# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_jb-uq6-fah
_database_code_depnum_ccdc_archive 'CCDC 1444965'
_audit_update_record             
;
2016-01-01 deposited with the CCDC.
2016-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '2-Fluoro-dibenzo[b,h][1,6]naphthyridine '
_chemical_name_common            ?
_chemical_melting_point          437-439
_chemical_formula_moiety         ?
_chemical_formula_sum            ' C16 H9 F N2'
_chemical_formula_weight         248.25

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'
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                   10.153(5)
_cell_length_b                   10.171(5)
_cell_length_c                   12.242(5)
_cell_angle_alpha                77.609(5)
_cell_angle_beta                 78.327(5)
_cell_angle_gamma                75.424(5)
_cell_volume                     1180.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1104
_cell_measurement_theta_min      3.0885
_cell_measurement_theta_max      29.0794

_exptl_crystal_description       cubic
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512.0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'

_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, Eos'
_diffrn_measurement_method       'CrysAlisPro, Agilent Technologies'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5540
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         29.12
_reflns_number_total             4321
_reflns_number_gt                2649
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL, PLATON, WINGX (Ferrugia, 2012)'

_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 > 2σ(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)+(0.0475P)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       0.0063(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4321
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C001 C 0.2973(2) 1.00026(19) 0.46247(16) 0.0379(4) Uani 1 1 d . . .
N1 N 0.20301(16) 0.97808(15) 0.55308(13) 0.0401(4) Uani 1 1 d . . .
C003 C 0.2819(2) 1.12345(19) 0.38016(16) 0.0419(5) Uani 1 1 d . . .
N2 N 0.50503(18) 1.04398(18) 0.27036(14) 0.0528(5) Uani 1 1 d . . .
C005 C 0.42242(19) 0.89581(19) 0.44449(15) 0.0386(5) Uani 1 1 d . . .
C006 C 0.0636(2) 1.20468(19) 0.48817(16) 0.0428(5) Uani 1 1 d . . .
C007 C 0.5215(2) 0.9226(2) 0.34967(16) 0.0437(5) Uani 1 1 d . . .
C008 C 0.0874(2) 1.07858(19) 0.56647(16) 0.0401(5) Uani 1 1 d . . .
C009 C 0.3922(2) 1.1357(2) 0.28628(17) 0.0527(6) Uani 1 1 d . . .
H009 H 0.3812 1.2162 0.2328 0.063 Uiso 1 1 calc R . .
C010 C 0.1640(2) 1.2248(2) 0.39406(17) 0.0480(5) Uani 1 1 d . . .
H010 H 0.1517 1.3058 0.3412 0.058 Uiso 1 1 calc R . .
F1 F 0.58917(14) 0.55424(13) 0.56801(12) 0.0889(5) Uani 1 1 d . . .
C012 C 0.6433(2) 0.8236(2) 0.33164(18) 0.0539(6) Uani 1 1 d . . .
H012 H 0.7096 0.8417 0.2692 0.065 Uiso 1 1 calc R . .
C013 C -0.0143(2) 1.0559(2) 0.66176(17) 0.0475(5) Uani 1 1 d . . .
H013 H -0.0002 0.9737 0.7130 0.057 Uiso 1 1 calc R . .
C014 C 0.6667(2) 0.7005(2) 0.40420(19) 0.0579(6) Uani 1 1 d . . .
H014 H 0.7479 0.6348 0.3921 0.070 Uiso 1 1 calc R . .
C015 C 0.4463(2) 0.7697(2) 0.51845(17) 0.0482(5) Uani 1 1 d . . .
H015 H 0.3816 0.7499 0.5817 0.058 Uiso 1 1 calc R . .
C016 C 0.5660(2) 0.6767(2) 0.49592(19) 0.0560(6) Uani 1 1 d . . .
C017 C -0.1552(2) 1.2772(2) 0.60232(19) 0.0601(6) Uani 1 1 d . . .
H017 H -0.2364 1.3426 0.6153 0.072 Uiso 1 1 calc R . .
C018 C -0.0610(2) 1.3032(2) 0.50974(19) 0.0560(6) Uani 1 1 d . . .
H018 H -0.0781 1.3862 0.4598 0.067 Uiso 1 1 calc R . .
C019 C -0.1320(2) 1.1523(2) 0.67947(18) 0.0554(6) Uani 1 1 d . . .
H019 H -0.1977 1.1361 0.7428 0.067 Uiso 1 1 calc R . .
C021 C 0.77823(19) 0.36834(18) 0.12473(16) 0.0406(5) Uani 1 1 d . . .
N4 N 0.90440(17) 0.44888(17) 0.23547(14) 0.0515(5) Uani 1 1 d . . .
C023 C 0.6549(2) 0.2852(2) 0.01565(17) 0.0441(5) Uani 1 1 d . . .
N3 N 0.71470(16) 0.51043(15) -0.05130(13) 0.0416(4) Uani 1 1 d . . .
C025 C 0.7175(2) 0.26669(19) 0.11016(17) 0.0474(5) Uani 1 1 d . . .
H025 H 0.7187 0.1864 0.1637 0.057 Uiso 1 1 calc R . .
C026 C 0.83873(18) 0.59368(18) 0.05761(15) 0.0377(5) Uani 1 1 d . . .
C027 C 0.8448(2) 0.3572(2) 0.21995(17) 0.0497(5) Uani 1 1 d . . .
H027 H 0.8452 0.2782 0.2748 0.060 Uiso 1 1 calc R . .
F2 F 0.90215(15) 0.93061(13) -0.07155(12) 0.0892(5) Uani 1 1 d . . .
C029 C 0.65524(19) 0.41006(19) -0.06377(16) 0.0420(5) Uani 1 1 d . . .
C030 C 0.77391(18) 0.48902(18) 0.04016(16) 0.0374(4) Uani 1 1 d . . .
C031 C 0.90175(19) 0.56855(19) 0.15346(16) 0.0410(5) Uani 1 1 d . . .
C032 C 0.5912(2) 0.4314(2) -0.16050(17) 0.0502(5) Uani 1 1 d . . .
H032 H 0.5908 0.5125 -0.2130 0.060 Uiso 1 1 calc R . .
C033 C 0.9661(2) 0.6675(2) 0.17093(17) 0.0501(5) Uani 1 1 d . . .
H033 H 1.0090 0.6508 0.2344 0.060 Uiso 1 1 calc R . .
C034 C 0.8388(2) 0.7176(2) -0.01913(17) 0.0482(5) Uani 1 1 d . . .
H034 H 0.7969 0.7363 -0.0833 0.058 Uiso 1 1 calc R . .
C035 C 0.9667(2) 0.7884(2) 0.09581(19) 0.0557(6) Uani 1 1 d . . .
H035 H 1.0096 0.8540 0.1072 0.067 Uiso 1 1 calc R . .
C036 C 0.5307(2) 0.2111(2) -0.0993(2) 0.0639(7) Uani 1 1 d . . .
H036 H 0.4889 0.1456 -0.1123 0.077 Uiso 1 1 calc R . .
C037 C 0.5908(2) 0.1860(2) -0.00577(19) 0.0572(6) Uani 1 1 d . . .
H037 H 0.5903 0.1035 0.0448 0.069 Uiso 1 1 calc R . .
C038 C 0.9021(2) 0.8100(2) 0.00309(18) 0.0539(6) Uani 1 1 d . . .
C039 C 0.5304(2) 0.3348(2) -0.17729(19) 0.0592(6) Uani 1 1 d . . .
H039 H 0.4881 0.3504 -0.2409 0.071 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C001 N1 1.330(2) . ?
C001 C003 1.426(3) . ?
C001 C005 1.449(3) . ?
N1 C008 1.356(2) . ?
C003 C010 1.377(3) . ?
C003 C009 1.441(3) . ?
N2 C009 1.293(3) . ?
N2 C007 1.393(2) . ?
C005 C015 1.399(3) . ?
C005 C007 1.401(3) . ?
C006 C010 1.392(3) . ?
C006 C018 1.420(3) . ?
C006 C008 1.426(3) . ?
C007 C012 1.396(3) . ?
C008 C013 1.413(3) . ?
C009 H009 0.9300 . ?
C010 H010 0.9300 . ?
F1 C016 1.360(2) . ?
C012 C014 1.368(3) . ?
C012 H012 0.9300 . ?
C013 C019 1.354(3) . ?
C013 H013 0.9300 . ?
C014 C016 1.381(3) . ?
C014 H014 0.9300 . ?
C015 C016 1.359(3) . ?
C015 H015 0.9300 . ?
C017 C018 1.352(3) . ?
C017 C019 1.409(3) . ?
C017 H017 0.9300 . ?
C018 H018 0.9300 . ?
C019 H019 0.9300 . ?
C021 C025 1.388(2) . ?
C021 C030 1.423(2) . ?
C021 C027 1.432(3) . ?
N4 C027 1.295(2) . ?
N4 C031 1.400(2) . ?
C023 C025 1.386(3) . ?
C023 C037 1.422(3) . ?
C023 C029 1.425(3) . ?
N3 C030 1.328(2) . ?
N3 C029 1.358(2) . ?
C025 H025 0.9300 . ?
C026 C031 1.394(3) . ?
C026 C034 1.402(2) . ?
C026 C030 1.456(2) . ?
C027 H027 0.9300 . ?
F2 C038 1.364(2) . ?
C029 C032 1.415(3) . ?
C031 C033 1.402(2) . ?
C032 C039 1.353(3) . ?
C032 H032 0.9300 . ?
C033 C035 1.369(3) . ?
C033 H033 0.9300 . ?
C034 C038 1.361(3) . ?
C034 H034 0.9300 . ?
C035 C038 1.375(3) . ?
C035 H035 0.9300 . ?
C036 C037 1.352(3) . ?
C036 C039 1.407(3) . ?
C036 H036 0.9300 . ?
C037 H037 0.9300 . ?
C039 H039 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
N1 C001 C003 123.14(18) . . ?
N1 C001 C005 119.58(17) . . ?
C003 C001 C005 117.27(17) . . ?
C001 N1 C008 117.59(16) . . ?
C010 C003 C001 118.96(17) . . ?
C010 C003 C009 123.19(19) . . ?
C001 C003 C009 117.84(19) . . ?
C009 N2 C007 117.59(17) . . ?
C015 C005 C007 119.50(19) . . ?
C015 C005 C001 121.95(17) . . ?
C007 C005 C001 118.55(18) . . ?
C010 C006 C018 123.3(2) . . ?
C010 C006 C008 118.19(19) . . ?
C018 C006 C008 118.54(18) . . ?
N2 C007 C012 117.31(18) . . ?
N2 C007 C005 123.39(19) . . ?
C012 C007 C005 119.3(2) . . ?
N1 C008 C013 118.23(18) . . ?
N1 C008 C006 122.91(17) . . ?
C013 C008 C006 118.86(18) . . ?
N2 C009 C003 125.34(19) . . ?
N2 C009 H009 117.3 . . ?
C003 C009 H009 117.3 . . ?
C003 C010 C006 119.20(19) . . ?
C003 C010 H010 120.4 . . ?
C006 C010 H010 120.4 . . ?
C014 C012 C007 121.1(2) . . ?
C014 C012 H012 119.4 . . ?
C007 C012 H012 119.4 . . ?
C019 C013 C008 120.9(2) . . ?
C019 C013 H013 119.6 . . ?
C008 C013 H013 119.6 . . ?
C012 C014 C016 118.0(2) . . ?
C012 C014 H014 121.0 . . ?
C016 C014 H014 121.0 . . ?
C016 C015 C005 118.57(19) . . ?
C016 C015 H015 120.7 . . ?
C005 C015 H015 120.7 . . ?
C015 C016 F1 118.5(2) . . ?
C015 C016 C014 123.5(2) . . ?
F1 C016 C014 118.0(2) . . ?
C018 C017 C019 120.9(2) . . ?
C018 C017 H017 119.5 . . ?
C019 C017 H017 119.5 . . ?
C017 C018 C006 120.5(2) . . ?
C017 C018 H018 119.7 . . ?
C006 C018 H018 119.7 . . ?
C013 C019 C017 120.2(2) . . ?
C013 C019 H019 119.9 . . ?
C017 C019 H019 119.9 . . ?
C025 C021 C030 117.85(18) . . ?
C025 C021 C027 123.27(18) . . ?
C030 C021 C027 118.88(16) . . ?
C027 N4 C031 117.28(18) . . ?
C025 C023 C037 123.34(19) . . ?
C025 C023 C029 118.04(16) . . ?
C037 C023 C029 118.6(2) . . ?
C030 N3 C029 117.27(16) . . ?
C021 C025 C023 119.83(18) . . ?
C021 C025 H025 120.1 . . ?
C023 C025 H025 120.1 . . ?
C031 C026 C034 119.87(17) . . ?
C031 C026 C030 118.51(17) . . ?
C034 C026 C030 121.61(18) . . ?
N4 C027 C021 124.99(18) . . ?
N4 C027 H027 117.5 . . ?
C021 C027 H027 117.5 . . ?
N3 C029 C032 118.01(18) . . ?
N3 C029 C023 123.01(18) . . ?
C032 C029 C023 118.98(17) . . ?
N3 C030 C021 124.00(16) . . ?
N3 C030 C026 119.39(17) . . ?
C021 C030 C026 116.61(18) . . ?
C026 C031 C033 119.29(18) . . ?
C026 C031 N4 123.71(16) . . ?
C033 C031 N4 117.00(18) . . ?
C039 C032 C029 120.5(2) . . ?
C039 C032 H032 119.7 . . ?
C029 C032 H032 119.7 . . ?
C035 C033 C031 120.9(2) . . ?
C035 C033 H033 119.6 . . ?
C031 C033 H033 119.6 . . ?
C038 C034 C026 118.0(2) . . ?
C038 C034 H034 121.0 . . ?
C026 C034 H034 121.0 . . ?
C033 C035 C038 118.05(18) . . ?
C033 C035 H035 121.0 . . ?
C038 C035 H035 121.0 . . ?
C037 C036 C039 120.99(19) . . ?
C037 C036 H036 119.5 . . ?
C039 C036 H036 119.5 . . ?
C036 C037 C023 120.3(2) . . ?
C036 C037 H037 119.9 . . ?
C023 C037 H037 119.9 . . ?
C034 C038 F2 118.0(2) . . ?
C034 C038 C035 123.90(19) . . ?
F2 C038 C035 118.11(18) . . ?
C032 C039 C036 120.6(2) . . ?
C032 C039 H039 119.7 . . ?
C036 C039 H039 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.683
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.98
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.031
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
