##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
1-(4-{[(E)-(4-Diethylamino-2-hydroxyphenyl)methylene]amino}phenyl)ethanone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H22 N2 O2'
_chemical_formula_sum     'C19 H22 N2 O2'
_chemical_formula_iupac     'C19 H22 N2 O2'
_chemical_formula_weight     310.39
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     16.0234(16)
_cell_length_b     7.6225(5)
_cell_length_c     15.0652(16)
_cell_angle_alpha     90.00
_cell_angle_beta     115.828(7)
_cell_angle_gamma     90.00
_cell_volume     1656.2(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     12807
_cell_measurement_theta_min     3.7
_cell_measurement_theta_max     25.6
_cell_measurement_temperature     173(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'orange brown'
_exptl_crystal_size_max     0.42
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.19
_exptl_crystal_density_diffrn     1.245
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     .
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ;
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Stoe IPDS II two-circle'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13407
_diffrn_reflns_av_R_equivalents     0.0490
_diffrn_reflns_av_sigmaI/netI     0.0312
_diffrn_reflns_theta_min     3.64
_diffrn_reflns_theta_max     25.62
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3092
_reflns_number_gt     2654
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0473
_refine_ls_R_factor_gt     0.0401
_refine_ls_wR_factor_gt     0.1044
_refine_ls_wR_factor_ref     0.1089
_refine_ls_goodness_of_fit_ref     1.029
_refine_ls_restrained_S_all     1.029
_refine_ls_number_reflns     3092
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0601P)²+0.3519P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.209
_refine_diff_density_min     -0.163
_refine_ls_extinction_method     'SHELXL (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.021(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'X-AREA (Stoe & Cie, 2001)'
_computing_cell_refinement     'X-AREA'
_computing_data_reduction     'X-AREA'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 1991)
;
_computing_publication_material     'PLATON and SHELXL97'
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
    N N1 0.48237(7) 0.31316(14) 0.38150(7) 0.0248(2) Uani d . 1 . .
    C C1 0.47354(8) 0.38747(16) 0.30007(9) 0.0250(3) Uani d . 1 . .
    H H1 0.5218 0.4612 0.3012 0.030 Uiso calc R 1 . .
    C C11 0.56015(8) 0.34157(16) 0.47302(9) 0.0231(3) Uani d . 1 . .
    C C12 0.56426(9) 0.23931(17) 0.55197(9) 0.0277(3) Uani d . 1 . .
    H H12 0.5157 0.1587 0.5418 0.033 Uiso calc R 1 . .
    C C13 0.63813(9) 0.25367(17) 0.64498(9) 0.0287(3) Uani d . 1 . .
    H H13 0.6398 0.1825 0.6975 0.034 Uiso calc R 1 . .
    C C14 0.71020(8) 0.37251(16) 0.66172(9) 0.0247(3) Uani d . 1 . .
    C C15 0.70476(9) 0.47758(18) 0.58314(9) 0.0296(3) Uani d . 1 . .
    H H15 0.7525 0.5604 0.5938 0.036 Uiso calc R 1 . .
    C C16 0.63127(9) 0.46361(18) 0.49013(9) 0.0294(3) Uani d . 1 . .
    H H16 0.6290 0.5365 0.4380 0.035 Uiso calc R 1 . .
    C C17 0.79289(8) 0.38894(17) 0.75984(9) 0.0286(3) Uani d . 1 . .
    O O17 0.85710(6) 0.48683(14) 0.77052(7) 0.0381(3) Uani d . 1 . .
    C C18 0.79640(10) 0.2787(2) 0.84472(10) 0.0380(3) Uani d . 1 . .
    H H18A 0.8526 0.3070 0.9044 0.057 Uiso calc R 1 . .
    H H18B 0.7971 0.1541 0.8289 0.057 Uiso calc R 1 . .
    H H18C 0.7417 0.3033 0.8560 0.057 Uiso calc R 1 . .
    C C21 0.39258(8) 0.36067(16) 0.20848(9) 0.0233(3) Uani d . 1 . .
    C C22 0.31639(8) 0.25651(15) 0.20272(8) 0.0230(3) Uani d . 1 . .
    C C23 0.23645(8) 0.24237(16) 0.11521(9) 0.0240(3) Uani d . 1 . .
    H H23 0.1868 0.1718 0.1133 0.029 Uiso calc R 1 . .
    C C24 0.22694(8) 0.33073(15) 0.02853(8) 0.0224(3) Uani d . 1 . .
    C C25 0.30439(8) 0.43048(17) 0.03326(9) 0.0255(3) Uani d . 1 . .
    H H25 0.3015 0.4875 -0.0241 0.031 Uiso calc R 1 . .
    C C26 0.38305(8) 0.44394(17) 0.12075(9) 0.0255(3) Uani d . 1 . .
    H H26 0.4333 0.5123 0.1223 0.031 Uiso calc R 1 . .
    O O22 0.32042(6) 0.16937(12) 0.28296(6) 0.0314(2) Uani d . 1 . .
    H H22 0.3796(14) 0.200(3) 0.3357(14) 0.064(6) Uiso d . 1 . .
    N N24 0.14626(7) 0.32124(14) -0.05657(7) 0.0258(3) Uani d . 1 . .
    C C27 0.06225(8) 0.23871(18) -0.05949(9) 0.0285(3) Uani d . 1 . .
    H H27A 0.0071 0.2981 -0.1101 0.034 Uiso calc R 1 . .
    H H27B 0.0611 0.2549 0.0052 0.034 Uiso calc R 1 . .
    C C28 0.05698(10) 0.04354(19) -0.08295(10) 0.0356(3) Uani d . 1 . .
    H H28A 0.0000 -0.0055 -0.0840 0.053 Uiso calc R 1 . .
    H H28B 0.1109 -0.0163 -0.0324 0.053 Uiso calc R 1 . .
    H H28C 0.0567 0.0268 -0.1476 0.053 Uiso calc R 1 . .
    C C29 0.13424(9) 0.41195(18) -0.14768(9) 0.0298(3) Uani d . 1 . .
    H H29A 0.0882 0.3477 -0.2053 0.036 Uiso calc R 1 . .
    H H29B 0.1939 0.4114 -0.1526 0.036 Uiso calc R 1 . .
    C C30 0.10206(10) 0.60023(19) -0.15030(11) 0.0392(4) Uani d . 1 . .
    H H30A 0.0949 0.6561 -0.2118 0.059 Uiso calc R 1 . .
    H H30B 0.1481 0.6649 -0.0940 0.059 Uiso calc R 1 . .
    H H30C 0.0424 0.6012 -0.1468 0.059 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    N1 C1 . 1.3018(16) ?
    N1 C11 . 1.4156(15) ?
    C1 C21 . 1.4383(16) ?
    C1 H1 . 0.9500 ?
    C11 C12 . 1.3995(17) ?
    C11 C16 . 1.4052(17) ?
    C12 C13 . 1.3897(17) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.4015(18) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.4002(18) ?
    C14 C17 . 1.4999(17) ?
    C15 C16 . 1.3870(18) ?
    C15 H15 . 0.9500 ?
    C16 H16 . 0.9500 ?
    C17 O17 . 1.2235(17) ?
    C17 C18 . 1.5108(19) ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C21 C26 . 1.4133(17) ?
    C21 C22 . 1.4268(17) ?
    C22 O22 . 1.3561(14) ?
    C22 C23 . 1.3852(16) ?
    C23 C24 . 1.4173(17) ?
    C23 H23 . 0.9500 ?
    C24 N24 . 1.3697(15) ?
    C24 C25 . 1.4305(17) ?
    C25 C26 . 1.3743(17) ?
    C25 H25 . 0.9500 ?
    C26 H26 . 0.9500 ?
    O22 H22 . 0.96(2) ?
    N24 C27 . 1.4691(15) ?
    N24 C29 . 1.4726(15) ?
    C27 C28 . 1.523(2) ?
    C27 H27A . 0.9900 ?
    C27 H27B . 0.9900 ?
    C28 H28A . 0.9800 ?
    C28 H28B . 0.9800 ?
    C28 H28C . 0.9800 ?
    C29 C30 . 1.520(2) ?
    C29 H29A . 0.9900 ?
    C29 H29B . 0.9900 ?
    C30 H30A . 0.9800 ?
    C30 H30B . 0.9800 ?
    C30 H30C . 0.9800 ?
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
    C1 N1 C11 . . 122.64(10) ?
    N1 C1 C21 . . 121.63(11) ?
    N1 C1 H1 . . 119.2 ?
    C21 C1 H1 . . 119.2 ?
    C12 C11 C16 . . 118.60(11) ?
    C12 C11 N1 . . 115.98(11) ?
    C16 C11 N1 . . 125.41(11) ?
    C13 C12 C11 . . 121.14(11) ?
    C13 C12 H12 . . 119.4 ?
    C11 C12 H12 . . 119.4 ?
    C12 C13 C14 . . 120.36(12) ?
    C12 C13 H13 . . 119.8 ?
    C14 C13 H13 . . 119.8 ?
    C15 C14 C13 . . 118.34(11) ?
    C15 C14 C17 . . 119.23(11) ?
    C13 C14 C17 . . 122.42(11) ?
    C16 C15 C14 . . 121.54(12) ?
    C16 C15 H15 . . 119.2 ?
    C14 C15 H15 . . 119.2 ?
    C15 C16 C11 . . 119.99(12) ?
    C15 C16 H16 . . 120.0 ?
    C11 C16 H16 . . 120.0 ?
    O17 C17 C14 . . 120.78(12) ?
    O17 C17 C18 . . 120.60(11) ?
    C14 C17 C18 . . 118.61(12) ?
    C17 C18 H18A . . 109.5 ?
    C17 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C17 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C26 C21 C22 . . 116.87(11) ?
    C26 C21 C1 . . 121.21(11) ?
    C22 C21 C1 . . 121.85(11) ?
    O22 C22 C23 . . 118.39(11) ?
    O22 C22 C21 . . 120.74(10) ?
    C23 C22 C21 . . 120.88(11) ?
    C22 C23 C24 . . 121.57(11) ?
    C22 C23 H23 . . 119.2 ?
    C24 C23 H23 . . 119.2 ?
    N24 C24 C23 . . 121.07(11) ?
    N24 C24 C25 . . 121.28(11) ?
    C23 C24 C25 . . 117.65(10) ?
    C26 C25 C24 . . 120.04(11) ?
    C26 C25 H25 . . 120.0 ?
    C24 C25 H25 . . 120.0 ?
    C25 C26 C21 . . 122.94(11) ?
    C25 C26 H26 . . 118.5 ?
    C21 C26 H26 . . 118.5 ?
    C22 O22 H22 . . 105.3(12) ?
    C24 N24 C27 . . 121.97(10) ?
    C24 N24 C29 . . 122.31(10) ?
    C27 N24 C29 . . 115.28(9) ?
    N24 C27 C28 . . 112.50(11) ?
    N24 C27 H27A . . 109.1 ?
    C28 C27 H27A . . 109.1 ?
    N24 C27 H27B . . 109.1 ?
    C28 C27 H27B . . 109.1 ?
    H27A C27 H27B . . 107.8 ?
    C27 C28 H28A . . 109.5 ?
    C27 C28 H28B . . 109.5 ?
    H28A C28 H28B . . 109.5 ?
    C27 C28 H28C . . 109.5 ?
    H28A C28 H28C . . 109.5 ?
    H28B C28 H28C . . 109.5 ?
    N24 C29 C30 . . 111.88(11) ?
    N24 C29 H29A . . 109.2 ?
    C30 C29 H29A . . 109.2 ?
    N24 C29 H29B . . 109.2 ?
    C30 C29 H29B . . 109.2 ?
    H29A C29 H29B . . 107.9 ?
    C29 C30 H30A . . 109.5 ?
    C29 C30 H30B . . 109.5 ?
    H30A C30 H30B . . 109.5 ?
    C29 C30 H30C . . 109.5 ?
    H30A C30 H30C . . 109.5 ?
    H30B C30 H30C . . 109.5 ?
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
    C11 N1 C1 C21 . . . . -178.13(11) ?
    C1 N1 C11 C12 . . . . -173.84(11) ?
    C1 N1 C11 C16 . . . . 6.92(19) ?
    C16 C11 C12 C13 . . . . -1.77(19) ?
    N1 C11 C12 C13 . . . . 178.94(11) ?
    C11 C12 C13 C14 . . . . 0.4(2) ?
    C12 C13 C14 C15 . . . . 1.14(19) ?
    C12 C13 C14 C17 . . . . -178.02(11) ?
    C13 C14 C15 C16 . . . . -1.25(19) ?
    C17 C14 C15 C16 . . . . 177.93(12) ?
    C14 C15 C16 C11 . . . . -0.2(2) ?
    C12 C11 C16 C15 . . . . 1.65(19) ?
    N1 C11 C16 C15 . . . . -179.13(12) ?
    C15 C14 C17 O17 . . . . -3.32(18) y
    C13 C14 C17 O17 . . . . 175.83(12) ?
    C15 C14 C17 C18 . . . . 178.17(12) ?
    C13 C14 C17 C18 . . . . -2.68(18) y
    N1 C1 C21 C26 . . . . 179.07(11) ?
    N1 C1 C21 C22 . . . . 2.27(18) ?
    C26 C21 C22 O22 . . . . 178.75(11) ?
    C1 C21 C22 O22 . . . . -4.32(18) ?
    C26 C21 C22 C23 . . . . -1.47(17) ?
    C1 C21 C22 C23 . . . . 175.46(11) ?
    O22 C22 C23 C24 . . . . 179.52(11) ?
    C21 C22 C23 C24 . . . . -0.27(18) ?
    C22 C23 C24 N24 . . . . -177.47(11) ?
    C22 C23 C24 C25 . . . . 2.31(17) ?
    N24 C24 C25 C26 . . . . 177.18(11) ?
    C23 C24 C25 C26 . . . . -2.60(17) ?
    C24 C25 C26 C21 . . . . 0.89(19) ?
    C22 C21 C26 C25 . . . . 1.16(18) ?
    C1 C21 C26 C25 . . . . -175.79(11) ?
    C23 C24 N24 C27 . . . . 7.78(17) y
    C25 C24 N24 C27 . . . . -171.99(11) ?
    C23 C24 N24 C29 . . . . 179.84(11) ?
    C25 C24 N24 C29 . . . . 0.07(18) y
    C24 N24 C27 C28 . . . . -90.03(14) ?
    C29 N24 C27 C28 . . . . 97.39(13) ?
    C24 N24 C29 C30 . . . . -86.08(14) ?
    C27 N24 C29 C30 . . . . 86.47(13) ?
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
    O22 H22 N1 . 0.96(2) 1.72(2) 2.6042(13) 151.8(18) yes
    C16 H16 Cg1 2_655 0.95 2.81 3.65 148 yes
    C25 H25 Cg2 2_655 0.95 3.17 3.89 135 yes
data_global
_journal_date_recd_electronic     2007-01-19
_journal_date_accepted     2007-01-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      2
_journal_page_first     o936
_journal_page_last     o938
_journal_paper_category     EO
_journal_coeditor_code     SG2121
_publ_contact_author_name     'Dr Michael Bolte'
_publ_contact_author_address
;
Institut fur Anorganische Chemie
J. W. Goethe-Universitat
Max-von-Laue-Strasse 7
60438 Frankfurt/Main
Germany
;
_publ_contact_author_email     bolte@chemie.uni-frankfurt.de
_publ_contact_author_fax     '49 69 798 29239'
_publ_contact_author_phone     '49 69 798 29136'
_publ_section_title
;\
1-(4-{[(E)-(4-Diethylamino-2-hydroxyphenyl)methylene]amino}phenyl)\
ethanone
;
loop_
    _publ_author_name
    _publ_author_address
    'Yathirajan, H. S.'
;
Department of Studies in Chemistry
University of Mysore
Manasagangotri
Mysore 570 006
India
;
    'Vijesh, A. M.'
;
Department of Chemistry
Mangalore University
Mangalagangotri 574 199
India
;
    'Narayana, B.'
;
Department of Chemistry
Mangalore University
Mangalagangotri 574 199
India
;
    'Sarojini, B. K.'
;
Department of Chemistry
P. A. College of Engineering
Nadupadavu
Mangalore 574 153
India
;
    'Bolte, Michael'
;
Institut für Anorganische Chemie
J. W. Goethe-Universität Frankfurt
Max-von-Laue-Strasse 7
60438 Frankfurt/Main
Germany
;
