# 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 2019

####################################################################### 
# 
# 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_DR-TF
_database_code_depnum_ccdc_archive 'CCDC 1896316'
loop_
_audit_author_name
_audit_author_address
'Binoy K. Saha'
;Pondicherry University
India
;
_audit_update_record             
;
2019-02-09 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;
_audit_creation_date             2019-02-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 F4 O2, C10 H14'
_chemical_formula_sum            'C16 H14 F4 O2'
_chemical_formula_weight         314.27
_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 0.0033 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'
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'

_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.
;
_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_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6907(6)
_cell_length_b                   6.9985(7)
_cell_length_c                   8.7933(8)
_cell_angle_alpha                110.856(9)
_cell_angle_beta                 105.889(8)
_cell_angle_gamma                96.533(8)
_cell_volume                     359.70(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1325
_cell_measurement_temperature    262(2)
_cell_measurement_theta_max      29.1567
_cell_measurement_theta_min      3.2137


_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             162
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.221
_diffrn_reflns_theta_min         3.220
_diffrn_ambient_temperature      262(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   20.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491  -99.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00    0.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491  -99.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -83.00  -36.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491 -178.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   88.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000   60.0000 90

#__ type_ start__ end____ width___ exp.time_
  5 omega  -50.00   47.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835  -77.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
  6 omega   -4.00   91.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   37.0000  -30.0000 95

#__ type_ start__ end____ width___ exp.time_
  7 omega  -93.00  -35.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491 -178.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega  -24.00   68.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   19.0000 -120.0000 92
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0636895000
_diffrn_orient_matrix_UB_12      -0.0549904000
_diffrn_orient_matrix_UB_13      -0.0884944000
_diffrn_orient_matrix_UB_21      0.0290864000
_diffrn_orient_matrix_UB_22      0.0904069000
_diffrn_orient_matrix_UB_23      -0.0152836000
_diffrn_orient_matrix_UB_31      0.0892039000
_diffrn_orient_matrix_UB_32      -0.0354021000
_diffrn_orient_matrix_UB_33      -0.0187229000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000


_reflns_number_gt                1320
_reflns_number_total             1672


_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1672
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.1089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+0.0919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1165
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.30821(16) 0.59559(16) 0.26674(13) 0.0604(3) Uani 1 1 d . . . . .
C5 C 0.9274(2) 0.7910(2) 0.45627(17) 0.0304(3) Uani 1 1 d . . . . .
H5 H 0.877568 0.648514 0.426412 0.037 Uiso 1 1 calc R . . . .
C4 C 0.9093(2) 0.8603(2) 0.32447(17) 0.0299(3) Uani 1 1 d . . . . .
O1 O 0.37874(18) 0.9077(2) 0.16271(14) 0.0535(4) Uani 1 1 d . . . . .
F2 F 0.42850(17) 0.68939(17) 0.61301(14) 0.0584(3) Uani 1 1 d . . . . .
C6 C 1.0166(2) 0.9246(2) 0.63077(17) 0.0298(3) Uani 1 1 d . . . . .
C1 C 0.4349(2) 0.9496(3) 0.31653(18) 0.0365(4) Uani 1 1 d . . . . .
C7 C 0.8157(3) 0.7072(3) 0.13691(19) 0.0464(4) Uani 1 1 d . . . . .
H7A H 0.923131 0.705514 0.083343 0.070 Uiso 1 1 calc GR . . . .
H7B H 0.697512 0.750010 0.078251 0.070 Uiso 1 1 calc GR . . . .
H7C H 0.767099 0.568966 0.129974 0.070 Uiso 1 1 calc GR . . . .
C8 C 1.0331(3) 0.8380(3) 0.7666(2) 0.0468(4) Uani 1 1 d . . . . .
H8A H 0.952410 0.901182 0.837810 0.070 Uiso 1 1 calc GR . . . .
H8B H 1.180305 0.869152 0.837034 0.070 Uiso 1 1 calc GR . . . .
H8C H 0.977258 0.688350 0.711657 0.070 Uiso 1 1 calc GR . . . .
C3 C 0.4593(2) 0.8349(2) 0.5522(2) 0.0370(4) Uani 1 1 d . . . . .
C2 C 0.4008(2) 0.7900(2) 0.38454(19) 0.0377(4) Uani 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 C2 1.3272(17) . ?
C5 H5 0.9300 . ?
C5 C4 1.389(2) . ?
C5 C6 1.3910(18) . ?
C4 C6 1.403(2) 2_776 ?
C4 C7 1.5112(19) . ?
O1 C1 1.2128(17) . ?
F2 C3 1.3283(18) . ?
C6 C8 1.505(2) . ?
C1 C3 1.476(2) 2_676 ?
C1 C2 1.466(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C3 C2 1.324(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
_geom_angle_publ_flag
C4 C5 H5 118.4 . . ?
C4 C5 C6 123.13(13) . . ?
C6 C5 H5 118.4 . . ?
C5 C4 C6 118.52(12) . 2_776 ?
C5 C4 C7 120.86(14) . . ?
C6 C4 C7 120.61(14) 2_776 . ?
C5 C6 C4 118.35(13) . 2_776 ?
C5 C6 C8 120.21(14) . . ?
C4 C6 C8 121.45(13) 2_776 . ?
O1 C1 C3 122.20(16) . 2_676 ?
O1 C1 C2 122.26(15) . . ?
C2 C1 C3 115.54(13) . 2_676 ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
F2 C3 C1 115.83(14) . 2_676 ?
C2 C3 F2 122.37(15) . . ?
C2 C3 C1 121.80(15) . 2_676 ?
F1 C2 C1 115.64(14) . . ?
C3 C2 F1 121.69(16) . . ?
C3 C2 C1 122.66(14) . . ?

####################################################################### 
# 
# 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_MS-PA
_database_code_depnum_ccdc_archive 'CCDC 1896318'
loop_
_audit_author_name
_audit_author_address
'Binoy K. Saha'
;Pondicherry University
India
;
_audit_update_record             
;
2019-02-09 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_STRVA01_MS-PA               
;
PROBLEM: Flack parameter is too small
RESPONSE: There is heavy atom. Therefore, Flack parameter is not reliable. Moreover, compounds are not chiral.
;
_vrf_PLAT242_MS-PA               
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         N3 Check
RESPONSE: Stability of the system is poor. This causes the data quality slightly poor.
;
# Added during the CSD deposition process: Saturday 09 February 2019 07:53 AM
# end Validation Reply Form

_audit_creation_date             2019-02-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H3 N3 O7, C9 H12'
_chemical_formula_sum            'C15 H15 N3 O7'
_chemical_formula_weight         349.30
_chemical_absolute_configuration ?
_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 0.0033 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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.435(2)
_cell_length_b                   7.636(2)
_cell_length_c                   14.212(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.87(2)
_cell_angle_gamma                90
_cell_volume                     802.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2392
_cell_measurement_temperature    226(2)
_cell_measurement_theta_max      29.3682
_cell_measurement_theta_min      3.2298

_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.62
_exptl_crystal_size_min          0.36
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.861
_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       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7572
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.787
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.433
_diffrn_reflns_theta_min         3.236
_diffrn_ambient_temperature      226(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -79.00  -53.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272 -178.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00   18.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -23.00   15.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000  -30.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega   -5.00   61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8397 -119.0000  -77.0000 66

#__ type_ start__ end____ width___ exp.time_
  5 omega   -6.00   73.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8397   37.0000  150.0000 79

#__ type_ start__ end____ width___ exp.time_
  6 omega   31.00   57.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8397   57.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  -53.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8397  -19.0000  -60.0000 117

#__ type_ start__ end____ width___ exp.time_
  8 omega  -38.00   48.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272   57.0000  120.0000 86
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0153261000
_diffrn_orient_matrix_UB_12      -0.0436884000
_diffrn_orient_matrix_UB_13      -0.0423431000
_diffrn_orient_matrix_UB_21      0.0514008000
_diffrn_orient_matrix_UB_22      -0.0651395000
_diffrn_orient_matrix_UB_23      0.0265244000
_diffrn_orient_matrix_UB_31      -0.0797071000
_diffrn_orient_matrix_UB_32      -0.0498995000
_diffrn_orient_matrix_UB_33      0.0027970000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.707

_reflns_number_gt                2622
_reflns_number_total             3510


_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 875 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.8(10)
_refine_ls_extinction_coef       0.013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3510
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0619P)²+0.0014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1352
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C10(H10), C12(H12), C8(H8)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
N1 N 1.1418(4) 0.3843(4) 0.2862(2) 0.0507(7) Uani 1 1 d . . . . .
O6 O 0.7900(5) 1.0038(5) 0.0790(2) 0.0912(11) Uani 1 1 d . . . . .
N3 N 0.8344(4) 0.8513(4) 0.0807(2) 0.0533(7) Uani 1 1 d . . . . .
N2 N 1.0034(4) 0.9566(5) 0.4143(2) 0.0627(8) Uani 1 1 d . . . . .
O1 O 0.9839(4) 0.5080(4) 0.10484(17) 0.0615(7) Uani 1 1 d . . . . .
H1 H 1.032713 0.412991 0.120108 0.092 Uiso 1 1 calc GR . . . .
O3 O 1.2130(4) 0.3481(4) 0.36418(19) 0.0712(8) Uani 1 1 d . . . . .
O2 O 1.1313(4) 0.2804(3) 0.2192(2) 0.0708(8) Uani 1 1 d . . . . .
O7 O 0.8147(5) 0.7592(4) 0.0133(2) 0.0937(11) Uani 1 1 d . . . . .
C3 C 1.0714(4) 0.6706(4) 0.3465(2) 0.0422(7) Uani 1 1 d . . . . .
H3 H 1.125362 0.634941 0.406080 0.051 Uiso 1 1 calc R . . . .
C1 C 0.9882(4) 0.6097(4) 0.1792(2) 0.0381(6) Uani 1 1 d . . . . .
O5 O 0.9106(5) 1.0889(4) 0.4036(2) 0.0906(10) Uani 1 1 d . . . . .
O4 O 1.0982(4) 0.9186(5) 0.4862(2) 0.0890(10) Uani 1 1 d . . . . .
C6 C 0.9158(4) 0.7800(4) 0.1718(2) 0.0407(7) Uani 1 1 d . . . . .
C11 C 0.4144(4) 0.7834(4) 0.1679(2) 0.0441(7) Uani 1 1 d . . . . .
C2 C 1.0642(4) 0.5601(4) 0.2700(2) 0.0388(7) Uani 1 1 d . . . . .
C5 C 0.9196(4) 0.8907(4) 0.2478(2) 0.0422(7) Uani 1 1 d . . . . .
H5 H 0.869241 1.003469 0.240966 0.051 Uiso 1 1 calc R . . . .
C4 C 0.9974(4) 0.8352(4) 0.3333(2) 0.0442(7) Uani 1 1 d . . . . .
C10 C 0.4374(4) 0.8570(5) 0.2567(3) 0.0519(8) Uani 1 1 d . . . . .
H10 H 0.399677 0.972973 0.265161 0.062 Uiso 1 1 calc R . . . .
C12 C 0.4698(4) 0.6125(5) 0.1577(2) 0.0494(8) Uani 1 1 d . . . . .
H12 H 0.453474 0.560728 0.097438 0.059 Uiso 1 1 calc R . . . .
C8 C 0.5695(5) 0.5919(6) 0.3192(3) 0.0646(12) Uani 1 1 d . . . . .
H8 H 0.622842 0.526390 0.370706 0.078 Uiso 1 1 calc R . . . .
C7 C 0.5476(5) 0.5159(5) 0.2319(3) 0.0568(10) Uani 1 1 d . . . . .
C9 C 0.5159(5) 0.7623(7) 0.3344(2) 0.0619(11) Uani 1 1 d . . . . .
C13 C 0.6074(7) 0.3298(6) 0.2195(5) 0.116(2) Uani 1 1 d . . . . .
H13A H 0.717565 0.329003 0.188321 0.174 Uiso 1 1 calc GR . . . .
H13B H 0.513539 0.266342 0.181135 0.174 Uiso 1 1 calc GR . . . .
H13C H 0.629694 0.274115 0.280890 0.174 Uiso 1 1 calc GR . . . .
C15 C 0.3310(5) 0.8882(7) 0.0854(3) 0.0838(15) Uani 1 1 d . . . . .
H15A H 0.424471 0.954017 0.058071 0.126 Uiso 1 1 calc GR . . . .
H15B H 0.242511 0.968520 0.106593 0.126 Uiso 1 1 calc GR . . . .
H15C H 0.272190 0.809835 0.038073 0.126 Uiso 1 1 calc GR . . . .
C14 C 0.5378(8) 0.8428(12) 0.4301(3) 0.130(3) Uani 1 1 d . . . . .
H14A H 0.441643 0.802562 0.466048 0.194 Uiso 1 1 calc GR . . . .
H14B H 0.532227 0.969289 0.424248 0.194 Uiso 1 1 calc GR . . . .
H14C H 0.653770 0.809032 0.462492 0.194 Uiso 1 1 calc GR . . . .


_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
N1 O3 1.210(4) . ?
N1 O2 1.236(4) . ?
N1 C2 1.470(4) . ?
O6 N3 1.210(4) . ?
N3 O7 1.186(4) . ?
N3 C6 1.475(4) . ?
N2 O5 1.224(5) . ?
N2 O4 1.215(4) . ?
N2 C4 1.475(4) . ?
O1 H1 0.8300 . ?
O1 C1 1.310(4) . ?
C3 H3 0.9400 . ?
C3 C2 1.373(4) . ?
C3 C4 1.378(4) . ?
C1 C6 1.407(4) . ?
C1 C2 1.406(4) . ?
C6 C5 1.370(4) . ?
C11 C10 1.376(4) . ?
C11 C12 1.380(5) . ?
C11 C15 1.500(4) . ?
C5 H5 0.9400 . ?
C5 C4 1.358(4) . ?
C10 H10 0.9400 . ?
C10 C9 1.397(5) . ?
C12 H12 0.9400 . ?
C12 C7 1.366(5) . ?
C8 H8 0.9400 . ?
C8 C7 1.364(6) . ?
C8 C9 1.385(7) . ?
C7 C13 1.505(6) . ?
C9 C14 1.486(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?

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
O3 N1 O2 123.1(3) . . ?
O3 N1 C2 118.7(3) . . ?
O2 N1 C2 118.1(3) . . ?
O6 N3 C6 117.3(3) . . ?
O7 N3 O6 122.9(3) . . ?
O7 N3 C6 119.7(3) . . ?
O5 N2 C4 116.7(3) . . ?
O4 N2 O5 124.9(4) . . ?
O4 N2 C4 118.4(3) . . ?
C1 O1 H1 109.5 . . ?
C2 C3 H3 121.0 . . ?
C2 C3 C4 118.1(3) . . ?
C4 C3 H3 121.0 . . ?
O1 C1 C6 120.7(3) . . ?
O1 C1 C2 123.7(3) . . ?
C2 C1 C6 115.7(3) . . ?
C1 C6 N3 121.8(3) . . ?
C5 C6 N3 116.0(3) . . ?
C5 C6 C1 122.3(3) . . ?
C10 C11 C12 118.2(3) . . ?
C10 C11 C15 120.1(4) . . ?
C12 C11 C15 121.8(4) . . ?
C3 C2 N1 117.0(3) . . ?
C3 C2 C1 122.7(3) . . ?
C1 C2 N1 120.3(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.5 . . ?
C3 C4 N2 119.2(3) . . ?
C5 C4 N2 118.6(3) . . ?
C5 C4 C3 122.3(3) . . ?
C11 C10 H10 119.5 . . ?
C11 C10 C9 121.1(4) . . ?
C9 C10 H10 119.5 . . ?
C11 C12 H12 118.8 . . ?
C7 C12 C11 122.5(3) . . ?
C7 C12 H12 118.8 . . ?
C7 C8 H8 118.9 . . ?
C7 C8 C9 122.1(3) . . ?
C9 C8 H8 118.9 . . ?
C12 C7 C13 121.7(5) . . ?
C8 C7 C12 118.3(3) . . ?
C8 C7 C13 120.0(4) . . ?
C10 C9 C14 120.5(5) . . ?
C8 C9 C10 117.8(3) . . ?
C8 C9 C14 121.7(5) . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 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
O6 N3 C6 C1 -173.6(3) . . . . ?
O6 N3 C6 C5 5.1(4) . . . . ?
N3 C6 C5 C4 -178.1(3) . . . . ?
O1 C1 C6 N3 -0.6(4) . . . . ?
O1 C1 C6 C5 -179.3(3) . . . . ?
O1 C1 C2 N1 -1.2(4) . . . . ?
O1 C1 C2 C3 178.3(3) . . . . ?
O3 N1 C2 C3 -2.6(4) . . . . ?
O3 N1 C2 C1 176.9(3) . . . . ?
O2 N1 C2 C3 177.5(3) . . . . ?
O2 N1 C2 C1 -3.0(4) . . . . ?
O7 N3 C6 C1 6.6(4) . . . . ?
O7 N3 C6 C5 -174.7(3) . . . . ?
C1 C6 C5 C4 0.6(4) . . . . ?
O5 N2 C4 C3 -168.2(3) . . . . ?
O5 N2 C4 C5 12.3(4) . . . . ?
O4 N2 C4 C3 11.6(4) . . . . ?
O4 N2 C4 C5 -168.0(3) . . . . ?
C6 C1 C2 N1 179.2(2) . . . . ?
C6 C1 C2 C3 -1.3(4) . . . . ?
C6 C5 C4 N2 179.0(2) . . . . ?
C6 C5 C4 C3 -0.5(4) . . . . ?
C11 C10 C9 C8 -0.1(5) . . . . ?
C11 C10 C9 C14 -179.2(3) . . . . ?
C11 C12 C7 C8 0.4(5) . . . . ?
C11 C12 C7 C13 -179.9(3) . . . . ?
C2 C3 C4 N2 180.0(2) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C2 C1 C6 N3 178.9(2) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
C4 C3 C2 N1 -179.1(2) . . . . ?
C4 C3 C2 C1 1.4(4) . . . . ?
C10 C11 C12 C7 -0.7(4) . . . . ?
C12 C11 C10 C9 0.5(4) . . . . ?
C7 C8 C9 C10 -0.1(5) . . . . ?
C7 C8 C9 C14 179.0(4) . . . . ?
C9 C8 C7 C12 0.0(5) . . . . ?
C9 C8 C7 C13 -179.7(3) . . . . ?
C15 C11 C10 C9 -179.5(3) . . . . ?
C15 C11 C12 C7 179.3(3) . . . . ?

####################################################################### 
# 
# 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_DR-TN
_database_code_depnum_ccdc_archive 'CCDC 1896317'
loop_
_audit_author_name
_audit_author_address
'Binoy K. Saha'
;Pondicherry University
India
;
_audit_update_record             
;
2019-02-09 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_DR-TN               
;
PROBLEM: Short Inter D...A Contact  O6       ..O6       .       2.89 Ang.
RESPONSE: Stability of the system is poor. This causes the data quality slightly poor.
;
# Added during the CSD deposition process: Saturday 09 February 2019 07:53 AM
# end Validation Reply Form

_audit_creation_date             2019-02-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H3 N3 O6, 2(C5 H7)'
_chemical_formula_sum            'C16 H17 N3 O6'
_chemical_formula_weight         347.32
_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 0.0033 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'

_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.
;
_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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0581(5)
_cell_length_b                   10.7355(4)
_cell_length_c                   15.7163(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.294(4)
_cell_angle_gamma                90
_cell_volume                     1692.28(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5803
_cell_measurement_temperature    226.00(14)
_cell_measurement_theta_max      29.0830
_cell_measurement_theta_min      3.1259


_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18964
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.147
_diffrn_reflns_theta_min         3.132
_diffrn_ambient_temperature      226.00(14)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -23.00    3.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -57.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00   21.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega  -42.00   53.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272   37.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
  4 omega  -23.00    3.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -81.00  -50.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272 -178.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega  -17.00   13.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega  -85.00    8.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -37.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
  8 omega  -25.00   17.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000   90.0000 42

#__ type_ start__ end____ width___ exp.time_
  9 omega   -6.00   20.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  -25.00    1.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega  -30.00    2.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272   37.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
 12 omega    9.00   36.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272   37.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega  -27.00    2.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  123.0000   70.0000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega  -84.00  -41.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -57.0000  120.0000 43
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0311577000
_diffrn_orient_matrix_UB_12      0.0012250000
_diffrn_orient_matrix_UB_13      -0.0390216000
_diffrn_orient_matrix_UB_21      -0.0618620000
_diffrn_orient_matrix_UB_22      -0.0142399000
_diffrn_orient_matrix_UB_23      -0.0225413000
_diffrn_orient_matrix_UB_31      -0.0142398000
_diffrn_orient_matrix_UB_32      0.0645022000
_diffrn_orient_matrix_UB_33      -0.0042366000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000


_reflns_number_gt                3216
_reflns_number_total             4100


_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0574P)²+1.9058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1755
_refine_ls_wR_factor_ref         0.1855
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C2(H2), C7(H7), C12(H12)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O6 O 0.43468(18) 0.0920(2) 0.44428(14) 0.0549(5) Uani 1 1 d . . . . .
O5 O 0.5771(2) 0.0222(2) 0.35919(13) 0.0657(7) Uani 1 1 d . . . . .
O3 O 1.0498(2) 0.3833(2) 0.44927(18) 0.0716(7) Uani 1 1 d . . . . .
N3 N 0.5455(2) 0.0888(2) 0.41777(13) 0.0410(5) Uani 1 1 d . . . . .
O4 O 0.9621(2) 0.2959(2) 0.33403(15) 0.0716(7) Uani 1 1 d . . . . .
O1 O 0.8104(2) 0.3859(2) 0.70253(14) 0.0680(7) Uani 1 1 d . . . . .
O2 O 0.6288(2) 0.2798(2) 0.70682(13) 0.0638(6) Uani 1 1 d . . . . .
N1 N 0.7227(3) 0.3191(2) 0.66984(14) 0.0463(5) Uani 1 1 d . . . . .
N2 N 0.9623(2) 0.3230(2) 0.40915(17) 0.0482(6) Uani 1 1 d . . . . .
C5 C 0.6489(2) 0.1690(2) 0.45951(14) 0.0306(5) Uani 1 1 d . . . . .
C4 C 0.7565(2) 0.2023(2) 0.41480(14) 0.0329(5) Uani 1 1 d . . . . .
H4 H 0.765945 0.173343 0.359122 0.039 Uiso 1 1 calc R . . . .
C3 C 0.8496(2) 0.2802(2) 0.45607(15) 0.0336(5) Uani 1 1 d . . . . .
C1 C 0.7324(2) 0.2813(2) 0.58045(14) 0.0333(5) Uani 1 1 d . . . . .
C6 C 0.6333(2) 0.2073(2) 0.54231(14) 0.0327(5) Uani 1 1 d . . . . .
H6 H 0.558619 0.183894 0.571109 0.039 Uiso 1 1 calc R . . . .
C2 C 0.8409(2) 0.3211(2) 0.53885(16) 0.0357(5) Uani 1 1 d . . . . .
H2 H 0.905924 0.373770 0.565652 0.043 Uiso 1 1 calc R . . . .
C9 C 0.4535(3) 0.4394(2) 0.42356(15) 0.0387(5) Uani 1 1 d . . . . .
C8 C 0.5694(2) 0.5113(2) 0.42549(16) 0.0389(5) Uani 1 1 d . . . . .
C7 C 0.6127(2) 0.5705(2) 0.50189(16) 0.0403(6) Uani 1 1 d . . . . .
H7 H 0.690424 0.619288 0.503030 0.048 Uiso 1 1 calc R . . . .
C11 C 0.4012(3) 0.3728(3) 0.34337(18) 0.0554(7) Uani 1 1 d . . . . .
H11A H 0.383256 0.432996 0.297926 0.083 Uiso 1 1 calc GR . . . .
H11B H 0.319490 0.329238 0.353851 0.083 Uiso 1 1 calc GR . . . .
H11C H 0.467097 0.313356 0.326770 0.083 Uiso 1 1 calc GR . . . .
C10 C 0.6467(3) 0.5266(3) 0.34727(19) 0.0583(8) Uani 1 1 d . . . . .
H10A H 0.664536 0.445258 0.323734 0.087 Uiso 1 1 calc GR . . . .
H10B H 0.730418 0.568524 0.362954 0.087 Uiso 1 1 calc GR . . . .
H10C H 0.594883 0.575738 0.304960 0.087 Uiso 1 1 calc GR . . . .
C14 C -0.0585(2) 0.9315(2) 0.43052(16) 0.0396(5) Uani 1 1 d . . . . .
C13 C 0.0541(2) 1.0045(2) 0.41957(15) 0.0385(5) Uani 1 1 d . . . . .
C12 C 0.1099(2) 1.0711(2) 0.48939(16) 0.0409(6) Uani 1 1 d . . . . .
H12 H 0.185686 1.120165 0.482283 0.049 Uiso 1 1 calc R . . . .
C15 C 0.1143(3) 1.0133(3) 0.33479(18) 0.0547(7) Uani 1 1 d . . . . .
H15A H 0.132283 0.930253 0.314279 0.082 Uiso 1 1 calc GR . . . .
H15B H 0.196885 1.060167 0.341525 0.082 Uiso 1 1 calc GR . . . .
H15C H 0.052432 1.055253 0.294005 0.082 Uiso 1 1 calc GR . . . .
C16 C -0.1245(3) 0.8558(3) 0.3579(2) 0.0579(8) Uani 1 1 d . . . . .
H16A H -0.145980 0.909777 0.309243 0.087 Uiso 1 1 calc GR . . . .
H16B H -0.205606 0.818438 0.375793 0.087 Uiso 1 1 calc GR . . . .
H16C H -0.064138 0.790825 0.341937 0.087 Uiso 1 1 calc GR . . . .


_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
O6 N3 1.220(3) . ?
O5 N3 1.226(3) . ?
O3 N2 1.228(3) . ?
N3 C5 1.466(3) . ?
O4 N2 1.216(3) . ?
O1 N1 1.220(3) . ?
O2 N1 1.221(3) . ?
N1 C1 1.473(3) . ?
N2 C3 1.471(3) . ?
C5 C4 1.381(3) . ?
C5 C6 1.385(3) . ?
C4 H4 0.9400 . ?
C4 C3 1.380(3) . ?
C3 C2 1.382(3) . ?
C1 C6 1.377(3) . ?
C1 C2 1.381(3) . ?
C6 H6 0.9400 . ?
C2 H2 0.9400 . ?
C9 C8 1.397(4) . ?
C9 C7 1.395(4) 3_666 ?
C9 C11 1.509(4) . ?
C8 C7 1.399(4) . ?
C8 C10 1.512(4) . ?
C7 H7 0.9400 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C14 C13 1.399(4) . ?
C14 C12 1.396(4) 3_576 ?
C14 C16 1.513(4) . ?
C13 C12 1.392(4) . ?
C13 C15 1.507(4) . ?
C12 H12 0.9400 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?

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
O6 N3 O5 124.6(2) . . ?
O6 N3 C5 117.8(2) . . ?
O5 N3 C5 117.6(2) . . ?
O1 N1 O2 124.3(2) . . ?
O1 N1 C1 117.8(2) . . ?
O2 N1 C1 117.9(2) . . ?
O3 N2 C3 117.2(2) . . ?
O4 N2 O3 125.0(2) . . ?
O4 N2 C3 117.8(2) . . ?
C4 C5 N3 118.7(2) . . ?
C4 C5 C6 123.3(2) . . ?
C6 C5 N3 117.9(2) . . ?
C5 C4 H4 121.7 . . ?
C3 C4 C5 116.6(2) . . ?
C3 C4 H4 121.7 . . ?
C4 C3 N2 118.3(2) . . ?
C4 C3 C2 123.1(2) . . ?
C2 C3 N2 118.6(2) . . ?
C6 C1 N1 118.5(2) . . ?
C6 C1 C2 123.0(2) . . ?
C2 C1 N1 118.6(2) . . ?
C5 C6 H6 121.6 . . ?
C1 C6 C5 116.8(2) . . ?
C1 C6 H6 121.6 . . ?
C3 C2 H2 121.5 . . ?
C1 C2 C3 117.1(2) . . ?
C1 C2 H2 121.5 . . ?
C8 C9 C11 121.2(2) . . ?
C7 C9 C8 118.3(2) 3_666 . ?
C7 C9 C11 120.5(2) 3_666 . ?
C9 C8 C7 118.4(2) . . ?
C9 C8 C10 121.4(3) . . ?
C7 C8 C10 120.1(3) . . ?
C9 C7 C8 123.3(2) 3_666 . ?
C9 C7 H7 118.3 3_666 . ?
C8 C7 H7 118.3 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C14 C16 121.4(2) . . ?
C12 C14 C13 118.7(2) 3_576 . ?
C12 C14 C16 119.9(3) 3_576 . ?
C14 C13 C15 121.8(2) . . ?
C12 C13 C14 118.2(2) . . ?
C12 C13 C15 120.0(2) . . ?
C14 C12 H12 118.5 3_576 . ?
C13 C12 C14 123.1(2) . 3_576 ?
C13 C12 H12 118.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O6 N3 C5 C4 -157.0(2) . . . . ?
O6 N3 C5 C6 23.2(3) . . . . ?
O5 N3 C5 C4 23.8(3) . . . . ?
O5 N3 C5 C6 -156.1(2) . . . . ?
O3 N2 C3 C4 -173.9(2) . . . . ?
O3 N2 C3 C2 7.0(3) . . . . ?
N3 C5 C4 C3 178.52(19) . . . . ?
N3 C5 C6 C1 179.27(19) . . . . ?
O4 N2 C3 C4 6.0(3) . . . . ?
O4 N2 C3 C2 -173.2(2) . . . . ?
O1 N1 C1 C6 -179.2(2) . . . . ?
O1 N1 C1 C2 1.2(3) . . . . ?
O2 N1 C1 C6 2.2(3) . . . . ?
O2 N1 C1 C2 -177.5(2) . . . . ?
N1 C1 C6 C5 -177.2(2) . . . . ?
N1 C1 C2 C3 177.7(2) . . . . ?
N2 C3 C2 C1 178.7(2) . . . . ?
C5 C4 C3 N2 -177.0(2) . . . . ?
C5 C4 C3 C2 2.2(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C3 C2 C1 -0.4(3) . . . . ?
C6 C5 C4 C3 -1.6(3) . . . . ?
C6 C1 C2 C3 -2.0(3) . . . . ?
C2 C1 C6 C5 2.5(3) . . . . ?
C9 C8 C7 C9 0.4(4) . . . 3_666 ?
C7 C9 C8 C7 -0.4(4) 3_666 . . . ?
C7 C9 C8 C10 -179.9(2) 3_666 . . . ?
C11 C9 C8 C7 -179.9(2) . . . . ?
C11 C9 C8 C10 0.5(4) . . . . ?
C10 C8 C7 C9 180.0(2) . . . 3_666 ?
C14 C13 C12 C14 -0.1(4) . . . 3_576 ?
C12 C14 C13 C12 0.1(4) 3_576 . . . ?
C12 C14 C13 C15 -179.2(2) 3_576 . . . ?
C15 C13 C12 C14 179.2(2) . . . 3_576 ?
C16 C14 C13 C12 -179.7(2) . . . . ?
C16 C14 C13 C15 1.0(4) . . . . ?

####################################################################### 
# 
# 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_NP-TF
_database_code_depnum_ccdc_archive 'CCDC 1896319'
loop_
_audit_author_name
_audit_author_address
'Binoy K. Saha'
;Pondicherry University
India
;
_audit_update_record             
;
2019-02-09 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT031_NP-TF               
;
PROBLEM: Refined Extinction Parameter Within Range ......      2.688 Sigma
RESPONSE: Stability of the system is poor. This causes the data quality slightly poor.
;
# Added during the CSD deposition process: Saturday 09 February 2019 07:53 AM
# end Validation Reply Form

_audit_creation_date             2019-02-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 F4 O2, C10 H8'
_chemical_formula_sum            'C16 H8 F4 O2'
_chemical_formula_weight         308.22
_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 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6927(14)
_cell_length_b                   7.6784(14)
_cell_length_c                   7.7214(14)
_cell_angle_alpha                106.506(16)
_cell_angle_beta                 105.114(17)
_cell_angle_gamma                107.889(18)
_cell_volume                     334.68(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    951
_cell_measurement_temperature    262.00(2)
_cell_measurement_theta_max      28.9802
_cell_measurement_theta_min      3.2973

_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3637
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.044
_diffrn_reflns_theta_min         3.304
_diffrn_ambient_temperature      262.00(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491  -99.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00    7.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491  -99.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega   10.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega   -6.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   37.0000   30.0000 92

#__ type_ start__ end____ width___ exp.time_
  5 omega    3.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
  6 omega  -52.00   45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835  -37.0000 -150.0000 97

#__ type_ start__ end____ width___ exp.time_
  7 omega  -93.00  -35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491 -178.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega   -2.00   54.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
  9 omega   35.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835  178.0000 -120.0000 61
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0613497000
_diffrn_orient_matrix_UB_12      -0.1036263000
_diffrn_orient_matrix_UB_13      -0.0579592000
_diffrn_orient_matrix_UB_21      0.0257692000
_diffrn_orient_matrix_UB_22      -0.0201527000
_diffrn_orient_matrix_UB_23      0.0853539000
_diffrn_orient_matrix_UB_31      -0.1004276000
_diffrn_orient_matrix_UB_32      0.0058910000
_diffrn_orient_matrix_UB_33      0.0098862000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000

_reflns_number_gt                934
_reflns_number_total             1526

_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.043(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1526
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0762P)²+0.0986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1903
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C5(H5), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.6792(3) 0.6586(3) 0.3997(2) 0.0790(6) Uani 1 1 d . . . . .
F2 F 0.7092(3) 0.9052(2) 0.2035(3) 0.0798(6) Uani 1 1 d . . . . .
O1 O 0.4712(4) 0.2615(3) 0.1904(3) 0.0816(7) Uani 1 1 d . . . . .
C4 C -0.0103(4) 0.4322(3) 0.0465(3) 0.0440(6) Uani 1 1 d . . . . .
C3 C 0.6095(4) 0.7085(3) 0.1114(4) 0.0525(6) Uani 1 1 d . . . . .
C7 C 0.2047(5) 0.8431(5) 0.2679(5) 0.0751(9) Uani 1 1 d . . . . .
H7 H 0.276365 0.979639 0.342520 0.090 Uiso 1 1 calc R . . . .
C2 C 0.5949(4) 0.5891(4) 0.2059(3) 0.0525(6) Uani 1 1 d . . . . .
C6 C 0.1851(5) 0.7104(5) 0.3597(4) 0.0747(9) Uani 1 1 d . . . . .
H6 H 0.243676 0.759136 0.495457 0.090 Uiso 1 1 calc R . . . .
C1 C 0.4844(4) 0.3702(4) 0.1031(4) 0.0530(6) Uani 1 1 d . . . . .
C5 C 0.0815(4) 0.5106(5) 0.2534(4) 0.0605(7) Uani 1 1 d . . . . .
H5 H 0.070626 0.424095 0.317201 0.073 Uiso 1 1 calc R . . . .
C8 C 0.1198(4) 0.7745(4) 0.0702(4) 0.0604(7) Uani 1 1 d . . . . .
H8 H 0.133803 0.864761 0.010596 0.073 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 C2 1.328(3) . ?
F2 C3 1.325(3) . ?
O1 C1 1.210(3) . ?
C4 C4 1.417(4) 2_565 ?
C4 C5 1.416(3) . ?
C4 C8 1.413(3) 2_565 ?
C3 C2 1.321(4) . ?
C3 C1 1.469(4) 2_665 ?
C7 H7 0.9300 . ?
C7 C6 1.391(5) . ?
C7 C8 1.355(4) . ?
C2 C1 1.474(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.357(4) . ?
C5 H5 0.9300 . ?
C8 H8 0.9300 . ?

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 C4 C4 118.2(3) . 2_565 ?
C8 C4 C4 118.9(3) 2_565 2_565 ?
C8 C4 C5 122.9(2) 2_565 . ?
F2 C3 C1 116.1(2) . 2_665 ?
C2 C3 F2 122.2(2) . . ?
C2 C3 C1 121.6(2) . 2_665 ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C8 C7 C6 120.4(3) . . ?
F1 C2 C1 115.7(2) . . ?
C3 C2 F1 122.1(2) . . ?
C3 C2 C1 122.2(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 C7 120.7(3) . . ?
C5 C6 H6 119.6 . . ?
O1 C1 C3 121.9(2) . 2_665 ?
O1 C1 C2 121.9(3) . . ?
C3 C1 C2 116.2(2) 2_665 . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C8 H8 119.5 2_565 . ?
C7 C8 C4 120.9(3) . 2_565 ?
C7 C8 H8 119.5 . . ?

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
F1 C2 C1 O1 0.3(3) . . . . ?
F1 C2 C1 C3 -179.98(18) . . . 2_665 ?
F2 C3 C2 F1 0.0(4) . . . . ?
F2 C3 C2 C1 -179.81(19) . . . . ?
C4 C4 C5 C6 0.5(4) 2_565 . . . ?
C3 C2 C1 O1 -179.9(2) . . . . ?
C3 C2 C1 C3 -0.1(4) . . . 2_665 ?
C7 C6 C5 C4 -0.3(4) . . . . ?
C6 C7 C8 C4 -0.1(4) . . . 2_565 ?
C1 C3 C2 F1 179.98(19) 2_665 . . . ?
C1 C3 C2 C1 0.1(4) 2_665 . . . ?
C8 C4 C5 C6 -179.9(2) 2_565 . . . ?
C8 C7 C6 C5 0.1(4) . . . . ?

####################################################################### 
# 
# 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_NP-TN
_database_code_depnum_ccdc_archive 'CCDC 1896320'
loop_
_audit_author_name
_audit_author_address
'Binoy K. Saha'
;Pondicherry University
India
;
_audit_update_record             
;
2019-02-09 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT242_NP-TN               
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         N1 Check
RESPONSE: Stability of the system is poor. This causes the data quality slightly poor.
;
# Added during the CSD deposition process: Saturday 09 February 2019 07:53 AM
# end Validation Reply Form

_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H3 N3 O6, C10 H8'
_chemical_formula_sum            'C16 H11 N3 O6'
_chemical_formula_weight         341.28
_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 0.0033 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'

_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.
;
_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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.1553(18)
_cell_length_b                   6.8900(7)
_cell_length_c                   15.942(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.683(12)
_cell_angle_gamma                90
_cell_volume                     1544.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1834
_cell_measurement_temperature    262.00(2)
_cell_measurement_theta_max      28.9309
_cell_measurement_theta_min      3.0903

_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9147
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.995
_diffrn_reflns_theta_min         3.097
_diffrn_ambient_temperature      262.00(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -32.00   34.00   1.0000   52.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491   57.0000   60.0000 66

#__ type_ start__ end____ width___ exp.time_
  2 omega  -35.00   42.00   1.0000   52.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491   57.0000  120.0000 77

#__ type_ start__ end____ width___ exp.time_
  3 omega   -8.00   24.00   1.0000   52.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491  -99.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -21.00   43.00   1.0000   52.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491   57.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
  5 omega   26.00   57.00   1.0000   52.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835  -99.0000   30.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega  -86.00  -57.00   1.0000   52.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9491  -57.0000   30.0000 29
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0022458000
_diffrn_orient_matrix_UB_12      0.0049922000
_diffrn_orient_matrix_UB_13      -0.0445955000
_diffrn_orient_matrix_UB_21      -0.0498725000
_diffrn_orient_matrix_UB_22      -0.0153793000
_diffrn_orient_matrix_UB_23      -0.0036387000
_diffrn_orient_matrix_UB_31      -0.0074382000
_diffrn_orient_matrix_UB_32      0.1017066000
_diffrn_orient_matrix_UB_33      0.0016931000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000

_reflns_number_gt                2107
_reflns_number_total             3618

_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3618
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0694
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1069P)²+0.4383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1930
_refine_ls_wR_factor_ref         0.2315
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C4(H4), C14(H14), C12(H12), C10(H10), C15(H15), C7(H7),
 C9(H9), C8(H8), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O5 O 0.00954(15) 0.8855(4) 0.6192(2) 0.1195(10) Uani 1 1 d . . . . .
O6 O 0.08724(17) 0.9469(4) 0.74102(19) 0.1143(10) Uani 1 1 d . . . . .
N3 N 0.08262(17) 0.9082(3) 0.6666(2) 0.0786(7) Uani 1 1 d . . . . .
C11 C 0.20245(15) 0.3623(3) 0.53307(14) 0.0481(5) Uani 1 1 d . . . . .
O1 O 0.50330(17) 0.8971(5) 0.6685(2) 0.1345(11) Uani 1 1 d . . . . .
N1 N 0.43040(16) 0.9206(4) 0.70097(19) 0.0807(7) Uani 1 1 d . . . . .
C16 C 0.27703(16) 0.3819(3) 0.59831(16) 0.0534(6) Uani 1 1 d . . . . .
C1 C 0.34074(15) 0.9010(3) 0.64611(15) 0.0518(6) Uani 1 1 d . . . . .
C6 C 0.25707(16) 0.9096(3) 0.68228(14) 0.0519(6) Uani 1 1 d . . . . .
H6 H 0.256995 0.924471 0.740251 0.062 Uiso 1 1 calc R . . . .
C5 C 0.17372(16) 0.8952(3) 0.62904(16) 0.0550(6) Uani 1 1 d . . . . .
O2 O 0.42790(17) 0.9645(5) 0.77359(18) 0.1276(11) Uani 1 1 d . . . . .
O3 O 0.3297(3) 0.8349(4) 0.39092(17) 0.1372(13) Uani 1 1 d . . . . .
C3 C 0.2553(2) 0.8618(3) 0.51138(15) 0.0631(7) Uani 1 1 d . . . . .
O4 O 0.1771(3) 0.8123(5) 0.37762(17) 0.1407(13) Uani 1 1 d . . . . .
C2 C 0.34213(19) 0.8771(3) 0.56043(17) 0.0594(6) Uani 1 1 d . . . . .
H2 H 0.399032 0.871486 0.536650 0.071 Uiso 1 1 calc R . . . .
C4 C 0.1709(2) 0.8705(3) 0.54370(17) 0.0628(7) Uani 1 1 d . . . . .
H4 H 0.113466 0.860214 0.509198 0.075 Uiso 1 1 calc R . . . .
N2 N 0.2551(3) 0.8342(4) 0.41884(18) 0.0962(10) Uani 1 1 d . . . . .
C14 C 0.3849(3) 0.3525(4) 0.4907(3) 0.0938(12) Uani 1 1 d . . . . .
H14 H 0.446346 0.349475 0.475487 0.113 Uiso 1 1 calc R . . . .
C12 C 0.2227(2) 0.3385(4) 0.44852(18) 0.0727(8) Uani 1 1 d . . . . .
H12 H 0.172761 0.326355 0.405480 0.087 Uiso 1 1 calc R . . . .
C10 C 0.10741(18) 0.3644(4) 0.5524(2) 0.0685(7) Uani 1 1 d . . . . .
H10 H 0.057588 0.350408 0.509369 0.082 Uiso 1 1 calc R . . . .
C15 C 0.3730(2) 0.3765(4) 0.5749(3) 0.0851(10) Uani 1 1 d . . . . .
H15 H 0.425268 0.388896 0.615601 0.102 Uiso 1 1 calc R . . . .
C7 C 0.2534(3) 0.4053(4) 0.68145(19) 0.0844(10) Uani 1 1 d . . . . .
H7 H 0.301532 0.419648 0.725966 0.101 Uiso 1 1 calc R . . . .
C9 C 0.0888(3) 0.3863(4) 0.6322(3) 0.0892(11) Uani 1 1 d . . . . .
H9 H 0.025924 0.387696 0.643917 0.107 Uiso 1 1 calc R . . . .
C8 C 0.1607(4) 0.4068(4) 0.6970(2) 0.1011(13) Uani 1 1 d . . . . .
H8 H 0.146135 0.421917 0.752037 0.121 Uiso 1 1 calc R . . . .
C13 C 0.3111(3) 0.3332(5) 0.4298(2) 0.0903(10) Uani 1 1 d . . . . .
H13 H 0.322545 0.315922 0.374044 0.108 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
O5 N3 1.218(3) . ?
O6 N3 1.211(4) . ?
N3 C5 1.486(3) . ?
C11 C16 1.400(3) . ?
C11 C12 1.420(4) . ?
C11 C10 1.415(3) . ?
O1 N1 1.218(3) . ?
N1 C1 1.461(3) . ?
N1 O2 1.201(3) . ?
C16 C15 1.450(4) . ?
C16 C7 1.413(4) . ?
C1 C6 1.377(3) . ?
C1 C2 1.378(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.374(3) . ?
C5 C4 1.367(4) . ?
O3 N2 1.193(4) . ?
C3 C2 1.382(4) . ?
C3 C4 1.356(4) . ?
C3 N2 1.487(4) . ?
O4 N2 1.227(4) . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.382(5) . ?
C14 C13 1.347(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.320(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.337(5) . ?
C15 H15 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.364(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.371(5) . ?
C8 H8 0.9300 . ?
C13 H13 0.9300 . ?

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
O5 N3 C5 117.2(3) . . ?
O6 N3 O5 125.6(3) . . ?
O6 N3 C5 117.2(3) . . ?
C16 C11 C12 119.9(2) . . ?
C16 C11 C10 119.4(2) . . ?
C10 C11 C12 120.7(2) . . ?
O1 N1 C1 117.0(3) . . ?
O2 N1 O1 124.4(3) . . ?
O2 N1 C1 118.6(2) . . ?
C11 C16 C15 117.0(3) . . ?
C11 C16 C7 117.9(3) . . ?
C7 C16 C15 125.1(3) . . ?
C6 C1 N1 118.3(2) . . ?
C6 C1 C2 122.2(2) . . ?
C2 C1 N1 119.5(2) . . ?
C1 C6 H6 121.4 . . ?
C5 C6 C1 117.2(2) . . ?
C5 C6 H6 121.4 . . ?
C6 C5 N3 118.0(2) . . ?
C4 C5 N3 118.8(2) . . ?
C4 C5 C6 123.1(2) . . ?
C2 C3 N2 118.0(3) . . ?
C4 C3 C2 123.1(2) . . ?
C4 C3 N2 118.9(3) . . ?
C1 C2 C3 117.1(2) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C5 C4 H4 121.3 . . ?
C3 C4 C5 117.3(2) . . ?
C3 C4 H4 121.3 . . ?
O3 N2 C3 118.1(4) . . ?
O3 N2 O4 125.6(3) . . ?
O4 N2 C3 116.4(4) . . ?
C15 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?
C13 C14 C15 122.6(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C10 H10 119.8 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C16 C15 H15 120.7 . . ?
C14 C15 C16 118.5(3) . . ?
C14 C15 H15 120.7 . . ?
C16 C7 H7 119.7 . . ?
C8 C7 C16 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C10 C9 H9 119.4 . . ?
C10 C9 C8 121.1(3) . . ?
C8 C9 H9 119.4 . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C14 C13 H13 119.6 . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13 119.6 . . ?

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
O5 N3 C5 C6 -176.5(2) . . . . ?
O5 N3 C5 C4 3.9(3) . . . . ?
O6 N3 C5 C6 6.0(3) . . . . ?
O6 N3 C5 C4 -173.7(3) . . . . ?
N3 C5 C4 C3 179.2(2) . . . . ?
C11 C16 C15 C14 0.0(3) . . . . ?
C11 C16 C7 C8 0.5(4) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C11 C10 C9 C8 -0.1(4) . . . . ?
O1 N1 C1 C6 174.4(3) . . . . ?
O1 N1 C1 C2 -6.4(4) . . . . ?
N1 C1 C6 C5 178.6(2) . . . . ?
N1 C1 C2 C3 -179.2(2) . . . . ?
C16 C11 C12 C13 0.4(4) . . . . ?
C16 C11 C10 C9 0.5(3) . . . . ?
C16 C7 C8 C9 -0.2(4) . . . . ?
C1 C6 C5 N3 -178.76(19) . . . . ?
C1 C6 C5 C4 0.9(3) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C6 C5 C4 C3 -0.5(3) . . . . ?
O2 N1 C1 C6 -8.1(4) . . . . ?
O2 N1 C1 C2 171.1(3) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 N2 O3 -3.1(4) . . . . ?
C2 C3 N2 O4 176.8(3) . . . . ?
C4 C3 C2 C1 0.5(3) . . . . ?
C4 C3 N2 O3 176.9(3) . . . . ?
C4 C3 N2 O4 -3.1(4) . . . . ?
N2 C3 C2 C1 -179.5(2) . . . . ?
N2 C3 C4 C5 179.7(2) . . . . ?
C12 C11 C16 C15 0.0(3) . . . . ?
C12 C11 C16 C7 -180.0(2) . . . . ?
C12 C11 C10 C9 179.8(2) . . . . ?
C10 C11 C16 C15 179.3(2) . . . . ?
C10 C11 C16 C7 -0.6(3) . . . . ?
C10 C11 C12 C13 -178.9(2) . . . . ?
C10 C9 C8 C7 0.0(5) . . . . ?
C15 C16 C7 C8 -179.4(2) . . . . ?
C15 C14 C13 C12 0.7(5) . . . . ?
C7 C16 C15 C14 179.9(2) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?

