# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_t1_a
_database_code_depnum_ccdc_archive 'CCDC 1531117'
_audit_update_record             
;
2017-02-06 deposited with the CCDC.
2017-06-05 downloaded from the CCDC.
;
_audit_creation_date             2017-01-25
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled Nov  7 2012 10:34:12, GUI svn.r4372)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H7 F3 N4 O6'
_chemical_formula_sum            'C13 H7 F3 N4 O6'
_chemical_formula_weight         372.22
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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                   8.0718(6)
_cell_length_b                   8.2115(7)
_cell_length_c                   11.4425(9)
_cell_angle_alpha                76.477(3)
_cell_angle_beta                 82.582(3)
_cell_angle_gamma                70.713(3)
_cell_volume                     694.9(1)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6862
_cell_measurement_theta_max      29.60
_cell_measurement_theta_min      2.68
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
? was used for absorption correction.
wR2(int) was 0.1325 before and 0.0628 after correction.
The Ratio of minimum to maximum transmission is 0.9035.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour_modifier   .
_exptl_crystal_density_diffrn    1.7788
_exptl_crystal_description       block
_exptl_crystal_F_000             376.3130
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21047
_diffrn_reflns_theta_full        28.6973
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         2.68
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9863
_diffrn_measured_fraction_theta_max 0.9866
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -10
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2603
_reflns_number_total             3529
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.5047
_refine_diff_density_min         -0.5785
_refine_diff_density_rms         0.1318
_refine_ls_d_res_high            0.7401
_refine_ls_d_res_low             7.6066
_refine_ls_goodness_of_fit_ref   0.9722
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    7
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3529
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      0.9722
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1423
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H00O of C00O, H00N of C00N, H00M of C00M, H00L of C00L, H00I of C00I, H00A
  of N00A, H00E of C00E
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
F001 F 0.91310(15) 0.75898(15) -0.13057(9) 0.0195(3) Uani 1.000000 .
F002 F 1.07266(14) 0.71742(16) 0.01606(10) 0.0219(3) Uani 1.000000 .
F003 F 0.86071(16) 0.95951(15) -0.02495(10) 0.0211(3) Uani 1.000000 .
O006 O 0.57519(17) 0.94905(17) -0.12194(12) 0.0171(3) Uani 1.000000 .
O009 O 0.42156(19) 0.7706(2) -0.10310(13) 0.0224(3) Uani 1.000000 .
N00A N 0.8215(2) 0.4066(2) 0.36832(14) 0.0126(3) Uani 1.000000 .
H00A H 0.873(3) 0.447(3) 0.407(2) 0.0152(4) Uiso 1.000000 R
N00B N 0.87816(19) 0.2529(2) 0.62496(13) 0.0110(3) Uani 1.000000 .
N00C N 0.5332(2) 0.8188(2) -0.06953(14) 0.0131(3) Uani 1.000000 .
N00D N 0.69748(19) -0.2377(2) 0.57974(14) 0.0126(3) Uani 1.000000 .
C00E C 0.8505(2) 0.5994(2) 0.17706(16) 0.0117(4) Uani 1.000000 .
H00E H 0.963(3) 0.582(3) 0.1984(19) 0.0140(4) Uiso 1.000000 R
C00F C 0.7856(2) 0.7012(2) 0.06790(16) 0.0111(4) Uani 1.000000 .
C00G C 0.7308(2) -0.0708(2) 0.52679(17) 0.0116(4) Uani 1.000000 .
C00H C 0.8159(2) 0.1723(2) 0.54620(16) 0.0101(4) Uani 1.000000 .
C00I C 0.7159(2) -0.0052(2) 0.40289(17) 0.0119(4) Uani 1.000000 .
H00I H 0.693(3) -0.072(3) 0.354(2) 0.0143(4) Uiso 1.000000 R
C00J C 0.7490(2) 0.5122(2) 0.25966(16) 0.0113(4) Uani 1.000000 .
C00K C 0.7953(2) 0.2495(2) 0.42162(16) 0.0101(4) Uani 1.000000 .
C00L C 0.5126(2) 0.6305(2) 0.12552(17) 0.0127(4) Uani 1.000000 .
H00L H 0.397(3) 0.644(3) 0.107(2) 0.0152(5) Uiso 1.000000 R
C00M C 0.5773(2) 0.5321(2) 0.23489(17) 0.0134(4) Uani 1.000000 .
H00M H 0.505(3) 0.479(3) 0.292(2) 0.0161(5) Uiso 1.000000 R
C00N C 0.7811(2) 0.0153(2) 0.59878(17) 0.0117(4) Uani 1.000000 .
H00N H 0.793(3) -0.028(3) 0.679(2) 0.0140(4) Uiso 1.000000 R
C00O C 0.7479(2) 0.1514(2) 0.35277(16) 0.0121(4) Uani 1.000000 .
H00O H 0.740(3) 0.198(3) 0.267(2) 0.0145(4) Uiso 1.000000 R
C00P C 0.6156(2) 0.7140(2) 0.04265(16) 0.0114(4) Uani 1.000000 .
C00Q C 0.9067(2) 0.7859(3) -0.01808(16) 0.0147(4) Uani 1.000000 .
O1 O 0.63999(17) -0.30519(18) 0.51531(13) 0.0172(3) Uani 1.000000 .
O2 O 0.72726(19) -0.30295(18) 0.68622(12) 0.0195(3) Uani 1.000000 .
O3 O 0.95673(17) 0.36145(17) 0.57796(12) 0.0144(3) Uani 1.000000 .
O4 O 0.85562(19) 0.20762(19) 0.73422(12) 0.0205(3) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F001 C00Q 1.348(2) .
F002 C00Q 1.341(2) .
F003 C00Q 1.335(2) .
O006 N00C 1.227(2) .
O009 N00C 1.230(2) .
N00A H00A 0.83(2) .
N00A C00J 1.410(2) .
N00A C00K 1.364(2) .
N00B C00H 1.456(2) .
N00B O3 1.244(2) .
N00B O4 1.226(2) .
N00C C00P 1.468(2) .
N00D C00G 1.460(2) .
N00D O1 1.231(2) .
N00D O2 1.231(2) .
C00E H00E 0.92(2) .
C00E C00F 1.387(3) .
C00E C00J 1.396(3) .
C00F C00P 1.404(2) .
C00F C00Q 1.512(3) .
C00G C00I 1.400(3) .
C00G C00N 1.376(3) .
C00H C00K 1.425(2) .
C00H C00N 1.391(3) .
C00I H00I 0.94(2) .
C00I C00O 1.373(3) .
C00J C00M 1.399(2) .
C00K C00O 1.412(2) .
C00L H00L 0.95(2) .
C00L C00M 1.381(3) .
C00L C00P 1.389(3) .
C00M H00M 0.95(2) .
C00N H00N 0.91(2) .
C00O H00O 0.97(2) .

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
C00J N00A H00A 118.5(16) . .
C00K N00A H00A 116.9(16) . .
C00K N00A C00J 124.07(16) . .
O3 N00B C00H 118.14(14) . .
O4 N00B C00H 118.90(15) . .
O4 N00B O3 122.92(15) . .
O009 N00C O006 124.20(16) . .
C00P N00C O006 119.24(15) . .
C00P N00C O009 116.54(15) . .
O1 N00D C00G 118.01(15) . .
O2 N00D C00G 118.48(14) . .
O2 N00D O1 123.51(16) . .
C00F C00E H00E 122.9(14) . .
C00J C00E H00E 116.3(14) . .
C00J C00E C00F 120.76(16) . .
C00P C00F C00E 118.33(17) . .
C00Q C00F C00E 117.29(16) . .
C00Q C00F C00P 124.35(16) . .
C00I C00G N00D 118.91(15) . .
C00N C00G N00D 119.43(16) . .
C00N C00G C00I 121.62(17) . .
C00K C00H N00B 121.36(16) . .
C00N C00H N00B 116.38(16) . .
C00N C00H C00K 122.25(16) . .
H00I C00I C00G 120.4(14) . .
C00O C00I C00G 119.03(16) . .
C00O C00I H00I 120.4(14) . .
C00E C00J N00A 118.95(16) . .
C00M C00J N00A 120.99(17) . .
C00M C00J C00E 120.05(17) . .
C00H C00K N00A 123.71(16) . .
C00O C00K N00A 120.35(16) . .
C00O C00K C00H 115.92(16) . .
C00M C00L H00L 120.7(14) . .
C00P C00L H00L 119.2(14) . .
C00P C00L C00M 120.03(17) . .
C00L C00M C00J 119.58(17) . .
H00M C00M C00J 120.7(13) . .
H00M C00M C00L 119.8(13) . .
C00H C00N C00G 118.60(17) . .
H00N C00N C00G 121.9(14) . .
H00N C00N C00H 119.5(14) . .
C00K C00O C00I 122.47(17) . .
H00O C00O C00I 120.0(13) . .
H00O C00O C00K 117.6(13) . .
C00F C00P N00C 123.02(16) . .
C00L C00P N00C 115.79(16) . .
C00L C00P C00F 121.16(17) . .
F002 C00Q F001 105.64(14) . .
F003 C00Q F001 107.64(15) . .
F003 C00Q F002 106.91(15) . .
C00F C00Q F001 112.42(14) . .
C00F C00Q F002 111.16(15) . .
C00F C00Q F003 112.66(15) . .
