# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1049284'
_audit_update_record             
;
2015-02-13 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            oxazine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 F N O3'
_chemical_formula_weight         309.29

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6164(5)
_cell_length_b                   8.1700(8)
_cell_length_c                   12.1539(12)
_cell_angle_alpha                92.548(8)
_cell_angle_beta                 103.893(8)
_cell_angle_gamma                108.383(8)
_cell_volume                     690.74(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2555
_cell_measurement_theta_min      3.8580
_cell_measurement_theta_max      28.3700

_exptl_crystal_description       cuboidal
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89765
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8110
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2420
_reflns_number_gt                2062
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;    
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-32 (Faruggia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0685P)²+0.3584P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2420
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1461
_refine_ls_wR_factor_gt          0.1405
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.051
_refine_ls_shift/su_mean         0.010

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
C1 C 0.2468(3) -0.0022(3) 0.51760(17) 0.0381(5) Uani 1 1 d . . .
C6 C 0.2474(3) -0.1390(2) 0.44474(17) 0.0383(5) Uani 1 1 d . . .
C10 C 0.2463(3) -0.0238(3) 0.63810(18) 0.0424(5) Uani 1 1 d . . .
C2 C 0.2515(3) 0.1553(3) 0.47733(19) 0.0451(5) Uani 1 1 d . . .
H2 H 0.2520 0.2470 0.5257 0.054 Uiso 1 1 calc R . .
O1 O 0.2583(3) 0.0976(2) 0.70519(13) 0.0621(5) Uani 1 1 d . . .
C8 C 0.2334(3) -0.3257(3) 0.60560(18) 0.0428(5) Uani 1 1 d . . .
C7 C 0.2443(3) -0.3075(3) 0.48633(18) 0.0425(5) Uani 1 1 d . . .
O3 O 0.2231(3) -0.4870(2) 0.63394(15) 0.0618(5) Uani 1 1 d . . .
C9 C 0.2354(3) -0.1933(3) 0.67650(17) 0.0417(5) Uani 1 1 d . . .
O2 O 0.2479(3) -0.4285(2) 0.42616(14) 0.0612(5) Uani 1 1 d . . .
C5 C 0.2523(3) -0.1159(3) 0.33290(19) 0.0466(5) Uani 1 1 d . . .
H5 H 0.2541 -0.2061 0.2842 0.056 Uiso 1 1 calc R . .
C3 C 0.2553(3) 0.1758(3) 0.3660(2) 0.0503(6) Uani 1 1 d . . .
H3 H 0.2586 0.2815 0.3396 0.060 Uiso 1 1 calc R . .
C4 C 0.2544(3) 0.0409(3) 0.29372(19) 0.0513(6) Uani 1 1 d . . .
H4 H 0.2552 0.0552 0.2183 0.062 Uiso 1 1 calc R . .
N N 0.2847(3) -0.3742(3) 0.82817(16) 0.0628(6) Uani 1 1 d . . .
C13 C 0.4847(4) -0.3505(3) 0.88026(18) 0.0502(6) Uani 1 1 d . . .
C11 C 0.2362(3) -0.2111(3) 0.79746(18) 0.0508(6) Uani 1 1 d . . .
H11A H 0.1112 -0.2207 0.8080 0.061 Uiso 1 1 calc R . .
H11B H 0.3310 -0.1094 0.8468 0.061 Uiso 1 1 calc R . .
F F 1.0534(3) -0.2600(3) 1.04546(15) 0.0928(6) Uani 1 1 d . . .
C18 C 0.5849(4) -0.4461(3) 0.8429(2) 0.0608(7) Uani 1 1 d . . .
H18 H 0.5240 -0.5302 0.7793 0.073 Uiso 1 1 calc R . .
C14 C 0.5792(4) -0.2280(3) 0.97591(19) 0.0559(6) Uani 1 1 d . . .
H14 H 0.5127 -0.1653 1.0038 0.067 Uiso 1 1 calc R . .
C16 C 0.8651(4) -0.2911(3) 0.9911(2) 0.0603(7) Uani 1 1 d . . .
C15 C 0.7692(4) -0.1966(3) 1.0308(2) 0.0605(7) Uani 1 1 d . . .
H15 H 0.8313 -0.1121 1.0941 0.073 Uiso 1 1 calc R . .
C12 C 0.1804(4) -0.5144(3) 0.7436(2) 0.0684(7) Uani 1 1 d . . .
H12A H 0.0445 -0.5363 0.7338 0.082 Uiso 1 1 calc R . .
H12B H 0.2080 -0.6171 0.7683 0.082 Uiso 1 1 calc R . .
C17 C 0.7756(5) -0.4177(3) 0.8994(2) 0.0665(7) Uani 1 1 d . . .
H17 H 0.8416 -0.4841 0.8750 0.080 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
C1 C2 1.390(3) . ?
C1 C6 1.396(3) . ?
C1 C10 1.484(3) . ?
C6 C5 1.388(3) . ?
C6 C7 1.483(3) . ?
C10 O1 1.222(2) . ?
C10 C9 1.465(3) . ?
C2 C3 1.376(3) . ?
C8 C9 1.347(3) . ?
C8 O3 1.360(2) . ?
C8 C7 1.483(3) . ?
C7 O2 1.214(3) . ?
O3 C12 1.456(3) . ?
C9 C11 1.482(3) . ?
C5 C4 1.383(3) . ?
C3 C4 1.376(3) . ?
N C12 1.389(3) . ?
N C13 1.449(3) . ?
N C11 1.529(3) . ?
C13 C18 1.381(4) . ?
C13 C14 1.383(3) . ?
F C16 1.363(3) . ?
C18 C17 1.389(4) . ?
C14 C15 1.376(4) . ?
C16 C15 1.361(4) . ?
C16 C17 1.366(4) . ?

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 C6 119.62(19) . . ?
C2 C1 C10 120.28(18) . . ?
C6 C1 C10 120.08(18) . . ?
C5 C6 C1 119.52(19) . . ?
C5 C6 C7 120.02(19) . . ?
C1 C6 C7 120.46(18) . . ?
O1 C10 C9 120.15(19) . . ?
O1 C10 C1 121.11(19) . . ?
C9 C10 C1 118.73(18) . . ?
C3 C2 C1 120.1(2) . . ?
C9 C8 O3 124.9(2) . . ?
C9 C8 C7 122.21(18) . . ?
O3 C8 C7 112.88(18) . . ?
O2 C7 C6 122.4(2) . . ?
O2 C7 C8 120.19(19) . . ?
C6 C7 C8 117.41(18) . . ?
C8 O3 C12 112.95(18) . . ?
C8 C9 C10 120.99(19) . . ?
C8 C9 C11 121.3(2) . . ?
C10 C9 C11 117.66(19) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C3 C2 120.4(2) . . ?
C3 C4 C5 120.1(2) . . ?
C12 N C13 118.0(2) . . ?
C12 N C11 111.26(19) . . ?
C13 N C11 116.83(18) . . ?
C18 C13 C14 118.1(2) . . ?
C18 C13 N 124.3(2) . . ?
C14 C13 N 117.6(2) . . ?
C9 C11 N 108.60(18) . . ?
C13 C18 C17 120.7(2) . . ?
C15 C14 C13 121.6(2) . . ?
C15 C16 F 119.1(2) . . ?
C15 C16 C17 121.3(3) . . ?
F C16 C17 119.6(2) . . ?
C16 C15 C14 119.1(2) . . ?
N C12 O3 113.2(2) . . ?
C16 C17 C18 119.3(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 C6 C5 -0.1(3) . . . . ?
C10 C1 C6 C5 -178.54(18) . . . . ?
C2 C1 C6 C7 179.44(18) . . . . ?
C10 C1 C6 C7 1.0(3) . . . . ?
C2 C1 C10 O1 -3.2(3) . . . . ?
C6 C1 C10 O1 175.2(2) . . . . ?
C2 C1 C10 C9 178.13(18) . . . . ?
C6 C1 C10 C9 -3.4(3) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C10 C1 C2 C3 178.85(19) . . . . ?
C5 C6 C7 O2 0.8(3) . . . . ?
C1 C6 C7 O2 -178.8(2) . . . . ?
C5 C6 C7 C8 -178.27(18) . . . . ?
C1 C6 C7 C8 2.2(3) . . . . ?
C9 C8 C7 O2 177.8(2) . . . . ?
O3 C8 C7 O2 -1.7(3) . . . . ?
C9 C8 C7 C6 -3.1(3) . . . . ?
O3 C8 C7 C6 177.39(17) . . . . ?
C9 C8 O3 C12 10.1(3) . . . . ?
C7 C8 O3 C12 -170.4(2) . . . . ?
O3 C8 C9 C10 -179.87(19) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
O3 C8 C9 C11 3.2(3) . . . . ?
C7 C8 C9 C11 -176.25(19) . . . . ?
O1 C10 C9 C8 -176.1(2) . . . . ?
C1 C10 C9 C8 2.6(3) . . . . ?
O1 C10 C9 C11 1.0(3) . . . . ?
C1 C10 C9 C11 179.66(18) . . . . ?
C1 C6 C5 C4 -0.7(3) . . . . ?
C7 C6 C5 C4 179.74(19) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C6 C5 C4 C3 1.2(3) . . . . ?
C12 N C13 C18 7.6(3) . . . . ?
C11 N C13 C18 -129.2(2) . . . . ?
C12 N C13 C14 -170.2(2) . . . . ?
C11 N C13 C14 53.0(3) . . . . ?
C8 C9 C11 N 13.9(3) . . . . ?
C10 C9 C11 N -163.13(18) . . . . ?
C12 N C11 C9 -45.6(3) . . . . ?
C13 N C11 C9 93.9(2) . . . . ?
C14 C13 C18 C17 -0.8(3) . . . . ?
N C13 C18 C17 -178.5(2) . . . . ?
C18 C13 C14 C15 2.2(3) . . . . ?
N C13 C14 C15 -179.9(2) . . . . ?
F C16 C15 C14 180.0(2) . . . . ?
C17 C16 C15 C14 -1.0(4) . . . . ?
C13 C14 C15 C16 -1.3(4) . . . . ?
C13 N C12 O3 -76.4(3) . . . . ?
C11 N C12 O3 62.6(3) . . . . ?
C8 O3 C12 N -43.8(3) . . . . ?
C15 C16 C17 C18 2.4(4) . . . . ?
F C16 C17 C18 -178.6(2) . . . . ?
C13 C18 C17 C16 -1.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.039
