#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/92/2229225.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_2229225
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Goh, Jia Hao'
'Maity, Annada C.'
'Goswami, Shyamaprosad'
_publ_section_title
;
 Bis(2,1,3-benzoselenadiazole-κN)dibromidocopper(II)
;
_journal_coeditor_code           SJ5081
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m181
_journal_page_last               m182
_journal_paper_doi               10.1107/S160053681005422X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu Br2 (C6 H4 N2 Se)2]'
_chemical_formula_moiety         'C12 H8 Br2 Cu1 N4 Se2'
_chemical_formula_sum            'C12 H8 Br2 Cu N4 Se2'
_chemical_formula_weight         589.50
_chemical_name_systematic
;
Bis(2,1,3-benzoselenadiazole-κN)dibromidocopper(II)
;
_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                94.6270(10)
_cell_angle_beta                 109.6400(10)
_cell_angle_gamma                102.6900(10)
_cell_formula_units_Z            2
_cell_length_a                   8.34060(10)
_cell_length_b                   9.58530(10)
_cell_length_c                   10.29080(10)
_cell_measurement_reflns_used    9451
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      39.80
_cell_measurement_theta_min      2.13
_cell_volume                     745.165(16)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_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  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            47530
_diffrn_reflns_theta_full        39.80
_diffrn_reflns_theta_max         39.80
_diffrn_reflns_theta_min         2.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    11.708
_exptl_absorpt_correction_T_max  0.5500
_exptl_absorpt_correction_T_min  0.0636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             550
_exptl_crystal_size_max          0.524
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.957
_refine_diff_density_min         -1.275
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         9041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0250P)²+0.1897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0658
_reflns_number_gt                6854
_reflns_number_total             9041
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5081.cif
_cod_data_source_block           I
_cod_original_cell_volume        745.165(14)
_cod_database_code               2229225
_cod_database_fobs_code          2229225
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
Cu Cu1 0.76323(3) 0.96053(2) 0.46923(2) 0.01342(4) Uani d . 1 . .
Se Se1 0.76418(3) 1.00702(2) 0.790290(19) 0.01462(4) Uani d . 1 . .
Se Se2 0.76370(3) 0.96029(2) 0.148426(18) 0.01419(4) Uani d . 1 . .
Br Br1 0.50628(3) 0.76430(2) 0.346275(19) 0.01659(4) Uani d . 1 . .
Br Br2 0.99180(3) 1.18054(2) 0.602981(19) 0.01630(4) Uani d . 1 . .
N N1 0.7843(2) 0.89074(17) 0.65184(16) 0.0145(3) Uani d . 1 . .
N N2 0.7949(2) 0.87760(18) 0.90445(16) 0.0157(3) Uani d . 1 . .
N N3 0.7309(2) 1.05001(17) 0.29546(16) 0.0145(3) Uani d . 1 . .
N N4 0.7204(2) 1.10188(18) 0.05009(16) 0.0156(3) Uani d . 1 . .
C C1 0.8108(2) 0.7679(2) 0.69755(18) 0.0141(3) Uani d . 1 . .
C C2 0.8325(3) 0.6474(2) 0.6210(2) 0.0168(3) Uani d . 1 . .
H H2 0.8267 0.6476 0.5292 0.020 Uiso calc R 1 . .
C C3 0.8621(3) 0.5318(2) 0.6854(2) 0.0188(3) Uani d . 1 . .
H H3 0.8784 0.4535 0.6365 0.023 Uiso calc R 1 . .
C C4 0.8690(3) 0.5269(2) 0.8263(2) 0.0188(3) Uani d . 1 . .
H H4 0.8888 0.4456 0.8660 0.023 Uiso calc R 1 . .
C C5 0.8472(3) 0.6385(2) 0.9022(2) 0.0180(3) Uani d . 1 . .
H H5 0.8509 0.6343 0.9931 0.022 Uiso calc R 1 . .
C C6 0.8185(2) 0.7628(2) 0.83934(19) 0.0149(3) Uani d . 1 . .
C C7 0.6893(2) 1.1727(2) 0.26414(18) 0.0139(3) Uani d . 1 . .
C C8 0.6457(3) 1.2712(2) 0.34984(19) 0.0168(3) Uani d . 1 . .
H H8 0.6437 1.2531 0.4368 0.020 Uiso calc R 1 . .
C C9 0.6071(3) 1.3927(2) 0.3011(2) 0.0188(3) Uani d . 1 . .
H H9 0.5777 1.4572 0.3560 0.023 Uiso calc R 1 . .
C C10 0.6102(3) 1.4242(2) 0.1680(2) 0.0199(4) Uani d . 1 . .
H H10 0.5866 1.5097 0.1401 0.024 Uiso calc R 1 . .
C C11 0.6472(3) 1.3311(2) 0.0817(2) 0.0181(3) Uani d . 1 . .
H H11 0.6471 1.3515 -0.0052 0.022 Uiso calc R 1 . .
C C12 0.6860(2) 1.2015(2) 0.12748(18) 0.0147(3) Uani d . 1 . .
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'
Cu Cu 0.3201 1.2651 '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'
Br Br -0.2901 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 Cu1 N1 . . 172.82(6) ?
N3 Cu1 Br1 . . 90.80(5) ?
N1 Cu1 Br1 . . 91.11(5) ?
N3 Cu1 Br2 . . 89.08(5) ?
N1 Cu1 Br2 . . 87.91(5) ?
Br1 Cu1 Br2 . . 170.661(12) ?
N2 Se1 N1 . . 92.13(7) ?
N4 Se2 N3 . . 92.13(7) ?
C1 N1 Se1 . . 108.34(12) ?
C1 N1 Cu1 . . 132.71(13) ?
Se1 N1 Cu1 . . 118.95(8) ?
C6 N2 Se1 . . 108.82(12) ?
C7 N3 Se2 . . 108.91(12) ?
C7 N3 Cu1 . . 131.38(13) ?
Se2 N3 Cu1 . . 119.70(8) ?
C12 N4 Se2 . . 108.23(12) ?
N1 C1 C2 . . 126.44(16) ?
N1 C1 C6 . . 114.38(16) ?
C2 C1 C6 . . 119.18(16) ?
C3 C2 C1 . . 118.50(17) ?
C3 C2 H2 . . 120.7 ?
C1 C2 H2 . . 120.7 ?
C2 C3 C4 . . 122.18(18) ?
C2 C3 H3 . . 118.9 ?
C4 C3 H3 . . 118.9 ?
C5 C4 C3 . . 121.22(18) ?
C5 C4 H4 . . 119.4 ?
C3 C4 H4 . . 119.4 ?
C4 C5 C6 . . 118.41(17) ?
C4 C5 H5 . . 120.8 ?
C6 C5 H5 . . 120.8 ?
N2 C6 C5 . . 123.19(17) ?
N2 C6 C1 . . 116.30(16) ?
C5 C6 C1 . . 120.50(17) ?
N3 C7 C8 . . 126.26(16) ?
N3 C7 C12 . . 114.19(16) ?
C8 C7 C12 . . 119.53(16) ?
C9 C8 C7 . . 118.33(17) ?
C9 C8 H8 . . 120.8 ?
C7 C8 H8 . . 120.8 ?
C8 C9 C10 . . 122.20(18) ?
C8 C9 H9 . . 118.9 ?
C10 C9 H9 . . 118.9 ?
C11 C10 C9 . . 121.24(18) ?
C11 C10 H10 . . 119.4 ?
C9 C10 H10 . . 119.4 ?
C10 C11 C12 . . 118.52(17) ?
C10 C11 H11 . . 120.7 ?
C12 C11 H11 . . 120.7 ?
N4 C12 C11 . . 123.37(17) ?
N4 C12 C7 . . 116.52(16) ?
C11 C12 C7 . . 120.11(17) ?
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
Cu1 N3 . 2.0077(15) ?
Cu1 N1 . 2.0106(15) ?
Cu1 Br1 . 2.3987(3) ?
Cu1 Br2 . 2.4449(3) ?
Se1 N2 . 1.7768(15) ?
Se1 N1 . 1.8131(16) ?
Se2 N4 . 1.7854(15) ?
Se2 N3 . 1.8097(15) ?
N1 C1 . 1.339(2) ?
N2 C6 . 1.328(2) ?
N3 C7 . 1.331(2) ?
N4 C12 . 1.334(2) ?
C1 C2 . 1.424(3) ?
C1 C6 . 1.444(2) ?
C2 C3 . 1.362(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.437(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.354(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.429(3) ?
C5 H5 . 0.9300 ?
C7 C8 . 1.426(3) ?
C7 C12 . 1.448(2) ?
C8 C9 . 1.365(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.433(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.363(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.428(3) ?
C11 H11 . 0.9300 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cu1 N3 2.0077(15) . . yes
Cu1 N1 2.0106(15) . . yes
Cu1 Br1 2.3987(3) . . yes
Cu1 Br2 2.4449(3) . . yes
Se1 N2 1.7768(15) . . yes
Se1 N1 1.8131(16) . . yes
Se2 N4 1.7854(15) . . yes
Se2 N3 1.8097(15) . . yes
Se1 Br1 3.5223(3) . 2_676 yes
Se2 N2 2.6848(16) . 1_554 yes
N2 N4 2.819(2) . 1_556 yes
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
_geom_hbond_publ_flag
C2 H2 Br2 2_776 0.93 2.74 3.464(2) 135 yes
C8 H8 Br1 2_676 0.93 2.90 3.762(2) 154 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N2 Se1 N1 C1 . . . . 0.24(14) ?
N2 Se1 N1 Cu1 . . . . 179.82(10) ?
Br1 Cu1 N1 C1 . . . . 61.95(18) ?
Br2 Cu1 N1 C1 . . . . -127.35(18) ?
Br1 Cu1 N1 Se1 . . . . -117.52(8) ?
Br2 Cu1 N1 Se1 . . . . 53.19(8) ?
N1 Se1 N2 C6 . . . . 0.48(14) ?
N4 Se2 N3 C7 . . . . 0.87(14) ?
N4 Se2 N3 Cu1 . . . . -178.25(10) ?
Br1 Cu1 N3 C7 . . . . 112.79(17) ?
Br2 Cu1 N3 C7 . . . . -57.87(17) ?
Br1 Cu1 N3 Se2 . . . . -68.31(9) ?
Br2 Cu1 N3 Se2 . . . . 121.03(9) ?
N3 Se2 N4 C12 . . . . -0.07(14) ?
Se1 N1 C1 C2 . . . . 179.64(16) ?
Cu1 N1 C1 C2 . . . . 0.1(3) ?
Se1 N1 C1 C6 . . . . -0.9(2) ?
Cu1 N1 C1 C6 . . . . 179.63(13) ?
N1 C1 C2 C3 . . . . 178.66(19) ?
C6 C1 C2 C3 . . . . -0.8(3) ?
C1 C2 C3 C4 . . . . 1.1(3) ?
C2 C3 C4 C5 . . . . -0.4(3) ?
C3 C4 C5 C6 . . . . -0.5(3) ?
Se1 N2 C6 C5 . . . . 179.91(16) ?
Se1 N2 C6 C1 . . . . -1.1(2) ?
C4 C5 C6 N2 . . . . 179.72(19) ?
C4 C5 C6 C1 . . . . 0.7(3) ?
N1 C1 C6 N2 . . . . 1.3(3) ?
C2 C1 C6 N2 . . . . -179.12(17) ?
N1 C1 C6 C5 . . . . -179.62(18) ?
C2 C1 C6 C5 . . . . -0.1(3) ?
Se2 N3 C7 C8 . . . . 177.08(16) ?
Cu1 N3 C7 C8 . . . . -3.9(3) ?
Se2 N3 C7 C12 . . . . -1.4(2) ?
Cu1 N3 C7 C12 . . . . 177.57(13) ?
N3 C7 C8 C9 . . . . 179.67(19) ?
C12 C7 C8 C9 . . . . -1.9(3) ?
C7 C8 C9 C10 . . . . -0.4(3) ?
C8 C9 C10 C11 . . . . 2.0(3) ?
C9 C10 C11 C12 . . . . -1.0(3) ?
Se2 N4 C12 C11 . . . . 179.34(16) ?
Se2 N4 C12 C7 . . . . -0.7(2) ?
C10 C11 C12 N4 . . . . 178.62(19) ?
C10 C11 C12 C7 . . . . -1.3(3) ?
N3 C7 C12 N4 . . . . 1.5(3) ?
C8 C7 C12 N4 . . . . -177.12(17) ?
N3 C7 C12 C11 . . . . -178.57(18) ?
C8 C7 C12 C11 . . . . 2.8(3) ?
