#------------------------------------------------------------------------------
#$Date: 2019-12-26 22:20:35 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246171 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/19/2311928.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_2311928
loop_
_publ_author_name
'Wang, Ai'
'Englert, Ulli'
_publ_section_title
;
 N-H...X (X = Cl and Br) hydrogen bonds in three isomorphous
 3,5-dichloropyridinium salts.
;
_journal_coeditor_code           YP3141
_journal_issue                   'Pt 10'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              803
_journal_page_last               809
_journal_paper_doi               10.1107/S2053229617013201
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          '(C5 H4 Cl2 N)2 [Zn Cl4]'
_chemical_formula_moiety         '2(C5 H4 Cl2 N +), Cl4 Zn 2-'
_chemical_formula_sum            'C10 H8 Cl8 N2 Zn'
_chemical_formula_weight         505.15
_chemical_name_common            a
_chemical_name_systematic
;
3,5-Dichloropyridinium tetrachloridozincate(II)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                85.5267(9)
_cell_angle_beta                 79.0539(10)
_cell_angle_gamma                80.1701(10)
_cell_formula_units_Z            4
_cell_length_a                   8.6181(6)
_cell_length_b                   12.8068(9)
_cell_length_c                   16.7622(12)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.53
_cell_volume                     1787.7(2)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2009)
;
_computing_data_collection
;
SMART (Bruker, 2001)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Bruker D8 goniometer with APEX CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27232
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.798
_diffrn_reflns_theta_min         1.239
_exptl_absorpt_coefficient_mu    2.560
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.877
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.811
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         10232
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0375P)²+0.4860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0745
_reflns_number_gt                8944
_reflns_number_total             10232
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yp3141sup1.cif
_cod_data_source_block           a
_cod_database_code               2311928
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.603
_shelx_estimated_absorpt_t_max   0.700
loop_
_space_group_symop_operation_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_occupancy
Zn Zn1 0.04124(2) 0.78927(2) 0.39906(2) 0.01146(5) Uani d 1
Cl Cl9 0.26668(5) 0.86528(4) 0.39903(3) 0.01472(9) Uani d 1
Cl Cl10 -0.14829(5) 0.85629(3) 0.50523(3) 0.01354(8) Uani d 1
Cl Cl11 0.09664(5) 0.61035(3) 0.41480(3) 0.01247(8) Uani d 1
Cl Cl12 -0.03922(5) 0.84000(3) 0.27916(2) 0.01314(8) Uani d 1
Zn Zn2 0.36013(2) 0.29703(2) 0.14760(2) 0.01090(5) Uani d 1
Cl Cl13 0.59505(5) 0.36103(3) 0.14726(2) 0.01451(9) Uani d 1
Cl Cl14 0.17331(5) 0.35504(3) 0.25770(2) 0.01274(8) Uani d 1
Cl Cl15 0.41474(5) 0.11842(3) 0.15994(3) 0.01330(8) Uani d 1
Cl Cl16 0.27101(5) 0.35377(3) 0.03059(2) 0.01191(8) Uani d 1
Cl Cl1 0.26683(5) 0.88582(4) 0.02446(3) 0.01907(9) Uani d 1
Cl Cl2 0.86632(5) 0.86925(4) 0.08192(3) 0.01723(9) Uani d 1
N N1 0.44948(19) 0.86663(12) 0.22309(9) 0.0150(3) Uani d 1
H H1 0.412(3) 0.8646(17) 0.2745(10) 0.018 Uiso d 1
C C1 0.3442(2) 0.87317(14) 0.17271(11) 0.0152(3) Uani d 1
H H1A 0.2333 0.8754 0.1935 0.018 Uiso calc 1
C C2 0.4009(2) 0.87664(13) 0.08998(11) 0.0137(3) Uani d 1
C C3 0.5630(2) 0.87447(13) 0.05965(11) 0.0125(3) Uani d 1
H H3A 0.6026 0.8764 0.0028 0.015 Uiso calc 1
C C4 0.6650(2) 0.86933(14) 0.11513(11) 0.0126(3) Uani d 1
C C5 0.6072(2) 0.86510(14) 0.19792(11) 0.0151(3) Uani d 1
H H5 0.6771 0.8612 0.2359 0.018 Uiso calc 1
Cl Cl3 0.48206(6) 0.91805(5) 0.62077(3) 0.03215(13) Uani d 1
Cl Cl4 0.01348(6) 0.85565(4) 0.87638(3) 0.02460(11) Uani d 1
N N2 0.02787(19) 0.90136(12) 0.64179(10) 0.0156(3) Uani d 1
H H2 -0.035(2) 0.9035(18) 0.6090(12) 0.019 Uiso d 1
C C6 0.1787(2) 0.91230(14) 0.61020(11) 0.0164(4) Uani d 1
H H6 0.2105 0.9249 0.5533 0.020 Uiso calc 1
C C7 0.2875(2) 0.90490(15) 0.66191(12) 0.0168(4) Uani d 1
C C8 0.2407(2) 0.88611(14) 0.74520(11) 0.0155(3) Uani d 1
H H8 0.3152 0.8799 0.7811 0.019 Uiso calc 1
C C9 0.0816(2) 0.87680(14) 0.77386(11) 0.0145(3) Uani d 1
C C10 -0.0261(2) 0.88468(14) 0.72147(11) 0.0147(3) Uani d 1
H H10 -0.1351 0.8785 0.7413 0.018 Uiso calc 1
Cl Cl5 0.58818(5) 0.38973(4) -0.23486(3) 0.01754(9) Uani d 1
Cl Cl6 1.16900(6) 0.41530(4) -0.16871(3) 0.02303(10) Uani d 1
N N3 0.7563(2) 0.38242(12) -0.03267(10) 0.0157(3) Uani d 1
H H3 0.719(3) 0.3781(17) 0.0183(10) 0.019 Uiso d 1
C C11 0.6548(2) 0.38432(14) -0.08452(12) 0.0156(4) Uani d 1
H H11 0.5447 0.3810 -0.0651 0.019 Uiso calc 1
C C12 0.7146(2) 0.39120(13) -0.16679(11) 0.0133(3) Uani d 1
C C13 0.8745(2) 0.39961(14) -0.19524(11) 0.0136(3) Uani d 1
H H13 0.9160 0.4046 -0.2519 0.016 Uiso calc 1
C C14 0.9714(2) 0.40048(14) -0.13817(11) 0.0146(3) Uani d 1
C C15 0.9111(2) 0.39063(14) -0.05576(11) 0.0157(4) Uani d 1
H H15 0.9780 0.3897 -0.0166 0.019 Uiso calc 1
Cl Cl7 0.81474(5) 0.36432(4) 0.36786(3) 0.02234(10) Uani d 1
Cl Cl8 0.34307(6) 0.35201(4) 0.63139(3) 0.02176(10) Uani d 1
N N4 0.35093(19) 0.37563(13) 0.39696(10) 0.0164(3) Uani d 1
H H4 0.284(2) 0.3783(17) 0.3626(12) 0.020 Uiso d 1
C C16 0.5047(2) 0.37287(15) 0.36260(11) 0.0168(4) Uani d 1
H H16 0.5360 0.3760 0.3051 0.020 Uiso calc 1
C C17 0.6175(2) 0.36545(14) 0.41234(11) 0.0151(3) Uani d 1
C C18 0.5707(2) 0.35942(14) 0.49646(11) 0.0149(3) Uani d 1
H H18 0.6470 0.3544 0.5313 0.018 Uiso calc 1
C C19 0.4098(2) 0.36094(14) 0.52803(11) 0.0131(3) Uani d 1
C C20 0.2979(2) 0.37024(14) 0.47730(11) 0.0141(3) Uani d 1
H H20 0.1872 0.3727 0.4989 0.017 Uiso calc 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'
Cl Cl 0.1484 0.1585 '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'
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
Cl12 Zn1 Cl11 111.420(17) y
Cl12 Zn1 Cl10 110.664(18) y
Cl11 Zn1 Cl10 110.214(17) y
Cl12 Zn1 Cl9 106.721(17) y
Cl11 Zn1 Cl9 110.837(17) y
Cl10 Zn1 Cl9 106.835(17) y
Cl15 Zn2 Cl16 112.014(17) y
Cl15 Zn2 Cl14 108.093(17) y
Cl16 Zn2 Cl14 110.582(17) y
Cl15 Zn2 Cl13 107.358(17) y
Cl16 Zn2 Cl13 108.789(17) y
Cl14 Zn2 Cl13 109.945(17) y
C1 N1 C5 123.88(16) ?
C1 N1 H1 117.2(15) ?
C5 N1 H1 118.9(15) ?
N1 C1 C2 118.41(16) ?
N1 C1 H1A 120.8 ?
C2 C1 H1A 120.8 ?
C1 C2 C3 120.78(17) ?
C1 C2 Cl1 118.93(14) ?
C3 C2 Cl1 120.29(14) ?
C4 C3 C2 117.85(16) ?
C4 C3 H3A 121.1 ?
C2 C3 H3A 121.1 ?
C5 C4 C3 120.92(16) ?
C5 C4 Cl2 118.72(14) ?
C3 C4 Cl2 120.36(13) ?
N1 C5 C4 118.16(17) ?
N1 C5 H5 120.9 ?
C4 C5 H5 120.9 ?
C6 N2 C10 123.99(17) ?
C6 N2 H2 117.0(16) ?
C10 N2 H2 119.0(16) ?
N2 C6 C7 118.61(17) ?
N2 C6 H6 120.7 ?
C7 C6 H6 120.7 ?
C6 C7 C8 120.61(17) ?
C6 C7 Cl3 118.40(14) ?
C8 C7 Cl3 120.98(15) ?
C9 C8 C7 117.63(17) ?
C9 C8 H8 121.2 ?
C7 C8 H8 121.2 ?
C10 C9 C8 121.15(17) ?
C10 C9 Cl4 118.38(14) ?
C8 C9 Cl4 120.47(14) ?
N2 C10 C9 118.01(17) ?
N2 C10 H10 121.0 ?
C9 C10 H10 121.0 ?
C15 N3 C11 123.98(16) ?
C15 N3 H3 118.0(15) ?
C11 N3 H3 118.0(15) ?
N3 C11 C12 118.21(17) ?
N3 C11 H11 120.9 ?
C12 C11 H11 120.9 ?
C11 C12 C13 120.92(17) ?
C11 C12 Cl5 119.22(14) ?
C13 C12 Cl5 119.86(14) ?
C14 C13 C12 117.74(16) ?
C14 C13 H13 121.1 ?
C12 C13 H13 121.1 ?
C15 C14 C13 120.82(17) ?
C15 C14 Cl6 118.79(14) ?
C13 C14 Cl6 120.39(14) ?
N3 C15 C14 118.28(17) ?
N3 C15 H15 120.9 ?
C14 C15 H15 120.9 ?
C16 N4 C20 124.11(17) ?
C16 N4 H4 115.3(15) ?
C20 N4 H4 120.5(15) ?
N4 C16 C17 118.76(17) ?
N4 C16 H16 120.6 ?
C17 C16 H16 120.6 ?
C16 C17 C18 120.15(16) ?
C16 C17 Cl7 118.59(14) ?
C18 C17 Cl7 121.27(14) ?
C19 C18 C17 118.11(17) ?
C19 C18 H18 120.9 ?
C17 C18 H18 120.9 ?
C18 C19 C20 120.99(17) ?
C18 C19 Cl8 120.83(14) ?
C20 C19 Cl8 118.18(14) ?
N4 C20 C19 117.86(16) ?
N4 C20 H20 121.1 ?
C19 C20 H20 121.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 Cl12 2.2615(5) y
Zn1 Cl11 2.2646(5) y
Zn1 Cl10 2.2863(5) y
Zn1 Cl9 2.3168(5) y
Zn2 Cl15 2.2566(5) y
Zn2 Cl16 2.2636(5) y
Zn2 Cl14 2.2863(5) y
Zn2 Cl13 2.3091(5) y
Cl1 C2 1.7237(19) ?
Cl2 C4 1.7181(18) ?
N1 C1 1.340(2) ?
N1 C5 1.341(2) ?
N1 H1 0.860(15) ?
C1 C2 1.380(3) ?
C1 H1A 0.9500 ?
C2 C3 1.389(2) ?
C3 C4 1.387(2) ?
C3 H3A 0.9500 ?
C4 C5 1.383(2) ?
C5 H5 0.9500 ?
Cl3 C7 1.7186(19) ?
Cl4 C9 1.7234(18) ?
N2 C6 1.333(2) ?
N2 C10 1.341(2) ?
N2 H2 0.841(15) ?
C6 C7 1.381(3) ?
C6 H6 0.9500 ?
C7 C8 1.392(3) ?
C8 C9 1.386(2) ?
C8 H8 0.9500 ?
C9 C10 1.381(3) ?
C10 H10 0.9500 ?
Cl5 C12 1.7236(19) ?
Cl6 C14 1.7211(18) ?
N3 C15 1.336(2) ?
N3 C11 1.341(2) ?
N3 H3 0.854(15) ?
C11 C12 1.379(3) ?
C11 H11 0.9500 ?
C12 C13 1.390(2) ?
C13 C14 1.386(3) ?
C13 H13 0.9500 ?
C14 C15 1.385(2) ?
C15 H15 0.9500 ?
Cl7 C17 1.7199(18) ?
Cl8 C19 1.7201(18) ?
N4 C16 1.337(2) ?
N4 C20 1.338(2) ?
N4 H4 0.886(15) ?
C16 C17 1.383(3) ?
C16 H16 0.9500 ?
C17 C18 1.391(3) ?
C18 C19 1.385(2) ?
C18 H18 0.9500 ?
C19 C20 1.387(2) ?
C20 H20 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 Cl9 0.860(15) 2.222(16) 3.0686(16) 168(2)
N2 H2 Cl10 0.841(15) 2.311(17) 3.1150(16) 160(2)
N3 H3 Cl13 0.854(15) 2.234(16) 3.0842(16) 173(2)
N4 H4 Cl14 0.886(15) 2.214(16) 3.0744(17) 164(2)
