#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/91/2019158.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_2019158
loop_
_publ_author_name
'Tampier, Stefan'
'Burzlaff, Nicolai'
_publ_section_title
;
 Heteroscorpionate complexes based on
 bis(3,5-di-tert-butylpyrazol-1-yl)dithioacetate
;
_journal_coeditor_code           YP3040
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              981
_journal_page_last               985
_journal_paper_doi               10.1107/S0108270113021148
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '[Zn (C24 H39 N4 S2) Cl]'
_chemical_formula_moiety         'C24 H39 Cl N4 S2 Zn'
_chemical_formula_sum            'C24 H39 Cl N4 S2 Zn'
_chemical_formula_weight         548.53
_chemical_name_systematic
;
[Bis(3,5-di-tert-butylpyrazol-1-yl)dithioacetato]chloridozinc(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.919(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2713(19)
_cell_length_b                   11.9298(17)
_cell_length_c                   16.8543(12)
_cell_measurement_reflns_used    238
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      6
_cell_volume                     2772.8(6)
_computing_cell_refinement       'EVALCCD (Duisenberg et al., 2003)'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method
;
φ- and ω-rotations with 2.00 ° and 120 sec per frame
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            68182
_diffrn_reflns_theta_full        28.52
_diffrn_reflns_theta_max         28.52
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    1.151
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.7400882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            'clear light red'
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.378
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         7007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0322P)²+1.3233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0745
_reflns_number_gt                5579
_reflns_number_total             7007
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            yp3040.cif
_cod_data_source_block           compound2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2019158
_cod_database_fobs_code          2019158
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Zn Zn 0.399158(13) 0.002463(16) 0.179063(11) 0.01772(6) Uani d . 1 1
S S1 0.50065(3) 0.14913(3) 0.23984(3) 0.02247(9) Uani d . 1 1
Cl Cl1 0.28048(3) 0.03791(4) 0.07121(3) 0.02954(10) Uani d . 1 1
S S2 0.62476(4) 0.13051(4) 0.41197(3) 0.02826(10) Uani d . 1 1
N N12 0.58399(9) -0.08936(11) 0.23786(8) 0.0147(2) Uani d . 1 1
N N21 0.39162(10) -0.06311(11) 0.28961(8) 0.0179(3) Uani d . 1 1
C C14 0.66718(11) -0.09750(12) 0.21208(9) 0.0154(3) Uani d . 1 1
N N22 0.48081(9) -0.10527(11) 0.33078(8) 0.0165(3) Uani d . 1 1
C C2 0.56349(11) 0.07628(13) 0.32396(10) 0.0180(3) Uani d . 1 1
C C12 0.53931(11) -0.16156(13) 0.11602(9) 0.0171(3) Uani d . 1 1
C C23 0.37361(12) -0.19120(14) 0.38172(10) 0.0204(3) Uani d . 1 1
H H23 0.3435 -0.2389 0.413 0.024 Uiso calc R 1 1
C C21 0.21892(12) -0.08815(14) 0.29195(10) 0.0200(3) Uani d . 1 1
N N11 0.50429(9) -0.12432(11) 0.17799(8) 0.0170(3) Uani d . 1 1
C C22 0.32635(11) -0.11457(13) 0.32109(9) 0.0171(3) Uani d . 1 1
C C15B 0.80332(14) -0.08969(18) 0.34548(11) 0.0323(4) Uani d . 1 1
H H15A 0.7644 -0.0525 0.3779 0.048 Uiso calc R 1 1
H H15B 0.8716 -0.0686 0.3667 0.048 Uiso calc R 1 1
H H15C 0.7968 -0.1711 0.3494 0.048 Uiso calc R 1 1
C C13 0.63954(12) -0.14540(14) 0.13506(10) 0.0194(3) Uani d . 1 1
H H13 0.6811 -0.164 0.1012 0.023 Uiso calc R 1 1
C C15 0.76767(11) -0.05344(13) 0.25537(10) 0.0181(3) Uani d . 1 1
C C11 0.47595(12) -0.22017(15) 0.04136(10) 0.0226(3) Uani d . 1 1
C C21B 0.20337(13) 0.03817(15) 0.27724(12) 0.0282(4) Uani d . 1 1
H H21A 0.2334 0.0789 0.3279 0.042 Uiso calc R 1 1
H H21B 0.1337 0.0544 0.2607 0.042 Uiso calc R 1 1
H H21C 0.2331 0.062 0.2337 0.042 Uiso calc R 1 1
C C24 0.47132(12) -0.18433(13) 0.38740(9) 0.0175(3) Uani d . 1 1
C C25 0.55343(12) -0.25046(14) 0.44289(10) 0.0215(3) Uani d . 1 1
C C15C 0.76737(12) 0.07563(14) 0.24991(11) 0.0224(3) Uani d . 1 1
H H15D 0.7421 0.0987 0.1926 0.034 Uiso calc R 1 1
H H15E 0.8337 0.1038 0.2707 0.034 Uiso calc R 1 1
H H15F 0.7261 0.1064 0.283 0.034 Uiso calc R 1 1
C C25A 0.61589(14) -0.30780(16) 0.39239(12) 0.0296(4) Uani d . 1 1
H H25A 0.575 -0.3574 0.3514 0.044 Uiso calc R 1 1
H H25B 0.6671 -0.3518 0.4291 0.044 Uiso calc R 1 1
H H25C 0.6452 -0.2506 0.3646 0.044 Uiso calc R 1 1
C C3 0.56773(11) -0.05290(13) 0.31698(9) 0.0156(3) Uani d . 1 1
H H3 0.6242 -0.0795 0.3614 0.019 Uiso calc R 1 1
C C15A 0.83961(12) -0.09765(16) 0.20881(13) 0.0300(4) Uani d . 1 1
H H15G 0.8396 -0.1798 0.2096 0.045 Uiso calc R 1 1
H H15H 0.9048 -0.07 0.2353 0.045 Uiso calc R 1 1
H H15I 0.8203 -0.0713 0.1518 0.045 Uiso calc R 1 1
C C25B 0.61513(13) -0.17492(16) 0.51056(10) 0.0276(4) Uani d . 1 1
H H25D 0.6452 -0.1155 0.4854 0.041 Uiso calc R 1 1
H H25E 0.6658 -0.2199 0.5471 0.041 Uiso calc R 1 1
H H25F 0.5737 -0.1413 0.5423 0.041 Uiso calc R 1 1
C C25C 0.50885(14) -0.34436(16) 0.48452(11) 0.0300(4) Uani d . 1 1
H H25G 0.4716 -0.311 0.5199 0.045 Uiso calc R 1 1
H H25H 0.5608 -0.3912 0.5177 0.045 Uiso calc R 1 1
H H25I 0.4658 -0.3905 0.4424 0.045 Uiso calc R 1 1
C C21A 0.17509(13) -0.15255(16) 0.21164(11) 0.0266(4) Uani d . 1 1
H H21D 0.2068 -0.1285 0.1694 0.04 Uiso calc R 1 1
H H21E 0.1054 -0.137 0.1932 0.04 Uiso calc R 1 1
H H21F 0.1852 -0.2332 0.2213 0.04 Uiso calc R 1 1
C C21C 0.16894(13) -0.12494(18) 0.35828(11) 0.0296(4) Uani d . 1 1
H H21G 0.1766 -0.206 0.3668 0.044 Uiso calc R 1 1
H H21H 0.0998 -0.1063 0.3406 0.044 Uiso calc R 1 1
H H21I 0.1986 -0.0859 0.4098 0.044 Uiso calc R 1 1
C C11A 0.38321(16) -0.2628(2) 0.05872(13) 0.0405(5) Uani d . 1 1
H H11A 0.3991 -0.3137 0.1059 0.061 Uiso calc R 1 1
H H11B 0.3449 -0.303 0.0105 0.061 Uiso calc R 1 1
H H11C 0.3457 -0.1993 0.071 0.061 Uiso calc R 1 1
C C11B 0.45095(19) -0.1394(2) -0.03125(12) 0.0526(7) Uani d . 1 1
H H11D 0.4125 -0.077 -0.0186 0.079 Uiso calc R 1 1
H H11E 0.4134 -0.179 -0.0801 0.079 Uiso calc R 1 1
H H11F 0.5109 -0.1103 -0.0417 0.079 Uiso calc R 1 1
C C11C 0.53461(19) -0.3171(3) 0.01992(18) 0.0717(10) Uani d . 1 1
H H11G 0.5943 -0.2881 0.009 0.108 Uiso calc R 1 1
H H11H 0.4962 -0.3557 -0.029 0.108 Uiso calc R 1 1
H H11I 0.551 -0.3699 0.066 0.108 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 0 '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'
N N 0.0061 0.0033 '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'
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
N21 Zn N11 86.49(5) y
N21 Zn S1 93.39(4) y
N11 Zn S1 100.19(4) y
Cl1 Zn S1 118.76(2) y
N21 Zn Cl1 128.32(4) y
N11 Zn Cl1 121.78(4) y
C2 S1 Zn 96.71(6) ?
C14 N12 N11 111.49(12) ?
C14 N12 C3 131.18(13) ?
N11 N12 C3 117.31(12) ?
C22 N21 N22 106.31(13) ?
C22 N21 Zn 137.95(11) ?
N22 N21 Zn 109.83(9) ?
N12 C14 C13 105.47(13) ?
N12 C14 C15 127.54(14) ?
C13 C14 C15 126.77(14) ?
C24 N22 N21 110.91(12) ?
C24 N22 C3 130.14(13) ?
N21 N22 C3 118.43(12) ?
C3 C2 S2 115.92(11) ?
C3 C2 S1 117.79(11) ?
S2 C2 S1 126.24(10) ?
N11 C12 C13 109.86(14) ?
N11 C12 C11 122.35(14) ?
C13 C12 C11 127.62(14) ?
C24 C23 C22 107.43(14) ?
C24 C23 H23 126.3 ?
C22 C23 H23 126.3 ?
C22 C21 C21B 110.38(13) ?
C22 C21 C21C 108.95(14) ?
C21B C21 C21C 108.86(14) ?
C22 C21 C21A 109.16(13) ?
C21B C21 C21A 109.78(15) ?
C21C C21 C21A 109.69(14) ?
C12 N11 N12 105.50(12) ?
C12 N11 Zn 130.08(11) ?
N12 N11 Zn 103.25(9) ?
N21 C22 C23 109.54(14) ?
N21 C22 C21 121.76(14) ?
C23 C22 C21 128.70(14) ?
C15 C15B H15A 109.5 ?
C15 C15B H15B 109.5 ?
H15A C15B H15B 109.5 ?
C15 C15B H15C 109.5 ?
H15A C15B H15C 109.5 ?
H15B C15B H15C 109.5 ?
C14 C13 C12 107.53(14) ?
C14 C13 H13 126.2 ?
C12 C13 H13 126.2 ?
C14 C15 C15B 114.06(13) ?
C14 C15 C15A 107.87(13) ?
C15B C15 C15A 108.29(15) ?
C14 C15 C15C 109.12(13) ?
C15B C15 C15C 109.60(14) ?
C15A C15 C15C 107.70(14) ?
C11A C11 C12 110.99(14) ?
C11A C11 C11C 110.56(19) ?
C12 C11 C11C 107.44(15) ?
C11A C11 C11B 109.36(17) ?
C12 C11 C11B 109.89(15) ?
C11C C11 C11B 108.6(2) ?
C21 C21B H21A 109.5 ?
C21 C21B H21B 109.5 ?
H21A C21B H21B 109.5 ?
C21 C21B H21C 109.5 ?
H21A C21B H21C 109.5 ?
H21B C21B H21C 109.5 ?
N22 C24 C23 105.80(14) ?
N22 C24 C25 125.89(14) ?
C23 C24 C25 128.30(14) ?
C24 C25 C25B 110.83(14) ?
C24 C25 C25A 110.77(13) ?
C25B C25 C25A 111.53(15) ?
C24 C25 C25C 108.30(14) ?
C25B C25 C25C 108.19(14) ?
C25A C25 C25C 107.07(14) ?
C15 C15C H15D 109.5 ?
C15 C15C H15E 109.5 ?
H15D C15C H15E 109.5 ?
C15 C15C H15F 109.5 ?
H15D C15C H15F 109.5 ?
H15E C15C H15F 109.5 ?
C25 C25A H25A 109.5 ?
C25 C25A H25B 109.5 ?
H25A C25A H25B 109.5 ?
C25 C25A H25C 109.5 ?
H25A C25A H25C 109.5 ?
H25B C25A H25C 109.5 ?
N22 C3 N12 110.81(12) ?
N22 C3 C2 111.26(13) ?
N12 C3 C2 112.34(12) ?
N22 C3 H3 107.4 ?
N12 C3 H3 107.4 ?
C2 C3 H3 107.4 ?
C15 C15A H15G 109.5 ?
C15 C15A H15H 109.5 ?
H15G C15A H15H 109.5 ?
C15 C15A H15I 109.5 ?
H15G C15A H15I 109.5 ?
H15H C15A H15I 109.5 ?
C25 C25B H25D 109.5 ?
C25 C25B H25E 109.5 ?
H25D C25B H25E 109.5 ?
C25 C25B H25F 109.5 ?
H25D C25B H25F 109.5 ?
H25E C25B H25F 109.5 ?
C25 C25C H25G 109.5 ?
C25 C25C H25H 109.5 ?
H25G C25C H25H 109.5 ?
C25 C25C H25I 109.5 ?
H25G C25C H25I 109.5 ?
H25H C25C H25I 109.5 ?
C21 C21A H21D 109.5 ?
C21 C21A H21E 109.5 ?
H21D C21A H21E 109.5 ?
C21 C21A H21F 109.5 ?
H21D C21A H21F 109.5 ?
H21E C21A H21F 109.5 ?
C21 C21C H21G 109.5 ?
C21 C21C H21H 109.5 ?
H21G C21C H21H 109.5 ?
C21 C21C H21I 109.5 ?
H21G C21C H21I 109.5 ?
H21H C21C H21I 109.5 ?
C11 C11A H11A 109.5 ?
C11 C11A H11B 109.5 ?
H11A C11A H11B 109.5 ?
C11 C11A H11C 109.5 ?
H11A C11A H11C 109.5 ?
H11B C11A H11C 109.5 ?
C11 C11B H11D 109.5 ?
C11 C11B H11E 109.5 ?
H11D C11B H11E 109.5 ?
C11 C11B H11F 109.5 ?
H11D C11B H11F 109.5 ?
H11E C11B H11F 109.5 ?
C11 C11C H11G 109.5 ?
C11 C11C H11H 109.5 ?
H11G C11C H11H 109.5 ?
C11 C11C H11I 109.5 ?
H11G C11C H11I 109.5 ?
H11H C11C H11I 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Zn N21 2.0490(13) y
Zn N11 2.1338(13) y
Zn Cl1 2.1832(5) y
Zn S1 2.3335(5) y
S1 C2 1.7073(17) ?
S2 C2 1.6480(16) ?
N12 C14 1.3686(19) ?
N12 N11 1.3766(17) ?
N12 C3 1.4768(19) ?
N21 C22 1.334(2) ?
N21 N22 1.3784(18) ?
C14 C13 1.380(2) ?
C14 C15 1.525(2) ?
N22 C24 1.373(2) ?
N22 C3 1.460(2) ?
C2 C3 1.548(2) ?
C12 N11 1.344(2) ?
C12 C13 1.396(2) ?
C12 C11 1.518(2) ?
C23 C24 1.375(2) ?
C23 C22 1.407(2) ?
C23 H23 0.95 ?
C21 C22 1.518(2) ?
C21 C21B 1.534(2) ?
C21 C21C 1.537(2) ?
C21 C21A 1.542(2) ?
C15B C15 1.534(2) ?
C15B H15A 0.98 ?
C15B H15B 0.98 ?
C15B H15C 0.98 ?
C13 H13 0.95 ?
C15 C15A 1.537(2) ?
C15 C15C 1.542(2) ?
C11 C11A 1.515(3) ?
C11 C11C 1.525(3) ?
C11 C11B 1.526(3) ?
C21B H21A 0.98 ?
C21B H21B 0.98 ?
C21B H21C 0.98 ?
C24 C25 1.519(2) ?
C25 C25B 1.540(2) ?
C25 C25A 1.542(2) ?
C25 C25C 1.543(2) ?
C15C H15D 0.98 ?
C15C H15E 0.98 ?
C15C H15F 0.98 ?
C25A H25A 0.98 ?
C25A H25B 0.98 ?
C25A H25C 0.98 ?
C3 H3 1 ?
C15A H15G 0.98 ?
C15A H15H 0.98 ?
C15A H15I 0.98 ?
C25B H25D 0.98 ?
C25B H25E 0.98 ?
C25B H25F 0.98 ?
C25C H25G 0.98 ?
C25C H25H 0.98 ?
C25C H25I 0.98 ?
C21A H21D 0.98 ?
C21A H21E 0.98 ?
C21A H21F 0.98 ?
C21C H21G 0.98 ?
C21C H21H 0.98 ?
C21C H21I 0.98 ?
C11A H11A 0.98 ?
C11A H11B 0.98 ?
C11A H11C 0.98 ?
C11B H11D 0.98 ?
C11B H11E 0.98 ?
C11B H11F 0.98 ?
C11C H11G 0.98 ?
C11C H11H 0.98 ?
C11C H11I 0.98 ?
