# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_b
_database_code_depnum_ccdc_archive 'CCDC 1420993'
_audit_update_record             
;
2015-08-28 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 Br F N O'
_chemical_formula_weight         396.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
Br Br -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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                   5.9396(12)
_cell_length_b                   11.302(2)
_cell_length_c                   13.413(3)
_cell_angle_alpha                96.05(3)
_cell_angle_beta                 99.59(3)
_cell_angle_gamma                101.21(3)
_cell_volume                     862.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3034
_cell_measurement_theta_min      1.5557
_cell_measurement_theta_max      27.4282

_exptl_crystal_description       plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.069
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    2.402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_T_max  0.852

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7905
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         27.40
_reflns_number_total             3856
_reflns_number_gt                3496
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (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)+(0.0689P)²+0.8767P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3856
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1315
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 1.12229(6) 0.38682(3) -0.19444(3) 0.04387(15) Uani 1 1 d . . .
F1 F 0.7159(4) 0.62498(17) 0.44820(16) 0.0481(5) Uani 1 1 d . . .
O1 O 0.3665(3) 0.1733(2) 0.11132(15) 0.0290(4) Uani 1 1 d . . .
N1 N 0.6583(4) 0.0630(2) 0.15614(18) 0.0274(5) Uani 1 1 d . . .
C1 C 0.3488(5) 0.0614(3) 0.2572(2) 0.0271(6) Uani 1 1 d . . .
C2 C 0.2302(5) 0.0125(3) 0.3293(2) 0.0296(6) Uani 1 1 d . . .
H2 H 0.1072 0.0469 0.3485 0.035 Uiso 1 1 calc R . .
C3 C 0.2884(5) -0.0865(3) 0.3742(2) 0.0319(6) Uani 1 1 d . . .
C4 C 0.4692(6) -0.1352(3) 0.3437(2) 0.0335(6) Uani 1 1 d . . .
H4 H 0.5106 -0.2028 0.3729 0.040 Uiso 1 1 calc R . .
C5 C 0.5902(5) -0.0869(3) 0.2716(2) 0.0323(6) Uani 1 1 d . . .
H5 H 0.7129 -0.1213 0.2521 0.039 Uiso 1 1 calc R . .
C6 C 0.5300(5) 0.0124(3) 0.2280(2) 0.0271(6) Uani 1 1 d . . .
C7 C 0.5703(5) 0.1380(3) 0.1049(2) 0.0256(6) Uani 1 1 d . . .
C8 C 0.2915(5) 0.1701(3) 0.2104(2) 0.0263(6) Uani 1 1 d . . .
H8 H 0.1180 0.1614 0.1983 0.032 Uiso 1 1 calc R . .
C9 C 0.4031(5) 0.2915(3) 0.2752(2) 0.0274(6) Uani 1 1 d . . .
C10 C 0.6314(5) 0.3119(3) 0.3322(2) 0.0331(6) Uani 1 1 d . . .
H10 H 0.7139 0.2478 0.3316 0.040 Uiso 1 1 calc R . .
C11 C 0.7380(6) 0.4242(3) 0.3891(2) 0.0366(7) Uani 1 1 d . . .
H11 H 0.8938 0.4384 0.4263 0.044 Uiso 1 1 calc R . .
C12 C 0.6131(6) 0.5148(3) 0.3907(2) 0.0367(7) Uani 1 1 d . . .
C13 C 0.3882(6) 0.4988(3) 0.3356(3) 0.0398(7) Uani 1 1 d . . .
H13 H 0.3068 0.5632 0.3372 0.048 Uiso 1 1 calc R . .
C14 C 0.2843(5) 0.3859(3) 0.2777(3) 0.0351(7) Uani 1 1 d . . .
H14 H 0.1299 0.3732 0.2393 0.042 Uiso 1 1 calc R . .
C15 C 0.6892(5) 0.1952(3) 0.0271(2) 0.0274(6) Uani 1 1 d . . .
C16 C 0.8550(5) 0.1422(3) -0.0118(2) 0.0288(6) Uani 1 1 d . . .
H16 H 0.8812 0.0669 0.0077 0.035 Uiso 1 1 calc R . .
C17 C 0.9827(5) 0.1973(3) -0.0786(2) 0.0313(6) Uani 1 1 d . . .
H17 H 1.0955 0.1607 -0.1051 0.038 Uiso 1 1 calc R . .
C18 C 0.9412(5) 0.3074(3) -0.1057(2) 0.0313(6) Uani 1 1 d . . .
C19 C 0.7733(6) 0.3616(3) -0.0702(3) 0.0383(7) Uani 1 1 d . . .
H19 H 0.7456 0.4361 -0.0911 0.046 Uiso 1 1 calc R . .
C20 C 0.6468(6) 0.3050(3) -0.0038(2) 0.0341(7) Uani 1 1 d . . .
H20 H 0.5309 0.3407 0.0209 0.041 Uiso 1 1 calc R . .
C21 C 0.1642(7) -0.1371(3) 0.4552(3) 0.0423(8) Uani 1 1 d . . .
H21A H 0.2397 -0.0905 0.5222 0.063 Uiso 1 1 calc R . .
H21B H 0.1723 -0.2228 0.4556 0.063 Uiso 1 1 calc R . .
H21C H 0.0002 -0.1307 0.4403 0.063 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 C18 1.912(3) . ?
F1 C12 1.366(4) . ?
O1 C7 1.359(3) . ?
O1 C8 1.472(3) . ?
N1 C7 1.280(4) . ?
N1 C6 1.424(4) . ?
C1 C2 1.388(4) . ?
C1 C6 1.394(4) . ?
C1 C8 1.507(4) . ?
C2 C3 1.399(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(5) . ?
C3 C21 1.511(4) . ?
C4 C5 1.393(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(4) . ?
C5 H5 0.9500 . ?
C7 C15 1.488(4) . ?
C8 C9 1.510(4) . ?
C8 H8 1.0000 . ?
C9 C14 1.390(4) . ?
C9 C10 1.404(4) . ?
C10 C11 1.385(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(5) . ?
C13 C14 1.392(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.391(4) . ?
C15 C20 1.404(4) . ?
C16 C17 1.388(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(5) . ?
C19 C20 1.387(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C7 O1 C8 116.2(2) . . ?
C7 N1 C6 116.5(2) . . ?
C2 C1 C6 120.3(3) . . ?
C2 C1 C8 121.6(3) . . ?
C6 C1 C8 118.1(3) . . ?
C1 C2 C3 121.2(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 117.8(3) . . ?
C4 C3 C21 121.0(3) . . ?
C2 C3 C21 121.1(3) . . ?
C5 C4 C3 121.6(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 N1 121.3(3) . . ?
C5 C6 N1 119.2(3) . . ?
N1 C7 O1 126.7(3) . . ?
N1 C7 C15 120.8(3) . . ?
O1 C7 C15 112.4(2) . . ?
O1 C8 C1 110.2(2) . . ?
O1 C8 C9 107.4(2) . . ?
C1 C8 C9 114.5(2) . . ?
O1 C8 H8 108.2 . . ?
C1 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
C14 C9 C10 118.8(3) . . ?
C14 C9 C8 120.7(3) . . ?
C10 C9 C8 120.5(3) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 118.5(3) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
F1 C12 C11 118.7(3) . . ?
F1 C12 C13 118.7(3) . . ?
C11 C12 C13 122.6(3) . . ?
C12 C13 C14 118.3(3) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C9 C14 C13 120.9(3) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C20 119.2(3) . . ?
C16 C15 C7 119.3(3) . . ?
C20 C15 C7 121.4(3) . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C18 C17 C16 118.2(3) . . ?
C18 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
C17 C18 C19 122.1(3) . . ?
C17 C18 Br1 118.7(2) . . ?
C19 C18 Br1 119.2(2) . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 C15 120.3(3) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
C3 C21 H21A 109.5 . . ?
C3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.40
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.090
