#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/41/4334109.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_4334109
loop_
_publ_author_name
'Hamid Reza Khavasi'
'Alireza Azhdari Tehrani'
_publ_section_title
;
 Influence of Halogen Bonding Interaction on Supramolecular Assembly of
 Coordination Compounds; Head-to-Tail N...X Synthon Repetitivity
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2891
_journal_page_last               2905
_journal_paper_doi               10.1021/ic3021113
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C11 H8 Br1 Hg1 I2 N3 O1'
_chemical_formula_sum            'C11 H8 Br Hg I2 N3 O'
_chemical_formula_weight         732.49
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 102.494(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.609(2)
_cell_length_b                   6.9070(10)
_cell_length_c                   17.596(3)
_cell_measurement_reflns_used    786
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.22
_cell_measurement_theta_min      2.37
_cell_volume                     1614.8(4)
_computing_cell_refinement       'SAINTPlus (Bruker, 1998a)'
_computing_data_collection       'SMART (Bruker, 1998b)'
_computing_data_reduction        'SAINTPlus (Bruker, 1998a)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker SMART 1000 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  0.1049
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6128
_diffrn_reflns_theta_full        29.22
_diffrn_reflns_theta_max         29.22
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    15.824
_exptl_absorpt_correction_T_max  0.776
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    3.013
_exptl_crystal_description       Block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         2.120
_refine_diff_density_min         -4.859
_refine_diff_density_rms         0.672
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.261
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         2328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.261
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0629
_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)+(0.1213P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1753
_refine_ls_wR_factor_ref         0.1949
_reflns_number_gt                2041
_reflns_number_total             2328
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic3021113_si_002_11.cif
_cod_data_source_block           11
_cod_original_formula_sum        'C11 H8 Br1 Hg1 I2 N3 O1'
_cod_database_code               4334109
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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
C1 C 0.5959(10) 0.0000 0.2052(7) 0.056(3) Uani 1 2 d S
H1 H 0.5259 0.0000 0.1920 0.068 Uiso 1 2 calc SR
C2 C 0.6527(10) 0.0000 0.1457(8) 0.057(3) Uani 1 2 d S
H2 H 0.6182 0.0000 0.0939 0.068 Uiso 1 2 calc SR
C3 C 0.7974(9) 0.0000 0.2374(7) 0.051(2) Uani 1 2 d S
H3 H 0.8673 0.0000 0.2516 0.061 Uiso 1 2 calc SR
C4 C 0.7417(10) 0.0000 0.2935(7) 0.049(2) Uani 1 2 d S
C5 C 0.7964(9) 0.0000 0.3778(7) 0.047(2) Uani 1 2 d S
C6 C 0.7556(9) 0.0000 0.5091(7) 0.045(2) Uani 1 2 d S
C7 C 0.6700(9) 0.0000 0.5429(7) 0.052(3) Uani 1 2 d S
H7 H 0.6051 0.0000 0.5122 0.063 Uiso 1 2 calc SR
C8 C 0.6869(10) 0.0000 0.6239(8) 0.052(2) Uani 1 2 d S
C9 C 0.7819(14) 0.0000 0.6708(8) 0.066(3) Uani 1 2 d S
H9 H 0.7908 0.0000 0.7247 0.079 Uiso 1 2 calc SR
C10 C 0.8649(11) 0.0000 0.6358(8) 0.060(3) Uani 1 2 d S
H10 H 0.9297 0.0000 0.6667 0.072 Uiso 1 2 calc SR
C11 C 0.8517(10) 0.0000 0.5557(7) 0.052(3) Uani 1 2 d S
H11 H 0.9074 0.0000 0.5330 0.063 Uiso 1 2 calc SR
N1 N 0.6434(8) 0.0000 0.2788(7) 0.055(2) Uani 1 2 d S
N2 N 0.7508(8) 0.0000 0.1609(6) 0.0483(19) Uani 1 2 d S
N3 N 0.7349(8) 0.0000 0.4275(6) 0.054(2) Uani 1 2 d S
H3A H 0.6719 0.0000 0.4057 0.065 Uiso 1 2 calc SR
O1 O 0.8899(8) 0.0000 0.3968(7) 0.068(3) Uani 1 2 d S
Hg1 Hg 0.83911(4) 0.0000 0.05193(3) 0.0595(2) Uani 1 2 d S
Br1 Br 0.57077(14) 0.0000 0.66774(10) 0.0769(5) Uani 1 2 d S
I1 I 0.68786(7) 0.0000 -0.07049(5) 0.0570(3) Uani 1 2 d S
I2 I 1.02559(7) 0.0000 0.12699(6) 0.0671(3) 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'
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'
Hg Hg -2.3894 9.2266 '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'
I I -0.4742 1.8119 '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
N1 C1 C2 119.4(12)
N1 C1 H1 120.3
C2 C1 H1 120.3
N2 C2 C1 122.8(13)
N2 C2 H2 118.6
C1 C2 H2 118.6
N2 C3 C4 120.1(11)
N2 C3 H3 119.9
C4 C3 H3 119.9
N1 C4 C3 124.0(12)
N1 C4 C5 117.4(10)
C3 C4 C5 118.5(11)
O1 C5 N3 125.1(13)
O1 C5 C4 121.5(11)
N3 C5 C4 113.5(11)
C11 C6 N3 124.1(10)
C11 C6 C7 120.5(11)
N3 C6 C7 115.4(11)
C8 C7 C6 117.4(12)
C8 C7 H7 121.3
C6 C7 H7 121.3
C9 C8 C7 122.6(11)
C9 C8 Br1 120.8(10)
C7 C8 Br1 116.6(10)
C8 C9 C10 118.7(12)
C8 C9 H9 120.7
C10 C9 H9 120.7
C11 C10 C9 120.6(13)
C11 C10 H10 119.7
C9 C10 H10 119.7
C10 C11 C6 120.2(11)
C10 C11 H11 119.9
C6 C11 H11 119.9
C4 N1 C1 117.4(11)
C2 N2 C3 116.2(11)
C2 N2 Hg1 119.3(8)
C3 N2 Hg1 124.5(8)
C5 N3 C6 131.0(11)
C5 N3 H3A 114.5
C6 N3 H3A 114.5
N2 Hg1 I2 101.0(2)
N2 Hg1 I1 102.0(2)
I2 Hg1 I1 156.92(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.317(17)
C1 C2 1.429(17)
C1 H1 0.9300
C2 N2 1.303(17)
C2 H2 0.9300
C3 N2 1.358(15)
C3 C4 1.368(16)
C3 H3 0.9300
C4 N1 1.306(16)
C4 C5 1.509(17)
C5 O1 1.244(16)
C5 N3 1.333(15)
C6 C11 1.385(18)
C6 N3 1.403(15)
C6 C7 1.418(15)
C7 C8 1.393(17)
C7 H7 0.9300
C8 C9 1.38(2)
C8 Br1 1.902(11)
C9 C10 1.40(2)
C9 H9 0.9300
C10 C11 1.381(17)
C10 H10 0.9300
C11 H11 0.9300
N2 Hg1 2.474(10)
N3 H3A 0.8600
Hg1 I2 2.5950(11)
Hg1 I1 2.6381(10)
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
N1 C1 C2 N2 0.000(2)
N2 C3 C4 N1 0.000(2)
N2 C3 C4 C5 180.000(2)
N1 C4 C5 O1 180.000(2)
C3 C4 C5 O1 0.000(2)
N1 C4 C5 N3 0.000(2)
C3 C4 C5 N3 180.000(2)
C11 C6 C7 C8 0.000(4)
N3 C6 C7 C8 180.000(4)
C6 C7 C8 C9 0.000(4)
C6 C7 C8 Br1 180.000(2)
C7 C8 C9 C10 0.000(6)
Br1 C8 C9 C10 180.000(4)
C8 C9 C10 C11 0.000(5)
C9 C10 C11 C6 0.000(4)
N3 C6 C11 C10 180.000(3)
C7 C6 C11 C10 0.000(4)
C3 C4 N1 C1 0.000(2)
C5 C4 N1 C1 180.000(2)
C2 C1 N1 C4 0.000(2)
C1 C2 N2 C3 0.000(1)
C1 C2 N2 Hg1 180.000(1)
C4 C3 N2 C2 0.000(1)
C4 C3 N2 Hg1 180.000(1)
O1 C5 N3 C6 0.000(4)
C4 C5 N3 C6 180.000(3)
C11 C6 N3 C5 0.000(3)
C7 C6 N3 C5 180.000(3)
C2 N2 Hg1 I2 180.0
C3 N2 Hg1 I2 0.0
C2 N2 Hg1 I1 0.0
C3 N2 Hg1 I1 180.0
