# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350

_publ_contact_author             
# Name and address of author for correspondence
;
Pr R. Goumont
Institut Lavoisier de Versailles, UMR 8180
Université de Versailles
45 Avenue des Etats Unis
78035 Versailles cedex
France
;
_publ_contact_author_phone       '(33) 01 39 25 44 72'
_publ_contact_author_fax         '(33) 01 39 25 44 52'
_publ_contact_author_email       goumont@chimie.uvsq.fr

_publ_requested_coeditor_name    ?

_publ_contact_letter             
;
;

#====================================================================

# 2. processing summary (iucr office use only)

_journal_date_recd_electronic    ?

_journal_date_to_coeditor        ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?

_journal_date_printers_first     ?
_journal_date_printers_final     ?
_journal_date_proofs_out         ?
_journal_date_proofs_in          ?

_journal_coeditor_name           ?
_journal_coeditor_code           ?
_journal_coeditor_notes          
;
;

_journal_techeditor_code         ?
_journal_techeditor_notes        
;
;

_journal_coden_ASTM              ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?

_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?

#====================================================================

# 3. title and author list

_publ_section_title              
;
Supramolecular association of 1,2,5-chalcogenadiazoles : an unexpected
self-assembled dissymetric [Se...N]2 four-membered ring
;

# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.

loop_
_publ_author_name
_publ_author_address
G.Berionni
; Institut Lavoisier de Versailles, UMR 8180
Université de Versailles
45 Avenue des Etats Unis
78035 Versailles cedex
France
;
B.Pegot
; Institut Lavoisier de Versailles, UMR 8180
Université de Versailles
45 Avenue des Etats Unis
78035 Versailles cedex
France
;
J.Marrot
; Institut Lavoisier de Versailles, UMR 8180
Université de Versailles
45 Avenue des Etats Unis
78035 Versailles cedex
France
;
R.Goumont
; Institut Lavoisier de Versailles, UMR 8180
Université de Versailles
45 Avenue des Etats Unis
78035 Versailles cedex
France
;

#====================================================================

# 4. text

_publ_section_abstract           
;

;
_publ_section_comment            
;

;
_publ_section_experimental       
;

;
_publ_section_references         
;
Sheldrick, G.M. (1993). SHELXL-93. Program for crystal structure
determination. Univ. of Göttingen, Federal Republic of Germany.

Sheldrick, G.M. (1997). SHELXS-86. Program for the solution of crystal
structures. Univ. of Göttingen, Federal Republic of Germany.
;
_publ_section_figure_captions    
;

;
_publ_section_acknowledgements   
;

;
_publ_contact_author_name        'Pr R. Goumont'
#====================================================================
data_4
_database_code_depnum_ccdc_archive 'CCDC 702658'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 B2 F8 N6 Se3'
_chemical_formula_weight         752.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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'
'-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                   15.8892(4)
_cell_length_b                   12.0225(4)
_cell_length_c                   13.5325(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.711(2)
_cell_angle_gamma                90.00
_cell_volume                     2584.89(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8577
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      28.68

_exptl_crystal_description       platelet
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    4.351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2750
_exptl_absorpt_correction_T_max  0.6233
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'

_exptl_special_details           
;
'Blessing, Acta Cryst. (1995) A51, 33-38'
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 512x512
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            49871
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         30.10
_reflns_number_total             3791
_reflns_number_gt                2911
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1050P)²+5.7251P] where P=(Fo²+2Fc²)/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_number_reflns         3791
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1698
_refine_ls_wR_factor_gt          0.1501
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.59067(12) 0.57469(17) 1.07823(14) 0.0448(5) Uani 1 1 d . . .
Se2A Se 0.630877(14) 0.45163(2) 1.025311(17) 0.04630(6) Uani 1 1 d . . .
N3A N 0.68005(12) 0.53730(16) 0.92816(14) 0.0431(5) Uani 1 1 d . . .
C4A C 0.68850(14) 0.7355(2) 0.88106(16) 0.0477(6) Uani 1 1 d . . .
H4A H 0.7214 0.7242 0.8256 0.057 Uiso 1 1 calc R . .
C5A C 0.66367(16) 0.8387(2) 0.9078(2) 0.0566(7) Uani 1 1 d . . .
H5A H 0.6801 0.8990 0.8697 0.068 Uiso 1 1 calc R . .
C6A C 0.61256(17) 0.8583(2) 0.9933(2) 0.0564(7) Uani 1 1 d . . .
H6A H 0.5957 0.9305 1.0080 0.068 Uiso 1 1 calc R . .
C7A C 0.58860(16) 0.7736(2) 1.0526(2) 0.0530(6) Uani 1 1 d . . .
H7A H 0.5576 0.7872 1.1092 0.064 Uiso 1 1 calc R . .
C8A C 0.61178(13) 0.6642(2) 1.02675(16) 0.0424(5) Uani 1 1 d . . .
C9A C 0.66267(13) 0.64506(19) 0.94056(15) 0.0405(5) Uani 1 1 d . . .
C10A C 0.73134(17) 0.4906(3) 0.8486(2) 0.0600(7) Uani 1 1 d . . .
H10A H 0.7108 0.5172 0.7860 0.090 Uiso 1 1 calc R . .
H10B H 0.7279 0.4109 0.8501 0.090 Uiso 1 1 calc R . .
H10C H 0.7889 0.5131 0.8578 0.090 Uiso 1 1 calc R . .
N1B N 0.54628(12) 0.37766(17) 1.17231(14) 0.0457(5) Uani 1 1 d . . .
Se2B Se 0.5000 0.48209(3) 1.2500 0.04755(8) Uani 1 2 d S . .
C6B C 0.52608(17) 0.0801(2) 1.2073(2) 0.0561(7) Uani 1 1 d . . .
H6B H 0.5424 0.0124 1.1803 0.067 Uiso 1 1 calc R . .
C7B C 0.55227(15) 0.1751(2) 1.16487(17) 0.0502(6) Uani 1 1 d . . .
H7B H 0.5865 0.1734 1.1097 0.060 Uiso 1 1 calc R . .
C8B C 0.52641(13) 0.27838(19) 1.20634(14) 0.0400(5) Uani 1 1 d . . .
B B 0.6560(2) 0.1796(3) 0.8688(2) 0.0607(8) Uani 1 1 d . . .
F1 F 0.73852(17) 0.2004(3) 0.8410(2) 0.1442(12) Uani 1 1 d . . .
F2 F 0.6548(3) 0.1237(4) 0.9536(3) 0.2095(19) Uani 1 1 d . . .
F3 F 0.6145(2) 0.2731(2) 0.8746(4) 0.1722(16) Uani 1 1 d . . .
F4 F 0.6269(4) 0.1163(3) 0.8012(3) 0.235(2) Uani 1 1 d . . .

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
N1A 0.0426(8) 0.0470(9) 0.0450(9) 0.0020(8) 0.0102(7) -0.0009(8)
Se2A 0.04915(11) 0.04477(12) 0.04526(11) 0.00342(8) 0.01257(9) 0.00103(9)
N3A 0.0411(8) 0.0506(10) 0.0380(8) 0.0027(7) 0.0094(7) -0.0002(7)
C4A 0.0471(11) 0.0549(12) 0.0410(10) 0.0072(9) 0.0019(9) -0.0077(10)
C5A 0.0569(13) 0.0559(13) 0.0570(13) 0.0134(11) -0.0060(11) -0.0085(11)
C6A 0.0590(13) 0.0475(12) 0.0626(14) 0.0006(11) -0.0016(12) 0.0029(11)
C7A 0.0519(12) 0.0511(12) 0.0562(12) -0.0054(11) 0.0054(10) 0.0047(10)
C8A 0.0374(9) 0.0502(11) 0.0397(9) 0.0027(8) 0.0040(8) 0.0022(9)
C9A 0.0397(9) 0.0450(10) 0.0368(9) 0.0008(8) 0.0010(8) -0.0043(8)
C10A 0.0588(13) 0.0696(16) 0.0522(12) -0.0046(12) 0.0245(10) 0.0030(12)
N1B 0.0434(8) 0.0515(10) 0.0425(8) 0.0024(8) 0.0121(7) 0.0024(8)
Se2B 0.04728(15) 0.04608(15) 0.04957(16) 0.000 0.01177(13) 0.000
C6B 0.0631(14) 0.0482(12) 0.0570(13) -0.0060(11) 0.0030(11) 0.0037(11)
C7B 0.0549(12) 0.0547(13) 0.0412(10) -0.0037(10) 0.0110(9) 0.0106(10)
C8B 0.0395(9) 0.0486(11) 0.0320(8) 0.0011(8) 0.0058(7) 0.0025(8)
B 0.0782(18) 0.0490(14) 0.0555(14) -0.0108(12) 0.0203(13) 0.0006(14)
F1 0.1057(16) 0.200(3) 0.1277(18) 0.045(2) 0.0478(14) 0.029(2)
F2 0.324(5) 0.183(4) 0.1237(19) 0.051(2) 0.107(2) 0.025(4)
F3 0.1230(19) 0.0661(14) 0.329(5) -0.022(2) 0.061(3) 0.0120(14)
F4 0.339(5) 0.178(3) 0.187(3) -0.097(2) -0.052(4) -0.055(4)

_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
N1A C8A 1.328(3) . ?
N1A Se2A 1.767(2) . ?
N1A Se2B 2.9666(19) . ?
Se2A N3A 1.8507(19) . ?
Se2A N1B 2.5732(19) . ?
Se2A F3 2.970(4) . ?
N3A C9A 1.336(3) . ?
N3A C10A 1.470(3) . ?
C4A C5A 1.352(4) . ?
C4A C9A 1.416(3) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.441(4) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.355(4) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.410(4) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.446(3) . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
N1B C8B 1.319(3) . ?
N1B Se2B 1.800(2) . ?
Se2B N1B 1.800(2) 2_657 ?
C6B C7B 1.347(4) . ?
C6B C6B 1.431(6) 2_657 ?
C6B H6B 0.9300 . ?
C7B C8B 1.425(3) . ?
C7B H7B 0.9300 . ?
C8B C8B 1.458(4) 2_657 ?
B F4 1.273(5) . ?
B F3 1.305(4) . ?
B F2 1.329(5) . ?
B F1 1.391(4) . ?

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
C8A N1A Se2A 111.80(15) . . ?
C8A N1A Se2B 147.54(15) . . ?
Se2A N1A Se2B 100.66(8) . . ?
N1A Se2A N3A 88.85(9) . . ?
N1A Se2A N1B 77.35(8) . . ?
N3A Se2A N1B 166.09(8) . . ?
N1A Se2A F3 148.71(9) . . ?
N3A Se2A F3 87.05(10) . . ?
N1B Se2A F3 103.82(9) . . ?
C9A N3A C10A 125.5(2) . . ?
C9A N3A Se2A 111.15(15) . . ?
C10A N3A Se2A 123.39(17) . . ?
C5A C4A C9A 117.7(2) . . ?
C5A C4A H4A 121.2 . . ?
C9A C4A H4A 121.2 . . ?
C4A C5A C6A 122.3(2) . . ?
C4A C5A H5A 118.9 . . ?
C6A C5A H5A 118.9 . . ?
C7A C6A C5A 121.2(3) . . ?
C7A C6A H6A 119.4 . . ?
C5A C6A H6A 119.4 . . ?
C6A C7A C8A 118.5(2) . . ?
C6A C7A H7A 120.7 . . ?
C8A C7A H7A 120.7 . . ?
N1A C8A C7A 123.8(2) . . ?
N1A C8A C9A 116.2(2) . . ?
C7A C8A C9A 120.0(2) . . ?
N3A C9A C4A 127.7(2) . . ?
N3A C9A C8A 112.00(19) . . ?
C4A C9A C8A 120.3(2) . . ?
N3A C10A H10A 109.5 . . ?
N3A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
N3A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C8B N1B Se2B 109.02(14) . . ?
C8B N1B Se2A 135.41(15) . . ?
Se2B N1B Se2A 115.56(10) . . ?
N1B Se2B N1B 91.57(13) . 2_657 ?
N1B Se2B N1A 66.32(8) . . ?
N1B Se2B N1A 157.67(8) 2_657 . ?
C7B C6B C6B 121.97(15) . 2_657 ?
C7B C6B H6B 119.0 . . ?
C6B C6B H6B 119.0 2_657 . ?
C6B C7B C8B 118.6(2) . . ?
C6B C7B H7B 120.7 . . ?
C8B C7B H7B 120.7 . . ?
N1B C8B C7B 125.41(19) . . ?
N1B C8B C8B 115.19(12) . 2_657 ?
C7B C8B C8B 119.40(13) . 2_657 ?
F4 B F3 112.2(4) . . ?
F4 B F2 108.0(4) . . ?
F3 B F2 111.8(4) . . ?
F4 B F1 104.4(4) . . ?
F3 B F1 109.8(3) . . ?
F2 B F1 110.4(4) . . ?
B F3 Se2A 128.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.10
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.287
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.234
#===END



