 
data_xr128
 
_audit_creation_method            'SHELXL-2016/4'
_shelx_SHELXL_version_number      '2016/4'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C6 H5 F2 N O3'
_chemical_formula_sum             'C6 H5 F2 N O3' 
_chemical_formula_weight          177.11

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            15
_space_group_name_H-M_alt         'C 2/c'
_space_group_name_Hall            '-C 2yc'
 
_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'
 '-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                    17.197(3)
_cell_length_b                    6.3032(12)
_cell_length_c                    14.879(3)
_cell_angle_alpha                 90
_cell_angle_beta                  119.429(6)
_cell_angle_gamma                 90
_cell_volume                      1404.7(5)
_cell_formula_units_Z             8
_cell_measurement_temperature     123(2)
_cell_measurement_reflns_used     804
_cell_measurement_theta_min       2.72
_cell_measurement_theta_max       27.17
_exptl_crystal_description        'prizm'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_diffrn     1.675          
_exptl_crystal_F_000              720
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.320
_exptl_crystal_size_mid           0.230
_exptl_crystal_size_min           0.190
_exptl_absorpt_coefficient_mu     0.166
_shelx_estimated_absorpt_T_min    0.949
_shelx_estimated_absorpt_T_max    0.969
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.79
_exptl_absorpt_correction_T_max   0.97
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       123(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'sealed tube'
_diffrn_radiation_monochromator   'graphite'
_diffrn_measurement_device_type   'CCD area detector'
_diffrn_measurement_method        'omega scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             7378
_diffrn_reflns_av_unetI/netI      0.0300
_diffrn_reflns_av_R_equivalents   0.0361
_diffrn_reflns_limit_h_min        -22
_diffrn_reflns_limit_h_max        22
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          2.720
_diffrn_reflns_theta_max          27.574
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              1622
_reflns_number_gt                 1308
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_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      'Bruker SMART'
_computing_cell_refinement      'Bruker SMART'
_computing_data_reduction       'Bruker SAINT'
_computing_structure_solution   'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics   'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_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)+(0.0460P)²+0.9539P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          1622
_refine_ls_number_parameters      113
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0485
_refine_ls_R_factor_gt            0.0364
_refine_ls_wR_factor_ref          0.0935
_refine_ls_wR_factor_gt           0.0867
_refine_ls_goodness_of_fit_ref    1.025
_refine_ls_restrained_S_all       1.025
_refine_ls_shift/su_max           0.002
_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
F1 F 0.59193(7) 0.56649(15) 0.44916(9) 0.0425(3) Uani 1 1 d . . . . .
F2 F 0.63873(7) 0.26836(16) 0.53272(7) 0.0353(3) Uani 1 1 d . . . . .
N1 N 0.43937(8) 0.37960(19) 0.31650(10) 0.0226(3) Uani 1 1 d . . . . .
O1 O 0.36753(6) 0.23776(16) 0.26689(8) 0.0225(3) Uani 1 1 d . . . . .
O2 O 0.31008(7) -0.06418(16) 0.08559(7) 0.0212(3) Uani 1 1 d . . . . .
O3 O 0.24785(7) -0.35222(17) 0.11223(8) 0.0229(3) Uani 1 1 d . . . . .
H3O H 0.2284(14) -0.375(3) 0.0445(18) 0.049(6) Uiso 1 1 d . . . . .
C1 C 0.59836(10) 0.3555(2) 0.43681(11) 0.0226(3) Uani 1 1 d . . . . .
H1 H 0.635090 0.329601 0.402633 0.027 Uiso 1 1 calc R U . . .
C2 C 0.50767(9) 0.2596(2) 0.37427(11) 0.0178(3) Uani 1 1 d . . . . .
C3 C 0.48551(10) 0.0419(2) 0.36574(11) 0.0194(3) Uani 1 1 d . . . . .
H3 H 0.523834 -0.074563 0.399945 0.023 Uiso 1 1 calc R U . . .
C4 C 0.39765(9) 0.0380(2) 0.29801(10) 0.0172(3) Uani 1 1 d . . . . .
C5 C 0.33127(10) -0.1364(2) 0.25528(11) 0.0194(3) Uani 1 1 d . . . . .
H5A H 0.280484 -0.101640 0.266408 0.023 Uiso 1 1 calc R U . . .
H5B H 0.359177 -0.268044 0.294060 0.023 Uiso 1 1 calc R U . . .
C6 C 0.29598(9) -0.1776(2) 0.14228(11) 0.0174(3) 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 C1 1.3543(18) . ?
F2 C1 1.3590(17) . ?
N1 C2 1.3034(19) . ?
N1 O1 1.4051(16) . ?
O1 C4 1.3535(17) . ?
O2 C6 1.2174(17) . ?
O3 C6 1.3165(18) . ?
C1 C2 1.496(2) . ?
C2 C3 1.413(2) . ?
C3 C4 1.343(2) . ?
C4 C5 1.484(2) . ?
C5 C6 1.503(2) . ?
 
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
C2 N1 O1 104.59(11) . . ?
C4 O1 N1 108.80(10) . . ?
F1 C1 F2 106.75(12) . . ?
F1 C1 C2 110.59(13) . . ?
F2 C1 C2 109.17(12) . . ?
N1 C2 C3 112.87(13) . . ?
N1 C2 C1 120.12(13) . . ?
C3 C2 C1 126.96(13) . . ?
C4 C3 C2 103.85(13) . . ?
C3 C4 O1 109.89(12) . . ?
C3 C4 C5 132.85(14) . . ?
O1 C4 C5 117.25(12) . . ?
C4 C5 C6 114.20(12) . . ?
O2 C6 O3 124.17(13) . . ?
O2 C6 C5 124.41(13) . . ?
O3 C6 C5 111.42(12) . . ?
 
_refine_diff_density_max    0.258
_refine_diff_density_min   -0.286
_refine_diff_density_rms    0.058



