 
data_4aa
  
_audit_creation_method            'SHELXL-2017/1' 
_shelx_SHELXL_version_number      '2017/1' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C15 H12 F3 N' 
_chemical_formula_sum 
 'C15 H12 F3 N' 
_chemical_formula_weight          263.26 
  
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' 
 'F'  'F'   0.0171   0.0103 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       orthorhombic 
_space_group_IT_number            33 
_space_group_name_H-M_alt         'P n a 21' 
_space_group_name_Hall            'P 2c -2n' 
  
_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. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, -y, z+1/2' 
 'x+1/2, -y+1/2, z' 
 '-x+1/2, y+1/2, z+1/2' 
  
_cell_length_a                    27.0703(18) 
_cell_length_b                    5.7522(4) 
_cell_length_c                    8.0156(5) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      1248.14(14) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     903 
_cell_measurement_theta_min       3.0040 
_cell_measurement_theta_max       27.7520 
  
_exptl_crystal_description        blocks 
_exptl_crystal_colour             Colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.401 
_exptl_crystal_F_000              544 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.48 
_exptl_crystal_size_mid           0.34 
_exptl_crystal_size_min           0.19 
_exptl_absorpt_coefficient_mu     0.113 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.965 
_exptl_absorpt_correction_T_max   0.980 
_exptl_absorpt_process_details     
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'Enhance (Mo) X-ray Source' 
_diffrn_measurement_device_type   'Agilent Xcalibur 3 E' 
_diffrn_measurement_method        'omega scans' 
_diffrn_detector_area_resol_mean  16.0382 
_diffrn_reflns_number             2890 
_diffrn_reflns_av_unetI/netI      0.0347 
_diffrn_reflns_av_R_equivalents   0.0219 
_diffrn_reflns_limit_h_min        -15 
_diffrn_reflns_limit_h_max        32 
_diffrn_reflns_limit_k_min        -5 
_diffrn_reflns_limit_k_max        7 
_diffrn_reflns_limit_l_min        -10 
_diffrn_reflns_limit_l_max        6 
_diffrn_reflns_theta_min          2.953 
_diffrn_reflns_theta_max          28.280 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.825 
_diffrn_measured_fraction_theta_full  0.988 
_diffrn_reflns_Laue_measured_fraction_max    0.825 
_diffrn_reflns_Laue_measured_fraction_full   0.988 
_diffrn_reflns_point_group_measured_fraction_max   0.519 
_diffrn_reflns_point_group_measured_fraction_full  0.640 
_reflns_number_total              1611 
_reflns_number_gt                 1477 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.177 
_reflns_Friedel_fraction_max      0.168 
_reflns_Friedel_fraction_full     0.233 
  
_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. 
; 
  
_computing_data_collection        'CrysAlisPro, Agilent Technologies' 
_computing_cell_refinement        'CrysAlisPro, Agilent Technologies' 
_computing_data_reduction         'CrysAlisPro, Agilent Technologies' 
_computing_structure_solution     'SHELXS-2013 (Sheldrick, 2013)' 
_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'CIFTAB-2013 (Sheldrick, 2013)' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0533P)²+0.4847P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 223 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    0.0(10) 
_chemical_absolute_configuration  . 
_refine_ls_number_reflns          1611 
_refine_ls_number_parameters      172 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0536 
_refine_ls_R_factor_gt            0.0489 
_refine_ls_wR_factor_ref          0.1228 
_refine_ls_wR_factor_gt           0.1187 
_refine_ls_goodness_of_fit_ref    1.136 
_refine_ls_restrained_S_all       1.136 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
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 
N1 N 0.28498(10) 0.2610(5) 0.3898(4) 0.0287(7) Uani 1 1 d . . . . . 
C2 C 0.24747(13) 0.3757(6) 0.4954(5) 0.0272(8) Uani 1 1 d . . . . . 
H2A H 0.259386 0.516208 0.556807 0.033 Uiso 1 1 calc R U . . . 
C3 C 0.27094(15) 0.1537(7) 0.5466(6) 0.0394(10) Uani 1 1 d . . . . . 
H3A H 0.295078 0.158680 0.639328 0.047 Uiso 1 1 calc R U . . . 
H3B H 0.250597 0.010823 0.541835 0.047 Uiso 1 1 calc R U . . . 
C4 C 0.33269(12) 0.3630(6) 0.3793(5) 0.0257(8) Uani 1 1 d . . . . . 
C5 C 0.37425(13) 0.2420(6) 0.4333(5) 0.0316(9) Uani 1 1 d . . . . . 
H5A H 0.370577 0.095408 0.486481 0.038 Uiso 1 1 calc R U . . . 
C6 C 0.42092(13) 0.3347(6) 0.4098(5) 0.0336(9) Uani 1 1 d . . . . . 
H6A H 0.449218 0.251311 0.446315 0.040 Uiso 1 1 calc R U . . . 
C7 C 0.42643(12) 0.5487(6) 0.3331(5) 0.0288(8) Uani 1 1 d . . . . . 
C8 C 0.38503(13) 0.6698(6) 0.2796(5) 0.0295(8) Uani 1 1 d . . . . . 
H8A H 0.388677 0.816094 0.225973 0.035 Uiso 1 1 calc R U . . . 
C9 C 0.33856(13) 0.5774(6) 0.3043(5) 0.0303(8) Uani 1 1 d . . . . . 
H9A H 0.310282 0.662209 0.269332 0.036 Uiso 1 1 calc R U . . . 
C10 C 0.47626(15) 0.6538(7) 0.3161(7) 0.0435(10) Uani 1 1 d . . . . . 
F10A F 0.48770(11) 0.7896(6) 0.4456(5) 0.0804(11) Uani 1 1 d . . . . . 
F10B F 0.51211(9) 0.5046(5) 0.3017(6) 0.0893(13) Uani 1 1 d . . . . . 
F10C F 0.48013(11) 0.7999(6) 0.1875(5) 0.0838(11) Uani 1 1 d . . . . . 
C11 C 0.19595(12) 0.3911(6) 0.4327(4) 0.0242(8) Uani 1 1 d . . . . . 
C12 C 0.16696(14) 0.5823(6) 0.4758(5) 0.0307(9) Uani 1 1 d . . . . . 
H12A H 0.180645 0.702140 0.542942 0.037 Uiso 1 1 calc R U . . . 
C13 C 0.11834(15) 0.5998(7) 0.4218(6) 0.0385(10) Uani 1 1 d . . . . . 
H13A H 0.098987 0.731176 0.451696 0.046 Uiso 1 1 calc R U . . . 
C14 C 0.09828(14) 0.4262(7) 0.3248(6) 0.0389(10) Uani 1 1 d . . . . . 
H14A H 0.064994 0.437276 0.288175 0.047 Uiso 1 1 calc R U . . . 
C15 C 0.12656(14) 0.2362(7) 0.2810(5) 0.0356(9) Uani 1 1 d . . . . . 
H15A H 0.112767 0.117179 0.213310 0.043 Uiso 1 1 calc R U . . . 
C16 C 0.17489(13) 0.2186(6) 0.3351(5) 0.0299(8) Uani 1 1 d . . . . . 
H16A H 0.193947 0.086395 0.305105 0.036 Uiso 1 1 calc R U . . . 
  
  
_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 
N1 C4 1.421(4) . ? 
N1 C3 1.451(5) . ? 
N1 C2 1.477(4) . ? 
C2 C3 1.484(5) . ? 
C2 C11 1.485(5) . ? 
C4 C9 1.381(5) . ? 
C4 C5 1.392(5) . ? 
C5 C6 1.384(5) . ? 
C6 C7 1.384(5) . ? 
C7 C8 1.387(5) . ? 
C7 C10 1.484(5) . ? 
C8 C9 1.380(5) . ? 
C10 F10B 1.301(5) . ? 
C10 F10C 1.334(5) . ? 
C10 F10A 1.336(6) . ? 
C11 C16 1.386(5) . ? 
C11 C12 1.394(5) . ? 
C12 C13 1.389(5) . ? 
C13 C14 1.377(6) . ? 
C14 C15 1.380(6) . ? 
C15 C16 1.382(5) . ? 
  
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 
C4 N1 C3 117.7(3) . . ? 
C4 N1 C2 118.3(3) . . ? 
C3 N1 C2 60.9(2) . . ? 
N1 C2 C3 58.7(2) . . ? 
N1 C2 C11 118.6(3) . . ? 
C3 C2 C11 123.2(3) . . ? 
N1 C3 C2 60.4(2) . . ? 
C9 C4 C5 119.3(3) . . ? 
C9 C4 N1 119.9(3) . . ? 
C5 C4 N1 120.7(3) . . ? 
C6 C5 C4 120.2(3) . . ? 
C7 C6 C5 120.1(3) . . ? 
C6 C7 C8 119.8(3) . . ? 
C6 C7 C10 120.1(3) . . ? 
C8 C7 C10 120.1(3) . . ? 
C9 C8 C7 119.9(3) . . ? 
C8 C9 C4 120.7(3) . . ? 
F10B C10 F10C 106.8(4) . . ? 
F10B C10 F10A 106.4(4) . . ? 
F10C C10 F10A 102.3(3) . . ? 
F10B C10 C7 114.7(4) . . ? 
F10C C10 C7 113.5(4) . . ? 
F10A C10 C7 112.2(4) . . ? 
C16 C11 C12 118.2(3) . . ? 
C16 C11 C2 122.3(3) . . ? 
C12 C11 C2 119.5(3) . . ? 
C13 C12 C11 120.9(3) . . ? 
C14 C13 C12 119.8(4) . . ? 
C13 C14 C15 120.0(4) . . ? 
C14 C15 C16 120.2(4) . . ? 
C15 C16 C11 120.9(3) . . ? 
  
_refine_diff_density_max    0.266 
_refine_diff_density_min   -0.287 
_refine_diff_density_rms    0.043 
  
  
  
#===END

 