#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:20:05 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180422 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/91/7209163.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_7209163
loop_
_publ_author_name
'Pandurangan, Komala'
'Kitchen, Jonathan A.'
'McCabe, Thomas'
'Gunnlaugsson, Thorfinnur'
_publ_section_title
;
 Hydrogen bonding interactions and supramolecular networks of
 pyridine-aryl based thiosemicarbazides and their Zn(ii) complexes
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1421
_journal_paper_doi               10.1039/c2ce26718g
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C26 H20 F6 N8 S2 Zn'
_chemical_formula_weight         687.99
_chemical_name_systematic
;
?
;
_space_group_IT_number           52
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2a 2bc'
_symmetry_space_group_name_H-M   'P n n a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.125(3)
_cell_length_b                   13.543(3)
_cell_length_c                   13.762(3)
_cell_measurement_reflns_used    14955
_cell_measurement_temperature    128(2)
_cell_measurement_theta_max      32.0330
_cell_measurement_theta_min      1.7317
_cell_volume                     3191.7(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      128(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku Saturn 724'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13352
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.965
_exptl_absorpt_correction_T_max  0.7875
_exptl_absorpt_correction_T_min  0.6706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Crystalclear
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.339
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.339
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0709
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1418P)²+9.6045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2327
_refine_ls_wR_factor_ref         0.2734
_reflns_number_gt                2673
_reflns_number_total             2795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26718g.txt
_cod_data_source_block           KP34
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pnna
_cod_database_code               7209163
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z'
'x, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x, y-1/2, z-1/2'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Zn1 Zn 0.2500 0.0000 -0.07434(7) 0.0193(4) Uani 1 2 d S
S1 S 0.21753(9) 0.14454(11) -0.15275(11) 0.0211(5) Uani 1 1 d .
N1 N 0.4475(3) 0.1048(4) 0.0801(4) 0.0262(12) Uani 1 1 d .
H1X H 0.4489 0.1655 0.0572 0.031 Uiso 1 1 calc R
N2 N 0.3294(3) 0.0805(4) -0.0011(4) 0.0230(12) Uani 1 1 d .
N3 N 0.3392(3) 0.1785(3) -0.0270(4) 0.0193(11) Uani 1 1 d .
N4 N 0.2963(3) 0.3096(4) -0.1213(4) 0.0232(12) Uani 1 1 d .
H4A H 0.2728 0.3229 -0.1767 0.028 Uiso 1 1 calc R
C1 C 0.5077(5) 0.0739(6) 0.1378(6) 0.0413(19) Uani 1 1 d .
H1 H 0.5489 0.1185 0.1526 0.050 Uiso 1 1 calc R
C2 C 0.5098(5) -0.0172(5) 0.1737(6) 0.0369(17) Uani 1 1 d .
H2 H 0.5526 -0.0390 0.2120 0.044 Uiso 1 1 calc R
C3 C 0.4457(5) -0.0814(5) 0.1529(5) 0.0370(18) Uani 1 1 d .
H3 H 0.4446 -0.1456 0.1806 0.044 Uiso 1 1 calc R
C4 C 0.3869(5) -0.0522(5) 0.0947(5) 0.0312(16) Uani 1 1 d .
H4 H 0.3461 -0.0971 0.0791 0.037 Uiso 1 1 calc R
C5 C 0.3853(4) 0.0466(4) 0.0559(4) 0.0211(13) Uani 1 1 d .
C6 C 0.2917(4) 0.2108(5) -0.0915(4) 0.0221(13) Uani 1 1 d .
C7 C 0.3330(4) 0.3911(5) -0.0758(4) 0.0217(13) Uani 1 1 d .
C8 C 0.3572(4) 0.3926(5) 0.0212(5) 0.0332(16) Uani 1 1 d .
H8 H 0.3520 0.3352 0.0603 0.040 Uiso 1 1 calc R
C9 C 0.3884(5) 0.4769(5) 0.0600(5) 0.0306(16) Uani 1 1 d .
H9 H 0.4057 0.4769 0.1256 0.037 Uiso 1 1 calc R
C10 C 0.3952(4) 0.5628(5) 0.0049(5) 0.0265(14) Uani 1 1 d .
C11 C 0.3723(4) 0.5625(5) -0.0932(5) 0.0228(13) Uani 1 1 d .
H11 H 0.3772 0.6200 -0.1322 0.027 Uiso 1 1 calc R
C12 C 0.3419(4) 0.4746(4) -0.1318(5) 0.0209(13) Uani 1 1 d .
H12 H 0.3272 0.4726 -0.1983 0.025 Uiso 1 1 calc R
C13 C 0.4227(4) 0.6561(5) 0.0485(6) 0.0328(16) Uani 1 1 d .
F1 F 0.4753(3) 0.6438(3) 0.1200(3) 0.0454(12) Uani 1 1 d .
F2 F 0.4565(3) 0.7175(3) -0.0156(3) 0.0447(12) Uani 1 1 d .
F3 F 0.3638(3) 0.7080(3) 0.0895(4) 0.0577(15) Uani 1 1 d .
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'
F F 0.0171 0.0103 '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
N2 Zn1 N2 119.9(3) 2 . y
N2 Zn1 S1 86.41(15) 2 2 y
N2 Zn1 S1 122.11(16) . 2 y
N2 Zn1 S1 122.11(16) 2 . y
N2 Zn1 S1 86.41(15) . . y
S1 Zn1 S1 124.13(9) 2 . y
C6 S1 Zn1 92.0(2) . . ?
C1 N1 C5 123.6(6) . . ?
C1 N1 H1X 118.2 . . ?
C5 N1 H1X 118.2 . . ?
C5 N2 N3 113.5(5) . . ?
C5 N2 Zn1 126.8(4) . . ?
N3 N2 Zn1 118.2(4) . . ?
C6 N3 N2 115.4(5) . . ?
C6 N4 C7 129.8(5) . . ?
C6 N4 H4A 115.1 . . ?
C7 N4 H4A 115.1 . . ?
C2 C1 N1 121.3(7) . . ?
C2 C1 H1 119.3 . . ?
N1 C1 H1 119.3 . . ?
C1 C2 C3 118.0(7) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 121.0(7) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.5(6) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N2 C5 N1 120.6(5) . . ?
N2 C5 C4 123.9(6) . . ?
N1 C5 C4 115.5(6) . . ?
N3 C6 N4 119.5(5) . . ?
N3 C6 S1 127.8(5) . . ?
N4 C6 S1 112.6(5) . . ?
C12 C7 C8 119.3(6) . . ?
C12 C7 N4 116.2(5) . . ?
C8 C7 N4 124.4(6) . . ?
C9 C8 C7 120.0(6) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 121.1(6) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 119.8(6) . . ?
C9 C10 C13 121.3(6) . . ?
C11 C10 C13 118.9(6) . . ?
C12 C11 C10 118.0(6) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C7 C12 C11 121.7(6) . . ?
C7 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
F1 C13 F2 105.6(6) . . ?
F1 C13 F3 105.0(6) . . ?
F2 C13 F3 105.8(6) . . ?
F1 C13 C10 113.9(6) . . ?
F2 C13 C10 113.6(6) . . ?
F3 C13 C10 112.1(6) . . ?
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
Zn1 N2 2.013(5) 2 y
Zn1 N2 2.013(5) . y
Zn1 S1 2.3034(16) 2 y
Zn1 S1 2.3034(16) . y
S1 C6 1.768(6) . y
N1 C1 1.367(9) . ?
N1 C5 1.367(8) . ?
N1 H1X 0.8800 . ?
N2 C5 1.320(8) . ?
N2 N3 1.384(7) . ?
N3 C6 1.282(8) . ?
N4 C6 1.401(8) . ?
N4 C7 1.417(8) . ?
N4 H4A 0.8800 . ?
C1 C2 1.330(11) . ?
C1 H1 0.9500 . ?
C2 C3 1.429(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.346(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.441(9) . ?
C4 H4 0.9500 . ?
C7 C12 1.377(9) . ?
C7 C8 1.399(9) . ?
C8 C9 1.368(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.405(9) . ?
C10 C13 1.476(9) . ?
C11 C12 1.403(9) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 F1 1.344(9) . ?
C13 F2 1.344(8) . ?
C13 F3 1.353(9) . ?
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
N1 H1X F2 0.88 2.34 3.046(7) 137.7 5_665
N4 H4A S1 0.88 2.57 3.445(6) 173.9 3_554
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
N2 Zn1 S1 C6 126.4(3) 2
N2 Zn1 S1 C6 3.0(3) .
S1 Zn1 S1 C6 -123.9(2) 2
N2 Zn1 N2 C5 64.8(5) 2
S1 Zn1 N2 C5 -41.2(6) 2
S1 Zn1 N2 C5 -169.8(5) .
N2 Zn1 N2 N3 -130.3(5) 2
S1 Zn1 N2 N3 123.7(4) 2
S1 Zn1 N2 N3 -5.0(4) .
C5 N2 N3 C6 171.9(6) .
Zn1 N2 N3 C6 5.1(7) .
C5 N1 C1 C2 0.9(12) .
N1 C1 C2 C3 -2.1(12) .
C1 C2 C3 C4 3.3(12) .
C2 C3 C4 C5 -3.2(12) .
N3 N2 C5 N1 -3.4(9) .
Zn1 N2 C5 N1 162.1(5) .
N3 N2 C5 C4 178.2(6) .
Zn1 N2 C5 C4 -16.4(10) .
C1 N1 C5 N2 -179.2(7) .
C1 N1 C5 C4 -0.6(10) .
C3 C4 C5 N2 -179.6(7) .
C3 C4 C5 N1 1.8(11) .
N2 N3 C6 N4 179.0(5) .
N2 N3 C6 S1 -1.8(8) .
C7 N4 C6 N3 -17.7(10) .
C7 N4 C6 S1 163.0(5) .
Zn1 S1 C6 N3 -1.7(6) .
Zn1 S1 C6 N4 177.5(4) .
C6 N4 C7 C12 166.8(6) .
C6 N4 C7 C8 -15.8(11) .
C12 C7 C8 C9 0.9(11) .
N4 C7 C8 C9 -176.5(7) .
C7 C8 C9 C10 1.3(12) .
C8 C9 C10 C11 -2.2(11) .
C8 C9 C10 C13 174.9(7) .
C9 C10 C11 C12 0.9(9) .
C13 C10 C11 C12 -176.2(6) .
C8 C7 C12 C11 -2.2(10) .
N4 C7 C12 C11 175.4(6) .
C10 C11 C12 C7 1.3(10) .
C9 C10 C13 F1 32.8(10) .
C11 C10 C13 F1 -150.1(6) .
C9 C10 C13 F2 153.8(7) .
C11 C10 C13 F2 -29.1(9) .
C9 C10 C13 F3 -86.3(8) .
C11 C10 C13 F3 90.8(8) .
