# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
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data_exp_5098
_database_code_depnum_ccdc_archive 'CCDC 1575270'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-05-10 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            'C15 H15 F2 N3 O3'
_chemical_formula_weight         323.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.3745(2)
_cell_length_b                   11.4530(3)
_cell_length_c                   13.8901(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1491.34(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    1.015
_shelx_estimated_absorpt_T_min   0.687
_shelx_estimated_absorpt_T_max   0.785
_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      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4726
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         5.005
_diffrn_reflns_theta_max         71.032
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2805
_reflns_number_gt                2743
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.965
_reflns_Friedel_fraction_full    0.996

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0499P)²+0.2390P] 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_abs_structure_details 
;
 Flack x determined using 1117 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2805
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0848
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_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
F1 F 0.25884(16) 0.96909(13) 0.97695(9) 0.0305(3) Uani 1 1 d . . . . .
F2 F 0.19663(15) 1.10688(11) 0.87672(10) 0.0285(3) Uani 1 1 d . . . . .
N3 N -0.0554(2) 0.85784(16) 0.49424(12) 0.0192(4) Uani 1 1 d . . . . .
O1 O 0.14529(18) 0.78895(14) 0.64319(11) 0.0252(4) Uani 1 1 d . . . . .
O2 O -0.0379(2) 0.79752(16) 0.96826(13) 0.0338(4) Uani 1 1 d . . . . .
C6 C -0.0262(2) 0.91689(18) 0.57748(15) 0.0170(4) Uani 1 1 d . . . . .
N1 N -0.0033(2) 0.77080(16) 0.88617(14) 0.0219(4) Uani 1 1 d . . . . .
O3 O -0.08641(18) 0.73562(15) 0.82464(14) 0.0317(4) Uani 1 1 d . . . . .
C3 C 0.1507(2) 0.78542(18) 0.85864(15) 0.0174(4) Uani 1 1 d . . . . .
H3A H 0.1750 0.7291 0.8091 0.021 Uiso 1 1 calc R U . . .
H3B H 0.2105 0.7702 0.9142 0.021 Uiso 1 1 calc R U . . .
C15 C 0.4389(2) 0.8414(2) 0.81724(16) 0.0224(4) Uani 1 1 d . . . . .
H15 H 0.4149 0.7856 0.8631 0.027 Uiso 1 1 calc R U . . .
C4 C 0.0700(2) 0.94822(18) 0.74460(15) 0.0182(4) Uani 1 1 d . . . . .
H4A H -0.0244 0.9441 0.7730 0.022 Uiso 1 1 calc R U . . .
H4B H 0.0877 1.0291 0.7275 0.022 Uiso 1 1 calc R U . . .
C10 C 0.3345(2) 0.91669(19) 0.78290(15) 0.0182(4) Uani 1 1 d . . . . .
N2 N -0.09795(19) 1.01683(16) 0.58240(13) 0.0192(4) Uani 1 1 d . . . . .
C5 C 0.0710(2) 0.87526(18) 0.65315(14) 0.0176(4) Uani 1 1 d . . . . .
C1 C 0.1645(2) 0.9962(2) 0.90588(15) 0.0210(5) Uani 1 1 d . . . . .
H1 H 0.0668 0.9934 0.9310 0.025 Uiso 1 1 calc R U . . .
C12 C 0.5146(3) 1.0077(2) 0.68329(18) 0.0310(5) Uani 1 1 d . . . . .
H12 H 0.5397 1.0644 0.6384 0.037 Uiso 1 1 calc R U . . .
C7 C -0.1747(3) 1.0215(2) 0.49924(16) 0.0251(5) Uani 1 1 d . . . . .
H7 H -0.2352 1.0824 0.4819 0.030 Uiso 1 1 calc R U . . .
C2 C 0.1803(2) 0.91084(18) 0.82082(14) 0.0165(4) Uani 1 1 d . . . . .
C9 C 0.0036(3) 0.7475(2) 0.45937(16) 0.0255(5) Uani 1 1 d . . . . .
H9A H 0.0971 0.7608 0.4334 0.038 Uiso 1 1 calc R U . . .
H9B H -0.0572 0.7163 0.4101 0.038 Uiso 1 1 calc R U . . .
H9C H 0.0096 0.6930 0.5117 0.038 Uiso 1 1 calc R U . . .
C11 C 0.3737(3) 1.0008(2) 0.71563(17) 0.0261(5) Uani 1 1 d . . . . .
H11 H 0.3058 1.0527 0.6921 0.031 Uiso 1 1 calc R U . . .
C8 C -0.1503(3) 0.9242(2) 0.44483(16) 0.0262(5) Uani 1 1 d . . . . .
H8 H -0.1908 0.9068 0.3854 0.031 Uiso 1 1 calc R U . . .
C13 C 0.6165(3) 0.9318(2) 0.71708(19) 0.0313(6) Uani 1 1 d . . . . .
H13 H 0.7099 0.9367 0.6950 0.038 Uiso 1 1 calc R U . . .
C14 C 0.5790(3) 0.8480(2) 0.78411(17) 0.0284(5) Uani 1 1 d . . . . .
H14 H 0.6473 0.7962 0.8071 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.361(3) . ?
F2 C1 1.365(3) . ?
N3 C8 1.356(3) . ?
N3 C6 1.367(3) . ?
N3 C9 1.462(3) . ?
O1 C5 1.217(3) . ?
O2 N1 1.224(3) . ?
C6 N2 1.329(3) . ?
C6 C5 1.470(3) . ?
N1 O3 1.225(3) . ?
N1 C3 1.503(3) . ?
C3 C2 1.555(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C15 C10 1.389(3) . ?
C15 C14 1.394(3) . ?
C15 H15 0.9300 . ?
C4 C5 1.520(3) . ?
C4 C2 1.540(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C10 C11 1.392(3) . ?
C10 C2 1.540(3) . ?
N2 C7 1.362(3) . ?
C1 C2 1.540(3) . ?
C1 H1 0.9800 . ?
C12 C13 1.375(4) . ?
C12 C11 1.397(3) . ?
C12 H12 0.9300 . ?
C7 C8 1.366(3) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 H11 0.9300 . ?
C8 H8 0.9300 . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 H14 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
C8 N3 C6 106.40(19) . . ?
C8 N3 C9 124.38(19) . . ?
C6 N3 C9 129.19(19) . . ?
N2 C6 N3 111.58(18) . . ?
N2 C6 C5 123.78(19) . . ?
N3 C6 C5 124.64(19) . . ?
O2 N1 O3 124.3(2) . . ?
O2 N1 C3 117.60(19) . . ?
O3 N1 C3 118.04(18) . . ?
N1 C3 C2 111.12(16) . . ?
N1 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
N1 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C10 C15 C14 121.1(2) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C5 C4 C2 114.67(17) . . ?
C5 C4 H4A 108.6 . . ?
C2 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C2 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C15 C10 C11 118.3(2) . . ?
C15 C10 C2 121.13(19) . . ?
C11 C10 C2 120.5(2) . . ?
C6 N2 C7 104.94(19) . . ?
O1 C5 C6 122.46(19) . . ?
O1 C5 C4 123.00(18) . . ?
C6 C5 C4 114.54(17) . . ?
F1 C1 F2 106.46(18) . . ?
F1 C1 C2 110.45(18) . . ?
F2 C1 C2 109.91(16) . . ?
F1 C1 H1 110.0 . . ?
F2 C1 H1 110.0 . . ?
C2 C1 H1 110.0 . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
N2 C7 C8 110.4(2) . . ?
N2 C7 H7 124.8 . . ?
C8 C7 H7 124.8 . . ?
C10 C2 C1 108.97(17) . . ?
C10 C2 C4 112.51(17) . . ?
C1 C2 C4 106.64(17) . . ?
C10 C2 C3 108.86(16) . . ?
C1 C2 C3 108.05(16) . . ?
C4 C2 C3 111.68(16) . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
N3 C8 C7 106.69(19) . . ?
N3 C8 H8 126.7 . . ?
C7 C8 H8 126.7 . . ?
C12 C13 C14 119.5(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?

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
C8 N3 C6 N2 -0.1(2) . . . . ?
C9 N3 C6 N2 177.8(2) . . . . ?
C8 N3 C6 C5 179.2(2) . . . . ?
C9 N3 C6 C5 -2.8(3) . . . . ?
O2 N1 C3 C2 -87.5(2) . . . . ?
O3 N1 C3 C2 90.9(2) . . . . ?
C14 C15 C10 C11 -1.2(3) . . . . ?
C14 C15 C10 C2 -178.9(2) . . . . ?
N3 C6 N2 C7 -0.3(2) . . . . ?
C5 C6 N2 C7 -179.6(2) . . . . ?
N2 C6 C5 O1 -173.1(2) . . . . ?
N3 C6 C5 O1 7.6(3) . . . . ?
N2 C6 C5 C4 7.3(3) . . . . ?
N3 C6 C5 C4 -171.94(18) . . . . ?
C2 C4 C5 O1 5.1(3) . . . . ?
C2 C4 C5 C6 -175.30(17) . . . . ?
C6 N2 C7 C8 0.6(3) . . . . ?
C15 C10 C2 C1 92.1(2) . . . . ?
C11 C10 C2 C1 -85.5(2) . . . . ?
C15 C10 C2 C4 -149.8(2) . . . . ?
C11 C10 C2 C4 32.5(3) . . . . ?
C15 C10 C2 C3 -25.5(3) . . . . ?
C11 C10 C2 C3 156.9(2) . . . . ?
F1 C1 C2 C10 -58.3(2) . . . . ?
F2 C1 C2 C10 58.9(2) . . . . ?
F1 C1 C2 C4 -179.99(17) . . . . ?
F2 C1 C2 C4 -62.8(2) . . . . ?
F1 C1 C2 C3 59.8(2) . . . . ?
F2 C1 C2 C3 177.00(16) . . . . ?
C5 C4 C2 C10 59.4(2) . . . . ?
C5 C4 C2 C1 178.82(17) . . . . ?
C5 C4 C2 C3 -63.4(2) . . . . ?
N1 C3 C2 C10 -173.54(16) . . . . ?
N1 C3 C2 C1 68.3(2) . . . . ?
N1 C3 C2 C4 -48.7(2) . . . . ?
C15 C10 C11 C12 0.6(3) . . . . ?
C2 C10 C11 C12 178.3(2) . . . . ?
C13 C12 C11 C10 0.1(4) . . . . ?
C6 N3 C8 C7 0.4(2) . . . . ?
C9 N3 C8 C7 -177.6(2) . . . . ?
N2 C7 C8 N3 -0.6(3) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C10 C15 C14 C13 1.0(4) . . . . ?

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.055

