# 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_hwj_160427
_database_code_depnum_ccdc_archive 'CCDC 1477406'
_audit_update_record             
;
2016-04-30 deposited with the CCDC.
2016-12-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 Br F3 N3 O4'
_chemical_formula_weight         552.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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

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

_cell_length_a                   20.7435(3)
_cell_length_b                   8.96370(14)
_cell_length_c                   14.2512(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.7537(15)
_cell_angle_gamma                90.00
_cell_volume                     2603.31(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5765
_cell_measurement_theta_min      3.1380
_cell_measurement_theta_max      72.5440

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    2.643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5579
_exptl_absorpt_correction_T_max  0.8792
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5861
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         72.37
_reflns_number_total             3695
_reflns_number_gt                3679
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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)+(0.2000P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_number_reflns         3695
_refine_ls_number_parameters     316
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.1226
_refine_ls_wR_factor_ref         0.3516
_refine_ls_wR_factor_gt          0.3510
_refine_ls_goodness_of_fit_ref   1.874
_refine_ls_restrained_S_all      1.874
_refine_ls_shift/su_max          0.151
_refine_ls_shift/su_mean         0.035

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 0.32614(4) 0.22726(15) 0.24559(7) 0.0409(5) Uani 1 1 d . . .
C19 C 0.3663(6) -0.2167(16) 0.2117(6) 0.043(3) Uani 1 1 d . . .
H19A H 0.3432 -0.3061 0.2078 0.051 Uiso 1 1 calc R . .
C15 C 0.4667(4) -0.0839(10) 0.2096(6) 0.0190(15) Uani 1 1 d . . .
C16 C 0.4359(4) 0.0526(12) 0.2222(5) 0.0237(17) Uani 1 1 d . . .
H16A H 0.4584 0.1428 0.2251 0.028 Uiso 1 1 calc R . .
C14 C 0.4299(4) -0.2137(12) 0.2045(6) 0.0271(18) Uani 1 1 d . . .
C17 C 0.3689(4) 0.0455(13) 0.2302(6) 0.029(2) Uani 1 1 d . . .
O1 O 0.5981(4) -0.3131(7) 0.3746(4) 0.0285(15) Uani 1 1 d . . .
C8 C 0.5927(4) -0.1790(13) 0.3741(7) 0.0298(19) Uani 1 1 d . . .
C5 C 0.5814(4) 0.2245(11) 0.2933(7) 0.0290(18) Uani 1 1 d . . .
H5A H 0.5846 0.2420 0.2301 0.035 Uiso 1 1 calc R . .
C6 C 0.5823(4) 0.0769(10) 0.3314(6) 0.0188(16) Uani 1 1 d . . .
C7 C 0.5902(3) -0.0729(10) 0.2886(5) 0.0184(15) Uani 1 1 d . . .
C13 C 0.5343(5) -0.2885(10) 0.1824(6) 0.0293(19) Uani 1 1 d . . .
C12 C 0.5366(4) -0.1163(10) 0.1983(6) 0.0210(16) Uani 1 1 d . . .
N1 N 0.5829(3) -0.0971(10) 0.4504(5) 0.0246(15) Uani 1 1 d . . .
C1 C 0.5801(4) 0.0564(13) 0.4295(6) 0.029(2) Uani 1 1 d . . .
N3 N 0.5592(4) -0.0453(10) 0.1205(5) 0.0294(16) Uani 1 1 d . . .
H1A H 0.5348 -0.0241 0.0665 0.035 Uiso 1 1 calc R . .
N2 N 0.4731(5) -0.3350(11) 0.1893(6) 0.0353(19) Uani 1 1 d . . .
O4 O 0.7218(3) -0.0556(9) 0.3915(5) 0.0302(15) Uani 1 1 d . . .
C22 C 0.7118(4) -0.0023(11) 0.3036(7) 0.0264(18) Uani 1 1 d . . .
C10 C 0.6534(4) -0.0796(12) 0.2435(6) 0.0284(18) Uani 1 1 d . . .
H10A H 0.6647 -0.1846 0.2360 0.034 Uiso 1 1 calc R . .
C11 C 0.6301(4) -0.0135(10) 0.1453(6) 0.0234(17) Uani 1 1 d . . .
H11A H 0.6351 0.0950 0.1512 0.028 Uiso 1 1 calc R . .
C3 C 0.5720(4) 0.3168(13) 0.4480(10) 0.043(3) Uani 1 1 d . . .
H3A H 0.5660 0.3985 0.4858 0.051 Uiso 1 1 calc R . .
C2 C 0.5772(5) 0.1784(13) 0.4888(7) 0.036(2) Uani 1 1 d . . .
H2A H 0.5787 0.1661 0.5540 0.043 Uiso 1 1 calc R . .
O2 O 0.5762(4) -0.3648(9) 0.1623(5) 0.0352(17) Uani 1 1 d . . .
C18 C 0.3377(5) -0.0899(15) 0.2246(7) 0.035(2) Uani 1 1 d . . .
H18A H 0.2937 -0.0918 0.2301 0.042 Uiso 1 1 calc R . .
O3 O 0.7424(4) 0.0973(12) 0.2768(6) 0.045(2) Uani 1 1 d . . .
F3 F 0.7290(3) -0.0367(14) 0.0882(5) 0.064(3) Uani 1 1 d . . .
C21 C 0.6670(6) -0.0645(16) 0.0664(8) 0.045(3) Uani 1 1 d . . .
F2 F 0.6422(3) -0.0020(9) -0.0151(4) 0.0439(16) Uani 1 1 d . . .
F1 F 0.6614(5) -0.2156(9) 0.0535(6) 0.0541(19) Uani 1 1 d . . .
C4 C 0.5753(4) 0.3405(12) 0.3560(9) 0.037(3) Uani 1 1 d . . .
H4A H 0.5734 0.4380 0.3333 0.044 Uiso 1 1 calc R . .
C9 C 0.5817(5) -0.1635(14) 0.5430(6) 0.033(2) Uani 1 1 d . . .
H9A H 0.5839 -0.2702 0.5382 0.050 Uiso 1 1 calc R . .
H9B H 0.5418 -0.1360 0.5635 0.050 Uiso 1 1 calc R . .
H9C H 0.6186 -0.1283 0.5886 0.050 Uiso 1 1 calc R . .
C24 C 0.7595(6) -0.003(2) 0.5564(9) 0.056(3) Uani 1 1 d . . .
H24A H 0.7925 0.0463 0.6021 0.084 Uiso 1 1 calc R . .
H24B H 0.7603 -0.1079 0.5697 0.084 Uiso 1 1 calc R . .
H24C H 0.7171 0.0368 0.5606 0.084 Uiso 1 1 calc R . .
C23 C 0.7721(5) 0.0211(16) 0.4630(9) 0.047(3) Uani 1 1 d . . .
H23A H 0.8153 -0.0170 0.4590 0.056 Uiso 1 1 calc R . .
H23B H 0.7715 0.1272 0.4495 0.056 Uiso 1 1 calc R . .
C20 C 0.4490(8) -0.4890(14) 0.1738(11) 0.050(3) Uani 1 1 d . . .
H20A H 0.4846 -0.5531 0.1655 0.075 Uiso 1 1 calc R . .
H20B H 0.4153 -0.4929 0.1177 0.075 Uiso 1 1 calc R . .
H20C H 0.4315 -0.5215 0.2282 0.075 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 C17 1.887(11) . ?
C19 C18 1.31(2) . ?
C19 C14 1.344(14) . ?
C15 C16 1.407(13) . ?
C15 C14 1.385(13) . ?
C15 C12 1.517(10) . ?
C16 C17 1.418(11) . ?
C14 N2 1.450(15) . ?
C17 C18 1.371(17) . ?
O1 C8 1.208(15) . ?
C8 N1 1.358(13) . ?
C8 C7 1.540(13) . ?
C5 C4 1.392(15) . ?
C5 C6 1.429(13) . ?
C6 C1 1.419(12) . ?
C6 C7 1.497(11) . ?
C7 C10 1.565(10) . ?
C7 C12 1.585(10) . ?
C13 O2 1.183(13) . ?
C13 N2 1.357(14) . ?
C13 C12 1.559(11) . ?
C12 N3 1.431(11) . ?
N1 C1 1.407(14) . ?
N1 C9 1.453(11) . ?
C1 C2 1.390(14) . ?
N3 C11 1.473(11) . ?
N2 C20 1.471(13) . ?
O4 C22 1.320(12) . ?
O4 C23 1.485(11) . ?
C22 O3 1.198(14) . ?
C22 C10 1.515(13) . ?
C10 C11 1.514(12) . ?
C11 C21 1.543(12) . ?
C3 C4 1.34(2) . ?
C3 C2 1.366(19) . ?
F3 C21 1.290(15) . ?
C21 F2 1.305(12) . ?
C21 F1 1.369(17) . ?
C24 C23 1.42(2) . ?

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
C18 C19 C14 118.0(11) . . ?
C16 C15 C14 118.6(7) . . ?
C16 C15 C12 130.2(8) . . ?
C14 C15 C12 111.2(8) . . ?
C15 C16 C17 116.5(9) . . ?
C19 C14 C15 123.4(11) . . ?
C19 C14 N2 129.8(10) . . ?
C15 C14 N2 106.8(7) . . ?
C18 C17 C16 119.6(10) . . ?
C18 C17 Br1 123.0(7) . . ?
C16 C17 Br1 117.4(8) . . ?
O1 C8 N1 124.2(9) . . ?
O1 C8 C7 127.5(9) . . ?
N1 C8 C7 108.2(9) . . ?
C4 C5 C6 116.4(9) . . ?
C5 C6 C1 119.6(9) . . ?
C5 C6 C7 132.0(7) . . ?
C1 C6 C7 108.2(8) . . ?
C6 C7 C8 102.7(7) . . ?
C6 C7 C10 111.5(7) . . ?
C8 C7 C10 113.3(7) . . ?
C6 C7 C12 115.9(7) . . ?
C8 C7 C12 113.9(7) . . ?
C10 C7 C12 99.9(6) . . ?
O2 C13 N2 125.4(9) . . ?
O2 C13 C12 127.2(9) . . ?
N2 C13 C12 107.3(8) . . ?
N3 C12 C15 117.1(7) . . ?
N3 C12 C13 109.5(7) . . ?
C15 C12 C13 101.6(7) . . ?
N3 C12 C7 103.7(6) . . ?
C15 C12 C7 114.0(6) . . ?
C13 C12 C7 111.0(7) . . ?
C8 N1 C1 111.5(8) . . ?
C8 N1 C9 122.4(9) . . ?
C1 N1 C9 125.9(8) . . ?
C2 C1 N1 130.2(9) . . ?
C2 C1 C6 120.7(10) . . ?
N1 C1 C6 109.1(8) . . ?
C12 N3 C11 110.9(7) . . ?
C13 N2 C14 113.1(8) . . ?
C13 N2 C20 125.0(11) . . ?
C14 N2 C20 121.6(10) . . ?
C22 O4 C23 116.7(8) . . ?
O3 C22 O4 125.0(9) . . ?
O3 C22 C10 125.2(9) . . ?
O4 C22 C10 109.7(8) . . ?
C11 C10 C22 115.3(8) . . ?
C11 C10 C7 102.5(6) . . ?
C22 C10 C7 113.1(7) . . ?
N3 C11 C10 106.2(7) . . ?
N3 C11 C21 112.1(8) . . ?
C10 C11 C21 116.2(8) . . ?
C4 C3 C2 123.0(9) . . ?
C3 C2 C1 117.7(9) . . ?
C19 C18 C17 123.7(9) . . ?
F2 C21 F3 110.0(10) . . ?
F2 C21 F1 107.2(11) . . ?
F3 C21 F1 106.2(10) . . ?
F2 C21 C11 110.8(9) . . ?
F3 C21 C11 112.0(10) . . ?
F1 C21 C11 110.5(9) . . ?
C3 C4 C5 122.4(11) . . ?
C24 C23 O4 110.1(10) . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        72.37
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         7.970
_refine_diff_density_min         -1.007
_refine_diff_density_rms         0.251
