##############################################################################
#                                                                            #
# 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
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(E)-N-(2,4-Dichlorobenzylidene)-2,5-dimethoxyaniline
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H13 Cl2 N O2'
_chemical_formula_sum     'C15 H13 Cl2 N O2'
_chemical_formula_iupac     'C15 H13 Cl2 N O2'
_chemical_formula_weight     310.16
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn '
loop_
    _symmetry_equiv_pos_as_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     13.2879(12)
_cell_length_b     5.1329(5)
_cell_length_c     21.1490(18)
_cell_angle_alpha     90.00
_cell_angle_beta     96.622(2)
_cell_angle_gamma     90.00
_cell_volume     1432.9(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5300
_cell_measurement_theta_min     1.26
_cell_measurement_theta_max     28.00
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.33
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.438
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     640
_exptl_absorpt_coefficient_mu     0.453
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.875
_exptl_absorpt_correction_T_max     0.917
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(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 area-detector'
_diffrn_measurement_method     'φ and ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7646
_diffrn_reflns_av_R_equivalents     0.0197
_diffrn_reflns_av_sigmaI/netI     0.0227
_diffrn_reflns_theta_min     1.72
_diffrn_reflns_theta_max     25.20
_diffrn_reflns_theta_full     25.20
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -25
_diffrn_reflns_limit_l_max     25
_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 >
σ(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     2545
_reflns_number_gt     2166
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0373
_refine_ls_R_factor_gt     0.0299
_refine_ls_wR_factor_gt     0.0860
_refine_ls_wR_factor_ref     0.0929
_refine_ls_goodness_of_fit_ref     1.042
_refine_ls_restrained_S_all     1.042
_refine_ls_number_reflns     2545
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0481P)²+0.4104P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.183
_refine_diff_density_min     -0.181
_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' 0.0033 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'
    '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, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.23947(13) 0.0926(3) 0.90147(8) 0.0410(4) Uani d . 1 1 . .
    C C2 0.31359(13) -0.0886(4) 0.88812(8) 0.0445(4) Uani d . 1 1 . .
    C C3 0.29198(16) -0.2578(4) 0.83778(9) 0.0534(5) Uani d . 1 1 . .
    H H3 0.3401 -0.3811 0.8295 0.064 Uiso calc R 1 1 . .
    C C4 0.20020(16) -0.2487(4) 0.79912(9) 0.0531(5) Uani d . 1 1 . .
    H H4 0.1869 -0.3651 0.7655 0.064 Uiso calc R 1 1 . .
    C C5 0.12894(14) -0.0656(4) 0.81105(8) 0.0479(4) Uani d . 1 1 . .
    C C6 0.14928(14) 0.1034(4) 0.86207(8) 0.0449(4) Uani d . 1 1 . .
    H H6 0.1010 0.2270 0.8699 0.054 Uiso calc R 1 1 . .
    C C7 0.19243(13) 0.3032(4) 0.98933(8) 0.0413(4) Uani d . 1 1 . .
    H H7 0.1331 0.2057 0.9830 0.050 Uiso calc R 1 1 . .
    C C8 0.20445(12) 0.4962(3) 1.04073(7) 0.0384(4) Uani d . 1 1 . .
    C C9 0.13326(13) 0.5323(3) 1.08379(8) 0.0395(4) Uani d . 1 1 . .
    C C10 0.14630(14) 0.7172(4) 1.13174(8) 0.0448(4) Uani d . 1 1 . .
    H H10 0.0982 0.7379 1.1600 0.054 Uiso calc R 1 1 . .
    C C11 0.23178(15) 0.8692(4) 1.13661(8) 0.0460(4) Uani d . 1 1 . .
    C C12 0.30436(16) 0.8415(4) 1.09520(9) 0.0526(5) Uani d . 1 1 . .
    H H12 0.3621 0.9453 1.0993 0.063 Uiso calc R 1 1 . .
    C C13 0.28939(14) 0.6569(4) 1.04783(8) 0.0480(4) Uani d . 1 1 . .
    H H13 0.3377 0.6390 1.0196 0.058 Uiso calc R 1 1 . .
    C C14 0.47361(16) -0.2867(5) 0.92139(12) 0.0679(6) Uani d . 1 1 . .
    H H14A 0.4417 -0.4528 0.9253 0.102 Uiso calc R 1 1 . .
    H H14B 0.5300 -0.2699 0.9538 0.102 Uiso calc R 1 1 . .
    H H14C 0.4971 -0.2736 0.8802 0.102 Uiso calc R 1 1 . .
    C C15 0.0017(2) -0.2339(6) 0.73297(11) 0.0803(8) Uani d . 1 1 . .
    H H15A 0.0448 -0.2478 0.6996 0.121 Uiso calc R 1 1 . .
    H H15B -0.0663 -0.1967 0.7148 0.121 Uiso calc R 1 1 . .
    H H15C 0.0028 -0.3952 0.7560 0.121 Uiso calc R 1 1 . .
    Cl Cl1 0.02571(3) 0.33712(10) 1.08021(2) 0.05366(16) Uani d . 1 1 . .
    Cl Cl2 0.24982(5) 1.10453(10) 1.19606(2) 0.06520(19) Uani d . 1 1 . .
    N N1 0.26115(11) 0.2661(3) 0.95328(7) 0.0441(4) Uani d . 1 1 . .
    O O1 0.40247(10) -0.0847(3) 0.92844(7) 0.0575(4) Uani d . 1 1 . .
    O O2 0.03701(11) -0.0305(3) 0.77496(7) 0.0662(4) Uani d . 1 1 . .
_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
    C1 C6 . 1.380(2) ?
    C1 C2 . 1.407(2) ?
    C1 N1 . 1.416(2) ?
    C2 O1 . 1.375(2) ?
    C2 C3 . 1.379(3) ?
    C3 C4 . 1.389(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.378(3) ?
    C4 H4 . 0.9300 ?
    C5 O2 . 1.376(2) ?
    C5 C6 . 1.387(3) ?
    C6 H6 . 0.9300 ?
    C7 N1 . 1.270(2) ?
    C7 C8 . 1.466(2) ?
    C7 H7 . 0.9300 ?
    C8 C13 . 1.392(3) ?
    C8 C9 . 1.399(2) ?
    C9 C10 . 1.385(3) ?
    C9 Cl1 . 1.7397(18) ?
    C10 C11 . 1.372(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.383(3) ?
    C11 Cl2 . 1.7399(18) ?
    C12 C13 . 1.376(3) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
    C14 O1 . 1.423(2) ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C15 O2 . 1.415(3) ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 0.9600 ?
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
    C6 C1 C2 . . 119.02(16) ?
    C6 C1 N1 . . 121.81(16) ?
    C2 C1 N1 . . 119.12(16) ?
    O1 C2 C3 . . 125.15(17) ?
    O1 C2 C1 . . 115.92(16) ?
    C3 C2 C1 . . 118.91(17) ?
    C2 C3 C4 . . 121.60(18) ?
    C2 C3 H3 . . 119.2 ?
    C4 C3 H3 . . 119.2 ?
    C5 C4 C3 . . 119.38(18) ?
    C5 C4 H4 . . 120.3 ?
    C3 C4 H4 . . 120.3 ?
    O2 C5 C4 . . 124.94(17) ?
    O2 C5 C6 . . 115.51(17) ?
    C4 C5 C6 . . 119.53(18) ?
    C1 C6 C5 . . 121.49(17) ?
    C1 C6 H6 . . 119.3 ?
    C5 C6 H6 . . 119.3 ?
    N1 C7 C8 . . 121.49(17) ?
    N1 C7 H7 . . 119.3 ?
    C8 C7 H7 . . 119.3 ?
    C13 C8 C9 . . 116.89(16) ?
    C13 C8 C7 . . 119.87(15) ?
    C9 C8 C7 . . 123.23(16) ?
    C10 C9 C8 . . 122.02(17) ?
    C10 C9 Cl1 . . 117.34(13) ?
    C8 C9 Cl1 . . 120.61(14) ?
    C11 C10 C9 . . 118.51(16) ?
    C11 C10 H10 . . 120.7 ?
    C9 C10 H10 . . 120.7 ?
    C10 C11 C12 . . 121.70(17) ?
    C10 C11 Cl2 . . 119.53(14) ?
    C12 C11 Cl2 . . 118.77(15) ?
    C13 C12 C11 . . 118.63(18) ?
    C13 C12 H12 . . 120.7 ?
    C11 C12 H12 . . 120.7 ?
    C12 C13 C8 . . 122.25(17) ?
    C12 C13 H13 . . 118.9 ?
    C8 C13 H13 . . 118.9 ?
    O1 C14 H14A . . 109.5 ?
    O1 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    O1 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    O2 C15 H15A . . 109.5 ?
    O2 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    O2 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C7 N1 C1 . . 117.58(15) ?
    C2 O1 C14 . . 117.26(17) ?
    C5 O2 C15 . . 117.40(19) ?
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
    C13 H13 O1 1_565 0.93 2.62 3.357(2) 137
    C7 H7 Cl1 . 0.93 2.72 3.1000(10)
                                   106
    C13 H13 N1 . 0.93 2.52 2.826(6) 100
data_global
_journal_date_recd_electronic     2013-01-26
_journal_date_accepted     2013-02-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      4
_journal_page_first     o469
_journal_page_last     o469
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813005552
_journal_coeditor_code     CQ2001
_publ_contact_author_name     'Hai-Fu, Guo'
_publ_contact_author_address
;
School of Chemistry and Chemical Engineering
Zhaoqing University
Zhaoqing 526061
People's Republic of China
;
_publ_contact_author_email     'guohaifu@zqu.edu.cn'
_publ_contact_author_fax     '86 758 2752796'
_publ_contact_author_phone     '86 758 2752796'
_publ_section_title
;
(E)-N-(2,4-Dichlorobenzylidene)-2,5-dimethoxyaniline
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Yong Pan' .
;
College of Chemical Engineering,
Inner Mongolia University of Technology,
Inner Mongolia 010051
People's Republic of China
School of Chemistry and Chemical Engineering
Zhaoqing University
Zhaoqing 526061
People's Republic of China
;
    'Hai-Fu Guo' .
;
School of Chemistry and Chemical Engineering
Zhaoqing University
Zhaoqing 526061
People's Republic of China
;
    'De-Yun Ma' .
;
School of Chemistry and Chemical Engineering
Zhaoqing University
Zhaoqing 526061
People's Republic of China
;
