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#$Date: 2016-03-25 10:09:59 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179742 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/38/7003801.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_7003801
loop_
_publ_author_name
'Dutton, Jason L.'
'Sutrisno, Andre'
'Schurko, Robert W.'
'Ragogna, Paul J.'
_publ_section_title
;
 Synthesis and characterization of cationic selenium--nitrogen
 heterocycles from tert-butyl-DAB (DAB =
 1,4-di-tert-butyl-1,3-diazabutadiene) and SeX4via the reductive
 elimination of X2 (X = Cl, Br): a distinct contrast with tellurium
;
_journal_issue                   26
_journal_name_full               'Dalton Transactions'
_journal_page_first              3470
_journal_page_last               3477
_journal_paper_doi               10.1039/b719779a
_journal_year                    2008
_chemical_formula_sum            'C6 H11 Br N2 Se'
_chemical_formula_weight         270.04
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 104.47(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7366(19)
_cell_length_b                   9.3214(19)
_cell_length_c                   10.070(2)
_cell_measurement_reflns_used    2112
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.70
_cell_volume                     884.9(3)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2001)'
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full .995
_diffrn_measured_fraction_theta_max .995
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_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  0.0634
_diffrn_reflns_av_sigmaI/netI    0.0688
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3767
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.689
_exptl_absorpt_correction_T_max  0.3556
_exptl_absorpt_correction_T_min  0.2754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            block
_exptl_crystal_density_diffrn    2.027
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       yellow
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.146
_refine_diff_density_min         -1.235
_refine_diff_density_rms         .224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         2022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0487
_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)+(0.0721P)²+0.4337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1323
_reflns_number_gt                1600
_reflns_number_total             2022
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b719779a.txt
_cod_data_source_block           06095
_cod_original_cell_volume        885.0(3)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7003801
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br1 Br -0.21127(6) -0.00832(6) 0.36769(6) 0.0238(2) Uani 1 1 d . . .
Se1 Se 0.02672(6) 0.03694(7) 0.26732(5) 0.0194(2) Uani 1 1 d . . .
N1 N -0.0881(5) 0.1346(5) 0.1284(5) 0.0233(10) Uani 1 1 d . . .
C1 C -0.0199(6) 0.1841(6) 0.0434(6) 0.0228(12) Uani 1 1 d . . .
H1A H -0.0669 0.2400 -0.0334 0.027 Uiso 1 1 calc R . .
C2 C 0.1267(6) 0.1531(6) 0.0674(5) 0.0207(12) Uani 1 1 d . . .
H2A H 0.1831 0.1846 0.0085 0.025 Uiso 1 1 calc R . .
N2 N 0.1767(5) 0.0783(5) 0.1765(4) 0.0179(10) Uani 1 1 d . . .
C3 C 0.3283(6) 0.0367(6) 0.2319(5) 0.0201(12) Uani 1 1 d . . .
C6 C 0.3329(6) -0.1135(7) 0.2925(6) 0.0278(13) Uani 1 1 d . . .
H6A H 0.2808 -0.1143 0.3641 0.042 Uiso 1 1 calc R . .
H6B H 0.4318 -0.1411 0.3322 0.042 Uiso 1 1 calc R . .
H6C H 0.2892 -0.1815 0.2201 0.042 Uiso 1 1 calc R . .
C5 C 0.3927(6) 0.1446(6) 0.3436(6) 0.0235(12) Uani 1 1 d . . .
H5A H 0.3740 0.2421 0.3073 0.035 Uiso 1 1 calc R . .
H5B H 0.4953 0.1290 0.3741 0.035 Uiso 1 1 calc R . .
H5C H 0.3501 0.1320 0.4214 0.035 Uiso 1 1 calc R . .
C4 C 0.4068(6) 0.0387(8) 0.1181(6) 0.0310(15) Uani 1 1 d . . .
H4A H 0.3552 -0.0202 0.0411 0.047 Uiso 1 1 calc R . .
H4B H 0.5026 0.0000 0.1534 0.047 Uiso 1 1 calc R . .
H4C H 0.4129 0.1375 0.0870 0.047 Uiso 1 1 calc R . .
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
Br1 0.0193(3) 0.0239(4) 0.0296(4) 0.0013(2) 0.0090(3) -0.0008(2)
Se1 0.0175(3) 0.0213(4) 0.0201(3) 0.0008(2) 0.0060(2) 0.0022(2)
N1 0.022(2) 0.021(3) 0.027(3) -0.004(2) 0.007(2) 0.002(2)
C1 0.025(3) 0.019(3) 0.022(3) 0.003(2) 0.002(2) 0.003(2)
C2 0.025(3) 0.015(3) 0.023(3) -0.002(2) 0.006(2) 0.001(2)
N2 0.019(2) 0.017(2) 0.020(2) 0.0014(19) 0.0097(18) -0.0002(19)
C3 0.016(3) 0.029(3) 0.016(3) 0.003(2) 0.004(2) 0.003(2)
C6 0.028(3) 0.021(3) 0.035(3) 0.003(3) 0.009(3) 0.004(3)
C5 0.025(3) 0.018(3) 0.028(3) 0.001(2) 0.008(2) 0.001(2)
C4 0.028(3) 0.043(4) 0.025(3) 0.000(3) 0.013(3) 0.000(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -.2901 2.4595 '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
N1 Se1 N2 85.9(2) . . ?
N1 Se1 Br1 86.97(15) . . ?
N2 Se1 Br1 172.76(13) . . ?
C1 N1 Se1 111.8(4) . . ?
N1 C1 C2 118.5(5) . . ?
N1 C1 H1A 120.8 . . ?
C2 C1 H1A 120.8 . . ?
N2 C2 C1 113.9(5) . . ?
N2 C2 H2A 123.0 . . ?
C1 C2 H2A 123.0 . . ?
C2 N2 C3 125.9(4) . . ?
C2 N2 Se1 109.9(4) . . ?
C3 N2 Se1 124.1(3) . . ?
N2 C3 C5 106.9(4) . . ?
N2 C3 C6 108.4(4) . . ?
C5 C3 C6 110.2(4) . . ?
N2 C3 C4 110.5(4) . . ?
C5 C3 C4 110.8(5) . . ?
C6 C3 C4 109.9(5) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
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
Br1 Se1 2.7820(10) . ?
Se1 N1 1.804(5) . ?
Se1 N2 1.945(4) . ?
N1 C1 1.293(7) . ?
C1 C2 1.417(7) . ?
C1 H1A 0.9500 . ?
C2 N2 1.289(7) . ?
C2 H2A 0.9500 . ?
N2 C3 1.493(7) . ?
C3 C5 1.522(8) . ?
C3 C6 1.523(8) . ?
C3 C4 1.528(7) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Se1 N1 C1 -1.3(4) . . . . ?
Br1 Se1 N1 C1 179.8(4) . . . . ?
Se1 N1 C1 C2 1.7(7) . . . . ?
N1 C1 C2 N2 -1.0(8) . . . . ?
C1 C2 N2 C3 -176.3(5) . . . . ?
C1 C2 N2 Se1 -0.1(6) . . . . ?
N1 Se1 N2 C2 0.8(4) . . . . ?
Br1 Se1 N2 C2 9.7(14) . . . . ?
N1 Se1 N2 C3 177.0(4) . . . . ?
Br1 Se1 N2 C3 -174.1(9) . . . . ?
C2 N2 C3 C5 97.4(6) . . . . ?
Se1 N2 C3 C5 -78.3(5) . . . . ?
C2 N2 C3 C6 -143.8(5) . . . . ?
Se1 N2 C3 C6 40.6(6) . . . . ?
C2 N2 C3 C4 -23.3(8) . . . . ?
Se1 N2 C3 C4 161.1(4) . . . . ?
