
data_xr26rt
 
_audit_creation_method            'SHELXL-2016/4'
_shelx_SHELXL_version_number      '2016/4'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C5 H3 F2 N O3'
_chemical_formula_sum             'C5 H3 F2 N O3' 
_chemical_formula_weight          163.08

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       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_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'
 
_cell_length_a                    5.093(2)
_cell_length_b                    5.618(2)
_cell_length_c                    11.155(5)
_cell_angle_alpha                 84.307(15)
_cell_angle_beta                  83.682(14)
_cell_angle_gamma                 78.046(15)
_cell_volume                      309.4(2)
_cell_formula_units_Z             2
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     461
_cell_measurement_theta_min       3.69
_cell_measurement_theta_max       26.13
 
_exptl_crystal_description        'block'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_diffrn     1.751          
_exptl_crystal_F_000              164
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.500
_exptl_crystal_size_mid           0.360
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.181
_shelx_estimated_absorpt_T_min    0.915
_shelx_estimated_absorpt_T_max    0.965
_exptl_absorpt_correction_type    numerical
_exptl_absorpt_correction_T_min   0.78
_exptl_absorpt_correction_T_max   0.96
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       293(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             4960
_diffrn_reflns_av_unetI/netI      0.0332
_diffrn_reflns_av_R_equivalents   0.0383
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          1.842
_diffrn_reflns_theta_max          27.578
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.983
_diffrn_measured_fraction_theta_full  0.992
_diffrn_reflns_Laue_measured_fraction_max    0.983
_diffrn_reflns_Laue_measured_fraction_full   0.992
_diffrn_reflns_point_group_measured_fraction_max   0.983
_diffrn_reflns_point_group_measured_fraction_full  0.992
_reflns_number_total              1414
_reflns_number_gt                 974
_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)+(0.0976P)²] 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          1414
_refine_ls_number_parameters      143
_refine_ls_number_restraints      6
_refine_ls_R_factor_all           0.0649
_refine_ls_R_factor_gt            0.0432
_refine_ls_wR_factor_ref          0.1517
_refine_ls_wR_factor_gt           0.1293
_refine_ls_goodness_of_fit_ref    1.040
_refine_ls_restrained_S_all       1.046

_refine_ls_shift/su_max           0.070
_refine_ls_shift/su_mean          0.010
 
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 0.6104(4) 0.8300(3) 0.73450(16) 0.0590(5) Uani 1 1 d . . . . .
O1 O 0.7618(3) 0.6618(2) 0.81196(13) 0.0602(5) Uani 1 1 d . . . . .
O2 O 0.2211(3) 1.0632(2) 0.58759(14) 0.0640(5) Uani 1 1 d . . . . .
O3 O 0.1569(3) 0.6995(3) 0.54845(13) 0.0594(4) Uani 1 1 d D . . . .
H3 H 0.019(5) 0.780(7) 0.517(4) 0.174(19) Uiso 1 1 d D . . . .
C1 C 0.4642(3) 0.7074(3) 0.68606(15) 0.0413(4) Uani 1 1 d . . . . .
C2 C 0.5142(4) 0.4594(3) 0.72793(16) 0.0451(5) Uani 1 1 d . . . . .
H2 H 0.438354 0.335290 0.705496 0.054 Uiso 1 1 calc R U . . .
C3 C 0.6961(4) 0.4434(3) 0.80747(16) 0.0450(5) Uani 1 1 d . . . . .
C4 C 0.2687(4) 0.8371(3) 0.60104(16) 0.0438(5) Uani 1 1 d . . . . .
C5 C 0.8231(4) 0.2392(4) 0.89008(19) 0.0559(5) Uani 1 1 d D . . . .
H5A H 0.773(5) 0.082(3) 0.883(2) 0.067 Uiso 1 1 d D U . . .
F1A F 0.7496(18) 0.2900(16) 1.0053(6) 0.069(2) Uani 0.5 1 d . . P A 1
F2A F 1.0906(12) 0.2070(11) 0.8791(7) 0.082(3) Uani 0.5 1 d . . P A 1
F1B F 0.661(2) 0.204(2) 0.9858(10) 0.125(5) Uani 0.25 1 d D . P A 2
F2B F 1.060(2) 0.281(2) 0.9119(18) 0.099(5) Uani 0.25 1 d D . P A 2
F1C F 0.840(4) 0.320(4) 0.9950(11) 0.077(5) Uani 0.25 1 d D . P A 3
F2C F 1.056(2) 0.123(2) 0.8426(13) 0.093(4) Uani 0.25 1 d D . P A 3
 
 
_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 C1 1.302(2) . ?
N1 O1 1.385(2) . ?
O1 C3 1.344(2) . ?
O2 C4 1.239(2) . ?
O3 C4 1.270(2) . ?
C1 C2 1.406(2) . ?
C1 C4 1.481(3) . ?
C2 C3 1.336(3) . ?
C3 C5 1.482(3) . ?
C5 F1B 1.301(8) . ?
C5 F2C 1.313(9) . ?
C5 F1C 1.315(10) . ?
C5 F2B 1.326(9) . ?
C5 F2A 1.330(7) . ?
C5 F1A 1.341(7) . ?
 
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
C1 N1 O1 105.42(14) . . ?
C3 O1 N1 108.52(14) . . ?
N1 C1 C2 112.02(17) . . ?
N1 C1 C4 119.32(16) . . ?
C2 C1 C4 128.62(16) . . ?
C3 C2 C1 103.81(16) . . ?
C2 C3 O1 110.19(17) . . ?
C2 C3 C5 132.39(17) . . ?
O1 C3 C5 117.38(16) . . ?
O2 C4 O3 125.07(18) . . ?
O2 C4 C1 120.15(16) . . ?
O3 C4 C1 114.76(16) . . ?
F2Cc C5 F1C 112.7(11) . . ?
F1B C5 F2B 115.1(10) . . ?
F2A C5 F1A 104.7(5) . . ?
F1B C5 C3 111.2(6) . . ?
F2C C5 C3 112.5(7) . . ?
F1C C5 C3 109.6(12) . . ?
F2B C5 C3 108.1(7) . . ?
F2A C5 C3 112.5(3) . . ?
F1A C5 C3 109.9(5) . . ?
 
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 
O3 H3 O2_$1  0.845(10) 1.814(16) 2.639(2) 165(4) 2_576
 
_refine_diff_density_max    0.186
_refine_diff_density_min   -0.231
_refine_diff_density_rms    0.050



