##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global 

_publ_contact_author_name
;
Edward R.T. Tiekink
;
_publ_contact_author_email 'edwardt@sunway.edu.my'
_publ_contact_author_phone
;
+60 3 7491 7173
;
_publ_contact_author_fax
;
+60 3 7491 8633
;
_publ_contact_author_id_iucr ?
_publ_contact_author_address
;
Faculty of Science and Technology,
Sunway University,
No. 5 Jalan Universiti,
47500 Bandar Sunway,
Selangor Darul Ehsan, Malaysia
;
_publ_contact_letter
;
Dear Sir/Madam,

   Please consider the following CIF as a contribution to Acta
   Crystallographica E (Research Communications).

   Yours sincerely,

   Edward RT Tiekink
   (on behalf of the authors)
;
_publ_requested_journal
;
Acta Crystallographica E (Research Communications)
;
_publ_requested_category EO

_publ_requested_coeditor_name ?

loop_
_publ_author_name
_publ_author_address
_publ_author_email
_publ_author_footnote
'Jotani, Mukesh M.'
;
Department of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad,
Gujarat 380 001, India
;
mmjotani@rediffmail.com
'Additional correspondence author, e-mail: mmjotani@rediffmail.com.'
'Hadi D. Arman'
;
Department of Chemistry, The University of Texas at San Antonio,
One UTSA Circle, San Antonio, Texas 78249-0698, USA
;
hadi.arman@utsa.edu .
'Pavel Poplaukhin'
;
Chemical Abstracts Service, 2540 Olentangy River Rd,
Columbus, Ohio, 43202, USA
;
paul.ppv@gmail.com .
'Tiekink, Edward R. T.'
;
Research Centre for Crystalline Materials,
Faculty of Science and Technology,
Sunway University, 47500 Bandar Sunway,
Selangor Darul Ehsan, Malaysia
;
edwardt@sunway.edu.my .

_publ_section_title
;\
Bis(N,N-diethyldithiocarbamato-κ²S,S')(3-\
hydroxypyridine-κN)zinc and
bis[N-(2-hydroxyethyl)-N-methyldithiocarbamato-\
κ²S,S'](3-hydroxypyridine-κN)zinc: 
crystal structures and Hirshfeld surface analysis
;

_publ_section_title_footnote .

_publ_section_synopsis 
;
Highly-distorted five-coordinate NS₄ coordination geometries are found in
each of Zn(S₂CNEt)₂(pyOH) and Zn[S₂CN(Me)CH₂CH₂OH]₂(pyOH); pyOH is
3-hydroxypyridine. In their respective crystals, hydrogen bonding leads to
dimeric aggregates in the former (O---H...S) and supramolecular chains in the
latter (O---H...O, S).
;

_publ_section_acknowledgements
;
We thank Sunway University for support of biological and crystal engineering
studies of metal dithiocarbamates.
;

_publ_section_references
;
Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C.
(1984). J. Chem. Soc. Dalton Trans. pp. 1349--1356.

Benson, R. E., Ellis, C. A., Lewis, C. E. & Tiekink, E. R. T. (2007).
CrystEngComm, 9, 930--941.

Bonamico, M., Mazzone, G., Vaciago, A. & Zambonelli, L. (1965). Acta
Cryst. 19, 898--909.

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.

Cardoso, L. N. F., Nogueira, T. C. M., Wardell, J. L., Wardell, S. M. S. V., de
Souza, M. V. N., Jotani, M. M. & Tiekink, E. R. T. (2016). Acta Cryst.
E72, 1025--1031.

Cox, M. J. & Tiekink, E. R. T. (2009). Z. Kristallogr. 214,
184--190.

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849--854.

Gans, J. & Shalloway, D. (2001). J. Mol. Graphics Modell. 19,
557--559.

Heard, P. J. (2005). Prog. Inorg. Chem. 53, 1--69.

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

Ivanov, A. V., Korneeva, E. V., Gerasimenko, A. V. & Forsling, W. (2005).
Russ. J. Coord. Chem. 31, 695--707.

Jamaludin, N. S., Halim, S. N. A., Khoo, C.-H., Chen, B.-J., See, T.-H., Sim,
J.-H., Cheah, Y.-K., Seng, H.-L. & Tiekink, E. R. T. (2016). Z.
Kristallogr. 231, 341--349.

Jotani, M. M., Tan, Y. S. & Tiekink, E. R. T. (2016). Z. Kristallogr.
231, 403--413.

Kang, J.-G., Shin, J.-S., Cho, D.-H., Jeong, Y.-K., Park, C., Soh, S. F., Lai,
C. S. & Tiekink, E. R. T. (2010). Cryst. Growth Des. 10,
1247--1256.

Lai, C. S. & Tiekink, E. R. T. (2003). Appl. Organomet. Chem. 17,
251--252.

Malik, M. A., Motevalli, M., O'Brien, P. & Walsh, J. R. (1997). Inorg.
Chem. 36, 1263--1264.

Manohar, A., Venkatachalam, V., Ramalingam, K., Thirumaran, S., Bocelli, G. &
Cantoni, A. (1998). J. Chem. Crystallogr. 28, 861--866.

McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun.
pp. 3814--3816.

Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The
Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.

Poplaukhin, P. & Tiekink, E. R. T. (2008). Acta Cryst. E64,
m1176.

Safbri, S. A. M., Halim, S. N. A. & Tiekink, E. R. T. (2016). Acta
Cryst. E72, 203--208.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.

Sheldrick, G. M. (2015). Acta Cryst. C71, 3--8.

Spek, A. L. (2009). Acta Cryst. D65, 148--155.

Tan, Y. S., Halim, S. N. A., Molloy, K. C., Sudlow, A. L., Otero-de-la-Roza, A.
& Tiekink, E. R. T. (2016a). CrystEngComm, 18,
1105--1117.

Tan, Y. S., Halim, S. N. A. & Tiekink, E. R. T. (2016b). Z.
Kristallogr. 231, 113--126.

Tan, Y. S., Ooi, K. K., Ang, K. P., Akim, A. M., Cheah, Y.-K., Halim, S. N. A.,
Seng, H.-L. & Tiekink, E. R. T. (2015). J. Inorg. Biochem. 150,
48--62.

Tan, Y. S., Sudlow, A. L., Molloy, K. C., Morishima, Y., Fujisawa, K., Jackson,
W. J., Henderson, W., Halim, S. N. B. A., Ng, S. W. & Tiekink, E. R. T.
(2013). Cryst. Growth Des. 13, 3046--3056.

Tiekink, E. R. T. (2000). Z. Kristallogr. - New Cryst. Struct.
215, 445--446.

Tiekink, E. R. T. (2003). CrystEngComm, 5, 101--113.

Tiekink, E. R. T. & Zukerman-Schpector, J. (2011). Chem. Commun.
47, 6623--6625.

Westrip, S. P. (2010). J. Appl. Cryst. 43, 920--925.

Zeng, D., Hampden-Smith, M. J. & Larson, E. M. (1994). Acta Cryst.
C50, 1000--1002.

Zha, M.-Q., Li, X., Bing, Y. & Lu, Y. (2010). Acta Cryst. E66,
m1465.

Zukerman-Schpector, J., Sousa Madureira, L., Poplaukhin, P., Arman, H. D.,
Miller, T. & Tiekink, E. R. T. (2015). Z. Kristallogr. 230,
531--541.
;

_publ_section_related_literature
;
For related literature, see:
Addison et al. (1984);
Benson et al. (2007);
Bonamico et al. (1965);
Cardoso et al. (2016);
Cox & Tiekink (2009);
Farrugia (2012);
Gans & Shalloway (2001);
Heard (2005);
Ivanov et al. (2005);
Jamaludin et al. (2016);
Jotani et al. (2016);
Kang et al. (2010);
Lai & Tiekink (2003);
Malik et al. (1997);
Manohar et al. (1998);
McKinnon et al. (2007);
Poplaukhin & Tiekink (2008);
Safbri et al. (2016);
Safbri et al. (2016);
Sheldrick (2008);
Sheldrick (2015);
Spek (2009);
Tan et al. (2016a);
Tan et al. (2016b);
Tan et al. (2015);
Tan et al. (2013);
Tiekink (2000);
Tiekink (2003);
Tiekink & Zukerman-Schpector (2011);
Westrip (2010);
Zeng et al. (1994);
Zha et al. (2010);
Zukerman-Schpector et al. (2015).
;

_publ_section_figure_captions
;


The molecular structures of the two independent molecules comprising the
asymmetric unit in (I), showing the atom-labelling scheme and displacement
ellipsoids at the 70% probability level.

The molecular structure of (II), showing the atom-labelling scheme and
displacement ellipsoids at the 70% probability level.

Overlay diagrams for the Zn1- and Zn2-molecules in (I) and the molecule in (II)
shown as red, green and blue images, respectively: (a) approximately
side-on to the pyOH ring and (b) along the N----Zn bond. The molecules
are overlapped so that the pyOH rings are coincident.

The molecular packing in (I), showing (a) detail of the
hydroxy-O---H...S(dithiocarbamate) hydrogen bonding, shown as orange dashed
lines, leading to dimeric aggregates, (b) supramolecular layer where
the aggregates in (a) are linked by C---H...π(chelate) interactions,
shown as purple dashed lines and (c) view of the unit-cell contents
shown in projection down the a axis, with links between layers being of
the type C---H...O,shown as blue dashed lines.

The molecular packing in (II), (a) supramolecular chain mediated by
hydroxy-O---H...O(hydroxy) hydrogen bonding, shown as orange and blue dashed
lines, respectively, and non-acidic H atoms omitted, (b) detail of
methylene-C---H...π(chelate) interactions shown as purple dashed lines and
(c) view of the unit-cell contents shown in projection down the
a axis, with one layer shown in space-filling mode.

Views of the Hirshfeld surfaces for (I) mapped over dnorm for the
(a) Zn1-molecule and, (b) and (c) Zn2-molecule.

Views of the Hirshfeld surfaces mapped over electrostatic potential for (I):
(a) Zn1-molecule and (b) Zn2-molecule.

(a) View of the Hirshfeld surface mapped over dnorm for (I)
showing O---H...S hydrogen bonds and short interatomic C...C and C...H/H...C
contacts, indicated by black, white and red dashed lines, respectively, about
the reference molecule. (b) and (c) Views of Hirshfeld surface
mapped with shape-index property about the Zn1 and Zn2-containing molecules,
respectively. The dotted blue lines labelled with 1-4 indicates
C---H...π(chelate) interactions and the red dotted line shows the π--π
stacking interaction.

Views of the Hirshfeld surfaces for (II) mapped over (a) and (b)
dnorm and (c) electrostatic potential.

(a) and (b) Views of the Hirshfeld surface mapped over
electrostatic potential for (II) showing O---H...S hydrogen bonds about the
reference molecule. The hydrogen bonds are indicated with black dashed lines
and labelled as `1' and `2' in (a). In (b), the intermolecular
C---H...O (labelled with a `6' and shown as red-dashed lines) and
C---H...π/π...H---C (`3', red and blue) interactions, and short interatomic
S...S (`4', black) and C...H (`5', white) contacts are indicated by arrows.

(a) The overall two-dimensional fingerprint plots for the Zn1-molecule
in (I), Zn2-molecule in (I), (I) and (II), respectively, and those delineated
into (b) H...H, (c) O...H/H...O, (d) S...H/H...S, (e)
C...H/H...C, (f) C...C and (g) S...S contacts.
;

_publ_section_table_legends
;
Hydrogen bond geometry (Å, °).
Cg1 and Cg2 are the ring centroids of the (Zn1,S1,S2,C1) and
(Zn2,S7,S8,C21) chelate rings, respectively. 

Hydrogen-bond geometry (Å, °).
Cg1 is the ring centroid of the (Zn,S3,S4,C5) chelate ring.
;

_journal_coden_ASTM               ACSEBH
_journal_coden_Cambridge ?
_journal_coeditor_address ?
_journal_coeditor_code            HB7628
_journal_paper_doi    10.1107/S205698901601728X
_journal_coeditor_email ?
_journal_coeditor_fax ?
_journal_coeditor_name ?
_journal_coeditor_notes ?
_journal_coeditor_phone ?
_journal_data_validation_number ?
_journal_date_accepted            2016-10-27
_journal_date_from_coeditor       2016-10-27
_journal_date_to_coeditor ?
_journal_date_printers_final ?
_journal_date_printers_first      2016-10-27
_journal_date_proofs_in ?
_journal_date_proofs_out          2016-10-27
_journal_date_recd_copyright ?
_journal_date_recd_electronic     2016-10-25
_journal_date_recd_hard_copy ?
_journal_issue                    12
_journal_language ?
_journal_name_full                'Acta Crystallographica, Section E'

_journal_page_first               1700
_journal_page_last                1709
_journal_paper_category          GM
_journal_suppl_publ_number ?
_journal_suppl_publ_pages ?
_journal_techeditor_address ?
_journal_techeditor_code          E161728
_journal_techeditor_email ?
_journal_techeditor_fax ?
_journal_techeditor_name ?
_journal_techeditor_notes ?
_journal_techeditor_phone ?
_journal_volume                   72
_journal_year                     2016
_iucr_compatibility_tag          ACTA95

#Added by publCIF

#Added by publCIF

#Added by publCIF


 
#=============================================================================
# 2. PROCESSING SUMMARY (IUCr Office Use Only)

#=============================================================================
#===========================================================================

# 3. TITLE AND AUTHOR LIST

#Added by publCIF

# Related literature generated by publCIF 2015-07-21







_audit_update_record
;
2014-04-24 # Formatted by publCIF

2015-07-21 # Formatted by IUCr publCIF system
;
_publcif_datablock.id '{92d4c804-1fc9-4242-84e8-84b0d42cfb38}'
# publcif _publ_body_element loop start
 
data_I
_database_code_depnum_ccdc_archive 'CCDC 1511864'
_publcif_datablock.id '{687b4131-b9e9-4956-8180-319fb9f745f5}'
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         
;\
Bis(N,N-diethyldithiocarbamato-κ²S,S')(3-\
hydroxypyridine-κN)zinc
;
_chemical_formula_iupac '[Zn (C5 H10 N S2)2 (C5 H5 N O)]'
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety         'C15 H25 N3 O S4 Zn'
_chemical_formula_sum            'C15 H25 N3 O S4 Zn' 
_chemical_formula_weight          456.99

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'


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 
O1  H1O  S8     0.841(17)  2.453(14)   3.289(2)     173(4)  2_655
O2  H2O  S2     0.844(17)  2.308(13)   3.143(2)     170(4)  2_645
C8  H8A  Cg2         0.98       2.98   3.855(3)        150  1_555
C13 H13  Cg2         0.95       2.79   3.631(3)        148  2_655
C20 H20C Cg1         0.98       2.97   3.850(3)        150  1_655
C28 H28  Cg1         0.95       2.96   3.738(3)        140  2_645
C19 H19A O2          0.99       2.56   3.321(3)        134  4_565

_iucr_geom_hbonds_special_details
;
Cg1 and Cg2 are the centroids of the (Zn1,S1,S2,C1) and 
(Zn2,S7,S8,C21) chelate rings, respectively.
;

_geom_extra_table_head_A
;
Geometric data (\%A, \%) for (I), unsolvated (I) and for (II)
;

loop_
_geom_extra_tablea_col_1
_geom_extra_tablea_col_2
_geom_extra_tablea_col_3
_geom_extra_tablea_col_4
'Parameter' 'Zn1-molecule in (I)' 'Zn2-molecule in (I)' '(II)'
'Zn---S1'     '2.3201 (8)'   '--'   '2.3319 (6)'
'Zn---S2'     '2.7461 (8)'   '--'   '2.7514 (8)'
'Zn---S3'     '2.3417 (8)'   '--'   '2.3437 (7)'
'Zn---S4'     '2.4932 (8)'   '--'   '2.5275 (6)'
'Zn---S5'     '--'   '2.3399 (8)'   '--'
'Zn---S6'     '--'   '2.5453 (8)'   '--'
'Zn---S7'     '--'   '2.3517 (8)'   '--'
'Zn---S8'     '--'   '2.6051 (8)'   '--'
'Zn---N3'     '2.069 (2)'   '--'   '2.0375 (16)'
'Zn---N6'     '--'   '2.070 (2)'   '--'
'C---S1, S2'  '1.736 (3), 1.721 (3)'   '--'   '1.733 (2), 1.7119 (19)'
'C---S3, S4'  '1.741 (3), 1.720 (3)'   '--'   '1.7364 (19), 1.7140 (19)'
'C---S5, S6'  '--'   '1.743 (3), 1.720 (3)'   '--'
'C---S7, S8'  '--'   '1.734 (3), 1.730 (3)'   '--'
'S1---Zn---S2'  '70.99 (3)'   '--'  '70.825 (18)'
'S3---Zn---S4'  '75.54 (3)'   '--'  '74.41 (2)'
'S1---Zn---S3'  '136.44 (3)'  '--'  '139.04 (2)'
'S2---Zn---S4'  '165.17 (2)'  '--'  '148.839 (18)'
'S5---Zn---S6'  '--'   '74.34 (3)'   '--'
'S7---Zn---S8'  '--'   '73.08 (3)'   '--'
'S5---Zn---S7'  '--'   '137.08 (3)'   '--'
'S6---Zn---S8'  '--'   '168.91 (2)'   '--'
'S1,S2,C1/S3,S4,C' '19.30 (12)' '--' '63.81 (15)' 
'S5,S6,C1/S7,S8,C' '--' '38.87 (22)' '--' 


_geom_extra_table_head_B
;
Summary of short interatomic contacts (\%A) in (I) and (II)
;

loop_
_geom_extra_tableb_col_1
_geom_extra_tableb_col_2
_geom_extra_tableb_col_3

'Contact' 'Distance' 'Symmetry operation'
'(I)' '' ''
'C13...C26' '3.314(4)' '1 - <i>x</i>, 1/2 + <i>y</i>, 1/2 - <i>z</i>'
'H5...H7<i>B</i>' '2.36' '-<i>x</i>, 1 - <i>y</i>, -<i>z</i>'
'O1...H18<i>B</i>' '2.61' '2 - <i>x</i>, 1 - <i>y</i>, 1 - <i>z</i>'
'S2...H20<i>B</i>' '2.96' '1 - <i>x</i>, 1 - <i>y</i>, -<i>z</i>'
'S4...H11' '2.98' '1 - <i>x</i>, 1 - <i>y</i>, 1 - <i>z</i>'
'S5...H7<i>A</i>' '2.97' '<i>x</i>, <i>y</i>, <i>z</i>'
'S5...H14' '2.94' '1 - <i>x</i>, 1 - <i>y</i>, -<i>z</i>'
'C1...H28' '2.75' '1 - <i>x</i>, 1/2 + <i>y</i>, 1/2 - <i>z</i>'
'C21...H13' '2.65' '1 - <i>x</i>, -1/2 + <i>y</i>, 1/2 - <i>z</i>'
'C29...H24<i>A</i>' '2.84' '1 + <i>x</i>, <i>y</i>, <i>z</i>'


'(II)' '' ''
'S4...S4' '3.4765(11)' '2 - <i>x</i>, 1 - <i>y</i>, 1 - <i>z</i>'
'C8...C8' '3.308(3)' '2 - <i>x</i>, -<i>y</i>, 1 - <i>z</i>'
'C1...H6<i>A</i>' '2.87' '<i>x</i>, 1 + <i>y</i>, <i>z</i>'
'C9...H7<i>B</i>' '2.57' '<i>x</i>, 1 + <i>y</i>, <i>z</i>'
'C10...H10<i>B</i>' '2.88' '<i>x</i>, 1+<i>y</i>, <i>z</i>'
'H1<i>O</i>...H2<i>O</i>' '2.37(4)' '1 - <i>x</i>, 1 - <i>y</i>, -<i>z</i>'
'H2<i>O</i>...H3<i>O</i>' '2.18(3)' '1 - <i>x</i>, 1 - <i>y</i>, 1 - <i>z</i>'
'S3...H1<i>O</i>' '2.91(3)' '1 - <i>x</i>, 1 - <i>y</i>, -<i>z</i>'
'S3...H7<i>A</i>' '2.99' '1 - <i>x</i>, 1 - <i>y</i>, -<i>z</i>'
'Zn...H2<i>B</i>' '3.06' '2 - <i>x</i>, 1 - <i>y</i>, -<i>z</i>'
'O1...H6<i>A</i>' '2.68' '<i>x</i>, 1 + <i>y</i>, <i>z</i>'



_geom_extra_table_head_C
;
Percentage contribution to interatomic contacts from the Hirshfeld surface
for (I) and (II)
;

loop_
_geom_extra_tablec_col_1
_geom_extra_tablec_col_2
_geom_extra_tablec_col_3
_geom_extra_tablec_col_4
_geom_extra_tablec_col_5

'Contact' 'Zn1-molecule in (I)' 'Zn2-molecule in (I)' '(I)'  '(II)'

'H...H' '55.3' '52.9' '55.3' '42.1'
'O...H/H...O' '4.1' '5.5' '5.3' '15.0'
'S...H/H...S' '23.8' '25.3' '22.7' '22.2'
'C...H/H...C' '9.9' '10.0' '10.0' '12.3'
'N...H/H...N' '2.6' '2.5' '2.7' '2.9'
'S...S' 1.2 '0.7' '1.1' '3.8'
'C...C' 1.6 '1.6' '1.8' '0.8'
'Zn...H/H...Zn' '0.8' '0.8' '0.4' '0.7'
'C...O/O...C' '0.4' '0.4' '0.4' '0.0'
'C...N/N...C' '0.2' '0.2' '0.3' '0.1'
'S...O/O...S' '0.1' '0.1' '0.0' '0.0'
'S...C/C...S' '0.0' '0.0' '0.0' '0.1'

 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_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.
;
 
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'
 
_cell_length_a                    10.032(2)
_cell_length_b                    31.955(7)
_cell_length_c                    13.233(3)
_cell_angle_alpha                 90
_cell_angle_beta                  105.920(2)
_cell_angle_gamma                 90
_cell_volume                      4079.4(15)
_cell_formula_units_Z             8
_cell_measurement_temperature     98(2)
_cell_measurement_reflns_used     16430
_cell_measurement_theta_min       2.47
_cell_measurement_theta_max       40.65
 
_exptl_crystal_description        slab
_exptl_crystal_colour             pink
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.488          
_exptl_crystal_F_000              1904
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.50
_exptl_crystal_size_mid           0.40
_exptl_crystal_size_min           0.15
_exptl_absorpt_coefficient_mu     1.621
_shelx_estimated_absorpt_T_min    0.498
_shelx_estimated_absorpt_T_max    0.793
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.6867
_exptl_absorpt_correction_T_max   1.0000
_exptl_absorpt_process_details    
;
(ABSCOR; Higashi, 1995)
;
 
_diffrn_ambient_temperature       98(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Rigaku AFC12κ/SATURN724' 
_diffrn_measurement_method        ω 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          0 
_diffrn_standards_interval_count  0 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         0
_diffrn_reflns_number             25139
_diffrn_reflns_av_unetI/netI      0.0401
_diffrn_reflns_av_R_equivalents   0.0371
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -41
_diffrn_reflns_limit_k_max        41
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          2.466
_diffrn_reflns_theta_max          27.500
_diffrn_reflns_theta_full         27.500
_diffrn_measured_fraction_theta_max   0.983
_diffrn_measured_fraction_theta_full  0.983
_diffrn_reflns_Laue_measured_fraction_max    0.983
_diffrn_reflns_Laue_measured_fraction_full   0.983
_diffrn_reflns_point_group_measured_fraction_max   0.983
_diffrn_reflns_point_group_measured_fraction_full  0.983
_reflns_number_total              9202
_reflns_number_gt                 8401
_reflns_threshold_expression      'I > 2σ(I)'
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        
;
CrystalClear (Molecular Structure Corporation & Rigaku, 2005)
;
_computing_cell_refinement
;
CrystalClear (Molecular Structure Corporation & Rigaku, 2005)
;
_computing_data_reduction
;
CrystalClear (Molecular Structure Corporation & Rigaku, 2005)
;
_computing_structure_solution     
;
SHELXS97 (Sheldrick, 2008)
;

_computing_structure_refinement   
;
SHELXL2014 (Sheldrick, 2015)
;

_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway,
2001),
DIAMOND (Brandenburg, 2006)
;
_computing_publication_material   
;
publCIF (Westrip, 2010)
;


_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0477P)²+4.2267P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          9202
_refine_ls_number_parameters      447
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0459
_refine_ls_R_factor_gt            0.0411
_refine_ls_wR_factor_ref          0.1060
_refine_ls_wR_factor_gt           0.1021
_refine_ls_goodness_of_fit_ref    1.062
_refine_ls_restrained_S_all       1.062
_refine_ls_shift/su_max           0.002
_refine_ls_shift/su_mean          0.000
 
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
Zn1 Zn 0.22939(3) 0.51145(2) 0.27529(3) 0.02233(8) Uani 1 1 d . . . . .
S1 S 0.06711(7) 0.51485(2) 0.37067(5) 0.02470(14) Uani 1 1 d . . . . .
S2 S -0.01500(6) 0.54220(2) 0.14827(5) 0.02127(13) Uani 1 1 d . . . . .
S3 S 0.27656(6) 0.46663(2) 0.14937(5) 0.02206(13) Uani 1 1 d . . . . .
S4 S 0.42106(7) 0.46582(2) 0.37705(5) 0.02349(14) Uani 1 1 d . . . . .
O1 O 0.5087(2) 0.64627(6) 0.45759(17) 0.0305(4) Uani 1 1 d D . . . .
H1O H 0.524(4) 0.6717(4) 0.449(3) 0.046 Uiso 1 1 d D U . . .
N1 N -0.1829(2) 0.54510(7) 0.27436(17) 0.0206(4) Uani 1 1 d . . . . .
N2 N 0.4941(2) 0.41780(7) 0.23507(18) 0.0218(4) Uani 1 1 d . . . . .
N3 N 0.3333(2) 0.56740(7) 0.27551(18) 0.0209(4) Uani 1 1 d . . . . .
C1 C -0.0580(3) 0.53538(8) 0.2645(2) 0.0194(5) Uani 1 1 d . . . . .
C2 C -0.2190(3) 0.54050(9) 0.3748(2) 0.0257(5) Uani 1 1 d . . . . .
H2A H -0.1631 0.5176 0.4162 0.031 Uiso 1 1 calc R U . . .
H2B H -0.3180 0.5327 0.3602 0.031 Uiso 1 1 calc R U . . .
C3 C -0.1933(3) 0.58063(10) 0.4389(2) 0.0339(7) Uani 1 1 d . . . . .
H3A H -0.0933 0.5856 0.4649 0.051 Uiso 1 1 calc R U . . .
H3B H -0.2330 0.5780 0.4985 0.051 Uiso 1 1 calc R U . . .
H3C H -0.2371 0.6041 0.3946 0.051 Uiso 1 1 calc R U . . .
C4 C -0.2961(3) 0.55989(9) 0.1855(2) 0.0265(5) Uani 1 1 d . . . . .
H4A H -0.2567 0.5750 0.1350 0.032 Uiso 1 1 calc R U . . .
H4B H -0.3553 0.5796 0.2114 0.032 Uiso 1 1 calc R U . . .
C5 C -0.3837(3) 0.52333(10) 0.1301(2) 0.0334(6) Uani 1 1 d . . . . .
H5A H -0.3275 0.5054 0.0978 0.050 Uiso 1 1 calc R U . . .
H5B H -0.4634 0.5340 0.0756 0.050 Uiso 1 1 calc R U . . .
H5C H -0.4166 0.5071 0.1813 0.050 Uiso 1 1 calc R U . . .
C6 C 0.4075(3) 0.44668(8) 0.2532(2) 0.0203(5) Uani 1 1 d . . . . .
C7 C 0.4939(3) 0.40561(9) 0.1276(2) 0.0268(6) Uani 1 1 d . . . . .
H7A H 0.5897 0.3983 0.1272 0.032 Uiso 1 1 calc R U . . .
H7B H 0.4644 0.4299 0.0804 0.032 Uiso 1 1 calc R U . . .
C8 C 0.3997(3) 0.36900(10) 0.0850(3) 0.0353(7) Uani 1 1 d . . . . .
H8A H 0.4218 0.3457 0.1350 0.053 Uiso 1 1 calc R U . . .
H8B H 0.4134 0.3602 0.0177 0.053 Uiso 1 1 calc R U . . .
H8C H 0.3030 0.3774 0.0748 0.053 Uiso 1 1 calc R U . . .
C9 C 0.6003(3) 0.39774(8) 0.3208(2) 0.0261(5) Uani 1 1 d . . . . .
H9A H 0.6182 0.3691 0.2992 0.031 Uiso 1 1 calc R U . . .
H9B H 0.5651 0.3954 0.3836 0.031 Uiso 1 1 calc R U . . .
C10 C 0.7353(3) 0.42242(10) 0.3491(2) 0.0313(6) Uani 1 1 d . . . . .
H10A H 0.7667 0.4266 0.2860 0.047 Uiso 1 1 calc R U . . .
H10B H 0.8060 0.4069 0.4015 0.047 Uiso 1 1 calc R U . . .
H10C H 0.7201 0.4497 0.3782 0.047 Uiso 1 1 calc R U . . .
C11 C 0.3950(3) 0.58787(8) 0.3647(2) 0.0236(5) Uani 1 1 d . . . . .
H11 H 0.4004 0.5749 0.4303 0.028 Uiso 1 1 calc R U . . .
C12 C 0.4514(3) 0.62776(8) 0.3636(2) 0.0236(5) Uani 1 1 d . . . . .
C13 C 0.4457(3) 0.64633(8) 0.2680(2) 0.0242(5) Uani 1 1 d . . . . .
H13 H 0.4834 0.6734 0.2653 0.029 Uiso 1 1 calc R U . . .
C14 C 0.3839(3) 0.62468(9) 0.1761(2) 0.0266(5) Uani 1 1 d . . . . .
H14 H 0.3798 0.6366 0.1096 0.032 Uiso 1 1 calc R U . . .
C15 C 0.3287(3) 0.58556(9) 0.1827(2) 0.0233(5) Uani 1 1 d . . . . .
H15 H 0.2859 0.5709 0.1197 0.028 Uiso 1 1 calc R U . . .
Zn2 Zn 0.68820(3) 0.27217(2) 0.19561(3) 0.02217(8) Uani 1 1 d . . . . .
S5 S 0.75317(6) 0.32449(2) 0.09483(5) 0.02196(13) Uani 1 1 d . . . . .
S6 S 0.89261(7) 0.30961(2) 0.31945(5) 0.02480(14) Uani 1 1 d . . . . .
S7 S 0.52971(7) 0.26483(2) 0.29651(5) 0.02464(14) Uani 1 1 d . . . . .
S8 S 0.45448(6) 0.24765(2) 0.06815(5) 0.02173(13) Uani 1 1 d . . . . .
O2 O 0.9810(2) 0.13960(6) 0.36656(16) 0.0293(4) Uani 1 1 d D . . . .
H2O H 0.997(4) 0.1141(4) 0.358(3) 0.044 Uiso 1 1 d D U . . .
N4 N 0.9764(2) 0.36702(7) 0.20279(18) 0.0214(4) Uani 1 1 d . . . . .
N5 N 0.2806(2) 0.23709(7) 0.18746(18) 0.0218(4) Uani 1 1 d . . . . .
N6 N 0.7917(2) 0.21685(7) 0.18654(18) 0.0214(4) Uani 1 1 d . . . . .
C16 C 0.8854(3) 0.33725(8) 0.2066(2) 0.0196(5) Uani 1 1 d . . . . .
C17 C 1.0857(3) 0.37985(9) 0.2973(2) 0.0270(6) Uani 1 1 d . . . . .
H17A H 1.0512 0.3764 0.3601 0.032 Uiso 1 1 calc R U . . .
H17B H 1.1075 0.4098 0.2914 0.032 Uiso 1 1 calc R U . . .
C18 C 1.2165(3) 0.35417(10) 0.3110(3) 0.0358(7) Uani 1 1 d . . . . .
H18A H 1.1964 0.3247 0.3211 0.054 Uiso 1 1 calc R U . . .
H18B H 1.2880 0.3642 0.3725 0.054 Uiso 1 1 calc R U . . .
H18C H 1.2497 0.3570 0.2482 0.054 Uiso 1 1 calc R U . . .
C19 C 0.9748(3) 0.38995(8) 0.1058(2) 0.0246(5) Uani 1 1 d . . . . .
H19A H 0.9319 0.3722 0.0442 0.030 Uiso 1 1 calc R U . . .
H19B H 1.0713 0.3959 0.1050 0.030 Uiso 1 1 calc R U . . .
C20 C 0.8951(3) 0.43075(9) 0.0970(2) 0.0284(6) Uani 1 1 d . . . . .
H20A H 0.7968 0.4248 0.0881 0.043 Uiso 1 1 calc R U . . .
H20B H 0.9056 0.4466 0.0362 0.043 Uiso 1 1 calc R U . . .
H20C H 0.9315 0.4473 0.1610 0.043 Uiso 1 1 calc R U . . .
C21 C 0.4063(3) 0.24864(8) 0.1840(2) 0.0206(5) Uani 1 1 d . . . . .
C22 C 0.2413(3) 0.23388(9) 0.2868(2) 0.0247(5) Uani 1 1 d . . . . .
H22A H 0.1416 0.2405 0.2736 0.030 Uiso 1 1 calc R U . . .
H22B H 0.2948 0.2546 0.3377 0.030 Uiso 1 1 calc R U . . .
C23 C 0.2691(3) 0.19034(10) 0.3332(2) 0.0310(6) Uani 1 1 d . . . . .
H23A H 0.2249 0.1696 0.2800 0.047 Uiso 1 1 calc R U . . .
H23B H 0.2311 0.1879 0.3937 0.047 Uiso 1 1 calc R U . . .
H23C H 0.3693 0.1853 0.3559 0.047 Uiso 1 1 calc R U . . .
C24 C 0.1702(3) 0.22577(9) 0.0921(2) 0.0262(6) Uani 1 1 d . . . . .
H24A H 0.1135 0.2028 0.1086 0.031 Uiso 1 1 calc R U . . .
H24B H 0.2125 0.2158 0.0371 0.031 Uiso 1 1 calc R U . . .
C25 C 0.0776(3) 0.26349(11) 0.0511(3) 0.0371(7) Uani 1 1 d . . . . .
H25A H 0.0353 0.2732 0.1053 0.056 Uiso 1 1 calc R U . . .
H25B H 0.0047 0.2554 -0.0118 0.056 Uiso 1 1 calc R U . . .
H25C H 0.1335 0.2860 0.0333 0.056 Uiso 1 1 calc R U . . .
C26 C 0.8547(3) 0.19591(8) 0.2743(2) 0.0225(5) Uani 1 1 d . . . . .
H26 H 0.8552 0.2078 0.3402 0.027 Uiso 1 1 calc R U . . .
C27 C 0.9194(3) 0.15755(8) 0.2729(2) 0.0223(5) Uani 1 1 d . . . . .
C28 C 0.9185(3) 0.14053(8) 0.1761(2) 0.0249(5) Uani 1 1 d . . . . .
H28 H 0.9612 0.1143 0.1720 0.030 Uiso 1 1 calc R U . . .
C29 C 0.8541(3) 0.16261(9) 0.0855(2) 0.0261(5) Uani 1 1 d . . . . .
H29 H 0.8533 0.1517 0.0185 0.031 Uiso 1 1 calc R U . . .
C30 C 0.7912(3) 0.20054(9) 0.0932(2) 0.0242(5) Uani 1 1 d . . . . .
H30 H 0.7466 0.2154 0.0308 0.029 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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 N3 2.069(2) . ?
Zn1 S1 2.3201(8) . ?
Zn1 S3 2.3417(8) . ?
Zn1 S4 2.4932(8) . ?
Zn1 S2 2.7461(8) . ?
S1 C1 1.736(3) . ?
S2 C1 1.721(3) . ?
S3 C6 1.741(3) . ?
S4 C6 1.720(3) . ?
O1 C12 1.355(3) . ?
O1 H1O 0.842(10) . ?
N1 C1 1.332(3) . ?
N1 C4 1.470(3) . ?
N1 C2 1.477(3) . ?
N2 C6 1.333(3) . ?
N2 C9 1.473(3) . ?
N2 C7 1.474(3) . ?
N3 C11 1.343(3) . ?
N3 C15 1.347(3) . ?
C2 C3 1.520(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.524(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 C8 1.512(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.523(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.397(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(4) . ?
C13 C14 1.388(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
Zn2 N6 2.070(2) . ?
Zn2 S5 2.3399(8) . ?
Zn2 S7 2.3517(8) . ?
Zn2 S6 2.5453(8) . ?
Zn2 S8 2.6051(8) . ?
S5 C16 1.743(3) . ?
S6 C16 1.720(3) . ?
S7 C21 1.734(3) . ?
S8 C21 1.730(3) . ?
O2 C27 1.352(3) . ?
O2 H2O 0.844(10) . ?
N4 C16 1.328(3) . ?
N4 C19 1.474(3) . ?
N4 C17 1.478(3) . ?
N5 C21 1.326(3) . ?
N5 C22 1.476(3) . ?
N5 C24 1.478(3) . ?
N6 C26 1.339(3) . ?
N6 C30 1.340(4) . ?
C17 C18 1.515(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.517(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C22 C23 1.515(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.528(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.390(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.389(4) . ?
C28 C29 1.389(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.383(4) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
 
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
N3 Zn1 S1 112.77(6) . . ?
N3 Zn1 S3 109.24(6) . . ?
S1 Zn1 S3 136.44(3) . . ?
N3 Zn1 S4 101.02(6) . . ?
S1 Zn1 S4 106.61(3) . . ?
S3 Zn1 S4 75.54(3) . . ?
N3 Zn1 S2 93.23(6) . . ?
S1 Zn1 S2 70.99(3) . . ?
S3 Zn1 S2 95.97(3) . . ?
S4 Zn1 S2 165.17(2) . . ?
C1 S1 Zn1 92.11(9) . . ?
C1 S2 Zn1 78.96(9) . . ?
C6 S3 Zn1 85.32(9) . . ?
C6 S4 Zn1 81.11(9) . . ?
C12 O1 H1O 110(3) . . ?
C1 N1 C4 122.5(2) . . ?
C1 N1 C2 122.3(2) . . ?
C4 N1 C2 115.2(2) . . ?
C6 N2 C9 122.1(2) . . ?
C6 N2 C7 121.9(2) . . ?
C9 N2 C7 116.0(2) . . ?
C11 N3 C15 118.9(2) . . ?
C11 N3 Zn1 122.19(18) . . ?
C15 N3 Zn1 118.67(18) . . ?
N1 C1 S2 122.1(2) . . ?
N1 C1 S1 119.98(19) . . ?
S2 C1 S1 117.91(14) . . ?
N1 C2 C3 111.8(2) . . ?
N1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 110.8(2) . . ?
N1 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 S4 122.2(2) . . ?
N2 C6 S3 120.0(2) . . ?
S4 C6 S3 117.86(14) . . ?
N2 C7 C8 113.5(2) . . ?
N2 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
N2 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 111.8(2) . . ?
N2 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C12 121.7(3) . . ?
N3 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
O1 C12 C13 123.6(3) . . ?
O1 C12 C11 117.4(3) . . ?
C13 C12 C11 119.1(3) . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
N3 C15 C14 122.3(3) . . ?
N3 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
N6 Zn2 S5 110.78(6) . . ?
N6 Zn2 S7 112.06(6) . . ?
S5 Zn2 S7 137.08(3) . . ?
N6 Zn2 S6 96.34(6) . . ?
S5 Zn2 S6 74.34(3) . . ?
S7 Zn2 S6 103.42(3) . . ?
N6 Zn2 S8 94.71(6) . . ?
S5 Zn2 S8 100.83(3) . . ?
S7 Zn2 S8 73.08(3) . . ?
S6 Zn2 S8 168.91(2) . . ?
C16 S5 Zn2 87.12(9) . . ?
C16 S6 Zn2 81.24(9) . . ?
C21 S7 Zn2 88.69(9) . . ?
C21 S8 Zn2 80.88(9) . . ?
C27 O2 H2O 110(3) . . ?
C16 N4 C19 123.1(2) . . ?
C16 N4 C17 121.7(2) . . ?
C19 N4 C17 115.3(2) . . ?
C21 N5 C22 122.6(2) . . ?
C21 N5 C24 122.4(2) . . ?
C22 N5 C24 115.0(2) . . ?
C26 N6 C30 119.1(2) . . ?
C26 N6 Zn2 120.10(18) . . ?
C30 N6 Zn2 120.70(18) . . ?
N4 C16 S6 122.3(2) . . ?
N4 C16 S5 120.4(2) . . ?
S6 C16 S5 117.23(14) . . ?
N4 C17 C18 111.6(2) . . ?
N4 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
N4 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N4 C19 C20 111.9(2) . . ?
N4 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
N4 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N5 C21 S8 121.7(2) . . ?
N5 C21 S7 121.0(2) . . ?
S8 C21 S7 117.32(15) . . ?
N5 C22 C23 111.1(2) . . ?
N5 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
N5 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N5 C24 C25 110.5(2) . . ?
N5 C24 H24A 109.5 . . ?
C25 C24 H24A 109.5 . . ?
N5 C24 H24B 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N6 C26 C27 122.7(3) . . ?
N6 C26 H26 118.7 . . ?
C27 C26 H26 118.7 . . ?
O2 C27 C28 124.4(2) . . ?
O2 C27 C26 117.3(2) . . ?
C28 C27 C26 118.3(3) . . ?
C27 C28 C29 118.7(3) . . ?
C27 C28 H28 120.6 . . ?
C29 C28 H28 120.6 . . ?
C30 C29 C28 119.7(3) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
N6 C30 C29 121.5(3) . . ?
N6 C30 H30 119.3 . . ?
C29 C30 H30 119.3 . . ?
 
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
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C4 N1 C1 S2 3.9(3) . . . . ?
C2 N1 C1 S2 -178.13(19) . . . . ?
C4 N1 C1 S1 -175.75(19) . . . . ?
C2 N1 C1 S1 2.2(3) . . . . ?
Zn1 S2 C1 N1 179.1(2) . . . . ?
Zn1 S2 C1 S1 -1.28(12) . . . . ?
Zn1 S1 C1 N1 -178.9(2) . . . . ?
Zn1 S1 C1 S2 1.49(14) . . . . ?
C1 N1 C2 C3 92.4(3) . . . . ?
C4 N1 C2 C3 -89.5(3) . . . . ?
C1 N1 C4 C5 91.2(3) . . . . ?
C2 N1 C4 C5 -86.9(3) . . . . ?
C9 N2 C6 S4 5.1(3) . . . . ?
C7 N2 C6 S4 -171.71(19) . . . . ?
C9 N2 C6 S3 -175.58(19) . . . . ?
C7 N2 C6 S3 7.6(3) . . . . ?
Zn1 S4 C6 N2 175.6(2) . . . . ?
Zn1 S4 C6 S3 -3.74(12) . . . . ?
Zn1 S3 C6 N2 -175.4(2) . . . . ?
Zn1 S3 C6 S4 3.94(13) . . . . ?
C6 N2 C7 C8 -91.5(3) . . . . ?
C9 N2 C7 C8 91.5(3) . . . . ?
C6 N2 C9 C10 -88.5(3) . . . . ?
C7 N2 C9 C10 88.5(3) . . . . ?
C15 N3 C11 C12 1.5(4) . . . . ?
Zn1 N3 C11 C12 -172.77(19) . . . . ?
N3 C11 C12 O1 178.6(2) . . . . ?
N3 C11 C12 C13 -1.2(4) . . . . ?
O1 C12 C13 C14 -179.7(2) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C11 N3 C15 C14 -0.7(4) . . . . ?
Zn1 N3 C15 C14 173.8(2) . . . . ?
C13 C14 C15 N3 -0.4(4) . . . . ?
C19 N4 C16 S6 177.68(19) . . . . ?
C17 N4 C16 S6 -3.3(3) . . . . ?
C19 N4 C16 S5 -1.8(3) . . . . ?
C17 N4 C16 S5 177.20(19) . . . . ?
Zn2 S6 C16 N4 -177.2(2) . . . . ?
Zn2 S6 C16 S5 2.33(12) . . . . ?
Zn2 S5 C16 N4 177.0(2) . . . . ?
Zn2 S5 C16 S6 -2.51(13) . . . . ?
C16 N4 C17 C18 89.7(3) . . . . ?
C19 N4 C17 C18 -91.2(3) . . . . ?
C16 N4 C19 C20 94.5(3) . . . . ?
C17 N4 C19 C20 -84.6(3) . . . . ?
C22 N5 C21 S8 174.11(19) . . . . ?
C24 N5 C21 S8 -4.8(3) . . . . ?
C22 N5 C21 S7 -5.2(3) . . . . ?
C24 N5 C21 S7 175.93(19) . . . . ?
Zn2 S8 C21 N5 -177.8(2) . . . . ?
Zn2 S8 C21 S7 1.50(12) . . . . ?
Zn2 S7 C21 N5 177.7(2) . . . . ?
Zn2 S7 C21 S8 -1.64(14) . . . . ?
C21 N5 C22 C23 -90.3(3) . . . . ?
C24 N5 C22 C23 88.7(3) . . . . ?
C21 N5 C24 C25 -95.2(3) . . . . ?
C22 N5 C24 C25 85.8(3) . . . . ?
C30 N6 C26 C27 -0.4(4) . . . . ?
Zn2 N6 C26 C27 176.51(19) . . . . ?
N6 C26 C27 O2 179.3(2) . . . . ?
N6 C26 C27 C28 0.2(4) . . . . ?
O2 C27 C28 C29 -178.6(2) . . . . ?
C26 C27 C28 C29 0.4(4) . . . . ?
C27 C28 C29 C30 -0.8(4) . . . . ?
C26 N6 C30 C29 0.1(4) . . . . ?
Zn2 N6 C30 C29 -176.88(19) . . . . ?
C28 C29 C30 N6 0.6(4) . . . . ?
 
_refine_diff_density_max    0.730
_refine_diff_density_min   -0.445
_refine_diff_density_rms    0.083



 
data_II
_database_code_depnum_ccdc_archive 'CCDC 1511865'
_publcif_datablock.id '{da9ee6d5-6e6c-4a13-80c9-1434e53164c0}'
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         
;\
Bis[N-(2-hydroxyethyl)-N-methyldithiocarbamato-\
κ²S,S'](3-hydroxypyridine-κN)zinc
;
_chemical_formula_iupac '[Zn (C4 H8 N O S2)2 (C5 H5 N O)]'
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety         'C13 H21 N3 O3 S4 Zn'
_chemical_formula_sum            'C13 H21 N3 O3 S4 Zn' 
_chemical_formula_weight          460.94

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'


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 
O1  H1O  S2       0.84(2)    2.61(2)   3.371(2)     152(3)  .
O2  H2O  O1       0.83(3)    1.94(3)   2.734(2)     161(3)  2_665
O3  H3O  O2       0.84(3)    1.79(2)   2.619(2)     170(3)  2_666
C2  H2B  Cg1         0.99       2.76   3.689(2)        156  2_765 

_iucr_geom_hbonds_special_details
;
Cg1 is the centroid of the (Zn,S3,S4,C5) chelate ring.
;

 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_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.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    8.8645(19)
_cell_length_b                    9.956(2)
_cell_length_c                    11.473(3)
_cell_angle_alpha                 102.154(4)
_cell_angle_beta                  106.989(4)
_cell_angle_gamma                 93.466(3)
_cell_volume                      938.6(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     98(2)
_cell_measurement_reflns_used     4145 
_cell_measurement_theta_min       2.49 
_cell_measurement_theta_max       40.57 
 
_exptl_crystal_description        'slab' 
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.631          
_exptl_crystal_F_000              476
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.37
_exptl_crystal_size_mid           0.25
_exptl_crystal_size_min           0.25
_exptl_absorpt_coefficient_mu     1.770
_shelx_estimated_absorpt_T_min    0.560
_shelx_estimated_absorpt_T_max    0.666
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.8603
_exptl_absorpt_correction_T_max   1.0000
_exptl_absorpt_process_details    
;
(ABSCOR; Higashi, 1995)
;
 
_diffrn_ambient_temperature       98(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Rigaku AFC12κ/SATURN724' 
_diffrn_measurement_method        ω 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          0 
_diffrn_standards_interval_count  0 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         0
_diffrn_reflns_number             6836
_diffrn_reflns_av_unetI/netI      0.0351
_diffrn_reflns_av_R_equivalents   0.0260
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          2.423
_diffrn_reflns_theta_max          27.499
_diffrn_reflns_theta_full         27.499
_diffrn_measured_fraction_theta_max   0.987
_diffrn_measured_fraction_theta_full  0.987
_diffrn_reflns_Laue_measured_fraction_max    0.987
_diffrn_reflns_Laue_measured_fraction_full   0.987
_diffrn_reflns_point_group_measured_fraction_max   0.987
_diffrn_reflns_point_group_measured_fraction_full  0.987
_reflns_number_total              4249
_reflns_number_gt                 4133
_reflns_threshold_expression      'I > 2σ(I)'
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        
;
CrystalClear (Molecular Structure Corporation & Rigaku, 2005)
;
_computing_cell_refinement
;
CrystalClear (Molecular Structure Corporation & Rigaku, 2005)
;
_computing_data_reduction
;
CrystalClear (Molecular Structure Corporation & Rigaku, 2005)
;
_computing_structure_solution     
;
SHELXS97 (Sheldrick, 2008)
;

_computing_structure_refinement   
;
SHELXL2014 (Sheldrick, 2015)
;

_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
; 
_computing_publication_material   
;
publCIF (Westrip, 2010)
;


_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0370P)²+0.6872P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4249
_refine_ls_number_parameters      228
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.0325
_refine_ls_R_factor_gt            0.0316
_refine_ls_wR_factor_ref          0.0795
_refine_ls_wR_factor_gt           0.0788
_refine_ls_goodness_of_fit_ref    1.057
_refine_ls_restrained_S_all       1.057
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
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
Zn Zn 0.76357(3) 0.49975(2) 0.25271(2) 0.01863(8) Uani 1 1 d . . . . .
S1 S 0.97385(5) 0.65936(5) 0.26357(4) 0.01674(11) Uani 1 1 d . . . . .
S2 S 0.69910(6) 0.58080(5) 0.03011(5) 0.01835(11) Uani 1 1 d . . . . .
S3 S 0.64889(6) 0.27205(5) 0.14638(4) 0.01739(11) Uani 1 1 d . . . . .
S4 S 0.90377(6) 0.34805(5) 0.38990(4) 0.01782(11) Uani 1 1 d . . . . .
O1 O 0.74043(18) 0.85049(17) -0.09808(15) 0.0260(3) Uani 1 1 d D . . . .
H1O H 0.695(3) 0.783(2) -0.083(3) 0.039 Uiso 1 1 d D U . . .
O2 O 0.45844(17) 0.01078(16) 0.24736(13) 0.0218(3) Uani 1 1 d D . . . .
H2O H 0.413(3) 0.051(3) 0.193(2) 0.033 Uiso 1 1 d D U . . .
O3 O 0.67339(19) 0.91603(16) 0.57620(15) 0.0285(3) Uani 1 1 d D . . . .
H3O H 0.624(3) 0.945(3) 0.627(2) 0.043 Uiso 1 1 d D U . . .
N1 N 0.98304(19) 0.70602(17) 0.04700(15) 0.0176(3) Uani 1 1 d . . . . .
N2 N 0.78664(19) 0.08741(16) 0.26777(15) 0.0161(3) Uani 1 1 d . . . . .
N3 N 0.62518(19) 0.59446(17) 0.35049(15) 0.0169(3) Uani 1 1 d . . . . .
C1 C 0.8924(2) 0.65371(18) 0.10539(18) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.9350(2) 0.6846(2) -0.09003(18) 0.0191(4) Uani 1 1 d . . . . .
H2A H 0.8502 0.6046 -0.1285 0.023 Uiso 1 1 calc R U . . .
H2B H 1.0271 0.6612 -0.1190 0.023 Uiso 1 1 calc R U . . .
C3 C 0.8749(2) 0.8097(2) -0.1355(2) 0.0221(4) Uani 1 1 d . . . . .
H3A H 0.9619 0.8882 -0.1017 0.027 Uiso 1 1 calc R U . . .
H3B H 0.8450 0.7881 -0.2282 0.027 Uiso 1 1 calc R U . . .
C4 C 1.1446(2) 0.7770(2) 0.1154(2) 0.0252(4) Uani 1 1 d . . . . .
H4A H 1.1454 0.8372 0.1951 0.038 Uiso 1 1 calc R U . . .
H4B H 1.1789 0.8330 0.0647 0.038 Uiso 1 1 calc R U . . .
H4C H 1.2175 0.7081 0.1321 0.038 Uiso 1 1 calc R U . . .
C5 C 0.7800(2) 0.22057(19) 0.26907(17) 0.0143(3) Uani 1 1 d . . . . .
C6 C 0.6826(2) -0.02451(19) 0.16625(18) 0.0181(4) Uani 1 1 d . . . . .
H6A H 0.7468 -0.0971 0.1421 0.022 Uiso 1 1 calc R U . . .
H6B H 0.6353 0.0126 0.0920 0.022 Uiso 1 1 calc R U . . .
C7 C 0.5502(2) -0.0887(2) 0.20439(18) 0.0193(4) Uani 1 1 d . . . . .
H7A H 0.4796 -0.1595 0.1316 0.023 Uiso 1 1 calc R U . . .
H7B H 0.5972 -0.1359 0.2718 0.023 Uiso 1 1 calc R U . . .
C8 C 0.8976(2) 0.0451(2) 0.3718(2) 0.0232(4) Uani 1 1 d . . . . .
H8A H 1.0069 0.0797 0.3796 0.035 Uiso 1 1 calc R U . . .
H8B H 0.8852 -0.0562 0.3554 0.035 Uiso 1 1 calc R U . . .
H8C H 0.8751 0.0837 0.4499 0.035 Uiso 1 1 calc R U . . .
C9 C 0.6861(2) 0.7161(2) 0.43240(18) 0.0175(4) Uani 1 1 d . . . . .
H9 H 0.7921 0.7530 0.4436 0.021 Uiso 1 1 calc R U . . .
C10 C 0.6007(2) 0.7911(2) 0.50204(18) 0.0194(4) Uani 1 1 d . . . . .
C11 C 0.4471(2) 0.7342(2) 0.48828(19) 0.0226(4) Uani 1 1 d . . . . .
H11 H 0.3855 0.7818 0.5347 0.027 Uiso 1 1 calc R U . . .
C12 C 0.3863(2) 0.6063(2) 0.4053(2) 0.0249(4) Uani 1 1 d . . . . .
H12 H 0.2826 0.5646 0.3953 0.030 Uiso 1 1 calc R U . . .
C13 C 0.4768(2) 0.5400(2) 0.33723(19) 0.0221(4) Uani 1 1 d . . . . .
H13 H 0.4331 0.4534 0.2794 0.027 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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
Zn N3 2.0375(16) . ?
Zn S1 2.3319(6) . ?
Zn S3 2.3437(7) . ?
Zn S4 2.5275(6) . ?
Zn S2 2.7514(8) . ?
S1 C1 1.733(2) . ?
S2 C1 1.7119(19) . ?
S3 C5 1.7364(19) . ?
S4 C5 1.7140(19) . ?
O1 C3 1.433(2) . ?
O1 H1O 0.833(10) . ?
O2 C7 1.418(2) . ?
O2 H2O 0.833(10) . ?
O3 C10 1.350(2) . ?
O3 H3O 0.834(10) . ?
N1 C1 1.333(2) . ?
N1 C4 1.468(2) . ?
N1 C2 1.468(2) . ?
N2 C5 1.328(2) . ?
N2 C8 1.464(2) . ?
N2 C6 1.466(2) . ?
N3 C9 1.337(3) . ?
N3 C13 1.345(3) . ?
C2 C3 1.516(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 C7 1.518(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.393(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
 
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
N3 Zn S1 109.72(5) . . ?
N3 Zn S3 110.80(5) . . ?
S1 Zn S3 139.04(2) . . ?
N3 Zn S4 103.07(5) . . ?
S1 Zn S4 102.00(2) . . ?
S3 Zn S4 74.41(2) . . ?
N3 Zn S2 107.89(5) . . ?
S1 Zn S2 70.825(18) . . ?
S3 Zn S2 91.20(2) . . ?
S4 Zn S2 148.839(18) . . ?
C1 S1 Zn 90.54(6) . . ?
C1 S2 Zn 77.85(7) . . ?
C5 S3 Zn 86.67(6) . . ?
C5 S4 Zn 81.43(7) . . ?
C3 O1 H1O 109(2) . . ?
C7 O2 H2O 113(2) . . ?
C10 O3 H3O 110(2) . . ?
C1 N1 C4 121.53(17) . . ?
C1 N1 C2 122.52(16) . . ?
C4 N1 C2 115.68(16) . . ?
C5 N2 C8 120.74(16) . . ?
C5 N2 C6 122.91(16) . . ?
C8 N2 C6 116.33(15) . . ?
C9 N3 C13 118.73(17) . . ?
C9 N3 Zn 118.04(13) . . ?
C13 N3 Zn 123.22(14) . . ?
N1 C1 S2 122.54(15) . . ?
N1 C1 S1 118.66(14) . . ?
S2 C1 S1 118.79(11) . . ?
N1 C2 C3 113.44(16) . . ?
N1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
N1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
O1 C3 C2 112.64(16) . . ?
O1 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
O1 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 S4 121.34(14) . . ?
N2 C5 S3 121.19(14) . . ?
S4 C5 S3 117.46(11) . . ?
N2 C6 C7 112.02(16) . . ?
N2 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O2 C7 C6 112.50(16) . . ?
O2 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
O2 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C10 122.79(18) . . ?
N3 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
O3 C10 C9 116.64(18) . . ?
O3 C10 C11 125.07(18) . . ?
C9 C10 C11 118.27(19) . . ?
C12 C11 C10 118.52(19) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C11 119.77(19) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
N3 C13 C12 121.87(19) . . ?
N3 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
 
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
 _geom_torsion_publ_flag
C4 N1 C1 S2 175.51(15) . . . . ?
C2 N1 C1 S2 -10.8(2) . . . . ?
C4 N1 C1 S1 -4.7(2) . . . . ?
C2 N1 C1 S1 169.02(14) . . . . ?
Zn S2 C1 N1 167.26(16) . . . . ?
Zn S2 C1 S1 -12.55(9) . . . . ?
Zn S1 C1 N1 -165.30(14) . . . . ?
Zn S1 C1 S2 14.52(10) . . . . ?
C1 N1 C2 C3 102.8(2) . . . . ?
C4 N1 C2 C3 -83.2(2) . . . . ?
N1 C2 C3 O1 -58.9(2) . . . . ?
C8 N2 C5 S4 1.6(3) . . . . ?
C6 N2 C5 S4 179.87(14) . . . . ?
C8 N2 C5 S3 -179.97(15) . . . . ?
C6 N2 C5 S3 -1.7(3) . . . . ?
Zn S4 C5 N2 176.79(16) . . . . ?
Zn S4 C5 S3 -1.66(9) . . . . ?
Zn S3 C5 N2 -176.68(15) . . . . ?
Zn S3 C5 S4 1.77(10) . . . . ?
C5 N2 C6 C7 -103.9(2) . . . . ?
C8 N2 C6 C7 74.4(2) . . . . ?
N2 C6 C7 O2 55.4(2) . . . . ?
C13 N3 C9 C10 -2.0(3) . . . . ?
Zn N3 C9 C10 178.55(14) . . . . ?
N3 C9 C10 O3 -176.43(17) . . . . ?
N3 C9 C10 C11 2.1(3) . . . . ?
O3 C10 C11 C12 177.9(2) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C9 N3 C13 C12 0.2(3) . . . . ?
Zn N3 C13 C12 179.67(16) . . . . ?
C11 C12 C13 N3 1.3(3) . . . . ?
 
_refine_diff_density_max    0.430
_refine_diff_density_min   -0.596
_refine_diff_density_rms    0.076



_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n

loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
"{687b4131-b9e9-4956-8180-319fb9f745f5}" "_geom_extra_table_headA"
"{687b4131-b9e9-4956-8180-319fb9f745f5}" "_geom_hbond_atom_site_label_D"
"{da9ee6d5-6e6c-4a13-80c9-1434e53164c0}" "_geom_hbond_atom_site_label_D"
"{687b4131-b9e9-4956-8180-319fb9f745f5}" "_geom_extra_table_headB"
"{687b4131-b9e9-4956-8180-319fb9f745f5}" "_geom_extra_table_headC"
"{92d4c804-1fc9-4242-84e8-84b0d42cfb38}" "_publcif_info_datablock.publ_exptl"

loop_
_publcif_info_cif.paper_type
 EE

loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
'{687b4131-b9e9-4956-8180-319fb9f745f5}' y y y
'{da9ee6d5-6e6c-4a13-80c9-1434e53164c0}' y y y
'{92d4c804-1fc9-4242-84e8-84b0d42cfb38}' ? ? ?

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



