##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 926756'
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
3-{(E)-[4-(4-Hydroxy-3-methoxyphenyl)butan-2-ylidene]amino}-1-phenylurea
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H21 N3 O3'
_chemical_formula_sum     'C18 H21 N3 O3'
_chemical_formula_iupac     'C18 H21 N3 O3'
_chemical_formula_weight     327.37
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_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'
_cell_length_a     16.5464(4)
_cell_length_b     9.2184(2)
_cell_length_c     22.3975(4)
_cell_angle_alpha     90
_cell_angle_beta     100.494(2)
_cell_angle_gamma     90
_cell_volume     3359.18(13)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9245
_cell_measurement_theta_min     3.6569
_cell_measurement_theta_max     71.2611
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'prism (cut)'
_exptl_crystal_colour     'light-yellow'
_exptl_crystal_size_max     0.250
_exptl_crystal_size_mid     0.160
_exptl_crystal_size_min     0.060
_exptl_crystal_density_diffrn     1.295
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1392
_exptl_absorpt_coefficient_mu     0.729
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2011)
;
_shelx_estimated_absorpt_T_min     0.839
_shelx_estimated_absorpt_T_max     0.958
_exptl_absorpt_correction_T_min     0.91691
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction Xcaliber Eos Gemini'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     16.1952
_diffrn_reflns_number     23815
_diffrn_reflns_av_R_equivalents     0.0194
_diffrn_reflns_theta_min     3.660
_diffrn_reflns_theta_max     71.397
_diffrn_reflns_theta_full     67.680
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -20
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     27
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     6481
_reflns_number_gt     5581
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0656
_refine_ls_R_factor_gt     0.0588
_refine_ls_wR_factor_gt     0.1711
_refine_ls_wR_factor_ref     0.1796
_refine_ls_goodness_of_fit_ref     1.045
_refine_ls_restrained_S_all     1.045
_refine_ls_number_reflns     6481
_refine_ls_number_parameters     455
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.1131P)²+1.5134P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.599
_refine_diff_density_min     -0.259
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Agilent, 2011)
;
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2011)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.50355(7) 0.34300(14) 0.28183(6) 0.0292(3) Uani d 1 . .
    O O2 0.22012(9) 0.87251(16) 0.56672(6) 0.0386(4) Uani d 1 . .
    O O3 0.09139(8) 1.04987(16) 0.54412(6) 0.0350(3) Uani d 1 . .
    H H3O 0.1190(15) 1.034(3) 0.5787(7) 0.053 Uiso d 1 . .
    N N1 0.40785(9) 0.29389(16) 0.34177(6) 0.0253(3) Uani d 1 . .
    H H1N 0.3694(10) 0.337(2) 0.3564(9) 0.030 Uiso d 1 . .
    N N2 0.40724(9) 0.51144(16) 0.29066(7) 0.0256(3) Uani d 1 . .
    H H2N 0.4313(12) 0.5727(19) 0.2696(8) 0.031 Uiso d 1 . .
    N N3 0.34334(9) 0.55389(17) 0.31934(7) 0.0284(3) Uani d 1 . .
    C C1 0.44364(10) 0.37902(19) 0.30419(7) 0.0238(3) Uani d 1 . .
    C C2 0.43316(10) 0.15426(19) 0.36316(8) 0.0259(4) Uani d 1 . .
    C C3 0.47454(13) 0.0593(2) 0.33074(9) 0.0360(4) Uani d 1 . .
    H H3 0.4884 0.0887 0.2932 0.043 Uiso calc 1 . .
    C C4 0.49550(13) -0.0785(2) 0.35355(10) 0.0407(5) Uani d 1 . .
    H H4 0.5243 -0.1425 0.3316 0.049 Uiso calc 1 . .
    C C5 0.47517(13) -0.1240(2) 0.40757(10) 0.0419(5) Uani d 1 . .
    H H5 0.4894 -0.2186 0.4227 0.050 Uiso calc 1 . .
    C C6 0.43353(14) -0.0291(2) 0.43949(10) 0.0442(5) Uani d 1 . .
    H H6 0.4192 -0.0594 0.4768 0.053 Uiso calc 1 . .
    C C7 0.41258(13) 0.1094(2) 0.41765(9) 0.0368(4) Uani d 1 . .
    H H7 0.3842 0.1734 0.4400 0.044 Uiso calc 1 . .
    C C8 0.29887(11) 0.6607(2) 0.29621(8) 0.0297(4) Uani d 1 . .
    C C9 0.23057(11) 0.7061(2) 0.32858(9) 0.0326(4) Uani d 1 . .
    H H9A 0.2323 0.6455 0.3653 0.039 Uiso calc 1 . .
    H H9B 0.1769 0.6900 0.3016 0.039 Uiso calc 1 . .
    C C10 0.23837(13) 0.8663(2) 0.34707(9) 0.0355(4) Uani d 1 . .
    H H10A 0.2974 0.8905 0.3592 0.043 Uiso calc 1 . .
    H H10B 0.2158 0.9266 0.3113 0.043 Uiso calc 1 . .
    C C11 0.19461(12) 0.9052(2) 0.39874(8) 0.0329(4) Uani d 1 . .
    C C12 0.22808(13) 0.8620(2) 0.45796(9) 0.0367(4) Uani d 1 . .
    H H12 0.2757 0.8024 0.4650 0.044 Uiso calc 1 . .
    C C13 0.19215(12) 0.9056(2) 0.50660(8) 0.0307(4) Uani d 1 . .
    C C14 0.12349(11) 0.99627(19) 0.49664(8) 0.0261(4) Uani d 1 . .
    C C15 0.08828(11) 1.0335(2) 0.43795(9) 0.0302(4) Uani d 1 . .
    H H15 0.0400 1.0915 0.4307 0.036 Uiso calc 1 . .
    C C16 0.12319(11) 0.9866(2) 0.38942(8) 0.0322(4) Uani d 1 . .
    H H16 0.0976 1.0108 0.3492 0.039 Uiso calc 1 . .
    C C17 0.31178(11) 0.7458(2) 0.24149(8) 0.0329(4) Uani d 1 . .
    H H17A 0.3595 0.8096 0.2526 0.049 Uiso calc 1 . .
    H H17B 0.2628 0.8043 0.2266 0.049 Uiso calc 1 . .
    H H17C 0.3214 0.6788 0.2095 0.049 Uiso calc 1 . .
    C C18 0.30011(18) 0.8105(4) 0.58127(11) 0.0742(10) Uani d 1 . .
    H H18A 0.2995 0.7133 0.5635 0.111 Uiso calc 1 . .
    H H18B 0.3167 0.8039 0.6255 0.111 Uiso calc 1 . .
    H H18C 0.3393 0.8718 0.5648 0.111 Uiso calc 1 . .
    O O4 0.99721(7) 0.19097(14) 0.27509(6) 0.0296(3) Uani d 1 . .
    O O5 0.74121(9) -0.41262(16) 0.57259(6) 0.0389(3) Uani d 1 . .
    O O6 0.59792(8) -0.55085(16) 0.54521(6) 0.0355(3) Uani d 1 . .
    H H6O 0.6277(14) -0.547(3) 0.5798(7) 0.053 Uiso d 1 . .
    N N4 0.90978(8) 0.23778(16) 0.34148(6) 0.0245(3) Uani d 1 . .
    H H4N 0.8743(10) 0.198(2) 0.3602(8) 0.029 Uiso d 1 . .
    N N5 0.90487(9) 0.02044(16) 0.28954(7) 0.0263(3) Uani d 1 . .
    H H5N 0.9267(12) -0.040(2) 0.2668(8) 0.032 Uiso d 1 . .
    N N6 0.84546(9) -0.02354(17) 0.32229(7) 0.0288(3) Uani d 1 . .
    C C19 0.94100(10) 0.15314(18) 0.30127(7) 0.0230(3) Uani d 1 . .
    C C20 0.93614(10) 0.37987(19) 0.35945(8) 0.0251(4) Uani d 1 . .
    C C21 0.96816(12) 0.4747(2) 0.32082(8) 0.0309(4) Uani d 1 . .
    H H21 0.9735 0.4440 0.2812 0.037 Uiso calc 1 . .
    C C22 0.99218(12) 0.6136(2) 0.34046(9) 0.0350(4) Uani d 1 . .
    H H22 1.0146 0.6768 0.3142 0.042 Uiso calc 1 . .
    C C23 0.98404(12) 0.6617(2) 0.39743(9) 0.0367(4) Uani d 1 . .
    H H23 1.0006 0.7571 0.4104 0.044 Uiso calc 1 . .
    C C24 0.95139(13) 0.5686(2) 0.43530(9) 0.0384(5) Uani d 1 . .
    H H24 0.9451 0.6008 0.4745 0.046 Uiso calc 1 . .
    C C25 0.92765(12) 0.4282(2) 0.41667(8) 0.0331(4) Uani d 1 . .
    H H25 0.9056 0.3653 0.4432 0.040 Uiso calc 1 . .
    C C26 0.79860(11) -0.1278(2) 0.30028(8) 0.0292(4) Uani d 1 . .
    C C27 0.73558(11) -0.1766(2) 0.33697(9) 0.0330(4) Uani d 1 . .
    H H27A 0.6797 -0.1593 0.3134 0.040 Uiso calc 1 . .
    H H27B 0.7417 -0.1189 0.3748 0.040 Uiso calc 1 . .
    C C28 0.74571(13) -0.3380(2) 0.35290(9) 0.0364(4) Uani d 1 . .
    H H28A 0.7238 -0.3958 0.3163 0.044 Uiso calc 1 . .
    H H28B 0.8051 -0.3600 0.3645 0.044 Uiso calc 1 . .
    C C29 0.70304(12) -0.3848(2) 0.40393(9) 0.0327(4) Uani d 1 . .
    C C30 0.74324(12) -0.3697(2) 0.46427(9) 0.0342(4) Uani d 1 . .
    H H30 0.7957 -0.3245 0.4729 0.041 Uiso calc 1 . .
    C C31 0.70709(12) -0.4203(2) 0.51172(8) 0.0307(4) Uani d 1 . .
    C C32 0.63080(11) -0.49006(19) 0.49940(8) 0.0265(4) Uani d 1 . .
    C C33 0.58946(11) -0.5002(2) 0.44001(9) 0.0320(4) Uani d 1 . .
    H H33 0.5367 -0.5443 0.4314 0.038 Uiso calc 1 . .
    C C34 0.62477(12) -0.4461(2) 0.39286(8) 0.0326(4) Uani d 1 . .
    H H34 0.5951 -0.4510 0.3524 0.039 Uiso calc 1 . .
    C C35 0.80405(11) -0.2075(2) 0.24253(8) 0.0329(4) Uani d 1 . .
    H H35A 0.8160 -0.1383 0.2120 0.049 Uiso calc 1 . .
    H H35B 0.7516 -0.2560 0.2274 0.049 Uiso calc 1 . .
    H H35C 0.8481 -0.2799 0.2506 0.049 Uiso calc 1 . .
    C C36 0.82787(14) -0.3844(3) 0.58750(10) 0.0481(6) Uani d 1 . .
    H H36A 0.8572 -0.4519 0.5652 0.072 Uiso calc 1 . .
    H H36B 0.8468 -0.3976 0.6312 0.072 Uiso calc 1 . .
    H H36C 0.8388 -0.2845 0.5762 0.072 Uiso calc 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
    O1 C1 . 1.235(2) ?
    O2 C13 . 1.376(2) ?
    O2 C18 . 1.424(3) ?
    O3 C14 . 1.365(2) ?
    O3 H3O . 0.838(10) ?
    N1 C1 . 1.363(2) ?
    N1 C2 . 1.410(2) ?
    N1 H1N . 0.862(9) ?
    N2 C1 . 1.371(2) ?
    N2 N3 . 1.3895(19) ?
    N2 H2N . 0.876(9) ?
    N3 C8 . 1.281(2) ?
    C2 C7 . 1.388(2) ?
    C2 C3 . 1.394(3) ?
    C3 C4 . 1.390(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.379(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.389(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.388(3) ?
    C6 H6 . 0.9500 ?
    C7 H7 . 0.9500 ?
    C8 C17 . 1.503(2) ?
    C8 C9 . 1.509(2) ?
    C9 C10 . 1.533(3) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C11 . 1.516(2) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 C16 . 1.383(3) ?
    C11 C12 . 1.399(3) ?
    C12 C13 . 1.392(2) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.395(3) ?
    C14 C15 . 1.381(3) ?
    C15 C16 . 1.389(3) ?
    C15 H15 . 0.9500 ?
    C16 H16 . 0.9500 ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    O4 C19 . 1.237(2) ?
    O5 C31 . 1.379(2) ?
    O5 C36 . 1.436(2) ?
    O6 C32 . 1.366(2) ?
    O6 H6O . 0.840(10) ?
    N4 C19 . 1.362(2) ?
    N4 C20 . 1.416(2) ?
    N4 H4N . 0.865(9) ?
    N5 C19 . 1.366(2) ?
    N5 N6 . 1.3899(19) ?
    N5 H5N . 0.878(9) ?
    N6 C26 . 1.276(2) ?
    C20 C25 . 1.388(2) ?
    C20 C21 . 1.400(3) ?
    C21 C22 . 1.389(3) ?
    C21 H21 . 0.9500 ?
    C22 C23 . 1.380(3) ?
    C22 H22 . 0.9500 ?
    C23 C24 . 1.384(3) ?
    C23 H23 . 0.9500 ?
    C24 C25 . 1.394(3) ?
    C24 H24 . 0.9500 ?
    C25 H25 . 0.9500 ?
    C26 C35 . 1.504(3) ?
    C26 C27 . 1.509(2) ?
    C27 C28 . 1.532(3) ?
    C27 H27A . 0.9900 ?
    C27 H27B . 0.9900 ?
    C28 C29 . 1.512(2) ?
    C28 H28A . 0.9900 ?
    C28 H28B . 0.9900 ?
    C29 C34 . 1.393(3) ?
    C29 C30 . 1.400(3) ?
    C30 C31 . 1.392(3) ?
    C30 H30 . 0.9500 ?
    C31 C32 . 1.399(3) ?
    C32 C33 . 1.384(3) ?
    C33 C34 . 1.389(3) ?
    C33 H33 . 0.9500 ?
    C34 H34 . 0.9500 ?
    C35 H35A . 0.9800 ?
    C35 H35B . 0.9800 ?
    C35 H35C . 0.9800 ?
    C36 H36A . 0.9800 ?
    C36 H36B . 0.9800 ?
    C36 H36C . 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
    C13 O2 C18 . . 116.47(15) ?
    C14 O3 H3O . . 115(2) ?
    C1 N1 C2 . . 126.87(14) ?
    C1 N1 H1N . . 113.9(15) ?
    C2 N1 H1N . . 118.8(15) ?
    C1 N2 N3 . . 119.30(14) ?
    C1 N2 H2N . . 117.9(14) ?
    N3 N2 H2N . . 121.7(14) ?
    C8 N3 N2 . . 117.32(15) ?
    O1 C1 N1 . . 124.55(16) ?
    O1 C1 N2 . . 120.18(15) ?
    N1 C1 N2 . . 115.26(14) ?
    C7 C2 C3 . . 119.56(17) ?
    C7 C2 N1 . . 117.72(16) ?
    C3 C2 N1 . . 122.67(15) ?
    C4 C3 C2 . . 119.74(17) ?
    C4 C3 H3 . . 120.1 ?
    C2 C3 H3 . . 120.1 ?
    C5 C4 C3 . . 121.05(19) ?
    C5 C4 H4 . . 119.5 ?
    C3 C4 H4 . . 119.5 ?
    C4 C5 C6 . . 118.92(19) ?
    C4 C5 H5 . . 120.5 ?
    C6 C5 H5 . . 120.5 ?
    C7 C6 C5 . . 120.86(19) ?
    C7 C6 H6 . . 119.6 ?
    C5 C6 H6 . . 119.6 ?
    C6 C7 C2 . . 119.87(19) ?
    C6 C7 H7 . . 120.1 ?
    C2 C7 H7 . . 120.1 ?
    N3 C8 C17 . . 125.06(16) ?
    N3 C8 C9 . . 116.39(16) ?
    C17 C8 C9 . . 118.50(16) ?
    C8 C9 C10 . . 111.32(16) ?
    C8 C9 H9A . . 109.4 ?
    C10 C9 H9A . . 109.4 ?
    C8 C9 H9B . . 109.4 ?
    C10 C9 H9B . . 109.4 ?
    H9A C9 H9B . . 108.0 ?
    C11 C10 C9 . . 113.94(16) ?
    C11 C10 H10A . . 108.8 ?
    C9 C10 H10A . . 108.8 ?
    C11 C10 H10B . . 108.8 ?
    C9 C10 H10B . . 108.8 ?
    H10A C10 H10B . . 107.7 ?
    C16 C11 C12 . . 118.52(17) ?
    C16 C11 C10 . . 121.80(17) ?
    C12 C11 C10 . . 119.66(17) ?
    C13 C12 C11 . . 120.53(18) ?
    C13 C12 H12 . . 119.7 ?
    C11 C12 H12 . . 119.7 ?
    O2 C13 C12 . . 125.91(17) ?
    O2 C13 C14 . . 114.09(15) ?
    C12 C13 C14 . . 119.94(17) ?
    O3 C14 C15 . . 119.68(16) ?
    O3 C14 C13 . . 120.88(16) ?
    C15 C14 C13 . . 119.44(16) ?
    C14 C15 C16 . . 120.25(17) ?
    C14 C15 H15 . . 119.9 ?
    C16 C15 H15 . . 119.9 ?
    C11 C16 C15 . . 121.08(17) ?
    C11 C16 H16 . . 119.5 ?
    C15 C16 H16 . . 119.5 ?
    C8 C17 H17A . . 109.5 ?
    C8 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C8 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    O2 C18 H18A . . 109.5 ?
    O2 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    O2 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C31 O5 C36 . . 116.80(15) ?
    C32 O6 H6O . . 115(2) ?
    C19 N4 C20 . . 125.70(14) ?
    C19 N4 H4N . . 116.7(15) ?
    C20 N4 H4N . . 117.3(14) ?
    C19 N5 N6 . . 119.11(14) ?
    C19 N5 H5N . . 118.1(14) ?
    N6 N5 H5N . . 121.7(15) ?
    C26 N6 N5 . . 117.01(15) ?
    O4 C19 N4 . . 124.09(15) ?
    O4 C19 N5 . . 120.13(15) ?
    N4 C19 N5 . . 115.77(14) ?
    C25 C20 C21 . . 118.93(17) ?
    C25 C20 N4 . . 118.80(16) ?
    C21 C20 N4 . . 122.24(15) ?
    C22 C21 C20 . . 119.91(17) ?
    C22 C21 H21 . . 120.0 ?
    C20 C21 H21 . . 120.0 ?
    C23 C22 C21 . . 121.23(18) ?
    C23 C22 H22 . . 119.4 ?
    C21 C22 H22 . . 119.4 ?
    C22 C23 C24 . . 118.82(18) ?
    C22 C23 H23 . . 120.6 ?
    C24 C23 H23 . . 120.6 ?
    C23 C24 C25 . . 120.83(18) ?
    C23 C24 H24 . . 119.6 ?
    C25 C24 H24 . . 119.6 ?
    C20 C25 C24 . . 120.26(18) ?
    C20 C25 H25 . . 119.9 ?
    C24 C25 H25 . . 119.9 ?
    N6 C26 C35 . . 124.91(16) ?
    N6 C26 C27 . . 116.46(16) ?
    C35 C26 C27 . . 118.58(16) ?
    C26 C27 C28 . . 111.04(15) ?
    C26 C27 H27A . . 109.4 ?
    C28 C27 H27A . . 109.4 ?
    C26 C27 H27B . . 109.4 ?
    C28 C27 H27B . . 109.4 ?
    H27A C27 H27B . . 108.0 ?
    C29 C28 C27 . . 114.03(16) ?
    C29 C28 H28A . . 108.7 ?
    C27 C28 H28A . . 108.7 ?
    C29 C28 H28B . . 108.7 ?
    C27 C28 H28B . . 108.7 ?
    H28A C28 H28B . . 107.6 ?
    C34 C29 C30 . . 118.35(17) ?
    C34 C29 C28 . . 121.90(18) ?
    C30 C29 C28 . . 119.74(17) ?
    C31 C30 C29 . . 120.59(17) ?
    C31 C30 H30 . . 119.7 ?
    C29 C30 H30 . . 119.7 ?
    O5 C31 C30 . . 125.60(17) ?
    O5 C31 C32 . . 114.27(16) ?
    C30 C31 C32 . . 120.10(17) ?
    O6 C32 C33 . . 119.97(16) ?
    O6 C32 C31 . . 120.60(16) ?
    C33 C32 C31 . . 119.41(16) ?
    C32 C33 C34 . . 120.25(17) ?
    C32 C33 H33 . . 119.9 ?
    C34 C33 H33 . . 119.9 ?
    C33 C34 C29 . . 121.09(17) ?
    C33 C34 H34 . . 119.5 ?
    C29 C34 H34 . . 119.5 ?
    C26 C35 H35A . . 109.5 ?
    C26 C35 H35B . . 109.5 ?
    H35A C35 H35B . . 109.5 ?
    C26 C35 H35C . . 109.5 ?
    H35A C35 H35C . . 109.5 ?
    H35B C35 H35C . . 109.5 ?
    O5 C36 H36A . . 109.5 ?
    O5 C36 H36B . . 109.5 ?
    H36A C36 H36B . . 109.5 ?
    O5 C36 H36C . . 109.5 ?
    H36A C36 H36C . . 109.5 ?
    H36B C36 H36C . . 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
    C1 N2 N3 C8 . . . . -164.49(16) ?
    C2 N1 C1 O1 . . . . 2.0(3) ?
    C2 N1 C1 N2 . . . . -179.42(15) ?
    N3 N2 C1 O1 . . . . -175.81(15) ?
    N3 N2 C1 N1 . . . . 5.6(2) ?
    C1 N1 C2 C7 . . . . 154.49(18) ?
    C1 N1 C2 C3 . . . . -28.1(3) ?
    C7 C2 C3 C4 . . . . -0.7(3) ?
    N1 C2 C3 C4 . . . . -178.00(18) ?
    C2 C3 C4 C5 . . . . 0.8(3) ?
    C3 C4 C5 C6 . . . . -0.4(3) ?
    C4 C5 C6 C7 . . . . 0.0(3) ?
    C5 C6 C7 C2 . . . . 0.2(3) ?
    C3 C2 C7 C6 . . . . 0.2(3) ?
    N1 C2 C7 C6 . . . . 177.68(18) ?
    N2 N3 C8 C17 . . . . -1.6(3) ?
    N2 N3 C8 C9 . . . . -179.23(15) ?
    N3 C8 C9 C10 . . . . 123.12(19) ?
    C17 C8 C9 C10 . . . . -54.7(2) ?
    C8 C9 C10 C11 . . . . -157.88(16) ?
    C9 C10 C11 C16 . . . . -108.0(2) ?
    C9 C10 C11 C12 . . . . 73.9(2) ?
    C16 C11 C12 C13 . . . . -2.8(3) ?
    C10 C11 C12 C13 . . . . 175.28(18) ?
    C18 O2 C13 C12 . . . . 11.7(3) ?
    C18 O2 C13 C14 . . . . -165.4(2) ?
    C11 C12 C13 O2 . . . . -178.72(19) ?
    C11 C12 C13 C14 . . . . -1.7(3) ?
    O2 C13 C14 O3 . . . . 2.7(3) ?
    C12 C13 C14 O3 . . . . -174.61(17) ?
    O2 C13 C14 C15 . . . . -178.04(16) ?
    C12 C13 C14 C15 . . . . 4.6(3) ?
    O3 C14 C15 C16 . . . . 176.25(16) ?
    C13 C14 C15 C16 . . . . -3.0(3) ?
    C12 C11 C16 C15 . . . . 4.5(3) ?
    C10 C11 C16 C15 . . . . -173.55(18) ?
    C14 C15 C16 C11 . . . . -1.6(3) ?
    C19 N5 N6 C26 . . . . 162.35(16) ?
    C20 N4 C19 O4 . . . . 0.0(3) ?
    C20 N4 C19 N5 . . . . -178.54(15) ?
    N6 N5 C19 O4 . . . . 175.95(15) ?
    N6 N5 C19 N4 . . . . -5.5(2) ?
    C19 N4 C20 C25 . . . . -151.84(17) ?
    C19 N4 C20 C21 . . . . 30.1(3) ?
    C25 C20 C21 C22 . . . . 1.1(3) ?
    N4 C20 C21 C22 . . . . 179.19(17) ?
    C20 C21 C22 C23 . . . . -1.0(3) ?
    C21 C22 C23 C24 . . . . 0.1(3) ?
    C22 C23 C24 C25 . . . . 0.5(3) ?
    C21 C20 C25 C24 . . . . -0.5(3) ?
    N4 C20 C25 C24 . . . . -178.64(16) ?
    C23 C24 C25 C20 . . . . -0.3(3) ?
    N5 N6 C26 C35 . . . . 1.1(3) ?
    N5 N6 C26 C27 . . . . 178.73(15) ?
    N6 C26 C27 C28 . . . . -122.47(19) ?
    C35 C26 C27 C28 . . . . 55.3(2) ?
    C26 C27 C28 C29 . . . . 162.93(17) ?
    C27 C28 C29 C34 . . . . 95.8(2) ?
    C27 C28 C29 C30 . . . . -85.6(2) ?
    C34 C29 C30 C31 . . . . 2.6(3) ?
    C28 C29 C30 C31 . . . . -176.05(18) ?
    C36 O5 C31 C30 . . . . -16.5(3) ?
    C36 O5 C31 C32 . . . . 161.41(18) ?
    C29 C30 C31 O5 . . . . 179.33(18) ?
    C29 C30 C31 C32 . . . . 1.5(3) ?
    O5 C31 C32 O6 . . . . -3.6(3) ?
    C30 C31 C32 O6 . . . . 174.50(17) ?
    O5 C31 C32 C33 . . . . 177.97(16) ?
    C30 C31 C32 C33 . . . . -4.0(3) ?
    O6 C32 C33 C34 . . . . -176.20(17) ?
    C31 C32 C33 C34 . . . . 2.3(3) ?
    C32 C33 C34 C29 . . . . 1.9(3) ?
    C30 C29 C34 C33 . . . . -4.4(3) ?
    C28 C29 C34 C33 . . . . 174.28(18) ?
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
    N1 H1N N3 . 0.864(18) 2.178(19) 2.635(2) 112.7(15)
    N4 H4N N6 . 0.863(17) 2.230(18) 2.637(2) 108.8(14)
    O3 H3O O2 . 0.837(18) 2.29(3) 2.660(2) 107.0(18)
    O6 H6O O5 . 0.840(17) 2.28(2) 2.663(2) 108.1(17)
    O3 H3O N6 3_666 0.837(18) 2.190(16) 2.994(2) 161(2)
    O6 H6O N3 3_656 0.840(17) 2.223(16) 3.013(2) 157(2)
    N2 H2N O4 2_655 0.877(19) 2.005(19) 2.873(2) 170.4(18)
    N4 H4N O2 3_666 0.863(17) 2.544(17) 3.390(2) 166.6(15)
    N5 H5N O1 2_645 0.876(19) 2.035(19) 2.900(2) 169.3(18)
    C33 H33 O6 3_646 0.95 2.54 3.212(2) 128
    C15 H15 O3 3_575 0.95 2.63 3.166(2) 113
    C33 H33 O6 3_666 0.95 2.54 3.212(2) 128
    C10 H10A Cg1 1_565 0.99 2.80 3.774(2) 168
    C18 H18A Cg2 3_656 0.98 2.66 3.603(4) 161
    C28 H28B Cg3 1_545 0.99 2.75 3.720(2) 166
data_global
_journal_date_recd_electronic     2017-11-27
_journal_date_accepted     2017-12-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2018
_journal_volume     74
_journal_issue      1
_journal_page_first     21
_journal_page_last     27
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989017017273
_journal_coeditor_code     HB7720
_publ_contact_author_name
;
Edward R.T. Tiekink
;
_publ_contact_author_address
;
Research Centre for Crystalline Materials,
School of Science and Technology,
Sunway University,
No.5 Jalan Universiti,
47500 Bandar Sunway,
Selangor Darul Ehsan, Malaysia
;
_publ_contact_author_email     'edwardt@sunway.edu.my'
_publ_contact_author_fax
;
+60 3 7491 8633
;
_publ_contact_author_phone
;
+60 3 7491 7173
;
_publ_section_title
;
3-{(E)-[4-(4-Hydroxy-3-methoxyphenyl)butan-2-ylidene]amino}-1-phenylurea:
crystal structure and Hirshfeld surface analysis
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ming Yueh Tan' .
;
Department of Physical Science, Faculty of Applied Sciences, Tunku Abdul Rahman
 University College, 50932 Setapak, Kuala Lumpur, Malaysia
;
    'Karen A. Crouse' .
;
Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400
UPM Serdang, Selangor Darul Ehsan,, Malaysia
Department of Chemistry, St. Francis Xavier University,
PO Box 5000,
Antigonish, NS B2G 2W5,
Canada
;
    'Thahira B. S. A. Ravoof'
                  'Additional correspondence author, e-mail: thahira@upm.edu.my'
;
Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400
UPM Serdang, Selangor Darul Ehsan, Malaysia
;
    'Jotani, Mukesh M.' .
;
Department of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad,
Gujarat 380001, India
;
    'Tiekink, Edward R. T.' .
;
Research Centre for Crystalline Materials,
School of Science and Technology,
Sunway University, 47500 Bandar Sunway,
Selangor Darul Ehsan, Malaysia
;
_publ_section_synopsis
;
The disubstituted urea molecule has a twisted conformation for each of the two
molecules comprising the asymmetric unit. Intramolecular
amine-N---H...N(imine) and hydroxy-O---H...O(methoxy) hydrogen bonds are
noted. In the molecular packing, amide-N---H...O(amide),
hydroxyl-O---H...N(imine) and phenylamine-N---H...O(methoxy) hydrogen bonding
leads to layers in the ac plane.
;
