#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/88/2228876.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_2228876
loop_
_publ_author_name
'Thenmozhi, M.'
'Philominal, A.'
'Dhanuskodi, S.'
'Ponnuswamy, M. N.'
_publ_section_title
;
 Dibromidobis(1-ethyl-2,6-dimethylpyridinium-4-olate-κO)zinc(II)
;
_journal_coeditor_code           SJ5050
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m103
_journal_page_last               m104
_journal_paper_doi               10.1107/S1600536810052190
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Zn Br2 (C9 H13 N O)2]'
_chemical_formula_moiety         'C18 H26 Br2 N2 O2 Zn'
_chemical_formula_sum            'C18 H26 Br2 N2 O2 Zn'
_chemical_formula_weight         527.60
_chemical_name_systematic
;
Dibromidobis(1-ethyl-2,6-dimethylpyridinium-4-olate-κO)zinc(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                93.131(6)
_cell_angle_beta                 97.871(7)
_cell_angle_gamma                90.210(8)
_cell_formula_units_Z            2
_cell_length_a                   8.4620(10)
_cell_length_b                   8.5180(10)
_cell_length_c                   14.418(3)
_cell_measurement_reflns_used    16553
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.43
_cell_volume                     1027.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII area-detector'
_diffrn_measurement_method       'ω and φ'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16553
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.095
_exptl_absorpt_correction_T_max  0.6041
_exptl_absorpt_correction_T_min  0.5799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.196
_refine_diff_density_min         -0.952
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         16553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0512P)²+13.5867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1809
_refine_ls_wR_factor_ref         0.1890
_reflns_number_gt                13614
_reflns_number_total             16553
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5050.cif
_cod_data_source_block           I
_cod_original_cell_volume        1027.9(2)
_cod_database_code               2228876
_cod_database_fobs_code          2228876
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
C C2 1.2061(5) 0.5686(6) 0.1164(3) 0.0379(11) Uani d . 1 . .
C C3 1.1571(5) 0.4291(5) 0.1424(3) 0.0369(11) Uani d . 1 . .
H H3 1.2321 0.3503 0.1536 0.044 Uiso calc R 1 . .
C C4 0.9992(5) 0.3972(5) 0.1532(3) 0.0350(10) Uani d . 1 . .
C C5 0.8909(5) 0.5207(5) 0.1318(3) 0.0372(11) Uani d . 1 . .
H H5 0.7830 0.5052 0.1351 0.045 Uiso calc R 1 . .
C C6 0.9418(5) 0.6608(6) 0.1066(3) 0.0383(11) Uani d . 1 . .
C C7 1.1564(7) 0.8459(6) 0.0842(4) 0.0565(15) Uani d . 1 . .
H H7A 1.0751 0.8990 0.0437 0.068 Uiso calc R 1 . .
H H7B 1.2507 0.8371 0.0530 0.068 Uiso calc R 1 . .
C C8 1.1965(8) 0.9428(7) 0.1766(5) 0.080(2) Uani d . 1 . .
H H8A 1.1046 0.9476 0.2089 0.120 Uiso calc R 1 . .
H H8B 1.2276 1.0473 0.1642 0.120 Uiso calc R 1 . .
H H8C 1.2828 0.8946 0.2149 0.120 Uiso calc R 1 . .
C C9 1.3764(6) 0.5978(6) 0.1057(4) 0.0535(14) Uani d . 1 . .
H H9A 1.4400 0.5118 0.1293 0.080 Uiso calc R 1 . .
H H9B 1.4132 0.6935 0.1404 0.080 Uiso calc R 1 . .
H H9C 1.3858 0.6069 0.0406 0.080 Uiso calc R 1 . .
C C10 0.8236(6) 0.7901(7) 0.0860(4) 0.0620(16) Uani d . 1 . .
H H10A 0.7186 0.7529 0.0922 0.093 Uiso calc R 1 . .
H H10B 0.8256 0.8212 0.0231 0.093 Uiso calc R 1 . .
H H10C 0.8513 0.8786 0.1293 0.093 Uiso calc R 1 . .
C C12 0.4359(5) 0.6653(5) 0.3969(3) 0.0337(10) Uani d . 1 . .
C C13 0.5639(5) 0.6198(5) 0.3569(3) 0.0360(10) Uani d . 1 . .
H H13 0.6383 0.6954 0.3469 0.043 Uiso calc R 1 . .
C C14 0.5894(5) 0.4615(5) 0.3295(3) 0.0339(10) Uani d . 1 . .
C C15 0.4688(5) 0.3538(5) 0.3449(3) 0.0331(10) Uani d . 1 . .
H H15 0.4788 0.2481 0.3273 0.040 Uiso calc R 1 . .
C C16 0.3392(5) 0.4008(5) 0.3848(3) 0.0317(9) Uani d . 1 . .
C C17 0.1813(5) 0.6083(6) 0.4556(3) 0.0429(11) Uani d . 1 . .
H H17A 0.2108 0.6970 0.4997 0.051 Uiso calc R 1 . .
H H17B 0.1447 0.5237 0.4900 0.051 Uiso calc R 1 . .
C C18 0.0477(6) 0.6553(7) 0.3824(4) 0.0587(15) Uani d . 1 . .
H H18A 0.0911 0.7110 0.3353 0.088 Uiso calc R 1 . .
H H18B -0.0248 0.7219 0.4114 0.088 Uiso calc R 1 . .
H H18C -0.0081 0.5628 0.3538 0.088 Uiso calc R 1 . .
C C19 0.4154(6) 0.8323(6) 0.4274(4) 0.0537(14) Uani d . 1 . .
H H19A 0.4116 0.8405 0.4938 0.080 Uiso calc R 1 . .
H H19B 0.3178 0.8707 0.3950 0.080 Uiso calc R 1 . .
H H19C 0.5036 0.8937 0.4133 0.080 Uiso calc R 1 . .
C C20 0.2141(6) 0.2841(6) 0.3993(4) 0.0513(13) Uani d . 1 . .
H H20A 0.2376 0.1835 0.3714 0.077 Uiso calc R 1 . .
H H20B 0.1118 0.3182 0.3706 0.077 Uiso calc R 1 . .
H H20C 0.2124 0.2755 0.4653 0.077 Uiso calc R 1 . .
O O1 0.9580(4) 0.2656(4) 0.1836(3) 0.0475(9) Uani d . 1 . .
O O2 0.7136(4) 0.4211(4) 0.2935(2) 0.0429(8) Uani d . 1 . .
Zn Zn1 0.75971(6) 0.21641(6) 0.23222(4) 0.03594(15) Uani d . 1 . .
Br Br1 0.81438(7) 0.03353(6) 0.34965(4) 0.05785(18) Uani d . 1 . .
Br Br2 0.55242(6) 0.15373(7) 0.10973(4) 0.05343(17) Uani d . 1 . .
N N1 1.0984(4) 0.6872(4) 0.1000(2) 0.0371(9) Uani d . 1 . .
N N11 0.3231(4) 0.5561(4) 0.4125(2) 0.0315(8) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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'
N N 0.0061 0.0033 '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
C3 C2 N1 . . 119.8(4) ?
C3 C2 C9 . . 121.2(4) ?
N1 C2 C9 . . 119.0(4) ?
C2 C3 C4 . . 123.0(4) ?
C2 C3 H3 . . 118.5 ?
C4 C3 H3 . . 118.5 ?
O1 C4 C3 . . 121.4(4) ?
O1 C4 C5 . . 123.3(4) ?
C3 C4 C5 . . 115.3(4) ?
C6 C5 C4 . . 121.1(4) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 N1 . . 121.1(4) ?
C5 C6 C10 . . 119.5(4) ?
N1 C6 C10 . . 119.4(4) ?
N1 C7 C8 . . 111.1(4) ?
N1 C7 H7A . . 109.4 ?
C8 C7 H7A . . 109.4 ?
N1 C7 H7B . . 109.4 ?
C8 C7 H7B . . 109.4 ?
H7A C7 H7B . . 108.0 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C2 C9 H9A . . 109.5 ?
C2 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C2 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C6 C10 H10A . . 109.5 ?
C6 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C6 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C13 C12 N11 . . 120.3(4) ?
C13 C12 C19 . . 120.9(4) ?
N11 C12 C19 . . 118.8(4) ?
C12 C13 C14 . . 122.4(4) ?
C12 C13 H13 . . 118.8 ?
C14 C13 H13 . . 118.8 ?
O2 C14 C13 . . 121.1(4) ?
O2 C14 C15 . . 123.5(4) ?
C13 C14 C15 . . 115.4(4) ?
C16 C15 C14 . . 121.9(4) ?
C16 C15 H15 . . 119.1 ?
C14 C15 H15 . . 119.1 ?
C15 C16 N11 . . 120.0(4) ?
C15 C16 C20 . . 120.3(4) ?
N11 C16 C20 . . 119.7(4) ?
N11 C17 C18 . . 111.4(4) ?
N11 C17 H17A . . 109.3 ?
C18 C17 H17A . . 109.3 ?
N11 C17 H17B . . 109.3 ?
C18 C17 H17B . . 109.3 ?
H17A C17 H17B . . 108.0 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C12 C19 H19A . . 109.5 ?
C12 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C12 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C16 C20 H20A . . 109.5 ?
C16 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C16 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C4 O1 Zn1 . . 127.6(3) ?
C14 O2 Zn1 . . 128.4(3) ?
O1 Zn1 O2 . . 101.12(13) ?
O1 Zn1 Br2 . . 111.24(11) ?
O2 Zn1 Br2 . . 108.65(10) ?
O1 Zn1 Br1 . . 108.88(10) ?
O2 Zn1 Br1 . . 108.20(10) ?
Br2 Zn1 Br1 . . 117.46(3) ?
C6 N1 C2 . . 119.7(4) ?
C6 N1 C7 . . 120.7(4) ?
C2 N1 C7 . . 119.4(4) ?
C16 N11 C12 . . 120.0(3) ?
C16 N11 C17 . . 120.3(4) ?
C12 N11 C17 . . 119.7(4) ?
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
C2 C3 . 1.347(6) ?
C2 N1 . 1.371(5) ?
C2 C9 . 1.492(6) ?
C3 C4 . 1.395(6) ?
C3 H3 . 0.9300 ?
C4 O1 . 1.289(5) ?
C4 C5 . 1.417(6) ?
C5 C6 . 1.352(6) ?
C5 H5 . 0.9300 ?
C6 N1 . 1.360(6) ?
C6 C10 . 1.504(6) ?
C7 N1 . 1.476(6) ?
C7 C8 . 1.525(9) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C12 C13 . 1.344(6) ?
C12 N11 . 1.379(5) ?
C12 C19 . 1.484(6) ?
C13 C14 . 1.410(6) ?
C13 H13 . 0.9300 ?
C14 O2 . 1.275(5) ?
C14 C15 . 1.418(6) ?
C15 C16 . 1.358(6) ?
C15 H15 . 0.9300 ?
C16 N11 . 1.374(5) ?
C16 C20 . 1.493(6) ?
C17 N11 . 1.483(5) ?
C17 C18 . 1.508(7) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
O1 Zn1 . 1.957(3) y
O2 Zn1 . 1.976(3) y
Zn1 Br2 . 2.3501(8) y
Zn1 Br1 . 2.3635(8) y
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
C5 H5 O2 1 0.93 2.57 3.093(5) 115.9
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C2 C3 C4 . . . . 0.5(7) ?
C9 C2 C3 C4 . . . . 179.9(5) ?
C2 C3 C4 O1 . . . . -175.8(5) ?
C2 C3 C4 C5 . . . . 2.1(7) ?
O1 C4 C5 C6 . . . . 175.2(5) ?
C3 C4 C5 C6 . . . . -2.7(7) ?
C4 C5 C6 N1 . . . . 0.7(7) ?
C4 C5 C6 C10 . . . . -178.9(5) ?
N11 C12 C13 C14 . . . . -0.2(7) ?
C19 C12 C13 C14 . . . . 178.2(5) ?
C12 C13 C14 O2 . . . . -178.5(4) ?
C12 C13 C14 C15 . . . . 1.5(7) ?
O2 C14 C15 C16 . . . . 179.0(4) ?
C13 C14 C15 C16 . . . . -1.0(6) ?
C14 C15 C16 N11 . . . . -0.8(6) ?
C14 C15 C16 C20 . . . . 179.6(4) ?
C3 C4 O1 Zn1 . . . . 164.0(3) ?
C5 C4 O1 Zn1 . . . . -13.8(7) ?
C13 C14 O2 Zn1 . . . . -169.5(3) ?
C15 C14 O2 Zn1 . . . . 10.5(6) ?
C4 O1 Zn1 O2 . . . . -33.4(4) ?
C4 O1 Zn1 Br2 . . . . 81.8(4) ?
C4 O1 Zn1 Br1 . . . . -147.2(4) ?
C14 O2 Zn1 O1 . . . . 172.7(4) ?
C14 O2 Zn1 Br2 . . . . 55.6(4) ?
C14 O2 Zn1 Br1 . . . . -72.9(4) ?
C5 C6 N1 C2 . . . . 2.1(7) ?
C10 C6 N1 C2 . . . . -178.3(5) ?
C5 C6 N1 C7 . . . . -172.2(5) ?
C10 C6 N1 C7 . . . . 7.4(7) ?
C3 C2 N1 C6 . . . . -2.6(7) ?
C9 C2 N1 C6 . . . . 177.9(4) ?
C3 C2 N1 C7 . . . . 171.7(5) ?
C9 C2 N1 C7 . . . . -7.7(7) ?
C8 C7 N1 C6 . . . . 85.7(6) ?
C8 C7 N1 C2 . . . . -88.6(5) ?
C15 C16 N11 C12 . . . . 2.2(6) ?
C20 C16 N11 C12 . . . . -178.2(4) ?
C15 C16 N11 C17 . . . . 179.7(4) ?
C20 C16 N11 C17 . . . . -0.8(6) ?
C13 C12 N11 C16 . . . . -1.8(6) ?
C19 C12 N11 C16 . . . . 179.9(4) ?
C13 C12 N11 C17 . . . . -179.2(4) ?
C19 C12 N11 C17 . . . . 2.5(6) ?
C18 C17 N11 C16 . . . . -89.8(5) ?
C18 C17 N11 C12 . . . . 87.6(5) ?
