##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 2.4.    #
#                                                                            #
# 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                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-01-13
_journal_date_accepted     2009-01-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      2
_journal_page_first     o362
_journal_page_last     o362
_journal_paper_category     QO
_journal_coeditor_code     PK2147
_publ_contact_author_name     'Simpson, Jim'
_publ_contact_author_address
;
Department of Chemistry,
University of Otago
P.O. Box 56,
Dunedin, 9054
New Zealand
;
_publ_contact_author_email     jsimpson@alkali.otago.ac.nz
_publ_contact_author_fax      6434797906
_publ_contact_author_phone      6434797914
_publ_section_title
;
(<i>E</i>)-4-Chloro-<i>N</i>-[(<i>E</i>)-2-methyl-3-phenylallylidene]aniline
;
loop_
    _publ_author_name
    _publ_author_address
    'Khalaji, Aliakbar D.'
;
Department of Science,
Gorgan University of Agricultural Sciences and Natural Resources,
Gorgan,
Iran
;
    'Simpson, Jim'
;
Department of Chemistry
University of Otago
PO Box 56
Dunedin
New Zealand
;
data_I
_chemical_name_systematic
;
(<i>E</i>)-4-Chloro-<i>N</i>-[(<i>E</i>)-2-methyl-3-phenylallylidene]aniline
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H14 Cl N'
_chemical_formula_sum     'C16 H14 Cl N'
_chemical_formula_iupac     'C16 H14 Cl N'
_chemical_formula_weight     255.73
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
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'
_cell_length_a     7.2486(10)
_cell_length_b     11.6637(17)
_cell_length_c     15.598(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1318.7(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5396
_cell_measurement_theta_min     2.61
_cell_measurement_theta_max     28.84
_cell_measurement_temperature     89(2)
_exptl_crystal_description     'rectangular plate'
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.288
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     536
_exptl_absorpt_coefficient_mu     0.270
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2006)'
_exptl_absorpt_correction_T_min     0.841
_exptl_absorpt_correction_T_max     0.992
_exptl_special_details
;
;
_diffrn_ambient_temperature     89(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     'Bruker APEXII CCD area-detector'
_diffrn_measurement_method     \w
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     21077
_diffrn_reflns_av_R_equivalents     0.0584
_diffrn_reflns_av_sigmaI/netI     0.0445
_diffrn_reflns_theta_min     3.14
_diffrn_reflns_theta_max     30.72
_diffrn_reflns_theta_full     30.72
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     4077
_reflns_number_gt     3517
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0483
_refine_ls_R_factor_gt     0.0394
_refine_ls_wR_factor_gt     0.1033
_refine_ls_wR_factor_ref     0.1086
_refine_ls_goodness_of_fit_ref     1.057
_refine_ls_restrained_S_all     1.057
_refine_ls_number_reflns     4077
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[\s^2^(Fo^2^)+(0.0649P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.301
_refine_diff_density_min     -0.356
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1742 Friedel pairs'
_refine_ls_abs_structure_Flack     0.01(6)
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2006)'
_computing_cell_refinement     'APEX2 (Bruker, 2006) and SAINT (Bruker, 2006)'
_computing_data_reduction     'SAINT (Bruker, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and TITAN (Hunter & Simpson, 1999)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae <i>et al.</i>,
2006)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), enCIFer (Allen <i>et al.</i>,
2004), PLATON (Spek, 2003)
and publCIF (Westrip, 2009)
;
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 0.5152(2) 0.52967(12) 0.68870(9) 0.0202(3) Uani d . 1 . .
    C C1 0.4972(2) 0.61272(13) 0.63497(9) 0.0183(3) Uani d . 1 . .
    H H1 0.4550 0.6848 0.6553 0.022 Uiso calc R 1 . .
    C C2 0.5394(2) 0.60026(13) 0.54384(9) 0.0172(3) Uani d . 1 . .
    C C3 0.6040(3) 0.48397(13) 0.51348(10) 0.0224(3) Uani d . 1 . .
    H H3A 0.5303 0.4601 0.4639 0.034 Uiso calc R 1 . .
    H H3B 0.5892 0.4280 0.5598 0.034 Uiso calc R 1 . .
    H H3C 0.7343 0.4884 0.4970 0.034 Uiso calc R 1 . .
    C C4 0.5161(2) 0.69557(13) 0.49535(10) 0.0178(3) Uani d . 1 . .
    H H4 0.4725 0.7602 0.5264 0.021 Uiso calc R 1 . .
    C C5 0.5458(2) 0.71712(13) 0.40389(10) 0.0166(3) Uani d . 1 . .
    C C6 0.6332(3) 0.64156(14) 0.34605(10) 0.0227(3) Uani d . 1 . .
    H H6 0.6771 0.5695 0.3659 0.027 Uiso calc R 1 . .
    C C7 0.6560(2) 0.67119(14) 0.26031(10) 0.0228(3) Uani d . 1 . .
    H H7 0.7151 0.6192 0.2223 0.027 Uiso calc R 1 . .
    C C8 0.5931(2) 0.77606(14) 0.22974(10) 0.0228(3) Uani d . 1 . .
    H H8 0.6072 0.7953 0.1709 0.027 Uiso calc R 1 . .
    C C9 0.5089(3) 0.85283(15) 0.28615(11) 0.0243(4) Uani d . 1 . .
    H H9 0.4672 0.9252 0.2660 0.029 Uiso calc R 1 . .
    C C10 0.4861(2) 0.82324(14) 0.37165(10) 0.0205(3) Uani d . 1 . .
    H H10 0.4286 0.8762 0.4094 0.025 Uiso calc R 1 . .
    C C11 0.4819(2) 0.55276(13) 0.77639(10) 0.0182(3) Uani d . 1 . .
    C C12 0.5526(2) 0.64996(13) 0.81773(10) 0.0203(3) Uani d . 1 . .
    H H12 0.6233 0.7040 0.7862 0.024 Uiso calc R 1 . .
    C C13 0.5200(2) 0.66792(13) 0.90454(10) 0.0207(3) Uani d . 1 . .
    H H13 0.5671 0.7342 0.9323 0.025 Uiso calc R 1 . .
    C C14 0.4183(2) 0.58807(13) 0.94995(10) 0.0193(3) Uani d . 1 . .
    Cl Cl1 0.38085(6) 0.60910(4) 1.05938(2) 0.02595(11) Uani d . 1 . .
    C C15 0.3494(2) 0.48964(13) 0.91081(11) 0.0206(3) Uani d . 1 . .
    H H15 0.2800 0.4354 0.9428 0.025 Uiso calc R 1 . .
    C C16 0.3841(2) 0.47222(13) 0.82400(10) 0.0199(3) Uani d . 1 . .
    H H16 0.3404 0.4045 0.7969 0.024 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    N1 0.0204(7) 0.0212(6) 0.0190(6) 0.0000(5) 0.0007(5) 0.0002(5)
    C1 0.0174(7) 0.0186(6) 0.0189(7) 0.0011(6) 0.0001(6) -0.0018(6)
    C2 0.0162(7) 0.0171(6) 0.0182(7) 0.0014(6) -0.0009(5) -0.0021(6)
    C3 0.0278(9) 0.0173(6) 0.0222(8) 0.0029(7) 0.0032(7) -0.0004(6)
    C4 0.0186(8) 0.0163(7) 0.0185(7) 0.0000(6) 0.0011(6) -0.0038(5)
    C5 0.0145(7) 0.0161(6) 0.0191(7) -0.0025(6) 0.0003(6) -0.0018(5)
    C6 0.0291(9) 0.0164(6) 0.0225(8) 0.0000(7) 0.0035(7) -0.0014(5)
    C7 0.0280(9) 0.0206(7) 0.0199(7) -0.0031(7) 0.0053(6) -0.0036(6)
    C8 0.0244(9) 0.0264(7) 0.0175(7) -0.0045(7) -0.0010(6) 0.0008(6)
    C9 0.0257(9) 0.0238(7) 0.0233(8) 0.0035(7) 0.0006(7) 0.0054(6)
    C10 0.0204(8) 0.0198(7) 0.0213(7) 0.0028(6) 0.0019(6) 0.0004(6)
    C11 0.0174(7) 0.0190(7) 0.0183(7) 0.0034(6) -0.0007(6) 0.0014(6)
    C12 0.0209(8) 0.0183(6) 0.0218(7) -0.0003(6) -0.0028(6) 0.0042(6)
    C13 0.0233(8) 0.0174(7) 0.0214(7) -0.0008(6) -0.0039(6) -0.0012(6)
    C14 0.0181(7) 0.0217(7) 0.0180(7) 0.0051(6) -0.0004(6) 0.0021(6)
    Cl1 0.0302(2) 0.02978(19) 0.01791(17) 0.00604(18) 0.00123(15) -0.00069(15)
    C15 0.0197(8) 0.0196(7) 0.0225(7) 0.0009(6) 0.0016(6) 0.0030(6)
    C16 0.0199(8) 0.0172(6) 0.0228(7) 0.0000(6) -0.0005(6) -0.0006(6)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 . 1.287(2) ?
    N1 C11 . 1.415(2) ?
    C1 C2 . 1.4612(19) ?
    C1 H1 . 0.9500 ?
    C2 C4 . 1.355(2) ?
    C2 C3 . 1.511(2) ?
    C3 H3A . 0.9800 ?
    C3 H3B . 0.9800 ?
    C3 H3C . 0.9800 ?
    C4 C5 . 1.464(2) ?
    C4 H4 . 0.9500 ?
    C5 C10 . 1.404(2) ?
    C5 C6 . 1.412(2) ?
    C6 C7 . 1.391(2) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.390(2) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.396(2) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.387(2) ?
    C9 H9 . 0.9500 ?
    C10 H10 . 0.9500 ?
    C11 C16 . 1.392(2) ?
    C11 C12 . 1.401(2) ?
    C12 C13 . 1.390(2) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.383(2) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.393(2) ?
    C14 Cl1 . 1.7456(16) ?
    C15 C16 . 1.392(2) ?
    C15 H15 . 0.9500 ?
    C16 H16 . 0.9500 ?
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 . . 117.96(14) ?
    N1 C1 C2 . . 122.50(14) ?
    N1 C1 H1 . . 118.8 ?
    C2 C1 H1 . . 118.8 ?
    C4 C2 C1 . . 115.80(14) ?
    C4 C2 C3 . . 126.88(13) ?
    C1 C2 C3 . . 117.32(13) ?
    C2 C3 H3A . . 109.5 ?
    C2 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 109.5 ?
    C2 C3 H3C . . 109.5 ?
    H3A C3 H3C . . 109.5 ?
    H3B C3 H3C . . 109.5 ?
    C2 C4 C5 . . 131.77(14) ?
    C2 C4 H4 . . 114.1 ?
    C5 C4 H4 . . 114.1 ?
    C10 C5 C6 . . 117.38(14) ?
    C10 C5 C4 . . 117.05(14) ?
    C6 C5 C4 . . 125.55(14) ?
    C7 C6 C5 . . 120.84(15) ?
    C7 C6 H6 . . 119.6 ?
    C5 C6 H6 . . 119.6 ?
    C8 C7 C6 . . 120.63(15) ?
    C8 C7 H7 . . 119.7 ?
    C6 C7 H7 . . 119.7 ?
    C7 C8 C9 . . 119.46(15) ?
    C7 C8 H8 . . 120.3 ?
    C9 C8 H8 . . 120.3 ?
    C10 C9 C8 . . 119.89(15) ?
    C10 C9 H9 . . 120.1 ?
    C8 C9 H9 . . 120.1 ?
    C9 C10 C5 . . 121.79(15) ?
    C9 C10 H10 . . 119.1 ?
    C5 C10 H10 . . 119.1 ?
    C16 C11 C12 . . 119.14(15) ?
    C16 C11 N1 . . 118.32(14) ?
    C12 C11 N1 . . 122.44(15) ?
    C13 C12 C11 . . 120.52(15) ?
    C13 C12 H12 . . 119.7 ?
    C11 C12 H12 . . 119.7 ?
    C14 C13 C12 . . 119.20(15) ?
    C14 C13 H13 . . 120.4 ?
    C12 C13 H13 . . 120.4 ?
    C13 C14 C15 . . 121.45(15) ?
    C13 C14 Cl1 . . 119.28(12) ?
    C15 C14 Cl1 . . 119.25(12) ?
    C16 C15 C14 . . 118.82(15) ?
    C16 C15 H15 . . 120.6 ?
    C14 C15 H15 . . 120.6 ?
    C11 C16 C15 . . 120.83(14) ?
    C11 C16 H16 . . 119.6 ?
    C15 C16 H16 . . 119.6 ?
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
    C7 H7 N1 2_664 0.95 2.67 3.524(2) 150.3
    C13 H13 Cl1 4_567 0.95 2.92 3.7311(17) 144.0