data_103-7072-7940_93
_audit_creation_date              2017-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number      '2014/7'
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_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.

Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst., 40, 786-790;
Palatinus, L. & van der Lee, A. (2008). J. Appl. Cryst. 41, 975-984;
Palatinus, L., Prathapa, S. J. & van Smaalen, S. (2012). J. Appl. Cryst. 45,
 575-580.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C19 H20 F3 N O'
_chemical_formula_sum             'C19 H20 F3 N O'
_chemical_formula_weight          335.36
_chemical_melting_point           ?
_chemical_oxdiff_formula          'F3 N O C17'
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'

_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       'triclinic'
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                    6.4856(5)
_cell_length_b                    10.5126(11)
_cell_length_c                    13.3256(13)
_cell_angle_alpha                 104.204(9)
_cell_angle_beta                  93.568(7)
_cell_angle_gamma                 97.731(7)
_cell_volume                      868.47(14)
_cell_formula_units_Z             2
_cell_measurement_reflns_used     1395
_cell_measurement_temperature     100(2)
_cell_measurement_theta_max       25.5810
_cell_measurement_theta_min       3.4960
_shelx_estimated_absorpt_T_max    ?
_shelx_estimated_absorpt_T_min    ?
_exptl_absorpt_coefficient_mu     0.101
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_T_min   0.88598
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             'clear colourless'
_exptl_crystal_colour_lustre      clear
_exptl_crystal_colour_modifier    .
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.282
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        prism
_exptl_crystal_F_000              352
_exptl_crystal_size_max           0.33
_exptl_crystal_size_mid           0.24
_exptl_crystal_size_min           0.21
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0188
_diffrn_reflns_av_unetI/netI      0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_number             6978
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full         25.242
_diffrn_reflns_theta_max          27.496
_diffrn_reflns_theta_min          2.872
_diffrn_ambient_temperature       100(2)
_diffrn_detector_area_resol_mean  16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -91.00   -1.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -57.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   47.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678   57.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega  -19.00    6.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -21.00   11.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega  -91.00  -25.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -77.0000 -180.0000 66

#__ type_ start__ end____ width___ exp.time_
  6 omega  -25.00   20.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
  7 omega  -43.00    7.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -19.0000 -180.0000 50
;
_diffrn_measurement_device_type   'Xcalibur, Eos'
_diffrn_measurement_method        'ω scans'
_diffrn_orient_matrix_UB_11       -0.0858260000
_diffrn_orient_matrix_UB_12       0.0258351000
_diffrn_orient_matrix_UB_13       0.0236069000
_diffrn_orient_matrix_UB_21       -0.0050417000
_diffrn_orient_matrix_UB_22       -0.0471615000
_diffrn_orient_matrix_UB_23       0.0301346000
_diffrn_orient_matrix_UB_31       0.0700748000
_diffrn_orient_matrix_UB_32       0.0455117000
_diffrn_orient_matrix_UB_33       0.0397408000
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 2160
_reflns_number_total              3965
_reflns_odcompleteness_completeness 98.99
_reflns_odcompleteness_iscentric  1
_reflns_odcompleteness_theta      28.51
_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_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max          1.345
_refine_diff_density_min          -0.327
_refine_diff_density_rms          0.071
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.046
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      222
_refine_ls_number_reflns          3965
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1517
_refine_ls_R_factor_gt            0.0976
_refine_ls_restrained_S_all       1.046
_refine_ls_shift/su_max           0.003
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1664P)²+0.6332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.2832
_refine_ls_wR_factor_ref          0.3317
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C11(H11), C13(H13), C14(H14), C17(H17)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      iterative
_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 0.6985(4) -0.0639(3) 0.17329(18) 0.0671(7) Uani 1 1 d . . . . .
 O2 O 1.0732(5) 0.1591(3) 0.0147(2) 0.0604(8) Uani 1 1 d . . . . .
 H2 H 1.0915 0.0952 -0.0341 0.091 Uiso 1 1 calc GR . . . .
 F3 F 0.4782(4) 0.0290(3) 0.2689(2) 0.0821(9) Uani 1 1 d . . . . .
 N4 N 0.9393(5) 0.1123(3) 0.0812(2) 0.0526(8) Uani 1 1 d . . . . .
 F5 F 0.4772(4) 0.0371(3) 0.1092(2) 0.0826(9) Uani 1 1 d . . . . .
 C1 C 0.7466(6) 0.1754(5) 0.2302(3) 0.0568(10) Uani 1 1 d . . . . .
 H1 H 0.6547 0.2456 0.2448 0.068 Uiso 1 1 calc R . . . .
 C2 C 0.8758(6) 0.1880(4) 0.3323(3) 0.0546(10) Uani 1 1 d . . . . .
 C3 C 0.8864(6) 0.2087(4) 0.1492(3) 0.0506(9) Uani 1 1 d . . . . .
 C4 C 0.6015(7) 0.0442(5) 0.1942(3) 0.0646(12) Uani 1 1 d . . . . .
 C5 C 1.1227(9) 0.2090(6) 0.5164(3) 0.0802(17) Uani 1 1 d . . . . .
 C6 C 1.1523(7) 0.1171(5) 0.4256(3) 0.0708(13) Uani 1 1 d . . . . .
 H6 H 1.2552 0.0608 0.4262 0.085 Uiso 1 1 calc R . . . .
 C7 C 0.8437(7) 0.2807(4) 0.4237(3) 0.0643(12) Uani 1 1 d . . . . .
 C8 C 1.1501(9) 0.4113(6) 0.2146(4) 0.0890(18) Uani 1 1 d . . . . .
 H8 H 1.2353 0.3604 0.2440 0.107 Uiso 1 1 calc R . . . .
 C9 C 0.9559(7) 0.3510(4) 0.1589(3) 0.0588(11) Uani 1 1 d . . . . .
 C10 C 0.6822(9) 0.3708(5) 0.4282(4) 0.0879(17) Uani 1 1 d . . . . .
 H10A H 0.7029 0.4215 0.3760 0.132 Uiso 1 1 calc GR . . . .
 H10B H 0.6958 0.4321 0.4975 0.132 Uiso 1 1 calc GR . . . .
 H10C H 0.5424 0.3177 0.4139 0.132 Uiso 1 1 calc GR . . . .
 C11 C 1.0294(7) 0.1085(5) 0.3338(3) 0.0638(12) Uani 1 1 d . . . . .
 H11 H 1.0513 0.0473 0.2714 0.077 Uiso 1 1 calc R . . . .
 C12 C 1.2662(10) 0.2182(8) 0.6158(4) 0.113(2) Uani 1 1 d . . . . .
 H12A H 1.2425 0.1335 0.6350 0.169 Uiso 1 1 calc GR . . . .
 H12B H 1.2343 0.2894 0.6727 0.169 Uiso 1 1 calc GR . . . .
 H12C H 1.4127 0.2374 0.6027 0.169 Uiso 1 1 calc GR . . . .
 C13 C 0.9721(9) 0.2891(6) 0.5146(3) 0.0790(15) Uani 1 1 d . . . . .
 H13 H 0.9545 0.3522 0.5768 0.095 Uiso 1 1 calc R . . . .
 C14 C 0.9098(14) 0.5589(6) 0.1272(5) 0.110(2) Uani 1 1 d . . . . .
 H14 H 0.8300 0.6117 0.0968 0.132 Uiso 1 1 calc R . . . .
 C15 C 0.8335(9) 0.4227(5) 0.1140(4) 0.0747(13) Uani 1 1 d . . . . .
 C16 C 1.1037(16) 0.6168(7) 0.1852(6) 0.118(3) Uani 1 1 d . . . . .
 C17 C 1.2128(13) 0.5384(10) 0.2257(7) 0.126(3) Uani 1 1 d . . . . .
 H17 H 1.3434 0.5772 0.2647 0.151 Uiso 1 1 calc R . . . .
 C18 C 0.6388(11) 0.3607(7) 0.0475(6) 0.109(2) Uani 1 1 d . . . . .
 H18A H 0.6458 0.2669 0.0163 0.163 Uiso 1 1 calc GR . . . .
 H18B H 0.6207 0.4062 -0.0076 0.163 Uiso 1 1 calc GR . . . .
 H18C H 0.5201 0.3675 0.0896 0.163 Uiso 1 1 calc GR . . . .
 C19 C 1.1849(19) 0.7593(9) 0.2038(7) 0.167(4) Uani 1 1 d . . . . .
 H19A H 1.1161 0.7950 0.1514 0.250 Uiso 1 1 calc GR . . . .
 H19B H 1.3361 0.7710 0.1989 0.250 Uiso 1 1 calc GR . . . .
 H19C H 1.1564 0.8067 0.2733 0.250 Uiso 1 1 calc GR . . . .


_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 C4 1.351(5) . ?
 O2 N4 1.405(4) . ?
 F3 C4 1.342(4) . ?
 N4 C3 1.284(5) . ?
 F5 C4 1.329(5) . ?
 C1 C2 1.519(6) . ?
 C1 C3 1.527(5) . ?
 C1 C4 1.512(7) . ?
 C2 C7 1.407(5) . ?
 C2 C11 1.386(6) . ?
 C3 C9 1.474(6) . ?
 C5 C6 1.392(7) . ?
 C5 C12 1.546(7) . ?
 C5 C13 1.376(8) . ?
 C6 C11 1.395(6) . ?
 C7 C10 1.498(7) . ?
 C7 C13 1.403(7) . ?
 C8 C9 1.406(7) . ?
 C8 C17 1.312(10) . ?
 C9 C15 1.371(7) . ?
 C14 C15 1.414(8) . ?
 C14 C16 1.411(11) . ?
 C15 C18 1.470(8) . ?
 C16 C17 1.341(12) . ?
 C16 C19 1.474(10) . ?

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 N4 O2 111.3(3) . . ?
 C2 C1 C3 110.7(3) . . ?
 C4 C1 C2 112.3(4) . . ?
 C4 C1 C3 114.7(3) . . ?
 C7 C2 C1 120.8(4) . . ?
 C11 C2 C1 119.0(3) . . ?
 C11 C2 C7 120.2(4) . . ?
 N4 C3 C1 118.2(4) . . ?
 N4 C3 C9 125.5(3) . . ?
 C9 C3 C1 116.3(3) . . ?
 F1 C4 C1 114.8(3) . . ?
 F3 C4 F1 105.8(4) . . ?
 F3 C4 C1 109.5(3) . . ?
 F5 C4 F1 106.6(3) . . ?
 F5 C4 F3 107.3(3) . . ?
 F5 C4 C1 112.4(4) . . ?
 C6 C5 C12 117.7(6) . . ?
 C13 C5 C6 119.7(5) . . ?
 C13 C5 C12 122.5(5) . . ?
 C5 C6 C11 119.3(5) . . ?
 C2 C7 C10 123.3(4) . . ?
 C13 C7 C2 117.7(5) . . ?
 C13 C7 C10 118.9(4) . . ?
 C17 C8 C9 119.6(7) . . ?
 C8 C9 C3 118.7(5) . . ?
 C15 C9 C3 120.5(4) . . ?
 C15 C9 C8 120.8(5) . . ?
 C2 C11 C6 121.0(4) . . ?
 C5 C13 C7 122.1(4) . . ?
 C16 C14 C15 120.5(7) . . ?
 C9 C15 C14 117.3(6) . . ?
 C9 C15 C18 122.3(5) . . ?
 C14 C15 C18 120.3(6) . . ?
 C14 C16 C19 122.0(10) . . ?
 C17 C16 C14 117.9(6) . . ?
 C17 C16 C19 120.1(9) . . ?
 C8 C17 C16 124.0(8) . . ?

_olex2_date_sample_data_collection 2017-11-18
_olex2_submission_special_instructions 'No special instructions were received'
