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#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/45/7014587.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_7014587
loop_
_publ_author_name
'Delgado, Salomé'
'Gallego, Almudena'
'Castillo, Oscar'
'Zamora, Félix'
_publ_section_title
;
 Unexpected multiple bond cleavage and rearrangement of organosulfide
 ligands in the presence of Cu(II) assisted by solvothermal and
 solvothermal-microwave conditions.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              847
_journal_page_last               852
_journal_paper_doi               10.1039/c0dt00973c
_journal_volume                  40
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C8 H6 N4 O S'
_chemical_formula_structural     'C8 H6 N4 O S'
_chemical_formula_sum            'C8 H6 N4 O S'
_chemical_formula_weight         206.23
_chemical_name_systematic
;
2-(pyrimidin-2-ylamino)-1,3-thiazole-4-carbaldehyde
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 120.377(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4675(4)
_cell_length_b                   21.7393(16)
_cell_length_c                   8.3532(5)
_cell_measurement_reflns_used    10249
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.06
_cell_measurement_theta_min      4.07
_cell_volume                     856.56(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10249
_diffrn_reflns_theta_full        71.06
_diffrn_reflns_theta_max         71.06
_diffrn_reflns_theta_min         4.07
_exptl_absorpt_coefficient_mu    3.124
_exptl_absorpt_correction_T_max  0.8790
_exptl_absorpt_correction_T_min  0.6921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker (2008). SADABS, APEX2 and SAINT.
Bruker AXS Inc., Madison, Wisconsin, USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0468P)²+0.4388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0852
_reflns_number_gt                1554
_reflns_number_total             1612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0DT00973C.TXT
_cod_data_source_block           compound-3
_cod_original_cell_volume        856.56(10)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7014587
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.25580(7) -0.089332(16) 0.78828(5) 0.01558(15) Uani 1 1 d . . .
C1 C 0.3819(3) -0.15233(7) 0.7242(2) 0.0172(3) Uani 1 1 d . . .
C2 C 0.4905(3) -0.13407(7) 0.6160(2) 0.0168(3) Uani 1 1 d . . .
H2 H 0.5679 -0.1625 0.5672 0.020 Uiso 1 1 calc R . .
C3 C 0.3643(3) -0.04329(7) 0.66651(19) 0.0140(3) Uani 1 1 d . . .
C4 C 0.3737(3) -0.21345(7) 0.7869(2) 0.0215(3) Uani 1 1 d . . .
H4 H 0.4420 -0.2462 0.7448 0.026 Uiso 1 1 calc R . .
C5 C 0.2233(3) 0.05661(7) 0.72893(19) 0.0145(3) Uani 1 1 d . . .
C6 C 0.0059(3) 0.06955(8) 0.8961(2) 0.0186(3) Uani 1 1 d . . .
H6 H -0.0707 0.0534 0.9672 0.022 Uiso 1 1 calc R . .
C7 C -0.0030(3) 0.13210(8) 0.8690(2) 0.0199(3) Uani 1 1 d . . .
H7 H -0.0860 0.1591 0.9175 0.024 Uiso 1 1 calc R . .
C8 C 0.1156(3) 0.15363(7) 0.7668(2) 0.0187(3) Uani 1 1 d . . .
H8 H 0.1138 0.1967 0.7464 0.022 Uiso 1 1 calc R . .
N1 N 0.4809(3) -0.07271(6) 0.58270(17) 0.0158(3) Uani 1 1 d . . .
N2 N 0.3372(3) 0.01878(6) 0.65118(17) 0.0152(3) Uani 1 1 d . . .
H2A H 0.3993 0.0368 0.5842 0.018 Uiso 1 1 calc R . .
N3 N 0.1177(2) 0.03052(6) 0.82695(16) 0.0140(3) Uani 1 1 d . . .
N4 N 0.2319(2) 0.11673(6) 0.69606(17) 0.0166(3) Uani 1 1 d . . .
O1 O 0.2847(3) -0.22611(6) 0.89074(17) 0.0290(3) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0197(2) 0.0138(2) 0.0182(2) -0.00020(12) 0.01330(17) -0.00127(12)
C1 0.0186(7) 0.0153(8) 0.0175(7) -0.0009(6) 0.0090(6) -0.0012(5)
C2 0.0184(7) 0.0145(8) 0.0188(7) -0.0007(5) 0.0102(6) 0.0000(5)
C3 0.0124(6) 0.0157(8) 0.0143(7) -0.0004(5) 0.0071(6) -0.0015(5)
C4 0.0286(8) 0.0152(8) 0.0229(8) -0.0021(6) 0.0146(7) -0.0027(6)
C5 0.0131(6) 0.0159(8) 0.0137(7) -0.0004(5) 0.0062(6) 0.0001(5)
C6 0.0182(7) 0.0217(9) 0.0193(7) -0.0012(6) 0.0120(6) -0.0005(6)
C7 0.0194(7) 0.0209(8) 0.0207(8) -0.0027(6) 0.0111(6) 0.0014(6)
C8 0.0189(7) 0.0148(8) 0.0217(8) -0.0010(6) 0.0097(6) 0.0006(5)
N1 0.0175(6) 0.0147(7) 0.0187(6) -0.0003(5) 0.0117(5) -0.0004(5)
N2 0.0190(6) 0.0130(7) 0.0192(6) 0.0015(5) 0.0137(5) -0.0007(4)
N3 0.0148(6) 0.0144(6) 0.0158(6) -0.0004(4) 0.0099(5) -0.0001(5)
N4 0.0172(6) 0.0158(7) 0.0184(6) 0.0004(5) 0.0102(5) -0.0002(5)
O1 0.0459(7) 0.0196(6) 0.0312(7) 0.0000(5) 0.0266(6) -0.0071(5)
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'
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
C3 S1 C1 88.14(7) . . ?
C2 C1 C4 127.83(14) . . ?
C2 C1 S1 110.36(11) . . ?
C4 C1 S1 121.79(12) . . ?
N1 C2 C1 115.82(13) . . ?
N1 C2 H2 122.1 . . ?
C1 C2 H2 122.1 . . ?
N1 C3 N2 119.26(13) . . ?
N1 C3 S1 115.50(11) . . ?
N2 C3 S1 125.25(11) . . ?
O1 C4 C1 124.34(15) . . ?
O1 C4 H4 117.8 . . ?
C1 C4 H4 117.8 . . ?
N4 C5 N3 127.36(13) . . ?
N4 C5 N2 114.49(13) . . ?
N3 C5 N2 118.15(13) . . ?
N3 C6 C7 122.85(14) . . ?
N3 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
C6 C7 C8 116.49(14) . . ?
C6 C7 H7 121.8 . . ?
C8 C7 H7 121.8 . . ?
N4 C8 C7 123.05(14) . . ?
N4 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
C3 N1 C2 110.18(12) . . ?
C3 N2 C5 127.12(12) . . ?
C3 N2 H2A 116.4 . . ?
C5 N2 H2A 116.4 . . ?
C6 N3 C5 115.29(13) . . ?
C8 N4 C5 114.94(12) . . ?
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
S1 C3 1.7315(14) . ?
S1 C1 1.7352(15) . ?
C1 C2 1.368(2) . ?
C1 C4 1.437(2) . ?
C2 N1 1.358(2) . ?
C2 H2 0.9500 . ?
C3 N1 1.3256(19) . ?
C3 N2 1.356(2) . ?
C4 O1 1.221(2) . ?
C4 H4 0.9500 . ?
C5 N4 1.341(2) . ?
C5 N3 1.3428(19) . ?
C5 N2 1.3766(19) . ?
C6 N3 1.3361(19) . ?
C6 C7 1.375(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(2) . ?
C7 H7 0.9500 . ?
C8 N4 1.333(2) . ?
C8 H8 0.9500 . ?
N2 H2A 0.8800 . ?
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
C3 S1 C1 C2 -0.75(11) . . . . ?
C3 S1 C1 C4 177.43(13) . . . . ?
C4 C1 C2 N1 -177.54(14) . . . . ?
S1 C1 C2 N1 0.50(17) . . . . ?
C1 S1 C3 N1 0.92(11) . . . . ?
C1 S1 C3 N2 -179.40(13) . . . . ?
C2 C1 C4 O1 176.46(16) . . . . ?
S1 C1 C4 O1 -1.4(2) . . . . ?
N3 C6 C7 C8 -1.0(2) . . . . ?
C6 C7 C8 N4 0.4(2) . . . . ?
N2 C3 N1 C2 179.50(12) . . . . ?
S1 C3 N1 C2 -0.80(15) . . . . ?
C1 C2 N1 C3 0.17(18) . . . . ?
N1 C3 N2 C5 -179.70(13) . . . . ?
S1 C3 N2 C5 0.6(2) . . . . ?
N4 C5 N2 C3 177.86(13) . . . . ?
N3 C5 N2 C3 -2.2(2) . . . . ?
C7 C6 N3 C5 0.3(2) . . . . ?
N4 C5 N3 C6 1.0(2) . . . . ?
N2 C5 N3 C6 -178.90(12) . . . . ?
C7 C8 N4 C5 0.7(2) . . . . ?
N3 C5 N4 C8 -1.6(2) . . . . ?
N2 C5 N4 C8 178.38(12) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652775
