#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/18/2231824.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_2231824
loop_
_publ_author_name
'Thirugnanasundar, A.'
'Suresh, J.'
'Meenakshi, C.'
'Chakkaravarthi, G.'
'Rajagopal, G.'
_publ_section_title
;
 N'-[(E)-2-Hydroxy-3,5-diiodobenzylidene]cyclohexane-1-carbohydrazide
;
_journal_coeditor_code           BT5637
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2620
_journal_paper_doi               10.1107/S1600536811036488
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H10 I2 N2 O2'
_chemical_formula_moiety         'C14 H10 I2 N2 O2'
_chemical_formula_sum            'C14 H10 I2 N2 O2'
_chemical_formula_weight         492.04
_chemical_name_systematic
;
N'-[(E)-2-Hydroxy-3,5-diiodobenzylidene]cyclohexane-1-
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                90.00
_cell_angle_beta                 103.052(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.7495(13)
_cell_length_b                   9.4273(6)
_cell_length_c                   9.4684(7)
_cell_measurement_reflns_used    13146
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.2
_cell_volume                     1543.42(19)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13146
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.16
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.077
_exptl_absorpt_correction_T_max  0.6859
_exptl_absorpt_correction_T_min  0.4961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.118
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.481
_refine_diff_density_min         -1.520
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0584
_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)+(0.0412P)²+42.3729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1718
_reflns_number_gt                2349
_reflns_number_total             2708
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            bt5637.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231824
_cod_database_fobs_code          2231824
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
I I1 0.89740(5) 0.16968(10) 0.83785(10) 0.0458(3) Uani d . 1 1
I I2 0.91863(7) -0.18253(14) 1.36905(13) 0.0777(5) Uani d . 1 1
O O1 0.5247(5) 0.3352(11) 0.8089(10) 0.052(3) Uani d . 1 1
O O2 0.7346(5) 0.2255(10) 0.9018(10) 0.044(2) Uani d . 1 1
H H2A 0.6895 0.2404 0.9145 0.065 Uiso d R 1 1
N N1 0.5428(6) 0.2182(13) 1.0250(11) 0.043(3) Uani d . 1 1
H H1 0.5244 0.1906 1.0969 0.052 Uiso calc R 1 1
N N2 0.6169(6) 0.1863(12) 1.0158(11) 0.040(3) Uani d . 1 1
C C1 0.4189(7) 0.3296(14) 0.9272(12) 0.036(3) Uani d . 1 1
C C2 0.3821(7) 0.4436(15) 0.8509(13) 0.043(3) Uani d . 1 1
H H2 0.4075 0.4988 0.7950 0.052 Uiso calc R 1 1
C C3 0.3079(9) 0.4755(18) 0.8577(16) 0.057(4) Uani d . 1 1
H H3 0.2836 0.5541 0.8082 0.068 Uiso calc R 1 1
C C4 0.2694(8) 0.3939(16) 0.9356(15) 0.047(3) Uani d . 1 1
H H4 0.2185 0.4156 0.9369 0.057 Uiso calc R 1 1
C C5 0.3052(7) 0.2777(15) 1.0138(13) 0.041(3) Uani d . 1 1
H H5 0.2790 0.2217 1.0678 0.049 Uiso calc R 1 1
C C6 0.3807(7) 0.2479(15) 1.0092(14) 0.041(3) Uani d . 1 1
H H6 0.4060 0.1719 1.0621 0.049 Uiso calc R 1 1
C C7 0.4996(7) 0.2964(14) 0.9137(11) 0.035(3) Uani d . 1 1
C C8 0.6579(7) 0.1120(14) 1.1159(12) 0.036(3) Uani d . 1 1
H H8 0.6375 0.0800 1.1924 0.043 Uiso calc R 1 1
C C9 0.7375(7) 0.0770(13) 1.1107(13) 0.034(3) Uani d . 1 1
C C10 0.7797(7) -0.0131(15) 1.2142(14) 0.042(3) Uani d . 1 1
H H10 0.7576 -0.0486 1.2872 0.051 Uiso calc R 1 1
C C11 0.8534(8) -0.0503(15) 1.2102(14) 0.043(3) Uani d . 1 1
C C12 0.8881(7) 0.0029(13) 1.1027(14) 0.040(3) Uani d . 1 1
H H12 0.9385 -0.0225 1.1010 0.048 Uiso calc R 1 1
C C13 0.8471(7) 0.0932(13) 0.9997(13) 0.034(3) Uani d . 1 1
C C14 0.7710(6) 0.1333(13) 1.0022(12) 0.031(2) 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
C14 O2 H2A 108.9
C7 N1 N2 116.6(10)
C7 N1 H1 121.7
N2 N1 H1 121.7
C8 N2 N1 118.1(10)
C2 C1 C6 119.8(11)
C2 C1 C7 117.9(12)
C6 C1 C7 122.2(11)
C3 C2 C1 119.8(14)
C3 C2 H2 120.1
C1 C2 H2 120.1
C4 C3 C2 120.7(14)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 120.7(13)
C3 C4 H4 119.6
C5 C4 H4 119.6
C6 C5 C4 118.3(12)
C6 C5 H5 120.9
C4 C5 H5 120.9
C1 C6 C5 120.7(12)
C1 C6 H6 119.7
C5 C6 H6 119.7
O1 C7 N1 122.6(11)
O1 C7 C1 122.2(11)
N1 C7 C1 115.2(10)
N2 C8 C9 119.7(11)
N2 C8 H8 120.1
C9 C8 H8 120.1
C10 C9 C14 120.1(11)
C10 C9 C8 119.2(11)
C14 C9 C8 120.8(11)
C11 C10 C9 120.5(12)
C11 C10 H10 119.7
C9 C10 H10 119.7
C10 C11 C12 120.8(12)
C10 C11 I2 120.9(10)
C12 C11 I2 118.3(9)
C13 C12 C11 119.4(11)
C13 C12 H12 120.3
C11 C12 H12 120.3
C12 C13 C14 120.7(11)
C12 C13 I1 119.6(9)
C14 C13 I1 119.7(9)
O2 C14 C9 123.3(10)
O2 C14 C13 118.1(10)
C9 C14 C13 118.5(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C13 2.070(12)
I2 C11 2.090(13)
O1 C7 1.231(14)
O2 C14 1.342(14)
O2 H2A 0.8480
N1 C7 1.370(15)
N1 N2 1.370(13)
N1 H1 0.8600
N2 C8 1.268(16)
C1 C2 1.375(18)
C1 C6 1.376(18)
C1 C7 1.500(16)
C2 C3 1.366(19)
C2 H2 0.9300
C3 C4 1.35(2)
C3 H3 0.9300
C4 C5 1.393(19)
C4 H4 0.9300
C5 C6 1.379(17)
C5 H5 0.9300
C6 H6 0.9300
C8 C9 1.463(16)
C8 H8 0.9300
C9 C10 1.382(17)
C9 C14 1.402(16)
C10 C11 1.363(18)
C10 H10 0.9300
C11 C12 1.397(18)
C12 C13 1.373(17)
C12 H12 0.9300
C13 C14 1.409(16)
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
_geom_hbond_publ_flag
O2 H2A N2 . 0.85 1.84 2.586(13) 145 y
N1 H1 O1 4_566 0.86 2.02 2.824(14) 155 y
C3 H3 O2 2_656 0.93 2.53 3.365(19) 150 y
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
C7 N1 N2 C8 -178.8(12)
C6 C1 C2 C3 0(2)
C7 C1 C2 C3 178.5(12)
C1 C2 C3 C4 -2(2)
C2 C3 C4 C5 2(2)
C3 C4 C5 C6 0(2)
C2 C1 C6 C5 1(2)
C7 C1 C6 C5 -177.0(12)
C4 C5 C6 C1 -1(2)
N2 N1 C7 O1 1.0(19)
N2 N1 C7 C1 -179.9(11)
C2 C1 C7 O1 -22.7(18)
C6 C1 C7 O1 155.4(13)
C2 C1 C7 N1 158.2(12)
C6 C1 C7 N1 -23.7(18)
N1 N2 C8 C9 -179.4(11)
N2 C8 C9 C10 -175.0(13)
N2 C8 C9 C14 4.9(19)
C14 C9 C10 C11 -1(2)
C8 C9 C10 C11 178.5(13)
C9 C10 C11 C12 1(2)
C9 C10 C11 I2 178.5(10)
C10 C11 C12 C13 0(2)
I2 C11 C12 C13 -178.1(10)
C11 C12 C13 C14 0.5(19)
C11 C12 C13 I1 -178.9(10)
C10 C9 C14 O2 -177.3(12)
C8 C9 C14 O2 2.8(18)
C10 C9 C14 C13 1.5(18)
C8 C9 C14 C13 -178.4(11)
C12 C13 C14 O2 177.8(11)
I1 C13 C14 O2 -2.8(15)
C12 C13 C14 C9 -1.1(18)
I1 C13 C14 C9 178.3(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 22938794
