#------------------------------------------------------------------------------
#$Date: 2016-05-04 21:42:30 +0300 (Wed, 04 May 2016) $
#$Revision: 182545 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/04/2020444.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_2020444
loop_
_publ_author_name
'Karthikeyan, Ammasai'
'Zeller, Matthias'
'Thomas Muthiah, Packianathan'
_publ_section_title
;
 Supramolecular hydrogen-bonding patterns in the organic--inorganic hybrid
 compound bis(4-amino-5-chloro-2,6-dimethylpyrimidinium)
 tetrathiocyanatozinc(II)--4-amino-5-chloro-2,6-dimethylpyrimidine--water
 (1/2/2)
;
_journal_coeditor_code           CU3096
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              337
_journal_page_last               340
_journal_paper_doi               10.1107/S2053229616004186
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac
'(C6 H9 Cl N3) [Zn (N C S)4], 2C6 H8 Cl N3, 2H2 O'
_chemical_formula_moiety
'2(C6 H9 Cl N3 +),  C4 N4 S4 Zn 2-, 2(C6 H8 Cl N3), 2(H2 O)'
_chemical_formula_sum            'C28 H38 Cl4 N16 O2 S4 Zn'
_chemical_formula_weight         966.15
_chemical_name_systematic
'Bis(4-amino-5-chloro-2,6-dimethylpyrimidinium) tetrathiocyanatozinc(II)--4-amino-5-chloro-2,6-dimethylpyrimidine--water (1/2/2)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL2013
_cell_angle_alpha                90
_cell_angle_beta                 119.4829(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.4354(7)
_cell_length_b                   16.7556(6)
_cell_length_c                   15.3266(6)
_cell_measurement_reflns_used    8426
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.4517
_cell_measurement_theta_min      2.4311
_cell_volume                     4344.8(3)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015) and
SHELXLE (Hübschle et al.,  2011)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker D8 Quest CMOS'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25175
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.547
_diffrn_reflns_theta_min         2.431
_exptl_absorpt_coefficient_mu    1.052
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(APEX2; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.413
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         6507
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0317P)²+7.8231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                4548
_reflns_number_total             6507
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cu3096sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2020444.cif.'
_cod_database_code               2020444
_cod_database_fobs_code          2020444
_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   0.764
_shelx_estimated_absorpt_t_max   0.875
_shelxl_version_number           .2013
loop_
_space_group_symop_operation_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_occupancy
C C1 0.11718(13) 0.10092(13) 0.38335(17) 0.0229(5) Uani d 1
C C2 0.04852(13) 0.36488(14) 0.15248(17) 0.0225(5) Uani d 1
N N1 0.08331(12) 0.15844(12) 0.34275(17) 0.0326(5) Uani d 1
N N2 0.03536(12) 0.30479(12) 0.17978(16) 0.0297(5) Uani d 1
O O1 0.24989(10) -0.01341(10) 0.21097(13) 0.0255(4) Uani d 1
H H1A 0.2945(12) -0.0248(17) 0.2575(17) 0.038 Uiso d 1
H H1B 0.2567(17) 0.0244(14) 0.180(2) 0.038 Uiso d 1
S S1 0.16709(4) 0.02232(3) 0.44438(5) 0.02800(14) Uani d 1
S S2 0.06662(4) 0.44762(3) 0.11161(4) 0.02462(13) Uani d 1
Zn Zn1 0.0000 0.23105(2) 0.2500 0.02289(10) Uani d 1
N N1A 0.34484(10) 0.36431(10) 0.37009(13) 0.0184(4) Uani d 1
H H1N 0.3164 0.4078 0.3593 0.022 Uiso calc 1
C C2A 0.41367(13) 0.36956(13) 0.36986(16) 0.0192(4) Uani d 1
N N3A 0.45872(10) 0.30678(10) 0.38336(13) 0.0179(4) Uani d 1
C C4A 0.43393(12) 0.23410(12) 0.39739(16) 0.0170(4) Uani d 1
C C5A 0.36274(13) 0.22810(12) 0.40210(16) 0.0174(4) Uani d 1
C C6A 0.31731(12) 0.29419(13) 0.38638(16) 0.0177(4) Uani d 1
C C7A 0.43807(14) 0.44973(13) 0.3525(2) 0.0269(5) Uani d 1
H H7AA 0.4931 0.4476 0.3672 0.040 Uiso calc 1
H H7AB 0.4331 0.4889 0.3965 0.040 Uiso calc 1
H H7AC 0.4040 0.4653 0.2824 0.040 Uiso calc 1
C C8A 0.23945(13) 0.29757(14) 0.38287(18) 0.0237(5) Uani d 1
H H8AA 0.2002 0.3220 0.3196 0.036 Uiso calc 1
H H8AB 0.2443 0.3296 0.4391 0.036 Uiso calc 1
H H8AC 0.2225 0.2434 0.3875 0.036 Uiso calc 1
Cl Cl1A 0.33386(3) 0.13573(3) 0.42265(5) 0.02680(13) Uani d 1
N N4A 0.47755(11) 0.17171(11) 0.40456(15) 0.0233(4) Uani d 1
H H4A1 0.5208 0.1779 0.4003 0.028 Uiso calc 1
H H4A2 0.4635 0.1238 0.4136 0.028 Uiso calc 1
N N1B 0.28300(10) 0.11725(11) 0.13255(14) 0.0191(4) Uani d 1
C C2B 0.35036(12) 0.12117(12) 0.12934(16) 0.0168(4) Uani d 1
N N3B 0.38674(10) 0.18820(10) 0.12723(13) 0.0167(4) Uani d 1
C C4B 0.35258(12) 0.25812(12) 0.12673(15) 0.0165(4) Uani d 1
C C5B 0.28012(12) 0.25815(12) 0.12759(16) 0.0170(4) Uani d 1
C C6B 0.24691(12) 0.18685(13) 0.13106(16) 0.0179(4) Uani d 1
C C7B 0.38767(14) 0.04338(13) 0.12699(19) 0.0244(5) Uani d 1
H H7BA 0.4131 0.0491 0.0858 0.037 Uiso calc 1
H H7BB 0.3469 0.0019 0.0983 0.037 Uiso calc 1
H H7BC 0.4273 0.0283 0.1953 0.037 Uiso calc 1
C C8B 0.17104(14) 0.17983(14) 0.13403(19) 0.0259(5) Uani d 1
H H8BA 0.1420 0.2304 0.1126 0.039 Uiso calc 1
H H8BB 0.1828 0.1675 0.2025 0.039 Uiso calc 1
H H8BC 0.1387 0.1370 0.0889 0.039 Uiso calc 1
Cl Cl1B 0.23541(3) 0.34875(3) 0.12316(4) 0.02473(13) Uani d 1
N N4B 0.38898(11) 0.32520(10) 0.12500(14) 0.0226(4) Uani d 1
H H4B1 0.4339 0.3228 0.1242 0.027 Uiso calc 1
H H4B2 0.3680 0.3718 0.1246 0.027 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
Cl Cl 0.1484 0.1585 '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 S1 . . 177.7(2)
N2 C2 S2 . . 178.4(2)
C1 N1 Zn1 . . 161.95(19)
C2 N2 Zn1 . . 159.1(2)
H1A O1 H1B . . 106(3)
N1 Zn1 N1 . 2 103.44(12)
N1 Zn1 N2 . 2 112.20(9)
N1 Zn1 N2 2 2 113.50(9)
N1 Zn1 N2 . . 113.50(9)
N1 Zn1 N2 2 . 112.20(9)
N2 Zn1 N2 2 . 102.37(12)
C2A N1A C6A . . 122.56(18)
C2A N1A H1N . . 118.7
C6A N1A H1N . . 118.7
N3A C2A N1A . . 122.2(2)
N3A C2A C7A . . 120.1(2)
N1A C2A C7A . . 117.66(19)
C2A N3A C4A . . 118.54(18)
N4A C4A N3A . . 117.31(19)
N4A C4A C5A . . 122.80(19)
N3A C4A C5A . . 119.88(18)
C6A C5A C4A . . 119.67(19)
C6A C5A Cl1A . . 121.35(17)
C4A C5A Cl1A . . 118.92(16)
C5A C6A N1A . . 117.02(19)
C5A C6A C8A . . 126.6(2)
N1A C6A C8A . . 116.35(19)
C2A C7A H7AA . . 109.5
C2A C7A H7AB . . 109.5
H7AA C7A H7AB . . 109.5
C2A C7A H7AC . . 109.5
H7AA C7A H7AC . . 109.5
H7AB C7A H7AC . . 109.5
C6A C8A H8AA . . 109.5
C6A C8A H8AB . . 109.5
H8AA C8A H8AB . . 109.5
C6A C8A H8AC . . 109.5
H8AA C8A H8AC . . 109.5
H8AB C8A H8AC . . 109.5
C4A N4A H4A1 . . 120.0
C4A N4A H4A2 . . 120.0
H4A1 N4A H4A2 . . 120.0
C2B N1B C6B . . 117.74(18)
N1B C2B N3B . . 125.61(19)
N1B C2B C7B . . 116.88(18)
N3B C2B C7B . . 117.51(18)
C2B N3B C4B . . 117.83(18)
N4B C4B N3B . . 117.94(19)
N4B C4B C5B . . 122.64(19)
N3B C4B C5B . . 119.42(18)
C6B C5B C4B . . 119.32(19)
C6B C5B Cl1B . . 121.87(16)
C4B C5B Cl1B . . 118.81(16)
N1B C6B C5B . . 120.05(19)
N1B C6B C8B . . 116.09(19)
C5B C6B C8B . . 123.9(2)
C2B C7B H7BA . . 109.5
C2B C7B H7BB . . 109.5
H7BA C7B H7BB . . 109.5
C2B C7B H7BC . . 109.5
H7BA C7B H7BC . . 109.5
H7BB C7B H7BC . . 109.5
C6B C8B H8BA . . 109.5
C6B C8B H8BB . . 109.5
H8BA C8B H8BB . . 109.5
C6B C8B H8BC . . 109.5
H8BA C8B H8BC . . 109.5
H8BB C8B H8BC . . 109.5
C4B N4B H4B1 . . 120.0
C4B N4B H4B2 . . 120.0
H4B1 N4B H4B2 . . 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.160(3)
C1 S1 . 1.630(2)
C2 N2 . 1.166(3)
C2 S2 . 1.629(3)
N1 Zn1 . 1.964(2)
N2 Zn1 . 1.971(2)
O1 H1A . 0.829(17)
O1 H1B . 0.840(17)
Zn1 N1 2 1.964(2)
Zn1 N2 2 1.971(2)
N1A C2A . 1.342(3)
N1A C6A . 1.364(3)
N1A H1N . 0.8800
C2A N3A . 1.318(3)
C2A C7A . 1.491(3)
N3A C4A . 1.365(3)
C4A N4A . 1.316(3)
C4A C5A . 1.424(3)
C5A C6A . 1.362(3)
C5A Cl1A . 1.727(2)
C6A C8A . 1.489(3)
C7A H7AA . 0.9800
C7A H7AB . 0.9800
C7A H7AC . 0.9800
C8A H8AA . 0.9800
C8A H8AB . 0.9800
C8A H8AC . 0.9800
N4A H4A1 . 0.8800
N4A H4A2 . 0.8800
N1B C2B . 1.336(3)
N1B C6B . 1.355(3)
C2B N3B . 1.336(3)
C2B C7B . 1.501(3)
N3B C4B . 1.345(3)
C4B N4B . 1.335(3)
C4B C5B . 1.415(3)
C5B C6B . 1.371(3)
C5B Cl1B . 1.734(2)
C6B C8B . 1.502(3)
C7B H7BA . 0.9800
C7B H7BB . 0.9800
C7B H7BC . 0.9800
C8B H8BA . 0.9800
C8B H8BB . 0.9800
C8B H8BC . 0.9800
N4B H4B1 . 0.8800
N4B H4B2 . 0.8800
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
O1 H1A S2 4_545 0.83(2) 2.49(2) 3.316(2) 175(3)
O1 H1B N1B . 0.84(3) 1.89(3) 2.723(2) 170(3)
N1A H1N O1 4 0.88 1.79 2.623(2) 158
N4A H4A1 N3B 2_655 0.88 2.05 2.922(3) 173
N4B H4B1 N3A 2_655 0.88 2.16 3.041(3) 175
N4B H4B2 S1 4 0.88 2.69 3.4766(18) 150
N4A H4A2 Cl1A . 0.88 2.60 3.000(2) 109
N4B H4B2 Cl1B . 0.88 2.60 2.997(2) 109
C8A H8AC Cl1A . 0.98 2.66 3.161(2) 112
C8B H8BA Cl1B . 0.98 2.64 3.132(2) 111
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
C6A N1A C2A N3A 1.4(3)
C6A N1A C2A C7A -179.2(2)
N1A C2A N3A C4A 0.4(3)
C7A C2A N3A C4A -178.9(2)
C2A N3A C4A N4A 176.0(2)
C2A N3A C4A C5A -3.1(3)
N4A C4A C5A C6A -174.9(2)
N3A C4A C5A C6A 4.0(3)
N4A C4A C5A Cl1A 2.4(3)
N3A C4A C5A Cl1A -178.60(15)
C4A C5A C6A N1A -2.2(3)
Cl1A C5A C6A N1A -179.51(16)
C4A C5A C6A C8A 176.3(2)
Cl1A C5A C6A C8A -1.0(3)
C2A N1A C6A C5A -0.4(3)
C2A N1A C6A C8A -179.1(2)
C6B N1B C2B N3B 1.7(3)
C6B N1B C2B C7B -177.67(19)
N1B C2B N3B C4B -1.1(3)
C7B C2B N3B C4B 178.3(2)
C2B N3B C4B N4B 179.76(19)
C2B N3B C4B C5B -0.5(3)
N4B C4B C5B C6B -178.9(2)
N3B C4B C5B C6B 1.4(3)
N4B C4B C5B Cl1B 1.6(3)
N3B C4B C5B Cl1B -178.10(15)
C2B N1B C6B C5B -0.8(3)
C2B N1B C6B C8B 179.6(2)
C4B C5B C6B N1B -0.7(3)
Cl1B C5B C6B N1B 178.75(16)
C4B C5B C6B C8B 178.9(2)
Cl1B C5B C6B C8B -1.6(3)
