# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1868734'
_audit_update_record             
;
2018-09-20 deposited with the CCDC.
2018-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H10 F N2 O5'
_chemical_formula_weight         221.17

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                   5.060(6)
_cell_length_b                   6.392(8)
_cell_length_c                   15.823(18)
_cell_angle_alpha                87.32(4)
_cell_angle_beta                 83.90(4)
_cell_angle_gamma                71.23(2)
_cell_volume                     481.8(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    566(2)
_cell_measurement_reflns_used    3968
_cell_measurement_theta_min      3.591
_cell_measurement_theta_max      24.993

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             230
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      566(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury375R/M CCD (XtaLAB mini)'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3968
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_av_R_equivalents  0.0739
_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       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.591
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1669
_reflns_number_gt                1330
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0875P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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_number_reflns         1669
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.2492(3) 0.2678(2) 0.17115(7) 0.0676(5) Uani 1 1 d . . . . .
O1 O -0.1725(3) 0.2888(2) 0.49702(9) 0.0539(4) Uani 1 1 d . . . . .
N1 N 0.0910(3) 0.4063(2) 0.39091(9) 0.0414(4) Uani 1 1 d . . . . .
O2 O 0.3500(3) 0.5351(2) 0.28797(9) 0.0547(4) Uani 1 1 d . . . . .
O5 O -0.4376(3) -0.1392(3) 0.38927(11) 0.0585(5) Uani 1 1 d . . . . .
N2 N -0.1138(3) 0.1425(3) 0.36517(10) 0.0427(4) Uani 1 1 d . . . . .
O3 O 0.2598(4) 0.1970(3) -0.20195(9) 0.0655(5) Uani 1 1 d . . . . .
C2 C 0.2067(4) 0.4131(3) 0.30882(11) 0.0400(5) Uani 1 1 d . . . . .
O4 O 0.4273(4) 0.4074(3) -0.13035(10) 0.0703(6) Uani 1 1 d . . . . .
C4 C -0.0083(4) 0.1363(3) 0.28133(12) 0.0467(5) Uani 1 1 d . . . . .
C7 C 0.0620(5) 0.0181(4) -0.04478(12) 0.0501(5) Uani 1 1 d . . . . .
C1 C -0.0719(4) 0.2782(3) 0.42231(11) 0.0397(5) Uani 1 1 d . . . . .
C3 C 0.1445(4) 0.2662(3) 0.25327(11) 0.0448(5) Uani 1 1 d . . . . .
C5 C 0.2829(4) 0.2700(3) -0.13562(12) 0.0466(5) Uani 1 1 d . . . . .
C6 C 0.1471(6) 0.2246(4) -0.05062(14) 0.0595(7) Uani 1 1 d . . . . .
H3 H -0.209(6) 0.053(5) 0.3845(17) 0.072(7) Uiso 1 1 d . . . . .
H9 H -0.553(6) -0.189(5) 0.4278(19) 0.089(9) Uiso 1 1 d . . . . .
H4 H 0.506(6) 0.419(4) -0.1849(19) 0.079(8) Uiso 1 1 d . . . . .
H1 H 0.115(5) 0.508(4) 0.4296(16) 0.067(7) Uiso 1 1 d . . . . .
H10 H -0.429(6) -0.195(5) 0.3433(19) 0.084(9) Uiso 1 1 d . . . . .
H2 H -0.053(4) 0.018(3) 0.2426(14) 0.057(6) Uiso 1 1 d . . . . .
H8 H 0.213(6) -0.094(5) -0.0571(18) 0.080(9) Uiso 1 1 d . . . . .
H7 H -0.076(5) 0.027(4) -0.0862(16) 0.069(7) Uiso 1 1 d . . . . .
H5 H -0.044(7) 0.371(6) -0.0429(19) 0.112(11) Uiso 1 1 d . . . . .
H6 H 0.258(7) 0.221(5) -0.011(2) 0.090(9) 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
F1 C3 1.351(2) . ?
O1 C1 1.232(3) . ?
N1 C2 1.372(3) . ?
N1 C1 1.380(2) . ?
O2 C2 1.238(2) . ?
N2 C1 1.359(3) . ?
N2 C4 1.374(3) . ?
O3 C5 1.200(3) . ?
C2 C3 1.442(3) . ?
O4 C5 1.321(3) . ?
C4 C3 1.338(3) . ?
C7 C6 1.511(3) . ?
C7 C7 1.526(4) 2 ?
C5 C6 1.503(3) . ?

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 C1 126.78(16) . . ?
C1 N2 C4 122.67(17) . . ?
O2 C2 N1 121.03(17) . . ?
O2 C2 C3 125.76(18) . . ?
N1 C2 C3 113.20(16) . . ?
C3 C4 N2 119.93(18) . . ?
C6 C7 C7 111.5(2) . 2 ?
O1 C1 N2 122.92(17) . . ?
O1 C1 N1 121.69(17) . . ?
N2 C1 N1 115.39(17) . . ?
C4 C3 F1 121.95(18) . . ?
C4 C3 C2 122.00(18) . . ?
F1 C3 C2 116.05(17) . . ?
O3 C5 O4 122.57(17) . . ?
O3 C5 C6 125.06(19) . . ?
O4 C5 C6 112.33(18) . . ?
C5 C6 C7 115.63(18) . . ?

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1868735'
_audit_update_record             
;
2018-09-20 deposited with the CCDC.
2018-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 F N2 O5'
_chemical_formula_weight         207.14

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'
F F 0.0171 0.0103 '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'

_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                   5.443(9)
_cell_length_b                   5.845(9)
_cell_length_c                   14.47(2)
_cell_angle_alpha                92.228(18)
_cell_angle_beta                 94.392(9)
_cell_angle_gamma                110.98(3)
_cell_volume                     427.5(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1998
_cell_measurement_theta_min      2.831
_cell_measurement_theta_max      27.505

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_F_000             214
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.153
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury375R/M CCD (XtaLAB mini)'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1998
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.831
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             1805
_reflns_number_gt                1232
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0962P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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_number_reflns         1805
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1537
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.956
_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
F1 F 0.9437(3) 0.1476(3) 0.13545(9) 0.0619(5) Uani 1 1 d . . . . .
O1 O 0.8220(3) 0.2078(3) 0.49785(11) 0.0515(5) Uani 1 1 d . . . . .
N1 N 0.9888(4) 0.0668(3) 0.37838(13) 0.0398(5) Uani 1 1 d . . . . .
O2 O 1.1553(3) -0.0879(3) 0.26331(11) 0.0536(5) Uani 1 1 d . . . . .
O3 O 1.4739(4) -0.3814(3) 0.16723(11) 0.0563(5) Uani 1 1 d . . . . .
O5 O 0.5509(4) 0.3910(4) 0.62711(15) 0.0585(5) Uani 1 1 d . . . . .
N2 N 0.7542(4) 0.3197(3) 0.35166(12) 0.0430(5) Uani 1 1 d . . . . .
C2 C 1.0297(4) 0.0398(4) 0.28734(15) 0.0393(5) Uani 1 1 d . . . . .
O4 O 1.2396(4) -0.1949(4) 0.09156(13) 0.0664(6) Uani 1 1 d . . . . .
C4 C 0.7830(5) 0.3032(4) 0.25924(16) 0.0453(5) Uani 1 1 d . . . . .
C3 C 0.9141(4) 0.1696(4) 0.22643(14) 0.0428(5) Uani 1 1 d . . . . .
C1 C 0.8524(4) 0.1999(4) 0.41507(15) 0.0392(5) Uani 1 1 d . . . . .
C6 C 1.4323(7) -0.4094(6) 0.00014(17) 0.0563(7) Uani 1 1 d . . . . .
C5 C 1.3883(5) -0.3310(4) 0.09492(15) 0.0441(5) Uani 1 1 d . . . . .
H2 H 0.702(5) 0.391(4) 0.2204(18) 0.050(7) Uiso 1 1 d . . . . .
H1 H 1.044(4) -0.012(4) 0.4171(16) 0.035(6) Uiso 1 1 d . . . . .
H3 H 0.662(5) 0.425(5) 0.3728(17) 0.054(7) Uiso 1 1 d . . . . .
H4 H 1.218(6) -0.161(5) 0.159(2) 0.073(9) Uiso 1 1 d . . . . .
H7 H 0.585(8) 0.339(7) 0.669(3) 0.095(15) Uiso 1 1 d . . . . .
H8 H 0.632(7) 0.330(6) 0.576(3) 0.102(12) Uiso 1 1 d . . . . .
H5 H 1.510(8) -0.281(7) -0.033(3) 0.105(13) Uiso 1 1 d . . . . .
H6 H 1.273(7) -0.467(6) -0.036(2) 0.089(11) 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
F1 C3 1.345(3) . ?
O1 C1 1.223(3) . ?
N1 C2 1.365(3) . ?
N1 C1 1.371(3) . ?
N1 H1 0.84(2) . ?
O2 C2 1.236(3) . ?
O3 C5 1.203(3) . ?
O5 H7 0.72(4) . ?
O5 H8 1.00(4) . ?
N2 C4 1.362(3) . ?
N2 C1 1.364(3) . ?
N2 H3 0.98(3) . ?
C2 C3 1.435(3) . ?
O4 C5 1.322(3) . ?
O4 H4 1.01(3) . ?
C4 C3 1.329(3) . ?
C4 H2 0.96(2) . ?
C6 C6 1.492(5) 2_845 ?
C6 C5 1.493(4) . ?
C6 H5 0.90(4) . ?
C6 H6 0.92(4) . ?

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 C1 127.23(18) . . ?
C2 N1 H1 118.3(16) . . ?
C1 N1 H1 114.3(16) . . ?
H7 O5 H8 106(4) . . ?
C4 N2 C1 122.80(19) . . ?
C4 N2 H3 117.9(15) . . ?
C1 N2 H3 119.3(15) . . ?
O2 C2 N1 120.69(19) . . ?
O2 C2 C3 125.5(2) . . ?
N1 C2 C3 113.79(19) . . ?
C5 O4 H4 104.3(16) . . ?
C3 C4 N2 120.8(2) . . ?
C3 C4 H2 123.1(15) . . ?
N2 C4 H2 116.1(15) . . ?
C4 C3 F1 122.24(19) . . ?
C4 C3 C2 120.9(2) . . ?
F1 C3 C2 116.82(19) . . ?
O1 C1 N2 123.53(19) . . ?
O1 C1 N1 122.08(19) . . ?
N2 C1 N1 114.4(2) . . ?
C6 C6 C5 113.8(3) 2_845 . ?
C6 C6 H5 112(2) 2_845 . ?
C5 C6 H5 112(2) . . ?
C6 C6 H6 112(2) 2_845 . ?
C5 C6 H6 109(2) . . ?
H5 C6 H6 96(3) . . ?
O3 C5 O4 122.2(2) . . ?
O3 C5 C6 125.9(2) . . ?
O4 C5 C6 111.9(2) . . ?

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
C1 N1 C2 O2 -179.4(2) . . . . ?
C1 N1 C2 C3 0.3(3) . . . . ?
C1 N2 C4 C3 -1.0(4) . . . . ?
N2 C4 C3 F1 179.3(2) . . . . ?
N2 C4 C3 C2 -0.2(4) . . . . ?
O2 C2 C3 C4 -179.8(2) . . . . ?
N1 C2 C3 C4 0.5(3) . . . . ?
O2 C2 C3 F1 0.7(3) . . . . ?
N1 C2 C3 F1 -179.02(18) . . . . ?
C4 N2 C1 O1 -178.0(2) . . . . ?
C4 N2 C1 N1 1.7(3) . . . . ?
C2 N1 C1 O1 178.3(2) . . . . ?
C2 N1 C1 N2 -1.4(3) . . . . ?
C6 C6 C5 O3 7.8(5) 2_845 . . . ?
C6 C6 C5 O4 -172.2(4) 2_845 . . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.054

