#------------------------------------------------------------------------------
#$Date: 2019-06-12 07:25:17 +0300 (Wed, 12 Jun 2019) $
#$Revision: 215867 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/16/2021665.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_2021665
loop_
_publ_author_name
'Castiñeiras, Alfonso'
'García-Santos, Isabel'
'Saa, Manuel'
_publ_section_title
;
 Design and synthesis of methyl
 2-{[4-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetate
 (phpy2NS) as a ligand for complexes of Group 12 elements: structural
 assessment and hydrogen-bonded supramolecular assembly analysis
;
_journal_coeditor_code           LG3239
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322961900682X
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          '[Hg Cl2 (C16 H14 N4 O2 S)]'
_chemical_formula_moiety         'C16 H14 Cl2 Hg N4 O2 S'
_chemical_formula_sum            'C16 H14 Cl2 Hg N4 O2 S'
_chemical_formula_weight         597.86
_chemical_name_systematic
;Dichlorido(methyl
2-{[4-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl-κ²N¹,N⁵]sulfanyl}acetato)mercury(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'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                105.050(3)
_cell_angle_beta                 95.083(3)
_cell_angle_gamma                115.081(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5198(3)
_cell_length_b                   9.4709(3)
_cell_length_c                   13.9682(7)
_cell_measurement_reflns_used    1863
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.317
_cell_measurement_theta_min      2.515
_cell_volume                     960.04(7)
_computing_cell_refinement
;
APEX2 (Bruker, 2005)
;
_computing_data_collection
;
APEX2 (Bruker, 2005)
;
_computing_data_reduction
;
APEX2 (Bruker, 2005)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2013 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8 KappaAPEXII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            21983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.011
_diffrn_reflns_theta_min         1.550
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    8.421
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    2.068
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.830
_refine_diff_density_min         -1.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0212P)²+3.2485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0576
_refine_ls_wR_factor_ref         0.0598
_reflns_number_gt                3341
_reflns_number_total             3765
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lg3239sup1.cif
_cod_data_source_block           Compound_4
_cod_database_code               2021665
_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   0.552
_shelx_estimated_absorpt_t_max   0.786
_shelxl_version_number           2.013
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
Hg Hg1 0.80705(3) 1.28547(2) 0.38893(2) 0.02077(7) Uani d 1
Cl Cl1 0.77534(17) 1.49373(15) 0.50670(10) 0.0263(3) Uani d 1
Cl Cl2 0.89922(18) 1.19938(19) 0.24002(11) 0.0355(3) Uani d 1
S S1 0.27962(19) 0.63277(16) 0.06736(10) 0.0282(3) Uani d 1
O O1 -0.0199(5) 0.6971(5) 0.1261(3) 0.0315(9) Uani d 1
O O2 -0.0380(6) 0.8222(5) 0.0114(3) 0.0432(11) Uani d 1
N N11 0.7903(5) 1.0968(5) 0.4808(3) 0.0202(9) Uani d 1
N N12 0.5208(5) 1.0074(5) 0.3150(3) 0.0210(9) Uani d 1
N N13 0.4136(6) 0.9344(5) 0.2172(3) 0.0215(9) Uani d 1
N N14 0.4766(5) 0.7521(5) 0.2602(3) 0.0181(9) Uani d 1
C C1 0.1837(7) 0.7405(7) 0.0148(4) 0.0264(12) Uani d 1
H H1A 0.2780 0.8535 0.0255 0.032 Uiso calc 1
H H1B 0.1382 0.6832 -0.0595 0.032 Uiso calc 1
C C2 0.0355(7) 0.7516(6) 0.0604(4) 0.0242(12) Uani d 1
C C3 -0.2014(10) 0.8255(9) 0.0422(6) 0.0533(19) Uani d 1
H H3A -0.2945 0.7122 0.0281 0.080 Uiso calc 1
H H3B -0.2439 0.8800 0.0034 0.080 Uiso calc 1
H H3C -0.1723 0.8864 0.1151 0.080 Uiso calc 1
C C11 0.8941(7) 1.1437(6) 0.5731(4) 0.0248(12) Uani d 1
H H11 0.9773 1.2570 0.6049 0.030 Uiso calc 1
C C12 0.8844(7) 1.0334(7) 0.6235(4) 0.0260(12) Uani d 1
H H12 0.9580 1.0706 0.6892 0.031 Uiso calc 1
C C13 0.7664(7) 0.8689(6) 0.5769(4) 0.0251(12) Uani d 1
H H13 0.7592 0.7904 0.6093 0.030 Uiso calc 1
C C14 0.6572(7) 0.8188(6) 0.4813(4) 0.0233(12) Uani d 1
H H14 0.5743 0.7060 0.4477 0.028 Uiso calc 1
C C15 0.6719(6) 0.9355(6) 0.4369(4) 0.0174(10) Uani d 1
C C16 0.5575(6) 0.8987(6) 0.3391(4) 0.0164(10) Uani d 1
C C17 0.3903(7) 0.7813(6) 0.1865(4) 0.0197(11) Uani d 1
C C18 0.4932(7) 0.6027(6) 0.2462(4) 0.0192(11) Uani d 1
C C19 0.6528(7) 0.6062(6) 0.2321(4) 0.0208(11) Uani d 1
H H19 0.7509 0.7061 0.2345 0.025 Uiso calc 1
C C110 0.6686(8) 0.4627(7) 0.2145(4) 0.0281(13) Uani d 1
H H110 0.7788 0.4644 0.2063 0.034 Uiso calc 1
C C111 0.5249(8) 0.3172(6) 0.2088(4) 0.0268(12) Uani d 1
H H111 0.5358 0.2187 0.1963 0.032 Uiso calc 1
C C112 0.3632(8) 0.3148(6) 0.2213(4) 0.0262(12) Uani d 1
H H112 0.2636 0.2140 0.2159 0.031 Uiso calc 1
C C113 0.3473(7) 0.4582(6) 0.2415(4) 0.0242(12) Uani d 1
H H113 0.2385 0.4578 0.2521 0.029 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'
Cl Cl 0.1484 0.1585 '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'
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'
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
Cl1 Hg1 Cl2 148.93(5) y
Cl1 Hg1 N11 103.23(10) y
Cl2 Hg1 N11 106.15(11) y
Cl1 Hg1 N12 114.52(10) y
Cl2 Hg1 N12 86.27(10) y
N11 Hg1 N12 67.54(14) y
C17 S1 C1 98.7(2) ?
C2 O2 C3 115.4(5) ?
C11 N11 C15 118.1(4) ?
C11 N11 Hg1 123.5(3) ?
C15 N11 Hg1 118.5(3) ?
C16 N12 N13 108.6(4) ?
C16 N12 Hg1 106.3(3) ?
N13 N12 Hg1 128.4(3) ?
C17 N13 N12 105.8(4) ?
C17 N14 C16 104.8(4) ?
C17 N14 C18 124.4(4) ?
C16 N14 C18 130.2(4) ?
C2 C1 S1 113.4(4) ?
C2 C1 H1A 108.9 ?
S1 C1 H1A 108.9 ?
C2 C1 H1B 108.9 ?
S1 C1 H1B 108.9 ?
H1A C1 H1B 107.7 ?
O1 C2 O2 124.0(5) ?
O1 C2 C1 126.2(5) ?
O2 C2 C1 109.6(5) ?
O2 C3 H3A 109.5 ?
O2 C3 H3B 109.5 ?
H3A C3 H3B 109.5 ?
O2 C3 H3C 109.5 ?
H3A C3 H3C 109.5 ?
H3B C3 H3C 109.5 ?
N11 C11 C12 122.5(5) ?
N11 C11 H11 118.8 ?
C12 C11 H11 118.8 ?
C13 C12 C11 118.9(5) ?
C13 C12 H12 120.6 ?
C11 C12 H12 120.6 ?
C12 C13 C14 119.1(5) ?
C12 C13 H13 120.5 ?
C14 C13 H13 120.5 ?
C15 C14 C13 118.7(5) ?
C15 C14 H14 120.6 ?
C13 C14 H14 120.6 ?
N11 C15 C14 122.7(5) ?
N11 C15 C16 113.8(4) ?
C14 C15 C16 123.5(4) ?
N12 C16 N14 109.8(4) ?
N12 C16 C15 123.2(4) ?
N14 C16 C15 127.0(4) ?
N13 C17 N14 111.0(4) ?
N13 C17 S1 127.4(4) ?
N14 C17 S1 121.5(4) ?
C19 C18 C113 121.5(5) ?
C19 C18 N14 118.6(4) ?
C113 C18 N14 119.8(5) ?
C18 C19 C110 119.3(5) ?
C18 C19 H19 120.4 ?
C110 C19 H19 120.4 ?
C111 C110 C19 120.2(5) ?
C111 C110 H110 119.9 ?
C19 C110 H110 119.9 ?
C110 C111 C112 119.9(5) ?
C110 C111 H111 120.0 ?
C112 C111 H111 120.0 ?
C113 C112 C111 120.3(5) ?
C113 C112 H112 119.8 ?
C111 C112 H112 119.8 ?
C112 C113 C18 118.7(5) ?
C112 C113 H113 120.7 ?
C18 C113 H113 120.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Hg1 Cl1 2.3483(12) y
Hg1 Cl2 2.3579(14) y
Hg1 N11 2.423(4) y
Hg1 N12 2.578(4) y
S1 C17 1.738(5) ?
S1 C1 1.799(5) ?
O1 C2 1.203(6) ?
O2 C2 1.351(7) ?
O2 C3 1.503(8) ?
N11 C11 1.345(7) ?
N11 C15 1.350(6) ?
N12 C16 1.305(6) ?
N12 N13 1.391(6) ?
N13 C17 1.321(6) ?
N14 C17 1.364(6) ?
N14 C16 1.370(6) ?
N14 C18 1.446(6) ?
C1 C2 1.494(8) ?
C1 H1A 0.9900 ?
C1 H1B 0.9900 ?
C3 H3A 0.9800 ?
C3 H3B 0.9800 ?
C3 H3C 0.9800 ?
C11 C12 1.383(7) ?
C11 H11 0.9500 ?
C12 C13 1.375(7) ?
C12 H12 0.9500 ?
C13 C14 1.397(7) ?
C13 H13 0.9500 ?
C14 C15 1.369(7) ?
C14 H14 0.9500 ?
C15 C16 1.472(7) ?
C18 C19 1.379(7) ?
C18 C113 1.386(7) ?
C19 C110 1.383(7) ?
C19 H19 0.9500 ?
C110 C111 1.379(8) ?
C110 H110 0.9500 ?
C111 C112 1.395(8) ?
C111 H111 0.9500 ?
C112 C113 1.381(7) ?
C112 H112 0.9500 ?
C113 H113 0.9500 ?
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
C3 H3C Cl2 1_455 0.98 2.79 3.583(8) 138.2
C19 H19 O1 1_655 0.95 2.59 3.172(6) 119.9
C113 H113 Cl2 1_445 0.95 2.84 3.551(6) 132.3
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
C16 N12 N13 C17 0.1(5)
Hg1 N12 N13 C17 130.2(4)
C17 S1 C1 C2 -71.7(4)
C3 O2 C2 O1 -1.6(8)
C3 O2 C2 C1 173.9(5)
S1 C1 C2 O1 0.2(7)
S1 C1 C2 O2 -175.2(4)
C15 N11 C11 C12 0.4(8)
Hg1 N11 C11 C12 -178.9(4)
N11 C11 C12 C13 1.1(8)
C11 C12 C13 C14 -1.4(8)
C12 C13 C14 C15 0.2(8)
C11 N11 C15 C14 -1.7(7)
Hg1 N11 C15 C14 177.6(4)
C11 N11 C15 C16 176.5(4)
Hg1 N11 C15 C16 -4.2(5)
C13 C14 C15 N11 1.4(8)
C13 C14 C15 C16 -176.6(5)
N13 N12 C16 N14 -0.5(5)
Hg1 N12 C16 N14 -141.8(3)
N13 N12 C16 C15 178.6(4)
Hg1 N12 C16 C15 37.3(5)
C17 N14 C16 N12 0.7(5)
C18 N14 C16 N12 172.3(5)
C17 N14 C16 C15 -178.4(5)
C18 N14 C16 C15 -6.7(8)
N11 C15 C16 N12 -25.5(7)
C14 C15 C16 N12 152.7(5)
N11 C15 C16 N14 153.4(5)
C14 C15 C16 N14 -28.4(8)
N12 N13 C17 N14 0.4(6)
N12 N13 C17 S1 -175.6(4)
C16 N14 C17 N13 -0.6(6)
C18 N14 C17 N13 -172.9(4)
C16 N14 C17 S1 175.6(4)
C18 N14 C17 S1 3.3(7)
C1 S1 C17 N13 -9.1(5)
C1 S1 C17 N14 175.2(4)
C17 N14 C18 C19 102.5(6)
C16 N14 C18 C19 -67.7(7)
C17 N14 C18 C113 -74.0(6)
C16 N14 C18 C113 115.8(6)
C113 C18 C19 C110 -0.9(8)
N14 C18 C19 C110 -177.4(4)
C18 C19 C110 C111 1.4(8)
C19 C110 C111 C112 -0.3(8)
C110 C111 C112 C113 -1.3(8)
C111 C112 C113 C18 1.8(8)
C19 C18 C113 C112 -0.7(8)
N14 C18 C113 C112 175.7(4)

_cod_database_fobs_code 2021665
