# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
# 
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data_nfjv1adry
_database_code_depnum_ccdc_archive 'CCDC 1401687'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2016-06-06 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         'C22 H18 Co N8 Se2, Cl O4, C2 O S'
_chemical_formula_sum            'C24 H18 Cl Co N8 O5 S Se2'
_chemical_formula_weight         782.82

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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      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                   10.3102(6)
_cell_length_b                   10.7772(6)
_cell_length_c                   14.5496(8)
_cell_angle_alpha                80.932(5)
_cell_angle_beta                 89.859(5)
_cell_angle_gamma                65.526(5)
_cell_volume                     1449.47(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8556
_cell_measurement_theta_min      3.2282
_cell_measurement_theta_max      29.1703

_exptl_crystal_description       tablets
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.318
_shelx_estimated_absorpt_T_min   0.754
_shelx_estimated_absorpt_T_max   0.777
_exptl_absorpt_correction_T_min  0.93544
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.710689
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measurement_method       'ω and φ'
_diffrn_reflns_number            21127
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.235
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6302
_reflns_number_gt                5185
_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       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED '
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'WinGX (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+1.3811P] 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         6302
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
Co1 Co 0.89210(4) 0.15286(4) 0.68055(3) 0.02127(11) Uani 1 1 d . . . . .
Se1 Se 0.92360(4) 0.16025(3) 0.52170(2) 0.02668(10) Uani 1 1 d . . . . .
Se2 Se 1.13524(4) 0.01505(3) 0.71757(2) 0.02927(10) Uani 1 1 d . . . . .
N1 N 0.8527(3) 0.1473(3) 0.81801(19) 0.0282(6) Uani 1 1 d . . . . .
N2 N 0.9479(3) 0.3037(3) 0.67275(18) 0.0229(6) Uani 1 1 d . . . . .
N3 N 0.9736(3) 0.3695(3) 0.58864(18) 0.0261(6) Uani 1 1 d . . . . .
N4 N 0.9963(3) 0.3649(3) 0.43241(19) 0.0319(7) Uani 1 1 d . . . . .
H41 H 1.0178 0.4346 0.4265 0.038 Uiso 1 1 calc R U . . .
H42 H 0.9929 0.3282 0.3846 0.038 Uiso 1 1 calc R U . . .
C2 C 0.7871(4) 0.0697(4) 0.8549(3) 0.0384(9) Uani 1 1 d . . . . .
H2 H 0.7536 0.0253 0.8135 0.046 Uiso 1 1 calc R U . . .
C3 C 0.7632(4) 0.0482(4) 0.9492(3) 0.0457(10) Uani 1 1 d . . . . .
H3 H 0.7154 -0.0103 0.9719 0.055 Uiso 1 1 calc R U . . .
C4 C 0.8074(5) 0.1098(4) 1.0088(3) 0.0470(10) Uani 1 1 d . . . . .
H4 H 0.7919 0.0956 1.0747 0.056 Uiso 1 1 calc R U . . .
C5 C 0.8760(4) 0.1947(4) 0.9738(2) 0.0381(9) Uani 1 1 d . . . . .
C6 C 0.9302(5) 0.2560(4) 1.0338(3) 0.0520(11) Uani 1 1 d . . . . .
H6 H 0.9189 0.2405 1.1002 0.062 Uiso 1 1 calc R U . . .
C7 C 0.9973(5) 0.3355(5) 1.0000(3) 0.0556(12) Uani 1 1 d . . . . .
H7 H 1.0369 0.3745 1.0420 0.067 Uiso 1 1 calc R U . . .
C8 C 1.0095(5) 0.3617(4) 0.9040(3) 0.0452(10) Uani 1 1 d . . . . .
H8 H 1.0539 0.4228 0.8801 0.054 Uiso 1 1 calc R U . . .
C9 C 0.9605(4) 0.3035(4) 0.8421(2) 0.0316(8) Uani 1 1 d . . . . .
C10 C 0.8958(4) 0.2136(3) 0.8768(2) 0.0297(7) Uani 1 1 d . . . . .
C11 C 0.9784(4) 0.3464(3) 0.7445(2) 0.0288(7) Uani 1 1 d . . . . .
H11 H 1.0175 0.4147 0.7320 0.035 Uiso 1 1 calc R U . . .
C12 C 0.9683(3) 0.3135(3) 0.5157(2) 0.0225(6) Uani 1 1 d . . . . .
N1A N 0.6824(3) 0.2800(3) 0.65086(19) 0.0264(6) Uani 1 1 d . . . . .
N2A N 0.8720(3) -0.0161(3) 0.67556(18) 0.0244(6) Uani 1 1 d . . . . .
N3A N 0.9848(3) -0.1474(3) 0.6982(2) 0.0286(6) Uani 1 1 d . . . . .
N4A N 1.2233(3) -0.2686(3) 0.7419(2) 0.0394(7) Uani 1 1 d . . . . .
H4A1 H 1.2152 -0.3452 0.7435 0.047 Uiso 1 1 calc R U . . .
H4A2 H 1.3049 -0.2696 0.7554 0.047 Uiso 1 1 calc R U . . .
C2A C 0.6391(4) 0.4136(3) 0.6551(3) 0.0335(8) Uani 1 1 d . . . . .
H2A H 0.7089 0.4421 0.6781 0.040 Uiso 1 1 calc R U . . .
C3A C 0.5012(4) 0.5163(4) 0.6289(3) 0.0386(9) Uani 1 1 d . . . . .
H3A H 0.4771 0.6122 0.6328 0.046 Uiso 1 1 calc R U . . .
C4A C 0.4026(4) 0.4773(4) 0.5979(3) 0.0408(9) Uani 1 1 d . . . . .
H4A H 0.3065 0.5461 0.5777 0.049 Uiso 1 1 calc R U . . .
C5A C 0.4393(4) 0.3373(4) 0.5951(3) 0.0363(8) Uani 1 1 d . . . . .
C6A C 0.3360(4) 0.2929(5) 0.5690(3) 0.0496(11) Uani 1 1 d . . . . .
H6A H 0.2397 0.3609 0.5486 0.059 Uiso 1 1 calc R U . . .
C7A C 0.3692(4) 0.1559(5) 0.5722(3) 0.0498(11) Uani 1 1 d . . . . .
H7A H 0.2966 0.1264 0.5557 0.060 Uiso 1 1 calc R U . . .
C8A C 0.5085(4) 0.0586(4) 0.5993(3) 0.0418(9) Uani 1 1 d . . . . .
H8A H 0.5305 -0.0386 0.6020 0.050 Uiso 1 1 calc R U . . .
C9A C 0.6172(4) 0.0946(4) 0.6228(2) 0.0302(7) Uani 1 1 d . . . . .
C10A C 0.5821(3) 0.2383(3) 0.6223(2) 0.0282(7) Uani 1 1 d . . . . .
C11A C 0.7545(4) -0.0204(4) 0.6489(2) 0.0308(8) Uani 1 1 d . . . . .
H11A H 0.7592 -0.1115 0.6461 0.037 Uiso 1 1 calc R U . . .
C12A C 1.1084(4) -0.1476(3) 0.7185(2) 0.0281(7) Uani 1 1 d . . . . .
Cl1 Cl 1.61995(17) -0.27651(16) 0.80507(12) 0.0849(5) Uani 1 1 d . . . . .
O2 O 1.6474(9) -0.1731(9) 0.8325(5) 0.188(3) Uani 1 1 d . . . . .
O3 O 1.6583(11) -0.2909(8) 0.7138(4) 0.215(4) Uani 1 1 d . . . . .
O4 O 1.4851(7) -0.2486(9) 0.8098(8) 0.247(5) Uani 1 1 d . . . . .
O5 O 1.6930(10) -0.3939(8) 0.8585(5) 0.270(6) Uani 1 1 d . . . . .
S1 S 1.39317(15) -0.65490(14) 0.82687(10) 0.0558(6) Uani 0.879(5) 1 d . . P . .
S1A S 1.321(4) -0.629(3) 0.897(3) 0.24(2) Uani 0.121(5) 1 d . . P . .
O1 O 1.2463(4) -0.5498(3) 0.7886(3) 0.0648(9) Uani 1 1 d . . . . .
C13 C 1.3761(8) -0.8068(7) 0.8766(8) 0.170(5) Uani 1 1 d . . . . .
C14 C 1.4401(10) -0.5896(10) 0.9214(7) 0.145(4) 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
Co1 N2 1.924(3) . ?
Co1 N2A 1.928(3) . ?
Co1 N1A 2.025(3) . ?
Co1 N1 2.036(3) . ?
Co1 Se1 2.3267(5) . ?
Co1 Se2 2.3345(6) . ?
Se1 C12 1.879(3) . ?
Se2 C12A 1.882(3) . ?
N1 C2 1.331(4) . ?
N1 C10 1.378(4) . ?
N2 C11 1.294(4) . ?
N2 N3 1.397(3) . ?
N3 C12 1.313(4) . ?
N4 C12 1.334(4) . ?
N4 H41 0.8600 . ?
N4 H42 0.8600 . ?
C2 C3 1.393(5) . ?
C2 H2 0.9700 . ?
C3 C4 1.354(6) . ?
C3 H3 0.9700 . ?
C4 C5 1.409(6) . ?
C4 H4 0.9700 . ?
C5 C6 1.414(6) . ?
C5 C10 1.420(5) . ?
C6 C7 1.346(6) . ?
C6 H6 0.9700 . ?
C7 C8 1.396(6) . ?
C7 H7 0.9700 . ?
C8 C9 1.379(5) . ?
C8 H8 0.9700 . ?
C9 C10 1.420(5) . ?
C9 C11 1.458(5) . ?
C11 H11 0.9700 . ?
N1A C2A 1.331(4) . ?
N1A C10A 1.375(4) . ?
N2A C11A 1.295(4) . ?
N2A N3A 1.399(4) . ?
N3A C12A 1.309(4) . ?
N4A C12A 1.342(4) . ?
N4A H4A1 0.8600 . ?
N4A H4A2 0.8600 . ?
C2A C3A 1.399(5) . ?
C2A H2A 0.9700 . ?
C3A C4A 1.353(5) . ?
C3A H3A 0.9700 . ?
C4A C5A 1.403(5) . ?
C4A H4A 0.9700 . ?
C5A C6A 1.410(5) . ?
C5A C10A 1.425(5) . ?
C6A C7A 1.364(6) . ?
C6A H6A 0.9700 . ?
C7A C8A 1.394(6) . ?
C7A H7A 0.9700 . ?
C8A C9A 1.388(5) . ?
C8A H8A 0.9700 . ?
C9A C10A 1.436(5) . ?
C9A C11A 1.443(5) . ?
C11A H11A 0.9700 . ?
Cl1 O5 1.295(6) . ?
Cl1 O4 1.299(7) . ?
Cl1 O2 1.372(6) . ?
Cl1 O3 1.399(7) . ?
S1 S1A 1.26(3) . ?
S1 O1 1.507(3) . ?
S1 C13 1.760(6) . ?
S1 C14 1.793(8) . ?
S1A C14 1.51(4) . ?
S1A O1 1.69(5) . ?
S1A C13 1.84(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
N2 Co1 N2A 168.08(11) . . ?
N2 Co1 N1A 93.44(11) . . ?
N2A Co1 N1A 95.77(11) . . ?
N2 Co1 N1 94.82(11) . . ?
N2A Co1 N1 93.14(11) . . ?
N1A Co1 N1 87.48(11) . . ?
N2 Co1 Se1 87.19(8) . . ?
N2A Co1 Se1 85.30(8) . . ?
N1A Co1 Se1 89.69(8) . . ?
N1 Co1 Se1 176.61(8) . . ?
N2 Co1 Se2 84.04(8) . . ?
N2A Co1 Se2 86.89(8) . . ?
N1A Co1 Se2 177.20(8) . . ?
N1 Co1 Se2 91.52(8) . . ?
Se1 Co1 Se2 91.39(2) . . ?
C12 Se1 Co1 91.49(10) . . ?
C12A Se2 Co1 91.51(11) . . ?
C2 N1 C10 117.5(3) . . ?
C2 N1 Co1 118.3(2) . . ?
C10 N1 Co1 124.1(2) . . ?
C11 N2 N3 112.7(3) . . ?
C11 N2 Co1 124.0(2) . . ?
N3 N2 Co1 123.0(2) . . ?
C12 N3 N2 114.8(2) . . ?
C12 N4 H41 120.0 . . ?
C12 N4 H42 120.0 . . ?
H41 N4 H42 120.0 . . ?
N1 C2 C3 124.3(4) . . ?
N1 C2 H2 117.9 . . ?
C3 C2 H2 117.9 . . ?
C4 C3 C2 119.4(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 C10 118.8(4) . . ?
C6 C5 C10 119.8(4) . . ?
C7 C6 C5 121.0(4) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 119.6(4) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 122.2(4) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 C10 119.1(3) . . ?
C8 C9 C11 114.3(3) . . ?
C10 C9 C11 126.5(3) . . ?
N1 C10 C5 120.9(3) . . ?
N1 C10 C9 121.0(3) . . ?
C5 C10 C9 118.1(3) . . ?
N2 C11 C9 127.3(3) . . ?
N2 C11 H11 116.3 . . ?
C9 C11 H11 116.3 . . ?
N3 C12 N4 119.9(3) . . ?
N3 C12 Se1 123.2(2) . . ?
N4 C12 Se1 116.8(2) . . ?
C2A N1A C10A 117.4(3) . . ?
C2A N1A Co1 118.4(2) . . ?
C10A N1A Co1 124.1(2) . . ?
C11A N2A N3A 112.8(3) . . ?
C11A N2A Co1 124.0(2) . . ?
N3A N2A Co1 123.3(2) . . ?
C12A N3A N2A 114.9(3) . . ?
C12A N4A H4A1 120.0 . . ?
C12A N4A H4A2 120.0 . . ?
H4A1 N4A H4A2 120.0 . . ?
N1A C2A C3A 125.3(3) . . ?
N1A C2A H2A 117.3 . . ?
C3A C2A H2A 117.3 . . ?
C4A C3A C2A 117.8(4) . . ?
C4A C3A H3A 121.1 . . ?
C2A C3A H3A 121.1 . . ?
C3A C4A C5A 119.9(3) . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A C6A 121.0(4) . . ?
C4A C5A C10A 119.2(3) . . ?
C6A C5A C10A 119.8(4) . . ?
C7A C6A C5A 121.1(4) . . ?
C7A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
C6A C7A C8A 119.3(4) . . ?
C6A C7A H7A 120.3 . . ?
C8A C7A H7A 120.3 . . ?
C9A C8A C7A 123.0(4) . . ?
C9A C8A H8A 118.5 . . ?
C7A C8A H8A 118.5 . . ?
C8A C9A C10A 118.0(3) . . ?
C8A C9A C11A 115.0(3) . . ?
C10A C9A C11A 127.0(3) . . ?
N1A C10A C5A 120.2(3) . . ?
N1A C10A C9A 120.9(3) . . ?
C5A C10A C9A 118.8(3) . . ?
N2A C11A C9A 127.6(3) . . ?
N2A C11A H11A 116.2 . . ?
C9A C11A H11A 116.2 . . ?
N3A C12A N4A 119.4(3) . . ?
N3A C12A Se2 123.3(2) . . ?
N4A C12A Se2 117.2(3) . . ?
O5 Cl1 O4 108.4(7) . . ?
O5 Cl1 O2 110.7(6) . . ?
O4 Cl1 O2 109.9(5) . . ?
O5 Cl1 O3 107.7(5) . . ?
O4 Cl1 O3 109.6(6) . . ?
O2 Cl1 O3 110.4(4) . . ?
S1A S1 C13 72.7(10) . . ?
O1 S1 C13 107.0(3) . . ?
S1A S1 C14 56.1(18) . . ?
O1 S1 C14 105.8(3) . . ?
C13 S1 C14 106.5(5) . . ?
C14 S1A O1 110.7(16) . . ?
C14 S1A C13 116(2) . . ?
O1 S1A C13 96(2) . . ?


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
C11 N2 N3 C12 168.7(3) . . . . ?
Co1 N2 N3 C12 -5.4(4) . . . . ?
C10 N1 C2 C3 -2.0(5) . . . . ?
Co1 N1 C2 C3 174.9(3) . . . . ?
N1 C2 C3 C4 0.6(6) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C4 C5 C6 -176.9(4) . . . . ?
C3 C4 C5 C10 0.4(6) . . . . ?
C4 C5 C6 C7 179.1(4) . . . . ?
C10 C5 C6 C7 1.8(6) . . . . ?
C5 C6 C7 C8 2.1(7) . . . . ?
C6 C7 C8 C9 -3.0(7) . . . . ?
C7 C8 C9 C10 -0.2(6) . . . . ?
C7 C8 C9 C11 178.1(4) . . . . ?
C2 N1 C10 C5 2.6(5) . . . . ?
Co1 N1 C10 C5 -174.1(2) . . . . ?
C2 N1 C10 C9 -177.0(3) . . . . ?
Co1 N1 C10 C9 6.3(4) . . . . ?
C4 C5 C10 N1 -1.9(5) . . . . ?
C6 C5 C10 N1 175.5(3) . . . . ?
C4 C5 C10 C9 177.8(3) . . . . ?
C6 C5 C10 C9 -4.8(5) . . . . ?
C8 C9 C10 N1 -176.4(3) . . . . ?
C11 C9 C10 N1 5.6(5) . . . . ?
C8 C9 C10 C5 4.0(5) . . . . ?
C11 C9 C10 C5 -174.0(3) . . . . ?
N3 N2 C11 C9 177.9(3) . . . . ?
Co1 N2 C11 C9 -8.1(5) . . . . ?
C8 C9 C11 N2 176.7(4) . . . . ?
C10 C9 C11 N2 -5.2(6) . . . . ?
N2 N3 C12 N4 -177.5(3) . . . . ?
N2 N3 C12 Se1 2.0(4) . . . . ?
Co1 Se1 C12 N3 1.2(3) . . . . ?
Co1 Se1 C12 N4 -179.2(2) . . . . ?
C11A N2A N3A C12A 174.9(3) . . . . ?
Co1 N2A N3A C12A -3.5(4) . . . . ?
C10A N1A C2A C3A -2.9(5) . . . . ?
Co1 N1A C2A C3A 174.1(3) . . . . ?
N1A C2A C3A C4A 1.0(6) . . . . ?
C2A C3A C4A C5A 1.6(6) . . . . ?
C3A C4A C5A C6A 175.7(4) . . . . ?
C3A C4A C5A C10A -2.0(6) . . . . ?
C4A C5A C6A C7A -175.6(4) . . . . ?
C10A C5A C6A C7A 2.1(6) . . . . ?
C5A C6A C7A C8A -1.6(7) . . . . ?
C6A C7A C8A C9A -0.7(7) . . . . ?
C7A C8A C9A C10A 2.5(6) . . . . ?
C7A C8A C9A C11A -179.8(4) . . . . ?
C2A N1A C10A C5A 2.4(5) . . . . ?
Co1 N1A C10A C5A -174.5(2) . . . . ?
C2A N1A C10A C9A -175.1(3) . . . . ?
Co1 N1A C10A C9A 8.0(4) . . . . ?
C4A C5A C10A N1A 0.0(5) . . . . ?
C6A C5A C10A N1A -177.7(4) . . . . ?
C4A C5A C10A C9A 177.5(3) . . . . ?
C6A C5A C10A C9A -0.2(5) . . . . ?
C8A C9A C10A N1A 175.5(3) . . . . ?
C11A C9A C10A N1A -1.8(5) . . . . ?
C8A C9A C10A C5A -1.9(5) . . . . ?
C11A C9A C10A C5A -179.3(3) . . . . ?
N3A N2A C11A C9A 178.3(3) . . . . ?
Co1 N2A C11A C9A -3.3(5) . . . . ?
C8A C9A C11A N2A -178.4(4) . . . . ?
C10A C9A C11A N2A -0.9(6) . . . . ?
N2A N3A C12A N4A 179.5(3) . . . . ?
N2A N3A C12A Se2 -0.2(4) . . . . ?
Co1 Se2 C12A N3A 2.6(3) . . . . ?
Co1 Se2 C12A N4A -177.0(3) . . . . ?

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
N4 H41 N3 0.86 2.13 2.974(4) 168.6 2_766
N4 H42 N3A 0.86 2.38 3.188(4) 156.6 2_756
N4A H4A1 O1 0.86 2.09 2.907(4) 159.5 .
N4A H4A2 O4 0.86 2.13 2.978(7) 168.4 .

_refine_diff_density_max         0.651
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1471189'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 N4 Se'
_chemical_formula_weight         277.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.8291(8)
_cell_length_b                   12.9308(8)
_cell_length_c                   10.1657(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.384(8)
_cell_angle_gamma                90
_cell_volume                     1150.97(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1877
_cell_measurement_theta_min      3.7340
_cell_measurement_theta_max      27.6380

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3328
_exptl_crystal_size_mid          0.2537
_exptl_crystal_size_min          0.1098
_exptl_absorpt_coefficient_mu    3.239
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71888
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_reflns_number            4093
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.151
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2025
_reflns_number_gt                1668
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    
'Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122'
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.0323P)²+0.4204P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2025
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0745
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.30259(4) 0.38776(2) -0.06082(3) 0.05290(14) Uani 1 1 d . . . . .
N2 N 0.5335(3) 0.39427(16) 0.3097(2) 0.0392(5) Uani 1 1 d . . . . .
N3 N 0.4802(3) 0.41642(19) 0.1799(2) 0.0427(6) Uani 1 1 d . . . . .
N4 N 0.3298(3) 0.2732(2) 0.1726(3) 0.0461(6) Uani 1 1 d . . . . .
N1 N 0.8467(3) 0.59432(18) 0.5009(3) 0.0452(6) Uani 1 1 d . . . . .
C12 C 0.3773(3) 0.3546(2) 0.1121(3) 0.0387(6) Uani 1 1 d . . . . .
C6 C 0.8000(3) 0.5129(2) 0.5714(3) 0.0365(6) Uani 1 1 d . . . . .
C11 C 0.6272(3) 0.4587(2) 0.3691(3) 0.0388(6) Uani 1 1 d . . . . .
C10 C 0.6889(3) 0.4437(2) 0.5072(3) 0.0357(6) Uani 1 1 d . . . . .
C9 C 0.6395(4) 0.3630(2) 0.5790(3) 0.0461(7) Uani 1 1 d . . . . .
H9 H 0.5670 0.3174 0.5377 0.055 Uiso 1 1 calc R U . . .
C5 C 0.8602(3) 0.4950(2) 0.7048(3) 0.0436(7) Uani 1 1 d . . . . .
C8 C 0.6957(4) 0.3481(2) 0.7123(3) 0.0546(8) Uani 1 1 d . . . . .
H8 H 0.6589 0.2938 0.7592 0.066 Uiso 1 1 calc R U . . .
C7 C 0.8038(4) 0.4123(2) 0.7737(3) 0.0549(8) Uani 1 1 d . . . . .
H7 H 0.8411 0.4015 0.8624 0.066 Uiso 1 1 calc R U . . .
C2 C 0.9532(4) 0.6543(2) 0.5616(4) 0.0558(8) Uani 1 1 d . . . . .
H2 H 0.9858 0.7097 0.5141 0.067 Uiso 1 1 calc R U . . .
C3 C 1.0211(4) 0.6414(3) 0.6923(4) 0.0614(9) Uani 1 1 d . . . . .
H3A H 1.0972 0.6862 0.7295 0.074 Uiso 1 1 calc R U . . .
C4 C 0.9735(4) 0.5620(3) 0.7635(3) 0.0574(9) Uani 1 1 d . . . . .
H4 H 1.0160 0.5520 0.8512 0.069 Uiso 1 1 calc R U . . .
H11 H 0.661(3) 0.514(2) 0.330(3) 0.036(7) Uiso 1 1 d . . . . .
H3 H 0.517(3) 0.469(2) 0.140(3) 0.052(9) Uiso 1 1 d . . . . .
H4A H 0.365(3) 0.261(2) 0.259(3) 0.053(9) Uiso 1 1 d . . . . .
H4B H 0.272(4) 0.235(2) 0.130(3) 0.052(10) Uiso 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 C12 1.847(3) . ?
N2 C11 1.271(3) . ?
N2 N3 1.372(3) . ?
N3 C12 1.334(4) . ?
N3 H3 0.87(3) . ?
N4 C12 1.315(4) . ?
N4 H4A 0.91(3) . ?
N4 H4B 0.79(3) . ?
N1 C2 1.311(4) . ?
N1 C6 1.367(3) . ?
C6 C5 1.411(4) . ?
C6 C10 1.422(4) . ?
C11 C10 1.453(4) . ?
C11 H11 0.89(3) . ?
C10 C9 1.377(4) . ?
C9 C8 1.396(4) . ?
C9 H9 0.9300 . ?
C5 C4 1.398(4) . ?
C5 C7 1.404(4) . ?
C8 C7 1.355(4) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
C2 C3 1.395(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(5) . ?
C3 H3A 0.9300 . ?
C4 H4 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
C11 N2 N3 116.2(2) . . ?
C12 N3 N2 119.9(2) . . ?
C12 N3 H3 120(2) . . ?
N2 N3 H3 120(2) . . ?
C12 N4 H4A 120.3(19) . . ?
C12 N4 H4B 118(2) . . ?
H4A N4 H4B 122(3) . . ?
C2 N1 C6 117.1(3) . . ?
N4 C12 N3 118.4(3) . . ?
N4 C12 Se1 122.3(2) . . ?
N3 C12 Se1 119.3(2) . . ?
N1 C6 C5 121.9(3) . . ?
N1 C6 C10 118.7(2) . . ?
C5 C6 C10 119.3(2) . . ?
N2 C11 C10 120.8(3) . . ?
N2 C11 H11 123.6(17) . . ?
C10 C11 H11 115.6(17) . . ?
C9 C10 C6 118.7(2) . . ?
C9 C10 C11 120.6(3) . . ?
C6 C10 C11 120.7(2) . . ?
C10 C9 C8 121.5(3) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C4 C5 C7 122.6(3) . . ?
C4 C5 C6 118.0(3) . . ?
C7 C5 C6 119.4(3) . . ?
C7 C8 C9 120.2(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C7 C5 120.7(3) . . ?
C8 C7 H7 119.6 . . ?
C5 C7 H7 119.6 . . ?
N1 C2 C3 124.9(3) . . ?
N1 C2 H2 117.5 . . ?
C3 C2 H2 117.5 . . ?
C4 C3 C2 118.3(3) . . ?
C4 C3 H3A 120.8 . . ?
C2 C3 H3A 120.8 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?

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
C11 N2 N3 C12 -177.6(2) . . . . ?
N2 N3 C12 N4 -0.1(4) . . . . ?
N2 N3 C12 Se1 178.20(19) . . . . ?
C2 N1 C6 C5 1.6(4) . . . . ?
C2 N1 C6 C10 -177.6(2) . . . . ?
N3 N2 C11 C10 179.0(2) . . . . ?
N1 C6 C10 C9 -178.6(3) . . . . ?
C5 C6 C10 C9 2.1(4) . . . . ?
N1 C6 C10 C11 0.6(4) . . . . ?
C5 C6 C10 C11 -178.7(2) . . . . ?
N2 C11 C10 C9 -4.3(4) . . . . ?
N2 C11 C10 C6 176.5(2) . . . . ?
C6 C10 C9 C8 0.1(4) . . . . ?
C11 C10 C9 C8 -179.1(3) . . . . ?
N1 C6 C5 C4 -1.7(4) . . . . ?
C10 C6 C5 C4 177.6(2) . . . . ?
N1 C6 C5 C7 177.6(3) . . . . ?
C10 C6 C5 C7 -3.1(4) . . . . ?
C10 C9 C8 C7 -1.4(5) . . . . ?
C9 C8 C7 C5 0.4(5) . . . . ?
C4 C5 C7 C8 -178.9(3) . . . . ?
C6 C5 C7 C8 1.9(5) . . . . ?
C6 N1 C2 C3 -0.4(5) . . . . ?
N1 C2 C3 C4 -0.8(5) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C7 C5 C4 C3 -178.9(3) . . . . ?
C6 C5 C4 C3 0.4(4) . . . . ?

_refine_diff_density_max         0.505
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.054

_shelxl_version_number           2014/6

