#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:07:09 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180375 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/44/7204428.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_7204428
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           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.5239(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.3534(4)
_cell_length_b                   5.3820(2)
_cell_length_c                   19.3559(6)
_cell_measurement_reflns_used    3249
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      1.00
_cell_volume                     1595.46(9)
_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      200(2)
_diffrn_detector_area_resol_mean 0.055
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method
;
346 frames in 4 sets of ω scans. Rotation/frame=1°.
Crystal-detector distance=25 mm. Measuring time=30 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  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5500
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.75
_exptl_absorpt_coefficient_mu    4.893
_exptl_absorpt_correction_T_max  0.854
_exptl_absorpt_correction_T_min  0.520
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
contained in maXus (Mackay et al., 1998)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.891
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.0011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2922
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0377P)²+1.0904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                2259
_reflns_number_total             2922
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b203317h.txt
_cod_data_source_block           12
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P 21/n'
_cod_database_code               7204428
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'
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
Se11 Se 0.74461(3) 0.10120(9) 0.02061(3) 0.03767(17) Uani 1 1 d . . .
C21 C 0.6596(3) 0.3523(8) -0.0120(2) 0.0309(10) Uani 1 1 d . . .
S11 S 0.64548(9) 0.5221(2) -0.08681(7) 0.0426(3) Uani 1 1 d . . .
N31 N 0.6131(2) 0.3702(6) 0.03426(19) 0.0278(8) Uani 1 1 d . . .
C31 C 0.5436(3) 0.5556(9) 0.0219(3) 0.0307(10) Uani 1 1 d D . .
H1 H 0.555(3) 0.677(8) 0.002(2) 0.016(11) Uiso 1 1 d D . .
H2 H 0.541(3) 0.604(8) 0.057(2) 0.014(11) Uiso 1 1 d D . .
C31A C 0.6325(3) 0.1968(8) 0.0921(2) 0.0284(9) Uani 1 1 d . . .
C41 C 0.5887(3) 0.1782(8) 0.1421(2) 0.0325(10) Uani 1 1 d . . .
H41 H 0.5423 0.2887 0.1393 0.039 Uiso 1 1 calc R . .
C51 C 0.6139(3) -0.0037(8) 0.1956(2) 0.0343(10) Uani 1 1 d . . .
H51 H 0.5847 -0.0172 0.2301 0.041 Uiso 1 1 calc R . .
C61 C 0.6812(3) -0.1678(8) 0.1999(2) 0.0342(10) Uani 1 1 d . . .
H61 H 0.6978 -0.2913 0.2374 0.041 Uiso 1 1 calc R . .
C71 C 0.7242(3) -0.1518(8) 0.1499(3) 0.0333(10) Uani 1 1 d . . .
H71 H 0.7695 -0.2657 0.1521 0.040 Uiso 1 1 calc R . .
C71A C 0.7004(3) 0.0325(8) 0.0965(2) 0.0291(10) Uani 1 1 d . . .
Se12 Se 0.97762(3) 1.00200(9) 0.22023(3) 0.03653(16) Uani 1 1 d . . .
C22 C 0.9696(3) 0.8717(7) 0.1285(2) 0.0278(9) Uani 1 1 d . . .
S22 S 0.90214(7) 0.6407(2) 0.08744(6) 0.0332(3) Uani 1 1 d . . .
N32 N 1.0255(2) 0.9916(6) 0.10162(19) 0.0256(7) Uani 1 1 d . . .
C32 C 1.0316(4) 0.9251(11) 0.0306(3) 0.0285(10) Uani 1 1 d D . .
H3 H 1.076(3) 0.944(7) 0.032(2) 0.012(12) Uiso 1 1 d D . .
H4 H 1.023(3) 0.807(7) 0.029(2) 0.006(13) Uiso 1 1 d D . .
C32A C 1.0749(3) 1.1872(8) 0.1449(2) 0.0267(9) Uani 1 1 d . . .
C42 C 1.1326(3) 1.3403(8) 0.1248(2) 0.0317(10) Uani 1 1 d . . .
H42 H 1.1425 1.3160 0.0798 0.038 Uiso 1 1 calc R . .
C52 C 1.1743(3) 1.5275(8) 0.1732(3) 0.0379(11) Uani 1 1 d . . .
H52 H 1.2131 1.6345 0.1606 0.045 Uiso 1 1 calc R . .
C62 C 1.1615(3) 1.5642(9) 0.2394(3) 0.0401(12) Uani 1 1 d . . .
H62 H 1.1917 1.6938 0.2715 0.048 Uiso 1 1 calc R . .
C72 C 1.1042(3) 1.4116(8) 0.2593(3) 0.0353(11) Uani 1 1 d . . .
H72 H 1.0950 1.4362 0.3046 0.042 Uiso 1 1 calc R . .
C72A C 1.0612(3) 1.2235(8) 0.2115(2) 0.0294(10) Uani 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
C21 Se11 C71A 87.87(19) . . ?
N31 C21 S11 126.4(3) . . ?
N31 C21 Se11 110.2(3) . . ?
S11 C21 Se11 123.3(2) . . ?
C21 N31 C31A 116.9(3) . . ?
C21 N31 C31 121.2(4) . . ?
C31A N31 C31 121.8(4) . . ?
N31 C31 C31 110.4(5) . 3_665 ?
N31 C31 H1 109(3) . . ?
C31 C31 H1 112(3) 3_665 . ?
N31 C31 H2 112(3) . . ?
C31 C31 H2 108(3) 3_665 . ?
H1 C31 H2 105(4) . . ?
C41 C31A C71A 120.2(4) . . ?
C41 C31A N31 124.9(4) . . ?
C71A C31A N31 114.9(4) . . ?
C51 C41 C31A 118.7(4) . . ?
C51 C41 H41 120.6 . . ?
C31A C41 H41 120.6 . . ?
C41 C51 C61 121.2(4) . . ?
C41 C51 H51 119.4 . . ?
C61 C51 H51 119.4 . . ?
C71 C61 C51 120.2(4) . . ?
C71 C61 H61 119.9 . . ?
C51 C61 H61 119.9 . . ?
C61 C71 C71A 119.2(4) . . ?
C61 C71 H71 120.4 . . ?
C71A C71 H71 120.4 . . ?
C71 C71A C31A 120.4(4) . . ?
C71 C71A Se11 129.5(3) . . ?
C31A C71A Se11 110.0(3) . . ?
C72A Se12 C22 87.92(18) . . ?
N32 C22 S22 126.3(3) . . ?
N32 C22 Se12 110.6(3) . . ?
S22 C22 Se12 123.1(2) . . ?
C22 N32 C32A 116.6(3) . . ?
C22 N32 C32 121.4(4) . . ?
C32A N32 C32 122.0(4) . . ?
N32 C32 C32 110.9(5) . 3_775 ?
N32 C32 H3 109(3) . . ?
C32 C32 H3 111(3) 3_775 . ?
N32 C32 H4 102(4) . . ?
C32 C32 H4 113(4) 3_775 . ?
H3 C32 H4 110(5) . . ?
C72A C32A C42 120.9(4) . . ?
C72A C32A N32 114.1(4) . . ?
C42 C32A N32 124.9(4) . . ?
C52 C42 C32A 117.3(4) . . ?
C52 C42 H42 121.3 . . ?
C32A C42 H42 121.3 . . ?
C42 C52 C62 122.2(4) . . ?
C42 C52 H52 118.9 . . ?
C62 C52 H52 118.9 . . ?
C52 C62 C72 120.4(4) . . ?
C52 C62 H62 119.8 . . ?
C72 C62 H62 119.8 . . ?
C72A C72 C62 118.6(4) . . ?
C72A C72 H72 120.7 . . ?
C62 C72 H72 120.7 . . ?
C72 C72A C32A 120.6(4) . . ?
C72 C72A Se12 128.6(3) . . ?
C32A C72A Se12 110.7(3) . . ?
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
Se11 C21 1.882(4) . ?
Se11 C71A 1.887(4) . ?
C21 N31 1.367(5) . ?
C21 S11 1.658(4) . ?
N31 C31A 1.406(5) . ?
N31 C31 1.467(6) . ?
C31 C31 1.505(10) 3_665 ?
C31 H1 0.82(4) . ?
C31 H2 0.75(4) . ?
C31A C41 1.395(6) . ?
C31A C71A 1.399(6) . ?
C41 C51 1.379(6) . ?
C41 H41 0.9500 . ?
C51 C61 1.391(6) . ?
C51 H51 0.9500 . ?
C61 C71 1.385(6) . ?
C61 H61 0.9500 . ?
C71 C71A 1.386(6) . ?
C71 H71 0.9500 . ?
Se12 C72A 1.865(4) . ?
Se12 C22 1.871(4) . ?
C22 N32 1.363(5) . ?
C22 S22 1.667(4) . ?
N32 C32A 1.410(5) . ?
N32 C32 1.457(6) . ?
C32 C32 1.506(10) 3_775 ?
C32 H3 0.72(4) . ?
C32 H4 0.65(4) . ?
C32A C72A 1.398(6) . ?
C32A C42 1.407(6) . ?
C42 C52 1.382(7) . ?
C42 H42 0.9500 . ?
C52 C62 1.384(7) . ?
C52 H52 0.9500 . ?
C62 C72 1.397(7) . ?
C62 H62 0.9500 . ?
C72 C72A 1.385(6) . ?
C72 H72 0.9500 . ?
