# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Pantelis Trikalitis'
_publ_contact_author_email       PTRIKAL@CHEMISTRY.UOC.GR

_publ_section_title              
;
(H2NC4H8NCH2CH2NH2)2Zn2Sn2Se7: A Hybrid Ternary Semiconductor Stabilized
by Amine Molecules Acting Simultaneously as Ligands and Counterions
;
loop_
_publ_author_name
'Pantelis Trikalitis'
'Thomas Bakas'
'Aggelos Philippidis'

# Attachment '(AEP)2Zn2Sn2Se7.cif'

data_(AEP)2Zn2Sn2Se7
_database_code_depnum_ccdc_archive 'CCDC 658784'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H32 N6 Se7 Sn2 Zn2'
_chemical_formula_weight         1181.28

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'
N N 0.0061 0.0033 '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'
Sn Sn -0.6537 1.4246 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'

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

_cell_length_a                   13.847(3)
_cell_length_b                   11.216(2)
_cell_length_c                   10.447(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.12(3)
_cell_angle_gamma                90.00
_cell_volume                     1523.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5084
_cell_measurement_theta_min      3.55
_cell_measurement_theta_max      32.4

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    11.551
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.0648
_exptl_absorpt_correction_T_max  0.3322
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23628
_diffrn_reflns_av_R_equivalents  0.1537
_diffrn_reflns_av_sigmaI/netI    0.2356
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         32.40
_reflns_number_total             10094
_reflns_number_gt                5168
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_number_reflns         10094
_refine_ls_number_parameters     262
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.1701
_refine_ls_R_factor_gt           0.0832
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1331
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_restrained_S_all      0.927
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.30574(5) 0.26123(6) 0.94674(8) 0.01839(17) Uani 1 1 d . . .
Sn2 Sn 0.83375(5) 0.45235(6) 1.04671(8) 0.01900(17) Uani 1 1 d . . .
Zn1 Zn 1.05510(9) 0.25821(13) 1.03025(15) 0.0255(3) Uani 1 1 d . . .
Zn2 Zn 0.53988(9) 0.46258(12) 0.93237(14) 0.0238(3) Uani 1 1 d . . .
Se1 Se 0.67785(9) 0.32874(10) 0.93058(14) 0.0290(3) Uani 1 1 d . . .
Se2 Se 0.97204(8) 0.31819(11) 1.19398(13) 0.0264(3) Uani 1 1 d . . .
Se3 Se 0.36883(8) 0.38676(10) 0.79057(12) 0.0238(3) Uani 1 1 d . . .
Se4 Se 0.90606(9) 0.55256(10) 0.88410(14) 0.0285(3) Uani 1 1 d . . .
Se5 Se 0.19915(9) 0.09984(10) 0.78299(14) 0.0257(3) Uani 1 1 d . . .
Se6 Se 0.45255(9) 0.17183(10) 1.14077(13) 0.0247(3) Uani 1 1 d . . .
Se7 Se 0.19612(9) 0.39006(11) 1.03486(17) 0.0425(4) Uani 1 1 d . . .
N1 N 0.5394(6) 0.4716(8) 1.1322(10) 0.021(2) Uani 1 1 d . . .
H1NA H 0.5256 0.3986 1.1574 0.025 Uiso 1 1 calc R . .
H1NB H 0.6026 0.4924 1.1880 0.025 Uiso 1 1 calc R . .
C2 C 0.4485(10) 0.5378(16) 1.2882(15) 0.046(4) Uani 1 1 d . . .
H2A H 0.3979 0.5936 1.2977 0.056 Uiso 1 1 calc R . .
H2B H 0.4240 0.4575 1.2931 0.056 Uiso 1 1 calc R . .
N2 N 0.4527(7) 0.0566(9) 0.6026(11) 0.028(2) Uani 1 1 d . . .
C3 C 0.4378(13) -0.0215(13) 1.4881(18) 0.064(6) Uani 1 1 d . . .
H3A H 0.4489 -0.1036 1.5190 0.077 Uiso 1 1 calc R . .
H3B H 0.4867 -0.0022 1.4435 0.077 Uiso 1 1 calc R . .
C4 C 0.6715(11) 0.4939(13) 0.6115(18) 0.048(3) Uani 1 1 d U . .
H4A H 0.6822 0.4434 0.6905 0.058 Uiso 1 1 calc R . .
H4B H 0.7204 0.4706 0.5682 0.058 Uiso 1 1 calc R . .
N3 N 0.6882(10) 0.6201(12) 0.6544(13) 0.053(4) Uani 1 1 d . . .
H3C H 0.7547 0.6300 0.7062 0.063 Uiso 1 1 calc R . .
H3D H 0.6500 0.6368 0.7066 0.063 Uiso 1 1 calc R . .
C5 C 0.3386(14) 0.2075(14) 0.4621(19) 0.063(6) Uani 1 1 d . . .
H5A H 0.3338 0.2884 0.4274 0.076 Uiso 1 1 calc R . .
H5B H 0.2907 0.1993 0.5110 0.076 Uiso 1 1 calc R . .
C6 C 0.4455(10) 0.1833(12) 0.5559(15) 0.039(3) Uani 1 1 d U . .
H6A H 0.4627 0.2364 0.6338 0.047 Uiso 1 1 calc R . .
H6B H 0.4939 0.1972 0.5088 0.047 Uiso 1 1 calc R . .
N4 N 0.9551(8) 0.2462(10) 0.8283(10) 0.035(3) Uani 1 1 d . . .
H4C H 0.9173 0.3134 0.8081 0.043 Uiso 1 1 calc R . .
H4D H 0.9931 0.2436 0.7737 0.043 Uiso 1 1 calc R . .
C7 C 0.1133(9) 0.6467(17) 0.2035(11) 0.074(6) Uani 1 1 d D . .
H7A H 0.1405 0.6387 0.1298 0.089 Uiso 1 1 calc R . .
H7B H 0.0722 0.5762 0.2012 0.089 Uiso 1 1 calc R . .
C8 C 0.2055(9) 0.643(2) 0.3380(12) 0.073(6) Uani 1 1 d D . .
H8A H 0.2400 0.5666 0.3462 0.087 Uiso 1 1 calc R . .
H8B H 0.2542 0.7049 0.3372 0.087 Uiso 1 1 calc R . .
N5 N 0.1719(8) 0.6604(11) 0.4544(12) 0.044(3) Uani 1 1 d . . .
C9 C 0.7334(12) 0.1926(19) 1.4286(18) 0.064(6) Uani 1 1 d . . .
H9A H 0.7040 0.2652 1.4498 0.077 Uiso 1 1 calc R . .
H9B H 0.6828 0.1295 1.4141 0.077 Uiso 1 1 calc R . .
C10 C 0.7587(11) 0.2104(16) 1.3011(15) 0.051(5) Uani 1 1 d . . .
H10A H 0.6954 0.2237 1.2252 0.061 Uiso 1 1 calc R . .
H10B H 0.8009 0.2812 1.3115 0.061 Uiso 1 1 calc R . .
N6 N 0.1876(9) 0.6102(12) 0.7301(13) 0.049(4) Uani 1 1 d . . .
H6C H 0.1666 0.6316 0.7993 0.059 Uiso 1 1 calc R . .
H6D H 0.2330 0.5503 0.7603 0.059 Uiso 1 1 calc R . .
C11 C 0.9021(12) 0.0633(18) 1.380(2) 0.073(7) Uani 1 1 d . . .
H11A H 0.9613 0.1141 1.3932 0.088 Uiso 1 1 calc R . .
H11B H 0.9185 -0.0163 1.3578 0.088 Uiso 1 1 calc R . .
C12 C 0.1256(13) 0.5600(18) 0.4853(18) 0.069(6) Uani 1 1 d . . .
H12A H 0.1710 0.4927 0.4915 0.082 Uiso 1 1 calc R . .
H12B H 0.0628 0.5448 0.4093 0.082 Uiso 1 1 calc R . .
C1 C 0.4639(8) 0.5571(10) 1.1499(12) 0.020(2) Uani 1 1 d U . .
H1A H 0.3987 0.5472 1.0764 0.024 Uiso 1 1 calc R . .
H1B H 0.4878 0.6378 1.1456 0.024 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Sn1 0.0167(3) 0.0157(3) 0.0241(4) 0.0003(3) 0.0087(3) -0.0012(3)
Sn2 0.0172(3) 0.0146(3) 0.0267(4) -0.0003(3) 0.0094(3) 0.0010(3)
Zn1 0.0224(5) 0.0259(6) 0.0293(7) -0.0038(6) 0.0103(5) -0.0017(5)
Zn2 0.0248(5) 0.0264(6) 0.0205(7) -0.0025(6) 0.0082(5) -0.0072(5)
Se1 0.0243(5) 0.0227(5) 0.0402(7) -0.0097(5) 0.0113(5) -0.0051(4)
Se2 0.0267(5) 0.0288(5) 0.0282(6) 0.0062(5) 0.0150(4) 0.0088(5)
Se3 0.0219(4) 0.0271(5) 0.0197(6) 0.0041(5) 0.0035(4) -0.0045(4)
Se4 0.0354(6) 0.0219(5) 0.0307(7) 0.0028(5) 0.0144(5) -0.0039(5)
Se5 0.0284(5) 0.0231(5) 0.0236(6) 0.0000(5) 0.0063(5) -0.0077(4)
Se6 0.0317(5) 0.0205(5) 0.0177(6) 0.0007(5) 0.0032(5) 0.0015(4)
Se7 0.0357(5) 0.0261(6) 0.0798(10) -0.0214(6) 0.0379(6) -0.0082(5)
N1 0.015(3) 0.025(5) 0.025(5) 0.009(4) 0.010(3) 0.002(3)
C2 0.032(6) 0.076(10) 0.029(8) 0.011(8) 0.007(6) 0.001(7)
N2 0.036(5) 0.034(5) 0.019(5) 0.011(4) 0.015(4) 0.012(4)
C3 0.078(11) 0.041(8) 0.047(10) -0.012(7) -0.011(9) 0.024(7)
C4 0.051(4) 0.047(4) 0.046(4) 0.003(3) 0.015(3) 0.003(3)
N3 0.059(7) 0.070(9) 0.022(7) -0.004(6) 0.004(6) 0.005(7)
C5 0.090(12) 0.031(7) 0.051(11) -0.012(7) 0.001(9) 0.010(8)
C6 0.042(4) 0.037(4) 0.037(4) -0.006(3) 0.013(3) 0.000(3)
N4 0.052(5) 0.041(6) 0.016(5) -0.002(5) 0.015(4) -0.016(5)
C7 0.075(9) 0.101(13) 0.037(10) -0.004(9) 0.009(8) 0.058(9)
C8 0.061(8) 0.123(18) 0.049(10) -0.008(11) 0.038(8) -0.010(10)
N5 0.037(5) 0.056(7) 0.035(7) 0.024(6) 0.007(5) 0.001(5)
C9 0.040(8) 0.093(13) 0.052(11) 0.006(10) 0.005(8) 0.001(9)
C10 0.044(8) 0.076(11) 0.021(8) 0.008(7) -0.003(6) 0.003(7)
N6 0.055(6) 0.066(8) 0.027(6) 0.006(6) 0.015(5) 0.024(6)
C11 0.035(7) 0.088(13) 0.095(15) 0.020(12) 0.020(9) 0.011(8)
C12 0.051(9) 0.108(14) 0.039(10) -0.035(10) 0.006(8) 0.012(9)
C1 0.022(3) 0.022(3) 0.014(3) -0.003(3) 0.003(3) 0.001(3)

_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
Sn1 Se7 2.4903(16) . ?
Sn1 Se3 2.5274(15) . ?
Sn1 Se6 2.5321(16) . ?
Sn1 Se5 2.5777(15) . ?
Sn2 Se1 2.5004(14) . ?
Sn2 Se2 2.5043(14) . ?
Sn2 Se4 2.5143(17) . ?
Sn2 Se5 2.5821(16) 2_657 ?
Zn1 N4 2.092(10) . ?
Zn1 Se7 2.4367(19) 1_655 ?
Zn1 Se2 2.461(2) . ?
Zn1 Se4 2.4657(19) 2_747 ?
Zn2 N1 2.092(10) . ?
Zn2 Se1 2.4349(18) . ?
Zn2 Se3 2.4725(18) . ?
Zn2 Se6 2.4816(19) 2_657 ?
Se4 Zn1 2.4657(19) 2_757 ?
Se5 Sn2 2.5821(16) 2_647 ?
Se6 Zn2 2.4816(19) 2_647 ?
Se7 Zn1 2.4367(19) 1_455 ?
N1 C1 1.477(14) . ?
C2 N2 1.464(16) 2_657 ?
C2 C1 1.55(2) . ?
N2 C3 1.439(19) 1_554 ?
N2 C2 1.464(16) 2_647 ?
N2 C6 1.495(17) . ?
C3 N2 1.439(19) 1_556 ?
C3 C4 1.52(2) 2_647 ?
C4 N3 1.48(2) . ?
C4 C3 1.52(2) 2_657 ?
N3 C5 1.51(2) 2_656 ?
C5 C6 1.49(2) . ?
C5 N3 1.51(2) 2_646 ?
N4 C7 1.428(18) 2_646 ?
C7 N4 1.428(18) 2_656 ?
C7 C8 1.540(9) . ?
C8 N5 1.46(2) . ?
N5 C12 1.39(2) . ?
N5 C9 1.498(19) 2_657 ?
C9 N5 1.498(19) 2_647 ?
C9 C10 1.50(2) . ?
C10 N6 1.45(2) 2_647 ?
N6 C10 1.45(2) 2_657 ?
N6 C11 1.47(2) 2_657 ?
C11 N6 1.47(2) 2_647 ?
C11 C12 1.58(3) 2_647 ?
C12 C11 1.58(3) 2_657 ?

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
Se7 Sn1 Se3 107.78(5) . . ?
Se7 Sn1 Se6 110.95(6) . . ?
Se3 Sn1 Se6 112.13(5) . . ?
Se7 Sn1 Se5 111.72(5) . . ?
Se3 Sn1 Se5 102.07(5) . . ?
Se6 Sn1 Se5 111.83(5) . . ?
Se1 Sn2 Se2 108.36(5) . . ?
Se1 Sn2 Se4 113.46(6) . . ?
Se2 Sn2 Se4 106.59(5) . . ?
Se1 Sn2 Se5 111.22(5) . 2_657 ?
Se2 Sn2 Se5 103.92(5) . 2_657 ?
Se4 Sn2 Se5 112.63(5) . 2_657 ?
N4 Zn1 Se7 107.9(3) . 1_655 ?
N4 Zn1 Se2 114.4(3) . . ?
Se7 Zn1 Se2 112.54(7) 1_655 . ?
N4 Zn1 Se4 107.0(3) . 2_747 ?
Se7 Zn1 Se4 119.17(7) 1_655 2_747 ?
Se2 Zn1 Se4 95.70(7) . 2_747 ?
N1 Zn2 Se1 108.0(2) . . ?
N1 Zn2 Se3 106.4(2) . . ?
Se1 Zn2 Se3 112.08(7) . . ?
N1 Zn2 Se6 106.1(3) . 2_657 ?
Se1 Zn2 Se6 117.67(7) . 2_657 ?
Se3 Zn2 Se6 105.91(6) . 2_657 ?
Zn2 Se1 Sn2 101.72(6) . . ?
Zn1 Se2 Sn2 100.30(6) . . ?
Zn2 Se3 Sn1 106.11(6) . . ?
Zn1 Se4 Sn2 105.12(7) 2_757 . ?
Sn1 Se5 Sn2 100.90(5) . 2_647 ?
Zn2 Se6 Sn1 103.62(5) 2_647 . ?
Zn1 Se7 Sn1 103.11(6) 1_455 . ?
C1 N1 Zn2 113.7(7) . . ?
N2 C2 C1 108.4(11) 2_657 . ?
C3 N2 C2 112.8(11) 1_554 2_647 ?
C3 N2 C6 109.4(11) 1_554 . ?
C2 N2 C6 109.3(11) 2_647 . ?
N2 C3 C4 108.8(13) 1_556 2_647 ?
N3 C4 C3 109.3(12) . 2_657 ?
C4 N3 C5 114.1(12) . 2_656 ?
C6 C5 N3 108.9(13) . 2_646 ?
C5 C6 N2 109.1(11) . . ?
C7 N4 Zn1 116.2(8) 2_646 . ?
N4 C7 C8 120.6(14) 2_656 . ?
N5 C8 C7 110.8(11) . . ?
C12 N5 C8 113.0(15) . . ?
C12 N5 C9 110.5(13) . 2_657 ?
C8 N5 C9 105.8(12) . 2_657 ?
N5 C9 C10 110.4(13) 2_647 . ?
N6 C10 C9 113.1(14) 2_647 . ?
C10 N6 C11 117.6(13) 2_657 2_657 ?
N6 C11 C12 107.9(14) 2_647 2_647 ?
N5 C12 C11 117.4(15) . 2_657 ?
N1 C1 C2 110.9(10) . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        32.40
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         2.040
_refine_diff_density_min         -2.680
_refine_diff_density_rms         0.318