# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1165-2
_database_code_depnum_ccdc_archive 'CCDC 1915197'
loop_
_audit_author_name
_audit_author_address
'Mingming Sun'
;The Cambridge Crystallographic Data Centre 
China
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 F2 N2 O3'
_chemical_formula_weight         298.29
_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 0.0181 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'

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_cell_length_a                   8.2790(5)
_cell_length_b                   8.8080(5)
_cell_length_c                   10.5654(6)
_cell_angle_alpha                110.521(5)
_cell_angle_beta                 98.070(5)
_cell_angle_gamma                95.404(5)
_cell_volume                     705.82(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8334
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      64.62
_cell_measurement_theta_min      4.53
_exptl_absorpt_coefficient_mu    0.998
_exptl_absorpt_correction_T_max  0.9068
_exptl_absorpt_correction_T_min  0.8253
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21113
_diffrn_reflns_theta_full        65.34
_diffrn_reflns_theta_max         65.34
_diffrn_reflns_theta_min         4.55
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1917
_reflns_number_total             2320
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0950P)²+0.2469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.1617
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.07886(17) 0.4897(2) 0.35761(13) 0.0662(5) Uani 1 1 d . . .
O2 O 0.85784(19) 0.8465(2) 0.37522(18) 0.0567(5) Uani 1 1 d . . .
O3 O 0.66476(19) 1.00913(19) 0.40711(18) 0.0554(5) Uani 1 1 d . . .
F2 F 0.36451(17) 0.3768(2) -0.00852(16) 0.0831(6) Uani 1 1 d . . .
N2 N -0.1965(2) 0.1347(2) -0.09224(18) 0.0469(5) Uani 1 1 d . . .
N1 N 0.3782(2) 0.5300(2) 0.26995(19) 0.0459(5) Uani 1 1 d . . .
C6 C -0.0589(3) 0.3187(3) 0.1370(2) 0.0444(5) Uani 1 1 d . . .
H1 H -0.1563 0.3074 0.1729 0.053 Uiso 1 1 calc R . .
C2 C 0.2292(3) 0.4389(3) 0.1790(2) 0.0443(5) Uani 1 1 d . . .
O1 O 0.4816(2) 0.3076(2) 0.2935(2) 0.0743(6) Uani 1 1 d . . .
C5 C -0.0585(2) 0.2362(3) -0.0035(2) 0.0413(5) Uani 1 1 d . . .
C1 C 0.0825(3) 0.4159(3) 0.2217(2) 0.0454(5) Uani 1 1 d . . .
C4 C 0.0876(3) 0.2600(3) -0.0510(2) 0.0523(6) Uani 1 1 d . . .
H5 H 0.0923 0.2085 -0.1456 0.063 Uiso 1 1 calc R . .
C3 C 0.2236(3) 0.3582(3) 0.0399(3) 0.0536(6) Uani 1 1 d . . .
C11 C 0.7212(3) 0.8682(3) 0.3935(2) 0.0431(5) Uani 1 1 d . . .
C9 C 0.5926(3) 0.7437(3) 0.4050(2) 0.0475(6) Uani 1 1 d . . .
H0aa H 0.5619 0.7881 0.4978 0.057 Uiso 1 1 calc R . .
C10 C 0.6492(3) 0.5795(3) 0.3849(3) 0.0539(6) Uani 1 1 d . . .
H9A H 0.7362 0.5626 0.3281 0.065 Uiso 1 1 calc R . .
H9B H 0.6934 0.5730 0.4746 0.065 Uiso 1 1 calc R . .
C13 C -0.3345(3) 0.0888(3) -0.0355(3) 0.0575(7) Uani 1 1 d . . .
H10A H -0.2977 0.0319 0.0256 0.086 Uiso 1 1 calc R . .
H10B H -0.4221 0.0158 -0.1105 0.086 Uiso 1 1 calc R . .
H10C H -0.3769 0.1876 0.0168 0.086 Uiso 1 1 calc R . .
C14 C -0.1766(3) 0.0169(3) -0.2236(2) 0.0541(6) Uani 1 1 d . . .
H11A H -0.1305 0.0755 -0.2772 0.081 Uiso 1 1 calc R . .
H11B H -0.2843 -0.0471 -0.2746 0.081 Uiso 1 1 calc R . .
H11C H -0.1016 -0.0569 -0.2077 0.081 Uiso 1 1 calc R . .
C8 C 0.4346(3) 0.7015(3) 0.2934(2) 0.0467(6) Uani 1 1 d . . .
H8 H 0.3511 0.7714 0.3272 0.056 Uiso 1 1 calc R . .
H7 H 0.4603 0.7140 0.2085 0.056 Uiso 1 1 calc R . .
C7 C 0.4976(3) 0.4539(3) 0.3130(3) 0.0529(6) Uani 1 1 d . . .
C12 C 0.7821(3) 1.1379(3) 0.3988(3) 0.0584(7) Uani 1 1 d . . .
H14A H 0.8783 1.1660 0.4730 0.088 Uiso 1 1 calc R . .
H14B H 0.7293 1.2353 0.4081 0.088 Uiso 1 1 calc R . .
H14C H 0.8177 1.0991 0.3098 0.088 Uiso 1 1 calc R . .


_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 C1 1.359(3) . ?
O2 C11 1.196(3) . ?
O3 C11 1.335(3) . ?
O3 C12 1.458(3) . ?
F2 C3 1.357(3) . ?
N2 C5 1.379(3) . ?
N2 C13 1.451(3) . ?
N2 C14 1.455(3) . ?
N1 C2 1.425(3) . ?
N1 C8 1.460(3) . ?
N1 C7 1.359(3) . ?
C6 H1 0.9500 . ?
C6 C5 1.406(3) . ?
C6 C1 1.373(3) . ?
C2 C1 1.376(3) . ?
C2 C3 1.381(3) . ?
O1 C7 1.222(3) . ?
C5 C4 1.399(3) . ?
C4 H5 0.9500 . ?
C4 C3 1.367(3) . ?
C11 C9 1.503(3) . ?
C9 H0aa 1.0000 . ?
C9 C10 1.515(3) . ?
C9 C8 1.552(3) . ?
C10 H9A 0.9900 . ?
C10 H9B 0.9900 . ?
C10 C7 1.503(3) . ?
C13 H10A 0.9800 . ?
C13 H10B 0.9800 . ?
C13 H10C 0.9800 . ?
C14 H11A 0.9800 . ?
C14 H11B 0.9800 . ?
C14 H11C 0.9800 . ?
C8 H8 0.9900 . ?
C8 H7 0.9900 . ?
C12 H14A 0.9800 . ?
C12 H14B 0.9800 . ?
C12 H14C 0.9800 . ?

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
C11 O3 C12 115.36(18) . . ?
C5 N2 C13 118.85(18) . . ?
C5 N2 C14 118.78(18) . . ?
C13 N2 C14 115.90(18) . . ?
C2 N1 C8 122.91(17) . . ?
C7 N1 C2 121.37(18) . . ?
C7 N1 C8 113.67(18) . . ?
C5 C6 H1 120.2 . . ?
C1 C6 H1 120.2 . . ?
C1 C6 C5 119.5(2) . . ?
C1 C2 N1 123.6(2) . . ?
C1 C2 C3 114.38(19) . . ?
C3 C2 N1 121.9(2) . . ?
N2 C5 C6 121.68(19) . . ?
N2 C5 C4 120.7(2) . . ?
C4 C5 C6 117.65(19) . . ?
F1 C1 C6 117.84(19) . . ?
F1 C1 C2 117.83(18) . . ?
C6 C1 C2 124.3(2) . . ?
C5 C4 H5 120.3 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H5 120.3 . . ?
F2 C3 C2 117.12(19) . . ?
F2 C3 C4 118.1(2) . . ?
C4 C3 C2 124.8(2) . . ?
O2 C11 O3 123.3(2) . . ?
O2 C11 C9 125.1(2) . . ?
O3 C11 C9 111.59(18) . . ?
C11 C9 H0aa 108.9 . . ?
C11 C9 C10 113.42(19) . . ?
C11 C9 C8 112.51(19) . . ?
C10 C9 H0aa 108.9 . . ?
C10 C9 C8 104.11(18) . . ?
C8 C9 H0aa 108.9 . . ?
C9 C10 H9A 110.7 . . ?
C9 C10 H9B 110.7 . . ?
H9A C10 H9B 108.8 . . ?
C7 C10 C9 105.20(18) . . ?
C7 C10 H9A 110.7 . . ?
C7 C10 H9B 110.7 . . ?
N2 C13 H10A 109.5 . . ?
N2 C13 H10B 109.5 . . ?
N2 C13 H10C 109.5 . . ?
H10A C13 H10B 109.5 . . ?
H10A C13 H10C 109.5 . . ?
H10B C13 H10C 109.5 . . ?
N2 C14 H11A 109.5 . . ?
N2 C14 H11B 109.5 . . ?
N2 C14 H11C 109.5 . . ?
H11A C14 H11B 109.5 . . ?
H11A C14 H11C 109.5 . . ?
H11B C14 H11C 109.5 . . ?
N1 C8 C9 102.29(17) . . ?
N1 C8 H8 111.3 . . ?
N1 C8 H7 111.3 . . ?
C9 C8 H8 111.3 . . ?
C9 C8 H7 111.3 . . ?
H8 C8 H7 109.2 . . ?
N1 C7 C10 108.17(19) . . ?
O1 C7 N1 124.7(2) . . ?
O1 C7 C10 127.1(2) . . ?
O3 C12 H14A 109.5 . . ?
O3 C12 H14B 109.5 . . ?
O3 C12 H14C 109.5 . . ?
H14A C12 H14B 109.5 . . ?
H14A C12 H14C 109.5 . . ?
H14B C12 H14C 109.5 . . ?

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
O2 C11 C9 C10 -2.5(3) . . . . ?
O2 C11 C9 C8 -120.4(2) . . . . ?
O3 C11 C9 C10 177.87(19) . . . . ?
O3 C11 C9 C8 60.0(2) . . . . ?
N2 C5 C4 C3 -178.4(2) . . . . ?
N1 C2 C1 F1 2.6(3) . . . . ?
N1 C2 C1 C6 -175.0(2) . . . . ?
N1 C2 C3 F2 -3.7(4) . . . . ?
N1 C2 C3 C4 175.4(2) . . . . ?
C6 C5 C4 C3 1.4(4) . . . . ?
C2 N1 C8 C9 176.64(19) . . . . ?
C2 N1 C7 O1 -9.6(4) . . . . ?
C2 N1 C7 C10 169.6(2) . . . . ?
C5 C6 C1 F1 -178.01(19) . . . . ?
C5 C6 C1 C2 -0.4(4) . . . . ?
C5 C4 C3 F2 178.9(2) . . . . ?
C5 C4 C3 C2 -0.3(4) . . . . ?
C1 C6 C5 N2 178.7(2) . . . . ?
C1 C6 C5 C4 -1.1(3) . . . . ?
C1 C2 C3 F2 179.7(2) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C3 C2 C1 F1 179.1(2) . . . . ?
C3 C2 C1 C6 1.5(3) . . . . ?
C11 C9 C10 C7 -145.2(2) . . . . ?
C11 C9 C8 N1 148.21(19) . . . . ?
C9 C10 C7 N1 11.6(3) . . . . ?
C9 C10 C7 O1 -169.2(3) . . . . ?
C10 C9 C8 N1 25.0(2) . . . . ?
C13 N2 C5 C6 -11.3(3) . . . . ?
C13 N2 C5 C4 168.5(2) . . . . ?
C14 N2 C5 C6 -162.0(2) . . . . ?
C14 N2 C5 C4 17.9(3) . . . . ?
C8 N1 C2 C1 -97.5(3) . . . . ?
C8 N1 C2 C3 86.2(3) . . . . ?
C8 N1 C7 O1 -173.8(2) . . . . ?
C8 N1 C7 C10 5.4(3) . . . . ?
C8 C9 C10 C7 -22.6(3) . . . . ?
C7 N1 C2 C1 99.8(3) . . . . ?
C7 N1 C2 C3 -76.5(3) . . . . ?
C7 N1 C8 C9 -19.5(3) . . . . ?
C12 O3 C11 O2 -0.2(3) . . . . ?
C12 O3 C11 C9 179.36(19) . . . . ?

####################################################################### 
# 
# 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_1243
_database_code_depnum_ccdc_archive 'CCDC 1904410'
loop_
_audit_author_name
_audit_author_address
sunmingming
;Sunshine Lake Pharmaceutical
China
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 F2 N2 O5'
_chemical_formula_weight         286.19
_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 0.0181 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'


loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_cell_length_a                   10.7705(4)
_cell_length_b                   9.1548(3)
_cell_length_c                   12.1836(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.428(4)
_cell_angle_gamma                90.00
_cell_volume                     1139.72(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1868
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      66.48
_cell_measurement_theta_min      4.74
_exptl_absorpt_coefficient_mu    1.353
_exptl_absorpt_correction_T_max  0.8765
_exptl_absorpt_correction_T_min  0.6869
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3929
_diffrn_reflns_theta_full        66.80
_diffrn_reflns_theta_max         66.80
_diffrn_reflns_theta_min         4.79
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1635
_reflns_number_total             1978
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1978
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0769P)²+0.3019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1398
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.33373(12) 0.18029(15) 0.50347(13) 0.0471(4) Uani 1 1 d . . .
F2 F -0.05949(13) 0.41361(16) 0.30503(16) 0.0577(5) Uani 1 1 d . . .
N2 N 0.20477(17) 0.4380(2) 0.41653(17) 0.0343(4) Uani 1 1 d . . .
C2 C 0.1410(2) 0.3022(2) 0.39963(19) 0.0326(5) Uani 1 1 d . . .
O1 O 0.14804(16) 0.50443(18) 0.22570(14) 0.0432(4) Uani 1 1 d . . .
O5 O -0.16761(16) -0.1111(2) 0.28886(17) 0.0540(5) Uani 1 1 d . . .
O3 O 0.42864(17) 0.85681(19) 0.58503(19) 0.0567(6) Uani 1 1 d . . .
H5 H 0.4944 0.8888 0.6336 0.085 Uiso 1 1 calc R . .
O4 O 0.01038(17) -0.21464(19) 0.39291(17) 0.0516(5) Uani 1 1 d . . .
O2 O 0.52819(16) 0.64331(19) 0.63833(17) 0.0496(5) Uani 1 1 d . . .
C5 C 0.0146(2) 0.0352(2) 0.36528(19) 0.0337(5) Uani 1 1 d . . .
C3 C 0.0077(2) 0.2900(3) 0.3409(2) 0.0374(5) Uani 1 1 d . . .
C1 C 0.2059(2) 0.1734(2) 0.4428(2) 0.0338(5) Uani 1 1 d . . .
C4 C -0.0575(2) 0.1589(3) 0.3216(2) 0.0390(6) Uani 1 1 d . . .
H5A H -0.1464 0.1537 0.2809 0.047 Uiso 1 1 calc R . .
N1 N -0.05159(18) -0.1072(2) 0.34819(18) 0.0387(5) Uani 1 1 d . . .
C7 C 0.2056(2) 0.5292(2) 0.32749(19) 0.0341(5) Uani 1 1 d . . .
C6 C 0.1463(2) 0.0391(3) 0.4268(2) 0.0351(5) Uani 1 1 d . . .
H0aa H 0.1926 -0.0456 0.4561 0.042 Uiso 1 1 calc R . .
C10 C 0.2905(2) 0.6577(2) 0.3786(2) 0.0386(5) Uani 1 1 d . . .
H8A H 0.2490 0.7484 0.3448 0.046 Uiso 1 1 calc R . .
H8B H 0.3749 0.6501 0.3662 0.046 Uiso 1 1 calc R . .
C11 C 0.4335(2) 0.7134(3) 0.5846(2) 0.0377(5) Uani 1 1 d . . .
C8 C 0.2888(2) 0.4890(3) 0.5302(2) 0.0403(6) Uani 1 1 d . . .
h8 H 0.3723 0.4387 0.5535 0.048 Uiso 1 1 calc R . .
h7 H 0.2467 0.4752 0.5890 0.048 Uiso 1 1 calc R . .
C9 C 0.3056(2) 0.6506(2) 0.5088(2) 0.0394(6) Uani 1 1 d . . .
H11 H 0.2336 0.7050 0.5225 0.047 Uiso 1 1 calc R . .


_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 C1 1.343(2) . ?
F2 C3 1.340(3) . ?
N2 C2 1.403(3) . ?
N2 C7 1.371(3) . ?
N2 C8 1.470(3) . ?
C2 C3 1.392(3) . ?
C2 C1 1.387(3) . ?
O1 C7 1.220(3) . ?
O5 N1 1.230(3) . ?
O3 H5 0.8200 . ?
O3 C11 1.314(3) . ?
O4 N1 1.216(3) . ?
O2 C11 1.208(3) . ?
C5 C4 1.381(3) . ?
C5 N1 1.469(3) . ?
C5 C6 1.380(3) . ?
C3 C4 1.372(3) . ?
C1 C6 1.372(3) . ?
C4 H5A 0.9300 . ?
C7 C10 1.499(3) . ?
C6 H0aa 0.9300 . ?
C10 H8A 0.9700 . ?
C10 H8B 0.9700 . ?
C10 C9 1.544(3) . ?
C11 C9 1.509(3) . ?
C8 h8 0.9700 . ?
C8 h7 0.9700 . ?
C8 C9 1.522(3) . ?
C9 H11 0.9800 . ?

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 N2 C8 123.14(18) . . ?
C7 N2 C2 123.27(19) . . ?
C7 N2 C8 113.28(18) . . ?
C3 C2 N2 121.63(19) . . ?
C1 C2 N2 122.22(19) . . ?
C1 C2 C3 116.1(2) . . ?
C11 O3 H5 109.5 . . ?
C4 C5 N1 118.99(19) . . ?
C6 C5 C4 123.0(2) . . ?
C6 C5 N1 118.0(2) . . ?
F2 C3 C2 117.5(2) . . ?
F2 C3 C4 119.21(19) . . ?
C4 C3 C2 123.2(2) . . ?
F1 C1 C2 118.32(19) . . ?
F1 C1 C6 118.23(19) . . ?
C6 C1 C2 123.5(2) . . ?
C5 C4 H5A 121.4 . . ?
C3 C4 C5 117.1(2) . . ?
C3 C4 H5A 121.4 . . ?
O5 N1 C5 117.8(2) . . ?
O4 N1 O5 123.5(2) . . ?
O4 N1 C5 118.77(18) . . ?
N2 C7 C10 107.76(19) . . ?
O1 C7 N2 124.2(2) . . ?
O1 C7 C10 128.0(2) . . ?
C5 C6 H0aa 121.5 . . ?
C1 C6 C5 117.0(2) . . ?
C1 C6 H0aa 121.5 . . ?
C7 C10 H8A 110.9 . . ?
C7 C10 H8B 110.9 . . ?
C7 C10 C9 104.24(18) . . ?
H8A C10 H8B 108.9 . . ?
C9 C10 H8A 110.9 . . ?
C9 C10 H8B 110.9 . . ?
O3 C11 C9 110.7(2) . . ?
O2 C11 O3 123.8(2) . . ?
O2 C11 C9 125.5(2) . . ?
N2 C8 h8 111.2 . . ?
N2 C8 h7 111.2 . . ?
N2 C8 C9 102.65(18) . . ?
h8 C8 h7 109.1 . . ?
C9 C8 h8 111.2 . . ?
C9 C8 h7 111.2 . . ?
C10 C9 H11 108.7 . . ?
C11 C9 C10 113.1(2) . . ?
C11 C9 C8 113.64(19) . . ?
C11 C9 H11 108.7 . . ?
C8 C9 C10 103.73(18) . . ?
C8 C9 H11 108.7 . . ?

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 H5 O1 0.82 1.94 2.752(2) 168.3 4_676

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
F1 C1 C6 C5 179.25(19) . . . . ?
F2 C3 C4 C5 -176.8(2) . . . . ?
N2 C2 C3 F2 -2.8(3) . . . . ?
N2 C2 C3 C4 179.2(2) . . . . ?
N2 C2 C1 F1 0.6(3) . . . . ?
N2 C2 C1 C6 -179.5(2) . . . . ?
N2 C7 C10 C9 -15.7(2) . . . . ?
N2 C8 C9 C10 -27.6(2) . . . . ?
N2 C8 C9 C11 -150.85(19) . . . . ?
C2 N2 C7 O1 2.5(3) . . . . ?
C2 N2 C7 C10 -176.19(19) . . . . ?
C2 N2 C8 C9 -166.62(19) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
O1 C7 C10 C9 165.6(2) . . . . ?
O3 C11 C9 C10 78.7(3) . . . . ?
O3 C11 C9 C8 -163.4(2) . . . . ?
O2 C11 C9 C10 -101.5(3) . . . . ?
O2 C11 C9 C8 16.5(3) . . . . ?
C3 C2 C1 F1 -177.8(2) . . . . ?
C3 C2 C1 C6 2.1(3) . . . . ?
C1 C2 C3 F2 175.6(2) . . . . ?
C1 C2 C3 C4 -2.4(4) . . . . ?
C4 C5 N1 O5 4.5(3) . . . . ?
C4 C5 N1 O4 -175.5(2) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
N1 C5 C4 C3 179.1(2) . . . . ?
N1 C5 C6 C1 -179.34(19) . . . . ?
C7 N2 C2 C3 -57.6(3) . . . . ?
C7 N2 C2 C1 124.1(2) . . . . ?
C7 N2 C8 C9 19.6(2) . . . . ?
C7 C10 C9 C11 150.46(19) . . . . ?
C7 C10 C9 C8 26.9(2) . . . . ?
C6 C5 C4 C3 0.5(4) . . . . ?
C6 C5 N1 O5 -176.8(2) . . . . ?
C6 C5 N1 O4 3.2(3) . . . . ?
C8 N2 C2 C3 129.2(2) . . . . ?
C8 N2 C2 C1 -49.1(3) . . . . ?
C8 N2 C7 O1 176.3(2) . . . . ?
C8 N2 C7 C10 -2.4(2) . . . . ?

