# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_Hqasesc
_database_code_depnum_ccdc_archive 'CCDC 1413656'
_audit_update_record             
;
2015-07-19 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;

_audit_creation_date             2015-06-02T10:09:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
; 2-quinolinealdehyde selenosemicarbazone
;
_chemical_name_common            
; 2-quinolinealdehyde selenosemicarbazone
;
_chemical_formula_moiety         'C11 H10 N4 Se'
_chemical_formula_sum            'C11 H10 N4 Se'
_chemical_formula_weight         277.19
_chemical_melting_point          ?
_chemical_compound_source        synthetic

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
_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_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.19022(13)
_cell_length_b                   11.07458(14)
_cell_length_c                   12.09766(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.6837(13)
_cell_angle_gamma                90
_cell_volume                     1096.09(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7816
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      29.093
_cell_oxdiff_length_a            8.1901(3)
_cell_oxdiff_length_b            11.0752(4)
_cell_oxdiff_length_c            12.0970(5)
_cell_oxdiff_angle_alpha         90.006(3)
_cell_oxdiff_angle_beta          92.674(3)
_cell_oxdiff_angle_gamma         89.981(3)
_cell_oxdiff_volume              1096.09(7)
_cell_oxdiff_measurement_reflns_used 7816

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.4739
_exptl_crystal_size_mid          0.3685
_exptl_crystal_size_min          0.2056
_exptl_crystal_density_diffrn    1.68
_exptl_crystal_F_000             552
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.1078
-1 0 -1 0.0978
-1 -1 1 0.1631
1 1 -1 0.1631
-1 1 1 0.1926
1 -1 -1 0.1926
3 -5 4 0.178
0 -5 1 0.1806
0 5 -1 0.1806
-2 -5 -1 0.1608
1 5 1 0.1839
1 5 5 0.1884
1 -4 5 0.1732
3 -5 -5 0.1866
4 1 -5 0.1799
-1 5 -3 0.1651
-1 0 5 0.2507
0 -5 -4 0.1797

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.402
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
; Analytical numeric absorption correction using a multifaceted crystal
 model based on expressions derived by R.C. Clark & J.S. Reid(Clark, R. C. & 
 Reid, J. S. (1995). Acta Cryst. A51, 887-897) followed by empirical absorption
 correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling
 algorithm. Computed by CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)
;
_exptl_absorpt_correction_T_min  0.341
_exptl_absorpt_correction_T_max  0.54

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) (Oxford Diffraction)'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Sapphire3 (Oxford Diffraction)'
_diffrn_detector_area_resol_mean 16.328
_diffrn_orient_matrix_ub_11      0.014822
_diffrn_orient_matrix_ub_12      -0.0629856
_diffrn_orient_matrix_ub_13      -0.0030854
_diffrn_orient_matrix_ub_21      -0.0798416
_diffrn_orient_matrix_ub_22      -0.0087967
_diffrn_orient_matrix_ub_23      -0.0239048
_diffrn_orient_matrix_ub_31      0.0303696
_diffrn_orient_matrix_ub_32      0.0075534
_diffrn_orient_matrix_ub_33      -0.0535212
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_number            19948
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.072
_diffrn_reflns_theta_max         28.964
_diffrn_reflns_theta_full        26.32
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.931
_reflns_Friedel_coverage         0
_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.
;
_reflns_number_total             2714
_reflns_number_gt                2368
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_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    'SHELXT 2014/4 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2015b)'
_shelxl_version_number           2014/6
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²+0.2771P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2714
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_restrained_S_all      1.206
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.1

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.34037(3) 1.07071(2) 0.34873(2) 0.04242(13) Uani 1 1 d . . . . .
N1 N 0.7528(2) 0.49670(16) 0.49143(14) 0.0313(4) Uani 1 1 d . . . . .
N2 N 0.5191(2) 0.73140(17) 0.36660(15) 0.0334(4) Uani 1 1 d . . . . .
N3 N 0.4794(3) 0.84774(18) 0.39086(16) 0.0367(4) Uani 1 1 d . . . . .
H3 H 0.513(3) 0.870(3) 0.456(2) 0.045(8) Uiso 1 1 d . . . . .
N4 N 0.3721(3) 0.8686(2) 0.21470(18) 0.0429(5) Uani 1 1 d . . . . .
H4A H 0.324(4) 0.900(3) 0.166(3) 0.056(10) Uiso 1 1 d . . . . .
H4B H 0.398(3) 0.799(3) 0.197(2) 0.042(8) Uiso 1 1 d . . . . .
C1 C 0.4015(3) 0.91612(19) 0.31281(19) 0.0314(4) Uani 1 1 d . . . . .
C2 C 0.6023(3) 0.6727(2) 0.44072(18) 0.0330(5) Uani 1 1 d . . . . .
H2 H 0.6367 0.7101 0.5066 0.04 Uiso 1 1 calc R U . . .
C3 C 0.6432(3) 0.5458(2) 0.42090(17) 0.0298(4) Uani 1 1 d . . . . .
C4 C 0.5634(3) 0.4823(2) 0.33157(18) 0.0356(5) Uani 1 1 d . . . . .
H4 H 0.486 0.5204 0.2849 0.043 Uiso 1 1 calc R U . . .
C5 C 0.6033(3) 0.3642(2) 0.31600(19) 0.0377(5) Uani 1 1 d . . . . .
H5 H 0.5501 0.3197 0.2599 0.045 Uiso 1 1 calc R U . . .
C6 C 0.7256(3) 0.3096(2) 0.38519(18) 0.0320(4) Uani 1 1 d . . . . .
C7 C 0.7975(3) 0.3791(2) 0.47288(17) 0.0304(4) Uani 1 1 d . . . . .
C8 C 0.9204(3) 0.3259(2) 0.5426(2) 0.0403(5) Uani 1 1 d . . . . .
H8 H 0.9669 0.3695 0.6018 0.048 Uiso 1 1 calc R U . . .
C9 C 0.9711(3) 0.2113(2) 0.5235(2) 0.0471(6) Uani 1 1 d . . . . .
H9 H 1.0549 0.1783 0.5684 0.057 Uiso 1 1 calc R U . . .
C10 C 0.8997(3) 0.1423(2) 0.4378(2) 0.0459(6) Uani 1 1 d . . . . .
H10 H 0.9354 0.0637 0.4266 0.055 Uiso 1 1 calc R U . . .
C11 C 0.7780(3) 0.1895(2) 0.3703(2) 0.0399(5) Uani 1 1 d . . . . .
H11 H 0.7293 0.1424 0.3142 0.048 Uiso 1 1 calc R U . . .


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C1 1.841(2) . ?
N1 C3 1.326(3) . ?
N1 C7 1.374(3) . ?
N2 C2 1.278(3) . ?
N2 N3 1.364(3) . ?
N3 C1 1.348(3) . ?
N3 H3 0.86(3) . ?
N4 C1 1.310(3) . ?
N4 H4A 0.77(4) . ?
N4 H4B 0.83(3) . ?
C2 C3 1.468(3) . ?
C2 H2 0.93 . ?
C3 C4 1.422(3) . ?
C4 C5 1.364(4) . ?
C4 H4 0.93 . ?
C5 C6 1.411(3) . ?
C5 H5 0.93 . ?
C6 C11 1.412(3) . ?
C6 C7 1.416(3) . ?
C7 C8 1.412(3) . ?
C8 C9 1.358(4) . ?
C8 H8 0.93 . ?
C9 C10 1.394(4) . ?
C9 H9 0.93 . ?
C10 C11 1.363(4) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?

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
C3 N1 C7 117.45(18) . . ?
C2 N2 N3 116.98(19) . . ?
C1 N3 N2 119.32(19) . . ?
C1 N3 H3 127(2) . . ?
N2 N3 H3 113(2) . . ?
C1 N4 H4A 125(3) . . ?
C1 N4 H4B 124(2) . . ?
H4A N4 H4B 111(3) . . ?
N4 C1 N3 118.0(2) . . ?
N4 C1 Se1 123.13(18) . . ?
N3 C1 Se1 118.83(17) . . ?
N2 C2 C3 119.4(2) . . ?
N2 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
N1 C3 C4 124.0(2) . . ?
N1 C3 C2 116.1(2) . . ?
C4 C3 C2 119.8(2) . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C11 122.6(2) . . ?
C5 C6 C7 118.1(2) . . ?
C11 C6 C7 119.3(2) . . ?
N1 C7 C8 119.1(2) . . ?
N1 C7 C6 122.20(19) . . ?
C8 C7 C6 118.7(2) . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C6 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?

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
C2 N2 N3 C1 175.5(2) . . . . ?
N2 N3 C1 N4 -2.4(3) . . . . ?
N2 N3 C1 Se1 177.24(16) . . . . ?
N3 N2 C2 C3 177.7(2) . . . . ?
C7 N1 C3 C4 3.5(3) . . . . ?
C7 N1 C3 C2 -177.92(18) . . . . ?
N2 C2 C3 N1 168.5(2) . . . . ?
N2 C2 C3 C4 -12.9(3) . . . . ?
N1 C3 C4 C5 -1.0(3) . . . . ?
C2 C3 C4 C5 -179.5(2) . . . . ?
C3 C4 C5 C6 -2.4(3) . . . . ?
C4 C5 C6 C11 -177.0(2) . . . . ?
C4 C5 C6 C7 3.1(3) . . . . ?
C3 N1 C7 C8 176.5(2) . . . . ?
C3 N1 C7 C6 -2.7(3) . . . . ?
C5 C6 C7 N1 -0.5(3) . . . . ?
C11 C6 C7 N1 179.6(2) . . . . ?
C5 C6 C7 C8 -179.8(2) . . . . ?
C11 C6 C7 C8 0.3(3) . . . . ?
N1 C7 C8 C9 -177.5(2) . . . . ?
C6 C7 C8 C9 1.7(4) . . . . ?
C7 C8 C9 C10 -2.3(4) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C9 C10 C11 C6 1.3(4) . . . . ?
C5 C6 C11 C10 178.3(2) . . . . ?
C7 C6 C11 C10 -1.8(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
N3 H3 Se1 0.86(3) 2.68(3) 3.533(2) 172(3) 3_676
N4 H4A N1 0.77(4) 2.45(4) 3.198(3) 163(3) 4_575
N4 H4B N2 0.83(3) 2.36(3) 2.632(3) 100(2) .

#----------------------------------------------------------------------------#
#                   REFLECTION DATA AND REFINEMENT INSTRUCTIONS              #
#----------------------------------------------------------------------------#


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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 1413657'
_audit_update_record             
;
2015-07-19 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;

_audit_creation_date             2014-09-19T21:16:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'bis(2-quinolinealdehyde selenosemicarbazone)zinc(II) perchlorate  ethanol solvate'
_chemical_name_common            
'bis(2-quinolinealdehyde selenosemicarbazone)zinc(II) perchlorate  ethanol solvate'
_chemical_formula_sum            'C24 H26 Cl2 N8 O9 Se2 Zn'
_chemical_formula_moiety         '(C22 H20 N8 Se2 Zn 2+), 2(Cl O4 1-), C2 H6 O'
_chemical_formula_weight         864.72

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.14856(17)
_cell_length_b                   13.88140(18)
_cell_length_c                   20.8541(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.5190(15)
_cell_angle_gamma                90
_cell_volume                     3191.73(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    13809
_cell_measurement_theta_min      3.275
_cell_measurement_theta_max      31.992

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.7045
_exptl_crystal_size_mid          0.5355
_exptl_crystal_size_min          0.2998
_exptl_crystal_density_diffrn    1.8
_exptl_crystal_F_000             1720
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.1449
-1 0 0 0.1549
0 1 2 0.2787
0 -1 -2 0.2367
0 -1 2 0.2576
0 1 -2 0.2576
-1 0 2 0.233
1 0 -2 0.233
-1 1 2 0.2491
1 1 -2 0.2406
5 0 1 0.1305
-1 -1 2 0.2857
3 2 5 0.2501


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.281
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model followed by empirical absorption correction 
using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm
in CrysAlisPro (Agilent Technologies, 2013).
;
_exptl_absorpt_correction_T_min  0.197
_exptl_absorpt_correction_T_max  0.432

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance Mo (Agilent Technologies)'
_diffrn_source_current           50
_diffrn_source_voltage           40
_diffrn_source_power             2
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 16.328
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_radiation_collimation    '0.8 mm'
_diffrn_orient_matrix_ub_11      0.0518438
_diffrn_orient_matrix_ub_12      0.0094822
_diffrn_orient_matrix_ub_13      0.0232233
_diffrn_orient_matrix_ub_21      -0.0364309
_diffrn_orient_matrix_ub_22      0.0264054
_diffrn_orient_matrix_ub_23      0.018943
_diffrn_orient_matrix_ub_31      -0.0110266
_diffrn_orient_matrix_ub_32      -0.0427221
_diffrn_orient_matrix_ub_33      0.0168707
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Agilent Technologies)'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_number            55626
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.097
_diffrn_reflns_theta_max         32.505
_diffrn_reflns_theta_full        26.32
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.942
_reflns_number_total             10890
_reflns_number_gt                8743
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+1.6812P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10890
_refine_ls_number_parameters     435
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.845
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.088

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
Zn Zn 0.2839 1.4301 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1A Se -0.02129(2) 0.54850(2) 0.28642(2) 0.04050(7) Uani 1 d . .
Se1 Se 0.11330(2) 0.78983(2) 0.23542(2) 0.04399(7) Uani 1 d . .
Zn1 Zn 0.01628(2) 0.71860(2) 0.33235(2) 0.03199(6) Uani 1 d . .
N1 N 0.03650(17) 0.66699(12) 0.43420(8) 0.0330(3) Uani 1 d . .
N2 N 0.20874(16) 0.68180(13) 0.35970(9) 0.0352(4) Uani 1 d . .
N1A N -0.04361(17) 0.86506(12) 0.35592(9) 0.0341(3) Uani 1 d . .
N3 N 0.29057(18) 0.68719(17) 0.31786(11) 0.0444(4) Uani 1 d . .
H3 H 0.363(2) 0.666(3) 0.3312(17) 0.068(10) Uiso 1 d . .
N2A N -0.16924(17) 0.73316(14) 0.28272(9) 0.0368(4) Uani 1 d . .
N4 N 0.3525(3) 0.7473(3) 0.22797(15) 0.0746(9) Uani 1 d . .
H4A H 0.4224 0.7224 0.2411 0.089 Uiso 1 calc . .
H4B H 0.3405 0.7789 0.1921 0.089 Uiso 1 calc . .
N3A N -0.22822(19) 0.66044(16) 0.24721(12) 0.0477(5) Uani 1 d . .
H3A H -0.298(2) 0.674(3) 0.2270(16) 0.070(10) Uiso 1 d . .
N4A N -0.2388(2) 0.50743(19) 0.21061(13) 0.0619(7) Uani 1 d . .
H4C H -0.3102 0.5204 0.1908 0.074 Uiso 1 calc . .
H4D H -0.2088 0.4508 0.2078 0.074 Uiso 1 calc . .
C1 C 0.2640(2) 0.73731(19) 0.26272(12) 0.0429(5) Uani 1 d . .
C2 C 0.2408(2) 0.64639(17) 0.41602(12) 0.0407(5) Uani 1 d . .
H2 H 0.3199 0.6256 0.4294 0.049 Uiso 1 calc . .
C1A C -0.1757(2) 0.57389(17) 0.24504(12) 0.0408(5) Uani 1 d . .
C3 C 0.1492(2) 0.63971(16) 0.45849(10) 0.0363(4) Uani 1 d . .
C2A C -0.2198(2) 0.81501(18) 0.28452(12) 0.0426(5) Uani 1 d . .
H2A H -0.2962 0.8271 0.2614 0.051 Uiso 1 calc . .
C4 C 0.1816(2) 0.60428(19) 0.52220(12) 0.0458(5) Uani 1 d . .
H4 H 0.2611 0.586 0.5371 0.055 Uiso 1 calc . .
C3A C -0.1525(2) 0.88930(16) 0.32450(11) 0.0377(4) Uani 1 d . .
C5 C 0.0949(3) 0.59742(19) 0.56121(11) 0.0474(6) Uani 1 d . .
H5 H 0.1151 0.5763 0.6038 0.057 Uiso 1 calc . .
C4A C -0.2041(2) 0.98136(18) 0.32770(14) 0.0479(6) Uani 1 d . .
H4E H -0.2805 0.995 0.305 0.058 Uiso 1 calc . .
C6 C -0.0250(2) 0.62221(17) 0.53724(11) 0.0414(5) Uani 1 d . .
C5A C -0.1405(3) 1.04941(18) 0.36447(15) 0.0531(6) Uani 1 d . .
H5A H -0.1736 1.1104 0.3676 0.064 Uiso 1 calc . .
C7 C -0.0526(2) 0.65634(15) 0.47197(10) 0.0350(4) Uani 1 d . .
C6A C -0.0246(3) 1.02882(17) 0.39807(13) 0.0461(5) Uani 1 d . .
C8 C -0.1739(2) 0.67747(19) 0.44634(12) 0.0451(5) Uani 1 d . .
H8 H -0.1923 0.7009 0.4043 0.054 Uiso 1 calc . .
C7A C 0.0219(2) 0.93420(16) 0.39268(11) 0.0377(4) Uani 1 d . .
C9 C -0.2647(3) 0.6637(2) 0.48283(15) 0.0547(6) Uani 1 d . .
H9 H -0.3447 0.6762 0.465 0.066 Uiso 1 calc . .
C8A C 0.1380(2) 0.91199(19) 0.42552(13) 0.0460(5) Uani 1 d . .
H8A H 0.1695 0.8504 0.4225 0.055 Uiso 1 calc . .
C10 C -0.2379(3) 0.6308(2) 0.54741(16) 0.0611(8) Uani 1 d . .
H10 H -0.3003 0.622 0.5719 0.073 Uiso 1 calc . .
C9A C 0.2049(3) 0.9808(2) 0.46204(15) 0.0579(7) Uani 1 d . .
H9A H 0.282 0.9659 0.4832 0.069 Uiso 1 calc . .
C11 C -0.1221(3) 0.6120(2) 0.57391(13) 0.0549(7) Uani 1 d . .
H11 H -0.1057 0.592 0.6169 0.066 Uiso 1 calc . .
C10A C 0.1577(3) 1.0735(2) 0.46757(17) 0.0655(8) Uani 1 d . .
H10A H 0.2034 1.1192 0.493 0.079 Uiso 1 calc . .
C11A C 0.0470(3) 1.0972(2) 0.43653(17) 0.0629(8) Uani 1 d . .
H11A H 0.0175 1.1592 0.4405 0.076 Uiso 1 calc . .
Cl1 Cl 0.51343(7) 0.48866(6) 0.33952(4) 0.06319(19) Uani 1 d . .
O1 O 0.4211(4) 0.4215(3) 0.32157(19) 0.1310(15) Uani 1 d . .
O2 O 0.4943(4) 0.5283(4) 0.3991(2) 0.1464(19) Uani 1 d . .
O3 O 0.5054(4) 0.5614(3) 0.2909(2) 0.1296(15) Uani 1 d . .
O4 O 0.6284(3) 0.4453(3) 0.34498(15) 0.1001(10) Uani 1 d . .
Cl2 Cl 0.51343(7) 0.86349(7) 0.38262(4) 0.0669(2) Uani 1 d . .
O5 O 0.4053(4) 0.8406(5) 0.4013(3) 0.201(3) Uani 1 d . .
O6 O 0.5999(4) 0.8943(4) 0.4309(2) 0.1471(18) Uani 1 d . .
O7 O 0.4927(5) 0.9353(4) 0.3340(3) 0.172(2) Uani 1 d . .
O8 O 0.5563(4) 0.7829(3) 0.3509(2) 0.1188(13) Uani 1 d . .
O9A O 0.4516(4) 0.1456(4) 0.33374(18) 0.0776(15) Uani 0.690(9) d A 1
H9A1 H 0.4832 0.0926 0.3314 0.116 Uiso 0.690(9) calc A 1
O9B O 0.4317(7) 0.2201(7) 0.3383(3) 0.067(3) Uani 0.310(9) d A 2
H9B H 0.4124 0.2761 0.344 0.1 Uiso 0.310(9) calc A 2
C12 C 0.4539(5) 0.1710(5) 0.3999(2) 0.1175(19) Uani 1 d . .
H12A H 0.433 0.1145 0.4233 0.141 Uiso 0.690(9) calc A 1
H12B H 0.3916 0.2191 0.4026 0.141 Uiso 0.690(9) calc A 1
H12C H 0.4588 0.102 0.3936 0.141 Uiso 0.310(9) calc A 2
H12D H 0.3894 0.1843 0.4252 0.141 Uiso 0.310(9) calc A 2
C13 C 0.5697(6) 0.2088(6) 0.4325(3) 0.162(3) Uani 1 d . .
H13A H 0.5859 0.2698 0.4139 0.194 Uiso 1 calc . .
H13B H 0.6335 0.1644 0.4271 0.194 Uiso 1 calc . .
H13C H 0.5658 0.2169 0.4778 0.194 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Se1A C1A 1.842(2) . ?
Se1A Zn1 2.5592(3) . ?
Se1 C1 1.842(3) . ?
Se1 Zn1 2.6233(3) . ?
Zn1 N2A 2.1808(18) . ?
Zn1 N2 2.1971(18) . ?
Zn1 N1A 2.2177(17) . ?
Zn1 N1 2.2211(17) . ?
N1 C3 1.338(3) . ?
N1 C7 1.364(3) . ?
N2 C2 1.275(3) . ?
N2 N3 1.355(3) . ?
N1A C3A 1.334(3) . ?
N1A C7A 1.370(3) . ?
N3 C1 1.339(3) . ?
N3 H3 0.866(18) . ?
N2A C2A 1.271(3) . ?
N2A N3A 1.362(3) . ?
N4 C1 1.316(3) . ?
N4 H4A 0.86 . ?
N4 H4B 0.86 . ?
N3A C1A 1.340(3) . ?
N3A H3A 0.846(18) . ?
N4A C1A 1.308(3) . ?
N4A H4C 0.86 . ?
N4A H4D 0.86 . ?
C2 C3 1.451(3) . ?
C2 H2 0.93 . ?
C3 C4 1.413(3) . ?
C2A C3A 1.462(4) . ?
C2A H2A 0.93 . ?
C4 C5 1.356(4) . ?
C4 H4 0.93 . ?
C3A C4A 1.407(3) . ?
C5 C6 1.399(4) . ?
C5 H5 0.93 . ?
C4A C5A 1.350(4) . ?
C4A H4E 0.93 . ?
C6 C11 1.422(4) . ?
C6 C7 1.431(3) . ?
C5A C6A 1.405(4) . ?
C5A H5A 0.93 . ?
C7 C8 1.409(3) . ?
C6A C11A 1.411(4) . ?
C6A C7A 1.423(3) . ?
C8 C9 1.367(4) . ?
C8 H8 0.93 . ?
C7A C8A 1.406(3) . ?
C9 C10 1.412(4) . ?
C9 H9 0.93 . ?
C8A C9A 1.371(4) . ?
C8A H8A 0.93 . ?
C10 C11 1.352(5) . ?
C10 H10 0.93 . ?
C9A C10A 1.401(5) . ?
C9A H9A 0.93 . ?
C11 H11 0.93 . ?
C10A C11A 1.346(5) . ?
C10A H10A 0.93 . ?
C11A H11A 0.93 . ?
Cl1 O1 1.399(3) . ?
Cl1 O2 1.404(3) . ?
Cl1 O4 1.405(3) . ?
Cl1 O3 1.425(4) . ?
Cl2 O6 1.356(3) . ?
Cl2 O5 1.358(4) . ?
Cl2 O7 1.417(5) . ?
Cl2 O8 1.418(4) . ?
O9A C12 1.420(4) . ?
O9A H9A1 0.82 . ?
O9B C12 1.442(5) . ?
O9B H9B 0.82 . ?
C12 C13 1.465(5) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C12 H12C 0.97 . ?
C12 H12D 0.97 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?

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
C1A Se1A Zn1 95.08(8) . . ?
C1 Se1 Zn1 94.23(8) . . ?
N2A Zn1 N2 164.97(7) . . ?
N2A Zn1 N1A 74.02(7) . . ?
N2 Zn1 N1A 118.04(7) . . ?
N2A Zn1 N1 116.01(7) . . ?
N2 Zn1 N1 73.74(7) . . ?
N1A Zn1 N1 94.30(7) . . ?
N2A Zn1 Se1A 79.44(5) . . ?
N2 Zn1 Se1A 88.97(5) . . ?
N1A Zn1 Se1A 152.98(5) . . ?
N1 Zn1 Se1A 92.76(5) . . ?
N2A Zn1 Se1 94.00(5) . . ?
N2 Zn1 Se1 77.84(5) . . ?
N1A Zn1 Se1 89.84(5) . . ?
N1 Zn1 Se1 149.70(5) . . ?
Se1A Zn1 Se1 97.048(12) . . ?
C3 N1 C7 118.30(18) . . ?
C3 N1 Zn1 114.20(15) . . ?
C7 N1 Zn1 127.42(14) . . ?
C2 N2 N3 119.42(19) . . ?
C2 N2 Zn1 117.29(16) . . ?
N3 N2 Zn1 123.02(14) . . ?
C3A N1A C7A 117.97(19) . . ?
C3A N1A Zn1 113.85(15) . . ?
C7A N1A Zn1 127.82(15) . . ?
C1 N3 N2 119.8(2) . . ?
C1 N3 H3 122(2) . . ?
N2 N3 H3 118(2) . . ?
C2A N2A N3A 119.9(2) . . ?
C2A N2A Zn1 117.52(16) . . ?
N3A N2A Zn1 122.47(14) . . ?
C1 N4 H4A 120 . . ?
C1 N4 H4B 120 . . ?
H4A N4 H4B 120 . . ?
C1A N3A N2A 120.31(19) . . ?
C1A N3A H3A 123(3) . . ?
N2A N3A H3A 116(3) . . ?
C1A N4A H4C 120 . . ?
C1A N4A H4D 120 . . ?
H4C N4A H4D 120 . . ?
N4 C1 N3 116.0(2) . . ?
N4 C1 Se1 120.8(2) . . ?
N3 C1 Se1 123.15(18) . . ?
N2 C2 C3 117.4(2) . . ?
N2 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
N4A C1A N3A 116.7(2) . . ?
N4A C1A Se1A 120.7(2) . . ?
N3A C1A Se1A 122.57(17) . . ?
N1 C3 C4 123.3(2) . . ?
N1 C3 C2 117.21(19) . . ?
C4 C3 C2 119.5(2) . . ?
N2A C2A C3A 117.1(2) . . ?
N2A C2A H2A 121.5 . . ?
C3A C2A H2A 121.5 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1A C3A C4A 123.7(2) . . ?
N1A C3A C2A 117.06(19) . . ?
C4A C3A C2A 119.2(2) . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5A C4A C3A 118.5(2) . . ?
C5A C4A H4E 120.7 . . ?
C3A C4A H4E 120.7 . . ?
C5 C6 C11 123.1(2) . . ?
C5 C6 C7 118.7(2) . . ?
C11 C6 C7 118.1(2) . . ?
C4A C5A C6A 120.5(2) . . ?
C4A C5A H5A 119.7 . . ?
C6A C5A H5A 119.7 . . ?
N1 C7 C8 119.89(19) . . ?
N1 C7 C6 120.8(2) . . ?
C8 C7 C6 119.3(2) . . ?
C5A C6A C11A 123.2(3) . . ?
C5A C6A C7A 117.9(2) . . ?
C11A C6A C7A 118.9(3) . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
N1A C7A C8A 119.7(2) . . ?
N1A C7A C6A 121.4(2) . . ?
C8A C7A C6A 119.0(2) . . ?
C8 C9 C10 120.5(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9A C8A C7A 120.2(3) . . ?
C9A C8A H8A 119.9 . . ?
C7A C8A H8A 119.9 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C8A C9A C10A 120.3(3) . . ?
C8A C9A H9A 119.8 . . ?
C10A C9A H9A 119.8 . . ?
C10 C11 C6 121.2(3) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
C11A C10A C9A 120.9(3) . . ?
C11A C10A H10A 119.5 . . ?
C9A C10A H10A 119.5 . . ?
C10A C11A C6A 120.7(3) . . ?
C10A C11A H11A 119.7 . . ?
C6A C11A H11A 119.7 . . ?
O1 Cl1 O2 107.2(3) . . ?
O1 Cl1 O4 111.3(3) . . ?
O2 Cl1 O4 110.7(2) . . ?
O1 Cl1 O3 108.4(3) . . ?
O2 Cl1 O3 110.5(3) . . ?
O4 Cl1 O3 108.8(2) . . ?
O6 Cl2 O5 115.1(3) . . ?
O6 Cl2 O7 109.4(3) . . ?
O5 Cl2 O7 108.2(4) . . ?
O6 Cl2 O8 110.1(3) . . ?
O5 Cl2 O8 108.9(3) . . ?
O7 Cl2 O8 104.6(3) . . ?
C12 O9A H9A1 109.5 . . ?
C12 O9B H9B 109.5 . . ?
O9A C12 C13 115.3(5) . . ?
O9B C12 C13 105.5(5) . . ?
O9A C12 H12A 108.5 . . ?
C13 C12 H12A 108.5 . . ?
O9A C12 H12B 108.5 . . ?
C13 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
O9B C12 H12C 110.6 . . ?
C13 C12 H12C 110.6 . . ?
O9B C12 H12D 110.6 . . ?
C13 C12 H12D 110.6 . . ?
H12C C12 H12D 108.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
C2 N2 N3 C1 -169.7(2) . . . . ?
Zn1 N2 N3 C1 16.3(3) . . . . ?
C2A N2A N3A C1A -180.0(2) . . . . ?
Zn1 N2A N3A C1A 4.4(3) . . . . ?
N2 N3 C1 N4 173.3(3) . . . . ?
N2 N3 C1 Se1 -6.9(3) . . . . ?
Zn1 Se1 C1 N4 176.7(3) . . . . ?
Zn1 Se1 C1 N3 -3.1(2) . . . . ?
N3 N2 C2 C3 -178.4(2) . . . . ?
Zn1 N2 C2 C3 -4.1(3) . . . . ?
N2A N3A C1A N4A 179.1(2) . . . . ?
N2A N3A C1A Se1A -2.3(4) . . . . ?
Zn1 Se1A C1A N4A 178.2(2) . . . . ?
Zn1 Se1A C1A N3A -0.4(2) . . . . ?
C7 N1 C3 C4 -2.8(3) . . . . ?
Zn1 N1 C3 C4 -179.75(18) . . . . ?
C7 N1 C3 C2 176.41(19) . . . . ?
Zn1 N1 C3 C2 -0.5(2) . . . . ?
N2 C2 C3 N1 3.1(3) . . . . ?
N2 C2 C3 C4 -177.7(2) . . . . ?
N3A N2A C2A C3A 178.9(2) . . . . ?
Zn1 N2A C2A C3A -5.2(3) . . . . ?
N1 C3 C4 C5 -0.1(4) . . . . ?
C2 C3 C4 C5 -179.3(2) . . . . ?
C7A N1A C3A C4A -0.8(3) . . . . ?
Zn1 N1A C3A C4A -174.46(19) . . . . ?
C7A N1A C3A C2A 178.8(2) . . . . ?
Zn1 N1A C3A C2A 5.2(3) . . . . ?
N2A C2A C3A N1A -0.1(3) . . . . ?
N2A C2A C3A C4A 179.5(2) . . . . ?
C3 C4 C5 C6 2.2(4) . . . . ?
N1A C3A C4A C5A 0.1(4) . . . . ?
C2A C3A C4A C5A -179.5(2) . . . . ?
C4 C5 C6 C11 176.4(3) . . . . ?
C4 C5 C6 C7 -1.3(4) . . . . ?
C3A C4A C5A C6A 0.8(4) . . . . ?
C3 N1 C7 C8 -175.2(2) . . . . ?
Zn1 N1 C7 C8 1.3(3) . . . . ?
C3 N1 C7 C6 3.6(3) . . . . ?
Zn1 N1 C7 C6 -179.86(15) . . . . ?
C5 C6 C7 N1 -1.7(3) . . . . ?
C11 C6 C7 N1 -179.5(2) . . . . ?
C5 C6 C7 C8 177.2(2) . . . . ?
C11 C6 C7 C8 -0.6(3) . . . . ?
C4A C5A C6A C11A 179.1(3) . . . . ?
C4A C5A C6A C7A -0.9(4) . . . . ?
N1 C7 C8 C9 177.6(2) . . . . ?
C6 C7 C8 C9 -1.3(4) . . . . ?
C3A N1A C7A C8A -178.8(2) . . . . ?
Zn1 N1A C7A C8A -6.2(3) . . . . ?
C3A N1A C7A C6A 0.7(3) . . . . ?
Zn1 N1A C7A C6A 173.36(17) . . . . ?
C5A C6A C7A N1A 0.1(4) . . . . ?
C11A C6A C7A N1A -179.9(2) . . . . ?
C5A C6A C7A C8A 179.6(2) . . . . ?
C11A C6A C7A C8A -0.3(4) . . . . ?
C7 C8 C9 C10 1.8(5) . . . . ?
N1A C7A C8A C9A 179.5(3) . . . . ?
C6A C7A C8A C9A -0.1(4) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C7A C8A C9A C10A 0.7(5) . . . . ?
C9 C10 C11 C6 -1.7(5) . . . . ?
C5 C6 C11 C10 -175.6(3) . . . . ?
C7 C6 C11 C10 2.2(4) . . . . ?
C8A C9A C10A C11A -1.0(5) . . . . ?
C9A C10A C11A C6A 0.6(5) . . . . ?
C5A C6A C11A C10A -179.9(3) . . . . ?
C7A C6A C11A C10A 0.1(5) . . . . ?

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
N3 H3 O3 0.866(18) 2.39(3) 3.082(4) 137(3) .
N4 H4A O3 0.86 2.58 3.259(5) 137.1 .
N4 H4A O9A 0.86 2.49 3.041(5) 122.7 2_655
N4 H4A O9B 0.86 2.49 2.970(8) 116.3 2_655
N4 H4B O4 0.86 2.48 3.164(5) 137.3 2_655
N3A H3A O9A 0.846(18) 2.01(2) 2.802(4) 155(4) 2
N3A H3A O9B 0.846(18) 1.97(2) 2.795(7) 163(4) 2
N4A H4C O7 0.86 2.34 3.017(5) 135.4 2_545
N4A H4C O9A 0.86 2.35 3.085(5) 143.4 2
N4A H4D Se1 0.86 2.67 3.447(3) 150.1 2_545
O9A H9A1 O7 0.82 2.19 2.955(8) 156.1 1_545
O9B H9B O1 0.82 2.08 2.818(11) 150.1 .

_shelxl_version_number           2014/6




# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_recrystallization_method 
'Crystallization from ethanolic solution'
_chemical_compound_source        synthetic
