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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_a
_database_code_depnum_ccdc_archive 'CCDC 1835504'
_audit_update_record             
;
2018-04-08 deposited with the CCDC.
2018-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 F2 N4 O8'
_chemical_formula_weight         352.22

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.1505(14)
_cell_length_b                   10.4710(13)
_cell_length_c                   10.2881(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1308.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3777
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.51
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.172
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7948
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.568
_diffrn_reflns_theta_max         25.004
_diffrn_reflns_theta_full        25.004
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1154
_reflns_number_gt                977
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0696P)²+0.9850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1154
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1420
_refine_ls_wR_factor_gt          0.1354
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0000 0.0912(3) 0.2500 0.0201(7) Uani 1 2 d S T P . .
C2 C 0.00036(18) 0.1729(2) 0.1274(2) 0.0231(5) Uani 1 1 d . . . . .
H2 H 0.0015 0.1193 0.0493 0.028 Uiso 1 1 calc R U . . .
C3 C -0.10249(18) 0.2605(2) 0.1284(3) 0.0283(6) Uani 1 1 d . . . . .
H3A H -0.1026 0.3135 0.0511 0.034 Uiso 1 1 calc R U . . .
H3B H -0.1685 0.2084 0.1273 0.034 Uiso 1 1 calc R U . . .
C4 C 0.10263(18) 0.2587(2) 0.1331(3) 0.0282(6) Uani 1 1 d . . . . .
C5 C 0.10278(17) 0.3456(2) 0.2502(3) 0.0299(6) Uani 1 1 d . . . . .
H5 H 0.1689 0.3992 0.2495 0.036 Uiso 1 1 calc R U . . .
C6 C 0.0000 0.4296(3) 0.2500 0.0363(9) Uani 1 2 d S T P . .
H6A H 0.0001 0.4839 0.1736 0.044 Uiso 0.5 1 calc R U P . .
H6B H -0.0001 0.4839 0.3264 0.044 Uiso 0.5 1 calc R U P . .
F1 F 0.19739(10) 0.18557(13) 0.12906(15) 0.0356(4) Uani 1 1 d . . . . .
N1 N 0.09609(13) -0.00673(17) 0.25119(19) 0.0227(5) Uani 1 1 d . . . . .
N2 N 0.11137(17) 0.3350(2) 0.0045(3) 0.0398(6) Uani 1 1 d . . . . .
O1 O 0.10821(13) -0.06795(16) 0.15154(17) 0.0315(5) Uani 1 1 d . . . . .
O2 O 0.14944(13) -0.01793(16) 0.35043(17) 0.0326(5) Uani 1 1 d . . . . .
O3 O 0.0809(2) 0.2838(2) -0.0945(2) 0.0598(7) Uani 1 1 d . . . . .
O4 O 0.15305(17) 0.4410(2) 0.0096(2) 0.0598(7) 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
C1 C2 1.524(3) . ?
C1 C2 1.524(3) 4 ?
C1 N1 1.554(2) . ?
C1 N1 1.554(2) 4 ?
C2 C4 1.535(3) . ?
C2 C3 1.550(3) . ?
C2 H2 0.9800 . ?
C3 C5 1.534(4) 4 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 F1 1.384(2) . ?
C4 C5 1.510(4) . ?
C4 N2 1.549(3) . ?
C5 C6 1.527(3) . ?
C5 C3 1.534(4) 4 ?
C5 H5 0.9800 . ?
C6 C5 1.527(3) 4 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
N1 O2 1.215(2) . ?
N1 O1 1.218(3) . ?
N2 O3 1.210(3) . ?
N2 O4 1.221(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2 111.7(2) . 4 ?
C2 C1 N1 112.01(11) . . ?
C2 C1 N1 111.47(11) 4 . ?
C2 C1 N1 111.47(11) . 4 ?
C2 C1 N1 112.01(11) 4 4 ?
N1 C1 N1 97.4(2) . 4 ?
C1 C2 C4 107.40(17) . . ?
C1 C2 C3 108.89(17) . . ?
C4 C2 C3 107.84(17) . . ?
C1 C2 H2 110.9 . . ?
C4 C2 H2 110.9 . . ?
C3 C2 H2 110.9 . . ?
C5 C3 C2 110.57(18) 4 . ?
C5 C3 H3A 109.5 4 . ?
C2 C3 H3A 109.5 . . ?
C5 C3 H3B 109.5 4 . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
F1 C4 C5 110.90(19) . . ?
F1 C4 C2 110.39(18) . . ?
C5 C4 C2 112.61(18) . . ?
F1 C4 N2 101.69(18) . . ?
C5 C4 N2 111.8(2) . . ?
C2 C4 N2 108.93(19) . . ?
C4 C5 C6 110.17(18) . . ?
C4 C5 C3 107.41(19) . 4 ?
C6 C5 C3 109.51(18) . 4 ?
C4 C5 H5 109.9 . . ?
C6 C5 H5 109.9 . . ?
C3 C5 H5 109.9 4 . ?
C5 C6 C5 109.7(3) . 4 ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 4 . ?
C5 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 4 . ?
H6A C6 H6B 108.2 . . ?
O2 N1 O1 126.30(18) . . ?
O2 N1 C1 118.10(16) . . ?
O1 N1 C1 115.57(16) . . ?
O3 N2 O4 124.5(2) . . ?
O3 N2 C4 118.0(2) . . ?
O4 N2 C4 117.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C2 C4 58.07(14) 4 . . . ?
N1 C1 C2 C4 -67.8(2) . . . . ?
N1 C1 C2 C4 -175.76(16) 4 . . . ?
C2 C1 C2 C3 -58.45(14) 4 . . . ?
N1 C1 C2 C3 175.68(16) . . . . ?
N1 C1 C2 C3 67.7(2) 4 . . . ?
C1 C2 C3 C5 58.6(2) . . . 4 ?
C4 C2 C3 C5 -57.6(2) . . . 4 ?
C1 C2 C4 F1 64.3(2) . . . . ?
C3 C2 C4 F1 -178.48(19) . . . . ?
C1 C2 C4 C5 -60.2(2) . . . . ?
C3 C2 C4 C5 57.0(2) . . . . ?
C1 C2 C4 N2 175.17(18) . . . . ?
C3 C2 C4 N2 -67.6(2) . . . . ?
F1 C4 C5 C6 177.62(17) . . . . ?
C2 C4 C5 C6 -58.1(2) . . . . ?
N2 C4 C5 C6 64.9(2) . . . . ?
F1 C4 C5 C3 -63.2(2) . . . 4 ?
C2 C4 C5 C3 61.1(2) . . . 4 ?
N2 C4 C5 C3 -175.90(17) . . . 4 ?
C4 C5 C6 C5 58.23(14) . . . 4 ?
C3 C5 C6 C5 -59.69(14) 4 . . 4 ?
C2 C1 N1 O2 134.34(18) . . . . ?
C2 C1 N1 O2 8.3(2) 4 . . . ?
N1 C1 N1 O2 -108.88(19) 4 . . . ?
C2 C1 N1 O1 -47.7(2) . . . . ?
C2 C1 N1 O1 -173.67(17) 4 . . . ?
N1 C1 N1 O1 69.13(15) 4 . . . ?
F1 C4 N2 O3 82.6(3) . . . . ?
C5 C4 N2 O3 -159.0(2) . . . . ?
C2 C4 N2 O3 -34.0(3) . . . . ?
F1 C4 N2 O4 -94.4(3) . . . . ?
C5 C4 N2 O4 24.0(3) . . . . ?
C2 C4 N2 O4 149.1(2) . . . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.071

