#------------------------------------------------------------------------------
#$Date: 2015-06-09 14:40:42 +0300 (Tue, 09 Jun 2015) $
#$Revision: 139001 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/04/1520480.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1520480
loop_
_publ_author_name
'Tizzard, G.'
'Threlfall, T.'
'Ling, S.'
'Coles, S.'
_publ_section_title
;
 (E)-3,5-difluoro-N-(4-fluorobenzylidene)aniline
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              1423
_journal_year                    2010
_chemical_formula_sum            'C13 H0 F3 N'
_chemical_formula_weight         227.14
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2066(3)
_cell_length_b                   7.7799(4)
_cell_length_c                   21.3938(11)
_cell_measurement_temperature    296(2)
_cell_volume                     1033.04(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11614
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         3.24
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9610
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.836
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.836
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1465P)²+0.6984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1655
_reflns_number_gt                1540
_reflns_number_total             1816
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-1423.cif
_cod_data_source_block           2010sl0005a
_cod_depositor_comments
;
Citation :
Tizzard, G and Threlfall, T and Ling, S and Coles, S (2010) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/1423)

More at:
http://ecrystals.chem.soton.ac.uk/1423/
;
_cod_database_code               1520480
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
F1 F 0.2826(4) 0.7639(3) 0.15349(9) 0.0409(6) Uani 1 1 d . . .
F2 F -0.2710(3) 0.0468(3) -0.30505(9) 0.0381(6) Uani 1 1 d . . .
F3 F -0.0963(3) 0.6050(3) 0.14222(9) 0.0455(6) Uani 1 1 d . . .
N1 N 0.1218(4) 0.3642(4) -0.05614(12) 0.0274(6) Uani 1 1 d . . .
C1 C -0.2224(5) 0.1237(4) -0.25005(15) 0.0286(7) Uani 1 1 d . . .
C2 C -0.0620(5) 0.3732(4) -0.08207(14) 0.0264(7) Uani 1 1 d . . .
H2 H -0.1668 0.4415 -0.0634 0.032 Uiso 1 1 calc R . .
C3 C -0.1173(5) 0.2828(4) -0.13916(15) 0.0254(7) Uani 1 1 d . . .
C4 C 0.1562(5) 0.4633(4) -0.00100(14) 0.0274(7) Uani 1 1 d . . .
C5 C 0.0008(6) 0.4807(4) 0.04569(15) 0.0295(8) Uani 1 1 d . . .
H5 H -0.1309 0.4243 0.0427 0.035 Uiso 1 1 calc R . .
C6 C 0.0475(6) 0.5844(4) 0.09677(14) 0.0294(8) Uani 1 1 d . . .
C7 C -0.0197(6) 0.0967(4) -0.22522(14) 0.0282(7) Uani 1 1 d . . .
H7 H 0.0788 0.0254 -0.2453 0.034 Uiso 1 1 calc R . .
C8 C 0.0332(5) 0.1783(4) -0.16968(14) 0.0266(7) Uani 1 1 d . . .
H8 H 0.1697 0.1636 -0.1526 0.032 Uiso 1 1 calc R . .
C9 C 0.2466(6) 0.6662(4) 0.10244(15) 0.0314(8) Uani 1 1 d . . .
C10 C -0.3218(5) 0.3043(4) -0.16556(15) 0.0269(7) Uani 1 1 d . . .
H10 H -0.4232 0.3725 -0.1453 0.032 Uiso 1 1 calc R . .
C11 C -0.3752(5) 0.2248(4) -0.22169(15) 0.0293(7) Uani 1 1 d . . .
H11 H -0.5106 0.2397 -0.2395 0.035 Uiso 1 1 calc R . .
C12 C 0.4010(6) 0.6455(4) 0.05780(16) 0.0322(8) Uani 1 1 d . . .
H12 H 0.5341 0.6992 0.0619 0.039 Uiso 1 1 calc R . .
C13 C 0.3569(5) 0.5425(4) 0.00581(16) 0.0301(7) Uani 1 1 d . . .
H13 H 0.4622 0.5265 -0.0246 0.036 Uiso 1 1 calc R . .
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'
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
C2 N1 C4 117.8(3) . .
F2 C1 C11 118.9(3) . .
F2 C1 C7 118.0(3) . .
C11 C1 C7 123.1(3) . .
N1 C2 C3 123.6(3) . .
N1 C2 H2 118.2 . .
C3 C2 H2 118.2 . .
C8 C3 C10 119.1(3) . .
C8 C3 C2 121.1(3) . .
C10 C3 C2 119.8(3) . .
C5 C4 C13 119.9(3) . .
C5 C4 N1 122.8(3) . .
C13 C4 N1 117.3(3) . .
C4 C5 C6 118.4(3) . .
C4 C5 H5 120.8 . .
C6 C5 H5 120.8 . .
F3 C6 C9 118.4(3) . .
F3 C6 C5 120.3(3) . .
C9 C6 C5 121.2(3) . .
C1 C7 C8 118.4(3) . .
C1 C7 H7 120.8 . .
C8 C7 H7 120.8 . .
C7 C8 C3 120.5(3) . .
C7 C8 H8 119.8 . .
C3 C8 H8 119.7 . .
F1 C9 C12 121.2(3) . .
F1 C9 C6 118.3(3) . .
C12 C9 C6 120.5(3) . .
C11 C10 C3 120.8(3) . .
C11 C10 H10 119.6 . .
C3 C10 H10 119.6 . .
C1 C11 C10 118.1(3) . .
C1 C11 H11 120.9 . .
C10 C11 H11 120.9 . .
C9 C12 C13 119.2(3) . .
C9 C12 H12 120.4 . .
C13 C12 H12 120.4 . .
C4 C13 C12 120.7(3) . .
C4 C13 H13 119.7 . .
C12 C13 H13 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C9 1.349(4) .
F2 C1 1.354(4) .
F3 C6 1.329(4) .
N1 C2 1.270(4) .
N1 C4 1.425(4) .
C1 C11 1.373(5) .
C1 C7 1.382(5) .
C2 C3 1.450(4) .
C2 H2 0.9300 .
C3 C8 1.400(4) .
C3 C10 1.399(4) .
C4 C5 1.395(5) .
C4 C13 1.397(5) .
C5 C6 1.389(5) .
C5 H5 0.9300 .
C6 C9 1.395(5) .
C7 C8 1.387(4) .
C7 H7 0.9300 .
C8 H8 0.9300 .
C9 C12 1.362(5) .
C10 C11 1.391(5) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 C13 1.398(5) .
C12 H12 0.9300 .
C13 H13 0.9300 .
