 
data_C14H13F4N3O
 
_audit_creation_method            'SHELXL-2016/6'
_shelx_SHELXL_version_number      '2016/6'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C14 H13 F4 N3 O'
_chemical_formula_sum
 'C14 H13 F4 N3 O'
_chemical_formula_weight          315.27

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'
 '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'
 'F'  'F'   0.0727   0.0534
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
 
_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+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    5.3574(2)
_cell_length_b                    9.2902(4)
_cell_length_c                    28.0903(10)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1398.09(9)
_cell_formula_units_Z             4
_cell_measurement_temperature     123(2)
_cell_measurement_reflns_used     9863
_cell_measurement_theta_min       3.15
_cell_measurement_theta_max       66.54
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       'not measured' 
_exptl_crystal_density_method     none
_exptl_crystal_density_diffrn     1.498          
_exptl_crystal_F_000              648
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.580
_exptl_crystal_size_mid           0.120
_exptl_crystal_size_min           0.080
_exptl_absorpt_coefficient_mu     1.168
_shelx_estimated_absorpt_T_min    0.551
_shelx_estimated_absorpt_T_max    0.912
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.6561
_exptl_absorpt_correction_T_max   0.7528
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2016). SADABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       123(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_source                    'microfocus sealed tube'
_diffrn_source_type               'Incoatec I\uS'
_diffrn_radiation_monochromator   mirrors 
_diffrn_measurement_device_type   'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             14342
_diffrn_reflns_av_unetI/netI      0.0180
_diffrn_reflns_av_R_equivalents   0.0292
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -33
_diffrn_reflns_limit_l_max        33
_diffrn_reflns_theta_min          3.146
_diffrn_reflns_theta_max          66.490
_diffrn_reflns_theta_full         66.490
_diffrn_measured_fraction_theta_max   1.000
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    1.000
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              2465
_reflns_number_gt                 2416
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.668
_reflns_Friedel_fraction_max      0.998
_reflns_Friedel_fraction_full     0.998
 
_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        'APEX2 (Bruker, 2014)'
_computing_cell_refinement        'SAINT (Bruker, 2014)'
_computing_data_reduction         'SAINT (Bruker, 2014)'
_computing_structure_solution     'SHELXT 2016/6 (Sheldrick, 2016)'
_computing_structure_refinement   'SHELXL-2016/6 (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)+(0.0491P)²+0.2711P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    difmap
_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 971 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.03(4)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          2465
_refine_ls_number_parameters      200
_refine_ls_number_restraints      194
_refine_ls_R_factor_all           0.0285
_refine_ls_R_factor_gt            0.0278
_refine_ls_wR_factor_ref          0.0755
_refine_ls_wR_factor_gt           0.0750
_refine_ls_goodness_of_fit_ref    1.053
_refine_ls_restrained_S_all       1.013
_refine_ls_shift/su_max           0.001
_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 0.9033(3) 0.52864(17) 0.78568(5) 0.0443(4) Uani 1 1 d . U . . .
F2 F 0.2366(2) 0.85022(15) 0.79899(5) 0.0359(3) Uani 1 1 d . U . . .
F3 F 0.7000(3) 0.77036(14) 0.54727(4) 0.0321(3) Uani 1 1 d . U . . .
F4 F 1.0708(3) 0.76471(14) 0.57980(4) 0.0322(3) Uani 1 1 d . U . . .
O1 O 1.0291(2) 0.47067(16) 0.59752(5) 0.0224(3) Uani 1 1 d . U . . .
H1 H 1.136994 0.519416 0.612029 0.034 Uiso 1 1 calc R U . . .
N1 N 0.6509(3) 0.70327(18) 0.70449(6) 0.0202(4) Uani 1 1 d . U . . .
N2 N 0.4277(3) 0.6564(2) 0.68977(6) 0.0221(4) Uani 1 1 d . U . . .
N3 N 0.4605(3) 0.60078(18) 0.64696(6) 0.0211(4) Uani 1 1 d . U . . .
C1 C 0.6414(6) 0.4144(3) 0.47456(9) 0.0423(6) Uani 1 1 d . U . . .
H1A H 0.495233 0.470673 0.470041 0.051 Uiso 1 1 calc R U . . .
H1B H 0.719745 0.369694 0.448075 0.051 Uiso 1 1 calc R U . . .
C2 C 0.7345(4) 0.3987(2) 0.51709(8) 0.0280(5) Uani 1 1 d . U . . .
H2 H 0.880856 0.341747 0.520277 0.034 Uiso 1 1 calc R U . . .
C3 C 0.6271(4) 0.4641(2) 0.56132(7) 0.0206(4) Uani 1 1 d . U . . .
H3A H 0.566941 0.386106 0.582422 0.025 Uiso 1 1 calc R U . . .
H3B H 0.481602 0.524186 0.552556 0.025 Uiso 1 1 calc R U . . .
C4 C 0.8157(4) 0.5571(2) 0.58878(7) 0.0187(4) Uani 1 1 d . U . . .
C5 C 0.7061(4) 0.6133(2) 0.63468(7) 0.0181(4) Uani 1 1 d . U . . .
C6 C 0.8270(4) 0.6792(2) 0.67183(7) 0.0209(4) Uani 1 1 d . U . . .
H6 H 0.999275 0.702728 0.673863 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6778(4) 0.7791(2) 0.75021(7) 0.0240(4) Uani 1 1 d . U . . .
H7A H 0.588026 0.872059 0.748435 0.029 Uiso 1 1 calc R U . . .
H7B H 0.856570 0.800047 0.755756 0.029 Uiso 1 1 calc R U . . .
C8 C 0.5783(4) 0.6940(2) 0.79139(7) 0.0209(4) Uani 1 1 d . U . . .
C9 C 0.6976(4) 0.5737(2) 0.80903(8) 0.0288(5) Uani 1 1 d . U . . .
C10 C 0.6149(6) 0.4989(2) 0.84871(9) 0.0437(7) Uani 1 1 d . U . . .
H10 H 0.701737 0.416491 0.859996 0.052 Uiso 1 1 calc R U . . .
C11 C 0.4007(6) 0.5482(3) 0.87150(8) 0.0441(7) Uani 1 1 d . U . . .
H11 H 0.341060 0.498478 0.898785 0.053 Uiso 1 1 calc R U . . .
C12 C 0.2739(5) 0.6667(3) 0.85548(8) 0.0368(5) Uani 1 1 d . U . . .
H12 H 0.128527 0.700273 0.871339 0.044 Uiso 1 1 calc R U . . .
C13 C 0.3641(4) 0.7354(2) 0.81573(7) 0.0259(4) Uani 1 1 d . U . . .
C14 C 0.8971(4) 0.6815(2) 0.55688(7) 0.0233(4) Uani 1 1 d . U . . .
H14 H 0.968505 0.643250 0.526518 0.028 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
F1 C9 1.349(3) . ?
F2 C13 1.351(3) . ?
F3 C14 1.368(2) . ?
F4 C14 1.370(2) . ?
O1 C4 1.418(2) . ?
O1 H1 0.8400 . ?
N1 C6 1.335(3) . ?
N1 N2 1.338(2) . ?
N1 C7 1.472(2) . ?
N2 N3 1.321(2) . ?
N3 C5 1.365(3) . ?
C1 C2 1.303(4) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C2 C3 1.498(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.537(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.510(3) . ?
C4 C14 1.525(3) . ?
C5 C6 1.373(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.499(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.380(3) . ?
C8 C13 1.390(3) . ?
C9 C10 1.386(4) . ?
C10 C11 1.391(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.370(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(3) . ?
C12 H12 0.9500 . ?
C14 H14 1.0000 . ?
 
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 O1 H1 109.5 . . ?
C6 N1 N2 111.40(15) . . ?
C6 N1 C7 127.64(17) . . ?
N2 N1 C7 120.84(16) . . ?
N3 N2 N1 106.83(15) . . ?
N2 N3 C5 108.99(16) . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C1 C2 C3 124.6(2) . . ?
C1 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
C2 C3 C4 113.06(16) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
O1 C4 C5 111.19(15) . . ?
O1 C4 C14 107.47(16) . . ?
C5 C4 C14 110.55(16) . . ?
O1 C4 C3 107.34(15) . . ?
C5 C4 C3 111.53(15) . . ?
C14 C4 C3 108.61(16) . . ?
N3 C5 C6 107.51(18) . . ?
N3 C5 C4 124.15(17) . . ?
C6 C5 C4 128.30(19) . . ?
N1 C6 C5 105.27(18) . . ?
N1 C6 H6 127.4 . . ?
C5 C6 H6 127.4 . . ?
N1 C7 C8 112.75(16) . . ?
N1 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C13 115.4(2) . . ?
C9 C8 C7 122.7(2) . . ?
C13 C8 C7 121.84(19) . . ?
F1 C9 C8 117.1(2) . . ?
F1 C9 C10 119.8(2) . . ?
C8 C9 C10 123.2(2) . . ?
C9 C10 C11 117.9(2) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 117.8(2) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
F2 C13 C12 118.2(2) . . ?
F2 C13 C8 117.66(19) . . ?
C12 C13 C8 124.2(2) . . ?
F3 C14 F4 106.05(16) . . ?
F3 C14 C4 110.64(16) . . ?
F4 C14 C4 110.21(16) . . ?
F3 C14 H14 110.0 . . ?
F4 C14 H14 110.0 . . ?
C4 C14 H14 110.0 . . ?
 
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
C6 N1 N2 N3 0.2(2) . . . . ?
C7 N1 N2 N3 176.58(17) . . . . ?
N1 N2 N3 C5 -0.2(2) . . . . ?
C1 C2 C3 C4 -124.2(2) . . . . ?
C2 C3 C4 O1 -54.3(2) . . . . ?
C2 C3 C4 C5 -176.34(17) . . . . ?
C2 C3 C4 C14 61.6(2) . . . . ?
N2 N3 C5 C6 0.1(2) . . . . ?
N2 N3 C5 C4 177.88(17) . . . . ?
O1 C4 C5 N3 -128.61(19) . . . . ?
C14 C4 C5 N3 112.1(2) . . . . ?
C3 C4 C5 N3 -8.8(3) . . . . ?
O1 C4 C5 C6 48.7(3) . . . . ?
C14 C4 C5 C6 -70.6(3) . . . . ?
C3 C4 C5 C6 168.4(2) . . . . ?
N2 N1 C6 C5 -0.1(2) . . . . ?
C7 N1 C6 C5 -176.19(19) . . . . ?
N3 C5 C6 N1 0.0(2) . . . . ?
C4 C5 C6 N1 -177.65(18) . . . . ?
C6 N1 C7 C8 -128.8(2) . . . . ?
N2 N1 C7 C8 55.5(3) . . . . ?
N1 C7 C8 C9 72.2(2) . . . . ?
N1 C7 C8 C13 -110.7(2) . . . . ?
C13 C8 C9 F1 178.63(17) . . . . ?
C7 C8 C9 F1 -4.1(3) . . . . ?
C13 C8 C9 C10 -1.0(3) . . . . ?
C7 C8 C9 C10 176.32(19) . . . . ?
F1 C9 C10 C11 -179.4(2) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 F2 178.4(2) . . . . ?
C11 C12 C13 C8 -1.4(3) . . . . ?
C9 C8 C13 F2 -178.17(17) . . . . ?
C7 C8 C13 F2 4.5(3) . . . . ?
C9 C8 C13 C12 1.6(3) . . . . ?
C7 C8 C13 C12 -175.69(19) . . . . ?
O1 C4 C14 F3 -179.52(14) . . . . ?
C5 C4 C14 F3 -58.0(2) . . . . ?
C3 C4 C14 F3 64.7(2) . . . . ?
O1 C4 C14 F4 -62.6(2) . . . . ?
C5 C4 C14 F4 59.0(2) . . . . ?
C3 C4 C14 F4 -178.37(16) . . . . ?
 
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 
 _geom_hbond_publ_flag
O1 H1 N3  0.84 2.13 2.955(2) 167.1 1_655 yes
 
_refine_diff_density_max    0.188
_refine_diff_density_min   -0.185
_refine_diff_density_rms    0.036



