##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
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# of the IUCr Commission on Journals.                                        #
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# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-12-17
_journal_date_accepted     2009-12-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      2
_journal_page_first     o271
_journal_page_last     o272
_journal_paper_category     QO
_journal_coeditor_code     HB5284
_publ_contact_author_name     ' Edward RT Tiekink '
_publ_contact_author_address
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email
;
edward.tiekink@gmail.com
;
_publ_contact_author_fax     ' +60 3 7967 4193 '
_publ_contact_author_phone     ' +60 3 7967 6775 '
_publ_section_title
;
5-{[(E)-2-(4-Iodophenyl)hydrazinylidene]methyl}thiophene-2-carbaldehyde
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Wardell, Solange M. S. V.' .
;
CHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland
;
    'Lima, Geraldo M. de' .
;
Departamento de Quimica, ICEx, Universidade Federal de Minas Gerais,
31270-901 Belo Horizonte, MG, Brazil
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Wardell, James L.'
;
Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.
;
;
Centro de Desenvolvimento Tecnológico em Saúde (CDTS),
Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos,
Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
5-{[(E)-2-(4-Iodophenyl)hydrazinylidene]methyl}thiophene-2-carbaldehyde
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H9 I N2 O S'
_chemical_formula_sum     'C12 H9 I N2 O S'
_chemical_formula_iupac     'C12 H9 I N2 O S'
_chemical_formula_weight     356.17
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     6.9291(9)
_cell_length_b     11.7602(10)
_cell_length_c     30.958(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2522.7(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     16555
_cell_measurement_theta_min     2.9
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     120(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.16
_exptl_crystal_size_mid     0.08
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.876
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1376
_exptl_absorpt_coefficient_mu     2.688
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2007)'
_exptl_absorpt_correction_T_min     0.616
_exptl_absorpt_correction_T_max     0.746
_exptl_special_details
;
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     '10 cm confocal mirrors'
_diffrn_measurement_device_type     'Nonius KappaCCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     15735
_diffrn_reflns_av_R_equivalents     0.095
_diffrn_reflns_av_sigmaI/netI     0.064
_diffrn_reflns_theta_min     3.2
_diffrn_reflns_theta_max     26.5
_diffrn_reflns_theta_full     26.5
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -38
_diffrn_reflns_limit_l_max     37
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
2σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2614
_reflns_number_gt     1674
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.107
_refine_ls_R_factor_gt     0.058
_refine_ls_wR_factor_gt     0.097
_refine_ls_wR_factor_ref     0.113
_refine_ls_goodness_of_fit_ref     1.04
_refine_ls_restrained_S_all     1.04
_refine_ls_number_reflns     2614
_refine_ls_number_parameters     157
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w=1/[σ²(Fo²)+(0.0257P)²+17.1487P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.08
_refine_diff_density_min     -0.60
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'S' 'S' 0.1246 0.1234
                         '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'
    'I' 'I' -0.4742 1.8119
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Hooft, 1998)'
_computing_cell_refinement
                    'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction
                    'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                      'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    I I1 -0.01127(8) 0.34335(4) 0.487908(18) 0.04277(19) Uani d . 1 . .
    S S1 0.1013(3) 0.10271(14) 0.21597(6) 0.0261(4) Uani d . 1 . .
    N N1 0.0936(8) -0.0324(5) 0.3466(2) 0.0282(14) Uani d D 1 . .
    H H1N 0.039(9) -0.099(3) 0.350(2) 0.034 Uiso d D 1 . .
    N N2 0.1043(8) 0.0033(5) 0.3048(2) 0.0266(13) Uani d . 1 . .
    O O1 0.1012(7) 0.2541(4) 0.13359(16) 0.0336(12) Uani d . 1 . .
    C C1 0.0410(10) 0.2143(6) 0.4423(2) 0.0323(18) Uani d . 1 . .
    C C2 0.1194(10) 0.2425(6) 0.4030(2) 0.0322(18) Uani d . 1 . .
    H H2 0.1610 0.3182 0.3976 0.039 Uiso calc R 1 . .
    C C3 0.1374(9) 0.1609(6) 0.3714(2) 0.0278(16) Uani d . 1 . .
    H H3 0.1900 0.1808 0.3441 0.033 Uiso calc R 1 . .
    C C4 0.0794(9) 0.0499(6) 0.3792(2) 0.0231(15) Uani d . 1 . .
    C C5 0.0110(10) 0.0198(5) 0.4197(2) 0.0284(16) Uani d . 1 . .
    H H5 -0.0202 -0.0573 0.4257 0.034 Uiso calc R 1 . .
    C C6 -0.0121(10) 0.1017(6) 0.4514(2) 0.0332(17) Uani d . 1 . .
    H H6 -0.0631 0.0820 0.4789 0.040 Uiso calc R 1 . .
    C C7 0.0949(10) -0.0729(6) 0.2752(2) 0.0275(17) Uani d . 1 . .
    H H7 0.0837 -0.1509 0.2827 0.033 Uiso calc R 1 . .
    C C8 0.1016(9) -0.0394(5) 0.2306(2) 0.0249(16) Uani d . 1 . .
    C C9 0.1085(9) 0.0672(6) 0.1616(2) 0.0239(15) Uani d . 1 . .
    C C10 0.1118(10) -0.0491(6) 0.1562(2) 0.0291(17) Uani d . 1 . .
    H H10 0.1177 -0.0849 0.1288 0.035 Uiso calc R 1 . .
    C C11 0.1057(10) -0.1090(6) 0.1951(2) 0.0292(16) Uani d . 1 . .
    H H11 0.1046 -0.1897 0.1968 0.035 Uiso calc R 1 . .
    C C12 0.1088(9) 0.1509(6) 0.1282(2) 0.0288(16) Uani d . 1 . .
    H H12 0.1156 0.1243 0.0993 0.035 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    I1 0.0425(3) 0.0365(3) 0.0493(3) -0.0005(3) 0.0024(3) -0.0128(3)
    S1 0.0228(9) 0.0219(8) 0.0336(10) -0.0006(8) 0.0004(8) -0.0049(8)
    N1 0.023(3) 0.020(3) 0.042(4) -0.002(3) 0.004(3) 0.001(3)
    N2 0.020(3) 0.030(3) 0.030(4) 0.001(3) 0.005(3) 0.003(3)
    O1 0.027(3) 0.025(3) 0.049(3) -0.003(2) -0.004(3) -0.001(2)
    C1 0.029(4) 0.033(4) 0.035(4) 0.001(3) -0.007(3) -0.003(3)
    C2 0.025(4) 0.027(4) 0.045(5) -0.005(3) -0.005(4) -0.002(3)
    C3 0.018(3) 0.026(4) 0.039(4) -0.002(3) -0.002(3) -0.001(3)
    C4 0.018(3) 0.024(4) 0.027(4) 0.001(3) -0.002(3) -0.001(3)
    C5 0.027(4) 0.020(3) 0.038(4) 0.001(3) -0.003(4) 0.003(3)
    C6 0.034(4) 0.032(4) 0.034(4) 0.002(4) 0.001(4) -0.001(3)
    C7 0.021(4) 0.022(4) 0.040(5) 0.000(3) 0.000(4) 0.001(3)
    C8 0.017(3) 0.018(3) 0.039(4) -0.002(3) 0.001(3) -0.005(3)
    C9 0.012(3) 0.031(4) 0.029(4) 0.002(3) 0.001(3) -0.006(3)
    C10 0.023(4) 0.025(4) 0.039(5) 0.001(3) -0.002(3) -0.011(3)
    C11 0.026(4) 0.018(3) 0.044(5) 0.000(3) 0.010(4) -0.006(3)
    C12 0.020(3) 0.027(4) 0.040(5) 0.005(4) -0.002(3) -0.007(3)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
    I1 C1 . 2.103(7) ?
    S1 C8 . 1.732(7) ?
    S1 C9 . 1.734(7) ?
    N1 N2 . 1.362(8) ?
    N1 C4 . 1.402(8) ?
    N1 H1N . 0.876(10) ?
    N2 C7 . 1.284(8) ?
    O1 C12 . 1.227(8) ?
    C1 C2 . 1.374(10) ?
    C1 C6 . 1.403(10) ?
    C2 C3 . 1.376(9) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.388(9) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.387(9) ?
    C5 C6 . 1.386(9) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.436(9) ?
    C7 H7 . 0.9500 ?
    C8 C11 . 1.371(9) ?
    C9 C10 . 1.378(9) ?
    C9 C12 . 1.429(9) ?
    C10 C11 . 1.395(10) ?
    C10 H10 . 0.9500 ?
    C11 H11 . 0.9500 ?
    C12 H12 . 0.9500 ?
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
    _geom_angle_publ_flag
    C8 S1 C9 . . 91.2(3) ?
    N2 N1 C4 . . 118.3(6) ?
    N2 N1 H1N . . 114(5) ?
    C4 N1 H1N . . 120(5) ?
    C7 N2 N1 . . 117.4(6) ?
    C2 C1 C6 . . 120.6(7) ?
    C2 C1 I1 . . 119.2(5) ?
    C6 C1 I1 . . 120.1(5) ?
    C1 C2 C3 . . 119.8(7) ?
    C1 C2 H2 . . 120.1 ?
    C3 C2 H2 . . 120.1 ?
    C2 C3 C4 . . 120.5(7) ?
    C2 C3 H3 . . 119.8 ?
    C4 C3 H3 . . 119.8 ?
    C3 C4 C5 . . 119.7(6) ?
    C3 C4 N1 . . 120.4(6) ?
    C5 C4 N1 . . 119.9(6) ?
    C6 C5 C4 . . 120.2(6) ?
    C6 C5 H5 . . 119.9 ?
    C4 C5 H5 . . 119.9 ?
    C5 C6 C1 . . 118.9(7) ?
    C5 C6 H6 . . 120.5 ?
    C1 C6 H6 . . 120.5 ?
    N2 C7 C8 . . 119.6(6) ?
    N2 C7 H7 . . 120.2 ?
    C8 C7 H7 . . 120.2 ?
    C11 C8 C7 . . 127.4(6) ?
    C11 C8 S1 . . 111.5(5) ?
    C7 C8 S1 . . 121.1(5) ?
    C10 C9 C12 . . 126.6(6) ?
    C10 C9 S1 . . 110.9(5) ?
    C12 C9 S1 . . 122.5(5) ?
    C9 C10 C11 . . 113.3(6) ?
    C9 C10 H10 . . 123.3 ?
    C11 C10 H10 . . 123.3 ?
    C8 C11 C10 . . 113.0(6) ?
    C8 C11 H11 . . 123.5 ?
    C10 C11 H11 . . 123.5 ?
    O1 C12 C9 . . 125.7(7) ?
    O1 C12 H12 . . 117.2 ?
    C9 C12 H12 . . 117.2 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C4 N1 N2 C7 . . . . -172.2(6) ?
    C6 C1 C2 C3 . . . . 3.2(11) ?
    I1 C1 C2 C3 . . . . -173.9(5) ?
    C1 C2 C3 C4 . . . . -0.9(10) ?
    C2 C3 C4 C5 . . . . -3.0(10) ?
    C2 C3 C4 N1 . . . . 178.4(6) ?
    N2 N1 C4 C3 . . . . -20.8(9) ?
    N2 N1 C4 C5 . . . . 160.6(6) ?
    C3 C4 C5 C6 . . . . 4.5(10) ?
    N1 C4 C5 C6 . . . . -176.9(6) ?
    C4 C5 C6 C1 . . . . -2.1(11) ?
    C2 C1 C6 C5 . . . . -1.7(11) ?
    I1 C1 C6 C5 . . . . 175.4(5) ?
    N1 N2 C7 C8 . . . . 178.7(6) ?
    N2 C7 C8 C11 . . . . 175.5(7) ?
    N2 C7 C8 S1 . . . . -5.6(9) ?
    C9 S1 C8 C11 . . . . -0.4(5) ?
    C9 S1 C8 C7 . . . . -179.4(6) ?
    C8 S1 C9 C10 . . . . -0.3(5) ?
    C8 S1 C9 C12 . . . . 179.2(6) ?
    C12 C9 C10 C11 . . . . -178.5(6) ?
    S1 C9 C10 C11 . . . . 0.9(8) ?
    C7 C8 C11 C10 . . . . 180.0(7) ?
    S1 C8 C11 C10 . . . . 1.0(8) ?
    C9 C10 C11 C8 . . . . -1.2(9) ?
    C10 C9 C12 O1 . . . . 178.2(7) ?
    S1 C9 C12 O1 . . . . -1.2(10) ?
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 H1n O1 3_545 0.88(4) 2.05(5) 2.916(8) 172(5)
