#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/26/1512649.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_1512649
loop_
_publ_author_name
'Kusai Alomar'
'Vincent Gaumet'
'Magali Allain'
'Pascal Richomme'
'Gilles Bouet'
_publ_section_title
;
 Complexes of thiophene-2,3-dicarboxaldehyde bis(oxime) (2,3BTCOH2) with
 nickel(II) and copper(II): Synthesis, characterization, crystal structure
 of 2,3BTCOH2. Rearrangement reaction with nickel(II) bromide
;
_journal_name_full
;
Inorganica Chimica Acta
;
_journal_page_first              433
_journal_page_last               439
_journal_paper_doi               10.1016/j.ica.2012.05.029
_journal_volume                  392
_journal_year                    2012
_chemical_formula_moiety         'C6 H6 N2 O2 S'
_chemical_formula_sum            'C6 H6 N2 O2 S'
_chemical_formula_weight         170.19
_chemical_name_common
; 
(1E,1'Z)-2-((Z)-(hydroxyimino)methyl)thiophene-3-carbaldehyde oxime
;
_chemical_name_systematic
; 
(1E,1'Z)-2-((Z)-(hydroxyimino)methyl)thiophene-3-carbaldehyde oxime
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 114.109(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.1796(7)
_cell_length_b                   4.22360(10)
_cell_length_c                   15.7219(4)
_cell_measurement_reflns_used    5270
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.45
_cell_measurement_theta_min      3.62
_cell_volume                     1465.54(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia,1997)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10892
_diffrn_reflns_theta_full        31.09
_diffrn_reflns_theta_max         31.09
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.387
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.83
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.055
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         2257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0576
_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)+(0.1204P)²+2.1332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1808
_refine_ls_wR_factor_ref         0.2130
_reflns_number_gt                1763
_reflns_number_total             2257
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2012-392-433-439-2.cif
_cod_data_source_block           C6
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1512649
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
S1 S 0.19273(3) 0.65196(17) 0.25123(5) 0.0448(3) Uani 1 1 d .
C4 C 0.12977(10) 0.4272(6) 0.23137(14) 0.0325(4) Uani 1 1 d .
C3 C 0.12961(10) 0.3109(6) 0.31424(14) 0.0334(5) Uani 1 1 d .
C5 C 0.08313(11) 0.1017(6) 0.31780(14) 0.0356(5) Uani 1 1 d .
H5 H 0.0538 0.0213 0.2628 0.043 Uiso 1 1 calc R
C6 C 0.08404(12) 0.3588(6) 0.13893(15) 0.0379(5) Uani 1 1 d .
H6 H 0.0537 0.2194 0.1368 0.046 Uiso 1 1 calc R
C2 C 0.18333(11) 0.4115(6) 0.39706(17) 0.0399(5) Uani 1 1 d .
H2 H 0.1914 0.3611 0.4586 0.048 Uiso 1 1 calc R
C1 C 0.21959(13) 0.5935(8) 0.36743(19) 0.0510(7) Uani 1 1 d .
H1 H 0.2563 0.6780 0.4087 0.061 Uiso 1 1 calc R
N1 N 0.08217(9) 0.0270(5) 0.39600(12) 0.0370(4) Uani 1 1 d .
N2 N 0.07954(10) 0.4642(6) 0.05932(13) 0.0426(5) Uani 1 1 d .
O1 O 0.03385(9) -0.1784(5) 0.38358(12) 0.0463(5) Uani 1 1 d .
H1O H 0.0404 -0.2706 0.4327 0.069 Uiso 1 1 calc R
O2 O 0.12580(10) 0.6693(6) 0.06764(13) 0.0542(6) Uani 1 1 d .
H2O H 0.1175 0.7613 0.0180 0.081 Uiso 1 1 calc R
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 0.0409(4) 0.0492(4) 0.0439(4) -0.0015(3) 0.0171(3) -0.0002(3)
C4 0.0361(10) 0.0353(10) 0.0273(9) -0.0013(8) 0.0144(8) 0.0040(8)
C3 0.0378(10) 0.0380(11) 0.0240(8) -0.0007(8) 0.0124(7) 0.0059(9)
C5 0.0409(11) 0.0423(12) 0.0234(9) 0.0018(8) 0.0129(8) 0.0045(9)
C6 0.0435(12) 0.0467(13) 0.0244(9) -0.0008(8) 0.0147(8) 0.0001(10)
C2 0.0381(11) 0.0443(12) 0.0355(11) -0.0020(9) 0.0131(9) 0.0044(10)
C1 0.0400(12) 0.0604(16) 0.0409(13) -0.0073(12) 0.0046(10) 0.0018(12)
N1 0.0457(10) 0.0408(10) 0.0246(8) 0.0021(7) 0.0146(7) 0.0053(8)
N2 0.0496(11) 0.0535(12) 0.0261(8) -0.0027(8) 0.0169(8) -0.0024(10)
O1 0.0498(10) 0.0585(12) 0.0302(8) 0.0112(8) 0.0159(7) -0.0035(9)
O2 0.0587(12) 0.0710(14) 0.0304(8) 0.0094(8) 0.0156(8) -0.0111(10)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S1 C4 92.10(13)
C3 C4 C6 125.0(2)
C3 C4 S1 111.52(17)
C6 C4 S1 123.39(17)
C4 C3 C5 123.3(2)
C4 C3 C2 112.7(2)
C5 C3 C2 123.94(19)
N1 C5 C3 120.4(2)
N1 C5 H5 119.8
C3 C5 H5 119.8
N2 C6 C4 129.1(2)
N2 C6 H6 115.4
C4 C6 H6 115.4
C1 C2 C3 108.3(2)
C1 C2 H2 125.9
C3 C2 H2 125.9
C2 C1 S1 115.4(2)
C2 C1 H1 122.3
S1 C1 H1 122.3
C5 N1 O1 111.09(19)
C6 N2 O2 112.4(2)
N1 O1 H1O 109.5
N2 O2 H2O 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.688(3)
S1 C4 1.711(2)
C4 C3 1.394(3)
C4 C6 1.451(3)
C3 C5 1.448(3)
C3 C2 1.477(3)
C5 N1 1.279(3)
C5 H5 0.9300
C6 N2 1.290(3)
C6 H6 0.9300
C2 C1 1.382(4)
C2 H2 0.9300
C1 H1 0.9300
N1 O1 1.404(3)
N2 O2 1.378(3)
O1 H1O 0.8200
O2 H2O 0.8200
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 N2 0.82 2.00 2.796(3) 164.4 6_556
O2 H2O N1 0.82 1.97 2.777(3) 169.6 6_565
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
C1 S1 C4 C3 0.46(19)
C1 S1 C4 C6 -177.2(2)
C6 C4 C3 C5 0.6(4)
S1 C4 C3 C5 -177.10(18)
C6 C4 C3 C2 177.8(2)
S1 C4 C3 C2 0.1(3)
C4 C3 C5 N1 -173.3(2)
C2 C3 C5 N1 9.8(4)
C3 C4 C6 N2 177.3(2)
S1 C4 C6 N2 -5.3(4)
C4 C3 C2 C1 -0.8(3)
C5 C3 C2 C1 176.4(2)
C3 C2 C1 S1 1.2(3)
C4 S1 C1 C2 -1.0(2)
C3 C5 N1 O1 -179.6(2)
C4 C6 N2 O2 -0.1(4)
