#------------------------------------------------------------------------------
#$Date: 2019-12-19 12:05:55 +0200 (Thu, 19 Dec 2019) $
#$Revision: 245381 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/66/1556662.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1556662
loop_
_publ_author_name
'Tuchler, M.'
'Rambock, M.'
'Glanzer, S.'
'Zangger, K.'
'Belaj, F.'
'Mosch-Zanetti, N.C.'
_publ_section_title
;
 Mono- and Hexanuclear Zinc Halide Complexes with Soft Thiopyridazine
 Based Scorpionate Ligands
;
_journal_name_full               Inorganics
_journal_page_first              24
_journal_paper_doi               10.3390/inorganics7020024
_journal_volume                  7
_journal_year                    2019
_chemical_compound_source        'synthetical product'
_chemical_formula_moiety         'C18 H28 Br2 N4 S2 Zn'
_chemical_formula_sum            'C18 H28 Br2 N4 S2 Zn'
_chemical_formula_weight         589.75
_chemical_name_common
' dibromo-bis(6-tert-butyl-4-methylpyridazine-3(2H)-thione)-zinc'
_chemical_name_systematic
' dibromo-bis(6-tert-butyl-4-methylpyridazine-3(2H)-thione)-zinc'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 96.6196(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2147(3)
_cell_length_b                   8.6489(2)
_cell_length_c                   27.2498(8)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.70
_cell_measurement_theta_min      2.47
_cell_volume                     2391.36(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'modified ORTEP (Johnson, 1965)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            38304
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        35.00
_diffrn_reflns_theta_max         35.00
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    4.554
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         10517
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0224
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0203P)²+0.9734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0481
_refine_ls_wR_factor_ref         0.0500
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9146
_reflns_number_total             10517
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Inorganics-2019-7-24.cif
_cod_data_source_block           MR38
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1556662
_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   0.342
_shelx_estimated_absorpt_t_max   0.548
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.88552(2) 0.67041(2) 0.65924(2) 0.01424(3) Uani 1 1 d . . . . .
Br2 Br 0.63604(2) 0.96169(2) 0.59070(2) 0.01467(3) Uani 1 1 d . . . . .
Zn1 Zn 0.65839(2) 0.74189(2) 0.64553(2) 0.01164(3) Uani 1 1 d . . . . .
S1 S 0.53102(3) 0.52831(3) 0.61303(2) 0.01431(5) Uani 1 1 d . . . . .
N11 N 0.81355(9) 0.39633(11) 0.53355(4) 0.01275(16) Uani 1 1 d . . . . .
N12 N 0.73902(9) 0.46033(11) 0.56603(3) 0.01303(16) Uani 1 1 d D . . . .
H12 H 0.7846(6) 0.5169(6) 0.58879(17) 0.016(3) Uiso 1 1 d D U . . .
C13 C 0.61027(10) 0.43872(12) 0.56884(4) 0.01113(17) Uani 1 1 d . . . . .
C14 C 0.54298(10) 0.33561(12) 0.53326(4) 0.01098(17) Uani 1 1 d . . . . .
C15 C 0.61558(10) 0.27148(12) 0.49938(4) 0.01122(17) Uani 1 1 d . . . . .
H15 H 0.5738 0.2044 0.4748 0.016(3) Uiso 1 1 calc R U . . .
C16 C 0.75237(10) 0.30323(12) 0.50027(4) 0.01030(16) Uani 1 1 d . . . . .
C11 C 0.40055(11) 0.29970(14) 0.53486(4) 0.01502(19) Uani 1 1 d . . . . .
H111 H 0.3684 0.2354 0.5064 0.021(2) Uiso 1 1 calc R U . . .
H112 H 0.3501 0.3962 0.5338 0.021(2) Uiso 1 1 calc R U . . .
H113 H 0.3897 0.2439 0.5654 0.021(2) Uiso 1 1 calc R U . . .
C10 C 0.83486(10) 0.22524(12) 0.46434(4) 0.01120(17) Uani 1 1 d . . . . .
C17 C 0.97737(11) 0.28326(14) 0.47158(4) 0.0155(2) Uani 1 1 d . . . . .
H171 H 0.9788 0.3949 0.4655 0.024(3) Uiso 1 1 calc R U . . .
H172 H 1.0286 0.2301 0.4484 0.024(3) Uiso 1 1 calc R U . . .
H173 H 1.0160 0.2619 0.5055 0.024(3) Uiso 1 1 calc R U . . .
C18 C 0.83037(12) 0.05058(13) 0.47422(5) 0.0176(2) Uani 1 1 d . . . . .
H181 H 0.8631 0.0300 0.5088 0.027(3) Uiso 1 1 calc R U . . .
H182 H 0.8858 -0.0035 0.4527 0.027(3) Uiso 1 1 calc R U . . .
H183 H 0.7393 0.0138 0.4674 0.027(3) Uiso 1 1 calc R U . . .
C19 C 0.77561(12) 0.25747(15) 0.41087(4) 0.0174(2) Uani 1 1 d . . . . .
H191 H 0.6851 0.2182 0.4058 0.022(2) Uiso 1 1 calc R U . . .
H192 H 0.8287 0.2057 0.3880 0.022(2) Uiso 1 1 calc R U . . .
H193 H 0.7753 0.3691 0.4047 0.022(2) Uiso 1 1 calc R U . . .
S2 S 0.56004(3) 0.77949(4) 0.71903(2) 0.01563(5) Uani 1 1 d . . . . .
N21 N 0.32278(9) 1.10264(11) 0.65493(3) 0.01253(16) Uani 1 1 d . . . . .
N22 N 0.42057(9) 1.00252(11) 0.66961(3) 0.01229(16) Uani 1 1 d D . . . .
H22 H 0.4869(3) 1.007(2) 0.65174(15) 0.022(3) Uiso 1 1 d D U . . .
C23 C 0.42547(10) 0.89778(12) 0.70590(4) 0.01121(17) Uani 1 1 d . . . . .
C24 C 0.31427(11) 0.89238(13) 0.73319(4) 0.01330(18) Uani 1 1 d . . . . .
C25 C 0.21316(11) 0.99300(13) 0.71933(4) 0.01404(19) Uani 1 1 d . . . . .
H25 H 0.1373 0.9920 0.7365 0.022(3) Uiso 1 1 calc R U . . .
C26 C 0.21966(10) 1.09905(12) 0.67972(4) 0.01145(17) Uani 1 1 d . . . . .
C21 C 0.31085(14) 0.77932(16) 0.77469(5) 0.0223(2) Uani 1 1 d . . . . .
H211 H 0.2279 0.7909 0.7892 0.033(3) Uiso 1 1 calc R U . . .
H212 H 0.3851 0.7993 0.8000 0.033(3) Uiso 1 1 calc R U . . .
H213 H 0.3173 0.6739 0.7620 0.033(3) Uiso 1 1 calc R U . . .
C20 C 0.10894(11) 1.21315(13) 0.66468(4) 0.01348(18) Uani 1 1 d . . . . .
C27 C 0.14078(12) 1.31395(15) 0.62154(5) 0.0187(2) Uani 1 1 d . . . . .
H271 H 0.2231 1.3703 0.6310 0.028(3) Uiso 1 1 calc R U . . .
H272 H 0.0690 1.3879 0.6131 0.028(3) Uiso 1 1 calc R U . . .
H273 H 0.1507 1.2483 0.5929 0.028(3) Uiso 1 1 calc R U . . .
C28 C -0.01916(12) 1.12266(17) 0.64926(5) 0.0232(2) Uani 1 1 d . . . . .
H281 H -0.0058 1.0523 0.6221 0.030(3) Uiso 1 1 calc R U . . .
H282 H -0.0903 1.1953 0.6384 0.030(3) Uiso 1 1 calc R U . . .
H283 H -0.0429 1.0629 0.6775 0.030(3) Uiso 1 1 calc R U . . .
C29 C 0.09159(14) 1.31680(16) 0.70914(5) 0.0233(3) Uani 1 1 d . . . . .
H291 H 0.0680 1.2530 0.7365 0.030(3) Uiso 1 1 calc R U . . .
H292 H 0.0214 1.3922 0.6999 0.030(3) Uiso 1 1 calc R U . . .
H293 H 0.1743 1.3715 0.7194 0.030(3) Uiso 1 1 calc R U . . .
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'
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S2 Zn1 S1 98.920(12) . . yes
S2 Zn1 Br1 113.767(9) . . yes
S1 Zn1 Br1 109.757(9) . . yes
S2 Zn1 Br2 113.402(9) . . yes
S1 Zn1 Br2 111.953(9) . . yes
Br1 Zn1 Br2 108.767(7) . . yes
C13 S1 Zn1 109.37(4) . . yes
C16 N11 N12 116.34(9) . . ?
C13 N12 N11 127.71(9) . . yes
C13 N12 H12 118.7(5) . . yes
N11 N12 H12 113.4(5) . . yes
N12 C13 C14 116.46(9) . . ?
N12 C13 S1 121.62(8) . . ?
C14 C13 S1 121.92(8) . . ?
C15 C14 C13 117.02(9) . . ?
C15 C14 C11 122.79(10) . . ?
C13 C14 C11 120.18(10) . . ?
C14 C15 C16 121.26(10) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
N11 C16 C15 121.19(10) . . ?
N11 C16 C10 117.44(9) . . ?
C15 C16 C10 121.32(9) . . ?
C14 C11 H111 109.5 . . ?
C14 C11 H112 109.5 . . ?
H111 C11 H112 109.5 . . ?
C14 C11 H113 109.5 . . ?
H111 C11 H113 109.5 . . ?
H112 C11 H113 109.5 . . ?
C16 C10 C17 111.15(9) . . ?
C16 C10 C18 107.06(9) . . ?
C17 C10 C18 110.30(9) . . ?
C16 C10 C19 110.04(9) . . ?
C17 C10 C19 109.10(9) . . ?
C18 C10 C19 109.15(9) . . ?
C10 C17 H171 109.5 . . ?
C10 C17 H172 109.5 . . ?
H171 C17 H172 109.5 . . ?
C10 C17 H173 109.5 . . ?
H171 C17 H173 109.5 . . ?
H172 C17 H173 109.5 . . ?
C10 C18 H181 109.5 . . ?
C10 C18 H182 109.5 . . ?
H181 C18 H182 109.5 . . ?
C10 C18 H183 109.5 . . ?
H181 C18 H183 109.5 . . ?
H182 C18 H183 109.5 . . ?
C10 C19 H191 109.5 . . ?
C10 C19 H192 109.5 . . ?
H191 C19 H192 109.5 . . ?
C10 C19 H193 109.5 . . ?
H191 C19 H193 109.5 . . ?
H192 C19 H193 109.5 . . ?
C23 S2 Zn1 108.26(4) . . yes
C26 N21 N22 116.26(9) . . ?
C23 N22 N21 128.16(9) . . yes
C23 N22 H22 118.5(9) . . yes
N21 N22 H22 113.4(8) . . yes
N22 C23 C24 116.28(9) . . ?
N22 C23 S2 121.21(8) . . ?
C24 C23 S2 122.50(8) . . ?
C25 C24 C23 117.08(10) . . ?
C25 C24 C21 122.69(10) . . ?
C23 C24 C21 120.23(10) . . ?
C24 C25 C26 121.24(10) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
N21 C26 C25 120.96(10) . . ?
N21 C26 C20 117.43(10) . . ?
C25 C26 C20 121.60(10) . . ?
C24 C21 H211 109.5 . . ?
C24 C21 H212 109.5 . . ?
H211 C21 H212 109.5 . . ?
C24 C21 H213 109.5 . . ?
H211 C21 H213 109.5 . . ?
H212 C21 H213 109.5 . . ?
C26 C20 C27 111.09(9) . . ?
C26 C20 C29 108.44(9) . . ?
C27 C20 C29 109.17(10) . . ?
C26 C20 C28 109.00(10) . . ?
C27 C20 C28 109.22(10) . . ?
C29 C20 C28 109.91(11) . . ?
C20 C27 H271 109.5 . . ?
C20 C27 H272 109.5 . . ?
H271 C27 H272 109.5 . . ?
C20 C27 H273 109.5 . . ?
H271 C27 H273 109.5 . . ?
H272 C27 H273 109.5 . . ?
C20 C28 H281 109.5 . . ?
C20 C28 H282 109.5 . . ?
H281 C28 H282 109.5 . . ?
C20 C28 H283 109.5 . . ?
H281 C28 H283 109.5 . . ?
H282 C28 H283 109.5 . . ?
C20 C29 H291 109.5 . . ?
C20 C29 H292 109.5 . . ?
H291 C29 H292 109.5 . . ?
C20 C29 H293 109.5 . . ?
H291 C29 H293 109.5 . . ?
H292 C29 H293 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Zn1 2.38838(18) . yes
Br2 Zn1 2.41252(18) . yes
Zn1 S2 2.3644(3) . yes
Zn1 S1 2.3715(3) . yes
S1 C13 1.7118(11) . yes
N11 C16 1.3156(14) . ?
N11 N12 1.3508(13) . ?
N12 C13 1.3393(14) . ?
N12 H12 0.88 . ?
C13 C14 1.4332(15) . ?
C14 C15 1.3667(15) . ?
C14 C11 1.4932(15) . ?
C15 C16 1.4215(15) . ?
C15 H15 0.95 . ?
C16 C10 1.5210(15) . ?
C11 H111 0.98 . ?
C11 H112 0.98 . ?
C11 H113 0.98 . ?
C10 C17 1.5309(15) . ?
C10 C18 1.5360(16) . ?
C10 C19 1.5375(16) . ?
C17 H171 0.98 . ?
C17 H172 0.98 . ?
C17 H173 0.98 . ?
C18 H181 0.98 . ?
C18 H182 0.98 . ?
C18 H183 0.98 . ?
C19 H191 0.98 . ?
C19 H192 0.98 . ?
C19 H193 0.98 . ?
S2 C23 1.7178(11) . yes
N21 C26 1.3157(14) . ?
N21 N22 1.3474(13) . ?
N22 C23 1.3378(14) . ?
N22 H22 0.88 . ?
C23 C24 1.4283(15) . ?
C24 C25 1.3700(15) . ?
C24 C21 1.4985(17) . ?
C25 C26 1.4237(16) . ?
C25 H25 0.95 . ?
C26 C20 1.5212(15) . ?
C21 H211 0.98 . ?
C21 H212 0.98 . ?
C21 H213 0.98 . ?
C20 C27 1.5284(17) . ?
C20 C29 1.5338(17) . ?
C20 C28 1.5410(17) . ?
C27 H271 0.98 . ?
C27 H272 0.98 . ?
C27 H273 0.98 . ?
C28 H281 0.98 . ?
C28 H282 0.98 . ?
C28 H283 0.98 . ?
C29 H291 0.98 . ?
C29 H292 0.98 . ?
C29 H293 0.98 . ?
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
_geom_hbond_site_symmetry_A
N12 H12 Br1 0.88 2.4606(13) 3.3341(9) 171.9(6) .
N22 H22 Br2 0.88 2.414(4) 3.2686(9) 163.8(12) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C16 N11 N12 C13 0.97(17) . . . .
N11 N12 C13 C14 -0.02(17) . . . .
N11 N12 C13 S1 179.37(9) . . . .
Zn1 S1 C13 N12 18.63(10) . . . .
Zn1 S1 C13 C14 -162.02(8) . . . .
N12 C13 C14 C15 -1.17(15) . . . .
S1 C13 C14 C15 179.45(8) . . . .
N12 C13 C14 C11 177.57(10) . . . .
S1 C13 C14 C11 -1.82(14) . . . .
C13 C14 C15 C16 1.42(15) . . . .
C11 C14 C15 C16 -177.28(10) . . . .
N12 N11 C16 C15 -0.70(15) . . . .
N12 N11 C16 C10 -177.94(9) . . . .
C14 C15 C16 N11 -0.48(16) . . . .
C14 C15 C16 C10 176.65(10) . . . .
N11 C16 C10 C17 -4.87(14) . . . .
C15 C16 C10 C17 177.90(10) . . . .
N11 C16 C10 C18 115.65(11) . . . .
C15 C16 C10 C18 -61.58(13) . . . .
N11 C16 C10 C19 -125.84(11) . . . .
C15 C16 C10 C19 56.92(13) . . . .
C26 N21 N22 C23 1.07(17) . . . .
N21 N22 C23 C24 -1.07(17) . . . .
N21 N22 C23 S2 179.93(9) . . . .
Zn1 S2 C23 N22 -28.74(10) . . . .
Zn1 S2 C23 C24 152.32(8) . . . .
N22 C23 C24 C25 0.75(15) . . . .
S2 C23 C24 C25 179.73(9) . . . .
N22 C23 C24 C21 -179.76(11) . . . .
S2 C23 C24 C21 -0.77(16) . . . .
C23 C24 C25 C26 -0.55(17) . . . .
C21 C24 C25 C26 179.96(11) . . . .
N22 N21 C26 C25 -0.75(16) . . . .
N22 N21 C26 C20 178.74(9) . . . .
C24 C25 C26 N21 0.58(17) . . . .
C24 C25 C26 C20 -178.89(11) . . . .
N21 C26 C20 C27 0.18(14) . . . .
C25 C26 C20 C27 179.66(10) . . . .
N21 C26 C20 C29 -119.79(12) . . . .
C25 C26 C20 C29 59.69(14) . . . .
N21 C26 C20 C28 120.57(11) . . . .
C25 C26 C20 C28 -59.95(14) . . . .
