# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_srinu
_database_code_depnum_ccdc_archive 'CCDC 1424012'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;
_audit_creation_date             2015-03-19
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.17(C6 H4 F8 N2 O6)'
_chemical_formula_sum            'C6 H4 F8 N2 O6'
_chemical_formula_weight         352.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H4 F8 N2 O6'
_chemical_oxdiff_usercomment     SRINU
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.1438(5)
_cell_length_b                   6.2912(9)
_cell_length_c                   9.9448(12)
_cell_angle_alpha                91.605(10)
_cell_angle_beta                 104.350(9)
_cell_angle_gamma                101.944(10)
_cell_volume                     303.96(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    743
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6240
_cell_measurement_theta_min      4.6560
_exptl_absorpt_coefficient_mu    2.203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.923
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             141
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.6
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0096
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1630
_diffrn_reflns_theta_full        70.22
_diffrn_reflns_theta_max         71.22
_diffrn_reflns_theta_min         4.61
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3291
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9487
_diffrn_measured_fraction_theta_max 0.9526
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   34.00   74.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6479   37.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
  2 omega   24.00  103.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6479   57.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
  3 omega   54.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
  4 omega   61.00   87.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   82.00  124.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   30.0000 42

#__ type_ start__ end____ width___ exp.time_
  6 omega   57.00  120.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -129.0000 -100.0000 63

#__ type_ start__ end____ width___ exp.time_
  7 omega   48.00  104.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
  8 omega   56.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
  9 omega   44.00   89.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
 10 omega   40.00   69.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega   46.00   75.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
 12 omega   41.00   81.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
 13 omega   50.00  114.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 64

#__ type_ start__ end____ width___ exp.time_
 14 omega   45.00   89.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6479 -129.0000 -100.0000 44

#__ type_ start__ end____ width___ exp.time_
 15 omega    3.00   39.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6479  -57.0000 -120.0000 36

#__ type_ start__ end____ width___ exp.time_
 16 omega  -14.00   43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6479  -57.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6479   57.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
 18 omega  126.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 51

#__ type_ start__ end____ width___ exp.time_
 19 omega  119.00  175.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
 20 omega   13.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6479   77.0000   30.0000 85

#__ type_ start__ end____ width___ exp.time_
 21 omega   39.00  171.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  150.0000 132

#__ type_ start__ end____ width___ exp.time_
 22 omega   12.00   92.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6479   77.0000 -180.0000 80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0541063000
_diffrn_orient_matrix_UB_12      -0.2314154000
_diffrn_orient_matrix_UB_13      -0.0710365000
_diffrn_orient_matrix_UB_21      0.0808495000
_diffrn_orient_matrix_UB_22      -0.0888148000
_diffrn_orient_matrix_UB_23      0.1436862000
_diffrn_orient_matrix_UB_31      -0.3016772000
_diffrn_orient_matrix_UB_32      -0.0405903000
_diffrn_orient_matrix_UB_33      0.0075212000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                993
_reflns_number_total             1126
_reflns_odcompleteness_completeness 97.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_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  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.900
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0755
_refine_ls_restrained_S_all      1.900
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2329
_refine_ls_wR_factor_ref         0.2417
_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 0.1664(4) 0.1753(3) 0.4227(2) 0.0536(7) Uani 1 1 d . . .
F2 F -0.2360(4) 0.2786(3) 0.5350(2) 0.0524(7) Uani 1 1 d . . .
F3 F -0.3070(4) 0.5071(3) 0.3780(2) 0.0564(7) Uani 1 1 d . . .
F4 F 0.0818(5) 0.3978(3) 0.2655(2) 0.0607(8) Uani 1 1 d . . .
O5 O -0.5565(5) -0.2518(4) 0.0945(3) 0.0544(8) Uani 1 1 d . . .
O6 O -0.1480(5) -0.0223(4) 0.1826(3) 0.0484(7) Uani 1 1 d . . .
O7 O -0.1744(6) -0.2912(5) 0.0308(3) 0.0633(9) Uani 1 1 d . . .
C8 C -0.0331(6) 0.2682(5) 0.3499(3) 0.0363(7) Uani 1 1 d . . .
N9 N -0.3148(6) -0.1972(4) 0.1009(3) 0.0458(8) Uani 1 1 d . . .
C10 C -0.2715(7) 0.0920(5) 0.2666(3) 0.0431(8) Uani 1 1 d . . .
H10A H -0.3515 -0.0039 0.3274 0.052 Uiso 1 1 calc R . .
H10B H -0.4133 0.1552 0.2093 0.052 Uiso 1 1 calc R . .
C11 C -0.1178(6) 0.4109(4) 0.4531(3) 0.0352(7) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0394(12) 0.0499(12) 0.0631(13) -0.0228(9) -0.0042(9) 0.0164(9)
F2 0.0519(13) 0.0429(11) 0.0570(12) -0.0162(8) 0.0237(9) -0.0101(9)
F3 0.0413(12) 0.0544(13) 0.0615(13) -0.0226(10) -0.0145(10) 0.0208(10)
F4 0.0809(17) 0.0438(12) 0.0539(12) -0.0134(8) 0.0312(11) -0.0085(10)
O5 0.0278(13) 0.0512(13) 0.0739(17) -0.0331(12) 0.0084(10) -0.0033(10)
O6 0.0344(13) 0.0423(12) 0.0614(14) -0.0291(10) 0.0122(10) -0.0026(9)
O7 0.0511(17) 0.0540(15) 0.0793(18) -0.0263(13) 0.0208(14) -0.0013(12)
C8 0.0293(15) 0.0308(13) 0.0423(15) -0.0120(11) 0.0045(12) 0.0000(11)
N9 0.0444(17) 0.0377(14) 0.0487(15) -0.0121(11) 0.0063(12) 0.0035(12)
C10 0.0293(15) 0.0433(17) 0.0493(16) -0.0235(13) 0.0046(12) 0.0022(12)
C11 0.0277(15) 0.0309(14) 0.0422(15) -0.0106(11) 0.0037(12) 0.0037(12)

_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 C8 1.350(4) . ?
F2 C11 1.342(4) . ?
F3 C11 1.333(4) . ?
F4 C8 1.342(4) . ?
O5 N9 1.204(4) . ?
O6 N9 1.350(3) . ?
O6 C10 1.427(4) . ?
O7 N9 1.326(4) . ?
C8 C10 1.517(4) . ?
C8 C11 1.543(4) . ?
C11 C11 1.554(5) 2_566 ?

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
N9 O6 C10 116.2(2) . . ?
F1 C8 C10 109.5(2) . . ?
F1 C8 C11 108.4(2) . . ?
F4 C8 F1 106.1(3) . . ?
F4 C8 C10 111.0(3) . . ?
F4 C8 C11 108.8(2) . . ?
C10 C8 C11 112.8(3) . . ?
O5 N9 O6 122.7(3) . . ?
O5 N9 O7 127.0(3) . . ?
O7 N9 O6 110.2(3) . . ?
O6 C10 C8 103.5(3) . . ?
F2 C11 C8 107.9(2) . . ?
F2 C11 C11 108.6(3) . 2_566 ?
F3 C11 F2 108.2(3) . . ?
F3 C11 C8 107.1(2) . . ?
F3 C11 C11 108.8(3) . 2_566 ?
C8 C11 C11 115.9(3) . 2_566 ?

####################################################################### 
# 
# 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_s2
_database_code_depnum_ccdc_archive 'CCDC 1428609'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;
_audit_creation_date             2015-03-11
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.2(C8 H6 F8 N4 O8)'
_chemical_formula_sum            'C8 H6 F8 N4 O8'
_chemical_formula_weight         438
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H6 N4 O8 F8'
_chemical_oxdiff_usercomment     SRINU
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   4.99141(16)
_cell_length_b                   20.7151(8)
_cell_length_c                   7.2618(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.263(3)
_cell_angle_gamma                90.00
_cell_volume                     733.72(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1518
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2710
_cell_measurement_theta_min      6.2620
_exptl_absorpt_coefficient_mu    2.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             310
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.6
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2526
_diffrn_reflns_theta_full        70.64
_diffrn_reflns_theta_max         71.64
_diffrn_reflns_theta_min         4.27
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3291
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9710
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    9.00   68.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       35.5136  -99.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
  2 omega   66.00  100.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       35.5136   57.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
  3 omega  -29.00   40.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       35.5136  -57.0000  150.0000 69

#__ type_ start__ end____ width___ exp.time_
  4 omega   58.00   94.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       35.5136   57.0000    0.0000 36

#__ type_ start__ end____ width___ exp.time_
  5 omega   78.00  103.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       35.5136   57.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00   60.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       35.5136   57.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
  7 omega   20.00   46.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       35.5136   57.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega  112.00  177.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega   45.00   72.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00  146.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   60.0000 107

#__ type_ start__ end____ width___ exp.time_
 11 omega   52.00   77.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega  134.00  178.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
 13 omega   60.00   91.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 14 omega   39.00  105.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 66

#__ type_ start__ end____ width___ exp.time_
 15 omega   49.00   98.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 49

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00   92.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0373907000
_diffrn_orient_matrix_UB_12      0.0555885000
_diffrn_orient_matrix_UB_13      0.1442418000
_diffrn_orient_matrix_UB_21      -0.0416569000
_diffrn_orient_matrix_UB_22      0.0494350000
_diffrn_orient_matrix_UB_23      -0.1620715000
_diffrn_orient_matrix_UB_31      -0.3107625000
_diffrn_orient_matrix_UB_32      0.0000444000
_diffrn_orient_matrix_UB_33      -0.0078040000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1304
_reflns_number_total             1389
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_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  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.537
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.537
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1758
_refine_ls_wR_factor_ref         0.1797
_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 0.2819(3) 0.43306(6) 0.46367(18) 0.0468(5) Uani 1 1 d . . .
F2 F 0.2733(3) 0.51535(6) 0.64906(18) 0.0474(4) Uani 1 1 d . . .
O3 O 0.3885(3) 0.34752(8) 1.1457(2) 0.0477(5) Uani 1 1 d . . .
O4 O 0.7089(3) 0.37367(10) 0.9832(2) 0.0511(5) Uani 1 1 d . . .
F5 F 0.8301(3) 0.41264(8) 0.6556(2) 0.0593(5) Uani 1 1 d . . .
F6 F 0.7772(4) 0.48950(8) 0.8430(2) 0.0645(5) Uani 1 1 d . . .
N7 N 0.8523(3) 0.32864(9) 1.2579(2) 0.0398(5) Uani 1 1 d . . .
H7 H 1.0101 0.3385 1.2363 0.048 Uiso 1 1 calc R . .
C8 C 0.6193(4) 0.34901(8) 1.1300(3) 0.0354(5) Uani 1 1 d . . .
C9 C 0.6404(4) 0.44400(10) 0.7279(3) 0.0382(5) Uani 1 1 d . . .
N10 N 0.8428(4) 0.29351(10) 1.4173(3) 0.0519(6) Uani 1 1 d . . .
C11 C 0.4354(4) 0.47862(9) 0.5666(3) 0.0342(5) Uani 1 1 d . . .
O12 O 1.0633(4) 0.27973(15) 1.5115(3) 0.0872(9) Uani 1 1 d . . .
O13 O 0.6245(4) 0.28100(13) 1.4520(3) 0.0816(8) Uani 1 1 d . . .
C14 C 0.4964(4) 0.39828(13) 0.8362(3) 0.0491(6) Uani 1 1 d . . .
H14A H 0.3589 0.4208 0.8881 0.059 Uiso 1 1 calc R . .
H14B H 0.4084 0.3636 0.7557 0.059 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0387(8) 0.0537(8) 0.0441(7) -0.0002(5) -0.0003(5) -0.0132(5)
F2 0.0410(8) 0.0582(8) 0.0481(7) 0.0064(5) 0.0208(5) 0.0130(5)
O3 0.0312(10) 0.0606(10) 0.0538(9) 0.0081(7) 0.0147(6) 0.0000(6)
O4 0.0316(9) 0.0758(11) 0.0470(9) 0.0244(7) 0.0109(6) 0.0056(7)
F5 0.0416(8) 0.0778(10) 0.0634(9) 0.0222(7) 0.0223(6) 0.0230(7)
F6 0.0630(10) 0.0691(9) 0.0490(8) 0.0036(6) -0.0164(7) -0.0172(7)
N7 0.0313(9) 0.0483(9) 0.0412(9) 0.0095(7) 0.0107(7) -0.0004(6)
C8 0.0324(11) 0.0362(9) 0.0399(10) 0.0015(7) 0.0125(7) -0.0008(6)
C9 0.0254(10) 0.0499(10) 0.0381(10) 0.0033(8) 0.0041(7) -0.0004(7)
N10 0.0428(12) 0.0601(12) 0.0555(11) 0.0201(9) 0.0165(8) 0.0061(8)
C11 0.0238(10) 0.0423(9) 0.0358(9) -0.0013(7) 0.0048(7) 0.0003(7)
O12 0.0492(13) 0.126(2) 0.0860(15) 0.0603(15) 0.0137(10) 0.0167(12)
O13 0.0457(12) 0.1134(18) 0.0916(16) 0.0551(14) 0.0277(10) 0.0049(11)
C14 0.0310(11) 0.0677(14) 0.0472(11) 0.0186(10) 0.0051(9) -0.0005(9)

_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 C11 1.339(2) . ?
F2 C11 1.341(2) . ?
O3 C8 1.182(3) . ?
O4 C8 1.342(2) . ?
O4 C14 1.430(2) . ?
F5 C9 1.344(3) . ?
F6 C9 1.346(2) . ?
N7 C8 1.390(3) . ?
N7 N10 1.377(3) . ?
C9 C11 1.557(3) . ?
C9 C14 1.507(3) . ?
N10 O12 1.200(3) . ?
N10 O13 1.198(3) . ?
C11 C11 1.550(4) 3_666 ?

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
C8 O4 C14 114.19(17) . . ?
N10 N7 C8 123.28(17) . . ?
O3 C8 O4 125.63(19) . . ?
O3 C8 N7 128.45(18) . . ?
O4 C8 N7 105.88(16) . . ?
F5 C9 F6 105.94(18) . . ?
F5 C9 C11 109.51(16) . . ?
F5 C9 C14 110.72(18) . . ?
F6 C9 C11 108.08(17) . . ?
F6 C9 C14 110.56(18) . . ?
C14 C9 C11 111.83(16) . . ?
O12 N10 N7 114.5(2) . . ?
O13 N10 N7 119.1(2) . . ?
O13 N10 O12 126.4(2) . . ?
F1 C11 F2 108.72(15) . . ?
F1 C11 C9 107.58(15) . . ?
F1 C11 C11 108.58(18) . 3_666 ?
F2 C11 C9 106.75(16) . . ?
F2 C11 C11 108.97(18) . 3_666 ?
C11 C11 C9 116.04(19) 3_666 . ?
O4 C14 C9 104.68(17) . . ?

####################################################################### 
# 
# 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_srinu
_database_code_depnum_ccdc_archive 'CCDC 1437815'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;
_audit_creation_date             2015-01-30
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.09(C6 H6 F4 N4 O8)'
_chemical_formula_sum            'C6 H6 F4 N4 O8'
_chemical_formula_weight         338
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H6 F4 N4 O8'
_chemical_oxdiff_usercomment     SRINIVAS
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   11.4164(17)
_cell_length_b                   13.6481(9)
_cell_length_c                   4.9679(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 130.54(3)
_cell_angle_gamma                90.00
_cell_volume                     588.28(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    705
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.5040
_cell_measurement_theta_min      3.2510
_exptl_absorpt_coefficient_mu    1.924
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.908
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             509
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.6
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0079
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            1137
_diffrn_reflns_theta_full        70.79
_diffrn_reflns_theta_max         71.79
_diffrn_reflns_theta_min         6.04
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3291
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.7395
_diffrn_measured_fraction_theta_max 0.7495
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -56.00  -23.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega  -99.00  -59.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega   -4.00   50.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5136  -99.0000  -30.0000 54

#__ type_ start__ end____ width___ exp.time_
  4 omega   54.00   80.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5136   57.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega    2.00   27.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5136  -99.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   41.00   66.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5136  -99.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   65.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5136   37.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00   90.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
  9 omega  138.00  175.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
 10 omega   44.00   89.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
 11 omega  107.00  133.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00   71.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
 13 omega   55.00  103.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0462132000
_diffrn_orient_matrix_UB_12      -0.1019895000
_diffrn_orient_matrix_UB_13      0.1742862000
_diffrn_orient_matrix_UB_21      -0.1708916000
_diffrn_orient_matrix_UB_22      -0.0304863000
_diffrn_orient_matrix_UB_23      -0.2485846000
_diffrn_orient_matrix_UB_31      0.0127200000
_diffrn_orient_matrix_UB_32      -0.0375963000
_diffrn_orient_matrix_UB_33      -0.2727125000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                824
_reflns_number_total             862
_reflns_odcompleteness_completeness 77.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_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  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         862
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      2.033
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2209
_refine_ls_wR_factor_ref         0.2222
_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 0.4746(2) 0.10678(14) 0.2758(6) 0.0553(7) Uani 1 1 d . . .
O2 O 0.1747(2) 0.07528(16) -0.0592(5) 0.0374(7) Uani 1 1 d . . .
F3 F 0.3956(2) -0.03922(17) 0.0645(5) 0.0534(7) Uani 1 1 d . . .
C5 C 0.0532(3) 0.11367(18) -0.1150(7) 0.0300(7) Uani 1 1 d . . .
N6 N -0.1746(3) 0.20332(17) -0.6015(6) 0.0387(8) Uani 1 1 d . . .
N7 N -0.0393(3) 0.1524(2) -0.4516(7) 0.0398(7) Uani 1 1 d . . .
H7 H -0.0118 0.1447 -0.5755 0.048 Uiso 1 1 calc R . .
O8 O -0.2311(3) 0.19853(18) -0.4651(7) 0.0517(8) Uani 1 1 d . . .
C9 C 0.4299(3) 0.02123(18) 0.3223(7) 0.0305(7) Uani 1 1 d . . .
O10 O -0.2248(3) 0.2475(2) -0.8671(7) 0.0644(9) Uani 1 1 d . . .
C1 C 0.2910(3) 0.0366(2) 0.2898(8) 0.0363(8) Uani 1 1 d . . .
H1A H 0.2576 -0.0248 0.3187 0.044 Uiso 1 1 calc R . .
H1B H 0.3138 0.0825 0.4675 0.044 Uiso 1 1 calc R . .
O4 O 0.0299(2) 0.11178(15) 0.0855(5) 0.0390(7) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0372(10) 0.0549(11) 0.0757(15) 0.0276(10) 0.0376(11) 0.0061(7)
O2 0.0272(10) 0.0563(13) 0.0327(11) 0.0094(8) 0.0213(10) 0.0102(8)
F3 0.0390(11) 0.0788(14) 0.0399(11) -0.0093(9) 0.0245(10) 0.0100(8)
C5 0.0252(13) 0.0343(13) 0.0332(14) -0.0019(10) 0.0202(12) -0.0014(9)
N6 0.0304(12) 0.0369(13) 0.0398(14) 0.0015(11) 0.0188(12) 0.0031(9)
N7 0.0284(13) 0.0590(15) 0.0347(13) 0.0094(11) 0.0218(12) 0.0115(10)
O8 0.0386(13) 0.0630(15) 0.0660(16) 0.0143(12) 0.0395(14) 0.0150(10)
C9 0.0266(14) 0.0363(13) 0.0342(14) 0.0035(10) 0.0223(13) 0.0014(9)
O10 0.0648(17) 0.0741(19) 0.0483(14) 0.0291(14) 0.0341(14) 0.0309(13)
C1 0.0263(13) 0.0510(15) 0.0351(15) 0.0094(12) 0.0214(13) 0.0086(10)
O4 0.0324(11) 0.0560(13) 0.0355(12) 0.0005(9) 0.0251(10) 0.0053(8)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C9 1.353(3) . ?
O2 C5 1.333(3) . ?
O2 C1 1.434(3) . ?
F3 C9 1.350(3) . ?
C5 N7 1.377(4) . ?
C5 O4 1.186(4) . ?
N6 N7 1.389(3) . ?
N6 O8 1.203(4) . ?
N6 O10 1.204(4) . ?
C9 C9 1.530(5) 3_656 ?
C9 C1 1.501(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
C5 O2 C1 114.6(2) . . ?
O2 C5 N7 106.0(2) . . ?
O4 C5 O2 126.0(3) . . ?
O4 C5 N7 127.9(2) . . ?
O8 N6 N7 119.2(3) . . ?
O8 N6 O10 126.6(3) . . ?
O10 N6 N7 114.2(3) . . ?
C5 N7 N6 123.4(3) . . ?
F1 C9 C9 107.2(3) . 3_656 ?
F1 C9 C1 110.5(2) . . ?
F3 C9 F1 106.0(3) . . ?
F3 C9 C9 107.7(3) . 3_656 ?
F3 C9 C1 110.4(2) . . ?
C1 C9 C9 114.6(3) . 3_656 ?
O2 C1 C9 105.3(2) . . ?

