#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/56/2005603.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_2005603
loop_
_publ_author_name
'Corden, J. P.'
'Bishop, P. R.'
'Errington, W.'
'Wallbridge, M. G. H.'
_publ_section_title
;
 2-{1-[(2-Amino-4,5-dimethylphenyl)imino]ethyl}phenol
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2777
_journal_page_last               2779
_journal_paper_doi               10.1107/S0108270196007159
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          'C16 H18 N2 O'
_chemical_formula_moiety         'C16 H18 N2 O'
_chemical_formula_sum            'C16 H18 N2 O'
_chemical_formula_weight         254.32
_chemical_name_systematic
;
 2-[1-[(4,5-dimethyl-2-aminophenyl)imino]ethyl]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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.
_cell_angle_beta                 90.
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   6.728(2)
_cell_length_b                   7.940(7)
_cell_length_c                   25.085(9)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.69
_cell_volume                     1340.0(13)
_computing_cell_refinement       MADNES
_computing_data_collection       'MADNES (Pflugrath & Messerschmidt, 1992)'
_computing_data_reduction        'SHELXTL-Plus (Sheldrick, 1990)'
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    SHELXTL-Plus
_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device
'Delft Instruments FAST TV area detector diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_sigmaI/netI    0.0665
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5958
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.69
_diffrn_standards_number         no
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.164
_refine_ls_abs_structure_details 'Flack (1983) parameter = -0.4(17)'
_refine_ls_abs_structure_Flack   -0.4(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.058
_refine_ls_goodness_of_fit_obs   1.127
_refine_ls_hydrogen_treatment    'H atoms: see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2105
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.406
_refine_ls_restrained_S_obs      1.126
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_obs          0.0382
_refine_ls_shift/esd_max         -0.003
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.0371P)^2^]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.1122
_refine_ls_wR_factor_obs         0.0831
_reflns_number_observed          1822
_reflns_number_total             2108
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            cf1102.cif
_cod_data_source_block           phil
_cod_database_code               2005603
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'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
O1 1 0.3193(2) 0.0326(2) 0.33213(5) 0.0337(4) Uani d D O
H1 1 0.2702(11) 0.0566(24) 0.30230(7) 0.051 Uiso calc RD H
N1 1 0.3484(3) 0.2858(2) 0.20153(7) 0.0446(5) Uani d . N
H1A 1 0.4440(3) 0.3255(2) 0.18117(7) 0.054 Uiso calc R H
H1B 1 0.3610(3) 0.2879(2) 0.23644(7) 0.054 Uiso calc R H
N2 1 0.0654(2) 0.1399(2) 0.26647(6) 0.0248(4) Uani d D N
C1 1 0.1780(3) 0.2197(2) 0.17864(8) 0.0256(5) Uani d . C
C2 1 0.1523(3) 0.2140(2) 0.12357(7) 0.0270(5) Uani d . C
H2 1 0.2525(3) 0.2609(2) 0.10138(7) 0.032 Uiso calc R H
C3 1 -0.0140(3) 0.1425(2) 0.09980(7) 0.0259(5) Uani d . C
C4 1 -0.1648(3) 0.0780(2) 0.13214(8) 0.0273(5) Uani d . C
C5 1 -0.1416(3) 0.0847(2) 0.18707(8) 0.0255(5) Uani d . C
H5 1 -0.2440(3) 0.0408(2) 0.20910(8) 0.031 Uiso calc R H
C6 1 0.0260(3) 0.1534(2) 0.21100(7) 0.0241(5) Uani d . C
C7 1 -0.0590(3) 0.1808(2) 0.30385(7) 0.0234(4) Uani d . C
C8 1 -0.2532(3) 0.2678(2) 0.29427(8) 0.0284(5) Uani d . C
H8A 1 -0.2620(8) 0.3679(9) 0.3170(4) 0.043 Uiso calc R H
H8B 1 -0.3626(3) 0.1909(6) 0.3027(5) 0.043 Uiso calc R H
H8C 1 -0.2619(8) 0.3017(14) 0.25677(13) 0.043 Uiso calc R H
C9 1 0.0007(3) 0.1424(2) 0.35908(7) 0.0245(5) Uani d . C
C10 1 -0.1283(3) 0.1740(2) 0.40204(8) 0.0320(5) Uani d . C
H10 1 -0.2549(3) 0.2224(2) 0.39517(8) 0.038 Uiso calc R H
C11 1 -0.0760(3) 0.1368(2) 0.45379(8) 0.0363(5) Uani d . C
H11 1 -0.1661(3) 0.1589(2) 0.48209(8) 0.044 Uiso calc R H
C12 1 0.1083(3) 0.0670(2) 0.46441(8) 0.0356(6) Uani d . C
H12 1 0.1455(3) 0.0423(2) 0.50010(8) 0.043 Uiso calc R H
C13 1 0.2377(3) 0.0333(2) 0.42326(8) 0.0324(5) Uani d . C
H13 1 0.3639(3) -0.0149(2) 0.43087(8) 0.039 Uiso calc R H
C14 1 0.1868(3) 0.0686(2) 0.37086(8) 0.0263(5) Uani d D C
C15 1 -0.3485(3) -0.0004(3) 0.10785(8) 0.0367(5) Uani d . C
H15A 1 -0.3109(4) -0.1010(9) 0.0876(4) 0.055 Uiso calc R H
H15B 1 -0.4122(11) 0.0810(6) 0.0840(4) 0.055 Uiso calc R H
H15C 1 -0.4414(9) -0.0318(15) 0.13625(9) 0.055 Uiso calc R H
C16 1 -0.0282(3) 0.1318(2) 0.04014(7) 0.0336(5) Uani d . C
H16A 1 -0.1572(8) 0.1757(15) 0.02849(8) 0.050 Uiso calc R H
H16B 1 -0.0152(20) 0.0140(3) 0.02898(8) 0.050 Uiso calc R H
H16C 1 0.0785(12) 0.1986(14) 0.02404(7) 0.050 Uiso calc R H
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C14 O1 H1 109.47(10) ?
C1 N1 H1A 120.00(11) ?
C1 N1 H1B 120.00(11) ?
H1A N1 H1B 120.0 ?
C7 N2 C6 124.6(2) y
N1 C1 C2 121.7(2) y
N1 C1 C6 120.2(2) y
C2 C1 C6 118.0(2) ?
C3 C2 C1 122.6(2) ?
C3 C2 H2 118.70(11) ?
C1 C2 H2 118.70(12) ?
C2 C3 C4 119.1(2) ?
C2 C3 C16 120.1(2) ?
C4 C3 C16 120.8(2) ?
C5 C4 C3 118.7(2) ?
C5 C4 C15 120.6(2) ?
C3 C4 C15 120.7(2) ?
C4 C5 C6 122.4(2) ?
C4 C5 H5 118.80(11) ?
C6 C5 H5 118.80(11) ?
C5 C6 C1 119.2(2) ?
C5 C6 N2 123.0(2) y
C1 C6 N2 117.2(2) y
N2 C7 C9 116.8(2) y
N2 C7 C8 124.2(2) y
C9 C7 C8 119.0(2) ?
C7 C8 H8A 109.47(11) ?
C7 C8 H8B 109.47(11) ?
H8A C8 H8B 109.5 ?
C7 C8 H8C 109.47(10) ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C10 C9 C14 117.4(2) ?
C10 C9 C7 121.0(2) ?
C14 C9 C7 121.6(2) ?
C11 C10 C9 121.8(2) ?
C11 C10 H10 119.11(13) ?
C9 C10 H10 119.11(12) ?
C10 C11 C12 119.7(2) ?
C10 C11 H11 120.13(13) ?
C12 C11 H11 120.13(12) ?
C13 C12 C11 120.0(2) ?
C13 C12 H12 119.99(13) ?
C11 C12 H12 119.99(12) ?
C12 C13 C14 121.0(2) ?
C12 C13 H13 119.51(13) ?
C14 C13 H13 119.51(12) ?
O1 C14 C13 118.4(2) y
O1 C14 C9 121.5(2) y
C13 C14 C9 120.1(2) ?
C4 C15 H15A 109.47(11) ?
C4 C15 H15B 109.47(11) ?
H15A C15 H15B 109.5 ?
C4 C15 H15C 109.47(11) ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C3 C16 H16A 109.47(11) ?
C3 C16 H16B 109.47(10) ?
H16A C16 H16B 109.5 ?
C3 C16 H16C 109.47(11) ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C14 1.349(2) y
O1 H1 0.84 no
N1 C1 1.385(3) y
N1 H1A 0.88 no
N1 H1B 0.88 no
N2 C7 1.298(2) y
N2 C6 1.421(2) y
C1 C2 1.393(3) ?
C1 C6 1.408(3) ?
C2 C3 1.389(3) ?
C2 H2 0.95 ?
C3 C4 1.397(3) ?
C3 C16 1.502(3) ?
C4 C5 1.388(3) ?
C4 C15 1.512(3) ?
C5 C6 1.389(3) ?
C5 H5 0.95 ?
C7 C9 1.474(3) ?
C7 C8 1.497(3) ?
C8 H8A 0.98 ?
C8 H8B 0.98 ?
C8 H8C 0.98 ?
C9 C10 1.406(3) ?
C9 C14 1.413(3) ?
C10 C11 1.377(3) ?
C10 H10 0.95 ?
C11 C12 1.384(3) ?
C11 H11 0.95 ?
C12 C13 1.377(3) ?
C12 H12 0.95 ?
C13 C14 1.387(3) ?
C13 H13 0.95 ?
C15 H15A 0.98 ?
C15 H15B 0.98 ?
C15 H15C 0.98 ?
C16 H16A 0.98 ?
C16 H16B 0.98 ?
C16 H16C 0.98 ?
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
_geom_torsion_publ_flag
N1 C1 C2 C3 177.5(2) ?
C6 C1 C2 C3 -1.5(3) ?
C1 C2 C3 C4 1.9(3) ?
C1 C2 C3 C16 -176.7(2) ?
C2 C3 C4 C5 -1.1(3) ?
C16 C3 C4 C5 177.5(2) ?
C2 C3 C4 C15 179.8(2) ?
C16 C3 C4 C15 -1.6(3) ?
C3 C4 C5 C6 0.0(3) ?
C15 C4 C5 C6 179.1(2) ?
C4 C5 C6 C1 0.3(3) ?
C4 C5 C6 N2 -170.7(2) ?
N1 C1 C6 C5 -178.7(2) ?
C2 C1 C6 C5 0.4(3) ?
N1 C1 C6 N2 -7.1(3) ?
C2 C1 C6 N2 171.9(2) ?
C7 N2 C6 C5 -52.2(3) ?
C7 N2 C6 C1 136.6(2) ?
C6 N2 C7 C9 174.18(15) y
C6 N2 C7 C8 -7.7(3) y
N2 C7 C9 C10 -176.7(2) ?
C8 C7 C9 C10 5.1(2) y
N2 C7 C9 C14 1.6(2) ?
C8 C7 C9 C14 -176.6(2) ?
C14 C9 C10 C11 0.7(3) ?
C7 C9 C10 C11 179.1(2) ?
C9 C10 C11 C12 0.3(3) ?
C10 C11 C12 C13 -0.7(3) ?
C11 C12 C13 C14 0.2(3) ?
C12 C13 C14 O1 -179.9(2) ?
C12 C13 C14 C9 0.9(3) ?
C10 C9 C14 O1 179.5(2) ?
C7 C9 C14 O1 1.2(3) ?
C10 C9 C14 C13 -1.3(3) ?
C7 C9 C14 C13 -179.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20124542
