#------------------------------------------------------------------------------
#$Date: 2017-02-04 05:55:42 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191418 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/06/2020690.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_2020690
loop_
_publ_author_name
'Ardan, Bohdan'
'Kinzhybalo, Vasyl'
'Slyvka, Yurii'
'Shyyka, Olga'
'Luk`yanov, Mykhaylo'
'Lis, Tadeusz'
'Mys`kiv, Marian'
_publ_section_title
;
 Ligand-forced dimerization of copper(I)--olefin complexes bearing a
 1,3,4-thiadiazole core
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              36
_journal_page_last               46
_journal_paper_doi               10.1107/S2053229616018751
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          '[Cu2 (N O3)2 (C6 H9 N3 S)2]'
_chemical_formula_moiety         'C12 H18 Cu2 N8 O6 S2'
_chemical_formula_sum            'C12 H18 Cu2 N8 O6 S2'
_chemical_formula_weight         561.54
_chemical_name_systematic
Bis[μ-5-methyl-N-(prop-2-en-1-yl)-1,3,4-thiadiazol-2-amine]bis[nitratocopper(I)]
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                105.42(3)
_cell_angle_beta                 98.15(3)
_cell_angle_gamma                112.43(3)
_cell_formula_units_Z            1
_cell_length_a                   7.235(3)
_cell_length_b                   7.548(3)
_cell_length_c                   10.297(4)
_cell_measurement_reflns_used    3143
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.4994
_cell_measurement_theta_min      3.1006
_cell_volume                     482.0(4)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.1956
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.807
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Xcalibur Onyx'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8459
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         38.502
_diffrn_reflns_theta_min         3.101
_exptl_absorpt_coefficient_mu    2.474
_exptl_absorpt_correction_T_max  0.768
_exptl_absorpt_correction_T_min  0.542
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis PRO (Rigaku OD, 2015), based on expressions
derived by Clark & Reid (1995)]
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.431
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.881
_refine_diff_density_min         -1.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         8459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0610P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0956
_reflns_number_gt                6900
_reflns_number_total             8459
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fn3225sup1.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 2020689--2020694.cif.'
_cod_database_code               2020690
_cod_database_fobs_code          2020690
_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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Cu Cu1 0.57775(3) 0.57834(3) 0.68133(2) 0.01261(7) Uani d 1
S S1 0.18975(7) -0.09982(7) 0.47322(5) 0.01402(10) Uani d 1
O O1 0.2950(3) 0.6861(3) 0.6800(2) 0.0308(4) Uani d 1
O O2 0.2567(3) 0.8531(3) 0.8713(2) 0.0348(4) Uani d 1
O O3 0.1088(3) 0.5240(3) 0.7949(2) 0.0312(4) Uani d 1
N N1 0.2182(3) 0.6865(3) 0.7824(2) 0.0193(4) Uani d 1
N N2 0.4533(3) 0.1392(3) 0.72781(19) 0.0161(3) Uani d 1
H H2 0.411(4) 0.037(4) 0.746(3) 0.019 Uiso d 1
N N3 0.4220(2) 0.2864(2) 0.55566(17) 0.0122(3) Uani d 1
N N4 0.3167(2) 0.2273(2) 0.41582(17) 0.0123(3) Uani d 1
C C2 0.3733(3) 0.1302(3) 0.6002(2) 0.0127(3) Uani d 1
C C5 0.1895(3) 0.0338(3) 0.3607(2) 0.0134(3) Uani d 1
C C6 0.0538(3) -0.0697(3) 0.2141(2) 0.0177(4) Uani d 1
H H6A 0.1375 -0.0900 0.1497 0.027 Uiso calc 1
H H6B -0.0103 0.0155 0.1914 0.027 Uiso calc 1
H H6C -0.0551 -0.2026 0.2048 0.027 Uiso calc 1
C C7 0.6182(3) 0.3254(3) 0.8338(2) 0.0161(4) Uani d 1
H H7A 0.7481 0.3591 0.8043 0.019 Uiso calc 1
H H7B 0.6431 0.3010 0.9231 0.019 Uiso calc 1
C C8 0.5662(3) 0.5039(3) 0.8573(2) 0.0150(4) Uani d 1
H H8 0.4246 0.4786 0.8447 0.018 Uiso calc 1
C C9 0.7131(3) 0.7002(3) 0.8957(2) 0.0177(4) Uani d 1
H H9A 0.8556 0.7289 0.9089 0.021 Uiso calc 1
H H9B 0.6733 0.8086 0.9095 0.021 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 13 0.0830
2 3 -14 0.1199
-2 -9 8 0.0806
-6 -2 13 0.1466
-1 10 0 0.0583
-1 0 -13 0.1039
7 2 -12 0.1990
2 -8 -4 0.0768
-1 5 -14 0.1192
1 -5 14 0.0867
4 7 -6 0.1363
-1 10 -6 0.0769
9 -8 0 0.1648
0 -9 1 0.0664
-8 1 -5 0.1786
-10 1 3 0.1970
8 -1 4 0.1518
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N3 Cu1 C8 . . 92.55(8)
N3 Cu1 C9 . . 129.43(8)
N4 Cu1 N3 2_666 . 114.48(7)
N4 Cu1 C8 2_666 . 152.33(8)
N4 Cu1 C9 2_666 . 113.75(9)
C8 Cu1 C9 . . 38.62(8)
C5 S1 C2 . . 87.58(10)
O2 N1 O1 . . 118.97(19)
O3 N1 O1 . . 120.4(2)
O3 N1 O2 . . 120.6(2)
C2 N2 H2 . . 118.5(18)
C2 N2 C7 . . 122.94(18)
C7 N2 H2 . . 118.6(18)
N4 N3 Cu1 . . 122.79(13)
C2 N3 Cu1 . . 123.96(14)
C2 N3 N4 . . 112.03(15)
N3 N4 Cu1 . 2_666 117.17(12)
C5 N4 Cu1 . 2_666 127.96(15)
C5 N4 N3 . . 113.16(17)
N2 C2 S1 . . 121.22(15)
N3 C2 S1 . . 113.25(15)
N3 C2 N2 . . 125.52(18)
N4 C5 S1 . . 113.95(16)
N4 C5 C6 . . 124.60(19)
C6 C5 S1 . . 121.45(14)
C5 C6 H6A . . 109.5
C5 C6 H6B . . 109.5
C5 C6 H6C . . 109.5
H6A C6 H6B . . 109.5
H6A C6 H6C . . 109.5
H6B C6 H6C . . 109.5
N2 C7 H7A . . 109.1
N2 C7 H7B . . 109.1
N2 C7 C8 . . 112.34(17)
H7A C7 H7B . . 107.9
C8 C7 H7A . . 109.1
C8 C7 H7B . . 109.1
Cu1 C8 H8 . . 92.0
C7 C8 Cu1 . . 105.91(14)
C7 C8 H8 . . 118.6
C9 C8 Cu1 . . 72.10(13)
C9 C8 C7 . . 122.76(19)
C9 C8 H8 . . 118.6
Cu1 C9 H9A . . 106.6
Cu1 C9 H9B . . 93.9
C8 C9 Cu1 . . 69.28(13)
C8 C9 H9A . . 120.0
C8 C9 H9B . . 120.0
H9A C9 H9B . . 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 N3 . 1.9940(19)
Cu1 N4 2_666 1.9690(18)
Cu1 C8 . 2.038(2)
Cu1 C9 . 2.073(2)
S1 C2 . 1.741(2)
S1 C5 . 1.727(2)
O1 N1 . 1.259(3)
O2 N1 . 1.243(2)
O3 N1 . 1.233(2)
N2 H2 . 0.80(3)
N2 C2 . 1.331(3)
N2 C7 . 1.458(3)
N3 N4 . 1.393(2)
N3 C2 . 1.319(3)
N4 Cu1 2_666 1.9690(18)
N4 C5 . 1.299(2)
C5 C6 . 1.491(3)
C6 H6A . 0.9800
C6 H6B . 0.9800
C6 H6C . 0.9800
C7 H7A . 0.9900
C7 H7B . 0.9900
C7 C8 . 1.502(3)
C8 H8 . 0.9500
C8 C9 . 1.360(3)
C9 H9A . 0.9500
C9 H9B . 0.9500
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
_geom_hbond_publ_flag
N2 H2 O1 1_545 0.80(3) 2.32(3) 3.034(3) 150(2) yes
N2 H2 O2 1_545 0.80(3) 2.24(3) 2.970(3) 153(2) yes
N2 H2 N1 1_545 0.80(3) 2.63(3) 3.426(3) 172(2) no
C6 H6B O2 2_566 0.98 2.44 3.391(3) 164.3 no
C6 H6C O3 2_556 0.98 2.31 3.142(3) 142.6 no
C7 H7A O3 1_655 0.99 2.45 3.415(3) 163.6 no
C8 H8 O3 . 0.95 2.44 3.350(3) 159.9 no
C8 H8 N1 . 0.95 2.68 3.391(3) 132.5 no
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
Cu1 N3 N4 Cu1 . 2_666 27.76(18)
Cu1 N3 N4 C5 . . -165.92(13)
Cu1 N3 C2 S1 . . 166.41(9)
Cu1 N3 C2 N2 . . -14.2(3)
Cu1 N4 C5 S1 2_666 . 162.81(10)
Cu1 N4 C5 C6 2_666 . -16.9(3)
N2 C7 C8 Cu1 . . -70.33(19)
N2 C7 C8 C9 . . -149.0(2)
N3 N4 C5 S1 . . -1.7(2)
N3 N4 C5 C6 . . 178.57(17)
N4 N3 C2 S1 . . -1.3(2)
N4 N3 C2 N2 . . 178.15(18)
C2 S1 C5 N4 . . 0.82(15)
C2 S1 C5 C6 . . -179.44(17)
C2 N2 C7 C8 . . 52.9(3)
C2 N3 N4 Cu1 . 2_666 -164.39(13)
C2 N3 N4 C5 . . 1.9(2)
C5 S1 C2 N2 . . -179.15(17)
C5 S1 C2 N3 . . 0.30(15)
C7 N2 C2 S1 . . 175.35(14)
C7 N2 C2 N3 . . -4.0(3)
C7 C8 C9 Cu1 . . 97.74(19)
