# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_try1_a
_database_code_depnum_ccdc_archive 'CCDC 1042078'
_audit_update_record             
;
2015-01-05 deposited with the CCDC.
2015-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H7 B Br F7 N2 O'
_chemical_formula_sum            'C16 H7 B Br F7 N2 O'
_chemical_formula_weight         466.95

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'
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'
B B 0.0013 0.0007 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   11.3455(12)
_cell_length_b                   10.2153(10)
_cell_length_c                   14.3393(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.725(5)
_cell_angle_gamma                90.00
_cell_volume                     1656.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      22.74

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912.0
_exptl_absorpt_coefficient_mu    2.567
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.365
_exptl_absorpt_correction_T_max  0.554
_exptl_absorpt_process_details   Multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3997
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         28.01
_reflns_number_total             3997
_reflns_number_gt                2011
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0480P)²+2.6204P] 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         2243
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
Br01 Br 0.67722(5) 1.14962(4) 0.54671(3) 0.0627(2) Uani 1 1 d . . .
F002 F 0.49905(17) 0.5768(2) 0.42339(14) 0.0464(5) Uani 1 1 d . . .
F003 F 0.90739(18) 0.4808(2) 0.43406(17) 0.0593(6) Uani 1 1 d . . .
F004 F 0.4543(2) 0.3756(3) 0.30887(16) 0.0655(7) Uani 1 1 d . . .
F005 F 0.6337(2) 0.2251(2) 0.25312(16) 0.0687(7) Uani 1 1 d . . .
O006 O 0.9006(2) 0.7435(2) 0.80290(16) 0.0459(6) Uani 1 1 d . . .
F007 F 0.8610(2) 0.2828(3) 0.31508(19) 0.0733(7) Uani 1 1 d . . .
F008 F 0.6880(3) 0.8961(3) 0.70345(15) 0.0758(8) Uani 1 1 d . . .
F009 F 0.8671(3) 0.9446(2) 0.6545(2) 0.0910(10) Uani 1 1 d . . .
N00A N 0.8092(2) 0.7195(3) 0.65533(18) 0.0323(6) Uani 1 1 d . . .
N00B N 0.7145(3) 0.8753(3) 0.53975(18) 0.0348(7) Uani 1 1 d . . .
C00C C 0.8651(3) 0.6661(3) 0.7316(2) 0.0360(8) Uani 1 1 d . . .
C00D C 0.7293(3) 0.6426(3) 0.5041(2) 0.0312(8) Uani 1 1 d . . .
C00E C 0.7836(3) 0.6170(3) 0.5913(2) 0.0326(8) Uani 1 1 d . . .
C00F C 0.7051(3) 0.5343(3) 0.4357(2) 0.0312(7) Uani 1 1 d . . .
C00G C 0.6963(3) 0.7712(3) 0.4774(2) 0.0337(8) Uani 1 1 d . . .
C00H C 0.5912(3) 0.5050(3) 0.3990(2) 0.0346(8) Uani 1 1 d . . .
C00I C 0.7944(3) 0.4568(3) 0.4046(2) 0.0389(8) Uani 1 1 d . . .
C00J C 0.8761(3) 0.5283(4) 0.7212(3) 0.0428(9) Uani 1 1 d . . .
C00K C 0.8253(3) 0.4993(4) 0.6355(3) 0.0399(9) Uani 1 1 d . . .
C00L C 0.7716(4) 0.3546(3) 0.3429(3) 0.0442(9) Uani 1 1 d . . .
C00M C 0.6572(4) 0.3267(3) 0.3110(2) 0.0446(9) Uani 1 1 d . . .
C00N C 0.5669(3) 0.4021(4) 0.3391(2) 0.0419(9) Uani 1 1 d . . .
C00O C 0.6479(3) 0.8205(4) 0.3920(3) 0.0427(9) Uani 1 1 d . . .
C00P C 0.6757(3) 0.9837(3) 0.4916(3) 0.0437(9) Uani 1 1 d . . .
C00Q C 0.6350(4) 0.9536(4) 0.4012(3) 0.0499(10) Uani 1 1 d . . .
C00R C 0.9609(4) 0.6847(4) 0.8813(3) 0.0550(11) Uani 1 1 d . . .
H00A H 0.9129 0.6132 0.9036 0.083 Uiso 1 1 calc R . .
H00B H 0.9752 0.7499 0.9311 0.083 Uiso 1 1 calc R . .
H00C H 1.0366 0.6499 0.8641 0.083 Uiso 1 1 calc R . .
B00S B 0.7704(4) 0.8650(4) 0.6419(3) 0.0445(11) Uani 1 1 d . . .
H2 H 0.819(3) 0.423(4) 0.611(2) 0.030(9) Uiso 1 1 d . . .
H3 H 0.632(3) 0.773(4) 0.341(3) 0.043(10) Uiso 1 1 d . . .
H1 H 0.910(3) 0.473(4) 0.764(3) 0.051(11) Uiso 1 1 d . . .
H4 H 0.588(4) 1.021(5) 0.357(3) 0.081(15) Uiso 1 1 d . . .


_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
Br01 C00P 1.869(4) . ?
F002 C00H 1.346(4) . ?
F003 C00I 1.339(4) . ?
F004 C00N 1.342(4) . ?
F005 C00M 1.342(4) . ?
O006 C00C 1.329(4) . ?
O006 C00R 1.402(5) . ?
F007 C00L 1.339(4) . ?
F008 B00S 1.375(5) . ?
F009 B00S 1.366(5) . ?
N00A C00C 1.335(4) . ?
N00A C00E 1.407(4) . ?
N00A B00S 1.558(5) . ?
N00B C00P 1.358(4) . ?
N00B C00G 1.394(4) . ?
N00B B00S 1.550(5) . ?
C00C C00J 1.422(5) . ?
C00D C00E 1.372(5) . ?
C00D C00G 1.411(5) . ?
C00D C00F 1.489(4) . ?
C00E C00K 1.422(5) . ?
C00F C00I 1.388(5) . ?
C00F C00H 1.388(5) . ?
C00G C00O 1.394(5) . ?
C00H C00N 1.371(5) . ?
C00I C00L 1.379(5) . ?
C00J C00K 1.347(5) . ?
C00L C00M 1.370(6) . ?
C00M C00N 1.368(6) . ?
C00O C00Q 1.375(6) . ?
C00P C00Q 1.375(5) . ?

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
C00C O006 C00R 117.3(3) . . ?
C00C N00A C00E 106.8(3) . . ?
C00C N00A B00S 127.0(3) . . ?
C00E N00A B00S 126.0(3) . . ?
C00P N00B C00G 105.7(3) . . ?
C00P N00B B00S 128.7(3) . . ?
C00G N00B B00S 125.6(3) . . ?
O006 C00C N00A 118.7(3) . . ?
O006 C00C C00J 130.2(3) . . ?
N00A C00C C00J 111.0(3) . . ?
C00E C00D C00G 121.0(3) . . ?
C00E C00D C00F 120.2(3) . . ?
C00G C00D C00F 118.8(3) . . ?
C00D C00E N00A 120.4(3) . . ?
C00D C00E C00K 132.4(3) . . ?
N00A C00E C00K 107.2(3) . . ?
C00I C00F C00H 115.9(3) . . ?
C00I C00F C00D 122.4(3) . . ?
C00H C00F C00D 121.7(3) . . ?
C00O C00G N00B 108.4(3) . . ?
C00O C00G C00D 130.7(3) . . ?
N00B C00G C00D 120.9(3) . . ?
F002 C00H C00N 117.4(3) . . ?
F002 C00H C00F 120.2(3) . . ?
C00N C00H C00F 122.4(3) . . ?
F003 C00I C00L 117.7(3) . . ?
F003 C00I C00F 119.9(3) . . ?
C00L C00I C00F 122.3(3) . . ?
C00K C00J C00C 106.2(3) . . ?
C00J C00K C00E 108.8(3) . . ?
F007 C00L C00M 120.4(3) . . ?
F007 C00L C00I 120.0(4) . . ?
C00M C00L C00I 119.6(3) . . ?
F005 C00M C00N 120.1(4) . . ?
F005 C00M C00L 120.1(4) . . ?
C00N C00M C00L 119.8(3) . . ?
F004 C00N C00M 120.5(3) . . ?
F004 C00N C00H 119.5(3) . . ?
C00M C00N C00H 119.9(3) . . ?
C00Q C00O C00G 108.0(3) . . ?
N00B C00P C00Q 111.5(3) . . ?
N00B C00P Br01 122.2(3) . . ?
C00Q C00P Br01 126.3(3) . . ?
C00P C00Q C00O 106.4(3) . . ?
F009 B00S F008 111.0(4) . . ?
F009 B00S N00B 110.3(3) . . ?
F008 B00S N00B 110.2(3) . . ?
F009 B00S N00A 109.6(3) . . ?
F008 B00S N00A 109.9(3) . . ?
N00B B00S N00A 105.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.058
