#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/65/2236551.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_2236551
loop_
_publ_author_name
'Al-Far, Rawhi'
'Ali, Basem F.'
'Haddad, Salim F.'
_publ_section_title
;
 Bis(2,6-dimethylpyridinium) dibromoiodate bromide
;
_journal_coeditor_code           PV2580
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2743
_journal_paper_doi               10.1107/S1600536812035702
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '2C7 H10 N +, Br2 I -, Br -'
_chemical_formula_moiety         '2(C7 H10 N +), Br2 I -, Br -'
_chemical_formula_sum            'C14 H20 Br3 I N2'
_chemical_formula_weight         582.92
_chemical_name_common            (2,6-DMPH)2.IBr2.Br
_chemical_name_systematic
;
Bis(2,6-dimethylpyridinium) dibromoiodate bromide
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.885(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8627(16)
_cell_length_b                   11.3622(9)
_cell_length_c                   13.8957(15)
_cell_measurement_reflns_used    1414
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3506
_cell_measurement_theta_min      2.9828
_cell_volume                     2070.9(4)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_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      293(2)
_diffrn_detector_area_resol_mean 16.0534
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Agilent Xcalibur Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4417
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.10
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    7.329
_exptl_absorpt_correction_T_max  0.733
_exptl_absorpt_correction_T_min  0.578
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.870
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.3360
_exptl_crystal_size_mid          0.2746
_exptl_crystal_size_min          0.1528
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.579
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0400
_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)+(0.0423P)²+1.4129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                1280
_reflns_number_total             1834
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            pv2580.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2236551
_cod_database_fobs_code          2236551
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
I I1 0.5000 0.56444(5) 0.2500 0.0633(2) Uani d S 1 2
Br Br1 0.31439(6) 0.56808(6) 0.10417(6) 0.0846(3) Uani d . 1 1
Br Br2 0.0000 0.55587(7) 0.2500 0.0665(3) Uani d S 1 2
N N1 0.1116(3) 0.3483(4) 0.1556(3) 0.0529(11) Uani d . 1 1
H H1A 0.0824 0.4027 0.1793 0.064 Uiso calc R 1 1
C C6 0.2531(5) 0.3799(6) 0.3092(5) 0.081(2) Uani d . 1 1
H H6A 0.2058 0.4369 0.3186 0.122 Uiso calc R 1 1
H H6B 0.3145 0.4188 0.3090 0.122 Uiso calc R 1 1
H H6C 0.2688 0.3237 0.3637 0.122 Uiso calc R 1 1
C C1 0.2069(5) 0.3183(5) 0.2109(5) 0.0614(16) Uani d . 1 1
C C5 0.0574(5) 0.2992(5) 0.0649(5) 0.0654(17) Uani d . 1 1
C C2 0.2529(6) 0.2305(6) 0.1722(6) 0.085(2) Uani d . 1 1
H H2A 0.3183 0.2057 0.2091 0.101 Uiso calc R 1 1
C C7 -0.0487(5) 0.3421(7) 0.0149(5) 0.093(2) Uani d . 1 1
H H7A -0.0643 0.4021 0.0563 0.140 Uiso calc R 1 1
H H7B -0.0955 0.2778 0.0069 0.140 Uiso calc R 1 1
H H7C -0.0544 0.3742 -0.0506 0.140 Uiso calc R 1 1
C C4 0.1058(8) 0.2137(6) 0.0278(6) 0.090(2) Uani d . 1 1
H H4A 0.0720 0.1780 -0.0341 0.108 Uiso calc R 1 1
C C3 0.2038(8) 0.1805(6) 0.0814(7) 0.098(3) Uani d . 1 1
H H3A 0.2363 0.1235 0.0550 0.117 Uiso calc R 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
Br1 I1 Br1 . 2_655 178.25(3)
Br2 Br2 Br2 2 1 0(10)
C1 N1 C5 . . 125.0(5)
C1 N1 H1A . . 117.5
C5 N1 H1A . . 117.5
C1 C6 H6A . . 109.5
C1 C6 H6B . . 109.5
H6A C6 H6B . . 109.5
C1 C6 H6C . . 109.5
H6A C6 H6C . . 109.5
H6B C6 H6C . . 109.5
N1 C1 C2 . . 117.0(6)
N1 C1 C6 . . 117.4(5)
C2 C1 C6 . . 125.6(6)
N1 C5 C4 . . 116.6(6)
N1 C5 C7 . . 117.6(6)
C4 C5 C7 . . 125.8(7)
C3 C2 C1 . . 120.7(7)
C3 C2 H2A . . 119.6
C1 C2 H2A . . 119.6
C5 C7 H7A . . 109.5
C5 C7 H7B . . 109.5
H7A C7 H7B . . 109.5
C5 C7 H7C . . 109.5
H7A C7 H7C . . 109.5
H7B C7 H7C . . 109.5
C5 C4 C3 . . 120.6(7)
C5 C4 H4A . . 119.7
C3 C4 H4A . . 119.7
C2 C3 C4 . . 120.1(7)
C2 C3 H3A . . 119.9
C4 C3 H3A . . 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
I1 Br1 . 2.7117(9)
I1 Br1 2_655 2.7117(9)
Br2 Br2 2 0.0000
Br2 Br2 1 0.0000
N1 C1 . 1.340(7)
N1 C5 . 1.361(7)
N1 H1A . 0.8600
C6 C1 . 1.483(8)
C6 H6A . 0.9600
C6 H6B . 0.9600
C6 H6C . 0.9600
C1 C2 . 1.383(9)
C5 C4 . 1.372(9)
C5 C7 . 1.490(9)
C2 C3 . 1.350(10)
C2 H2A . 0.9300
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
C4 C3 . 1.373(10)
C4 H4A . 0.9300
C3 H3A . 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
N1 H1A Br2 1 0.86 2.45 3.315(5) 178.9
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
C5 N1 C1 C2 -0.2(9)
C5 N1 C1 C6 -178.7(5)
C1 N1 C5 C4 -0.9(9)
C1 N1 C5 C7 178.9(5)
N1 C1 C2 C3 1.8(9)
C6 C1 C2 C3 -179.9(7)
N1 C5 C4 C3 0.4(9)
C7 C5 C4 C3 -179.4(7)
C1 C2 C3 C4 -2.2(11)
C5 C4 C3 C2 1.1(11)
