# 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 2016

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

data_sw1
_database_code_depnum_ccdc_archive 'CCDC 1431240'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 F N7 O'
_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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   15.3861(12)
_cell_length_b                   7.2041(7)
_cell_length_c                   15.4751(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.318(4)
_cell_angle_gamma                90.00
_cell_volume                     1524.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1937
_cell_measurement_theta_min      6.48
_cell_measurement_theta_max      64.61

_exptl_crystal_description       Rectangle
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7774
_exptl_absorpt_correction_T_max  0.8293
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       '\\\f and \\\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8094
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_sigmaI/netI    0.0726
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         6.48
_diffrn_reflns_theta_max         64.61
_reflns_number_total             1937
_reflns_number_gt                1369
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2 (Bruker, 2013)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS(Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL(Sheldrick, 2008)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0640P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0101(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1937
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F7 F 0.20023(13) 0.2924(2) 0.11687(12) 0.0731(5) Uani 1 1 d . . .
N13 N 0.78176(15) 0.2987(2) 0.57917(14) 0.0433(5) Uani 1 1 d . . .
O11 O 0.55208(13) 0.1946(3) 0.65074(13) 0.0591(5) Uani 1 1 d . . .
N18 N 0.88770(14) 0.3266(3) 0.74663(15) 0.0495(5) Uani 1 1 d . . .
N9 N 0.57740(13) 0.2813(3) 0.52755(14) 0.0468(5) Uani 1 1 d . . .
N1 N 0.31490(15) 0.2133(3) 0.37331(17) 0.0527(6) Uani 1 1 d . . .
N4 N 0.45991(16) 0.1889(3) 0.56663(16) 0.0598(6) Uani 1 1 d . . .
C12 C 0.79160(17) 0.2959(3) 0.67434(17) 0.0437(6) Uani 1 1 d . . .
N15 N 0.7515(2) 0.2031(3) 0.43291(17) 0.0708(7) Uani 1 1 d . . .
C14 C 0.75759(18) 0.1535(3) 0.51601(17) 0.0480(6) Uani 1 1 d . . .
H14 H 0.7468 0.0332 0.5307 0.058 Uiso 1 1 calc R . .
C6 C 0.40740(15) 0.2561(3) 0.39493(17) 0.0448(6) Uani 1 1 d . . .
C11 C 0.71675(18) 0.2680(3) 0.69409(18) 0.0484(6) Uani 1 1 d . . .
H11 H 0.7298 0.2594 0.7589 0.058 Uiso 1 1 calc R . .
C8 C 0.48014(17) 0.2419(3) 0.49758(18) 0.0452(6) Uani 1 1 d . . .
C3 C 0.27195(19) 0.2826(3) 0.2098(2) 0.0532(6) Uani 1 1 d . . .
N20 N 1.04940(18) 0.3446(4) 0.8175(2) 0.0809(8) Uani 1 1 d . . .
C2 C 0.2485(2) 0.2272(4) 0.2802(2) 0.0577(7) Uani 1 1 d . . .
H2 H 0.1837 0.1979 0.2630 0.069 Uiso 1 1 calc R . .
C10 C 0.61674(18) 0.2506(3) 0.62001(18) 0.0444(6) Uani 1 1 d . . .
C22 C 0.91891(19) 0.3623(4) 0.84422(19) 0.0629(7) Uani 1 1 d . . .
H22 H 0.8799 0.3770 0.8751 0.075 Uiso 1 1 calc R . .
C5 C 0.43569(19) 0.3114(4) 0.3263(2) 0.0563(7) Uani 1 1 d . . .
H5 H 0.5009 0.3388 0.3447 0.068 Uiso 1 1 calc R . .
C17 C 0.7897(3) 0.4509(4) 0.5306(2) 0.0836(10) Uani 1 1 d . . .
H17 H 0.8048 0.5717 0.5539 0.100 Uiso 1 1 calc R . .
C21 C 1.0160(2) 0.3712(5) 0.8850(2) 0.0758(8) Uani 1 1 d . . .
H21 H 1.0562 0.3927 0.9508 0.091 Uiso 1 1 calc R . .
C4 C 0.3663(2) 0.3257(4) 0.2301(2) 0.0616(7) Uani 1 1 d . . .
H4 H 0.3826 0.3625 0.1818 0.074 Uiso 1 1 calc R . .
C19 C 0.9716(2) 0.3183(4) 0.7364(2) 0.0686(8) Uani 1 1 d . . .
H19 H 0.9723 0.2962 0.6775 0.082 Uiso 1 1 calc R . .
C16 C 0.7712(4) 0.3894(5) 0.4430(2) 0.1018(14) Uani 1 1 d . . .
H16 H 0.7715 0.4642 0.3942 0.122 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
F7 C3 1.354(3) . ?
N13 C14 1.362(3) . ?
N13 C17 1.366(3) . ?
N13 C12 1.410(3) . ?
O11 C10 1.347(3) . ?
O11 N4 1.419(3) . ?
N18 C19 1.372(3) . ?
N18 C22 1.383(3) . ?
N18 C12 1.403(3) . ?
N9 C10 1.291(3) . ?
N9 C8 1.378(3) . ?
N1 C2 1.334(4) . ?
N1 C6 1.340(3) . ?
N4 C8 1.300(3) . ?
C12 C11 1.335(3) . ?
N15 C14 1.296(3) . ?
N15 C16 1.369(4) . ?
C14 H14 0.9300 . ?
C6 C5 1.378(4) . ?
C6 C8 1.468(3) . ?
C11 C10 1.442(4) . ?
C11 H11 0.9300 . ?
C3 C2 1.356(4) . ?
C3 C4 1.372(4) . ?
N20 C19 1.291(4) . ?
N20 C21 1.372(4) . ?
C2 H2 0.9300 . ?
C22 C21 1.330(4) . ?
C22 H22 0.9300 . ?
C5 C4 1.381(4) . ?
C5 H5 0.9300 . ?
C17 C16 1.326(4) . ?
C17 H17 0.9300 . ?
C21 H21 0.9300 . ?
C4 H4 0.9300 . ?
C19 H19 0.9300 . ?
C16 H16 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
C14 N13 C17 106.6(2) . . ?
C14 N13 C12 127.00(19) . . ?
C17 N13 C12 126.3(2) . . ?
C10 O11 N4 105.91(18) . . ?
C19 N18 C22 105.1(2) . . ?
C19 N18 C12 127.1(2) . . ?
C22 N18 C12 127.7(2) . . ?
C10 N9 C8 102.83(19) . . ?
C2 N1 C6 116.9(2) . . ?
C8 N4 O11 103.29(18) . . ?
C11 C12 N18 123.0(2) . . ?
C11 C12 N13 123.4(2) . . ?
N18 C12 N13 113.54(19) . . ?
C14 N15 C16 104.2(2) . . ?
N15 C14 N13 111.8(2) . . ?
N15 C14 H14 124.1 . . ?
N13 C14 H14 124.1 . . ?
N1 C6 C5 123.3(2) . . ?
N1 C6 C8 116.7(2) . . ?
C5 C6 C8 120.0(2) . . ?
C12 C11 C10 123.3(2) . . ?
C12 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
N4 C8 N9 114.6(2) . . ?
N4 C8 C6 124.0(2) . . ?
N9 C8 C6 121.4(2) . . ?
F7 C3 C2 118.7(2) . . ?
F7 C3 C4 119.5(2) . . ?
C2 C3 C4 121.7(3) . . ?
C19 N20 C21 104.9(2) . . ?
N1 C2 C3 122.4(2) . . ?
N1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
N9 C10 O11 113.3(2) . . ?
N9 C10 C11 130.7(2) . . ?
O11 C10 C11 115.9(2) . . ?
C21 C22 N18 106.2(2) . . ?
C21 C22 H22 126.9 . . ?
N18 C22 H22 126.9 . . ?
C6 C5 C4 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C16 C17 N13 105.2(3) . . ?
C16 C17 H17 127.4 . . ?
N13 C17 H17 127.4 . . ?
C22 C21 N20 111.3(3) . . ?
C22 C21 H21 124.3 . . ?
N20 C21 H21 124.3 . . ?
C3 C4 C5 116.4(2) . . ?
C3 C4 H4 121.8 . . ?
C5 C4 H4 121.8 . . ?
N20 C19 N18 112.5(3) . . ?
N20 C19 H19 123.8 . . ?
N18 C19 H19 123.8 . . ?
C17 C16 N15 112.1(2) . . ?
C17 C16 H16 123.9 . . ?
N15 C16 H16 123.9 . . ?

_diffrn_measured_fraction_theta_max 0.755
_diffrn_reflns_theta_full        64.61
_diffrn_measured_fraction_theta_full 0.755
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038
