#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/57/2225769.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_2225769
loop_
_publ_author_name
'Dorn, Angelika'
'Schollmeyer, Dieter'
'Laufer, Stefan A.'
_publ_section_title
;
 1-[4-(2-Aminoanilino)phenyl]-2,2,2-trifluoroethanone
;
_journal_coeditor_code           BT5212
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1149
_journal_paper_doi               10.1107/S1600536810008937
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H11 F3 N2 O'
_chemical_formula_moiety         'C14 H11 F3 N2 O'
_chemical_formula_sum            'C14 H11 F3 N2 O'
_chemical_formula_weight         280.25
_chemical_name_systematic
;
1-[4-(2-Aminoanilino)phenyl]-2,2,2-trifluoroethanone
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.0385(13)
_cell_length_b                   8.7129(7)
_cell_length_c                   22.424(2)
_cell_measurement_reflns_used    7908
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      2.4
_cell_volume                     2547.4(4)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       'CCD scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21134
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.285
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0446
_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)+(0.0601P)²+1.4118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1174
_refine_ls_wR_factor_ref         0.1273
_reflns_number_gt                2498
_reflns_number_total             3033
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5212.cif
_cod_data_source_block           I
_cod_database_code               2225769
_cod_database_fobs_code          2225769
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 0.18780(11) 0.80106(18) 0.63368(7) 0.0277(3) Uani d . 1 . .
C C2 0.19637(13) 0.7530(2) 0.69312(7) 0.0330(4) Uani d . 1 . .
C C3 0.11693(16) 0.7953(2) 0.73256(8) 0.0479(5) Uani d . 1 . .
H H3 0.1203 0.7641 0.7731 0.057 Uiso calc R 1 . .
C C4 0.03490(16) 0.8806(3) 0.71344(11) 0.0580(6) Uani d . 1 . .
H H4 -0.0181 0.9060 0.7408 0.070 Uiso calc R 1 . .
C C5 0.02813(15) 0.9299(3) 0.65535(11) 0.0546(6) Uani d . 1 . .
H H5 -0.0282 0.9908 0.6427 0.065 Uiso calc R 1 . .
C C6 0.10447(13) 0.8895(2) 0.61572(8) 0.0381(4) Uani d . 1 . .
H H6 0.1000 0.9226 0.5754 0.046 Uiso calc R 1 . .
N N7 0.27946(14) 0.6728(2) 0.71200(7) 0.0486(4) Uani d . 1 . .
H H7A 0.3249 0.6275 0.6871 0.073 Uiso d R 1 . .
H H7B 0.2675 0.6308 0.7483 0.073 Uiso d R 1 . .
N N8 0.26108(10) 0.75201(16) 0.59059(5) 0.0291(3) Uani d . 1 . .
H H8 0.2297 0.6912 0.5600 0.035 Uiso d R 1 . .
C C9 0.35838(11) 0.80793(18) 0.58519(6) 0.0255(3) Uani d . 1 . .
C C10 0.39963(12) 0.91396(18) 0.62580(6) 0.0271(3) Uani d . 1 . .
H H10 0.3594 0.9488 0.6584 0.033 Uiso calc R 1 . .
C C11 0.49855(12) 0.96782(18) 0.61856(6) 0.0272(3) Uani d . 1 . .
H H11 0.5256 1.0394 0.6464 0.033 Uiso calc R 1 . .
C C12 0.55966(11) 0.91856(17) 0.57084(6) 0.0253(3) Uani d . 1 . .
C C13 0.51717(12) 0.81270(19) 0.53022(6) 0.0284(3) Uani d . 1 . .
H H13 0.5571 0.7789 0.4973 0.034 Uiso calc R 1 . .
C C14 0.41990(12) 0.75778(19) 0.53712(6) 0.0288(3) Uani d . 1 . .
H H14 0.3934 0.6854 0.5094 0.035 Uiso calc R 1 . .
C C15 0.66340(11) 0.97035(18) 0.55983(6) 0.0266(3) Uani d . 1 . .
O O16 0.71615(9) 0.93617(15) 0.51702(5) 0.0362(3) Uani d . 1 . .
C C17 0.71528(12) 1.0765(2) 0.60606(7) 0.0322(3) Uani d . 1 . .
F F18 0.81079(8) 1.10979(14) 0.59054(5) 0.0480(3) Uani d . 1 . .
F F19 0.72009(9) 1.00909(14) 0.65988(4) 0.0457(3) Uani d . 1 . .
F F20 0.66562(9) 1.20895(13) 0.61292(6) 0.0490(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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 120.18(15) ?
C6 C1 N8 . . 119.58(15) ?
C2 C1 N8 . . 120.13(14) ?
N7 C2 C1 . . 120.94(15) ?
N7 C2 C3 . . 121.67(16) ?
C1 C2 C3 . . 117.36(17) ?
C4 C3 C2 . . 121.20(19) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C3 C4 C5 . . 121.06(18) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C4 C5 C6 . . 119.0(2) ?
C4 C5 H5 . . 120.5 ?
C6 C5 H5 . . 120.5 ?
C5 C6 C1 . . 121.21(18) ?
C5 C6 H6 . . 119.4 ?
C1 C6 H6 . . 119.4 ?
C2 N7 H7A . . 123.8 ?
C2 N7 H7B . . 110.6 ?
H7A N7 H7B . . 119.4 ?
C9 N8 C1 . . 125.23(12) ?
C9 N8 H8 . . 122.1 ?
C1 N8 H8 . . 111.3 ?
N8 C9 C10 . . 122.24(13) ?
N8 C9 C14 . . 119.02(13) ?
C10 C9 C14 . . 118.74(14) ?
C11 C10 C9 . . 120.30(13) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C10 C11 C12 . . 121.08(14) ?
C10 C11 H11 . . 119.5 ?
C12 C11 H11 . . 119.5 ?
C11 C12 C13 . . 118.05(14) ?
C11 C12 C15 . . 124.48(14) ?
C13 C12 C15 . . 117.46(13) ?
C14 C13 C12 . . 121.44(13) ?
C14 C13 H13 . . 119.3 ?
C12 C13 H13 . . 119.3 ?
C13 C14 C9 . . 120.38(14) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
O16 C15 C12 . . 125.88(14) ?
O16 C15 C17 . . 115.33(14) ?
C12 C15 C17 . . 118.78(13) ?
F18 C17 F20 . . 107.33(14) ?
F18 C17 F19 . . 106.72(14) ?
F20 C17 F19 . . 107.33(13) ?
F18 C17 C15 . . 111.47(13) ?
F20 C17 C15 . . 112.54(13) ?
F19 C17 C15 . . 111.16(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.391(2) ?
C1 C2 . 1.402(2) ?
C1 N8 . 1.4244(19) ?
C2 N7 . 1.357(2) ?
C2 C3 . 1.411(2) ?
C3 C4 . 1.371(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.374(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.380(3) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
N7 H7A . 0.9044 ?
N7 H7B . 0.9069 ?
N8 C9 . 1.364(2) ?
N8 H8 . 0.9582 ?
C9 C10 . 1.404(2) ?
C9 C14 . 1.413(2) ?
C10 C11 . 1.382(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.402(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.410(2) ?
C12 C15 . 1.447(2) ?
C13 C14 . 1.364(2) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 O16 . 1.2180(18) ?
C15 C17 . 1.545(2) ?
C17 F18 . 1.3251(18) ?
C17 F20 . 1.332(2) ?
C17 F19 . 1.3437(19) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N7 H7B F19 3_646 0.91 2.32 3.2077(19) 166
N8 H8 O16 4_466 0.96 2.06 2.9757(17) 159
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 N7 . . . . -176.94(16) ?
N8 C1 C2 N7 . . . . 6.8(2) ?
C6 C1 C2 C3 . . . . 1.2(2) ?
N8 C1 C2 C3 . . . . -175.01(15) ?
N7 C2 C3 C4 . . . . 177.89(19) ?
C1 C2 C3 C4 . . . . -0.3(3) ?
C2 C3 C4 C5 . . . . -1.1(3) ?
C3 C4 C5 C6 . . . . 1.4(3) ?
C4 C5 C6 C1 . . . . -0.4(3) ?
C2 C1 C6 C5 . . . . -0.9(3) ?
N8 C1 C6 C5 . . . . 175.34(17) ?
C6 C1 N8 C9 . . . . 107.87(18) ?
C2 C1 N8 C9 . . . . -75.9(2) ?
C1 N8 C9 C10 . . . . 5.3(2) ?
C1 N8 C9 C14 . . . . -174.67(15) ?
N8 C9 C10 C11 . . . . -179.88(14) ?
C14 C9 C10 C11 . . . . 0.1(2) ?
C9 C10 C11 C12 . . . . 0.1(2) ?
C10 C11 C12 C13 . . . . 0.2(2) ?
C10 C11 C12 C15 . . . . 179.43(14) ?
C11 C12 C13 C14 . . . . -0.7(2) ?
C15 C12 C13 C14 . . . . -179.98(14) ?
C12 C13 C14 C9 . . . . 0.9(2) ?
N8 C9 C14 C13 . . . . 179.40(14) ?
C10 C9 C14 C13 . . . . -0.5(2) ?
C11 C12 C15 O16 . . . . -175.65(16) ?
C13 C12 C15 O16 . . . . 3.6(2) ?
C11 C12 C15 C17 . . . . 5.5(2) ?
C13 C12 C15 C17 . . . . -175.33(14) ?
O16 C15 C17 F18 . . . . -1.0(2) ?
C12 C15 C17 F18 . . . . 178.04(14) ?
O16 C15 C17 F20 . . . . 119.68(16) ?
C12 C15 C17 F20 . . . . -61.32(19) ?
O16 C15 C17 F19 . . . . -119.90(15) ?
C12 C15 C17 F19 . . . . 59.11(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744664
