# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 725885'
_audit_update_record             
;
2017-06-29 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 Co N8 O4'
_chemical_formula_sum            'C6 H6 Co N8 O4'
_chemical_formula_weight         313.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   14.4184(16)
_cell_length_b                   8.3825(8)
_cell_length_c                   9.4836(9)
_cell_angle_alpha                90
_cell_angle_beta                 118.5310(10)
_cell_angle_gamma                90
_cell_volume                     1007.01(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1251
_cell_measurement_theta_min      4
_cell_measurement_theta_max      28.285

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.065
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.736
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4191
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.914
_diffrn_reflns_theta_max         28.285
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1197
_reflns_number_gt                1174
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+1.2867P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1197
_refine_ls_number_parameters     87
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0230
_refine_ls_wR_factor_ref         0.0624
_refine_ls_wR_factor_gt          0.0617
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 0.03875(3) 0.7500 0.01303(11) Uani 1 2 d S T P . .
O1 O 0.53570(9) -0.21900(13) 0.42022(12) 0.0227(2) Uani 1 1 d . . . . .
O2 O 0.46833(8) -0.13357(13) 0.57594(12) 0.0178(2) Uani 1 1 d . . . . .
N1 N 0.67999(9) -0.40867(15) 0.65642(14) 0.0159(2) Uani 1 1 d . . . . .
N2 N 0.66545(11) -0.51264(18) 0.53987(18) 0.0267(3) Uani 1 1 d . . . . .
N3 N 0.75757(11) -0.54237(17) 0.55451(18) 0.0272(3) Uani 1 1 d . . . . .
N4 N 0.83283(10) -0.45923(14) 0.68005(16) 0.0188(3) Uani 1 1 d . . . . .
C1 C 0.78238(11) -0.37785(19) 0.74103(17) 0.0206(3) Uani 1 1 d . . . . .
H1A H 0.8134 -0.3099 0.8290 0.025 Uiso 1 1 calc R U . . .
C2 C 0.59144(10) -0.34514(18) 0.67310(16) 0.0168(3) Uani 1 1 d . . . . .
H2A H 0.6181 -0.2975 0.7786 0.020 Uiso 1 1 calc R U . . .
H2B H 0.5450 -0.4323 0.6656 0.020 Uiso 1 1 calc R U . . .
C3 C 0.52780(10) -0.22003(16) 0.54560(15) 0.0140(3) Uani 1 1 d . . . . .

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 0.01195(15) 0.01709(16) 0.01131(15) 0.000 0.00658(11) 0.000
O1 0.0318(6) 0.0248(5) 0.0170(5) 0.0057(4) 0.0160(4) 0.0105(4)
O2 0.0149(5) 0.0225(5) 0.0155(5) -0.0025(4) 0.0069(4) 0.0043(4)
N1 0.0130(5) 0.0198(6) 0.0146(5) 0.0000(4) 0.0062(4) 0.0032(4)
N2 0.0171(6) 0.0296(7) 0.0306(7) -0.0138(6) 0.0092(6) -0.0002(5)
N3 0.0170(6) 0.0332(8) 0.0298(7) -0.0127(6) 0.0097(6) 0.0008(5)
N4 0.0144(6) 0.0241(6) 0.0177(6) -0.0028(4) 0.0075(5) 0.0013(4)
C1 0.0139(6) 0.0281(7) 0.0180(6) -0.0049(6) 0.0061(5) 0.0015(5)
C2 0.0142(6) 0.0233(7) 0.0159(6) 0.0041(5) 0.0095(5) 0.0059(5)
C3 0.0114(5) 0.0168(6) 0.0125(6) -0.0008(5) 0.0048(5) 0.0004(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
Co1 O2 2.0736(10) . ?
Co1 O2 2.0736(10) 2_656 ?
Co1 O1 2.0880(11) 6_556 ?
Co1 O1 2.0880(11) 5_656 ?
Co1 N4 2.1731(13) 4_656 ?
Co1 N4 2.1731(13) 3_455 ?
O1 C3 1.2476(16) . ?
O1 Co1 2.0881(11) 5_656 ?
O2 C3 1.2565(16) . ?
N1 C1 1.3261(18) . ?
N1 N2 1.3431(18) . ?
N1 C2 1.4599(16) . ?
N2 N3 1.2921(19) . ?
N3 N4 1.3589(18) . ?
N4 C1 1.3156(19) . ?
N4 Co1 2.1731(13) 3_545 ?
C1 H1A 0.9300 . ?
C2 C3 1.5310(18) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Co1 O2 91.69(6) . 2_656 ?
O2 Co1 O1 177.12(4) . 6_556 ?
O2 Co1 O1 90.54(4) 2_656 6_556 ?
O2 Co1 O1 90.54(4) . 5_656 ?
O2 Co1 O1 177.12(4) 2_656 5_656 ?
O1 Co1 O1 87.30(6) 6_556 5_656 ?
O2 Co1 N4 92.23(4) . 4_656 ?
O2 Co1 N4 88.40(4) 2_656 4_656 ?
O1 Co1 N4 86.01(5) 6_556 4_656 ?
O1 Co1 N4 93.34(5) 5_656 4_656 ?
O2 Co1 N4 88.40(4) . 3_455 ?
O2 Co1 N4 92.23(4) 2_656 3_455 ?
O1 Co1 N4 93.34(4) 6_556 3_455 ?
O1 Co1 N4 86.01(5) 5_656 3_455 ?
N4 Co1 N4 179.11(6) 4_656 3_455 ?
C3 O1 Co1 129.86(10) . 5_656 ?
C3 O2 Co1 132.00(9) . . ?
C1 N1 N2 108.38(12) . . ?
C1 N1 C2 129.93(12) . . ?
N2 N1 C2 121.67(12) . . ?
N3 N2 N1 106.76(12) . . ?
N2 N3 N4 110.18(12) . . ?
C1 N4 N3 105.86(12) . . ?
C1 N4 Co1 129.45(10) . 3_545 ?
N3 N4 Co1 124.65(10) . 3_545 ?
N4 C1 N1 108.82(13) . . ?
N4 C1 H1A 125.6 . . ?
N1 C1 H1A 125.6 . . ?
N1 C2 C3 112.93(11) . . ?
N1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
O1 C3 O2 126.67(13) . . ?
O1 C3 C2 117.67(12) . . ?
O2 C3 C2 115.56(11) . . ?

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.095

_shelx_res_file                  
;

    1.res created by SHELXL-2014/7

TITL    1 in C2/c
CELL 0.71073  14.4184   8.3825   9.4836  90.000 118.531  90.000
ZERR    4.00   0.0016   0.0008   0.0009   0.000   0.001   0.000
LATT  7
SYMM -X,Y, 0.50000-Z
SFAC    C   H   N   O   CO
UNIT    24  24  32  16   4
MERG    2
L.S.    4
acta 55
bond $h
FMAP    2
PLAN    25
WGHT    0.040200    1.286700
FVAR       0.56343
CO1   5    0.500000    0.038748    0.750000    10.50000    0.01195    0.01709 =
         0.01131    0.00000    0.00658    0.00000
O1    4    0.535704   -0.218997    0.420220    11.00000    0.03181    0.02476 =
         0.01703    0.00566    0.01603    0.01046
O2    4    0.468331   -0.133573    0.575944    11.00000    0.01485    0.02253 =
         0.01551   -0.00251    0.00687    0.00428
N1    3    0.679989   -0.408667    0.656422    11.00000    0.01301    0.01975 =
         0.01458   -0.00002    0.00617    0.00318
N2    3    0.665452   -0.512637    0.539875    11.00000    0.01712    0.02957 =
         0.03065   -0.01378    0.00917   -0.00017
N3    3    0.757572   -0.542367    0.554508    11.00000    0.01699    0.03318 =
         0.02978   -0.01269    0.00974    0.00079
N4    3    0.832833   -0.459227    0.680051    11.00000    0.01439    0.02407 =
         0.01767   -0.00284    0.00747    0.00135
C1    1    0.782382   -0.377848    0.741029    11.00000    0.01388    0.02807 =
         0.01803   -0.00491    0.00611    0.00155
AFIX  43
H1A   2    0.813433   -0.309857    0.829036    11.00000   -1.20000
AFIX   0
C2    1    0.591441   -0.345143    0.673098    11.00000    0.01418    0.02326 =
         0.01588    0.00412    0.00947    0.00588
AFIX  23
H2A   2    0.618108   -0.297528    0.778611    11.00000   -1.20000
H2B   2    0.545030   -0.432291    0.665565    11.00000   -1.20000
AFIX   0
C3    1    0.527800   -0.220030    0.545605    11.00000    0.01142    0.01682 =
         0.01252   -0.00078    0.00479    0.00041

HKLF      4

REM     1 in C2/c
REM R1 =  0.0230 for    1174 Fo > 4sig(Fo)  and  0.0236 for all    1197 data
REM     87 parameters refined using      0 restraints

END

WGHT      0.0303      1.2066

REM Highest difference peak  0.451,  deepest hole -0.558,  1-sigma level  0.095
Q1    1   0.5696 -0.2761  0.6164  11.00000  0.05    0.45
Q2    1   0.6367 -0.3766  0.6620  11.00000  0.05    0.32
Q3    1   0.3993 -0.1008  0.4583  11.00000  0.05    0.24
Q4    1   0.7331 -0.4087  0.7252  11.00000  0.05    0.21
Q5    1   0.3740 -0.0187  0.4409  11.00000  0.05    0.21
Q6    1   0.6017 -0.3672  0.7635  11.00000  0.05    0.20
Q7    1   0.8116 -0.3804  0.8505  11.00000  0.05    0.20
Q8    1   0.5616 -0.1927  0.4995  11.00000  0.05    0.20
Q9    1   0.8108 -0.4405  0.7319  11.00000  0.05    0.19
Q10   1   0.8370 -0.5365  0.9021  11.00000  0.05    0.19
Q11   1   0.6025 -0.0623  0.5195  11.00000  0.05    0.18
Q12   1   0.6554 -0.5391  0.7962  11.00000  0.05    0.18
Q13   1   0.5748 -0.3321  0.3012  11.00000  0.05    0.18
Q14   1   0.6293 -0.4630  0.7710  11.00000  0.05    0.17
Q15   1   0.5610 -0.5501  0.7830  11.00000  0.05    0.17
Q16   1   0.5001 -0.1608  0.5616  11.00000  0.05    0.17
Q17   1   0.5849 -0.4529  0.3529  11.00000  0.05    0.17
Q18   1   0.7729 -0.5145  0.8400  11.00000  0.05    0.17
Q19   1   0.5506 -0.4414  0.7823  11.00000  0.05    0.16
Q20   1   0.5900 -0.2466  0.4344  11.00000  0.05    0.16
Q21   1   0.7863 -0.5482  0.4173  11.00000  0.05    0.16
Q22   1   0.5951 -0.3571  0.3863  11.00000  0.05    0.16
Q23   1   0.7402 -0.4508  0.8181  11.00000  0.05    0.16
Q24   1   0.4707 -0.0062  0.4869  11.00000  0.05    0.16
Q25   1   0.8780 -0.1398  0.7627  11.00000  0.05    0.15
;
_shelx_res_checksum              47865
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 725886'
_audit_update_record             
;
2017-06-29 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 Mn N8O4'
_chemical_formula_sum            'C6 H6 Mn N8 O4'
_chemical_formula_weight         309.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   14.7220(15)
_cell_length_b                   8.4723(9)
_cell_length_c                   9.6326(10)
_cell_angle_alpha                90
_cell_angle_beta                 119.0620(10)
_cell_angle_gamma                90
_cell_volume                     1050.19(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1228
_cell_measurement_theta_min      4
_cell_measurement_theta_max      28.262

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.955
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.287
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD areadetector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3286
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.879
_diffrn_reflns_theta_max         28.262
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             1228
_reflns_number_gt                1174
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+1.1146P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1228
_refine_ls_number_parameters     87
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0640
_refine_ls_wR_factor_gt          0.0634
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 1.0000 0.04063(3) 0.7500 0.01568(11) Uani 1 2 d S T P . .
O1 O 1.03602(9) 0.22323(14) 0.92452(12) 0.0300(3) Uani 1 1 d . . . . .
O2 O 0.96769(7) 0.14166(12) 1.07439(11) 0.0216(2) Uani 1 1 d . . . . .
N1 N 1.32662(9) 0.46068(14) 1.17991(16) 0.0240(3) Uani 1 1 d . . . . .
N2 N 1.25181(10) 0.54206(16) 1.05498(17) 0.0303(3) Uani 1 1 d . . . . .
N3 N 1.16178(10) 0.51362(17) 1.04137(17) 0.0295(3) Uani 1 1 d . . . . .
N4 N 1.17692(8) 0.41195(14) 1.15792(13) 0.0182(2) Uani 1 1 d . . . . .
C1 C 1.27784(10) 0.38160(19) 1.24163(17) 0.0243(3) Uani 1 1 d . . . . .
H1B H 1.3090 0.3153 1.3295 0.029 Uiso 1 1 calc R U . . .
C2 C 1.09029(10) 0.34878(17) 1.17398(16) 0.0196(3) Uani 1 1 d . . . . .
H2B H 1.0449 0.4349 1.1671 0.024 Uiso 1 1 calc R U . . .
H2C H 1.1170 0.3008 1.2780 0.024 Uiso 1 1 calc R U . . .
C3 C 1.02697(10) 0.22571(15) 1.04657(15) 0.0170(3) Uani 1 1 d . . . . .

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
Mn1 0.01370(16) 0.02069(17) 0.01370(16) 0.000 0.00748(12) 0.000
O1 0.0440(6) 0.0320(6) 0.0218(5) -0.0091(4) 0.0223(5) -0.0153(5)
O2 0.0171(4) 0.0266(5) 0.0186(5) 0.0032(4) 0.0067(4) -0.0044(4)
N1 0.0156(6) 0.0318(7) 0.0230(6) 0.0043(5) 0.0081(5) -0.0008(4)
N2 0.0197(6) 0.0368(8) 0.0325(7) 0.0131(5) 0.0110(6) -0.0008(5)
N3 0.0188(6) 0.0327(7) 0.0343(8) 0.0146(6) 0.0107(5) 0.0007(5)
N4 0.0144(5) 0.0227(5) 0.0165(5) 0.0006(4) 0.0066(4) -0.0024(4)
C1 0.0153(6) 0.0336(8) 0.0206(7) 0.0061(6) 0.0061(5) -0.0012(5)
C2 0.0155(6) 0.0277(7) 0.0180(6) -0.0037(5) 0.0101(5) -0.0056(5)
C3 0.0151(5) 0.0197(6) 0.0144(6) 0.0008(5) 0.0059(5) -0.0006(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
Mn1 O1 2.1528(11) 2_756 ?
Mn1 O1 2.1528(11) . ?
Mn1 O2 2.1659(10) 6 ?
Mn1 O2 2.1659(10) 5_757 ?
Mn1 N1 2.3015(12) 8_455 ?
Mn1 N1 2.3015(12) 7_757 ?
O1 C3 1.2459(16) . ?
O2 C3 1.2521(16) . ?
O2 Mn1 2.1659(10) 5_757 ?
N1 C1 1.3165(19) . ?
N1 N2 1.3598(18) . ?
N1 Mn1 2.3015(12) 7_757 ?
N2 N3 1.2896(18) . ?
N3 N4 1.3450(17) . ?
N4 C1 1.3266(17) . ?
N4 C2 1.4589(16) . ?
C1 H1B 0.9300 . ?
C2 C3 1.5333(18) . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O1 88.12(6) 2_756 . ?
O1 Mn1 O2 91.44(4) 2_756 6 ?
O1 Mn1 O2 178.44(4) . 6 ?
O1 Mn1 O2 178.44(4) 2_756 5_757 ?
O1 Mn1 O2 91.45(4) . 5_757 ?
O2 Mn1 O2 89.03(6) 6 5_757 ?
O1 Mn1 N1 87.54(5) 2_756 8_455 ?
O1 Mn1 N1 92.86(4) . 8_455 ?
O2 Mn1 N1 88.62(4) 6 8_455 ?
O2 Mn1 N1 90.99(4) 5_757 8_455 ?
O1 Mn1 N1 92.86(4) 2_756 7_757 ?
O1 Mn1 N1 87.54(5) . 7_757 ?
O2 Mn1 N1 90.99(4) 6 7_757 ?
O2 Mn1 N1 88.62(4) 5_757 7_757 ?
N1 Mn1 N1 179.45(6) 8_455 7_757 ?
C3 O1 Mn1 130.56(9) . . ?
C3 O2 Mn1 131.39(8) . 5_757 ?
C1 N1 N2 105.82(12) . . ?
C1 N1 Mn1 129.47(10) . 7_757 ?
N2 N1 Mn1 124.62(9) . 7_757 ?
N3 N2 N1 110.24(12) . . ?
N2 N3 N4 106.82(12) . . ?
C1 N4 N3 108.30(11) . . ?
C1 N4 C2 130.02(12) . . ?
N3 N4 C2 121.63(11) . . ?
N1 C1 N4 108.81(13) . . ?
N1 C1 H1B 125.6 . . ?
N4 C1 H1B 125.6 . . ?
N4 C2 C3 112.80(11) . . ?
N4 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
N4 C2 H2C 109.0 . . ?
C3 C2 H2C 109.0 . . ?
H2B C2 H2C 107.8 . . ?
O1 C3 O2 126.69(12) . . ?
O1 C3 C2 117.69(12) . . ?
O2 C3 C2 115.55(11) . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.078

_shelx_res_file                  
;

    1.res created by SHELXL-2014/7

TITL    1 in C2/c
CELL 0.71073  14.7220   8.4723   9.6326  90.000 119.062  90.000
ZERR    4.00   0.0015   0.0009   0.0010   0.000   0.001   0.000
LATT  7
SYMM -X,Y, 0.50000-Z
SFAC    C   H   N   O   Mn
UNIT    24  24  32  16   4
MERG    2
L.S.    10
bond $h
acta 55
FMAP    2
PLAN    25
WGHT    0.037700    1.114600
FVAR       0.56388
MN1   5    1.000000    0.040627    0.750000    10.50000    0.01370    0.02069 =
         0.01370    0.00000    0.00748    0.00000
O1    4    1.036015    0.223232    0.924521    11.00000    0.04400    0.03204 =
         0.02185   -0.00909    0.02225   -0.01529
O2    4    0.967691    0.141663    1.074393    11.00000    0.01708    0.02658 =
         0.01857    0.00318    0.00672   -0.00437
N1    3    1.326623    0.460683    1.179911    11.00000    0.01561    0.03181 =
         0.02298    0.00434    0.00814   -0.00084
N2    3    1.251809    0.542058    1.054979    11.00000    0.01965    0.03676 =
         0.03252    0.01308    0.01101   -0.00079
N3    3    1.161781    0.513624    1.041369    11.00000    0.01881    0.03270 =
         0.03434    0.01456    0.01072    0.00065
N4    3    1.176919    0.411946    1.157921    11.00000    0.01441    0.02267 =
         0.01651    0.00060    0.00663   -0.00243
C1    1    1.277838    0.381599    1.241632    11.00000    0.01529    0.03356 =
         0.02061    0.00607    0.00606   -0.00118
AFIX  43
H1B   2    1.309010    0.315329    1.329502    11.00000   -1.20000
AFIX   0
C2    1    1.090290    0.348782    1.173975    11.00000    0.01553    0.02766 =
         0.01803   -0.00372    0.01008   -0.00562
AFIX  23
H2B   2    1.044872    0.434901    1.167120    11.00000   -1.20000
H2C   2    1.117036    0.300844    1.278010    11.00000   -1.20000
AFIX   0
C3    1    1.026970    0.225711    1.046566    11.00000    0.01513    0.01974 =
         0.01444    0.00078    0.00585   -0.00063

HKLF      4

REM     1 in C2/c
REM R1 =  0.0234 for    1174 Fo > 4sig(Fo)  and  0.0243 for all    1228 data
REM     87 parameters refined using      0 restraints

END

WGHT      0.0275      1.1015

REM Highest difference peak  0.377,  deepest hole -0.326,  1-sigma level  0.078
Q1    1   1.0592  0.2863  1.1069  11.00000  0.05    0.38
Q2    1   1.1358  0.3719  1.1596  11.00000  0.05    0.22
Q3    1   0.9137  0.0613  0.9542  11.00000  0.05    0.20
Q4    1   1.0721  0.1930  0.9975  11.00000  0.05    0.19
Q5    1   1.0000  0.5209  1.2500  10.50000  0.05    0.19
Q6    1   0.9415  0.5488  1.1392  11.00000  0.05    0.17
Q7    1   1.0823  0.3702  1.2393  11.00000  0.05    0.17
Q8    1   1.0903  0.0506  1.0014  11.00000  0.05    0.17
Q9    1   1.0186  0.3509  0.7815  11.00000  0.05    0.16
Q10   1   1.2259  0.4061  1.2246  11.00000  0.05    0.16
Q11   1   1.2224  0.3636  1.1790  11.00000  0.05    0.15
Q12   1   1.3473  0.4919  1.4626  11.00000  0.05    0.15
Q13   1   0.9997  0.1548  1.0621  11.00000  0.05    0.15
Q14   1   1.2687  0.5184  1.3260  11.00000  0.05    0.15
Q15   1   1.3039  0.4445  1.2326  11.00000  0.05    0.14
Q16   1   1.0731  0.2799  0.9153  11.00000  0.05    0.14
Q17   1   1.0694  0.5144  1.2780  11.00000  0.05    0.14
Q18   1   1.0552  0.4493  1.2958  11.00000  0.05    0.14
Q19   1   0.9279  0.1909  1.1011  11.00000  0.05    0.14
Q20   1   1.1223  0.1109  1.0576  11.00000  0.05    0.13
Q21   1   1.0106  0.2463  0.9578  11.00000  0.05    0.13
Q22   1   1.0697  0.6389  1.2587  11.00000  0.05    0.13
Q23   1   1.1112  0.5914  1.3212  11.00000  0.05    0.12
Q24   1   1.2603  0.5926  0.9975  11.00000  0.05    0.12
Q25   1   1.2500  0.7500  1.0000  10.50000  0.05    0.12
;
_shelx_res_checksum              56812
####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 725887'
_audit_update_record             
;
2017-06-29 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N8 Ni O4'
_chemical_formula_sum            'C6 H6 N8 Ni O4'
_chemical_formula_weight         312.90

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   14.285(2)
_cell_length_b                   8.3073(14)
_cell_length_c                   9.4700(16)
_cell_angle_alpha                90
_cell_angle_beta                 118.178(2)
_cell_angle_gamma                90
_cell_volume                     990.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1231
_cell_measurement_theta_min      4
_cell_measurement_theta_max      28.328

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.098
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.991
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2986
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.938
_diffrn_reflns_theta_max         28.328
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             1150
_reflns_number_gt                1032
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+1.1225P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1150
_refine_ls_number_parameters     87
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0695
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.04144(4) 0.7500 0.01709(14) Uani 1 2 d S T P . .
O2 O 0.46783(10) 0.13037(18) 1.07486(16) 0.0212(3) Uani 1 1 d . . . . .
O1 O 0.53380(12) 0.22200(18) 0.91730(17) 0.0251(3) Uani 1 1 d . . . . .
N4 N 0.83640(13) 0.4568(2) 1.1808(2) 0.0219(4) Uani 1 1 d . . . . .
N3 N 0.76123(15) 0.5414(2) 1.0545(2) 0.0309(5) Uani 1 1 d . . . . .
N1 N 0.68173(13) 0.4078(2) 1.1563(2) 0.0203(4) Uani 1 1 d . . . . .
C2 C 0.59171(15) 0.3443(3) 1.1725(2) 0.0213(4) Uani 1 1 d . . . . .
H2A H 0.5455 0.4329 1.1659 0.026 Uiso 1 1 calc R U . . .
H2B H 0.6179 0.2955 1.2775 0.026 Uiso 1 1 calc R U . . .
N2 N 0.66838(15) 0.5124(2) 1.0400(3) 0.0309(4) Uani 1 1 d . . . . .
C1 C 0.78476(15) 0.3756(3) 1.2410(3) 0.0247(4) Uani 1 1 d . . . . .
H1A H 0.8153 0.3066 1.3286 0.030 Uiso 1 1 calc R U . . .
C3 C 0.52697(14) 0.2194(2) 1.0444(2) 0.0184(4) Uani 1 1 d . . . . .

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 0.01467(19) 0.0218(2) 0.0168(2) 0.000 0.00915(15) 0.000
O2 0.0171(7) 0.0270(8) 0.0202(7) 0.0024(6) 0.0093(6) -0.0041(6)
O1 0.0318(8) 0.0279(8) 0.0208(7) -0.0048(6) 0.0167(6) -0.0094(6)
N4 0.0171(8) 0.0262(9) 0.0223(9) 0.0026(7) 0.0093(7) -0.0011(6)
N3 0.0200(9) 0.0369(11) 0.0348(11) 0.0119(9) 0.0120(8) -0.0009(8)
N1 0.0167(8) 0.0240(9) 0.0203(9) -0.0003(7) 0.0088(7) -0.0034(7)
C2 0.0170(9) 0.0298(11) 0.0205(10) -0.0033(8) 0.0117(8) -0.0057(8)
N2 0.0202(9) 0.0360(10) 0.0359(11) 0.0130(9) 0.0128(8) 0.0003(8)
C1 0.0171(9) 0.0323(11) 0.0227(10) 0.0056(9) 0.0078(8) -0.0004(8)
C3 0.0147(8) 0.0218(10) 0.0181(9) 0.0012(7) 0.0071(7) 0.0006(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 2.0665(15) . ?
Ni1 O1 2.0665(15) 2_656 ?
Ni1 O2 2.0687(14) 6 ?
Ni1 O2 2.0687(14) 5_657 ?
Ni1 N4 2.1082(17) 8_455 ?
Ni1 N4 2.1082(17) 7_657 ?
O2 C3 1.254(2) . ?
O2 Ni1 2.0686(14) 5_657 ?
O1 C3 1.253(2) . ?
N4 C1 1.312(3) . ?
N4 N3 1.365(3) . ?
N4 Ni1 2.1082(17) 7_657 ?
N3 N2 1.290(3) . ?
N1 C1 1.329(3) . ?
N1 N2 1.345(3) . ?
N1 C2 1.463(2) . ?
C2 C3 1.531(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O1 86.93(8) . 2_656 ?
O1 Ni1 O2 176.85(5) . 6 ?
O1 Ni1 O2 90.18(6) 2_656 6 ?
O1 Ni1 O2 90.18(6) . 5_657 ?
O1 Ni1 O2 176.85(5) 2_656 5_657 ?
O2 Ni1 O2 92.75(8) 6 5_657 ?
O1 Ni1 N4 93.25(6) . 8_455 ?
O1 Ni1 N4 86.17(6) 2_656 8_455 ?
O2 Ni1 N4 87.80(6) 6 8_455 ?
O2 Ni1 N4 92.75(6) 5_657 8_455 ?
O1 Ni1 N4 86.17(6) . 7_657 ?
O1 Ni1 N4 93.25(6) 2_656 7_657 ?
O2 Ni1 N4 92.75(6) 6 7_657 ?
O2 Ni1 N4 87.80(6) 5_657 7_657 ?
N4 Ni1 N4 179.20(10) 8_455 7_657 ?
C3 O2 Ni1 132.23(12) . 5_657 ?
C3 O1 Ni1 128.90(13) . . ?
C1 N4 N3 105.91(17) . . ?
C1 N4 Ni1 129.54(15) . 7_657 ?
N3 N4 Ni1 124.51(14) . 7_657 ?
N2 N3 N4 109.96(18) . . ?
C1 N1 N2 108.22(16) . . ?
C1 N1 C2 129.94(18) . . ?
N2 N1 C2 121.82(17) . . ?
N1 C2 C3 113.14(16) . . ?
N1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N3 N2 N1 106.99(17) . . ?
N4 C1 N1 108.91(18) . . ?
N4 C1 H1A 125.5 . . ?
N1 C1 H1A 125.5 . . ?
O1 C3 O2 126.68(18) . . ?
O1 C3 C2 117.22(17) . . ?
O2 C3 C2 115.97(17) . . ?

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.075

_shelx_res_file                  
;

    1.res created by SHELXL-2014/7

TITL    1 in C2/c
CELL 0.71073  14.2848   8.3073   9.4700  90.000 118.178  90.000
ZERR    4.00   0.0024   0.0014   0.0016   0.000   0.002   0.000
LATT  7
SYMM -X,Y, 0.50000-Z
SFAC    C   H   N   O   NI
UNIT    24  24  32  16   4
MERG    2
L.S.    10
acta 55
bond $h
FMAP    2
PLAN    1
WGHT    0.043300    1.122500
FVAR       0.47450
NI1   5    0.500000    0.041444    0.750000    10.50000    0.01467    0.02184 =
         0.01685    0.00000    0.00915    0.00000
O2    4    0.467826    0.130368    1.074863    11.00000    0.01706    0.02705 =
         0.02022    0.00242    0.00932   -0.00415
O1    4    0.533800    0.221997    0.917298    11.00000    0.03182    0.02785 =
         0.02083   -0.00483    0.01675   -0.00940
N4    3    0.836404    0.456788    1.180797    11.00000    0.01707    0.02622 =
         0.02234    0.00262    0.00931   -0.00109
N3    3    0.761232    0.541429    1.054547    11.00000    0.02005    0.03693 =
         0.03477    0.01189    0.01205   -0.00089
N1    3    0.681734    0.407799    1.156333    11.00000    0.01667    0.02402 =
         0.02033   -0.00029    0.00882   -0.00342
C2    1    0.591714    0.344349    1.172528    11.00000    0.01704    0.02983 =
         0.02053   -0.00326    0.01171   -0.00573
AFIX  23
H2A   2    0.545523    0.432864    1.165900    11.00000   -1.20000
H2B   2    0.617932    0.295528    1.277471    11.00000   -1.20000
AFIX   0
N2    3    0.668383    0.512447    1.039972    11.00000    0.02024    0.03603 =
         0.03586    0.01305    0.01276    0.00031
C1    1    0.784761    0.375558    1.240958    11.00000    0.01709    0.03231 =
         0.02275    0.00560    0.00784   -0.00042
AFIX  43
H1A   2    0.815288    0.306621    1.328579    11.00000   -1.20000
AFIX   0
C3    1    0.526973    0.219383    1.044426    11.00000    0.01467    0.02176 =
         0.01812    0.00117    0.00712    0.00064

HKLF      4

REM     1 in C2/c
REM R1 =  0.0271 for    1032 Fo > 4sig(Fo)  and  0.0319 for all    1150 data
REM     87 parameters refined using      0 restraints

END

WGHT      0.0346      1.2088

REM Highest difference peak  0.452,  deepest hole -0.473,  1-sigma level  0.075
Q1    1   0.5384 -0.0447  0.8008  11.00000  0.05    0.45
;
_shelx_res_checksum              2131
