# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#============================================================================== 

data_New_Global_Publ_Block

# publcif _publ_body_element loop start
loop_
_publ_body_element
_publ_body_title
_publ_body_contents

section ? ?
# publcif _publ_body_element loop end

_publ_section_related_literature ?

# Added by publCIF - use a unique identifier for each data block

#==============================================================================


# SUBMISSION DETAILS

_publ_contact_author_name        
'William H. Ojala' # Name of author for correspondence
_publ_contact_author_address     # Address of author for correspondence


;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079 USA
;


_publ_contact_author_email       whojala@stthomas.edu
_publ_contact_author_fax         (651)-962-5209
_publ_contact_author_phone       (651)-962-5585

_publ_contact_letter             
;
Please consider this CIF for publication. I certify that this contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;

_publ_requested_journal          CrystEngComm
_publ_requested_category         FA

#==============================================================================

# TITLE AND AUTHOR LIST

_publ_section_title              
;
Fluorine-Containing Supramolecular Synthons as Structure-Differentiating Agents
in Some "Bridge-Flipped" Isomeric bis-Benzylideneanilines
;
_publ_section_title_footnote     # remove if not required
.

# The loop structure below should contain the names and addresses of all 
# authors, in the required order of publication. Repeat as necessary.

# NB if using publCIF, the Author database tool might prove useful
# (see the Tools menu in publCIF)

loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
_publ_author_email
'Ojala, William H.'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
whojala@stthomas.edu
;
'Balidemaj, Barjeta'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
barjeta.b@gmail.com
;
'Johnson, Jenna A.'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
john8308@stthomas.edu
;
'Larson, Sarah N.'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
lars7752@stthomas.edu
;
'Ojala, Charles R.'
;
Department of Chemistry
Normandale Community College
9700 France Avenue South
Bloomington, MN 55431 
USA
;
.
;
Chuck.Ojala@normandale.edu
;













#==============================================================================

# TEXT

_publ_section_synopsis           .
_publ_section_abstract           
;
(type here to add abstract)
;

_publ_section_comment            
;
(type here to add)
;

_publ_section_acknowledgements   # remove if not required
;
?
;




















_publ_section_references         
;
?
;




















_publ_section_figure_captions    
;

;

_publ_section_exptl_prep         
;
(type here to add preparation details)
;

_publ_section_exptl_refinement   
;
(type here to add refinement details)
;

#==============================================================================



data_1


_symmetry_space_group_name_hall  '-P 2yn'
#Added by publCIF




_cell_special_details            ?
#Added by publCIF



_audit_update_record             
;
2013-09-17 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
N,N'-(1,4-phenylenedimethylidyne)bis[2-fluorobenzenamine]
;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_melting_point_lt       422
_chemical_melting_point_gt       421
_chemical_formula_moiety         'C20 H14 F2 N2'
_chemical_formula_sum            'C20 H14 F2 N2'
_chemical_formula_weight         320.33

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

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                   5.8090(7)
_cell_length_b                   20.942(3)
_cell_length_c                   6.6746(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.509(2)
_cell_angle_gamma                90
_cell_volume                     774.35(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3431
_cell_measurement_theta_min      3.345
_cell_measurement_theta_max      27.384

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Siemens SMART platform CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8930
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1781
_reflns_number_gt                1348
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART, Bruker'
_computing_cell_refinement       'SAINTPLUS, Bruker'
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0401P)²+0.2341P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1781
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8943(2) 0.63095(6) 0.6469(2) 0.0239(3) Uani 1 1 d . . .
C2 C 1.0938(2) 0.67096(7) 0.6809(2) 0.0266(3) Uani 1 1 d . . .
C3 C 1.1755(3) 0.70950(7) 0.8544(2) 0.0307(3) Uani 1 1 d . . .
H3 H 1.3116 0.7364 0.8711 0.037 Uiso 1 1 calc R . .
C4 C 1.0547(3) 0.70811(7) 1.0045(2) 0.0320(3) Uani 1 1 d . . .
H4 H 1.1087 0.7340 1.1266 0.038 Uiso 1 1 calc R . .
C5 C 0.8551(3) 0.66899(7) 0.9764(2) 0.0315(3) Uani 1 1 d . . .
H5 H 0.7722 0.6684 1.0793 0.038 Uiso 1 1 calc R . .
C6 C 0.7753(3) 0.63063(6) 0.7991(2) 0.0274(3) Uani 1 1 d . . .
H6 H 0.6384 0.6040 0.7818 0.033 Uiso 1 1 calc R . .
C7 C 0.6211(2) 0.58058(6) 0.3642(2) 0.0265(3) Uani 1 1 d . . .
H7 H 0.4958 0.6009 0.4046 0.032 Uiso 1 1 calc R . .
C8 C 0.5597(2) 0.53817(6) 0.1804(2) 0.0238(3) Uani 1 1 d . . .
C9 C 0.3253(2) 0.53841(7) 0.0417(2) 0.0271(3) Uani 1 1 d . . .
H9 H 0.2054 0.5645 0.0707 0.033 Uiso 1 1 calc R . .
C10 C 0.2661(2) 0.50095(6) -0.1374(2) 0.0268(3) Uani 1 1 d . . .
H10 H 0.1066 0.5018 -0.2313 0.032 Uiso 1 1 calc R . .
F1 F 1.21019(16) 0.67254(5) 0.53281(14) 0.0402(3) Uani 1 1 d . . .
N1 N 0.8398(2) 0.59034(5) 0.46980(17) 0.0266(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0268(7) 0.0216(6) 0.0200(6) -0.0001(5) 0.0020(5) 0.0033(5)
C2 0.0279(7) 0.0291(7) 0.0234(7) 0.0009(6) 0.0085(6) 0.0022(6)
C3 0.0312(8) 0.0272(7) 0.0303(7) -0.0035(6) 0.0041(6) -0.0042(6)
C4 0.0401(9) 0.0282(7) 0.0242(7) -0.0053(6) 0.0041(6) 0.0011(6)
C5 0.0392(8) 0.0324(8) 0.0243(7) -0.0008(6) 0.0115(6) 0.0018(6)
C6 0.0296(7) 0.0253(7) 0.0259(7) 0.0013(6) 0.0062(6) -0.0010(6)
C7 0.0291(7) 0.0252(7) 0.0245(7) -0.0010(6) 0.0069(6) 0.0023(6)
C8 0.0267(7) 0.0214(6) 0.0223(6) 0.0005(5) 0.0059(5) -0.0011(5)
C9 0.0251(7) 0.0262(7) 0.0292(7) -0.0032(6) 0.0069(6) 0.0035(5)
C10 0.0236(7) 0.0265(7) 0.0261(7) -0.0018(6) 0.0013(5) 0.0009(5)
F1 0.0381(5) 0.0512(6) 0.0357(5) -0.0097(4) 0.0177(4) -0.0101(4)
N1 0.0300(6) 0.0251(6) 0.0220(6) -0.0032(5) 0.0039(5) 0.0005(5)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3903(19) . ?
C1 C2 1.3920(19) . ?
C1 N1 1.4126(17) . ?
C2 F1 1.3555(15) . ?
C2 C3 1.3738(19) . ?
C3 C4 1.386(2) . ?
C3 H3 0.95 . ?
C4 C5 1.386(2) . ?
C4 H4 0.95 . ?
C5 C6 1.3895(19) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 N1 1.2706(18) . ?
C7 C8 1.4691(19) . ?
C7 H7 0.95 . ?
C8 C10 1.3970(19) 3_665 ?
C8 C9 1.3973(18) . ?
C9 C10 1.3838(19) . ?
C9 H9 0.95 . ?
C10 C8 1.3970(19) 3_665 ?
C10 H10 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.14(12) . . ?
C6 C1 N1 124.97(12) . . ?
C2 C1 N1 117.70(12) . . ?
F1 C2 C3 118.60(12) . . ?
F1 C2 C1 117.98(12) . . ?
C3 C2 C1 123.41(13) . . ?
C2 C3 C4 118.39(13) . . ?
C2 C3 H3 120. . . ?
C4 C3 H3 120. . . ?
C3 C4 C5 119.99(13) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.54(14) . . ?
C4 C5 H5 120 . . ?
C6 C5 H5 120 . . ?
C5 C6 C1 120.52(13) . . ?
C5 C6 H6 120 . . ?
C1 C6 H6 120 . . ?
N1 C7 C8 120.77(13) . . ?
N1 C7 H7 120 . . ?
C8 C7 H7 120 . . ?
C10 C8 C9 119.19(12) 3_665 . ?
C10 C8 C7 121.15(12) 3_665 . ?
C9 C8 C7 119.62(12) . . ?
C10 C9 C8 120.63(12) . . ?
C10 C9 H9 120 . . ?
C8 C9 H9 120 . . ?
C9 C10 C8 120.18(12) . 3_665 ?
C9 C10 H10 120 . . ?
C8 C10 H10 120 3_665 . ?
C7 N1 C1 119.74(12) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag

N1 C7 C8 C10 11.2(2) . . . 3_665 ?
N1 C7 C8 C9 -166.62(13) . . . . ?
C6 C1 N1 C7 43.8(2) . . . . ?
C2 C1 N1 C7 -141.44(14) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.039
_iucr_refine_instructions_details 
;
TITL 07171m in P2(1)/n 
CELL 0.71073   5.8090  20.9418   6.6746  90.000 107.509  90.000 
ZERR    2.00   0.0007   0.0026   0.0008   0.000   0.002   0.000 
LATT 1 
SYMM 0.5-X, 0.5+Y, 0.5-Z 
SFAC C  H  N  F  
UNIT 40 28 4 4 
L.S. 4
ACTA
BOND $H 
FMAP 2
PLAN 20
HTAB 
CONF 
MPLA 3 C8 C9 C10 
MPLA 4 C7 C8 N1 C1 
MPLA 6 C1 C2 C3 C4 C5 C6 
WGHT  0.040100  0.234100 
FVAR  1.164230
TEMP -100 
MOLE 1
C1     1   0.894345  0.630951  0.646890 11.000000  0.026830  0.021620 = 
           0.020020 -0.000100  0.001960  0.003250
C2     1   1.093789  0.670965  0.680897 11.000000  0.027900  0.029120 = 
           0.023390  0.000870  0.008490  0.002240
C3     1   1.175513  0.709502  0.854431 11.000000  0.031200  0.027230 = 
           0.030290 -0.003530  0.004060 -0.004160
AFIX 43
H3     2   1.311565  0.736449  0.871130 11.000000 -1.200000
AFIX 0
C4     1   1.054695  0.708113  1.004494 11.000000  0.040120  0.028170 = 
           0.024170 -0.005290  0.004100  0.001110
AFIX 43
H4     2   1.108683  0.733985  1.126616 11.000000 -1.200000
AFIX 0
C5     1   0.855132  0.668988  0.976437 11.000000  0.039150  0.032400 = 
           0.024280 -0.000830  0.011530  0.001800
AFIX 43
H5     2   0.772173  0.668383  1.079268 11.000000 -1.200000
AFIX 0
C6     1   0.775342  0.630628  0.799123 11.000000  0.029580  0.025310 = 
           0.025930  0.001310  0.006200 -0.001040
AFIX 43
H6     2   0.638394  0.603971  0.781777 11.000000 -1.200000
AFIX 0
C7     1   0.621100  0.580577  0.364202 11.000000  0.029150  0.025200 = 
           0.024450 -0.001030  0.006930  0.002250
AFIX 43
H7     2   0.495779  0.600934  0.404597 11.000000 -1.200000
AFIX 0
C8     1   0.559723  0.538169  0.180358 11.000000  0.026670  0.021420 = 
           0.022320  0.000480  0.005930 -0.001120
C9     1   0.325309  0.538406  0.041716 11.000000  0.025090  0.026200 = 
           0.029180 -0.003190  0.006940  0.003520
AFIX 43
H9     2   0.205432  0.564527  0.070676 11.000000 -1.200000
AFIX 0
C10    1   0.266118  0.500954 -0.137372 11.000000  0.023640  0.026490 = 
           0.026060 -0.001830  0.001340  0.000900
AFIX 43
H10    2   0.106622  0.501849 -0.231342 11.000000 -1.200000
AFIX 0
F1     4   1.210194  0.672544  0.532814 11.000000  0.038120  0.051200 = 
           0.035730 -0.009700  0.017730 -0.010070
N1     3   0.839846  0.590345  0.469800 11.000000  0.030010  0.025120 = 
           0.021970 -0.003210  0.003890  0.000550
Q1     1   1.028200  0.638800  0.697900 11.000000  0.050000      0.21
Q2     1   1.171000  0.674400  0.795000 11.000000  0.050000      0.20
Q3     1   0.637100  0.518000  0.156900 11.000000  0.050000      0.17
Q4     1   0.586100  0.548700  0.279200 11.000000  0.050000      0.16
Q5     1   0.504600  0.625800  0.340300 11.000000  0.050000      0.15
Q6     1   1.060500  0.705000  0.726400 11.000000  0.050000      0.15
Q7     1   0.903700  0.705500  0.941000 11.000000  0.050000      0.15
Q8     1   0.283700  0.500600  0.001100 11.000000  0.050000      0.14
Q9     1   0.467600  0.547300  0.092000 11.000000  0.050000      0.14
Q10    1   0.864700  0.621600  0.738900 11.000000  0.050000      0.14
Q11    1   0.315700  0.530700 -0.072200 11.000000  0.050000      0.13
Q12    1   0.956500  0.559200  0.495600 11.000000  0.050000      0.13
Q13    1   0.445100  0.528400  0.133500 11.000000  0.050000      0.13
Q14    1   1.394700  0.678400  0.661400 11.000000  0.050000      0.13
Q15    1   0.938400  0.665500  0.617000 11.000000  0.050000      0.13
Q16    1   0.998000  0.674500  1.026800 11.000000  0.050000      0.12
Q17    1   1.124800  0.694900  0.940800 11.000000  0.050000      0.12
Q18    1   0.857000  0.613900  0.558300 11.000000  0.050000      0.12
Q19    1   1.257500  0.626300  0.467800 11.000000  0.050000      0.12
Q20    1   0.385800  0.616600  0.380900 11.000000  0.050000      0.11
HKLF 4 
END  
;
_database_code_depnum_ccdc_archive 'CCDC 974614'
#============================================================================== 

data_New_Global_Publ_Block

# publcif _publ_body_element loop start
loop_
_publ_body_element
_publ_body_title
_publ_body_contents

section ? ?
# publcif _publ_body_element loop end

_publ_section_related_literature ?

# Added by publCIF - use a unique identifier for each data block

#==============================================================================


# SUBMISSION DETAILS

_publ_contact_author_name        
'William H. Ojala' # Name of author for correspondence
_publ_contact_author_address     # Address of author for correspondence


;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079 USA
;


_publ_contact_author_email       whojala@stthomas.edu
_publ_contact_author_fax         (651)-962-5209
_publ_contact_author_phone       (651)-962-5585

_publ_contact_letter             
;
Please consider this CIF for publication. I certify that this contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;

_publ_requested_journal          CrystEngComm
_publ_requested_category         FA

#==============================================================================

# TITLE AND AUTHOR LIST

_publ_section_title              
;
Fluorine-Containing Supramolecular Synthons as Structure-Differentiating Agents
in Some "Bridge-Flipped" Isomeric bis-Benzylideneanilines
;
_publ_section_title_footnote     # remove if not required
.

# The loop structure below should contain the names and addresses of all 
# authors, in the required order of publication. Repeat as necessary.

# NB if using publCIF, the Author database tool might prove useful
# (see the Tools menu in publCIF)

loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
_publ_author_email
'Ojala, William H.'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
whojala@stthomas.edu
;
'Balidemaj, Barjeta'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
barjeta.b@gmail.com
;
'Johnson, Jenna A.'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
john8308@stthomas.edu
;
'Larson, Sarah N.'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
lars7752@stthomas.edu
;
'Ojala, Charles R.'
;
Department of Chemistry
Normandale Community College
9700 France Avenue South
Bloomington, MN 55431 
USA
;
.
;
Chuck.Ojala@normandale.edu
;













#==============================================================================

# TEXT

_publ_section_synopsis           .
_publ_section_abstract           
;
(type here to add abstract)
;

_publ_section_comment            
;
(type here to add)
;

_publ_section_acknowledgements   # remove if not required
;
?
;




















_publ_section_references         
;
?
;




















_publ_section_figure_captions    
;

;

_publ_section_exptl_prep         
;
(type here to add preparation details)
;

_publ_section_exptl_refinement   
;
(type here to add refinement details)
;
#==============================================================================

data_2

_symmetry_space_group_name_hall  '-P 2yn'
#Added by publCIF

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
N,N'-(1,4-phenylenedimethylidyne)bis[3-fluorobenzenamine]  
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_melting_point_lt       396
_chemical_melting_point_gt       395
_chemical_formula_moiety         'C20 H14 F2 N2'
_chemical_formula_sum            'C20 H14 F2 N2'
_chemical_formula_weight         320.33

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

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                   9.4317(14)
_cell_length_b                   3.9520(6)
_cell_length_c                   20.303(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.204(2)
_cell_angle_gamma                90
_cell_volume                     754.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2971
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.33

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9513
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8607
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         27.36
_reflns_number_total             1697
_reflns_number_gt                1445
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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.
 A small residual peak suggested disorder of the fluorophenyl group by 
 rotation about the C-N bond.  This was modeled by allowing for two
 positions of the fluorine atom with equal ADPs. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0364P)²+0.9066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1697
_refine_ls_number_parameters     114
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1416
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.259
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4220(2) 0.6531(6) 0.87675(11) 0.0312(5) Uani 1 1 d D B .
C2 C 0.3920(2) 0.7320(6) 0.81035(11) 0.0343(5) Uani 1 1 d D . .
H2 H 0.3085 0.8539 0.7961 0.041 Uiso 1 1 calc R A 1
C3 C 0.4862(2) 0.6292(6) 0.76600(11) 0.0361(5) Uani 0.951(3) 1 d PD B 1
C4 C 0.6074(2) 0.4520(6) 0.78317(12) 0.0375(5) Uani 1 1 d D . .
H4 H 0.6698 0.3837 0.7510 0.045 Uiso 1 1 calc R B 1
C5 C 0.6359(2) 0.3756(6) 0.84944(12) 0.0382(5) Uani 0.951(3) 1 d P B 1
H5 H 0.7193 0.2516 0.8629 0.046 Uiso 0.951(3) 1 calc PR B 1
C6 C 0.5459(2) 0.4754(6) 0.89606(11) 0.0351(5) Uani 1 1 d D . .
H6 H 0.5680 0.4235 0.9413 0.042 Uiso 1 1 calc R B 1
C7 C 0.2001(2) 0.7502(6) 0.91287(10) 0.0302(5) Uani 1 1 d . B .
H7 H 0.1644 0.6520 0.8723 0.036 Uiso 1 1 calc R . .
C8 C 0.0989(2) 0.8805(5) 0.95799(10) 0.0277(5) Uani 1 1 d . . .
C9 C -0.0459(2) 0.8316(6) 0.94265(10) 0.0308(5) Uani 1 1 d . . .
H9 H -0.0773 0.7167 0.9031 0.037 Uiso 1 1 calc R . .
C10 C -0.1443(2) 0.9487(6) 0.98433(10) 0.0297(5) Uani 1 1 d . . .
H10 H -0.2429 0.9126 0.9736 0.036 Uiso 1 1 calc R . .
C3' C 0.6359(2) 0.3756(6) 0.84944(12) 0.0382(5) Uani 0.049(3) 1 d PD B 2
C5' C 0.4862(2) 0.6292(6) 0.76600(11) 0.0361(5) Uani 0.049(3) 1 d PD B 2
H5' H 0.4658 0.6846 0.7208 2.0(7) Uiso 0.049(3) 1 calc PR B 2
F1 F 0.45899(17) 0.7131(5) 0.70174(7) 0.0508(5) Uani 0.951(3) 1 d PD B 1
F1' F 0.7529(14) 0.208(4) 0.8639(8) 0.0508(5) Uani 0.049(3) 1 d PD B 2
N1 N 0.33356(18) 0.7635(5) 0.92584(9) 0.0321(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0309(11) 0.0284(11) 0.0347(11) -0.0028(9) 0.0047(8) -0.0047(9)
C2 0.0316(11) 0.0339(12) 0.0375(12) 0.0004(9) 0.0038(9) 0.0004(9)
C3 0.0416(12) 0.0358(13) 0.0313(11) 0.0010(10) 0.0055(9) -0.0053(10)
C4 0.0351(11) 0.0325(12) 0.0462(13) -0.0042(10) 0.0129(10) -0.0032(10)
C5 0.0310(11) 0.0367(13) 0.0472(13) -0.0014(11) 0.0048(9) -0.0005(10)
C6 0.0326(11) 0.0365(13) 0.0359(11) -0.0005(10) 0.0008(9) -0.0030(10)
C7 0.0339(11) 0.0278(11) 0.0291(10) -0.0007(8) 0.0027(8) -0.0011(9)
C8 0.0322(10) 0.0243(10) 0.0269(10) 0.0041(8) 0.0045(8) 0.0013(8)
C9 0.0351(11) 0.0293(11) 0.0279(10) -0.0019(8) 0.0007(8) -0.0007(9)
C10 0.0281(10) 0.0298(11) 0.0312(10) 0.0013(9) 0.0019(8) -0.0006(9)
C3' 0.0310(11) 0.0367(13) 0.0472(13) -0.0014(11) 0.0048(9) -0.0005(10)
C5' 0.0416(12) 0.0358(13) 0.0313(11) 0.0010(10) 0.0055(9) -0.0053(10)
F1 0.0591(10) 0.0639(11) 0.0301(8) 0.0051(7) 0.0077(6) 0.0097(8)
F1' 0.0591(10) 0.0639(11) 0.0301(8) 0.0051(7) 0.0077(6) 0.0097(8)
N1 0.0321(9) 0.0334(10) 0.0311(9) -0.0017(8) 0.0051(7) -0.0006(8)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.392(3) . ?
C1 C6 1.395(3) . ?
C1 N1 1.414(3) . ?
C2 C3 1.372(3) . ?
C2 H2 0.95 . ?
C3 F1 1.352(3) . ?
C3 C4 1.364(3) . ?
C4 C5 1.386(3) . ?
C4 H4 0.95 . ?
C5 C6 1.375(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 N1 1.268(3) . ?
C7 C8 1.464(3) . ?
C7 H7 0.95 . ?
C8 C10 1.392(3) 3_577 ?
C8 C9 1.392(3) . ?
C9 C10 1.381(3) . ?
C9 H9 0.95 . ?
C10 C8 1.392(3) 3_577 ?
C10 H10 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.4(2) . . ?
C2 C1 N1 121.7(2) . . ?
C6 C1 N1 118.8(2) . . ?
C3 C2 C1 118.3(2) . . ?
C3 C2 H2 121 . . ?
C1 C2 H2 121 . . ?
F1 C3 C4 117.9(2) . . ?
F1 C3 C2 118.3(2) . . ?
C4 C3 C2 123.7(2) . . ?
C3 C4 C5 117.3(2) . . ?
C3 C4 H4 121. . . ?
C5 C4 H4 121. . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119. . . ?
C4 C5 H5 119. . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 H6 120. . . ?
C1 C6 H6 120. . . ?
N1 C7 C8 122.6(2) . . ?
N1 C7 H7 119 . . ?
C8 C7 H7 119 . . ?
C10 C8 C9 119.47(19) 3_577 . ?
C10 C8 C7 121.51(19) 3_577 . ?
C9 C8 C7 119.03(19) . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 120 . . ?
C8 C9 H9 120 . . ?
C9 C10 C8 119.92(19) . 3_577 ?
C9 C10 H10 120. . . ?
C8 C10 H10 120. 3_577 . ?
C7 N1 C1 117.94(18) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag


N1 C7 C8 C10 5.2(3) . . . 3_577 ?
N1 C7 C8 C9 -174.8(2) . . . . ?
C2 C1 N1 C7 41.2(3) . . . . ?
C6 C1 N1 C7 -142.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.36
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.056
_iucr_refine_instructions_details 
;
TITL 12148a in P2(1)/n 
CELL 0.71073   9.4317   3.9520  20.3028  90.000  94.204  90.000 
ZERR    2.00   0.0014   0.0006   0.0031   0.000   0.002   0.000 
LATT 1 
SYMM 0.5-X, 0.5+Y, 0.5-Z 
SFAC C  H  N  F  
UNIT 40 28 4 4 
L.S. 8
ACTA
BOND $H 
FMAP 2
PLAN 20
SIZE 0.080 0.150 0.500 
CONF 
EADP F1 F1' 
SADI C2 F1 C4 F1 C6 F1' C4 F1' 
SADI C3 F1 C3' F1' 
EXYZ C3 C5' 
EADP C3 C5' 
EXYZ C5 C3' 
EADP C5 C3' 
FLAT C6 C5' F1' C4 C1 C2 C3' 
MPLA 3 C8 C9 C10 
MPLA 4 C7 C8 N1 C1 
MPLA 6 C1 C2 C3 C4 C5 C6 
WGHT  0.036400  0.906600 
FVAR  1.081560  0.950980
TEMP -100 
MOLE 1
C1     1   0.421971  0.653117  0.876751 11.000000  0.030890  0.028420 = 
           0.034660 -0.002800  0.004720 -0.004750
C2     1   0.391991  0.732029  0.810352 11.000000  0.031590  0.033860 = 
           0.037540  0.000360  0.003770  0.000380
AFIX 43
H2     2   0.308479  0.853920  0.796128 11.000000 -1.200000
PART 1
AFIX 0
C3     1   0.486157  0.629224  0.766001 21.000000  0.041640  0.035810 = 
           0.031270  0.000990  0.005530 -0.005320
PART 0
C4     1   0.607380  0.451982  0.783171 11.000000  0.035140  0.032480 = 
           0.046210 -0.004210  0.012930 -0.003200
AFIX 43
H4     2   0.669776  0.383667  0.750990 11.000000 -1.200000
PART 1
AFIX 0
C5     1   0.635866  0.375564  0.849442 21.000000  0.031000  0.036680 = 
           0.047150 -0.001440  0.004780 -0.000540
AFIX 43
H5     2   0.719296  0.251623  0.862930 21.000000 -1.200000
PART 0
AFIX 0
C6     1   0.545879  0.475425  0.896059 11.000000  0.032580  0.036540 = 
           0.035950 -0.000520  0.000760 -0.002960
AFIX 43
H6     2   0.568039  0.423517  0.941333 11.000000 -1.200000
AFIX 0
C7     1   0.200119  0.750243  0.912874 11.000000  0.033870  0.027840 = 
           0.029080 -0.000730  0.002750 -0.001100
AFIX 43
H7     2   0.164401  0.651972  0.872291 11.000000 -1.200000
AFIX 0
C8     1   0.098932  0.880482  0.957990 11.000000  0.032210  0.024300 = 
           0.026870  0.004070  0.004500  0.001290
C9     1  -0.045874  0.831598  0.942652 11.000000  0.035070  0.029260 = 
           0.027860 -0.001930  0.000710 -0.000730
AFIX 43
H9     2  -0.077281  0.716657  0.903149 11.000000 -1.200000
AFIX 0
C10    1  -0.144328  0.948655  0.984333 11.000000  0.028110  0.029820 = 
           0.031210  0.001320  0.001870 -0.000570
AFIX 43
H10    2  -0.242919  0.912583  0.973645 11.000000 -1.200000
PART 2
AFIX 0
C3'    1   0.635866  0.375564  0.849442 -21.000000  0.031000  0.036680 = 
           0.047150 -0.001440  0.004780 -0.000540
C5'    1   0.486157  0.629224  0.766001 -21.000000  0.041640  0.035810 = 
           0.031270  0.000990  0.005530 -0.005320
AFIX 43
H5'    2   0.465793  0.684604  0.720762 -21.000000  2.000000
PART 1
AFIX 0
F1     4   0.458994  0.713054  0.701738 21.000000  0.059110  0.063920 = 
           0.030110  0.005140  0.007660  0.009730
PART 2
F1'    4   0.752949  0.207855  0.863884 -21.000000  0.059110  0.063920 = 
           0.030110  0.005140  0.007660  0.009730
PART 0
N1     3   0.333561  0.763462  0.925840 11.000000  0.032090  0.033440 = 
           0.031070 -0.001660  0.005090 -0.000550
HKLF 4 
END   
;
# start Validation Reply Form
_vrf_SHFSU01_2                   
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: We believe this is a result of our modeling of the disorder in the fluorine position.
;
_vrf_PLAT080_2                   
;
PROBLEM: Maximum Shift/Error ............................ 0.26
RESPONSE: We believe this is a result of our modeling of the disorder in the fluorine position.
;
_vrf_PLAT222_2                   
;
PROBLEM: Large Non-Solvent H Uiso(max)/Uiso(min) .. 10.0 Ratio
RESPONSE: We believe this is a result of our modeling of the disorder in the fluorine position.
;
_database_code_depnum_ccdc_archive 'CCDC 974615'
#============================================================================== 

data_New_Global_Publ_Block

# publcif _publ_body_element loop start
loop_
_publ_body_element
_publ_body_title
_publ_body_contents

section ? ?
# publcif _publ_body_element loop end

_publ_section_related_literature ?

# Added by publCIF - use a unique identifier for each data block

#==============================================================================


# SUBMISSION DETAILS

_publ_contact_author_name        
'William H. Ojala' # Name of author for correspondence
_publ_contact_author_address     # Address of author for correspondence


;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079 USA
;


_publ_contact_author_email       whojala@stthomas.edu
_publ_contact_author_fax         (651)-962-5209
_publ_contact_author_phone       (651)-962-5585

_publ_contact_letter             
;
Please consider this CIF for publication. I certify that this contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;

_publ_requested_journal          CrystEngComm
_publ_requested_category         FA

#==============================================================================

# TITLE AND AUTHOR LIST

_publ_section_title              
;
Fluorine-Containing Supramolecular Synthons as Structure-Differentiating Agents
in Some "Bridge-Flipped" Isomeric bis-Benzylideneanilines
;
_publ_section_title_footnote     # remove if not required
.

# The loop structure below should contain the names and addresses of all 
# authors, in the required order of publication. Repeat as necessary.

# NB if using publCIF, the Author database tool might prove useful
# (see the Tools menu in publCIF)

loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
_publ_author_email
'Ojala, William H.'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
whojala@stthomas.edu
;
'Balidemaj, Barjeta'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
barjeta.b@gmail.com
;
'Johnson, Jenna A.'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
john8308@stthomas.edu
;
'Larson, Sarah N.'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
lars7752@stthomas.edu
;
'Ojala, Charles R.'
;
Department of Chemistry
Normandale Community College
9700 France Avenue South
Bloomington, MN 55431 
USA
;
.
;
Chuck.Ojala@normandale.edu
;













#==============================================================================

# TEXT

_publ_section_synopsis           .
_publ_section_abstract           
;
(type here to add abstract)
;

_publ_section_comment            
;
(type here to add)
;

_publ_section_acknowledgements   # remove if not required
;
?
;




















_publ_section_references         
;
?
;




















_publ_section_figure_captions    
;

;

_publ_section_exptl_prep         
;
(type here to add preparation details)
;

_publ_section_exptl_refinement   
;
(type here to add refinement details)
;
# end Validation Reply Form
#==============================================================================


data_3


_cell_special_details            ?
#Added by publCIF




_symmetry_space_group_name_hall  '-P 2ybc'
#Added by publCIF



_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 N,N'-(1,4-phenylenedimethylidyne)bis[4-fluorobenzenamine]
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_melting_point_lt       424
_chemical_melting_point_gt       423
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 F2 N2'
_chemical_formula_weight         320.33

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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                   7.4680(11)
_cell_length_b                   5.6986(8)
_cell_length_c                   36.149(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.239(2)
_cell_angle_gamma                90
_cell_volume                     1532.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2971
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9473
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17753
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         27.59
_reflns_number_total             3550
_reflns_number_gt                2728
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0557P)²+0.5585P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0048(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3550
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.00040(16) 0.5043(2) 0.11632(3) 0.0226(3) Uani 1 1 d . . .
C2 C 0.03015(17) 0.6903(2) 0.09254(3) 0.0246(3) Uani 1 1 d . . .
H2 H 0.1015 0.8198 0.1015 0.030 Uiso 1 1 calc R . .
C3 C -0.04317(18) 0.6870(2) 0.05587(4) 0.0271(3) Uani 1 1 d . . .
H3 H -0.0221 0.8122 0.0395 0.032 Uiso 1 1 calc R . .
C4 C -0.14759(18) 0.4970(2) 0.04387(3) 0.0258(3) Uani 1 1 d . . .
C5 C -0.18028(17) 0.3102(2) 0.06645(4) 0.0259(3) Uani 1 1 d . . .
H5 H -0.2536 0.1828 0.0574 0.031 Uiso 1 1 calc R . .
C6 C -0.10334(17) 0.3132(2) 0.10276(3) 0.0247(3) Uani 1 1 d . . .
H6 H -0.1208 0.1839 0.1186 0.030 Uiso 1 1 calc R . .
C7 C 0.09232(17) 0.6771(2) 0.17318(3) 0.0249(3) Uani 1 1 d . . .
H7 H 0.0486 0.8213 0.1627 0.030 Uiso 1 1 calc R . .
C8 C 0.17526(16) 0.6739(2) 0.21158(3) 0.0227(3) Uani 1 1 d . . .
C9 C 0.15283(17) 0.8650(2) 0.23486(3) 0.0253(3) Uani 1 1 d . . .
H9 H 0.0889 0.9997 0.2255 0.030 Uiso 1 1 calc R . .
C10 C 0.22347(17) 0.8587(2) 0.27161(3) 0.0251(3) Uani 1 1 d . . .
H10 H 0.2082 0.9897 0.2873 0.030 Uiso 1 1 calc R . .
C11 C 0.50921(17) 0.4886(2) 0.37963(3) 0.0230(3) Uani 1 1 d . . .
C12 C 0.61396(17) 0.6768(2) 0.39367(3) 0.0251(3) Uani 1 1 d . . .
H12 H 0.6412 0.8010 0.3776 0.030 Uiso 1 1 calc R . .
C13 C 0.67867(17) 0.6843(2) 0.43081(4) 0.0260(3) Uani 1 1 d . . .
H13 H 0.7503 0.8121 0.4404 0.031 Uiso 1 1 calc R . .
C14 C 0.63647(17) 0.5016(2) 0.45347(3) 0.0244(3) Uani 1 1 d . . .
C15 C 0.53537(17) 0.3112(2) 0.44057(4) 0.0263(3) Uani 1 1 d . . .
H15 H 0.5091 0.1876 0.4569 0.032 Uiso 1 1 calc R . .
C16 C 0.47306(17) 0.3043(2) 0.40333(3) 0.0255(3) Uani 1 1 d . . .
H16 H 0.4051 0.1731 0.3938 0.031 Uiso 1 1 calc R . .
C17 C 0.38524(16) 0.6582(2) 0.32511(3) 0.0238(3) Uani 1 1 d . . .
H17 H 0.3879 0.8009 0.3387 0.029 Uiso 1 1 calc R . .
C18 C 0.31683(16) 0.6617(2) 0.28578(3) 0.0224(3) Uani 1 1 d . . .
C19 C 0.34331(17) 0.4722(2) 0.26222(3) 0.0233(3) Uani 1 1 d . . .
H19 H 0.4097 0.3392 0.2715 0.028 Uiso 1 1 calc R . .
C20 C 0.27335(17) 0.4783(2) 0.22564(3) 0.0239(3) Uani 1 1 d . . .
H20 H 0.2916 0.3491 0.2098 0.029 Uiso 1 1 calc R . .
F1 F -0.22004(12) 0.49398(15) 0.00806(2) 0.0379(2) Uani 1 1 d . . .
F2 F 0.70080(11) 0.50723(15) 0.48979(2) 0.0352(2) Uani 1 1 d . . .
N1 N 0.07745(14) 0.49196(19) 0.15357(3) 0.0252(3) Uani 1 1 d . . .
N2 N 0.44109(15) 0.4717(2) 0.34172(3) 0.0261(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0213(6) 0.0257(7) 0.0206(6) -0.0009(5) 0.0010(5) 0.0032(5)
C2 0.0239(6) 0.0253(6) 0.0244(6) -0.0022(5) 0.0013(5) -0.0021(5)
C3 0.0302(7) 0.0266(7) 0.0244(6) 0.0031(5) 0.0029(5) 0.0017(5)
C4 0.0274(6) 0.0305(7) 0.0186(6) -0.0028(5) -0.0025(5) 0.0044(5)
C5 0.0247(6) 0.0255(7) 0.0271(7) -0.0046(5) 0.0006(5) -0.0019(5)
C6 0.0266(6) 0.0239(6) 0.0238(6) 0.0005(5) 0.0035(5) 0.0011(5)
C7 0.0253(6) 0.0271(7) 0.0219(6) 0.0017(5) 0.0000(5) 0.0017(5)
C8 0.0217(6) 0.0266(7) 0.0196(6) -0.0005(5) 0.0008(5) -0.0015(5)
C9 0.0253(6) 0.0245(6) 0.0257(6) 0.0014(5) 0.0007(5) 0.0022(5)
C10 0.0261(6) 0.0255(6) 0.0237(6) -0.0044(5) 0.0025(5) 0.0000(5)
C11 0.0226(6) 0.0266(7) 0.0197(6) -0.0008(5) 0.0004(5) 0.0014(5)
C12 0.0254(6) 0.0261(7) 0.0237(6) 0.0034(5) 0.0016(5) -0.0018(5)
C13 0.0248(6) 0.0265(7) 0.0263(7) -0.0024(5) -0.0009(5) -0.0029(5)
C14 0.0248(6) 0.0296(7) 0.0182(6) -0.0006(5) -0.0009(5) 0.0040(5)
C15 0.0275(6) 0.0258(7) 0.0255(6) 0.0046(5) 0.0021(5) 0.0002(5)
C16 0.0254(6) 0.0241(6) 0.0266(7) -0.0003(5) -0.0010(5) -0.0018(5)
C17 0.0242(6) 0.0281(7) 0.0189(6) -0.0024(5) 0.0013(5) -0.0016(5)
C18 0.0209(6) 0.0265(7) 0.0196(6) -0.0002(5) 0.0014(4) -0.0027(5)
C19 0.0236(6) 0.0234(6) 0.0225(6) 0.0007(5) 0.0001(5) 0.0018(5)
C20 0.0256(6) 0.0245(6) 0.0215(6) -0.0035(5) 0.0015(5) -0.0001(5)
F1 0.0505(5) 0.0386(5) 0.0222(4) -0.0015(3) -0.0099(4) -0.0002(4)
F2 0.0449(5) 0.0387(5) 0.0202(4) 0.0012(3) -0.0068(3) -0.0014(4)
N1 0.0248(5) 0.0293(6) 0.0209(5) -0.0005(4) -0.0007(4) 0.0005(5)
N2 0.0267(6) 0.0300(6) 0.0212(5) 0.0002(4) -0.0003(4) -0.0020(5)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3956(18) . ?
C1 C2 1.3966(18) . ?
C1 N1 1.4190(15) . ?
C2 C3 1.3872(17) . ?
C2 H2 0.95 . ?
C3 C4 1.3808(19) . ?
C3 H3 0.95 . ?
C4 F1 1.3565(14) . ?
C4 C5 1.3768(19) . ?
C5 C6 1.3843(17) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 N1 1.2701(17) . ?
C7 C8 1.4675(16) . ?
C7 H7 0.95 . ?
C8 C9 1.3957(18) . ?
C8 C20 1.4034(18) . ?
C9 C10 1.3843(17) . ?
C9 H9 0.95 . ?
C10 C18 1.3943(18) . ?
C10 H10 0.95 . ?
C11 C12 1.3953(18) . ?
C11 C16 1.3972(18) . ?
C11 N2 1.4208(15) . ?
C12 C13 1.3855(17) . ?
C12 H12 0.95 . ?
C13 C14 1.3793(18) . ?
C13 H13 0.95 . ?
C14 F2 1.3568(14) . ?
C14 C15 1.3784(19) . ?
C15 C16 1.3840(17) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C17 N2 1.2720(17) . ?
C17 C18 1.4665(16) . ?
C17 H17 0.95 . ?
C18 C19 1.4004(17) . ?
C19 C20 1.3772(17) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.45(11) . . ?
C6 C1 N1 117.35(11) . . ?
C2 C1 N1 123.09(11) . . ?
C3 C2 C1 120.36(12) . . ?
C3 C2 H2 120 . . ?
C1 C2 H2 120 . . ?
C4 C3 C2 118.24(12) . . ?
C4 C3 H3 120. . . ?
C2 C3 H3 120. . . ?
F1 C4 C5 118.61(11) . . ?
F1 C4 C3 118.33(12) . . ?
C5 C4 C3 123.06(12) . . ?
C4 C5 C6 118.17(12) . . ?
C4 C5 H5 120. . . ?
C6 C5 H5 120. . . ?
C5 C6 C1 120.68(12) . . ?
C5 C6 H6 120 . . ?
C1 C6 H6 120 . . ?
N1 C7 C8 121.70(12) . . ?
N1 C7 H7 120 . . ?
C8 C7 H7 120 . . ?
C9 C8 C20 119.26(11) . . ?
C9 C8 C7 119.81(11) . . ?
C20 C8 C7 120.91(11) . . ?
C10 C9 C8 120.16(12) . . ?
C10 C9 H9 120 . . ?
C8 C9 H9 120 . . ?
C9 C10 C18 120.47(12) . . ?
C9 C10 H10 120 . . ?
C18 C10 H10 120 . . ?
C12 C11 C16 119.21(11) . . ?
C12 C11 N2 122.84(11) . . ?
C16 C11 N2 117.93(11) . . ?
C13 C12 C11 120.71(12) . . ?
C13 C12 H12 120 . . ?
C11 C12 H12 120 . . ?
C14 C13 C12 118.27(12) . . ?
C14 C13 H13 120. . . ?
C12 C13 H13 120. . . ?
F2 C14 C15 118.73(11) . . ?
F2 C14 C13 118.48(11) . . ?
C15 C14 C13 122.76(12) . . ?
C14 C15 C16 118.46(12) . . ?
C14 C15 H15 120. . . ?
C16 C15 H15 120. . . ?
C15 C16 C11 120.56(12) . . ?
C15 C16 H16 120 . . ?
C11 C16 H16 120 . . ?
N2 C17 C18 122.64(12) . . ?
N2 C17 H17 120 . . ?
C18 C17 H17 120 . . ?
C10 C18 C19 119.43(11) . . ?
C10 C18 C17 119.04(11) . . ?
C19 C18 C17 121.53(11) . . ?
C20 C19 C18 120.15(12) . . ?
C20 C19 H19 120 . . ?
C18 C19 H19 120 . . ?
C19 C20 C8 120.49(11) . . ?
C19 C20 H20 120 . . ?
C8 C20 H20 120 . . ?
C7 N1 C1 119.74(11) . . ?
C17 N2 C11 118.15(11) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag

N1 C7 C8 C9 -165.32(13) . . . . ?
N1 C7 C8 C20 13.00(19) . . . . ?
N2 C17 C18 C10 166.47(12) . . . . ?
N2 C17 C18 C19 -13.59(19) . . . . ?
C6 C1 N1 C7 -145.19(13) . . . . ?
C2 C1 N1 C7 38.62(18) . . . . ?
C12 C11 N2 C17 -38.78(18) . . . . ?
C16 C11 N2 C17 143.11(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042
_iucr_refine_instructions_details 
;
TITL 12241a in P2(1)/c 
CELL 0.71073   7.4680   5.6986  36.1492  90.000  95.239  90.000 
ZERR    4.00   0.0011   0.0008   0.0052   0.000   0.002   0.000 
LATT 1 
SYMM -X, 0.5+Y, 0.5-Z 
SFAC C  H  N  F  
UNIT 80 56 8 8 
L.S. 4
EXTI  0.00475
ACTA
BOND $H 
FMAP 2
PLAN 20
MPLA 6 C1 C2 C3 C4 C5 C6 
MPLA 6 C8 C9 C10 C18 C19 C20 
MPLA 6 C11 C12 C13 C14 C15 C16 
MPLA 4 N1 C7 C8 C1 
MPLA 4 N2 C17 C18 C11 
CONF 
SIZE 0.050 0.200 0.550 
WGHT  0.055700  0.558500 
FVAR  0.338540
TEMP -100 
C1     1  -0.000398  0.504275  0.116319 11.000000  0.021270  0.025650 = 
           0.020620 -0.000880  0.001020  0.003220
C2     1   0.030150  0.690291  0.092538 11.000000  0.023890  0.025260 = 
           0.024450 -0.002180  0.001270 -0.002150
AFIX 43
H2     2   0.101534  0.819778  0.101520 11.000000 -1.200000
AFIX 0
C3     1  -0.043171  0.687016  0.055872 11.000000  0.030200  0.026630 = 
           0.024440  0.003130  0.002860  0.001690
AFIX 43
H3     2  -0.022095  0.812157  0.039456 11.000000 -1.200000
AFIX 0
C4     1  -0.147595  0.497046  0.043867 11.000000  0.027380  0.030460 = 
           0.018610 -0.002780 -0.002490  0.004360
C5     1  -0.180283  0.310235  0.066449 11.000000  0.024710  0.025530 = 
           0.027140 -0.004560  0.000610 -0.001880
AFIX 43
H5     2  -0.253624  0.182798  0.057358 11.000000 -1.200000
AFIX 0
C6     1  -0.103336  0.313224  0.102765 11.000000  0.026550  0.023910 = 
           0.023840  0.000460  0.003460  0.001070
AFIX 43
H6     2  -0.120781  0.183890  0.118624 11.000000 -1.200000
AFIX 0
C7     1   0.092322  0.677059  0.173185 11.000000  0.025300  0.027130 = 
           0.021870  0.001750  0.000050  0.001740
AFIX 43
H7     2   0.048624  0.821298  0.162727 11.000000 -1.200000
AFIX 0
C8     1   0.175262  0.673870  0.211581 11.000000  0.021700  0.026560 = 
           0.019620 -0.000510  0.000770 -0.001520
C9     1   0.152832  0.864977  0.234860 11.000000  0.025310  0.024490 = 
           0.025690  0.001390  0.000670  0.002220
AFIX 43
H9     2   0.088935  0.999654  0.225463 11.000000 -1.200000
AFIX 0
C10    1   0.223471  0.858750  0.271609 11.000000  0.026090  0.025540 = 
           0.023720 -0.004420  0.002510 -0.000010
AFIX 43
H10    2   0.208230  0.989667  0.287286 11.000000 -1.200000
AFIX 0
C11    1   0.509212  0.488579  0.379630 11.000000  0.022570  0.026610 = 
           0.019650 -0.000840  0.000430  0.001370
C12    1   0.613960  0.676759  0.393665 11.000000  0.025360  0.026120 = 
           0.023750  0.003350  0.001630 -0.001790
AFIX 43
H12    2   0.641200  0.801025  0.377581 11.000000 -1.200000
AFIX 0
C13    1   0.678674  0.684339  0.430806 11.000000  0.024810  0.026460 = 
           0.026260 -0.002360 -0.000940 -0.002880
AFIX 43
H13    2   0.750251  0.812096  0.440414 11.000000 -1.200000
AFIX 0
C14    1   0.636470  0.501565  0.453468 11.000000  0.024820  0.029620 = 
           0.018220 -0.000560 -0.000850  0.003980
C15    1   0.535366  0.311201  0.440568 11.000000  0.027490  0.025760 = 
           0.025520  0.004610  0.002060  0.000180
AFIX 43
H15    2   0.509062  0.187613  0.456858 11.000000 -1.200000
AFIX 0
C16    1   0.473065  0.304293  0.403334 11.000000  0.025370  0.024050 = 
           0.026570 -0.000300 -0.000970 -0.001820
AFIX 43
H16    2   0.405145  0.173138  0.393811 11.000000 -1.200000
AFIX 0
C17    1   0.385236  0.658169  0.325111 11.000000  0.024170  0.028150 = 
           0.018940 -0.002410  0.001290 -0.001550
AFIX 43
H17    2   0.387949  0.800881  0.338735 11.000000 -1.200000
AFIX 0
C18    1   0.316826  0.661708  0.285777 11.000000  0.020920  0.026510 = 
           0.019590 -0.000190  0.001440 -0.002690
C19    1   0.343312  0.472205  0.262221 11.000000  0.023590  0.023410 = 
           0.022470  0.000700  0.000110  0.001790
AFIX 43
H19    2   0.409687  0.339173  0.271497 11.000000 -1.200000
AFIX 0
C20    1   0.273353  0.478264  0.225641 11.000000  0.025570  0.024550 = 
           0.021540 -0.003520  0.001480 -0.000080
AFIX 43
H20    2   0.291632  0.349074  0.209808 11.000000 -1.200000
AFIX 0
F1     4  -0.220036  0.493983  0.008065 11.000000  0.050510  0.038630 = 
           0.022180 -0.001500 -0.009940 -0.000220
F2     4   0.700800  0.507234  0.489794 11.000000  0.044920  0.038680 = 
           0.020180  0.001170 -0.006760 -0.001410
N1     3   0.077449  0.491956  0.153572 11.000000  0.024770  0.029270 = 
           0.020940 -0.000510 -0.000670  0.000480
N2     3   0.441085  0.471689  0.341721 11.000000  0.026680  0.029980 = 
           0.021220  0.000200 -0.000320 -0.002010
Q1     1   0.353900  0.664700  0.303800 11.000000  0.050000      0.36
Q2     1   0.151800  0.675900  0.193400 11.000000  0.050000      0.33
Q3     1   0.474200  0.484600  0.361300 11.000000  0.050000      0.28
Q4     1   0.555000  0.578200  0.388000 11.000000  0.050000      0.26
Q5     1  -0.005500  0.600400  0.105400 11.000000  0.050000      0.26
Q6     1   0.619700  0.621100  0.444800 11.000000  0.050000      0.26
Q7     1   0.039300  0.498500  0.136100 11.000000  0.050000      0.25
Q8     1   0.310800  0.779000  0.277200 11.000000  0.050000      0.25
Q9     1  -0.129700  0.611600  0.052500 11.000000  0.050000      0.25
Q10    1   0.197000  0.797300  0.219700 11.000000  0.050000      0.25
Q11    1   0.238600  0.595400  0.217600 11.000000  0.050000      0.24
Q12    1   0.294100  0.482900  0.244600 11.000000  0.050000      0.24
Q13    1   0.674700  0.575900  0.441000 11.000000  0.050000      0.24
Q14    1   0.581600  0.419800  0.446400 11.000000  0.050000      0.24
Q15    1  -0.025100  0.392500  0.108100 11.000000  0.050000      0.23
Q16    1   0.455600  0.431400  0.393900 11.000000  0.050000      0.23
Q17    1   0.330000  0.575400  0.274400 11.000000  0.050000      0.22
Q18    1   0.611000  0.683600  0.413900 11.000000  0.050000      0.21
Q19    1   0.226500  0.878400  0.250900 11.000000  0.050000      0.21
Q20    1  -0.131100  0.386300  0.053100 11.000000  0.050000      0.21
HKLF 4 
END  
;
_database_code_depnum_ccdc_archive 'CCDC 974616'
#============================================================================== 

data_New_Global_Publ_Block

# publcif _publ_body_element loop start
loop_
_publ_body_element
_publ_body_title
_publ_body_contents

section ? ?
# publcif _publ_body_element loop end

_publ_section_related_literature ?

# Added by publCIF - use a unique identifier for each data block

#==============================================================================


# SUBMISSION DETAILS

_publ_contact_author_name        
'William H. Ojala' # Name of author for correspondence
_publ_contact_author_address     # Address of author for correspondence


;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079 USA
;


_publ_contact_author_email       whojala@stthomas.edu
_publ_contact_author_fax         (651)-962-5209
_publ_contact_author_phone       (651)-962-5585

_publ_contact_letter             
;
Please consider this CIF for publication. I certify that this contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;

_publ_requested_journal          CrystEngComm
_publ_requested_category         FA

#==============================================================================

# TITLE AND AUTHOR LIST

_publ_section_title              
;
Fluorine-Containing Supramolecular Synthons as Structure-Differentiating Agents
in Some "Bridge-Flipped" Isomeric bis-Benzylideneanilines
;
_publ_section_title_footnote     # remove if not required
.

# The loop structure below should contain the names and addresses of all 
# authors, in the required order of publication. Repeat as necessary.

# NB if using publCIF, the Author database tool might prove useful
# (see the Tools menu in publCIF)

loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
_publ_author_email
'Ojala, William H.'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
whojala@stthomas.edu
;
'Balidemaj, Barjeta'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
barjeta.b@gmail.com
;
'Johnson, Jenna A.'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
john8308@stthomas.edu
;
'Larson, Sarah N.'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
lars7752@stthomas.edu
;
'Ojala, Charles R.'
;
Department of Chemistry
Normandale Community College
9700 France Avenue South
Bloomington, MN 55431 
USA
;
.
;
Chuck.Ojala@normandale.edu
;













#==============================================================================

# TEXT

_publ_section_synopsis           .
_publ_section_abstract           
;
(type here to add abstract)
;

_publ_section_comment            
;
(type here to add)
;

_publ_section_acknowledgements   # remove if not required
;
?
;




















_publ_section_references         
;
?
;




















_publ_section_figure_captions    
;

;

_publ_section_exptl_prep         
;
(type here to add preparation details)
;

_publ_section_exptl_refinement   
;
(type here to add refinement details)
;
#==============================================================================

data_4

_symmetry_space_group_name_hall  '-P 2ybc'
#Added by publCIF

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
N,N'-bis[(2-fluorophenyl)methylene]-1,4-benzenediamine 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_melting_point_lt       391
_chemical_melting_point_gt       390
_chemical_formula_moiety         'C20 H14 F2 N2'
_chemical_formula_sum            'C20 H14 F2 N2'
_chemical_formula_weight         320.33

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'


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                   6.9517(6)
_cell_length_b                   11.5713(10)
_cell_length_c                   10.0545(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.6180(10)
_cell_angle_gamma                90
_cell_volume                     782.61(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2972
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      27.38

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8953
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         27.49
_reflns_number_total             1786
_reflns_number_gt                1438
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0368P)²+0.2320P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1786
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.75576(18) 0.51709(11) 1.01834(12) 0.0280(3) Uani 1 1 d . . .
C2 C 0.82683(19) 0.43489(11) 1.11914(13) 0.0316(3) Uani 1 1 d . . .
C3 C 0.8826(2) 0.45967(13) 1.25733(13) 0.0376(3) Uani 1 1 d . . .
H3 H 0.9307 0.4007 1.3230 0.045 Uiso 1 1 calc R . .
C4 C 0.8668(2) 0.57231(14) 1.29811(14) 0.0406(4) Uani 1 1 d . . .
H4 H 0.9034 0.5913 1.3931 0.049 Uiso 1 1 calc R . .
C5 C 0.7980(2) 0.65782(13) 1.20160(14) 0.0406(4) Uani 1 1 d . . .
H5 H 0.7880 0.7353 1.2304 0.049 Uiso 1 1 calc R . .
C6 C 0.7437(2) 0.63039(12) 1.06325(13) 0.0347(3) Uani 1 1 d . . .
H6 H 0.6974 0.6897 0.9976 0.042 Uiso 1 1 calc R . .
C7 C 0.69053(18) 0.48462(11) 0.87318(12) 0.0295(3) Uani 1 1 d . . .
H7 H 0.6894 0.4053 0.8484 0.035 Uiso 1 1 calc R . .
C8 C 0.57159(18) 0.52557(10) 0.64009(12) 0.0279(3) Uani 1 1 d . . .
C9 C 0.45645(19) 0.60515(11) 0.55013(12) 0.0303(3) Uani 1 1 d . . .
H9 H 0.4272 0.6779 0.5842 0.036 Uiso 1 1 calc R . .
C10 C 0.38400(19) 0.58001(11) 0.41213(12) 0.0311(3) Uani 1 1 d . . .
H10 H 0.3037 0.6348 0.3527 0.037 Uiso 1 1 calc R . .
F1 F 0.84222(14) 0.32383(7) 1.07930(8) 0.0472(3) Uani 1 1 d . . .
N1 N 0.63553(16) 0.55999(9) 0.77971(10) 0.0311(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0256(6) 0.0337(7) 0.0249(6) -0.0002(5) 0.0066(5) -0.0034(5)
C2 0.0300(6) 0.0329(7) 0.0316(7) -0.0003(5) 0.0072(5) -0.0035(5)
C3 0.0338(7) 0.0498(9) 0.0274(7) 0.0060(6) 0.0043(5) -0.0007(6)
C4 0.0367(7) 0.0585(9) 0.0249(7) -0.0065(6) 0.0044(6) -0.0024(6)
C5 0.0423(8) 0.0432(8) 0.0351(7) -0.0112(6) 0.0077(6) -0.0011(6)
C6 0.0379(7) 0.0348(7) 0.0302(7) -0.0005(5) 0.0066(5) 0.0003(6)
C7 0.0316(7) 0.0296(6) 0.0272(6) -0.0021(5) 0.0075(5) -0.0025(5)
C8 0.0291(6) 0.0299(6) 0.0246(6) -0.0003(5) 0.0065(5) -0.0030(5)
C9 0.0354(7) 0.0277(6) 0.0278(6) -0.0020(5) 0.0080(5) 0.0017(5)
C10 0.0344(7) 0.0313(7) 0.0262(6) 0.0033(5) 0.0047(5) 0.0038(5)
F1 0.0660(6) 0.0324(5) 0.0388(5) 0.0033(3) 0.0051(4) 0.0013(4)
N1 0.0349(6) 0.0328(6) 0.0242(5) -0.0010(4) 0.0049(4) 0.0004(4)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3868(18) . ?
C1 C6 1.3960(18) . ?
C1 C7 1.4639(17) . ?
C2 F1 1.3584(15) . ?
C2 C3 1.3752(18) . ?
C3 C4 1.379(2) . ?
C3 H3 0.95 . ?
C4 C5 1.384(2) . ?
C4 H4 0.95 . ?
C5 C6 1.3832(18) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 N1 1.2683(16) . ?
C7 H7 0.95 . ?
C8 C9 1.3933(17) . ?
C8 C10 1.3947(17) 3_666 ?
C8 N1 1.4184(15) . ?
C9 C10 1.3824(17) . ?
C9 H9 0.95 . ?
C10 C8 1.3947(17) 3_666 ?
C10 H10 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 116.56(11) . . ?
C2 C1 C7 121.08(12) . . ?
C6 C1 C7 122.33(12) . . ?
F1 C2 C3 118.17(12) . . ?
F1 C2 C1 118.25(11) . . ?
C3 C2 C1 123.57(13) . . ?
C2 C3 C4 118.30(13) . . ?
C2 C3 H3 121 . . ?
C4 C3 H3 121 . . ?
C3 C4 C5 120.44(12) . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
C6 C5 C4 119.96(13) . . ?
C6 C5 H5 120. . . ?
C4 C5 H5 120. . . ?
C5 C6 C1 121.16(13) . . ?
C5 C6 H6 119. . . ?
C1 C6 H6 119. . . ?
N1 C7 C1 121.46(12) . . ?
N1 C7 H7 119. . . ?
C1 C7 H7 119. . . ?
C9 C8 C10 118.69(11) . 3_666 ?
C9 C8 N1 116.24(11) . . ?
C10 C8 N1 125.07(11) 3_666 . ?
C10 C9 C8 121.10(12) . . ?
C10 C9 H9 119. . . ?
C8 C9 H9 119. . . ?
C9 C10 C8 120.20(12) . 3_666 ?
C9 C10 H10 120 . . ?
C8 C10 H10 120 3_666 . ?
C7 N1 C8 120.06(11) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag

C2 C1 C7 N1 -176.12(12) . . . . ?
C6 C1 C7 N1 6.15(19) . . . . ?
C9 C8 N1 C7 160.19(12) . . . . ?
C10 C8 N1 C7 -20.11(19) 3_666 . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040
_iucr_refine_instructions_details 
; 
TITL 13200a in P2(1)/c 
CELL 0.71073   6.9517  11.5713  10.0545  90.000 104.618  90.000 
ZERR    2.00   0.0006   0.0010   0.0008   0.000   0.001   0.000 
LATT 1 
SYMM -X, 0.5+Y, 0.5-Z 
SFAC C  H  N  F  
UNIT 40 28 4 4 
L.S. 8
EXTI  0.01714
ACTA
BOND $H 
FMAP 2
PLAN 5
LIST 4
MPLA 4 C1 C7 N1 C8 
MPLA 3 C8 C9 C10 
MPLA 6 C1 C2 C3 C4 C5 C6 
CONF 
SIZE 0.060 0.250 0.420 
WGHT  0.036800  0.232000 
FVAR  0.208360
TEMP -100 
C1     1   0.755760  0.517090  1.018337 11.000000  0.025560  0.033740 = 
           0.024930 -0.000170  0.006570 -0.003450
C2     1   0.826829  0.434892  1.119141 11.000000  0.030030  0.032940 = 
           0.031570 -0.000340  0.007230 -0.003500
C3     1   0.882578  0.459666  1.257334 11.000000  0.033760  0.049800 = 
           0.027370  0.006000  0.004310 -0.000720
AFIX 43
H3     2   0.930743  0.400691  1.323030 11.000000 -1.200000
AFIX 0
C4     1   0.866779  0.572309  1.298107 11.000000  0.036710  0.058480 = 
           0.024930 -0.006490  0.004430 -0.002390
AFIX 43
H4     2   0.903381  0.591334  1.393085 11.000000 -1.200000
AFIX 0
C5     1   0.797969  0.657815  1.201604 11.000000  0.042310  0.043170 = 
           0.035120 -0.011160  0.007710 -0.001120
AFIX 43
H5     2   0.788001  0.735305  1.230360 11.000000 -1.200000
AFIX 0
C6     1   0.743710  0.630388  1.063248 11.000000  0.037880  0.034810 = 
           0.030190 -0.000500  0.006570  0.000300
AFIX 43
H6     2   0.697432  0.689695  0.997637 11.000000 -1.200000
AFIX 0
C7     1   0.690525  0.484625  0.873177 11.000000  0.031620  0.029640 = 
           0.027230 -0.002060  0.007540 -0.002550
AFIX 43
H7     2   0.689361  0.405345  0.848436 11.000000 -1.200000
AFIX 0
C8     1   0.571590  0.525575  0.640086 11.000000  0.029110  0.029910 = 
           0.024570 -0.000310  0.006460 -0.003040
C9     1   0.456453  0.605152  0.550132 11.000000  0.035390  0.027670 = 
           0.027780 -0.001990  0.007990  0.001700
AFIX 43
H9     2   0.427249  0.677909  0.584206 11.000000 -1.200000
AFIX 0
C10    1   0.384002  0.580006  0.412127 11.000000  0.034350  0.031270 = 
           0.026190  0.003310  0.004700  0.003820
AFIX 43
H10    2   0.303722  0.634805  0.352671 11.000000 -1.200000
AFIX 0
F1     4   0.842223  0.323826  1.079296 11.000000  0.065980  0.032430 = 
           0.038780  0.003330  0.005110  0.001310
N1     3   0.635526  0.559988  0.779708 11.000000  0.034940  0.032830 = 
           0.024250 -0.001030  0.004870  0.000380
HKLF 4 
END   
;
_database_code_depnum_ccdc_archive 'CCDC 974617'
#============================================================================== 

data_New_Global_Publ_Block

# publcif _publ_body_element loop start
loop_
_publ_body_element
_publ_body_title
_publ_body_contents

section ? ?
# publcif _publ_body_element loop end

_publ_section_related_literature ?

# Added by publCIF - use a unique identifier for each data block

#==============================================================================


# SUBMISSION DETAILS

_publ_contact_author_name        
'William H. Ojala' # Name of author for correspondence
_publ_contact_author_address     # Address of author for correspondence


;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079 USA
;


_publ_contact_author_email       whojala@stthomas.edu
_publ_contact_author_fax         (651)-962-5209
_publ_contact_author_phone       (651)-962-5585

_publ_contact_letter             
;
Please consider this CIF for publication. I certify that this contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;

_publ_requested_journal          CrystEngComm
_publ_requested_category         FA

#==============================================================================

# TITLE AND AUTHOR LIST

_publ_section_title              
;
Fluorine-Containing Supramolecular Synthons as Structure-Differentiating Agents
in Some "Bridge-Flipped" Isomeric bis-Benzylideneanilines
;
_publ_section_title_footnote     # remove if not required
.

# The loop structure below should contain the names and addresses of all 
# authors, in the required order of publication. Repeat as necessary.

# NB if using publCIF, the Author database tool might prove useful
# (see the Tools menu in publCIF)

loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
_publ_author_email
'Ojala, William H.'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
whojala@stthomas.edu
;
'Balidemaj, Barjeta'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
barjeta.b@gmail.com
;
'Johnson, Jenna A.'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
john8308@stthomas.edu
;
'Larson, Sarah N.'
;
Department of Chemistry
University of St. Thomas
2115 Summit Avenue
St. Paul, MN 55105-1079
USA
;
.
;
lars7752@stthomas.edu
;
'Ojala, Charles R.'
;
Department of Chemistry
Normandale Community College
9700 France Avenue South
Bloomington, MN 55431 
USA
;
.
;
Chuck.Ojala@normandale.edu
;













#==============================================================================

# TEXT

_publ_section_synopsis           .
_publ_section_abstract           
;
(type here to add abstract)
;

_publ_section_comment            
;
(type here to add)
;

_publ_section_acknowledgements   # remove if not required
;
?
;




















_publ_section_references         
;
?
;




















_publ_section_figure_captions    
;

;

_publ_section_exptl_prep         
;
(type here to add preparation details)
;

_publ_section_exptl_refinement   
;
(type here to add refinement details)
;
#==============================================================================


data_5

_symmetry_space_group_name_hall  '-P 2ybc'
#Added by publCIF

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
N,N'-bis[(3-fluorophenyl)methylene]-1,4-benzenediamine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_melting_point_lt       403
_chemical_melting_point_gt       401
_chemical_formula_moiety         'C20 H14 F2 N2'
_chemical_formula_sum            'C20 H14 F2 N2'
_chemical_formula_weight         320.33

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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                   17.2826(17)
_cell_length_b                   6.1796(6)
_cell_length_c                   7.0765(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.710(1)
_cell_angle_gamma                90
_cell_volume                     754.92(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2344
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.51

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9513
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4277
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         27.53
_reflns_number_total             1692
_reflns_number_gt                1421
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0530P)²+0.2221P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1692
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1092
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.25151(7) 0.0968(2) 0.41074(17) 0.0268(3) Uani 1 1 d . . .
C2 C 0.31238(7) 0.2439(2) 0.43508(18) 0.0298(3) Uani 1 1 d . . .
H2 H 0.3032 0.3883 0.4743 0.036 Uiso 1 1 calc R . .
C3 C 0.38591(7) 0.1743(2) 0.4008(2) 0.0345(3) Uani 1 1 d . . .
C4 C 0.40231(8) -0.0324(3) 0.3426(2) 0.0378(3) Uani 1 1 d . . .
H4 H 0.4538 -0.0740 0.3182 0.045 Uiso 1 1 calc R . .
C5 C 0.34176(8) -0.1781(2) 0.3205(2) 0.0366(3) Uani 1 1 d . . .
H5 H 0.3516 -0.3217 0.2803 0.044 Uiso 1 1 calc R . .
C6 C 0.26658(8) -0.1157(2) 0.35675(19) 0.0320(3) Uani 1 1 d . . .
H6 H 0.2255 -0.2177 0.3448 0.038 Uiso 1 1 calc R . .
C7 C 0.17167(7) 0.1668(2) 0.43934(17) 0.0266(3) Uani 1 1 d . . .
H7 H 0.1326 0.0606 0.4528 0.032 Uiso 1 1 calc R . .
C8 C 0.07545(7) 0.4255(2) 0.47087(16) 0.0233(3) Uani 1 1 d . . .
C9 C 0.06307(7) 0.6229(2) 0.56181(17) 0.0240(3) Uani 1 1 d . . .
H9 H 0.1063 0.7083 0.6033 0.029 Uiso 1 1 calc R . .
C10 C -0.01111(7) 0.6959(2) 0.59243(16) 0.0240(3) Uani 1 1 d . . .
H10 H -0.0182 0.8289 0.6567 0.029 Uiso 1 1 calc R . .
F1 F 0.44518(5) 0.31740(16) 0.42372(15) 0.0529(3) Uani 1 1 d . . .
N1 N 0.15353(6) 0.36598(17) 0.44659(15) 0.0258(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0259(6) 0.0302(7) 0.0245(6) 0.0025(5) 0.0027(5) 0.0037(5)
C2 0.0275(6) 0.0316(7) 0.0306(6) -0.0010(5) 0.0033(5) 0.0013(5)
C3 0.0242(6) 0.0433(8) 0.0364(7) 0.0024(6) 0.0042(5) -0.0011(5)
C4 0.0289(7) 0.0474(9) 0.0375(7) 0.0053(6) 0.0069(6) 0.0130(6)
C5 0.0389(8) 0.0339(8) 0.0374(7) 0.0017(6) 0.0055(6) 0.0132(6)
C6 0.0325(7) 0.0290(7) 0.0345(7) 0.0017(5) 0.0008(5) 0.0036(6)
C7 0.0230(6) 0.0289(7) 0.0282(6) 0.0011(5) 0.0021(5) -0.0004(5)
C8 0.0222(6) 0.0257(6) 0.0222(5) 0.0018(5) 0.0036(4) 0.0005(5)
C9 0.0228(6) 0.0235(6) 0.0257(6) 0.0005(5) 0.0005(4) -0.0023(5)
C10 0.0266(6) 0.0219(6) 0.0237(6) -0.0016(4) 0.0025(4) 0.0012(5)
F1 0.0269(5) 0.0578(6) 0.0747(7) -0.0054(5) 0.0084(4) -0.0075(4)
N1 0.0215(5) 0.0286(6) 0.0276(5) -0.0014(4) 0.0037(4) 0.0006(4)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3949(18) . ?
C1 C6 1.3954(18) . ?
C1 C7 1.4693(16) . ?
C2 C3 1.3743(17) . ?
C2 H2 0.95 . ?
C3 F1 1.3573(16) . ?
C3 C4 1.375(2) . ?
C4 C5 1.384(2) . ?
C4 H4 0.95 . ?
C5 C6 1.3907(18) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 N1 1.2718(17) . ?
C7 H7 0.95 . ?
C8 C10 1.3973(17) 3_566 ?
C8 C9 1.4005(17) . ?
C8 N1 1.4169(15) . ?
C9 C10 1.3858(16) . ?
C9 H9 0.95 . ?
C10 C8 1.3973(17) 3_566 ?
C10 H10 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.85(12) . . ?
C2 C1 C7 119.90(12) . . ?
C6 C1 C7 120.24(12) . . ?
C3 C2 C1 118.18(13) . . ?
C3 C2 H2 120. . . ?
C1 C2 H2 120. . . ?
F1 C3 C2 118.28(13) . . ?
F1 C3 C4 118.42(12) . . ?
C2 C3 C4 123.30(13) . . ?
C3 C4 C5 118.19(12) . . ?
C3 C4 H4 120. . . ?
C5 C4 H4 120. . . ?
C4 C5 C6 120.47(13) . . ?
C4 C5 H5 120 . . ?
C6 C5 H5 120 . . ?
C5 C6 C1 119.96(13) . . ?
C5 C6 H6 120. . . ?
C1 C6 H6 120. . . ?
N1 C7 C1 121.71(12) . . ?
N1 C7 H7 120 . . ?
C1 C7 H7 120 . . ?
C10 C8 C9 118.59(11) 3_566 . ?
C10 C8 N1 124.74(11) 3_566 . ?
C9 C8 N1 116.66(11) . . ?
C10 C9 C8 121.20(11) . . ?
C10 C9 H9 120 . . ?
C8 C9 H9 120 . . ?
C9 C10 C8 120.21(11) . 3_566 ?
C9 C10 H10 120 . . ?
C8 C10 H10 120 3_566 . ?
C7 N1 C8 119.61(11) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag

C2 C1 C7 N1 15.10(18) . . . . ?
C6 C1 C7 N1 -164.02(13) . . . . ?
C10 C8 N1 C7 -29.80(18) 3_566 . . . ?
C9 C8 N1 C7 151.56(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.040
_iucr_refine_instructions_details 
;
TITL 12157a in P2(1)/c 
CELL 0.71073  17.2826   6.1796   7.0765  90.000  92.710  90.000 
ZERR    2.00   0.0017   0.0006   0.0007   0.000   0.001   0.000 
LATT 1 
SYMM -X, 0.5+Y, 0.5-Z 
SFAC C  H  N  F  
UNIT 40 28 4 4 
L.S. 4
ACTA
BOND $H 
FMAP 2
PLAN 20
SIZE 0.08 0.15 0.50 
CONF 
MPLA 6 C1 C2 C3 C4 C5 C6 
MPLA 3 C8 C9 C10 
MPLA 4 C1 C7 N1 C8 
WGHT  0.053100  0.222100 
FVAR  0.225950
TEMP -100 
MOLE 1
C1     1   0.251512  0.096755  0.410736 11.000000  0.025940  0.030150 = 
           0.024470  0.002510  0.002700  0.003650
C2     1   0.312375  0.243905  0.435085 11.000000  0.027540  0.031570 = 
           0.030620 -0.000980  0.003330  0.001350
AFIX 43
H2     2   0.303239  0.388317  0.474306 11.000000 -1.200000
AFIX 0
C3     1   0.385914  0.174263  0.400787 11.000000  0.024170  0.043260 = 
           0.036380  0.002350  0.004160 -0.001110
C4     1   0.402313 -0.032402  0.342601 11.000000  0.028920  0.047400 = 
           0.037470  0.005330  0.006940  0.013050
AFIX 43
H4     2   0.453815 -0.073992  0.318249 11.000000 -1.200000
AFIX 0
C5     1   0.341756 -0.178088  0.320498 11.000000  0.038860  0.033890 = 
           0.037380  0.001700  0.005470  0.013240
AFIX 43
H5     2   0.351608 -0.321727  0.280269 11.000000 -1.200000
AFIX 0
C6     1   0.266580 -0.115724  0.356755 11.000000  0.032530  0.028960 = 
           0.034510  0.001720  0.000780  0.003570
AFIX 43
H6     2   0.225510 -0.217710  0.344781 11.000000 -1.200000
AFIX 0
C7     1   0.171668  0.166809  0.439336 11.000000  0.022960  0.028860 = 
           0.028200  0.001050  0.002150 -0.000370
AFIX 43
H7     2   0.132582  0.060559  0.452758 11.000000 -1.200000
AFIX 0
C8     1   0.075445  0.425476  0.470867 11.000000  0.022160  0.025680 = 
           0.022240  0.001800  0.003610  0.000540
C9     1   0.063070  0.622904  0.561807 11.000000  0.022840  0.023530 = 
           0.025690  0.000520  0.000520 -0.002350
AFIX 43
H9     2   0.106314  0.708329  0.603251 11.000000 -1.200000
AFIX 0
C10    1  -0.011110  0.695908  0.592435 11.000000  0.026590  0.021890 = 
           0.023730 -0.001560  0.002540  0.001220
AFIX 43
H10    2  -0.018246  0.828896  0.656668 11.000000 -1.200000
AFIX 0
F1     4   0.445183  0.317401  0.423720 11.000000  0.026900  0.057770 = 
           0.074740 -0.005400  0.008360 -0.007540
N1     3   0.153525  0.365983  0.446589 11.000000  0.021480  0.028640 = 
           0.027570 -0.001440  0.003710  0.000640
Q1     1   0.214300  0.135500  0.417900 11.000000  0.050000      0.28
Q2     1   0.113900  0.389200  0.462300 11.000000  0.050000      0.27
Q3     1   0.025100  0.649000  0.589800 11.000000  0.050000      0.26
Q4     1   0.044300  0.383000  0.419600 11.000000  0.050000      0.25
Q5     1   0.307900 -0.123400  0.336700 11.000000  0.050000      0.23
Q6     1   0.071000  0.502700  0.541700 11.000000  0.050000      0.22
Q7     1   0.347600  0.213300  0.385700 11.000000  0.050000      0.20
Q8     1   0.351300  0.182500  0.448600 11.000000  0.050000      0.20
Q9     1   0.284300  0.144800  0.453500 11.000000  0.050000      0.19
Q10    1   0.369500 -0.094500  0.288400 11.000000  0.050000      0.19
Q11    1   0.273300  0.174600  0.364000 11.000000  0.050000      0.16
Q12    1   0.401100  0.036200  0.437900 11.000000  0.050000      0.16
Q13    1   0.375800 -0.112900  0.375100 11.000000  0.050000      0.15
Q14    1   0.259600  0.006100  0.349800 11.000000  0.050000      0.15
Q15    1   0.182000  0.459300  0.398600 11.000000  0.050000      0.15
Q16    1   0.261200 -0.021900  0.428900 11.000000  0.050000      0.15
Q17    1   0.389900  0.090000  0.316700 11.000000  0.050000      0.14
Q18    1   0.184100  0.425700  0.534800 11.000000  0.050000      0.12
Q19    1   0.118700 -0.007000  0.371500 11.000000  0.050000      0.10
Q20    1   0.091400  0.639500  0.622400 11.000000  0.050000      0.10
HKLF 4 
END  
;
#==============================================================================

_database_code_depnum_ccdc_archive 'CCDC 974618'
