#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:43:24 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180312 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/26/7152651.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_7152651
loop_
_publ_author_name
'Lamani, Devappa S.'
'Bhowmick, Debasish'
'Mugesh, Govindasamy'
_publ_section_title
;
 Spirodiazaselenuranes: synthesis, structure and antioxidant activity.
;
_journal_issue                   39
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7933
_journal_page_last               7943
_journal_paper_doi               10.1039/c2ob26156a
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C27 H16 Br2 N2 O6 Se'
_chemical_formula_sum            'C27 H16 Br2 N2 O6 Se'
_chemical_formula_weight         703.20
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 121.836(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.023(2)
_cell_length_b                   13.153(2)
_cell_length_c                   11.8836(18)
_cell_measurement_temperature    293(2)
_cell_volume                     2791.7(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1999)'
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0803
_diffrn_reflns_av_sigmaI/netI    0.1168
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10237
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    4.250
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5105
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.1612
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0875P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1843
_reflns_number_gt                1501
_reflns_number_total             3218
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2ob26156a.txt
_cod_data_source_block           c18
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7152651
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'
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
Se1 Se 0.5000 0.06856(6) 0.7500 0.0513(3) Uani 1 2 d S
Br1 Br 0.84081(6) -0.19680(7) 0.90628(13) 0.1304(5) Uani 1 1 d .
N1 N 0.5670(3) 0.0780(3) 0.6712(5) 0.0535(12) Uani 1 1 d .
O1 O 0.5505(2) 0.1143(4) 0.4667(4) 0.0784(13) Uani 1 1 d .
O2 O 0.4676(6) 0.4467(7) 0.8254(12) 0.229(5) Uani 1 1 d .
O3 O 0.5756(11) 0.5526(12) 0.8217(13) 0.460(16) Uani 1 1 d .
C1 C 0.4394(3) 0.1641(4) 0.6085(6) 0.0539(15) Uani 1 1 d .
C2 C 0.3773(4) 0.2128(5) 0.5936(7) 0.0728(19) Uani 1 1 d .
H2 H 0.3620 0.2038 0.6536 0.087 Uiso 1 1 calc R
C3 C 0.3388(4) 0.2758(6) 0.4842(9) 0.096(3) Uani 1 1 d .
H3 H 0.2969 0.3111 0.4702 0.115 Uiso 1 1 calc R
C4 C 0.3621(5) 0.2867(6) 0.3958(8) 0.102(3) Uani 1 1 d .
H4 H 0.3355 0.3298 0.3235 0.123 Uiso 1 1 calc R
C5 C 0.4232(4) 0.2359(6) 0.4115(8) 0.084(2) Uani 1 1 d .
H5 H 0.4371 0.2424 0.3495 0.101 Uiso 1 1 calc R
C6 C 0.4636(4) 0.1748(4) 0.5220(7) 0.0608(17) Uani 1 1 d .
C7 C 0.5305(3) 0.1198(4) 0.5470(6) 0.0563(15) Uani 1 1 d .
C8 C 0.6318(3) 0.0175(4) 0.7249(6) 0.0565(15) Uani 1 1 d .
C9 C 0.6498(4) -0.0491(6) 0.8292(7) 0.087(2) Uani 1 1 d .
H9 H 0.6180 -0.0531 0.8613 0.104 Uiso 1 1 calc R
C10 C 0.7124(4) -0.1085(6) 0.8856(8) 0.092(2) Uani 1 1 d .
H10 H 0.7236 -0.1500 0.9571 0.110 Uiso 1 1 calc R
C11 C 0.7590(4) -0.1071(6) 0.8373(8) 0.082(2) Uani 1 1 d .
C12 C 0.7443(4) -0.0431(6) 0.7374(9) 0.093(3) Uani 1 1 d .
H12 H 0.7763 -0.0414 0.7055 0.111 Uiso 1 1 calc R
C13 C 0.6820(4) 0.0200(5) 0.6819(8) 0.076(2) Uani 1 1 d .
H13 H 0.6736 0.0648 0.6149 0.092 Uiso 1 1 calc R
C14 C 0.5000 0.4939(11) 0.7500 0.134(5) Uani 1 2 d S
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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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
C1 Se1 C1 99.3(3) 2_656 .
C1 Se1 N1 93.5(2) 2_656 .
C1 Se1 N1 82.0(2) . .
C1 Se1 N1 82.0(2) 2_656 2_656
C1 Se1 N1 93.5(2) . 2_656
N1 Se1 N1 173.1(3) . 2_656
C7 N1 C8 125.2(5) . .
C7 N1 Se1 112.5(4) . .
C8 N1 Se1 119.2(4) . .
C6 C1 C2 123.7(6) . .
C6 C1 Se1 112.5(4) . .
C2 C1 Se1 123.7(5) . .
C1 C2 C3 116.2(7) . .
C4 C3 C2 120.7(7) . .
C5 C4 C3 121.9(7) . .
C4 C5 C6 118.3(7) . .
C1 C6 C5 119.1(6) . .
C1 C6 C7 119.4(6) . .
C5 C6 C7 121.4(6) . .
O1 C7 N1 125.8(6) . .
O1 C7 C6 123.8(6) . .
N1 C7 C6 110.5(5) . .
C13 C8 C9 115.9(6) . .
C13 C8 N1 123.9(6) . .
C9 C8 N1 120.2(5) . .
C10 C9 C8 122.3(6) . .
C9 C10 C11 120.2(7) . .
C12 C11 C10 119.6(7) . .
C12 C11 Br1 120.4(5) . .
C10 C11 Br1 120.0(6) . .
C11 C12 C13 120.7(6) . .
C12 C13 C8 121.2(7) . .
O2 C14 O2 131.7(12) 2_656 .
O2 C14 O3 83.1(8) 2_656 .
O2 C14 O3 121.8(7) . .
O2 C14 O3 121.8(7) 2_656 2_656
O2 C14 O3 83.1(8) . 2_656
O3 C14 O3 120.4(18) . 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 C1 1.941(6) 2_656
Se1 C1 1.941(6) .
Se1 N1 2.067(4) .
Se1 N1 2.067(4) 2_656
Br1 C11 1.881(7) .
N1 C7 1.369(7) .
N1 C8 1.406(8) .
O1 C7 1.231(6) .
O2 C14 1.515(9) .
O3 C14 1.555(17) .
C1 C6 1.373(8) .
C1 C2 1.381(9) .
C2 C3 1.387(10) .
C3 C4 1.379(11) .
C4 C5 1.371(10) .
C5 C6 1.384(9) .
C6 C7 1.466(8) .
C8 C13 1.396(8) .
C8 C9 1.397(9) .
C9 C10 1.365(9) .
C10 C11 1.371(9) .
C11 C12 1.351(10) .
C12 C13 1.389(9) .
C14 O2 1.515(9) 2_656
C14 O3 1.555(17) 2_656
