#------------------------------------------------------------------------------
#$Date: 2022-03-18 12:36:28 +0200 (Fri, 18 Mar 2022) $
#$Revision: 273810 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104809.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_8104809
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 Crystal structure of N-(2-(trifluoromethyl)phenyl)hexanamide, C13H16F3NO
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              291
_journal_page_last               292
_journal_paper_doi               10.1515/ncrs-2020-0530
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C13 H16 F3 N O'
_chemical_formula_sum            'C13 H16 F3 N O'
_chemical_formula_weight         259.27
_chemical_name_common            ortho-trifluoromethyl-hexylanilide
_chemical_name_systematic        ortho-trifluoromethyl-hexylanilide
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                100.762(5)
_cell_angle_beta                 100.232(4)
_cell_angle_gamma                100.683(4)
_cell_formula_units_Z            2
_cell_length_a                   4.7889(4)
_cell_length_b                   11.7867(10)
_cell_length_c                   12.5323(11)
_cell_measurement_reflns_used    4072
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.74
_cell_volume                     666.19(10)
_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 0.994
_diffrn_measured_fraction_theta_max 0.987
_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  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11441
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.355
_diffrn_reflns_theta_min         1.695
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9009
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       rods
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.524
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0531
_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)+(0.0987P)²+0.1175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.1760
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2248
_reflns_number_total             3290
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0530_suppl.cif
_cod_data_source_block           g
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8104809
_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   0.935
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
F1 F 0.5693(4) 0.99393(11) 0.67521(13) 0.0829(5) Uani 1 1 d . . . . .
F2 F 0.3480(3) 0.83849(11) 0.71363(11) 0.0579(4) Uani 1 1 d . . . . .
F3 F 0.7950(3) 0.90673(13) 0.78576(10) 0.0677(4) Uani 1 1 d . . . . .
O1 O 1.0355(3) 0.57740(13) 0.71629(12) 0.0468(4) Uani 1 1 d . . . . .
N1 N 0.6219(3) 0.64221(13) 0.67946(12) 0.0313(3) Uani 1 1 d . . . . .
C1 C 0.5987(4) 0.88805(16) 0.69172(16) 0.0413(4) Uani 1 1 d . . . . .
C2 C 0.7965(3) 0.58452(15) 0.73483(14) 0.0318(4) Uani 1 1 d . . . . .
C3 C 0.6799(4) 0.52981(16) 0.82187(15) 0.0349(4) Uani 1 1 d . . . . .
H3A H 0.465268 0.518276 0.805753 0.042 Uiso 1 1 calc R U . . .
H3B H 0.758916 0.584990 0.895602 0.042 Uiso 1 1 calc R U . . .
C4 C 0.7583(4) 0.41162(15) 0.82640(14) 0.0344(4) Uani 1 1 d . . . . .
H4A H 0.973060 0.423667 0.843630 0.041 Uiso 1 1 calc R U . . .
H4B H 0.682652 0.357210 0.752120 0.041 Uiso 1 1 calc R U . . .
C5 C 0.6383(4) 0.35383(17) 0.91227(16) 0.0391(4) Uani 1 1 d . . . . .
H5A H 0.715535 0.407846 0.986675 0.047 Uiso 1 1 calc R U . . .
H5B H 0.423650 0.342488 0.895502 0.047 Uiso 1 1 calc R U . . .
C6 C 0.7143(5) 0.23541(19) 0.91577(19) 0.0552(5) Uani 1 1 d . . . . .
H6A H 0.928651 0.246373 0.929609 0.066 Uiso 1 1 calc R U . . .
H6B H 0.630783 0.180630 0.842075 0.066 Uiso 1 1 calc R U . . .
C7 C 0.6048(7) 0.1789(3) 1.0041(3) 0.0845(9) Uani 1 1 d . . . . .
H7A H 0.391362 0.159790 0.986658 0.127 Uiso 1 1 calc R U . . .
H7B H 0.677578 0.234194 1.076956 0.127 Uiso 1 1 calc R U . . .
H7C H 0.674783 0.106046 1.005868 0.127 Uiso 1 1 calc R U . . .
C11 C 0.6950(3) 0.69789(14) 0.59371(13) 0.0291(4) Uani 1 1 d . . . . .
C12 C 0.6767(3) 0.81467(15) 0.59592(14) 0.0325(4) Uani 1 1 d . . . . .
C13 C 0.7455(4) 0.86563(17) 0.50970(16) 0.0429(4) Uani 1 1 d . . . . .
H13 H 0.729028 0.944776 0.510025 0.051 Uiso 1 1 calc R U . . .
C14 C 0.8370(5) 0.80259(19) 0.42404(17) 0.0503(5) Uani 1 1 d . . . . .
H14 H 0.885008 0.838344 0.365764 0.060 Uiso 1 1 calc R U . . .
C15 C 0.8591(4) 0.68748(18) 0.42268(16) 0.0456(5) Uani 1 1 d . . . . .
H15 H 0.925129 0.644236 0.364020 0.055 Uiso 1 1 calc R U . . .
C16 C 0.7855(4) 0.63497(16) 0.50648(15) 0.0364(4) Uani 1 1 d . . . . .
H16 H 0.797021 0.554994 0.504312 0.044 Uiso 1 1 calc R U . . .
H1 H 0.463(4) 0.6438(17) 0.6963(16) 0.035(5) Uiso 1 1 d . . . . .
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'
O O 0.0106 0.0060 '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 C11 123.58(13) . .
C2 N1 H1 117.4(13) . .
C11 N1 H1 119.0(13) . .
F3 C1 F1 107.00(17) . .
F3 C1 F2 105.11(15) . .
F1 C1 F2 105.62(16) . .
F3 C1 C12 112.57(15) . .
F1 C1 C12 112.62(15) . .
F2 C1 C12 113.32(15) . .
O1 C2 N1 122.42(15) . .
O1 C2 C3 121.70(14) . .
N1 C2 C3 115.88(13) . .
C2 C3 C4 112.54(13) . .
C2 C3 H3A 109.1 . .
C4 C3 H3A 109.1 . .
C2 C3 H3B 109.1 . .
C4 C3 H3B 109.1 . .
H3A C3 H3B 107.8 . .
C3 C4 C5 113.41(14) . .
C3 C4 H4A 108.9 . .
C5 C4 H4A 108.9 . .
C3 C4 H4B 108.9 . .
C5 C4 H4B 108.9 . .
H4A C4 H4B 107.7 . .
C6 C5 C4 113.28(16) . .
C6 C5 H5A 108.9 . .
C4 C5 H5A 108.9 . .
C6 C5 H5B 108.9 . .
C4 C5 H5B 108.9 . .
H5A C5 H5B 107.7 . .
C5 C6 C7 113.8(2) . .
C5 C6 H6A 108.8 . .
C7 C6 H6A 108.8 . .
C5 C6 H6B 108.8 . .
C7 C6 H6B 108.8 . .
H6A C6 H6B 107.7 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C16 C11 C12 119.41(15) . .
C16 C11 N1 119.57(15) . .
C12 C11 N1 121.02(14) . .
C13 C12 C11 119.43(16) . .
C13 C12 C1 119.31(16) . .
C11 C12 C1 121.19(14) . .
C14 C13 C12 120.60(18) . .
C14 C13 H13 119.7 . .
C12 C13 H13 119.7 . .
C13 C14 C15 119.96(17) . .
C13 C14 H14 120.0 . .
C15 C14 H14 120.0 . .
C14 C15 C16 120.04(17) . .
C14 C15 H15 120.0 . .
C16 C15 H15 120.0 . .
C15 C16 C11 120.54(17) . .
C15 C16 H16 119.7 . .
C11 C16 H16 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C1 1.331(2) .
F2 C1 1.333(2) .
F3 C1 1.324(2) .
O1 C2 1.2222(19) .
N1 C2 1.351(2) .
N1 C11 1.421(2) .
N1 H1 0.83(2) .
C1 C12 1.490(2) .
C2 C3 1.504(2) .
C3 C4 1.517(2) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.517(2) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.513(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.516(3) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C11 C16 1.385(2) .
C11 C12 1.391(2) .
C12 C13 1.390(2) .
C13 C14 1.374(3) .
C13 H13 0.9500 .
C14 C15 1.377(3) .
C14 H14 0.9500 .
C15 C16 1.380(3) .
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
N1 H1 F2 0.83(2) 2.439(19) 2.8655(18) 113.1(16) .
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
C11 N1 C2 O1 1.2(3) . . . .
C11 N1 C2 C3 -179.21(15) . . . .
O1 C2 C3 C4 -37.7(2) . . . .
N1 C2 C3 C4 142.69(16) . . . .
C2 C3 C4 C5 -178.99(15) . . . .
C3 C4 C5 C6 179.42(16) . . . .
C4 C5 C6 C7 177.9(2) . . . .
C2 N1 C11 C16 50.9(2) . . . .
C2 N1 C11 C12 -129.18(18) . . . .
C16 C11 C12 C13 0.9(2) . . . .
N1 C11 C12 C13 -178.96(16) . . . .
C16 C11 C12 C1 -176.05(16) . . . .
N1 C11 C12 C1 4.0(2) . . . .
F3 C1 C12 C13 -113.06(19) . . . .
F1 C1 C12 C13 8.0(3) . . . .
F2 C1 C12 C13 127.84(18) . . . .
F3 C1 C12 C11 63.9(2) . . . .
F1 C1 C12 C11 -174.98(16) . . . .
F2 C1 C12 C11 -55.2(2) . . . .
C11 C12 C13 C14 -1.4(3) . . . .
C1 C12 C13 C14 175.62(17) . . . .
C12 C13 C14 C15 0.5(3) . . . .
C13 C14 C15 C16 0.9(3) . . . .
C14 C15 C16 C11 -1.4(3) . . . .
C12 C11 C16 C15 0.5(3) . . . .
N1 C11 C16 C15 -179.64(16) . . . .
