#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/02/2220237.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_2220237
loop_
_publ_author_name
'Kalateh, Khadijeh'
'Norouzi, Ali'
'Ebadi, Amin'
'Ahmadi, Roya'
'Amani, Vahid'
_publ_section_title
;
 Dibromido(di-2-pyridylamine-κ²N,N')mercury(II)
;
_journal_coeditor_code           HK2575
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1583
_journal_page_last               m1584
_journal_paper_doi               10.1107/S1600536808038129
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Hg Br2 (C10 H9 N3)]'
_chemical_formula_moiety         'C10 H9 Br2 Hg N3'
_chemical_formula_sum            'C10 H9 Br2 Hg N3'
_chemical_formula_weight         531.59
_chemical_name_systematic
;
Dibromido(di-2-pyridylamine-κ²N,N')mercury(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                113.45(3)
_cell_angle_beta                 98.41(3)
_cell_angle_gamma                97.79(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1284(16)
_cell_length_b                   8.7645(18)
_cell_length_c                   9.912(2)
_cell_measurement_reflns_used    1657
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.19
_cell_measurement_theta_min      2.30
_cell_volume                     626.1(3)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART 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  0.0874
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7839
_diffrn_reflns_theta_full        29.19
_diffrn_reflns_theta_max         29.19
_diffrn_reflns_theta_min         2.30
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    18.649
_exptl_absorpt_correction_T_max  0.080
_exptl_absorpt_correction_T_min  0.016
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(shape of crystal determined optically)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.820
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         4.325
_refine_diff_density_min         -6.537
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.059
_refine_ls_shift/su_mean         1.231
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0882P)²+2.3955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1403
_reflns_number_gt                3234
_reflns_number_total             3350
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2575.cif
_cod_data_source_block           I
_cod_database_code               2220237
_cod_database_fobs_code          2220237
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
Hg Hg1 0.28140(3) 0.22806(4) 0.84793(3) 0.02226(15) Uani d . 1
Br Br1 0.03376(10) 0.29535(11) 0.71493(10) 0.0259(2) Uani d . 1
Br Br2 0.58403(10) 0.34148(10) 0.83842(9) 0.0219(2) Uani d . 1
N N1 0.2053(9) 0.1755(9) 1.0425(8) 0.0195(12) Uani d . 1
N N2 0.3018(9) -0.0818(8) 0.9915(8) 0.0190(12) Uani d . 1
H H2A 0.3426 -0.1362 1.0395 0.023 Uiso calc R 1
N N3 0.3006(9) -0.0591(8) 0.7601(8) 0.0192(12) Uani d . 1
C C1 0.1347(11) 0.2988(10) 1.1369(11) 0.0239(15) Uani d . 1
H H1 0.1098 0.3845 1.1096 0.029 Uiso calc R 1
C C2 0.0991(11) 0.3023(11) 1.2678(11) 0.0248(16) Uani d . 1
H H2 0.0516 0.3881 1.3288 0.030 Uiso calc R 1
C C3 0.1363(11) 0.1728(11) 1.3080(10) 0.0247(15) Uani d . 1
H H3 0.1151 0.1727 1.3977 0.030 Uiso calc R 1
C C4 0.2037(11) 0.0462(11) 1.2157(10) 0.0225(14) Uani d . 1
H H4 0.2279 -0.0412 1.2407 0.027 Uiso calc R 1
C C5 0.2355(9) 0.0519(10) 1.0815(9) 0.0178(13) Uani d . 1
C C6 0.3175(9) -0.1477(10) 0.8430(9) 0.0172(13) Uani d . 1
C C7 0.3535(10) -0.3113(10) 0.7834(10) 0.0215(14) Uani d . 1
H H7 0.3679 -0.3693 0.8437 0.026 Uiso calc R 1
C C8 0.3671(11) -0.3850(11) 0.6355(10) 0.0249(15) Uani d . 1
H H8 0.3886 -0.4940 0.5944 0.030 Uiso calc R 1
C C9 0.3485(12) -0.2952(11) 0.5481(10) 0.0262(16) Uani d . 1
H H9 0.3575 -0.3414 0.4479 0.031 Uiso calc R 1
C C10 0.3158(11) -0.1340(12) 0.6165(10) 0.0248(16) Uani d . 1
H H10 0.3034 -0.0731 0.5587 0.030 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Hg1 0.0242(2) 0.0212(2) 0.0290(2) 0.00845(13) 0.00573(13) 0.01720(14)
Br1 0.0239(4) 0.0253(4) 0.0341(4) 0.0070(3) 0.0012(3) 0.0194(3)
Br2 0.0237(4) 0.0208(4) 0.0267(4) 0.0057(3) 0.0061(3) 0.0151(3)
N1 0.023(3) 0.016(3) 0.019(3) 0.006(2) 0.001(2) 0.008(2)
N2 0.026(3) 0.015(3) 0.022(3) 0.007(2) 0.004(2) 0.013(2)
N3 0.024(3) 0.016(3) 0.018(3) 0.005(2) 0.002(2) 0.009(2)
C1 0.025(4) 0.015(3) 0.032(4) 0.005(3) 0.003(3) 0.011(3)
C2 0.024(3) 0.020(3) 0.030(4) 0.007(3) 0.007(3) 0.009(3)
C3 0.029(4) 0.024(4) 0.022(3) 0.006(3) 0.009(3) 0.010(3)
C4 0.026(3) 0.021(3) 0.024(4) 0.005(3) 0.003(3) 0.012(3)
C5 0.014(3) 0.017(3) 0.020(3) 0.001(2) 0.002(2) 0.007(3)
C6 0.013(3) 0.016(3) 0.020(3) -0.002(2) -0.002(2) 0.009(3)
C7 0.024(3) 0.017(3) 0.024(4) 0.004(3) 0.004(3) 0.010(3)
C8 0.027(4) 0.022(4) 0.023(4) 0.005(3) 0.002(3) 0.008(3)
C9 0.037(4) 0.021(4) 0.017(3) 0.005(3) 0.003(3) 0.006(3)
C10 0.030(4) 0.029(4) 0.020(3) 0.008(3) 0.004(3) 0.015(3)
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'
O O 0.0106 0.0060 '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'
Hg Hg -2.3894 9.2266 '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
N1 Hg1 N3 81.1(2) yes
N1 Hg1 Br1 109.13(17) yes
N3 Hg1 Br1 117.16(17) yes
N1 Hg1 Br2 125.41(17) yes
N3 Hg1 Br2 96.23(18) yes
Br1 Hg1 Br2 119.68(3) yes
C1 N1 Hg1 114.3(5) ?
C5 N1 Hg1 128.2(6) ?
C5 N1 C1 117.2(7) ?
C6 N2 C5 135.0(7) ?
C6 N2 H2A 112.5 ?
C5 N2 H2A 112.5 ?
C6 N3 Hg1 126.5(5) ?
C10 N3 Hg1 115.6(6) ?
C10 N3 C6 117.4(7) ?
C2 C1 N1 123.6(8) ?
C2 C1 H1 118.1 ?
N1 C1 H1 118.3 ?
C1 C2 C3 117.9(8) ?
C1 C2 H2 121.0 ?
C3 C2 H2 121.1 ?
C4 C3 C2 120.2(8) ?
C4 C3 H3 120.0 ?
C2 C3 H3 119.9 ?
C3 C4 C5 118.2(8) ?
C3 C4 H4 120.9 ?
C5 C4 H4 120.9 ?
N1 C5 N2 121.7(7) ?
N1 C5 C4 122.9(7) ?
N2 C5 C4 115.4(7) ?
N3 C6 N2 121.6(7) ?
N3 C6 C7 121.6(7) ?
N2 C6 C7 116.9(7) ?
C8 C7 C6 119.6(8) ?
C8 C7 H7 120.2 ?
C6 C7 H7 120.2 ?
C7 C8 C9 119.4(8) ?
C7 C8 H8 120.3 ?
C9 C8 H8 120.3 ?
C8 C9 C10 117.2(8) ?
C8 C9 H9 121.4 ?
C10 C9 H9 121.4 ?
N3 C10 C9 124.8(8) ?
N3 C10 H10 117.5 ?
C9 C10 H10 117.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 Hg1 2.5106(11) yes
Br2 Hg1 2.5549(11) yes
N1 Hg1 2.301(7) yes
N2 H2A 0.8600 ?
N3 Hg1 2.350(7) yes
C1 C2 1.360(13) ?
C1 N1 1.376(11) ?
C1 H1 0.9300 ?
C2 C3 1.398(13) ?
C2 H2 0.9300 ?
C3 C4 1.368(12) ?
C3 H3 0.9300 ?
C4 C5 1.410(11) ?
C4 H4 0.9300 ?
C5 N1 1.327(10) ?
C5 N2 1.393(10) ?
C6 N3 1.342(10) ?
C6 N2 1.384(10) ?
C6 C7 1.408(11) ?
C7 C8 1.376(12) ?
C7 H7 0.9300 ?
C8 C9 1.389(13) ?
C8 H8 0.9300 ?
C9 C10 1.385(12) ?
C9 H9 0.9300 ?
C10 N3 1.342(11) ?
C10 H10 0.9300 ?
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
N2 H2A Br2 2_657 0.86 2.620 3.472(3) 170 yes
C2 H2 Cg3 2_755 0.93 3.197 3.587(3) 107 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
C1 N1 Hg1 N3 -166.6(6)
C5 N1 Hg1 N3 20.2(6)
C1 N1 Hg1 Br1 -50.8(6)
C5 N1 Hg1 Br1 136.0(6)
C1 N1 Hg1 Br2 102.0(5)
C5 N1 Hg1 Br2 -71.1(7)
C10 N3 Hg1 N1 168.0(6)
C6 N3 Hg1 N1 -20.2(6)
C6 N3 Hg1 Br1 -127.2(6)
C10 N3 Hg1 Br1 61.0(6)
C6 N3 Hg1 Br2 104.8(6)
C10 N3 Hg1 Br2 -67.0(6)
N1 C1 C2 C3 -0.2(13)
C1 C2 C3 C4 -1.0(13)
C2 C3 C4 C5 0.6(12)
C3 C4 C5 N1 1.0(12)
C3 C4 C5 N2 -179.1(7)
N3 C6 C7 C8 -1.8(11)
N2 C6 C7 C8 178.7(7)
C6 C7 C8 C9 1.3(12)
C7 C8 C9 C10 -0.3(13)
C8 C9 C10 N3 -0.1(14)
N2 C5 N1 C1 178.0(7)
C4 C5 N1 C1 -2.2(11)
N2 C5 N1 Hg1 -9.0(10)
C4 C5 N1 Hg1 170.8(6)
C2 C1 N1 C5 1.8(12)
C2 C1 N1 Hg1 -172.2(7)
N3 C6 N2 C5 16.3(13)
C7 C6 N2 C5 -164.2(8)
N1 C5 N2 C6 -16.8(13)
C4 C5 N2 C6 163.3(8)
C9 C10 N3 C6 -0.4(13)
C9 C10 N3 Hg1 172.2(7)
N2 C6 N3 C10 -179.2(7)
C7 C6 N3 C10 1.4(11)
N2 C6 N3 Hg1 9.2(10)
C7 C6 N3 Hg1 -170.3(5)
