##############################################################################
#                                                                            #
# 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_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2011-10-24
_journal_date_accepted     2011-10-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue     11
_journal_page_first     o3107
_journal_page_last     o3107
_journal_paper_category     QO
_journal_coeditor_code     SU2335
_publ_contact_author_name     'Dr. Mohammad Khaledi'
_publ_contact_author_address
;
Department of Chemistry,
Faculty of Science,
Islamic  Azad University,
Shahrekord Branch
Box 166,
Iran
;
_publ_contact_author_email     'khaledi1974@yahoo.com'
_publ_contact_author_fax     '+98-'
_publ_contact_author_phone     '+98-'
_publ_section_title
;\
(<i>E</i>,<i>E</i>)-<i>N</i>^1^,<i>N</i>^2^-Bis(2,6-difluorobenzylidene)ethane-\
1,2-diamine
;
loop_
    _publ_author_name
    _publ_author_address
    'Khaledi, Mohammad'
;
Department of Chemistry
Faculty of Science
Islamic  Azad University
Shahrekord Branch
Box 166
Tehran
Iran
;
    'Kia, Reza'
;
Department of Chemistry
Science and Research Branch
Islamic Azad University
Tehran
Iran
;
    'Clegg, William'
;
School of Chemistry
Newcastle University
Newcastle upon Tyne NE1 7RU
England
;
    'Harrington, Ross W.'
;
School of Chemistry
Newcastle University
Newcastle upon Tyne NE1 7RU
England
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(<i>E</i>,<i>E</i>)-<i>N</i>^1^,<i>N</i>^2^-Bis(2,6-
difluorobenzylidene)ethane-1,2-diamine
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C16 H12 F4 N2'
_chemical_formula_sum     'C16 H12 F4 N2'
_chemical_formula_iupac     'C16 H12 F4 N2'
_chemical_formula_weight     308.28
_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     7.3304(10)
_cell_length_b     10.5414(15)
_cell_length_c     9.2106(13)
_cell_angle_alpha     90.00
_cell_angle_beta     105.487(2)
_cell_angle_gamma     90.00
_cell_volume     685.89(17)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4055
_cell_measurement_theta_min     2.88
_cell_measurement_theta_max     28.27
_cell_measurement_temperature     150(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.34
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.493
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     316
_exptl_absorpt_coefficient_mu     0.127
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.958
_exptl_absorpt_correction_T_max     0.987
_exptl_special_details
;
The low-temperature data were collected with the Oxford Cyrosystems Cryostream
low-temperature attachment.
;
_diffrn_ambient_temperature     150(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 SMART 1K CCD area-detector
;
_diffrn_measurement_method     '\w scans'
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     4573
_diffrn_reflns_av_R_equivalents     0.0305
_diffrn_reflns_av_sigmaI/netI     0.0232
_diffrn_reflns_theta_min     3.00
_diffrn_reflns_theta_max     24.99
_diffrn_reflns_theta_full     24.99
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_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     1203
_reflns_number_gt     1057
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0490
_refine_ls_R_factor_gt     0.0431
_refine_ls_wR_factor_gt     0.1176
_refine_ls_wR_factor_ref     0.1241
_refine_ls_goodness_of_fit_ref     1.151
_refine_ls_restrained_S_all     1.151
_refine_ls_number_reflns     1203
_refine_ls_number_parameters     100
_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^)+(0.0646P)^2^+0.2701P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.267
_refine_diff_density_min     -0.227
_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'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    F F1 0.24616(17) 0.28505(10) 0.59397(12) 0.0409(4) Uani d . 1 1 . .
    F F2 0.29841(19) 0.71120(10) 0.45850(14) 0.0434(4) Uani d . 1 1 . .
    N N1 0.4481(2) 0.46153(14) 0.79618(16) 0.0297(4) Uani d . 1 1 . .
    C C1 0.5503(3) 0.51558(19) 0.9411(2) 0.0334(5) Uani d . 1 1 . .
    H H1A 0.5590 0.6088 0.9317 0.040 Uiso calc R 1 1 . .
    H H1B 0.6805 0.4809 0.9717 0.040 Uiso calc R 1 1 . .
    C C2 0.3868(2) 0.53796(16) 0.6894(2) 0.0277(4) Uani d . 1 1 . .
    H H2 0.4123 0.6256 0.7087 0.033 Uiso calc R 1 1 . .
    C C3 0.2783(2) 0.50109(15) 0.53673(18) 0.0244(4) Uani d . 1 1 . .
    C C4 0.2091(2) 0.37948(16) 0.49141(19) 0.0272(4) Uani d . 1 1 . .
    C C5 0.1031(2) 0.35046(18) 0.3480(2) 0.0311(5) Uani d . 1 1 . .
    H H5 0.0594 0.2664 0.3225 0.037 Uiso calc R 1 1 . .
    C C6 0.0615(3) 0.44634(19) 0.2419(2) 0.0332(5) Uani d . 1 1 . .
    H H6 -0.0123 0.4279 0.1426 0.040 Uiso calc R 1 1 . .
    C C7 0.1257(3) 0.56853(19) 0.2780(2) 0.0330(5) Uani d . 1 1 . .
    H H7 0.0974 0.6345 0.2052 0.040 Uiso calc R 1 1 . .
    C C8 0.2317(2) 0.59168(16) 0.4228(2) 0.0287(4) Uani d . 1 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
    F1 0.0569(8) 0.0217(6) 0.0346(6) -0.0067(5) -0.0046(5) 0.0054(4)
    F2 0.0677(8) 0.0190(6) 0.0419(7) 0.0003(5) 0.0118(6) 0.0036(5)
    N1 0.0339(8) 0.0273(8) 0.0247(8) 0.0032(6) 0.0022(6) -0.0038(6)
    C1 0.0331(10) 0.0355(10) 0.0280(10) -0.0021(8) 0.0020(8) -0.0042(8)
    C2 0.0331(9) 0.0210(9) 0.0287(9) -0.0031(7) 0.0077(7) -0.0021(7)
    C3 0.0259(8) 0.0230(9) 0.0248(9) 0.0035(7) 0.0075(7) -0.0012(7)
    C4 0.0306(9) 0.0228(9) 0.0271(9) 0.0030(7) 0.0059(7) 0.0027(7)
    C5 0.0312(9) 0.0292(10) 0.0308(10) -0.0017(7) 0.0044(8) -0.0059(7)
    C6 0.0300(9) 0.0421(11) 0.0251(9) 0.0044(8) 0.0032(7) -0.0014(8)
    C7 0.0370(10) 0.0349(10) 0.0278(10) 0.0101(8) 0.0098(8) 0.0082(8)
    C8 0.0357(10) 0.0198(9) 0.0324(10) 0.0042(7) 0.0124(8) 0.0007(7)
_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
    F1 C4 . 1.349(2) ?
    F2 C8 . 1.360(2) ?
    N1 C2 . 1.258(2) ?
    N1 C1 . 1.461(2) ?
    C1 C1 3_667 1.502(4) ?
    C1 H1A . 0.990 ?
    C1 H1B . 0.990 ?
    C2 C3 . 1.471(2) ?
    C2 H2 . 0.950 ?
    C3 C8 . 1.392(2) ?
    C3 C4 . 1.401(3) ?
    C4 C5 . 1.376(3) ?
    C5 C6 . 1.382(3) ?
    C5 H5 . 0.950 ?
    C6 C7 . 1.381(3) ?
    C6 H6 . 0.950 ?
    C7 C8 . 1.374(3) ?
    C7 H7 . 0.950 ?
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
    C2 N1 C1 . . 116.98(16) ?
    N1 C1 C1 . 3_667 110.12(19) ?
    N1 C1 H1A . . 109.6 ?
    C1 C1 H1A 3_667 . 109.6 ?
    N1 C1 H1B . . 109.6 ?
    C1 C1 H1B 3_667 . 109.6 ?
    H1A C1 H1B . . 108.1 ?
    N1 C2 C3 . . 124.56(16) ?
    N1 C2 H2 . . 117.7 ?
    C3 C2 H2 . . 117.7 ?
    C8 C3 C4 . . 114.00(15) ?
    C8 C3 C2 . . 120.03(15) ?
    C4 C3 C2 . . 125.95(15) ?
    F1 C4 C5 . . 117.69(16) ?
    F1 C4 C3 . . 118.52(15) ?
    C5 C4 C3 . . 123.79(16) ?
    C4 C5 C6 . . 118.53(17) ?
    C4 C5 H5 . . 120.7 ?
    C6 C5 H5 . . 120.7 ?
    C7 C6 C5 . . 120.98(17) ?
    C7 C6 H6 . . 119.5 ?
    C5 C6 H6 . . 119.5 ?
    C8 C7 C6 . . 117.89(18) ?
    C8 C7 H7 . . 121.1 ?
    C6 C7 H7 . . 121.1 ?
    F2 C8 C7 . . 118.23(17) ?
    F2 C8 C3 . . 116.95(16) ?
    C7 C8 C3 . . 124.81(17) ?
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
    C2 N1 C1 C1 . . . 3_667 119.1(2) ?
    C1 N1 C2 C3 . . . . -178.90(15) ?
    N1 C2 C3 C8 . . . . -174.14(17) ?
    N1 C2 C3 C4 . . . . 7.6(3) ?
    C8 C3 C4 F1 . . . . -179.76(15) ?
    C2 C3 C4 F1 . . . . -1.4(3) ?
    C8 C3 C4 C5 . . . . -0.5(3) ?
    C2 C3 C4 C5 . . . . 177.93(16) ?
    F1 C4 C5 C6 . . . . 179.17(15) ?
    C3 C4 C5 C6 . . . . -0.1(3) ?
    C4 C5 C6 C7 . . . . 0.4(3) ?
    C5 C6 C7 C8 . . . . -0.1(3) ?
    C6 C7 C8 F2 . . . . 178.75(15) ?
    C6 C7 C8 C3 . . . . -0.6(3) ?
    C4 C3 C8 F2 . . . . -178.50(14) ?
    C2 C3 C8 F2 . . . . 3.0(2) ?
    C4 C3 C8 C7 . . . . 0.8(3) ?
    C2 C3 C8 C7 . . . . -177.67(16) ?
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
    C5 H5 N1 4_565 0.95 2.53 3.471(2) 171 y