#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/36/2013606.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_2013606
loop_
_publ_author_name
'Marek, Jaromír'
'Kopel, Pavel'
'Trávníček, Zdeněk'
_publ_section_title
;[N,N'-Bis(3-aminopropyl)ethylenediamine-κ⁴N,N',N'',N'''](trithiocyanurato-κ²N,S)zinc(II)
 ethanol solvate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m558
_journal_page_last               m560
_journal_paper_doi               10.1107/S0108270103025836
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          '[Zn (C8 H22 N4)2 (C3 H N3 S3)] , C2 H6 O'
_chemical_formula_moiety         'C11 H23 N7 S3 Zn , C2 H6 O'
_chemical_formula_sum            'C13 H29 N7 O S3 Zn'
_chemical_formula_weight         460.98
_chemical_name_systematic
;
[N,N'-bis(3-aminopropyl)ethylenediamine-κ⁴N,N',N'',N'''][1,3,5-triazine-
2,4,6(1H,3H,5H)-trithioneκ²N,S]zinc(II) ethanol solvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                93.592(10)
_cell_angle_beta                 102.316(11)
_cell_angle_gamma                112.167(14)
_cell_formula_units_Z            2
_cell_length_a                   9.0791(14)
_cell_length_b                   11.0455(15)
_cell_length_c                   11.3580(11)
_cell_measurement_reflns_used    2410
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      2.160
_cell_measurement_theta_min      26.5
_cell_volume                     1017.6(3)
_computing_cell_refinement       'CrysAlisRED (Oxford Diffraction, 2002)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2002)'
_computing_data_reduction        CrysAlisRED
_computing_molecular_graphics    'ORTEPIII (Johnson & Burnett, 1996)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 16.3
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device_type  'Kuma KM4 with CCD area detector'
_diffrn_measurement_method       'rotation method, ω scan'
_diffrn_radiation_monochromator  'Enhance (Oxford Diffraction)'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_sigmaI/netI    0.017
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6681
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         2.51
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.532
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         1.08
_refine_diff_density_min         -0.66
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.037
_refine_ls_R_factor_gt           0.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.055P)²+1.75P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.097
_refine_ls_wR_factor_ref         0.097
_reflns_number_gt                4279
_reflns_number_total             4458
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd1284.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (9 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (9
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (26 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2013606
_cod_database_fobs_code          2013606
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Zn 0.44691(3) 0.21844(2) 0.69155(2) 0.01459(9) Uani d . 1 . . Zn
S1 0.31572(7) 0.06521(5) 0.48436(5) 0.01884(13) Uani d . 1 . . S
S2 0.85613(7) 0.50263(6) 0.62917(5) 0.02149(13) Uani d . 1 . . S
S3 0.73699(7) 0.20877(6) 0.20745(5) 0.02066(13) Uani d . 1 . . S
N1 0.2868(2) 0.11116(19) 0.79283(18) 0.0182(4) Uani d . 1 . . N
H1A 0.2982 0.0324 0.7997 0.022 Uiso calc R 1 . . H
H1B 0.3198 0.1582 0.8703 0.022 Uiso calc R 1 . . H
N2 0.3020(2) 0.3349(2) 0.63181(18) 0.0191(4) Uani d . 1 . . N
H2 0.3130 0.3494 0.5538 0.023 Uiso calc R 1 . . H
N3 0.5945(2) 0.39975(17) 0.81964(16) 0.0143(3) Uani d . 1 . . N
H3 0.6691 0.4543 0.7811 0.017 Uiso calc R 1 . . H
N4 0.6261(2) 0.14065(18) 0.75268(18) 0.0175(4) Uani d . 1 . . N
H4A 0.5749 0.0499 0.7332 0.021 Uiso calc R 1 . . H
H4B 0.7032 0.1686 0.7083 0.021 Uiso calc R 1 . . H
N5 0.5826(2) 0.28271(18) 0.54067(17) 0.0154(4) Uani d . 1 . . N
N6 0.5283(2) 0.14832(18) 0.34803(17) 0.0175(4) Uani d . 1 . . N
N7 0.7781(2) 0.33083(18) 0.42804(17) 0.0151(3) Uani d . 1 . . N
H7 0.8787 0.3775 0.4229 0.018 Uiso calc R 1 . . H
C1 0.1092(3) 0.0811(2) 0.7426(2) 0.0252(5) Uani d . 1 . . C
H1C 0.0463 0.0314 0.7978 0.030 Uiso calc R 1 . . H
H1D 0.0697 0.0236 0.6622 0.030 Uiso calc R 1 . . H
C2 0.0754(3) 0.2048(3) 0.7274(2) 0.0253(5) Uani d . 1 . . C
H2A -0.0434 0.1812 0.7189 0.030 Uiso calc R 1 . . H
H2B 0.1365 0.2702 0.8028 0.030 Uiso calc R 1 . . H
C3 0.1217(3) 0.2701(3) 0.6193(2) 0.0258(5) Uani d . 1 . . C
H3A 0.0709 0.2022 0.5450 0.031 Uiso calc R 1 . . H
H3B 0.0746 0.3373 0.6075 0.031 Uiso calc R 1 . . H
C4 0.3832(3) 0.4676(2) 0.7085(2) 0.0225(5) Uani d . 1 . . C
H4C 0.2985 0.5007 0.7185 0.027 Uiso calc R 1 . . H
H4D 0.4576 0.5300 0.6669 0.027 Uiso calc R 1 . . H
C5 0.4817(3) 0.4636(2) 0.8340(2) 0.0187(4) Uani d . 1 . . C
H5A 0.5455 0.5548 0.8790 0.022 Uiso calc R 1 . . H
H5B 0.4059 0.4134 0.8815 0.022 Uiso calc R 1 . . H
C6 0.6916(3) 0.3923(2) 0.9390(2) 0.0176(4) Uani d . 1 . . C
H6A 0.6155 0.3446 0.9873 0.021 Uiso calc R 1 . . H
H6B 0.7587 0.4831 0.9839 0.021 Uiso calc R 1 . . H
C7 0.8049(3) 0.3221(2) 0.9270(2) 0.0193(4) Uani d . 1 . . C
H7A 0.8832 0.3374 1.0073 0.023 Uiso calc R 1 . . H
H7B 0.8697 0.3622 0.8690 0.023 Uiso calc R 1 . . H
C8 0.7150(3) 0.1731(2) 0.8832(2) 0.0203(4) Uani d . 1 . . C
H8A 0.7957 0.1319 0.8968 0.024 Uiso calc R 1 . . H
H8B 0.6356 0.1348 0.9322 0.024 Uiso calc R 1 . . H
C9 0.4900(3) 0.1734(2) 0.4534(2) 0.0161(4) Uani d . 1 . . C
C10 0.6752(3) 0.2278(2) 0.33580(19) 0.0151(4) Uani d . 1 . . C
C11 0.7298(3) 0.3637(2) 0.5281(2) 0.0153(4) Uani d . 1 . . C
O1 0.3590(2) 0.1850(2) 1.06990(17) 0.0285(4) Uani d D 1 . . O
C13 0.1115(4) 0.2027(4) 1.0840(4) 0.0501(9) Uani d . 1 . . C
H13A 0.1484 0.2842 1.0485 0.075 Uiso calc R 1 . . H
H13B 0.0469 0.2107 1.1408 0.075 Uiso calc R 1 . . H
H13C 0.0432 0.1276 1.0188 0.075 Uiso calc R 1 . . H
C12 0.2555(4) 0.1812(3) 1.1500(3) 0.0422(8) Uani d . 1 . . C
H12A 0.3175 0.2509 1.2223 0.051 Uiso calc R 1 . . H
H12B 0.2192 0.0942 1.1783 0.051 Uiso calc R 1 . . H
H1O 0.451(4) 0.180(4) 1.121(3) 0.060(12) Uiso d D 1 . . H
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_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N1 Zn N4 94.66(8) y
N1 Zn N3 100.92(7) y
N4 Zn N3 90.46(7) y
N1 Zn N2 93.77(8) y
N4 Zn N2 169.06(8) y
N3 Zn N2 81.09(7) y
N1 Zn N5 163.89(7) y
N4 Zn N5 84.67(7) y
N3 Zn N5 95.18(7) y
N2 Zn N5 89.15(7) y
N1 Zn S1 99.81(6) y
N4 Zn S1 95.51(5) y
N3 Zn S1 157.87(5) y
N2 Zn S1 89.91(6) y
N5 Zn S1 64.32(5) y
C9 S1 Zn 80.99(8) y
C1 N1 Zn 116.11(15) y
C1 N1 H1A 108.3 n
Zn N1 H1A 108.3 n
C1 N1 H1B 108.3 n
Zn N1 H1B 108.3 n
H1A N1 H1B 107.4 n
C4 N2 C3 113.98(19) n
C4 N2 Zn 108.50(14) n
C3 N2 Zn 116.68(15) n
C4 N2 H2 105.6 n
C3 N2 H2 105.6 n
Zn N2 H2 105.6 n
C5 N3 C6 111.55(17) n
C5 N3 Zn 105.99(13) n
C6 N3 Zn 118.77(13) n
C5 N3 H3 106.6 n
C6 N3 H3 106.6 n
Zn N3 H3 106.6 n
C8 N4 Zn 118.67(14) n
C8 N4 H4A 107.6 n
Zn N4 H4A 107.6 n
C8 N4 H4B 107.6 n
Zn N4 H4B 107.6 n
H4A N4 H4B 107.1 n
C11 N5 C9 118.13(19) n
C11 N5 Zn 140.07(15) n
C9 N5 Zn 98.37(13) n
C10 N6 C9 117.14(19) n
C11 N7 C10 122.54(18) n
C11 N7 H7 118.7 n
C10 N7 H7 118.7 n
N1 C1 C2 112.9(2) n
N1 C1 H1C 109.0 n
C2 C1 H1C 109.0 n
N1 C1 H1D 109.0 n
C2 C1 H1D 109.0 n
H1C C1 H1D 107.8 n
C3 C2 C1 115.1(2) n
C3 C2 H2A 108.5 n
C1 C2 H2A 108.5 n
C3 C2 H2B 108.5 n
C1 C2 H2B 108.5 n
H2A C2 H2B 107.5 n
N2 C3 C2 114.4(2) n
N2 C3 H3A 108.6 n
C2 C3 H3A 108.6 n
N2 C3 H3B 108.6 n
C2 C3 H3B 108.6 n
H3A C3 H3B 107.6 n
N2 C4 C5 111.68(18) n
N2 C4 H4C 109.3 n
C5 C4 H4C 109.3 n
N2 C4 H4D 109.3 n
C5 C4 H4D 109.3 n
H4C C4 H4D 107.9 n
N3 C5 C4 109.54(18) n
N3 C5 H5A 109.8 n
C4 C5 H5A 109.8 n
N3 C5 H5B 109.8 n
C4 C5 H5B 109.8 n
H5A C5 H5B 108.2 n
N3 C6 C7 112.71(18) n
N3 C6 H6A 109.1 n
C7 C6 H6A 109.1 n
N3 C6 H6B 109.1 n
C7 C6 H6B 109.1 n
H6A C6 H6B 107.8 n
C6 C7 C8 114.09(19) n
C6 C7 H7A 108.7 n
C8 C7 H7A 108.7 n
C6 C7 H7B 108.7 n
C8 C7 H7B 108.7 n
H7A C7 H7B 107.6 n
N4 C8 C7 112.60(19) n
N4 C8 H8A 109.1 n
C7 C8 H8A 109.1 n
N4 C8 H8B 109.1 n
C7 C8 H8B 109.1 n
H8A C8 H8B 107.8 n
N6 C9 N5 124.5(2) y
N6 C9 S1 120.12(16) y
N5 C9 S1 115.42(16) y
N6 C10 N7 119.33(19) y
N6 C10 S3 121.87(17) y
N7 C10 S3 118.77(17) y
N5 C11 N7 117.62(19) y
N5 C11 S2 122.90(17) y
N7 C11 S2 119.48(16) y
C12 O1 H1O 103(3) n
C12 C13 H13A 109.5 n
C12 C13 H13B 109.5 n
H13A C13 H13B 109.5 n
C12 C13 H13C 109.5 n
H13A C13 H13C 109.5 n
H13B C13 H13C 109.5 n
O1 C12 C13 109.1(3) n
O1 C12 H12A 109.9 n
C13 C12 H12A 109.9 n
O1 C12 H12B 109.9 n
C13 C12 H12B 109.9 n
H12A C12 H12B 108.3 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zn N1 . 2.104(2) y
Zn N4 . 2.1249(19) y
Zn N3 . 2.1682(19) y
Zn N2 . 2.2031(19) y
Zn N5 . 2.3132(18) y
Zn S1 . 2.5700(7) y
S1 C9 . 1.708(2) y
S2 C11 . 1.697(2) y
S3 C10 . 1.698(2) y
N1 C1 . 1.488(3) n
N1 H1A . 0.9200 n
N1 H1B . 0.9200 n
N2 C4 . 1.484(3) n
N2 C3 . 1.488(3) n
N2 H2 . 0.9300 n
N3 C5 . 1.475(3) n
N3 C6 . 1.476(3) n
N3 H3 . 0.9300 n
N4 C8 . 1.477(3) n
N4 H4A . 0.9200 n
N4 H4B . 0.9200 n
N5 C11 . 1.343(3) n
N5 C9 . 1.370(3) n
N6 C10 . 1.334(3) n
N6 C9 . 1.355(3) n
N7 C11 . 1.377(3) n
N7 C10 . 1.377(3) n
N7 H7 . 0.8800 n
C1 C2 . 1.521(4) n
C1 H1C . 0.9900 n
C1 H1D . 0.9900 n
C2 C3 . 1.520(4) n
C2 H2A . 0.9900 n
C2 H2B . 0.9900 n
C3 H3A . 0.9900 n
C3 H3B . 0.9900 n
C4 C5 . 1.525(3) n
C4 H4C . 0.9900 n
C4 H4D . 0.9900 n
C5 H5A . 0.9900 n
C5 H5B . 0.9900 n
C6 C7 . 1.526(3) n
C6 H6A . 0.9900 n
C6 H6B . 0.9900 n
C7 C8 . 1.527(3) n
C7 H7A . 0.9900 n
C7 H7B . 0.9900 n
C8 H8A . 0.9900 n
C8 H8B . 0.9900 n
O1 C12 . 1.432(4) n
O1 H1O . 0.93(4) n
C13 C12 . 1.472(5) n
C13 H13A . 0.9800 n
C13 H13B . 0.9800 n
C13 H13C . 0.9800 n
C12 H12A . 0.9900 n
C12 H12B . 0.9900 n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1B O1 . 0.92 2.20 3.065(3) 156
N1 H1A S3 2_656 0.92 2.55 3.458(2) 167
N3 H3 S2 . 0.93 2.61 3.475(2) 154
N4 H4A N6 2_656 0.92 2.09 2.991(3) 167
N7 H7 S2 2_766 0.88 2.49 3.361(2) 170
O1 H1O S3 1_556 0.93(4) 2.46(4) 3.357(2) 161(3)
O1 H1O N6 1_556 0.93(4) 2.61(3) 3.326(3) 135(3)
