# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_sh17035
_database_code_depnum_ccdc_archive 'CCDC 1909059'
loop_
_audit_author_name
_audit_author_address
'Vincent Lynch'
;University of Texas at Austin
United States of America
;
_audit_update_record             
;
2019-09-26 deposited with the CCDC.	2019-12-23 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT090_sh17035             
;
PROBLEM: Poor Data / Parameter Ratio (Zmax > 18) ........       7.98 Note  
RESPONSE: The data to parameter ratio is calculated based on the number 
of reflections that have been averaged ignoring anomalous scattering 
considerations (748) whereas the model was refined using 1278 reflections.  
Using this number, the data/parameter ratio is 13.9.
;
_vrf_PLAT341_sh17035             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.009 Ang.  
RESPONSE: The scattering is dominated by the Se atom.
;
_vrf_PLAT911_sh17035             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: The data collection strategy was set to collect 99.5% of the data 
available.  
;


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H5 N O2 Se'
_chemical_formula_sum            'C6 H5 N O2 Se'
_chemical_formula_weight         202.07

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'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   8.3732(5)
_cell_length_b                   13.5112(7)
_cell_length_c                   5.8925(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     666.63(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1983
_cell_measurement_theta_min      6.20
_cell_measurement_theta_max      73.1

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.013
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    7.095
_shelx_estimated_absorpt_T_min   0.102
_shelx_estimated_absorpt_T_max   0.815
_exptl_absorpt_correction_type   'gaussian and multi-scan'
_exptl_absorpt_correction_T_min  0.396
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Agilent SuperNova with an Atlas S2 CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3348
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         6.218
_diffrn_reflns_theta_max         74.070
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             1287
_reflns_number_gt                1268
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_max     0.904
_reflns_Friedel_fraction_full    0.951

_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       
'CrysAlisPro V 1.171.40.53, Rigaku Oxford Diffraction'
_computing_cell_refinement       
'CrysAlisPro V 1.171.40.53, Rigaku Oxford Diffraction'
_computing_data_reduction        
'CrysAlisPro V 1.171.40.53, Rigaku Oxford Diffraction'


_computing_structure_solution    
;

SHELXT. Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8. 
;
_computing_structure_refinement  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'Shelxl-2016/6, Sheldrick, G. M.'







_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)+(0.0669P)²+0.5547P] 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_abs_structure_details 
;
 Flack x determined using 524 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1287
_refine_ls_number_parameters     92
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0877
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.015
_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
Se1 Se 0.67291(6) 0.09564(3) 0.3119(2) 0.0234(2) Uani 1 1 d . . . . .
N1 N 0.7572(6) 0.2841(3) 0.1792(8) 0.0219(9) Uani 1 1 d . . . . .
H1N H 0.809254 0.249407 0.076627 0.026 Uiso 1 1 calc R U . . .
O1 O 0.4718(6) 0.1541(3) 0.7095(7) 0.0299(9) Uani 1 1 d . . . . .
H1A H 0.524352 0.125163 0.607779 0.045 Uiso 1 1 calc R U . . .
O2 O 0.4324(5) 0.3059(3) 0.8342(9) 0.0301(9) Uani 1 1 d . . . . .
C2 C 0.6711(5) 0.2334(4) 0.3361(17) 0.0215(14) Uani 1 1 d . . . . .
C3 C 0.5920(6) 0.2910(4) 0.5022(9) 0.0187(10) Uani 1 1 d . . . . .
C4 C 0.6021(7) 0.3936(4) 0.4909(10) 0.0210(11) Uani 1 1 d . . . . .
H4 H 0.546524 0.432103 0.600265 0.025 Uiso 1 1 calc R U . . .
C5 C 0.6900(5) 0.4412(4) 0.3268(18) 0.0218(11) Uani 1 1 d . . . . .
H5 H 0.696235 0.511334 0.321932 0.026 Uiso 1 1 calc R U . . .
C6 C 0.7691(7) 0.3832(4) 0.1687(9) 0.0222(10) Uani 1 1 d . . . . .
H6 H 0.831459 0.413401 0.053223 0.027 Uiso 1 1 calc R U . . .
C7 C 0.4948(7) 0.2506(4) 0.6941(9) 0.0228(11) Uani 1 1 d . . . . .


_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
Se1 C2 1.867(5) . ?
N1 C6 1.344(8) . ?
N1 C2 1.358(9) . ?
N1 H1N 0.8800 . ?
O1 C7 1.321(7) . ?
O1 H1A 0.8400 . ?
O2 C7 1.230(7) . ?
C2 C3 1.415(9) . ?
C3 C4 1.390(7) . ?
C3 C7 1.497(7) . ?
C4 C5 1.374(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(10) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?

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
C6 N1 C2 124.9(5) . . ?
C6 N1 H1N 117.5 . . ?
C2 N1 H1N 117.5 . . ?
C7 O1 H1A 109.5 . . ?
N1 C2 C3 116.2(5) . . ?
N1 C2 Se1 116.5(5) . . ?
C3 C2 Se1 127.3(5) . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 C7 115.7(5) . . ?
C2 C3 C7 125.2(5) . . ?
C5 C4 C3 122.1(5) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 117.7(5) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
N1 C6 C5 119.8(5) . . ?
N1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
O2 C7 O1 119.5(5) . . ?
O2 C7 C3 121.1(5) . . ?
O1 C7 C3 119.4(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 -1.5(9) . . . . ?
C6 N1 C2 Se1 179.5(4) . . . . ?
N1 C2 C3 C4 2.2(8) . . . . ?
Se1 C2 C3 C4 -179.0(5) . . . . ?
N1 C2 C3 C7 -178.2(5) . . . . ?
Se1 C2 C3 C7 0.7(9) . . . . ?
C2 C3 C4 C5 -1.7(9) . . . . ?
C7 C3 C4 C5 178.6(6) . . . . ?
C3 C4 C5 C6 0.4(9) . . . . ?
C2 N1 C6 C5 0.3(9) . . . . ?
C4 C5 C6 N1 0.4(9) . . . . ?
C4 C3 C7 O2 -1.8(8) . . . . ?
C2 C3 C7 O2 178.6(6) . . . . ?
C4 C3 C7 O1 176.2(5) . . . . ?
C2 C3 C7 O1 -3.5(9) . . . . ?

_refine_diff_density_max         0.651
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_sh17045
_database_code_depnum_ccdc_archive 'CCDC 1909060'
loop_
_audit_author_name
_audit_author_address
'Vincent Lynch'
;University of Texas at Austin
United States of America
;
_audit_update_record             
;
2019-04-09 deposited with the CCDC.	2019-12-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT973_sh17045             
;
PROBLEM: Check Calcd Positive Resid. Density on       Ni1       1.73 eA-3  
RESPONSE: The residual electron density on Ni is probably due to series termination 
affects.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H6 N2 Ni O5 Se3'
_chemical_formula_weight         553.78

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'
Se Se -0.7943 1.1372 '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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           138
_space_group_name_H-M_alt        'P 42/n c m'
_space_group_name_Hall           '-P 4ac 2ac'

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

_cell_length_a                   17.22940(10)
_cell_length_b                   17.22940(10)
_cell_length_c                   14.7730(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4385.40(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7384
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      74.1

_exptl_crystal_description       rod
_exptl_crystal_colour            'deep green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             2096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.093
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    7.153
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'numerical and multi-scan'
_exptl_absorpt_correction_T_min  0.356
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed micro-focus tube'
_diffrn_measurement_device_type  'Agilent SuperNova with Atlas S2 CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23322
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.628
_diffrn_reflns_theta_max         74.489
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2346
_reflns_number_gt                2111
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
# SQUEEZE RESULTS (Version = 300517)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 0.250 0.016 426 120 ' '
2 0.250 0.750 -0.008 282 88 ' '
3 0.750 0.750 -0.054 426 120 ' '
4 0.750 0.250 -0.008 282 88 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?



_computing_data_collection       
'CrysAlisPro V 1.171.40.37a, Rigaku Oxford Diffraction'
_computing_cell_refinement       
'CrysAlisPro V 1.171.40.37a, Rigaku Oxford Diffraction'
_computing_data_reduction        
'CrysAlisPro V 1.171.40.37a, Rigaku Oxford Diffraction'

_computing_structure_solution    
;

Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8. SHELXT.  An Integrated Space Group 
and Crystal Structure Determination Program.  

;
_computing_structure_refinement  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'Shelxl-2016/6, Sheldrick, G. M.'

_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.

 
 Two cylindrical solvent voids were observed parallel to the c-axis along 
1/4, 1/4, z and 1/4, 3/4, z.  The solvent contained therein was severely 
disordered.  Attempts to model the disorder were unsatisfactory.  
The contributions to the 
scattering factors due to these solvent molecules were removed by use of 
the utility SQUEEZE (Sluis and Spek, 1990) in PLATON (Spek, 2009).  
PLATON98 was used as incorporated in WinGX (Farrugia, 1999).

The seleno-pyridine-carboxylate group was disordered.  The seleno-pyridine 
group was modeled separately from the carboxylate group.  The disorder 
was modeled in the same fashion for each grouping.  For example, the 
site occupancy for one component of the disordered carboxylate was 
assigned to the variable x.  The site occupancy for atoms of the alternate 
component was assigend to (1-x).  A common isotropic displacement 
parameter was refined for all six atoms while refining x.  Upon 
convergence of x, the site occupancy factors were fixed and the 
displacement parameters were refined.  Anisotropic displacement parameters 
were for the affected atoms were restrained to be approximately 
isotropic.  The geometry of the two groups were restrained to be 
equivalent throughout the refinement process.  

;








_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1045P)²+21.4266P] 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         2346
_refine_ls_number_parameters     191
_refine_ls_number_restraints     334
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1638
_refine_ls_wR_factor_gt          0.1583
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.019
_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 0.50020(4) -0.00020(4) 0.26964(7) 0.0117(3) Uani 1 2 d S TU P . .
N1 N 0.5008(15) 0.115(2) 0.312(3) 0.0283(19) Uani 0.51 1 d . U P A 1
Se1 Se 0.49190(11) 0.17523(15) 0.13255(17) 0.0217(5) Uani 0.51 1 d D U P A 1
C2 C 0.5060(3) 0.1794(19) 0.2634(6) 0.031(2) Uani 0.51 1 d D U P A 1
C3 C 0.5022(4) 0.2542(12) 0.2973(13) 0.032(2) Uani 0.51 1 d . U P A 1
C4 C 0.5123(5) 0.2611(8) 0.3913(9) 0.033(2) Uani 0.51 1 d . U P A 1
H4 H 0.510969 0.310615 0.419613 0.040 Uiso 0.51 1 calc R U P A 1
C5 C 0.5242(7) 0.1937(11) 0.4424(14) 0.039(2) Uani 0.51 1 d . U P A 1
H5 H 0.530275 0.197249 0.506219 0.047 Uiso 0.51 1 calc R U P A 1
C6 C 0.5270(8) 0.128(2) 0.404(2) 0.041(3) Uani 0.51 1 d . U P A 1
H6 H 0.546954 0.084566 0.436771 0.049 Uiso 0.51 1 calc R U P A 1
N1A N 0.5130(16) 0.117(3) 0.313(3) 0.0283(19) Uani 0.49 1 d . U P A 2
Se1A Se 0.46198(12) 0.17184(16) 0.13630(19) 0.0237(5) Uani 0.49 1 d D U P A 2
C2A C 0.4971(4) 0.182(2) 0.2613(6) 0.031(2) Uani 0.49 1 d D U P A 2
C3A C 0.5236(5) 0.2563(12) 0.3011(13) 0.030(2) Uani 0.49 1 d . U P A 2
C4A C 0.5474(5) 0.2620(8) 0.3878(8) 0.027(2) Uani 0.49 1 d . U P A 2
H4A H 0.563297 0.310863 0.411200 0.032 Uiso 0.49 1 calc R U P A 2
C5A C 0.5486(7) 0.1980(12) 0.4418(14) 0.037(2) Uani 0.49 1 d . U P A 2
H5A H 0.565852 0.199855 0.502822 0.045 Uiso 0.49 1 calc R U P A 2
C6A C 0.5200(9) 0.122(2) 0.397(2) 0.042(3) Uani 0.49 1 d . U P A 2
H6A H 0.507550 0.078522 0.433965 0.051 Uiso 0.49 1 calc R U P A 2
Se2 Se 0.45992(3) 0.04008(3) 0.11730(5) 0.0169(2) Uani 1 2 d S TU P A .
O1 O 0.4725(7) 0.3163(5) 0.1617(7) 0.036(2) Uani 0.51 1 d D U P A 1
O2 O 0.4981(6) 0.3888(11) 0.2830(10) 0.016(2) Uani 0.51 1 d D U P A 1
C7 C 0.4888(6) 0.3262(7) 0.2436(8) 0.016(2) Uani 0.51 1 d . U P A 1
O1A O 0.5186(6) 0.3180(5) 0.1568(6) 0.029(2) Uani 0.49 1 d D U P A 2
O2A O 0.5207(7) 0.3913(12) 0.2810(10) 0.016(2) Uani 0.49 1 d D U P A 2
C7A C 0.5228(6) 0.3284(7) 0.2396(9) 0.015(2) Uani 0.49 1 d . U P A 2
O3 O 0.54398(19) -0.04398(19) 0.3910(3) 0.0196(11) Uani 1 2 d S TU P A .


_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 O2A 2.05(2) 5_645 ?
Ni1 O2A 2.05(2) 12_656 ?
Ni1 O2 2.06(2) 5_645 ?
Ni1 O2 2.06(2) 12_656 ?
Ni1 O3 2.087(5) . ?
Ni1 N1 2.09(4) 15_665 ?
Ni1 N1 2.09(4) . ?
Ni1 N1A 2.13(4) . ?
Ni1 N1A 2.13(4) 15_665 ?
Ni1 Se2 2.4553(13) . ?
N1 C2 1.32(5) . ?
N1 C6 1.45(6) . ?
Se1 C2 1.950(8) . ?
Se1 Se2 2.403(2) . ?
C2 C3 1.38(4) . ?
C3 C4 1.40(2) . ?
C3 C7 1.49(2) . ?
C4 C5 1.40(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.27(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N1A C6A 1.24(6) . ?
N1A C2A 1.38(6) . ?
Se1A C2A 1.950(8) . ?
Se1A Se2 2.288(3) . ?
C2A C3A 1.49(4) . ?
C3A C4A 1.35(2) . ?
C3A C7A 1.54(2) . ?
C4A C5A 1.36(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.55(4) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
O1 C7 1.254(16) . ?
O2 C7 1.237(17) . ?
O1A C7A 1.239(15) . ?
O2A C7A 1.245(18) . ?

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
O2A Ni1 O2 11.0(6) 5_645 5_645 ?
O2A Ni1 O2 90.7(3) 12_656 5_645 ?
O2 Ni1 O2 80.3(6) 5_645 12_656 ?
O2A Ni1 O3 92.7(3) 5_645 . ?
O2A Ni1 O3 92.7(3) 12_656 . ?
O2 Ni1 O3 89.1(3) 5_645 . ?
O2 Ni1 O3 89.1(3) 12_656 . ?
O2A Ni1 N1 86.4(9) 5_645 15_665 ?
O2A Ni1 N1 169.2(8) 12_656 15_665 ?
O2 Ni1 N1 97.0(9) 5_645 15_665 ?
O2 Ni1 N1 175.1(12) 12_656 15_665 ?
O3 Ni1 N1 94.9(11) . 15_665 ?
O2 Ni1 N1 175.1(12) 5_645 . ?
O2 Ni1 N1 97.0(9) 12_656 . ?
O3 Ni1 N1 94.9(11) . . ?
N1 Ni1 N1 85.4(15) 15_665 . ?
O2A Ni1 N1A 174.2(10) 5_645 . ?
O2A Ni1 N1A 81.3(9) 12_656 . ?
O3 Ni1 N1A 92.5(11) . . ?
O2A Ni1 N1A 81.3(9) 5_645 15_665 ?
O2A Ni1 N1A 174.2(10) 12_656 15_665 ?
O2 Ni1 N1A 91.8(9) 5_645 15_665 ?
O2 Ni1 N1A 171.9(10) 12_656 15_665 ?
O3 Ni1 N1A 92.5(11) . 15_665 ?
N1 Ni1 N1A 5.7(14) 15_665 15_665 ?
N1 Ni1 N1A 90.7(3) . 15_665 ?
N1A Ni1 N1A 96.0(16) . 15_665 ?
O2A Ni1 Se2 82.7(3) 5_645 . ?
O2A Ni1 Se2 82.7(3) 12_656 . ?
O2 Ni1 Se2 85.4(3) 5_645 . ?
O2 Ni1 Se2 85.4(3) 12_656 . ?
O3 Ni1 Se2 172.82(15) . . ?
N1 Ni1 Se2 90.3(11) 15_665 . ?
N1 Ni1 Se2 90.3(11) . . ?
N1A Ni1 Se2 92.3(11) . . ?
N1A Ni1 Se2 92.3(11) 15_665 . ?
C2 N1 C6 112(3) . . ?
C2 N1 Ni1 129(3) . . ?
C6 N1 Ni1 115(3) . . ?
C2 Se1 Se2 99.1(9) . . ?
N1 C2 C3 125(2) . . ?
N1 C2 Se1 120(2) . . ?
C3 C2 Se1 112.8(19) . . ?
C2 C3 C4 115.6(17) . . ?
C2 C3 C7 126.1(16) . . ?
C4 C3 C7 118.3(15) . . ?
C5 C4 C3 118.7(15) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 120(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 N1 122(4) . . ?
C5 C6 H6 118.8 . . ?
N1 C6 H6 118.8 . . ?
C6A N1A C2A 121(4) . . ?
C6A N1A Ni1 112(3) . . ?
C2A N1A Ni1 125(3) . . ?
C2A Se1A Se2 101.9(10) . . ?
N1A C2A C3A 114.7(19) . . ?
N1A C2A Se1A 121(3) . . ?
C3A C2A Se1A 123(2) . . ?
C4A C3A C2A 122.2(18) . . ?
C4A C3A C7A 120.2(16) . . ?
C2A C3A C7A 117.6(15) . . ?
C3A C4A C5A 120.1(15) . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A C6A 116(2) . . ?
C4A C5A H5A 122.2 . . ?
C6A C5A H5A 122.2 . . ?
N1A C6A C5A 121(4) . . ?
N1A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
Se1A Se2 Se1A 90.90(11) 15_665 . ?
Se1A Se2 Se1 12.46(6) 15_665 15_665 ?
Se1A Se2 Se1 103.36(8) . 15_665 ?
Se1 Se2 Se1 115.81(10) . 15_665 ?
Se1A Se2 Ni1 99.42(7) 15_665 . ?
Se1A Se2 Ni1 99.42(7) . . ?
Se1 Se2 Ni1 97.07(6) . . ?
Se1 Se2 Ni1 97.07(6) 15_665 . ?
C7 O2 Ni1 129.2(13) . 11_666 ?
O2 C7 O1 127.0(14) . . ?
O2 C7 C3 117.1(15) . . ?
O1 C7 C3 115.8(12) . . ?
C7A O2A Ni1 128.4(13) . 11_666 ?
O1A C7A O2A 127.6(15) . . ?
O1A C7A C3A 117.8(12) . . ?
O2A C7A C3A 114.4(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 -28(3) . . . . ?
Ni1 N1 C2 C3 176.8(11) . . . . ?
C6 N1 C2 Se1 169.3(13) . . . . ?
Ni1 N1 C2 Se1 14(3) . . . . ?
N1 C2 C3 C4 16.0(15) . . . . ?
Se1 C2 C3 C4 -179.78(19) . . . . ?
N1 C2 C3 C7 -164.2(15) . . . . ?
Se1 C2 C3 C7 0.1(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C7 C3 C4 C5 179.5(3) . . . . ?
C3 C4 C5 C6 1.0(6) . . . . ?
C4 C5 C6 N1 -14.6(18) . . . . ?
C2 N1 C6 C5 27(3) . . . . ?
Ni1 N1 C6 C5 -173.6(11) . . . . ?
C6A N1A C2A C3A 26(3) . . . . ?
Ni1 N1A C2A C3A -169.8(13) . . . . ?
C6A N1A C2A Se1A -165.3(18) . . . . ?
Ni1 N1A C2A Se1A -1(3) . . . . ?
N1A C2A C3A C4A -12.2(16) . . . . ?
Se1A C2A C3A C4A 179.7(2) . . . . ?
N1A C2A C3A C7A 168.1(16) . . . . ?
Se1A C2A C3A C7A -0.01(18) . . . . ?
C2A C3A C4A C5A 0.8(5) . . . . ?
C7A C3A C4A C5A -179.5(3) . . . . ?
C3A C4A C5A C6A -1.1(6) . . . . ?
C2A N1A C6A C5A -28(3) . . . . ?
Ni1 N1A C6A C5A 165.8(11) . . . . ?
C4A C5A C6A N1A 15(2) . . . . ?
Ni1 O2 C7 O1 -5.7(19) 11_666 . . . ?
Ni1 O2 C7 C3 171.0(6) 11_666 . . . ?
C2 C3 C7 O2 -170.1(9) . . . . ?
C4 C3 C7 O2 9.8(10) . . . . ?
C2 C3 C7 O1 7.0(9) . . . . ?
C4 C3 C7 O1 -173.1(9) . . . . ?
Ni1 O2A C7A O1A 6(2) 11_666 . . . ?
Ni1 O2A C7A C3A -168.1(7) 11_666 . . . ?
C4A C3A C7A O1A 163.3(9) . . . . ?
C2A C3A C7A O1A -17.0(9) . . . . ?
C4A C3A C7A O2A -21.9(10) . . . . ?
C2A C3A C7A O2A 157.9(9) . . . . ?

_refine_diff_density_max         2.523
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.150



####################################################################### 
# 
# 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_sh18025
_database_code_depnum_ccdc_archive 'CCDC 1909061'
loop_
_audit_author_name
_audit_author_address
'Vincent Lynch'
;University of Texas at Austin
United States of America
;
_audit_update_record             
;
2019-04-09 deposited with the CCDC.	2019-12-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_sh18025             
;
PROBLEM: Short Inter D...A Contact  Se1      ..O2       .       2.90 Ang.  
RESPONSE: Short Se...O contacts have been observed in several other structures 
with similar environments around Se.  Such contacts are more common in 
analogous S compounds.
;
_vrf_PLAT341_sh18025             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.017 Ang.  
RESPONSE: The low precision is probably due to the presence of Ni and Se 
in the material and the small size/poor scattering quality of the data 
crystal.
;


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2 C6 H4 N O4 Se, 4 H2 O, Ni'
_chemical_formula_sum            'C12 H16 N2 Ni O12 Se2'
_chemical_formula_weight         596.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.7387(8)
_cell_length_b                   7.6141(11)
_cell_length_c                   9.7024(11)
_cell_angle_alpha                104.872(12)
_cell_angle_beta                 91.645(10)
_cell_angle_gamma                109.701(12)
_cell_volume                     449.33(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    512
_cell_measurement_theta_min      6.78
_cell_measurement_theta_max      68.1

_exptl_crystal_description       shard
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.206
_exptl_crystal_F_000             294
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.079
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.031
_exptl_absorpt_coefficient_mu    6.864
_shelx_estimated_absorpt_T_min   0.613
_shelx_estimated_absorpt_T_max   0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.394
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_measurement_device_type  'Agilent SuperNova with an Atlas S2 CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2521
_diffrn_reflns_av_unetI/netI     0.1380
_diffrn_reflns_av_R_equivalents  0.1015
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.754
_diffrn_reflns_theta_max         68.368
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             1613
_reflns_number_gt                1069
_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       
'CrysAlisPro V 1.171.39.46, Agilent Technologies'
_computing_cell_refinement       
'CrysAlisPro V 1.171.39.46, Agilent Technologies'
_computing_data_reduction        
'CrysAlisPro V 1.171.39.46, Agilent Technologies'

_computing_structure_solution    
;

SHELXT. Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8. 
;
_computing_structure_refinement  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'Shelxl-2016/6, Sheldrick, G. M.'







_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)+(0.0659P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1613
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0754
_refine_ls_wR_factor_ref         0.2036
_refine_ls_wR_factor_gt          0.1722
_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_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 0.4980(17) 0.3243(15) 0.6858(12) 0.046(2) Uani 1 1 d . . . . .
C2 C 0.5487(17) 0.2978(15) 0.5469(12) 0.045(2) Uani 1 1 d . . . . .
C3 C 0.7233(18) 0.4407(16) 0.5210(14) 0.054(3) Uani 1 1 d . . . . .
H3 H 0.762208 0.433323 0.426932 0.065 Uiso 1 1 calc R U . . .
C4 C 0.8406(17) 0.5976(15) 0.6403(15) 0.055(3) Uani 1 1 d . . . . .
H4 H 0.961210 0.697931 0.626425 0.066 Uiso 1 1 calc R U . . .
C5 C 0.7832(17) 0.6076(14) 0.7768(13) 0.051(3) Uani 1 1 d . . . . .
H5 H 0.867568 0.711550 0.856254 0.061 Uiso 1 1 calc R U . . .
C6 C 0.4157(17) 0.1259(16) 0.4259(12) 0.049(3) Uani 1 1 d . . . . .
O1 O 0.2411(12) 0.0256(10) 0.4580(8) 0.0519(19) Uani 1 1 d . . . . .
H1O H 0.142478 -0.063271 0.408612 0.062 Uiso 1 1 d R U . . .
O2 O 0.4826(12) 0.0923(11) 0.3085(9) 0.0527(19) Uani 1 1 d . . . . .
O1W O 0.2231(13) -0.0726(10) 1.0505(9) 0.0505(18) Uani 1 1 d G . . . .
H1WA H 0.296640 -0.030220 1.132675 0.076 Uiso 1 1 d G U . . .
H1WB H 0.237312 0.028261 1.023532 0.076 Uiso 1 1 d G U . . .
O3 O 0.3072(12) 0.2185(10) 0.9109(9) 0.0493(18) Uani 1 1 d . . . . .
O4 O 0.0758(12) 0.2598(10) 0.7004(8) 0.0487(17) Uani 1 1 d . . . . .
O5 O 0.2713(15) 0.5924(12) 0.9290(10) 0.063(2) Uani 1 1 d G . . . .
H5A H 0.231806 0.578886 0.841779 0.095 Uiso 1 1 d G U . . .
H5B H 0.314006 0.714010 0.969647 0.095 Uiso 1 1 d G U . . .
Se1 Se 0.24472(18) 0.13579(16) 0.73392(13) 0.0471(4) Uani 1 1 d . . . . .
Ni1 Ni 0.500000 0.500000 1.000000 0.0470(7) Uani 1 2 d S . P . .
N1 N 0.6085(14) 0.4711(13) 0.7976(10) 0.049(2) Uani 1 1 d . . . . .


_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 1.323(14) . ?
C1 C2 1.381(16) . ?
C1 Se1 1.982(11) . ?
C2 C3 1.388(17) . ?
C2 C6 1.502(15) . ?
C3 C4 1.411(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(17) . ?
C4 H4 0.9500 . ?
C5 N1 1.343(15) . ?
C5 H5 0.9500 . ?
C6 O2 1.235(14) . ?
C6 O1 1.265(14) . ?
O1 H1O 0.8006 . ?
O1W H1WA 0.8501 . ?
O1W H1WB 0.8500 . ?
O3 Se1 1.657(8) . ?
O3 Ni1 2.034(7) . ?
O4 Se1 1.776(7) . ?
O5 Ni1 2.064(8) . ?
O5 H5A 0.8499 . ?
O5 H5B 0.8500 . ?
Ni1 N1 2.100(10) . ?
Ni1 N1 2.100(10) 2_667 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 125.1(10) . . ?
N1 C1 Se1 113.8(8) . . ?
C2 C1 Se1 121.2(8) . . ?
C1 C2 C3 117.6(10) . . ?
C1 C2 C6 121.8(10) . . ?
C3 C2 C6 120.6(11) . . ?
C2 C3 C4 117.2(12) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C5 C4 C3 121.1(10) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
N1 C5 C4 120.3(10) . . ?
N1 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
O2 C6 O1 126.1(10) . . ?
O2 C6 C2 119.6(10) . . ?
O1 C6 C2 114.3(10) . . ?
C6 O1 H1O 130.7 . . ?
H1WA O1W H1WB 104.9 . . ?
Se1 O3 Ni1 119.2(4) . . ?
Ni1 O5 H5A 125.7 . . ?
Ni1 O5 H5B 105.4 . . ?
H5A O5 H5B 105.3 . . ?
O3 Se1 O4 102.5(3) . . ?
O3 Se1 C1 96.6(4) . . ?
O4 Se1 C1 93.2(4) . . ?
O3 Ni1 O3 180.0 . 2_667 ?
O3 Ni1 O5 90.0(3) . 2_667 ?
O3 Ni1 O5 90.0(3) 2_667 2_667 ?
O3 Ni1 O5 90.0(3) . . ?
O3 Ni1 O5 90.0(3) 2_667 . ?
O5 Ni1 O5 180.0 2_667 . ?
O3 Ni1 N1 83.7(3) . . ?
O3 Ni1 N1 96.3(3) 2_667 . ?
O5 Ni1 N1 90.4(4) 2_667 . ?
O5 Ni1 N1 89.6(4) . . ?
O3 Ni1 N1 96.3(3) . 2_667 ?
O3 Ni1 N1 83.7(3) 2_667 2_667 ?
O5 Ni1 N1 89.6(4) 2_667 2_667 ?
O5 Ni1 N1 90.4(4) . 2_667 ?
N1 Ni1 N1 180.0(5) . 2_667 ?
C1 N1 C5 118.6(11) . . ?
C1 N1 Ni1 120.4(8) . . ?
C5 N1 Ni1 120.8(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -3.2(16) . . . . ?
Se1 C1 C2 C3 177.2(8) . . . . ?
N1 C1 C2 C6 179.5(9) . . . . ?
Se1 C1 C2 C6 -0.1(14) . . . . ?
C1 C2 C3 C4 2.7(15) . . . . ?
C6 C2 C3 C4 -179.9(9) . . . . ?
C2 C3 C4 C5 -0.1(16) . . . . ?
C3 C4 C5 N1 -2.6(16) . . . . ?
C1 C2 C6 O2 -169.4(10) . . . . ?
C3 C2 C6 O2 13.3(15) . . . . ?
C1 C2 C6 O1 9.5(14) . . . . ?
C3 C2 C6 O1 -167.7(10) . . . . ?
Ni1 O3 Se1 O4 -69.8(5) . . . . ?
Ni1 O3 Se1 C1 25.0(5) . . . . ?
C2 C1 N1 C5 0.5(16) . . . . ?
Se1 C1 N1 C5 -179.8(7) . . . . ?
C2 C1 N1 Ni1 176.2(8) . . . . ?
Se1 C1 N1 Ni1 -4.2(10) . . . . ?
C4 C5 N1 C1 2.4(15) . . . . ?
C4 C5 N1 Ni1 -173.3(8) . . . . ?

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
O1W H1WB O3 0.85 1.97 2.795(11) 161.8 .
O1W H1WA O2 0.85 1.90 2.748(11) 172.6 1_556
O5 H5B O1W 0.85 1.92 2.653(11) 144.2 1_565
O1 H1O O4 0.80 1.77 2.571(10) 179.9 2_556

_refine_diff_density_max         1.004
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.161

