#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:59:47 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228987 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/06/7230686.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_7230686
loop_
_publ_author_name
'Hassanpoor, Azam'
'Mirzaei, Masoud'
'Eshtiagh-Hosseini, Hossein'
'Majcher, Anna'
_publ_section_title
;
 Constructing two 1D coordination polymers and one mononuclear complex by
 pyrazine- and pyridinedicarboxylic acids under mild and sonochemical
 conditions: magnetic and CSD studies
;
_journal_issue                   26
_journal_name_full               CrystEngComm
_journal_page_first              3711
_journal_paper_doi               10.1039/C8CE00573G
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C14 H6 Cu N2 O8, 2(C3 H5 N2 S)'
_chemical_formula_sum            'C20 H16 Cu N6 O8 S2'
_chemical_formula_weight         596.08
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2918 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2017-05-22 deposited with the CCDC.
2018-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                70.675(4)
_cell_angle_beta                 85.308(4)
_cell_angle_gamma                81.872(4)
_cell_formula_units_Z            1
_cell_length_a                   6.4091(3)
_cell_length_b                   8.0567(4)
_cell_length_c                   11.3265(5)
_cell_measurement_reflns_used    7687
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      76.1590
_cell_measurement_theta_min      4.1190
_cell_volume                     545.98(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1386464000
_diffrn_orient_matrix_UB_12      -0.1799826000
_diffrn_orient_matrix_UB_13      0.0452825000
_diffrn_orient_matrix_UB_21      -0.0924003000
_diffrn_orient_matrix_UB_22      -0.0589246000
_diffrn_orient_matrix_UB_23      -0.0989801000
_diffrn_orient_matrix_UB_31      0.1768593000
_diffrn_orient_matrix_UB_32      0.0762173000
_diffrn_orient_matrix_UB_33      -0.0946383000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10888
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.045
_diffrn_reflns_theta_min         4.139
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.789
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_description       rod
_exptl_crystal_F_000             303
_exptl_crystal_size_max          0.3004
_exptl_crystal_size_mid          0.1317
_exptl_crystal_size_min          0.0509
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0317
_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)+(0.0481P)²+0.5971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0839
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2151
_reflns_number_total             2253
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00573g2.cif
_cod_data_source_block           aht082
_cod_depositor_comments
'Adding full bibliography for 7230684--7230686.cif.'
_cod_database_code               7230686
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C10 H10 N4 O4 S1 Cu1'
_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.
;
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C3(H3), C10(H10), C4(H4)
;
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Cu1 Cu 0.5000 0.5000 0.0000 0.01332(13) Uani 1 2 d S T P
S1 S 0.21785(7) 0.90826(6) 0.39182(4) 0.01549(13) Uani 1 1 d . . .
O3 O 1.3460(2) 0.46378(18) 0.22638(12) 0.0169(3) Uani 1 1 d . . .
O4 O 1.0973(2) 0.38908(18) 0.37970(12) 0.0170(3) Uani 1 1 d . . .
O1 O 0.6934(2) 0.29103(16) 0.08351(12) 0.0139(3) Uani 1 1 d . . .
O2 O 0.9842(2) 0.20835(17) 0.19554(12) 0.0160(3) Uani 1 1 d . . .
N1 N 0.6973(2) 0.6252(2) 0.05168(14) 0.0125(3) Uani 1 1 d . . .
N3 N 0.3452(3) 0.6221(2) 0.58805(16) 0.0180(3) Uani 1 1 d . . .
N2 N 0.5931(2) 0.7985(2) 0.46146(15) 0.0141(3) Uani 1 1 d . . .
C9 C 0.6071(3) 0.9498(2) 0.35782(17) 0.0159(4) Uani 1 1 d . . .
H9 H 0.7364 0.9954 0.3256 0.019 Uiso 1 1 calc R . .
C5 C 0.6793(3) 0.7991(2) 0.03181(17) 0.0135(3) Uani 1 1 d . . .
H5 H 0.5699 0.8743 -0.0188 0.016 Uiso 1 1 calc R . .
C3 C 0.9740(3) 0.7609(2) 0.15705(17) 0.0149(4) Uani 1 1 d . . .
H3 H 1.0712 0.8085 0.1922 0.018 Uiso 1 1 calc R . .
C10 C 0.4208(3) 1.0247(3) 0.30806(18) 0.0172(4) Uani 1 1 d . . .
H10 H 0.4019 1.1277 0.2365 0.021 Uiso 1 1 calc R . .
C4 C 0.8164(3) 0.8732(2) 0.08334(18) 0.0152(4) Uani 1 1 d . . .
H4 H 0.8023 0.9973 0.0684 0.018 Uiso 1 1 calc R . .
C8 C 0.3972(3) 0.7577(2) 0.49233(17) 0.0144(4) Uani 1 1 d . . .
C1 C 0.8492(3) 0.5146(2) 0.12450(16) 0.0118(3) Uani 1 1 d . . .
C2 C 0.9912(3) 0.5785(2) 0.18003(16) 0.0123(3) Uani 1 1 d . . .
C6 C 0.8463(3) 0.3211(2) 0.13756(16) 0.0123(3) Uani 1 1 d . . .
C7 C 1.1595(3) 0.4634(2) 0.26837(17) 0.0135(3) Uani 1 1 d . . .
H2 H 0.695(4) 0.739(3) 0.509(2) 0.016 Uiso 1 1 d R . .
H3A H 0.431(4) 0.577(3) 0.643(2) 0.016 Uiso 1 1 d R . .
H3B H 0.213(4) 0.608(3) 0.602(2) 0.016 Uiso 1 1 d R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 2 -5 0.0630 -0.0069 1.9992 -4.9960 -0.5870 0.3773 0.6240
0 -2 5 0.0689 0.0069 -1.9992 4.9960 0.5870 -0.3773 -0.6240
4 0 1 0.1157 4.0006 -0.0053 0.9922 0.6005 -0.4676 0.6132
-3 -1 3 0.1399 -2.9956 -0.9955 3.0038 -0.1001 0.0381 -0.8899
0 5 5 0.0427 0.0026 4.9999 5.0107 -0.6726 -0.7908 -0.0927
0 -5 -5 0.0082 -0.0026 -4.9999 -5.0107 0.6726 0.7908 0.0927
3 1 -4 0.1065 2.9944 0.9954 -4.0039 0.0547 0.0610 0.9844
0 -2 -7 0.0368 -0.0067 -2.0005 -7.0045 0.0420 0.8118 0.5092
0 2 7 0.0514 0.0067 2.0005 7.0045 -0.0420 -0.8118 -0.5092
-4 -1 1 0.1534 -3.9977 -0.9944 1.0057 -0.3298 0.3284 -0.8780
0 5 2 0.0473 -0.0008 4.9995 2.0106 -0.8089 -0.4935 0.1906
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
O1 Cu1 O1 180.0 . 2_665
O1 Cu1 N1 96.70(6) 2_665 .
O1 Cu1 N1 83.31(6) . .
O1 Cu1 N1 96.69(6) . 2_665
O1 Cu1 N1 83.31(6) 2_665 2_665
N1 Cu1 N1 180.0 2_665 .
C8 S1 C10 90.51(9) . .
C6 O1 Cu1 115.13(11) . .
C5 N1 Cu1 126.08(12) . .
C5 N1 C1 120.64(15) . .
C1 N1 Cu1 112.91(12) . .
C8 N3 H3A 117.3(17) . .
C8 N3 H3B 118.0(16) . .
H3A N3 H3B 122(2) . .
C9 N2 H2 126.1(16) . .
C8 N2 C9 113.93(16) . .
C8 N2 H2 119.7(16) . .
N2 C9 H9 123.3 . .
C10 C9 N2 113.43(17) . .
C10 C9 H9 123.3 . .
N1 C5 H5 119.2 . .
N1 C5 C4 121.62(16) . .
C4 C5 H5 119.2 . .
C4 C3 H3 119.8 . .
C4 C3 C2 120.47(16) . .
C2 C3 H3 119.8 . .
S1 C10 H10 124.5 . .
C9 C10 S1 110.93(15) . .
C9 C10 H10 124.5 . .
C5 C4 H4 120.9 . .
C3 C4 C5 118.14(17) . .
C3 C4 H4 120.9 . .
N3 C8 S1 124.08(15) . .
N3 C8 N2 124.72(17) . .
N2 C8 S1 111.19(14) . .
N1 C1 C2 121.09(16) . .
N1 C1 C6 113.67(15) . .
C2 C1 C6 125.25(16) . .
C3 C2 C7 117.24(16) . .
C1 C2 C3 118.02(16) . .
C1 C2 C7 124.69(16) . .
O1 C6 C1 114.63(15) . .
O2 C6 O1 125.46(17) . .
O2 C6 C1 119.91(16) . .
O3 C7 O4 126.79(17) . .
O3 C7 C2 116.86(16) . .
O4 C7 C2 116.07(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9529(12) .
Cu1 O1 1.9529(12) 2_665
Cu1 N1 1.9576(15) .
Cu1 N1 1.9576(15) 2_665
S1 C10 1.740(2) .
S1 C8 1.7305(18) .
O3 C7 1.250(2) .
O4 C7 1.262(2) .
O1 C6 1.287(2) .
O2 C6 1.229(2) .
N1 C5 1.333(2) .
N1 C1 1.350(2) .
N3 C8 1.320(3) .
N3 H3A 0.82(3) .
N3 H3B 0.87(3) .
N2 C9 1.392(2) .
N2 C8 1.332(3) .
N2 H2 0.86(3) .
C9 H9 0.9500 .
C9 C10 1.338(3) .
C5 H5 0.9500 .
C5 C4 1.390(3) .
C3 H3 0.9500 .
C3 C4 1.384(3) .
C3 C2 1.395(2) .
C10 H10 0.9500 .
C4 H4 0.9500 .
C1 C2 1.390(2) .
C1 C6 1.519(2) .
C2 C7 1.518(2) .
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
Cu1 O1 C6 O2 179.66(14)
Cu1 O1 C6 C1 -0.86(19)
Cu1 N1 C5 C4 173.31(13)
Cu1 N1 C1 C2 -173.75(13)
Cu1 N1 C1 C6 6.35(18)
N1 C5 C4 C3 -0.2(3)
N1 C1 C2 C3 -0.8(3)
N1 C1 C2 C7 176.73(16)
N1 C1 C6 O1 -3.7(2)
N1 C1 C6 O2 175.78(16)
N2 C9 C10 S1 0.8(2)
C9 N2 C8 S1 0.1(2)
C9 N2 C8 N3 -178.92(18)
C5 N1 C1 C2 -0.4(3)
C5 N1 C1 C6 179.71(15)
C3 C2 C7 O3 -75.2(2)
C3 C2 C7 O4 99.1(2)
C10 S1 C8 N3 179.33(17)
C10 S1 C8 N2 0.27(14)
C4 C3 C2 C1 1.5(3)
C4 C3 C2 C7 -176.23(16)
C8 S1 C10 C9 -0.62(15)
C8 N2 C9 C10 -0.6(2)
C1 N1 C5 C4 0.9(3)
C1 C2 C7 O3 107.2(2)
C1 C2 C7 O4 -78.4(2)
C2 C3 C4 C5 -1.0(3)
C2 C1 C6 O1 176.38(16)
C2 C1 C6 O2 -4.1(3)
C6 C1 C2 C3 179.11(16)
C6 C1 C2 C7 -3.4(3)
