) 5 8_655 ?
O3 Co1 O2 94.76(5) . 8_655 ?
O3 Co1 O2 94.76(5) 5 4_455 ?
O3 Co1 O2 85.24(5) . 4_455 ?
O2 Co1 O2 180.00(6) 8_655 4_455 ?
O3 Co1 O1 92.56(4) 5 . ?
O3 Co1 O1 87.44(4) . . ?
O2 Co1 O1 89.67(4) 8_655 . ?
O2 Co1 O1 90.33(4) 4_455 . ?
O3 Co1 O1 87.44(4) 5 5 ?
O3 Co1 O1 92.56(4) . 5 ?
O2 Co1 O1 90.33(4) 8_655 5 ?
O2 Co1 O1 89.67(4) 4_455 5 ?
O1 Co1 O1 180.00(6) . 5 ?
C1 O1 Co1 119.99(10) . . ?
C1 O2 Co1 122.73(10) . 4 ?
C2 O3 Co1 129.29(11) . . ?
O1 C1 O2 124.74(14) . . ?
O1 C1 H1 117.6 . . ?
O2 C1 H1 117.6 . . ?
O4 C2 O3 125.56(16) . . ?
O4 C2 H2 117.2 . . ?
O3 C2 H2 117.2 . . ?
N1 C3 N2 121.92(16) . . ?
N1 C3 C4 118.96(16) . . ?
N2 C3 C4 119.12(16) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.95 2.44 2.9900(19) 116.3 4
C4 H4C O1 0.98 2.54 3.510(2) 169.2 5_556
N1 H1A O3 0.88 2.01 2.8837(18) 169.2 .
N1 H1B O2 0.88 2.00 2.8819(18) 174.3 5_556
N2 H2A O4 0.88 2.00 2.878(2) 171.7 .
N2 H2B O4 0.88 2.00 2.868(2) 171.1 7_566

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        76.60
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_1Co-440K
_database_code_depnum_ccdc_archive 'CCDC 1840733'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 Co N4 O8'
_chemical_formula_weight         357.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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 ccn'

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                   7.9479(3)
_cell_length_b                   22.1124(11)
_cell_length_c                   8.6127(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1513.66(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    440.0
_cell_measurement_reflns_used    2570
_cell_measurement_theta_min      7.8350
_cell_measurement_theta_max      76.2550

_exptl_crystal_description       block
_exptl_crystal_colour            purple-red
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             740
_exptl_absorpt_coefficient_mu    9.317
_exptl_absorpt_correction_T_min  0.326
_exptl_absorpt_correction_T_max  0.554
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      440.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10751
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         76.48
_reflns_number_total             1550
_reflns_number_gt                1022
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0404P)²+1.8585P] 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     SHELXL
_refine_ls_extinction_coef       0.00063(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1550
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
Co1 Co 0.0000 0.0000 0.0000 0.0340(2) Uani 1 2 d S . .
O1 O 0.0730(3) -0.02451(11) 0.2264(2) 0.0451(6) Uani 1 1 d . . .
O2 O 0.2529(3) -0.01669(11) 0.4219(3) 0.0510(6) Uani 1 1 d . . .
O3 O 0.0469(4) 0.09024(11) 0.0651(3) 0.0584(7) Uani 1 1 d . . .
O4 O 0.0776(6) 0.18756(14) 0.0272(4) 0.0989(13) Uani 1 1 d . . .
C1 C 0.1986(4) -0.00314(15) 0.2902(4) 0.0417(8) Uani 1 1 d . . .
H1 H 0.2586 0.0258 0.2349 0.050 Uiso 1 1 calc R . .
C2 C 0.0831(7) 0.1344(2) -0.0128(5) 0.0693(13) Uani 1 1 d . . .
H2 H 0.1190 0.1269 -0.1138 0.083 Uiso 1 1 calc R . .
C3 C -0.0470(6) 0.15886(19) 0.4391(5) 0.0597(10) Uani 1 1 d . . .
C4 C -0.0894(8) 0.1706(2) 0.6035(5) 0.100(2) Uani 1 1 d . . .
H4A H -0.2023 0.1857 0.6104 0.149 Uiso 1 1 calc R . .
H4B H -0.0129 0.2000 0.6452 0.149 Uiso 1 1 calc R . .
H4C H -0.0804 0.1337 0.6617 0.149 Uiso 1 1 calc R . .
N1 N -0.0768(5) 0.10598(15) 0.3816(4) 0.0668(10) Uani 1 1 d . . .
H1A H -0.0528 0.0985 0.2861 0.080 Uiso 1 1 calc R . .
H1B H -0.1205 0.0782 0.4388 0.080 Uiso 1 1 calc R . .
N2 N 0.0189(5) 0.20179(16) 0.3560(4) 0.0784(12) Uani 1 1 d . . .
H2A H 0.0439 0.1953 0.2602 0.094 Uiso 1 1 calc R . .
H2B H 0.0376 0.2367 0.3967 0.094 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.0402(4) 0.0384(4) 0.0233(3) -0.0005(3) 0.0005(3) 0.0007(3)
O1 0.0450(12) 0.0583(15) 0.0319(11) 0.0037(10) -0.0084(10) -0.0040(12)
O2 0.0497(14) 0.0706(17) 0.0327(11) 0.0072(11) -0.0077(11) -0.0050(13)
O3 0.089(2) 0.0416(15) 0.0443(14) -0.0003(12) 0.0023(14) -0.0061(14)
O4 0.179(4) 0.0395(19) 0.078(2) 0.0022(15) 0.027(2) -0.003(2)
C1 0.0425(17) 0.050(2) 0.0330(15) 0.0038(15) -0.0015(14) 0.0020(15)
C2 0.107(4) 0.052(3) 0.049(2) 0.0035(19) 0.011(2) -0.002(3)
C3 0.080(3) 0.053(3) 0.046(2) -0.0021(19) -0.001(2) -0.004(2)
C4 0.171(6) 0.075(4) 0.052(3) -0.010(2) 0.020(3) -0.016(4)
N1 0.095(3) 0.054(2) 0.0513(19) -0.0038(15) 0.0085(19) -0.011(2)
N2 0.127(4) 0.050(2) 0.058(2) -0.0016(17) 0.012(2) -0.012(2)

_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
Co1 O1 2.106(2) 5 ?
Co1 O1 2.106(2) . ?
Co1 O3 2.106(3) . ?
Co1 O3 2.106(3) 5 ?
Co1 O2 2.108(2) 4_455 ?
Co1 O2 2.108(2) 8_655 ?
O1 C1 1.233(4) . ?
O2 C1 1.250(4) . ?
O2 Co1 2.108(2) 4 ?
O3 C2 1.219(5) . ?
O4 C2 1.226(5) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 N1 1.291(5) . ?
C3 N2 1.299(5) . ?
C3 C4 1.478(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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 Co1 O1 180.00(18) 5 . ?
O1 Co1 O3 92.95(10) 5 . ?
O1 Co1 O3 87.05(10) . . ?
O1 Co1 O3 87.05(10) 5 5 ?
O1 Co1 O3 92.95(10) . 5 ?
O3 Co1 O3 180.00(4) . 5 ?
O1 Co1 O2 89.64(9) 5 4_455 ?
O1 Co1 O2 90.36(9) . 4_455 ?
O3 Co1 O2 85.06(11) . 4_455 ?
O3 Co1 O2 94.94(11) 5 4_455 ?
O1 Co1 O2 90.36(9) 5 8_655 ?
O1 Co1 O2 89.64(9) . 8_655 ?
O3 Co1 O2 94.94(11) . 8_655 ?
O3 Co1 O2 85.06(11) 5 8_655 ?
O2 Co1 O2 180.00(5) 4_455 8_655 ?
C1 O1 Co1 122.5(2) . . ?
C1 O2 Co1 124.7(2) . 4 ?
C2 O3 Co1 130.8(3) . . ?
O1 C1 O2 126.3(3) . . ?
O1 C1 H1 116.9 . . ?
O2 C1 H1 116.9 . . ?
O3 C2 O4 127.2(4) . . ?
O3 C2 H2 116.4 . . ?
O4 C2 H2 116.4 . . ?
N1 C3 N2 121.6(4) . . ?
N1 C3 C4 119.0(4) . . ?
N2 C3 C4 119.4(4) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.93 2.52 3.042(4) 115.7 4
C4 H4C O1 0.96 2.60 3.550(6) 169.8 5_556
N1 H1A O3 0.86 2.07 2.918(4) 168.8 .
N1 H1B O2 0.86 2.10 2.954(4) 173.3 5_556
N2 H2A O4 0.86 2.03 2.887(5) 172.5 .
N2 H2B O4 0.86 2.04 2.895(5) 170.7 7_566

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        76.48
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_2Ni-440K
_database_code_depnum_ccdc_archive 'CCDC 1840723'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 Ni O8'
_chemical_formula_weight         356.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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 ccn'

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                   7.8983(2)
_cell_length_b                   22.0866(4)
_cell_length_c                   8.5326(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1488.48(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    440.0
_cell_measurement_reflns_used    5543
_cell_measurement_theta_min      3.9820
_cell_measurement_theta_max      76.3720

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.049
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.315
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      440.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21422
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         76.63
_reflns_number_total             1561
_reflns_number_gt                1270
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0462P)²+0.7780P] 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     SHELXL
_refine_ls_extinction_coef       0.00063(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1561
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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 0.0000 0.0000 0.02763(15) Uani 1 2 d S . .
O1 O 0.07422(16) -0.02446(6) 0.22360(14) 0.0368(3) Uani 1 1 d . . .
O2 O 0.25474(18) -0.01653(6) 0.42067(15) 0.0417(3) Uani 1 1 d . . .
O3 O 0.0457(2) 0.08907(6) 0.06424(18) 0.0490(4) Uani 1 1 d . . .
O4 O 0.0810(4) 0.18605(8) 0.0240(2) 0.0887(8) Uani 1 1 d . . .
C1 C 0.2023(2) -0.00306(8) 0.2867(2) 0.0335(4) Uani 1 1 d . . .
H1 H 0.2644 0.0252 0.2300 0.040 Uiso 1 1 calc R . .
C2 C 0.0844(4) 0.13272(10) -0.0154(3) 0.0574(6) Uani 1 1 d . . .
H2 H 0.1205 0.1247 -0.1171 0.069 Uiso 1 1 calc R . .
C3 C -0.0481(3) 0.15891(10) 0.4393(3) 0.0517(5) Uani 1 1 d . . .
C4 C -0.0927(6) 0.17122(14) 0.6047(3) 0.0927(12) Uani 1 1 d . . .
H4A H -0.1825 0.2005 0.6087 0.139 Uiso 1 1 calc R . .
H4B H 0.0046 0.1868 0.6588 0.139 Uiso 1 1 calc R . .
H4C H -0.1292 0.1344 0.6540 0.139 Uiso 1 1 calc R . .
N1 N -0.0770(3) 0.10567(8) 0.3828(2) 0.0601(5) Uani 1 1 d . . .
H1A H -0.0518 0.0977 0.2869 0.072 Uiso 1 1 calc R . .
H1B H -0.1215 0.0781 0.4410 0.072 Uiso 1 1 calc R . .
N2 N 0.0190(3) 0.20180(9) 0.3550(3) 0.0685(7) Uani 1 1 d . . .
H2A H 0.0454 0.1951 0.2588 0.082 Uiso 1 1 calc R . .
H2B H 0.0369 0.2369 0.3956 0.082 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.0304(2) 0.0319(2) 0.0206(2) 0.00003(14) 0.00024(15) 0.00023(15)
O1 0.0356(7) 0.0480(7) 0.0267(6) 0.0033(5) -0.0054(5) -0.0047(6)
O2 0.0372(7) 0.0601(8) 0.0279(6) 0.0058(6) -0.0065(5) -0.0060(6)
O3 0.0739(10) 0.0357(7) 0.0372(7) -0.0018(6) 0.0012(8) -0.0054(7)
O4 0.159(2) 0.0361(8) 0.0705(12) 0.0017(8) 0.0254(14) -0.0049(12)
C1 0.0342(9) 0.0393(8) 0.0269(8) 0.0031(7) -0.0010(7) -0.0010(7)
C2 0.0888(19) 0.0397(11) 0.0438(12) 0.0012(9) 0.0092(12) -0.0028(12)
C3 0.0673(14) 0.0452(11) 0.0426(11) -0.0020(9) -0.0014(11) -0.0013(10)
C4 0.164(4) 0.0642(16) 0.0499(15) -0.0107(12) 0.0206(19) -0.014(2)
N1 0.0873(15) 0.0466(10) 0.0462(10) -0.0055(8) 0.0095(11) -0.0129(10)
N2 0.107(2) 0.0440(10) 0.0542(12) -0.0011(9) 0.0080(12) -0.0130(11)

_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 2.0678(12) . ?
Ni1 O1 2.0678(12) 5 ?
Ni1 O3 2.0738(13) 5 ?
Ni1 O3 2.0738(13) . ?
Ni1 O2 2.0842(14) 4_455 ?
Ni1 O2 2.0842(14) 8_655 ?
O1 C1 1.240(2) . ?
O2 C1 1.252(2) . ?
O2 Ni1 2.0842(14) 4 ?
O3 C2 1.219(3) . ?
O4 C2 1.225(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 N1 1.292(3) . ?
C3 N2 1.302(3) . ?
C3 C4 1.480(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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 180.00(7) . 5 ?
O1 Ni1 O3 92.60(6) . 5 ?
O1 Ni1 O3 87.40(6) 5 5 ?
O1 Ni1 O3 87.40(6) . . ?
O1 Ni1 O3 92.60(6) 5 . ?
O3 Ni1 O3 180.00(10) 5 . ?
O1 Ni1 O2 90.55(5) . 4_455 ?
O1 Ni1 O2 89.45(5) 5 4_455 ?
O3 Ni1 O2 95.17(6) 5 4_455 ?
O3 Ni1 O2 84.83(6) . 4_455 ?
O1 Ni1 O2 89.45(5) . 8_655 ?
O1 Ni1 O2 90.55(5) 5 8_655 ?
O3 Ni1 O2 84.83(6) 5 8_655 ?
O3 Ni1 O2 95.17(6) . 8_655 ?
O2 Ni1 O2 180.00(3) 4_455 8_655 ?
C1 O1 Ni1 122.17(12) . . ?
C1 O2 Ni1 124.22(13) . 4 ?
C2 O3 Ni1 130.29(15) . . ?
O1 C1 O2 125.17(18) . . ?
O1 C1 H1 117.4 . . ?
O2 C1 H1 117.4 . . ?
O3 C2 O4 127.0(2) . . ?
O3 C2 H2 116.5 . . ?
O4 C2 H2 116.5 . . ?
N1 C3 N2 121.9(2) . . ?
N1 C3 C4 118.8(2) . . ?
N2 C3 C4 119.3(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.93 2.48 3.001(2) 115.6 4
C4 H4C O1 0.96 2.68 3.560(3) 152.9 5_556
N1 H1A O3 0.86 2.06 2.909(3) 169.5 .
N1 H1B O2 0.86 2.09 2.943(2) 173.6 5_556
N2 H2A O4 0.86 2.03 2.888(3) 172.4 .
N2 H2B O4 0.86 2.05 2.907(3) 171.4 7_566

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        76.63
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_1Co-100K
_database_code_depnum_ccdc_archive 'CCDC 1840724'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 Co N4 O8'
_chemical_formula_weight         357.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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 ccn'

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                   7.8265(2)
_cell_length_b                   22.0990(6)
_cell_length_c                   8.5484(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1478.51(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0
_cell_measurement_reflns_used    7307
_cell_measurement_theta_min      5.9790
_cell_measurement_theta_max      75.9200

_exptl_crystal_description       block
_exptl_crystal_colour            purple-red
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             740
_exptl_absorpt_coefficient_mu    9.538
_exptl_absorpt_correction_T_min  0.316
_exptl_absorpt_correction_T_max  0.558
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20755
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         76.62
_reflns_number_total             1539
_reflns_number_gt                1389
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0434P)²+1.0567P] 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     SHELXL
_refine_ls_extinction_coef       0.00037(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1539
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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
Co1 Co 0.0000 0.0000 0.0000 0.00939(13) Uani 1 2 d S . .
O1 O 0.06675(13) -0.02633(5) 0.22837(12) 0.0135(2) Uani 1 1 d . . .
O2 O 0.24890(13) -0.01729(5) 0.42688(12) 0.0148(2) Uani 1 1 d . . .
O3 O 0.04958(14) 0.08942(5) 0.06823(12) 0.0159(2) Uani 1 1 d . . .
O4 O 0.07860(19) 0.18812(6) 0.02812(15) 0.0262(3) Uani 1 1 d . . .
C1 C 0.1956(2) -0.00363(6) 0.29220(18) 0.0128(3) Uani 1 1 d . . .
H1 H 0.2577 0.0260 0.2351 0.015 Uiso 1 1 calc R . .
C2 C 0.0864(2) 0.13452(8) -0.01479(18) 0.0172(3) Uani 1 1 d . . .
H2 H 0.1233 0.1270 -0.1189 0.021 Uiso 1 1 calc R . .
C3 C -0.0509(2) 0.15859(7) 0.44045(18) 0.0167(3) Uani 1 1 d . . .
C4 C -0.1035(3) 0.17068(8) 0.6057(2) 0.0263(4) Uani 1 1 d . . .
H4A H -0.2201 0.1868 0.6072 0.040 Uiso 1 1 calc R . .
H4B H -0.0254 0.2003 0.6525 0.040 Uiso 1 1 calc R . .
H4C H -0.0993 0.1329 0.6658 0.040 Uiso 1 1 calc R . .
N1 N -0.07887(18) 0.10514(6) 0.38118(15) 0.0178(3) Uani 1 1 d . . .
H1A H -0.0506 0.0975 0.2835 0.021 Uiso 1 1 calc R . .
H1B H -0.1261 0.0767 0.4388 0.021 Uiso 1 1 calc R . .
N2 N 0.01936(18) 0.20237(7) 0.35831(17) 0.0204(3) Uani 1 1 d . . .
H2A H 0.0489 0.1960 0.2604 0.025 Uiso 1 1 calc R . .
H2B H 0.0368 0.2380 0.4013 0.025 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.0099(2) 0.0119(2) 0.00633(19) -0.00007(12) 0.00023(11) 0.00019(12)
O1 0.0127(5) 0.0183(6) 0.0096(5) 0.0008(4) -0.0017(4) -0.0006(4)
O2 0.0127(5) 0.0222(6) 0.0096(5) 0.0010(4) -0.0018(4) -0.0014(4)
O3 0.0219(5) 0.0139(5) 0.0119(5) -0.0003(4) 0.0000(4) -0.0011(4)
O4 0.0436(8) 0.0152(6) 0.0198(6) 0.0010(5) 0.0071(5) -0.0003(5)
C1 0.0126(7) 0.0149(8) 0.0108(7) 0.0002(5) 0.0011(6) 0.0004(5)
C2 0.0219(8) 0.0161(8) 0.0137(7) 0.0008(5) 0.0013(6) 0.0006(6)
C3 0.0188(7) 0.0180(8) 0.0133(7) 0.0016(6) -0.0015(6) 0.0012(6)
C4 0.0442(10) 0.0209(9) 0.0139(8) -0.0024(6) 0.0058(7) -0.0007(7)
N1 0.0238(7) 0.0174(7) 0.0122(6) -0.0005(5) 0.0029(5) -0.0027(5)
N2 0.0305(7) 0.0153(7) 0.0155(7) -0.0020(5) 0.0036(5) -0.0022(5)

_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
Co1 O3 2.0965(11) . ?
Co1 O3 2.0965(11) 5 ?
Co1 O2 2.0973(10) 4_455 ?
Co1 O2 2.0973(10) 8_655 ?
Co1 O1 2.1030(10) 5 ?
Co1 O1 2.1030(10) . ?
O1 C1 1.2517(19) . ?
O2 C1 1.2612(19) . ?
O2 Co1 2.0973(10) 4 ?
O3 C2 1.257(2) . ?
O4 C2 1.242(2) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 N1 1.304(2) . ?
C3 N2 1.316(2) . ?
C3 C4 1.496(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?

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
O3 Co1 O3 180.00(6) . 5 ?
O3 Co1 O2 85.34(4) . 4_455 ?
O3 Co1 O2 94.66(4) 5 4_455 ?
O3 Co1 O2 94.66(4) . 8_655 ?
O3 Co1 O2 85.34(4) 5 8_655 ?
O2 Co1 O2 180.0 4_455 8_655 ?
O3 Co1 O1 92.49(4) . 5 ?
O3 Co1 O1 87.51(4) 5 5 ?
O2 Co1 O1 89.62(4) 4_455 5 ?
O2 Co1 O1 90.38(4) 8_655 5 ?
O3 Co1 O1 87.51(4) . . ?
O3 Co1 O1 92.49(4) 5 . ?
O2 Co1 O1 90.38(4) 4_455 . ?
O2 Co1 O1 89.62(4) 8_655 . ?
O1 Co1 O1 180.00(8) 5 . ?
C1 O1 Co1 119.60(10) . . ?
C1 O2 Co1 122.57(10) . 4 ?
C2 O3 Co1 129.25(10) . . ?
O1 C1 O2 124.65(14) . . ?
O1 C1 H1 117.7 . . ?
O2 C1 H1 117.7 . . ?
O4 C2 O3 125.34(15) . . ?
O4 C2 H2 117.3 . . ?
O3 C2 H2 117.3 . . ?
N1 C3 N2 121.94(15) . . ?
N1 C3 C4 118.87(15) . . ?
N2 C3 C4 119.18(15) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.95 2.44 2.9843(19) 116.3 4
C4 H4C O1 0.98 2.54 3.503(2) 168.8 5_556
N1 H1A O3 0.88 2.01 2.8789(17) 169.9 .
N1 H1B O2 0.88 1.99 2.8692(17) 175.1 5_556
N2 H2A O4 0.88 2.01 2.8777(19) 170.3 .
N2 H2B O4 0.88 1.99 2.8598(19) 171.5 7_566

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        76.62
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_2Ni-400K
_database_code_depnum_ccdc_archive 'CCDC 1840722'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 Ni O8'
_chemical_formula_weight         356.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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 ccn'

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                   7.8802(2)
_cell_length_b                   22.0783(4)
_cell_length_c                   8.5264(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1483.43(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    400.0
_cell_measurement_reflns_used    6307
_cell_measurement_theta_min      5.9520
_cell_measurement_theta_max      76.4890

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.049
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.323
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      400.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21351
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         76.53
_reflns_number_total             1554
_reflns_number_gt                1313
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0440P)²+0.8083P] 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     SHELXL
_refine_ls_extinction_coef       0.00070(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1554
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0777
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.0000 0.0000 0.02489(15) Uani 1 2 d S . .
O1 O 0.07346(15) -0.02470(6) 0.22359(13) 0.0331(3) Uani 1 1 d . . .
O2 O 0.25410(17) -0.01664(6) 0.42109(14) 0.0376(3) Uani 1 1 d . . .
O3 O 0.0459(2) 0.08896(6) 0.06478(16) 0.0441(3) Uani 1 1 d . . .
O4 O 0.0814(4) 0.18618(7) 0.0240(2) 0.0807(7) Uani 1 1 d . . .
C1 C 0.2020(2) -0.00314(7) 0.28697(19) 0.0304(3) Uani 1 1 d . . .
H1 H 0.2642 0.0252 0.2304 0.036 Uiso 1 1 calc R . .
C2 C 0.0853(4) 0.13266(9) -0.0154(2) 0.0515(6) Uani 1 1 d . . .
H2 H 0.1221 0.1246 -0.1169 0.062 Uiso 1 1 calc R . .
C3 C -0.0482(3) 0.15893(9) 0.4395(2) 0.0466(5) Uani 1 1 d . . .
C4 C -0.0939(5) 0.17127(12) 0.6051(3) 0.0820(10) Uani 1 1 d . . .
H4A H -0.1932 0.1964 0.6085 0.123 Uiso 1 1 calc R . .
H4B H -0.0015 0.1916 0.6561 0.123 Uiso 1 1 calc R . .
H4C H -0.1167 0.1337 0.6579 0.123 Uiso 1 1 calc R . .
N1 N -0.0771(3) 0.10561(8) 0.3829(2) 0.0536(5) Uani 1 1 d . . .
H1A H -0.0520 0.0977 0.2869 0.064 Uiso 1 1 calc R . .
H1B H -0.1215 0.0780 0.4412 0.064 Uiso 1 1 calc R . .
N2 N 0.0188(3) 0.20200(8) 0.3550(3) 0.0623(6) Uani 1 1 d . . .
H2A H 0.0452 0.1953 0.2587 0.075 Uiso 1 1 calc R . .
H2B H 0.0367 0.2371 0.3957 0.075 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.0274(2) 0.0286(2) 0.0186(2) -0.00003(13) 0.00036(14) 0.00014(14)
O1 0.0326(6) 0.0427(6) 0.0239(5) 0.0036(5) -0.0052(5) -0.0047(5)
O2 0.0336(6) 0.0546(7) 0.0246(5) 0.0058(5) -0.0061(5) -0.0060(6)
O3 0.0669(9) 0.0316(6) 0.0339(7) -0.0014(5) 0.0015(7) -0.0054(6)
O4 0.147(2) 0.0326(8) 0.0626(11) 0.0019(7) 0.0234(12) -0.0037(10)
C1 0.0300(8) 0.0356(8) 0.0255(7) 0.0028(6) -0.0002(7) -0.0007(6)
C2 0.0787(17) 0.0363(10) 0.0395(10) 0.0014(8) 0.0073(10) -0.0018(10)
C3 0.0592(12) 0.0402(10) 0.0404(10) -0.0010(8) -0.0015(10) 0.0006(9)
C4 0.144(3) 0.0573(14) 0.0446(13) -0.0102(11) 0.0174(16) -0.0120(17)
N1 0.0773(13) 0.0422(9) 0.0414(9) -0.0046(7) 0.0088(9) -0.0118(9)
N2 0.0985(17) 0.0389(9) 0.0494(11) -0.0013(8) 0.0089(11) -0.0121(9)

_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 2.0656(11) 5 ?
Ni1 O1 2.0656(11) . ?
Ni1 O3 2.0720(12) . ?
Ni1 O3 2.0720(12) 5 ?
Ni1 O2 2.0839(13) 4_455 ?
Ni1 O2 2.0839(13) 8_655 ?
O1 C1 1.242(2) . ?
O2 C1 1.251(2) . ?
O2 Ni1 2.0839(13) 4 ?
O3 C2 1.223(2) . ?
O4 C2 1.229(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 N1 1.293(3) . ?
C3 N2 1.305(3) . ?
C3 C4 1.483(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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 180.00(9) 5 . ?
O1 Ni1 O3 92.57(5) 5 . ?
O1 Ni1 O3 87.43(5) . . ?
O1 Ni1 O3 87.43(5) 5 5 ?
O1 Ni1 O3 92.57(5) . 5 ?
O3 Ni1 O3 180.00(8) . 5 ?
O1 Ni1 O2 89.47(5) 5 4_455 ?
O1 Ni1 O2 90.53(5) . 4_455 ?
O3 Ni1 O2 84.79(6) . 4_455 ?
O3 Ni1 O2 95.21(6) 5 4_455 ?
O1 Ni1 O2 90.53(5) 5 8_655 ?
O1 Ni1 O2 89.47(5) . 8_655 ?
O3 Ni1 O2 95.21(6) . 8_655 ?
O3 Ni1 O2 84.79(6) 5 8_655 ?
O2 Ni1 O2 180.00(6) 4_455 8_655 ?
C1 O1 Ni1 121.92(11) . . ?
C1 O2 Ni1 123.95(12) . 4 ?
C2 O3 Ni1 130.03(14) . . ?
O1 C1 O2 125.02(16) . . ?
O1 C1 H1 117.5 . . ?
O2 C1 H1 117.5 . . ?
O3 C2 O4 126.8(2) . . ?
O3 C2 H2 116.6 . . ?
O4 C2 H2 116.6 . . ?
N1 C3 N2 121.9(2) . . ?
N1 C3 C4 118.7(2) . . ?
N2 C3 C4 119.4(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.93 2.47 2.993(2) 115.8 4
C4 H4C O1 0.96 2.63 3.554(3) 160.9 5_556
N1 H1A O3 0.86 2.05 2.903(2) 169.4 .
N1 H1B O2 0.86 2.08 2.932(2) 173.6 5_556
N2 H2A O4 0.86 2.03 2.886(3) 172.7 .
N2 H2B O4 0.86 2.05 2.901(3) 171.4 7_566

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        76.53
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_1Co-140K
_database_code_depnum_ccdc_archive 'CCDC 1840725'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 Co N4 O8'
_chemical_formula_weight         357.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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 ccn'

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                   7.8332(1)
_cell_length_b                   22.0928(5)
_cell_length_c                   8.5556(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1480.61(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    140
_cell_measurement_reflns_used    7020
_cell_measurement_theta_min      5.9740
_cell_measurement_theta_max      76.4450

_exptl_crystal_description       block
_exptl_crystal_colour            purple-red
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             740
_exptl_absorpt_coefficient_mu    9.524
_exptl_absorpt_correction_T_min  0.317
_exptl_absorpt_correction_T_max  0.559
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20810
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         76.39
_reflns_number_total             1538
_reflns_number_gt                1360
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0391P)²+1.0180P] 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     SHELXL
_refine_ls_extinction_coef       0.00034(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1538
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0712
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
Co1 Co 0.0000 0.0000 0.0000 0.01116(12) Uani 1 2 d S . .
O1 O 0.06713(13) -0.02623(5) 0.22809(12) 0.0158(2) Uani 1 1 d . . .
O2 O 0.24902(14) -0.01728(5) 0.42654(12) 0.0175(2) Uani 1 1 d . . .
O3 O 0.04933(15) 0.08949(5) 0.06810(13) 0.0197(2) Uani 1 1 d . . .
O4 O 0.0792(2) 0.18805(6) 0.02776(15) 0.0334(3) Uani 1 1 d . . .
C1 C 0.1959(2) -0.00361(7) 0.29199(17) 0.0150(3) Uani 1 1 d . . .
H1 H 0.2582 0.0260 0.2350 0.018 Uiso 1 1 calc R . .
C2 C 0.0865(2) 0.13439(8) -0.01456(18) 0.0213(4) Uani 1 1 d . . .
H2 H 0.1235 0.1267 -0.1184 0.026 Uiso 1 1 calc R . .
C3 C -0.0502(2) 0.15864(8) 0.44004(18) 0.0206(3) Uani 1 1 d . . .
C4 C -0.1006(3) 0.17076(9) 0.6053(2) 0.0334(4) Uani 1 1 d . . .
H4A H -0.2164 0.1875 0.6078 0.050 Uiso 1 1 calc R . .
H4B H -0.0209 0.1998 0.6518 0.050 Uiso 1 1 calc R . .
H4C H -0.0977 0.1329 0.6649 0.050 Uiso 1 1 calc R . .
N1 N -0.07846(18) 0.10520(6) 0.38116(16) 0.0217(3) Uani 1 1 d . . .
H1A H -0.0510 0.0976 0.2834 0.026 Uiso 1 1 calc R . .
H1B H -0.1250 0.0767 0.4392 0.026 Uiso 1 1 calc R . .
N2 N 0.01905(19) 0.20244(7) 0.35750(18) 0.0258(3) Uani 1 1 d . . .
H2A H 0.0478 0.1961 0.2594 0.031 Uiso 1 1 calc R . .
H2B H 0.0367 0.2381 0.4003 0.031 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.01172(19) 0.0140(2) 0.00779(18) -0.00023(12) 0.00024(11) 0.00000(12)
O1 0.0149(5) 0.0212(6) 0.0114(5) 0.0010(4) -0.0021(4) -0.0008(4)
O2 0.0151(5) 0.0254(6) 0.0119(5) 0.0021(4) -0.0022(4) -0.0022(4)
O3 0.0281(6) 0.0161(5) 0.0149(5) -0.0002(4) 0.0005(5) -0.0017(4)
O4 0.0585(9) 0.0173(7) 0.0245(6) 0.0009(5) 0.0102(6) 0.0000(6)
C1 0.0141(7) 0.0174(8) 0.0134(7) 0.0007(5) 0.0001(6) 0.0001(5)
C2 0.0289(9) 0.0187(9) 0.0163(7) 0.0016(6) 0.0025(6) 0.0006(7)
C3 0.0234(7) 0.0212(8) 0.0171(7) 0.0010(6) -0.0013(6) 0.0018(6)
C4 0.0571(12) 0.0252(9) 0.0181(8) -0.0034(6) 0.0076(8) -0.0023(8)
N1 0.0297(7) 0.0195(7) 0.0159(6) -0.0010(5) 0.0030(5) -0.0034(5)
N2 0.0399(8) 0.0178(8) 0.0197(7) -0.0016(6) 0.0040(6) -0.0033(6)

_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
Co1 O3 2.0971(11) . ?
Co1 O3 2.0971(11) 5 ?
Co1 O2 2.0991(11) 4_455 ?
Co1 O2 2.0991(11) 8_655 ?
Co1 O1 2.1025(10) . ?
Co1 O1 2.1025(10) 5 ?
O1 C1 1.2517(19) . ?
O2 C1 1.2607(19) . ?
O2 Co1 2.0991(11) 4 ?
O3 C2 1.253(2) . ?
O4 C2 1.241(2) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 N1 1.303(2) . ?
C3 N2 1.315(2) . ?
C3 C4 1.492(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?

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
O3 Co1 O3 180.00(2) . 5 ?
O3 Co1 O2 85.29(4) . 4_455 ?
O3 Co1 O2 94.71(4) 5 4_455 ?
O3 Co1 O2 94.71(4) . 8_655 ?
O3 Co1 O2 85.29(4) 5 8_655 ?
O2 Co1 O2 180.00(6) 4_455 8_655 ?
O3 Co1 O1 87.47(4) . . ?
O3 Co1 O1 92.53(4) 5 . ?
O2 Co1 O1 90.37(4) 4_455 . ?
O2 Co1 O1 89.63(4) 8_655 . ?
O3 Co1 O1 92.53(4) . 5 ?
O3 Co1 O1 87.47(4) 5 5 ?
O2 Co1 O1 89.63(4) 4_455 5 ?
O2 Co1 O1 90.37(4) 8_655 5 ?
O1 Co1 O1 180.00(6) . 5 ?
C1 O1 Co1 119.80(10) . . ?
C1 O2 Co1 122.59(10) . 4 ?
C2 O3 Co1 129.24(10) . . ?
O1 C1 O2 124.68(14) . . ?
O1 C1 H1 117.7 . . ?
O2 C1 H1 117.7 . . ?
O4 C2 O3 125.51(15) . . ?
O4 C2 H2 117.2 . . ?
O3 C2 H2 117.2 . . ?
N1 C3 N2 121.97(15) . . ?
N1 C3 C4 118.95(15) . . ?
N2 C3 C4 119.08(16) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.95 2.44 2.9864(19) 116.4 4
C4 H4C O1 0.98 2.54 3.506(2) 169.1 5_556
N1 H1A O3 0.88 2.01 2.8804(18) 169.5 .
N1 H1B O2 0.88 2.00 2.8747(17) 174.7 5_556
N2 H2A O4 0.88 2.01 2.878(2) 171.1 .
N2 H2B O4 0.88 1.99 2.863(2) 171.3 7_566

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        76.39
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_2Ni-360K
_database_code_depnum_ccdc_archive 'CCDC 1840721'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 Ni O8'
_chemical_formula_weight         356.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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 ccn'

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                   7.8655(2)
_cell_length_b                   22.0691(4)
_cell_length_c                   8.5179(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1478.58(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    360.0
_cell_measurement_reflns_used    6674
_cell_measurement_theta_min      3.9910
_cell_measurement_theta_max      75.8610

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.049
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.331
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      360.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21283
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.01
_diffrn_reflns_theta_max         76.39
_reflns_number_total             1551
_reflns_number_gt                1321
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0447P)²+0.7443P] 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     SHELXL
_refine_ls_extinction_coef       0.00063(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1551
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.0000 0.0000 0.02303(14) Uani 1 2 d S . .
O1 O 0.07283(14) -0.02490(5) 0.22391(13) 0.0306(3) Uani 1 1 d . . .
O2 O 0.25382(16) -0.01672(6) 0.42171(13) 0.0347(3) Uani 1 1 d . . .
O3 O 0.04625(19) 0.08892(5) 0.06522(15) 0.0407(3) Uani 1 1 d . . .
O4 O 0.0817(3) 0.18632(7) 0.0242(2) 0.0726(6) Uani 1 1 d . . .
C1 C 0.2016(2) -0.00320(7) 0.28708(18) 0.0278(3) Uani 1 1 d . . .
H1 H 0.2638 0.0252 0.2303 0.033 Uiso 1 1 calc R . .
C2 C 0.0859(3) 0.13272(9) -0.0156(2) 0.0469(5) Uani 1 1 d . . .
H2 H 0.1230 0.1246 -0.1171 0.056 Uiso 1 1 calc R . .
C3 C -0.0483(3) 0.15894(9) 0.4399(2) 0.0432(4) Uani 1 1 d . . .
C4 C -0.0951(5) 0.17128(11) 0.6055(3) 0.0741(9) Uani 1 1 d . . .
H4A H -0.1924 0.1975 0.6084 0.111 Uiso 1 1 calc R . .
H4B H -0.0014 0.1905 0.6579 0.111 Uiso 1 1 calc R . .
H4C H -0.1218 0.1338 0.6572 0.111 Uiso 1 1 calc R . .
N1 N -0.0772(3) 0.10553(7) 0.3829(2) 0.0486(4) Uani 1 1 d . . .
H1A H -0.0520 0.0977 0.2868 0.058 Uiso 1 1 calc R . .
H1B H -0.1216 0.0779 0.4412 0.058 Uiso 1 1 calc R . .
N2 N 0.0190(3) 0.20208(8) 0.3554(2) 0.0562(5) Uani 1 1 d . . .
H2A H 0.0454 0.1954 0.2589 0.067 Uiso 1 1 calc R . .
H2B H 0.0368 0.2372 0.3961 0.067 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.0252(2) 0.0264(2) 0.0175(2) 0.00006(12) 0.00026(13) 0.00012(13)
O1 0.0295(6) 0.0398(6) 0.0225(5) 0.0034(4) -0.0049(4) -0.0039(5)
O2 0.0309(6) 0.0498(6) 0.0234(5) 0.0049(5) -0.0055(5) -0.0053(5)
O3 0.0614(8) 0.0298(6) 0.0310(6) -0.0016(5) 0.0016(6) -0.0040(6)
O4 0.1294(18) 0.0305(7) 0.0578(10) 0.0018(6) 0.0210(11) -0.0031(9)
C1 0.0281(8) 0.0323(7) 0.0231(7) 0.0026(6) 0.0004(6) -0.0005(6)
C2 0.0710(15) 0.0331(9) 0.0366(9) 0.0016(7) 0.0066(9) -0.0012(9)
C3 0.0558(11) 0.0376(9) 0.0360(9) -0.0017(8) -0.0010(9) 0.0000(8)
C4 0.129(3) 0.0533(12) 0.0401(12) -0.0092(9) 0.0172(14) -0.0105(15)
N1 0.0694(12) 0.0389(8) 0.0376(8) -0.0037(7) 0.0074(8) -0.0105(8)
N2 0.0887(15) 0.0356(8) 0.0443(10) -0.0016(7) 0.0069(9) -0.0100(8)

_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 2.0659(11) . ?
Ni1 O1 2.0659(11) 5 ?
Ni1 O3 2.0716(12) . ?
Ni1 O3 2.0716(12) 5 ?
Ni1 O2 2.0809(12) 8_655 ?
Ni1 O2 2.0809(12) 4_455 ?
O1 C1 1.243(2) . ?
O2 C1 1.254(2) . ?
O2 Ni1 2.0809(12) 4 ?
O3 C2 1.227(2) . ?
O4 C2 1.231(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 N1 1.295(2) . ?
C3 N2 1.306(3) . ?
C3 C4 1.483(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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 180.00(7) . 5 ?
O1 Ni1 O3 87.46(5) . . ?
O1 Ni1 O3 92.54(5) 5 . ?
O1 Ni1 O3 92.54(5) . 5 ?
O1 Ni1 O3 87.46(5) 5 5 ?
O3 Ni1 O3 180.00(7) . 5 ?
O1 Ni1 O2 89.46(4) . 8_655 ?
O1 Ni1 O2 90.54(4) 5 8_655 ?
O3 Ni1 O2 95.19(5) . 8_655 ?
O3 Ni1 O2 84.81(5) 5 8_655 ?
O1 Ni1 O2 90.54(4) . 4_455 ?
O1 Ni1 O2 89.46(4) 5 4_455 ?
O3 Ni1 O2 84.81(5) . 4_455 ?
O3 Ni1 O2 95.19(5) 5 4_455 ?
O2 Ni1 O2 180.00(7) 8_655 4_455 ?
C1 O1 Ni1 121.55(10) . . ?
C1 O2 Ni1 123.76(11) . 4 ?
C2 O3 Ni1 129.83(13) . . ?
O1 C1 O2 124.84(15) . . ?
O1 C1 H1 117.6 . . ?
O2 C1 H1 117.6 . . ?
O3 C2 O4 126.6(2) . . ?
O3 C2 H2 116.7 . . ?
O4 C2 H2 116.7 . . ?
N1 C3 N2 121.89(19) . . ?
N1 C3 C4 118.70(19) . . ?
N2 C3 C4 119.41(19) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.93 2.46 2.987(2) 115.8 4
C4 H4C O1 0.96 2.64 3.547(3) 158.3 5_556
N1 H1A O3 0.86 2.05 2.898(2) 169.4 .
N1 H1B O2 0.86 2.07 2.922(2) 173.6 5_556
N2 H2A O4 0.86 2.03 2.885(3) 172.7 .
N2 H2B O4 0.86 2.04 2.894(2) 171.4 7_566

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        76.39
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_2Ni-180K
_database_code_depnum_ccdc_archive 'CCDC 1840716'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 Ni O8'
_chemical_formula_weight         356.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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 ccn'

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                   7.8046(1)
_cell_length_b                   22.0464(3)
_cell_length_c                   8.4805(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1459.18(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    180.0
_cell_measurement_reflns_used    8745
_cell_measurement_theta_min      3.9870
_cell_measurement_theta_max      76.4340

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.049
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.362
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21004
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0125
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.01
_diffrn_reflns_theta_max         76.53
_reflns_number_total             1537
_reflns_number_gt                1399
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0366P)²+0.9913P] 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     SHELXL
_refine_ls_extinction_coef       0.00069(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1537
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0694
_refine_ls_wR_factor_gt          0.0671
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.0000 0.0000 0.01302(12) Uani 1 2 d S . .
O1 O 0.06995(12) -0.02574(4) 0.22427(11) 0.0171(2) Uani 1 1 d . . .
O2 O 0.25220(13) -0.01686(4) 0.42385(11) 0.0191(2) Uani 1 1 d . . .
O3 O 0.04717(14) 0.08847(4) 0.06706(12) 0.0222(2) Uani 1 1 d . . .
O4 O 0.0823(2) 0.18676(5) 0.02558(15) 0.0384(3) Uani 1 1 d . . .
C1 C 0.19997(18) -0.00337(6) 0.28787(16) 0.0161(3) Uani 1 1 d . . .
H1 H 0.2636 0.0258 0.2297 0.019 Uiso 1 1 calc R . .
C2 C 0.0875(2) 0.13289(7) -0.01611(18) 0.0243(3) Uani 1 1 d . . .
H2 H 0.1253 0.1247 -0.1204 0.029 Uiso 1 1 calc R . .
C3 C -0.0498(2) 0.15887(7) 0.44135(17) 0.0234(3) Uani 1 1 d . . .
C4 C -0.1012(3) 0.17133(8) 0.6074(2) 0.0400(5) Uani 1 1 d . . .
H4A H -0.2142 0.1907 0.6087 0.060 Uiso 1 1 calc R . .
H4B H -0.0170 0.1983 0.6566 0.060 Uiso 1 1 calc R . .
H4C H -0.1064 0.1331 0.6662 0.060 Uiso 1 1 calc R . .
N1 N -0.07815(18) 0.10513(6) 0.38286(15) 0.0259(3) Uani 1 1 d . . .
H1A H -0.0508 0.0972 0.2843 0.031 Uiso 1 1 calc R . .
H1B H -0.1246 0.0767 0.4419 0.031 Uiso 1 1 calc R . .
N2 N 0.01916(19) 0.20244(6) 0.35732(17) 0.0295(3) Uani 1 1 d . . .
H2A H 0.0477 0.1958 0.2584 0.035 Uiso 1 1 calc R . .
H2B H 0.0369 0.2383 0.3998 0.035 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.0144(2) 0.01475(19) 0.00997(18) -0.00013(11) 0.00021(11) 0.00008(11)
O1 0.0168(5) 0.0214(5) 0.0131(4) 0.0012(3) -0.0021(4) -0.0014(4)
O2 0.0173(4) 0.0269(5) 0.0132(4) 0.0023(4) -0.0026(4) -0.0024(4)
O3 0.0324(5) 0.0169(4) 0.0173(5) -0.0006(4) 0.0008(4) -0.0020(4)
O4 0.0674(9) 0.0177(5) 0.0300(6) 0.0011(4) 0.0115(6) -0.0015(6)
C1 0.0163(6) 0.0179(6) 0.0141(6) 0.0008(5) 0.0009(5) 0.0003(5)
C2 0.0332(8) 0.0196(7) 0.0201(7) 0.0001(5) 0.0030(6) 0.0000(6)
C3 0.0279(7) 0.0220(7) 0.0202(7) -0.0002(6) -0.0010(6) 0.0014(6)
C4 0.0699(13) 0.0278(8) 0.0223(8) -0.0037(6) 0.0088(8) -0.0032(8)
N1 0.0364(7) 0.0218(6) 0.0194(6) -0.0016(5) 0.0038(5) -0.0052(5)
N2 0.0463(8) 0.0186(6) 0.0236(7) -0.0015(5) 0.0040(6) -0.0046(5)

_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 2.0585(9) . ?
Ni1 O1 2.0585(9) 5 ?
Ni1 O3 2.0647(10) 5 ?
Ni1 O3 2.0647(10) . ?
Ni1 O2 2.0726(10) 8_655 ?
Ni1 O2 2.0726(10) 4_455 ?
O1 C1 1.2506(17) . ?
O2 C1 1.2588(17) . ?
O2 Ni1 2.0726(10) 4 ?
O3 C2 1.2473(18) . ?
O4 C2 1.240(2) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 N1 1.3033(19) . ?
C3 N2 1.312(2) . ?
C3 C4 1.490(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?

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 180.00(5) . 5 ?
O1 Ni1 O3 92.37(4) . 5 ?
O1 Ni1 O3 87.63(4) 5 5 ?
O1 Ni1 O3 87.63(4) . . ?
O1 Ni1 O3 92.37(4) 5 . ?
O3 Ni1 O3 180.000(17) 5 . ?
O1 Ni1 O2 89.48(4) . 8_655 ?
O1 Ni1 O2 90.52(4) 5 8_655 ?
O3 Ni1 O2 84.90(4) 5 8_655 ?
O3 Ni1 O2 95.10(4) . 8_655 ?
O1 Ni1 O2 90.52(4) . 4_455 ?
O1 Ni1 O2 89.48(4) 5 4_455 ?
O3 Ni1 O2 95.10(4) 5 4_455 ?
O3 Ni1 O2 84.90(4) . 4_455 ?
O2 Ni1 O2 180.0 8_655 4_455 ?
C1 O1 Ni1 120.33(9) . . ?
C1 O2 Ni1 123.04(9) . 4 ?
C2 O3 Ni1 129.12(10) . . ?
O1 C1 O2 124.38(13) . . ?
O1 C1 H1 117.8 . . ?
O2 C1 H1 117.8 . . ?
O4 C2 O3 125.65(14) . . ?
O4 C2 H2 117.2 . . ?
O3 C2 H2 117.2 . . ?
N1 C3 N2 121.92(14) . . ?
N1 C3 C4 118.79(14) . . ?
N2 C3 C4 119.28(14) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.95 2.42 2.9597(18) 115.6 4
C4 H4C O1 0.98 2.56 3.521(2) 167.4 5_556
N1 H1A O3 0.88 2.00 2.8747(17) 170.0 .
N1 H1B O2 0.88 2.01 2.8843(16) 174.3 5_556
N2 H2A O4 0.88 2.00 2.8771(18) 172.0 .
N2 H2B O4 0.88 2.00 2.8715(18) 171.7 7_566

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        76.53
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_2Ni-260K
_database_code_depnum_ccdc_archive 'CCDC 1840718'
_audit_update_record             
;
2018-05-01 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N4 Ni O8'
_chemical_formula_weight         356.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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 ccn'

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                   7.8287(1)
_cell_length_b                   22.0521(3)
_cell_length_c                   8.4976(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1467.02(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    260.0
_cell_measurement_reflns_used    7753
_cell_measurement_theta_min      3.9910
_cell_measurement_theta_max      76.3680

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.049
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.349
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      260.0
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21139
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.01
_diffrn_reflns_theta_max         76.46
_reflns_number_total             1543
_reflns_number_gt                1380
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0401P)²+0.8536P] 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     SHELXL
_refine_ls_extinction_coef       0.00072(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1543
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0741
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 0.0000 0.0000 0.01664(13) Uani 1 2 d S . .
O1 O 0.07104(13) -0.02541(5) 0.22404(11) 0.0219(2) Uani 1 1 d . . .
O2 O 0.25273(14) -0.01682(5) 0.42311(12) 0.0253(2) Uani 1 1 d . . .
O3 O 0.04684(16) 0.08872(5) 0.06645(13) 0.0293(3) Uani 1 1 d . . .
O4 O 0.0824(3) 0.18655(6) 0.02499(17) 0.0526(4) Uani 1 1 d . . .
C1 C 0.20046(19) -0.00334(6) 0.28761(17) 0.0206(3) Uani 1 1 d . . .
H1 H 0.2628 0.0251 0.2308 0.025 Uiso 1 1 calc R . .
C2 C 0.0871(3) 0.13275(7) -0.01585(19) 0.0337(4) Uani 1 1 d . . .
H2 H 0.1242 0.1246 -0.1177 0.040 Uiso 1 1 calc R . .
C3 C -0.0491(2) 0.15899(7) 0.44047(19) 0.0311(3) Uani 1 1 d . . .
C4 C -0.0973(4) 0.17131(9) 0.6066(2) 0.0540(6) Uani 1 1 d . . .
H4A H -0.2065 0.1911 0.6095 0.081 Uiso 1 1 calc R . .
H4B H -0.0129 0.1970 0.6542 0.081 Uiso 1 1 calc R . .
H4C H -0.1037 0.1338 0.6635 0.081 Uiso 1 1 calc R . .
N1 N -0.0777(2) 0.10534(6) 0.38278(17) 0.0346(3) Uani 1 1 d . . .
H1A H -0.0518 0.0975 0.2865 0.042 Uiso 1 1 calc R . .
H1B H -0.1226 0.0777 0.4408 0.042 Uiso 1 1 calc R . .
N2 N 0.0189(2) 0.20236(6) 0.35613(19) 0.0405(4) Uani 1 1 d . . .
H2A H 0.0461 0.1958 0.2596 0.049 Uiso 1 1 calc R . .
H2B H 0.0364 0.2374 0.3973 0.049 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.0184(2) 0.0192(2) 0.01232(19) -0.00011(11) 0.00025(12) 0.00008(12)
O1 0.0217(5) 0.0282(5) 0.0159(4) 0.0022(4) -0.0030(4) -0.0023(4)
O2 0.0228(5) 0.0367(5) 0.0165(4) 0.0034(4) -0.0035(4) -0.0036(4)
O3 0.0439(6) 0.0218(5) 0.0223(5) -0.0008(4) 0.0014(5) -0.0028(5)
O4 0.0951(13) 0.0221(6) 0.0406(7) 0.0018(5) 0.0153(8) -0.0022(7)
C1 0.0208(7) 0.0239(6) 0.0173(6) 0.0019(5) 0.0007(6) -0.0001(5)
C2 0.0493(10) 0.0251(8) 0.0267(8) 0.0006(6) 0.0053(7) -0.0001(7)
C3 0.0392(9) 0.0281(7) 0.0259(8) -0.0006(6) -0.0014(7) 0.0010(7)
C4 0.0956(18) 0.0367(9) 0.0297(9) -0.0056(7) 0.0122(10) -0.0045(11)
N1 0.0495(9) 0.0281(6) 0.0263(7) -0.0022(5) 0.0059(6) -0.0071(6)
N2 0.0643(11) 0.0250(7) 0.0321(8) -0.0016(6) 0.0057(7) -0.0066(6)

_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 2.0610(9) 5 ?
Ni1 O1 2.0610(9) . ?
Ni1 O3 2.0691(10) 5 ?
Ni1 O3 2.0691(10) . ?
Ni1 O2 2.0765(11) 8_655 ?
Ni1 O2 2.0765(11) 4_455 ?
O1 C1 1.2471(18) . ?
O2 C1 1.2576(18) . ?
O2 Ni1 2.0765(11) 4 ?
O3 C2 1.237(2) . ?
O4 C2 1.237(2) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 N1 1.300(2) . ?
C3 N2 1.308(2) . ?
C3 C4 1.486(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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 180.00(6) 5 . ?
O1 Ni1 O3 87.55(4) 5 5 ?
O1 Ni1 O3 92.45(4) . 5 ?
O1 Ni1 O3 92.45(4) 5 . ?
O1 Ni1 O3 87.55(4) . . ?
O3 Ni1 O3 180.000(19) 5 . ?
O1 Ni1 O2 90.54(4) 5 8_655 ?
O1 Ni1 O2 89.46(4) . 8_655 ?
O3 Ni1 O2 84.86(5) 5 8_655 ?
O3 Ni1 O2 95.14(5) . 8_655 ?
O1 Ni1 O2 89.46(4) 5 4_455 ?
O1 Ni1 O2 90.54(4) . 4_455 ?
O3 Ni1 O2 95.14(5) 5 4_455 ?
O3 Ni1 O2 84.86(5) . 4_455 ?
O2 Ni1 O2 180.0 8_655 4_455 ?
C1 O1 Ni1 120.88(9) . . ?
C1 O2 Ni1 123.31(10) . 4 ?
C2 O3 Ni1 129.26(11) . . ?
O1 C1 O2 124.66(13) . . ?
O1 C1 H1 117.7 . . ?
O2 C1 H1 117.7 . . ?
O4 C2 O3 125.93(16) . . ?
O4 C2 H2 117.0 . . ?
O3 C2 H2 117.0 . . ?
N1 C3 N2 121.92(16) . . ?
N1 C3 C4 118.75(16) . . ?
N2 C3 C4 119.33(16) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
C1 H1 O1 0.93 2.44 2.9713(18) 116.0 4
C4 H4C O1 0.96 2.59 3.531(2) 167.9 5_556
N1 H1A O3 0.86 2.03 2.8829(18) 169.7 .
N1 H1B O2 0.86 2.04 2.8997(17) 174.0 5_556
N2 H2A O4 0.86 2.02 2.879(2) 172.5 .
N2 H2B O4 0.86 2.03 2.882(2) 171.4 7_566

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        76.46
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.050
