#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/56/2225682.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2225682
loop_
_publ_author_name
'Zhang, Mei-Lin'
'Yang, Jie'
_publ_section_title
;
 N-[Bis(4-fluorophenyl)methylene]aniline
;
_journal_coeditor_code           RZ2421
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o727
_journal_paper_doi               10.1107/S1600536810007099
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H13 F2 N'
_chemical_formula_moiety         'C19 H13 F2 N'
_chemical_formula_sum            'C19 H13 F2 N'
_chemical_formula_weight         293.30
_chemical_name_systematic
;
N-[Bis(4-fluorophenyl)methylene]aniline
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   18.104(6)
_cell_length_b                   8.612(3)
_cell_length_c                   18.985(6)
_cell_measurement_reflns_used    1417
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.10
_cell_measurement_theta_min      2.36
_cell_volume                     2960.0(17)
_computing_cell_refinement       'SAINT (Bruker, 1996)'
_computing_data_collection       'SMART (Bruker, 1996)'
_computing_data_reduction        'SAINT (Bruker, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13881
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.168
_refine_ls_extinction_coef       0.0017(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0354
_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)+(0.0728P)²+0.3185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                2060
_reflns_number_total             2612
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz2421.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               2225682
_cod_database_fobs_code          2225682
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'
'-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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.20644(7) 0.24801(15) 0.27677(8) 0.0490(3) Uani d . 1 . .
C C2 0.26143(8) 0.25396(15) 0.33496(8) 0.0505(4) Uani d . 1 . .
C C3 0.33329(8) 0.20396(17) 0.32292(9) 0.0591(4) Uani d . 1 . .
H H3 0.3463 0.1672 0.2786 0.071 Uiso calc R 1 . .
C C4 0.38557(10) 0.20799(19) 0.37563(10) 0.0676(5) Uani d . 1 . .
H H4 0.4335 0.1733 0.3675 0.081 Uiso calc R 1 . .
C C5 0.36536(9) 0.2642(2) 0.44019(9) 0.0645(4) Uani d . 1 . .
C C6 0.29542(9) 0.3134(2) 0.45459(9) 0.0683(5) Uani d . 1 . .
H H6 0.2831 0.3498 0.4992 0.082 Uiso calc R 1 . .
C C7 0.24335(9) 0.30831(19) 0.40158(8) 0.0608(4) Uani d . 1 . .
H H7 0.1954 0.3418 0.4106 0.073 Uiso calc R 1 . .
C C8 0.12682(7) 0.23425(15) 0.29640(7) 0.0463(3) Uani d . 1 . .
C C9 0.07420(8) 0.33442(17) 0.26868(8) 0.0538(4) Uani d . 1 . .
H H9 0.0887 0.4115 0.2373 0.065 Uiso calc R 1 . .
C C10 0.00099(8) 0.32128(18) 0.28699(8) 0.0576(4) Uani d . 1 . .
H H10 -0.0340 0.3894 0.2688 0.069 Uiso calc R 1 . .
C C11 -0.01927(8) 0.20545(17) 0.33273(8) 0.0527(4) Uani d . 1 . .
C C12 0.03040(8) 0.10401(17) 0.36102(8) 0.0559(4) Uani d . 1 . .
H H12 0.0151 0.0259 0.3916 0.067 Uiso calc R 1 . .
C C13 0.10393(8) 0.12022(16) 0.34313(8) 0.0533(4) Uani d . 1 . .
H H13 0.1387 0.0535 0.3628 0.064 Uiso calc R 1 . .
C C14 0.18353(8) 0.22899(17) 0.15481(8) 0.0531(4) Uani d . 1 . .
C C15 0.16862(9) 0.35005(19) 0.10865(8) 0.0634(4) Uani d . 1 . .
H H15 0.1886 0.4479 0.1168 0.076 Uiso calc R 1 . .
C C16 0.12419(10) 0.3250(2) 0.05081(9) 0.0710(5) Uani d . 1 . .
H H16 0.1133 0.4069 0.0207 0.085 Uiso calc R 1 . .
C C17 0.09587(10) 0.1799(2) 0.03724(9) 0.0722(5) Uani d . 1 . .
H H17 0.0659 0.1638 -0.0018 0.087 Uiso calc R 1 . .
C C18 0.11214(10) 0.0590(2) 0.08170(9) 0.0725(5) Uani d . 1 . .
H H18 0.0936 -0.0395 0.0722 0.087 Uiso calc R 1 . .
C C19 0.15577(9) 0.08234(19) 0.14032(9) 0.0640(4) Uani d . 1 . .
H H19 0.1666 -0.0003 0.1701 0.077 Uiso calc R 1 . .
F F1 0.41742(6) 0.27364(14) 0.49157(6) 0.0917(4) Uani d . 1 . .
F F2 -0.09151(5) 0.19054(12) 0.34959(5) 0.0732(3) Uani d . 1 . .
N N1 0.23085(7) 0.25324(14) 0.21332(7) 0.0575(3) Uani d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 117.71(13) ?
N1 C1 C8 . . 124.69(13) ?
C2 C1 C8 . . 117.59(12) ?
C7 C2 C3 . . 118.38(15) ?
C7 C2 C1 . . 122.04(14) ?
C3 C2 C1 . . 119.58(14) ?
C4 C3 C2 . . 121.07(16) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C5 C4 C3 . . 118.42(16) ?
C5 C4 H4 . . 120.8 ?
C3 C4 H4 . . 120.8 ?
F1 C5 C6 . . 118.79(17) ?
F1 C5 C4 . . 118.62(16) ?
C6 C5 C4 . . 122.58(16) ?
C5 C6 C7 . . 118.58(17) ?
C5 C6 H6 . . 120.7 ?
C7 C6 H6 . . 120.7 ?
C6 C7 C2 . . 120.97(16) ?
C6 C7 H7 . . 119.5 ?
C2 C7 H7 . . 119.5 ?
C13 C8 C9 . . 118.51(13) ?
C13 C8 C1 . . 120.28(12) ?
C9 C8 C1 . . 121.21(13) ?
C10 C9 C8 . . 120.95(14) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C9 C10 C11 . . 118.51(13) ?
C9 C10 H10 . . 120.7 ?
C11 C10 H10 . . 120.7 ?
F2 C11 C12 . . 118.91(14) ?
F2 C11 C10 . . 118.50(13) ?
C12 C11 C10 . . 122.59(14) ?
C11 C12 C13 . . 118.29(14) ?
C11 C12 H12 . . 120.9 ?
C13 C12 H12 . . 120.9 ?
C12 C13 C8 . . 121.13(13) ?
C12 C13 H13 . . 119.4 ?
C8 C13 H13 . . 119.4 ?
C15 C14 C19 . . 119.22(15) ?
C15 C14 N1 . . 120.08(14) ?
C19 C14 N1 . . 120.55(14) ?
C16 C15 C14 . . 119.91(16) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C17 C16 C15 . . 120.63(17) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C16 C17 C18 . . 119.62(17) ?
C16 C17 H17 . . 120.2 ?
C18 C17 H17 . . 120.2 ?
C19 C18 C17 . . 120.55(17) ?
C19 C18 H18 . . 119.7 ?
C17 C18 H18 . . 119.7 ?
C18 C19 C14 . . 120.02(16) ?
C18 C19 H19 . . 120.0 ?
C14 C19 H19 . . 120.0 ?
C1 N1 C14 . . 121.45(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.2839(19) ?
C1 C2 . 1.488(2) ?
C1 C8 . 1.494(2) ?
C2 C7 . 1.388(2) ?
C2 C3 . 1.389(2) ?
C3 C4 . 1.378(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.368(3) ?
C4 H4 . 0.9300 ?
C5 F1 . 1.3589(19) ?
C5 C6 . 1.363(3) ?
C6 C7 . 1.380(2) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C13 . 1.3868(19) ?
C8 C9 . 1.389(2) ?
C9 C10 . 1.375(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.372(2) ?
C10 H10 . 0.9300 ?
C11 F2 . 1.3527(17) ?
C11 C12 . 1.364(2) ?
C12 C13 . 1.381(2) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 C15 . 1.388(2) ?
C14 C19 . 1.387(2) ?
C14 N1 . 1.418(2) ?
C15 C16 . 1.378(2) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.375(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.373(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.379(2) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C18 H18 F1 2_554 0.93 2.54 3.379(2) 150
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1731758
