#------------------------------------------------------------------------------
#$Date: 2022-03-21 11:49:40 +0200 (Mon, 21 Mar 2022) $
#$Revision: 273869 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104821.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_8104821
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of para-trifluoromethyl-aniline hemihydrate,
 C14H14F6N2O
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              329
_journal_page_last               331
_journal_paper_doi               10.1515/ncrs-2020-0512
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         '2(C7 H6 F3 N), H2 O'
_chemical_formula_sum            'C14 H14 F6 N2 O'
_chemical_formula_weight         340.27
_chemical_name_common
'para-trifluoromethyl-aniline hemihydrate'
_chemical_name_systematic
'para-trifluoromethyl-aniline hemihydrate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7552(12)
_cell_length_b                   10.7574(9)
_cell_length_c                   8.0207(7)
_cell_measurement_reflns_used    3052
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      2.21
_cell_volume                     1532.0(2)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12771
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_min         2.214
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9010
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.521
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.286
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1906
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0430P)²+0.4873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1330
_reflns_number_total             1906
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0512_suppl.cif
_cod_data_source_block           g
_cod_database_code               8104821
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.891
_shelx_estimated_absorpt_t_max   0.960
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.500000 0.49124(17) 0.750000 0.0573(5) Uani 1 2 d DS T P . .
N1 N 0.57698(7) 0.34368(15) 0.4965(2) 0.0520(4) Uani 1 1 d . . . . .
C1 C 0.89510(9) 0.39375(17) 0.5090(2) 0.0564(4) Uani 1 1 d D . . . .
C11 C 0.65549(7) 0.35450(12) 0.49763(16) 0.0366(3) Uani 1 1 d . . . . .
C12 C 0.69036(7) 0.45499(12) 0.41937(18) 0.0374(3) Uani 1 1 d . . . . .
H12 H 0.660770 0.515151 0.362563 0.045 Uiso 1 1 calc R U . . .
C13 C 0.76765(7) 0.46730(12) 0.42416(18) 0.0383(3) Uani 1 1 d . . . . .
H13 H 0.791011 0.535818 0.370226 0.046 Uiso 1 1 calc R U . . .
C14 C 0.81141(7) 0.38059(13) 0.50697(17) 0.0386(3) Uani 1 1 d . . . . .
C15 C 0.77703(8) 0.28104(13) 0.58534(19) 0.0445(4) Uani 1 1 d . . . . .
H15 H 0.806777 0.221108 0.642183 0.053 Uiso 1 1 calc R U . . .
C16 C 0.70005(8) 0.26853(12) 0.58129(19) 0.0434(4) Uani 1 1 d . . . . .
H16 H 0.676985 0.200246 0.636369 0.052 Uiso 1 1 calc R U . . .
H1 H 0.5234(10) 0.4423(11) 0.6858(19) 0.081(7) Uiso 1 1 d D . . . .
H1A H 0.5533(10) 0.3855(17) 0.416(2) 0.064(6) Uiso 1 1 d . . . . .
H1B H 0.5623(10) 0.2714(19) 0.510(2) 0.060(6) Uiso 1 1 d . . . . .
F1 F 0.9293(2) 0.3371(5) 0.6340(6) 0.0993(13) Uani 0.742(11) 1 d D . P A 1
F2 F 0.91733(18) 0.5102(2) 0.5155(7) 0.1009(15) Uani 0.742(11) 1 d D . P A 1
F3 F 0.9292(2) 0.3455(4) 0.3779(4) 0.0863(11) Uani 0.742(11) 1 d D . P A 1
F4 F 0.9165(7) 0.389(2) 0.6614(12) 0.142(6) Uani 0.258(11) 1 d D . P A 2
F5 F 0.9194(6) 0.4923(17) 0.439(3) 0.181(8) Uani 0.258(11) 1 d D . P A 2
F6 F 0.9244(7) 0.302(2) 0.430(3) 0.171(8) Uani 0.258(11) 1 d D . P A 2
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'
O O 0.0106 0.0060 '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
H1 O1 H1 102.9(18) . 3_656
C11 N1 H1A 115.5(12) . .
C11 N1 H1B 113.0(13) . .
H1A N1 H1B 115.0(18) . .
F5 C1 F4 110.6(10) . .
F5 C1 F6 106.7(9) . .
F4 C1 F6 108.7(9) . .
F2 C1 F3 105.6(3) . .
F2 C1 F1 105.8(3) . .
F3 C1 F1 102.2(3) . .
F5 C1 C14 114.2(6) . .
F4 C1 C14 107.6(6) . .
F6 C1 C14 108.9(7) . .
F2 C1 C14 113.0(2) . .
F3 C1 C14 114.2(2) . .
F1 C1 C14 115.0(2) . .
C16 C11 C12 118.70(12) . .
C16 C11 N1 121.00(14) . .
C12 C11 N1 120.26(13) . .
C13 C12 C11 120.23(12) . .
C13 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C12 C13 C14 120.49(13) . .
C12 C13 H13 119.8 . .
C14 C13 H13 119.8 . .
C15 C14 C13 119.47(13) . .
C15 C14 C1 120.50(13) . .
C13 C14 C1 120.02(14) . .
C16 C15 C14 120.27(13) . .
C16 C15 H15 119.9 . .
C14 C15 H15 119.9 . .
C15 C16 C11 120.84(13) . .
C15 C16 H16 119.6 . .
C11 C16 H16 119.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 H1 0.846(6) .
O1 H1 0.846(6) 3_656
N1 C11 1.3988(18) .
N1 H1A 0.894(19) .
N1 H1B 0.83(2) .
C1 F5 1.276(9) .
C1 F4 1.281(9) .
C1 F6 1.285(10) .
C1 F2 1.314(3) .
C1 F3 1.320(3) .
C1 F1 1.321(3) .
C1 C14 1.493(2) .
C11 C16 1.390(2) .
C11 C12 1.3949(18) .
C12 C13 1.3791(18) .
C12 H12 0.9500 .
C13 C14 1.3839(19) .
C13 H13 0.9500 .
C14 C15 1.384(2) .
C15 C16 1.374(2) .
C15 H15 0.9500 .
C16 H16 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.846(6) 2.082(7) 2.9193(17) 170.3(16) .
N1 H1A O1 0.894(19) 2.10(2) 2.988(2) 170.9(17) 5_666
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
C16 C11 C12 C13 0.6(2) . . . .
N1 C11 C12 C13 178.35(14) . . . .
C11 C12 C13 C14 -0.2(2) . . . .
C12 C13 C14 C15 0.0(2) . . . .
C12 C13 C14 C1 179.02(14) . . . .
F5 C1 C14 C15 -177.0(16) . . . .
F4 C1 C14 C15 -53.8(12) . . . .
F6 C1 C14 C15 63.9(15) . . . .
F2 C1 C14 C15 -145.6(3) . . . .
F3 C1 C14 C15 93.7(3) . . . .
F1 C1 C14 C15 -24.0(4) . . . .
F5 C1 C14 C13 3.9(16) . . . .
F4 C1 C14 C13 127.1(12) . . . .
F6 C1 C14 C13 -115.2(15) . . . .
F2 C1 C14 C13 35.4(3) . . . .
F3 C1 C14 C13 -85.3(3) . . . .
F1 C1 C14 C13 156.9(3) . . . .
C13 C14 C15 C16 -0.1(2) . . . .
C1 C14 C15 C16 -179.19(15) . . . .
C14 C15 C16 C11 0.6(2) . . . .
C12 C11 C16 C15 -0.8(2) . . . .
N1 C11 C16 C15 -178.50(14) . . . .
