#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/49/2234901.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_2234901
loop_
_publ_author_name
'Vesek, Hilal'
'Kazak, Canan'
'Ağar, Erbil'
'Gümüş, Sümeyye'
_publ_section_title
;
 5-Diethylamino-2-{(E)-[(3-iodophenyl)imino]methyl}phenol
;
_journal_coeditor_code           BH2429
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1963
_journal_paper_doi               10.1107/S1600536812022556
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H19 I N2 O'
_chemical_formula_moiety         'C17 H19 I N2 O'
_chemical_formula_sum            'C17 H19 I N2 O'
_chemical_formula_weight         394.24
_chemical_melting_point          394
_chemical_name_systematic
;
5-Diethylamino-2-{(E)-[(3-iodophenyl)imino]methyl}phenol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6999(6)
_cell_length_b                   15.248(2)
_cell_length_c                   16.1195(15)
_cell_measurement_reflns_used    8061
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      1.84
_cell_volume                     1646.8(3)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       'rotation method'
_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  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0952
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6072
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    1.945
_exptl_absorpt_correction_T_max  0.6033
_exptl_absorpt_correction_T_min  0.4514
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.631
_refine_ls_abs_structure_details 'Flack (1983), 1355 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.862
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0337P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0735
_reflns_number_gt                2417
_reflns_number_total             3225
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2429.cif
_cod_data_source_block           I
_cod_original_cell_volume        1646.7(3)
_cod_database_code               2234901
_cod_database_fobs_code          2234901
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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 0.5355(9) 0.7994(3) 0.3130(3) 0.0424(14) Uani d . 1 1
C C2 0.6547(9) 0.8639(3) 0.2779(3) 0.0438(13) Uani d . 1 1
H H2 0.7869 0.8699 0.2946 0.053 Uiso calc R 1 1
C C3 0.5784(8) 0.9186(3) 0.2188(3) 0.0411(13) Uani d . 1 1
C C4 0.3846(10) 0.9108(4) 0.1905(4) 0.0539(16) Uani d . 1 1
H H4 0.3353 0.9477 0.1494 0.065 Uiso calc R 1 1
C C5 0.2675(12) 0.8468(4) 0.2254(4) 0.0648(16) Uani d . 1 1
H H5 0.1361 0.8409 0.2077 0.078 Uiso calc R 1 1
C C6 0.3395(9) 0.7908(4) 0.2860(4) 0.0513(15) Uani d . 1 1
H H6 0.2573 0.7478 0.3085 0.062 Uiso calc R 1 1
C C7 0.5263(10) 0.7053(4) 0.4284(3) 0.0463(16) Uani d . 1 1
H H7 0.3934 0.7205 0.4366 0.056 Uiso calc R 1 1
C C8 0.6183(8) 0.6397(4) 0.4808(4) 0.0398(14) Uani d . 1 1
C C9 0.5079(9) 0.5976(4) 0.5432(4) 0.0470(14) Uani d . 1 1
H H9 0.3765 0.6148 0.5522 0.056 Uiso calc R 1 1
C C10 0.5856(9) 0.5330(4) 0.5909(3) 0.0474(15) Uani d . 1 1
H H10 0.5071 0.5067 0.6314 0.057 Uiso calc R 1 1
C C11 0.7872(8) 0.5048(3) 0.5794(3) 0.0396(12) Uani d . 1 1
C C12 0.8970(8) 0.5476(4) 0.5182(3) 0.0429(13) Uani d . 1 1
H H12 1.0285 0.5305 0.5091 0.052 Uiso calc R 1 1
C C13 0.8187(8) 0.6140(4) 0.4706(3) 0.0382(14) Uani d . 1 1
C C14 1.0628(11) 0.4029(4) 0.6072(4) 0.0602(17) Uani d . 1 1
H H14A 1.1138 0.3722 0.6555 0.072 Uiso calc R 1 1
H H14B 1.1530 0.4512 0.5956 0.072 Uiso calc R 1 1
C C15 1.0651(14) 0.3412(6) 0.5345(5) 0.098(3) Uani d . 1 1
H H15A 1.1984 0.3200 0.5259 0.147 Uiso calc R 1 1
H H15B 1.0204 0.3715 0.4858 0.147 Uiso calc R 1 1
H H15C 0.9779 0.2926 0.5455 0.147 Uiso calc R 1 1
C C16 0.7536(12) 0.3977(4) 0.6930(3) 0.0594(15) Uani d . 1 1
H H16A 0.6713 0.4420 0.7194 0.071 Uiso calc R 1 1
H H16B 0.8452 0.3752 0.7345 0.071 Uiso calc R 1 1
C C17 0.6208(11) 0.3235(5) 0.6640(6) 0.085(2) Uani d . 1 1
H H17A 0.5497 0.2997 0.7105 0.127 Uiso calc R 1 1
H H17B 0.7012 0.2785 0.6392 0.127 Uiso calc R 1 1
H H17C 0.5273 0.3454 0.6239 0.127 Uiso calc R 1 1
I I1 0.76828(6) 1.01529(2) 0.16772(2) 0.05438(13) Uani d . 1 1
N N1 0.6279(7) 0.7428(3) 0.3703(3) 0.0431(11) Uani d . 1 1
N N2 0.8680(7) 0.4386(3) 0.6273(3) 0.0478(12) Uani d . 1 1
O O1 0.9360(6) 0.6522(3) 0.4129(2) 0.0532(11) Uani d . 1 1
H H1 0.8727 0.6905 0.3888 0.080 Uiso calc R 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'
I I -0.4742 1.8119 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 118.8(5)
C2 C1 N1 116.7(5)
C6 C1 N1 124.3(5)
C3 C2 C1 120.1(5)
C3 C2 H2 119.9
C1 C2 H2 119.9
C2 C3 C4 122.0(5)
C2 C3 I1 118.2(4)
C4 C3 I1 119.8(4)
C5 C4 C3 117.6(5)
C5 C4 H4 121.2
C3 C4 H4 121.2
C4 C5 C6 121.9(6)
C4 C5 H5 119.0
C6 C5 H5 119.0
C5 C6 C1 119.5(6)
C5 C6 H6 120.3
C1 C6 H6 120.3
N1 C7 C8 120.3(6)
N1 C7 H7 119.8
C8 C7 H7 119.8
C9 C8 C13 117.3(6)
C9 C8 C7 120.6(5)
C13 C8 C7 122.0(6)
C10 C9 C8 122.5(6)
C10 C9 H9 118.8
C8 C9 H9 118.8
C9 C10 C11 120.6(5)
C9 C10 H10 119.7
C11 C10 H10 119.7
N2 C11 C12 122.1(5)
N2 C11 C10 121.2(4)
C12 C11 C10 116.7(5)
C13 C12 C11 122.6(5)
C13 C12 H12 118.7
C11 C12 H12 118.7
O1 C13 C12 118.7(5)
O1 C13 C8 121.0(6)
C12 C13 C8 120.2(5)
N2 C14 C15 114.7(6)
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 114.0(5)
N2 C16 H16A 108.8
C17 C16 H16A 108.8
N2 C16 H16B 108.8
C17 C16 H16B 108.8
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
C7 N1 C1 121.0(5)
C11 N2 C16 121.0(5)
C11 N2 C14 120.2(5)
C16 N2 C14 118.6(5)
C13 O1 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.388(7)
C1 C6 1.390(8)
C1 N1 1.407(7)
C2 C3 1.365(7)
C2 H2 0.9300
C3 C4 1.381(8)
C3 I1 2.114(5)
C4 C5 1.373(8)
C4 H4 0.9300
C5 C6 1.384(8)
C5 H5 0.9300
C6 H6 0.9300
C7 N1 1.292(7)
C7 C8 1.446(8)
C7 H7 0.9300
C8 C9 1.404(8)
C8 C13 1.409(8)
C9 C10 1.354(8)
C9 H9 0.9300
C10 C11 1.430(9)
C10 H10 0.9300
C11 N2 1.381(7)
C11 C12 1.393(7)
C12 C13 1.374(7)
C12 H12 0.9300
C13 O1 1.349(6)
C14 N2 1.450(8)
C14 C15 1.503(10)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 N2 1.449(7)
C16 C17 1.512(9)
C16 H16A 0.9700
C16 H16B 0.9700
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
O1 H1 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_publ_flag
O1 H1 N1 0.82 1.85 2.577(6) 147.4 yes
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 1.1(8)
N1 C1 C2 C3 176.8(5)
C1 C2 C3 C4 -1.7(8)
C1 C2 C3 I1 -179.9(4)
C2 C3 C4 C5 1.5(9)
I1 C3 C4 C5 179.7(4)
C3 C4 C5 C6 -0.8(9)
C4 C5 C6 C1 0.3(9)
C2 C1 C6 C5 -0.4(8)
N1 C1 C6 C5 -175.8(5)
N1 C7 C8 C9 -179.0(6)
N1 C7 C8 C13 -0.4(9)
C13 C8 C9 C10 -1.9(9)
C7 C8 C9 C10 176.7(6)
C8 C9 C10 C11 0.3(9)
C9 C10 C11 N2 -179.6(5)
C9 C10 C11 C12 0.6(7)
N2 C11 C12 C13 -179.5(5)
C10 C11 C12 C13 0.2(8)
C11 C12 C13 O1 179.6(5)
C11 C12 C13 C8 -1.9(9)
C9 C8 C13 O1 -178.9(5)
C7 C8 C13 O1 2.5(8)
C9 C8 C13 C12 2.7(8)
C7 C8 C13 C12 -175.9(5)
C8 C7 N1 C1 172.9(5)
C2 C1 N1 C7 152.9(5)
C6 C1 N1 C7 -31.6(8)
C12 C11 N2 C16 177.3(5)
C10 C11 N2 C16 -2.5(8)
C12 C11 N2 C14 -8.6(8)
C10 C11 N2 C14 171.6(5)
C17 C16 N2 C11 85.1(7)
C17 C16 N2 C14 -89.0(7)
C15 C14 N2 C11 -76.5(8)
C15 C14 N2 C16 97.7(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657729
