#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/82/2228230.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_2228230
loop_
_publ_author_name
'Thirugnan Sundar, A.'
'Rajagopal, G.'
'Murugavel, S.'
'Subbiah Pandi, A.'
_publ_section_title
;
 2-{[4-(Diethylamino)phenyl]iminomethyl}-4,6-diiodophenol
;
_journal_coeditor_code           BT5392
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3089
_journal_paper_doi               10.1107/S160053681004417X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H18 I2 N2 O'
_chemical_formula_moiety         'C17 H18 I2 N2 O'
_chemical_formula_sum            'C17 H18 I2 N2 O'
_chemical_formula_weight         520.13
_chemical_name_systematic
;
2-{[4-(Diethylamino)phenyl]iminomethyl}-4,6-diiodophenol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 111.958(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5562(5)
_cell_length_b                   11.1325(5)
_cell_length_c                   15.1207(6)
_cell_measurement_reflns_used    7076
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.5
_cell_measurement_theta_min      1.9
_cell_volume                     1804.16(14)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'XPREP (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_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '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  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26163
_diffrn_reflns_theta_full        33.51
_diffrn_reflns_theta_max         33.51
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    3.489
_exptl_absorpt_correction_T_max  0.572
_exptl_absorpt_correction_T_min  0.450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.139
_refine_diff_density_min         -1.244
_refine_ls_extinction_coef       0.00078(19)
_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   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         7041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0359
_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)+(0.0437P)²+1.1802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                4445
_reflns_number_total             7041
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5392.cif
_cod_data_source_block           I
_cod_original_cell_volume        1804.15(13)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228230
_cod_database_fobs_code          2228230
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_disorder_assembly
_atom_site_disorder_group
I I1 0.33796(2) 0.47955(2) 0.048244(18) 0.06508(9) Uani d . 1 . .
I I2 -0.17213(2) 0.45975(3) -0.257569(17) 0.07853(11) Uani d . 1 . .
O O1 -0.18770(18) 0.2470(2) -0.12546(15) 0.0561(5) Uani d . 1 . .
H H1 -0.1935 0.1911 -0.0920 0.084 Uiso calc R 1 . .
N N1 -0.1205(2) 0.10225(19) 0.01926(16) 0.0424(5) Uani d . 1 . .
N N2 -0.2604(2) -0.2797(2) 0.20106(18) 0.0502(5) Uani d . 1 . .
C C1 -0.0432(2) 0.3956(2) -0.12942(18) 0.0418(5) Uani d . 1 . .
C C2 -0.0754(2) 0.2987(2) -0.08510(19) 0.0401(5) Uani d . 1 . .
C C3 0.0127(2) 0.2571(2) 0.00140(18) 0.0384(5) Uani d . 1 . .
C C4 0.1298(2) 0.3106(2) 0.0396(2) 0.0434(5) Uani d . 1 . .
H H4 0.1882 0.2827 0.0969 0.052 Uiso calc R 1 . .
C C5 0.1596(2) 0.4050(2) -0.00723(19) 0.0413(5) Uani d . 1 . .
C C6 0.0732(2) 0.4483(2) -0.09115(19) 0.0424(5) Uani d . 1 . .
H H6 0.0931 0.5128 -0.1220 0.051 Uiso calc R 1 . .
C C7 -0.0155(3) 0.1572(2) 0.0516(2) 0.0435(5) Uani d . 1 . .
H H7 0.0447 0.1321 0.1091 0.052 Uiso calc R 1 . .
C C8 -0.1490(2) 0.0059(2) 0.06823(19) 0.0393(5) Uani d . 1 . .
C C9 -0.0659(2) -0.0478(2) 0.1498(2) 0.0448(6) Uani d . 1 . .
H H9 0.0160 -0.0206 0.1753 0.054 Uiso calc R 1 . .
C C10 -0.1022(3) -0.1412(3) 0.1942(2) 0.0460(6) Uani d . 1 . .
H H10 -0.0442 -0.1752 0.2490 0.055 Uiso calc R 1 . .
C C11 -0.2248(2) -0.1854(2) 0.15812(19) 0.0414(5) Uani d . 1 . .
C C12 -0.3081(3) -0.1300(3) 0.0757(2) 0.0474(6) Uani d . 1 . .
H H12 -0.3906 -0.1557 0.0501 0.057 Uiso calc R 1 . .
C C13 -0.2698(3) -0.0380(2) 0.03204(19) 0.0442(6) Uani d . 1 . .
H H13 -0.3268 -0.0044 -0.0234 0.053 Uiso calc R 1 . .
C C14 -0.3909(3) -0.3145(3) 0.1708(2) 0.0564(7) Uani d . 1 . .
H H14A -0.3951 -0.3952 0.1936 0.068 Uiso calc R 1 . .
H H14B -0.4266 -0.3168 0.1017 0.068 Uiso calc R 1 . .
C C15 -0.4696(4) -0.2328(4) 0.2052(3) 0.0820(12) Uani d . 1 . .
H H15A -0.4382 -0.2334 0.2737 0.123 Uiso calc R 1 . .
H H15B -0.5544 -0.2605 0.1808 0.123 Uiso calc R 1 . .
H H15C -0.4662 -0.1525 0.1832 0.123 Uiso calc R 1 . .
C C16 -0.1740(3) -0.3316(3) 0.2895(3) 0.0681(9) Uani d . 1 . .
H H16A -0.0935 -0.3421 0.2842 0.082 Uiso calc R 1 . .
H H16B -0.2042 -0.4105 0.2977 0.082 Uiso calc R 1 . .
C C17 -0.1568(4) -0.2583(5) 0.3760(3) 0.0930(15) Uani d . 1 . .
H H17A -0.1348 -0.1777 0.3662 0.140 Uiso calc R 1 . .
H H17B -0.0914 -0.2926 0.4300 0.140 Uiso calc R 1 . .
H H17C -0.2331 -0.2575 0.3874 0.140 Uiso calc R 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'
I I -0.4742 1.8119 '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'
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
C2 O1 H1 . . 109.5 ?
C7 N1 C8 . . 122.5(2) ?
C11 N2 C14 . . 120.8(2) ?
C11 N2 C16 . . 120.9(2) ?
C14 N2 C16 . . 117.2(2) ?
C6 C1 C2 . . 121.4(2) ?
C6 C1 I2 . . 119.38(19) ?
C2 C1 I2 . . 119.18(19) ?
O1 C2 C1 . . 120.1(2) ?
O1 C2 C3 . . 121.6(2) ?
C1 C2 C3 . . 118.3(2) ?
C4 C3 C2 . . 120.0(2) ?
C4 C3 C7 . . 119.0(2) ?
C2 C3 C7 . . 121.0(2) ?
C5 C4 C3 . . 120.2(2) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C6 C5 C4 . . 120.4(2) ?
C6 C5 I1 . . 119.91(19) ?
C4 C5 I1 . . 119.71(19) ?
C5 C6 C1 . . 119.6(2) ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
N1 C7 C3 . . 122.2(3) ?
N1 C7 H7 . . 118.9 ?
C3 C7 H7 . . 118.9 ?
C9 C8 C13 . . 117.5(2) ?
C9 C8 N1 . . 125.2(2) ?
C13 C8 N1 . . 117.4(2) ?
C8 C9 C10 . . 121.4(3) ?
C8 C9 H9 . . 119.3 ?
C10 C9 H9 . . 119.3 ?
C9 C10 C11 . . 121.3(3) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
N2 C11 C12 . . 121.9(2) ?
N2 C11 C10 . . 121.4(3) ?
C12 C11 C10 . . 116.7(2) ?
C13 C12 C11 . . 121.1(2) ?
C13 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C12 C13 C8 . . 122.0(3) ?
C12 C13 H13 . . 119.0 ?
C8 C13 H13 . . 119.0 ?
N2 C14 C15 . . 114.7(3) ?
N2 C14 H14A . . 108.6 ?
C15 C14 H14A . . 108.6 ?
N2 C14 H14B . . 108.6 ?
C15 C14 H14B . . 108.6 ?
H14A C14 H14B . . 107.6 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N2 C16 C17 . . 114.2(3) ?
N2 C16 H16A . . 108.7 ?
C17 C16 H16A . . 108.7 ?
N2 C16 H16B . . 108.7 ?
C17 C16 H16B . . 108.7 ?
H16A C16 H16B . . 107.6 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
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 C5 . 2.085(2) ?
I2 C1 . 2.080(3) ?
O1 C2 . 1.340(3) ?
O1 H1 . 0.8200 ?
N1 C7 . 1.281(3) ?
N1 C8 . 1.411(3) ?
N2 C11 . 1.375(3) ?
N2 C14 . 1.456(4) ?
N2 C16 . 1.457(4) ?
C1 C6 . 1.381(4) ?
C1 C2 . 1.391(4) ?
C2 C3 . 1.402(4) ?
C3 C4 . 1.391(3) ?
C3 C7 . 1.450(3) ?
C4 C5 . 1.381(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.376(4) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.383(4) ?
C8 C13 . 1.384(4) ?
C9 C10 . 1.385(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.403(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.401(4) ?
C12 C13 . 1.378(4) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 C15 . 1.510(5) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 C17 . 1.489(6) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
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 H1 N1 1 0.82 1.86 2.592(3) 148
C16 H16B Cg1^i^ 2_445 0.97 2.94 3.845(4) 155
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
C6 C1 C2 O1 . . . . -177.9(2) ?
I2 C1 C2 O1 . . . . 0.8(3) ?
C6 C1 C2 C3 . . . . 1.6(4) ?
I2 C1 C2 C3 . . . . -179.80(18) ?
O1 C2 C3 C4 . . . . 177.9(2) ?
C1 C2 C3 C4 . . . . -1.5(4) ?
O1 C2 C3 C7 . . . . -1.1(4) ?
C1 C2 C3 C7 . . . . 179.5(2) ?
C2 C3 C4 C5 . . . . 0.2(4) ?
C7 C3 C4 C5 . . . . 179.2(2) ?
C3 C4 C5 C6 . . . . 1.1(4) ?
C3 C4 C5 I1 . . . . -177.55(19) ?
C4 C5 C6 C1 . . . . -1.1(4) ?
I1 C5 C6 C1 . . . . 177.6(2) ?
C2 C1 C6 C5 . . . . -0.3(4) ?
I2 C1 C6 C5 . . . . -178.9(2) ?
C8 N1 C7 C3 . . . . -179.3(2) ?
C4 C3 C7 N1 . . . . -178.5(2) ?
C2 C3 C7 N1 . . . . 0.6(4) ?
C7 N1 C8 C9 . . . . -6.6(4) ?
C7 N1 C8 C13 . . . . 173.1(2) ?
C13 C8 C9 C10 . . . . -0.6(4) ?
N1 C8 C9 C10 . . . . 179.1(3) ?
C8 C9 C10 C11 . . . . 0.2(4) ?
C14 N2 C11 C12 . . . . -9.1(4) ?
C16 N2 C11 C12 . . . . -176.7(3) ?
C14 N2 C11 C10 . . . . 171.8(3) ?
C16 N2 C11 C10 . . . . 4.3(4) ?
C9 C10 C11 N2 . . . . 178.7(3) ?
C9 C10 C11 C12 . . . . -0.4(4) ?
N2 C11 C12 C13 . . . . -178.0(3) ?
C10 C11 C12 C13 . . . . 1.1(4) ?
C11 C12 C13 C8 . . . . -1.6(4) ?
C9 C8 C13 C12 . . . . 1.3(4) ?
N1 C8 C13 C12 . . . . -178.4(2) ?
C11 N2 C14 C15 . . . . -76.2(4) ?
C16 N2 C14 C15 . . . . 91.8(4) ?
C11 N2 C16 C17 . . . . 76.8(4) ?
C14 N2 C16 C17 . . . . -91.2(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656332
