#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/25/2232556.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_2232556
loop_
_publ_author_name
'Zhang, Wen-Shen'
'Liu, Zhi-Juan'
'Xu, Feng'
'Xun, Qi-Ning'
_publ_section_title
;
 Dibromidobis{1-[4-(pyridin-4-yl)phenyl]ethanone-κN}mercury(II)
;
_journal_coeditor_code           BH2387
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1849
_journal_paper_doi               10.1107/S1600536811049993
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Hg Br2 (C13 H11 N O)2]'
_chemical_formula_moiety         'C26 H22 Br2 Hg N2 O2'
_chemical_formula_sum            'C26 H22 Br2 Hg N2 O2'
_chemical_formula_weight         754.87
_chemical_name_systematic
;
Dibromidobis{1-[4-(pyridin-4-yl)phenyl]ethanone-κN}mercury(II)
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 102.453(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.656(6)
_cell_length_b                   5.296(2)
_cell_length_c                   29.442(11)
_cell_measurement_reflns_used    1208
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18.548
_cell_measurement_theta_min      2.504
_cell_volume                     2536.0(16)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω 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  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            6208
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    9.246
_exptl_absorpt_correction_T_max  0.3376
_exptl_absorpt_correction_T_min  0.3376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.977
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.028
_refine_diff_density_min         -0.412
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0520
_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)+(0.0626P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1305
_reflns_number_gt                1339
_reflns_number_total             2358
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2387.cif
_cod_data_source_block           I
_cod_original_cell_volume        2535.8(16)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2232556
_cod_database_fobs_code          2232556
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_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_symmetry_multiplicity
Br Br1 1.09304(9) 1.3414(3) 0.69925(5) 0.1331(5) Uani d . 1 1
C C1 0.9296(7) 0.848(2) 0.6587(5) 0.114(4) Uani d . 1 1
H H1 0.9746 0.9148 0.6488 0.137 Uiso calc R 1 1
C C2 0.8806(8) 0.675(2) 0.6305(5) 0.115(4) Uani d U 1 1
H H2 0.8933 0.6333 0.6021 0.138 Uiso calc R 1 1
C C3 0.8158(5) 0.5649(18) 0.6421(3) 0.069(2) Uani d . 1 1
C C4 0.8052(8) 0.640(3) 0.6837(5) 0.118(4) Uani d U 1 1
H H4 0.7634 0.5656 0.6955 0.142 Uiso calc R 1 1
C C5 0.8535(8) 0.823(3) 0.7101(4) 0.120(4) Uani d . 1 1
H H5 0.8398 0.8759 0.7376 0.145 Uiso calc R 1 1
C C6 0.7626(6) 0.3795(17) 0.6137(3) 0.073(2) Uani d . 1 1
C C7 0.7812(8) 0.257(2) 0.5769(5) 0.123(4) Uani d U 1 1
H H7 0.8308 0.2937 0.5688 0.147 Uiso calc R 1 1
C C8 0.7310(8) 0.081(3) 0.5511(5) 0.130(5) Uani d . 1 1
H H8 0.7470 0.0032 0.5262 0.156 Uiso calc R 1 1
C C9 0.6581(6) 0.0203(17) 0.5617(3) 0.079(3) Uani d . 1 1
C C10 0.6395(8) 0.137(2) 0.5987(5) 0.112(4) Uani d . 1 1
H H10 0.5907 0.0956 0.6075 0.134 Uiso calc R 1 1
C C11 0.6896(8) 0.313(2) 0.6235(5) 0.118(4) Uani d . 1 1
H H11 0.6732 0.3910 0.6483 0.142 Uiso calc R 1 1
C C12 0.6030(7) -0.170(2) 0.5337(4) 0.103(3) Uani d U 1 1
C C13 0.5286(8) -0.260(2) 0.5499(5) 0.122(4) Uani d U 1 1
H H13A 0.4970 -0.3703 0.5269 0.183 Uiso calc R 1 1
H H13B 0.4956 -0.1182 0.5546 0.183 Uiso calc R 1 1
H H13C 0.5455 -0.3508 0.5786 0.183 Uiso calc R 1 1
Hg Hg1 1.0000 1.21208(11) 0.7500 0.0886(3) Uani d S 1 2
N N1 0.9161(5) 0.9236(15) 0.6984(3) 0.080(2) Uani d . 1 1
O O1 0.6156(6) -0.2498(18) 0.4976(4) 0.147(4) Uani d . 1 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N1 C1 C2 . . 123.4(10)
N1 C1 H1 . . 118.3
C2 C1 H1 . . 118.3
C3 C2 C1 . . 122.8(11)
C3 C2 H2 . . 118.6
C1 C2 H2 . . 118.6
C2 C3 C4 . . 112.3(10)
C2 C3 C6 . . 124.9(9)
C4 C3 C6 . . 122.7(9)
C3 C4 C5 . . 123.2(11)
C3 C4 H4 . . 118.4
C5 C4 H4 . . 118.4
N1 C5 C4 . . 123.0(11)
N1 C5 H5 . . 118.5
C4 C5 H5 . . 118.5
C11 C6 C7 . . 114.5(10)
C11 C6 C3 . . 121.0(9)
C7 C6 C3 . . 124.4(10)
C6 C7 C8 . . 123.6(12)
C6 C7 H7 . . 118.2
C8 C7 H7 . . 118.2
C9 C8 C7 . . 120.4(12)
C9 C8 H8 . . 119.8
C7 C8 H8 . . 119.8
C10 C9 C8 . . 116.7(10)
C10 C9 C12 . . 122.5(11)
C8 C9 C12 . . 120.8(11)
C9 C10 C11 . . 122.0(11)
C9 C10 H10 . . 119.0
C11 C10 H10 . . 119.0
C10 C11 C6 . . 122.7(11)
C10 C11 H11 . . 118.6
C6 C11 H11 . . 118.6
O1 C12 C9 . . 121.4(12)
O1 C12 C13 . . 118.9(11)
C9 C12 C13 . . 119.6(11)
C12 C13 H13A . . 109.5
C12 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C12 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
N1 Hg1 N1 . 2_756 100.3(4)
N1 Hg1 Br1 . . 98.7(2)
N1 Hg1 Br1 2_756 . 101.8(2)
N1 Hg1 Br1 . 2_756 101.8(2)
N1 Hg1 Br1 2_756 2_756 98.7(2)
Br1 Hg1 Br1 . 2_756 147.81(9)
C5 N1 C1 . . 115.1(9)
C5 N1 Hg1 . . 119.5(7)
C1 N1 Hg1 . . 125.3(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 Hg1 . 2.4701(14)
C1 N1 . 1.301(13)
C1 C2 . 1.381(16)
C1 H1 . 0.9300
C2 C3 . 1.335(13)
C2 H2 . 0.9300
C3 C4 . 1.336(14)
C3 C6 . 1.459(12)
C4 C5 . 1.388(16)
C4 H4 . 0.9300
C5 N1 . 1.282(13)
C5 H5 . 0.9300
C6 C11 . 1.356(14)
C6 C7 . 1.356(15)
C7 C8 . 1.364(16)
C7 H7 . 0.9300
C8 C9 . 1.357(14)
C8 H8 . 0.9300
C9 C10 . 1.346(14)
C9 C12 . 1.487(14)
C10 C11 . 1.355(16)
C10 H10 . 0.9300
C11 H11 . 0.9300
C12 O1 . 1.203(14)
C12 C13 . 1.498(17)
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
Hg1 N1 . 2.383(8)
Hg1 N1 2_756 2.383(8)
Hg1 Br1 2_756 2.4701(14)
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
C10 H10 Br1 3_435 0.93 3.01 3.579(13) 121
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
N1 C1 C2 C3 . -2(2)
C1 C2 C3 C4 . -0.6(19)
C1 C2 C3 C6 . -179.5(12)
C2 C3 C4 C5 . 4(2)
C6 C3 C4 C5 . -177.4(12)
C3 C4 C5 N1 . -5(2)
C2 C3 C6 C11 . -167.2(12)
C4 C3 C6 C11 . 14.0(16)
C2 C3 C6 C7 . 14.3(16)
C4 C3 C6 C7 . -164.5(12)
C11 C6 C7 C8 . 1(2)
C3 C6 C7 C8 . 179.1(12)
C6 C7 C8 C9 . 0(2)
C7 C8 C9 C10 . -1(2)
C7 C8 C9 C12 . 179.9(12)
C8 C9 C10 C11 . 2(2)
C12 C9 C10 C11 . -179.1(12)
C9 C10 C11 C6 . -2(2)
C7 C6 C11 C10 . 0(2)
C3 C6 C11 C10 . -178.3(12)
C10 C9 C12 O1 . 170.9(13)
C8 C9 C12 O1 . -10.3(18)
C10 C9 C12 C13 . -7.3(16)
C8 C9 C12 C13 . 171.5(12)
C4 C5 N1 C1 . 3(2)
C4 C5 N1 Hg1 . -175.1(11)
C2 C1 N1 C5 . 1(2)
C2 C1 N1 Hg1 . 178.0(10)
N1 Hg1 N1 C5 2_756 81.6(9)
Br1 Hg1 N1 C5 . -174.7(9)
Br1 Hg1 N1 C5 2_756 -19.6(9)
N1 Hg1 N1 C1 2_756 -95.9(10)
Br1 Hg1 N1 C1 . 7.9(10)
Br1 Hg1 N1 C1 2_756 162.9(9)
