#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/14/2231408.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_2231408
loop_
_publ_author_name
'Thirugnanasundar, A.'
'Suresh, J.'
'Ramu, A.'
'RajaGopal, G.'
_publ_section_title
;
 N'-[(E)-2-Hydroxy-3,5-diiodobenzylidene]pyridine-3-carbohydrazide
;
_journal_coeditor_code           BT5587
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2303
_journal_paper_doi               10.1107/S160053681103176X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H9 I2 N3 O2'
_chemical_formula_moiety         'C13 H9 I2 N3 O2'
_chemical_formula_sum            'C13 H9 I2 N3 O2'
_chemical_formula_weight         493.03
_chemical_name_systematic
;
N'-[(E)-2-Hydroxy-3,5-diiodobenzylidene]pyridine-3-carbohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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           SHELXL-97
_cell_angle_alpha                90.000
_cell_angle_beta                 90.451(4)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   17.4800(5)
_cell_length_b                   8.5710(4)
_cell_length_c                   9.8650(3)
_cell_measurement_reflns_used    4867
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.6
_cell_measurement_theta_min      1.2
_cell_volume                     1477.94(9)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19735
_diffrn_reflns_theta_full        31.58
_diffrn_reflns_theta_max         31.58
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    4.260
_exptl_absorpt_correction_T_max  0.445
_exptl_absorpt_correction_T_min  0.359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    2.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.678
_refine_diff_density_min         -1.167
_refine_ls_extinction_coef       0.0015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         4866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0525P)²+1.9568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1056
_reflns_number_gt                3640
_reflns_number_total             4866
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5587.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231408
_cod_database_fobs_code          2231408
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_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_symmetry_multiplicity
C C1 0.28906(18) 0.3439(4) 0.7602(3) 0.0383(7) Uani d . 1 1
H H1 0.2713 0.2819 0.6892 0.046 Uiso calc R 1 1
C C2 0.36332(17) 0.3990(4) 0.7591(3) 0.0364(6) Uani d . 1 1
C C3 0.39014(17) 0.4933(4) 0.8622(3) 0.0367(6) Uani d . 1 1
H H3 0.4397 0.5328 0.8598 0.044 Uiso calc R 1 1
C C4 0.34258(17) 0.5285(4) 0.9691(3) 0.0371(6) Uani d . 1 1
C C5 0.26788(16) 0.4720(4) 0.9750(3) 0.0347(6) Uani d . 1 1
C C6 0.24076(16) 0.3806(4) 0.8670(3) 0.0343(6) Uani d . 1 1
C C7 0.16298(17) 0.3211(4) 0.8627(3) 0.0381(7) Uani d . 1 1
H H7 0.1459 0.2645 0.7880 0.046 Uiso calc R 1 1
C C8 0.00141(15) 0.2795(4) 1.0619(3) 0.0347(6) Uani d . 1 1
C C9 -0.07420(15) 0.2011(4) 1.0435(3) 0.0338(6) Uani d . 1 1
C C10 -0.13285(18) 0.2377(5) 1.1314(4) 0.0491(9) Uani d . 1 1
H H10 -0.1259 0.3125 1.1987 0.059 Uiso calc R 1 1
C C11 -0.2021(2) 0.1607(5) 1.1169(4) 0.0559(10) Uani d . 1 1
H H11 -0.2425 0.1819 1.1748 0.067 Uiso calc R 1 1
C C12 -0.2097(2) 0.0528(5) 1.0153(4) 0.0548(9) Uani d . 1 1
H H12 -0.2569 0.0043 1.0046 0.066 Uiso calc R 1 1
C C13 -0.08758(17) 0.0874(4) 0.9470(3) 0.0419(7) Uani d . 1 1
H H13 -0.0477 0.0612 0.8894 0.050 Uiso calc R 1 1
N N1 0.11794(15) 0.3469(3) 0.9622(3) 0.0394(6) Uani d . 1 1
N N2 0.04524(14) 0.2851(4) 0.9506(3) 0.0385(6) Uani d . 1 1
H H2 0.0284 0.2511 0.8740 0.046 Uiso calc R 1 1
N N3 -0.15404(18) 0.0128(4) 0.9311(4) 0.0546(8) Uani d . 1 1
O O1 0.22488(13) 0.5069(3) 1.0828(2) 0.0458(6) Uani d . 1 1
H H1A 0.1816 0.4722 1.0714 0.069 Uiso calc R 1 1
O O2 0.02167(13) 0.3328(3) 1.1712(2) 0.0481(6) Uani d . 1 1
I I1 0.434960(14) 0.34479(3) 0.59728(3) 0.05286(10) Uani d . 1 1
I I2 0.385470(15) 0.66245(4) 1.12850(3) 0.06771(12) Uani d . 1 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'
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'
I I -0.4742 1.8119 '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
C2 C1 C6 120.3(3)
C2 C1 H1 119.9
C6 C1 H1 119.9
C1 C2 C3 120.6(3)
C1 C2 I1 119.9(2)
C3 C2 I1 119.5(2)
C4 C3 C2 119.2(3)
C4 C3 H3 120.4
C2 C3 H3 120.4
C3 C4 C5 121.7(3)
C3 C4 I2 118.8(2)
C5 C4 I2 119.5(2)
O1 C5 C4 119.1(3)
O1 C5 C6 122.6(3)
C4 C5 C6 118.3(3)
C1 C6 C5 119.9(3)
C1 C6 C7 118.2(3)
C5 C6 C7 121.9(3)
N1 C7 C6 119.8(3)
N1 C7 H7 120.1
C6 C7 H7 120.1
O2 C8 N2 123.0(3)
O2 C8 C9 121.8(3)
N2 C8 C9 115.3(3)
C13 C9 C10 118.0(3)
C13 C9 C8 123.1(3)
C10 C9 C8 118.8(3)
C11 C10 C9 118.6(4)
C11 C10 H10 120.7
C9 C10 H10 120.7
C12 C11 C10 118.5(3)
C12 C11 H11 120.7
C10 C11 H11 120.7
N3 C12 C11 124.3(3)
N3 C12 H12 117.8
C11 C12 H12 117.8
N3 C13 C9 124.2(3)
N3 C13 H13 117.9
C9 C13 H13 117.9
C7 N1 N2 116.2(3)
C8 N2 N1 118.5(3)
C8 N2 H2 120.8
N1 N2 H2 120.8
C12 N3 C13 116.4(3)
C5 O1 H1A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.382(4)
C1 C6 1.391(4)
C1 H1 0.9300
C2 C3 1.378(4)
C2 I1 2.089(3)
C3 C4 1.381(4)
C3 H3 0.9300
C4 C5 1.394(4)
C4 I2 2.082(3)
C5 O1 1.341(4)
C5 C6 1.402(4)
C6 C7 1.452(4)
C7 N1 1.282(4)
C7 H7 0.9300
C8 O2 1.221(4)
C8 N2 1.344(4)
C8 C9 1.492(4)
C9 C13 1.381(5)
C9 C10 1.384(4)
C10 C11 1.385(5)
C10 H10 0.9300
C11 C12 1.369(6)
C11 H11 0.9300
C12 N3 1.329(5)
C12 H12 0.9300
C13 N3 1.334(4)
C13 H13 0.9300
N1 N2 1.381(3)
N2 H2 0.8600
O1 H1A 0.8200
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
O1 H1A N1 . 0.82 1.88 2.599(4) 146
N2 H2 O2 4_565 0.86 2.13 2.962(4) 163.1
C7 H7 O2 4_565 0.93 2.59 3.367(4) 141.7
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
C6 C1 C2 C3 -1.2(5)
C6 C1 C2 I1 -179.4(2)
C1 C2 C3 C4 1.9(5)
I1 C2 C3 C4 -179.8(2)
C2 C3 C4 C5 -0.5(5)
C2 C3 C4 I2 177.2(2)
C3 C4 C5 O1 178.5(3)
I2 C4 C5 O1 0.8(4)
C3 C4 C5 C6 -1.6(5)
I2 C4 C5 C6 -179.3(2)
C2 C1 C6 C5 -1.0(5)
C2 C1 C6 C7 179.4(3)
O1 C5 C6 C1 -177.7(3)
C4 C5 C6 C1 2.3(5)
O1 C5 C6 C7 1.9(5)
C4 C5 C6 C7 -178.0(3)
C1 C6 C7 N1 177.0(3)
C5 C6 C7 N1 -2.7(5)
O2 C8 C9 C13 -152.5(3)
N2 C8 C9 C13 26.8(5)
O2 C8 C9 C10 24.1(5)
N2 C8 C9 C10 -156.6(3)
C13 C9 C10 C11 -1.0(5)
C8 C9 C10 C11 -177.8(3)
C9 C10 C11 C12 -0.6(6)
C10 C11 C12 N3 2.1(7)
C10 C9 C13 N3 1.5(5)
C8 C9 C13 N3 178.1(3)
C6 C7 N1 N2 -179.4(3)
O2 C8 N2 N1 3.4(5)
C9 C8 N2 N1 -175.9(3)
C7 N1 N2 C8 166.1(3)
C11 C12 N3 C13 -1.7(6)
C9 C13 N3 C12 -0.2(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12271549
