# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1438897'
_audit_update_record             
;
2015-11-25 deposited with the CCDC.
2016-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 Br F N2 O'
_chemical_formula_weight         383.22

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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

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

_cell_length_a                   17.326(3)
_cell_length_b                   17.185(3)
_cell_length_c                   11.370(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.741(2)
_cell_angle_gamma                90.00
_cell_volume                     3205.9(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1276
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      18.34

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    2.583
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.4920
_exptl_absorpt_correction_T_max  0.6536
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15065
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_av_sigmaI/netI    0.0988
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         28.24
_reflns_number_total             3819
_reflns_number_gt                1665
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0552P)²+0.4571P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3819
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1492
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_restrained_S_all      0.919
_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
Br1 Br 0.45966(3) 0.12973(3) 1.08967(4) 0.0681(2) Uani 1 1 d . . .
F1 F 0.3474(2) 0.71378(16) 0.5494(3) 0.0964(10) Uani 1 1 d . . .
N1 N 0.3716(2) 0.3944(2) 0.5767(3) 0.0545(10) Uani 1 1 d . . .
N2 N 0.3573(2) 0.1271(2) 0.5279(3) 0.0577(10) Uani 1 1 d . . .
O1 O 0.4132(2) 0.38035(16) 0.7900(3) 0.0685(10) Uani 1 1 d . . .
C1 C 0.3544(4) 0.6344(3) 0.5554(4) 0.0657(14) Uani 1 1 d . . .
C2 C 0.2844(3) 0.5929(3) 0.5307(4) 0.0664(14) Uani 1 1 d . . .
H2 H 0.2339 0.6174 0.5081 0.080 Uiso 1 1 calc R . .
C3 C 0.2909(3) 0.5127(3) 0.5402(4) 0.0638(13) Uani 1 1 d . . .
H3 H 0.2444 0.4823 0.5264 0.077 Uiso 1 1 calc R . .
C4 C 0.3665(3) 0.4778(3) 0.5702(4) 0.0542(12) Uani 1 1 d . . .
C5 C 0.4355(3) 0.5213(3) 0.5954(4) 0.0644(14) Uani 1 1 d . . .
H5 H 0.4863 0.4973 0.6172 0.077 Uiso 1 1 calc R . .
C6 C 0.4297(4) 0.6016(3) 0.5884(5) 0.0704(15) Uani 1 1 d . . .
H6 H 0.4762 0.6323 0.6059 0.084 Uiso 1 1 calc R . .
C7 C 0.3310(3) 0.3711(3) 0.3547(4) 0.0756(16) Uani 1 1 d . . .
H7A H 0.3301 0.4243 0.3394 0.091 Uiso 1 1 calc R . .
H7B H 0.3180 0.3361 0.2888 0.091 Uiso 1 1 calc R . .
C8 C 0.3509(3) 0.3450(3) 0.4705(4) 0.0538(12) Uani 1 1 d . . .
C9 C 0.3597(2) 0.2651(3) 0.5207(4) 0.0494(11) Uani 1 1 d . . .
C10 C 0.3845(2) 0.2695(2) 0.6484(4) 0.0474(11) Uani 1 1 d . . .
C11 C 0.3928(3) 0.3524(3) 0.6867(4) 0.0518(12) Uani 1 1 d . . .
C12 C 0.3959(2) 0.2021(2) 0.7226(4) 0.0471(11) Uani 1 1 d . . .
C13 C 0.3812(3) 0.1310(3) 0.6562(4) 0.0504(11) Uani 1 1 d . . .
C14 C 0.3894(3) 0.0612(3) 0.7226(5) 0.0603(13) Uani 1 1 d . . .
H14 H 0.3793 0.0143 0.6797 0.072 Uiso 1 1 calc R . .
C15 C 0.4118(3) 0.0608(3) 0.8489(5) 0.0609(13) Uani 1 1 d . . .
H15 H 0.4170 0.0140 0.8920 0.073 Uiso 1 1 calc R . .
C16 C 0.4268(3) 0.1317(3) 0.9132(4) 0.0504(11) Uani 1 1 d . . .
C17 C 0.4206(3) 0.2013(3) 0.8539(4) 0.0508(11) Uani 1 1 d . . .
H17 H 0.4323 0.2475 0.8988 0.061 Uiso 1 1 calc R . .
C18 C 0.3463(3) 0.1905(3) 0.4612(4) 0.0540(12) Uani 1 1 d . . .
C19 C 0.3177(3) 0.1808(3) 0.3215(4) 0.0714(15) Uani 1 1 d . . .
H19A H 0.3132 0.1264 0.3012 0.107 Uiso 1 1 calc R . .
H19B H 0.3563 0.2046 0.2882 0.107 Uiso 1 1 calc R . .
H19C H 0.2655 0.2053 0.2865 0.107 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
Br1 C16 1.902(4) . ?
F1 C1 1.369(5) . ?
N1 C11 1.387(5) . ?
N1 C8 1.424(5) . ?
N1 C4 1.436(5) . ?
N2 C18 1.307(5) . ?
N2 C13 1.385(5) . ?
O1 C11 1.211(5) . ?
C1 C2 1.357(7) . ?
C1 C6 1.358(7) . ?
C2 C3 1.384(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.361(6) . ?
C5 C6 1.383(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.327(6) . ?
C7 H7A 0.9300 . ?
C7 H7B 0.9300 . ?
C8 C9 1.476(6) . ?
C9 C10 1.378(5) . ?
C9 C18 1.434(6) . ?
C10 C12 1.409(6) . ?
C10 C11 1.483(6) . ?
C12 C17 1.415(5) . ?
C12 C13 1.415(5) . ?
C13 C14 1.400(6) . ?
C14 C15 1.362(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.402(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.361(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.513(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
C11 N1 C8 112.1(4) . . ?
C11 N1 C4 124.0(4) . . ?
C8 N1 C4 123.8(4) . . ?
C18 N2 C13 120.6(4) . . ?
C2 C1 C6 123.6(5) . . ?
C2 C1 F1 117.0(5) . . ?
C6 C1 F1 119.4(5) . . ?
C1 C2 C3 117.6(5) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 119.9(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.9(5) . . ?
C5 C4 N1 120.1(5) . . ?
C3 C4 N1 119.0(4) . . ?
C4 C5 C6 119.5(5) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 118.4(5) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C8 C7 H7A 120.0 . . ?
C8 C7 H7B 120.0 . . ?
H7A C7 H7B 120.0 . . ?
C7 C8 N1 123.7(5) . . ?
C7 C8 C9 131.2(4) . . ?
N1 C8 C9 105.1(4) . . ?
C10 C9 C18 119.6(4) . . ?
C10 C9 C8 108.4(4) . . ?
C18 C9 C8 132.0(4) . . ?
C9 C10 C12 121.5(4) . . ?
C9 C10 C11 109.3(4) . . ?
C12 C10 C11 129.3(4) . . ?
O1 C11 N1 125.3(4) . . ?
O1 C11 C10 129.4(4) . . ?
N1 C11 C10 105.2(4) . . ?
C10 C12 C17 125.1(4) . . ?
C10 C12 C13 115.1(4) . . ?
C17 C12 C13 119.8(4) . . ?
N2 C13 C14 118.1(4) . . ?
N2 C13 C12 123.1(4) . . ?
C14 C13 C12 118.8(4) . . ?
C15 C14 C13 121.2(4) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 119.1(4) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 122.3(4) . . ?
C17 C16 Br1 119.2(3) . . ?
C15 C16 Br1 118.5(3) . . ?
C16 C17 C12 118.7(4) . . ?
C16 C17 H17 120.7 . . ?
C12 C17 H17 120.7 . . ?
N2 C18 C9 120.1(4) . . ?
N2 C18 C19 117.0(4) . . ?
C9 C18 C19 122.8(4) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
C6 C1 C2 C3 0.1(7) . . . . ?
F1 C1 C2 C3 -178.1(4) . . . . ?
C1 C2 C3 C4 -1.9(7) . . . . ?
C2 C3 C4 C5 2.5(7) . . . . ?
C2 C3 C4 N1 -178.5(4) . . . . ?
C11 N1 C4 C5 78.4(6) . . . . ?
C8 N1 C4 C5 -105.5(5) . . . . ?
C11 N1 C4 C3 -100.6(5) . . . . ?
C8 N1 C4 C3 75.5(6) . . . . ?
C3 C4 C5 C6 -1.3(7) . . . . ?
N1 C4 C5 C6 179.8(4) . . . . ?
C2 C1 C6 C5 1.1(8) . . . . ?
F1 C1 C6 C5 179.2(4) . . . . ?
C4 C5 C6 C1 -0.5(7) . . . . ?
C11 N1 C8 C7 -177.8(5) . . . . ?
C4 N1 C8 C7 5.7(7) . . . . ?
C11 N1 C8 C9 0.5(5) . . . . ?
C4 N1 C8 C9 -176.0(4) . . . . ?
C7 C8 C9 C10 177.8(5) . . . . ?
N1 C8 C9 C10 -0.3(5) . . . . ?
C7 C8 C9 C18 -3.1(9) . . . . ?
N1 C8 C9 C18 178.8(4) . . . . ?
C18 C9 C10 C12 -1.0(6) . . . . ?
C8 C9 C10 C12 178.2(4) . . . . ?
C18 C9 C10 C11 -179.2(4) . . . . ?
C8 C9 C10 C11 0.1(5) . . . . ?
C8 N1 C11 O1 179.7(4) . . . . ?
C4 N1 C11 O1 -3.8(7) . . . . ?
C8 N1 C11 C10 -0.4(5) . . . . ?
C4 N1 C11 C10 176.1(4) . . . . ?
C9 C10 C11 O1 -179.9(5) . . . . ?
C12 C10 C11 O1 2.1(8) . . . . ?
C9 C10 C11 N1 0.2(5) . . . . ?
C12 C10 C11 N1 -177.7(4) . . . . ?
C9 C10 C12 C17 -179.4(4) . . . . ?
C11 C10 C12 C17 -1.7(7) . . . . ?
C9 C10 C12 C13 0.9(6) . . . . ?
C11 C10 C12 C13 178.6(4) . . . . ?
C18 N2 C13 C14 177.9(4) . . . . ?
C18 N2 C13 C12 -0.6(6) . . . . ?
C10 C12 C13 N2 -0.1(6) . . . . ?
C17 C12 C13 N2 -179.8(4) . . . . ?
C10 C12 C13 C14 -178.6(4) . . . . ?
C17 C12 C13 C14 1.7(6) . . . . ?
N2 C13 C14 C15 -179.2(4) . . . . ?
C12 C13 C14 C15 -0.6(7) . . . . ?
C13 C14 C15 C16 0.0(7) . . . . ?
C14 C15 C16 C17 -0.6(7) . . . . ?
C14 C15 C16 Br1 -179.0(3) . . . . ?
C15 C16 C17 C12 1.7(7) . . . . ?
Br1 C16 C17 C12 -179.9(3) . . . . ?
C10 C12 C17 C16 178.1(4) . . . . ?
C13 C12 C17 C16 -2.3(6) . . . . ?
C13 N2 C18 C9 0.5(6) . . . . ?
C13 N2 C18 C19 -178.3(4) . . . . ?
C10 C9 C18 N2 0.3(6) . . . . ?
C8 C9 C18 N2 -178.7(4) . . . . ?
C10 C9 C18 C19 179.0(4) . . . . ?
C8 C9 C18 C19 0.0(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        28.24
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.067
