data_global
_audit_creation_method            'APEX3 v2018.7-2'
_publ_requested_journal           ?
_publ_contact_author_name         ?
_publ_contact_author_address
;
;
_publ_contact_author_email        ?
_publ_contact_author_fax          ?
_publ_contact_author_phone        ?
_publ_section_title
;
;
_publ_section_abstract
;
;
_publ_section_references
;
;
_publ_section_comment
;
;
data_20200113aL
_audit_creation_date              2020-02-28
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_iupac           ?
_chemical_formula_moiety          'C5 H2 F3 N7 O2, H2 O'
_chemical_formula_sum             'C5 H4 F3 N7 O3'
_chemical_formula_weight          267.15
_chemical_absolute_configuration  ?
_chemical_melting_point           ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 O O 0.0389 0.0241 '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'

_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'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'

_cell_length_a                    5.2854(14)
_cell_length_b                    12.560(3)
_cell_length_c                    14.308(4)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      949.8(4)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     3805
_cell_measurement_temperature     150.(2)
_cell_measurement_theta_max       53.0304
_cell_measurement_theta_min       2.6868
_exptl_absorpt_coefficient_mu     1.091
_exptl_absorpt_correction_T_max   0.7505
_exptl_absorpt_correction_T_min   0.3320
_exptl_absorpt_correction_type    Multi-Scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour             colourless
_exptl_crystal_density_diffrn     1.868
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_description        noodle
_exptl_crystal_F_000              536
_exptl_crystal_size_max           0.300
_exptl_crystal_size_mid           0.100
_exptl_crystal_size_min           0.100
_exptl_special_details
;
;
_diffrn_reflns_av_R_equivalents   0.0526
_diffrn_reflns_av_unetI/netI      0.0651
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_limit_l_min        -8
_diffrn_reflns_number             3606
_diffrn_reflns_theta_full         53.13
_diffrn_reflns_theta_max          53.13
_diffrn_reflns_theta_min          4.08
_diffrn_ambient_temperature       150(2)
_diffrn_detector_area_resol_mean  7.3910
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type   'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method        ?
_diffrn_radiation_monochromator   'HELIOS MX OPTIC'
_diffrn_radiation_type            'Ga K\a'
_diffrn_radiation_wavelength      1.34139
_diffrn_source                    Metaljet
_diffrn_source_type               'Liquild X-ray Source'
_reflns_number_gt                 1533
_reflns_number_total              1613
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection        'Bruker Instrument Service vV6.2.10'
_computing_data_reduction         'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max          0.357
_refine_diff_density_min          -0.367
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack    0.3(8)
_refine_ls_extinction_coef        ?
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.105
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_constraints     ?
_refine_ls_number_parameters      172
_refine_ls_number_reflns          1613
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0741
_refine_ls_R_factor_gt            0.0713
_refine_ls_restrained_S_all       1.105
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1496P)²+0.3591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.2058
_refine_ls_wR_factor_ref          0.2129
_refine_special_details
;
Refined as a 2-component inversion twin.
;
_atom_sites_solution_hydrogens    mixed
_atom_sites_solution_primary      iterative
_atom_sites_solution_secondary    ?
loop_
  _atom_site_type_symbol
  _atom_site_label
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_calc_flag
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_refinement_flags_posn
  _atom_site_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 C C1 0.0217(13) -0.2101(4) 0.3732(4) 0.0511(13) Uani d . . . 1 . .
 C C2 -0.0965(12) -0.1898(4) 0.2798(4) 0.0493(13) Uani d . . . 1 . .
 C C3 -0.3366(12) -0.2041(4) 0.1656(4) 0.0488(13) Uani d . . . 1 . .
 C C4 -0.1227(11) -0.0807(4) 0.0623(4) 0.0450(12) Uani d . . . 1 . .
 C C5 -0.3196(13) -0.1128(4) 0.0012(4) 0.0478(13) Uani d . . . 1 . .
 F F1 0.1763(11) -0.1333(3) 0.3978(3) 0.0804(14) Uani d . . . 1 . .
 F F2 -0.1537(10) -0.2208(4) 0.4388(3) 0.0865(14) Uani d . . . 1 . .
 F F3 0.1519(9) -0.3005(3) 0.3731(3) 0.0692(11) Uani d . . . 1 . .
 N N1 -0.3296(11) -0.0713(4) -0.0937(3) 0.0529(12) Uani d . . . 1 . .
 N N2 0.0613(9) -0.0121(3) 0.0505(3) 0.0494(11) Uani d . . . 1 . .
 H N2HA 0.169559 -8.7e-05 0.096017 0.059 Uiso calc U . R 1 . .
 H N2HB 0.076691 0.021936 -0.002966 0.059 Uiso calc U . R 1 . .
 N N3 -0.4999(10) -0.1828(3) 0.0204(3) 0.0508(12) Uani d . . . 1 . .
 N N4 -0.5185(10) -0.2294(4) 0.1023(4) 0.0509(11) Uani d . . . 1 . .
 N N6 -0.1463(9) -0.1333(3) 0.1451(3) 0.0425(10) Uani d . . . 1 . .
 N N7 0.0154(10) -0.1237(3) 0.2200(3) 0.0483(11) Uani d . . . 1 . .
 N N8 -0.3090(10) -0.2400(4) 0.2517(3) 0.0493(11) Uani d . . . 1 . .
 O O1 -0.1631(9) -0.0069(3) -0.1164(3) 0.0599(11) Uani d . . . 1 . .
 O O1W 0.4309(9) 0.0414(4) 0.1794(3) 0.0572(11) Uani d . . . 1 . .
 H H1W 0.423(12) 0.009(5) 0.228(6) 0.048(18) Uiso d . . . 1 . .
 H H2W 0.437(15) 0.099(6) 0.199(5) 0.06(2) Uiso d . . . 1 . .
 O O2 -0.5011(12) -0.0999(4) -0.1451(3) 0.0686(14) Uani d . . . 1 . .


_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_site_symmetry_2
  _geom_bond_distance
  _geom_bond_publ_flag
 C1 C2 . 1.496(8) ?
 C4 C5 . 1.418(8) ?
 F1 C1 . 1.312(7) ?
 F2 C1 . 1.327(8) ?
 F3 C1 . 1.328(7) ?
 N1 C5 . 1.455(7) ?
 N2 C4 . 1.310(7) ?
 N2 N2HA . 0.88 ?
 N2 N2HB . 0.88 ?
 N3 C5 . 1.325(8) ?
 N3 N4 . 1.314(7) ?
 N4 C3 . 1.358(8) ?
 N6 C3 . 1.375(7) ?
 N6 C4 . 1.362(7) ?
 N6 N7 . 1.376(7) ?
 N7 C2 . 1.331(7) ?
 N8 C2 . 1.349(8) ?
 N8 C3 . 1.321(8) ?
 O1 N1 . 1.239(7) ?
 O1W H1W . 0.80(8) ?
 O1W H2W . 0.78(8) ?
 O2 N1 . 1.221(7) ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle
  _geom_angle_publ_flag
 F1 C1 C2 . . 112.0(5) ?
 F1 C1 F2 . . 108.6(5) ?
 F1 C1 F3 . . 107.8(6) ?
 F2 C1 C2 . . 110.9(5) ?
 F2 C1 F3 . . 106.0(5) ?
 F3 C1 C2 . . 111.2(5) ?
 N7 C2 C1 . . 119.7(5) ?
 N7 C2 N8 . . 118.0(5) ?
 N8 C2 C1 . . 122.3(5) ?
 N4 C3 N6 . . 121.8(5) ?
 N8 C3 N4 . . 128.3(5) ?
 N8 C3 N6 . . 109.9(5) ?
 N2 C4 C5 . . 130.7(5) ?
 N2 C4 N6 . . 119.9(5) ?
 N6 C4 C5 . . 109.3(5) ?
 C4 C5 N1 . . 120.0(5) ?
 N3 C5 C4 . . 126.0(5) ?
 N3 C5 N1 . . 113.9(5) ?
 O1 N1 C5 . . 116.9(5) ?
 O2 N1 C5 . . 118.9(5) ?
 O2 N1 O1 . . 124.2(5) ?
 C4 N2 N2HA . . 120.0 ?
 C4 N2 N2HB . . 120.0 ?
 N2HA N2 N2HB . . 120.0 ?
 N4 N3 C5 . . 122.3(5) ?
 N3 N4 C3 . . 115.9(5) ?
 C3 N6 N7 . . 110.1(4) ?
 C4 N6 C3 . . 124.5(5) ?
 C4 N6 N7 . . 125.3(5) ?
 C2 N7 N6 . . 99.9(5) ?
 C3 N8 C2 . . 102.1(5) ?
 H2W O1W H1W . . 100.(7) ?

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_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion
  _geom_torsion_publ_flag
 C2 N8 C3 N4 . . . . 178.7(5) ?
 C2 N8 C3 N6 . . . . -1.0(6) ?
 C3 N6 C4 C5 . . . . -1.6(7) ?
 C3 N6 C4 N2 . . . . 177.9(5) ?
 C3 N6 N7 C2 . . . . -0.7(5) ?
 C3 N8 C2 C1 . . . . -176.4(5) ?
 C3 N8 C2 N7 . . . . 0.6(7) ?
 C4 N6 C3 N4 . . . . 1.3(8) ?
 C4 N6 C3 N8 . . . . -178.9(5) ?
 C4 N6 N7 C2 . . . . 179.4(5) ?
 C5 N3 N4 C3 . . . . -2.0(8) ?
 F1 C1 C2 N7 . . . . 21.9(8) ?
 F1 C1 C2 N8 . . . . -161.1(6) ?
 F2 C1 C2 N7 . . . . 143.5(5) ?
 F2 C1 C2 N8 . . . . -39.6(7) ?
 F3 C1 C2 N7 . . . . -98.8(6) ?
 F3 C1 C2 N8 . . . . 78.2(7) ?
 N2 C4 C5 N1 . . . . 3.4(9) ?
 N2 C4 C5 N3 . . . . -179.3(5) ?
 N3 N4 C3 N6 . . . . 0.6(8) ?
 N3 N4 C3 N8 . . . . -179.1(5) ?
 N4 N3 C5 C4 . . . . 1.8(9) ?
 N4 N3 C5 N1 . . . . 179.3(5) ?
 N6 C4 C5 N1 . . . . -177.2(4) ?
 N6 C4 C5 N3 . . . . 0.1(7) ?
 N6 N7 C2 C1 . . . . 177.2(5) ?
 N6 N7 C2 N8 . . . . 0.1(6) ?
 N7 N6 C3 N4 . . . . -178.6(5) ?
 N7 N6 C3 N8 . . . . 1.2(6) ?
 N7 N6 C4 C5 . . . . 178.3(4) ?
 N7 N6 C4 N2 . . . . -2.2(7) ?
 O1 N1 C5 C4 . . . . -1.1(7) ?
 O1 N1 C5 N3 . . . . -178.8(5) ?
 O2 N1 C5 C4 . . . . -179.8(5) ?
 O2 N1 C5 N3 . . . . 2.5(7) ?

