#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:07:09 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180375 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/44/7204427.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7204427
loop_
_publ_author_name
'Zdenko Časar'
'Ivan Leban'
'Alenka Majcen-Le Maréchal'
'Dominique Lorcy'
_publ_section_title
;
 Synthesis of diselenadiazafulvalenes and influence of steric strain on
 their anodic behavior
;
_journal_issue                   13
_journal_name_full               'J. Chem. Soc., Perkin Trans. 1'
_journal_page_first              1568
_journal_page_last               1573
_journal_paper_doi               10.1039/b203317h
_journal_year                    2002
_chemical_formula_moiety         'C16 H12 N2 S2 Se2'
_chemical_formula_sum            'C16 H12 N2 S2 Se2'
_chemical_formula_weight         454.32
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.747(3)
_cell_angle_beta                 104.027(3)
_cell_angle_gamma                103.336(3)
_cell_formula_units_Z            3
_cell_length_a                   9.8982(3)
_cell_length_b                   10.0070(3)
_cell_length_c                   13.9470(3)
_cell_measurement_reflns_used    5305
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1246.92(7)
_computing_cell_refinement
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
KappaCCD Reference Manual (Nonius, 1998)
;
_computing_data_reduction
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
;
ORTEPII (Johnson, 1971), PLATON (Spek, 1998),
ORTEP-3 (Farugia, 1999)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.055
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method
;
563 frames in 6 sets of ω and φ scans. Rotation/frame=1°.
Crystal-detector distance=32 mm. Measuring time=65 s/°.
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9637
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    4.695
_exptl_absorpt_correction_T_max  0.775
_exptl_absorpt_correction_T_min  0.412
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
contained in maXus (Mackay et al., 1998)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             666
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.984
_refine_diff_density_min         -1.600
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0864P)²+1.0011P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1387
_reflns_number_gt                4728
_reflns_number_total             5628
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b203317h.txt
_cod_data_source_block           10
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1246.92(6)
_cod_database_code               7204427
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C11 C 0.4933(4) 0.5063(4) 0.9465(3) 0.0404(8) Uani 1 1 d . . .
S1 S 0.30780(11) 0.42622(10) 0.86100(8) 0.0457(2) Uani 1 1 d . . .
Se1 Se 0.09961(4) 0.11381(4) 0.77922(3) 0.04344(15) Uani 1 1 d . . .
C21 C 0.2905(4) 0.2435(4) 0.8416(2) 0.0358(7) Uani 1 1 d . . .
N31 N 0.3943(3) 0.1900(3) 0.8681(2) 0.0379(6) Uani 1 1 d . . .
C31A C 0.3443(4) 0.0410(4) 0.8433(3) 0.0362(7) Uani 1 1 d . . .
C41 C 0.4359(5) -0.0435(5) 0.8636(3) 0.0495(9) Uani 1 1 d . . .
H21 H 0.5359 -0.0012 0.8949 0.059 Uiso 1 1 calc R . .
C51 C 0.3760(6) -0.1908(5) 0.8367(4) 0.0578(11) Uani 1 1 d . . .
H28 H 0.4367 -0.2475 0.8496 0.069 Uiso 1 1 calc R . .
C61 C 0.2255(5) -0.2565(5) 0.7903(3) 0.0526(10) Uani 1 1 d . . .
H19 H 0.1870 -0.3556 0.7740 0.063 Uiso 1 1 calc R . .
C71 C 0.1345(4) -0.1746(4) 0.7688(3) 0.0420(8) Uani 1 1 d . . .
H12 H 0.0346 -0.2176 0.7375 0.050 Uiso 1 1 calc R . .
C71A C 0.1943(4) -0.0265(4) 0.7945(2) 0.0344(7) Uani 1 1 d . . .
C12 C 0.0146(5) 0.5766(5) -0.0013(3) 0.0473(9) Uani 1 1 d . . .
S2 S 0.20566(11) 0.68018(12) 0.05906(7) 0.0475(2) Uani 1 1 d . . .
Se2 Se 0.41065(4) 0.80082(5) 0.28714(3) 0.04855(16) Uani 1 1 d . . .
C22 C 0.2210(4) 0.7080(4) 0.1899(3) 0.0396(8) Uani 1 1 d . . .
N32 N 0.1159(4) 0.6694(4) 0.2266(2) 0.0443(7) Uani 1 1 d . . .
C32A C 0.1637(4) 0.7066(5) 0.3344(3) 0.0445(8) Uani 1 1 d . . .
C42 C 0.0696(5) 0.6790(6) 0.3924(3) 0.0610(12) Uani 1 1 d . . .
H29 H -0.0294 0.6318 0.3601 0.073 Uiso 1 1 calc R . .
C52 C 0.1263(6) 0.7232(7) 0.4988(4) 0.0725(15) Uani 1 1 d . . .
H30 H 0.0644 0.7063 0.5383 0.087 Uiso 1 1 calc R . .
C62 C 0.2755(6) 0.7933(7) 0.5482(3) 0.0671(14) Uani 1 1 d . . .
H32 H 0.3109 0.8226 0.6200 0.081 Uiso 1 1 calc R . .
C72 C 0.3702(5) 0.8192(5) 0.4924(3) 0.0545(10) Uani 1 1 d . . .
H22 H 0.4695 0.8642 0.5252 0.065 Uiso 1 1 calc R . .
C72A C 0.3125(4) 0.7759(4) 0.3842(3) 0.0427(8) Uani 1 1 d . . .
C13 C 0.9248(4) 1.0088(4) 0.9820(3) 0.0409(8) Uani 1 1 d . . .
S3 S 0.78518(12) 0.83571(13) 0.93248(8) 0.0523(3) Uani 1 1 d . . .
Se3 Se 0.69001(7) 0.59691(5) 0.72452(4) 0.06719(19) Uani 1 1 d . . .
C23 C 0.7643(4) 0.7934(4) 0.8006(3) 0.0402(8) Uani 1 1 d . . .
N33 N 0.7936(3) 0.8831(4) 0.7491(2) 0.0422(7) Uani 1 1 d . . .
C33A C 0.7633(4) 0.8132(4) 0.6440(3) 0.0420(8) Uani 1 1 d . . .
C43 C 0.7850(5) 0.8873(6) 0.5722(3) 0.0546(10) Uani 1 1 d . . .
H25 H 0.8191 0.9870 0.5922 0.066 Uiso 1 1 calc R . .
C53 C 0.7541(5) 0.8075(7) 0.4700(4) 0.0676(14) Uani 1 1 d . . .
H31 H 0.7696 0.8548 0.4215 0.081 Uiso 1 1 calc R . .
C63 C 0.7005(6) 0.6586(7) 0.4391(4) 0.0725(16) Uani 1 1 d . . .
H26 H 0.6800 0.6077 0.3703 0.087 Uiso 1 1 calc R . .
C73 C 0.6778(6) 0.5868(6) 0.5084(4) 0.0686(14) Uani 1 1 d . . .
H33 H 0.6421 0.4871 0.4874 0.082 Uiso 1 1 calc R . .
C73A C 0.7086(5) 0.6641(5) 0.6120(3) 0.0507(9) Uani 1 1 d . . .
H2A H 0.516(5) 0.594(6) 0.955(4) 0.050(13) Uiso 1 1 d . . .
H3A H 0.550(6) 0.462(6) 0.919(4) 0.055(13) Uiso 1 1 d . . .
H4A H 0.904(5) 1.070(5) 1.038(3) 0.044(11) Uiso 1 1 d . . .
H5A H -0.034(6) 0.626(6) 0.032(4) 0.060(14) Uiso 1 1 d . . .
H6A H 0.925(4) 1.062(4) 0.933(3) 0.031(9) Uiso 1 1 d . . .
H7A H -0.015(6) 0.591(6) -0.066(5) 0.066(15) Uiso 1 1 d . . .
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'
S S 0.1246 0.1234 '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_
_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 C11 S1 112.0(4) 2_667 . ?
C11 C11 H2A 104(3) 2_667 . ?
S1 C11 H2A 108(3) . . ?
C11 C11 H3A 110(3) 2_667 . ?
S1 C11 H3A 108(3) . . ?
H2A C11 H3A 115(5) . . ?
C21 S1 C11 100.88(18) . . ?
C71A Se1 C21 83.90(16) . . ?
N31 C21 S1 126.0(3) . . ?
N31 C21 Se1 117.1(3) . . ?
S1 C21 Se1 116.9(2) . . ?
C21 N31 C31A 111.9(3) . . ?
N31 C31A C41 123.3(3) . . ?
N31 C31A C71A 117.7(3) . . ?
C41 C31A C71A 119.0(4) . . ?
C51 C41 C31A 119.2(4) . . ?
C51 C41 H21 120.4 . . ?
C31A C41 H21 120.4 . . ?
C41 C51 C61 121.2(4) . . ?
C41 C51 H28 119.4 . . ?
C61 C51 H28 119.4 . . ?
C71 C61 C51 120.1(4) . . ?
C71 C61 H19 119.9 . . ?
C51 C61 H19 119.9 . . ?
C61 C71 C71A 118.9(4) . . ?
C61 C71 H12 120.6 . . ?
C71A C71 H12 120.6 . . ?
C71 C71A C31A 121.6(3) . . ?
C71 C71A Se1 129.1(3) . . ?
C31A C71A Se1 109.3(3) . . ?
C12 C12 S2 112.6(4) 2_565 . ?
C12 C12 H5A 114(3) 2_565 . ?
S2 C12 H5A 105(3) . . ?
C12 C12 H7A 117(3) 2_565 . ?
S2 C12 H7A 107(3) . . ?
H5A C12 H7A 100(5) . . ?
C22 S2 C12 101.3(2) . . ?
C72A Se2 C22 83.55(16) . . ?
N32 C22 S2 125.8(3) . . ?
N32 C22 Se2 116.9(3) . . ?
S2 C22 Se2 117.3(2) . . ?
C22 N32 C32A 112.0(3) . . ?
N32 C32A C42 122.8(4) . . ?
N32 C32A C72A 117.3(3) . . ?
C42 C32A C72A 119.9(4) . . ?
C52 C42 C32A 118.7(4) . . ?
C52 C42 H29 120.7 . . ?
C32A C42 H29 120.7 . . ?
C42 C52 C62 121.1(4) . . ?
C42 C52 H30 119.4 . . ?
C62 C52 H30 119.4 . . ?
C72 C62 C52 121.1(4) . . ?
C72 C62 H32 119.5 . . ?
C52 C62 H32 119.5 . . ?
C62 C72 C72A 117.9(4) . . ?
C62 C72 H22 121.0 . . ?
C72A C72 H22 121.0 . . ?
C32A C72A C72 121.3(4) . . ?
C32A C72A Se2 110.4(3) . . ?
C72 C72A Se2 128.3(3) . . ?
C13 C13 S3 110.8(4) 2_777 . ?
C13 C13 H4A 111(3) 2_777 . ?
S3 C13 H4A 109(3) . . ?
C13 C13 H6A 108(2) 2_777 . ?
S3 C13 H6A 113(2) . . ?
H4A C13 H6A 103(3) . . ?
C23 S3 C13 101.92(18) . . ?
C73A Se3 C23 84.30(17) . . ?
N33 C23 S3 126.6(3) . . ?
N33 C23 Se3 116.5(3) . . ?
S3 C23 Se3 117.0(2) . . ?
C23 N33 C33A 111.9(3) . . ?
C73A C33A C43 120.1(4) . . ?
C73A C33A N33 117.3(4) . . ?
C43 C33A N33 122.7(4) . . ?
C53 C43 C33A 118.1(5) . . ?
C53 C43 H25 120.9 . . ?
C33A C43 H25 120.9 . . ?
C63 C53 C43 121.3(5) . . ?
C63 C53 H31 119.4 . . ?
C43 C53 H31 119.4 . . ?
C73 C63 C53 120.6(4) . . ?
C73 C63 H26 119.7 . . ?
C53 C63 H26 119.7 . . ?
C63 C73 C73A 119.5(5) . . ?
C63 C73 H33 120.3 . . ?
C73A C73 H33 120.3 . . ?
C33A C73A C73 120.5(5) . . ?
C33A C73A Se3 110.0(3) . . ?
C73 C73A Se3 129.5(4) . . ?
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
C11 C11 1.502(7) 2_667 ?
C11 S1 1.810(4) . ?
C11 H2A 0.83(5) . ?
C11 H3A 0.89(5) . ?
S1 C21 1.749(4) . ?
Se1 C71A 1.881(4) . ?
Se1 C21 1.893(3) . ?
C21 N31 1.280(5) . ?
N31 C31A 1.392(5) . ?
C31A C41 1.397(5) . ?
C31A C71A 1.403(5) . ?
C41 C51 1.382(6) . ?
C41 H21 0.9300 . ?
C51 C61 1.401(7) . ?
C51 H28 0.9300 . ?
C61 C71 1.374(6) . ?
C61 H19 0.9300 . ?
C71 C71A 1.391(5) . ?
C71 H12 0.9300 . ?
C12 C12 1.503(9) 2_565 ?
C12 S2 1.816(4) . ?
C12 H5A 0.90(5) . ?
C12 H7A 0.94(6) . ?
S2 C22 1.746(4) . ?
Se2 C72A 1.874(4) . ?
Se2 C22 1.906(4) . ?
C22 N32 1.286(5) . ?
N32 C32A 1.397(5) . ?
C32A C42 1.395(6) . ?
C32A C72A 1.398(5) . ?
C42 C52 1.379(7) . ?
C42 H29 0.9300 . ?
C52 C62 1.401(8) . ?
C52 H30 0.9300 . ?
C62 C72 1.372(7) . ?
C62 H32 0.9300 . ?
C72 C72A 1.404(5) . ?
C72 H22 0.9300 . ?
C13 C13 1.516(8) 2_777 ?
C13 S3 1.814(4) . ?
C13 H4A 0.98(4) . ?
C13 H6A 0.95(4) . ?
S3 C23 1.743(4) . ?
Se3 C73A 1.870(5) . ?
Se3 C23 1.889(4) . ?
C23 N33 1.293(5) . ?
N33 C33A 1.403(5) . ?
C33A C73A 1.391(6) . ?
C33A C43 1.398(6) . ?
C43 C53 1.392(7) . ?
C43 H25 0.9300 . ?
C53 C63 1.389(9) . ?
C53 H31 0.9300 . ?
C63 C73 1.355(9) . ?
C63 H26 0.9300 . ?
C73 C73A 1.400(6) . ?
C73 H33 0.9300 . ?
