#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/14/2201475.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2201475
loop_
_publ_author_name
'Dupont, Léon'
'Messali, Mouslim'
'Christiaens, Léon'
'Evrard, Guy'
_publ_section_title
;
 2-(2,4-Dibromophenylamino)-7-nitrobenzisoselenazol-3-one
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o828
_journal_page_last               o830
_journal_paper_doi               10.1107/S1600536802011716
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C13 H7 Br2 N3 O3 Se1'
_chemical_formula_moiety         'C13 H7 Br2 N3 O3 Se1'
_chemical_formula_structural     'C13 H7 BR2 N3 O3 Se1'
_chemical_formula_sum            'C13 H7 Br2 N3 O3 Se'
_chemical_formula_weight         492.00
_chemical_name_systematic
;
2-(2,4-Dibromophenylamino)-7-nitrobenzisoselenazol-3-one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.8685(10)
_cell_length_b                   8.6075(10)
_cell_length_c                   25.233(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42
_cell_measurement_theta_min      30
_cell_volume                     3012.1(5)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1992)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and MERCURY 1.1 (Bruno et al., 2002)
;
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3587
_diffrn_reflns_theta_full        74.21
_diffrn_reflns_theta_max         74.21
_diffrn_reflns_theta_min         3.50
_diffrn_standards_decay_%        4
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    9.748
_exptl_absorpt_correction_T_max  0.39
_exptl_absorpt_correction_T_min  0.12
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.170
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.479
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3075
_refine_ls_number_restraints     65
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0307P)²+4.0625P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0850
_reflns_number_gt                2634
_reflns_number_total             3075
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn6034.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C13 H7 Br2 N3 O3 Se1'
_cod_database_code               2201475
_cod_database_fobs_code          2201475
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Br1 0.45930(3) -0.43090(5) 0.685078(19) 0.05383(13) Uani d U 1 . . Br
Se1 0.07210(3) -0.55331(5) 0.625799(16) 0.04735(12) Uani d U 1 . . Se
O1 -0.1873(2) -0.6805(5) 0.53508(13) 0.0817(11) Uani d U 1 . . O
O2 -0.0802(2) -0.7089(4) 0.59704(14) 0.0754(10) Uani d U 1 . . O
O3 0.1866(2) -0.1479(3) 0.58398(12) 0.0601(7) Uani d U 1 . . O
N1 -0.1204(2) -0.6321(5) 0.56236(14) 0.0573(9) Uani d U 1 . . N
N2 0.1609(2) -0.3858(4) 0.62195(13) 0.0458(7) Uani d U 1 . . N
N3 0.2508(2) -0.3935(4) 0.64584(14) 0.0586(9) Uani d U 1 . . N
C1 0.0009(2) -0.4341(4) 0.57868(13) 0.0363(7) Uani d U 1 . . C
C2 -0.0842(2) -0.4770(5) 0.55293(14) 0.0437(8) Uani d U 1 . . C
C3 -0.1287(3) -0.3774(6) 0.51788(15) 0.0558(10) Uani d U 1 . . C
H3 -0.1855 -0.4066 0.5011 0.067 Uiso calc R 1 . . H
C4 -0.0886(3) -0.2354(6) 0.50804(18) 0.0642(11) Uani d U 1 . . C
H4 -0.1192 -0.1669 0.4851 0.077 Uiso calc R 1 . . H
C5 -0.0030(3) -0.1925(5) 0.53181(17) 0.0594(10) Uani d U 1 . . C
H5 0.0243 -0.0964 0.5243 0.071 Uiso calc R 1 . . H
C6 0.0419(2) -0.2927(4) 0.56680(13) 0.0393(7) Uani d U 1 . . C
C7 0.1369(2) -0.2630(4) 0.59101(14) 0.0405(7) Uani d U 1 . . C
C8 0.2624(2) -0.3346(4) 0.69654(14) 0.0385(7) Uani d U 1 A . C
C9 0.3540(2) -0.3362(4) 0.71998(14) 0.0409(7) Uani d U 1 . . C
C10 0.3698(3) -0.2662(5) 0.76868(14) 0.0501(9) Uani d DU 1 A . C
H10 0.4310 -0.2674 0.7838 0.060 Uiso calc R 1 . . H
C11 0.2948(3) -0.1954(5) 0.79452(14) 0.0527(10) Uani d DU 1 . . C
C12 0.2028(3) -0.1971(5) 0.77336(15) 0.0502(9) Uani d DU 1 A . C
H12 0.1518 -0.1527 0.7918 0.060 Uiso calc R 1 . . H
Br2A 0.3242(5) -0.1240(5) 0.8616(2) 0.0771(11) Uani d PDU 0.45 A 1 Br
Br2B 0.3151(4) -0.0715(4) 0.85772(16) 0.0672(7) Uani d PDU 0.55 A 2 Br
C13 0.1874(2) -0.2655(5) 0.72455(15) 0.0480(9) Uani d U 1 . . C
H13 0.1256 -0.2652 0.7101 0.058 Uiso calc R 1 A . H
H30 0.291(3) -0.467(5) 0.6308(16) 0.058 Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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_publ_flag
C1 Se1 N2 83.82(14) yes
O1 N1 O2 123.9(4) yes
O1 N1 C2 118.9(4) ?
O2 N1 C2 117.1(3) ?
C7 N2 N3 120.6(3) yes
C7 N2 Se1 117.5(2) yes
N3 N2 Se1 121.6(3) yes
C8 N3 N2 119.3(3) yes
C6 C1 C2 118.8(3) ?
C6 C1 Se1 114.2(2) ?
C2 C1 Se1 127.0(3) ?
C3 C2 C1 120.8(4) ?
C3 C2 N1 121.7(3) ?
C1 C2 N1 117.4(3) ?
C4 C3 C2 119.4(4) ?
C3 C4 C5 120.7(4) ?
C4 C5 C6 119.9(4) ?
C1 C6 C5 120.3(3) ?
C1 C6 C7 115.6(3) ?
C5 C6 C7 124.0(4) ?
O3 C7 N2 125.3(3) ?
O3 C7 C6 125.8(3) ?
N2 C7 C6 108.9(3) ?
N3 C8 C13 122.6(3) ?
N3 C8 C9 119.5(3) ?
C13 C8 C9 117.9(3) ?
C10 C9 C8 120.9(3) ?
C10 C9 Br1 118.6(2) ?
C8 C9 Br1 120.5(3) ?
C11 C10 C9 119.7(3) ?
C10 C11 C12 120.7(4) ?
C10 C11 Br2A 114.6(3) ?
C12 C11 Br2A 124.1(4) ?
C10 C11 Br2B 121.7(3) ?
C12 C11 Br2B 117.2(4) ?
Br2A C11 Br2B 14.3(2) ?
C13 C12 C11 119.5(4) ?
C12 C13 C8 121.2(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C9 . 1.890(4) yes
Se1 C1 . 1.855(3) yes
Se1 N2 . 1.899(3) yes
O1 N1 . 1.228(4) yes
O2 N1 . 1.230(5) yes
O3 C7 . 1.220(4) yes
N1 C2 . 1.446(5) yes
N2 C7 . 1.355(5) yes
N2 N3 . 1.386(4) yes
N3 C8 . 1.385(5) yes
C1 C6 . 1.376(5) ?
C1 C2 . 1.397(4) ?
C2 C3 . 1.377(6) ?
C3 C4 . 1.365(7) ?
C4 C5 . 1.380(6) ?
C5 C6 . 1.382(5) ?
C6 C7 . 1.475(4) ?
C8 C13 . 1.392(5) ?
C8 C9 . 1.401(4) ?
C9 C10 . 1.386(5) ?
C10 C11 . 1.370(6) ?
C11 C12 . 1.383(5) ?
C11 Br2A . 1.847(6) yes
C11 Br2B . 1.939(6) yes
C12 C13 . 1.382(5) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H30 O3 8_655 0.93(4) 1.98(4) 2.826(4) 151(4)
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_publ_flag
C1 Se1 N2 C7 1.2(3) yes
C1 Se1 N2 N3 -173.1(3) yes
Se1 N2 N3 C8 -93.8(4) yes
