data_v18651
_audit_creation_date               2019-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506),
 SHELXL-2018/3, and manual edit
;
_database_code_depnum_ccdc_archive ?
_audit_contact_author_name         'Xray Staff'
_audit_contact_author_email        xray@caltech.edu
_audit_contact_author_address      
;
Beckman Institute
Caltech 139-74
Pasadena CA 91125
USA
;
_audit_contact_author_phone        16263952741
_shelx_SHELXL_version_number       2018/3
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C14 H16 F5 N O'
_chemical_formula_sum              'C14 H16 F5 N O'
_chemical_formula_weight           309.28
_chemical_absolute_configuration   ad
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 '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' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     8.7849(11)
_cell_length_b                     5.4108(8)
_cell_length_c                     14.8752(19)
_cell_angle_alpha                  90
_cell_angle_beta                   98.627(7)
_cell_angle_gamma                  90
_cell_volume                       699.07(16)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      9848
_cell_measurement_temperature      100
_cell_measurement_theta_max        79.05
_cell_measurement_theta_min        3.00
_shelx_estimated_absorpt_T_max     0.868
_shelx_estimated_absorpt_T_min     0.760
_exptl_absorpt_coefficient_mu      1.212
_exptl_absorpt_correction_T_max    1.0000
_exptl_absorpt_correction_T_min    0.6450
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1210 before and 0.0849 after correction.
The Ratio of minimum to maximum transmission is 0.6450.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'colourless'
_exptl_crystal_density_diffrn      1.469
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         'block'
_exptl_crystal_F_000               320
_exptl_crystal_size_max            0.24
_exptl_crystal_size_mid            0.23
_exptl_crystal_size_min            0.12
loop_
 _exptl_crystal_face_index_h
 _exptl_crystal_face_index_k
 _exptl_crystal_face_index_l
 _exptl_crystal_face_perp_dist
   -1.00    0.00    1.00    0.0540
    1.00    0.00   -1.00    0.0840
    0.00   -1.00    0.00    0.1120
    0.00    0.00   -1.00    0.0160
    0.00    0.00    1.00    0.0580
    0.00    2.00    1.00    0.1100
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0414
_diffrn_reflns_av_unetI/netI       0.0219
_diffrn_reflns_Laue_measured_fraction_full  0.985
_diffrn_reflns_Laue_measured_fraction_max  0.967
_diffrn_reflns_limit_h_max         11
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         6
_diffrn_reflns_limit_k_min         -6
_diffrn_reflns_limit_l_max         18
_diffrn_reflns_limit_l_min         -18
_diffrn_reflns_number              22266
_diffrn_reflns_point_group_measured_fraction_full  0.979
_diffrn_reflns_point_group_measured_fraction_max  0.936
_diffrn_reflns_theta_full          67.679
_diffrn_reflns_theta_max           79.309
_diffrn_reflns_theta_min           3.005
_diffrn_ambient_temperature        100
_diffrn_detector                   'CPAD Area Detector'
_diffrn_detector_area_resol_mean   7.69
_diffrn_detector_type              'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full  0.985
_diffrn_measured_fraction_theta_max  0.967
_diffrn_measurement_device         'κ-geometry diffractometer'
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_monochromator    'multilayer mirrors'
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     'microfocus sealed tube'
_diffrn_source_current             1
_diffrn_source_power               0.05
_diffrn_source_type                'Incoatec I\mS HB'
_diffrn_source_voltage             50
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.748
_reflns_Friedel_fraction_full      0.972
_reflns_Friedel_fraction_max       0.899
_reflns_number_gt                  2809
_reflns_number_total               2842
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_data_collection        'BIS V6.2.9/2018-03-16 & APEX3 v2018.7-2 (Bruker-AXS, 2018)'
_computing_cell_refinement        'SAINT V8.38A (Bruker-AXS, 2016)'
_computing_data_reduction         'SAINT V8.38A (Bruker-AXS, 2016)'
_computing_structure_solution     'SHELXT-2014/5 (Sheldrick, 2013)'
_computing_structure_refinement   'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics     'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_refine_diff_density_max           0.213
_refine_diff_density_min           -0.137
_refine_diff_density_rms           0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1190 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.15(4)
_refine_ls_abs_structure_Hooft     0.17(3)
_refine_ls_extinction_coef         0.0038(9)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref     1.046
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       192
_refine_ls_number_reflns           2842
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0279
_refine_ls_R_factor_gt             0.0276
_refine_ls_restrained_S_all        1.046
_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)+(0.0283P)²+0.2093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0694
_refine_ls_wR_factor_ref           0.0696
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       ?
_atom_sites_solution_secondary     ?
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 0.73321(16) 0.1607(2) 0.16661(9) 0.0395(3) Uani 1 1 d . . . . .
 F2 F 0.57808(13) 0.2920(3) 0.04834(8) 0.0366(3) Uani 1 1 d . . . . .
 F3 F 0.95414(14) 0.4795(3) 0.12839(9) 0.0510(4) Uani 1 1 d . . . . .
 F4 F 0.86937(15) 0.2356(3) 0.01812(9) 0.0502(4) Uani 1 1 d . . . . .
 F5 F 0.80130(17) 0.6170(3) 0.01209(9) 0.0486(4) Uani 1 1 d . . . . .
 O1 O 0.90483(14) 0.6254(3) 0.63584(9) 0.0254(3) Uani 1 1 d . . . . .
 N1 N 0.51930(18) 0.6832(3) 0.30176(11) 0.0264(4) Uani 1 1 d . . . . .
 C1 C 0.7296(2) 0.4748(4) 0.39972(13) 0.0228(4) Uani 1 1 d . . . . .
 H1 H 0.739885 0.359297 0.352887 0.027 Uiso 1 1 calc R . . . .
 C2 C 0.82724(19) 0.4575(4) 0.48236(13) 0.0220(4) Uani 1 1 d . . . . .
 H2 H 0.902623 0.330433 0.491443 0.026 Uiso 1 1 calc R . . . .
 C3 C 0.81485(19) 0.6250(4) 0.55148(12) 0.0207(4) Uani 1 1 d . . . . .
 C4 C 0.70294(19) 0.8088(3) 0.53720(13) 0.0217(4) Uani 1 1 d . . . . .
 H4 H 0.693558 0.923973 0.584272 0.026 Uiso 1 1 calc R . . . .
 C5 C 0.60512(19) 0.8261(3) 0.45528(13) 0.0216(4) Uani 1 1 d . . . . .
 H5 H 0.529293 0.952537 0.447040 0.026 Uiso 1 1 calc R . . . .
 C6 C 0.61635(19) 0.6593(4) 0.38416(12) 0.0209(4) Uani 1 1 d . . . . .
 C7 C 1.0147(2) 0.4310(4) 0.65313(14) 0.0278(4) Uani 1 1 d . . . . .
 H7A H 1.090139 0.444755 0.611046 0.042 Uiso 1 1 calc GR . . . .
 H7B H 0.962055 0.271237 0.644392 0.042 Uiso 1 1 calc GR . . . .
 H7C H 1.067650 0.443325 0.715832 0.042 Uiso 1 1 calc GR . . . .
 C8 C 0.3830(2) 0.8396(4) 0.29123(13) 0.0244(4) Uani 1 1 d . . . . .
 H8A H 0.411033 1.014968 0.303430 0.029 Uiso 1 1 calc R . . . .
 H8B H 0.310757 0.787084 0.332630 0.029 Uiso 1 1 calc R . . . .
 C9 C 0.3132(2) 0.8019(4) 0.19252(14) 0.0289(4) Uani 1 1 d . . . . .
 H9A H 0.359414 0.915838 0.152071 0.035 Uiso 1 1 calc R . . . .
 H9B H 0.200336 0.827008 0.183670 0.035 Uiso 1 1 calc R . . . .
 C10 C 0.3537(2) 0.5323(4) 0.17482(15) 0.0278(4) Uani 1 1 d . . . . .
 H10A H 0.352387 0.501508 0.109098 0.033 Uiso 1 1 calc R . . . .
 H10B H 0.281269 0.417084 0.198136 0.033 Uiso 1 1 calc R . . . .
 C11 C 0.5171(2) 0.5052(4) 0.22767(12) 0.0228(4) Uani 1 1 d . . . . .
 H11 H 0.532897 0.333945 0.252609 0.027 Uiso 1 1 calc R . . . .
 C12 C 0.6456(2) 0.5719(4) 0.17136(13) 0.0232(4) Uani 1 1 d . . . . .
 H12A H 0.609734 0.711466 0.130603 0.028 Uiso 1 1 calc R . . . .
 H12B H 0.736896 0.629043 0.213422 0.028 Uiso 1 1 calc R . . . .
 C13 C 0.6934(2) 0.3646(4) 0.11502(14) 0.0261(4) Uani 1 1 d . . . . .
 C14 C 0.8326(2) 0.4246(5) 0.06716(14) 0.0347(5) Uani 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 F1 C13 1.359(2) . ?
 F2 C13 1.365(2) . ?
 F3 C14 1.329(2) . ?
 F4 C14 1.324(3) . ?
 F5 C14 1.328(3) . ?
 O1 C3 1.379(2) . ?
 O1 C7 1.425(2) . ?
 N1 C6 1.390(2) . ?
 N1 C8 1.456(2) . ?
 N1 C11 1.462(2) . ?
 C1 H1 0.9500 . ?
 C1 C2 1.393(3) . ?
 C1 C6 1.404(2) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.387(3) . ?
 C3 C4 1.392(2) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.385(3) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.405(3) . ?
 C7 H7A 0.9800 . ?
 C7 H7B 0.9800 . ?
 C7 H7C 0.9800 . ?
 C8 H8A 0.9900 . ?
 C8 H8B 0.9900 . ?
 C8 C9 1.518(3) . ?
 C9 H9A 0.9900 . ?
 C9 H9B 0.9900 . ?
 C9 C10 1.534(3) . ?
 C10 H10A 0.9900 . ?
 C10 H10B 0.9900 . ?
 C10 C11 1.537(3) . ?
 C11 H11 1.0000 . ?
 C11 C12 1.546(2) . ?
 C12 H12A 0.9900 . ?
 C12 H12B 0.9900 . ?
 C12 C13 1.497(3) . ?
 C13 C14 1.539(3) . ?

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
  _geom_angle_publ_flag
 C3 O1 C7 116.32(14) . . ?
 C6 N1 C8 122.33(15) . . ?
 C6 N1 C11 122.73(15) . . ?
 C8 N1 C11 112.61(15) . . ?
 C2 C1 H1 119.3 . . ?
 C2 C1 C6 121.37(17) . . ?
 C6 C1 H1 119.3 . . ?
 C1 C2 H2 119.9 . . ?
 C3 C2 C1 120.27(17) . . ?
 C3 C2 H2 119.9 . . ?
 O1 C3 C2 125.28(16) . . ?
 O1 C3 C4 115.65(16) . . ?
 C2 C3 C4 119.07(16) . . ?
 C3 C4 H4 119.6 . . ?
 C5 C4 C3 120.87(16) . . ?
 C5 C4 H4 119.6 . . ?
 C4 C5 H5 119.5 . . ?
 C4 C5 C6 120.98(16) . . ?
 C6 C5 H5 119.5 . . ?
 N1 C6 C1 122.49(17) . . ?
 N1 C6 C5 120.07(16) . . ?
 C1 C6 C5 117.43(16) . . ?
 O1 C7 H7A 109.5 . . ?
 O1 C7 H7B 109.5 . . ?
 O1 C7 H7C 109.5 . . ?
 H7A C7 H7B 109.5 . . ?
 H7A C7 H7C 109.5 . . ?
 H7B C7 H7C 109.5 . . ?
 N1 C8 H8A 111.1 . . ?
 N1 C8 H8B 111.1 . . ?
 N1 C8 C9 103.42(15) . . ?
 H8A C8 H8B 109.0 . . ?
 C9 C8 H8A 111.1 . . ?
 C9 C8 H8B 111.1 . . ?
 C8 C9 H9A 111.2 . . ?
 C8 C9 H9B 111.2 . . ?
 C8 C9 C10 102.93(16) . . ?
 H9A C9 H9B 109.1 . . ?
 C10 C9 H9A 111.2 . . ?
 C10 C9 H9B 111.2 . . ?
 C9 C10 H10A 111.2 . . ?
 C9 C10 H10B 111.2 . . ?
 C9 C10 C11 103.05(15) . . ?
 H10A C10 H10B 109.1 . . ?
 C11 C10 H10A 111.2 . . ?
 C11 C10 H10B 111.2 . . ?
 N1 C11 C10 103.22(15) . . ?
 N1 C11 H11 110.2 . . ?
 N1 C11 C12 109.07(15) . . ?
 C10 C11 H11 110.2 . . ?
 C10 C11 C12 113.73(16) . . ?
 C12 C11 H11 110.2 . . ?
 C11 C12 H12A 108.6 . . ?
 C11 C12 H12B 108.6 . . ?
 H12A C12 H12B 107.6 . . ?
 C13 C12 C11 114.69(16) . . ?
 C13 C12 H12A 108.6 . . ?
 C13 C12 H12B 108.6 . . ?
 F1 C13 F2 106.04(16) . . ?
 F1 C13 C12 111.21(16) . . ?
 F1 C13 C14 106.13(17) . . ?
 F2 C13 C12 112.47(16) . . ?
 F2 C13 C14 106.21(16) . . ?
 C12 C13 C14 114.22(16) . . ?
 F3 C14 C13 110.02(17) . . ?
 F4 C14 F3 108.21(18) . . ?
 F4 C14 F5 108.10(17) . . ?
 F4 C14 C13 111.63(19) . . ?
 F5 C14 F3 108.6(2) . . ?
 F5 C14 C13 110.23(17) . . ?

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
  _geom_torsion_publ_flag
 F1 C13 C14 F3 -62.8(2) . . . . ?
 F1 C13 C14 F4 57.4(2) . . . . ?
 F1 C13 C14 F5 177.53(17) . . . . ?
 F2 C13 C14 F3 -175.34(19) . . . . ?
 F2 C13 C14 F4 -55.2(2) . . . . ?
 F2 C13 C14 F5 65.0(2) . . . . ?
 O1 C3 C4 C5 -179.64(15) . . . . ?
 N1 C8 C9 C10 33.01(19) . . . . ?
 N1 C11 C12 C13 159.80(15) . . . . ?
 C1 C2 C3 O1 179.89(16) . . . . ?
 C1 C2 C3 C4 0.5(3) . . . . ?
 C2 C1 C6 N1 178.85(17) . . . . ?
 C2 C1 C6 C5 0.0(3) . . . . ?
 C2 C3 C4 C5 -0.2(3) . . . . ?
 C3 C4 C5 C6 -0.2(3) . . . . ?
 C4 C5 C6 N1 -178.57(16) . . . . ?
 C4 C5 C6 C1 0.3(2) . . . . ?
 C6 N1 C8 C9 -178.58(17) . . . . ?
 C6 N1 C11 C10 154.41(17) . . . . ?
 C6 N1 C11 C12 -84.3(2) . . . . ?
 C6 C1 C2 C3 -0.4(3) . . . . ?
 C7 O1 C3 C2 -2.5(3) . . . . ?
 C7 O1 C3 C4 176.98(16) . . . . ?
 C8 N1 C6 C1 167.29(17) . . . . ?
 C8 N1 C6 C5 -13.9(3) . . . . ?
 C8 N1 C11 C10 -8.6(2) . . . . ?
 C8 N1 C11 C12 112.65(17) . . . . ?
 C8 C9 C10 C11 -38.47(19) . . . . ?
 C9 C10 C11 N1 28.85(19) . . . . ?
 C9 C10 C11 C12 -89.18(19) . . . . ?
 C10 C11 C12 C13 -85.6(2) . . . . ?
 C11 N1 C6 C1 5.9(3) . . . . ?
 C11 N1 C6 C5 -175.22(16) . . . . ?
 C11 N1 C8 C9 -15.5(2) . . . . ?
 C11 C12 C13 F1 -53.9(2) . . . . ?
 C11 C12 C13 F2 64.9(2) . . . . ?
 C11 C12 C13 C14 -173.93(16) . . . . ?
 C12 C13 C14 F3 60.1(2) . . . . ?
 C12 C13 C14 F4 -179.74(17) . . . . ?
 C12 C13 C14 F5 -59.6(2) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
