# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wie9886
_database_code_depnum_ccdc_archive 'CCDC 2130259'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2021-12-21 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2019.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H5 F3 N2 O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         282.14

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.15030(10)
_cell_length_b                   12.5829(3)
_cell_length_c                   13.1818(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.6830(10)
_cell_angle_gamma                90
_cell_volume                     1018.01(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      6.7311
_cell_measurement_theta_max      68.1600
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.049
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568

_exptl_absorpt_coefficient_mu    1.724
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 Bruker AXS area detector scaling and absorption correction.
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu Ims'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON III Diffractometer'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            16992
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_theta_min         6.73
_diffrn_reflns_theta_max         68.15
_diffrn_reflns_theta_full        68.15
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

Structure factors included contributions from the .fab file.

_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.
;

_reflns_number_total             1797
_reflns_number_gt                1736
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0753
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_number_reflns         1797
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+0.5418P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0727 0.0534 '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'

_computing_data_collection       'APEX3 v2019.1-0'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

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 0.1913(2) 0.69869(10) 0.45982(10) 0.0154(3) Uani d . . . 1 . .
O O1 -0.03487(14) 0.68840(8) 0.45601(7) 0.0191(2) Uani d . . . 1 . .
H H1 -0.073(3) 0.7189(16) 0.5067(17) 0.041(5) Uiso d . . . 1 . .
O O2 0.26266(15) 0.80173(7) 0.48235(7) 0.0177(2) Uani d . . . 1 . .
H H2 0.204(4) 0.8432(17) 0.4353(17) 0.048(6) Uiso d . . . 1 . .
C C2 0.2915(2) 0.63060(10) 0.54798(10) 0.0175(3) Uani d . . . 1 . .
F F1 0.50954(12) 0.63720(6) 0.55573(6) 0.0221(2) Uani d . . . 1 . .
F F2 0.22005(13) 0.66156(6) 0.63717(6) 0.0232(2) Uani d . . . 1 . .
F F3 0.23935(13) 0.52826(6) 0.53568(6) 0.0233(2) Uani d . . . 1 . .
C C11 0.2709(2) 0.65865(10) 0.35921(9) 0.0150(3) Uani d . . . 1 . .
C C12 0.4629(2) 0.70049(10) 0.32538(10) 0.0161(3) Uani d . . . 1 . .
H H12 0.543829 0.752166 0.364416 0.019 Uiso calc U . R 1 . .
C C13 0.5333(2) 0.66512(10) 0.23355(9) 0.0157(3) Uani d . . . 1 . .
C C14 0.4241(2) 0.58967(10) 0.17400(9) 0.0162(3) Uani d . . . 1 . .
H H14 0.477334 0.565397 0.112017 0.019 Uiso calc U . R 1 . .
C C15 0.2324(2) 0.55132(10) 0.20974(9) 0.0161(3) Uani d . . . 1 . .
C C16 0.1527(2) 0.58340(10) 0.30101(9) 0.0162(3) Uani d . . . 1 . .
H H16 0.02088 0.554812 0.323223 0.019 Uiso calc U . R 1 . .
N N1 0.72460(17) 0.71671(9) 0.19332(8) 0.0172(3) Uani d . . . 1 . .
O O3 0.80186(16) 0.79414(8) 0.23820(7) 0.0258(3) Uani d . . . 1 . .
O O4 0.79330(15) 0.68005(7) 0.11478(7) 0.0210(2) Uani d . . . 1 . .
N N2 0.10317(18) 0.47720(8) 0.14394(8) 0.0180(3) Uani d . . . 1 . .
O O5 0.18578(17) 0.44199(8) 0.06877(7) 0.0265(3) Uani d . . . 1 . .
O O6 -0.08241(15) 0.45504(7) 0.16712(7) 0.0201(2) 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 O2 . 1.3946(15) ?
C1 O1 . 1.3948(15) ?
C1 C11 . 1.5284(17) ?
C1 C2 . 1.5401(18) ?
O1 H1 . 0.82(2) ?
O2 H2 . 0.87(2) ?
C2 F3 . 1.3344(15) ?
C2 F2 . 1.3390(14) ?
C2 F1 . 1.3412(15) ?
C11 C12 . 1.3921(18) ?
C11 C16 . 1.3937(18) ?
C12 C13 . 1.3849(18) ?
C12 H12 . 0.95 ?
C13 C14 . 1.3789(19) ?
C13 N1 . 1.4719(16) ?
C14 C15 . 1.3843(18) ?
C14 H14 . 0.95 ?
C15 C16 . 1.3880(18) ?
C15 N2 . 1.4715(16) ?
C16 H16 . 0.95 ?
N1 O3 . 1.2202(15) ?
N1 O4 . 1.2326(14) ?
N2 O5 . 1.2251(14) ?
N2 O6 . 1.2323(15) ?

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
O2 C1 O1 . . 113.17(10) ?
O2 C1 C11 . . 112.17(10) ?
O1 C1 C11 . . 108.21(10) ?
O2 C1 C2 . . 104.56(10) ?
O1 C1 C2 . . 108.97(10) ?
C11 C1 C2 . . 109.67(10) ?
C1 O1 H1 . . 105.4(14) ?
C1 O2 H2 . . 107.2(14) ?
F3 C2 F2 . . 107.32(10) ?
F3 C2 F1 . . 107.47(10) ?
F2 C2 F1 . . 107.33(10) ?
F3 C2 C1 . . 111.34(11) ?
F2 C2 C1 . . 111.28(10) ?
F1 C2 C1 . . 111.87(10) ?
C12 C11 C16 . . 120.27(11) ?
C12 C11 C1 . . 118.61(11) ?
C16 C11 C1 . . 121.11(11) ?
C13 C12 C11 . . 118.54(12) ?
C13 C12 H12 . . 120.7 ?
C11 C12 H12 . . 120.7 ?
C14 C13 C12 . . 123.40(12) ?
C14 C13 N1 . . 118.03(11) ?
C12 C13 N1 . . 118.38(11) ?
C13 C14 C15 . . 116.15(11) ?
C13 C14 H14 . . 121.9 ?
C15 C14 H14 . . 121.9 ?
C14 C15 C16 . . 123.34(12) ?
C14 C15 N2 . . 117.38(11) ?
C16 C15 N2 . . 119.19(11) ?
C15 C16 C11 . . 118.27(11) ?
C15 C16 H16 . . 120.9 ?
C11 C16 H16 . . 120.9 ?
O3 N1 O4 . . 124.21(11) ?
O3 N1 C13 . . 118.21(10) ?
O4 N1 C13 . . 117.55(11) ?
O5 N2 O6 . . 123.89(11) ?
O5 N2 C15 . . 118.01(11) ?
O6 N2 C15 . . 118.10(10) ?

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
O2 C1 C2 F3 . . . . -178.96(9) ?
O1 C1 C2 F3 . . . . 59.77(13) ?
C11 C1 C2 F3 . . . . -58.50(13) ?
O2 C1 C2 F2 . . . . 61.37(13) ?
O1 C1 C2 F2 . . . . -59.90(13) ?
C11 C1 C2 F2 . . . . -178.18(10) ?
O2 C1 C2 F1 . . . . -58.69(13) ?
O1 C1 C2 F1 . . . . -179.96(10) ?
C11 C1 C2 F1 . . . . 61.77(13) ?
O2 C1 C11 C12 . . . . 26.78(15) ?
O1 C1 C11 C12 . . . . 152.31(11) ?
C2 C1 C11 C12 . . . . -88.94(13) ?
O2 C1 C11 C16 . . . . -151.95(11) ?
O1 C1 C11 C16 . . . . -26.42(15) ?
C2 C1 C11 C16 . . . . 92.33(14) ?
C16 C11 C12 C13 . . . . -0.44(18) ?
C1 C11 C12 C13 . . . . -179.18(11) ?
C11 C12 C13 C14 . . . . -0.60(19) ?
C11 C12 C13 N1 . . . . 174.28(11) ?
C12 C13 C14 C15 . . . . 1.50(19) ?
N1 C13 C14 C15 . . . . -173.40(11) ?
C13 C14 C15 C16 . . . . -1.45(19) ?
C13 C14 C15 N2 . . . . 175.20(11) ?
C14 C15 C16 C11 . . . . 0.49(19) ?
N2 C15 C16 C11 . . . . -176.09(11) ?
C12 C11 C16 C15 . . . . 0.49(18) ?
C1 C11 C16 C15 . . . . 179.20(11) ?
C14 C13 N1 O3 . . . . 169.17(11) ?
C12 C13 N1 O3 . . . . -6.00(17) ?
C14 C13 N1 O4 . . . . -9.20(17) ?
C12 C13 N1 O4 . . . . 175.64(11) ?
C14 C15 N2 O5 . . . . 10.14(17) ?
C16 C15 N2 O5 . . . . -173.07(11) ?
C14 C15 N2 O6 . . . . -169.15(11) ?
C16 C15 N2 O6 . . . . 7.63(17) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O4 4_476 0.82(2) 2.11(2) 2.9191(14) 168.(2) ?
O2 H2 O6 2 0.87(2) 2.06(2) 2.9244(13) 174.(2) ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5j
_database_code_depnum_ccdc_archive 'CCDC 2141905'
loop_
_audit_author_name
_audit_author_address
'Dieter Schollmeyer'
;University of Mainz Department of Chemistry
Germany
;
_audit_update_record             
;
2022-01-13 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
((2R,4S)-4-(4-bromophenyl)-2-(3,5-dinitrophenyl)-2-(trifluoromethyl)-1,3-dioxolan-4-yl)methanol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 Br F3 N2 O7'
_chemical_formula_sum            'C17 H12 Br F3 N2 O7'
_chemical_formula_weight         493.20

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'
Br Br -0.2901 2.4595 '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                   10.9727(5)
_cell_length_b                   11.7950(4)
_cell_length_c                   14.1878(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1836.23(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9257
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      28.47

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.314
_shelx_estimated_absorpt_T_min   0.563
_shelx_estimated_absorpt_T_max   0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5223
_exptl_absorpt_correction_T_max  0.8306
_exptl_absorpt_process_details   
; 
STOE LANA, absorption correction by scaling of reflection intensities. 
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            7188
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.871
_diffrn_reflns_theta_max         27.957
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4369
_reflns_number_gt                4002
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.999

_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       'X-Area WinXpose 2.0.22.0 (STOE, 2016)'
_computing_cell_refinement       'X-Area Recipe 1.36.0.0 (STOE, 2020)'
_computing_data_reduction        'X-Area Integrate 1.77.0.0 (STOE, 2019)'
_computing_structure_solution    'SHELXT-2014 (Shelxdrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0294P)²+3.2125P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1575 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.013(8)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4369
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
Br1 Br 0.49389(4) 0.28240(4) -0.06166(3) 0.01872(11) Uani 1 1 d . . . . .
F1 F 0.1612(3) 0.8920(3) 0.2806(2) 0.0242(6) Uani 1 1 d . . . . .
F2 F 0.2831(3) 0.8560(3) 0.39619(19) 0.0229(6) Uani 1 1 d . . . . .
F3 F 0.3455(3) 0.9546(2) 0.2775(2) 0.0232(6) Uani 1 1 d . . . . .
O1 O 0.3003(3) 0.7704(3) 0.1559(2) 0.0157(6) Uani 1 1 d . . . . .
O2 O 0.2443(3) 0.6668(3) 0.2849(2) 0.0171(7) Uani 1 1 d . . . . .
O3 O 0.1963(3) 0.7831(3) -0.0263(2) 0.0233(7) Uani 1 1 d . . . . .
H3 H 0.243(7) 0.832(6) -0.012(5) 0.04(2) Uiso 1 1 d . . . . .
N1 N 0.6345(4) 0.5319(3) 0.4211(3) 0.0180(8) Uani 1 1 d . . . . .
O4 O 0.7428(3) 0.5108(3) 0.4335(3) 0.0243(7) Uani 1 1 d . . . . .
O5 O 0.5524(3) 0.4794(3) 0.4591(3) 0.0305(9) Uani 1 1 d . . . . .
N2 N 0.7589(4) 0.8394(4) 0.2101(3) 0.0222(9) Uani 1 1 d . . . . .
O6 O 0.7287(3) 0.9208(3) 0.1634(3) 0.0269(8) Uani 1 1 d . . . . .
O7 O 0.8646(3) 0.8113(4) 0.2250(3) 0.0437(12) Uani 1 1 d . . . . .
C1 C 0.3177(4) 0.7556(4) 0.2539(3) 0.0158(10) Uani 1 1 d . . . . .
C2 C 0.2758(4) 0.8659(4) 0.3021(3) 0.0175(9) Uani 1 1 d . . . . .
C3 C 0.4509(4) 0.7319(4) 0.2766(3) 0.0163(9) Uani 1 1 d . . . . .
C4 C 0.4804(4) 0.6458(4) 0.3388(3) 0.0164(9) Uani 1 1 d . . . . .
H4 H 0.422(5) 0.609(5) 0.359(4) 0.015(14) Uiso 1 1 d . . . . .
C5 C 0.6019(4) 0.6250(4) 0.3568(3) 0.0166(9) Uani 1 1 d . . . . .
C6 C 0.6964(4) 0.6860(4) 0.3159(3) 0.0167(9) Uani 1 1 d . . . . .
H6 H 0.772(5) 0.672(5) 0.330(4) 0.019(14) Uiso 1 1 d . . . . .
C7 C 0.6625(4) 0.7706(5) 0.2546(3) 0.0170(9) Uani 1 1 d . . . . .
C8 C 0.5429(4) 0.7953(4) 0.2335(3) 0.0169(9) Uani 1 1 d . . . . .
H8 H 0.524(5) 0.847(5) 0.188(4) 0.016(13) Uiso 1 1 d . . . . .
C9 C 0.1510(4) 0.6503(4) 0.2148(3) 0.0189(9) Uani 1 1 d . . . . .
H9A H 0.078(5) 0.706(5) 0.225(4) 0.015(9) Uiso 1 1 d . U . . .
H9B H 0.125(5) 0.568(5) 0.214(4) 0.015(9) Uiso 1 1 d . U . . .
C10 C 0.2177(4) 0.6831(4) 0.1234(3) 0.0161(9) Uani 1 1 d . . . . .
C11 C 0.1327(4) 0.7398(4) 0.0528(3) 0.0200(9) Uani 1 1 d . . . . .
H11A H 0.072(5) 0.688(5) 0.030(4) 0.022(11) Uiso 1 1 d . U . . .
H11B H 0.086(5) 0.805(5) 0.083(4) 0.022(11) Uiso 1 1 d . U . . .
C12 C 0.2872(4) 0.5839(4) 0.0809(3) 0.0156(9) Uani 1 1 d . . . . .
C13 C 0.2265(4) 0.4842(4) 0.0575(3) 0.0171(8) Uani 1 1 d . . . . .
H13 H 0.145(5) 0.477(4) 0.070(4) 0.014(12) Uiso 1 1 d . . . . .
C14 C 0.2872(4) 0.3937(4) 0.0160(3) 0.0183(9) Uani 1 1 d . . . . .
H14 H 0.244(5) 0.323(5) 0.002(4) 0.018(14) Uiso 1 1 d . . . . .
C15 C 0.4103(4) 0.4042(4) -0.0019(3) 0.0159(9) Uani 1 1 d . . . . .
C16 C 0.4734(4) 0.5014(5) 0.0210(4) 0.0198(10) Uani 1 1 d . . . . .
H16 H 0.548(5) 0.502(5) 0.006(4) 0.011(14) Uiso 1 1 d . . . . .
C17 C 0.4115(4) 0.5915(4) 0.0621(3) 0.0178(8) Uani 1 1 d . . . . .
H17 H 0.460(5) 0.656(5) 0.076(4) 0.015(13) Uiso 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
Br1 C15 1.904(4) . ?
F1 C2 1.330(5) . ?
F2 C2 1.343(5) . ?
F3 C2 1.342(5) . ?
O1 C1 1.414(5) . ?
O1 C10 1.447(5) . ?
O2 C1 1.392(6) . ?
O2 C9 1.441(6) . ?
O3 C11 1.416(6) . ?
O3 H3 0.80(7) . ?
N1 O5 1.219(5) . ?
N1 O4 1.227(5) . ?
N1 C5 1.472(6) . ?
N2 O6 1.213(6) . ?
N2 O7 1.225(6) . ?
N2 C7 1.475(6) . ?
C1 C3 1.523(6) . ?
C1 C2 1.540(6) . ?
C3 C4 1.383(6) . ?
C3 C8 1.397(6) . ?
C4 C5 1.379(7) . ?
C4 H4 0.82(6) . ?
C5 C6 1.389(7) . ?
C6 C7 1.375(7) . ?
C6 H6 0.87(6) . ?
C7 C8 1.378(6) . ?
C8 H8 0.91(5) . ?
C9 C10 1.539(6) . ?
C9 H9A 1.04(5) . ?
C9 H9B 1.01(6) . ?
C10 C12 1.522(6) . ?
C10 C11 1.524(6) . ?
C11 H11A 0.97(6) . ?
C11 H11B 1.03(6) . ?
C12 C13 1.392(6) . ?
C12 C17 1.392(6) . ?
C13 C14 1.389(7) . ?
C13 H13 0.91(5) . ?
C14 C15 1.380(7) . ?
C14 H14 0.98(6) . ?
C15 C16 1.379(7) . ?
C16 C17 1.390(7) . ?
C16 H16 0.84(6) . ?
C17 H17 0.95(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
C1 O1 C10 108.1(3) . . ?
C1 O2 C9 107.2(3) . . ?
C11 O3 H3 112(5) . . ?
O5 N1 O4 123.3(4) . . ?
O5 N1 C5 118.3(4) . . ?
O4 N1 C5 118.5(4) . . ?
O6 N2 O7 124.6(4) . . ?
O6 N2 C7 118.2(4) . . ?
O7 N2 C7 117.2(4) . . ?
O2 C1 O1 109.0(4) . . ?
O2 C1 C3 110.5(4) . . ?
O1 C1 C3 111.1(4) . . ?
O2 C1 C2 108.8(4) . . ?
O1 C1 C2 107.0(4) . . ?
C3 C1 C2 110.3(4) . . ?
F1 C2 F3 107.4(4) . . ?
F1 C2 F2 107.7(4) . . ?
F3 C2 F2 107.0(4) . . ?
F1 C2 C1 112.1(4) . . ?
F3 C2 C1 111.9(4) . . ?
F2 C2 C1 110.5(4) . . ?
C4 C3 C8 120.2(4) . . ?
C4 C3 C1 119.6(4) . . ?
C8 C3 C1 120.1(4) . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 H4 126(4) . . ?
C3 C4 H4 115(4) . . ?
C4 C5 C6 123.5(4) . . ?
C4 C5 N1 118.8(4) . . ?
C6 C5 N1 117.6(4) . . ?
C7 C6 C5 116.0(4) . . ?
C7 C6 H6 123(4) . . ?
C5 C6 H6 121(4) . . ?
C6 C7 C8 123.3(5) . . ?
C6 C7 N2 118.4(4) . . ?
C8 C7 N2 118.3(4) . . ?
C7 C8 C3 118.6(4) . . ?
C7 C8 H8 121(3) . . ?
C3 C8 H8 120(3) . . ?
O2 C9 C10 102.1(4) . . ?
O2 C9 H9A 111(3) . . ?
C10 C9 H9A 109(3) . . ?
O2 C9 H9B 110(3) . . ?
C10 C9 H9B 111(3) . . ?
H9A C9 H9B 113(4) . . ?
O1 C10 C12 111.1(4) . . ?
O1 C10 C11 106.3(3) . . ?
C12 C10 C11 112.5(4) . . ?
O1 C10 C9 102.0(3) . . ?
C12 C10 C9 112.3(4) . . ?
C11 C10 C9 111.9(4) . . ?
O3 C11 C10 112.2(4) . . ?
O3 C11 H11A 108(3) . . ?
C10 C11 H11A 111(3) . . ?
O3 C11 H11B 108(3) . . ?
C10 C11 H11B 111(3) . . ?
H11A C11 H11B 106(5) . . ?
C13 C12 C17 118.5(4) . . ?
C13 C12 C10 120.3(4) . . ?
C17 C12 C10 121.1(4) . . ?
C14 C13 C12 121.4(4) . . ?
C14 C13 H13 119(3) . . ?
C12 C13 H13 120(3) . . ?
C15 C14 C13 118.6(4) . . ?
C15 C14 H14 121(3) . . ?
C13 C14 H14 121(3) . . ?
C16 C15 C14 121.5(4) . . ?
C16 C15 Br1 119.4(4) . . ?
C14 C15 Br1 119.1(4) . . ?
C15 C16 C17 119.3(4) . . ?
C15 C16 H16 116(4) . . ?
C17 C16 H16 125(4) . . ?
C16 C17 C12 120.6(4) . . ?
C16 C17 H17 116(3) . . ?
C12 C17 H17 124(3) . . ?

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
C9 O2 C1 O1 -19.1(5) . . . . ?
C9 O2 C1 C3 -141.5(4) . . . . ?
C9 O2 C1 C2 97.2(4) . . . . ?
C10 O1 C1 O2 -3.3(5) . . . . ?
C10 O1 C1 C3 118.8(4) . . . . ?
C10 O1 C1 C2 -120.8(4) . . . . ?
O2 C1 C2 F1 -61.3(5) . . . . ?
O1 C1 C2 F1 56.4(5) . . . . ?
C3 C1 C2 F1 177.4(4) . . . . ?
O2 C1 C2 F3 178.0(3) . . . . ?
O1 C1 C2 F3 -64.4(5) . . . . ?
C3 C1 C2 F3 56.6(5) . . . . ?
O2 C1 C2 F2 58.9(5) . . . . ?
O1 C1 C2 F2 176.5(4) . . . . ?
C3 C1 C2 F2 -62.5(5) . . . . ?
O2 C1 C3 C4 -13.6(6) . . . . ?
O1 C1 C3 C4 -134.7(4) . . . . ?
C2 C1 C3 C4 106.8(5) . . . . ?
O2 C1 C3 C8 165.1(4) . . . . ?
O1 C1 C3 C8 43.9(6) . . . . ?
C2 C1 C3 C8 -74.5(5) . . . . ?
C8 C3 C4 C5 0.2(6) . . . . ?
C1 C3 C4 C5 178.9(4) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?
C3 C4 C5 N1 -178.6(4) . . . . ?
O5 N1 C5 C4 -2.9(6) . . . . ?
O4 N1 C5 C4 176.9(4) . . . . ?
O5 N1 C5 C6 178.4(4) . . . . ?
O4 N1 C5 C6 -1.9(6) . . . . ?
C4 C5 C6 C7 -0.1(7) . . . . ?
N1 C5 C6 C7 178.5(4) . . . . ?
C5 C6 C7 C8 0.0(7) . . . . ?
C5 C6 C7 N2 179.0(4) . . . . ?
O6 N2 C7 C6 -172.9(5) . . . . ?
O7 N2 C7 C6 5.5(7) . . . . ?
O6 N2 C7 C8 6.2(7) . . . . ?
O7 N2 C7 C8 -175.3(5) . . . . ?
C6 C7 C8 C3 0.3(7) . . . . ?
N2 C7 C8 C3 -178.8(4) . . . . ?
C4 C3 C8 C7 -0.4(7) . . . . ?
C1 C3 C8 C7 -179.0(4) . . . . ?
C1 O2 C9 C10 32.0(4) . . . . ?
C1 O1 C10 C12 -97.5(4) . . . . ?
C1 O1 C10 C11 139.7(4) . . . . ?
C1 O1 C10 C9 22.3(4) . . . . ?
O2 C9 C10 O1 -32.6(4) . . . . ?
O2 C9 C10 C12 86.3(4) . . . . ?
O2 C9 C10 C11 -145.9(4) . . . . ?
O1 C10 C11 O3 61.9(5) . . . . ?
C12 C10 C11 O3 -59.9(5) . . . . ?
C9 C10 C11 O3 172.5(4) . . . . ?
O1 C10 C12 C13 170.9(4) . . . . ?
C11 C10 C12 C13 -70.0(5) . . . . ?
C9 C10 C12 C13 57.4(5) . . . . ?
O1 C10 C12 C17 -10.9(6) . . . . ?
C11 C10 C12 C17 108.2(5) . . . . ?
C9 C10 C12 C17 -124.4(5) . . . . ?
C17 C12 C13 C14 -0.2(7) . . . . ?
C10 C12 C13 C14 178.1(4) . . . . ?
C12 C13 C14 C15 0.0(7) . . . . ?
C13 C14 C15 C16 0.5(7) . . . . ?
C13 C14 C15 Br1 -178.4(3) . . . . ?
C14 C15 C16 C17 -0.8(7) . . . . ?
Br1 C15 C16 C17 178.1(4) . . . . ?
C15 C16 C17 C12 0.6(7) . . . . ?
C13 C12 C17 C16 -0.1(7) . . . . ?
C10 C12 C17 C16 -178.4(4) . . . . ?

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
O3 H3 O4 0.80(7) 2.39(7) 3.064(5) 143(7) 3_655 yes

_refine_diff_density_max         0.605
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.079

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wie9750
_database_code_depnum_ccdc_archive 'CCDC 2130260'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2021-12-21 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 F3 N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         327.26

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   13.5889(3)
_cell_length_b                   9.9317(2)
_cell_length_c                   20.9678(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2829.83(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      4.2170
_cell_measurement_theta_max      68.3384
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.058
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344

_exptl_absorpt_coefficient_mu    1.198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            22240
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_theta_min         4.22
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_full        68.36
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

_refine_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.

The hydrogen at O2 atom was refined freely.
;

_reflns_number_total             2578
_reflns_number_gt                2349
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0827
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_number_reflns         2578
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0317P)²+1.4456P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

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 0.57497(10) 0.64451(13) 0.64723(6) 0.0166(3) Uani d . . . 1 . .
O O1 0.57958(7) 0.68339(9) 0.71167(4) 0.0166(2) Uani d . . . 1 . .
O O2 0.63916(7) 0.71685(11) 0.60836(5) 0.0208(2) Uani d . . . 1 . .
H H2 0.6326(14) 0.797(2) 0.6162(9) 0.032(5) Uiso d . . . 1 . .
C C2 0.46821(11) 0.67967(14) 0.62852(7) 0.0212(3) Uani d . . . 1 . .
F F1 0.40243(6) 0.62316(9) 0.66759(4) 0.0261(2) Uani d . . . 1 . .
F F2 0.45363(7) 0.81270(9) 0.63010(5) 0.0312(2) Uani d . . . 1 . .
F F3 0.44795(7) 0.63852(9) 0.56923(4) 0.0293(2) Uani d . . . 1 . .
C C3 0.67807(10) 0.68572(14) 0.73815(7) 0.0189(3) Uani d . . . 1 . .
H H3A 0.7161 0.7615 0.7199 0.023 Uiso calc U . R 1 . .
H H3B 0.7128 0.6007 0.7282 0.023 Uiso calc U . R 1 . .
C C11 0.66816(9) 0.70232(14) 0.80896(7) 0.0171(3) Uani d . . . 1 . .
C C12 0.68879(10) 0.82477(14) 0.83785(7) 0.0218(3) Uani d . . . 1 . .
H H12 0.7103 0.8986 0.8127 0.026 Uiso calc U . R 1 . .
C C13 0.67813(11) 0.84015(15) 0.90339(8) 0.0263(3) Uani d . . . 1 . .
H H13 0.6928 0.9242 0.9228 0.032 Uiso calc U . R 1 . .
C C14 0.64618(11) 0.73321(16) 0.94041(7) 0.0255(3) Uani d . . . 1 . .
H H14 0.6386 0.7438 0.9852 0.031 Uiso calc U . R 1 . .
C C15 0.62528(11) 0.61027(15) 0.91174(7) 0.0241(3) Uani d . . . 1 . .
H H15 0.6033 0.5366 0.9369 0.029 Uiso calc U . R 1 . .
C C16 0.63647(10) 0.59522(14) 0.84656(7) 0.0202(3) Uani d . . . 1 . .
H H16 0.6224 0.5109 0.8272 0.024 Uiso calc U . R 1 . .
C C21 0.59309(9) 0.49448(13) 0.63707(6) 0.0155(3) Uani d . . . 1 . .
C C22 0.56702(9) 0.40314(14) 0.68465(6) 0.0167(3) Uani d . . . 1 . .
H H22 0.5398 0.4349 0.7236 0.02 Uiso calc U . R 1 . .
C C23 0.58061(10) 0.26624(14) 0.67541(7) 0.0172(3) Uani d . . . 1 . .
H H23 0.5647 0.2034 0.708 0.021 Uiso calc U . R 1 . .
C C24 0.61794(10) 0.22361(13) 0.61743(7) 0.0171(3) Uani d . . . 1 . .
C C25 0.64305(10) 0.31139(14) 0.56880(7) 0.0189(3) Uani d . . . 1 . .
H H25 0.668 0.2788 0.5294 0.023 Uiso calc U . R 1 . .
C C26 0.63080(10) 0.44805(14) 0.57922(7) 0.0186(3) Uani d . . . 1 . .
H H26 0.6482 0.5105 0.5468 0.022 Uiso calc U . R 1 . .
N N1 0.63076(9) 0.07872(12) 0.60657(6) 0.0212(3) Uani d . . . 1 . .
O O3 0.62895(8) 0.00250(10) 0.65297(5) 0.0275(3) Uani d . . . 1 . .
O O4 0.64296(8) 0.03868(11) 0.55170(5) 0.0308(3) 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 O2 . 1.3932(17) ?
C1 O1 . 1.4068(16) ?
C1 C21 . 1.5252(18) ?
C1 C2 . 1.5429(19) ?
O1 C3 . 1.4491(16) ?
O2 H2 . 0.82(2) ?
C2 F1 . 1.3361(18) ?
C2 F2 . 1.3364(17) ?
C2 F3 . 1.3371(17) ?
C3 C11 . 1.500(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C11 C12 . 1.387(2) ?
C11 C16 . 1.392(2) ?
C12 C13 . 1.390(2) ?
C12 H12 . 0.95 ?
C13 C14 . 1.385(2) ?
C13 H13 . 0.95 ?
C14 C15 . 1.390(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.383(2) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C21 C22 . 1.3942(19) ?
C21 C26 . 1.3953(19) ?
C22 C23 . 1.386(2) ?
C22 H22 . 0.95 ?
C23 C24 . 1.384(2) ?
C23 H23 . 0.95 ?
C24 C25 . 1.384(2) ?
C24 N1 . 1.4672(18) ?
C25 C26 . 1.385(2) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
N1 O4 . 1.2286(16) ?
N1 O3 . 1.2330(17) ?

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
O2 C1 O1 . . 113.10(11) ?
O2 C1 C21 . . 108.73(11) ?
O1 C1 C21 . . 113.27(11) ?
O2 C1 C2 . . 108.86(11) ?
O1 C1 C2 . . 102.95(10) ?
C21 C1 C2 . . 109.72(11) ?
C1 O1 C3 . . 114.43(10) ?
C1 O2 H2 . . 108.5(14) ?
F1 C2 F2 . . 107.51(11) ?
F1 C2 F3 . . 107.69(11) ?
F2 C2 F3 . . 107.14(12) ?
F1 C2 C1 . . 112.22(11) ?
F2 C2 C1 . . 110.90(12) ?
F3 C2 C1 . . 111.15(11) ?
O1 C3 C11 . . 107.35(10) ?
O1 C3 H3A . . 110.2 ?
C11 C3 H3A . . 110.2 ?
O1 C3 H3B . . 110.2 ?
C11 C3 H3B . . 110.2 ?
H3A C3 H3B . . 108.5 ?
C12 C11 C16 . . 119.01(13) ?
C12 C11 C3 . . 120.69(13) ?
C16 C11 C3 . . 120.29(12) ?
C11 C12 C13 . . 120.46(14) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C14 C13 C12 . . 120.15(14) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 119.67(14) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C16 C15 C14 . . 119.98(14) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C15 C16 C11 . . 120.73(13) ?
C15 C16 H16 . . 119.6 ?
C11 C16 H16 . . 119.6 ?
C22 C21 C26 . . 120.03(12) ?
C22 C21 C1 . . 119.66(12) ?
C26 C21 C1 . . 120.23(12) ?
C23 C22 C21 . . 120.30(13) ?
C23 C22 H22 . . 119.8 ?
C21 C22 H22 . . 119.8 ?
C24 C23 C22 . . 118.16(13) ?
C24 C23 H23 . . 120.9 ?
C22 C23 H23 . . 120.9 ?
C23 C24 C25 . . 123.01(13) ?
C23 C24 N1 . . 118.68(12) ?
C25 C24 N1 . . 118.31(12) ?
C24 C25 C26 . . 118.13(13) ?
C24 C25 H25 . . 120.9 ?
C26 C25 H25 . . 120.9 ?
C25 C26 C21 . . 120.34(13) ?
C25 C26 H26 . . 119.8 ?
C21 C26 H26 . . 119.8 ?
O4 N1 O3 . . 122.88(12) ?
O4 N1 C24 . . 118.60(12) ?
O3 N1 C24 . . 118.51(12) ?

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
O2 C1 O1 C3 . . . . -51.21(15) ?
C21 C1 O1 C3 . . . . 73.08(14) ?
C2 C1 O1 C3 . . . . -168.51(10) ?
O2 C1 C2 F1 . . . . -174.40(11) ?
O1 C1 C2 F1 . . . . -54.14(14) ?
C21 C1 C2 F1 . . . . 66.72(14) ?
O2 C1 C2 F2 . . . . -54.14(15) ?
O1 C1 C2 F2 . . . . 66.12(14) ?
C21 C1 C2 F2 . . . . -173.02(11) ?
O2 C1 C2 F3 . . . . 64.94(14) ?
O1 C1 C2 F3 . . . . -174.80(11) ?
C21 C1 C2 F3 . . . . -53.94(15) ?
C1 O1 C3 C11 . . . . -169.21(11) ?
O1 C3 C11 C12 . . . . -105.24(14) ?
O1 C3 C11 C16 . . . . 73.71(15) ?
C16 C11 C12 C13 . . . . 0.1(2) ?
C3 C11 C12 C13 . . . . 179.07(13) ?
C11 C12 C13 C14 . . . . -0.4(2) ?
C12 C13 C14 C15 . . . . 0.3(2) ?
C13 C14 C15 C16 . . . . 0.0(2) ?
C14 C15 C16 C11 . . . . -0.3(2) ?
C12 C11 C16 C15 . . . . 0.2(2) ?
C3 C11 C16 C15 . . . . -178.74(12) ?
O2 C1 C21 C22 . . . . 156.42(11) ?
O1 C1 C21 C22 . . . . 29.79(17) ?
C2 C1 C21 C22 . . . . -84.62(15) ?
O2 C1 C21 C26 . . . . -26.90(16) ?
O1 C1 C21 C26 . . . . -153.54(12) ?
C2 C1 C21 C26 . . . . 92.06(14) ?
C26 C21 C22 C23 . . . . 1.58(19) ?
C1 C21 C22 C23 . . . . 178.26(12) ?
C21 C22 C23 C24 . . . . -1.71(19) ?
C22 C23 C24 C25 . . . . 0.7(2) ?
C22 C23 C24 N1 . . . . -178.77(11) ?
C23 C24 C25 C26 . . . . 0.5(2) ?
N1 C24 C25 C26 . . . . 179.97(12) ?
C24 C25 C26 C21 . . . . -0.7(2) ?
C22 C21 C26 C25 . . . . -0.3(2) ?
C1 C21 C26 C25 . . . . -177.00(12) ?
C23 C24 N1 O4 . . . . 164.32(12) ?
C25 C24 N1 O4 . . . . -15.13(18) ?
C23 C24 N1 O3 . . . . -15.77(18) ?
C25 C24 N1 O3 . . . . 164.77(12) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 O3 1_565 0.82(2) 2.18(2) 2.9904(15) 169.6(19) ?

