# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 1898603'
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-04-11 downloaded from the CCDC.
;

_vrf_PLAT420_1                   
;
PROBLEM: D-H Without Acceptor       O2       --H2A            Please Check 
RESPONSE: The acceptors of H2A and H4A are N2 and N1, respectively.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 Mn N4 Ni O2, 4(H2 O)'
_chemical_formula_sum            'C4 H12 Mn N4 Ni O6'
_chemical_formula_weight         325.83

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   12.1445(9)
_cell_length_b                   14.1014(12)
_cell_length_c                   7.3111(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1252.06(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1513
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      25.26

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_F_000             660
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    2.529
_shelx_estimated_absorpt_T_min   0.718
_shelx_estimated_absorpt_T_max   0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5588
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.139
_diffrn_reflns_theta_max         25.356
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1192
_reflns_number_gt                867
_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)+(0.0266P)²+0.5928P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1192
_refine_ls_number_parameters     85
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0660
_refine_ls_wR_factor_gt          0.0582
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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 0.56988(4) 0.2500 0.98877(7) 0.01049(16) Uani 1 2 d S T P . .
Mn2 Mn 0.5000 0.5000 0.5000 0.00969(18) Uani 1 2 d S . P . .
C1 C 0.5761(3) 0.3433(2) 0.8080(4) 0.0125(7) Uani 1 1 d . . . . .
C2 C 0.5452(3) 0.3426(2) 1.1660(4) 0.0141(8) Uani 1 1 d . . . . .
N1 N 0.5727(2) 0.4004(2) 0.6970(3) 0.0181(6) Uani 1 1 d . . . . .
N2 N 0.5267(2) 0.3989(2) 1.2750(4) 0.0203(7) Uani 1 1 d . . . . .
O1 O 0.33664(18) 0.43708(16) 0.5691(3) 0.0178(5) Uani 1 1 d . . . . .
H1A H 0.2803 0.4768 0.5561 0.053(14) Uiso 1 1 d R . . . .
H1B H 0.3259 0.3891 0.5011 0.064 Uiso 0.5 1 d R U P . .
H1C H 0.3382 0.4178 0.6793 0.064 Uiso 0.5 1 d R U P . .
O2 O 0.17894(19) 0.56815(17) 0.4560(3) 0.0234(6) Uani 1 1 d D . . . .
H2A H 0.1209(17) 0.566(2) 0.514(3) 0.028 Uiso 1 1 d D U . . .
H2B H 0.1642 0.5562 0.3452 0.028 Uiso 0.5 1 d R U P . .
H2C H 0.2082 0.6197 0.4680 0.028 Uiso 0.5 1 d R U P . .
O3 O 0.7887(3) 0.2500 0.0564(4) 0.0247(8) Uani 1 2 d DS T P . .
H3A H 0.785(3) 0.2500 0.167(3) 0.030 Uiso 1 2 d DS U P . .
H3D H 0.8017 0.1944 -0.0033 0.030 Uiso 0.5 1 d R U P . .
O4 O 0.7477(3) 0.2500 0.4413(5) 0.0282(9) Uani 1 2 d S T P . .
H4A H 0.6844 0.2500 0.4972 0.034 Uiso 1 2 d R U P . .
H4B H 0.7785 0.3030 0.4624 0.034 Uiso 0.5 1 d R U P . .

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 0.0185(3) 0.0065(3) 0.0064(3) 0.000 0.0010(3) 0.000
Mn2 0.0163(4) 0.0070(3) 0.0058(3) 0.0002(3) 0.0006(3) 0.0009(2)
C1 0.0141(17) 0.014(2) 0.0095(16) -0.0024(14) 0.0021(14) 0.0020(15)
C2 0.020(2) 0.011(2) 0.0105(16) 0.0047(14) -0.0009(15) -0.0012(15)
N1 0.0202(16) 0.0214(17) 0.0128(14) 0.0058(13) 0.0007(13) 0.0025(14)
N2 0.0303(18) 0.0170(16) 0.0135(15) -0.0038(13) 0.0019(13) 0.0021(14)
O1 0.0188(13) 0.0153(13) 0.0193(12) 0.0013(10) 0.0026(10) -0.0004(11)
O2 0.0185(13) 0.0291(15) 0.0228(15) -0.0030(11) 0.0023(10) 0.0013(11)
O3 0.030(2) 0.022(2) 0.0217(19) 0.000 -0.0015(16) 0.000
O4 0.0262(19) 0.027(2) 0.031(2) 0.000 0.0029(16) 0.000

_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 C2 1.864(3) 7_565 ?
Ni1 C2 1.864(3) . ?
Ni1 C1 1.867(3) . ?
Ni1 C1 1.867(3) 7_565 ?
Mn2 N1 2.197(3) . ?
Mn2 N1 2.197(3) 5_666 ?
Mn2 N2 2.201(3) 5_667 ?
Mn2 N2 2.201(3) 1_554 ?
Mn2 O1 2.231(2) . ?
Mn2 O1 2.231(2) 5_666 ?
C1 N1 1.144(4) . ?
C2 N2 1.147(4) . ?
N2 Mn2 2.201(3) 1_556 ?
O1 H1A 0.8887 . ?
O1 H1B 0.8500 . ?
O1 H1C 0.8500 . ?
O2 H2A 0.824(14) . ?
O2 H2B 0.8463 . ?
O2 H2C 0.8141 . ?
O3 H3A 0.813(19) . ?
O3 H3D 0.9110 . ?
O4 H4A 0.8701 . ?
O4 H4B 0.8500 . ?

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
C2 Ni1 C2 88.96(19) 7_565 . ?
C2 Ni1 C1 173.05(15) 7_565 . ?
C2 Ni1 C1 90.26(13) . . ?
C2 Ni1 C1 90.26(13) 7_565 7_565 ?
C2 Ni1 C1 173.05(15) . 7_565 ?
C1 Ni1 C1 89.69(18) . 7_565 ?
N1 Mn2 N1 180.0 . 5_666 ?
N1 Mn2 N2 89.04(10) . 5_667 ?
N1 Mn2 N2 90.96(10) 5_666 5_667 ?
N1 Mn2 N2 90.96(10) . 1_554 ?
N1 Mn2 N2 89.04(10) 5_666 1_554 ?
N2 Mn2 N2 180.0 5_667 1_554 ?
N1 Mn2 O1 87.39(10) . . ?
N1 Mn2 O1 92.61(10) 5_666 . ?
N2 Mn2 O1 87.56(9) 5_667 . ?
N2 Mn2 O1 92.44(9) 1_554 . ?
N1 Mn2 O1 92.61(10) . 5_666 ?
N1 Mn2 O1 87.39(10) 5_666 5_666 ?
N2 Mn2 O1 92.44(9) 5_667 5_666 ?
N2 Mn2 O1 87.56(9) 1_554 5_666 ?
O1 Mn2 O1 180.00(11) . 5_666 ?
N1 C1 Ni1 175.6(3) . . ?
N2 C2 Ni1 177.9(3) . . ?
C1 N1 Mn2 158.4(3) . . ?
C2 N2 Mn2 175.2(3) . 1_556 ?
Mn2 O1 H1A 114.2 . . ?
Mn2 O1 H1B 108.7 . . ?
H1A O1 H1B 108.7 . . ?
Mn2 O1 H1C 108.8 . . ?
H1A O1 H1C 108.7 . . ?
H1B O1 H1C 107.6 . . ?
H2A O2 H2B 107.7 . . ?
H2A O2 H2C 110.9 . . ?
H2B O2 H2C 111.9 . . ?
H3A O3 H3D 119.2 . . ?
H4A O4 H4B 107.7 . . ?

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.092

_shelx_res_file                  
;

    1.res created by SHELXL-2014/7


TITL 1 in Pnma
CELL 0.71073  12.1445  14.1014   7.3111  90.000  90.000  90.000
ZERR    4.00   0.0009   0.0012   0.0005   0.000   0.000   0.000
LATT 1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, -Z
SYMM 0.5+X, 0.5-Y, 0.5-Z
SFAC C  H  N  O  Mn Ni
UNIT 16 48 16 24 4 4
L.S. 10
BOND $h
size 0.14 0.08 0.07
acta
dfix .82 o2 h2a o3 h3a
dfix 2.63 h2a n2_$1
eqiv $1 .5-x,1-y,-.5+z
FMAP 2
PLAN 20
TEMP -100.050
WGHT    0.026550    0.592810
FVAR       0.12139
NI1   6    0.569877    0.250000    0.988774    10.50000    0.01850    0.00653 =
         0.00642    0.00000    0.00099    0.00000
MN2   5    0.500000    0.500000    0.500000    10.50000    0.01629    0.00696 =
         0.00584    0.00017    0.00064    0.00090
C1    1    0.576079    0.343342    0.808042    11.00000    0.01408    0.01388 =
         0.00951   -0.00239    0.00206    0.00200
C2    1    0.545192    0.342623    1.166020    11.00000    0.02033    0.01149 =
         0.01052    0.00471   -0.00089   -0.00119
N1    3    0.572669    0.400416    0.696972    11.00000    0.02019    0.02142 =
         0.01281    0.00582    0.00072    0.00248
N2    3    0.526661    0.398878    1.274981    11.00000    0.03031    0.01702 =
         0.01348   -0.00378    0.00187    0.00208
O1    4    0.336645    0.437085    0.569147    11.00000    0.01882    0.01533 =
         0.01934    0.00126    0.00263   -0.00042
AFIX   3
H1A   2    0.280335    0.476765    0.556127    11.00000    0.05299
H1B   2    0.325865    0.389085    0.501147    10.50000   -1.20000
H1C   2    0.338215    0.417795    0.679257    10.50000   -1.20000
AFIX   0
O2    4    0.178939    0.568150    0.456006    11.00000    0.01850    0.02907 =
         0.02277   -0.00298    0.00226    0.00127
H2A   2    0.120874    0.565635    0.514153    11.00000   -1.20000
AFIX   3
H2B   2    0.164194    0.556245    0.345223    10.50000   -1.20000
H2C   2    0.208174    0.619725    0.468003    10.50000   -1.20000
AFIX   0
O3    4    0.788687    0.250000    0.056353    10.50000    0.03045    0.02208 =
         0.02168    0.00000   -0.00146    0.00000
H3A   2    0.785016    0.250000    0.167442    10.50000   -1.20000
AFIX   3
H3D   2    0.801736    0.194420   -0.003338    10.50000   -1.20000
AFIX   0
O4    4    0.747656    0.250000    0.441254    10.50000    0.02618    0.02706 =
         0.03129    0.00000    0.00286    0.00000
AFIX   3
H4A   2    0.684426    0.250000    0.497204    10.50000   -1.20000
H4B   2    0.778526    0.302980    0.462354    10.50000   -1.20000

AFIX   0
HKLF 4

REM  1 in Pnma
REM R1 =  0.0335 for     867 Fo > 4sig(Fo)  and  0.0634 for all    1192 data
REM     85 parameters refined using      3 restraints

END

WGHT      0.0235      0.6319

REM Highest difference peak  0.474,  deepest hole -0.339,  1-sigma level  0.092
Q1    1   0.6785  0.2500  0.3268  10.50000  0.05    0.47
Q2    1   0.7122  0.2500 -0.1725  10.50000  0.05    0.41
Q3    1   0.8573  0.2500 -0.1320  10.50000  0.05    0.34
Q4    1   0.8575  0.2500  0.1102  10.50000  0.05    0.33
Q5    1   0.8981  0.3300  0.1799  11.00000  0.05    0.32
Q6    1   0.6972  0.2500  0.6808  10.50000  0.05    0.30
Q7    1   0.6784  0.3586  0.4116  11.00000  0.05    0.30
Q8    1   0.7595  0.2500  0.5763  10.50000  0.05    0.30
Q9    1   0.6053  0.2803  0.8382  11.00000  0.05    0.29
Q10   1   0.6651  0.3393  0.4305  11.00000  0.05    0.28
Q11   1   0.3122  0.6085  0.4628  11.00000  0.05    0.27
Q12   1   0.8988  0.2500  0.1664  10.50000  0.05    0.27
Q13   1   0.2253  0.4144  0.3791  11.00000  0.05    0.27
Q14   1   0.3754  0.4566  0.4936  11.00000  0.05    0.27
Q15   1   0.8664  0.2068  0.0005  11.00000  0.05    0.27
Q16   1   0.6423  0.3169  0.5688  11.00000  0.05    0.27
Q17   1   0.9365  0.2062 -0.0983  11.00000  0.05    0.27
Q18   1   0.1948  0.5696  0.6114  11.00000  0.05    0.27
Q19   1   0.5065  0.2500  0.6370  10.50000  0.05    0.26
Q20   1   0.7779  0.2500  0.7176  10.50000  0.05    0.26
;
_shelx_res_checksum              13005
####################################################################### 
# 
# 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 1898604'
_audit_update_record             
;
2019-02-21 deposited with the CCDC.	2019-04-11 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_1                   
;
PROBLEM: D-H Without Acceptor       O2       --H2A            Please Check 
RESPONSE: H2A and H4A were found from the Fourier maps. Cyano N atoms
are their H-bonding acceptors. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 Co N4 Ni O2, 4(H2 O)'
_chemical_formula_sum            'C4 H12 Co N4 Ni O6'
_chemical_formula_weight         329.82

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   12.0628(12)
_cell_length_b                   13.8833(9)
_cell_length_c                   7.1686(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1200.54(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2768
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      26.39

_exptl_crystal_description       sheet
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.968
_shelx_estimated_absorpt_T_min   0.681
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6345
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12322
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.934
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1277
_reflns_number_gt                935
_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)+(0.0242P)²+0.2587P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1277
_refine_ls_number_parameters     107
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0576
_refine_ls_wR_factor_gt          0.0505
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.0740(3) 0.34483(18) 0.3073(3) 0.0112(6) Uani 1 1 d . . . . .
C2 C 0.0454(2) 0.34390(18) 0.6724(4) 0.0119(6) Uani 1 1 d . . . . .
Co1 Co 0.0000 0.5000 0.0000 0.00870(14) Uani 1 2 d S . P . .
N1 N 0.0679(2) 0.40344(15) 0.1951(3) 0.0138(5) Uani 1 1 d . . . . .
N2 N 0.0270(2) 0.40029(16) 0.7855(3) 0.0150(5) Uani 1 1 d . . . . .
Ni1 Ni 0.07010(4) 0.2500 0.49141(6) 0.00935(13) Uani 1 2 d S T P . .
O1 O -0.15781(18) 0.43873(13) 0.0639(3) 0.0154(4) Uani 1 1 d D . . . .
H1A H -0.205(2) 0.4741(18) 0.019(4) 0.018 Uiso 1 1 d D U . . .
H1B H -0.166(5) 0.439(4) 0.178(3) 0.018 Uiso 0.5 1 d D U P . .
H1C H -0.162(5) 0.387(2) 0.012(7) 0.018 Uiso 0.5 1 d D U P . .
O2 O 0.67899(19) 0.56680(15) 0.9547(3) 0.0207(5) Uani 1 1 d D . . . .
H2A H 0.625(2) 0.550(2) 1.013(4) 0.025 Uiso 1 1 d D U . . .
H2B H 0.698(5) 0.619(2) 0.997(8) 0.025 Uiso 0.5 1 d D U P . .
H2C H 0.669(5) 0.562(4) 0.842(3) 0.025 Uiso 0.5 1 d D U P . .
O3 O 0.2905(3) 0.2500 0.5577(4) 0.0243(7) Uani 1 2 d DS T P . .
H3A H 0.286(4) 0.2500 0.670(3) 0.029 Uiso 1 2 d DS U P . .
H3B H 0.315(5) 0.299(3) 0.514(8) 0.029 Uiso 0.5 1 d D U P . .
O4 O 0.2517(3) 0.7500 0.4477(4) 0.0235(7) Uani 1 2 d DS T P . .
H4A H 0.3175(17) 0.7500 0.464(6) 0.028 Uiso 1 2 d DS U P . .
H4B H 0.224(5) 0.703(3) 0.500(8) 0.028 Uiso 0.5 1 d D U P . .

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
C1 0.0117(15) 0.0111(15) 0.0108(13) -0.0037(10) -0.0009(11) 0.0016(12)
C2 0.0154(18) 0.0078(15) 0.0124(14) 0.0034(10) -0.0008(11) -0.0009(11)
Co1 0.0157(3) 0.0045(2) 0.0059(2) 0.00032(19) 0.0010(2) 0.00110(18)
N1 0.0174(14) 0.0112(11) 0.0128(11) 0.0027(9) -0.0004(10) 0.0014(11)
N2 0.0199(15) 0.0123(12) 0.0129(12) -0.0011(9) 0.0007(11) 0.0009(11)
Ni1 0.0185(3) 0.0046(2) 0.0050(2) 0.000 0.0006(3) 0.000
O1 0.0170(13) 0.0118(10) 0.0175(10) 0.0020(8) 0.0007(9) 0.0000(9)
O2 0.0215(13) 0.0218(12) 0.0189(12) -0.0022(9) -0.0002(9) -0.0007(10)
O3 0.031(2) 0.0228(18) 0.0195(16) 0.000 0.0014(15) 0.000
O4 0.026(2) 0.0206(17) 0.0239(17) 0.000 0.0004(14) 0.000

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.147(3) . ?
C1 Ni1 1.865(3) . ?
C2 N2 1.149(3) . ?
C2 Ni1 1.863(3) . ?
Co1 N2 2.095(2) 5_566 ?
Co1 N2 2.095(2) 1_554 ?
Co1 N1 2.103(2) 5_565 ?
Co1 N1 2.103(2) . ?
Co1 O1 2.135(2) . ?
Co1 O1 2.135(2) 5_565 ?
N2 Co1 2.095(2) 1_556 ?
Ni1 C2 1.863(3) 7_565 ?
Ni1 C1 1.865(3) 7_565 ?
O1 H1A 0.816(17) . ?
O1 H1B 0.82(2) . ?
O1 H1C 0.81(2) . ?
O2 H2A 0.806(18) . ?
O2 H2B 0.82(2) . ?
O2 H2C 0.82(2) . ?
O3 H3A 0.805(19) . ?
O3 H3B 0.80(2) . ?
O4 H4A 0.803(19) . ?
O4 H4B 0.82(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 Ni1 174.8(3) . . ?
N2 C2 Ni1 177.7(3) . . ?
N2 Co1 N2 180.00(9) 5_566 1_554 ?
N2 Co1 N1 90.38(8) 5_566 5_565 ?
N2 Co1 N1 89.62(8) 1_554 5_565 ?
N2 Co1 N1 89.62(8) 5_566 . ?
N2 Co1 N1 90.38(8) 1_554 . ?
N1 Co1 N1 180.0 5_565 . ?
N2 Co1 O1 88.13(8) 5_566 . ?
N2 Co1 O1 91.87(8) 1_554 . ?
N1 Co1 O1 92.84(9) 5_565 . ?
N1 Co1 O1 87.15(9) . . ?
N2 Co1 O1 91.87(8) 5_566 5_565 ?
N2 Co1 O1 88.13(8) 1_554 5_565 ?
N1 Co1 O1 87.15(9) 5_565 5_565 ?
N1 Co1 O1 92.85(9) . 5_565 ?
O1 Co1 O1 180.0 . 5_565 ?
C1 N1 Co1 160.8(3) . . ?
C2 N2 Co1 177.0(2) . 1_556 ?
C2 Ni1 C2 88.81(15) . 7_565 ?
C2 Ni1 C1 172.27(13) . 7_565 ?
C2 Ni1 C1 90.16(10) 7_565 7_565 ?
C2 Ni1 C1 90.16(10) . . ?
C2 Ni1 C1 172.27(13) 7_565 . ?
C1 Ni1 C1 89.83(14) 7_565 . ?
Co1 O1 H1A 107(2) . . ?
Co1 O1 H1B 109(4) . . ?
H1A O1 H1B 108(5) . . ?
Co1 O1 H1C 108(4) . . ?
H1A O1 H1C 108(5) . . ?
H1B O1 H1C 117(5) . . ?
H2A O2 H2B 107(5) . . ?
H2A O2 H2C 111(5) . . ?
H2B O2 H2C 119(6) . . ?
H3A O3 H3B 115(5) . . ?
H4A O4 H4B 109(5) . . ?

_refine_diff_density_max         0.430
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.094

_shelx_res_file                  
;

    1.res created by SHELXL-2014/7

TITL 1 in Pnma
CELL 0.71073  12.0628  13.8833   7.1686  90.000  90.000  90.000
ZERR    4.00   0.0012   0.0009   0.0005   0.000   0.000   0.000
LATT 1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, -Z
SYMM 0.5+X, 0.5-Y, 0.5-Z
SFAC C  H  N  O  Co Ni
UNIT 16 48 16 24 4 4
L.S. 10
BOND $h
acta
size 0.14 0.10 0.03
FMAP 2
PLAN 10
dfix .82 o4 h4a o4 h4b
dfix .82 o3 h3a o3 h3b o1 h1a o1 h1b o1 h1c o2 h2a o2 h2b o2 h2c
TEMP -100.150
WGHT    0.024200    0.258700
FVAR       0.11320
MOLE 1
C1    1    0.074027    0.344835    0.307319    11.00000    0.01168    0.01106 =
         0.01078   -0.00368   -0.00091    0.00159
C2    1    0.045449    0.343904    0.672416    11.00000    0.01535    0.00784 =
         0.01242    0.00338   -0.00081   -0.00094
CO1   5    0.000000    0.500000    0.000000    10.50000    0.01571    0.00453 =
         0.00586    0.00032    0.00096    0.00110
N1    3    0.067853    0.403441    0.195102    11.00000    0.01737    0.01124 =
         0.01276    0.00270   -0.00039    0.00143
N2    3    0.026951    0.400292    0.785463    11.00000    0.01994    0.01232 =
         0.01287   -0.00107    0.00072    0.00089
NI1   6    0.070101    0.250000    0.491415    10.50000    0.01847    0.00456 =
         0.00501    0.00000    0.00063    0.00000
O1    4   -0.157807    0.438732    0.063897    11.00000    0.01696    0.01175 =
         0.01747    0.00201    0.00067    0.00000
H1A   2   -0.204712    0.474122    0.018698    11.00000   -1.20000
H1B   2   -0.166180    0.439418    0.177699    10.50000   -1.20000
H1C   2   -0.162304    0.387062    0.012186    10.50000   -1.20000
O2    4    0.678989    0.566796    0.954656    11.00000    0.02149    0.02185 =
         0.01887   -0.00217   -0.00023   -0.00070
H2A   2    0.625215    0.549959    1.012982    11.00000   -1.20000
H2B   2    0.698491    0.618860    0.997282    10.50000   -1.20000
H2C   2    0.668873    0.561796    0.842434    10.50000   -1.20000
MOLE 2
O3    4    0.290491    0.250000    0.557706    10.50000    0.03076    0.02278 =
         0.01947    0.00000    0.00144    0.00000
H3A   2    0.286192    0.250000    0.669718    10.50000   -1.20000
H3B   2    0.314554    0.298683    0.513773    10.50000   -1.20000
MOLE 1
O4    4    0.251651    0.750000    0.447739    10.50000    0.02600    0.02056 =
         0.02392    0.00000    0.00035    0.00000
H4A   2    0.317473    0.750000    0.464141    10.50000   -1.20000
H4B   2    0.224201    0.703151    0.500141    10.50000   -1.20000
HKLF 4

REM  1 in Pnma
REM R1 =  0.0303 for     935 Fo > 4sig(Fo)  and  0.0563 for all    1277 data
REM    107 parameters refined using     10 restraints

END

WGHT      0.0218      0.3468

REM Highest difference peak  0.430,  deepest hole -0.585,  1-sigma level  0.094
Q1    1   0.0226  0.2500  0.3445  10.50000  0.05    0.43
Q2    1   0.2830  0.2500  0.8085  10.50000  0.05    0.39
Q3    1   0.0216  0.2925  0.3643  11.00000  0.05    0.39
Q4    1   0.1232  0.2500  0.3697  10.50000  0.05    0.38
Q5    1   0.3438  0.2500  0.6782  10.50000  0.05    0.38
Q6    1  -0.0225  0.2500  0.5509  10.50000  0.05    0.35
Q7    1   0.1571  0.2500  0.5029  10.50000  0.05    0.35
Q8    1   0.4354  0.2500  0.6456  10.50000  0.05    0.31
Q9    1   0.1395  0.2500  0.6238  10.50000  0.05    0.31
Q10   1   0.6539  0.5198  1.1326  11.00000  0.05    0.30
;
_shelx_res_checksum              44388
