# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_cd212454
_database_code_depnum_ccdc_archive 'CCDC 1060973'
_audit_update_record             
;
2015-04-22 deposited with the CCDC.
2015-06-08 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 H17 Br F3 N O2'
_chemical_formula_weight         452.27

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.1964(10)
_cell_length_b                   13.4028(16)
_cell_length_c                   15.6110(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1924.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1471
_cell_measurement_theta_min      5.140
_cell_measurement_theta_max      50.735

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.101
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    2.181
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.25258
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_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            11763
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0851
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3776
_reflns_number_gt                2144
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0196P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3776
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_restrained_S_all      0.946
_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
Br1 Br 0.82869(7) 0.21879(4) -0.00335(4) 0.1008(2) Uani 1 1 d . . .
F1 F 0.5221(3) 0.6041(2) -0.19030(14) 0.0862(8) Uani 1 1 d . . .
F2 F 0.7019(3) 0.5876(2) -0.10502(16) 0.0826(8) Uani 1 1 d . . .
F3 F 0.5964(3) 0.7285(2) -0.11745(16) 0.0852(8) Uani 1 1 d . . .
N1 N 0.4979(3) 0.6320(2) 0.0365(2) 0.0464(8) Uani 1 1 d . . .
O1 O 0.5683(4) 0.8019(2) 0.04892(17) 0.0702(9) Uani 1 1 d . . .
O2 O 0.3704(4) 0.5432(3) -0.0615(2) 0.0849(10) Uani 1 1 d . . .
C1 C 0.4932(4) 0.6365(3) 0.1832(2) 0.0471(10) Uani 1 1 d . . .
C2 C 0.4319(5) 0.6214(3) 0.2633(3) 0.0603(12) Uani 1 1 d . . .
H2 H 0.4789 0.6436 0.3125 0.072 Uiso 1 1 calc R . .
C3 C 0.2981(6) 0.5722(3) 0.2689(3) 0.0753(15) Uani 1 1 d . . .
H3 H 0.2551 0.5618 0.3221 0.090 Uiso 1 1 calc R . .
C4 C 0.2307(5) 0.5396(4) 0.1961(4) 0.0773(14) Uani 1 1 d . . .
H4 H 0.1425 0.5062 0.2011 0.093 Uiso 1 1 calc R . .
C5 C 0.2878(5) 0.5541(3) 0.1162(3) 0.0646(12) Uani 1 1 d . . .
H5 H 0.2406 0.5315 0.0672 0.078 Uiso 1 1 calc R . .
C6 C 0.4191(4) 0.6041(3) 0.1118(3) 0.0497(10) Uani 1 1 d . . .
C7 C 0.6130(4) 0.7028(3) 0.0620(2) 0.0463(10) Uani 1 1 d . . .
H7 H 0.7033 0.6890 0.0308 0.056 Uiso 1 1 calc R . .
C8 C 0.5459(5) 0.8494(3) 0.1301(3) 0.0694(13) Uani 1 1 d . . .
H8A H 0.4448 0.8448 0.1472 0.083 Uiso 1 1 calc R . .
H8B H 0.5732 0.9193 0.1273 0.083 Uiso 1 1 calc R . .
C9 C 0.6412(4) 0.7944(3) 0.1920(2) 0.0556(10) Uani 1 1 d . . .
H9A H 0.6037 0.7990 0.2499 0.067 Uiso 1 1 calc R . .
H9B H 0.7399 0.8199 0.1909 0.067 Uiso 1 1 calc R . .
C10 C 0.6348(4) 0.6874(3) 0.1589(2) 0.0475(10) Uani 1 1 d . . .
C11 C 0.7746(4) 0.6275(3) 0.1797(2) 0.0486(10) Uani 1 1 d . . .
H11 H 0.8562 0.6673 0.1582 0.058 Uiso 1 1 calc R . .
C12 C 0.7971(5) 0.6175(3) 0.2742(3) 0.0636(12) Uani 1 1 d . . .
H12 H 0.7320 0.5778 0.3045 0.076 Uiso 1 1 calc R . .
C13 C 0.9016(6) 0.6605(4) 0.3171(3) 0.0906(17) Uani 1 1 d . . .
H13A H 0.9686 0.7007 0.2889 0.109 Uiso 1 1 calc R . .
H13B H 0.9090 0.6509 0.3760 0.109 Uiso 1 1 calc R . .
C14 C 0.4699(5) 0.5987(3) -0.0440(3) 0.0563(11) Uani 1 1 d . . .
C15 C 0.5728(5) 0.6309(4) -0.1150(3) 0.0610(12) Uani 1 1 d . . .
C16 C 0.7829(4) 0.5270(3) 0.1341(2) 0.0465(10) Uani 1 1 d . . .
C17 C 0.8819(5) 0.5126(3) 0.0701(3) 0.0614(12) Uani 1 1 d . . .
H17 H 0.9411 0.5658 0.0542 0.074 Uiso 1 1 calc R . .
C18 C 0.8983(5) 0.4221(4) 0.0276(2) 0.0689(13) Uani 1 1 d . . .
H18 H 0.9670 0.4142 -0.0155 0.083 Uiso 1 1 calc R . .
C19 C 0.8091(6) 0.3447(3) 0.0517(3) 0.0639(12) Uani 1 1 d . . .
C20 C 0.7090(5) 0.3565(3) 0.1159(3) 0.0758(13) Uani 1 1 d . . .
H20 H 0.6497 0.3034 0.1318 0.091 Uiso 1 1 calc R . .
C21 C 0.6967(5) 0.4470(3) 0.1567(3) 0.0654(12) Uani 1 1 d . . .
H21 H 0.6289 0.4544 0.2005 0.079 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 C19 1.902(4) . ?
F1 C15 1.315(4) . ?
F2 C15 1.331(5) . ?
F3 C15 1.326(5) . ?
N1 C14 1.358(5) . ?
N1 C6 1.431(4) . ?
N1 C7 1.476(5) . ?
O1 C7 1.406(4) . ?
O1 C8 1.433(5) . ?
O2 C14 1.211(5) . ?
C1 C6 1.376(5) . ?
C1 C2 1.388(5) . ?
C1 C10 1.518(5) . ?
C2 C3 1.398(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(6) . ?
C5 H5 0.9300 . ?
C7 C10 1.541(5) . ?
C7 H7 0.9800 . ?
C8 C9 1.499(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.525(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.550(5) . ?
C11 C12 1.495(5) . ?
C11 C16 1.526(5) . ?
C11 H11 0.9800 . ?
C12 C13 1.306(6) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C14 C15 1.520(6) . ?
C16 C17 1.365(5) . ?
C16 C21 1.380(5) . ?
C17 C18 1.391(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.370(6) . ?
C20 C21 1.376(6) . ?
C20 H20 0.9300 . ?
C21 H21 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
C14 N1 C6 125.4(4) . . ?
C14 N1 C7 126.6(3) . . ?
C6 N1 C7 108.0(3) . . ?
C7 O1 C8 109.5(3) . . ?
C6 C1 C2 118.8(4) . . ?
C6 C1 C10 111.4(3) . . ?
C2 C1 C10 129.8(4) . . ?
C1 C2 C3 118.9(4) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 122.6(4) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C4 C5 C6 116.6(4) . . ?
C4 C5 H5 121.7 . . ?
C6 C5 H5 121.7 . . ?
C1 C6 C5 123.1(4) . . ?
C1 C6 N1 109.4(3) . . ?
C5 C6 N1 127.5(4) . . ?
O1 C7 N1 111.0(3) . . ?
O1 C7 C10 107.9(3) . . ?
N1 C7 C10 105.8(3) . . ?
O1 C7 H7 110.7 . . ?
N1 C7 H7 110.7 . . ?
C10 C7 H7 110.7 . . ?
O1 C8 C9 105.5(3) . . ?
O1 C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
O1 C8 H8B 110.6 . . ?
C9 C8 H8B 110.6 . . ?
H8A C8 H8B 108.8 . . ?
C8 C9 C10 102.8(3) . . ?
C8 C9 H9A 111.2 . . ?
C10 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
C10 C9 H9B 111.2 . . ?
H9A C9 H9B 109.1 . . ?
C1 C10 C9 111.8(3) . . ?
C1 C10 C7 101.2(3) . . ?
C9 C10 C7 102.2(3) . . ?
C1 C10 C11 115.3(3) . . ?
C9 C10 C11 112.6(3) . . ?
C7 C10 C11 112.5(3) . . ?
C12 C11 C16 112.0(3) . . ?
C12 C11 C10 111.6(3) . . ?
C16 C11 C10 113.6(3) . . ?
C12 C11 H11 106.4 . . ?
C16 C11 H11 106.4 . . ?
C10 C11 H11 106.4 . . ?
C13 C12 C11 124.6(5) . . ?
C13 C12 H12 117.7 . . ?
C11 C12 H12 117.7 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
O2 C14 N1 123.6(4) . . ?
O2 C14 C15 118.7(4) . . ?
N1 C14 C15 117.6(4) . . ?
F1 C15 F3 107.6(4) . . ?
F1 C15 F2 107.6(4) . . ?
F3 C15 F2 106.7(4) . . ?
F1 C15 C14 110.7(4) . . ?
F3 C15 C14 113.7(4) . . ?
F2 C15 C14 110.3(4) . . ?
C17 C16 C21 117.5(4) . . ?
C17 C16 C11 120.0(4) . . ?
C21 C16 C11 122.5(4) . . ?
C16 C17 C18 123.0(4) . . ?
C16 C17 H17 118.5 . . ?
C18 C17 H17 118.5 . . ?
C19 C18 C17 117.6(4) . . ?
C19 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?
C20 C19 C18 120.9(4) . . ?
C20 C19 Br1 119.8(4) . . ?
C18 C19 Br1 119.3(4) . . ?
C19 C20 C21 119.8(4) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 121.3(4) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?

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 1.1(6) . . . . ?
C10 C1 C2 C3 179.7(4) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C3 C4 C5 -0.9(7) . . . . ?
C3 C4 C5 C6 0.0(7) . . . . ?
C2 C1 C6 C5 -2.1(6) . . . . ?
C10 C1 C6 C5 179.1(4) . . . . ?
C2 C1 C6 N1 176.9(3) . . . . ?
C10 C1 C6 N1 -1.9(4) . . . . ?
C4 C5 C6 C1 1.5(6) . . . . ?
C4 C5 C6 N1 -177.3(4) . . . . ?
C14 N1 C6 C1 168.7(4) . . . . ?
C7 N1 C6 C1 -11.5(4) . . . . ?
C14 N1 C6 C5 -12.3(6) . . . . ?
C7 N1 C6 C5 167.4(4) . . . . ?
C8 O1 C7 N1 110.0(4) . . . . ?
C8 O1 C7 C10 -5.5(5) . . . . ?
C14 N1 C7 O1 82.8(5) . . . . ?
C6 N1 C7 O1 -96.9(4) . . . . ?
C14 N1 C7 C10 -160.4(4) . . . . ?
C6 N1 C7 C10 19.9(4) . . . . ?
C7 O1 C8 C9 25.6(5) . . . . ?
O1 C8 C9 C10 -34.8(4) . . . . ?
C6 C1 C10 C9 121.7(4) . . . . ?
C2 C1 C10 C9 -56.9(5) . . . . ?
C6 C1 C10 C7 13.6(4) . . . . ?
C2 C1 C10 C7 -165.1(4) . . . . ?
C6 C1 C10 C11 -108.1(4) . . . . ?
C2 C1 C10 C11 73.3(5) . . . . ?
C8 C9 C10 C1 -77.1(4) . . . . ?
C8 C9 C10 C7 30.3(4) . . . . ?
C8 C9 C10 C11 151.3(3) . . . . ?
O1 C7 C10 C1 99.3(3) . . . . ?
N1 C7 C10 C1 -19.6(4) . . . . ?
O1 C7 C10 C9 -16.2(4) . . . . ?
N1 C7 C10 C9 -135.0(3) . . . . ?
O1 C7 C10 C11 -137.2(3) . . . . ?
N1 C7 C10 C11 104.0(3) . . . . ?
C1 C10 C11 C12 -67.2(4) . . . . ?
C9 C10 C11 C12 62.6(4) . . . . ?
C7 C10 C11 C12 177.5(3) . . . . ?
C1 C10 C11 C16 60.5(4) . . . . ?
C9 C10 C11 C16 -169.7(3) . . . . ?
C7 C10 C11 C16 -54.8(4) . . . . ?
C16 C11 C12 C13 119.9(5) . . . . ?
C10 C11 C12 C13 -111.5(5) . . . . ?
C6 N1 C14 O2 2.4(7) . . . . ?
C7 N1 C14 O2 -177.3(4) . . . . ?
C6 N1 C14 C15 -175.6(4) . . . . ?
C7 N1 C14 C15 4.7(6) . . . . ?
O2 C14 C15 F1 10.1(6) . . . . ?
N1 C14 C15 F1 -171.9(4) . . . . ?
O2 C14 C15 F3 131.3(4) . . . . ?
N1 C14 C15 F3 -50.6(5) . . . . ?
O2 C14 C15 F2 -108.9(5) . . . . ?
N1 C14 C15 F2 69.2(5) . . . . ?
C12 C11 C16 C17 -122.4(4) . . . . ?
C10 C11 C16 C17 110.1(4) . . . . ?
C12 C11 C16 C21 55.3(5) . . . . ?
C10 C11 C16 C21 -72.2(5) . . . . ?
C21 C16 C17 C18 0.2(6) . . . . ?
C11 C16 C17 C18 178.0(4) . . . . ?
C16 C17 C18 C19 0.4(6) . . . . ?
C17 C18 C19 C20 -0.7(7) . . . . ?
C17 C18 C19 Br1 -179.2(3) . . . . ?
C18 C19 C20 C21 0.3(7) . . . . ?
Br1 C19 C20 C21 178.8(3) . . . . ?
C19 C20 C21 C16 0.4(7) . . . . ?
C17 C16 C21 C20 -0.6(6) . . . . ?
C11 C16 C21 C20 -178.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.043
