# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_FAK_WIN573_121118
_database_code_depnum_ccdc_archive 'CCDC 1911986'
loop_
_audit_author_name
_audit_author_address
'Kirill Faust'
;Johannes Kepler University Linz
Austria
;
_audit_update_record             
;
2019-04-24 deposited with the CCDC.	2019-05-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            WIN573
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H21 Br F3 N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         572.37

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1546(3)
_cell_length_b                   10.8743(4)
_cell_length_c                   13.3084(5)
_cell_angle_alpha                85.375(2)
_cell_angle_beta                 77.4740(10)
_cell_angle_gamma                63.9990(10)
_cell_volume                     1289.22(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9941
_cell_measurement_theta_min      2.5586
_cell_measurement_theta_max      23.8843
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'lustrous colourless'
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.371
_exptl_crystal_size_min          0.272
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580

_exptl_absorpt_coefficient_mu    1.650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_T_max  0.66

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              'sealed tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 Quest Eco'
_diffrn_measurement_method       omega

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            110108
_diffrn_reflns_av_R_equivalents  0.1247
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             4719
_reflns_number_gt                3229
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1055
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_refine_ls_number_reflns         4719
_refine_ls_number_parameters     339
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+0.6806P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.353
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Br Br -0.2901 2.4595 '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'
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'

_computing_data_collection       'APEX3 v2016.9-0'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'
_computing_publication_material  'publCIF, Diamond 3.2k'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.03977(4) 0.27257(5) 0.94723(3) 0.06890(17) Uani d . . . 1 . .
H H1 0.842(4) 0.317(3) 0.7547(16) 0.046(10) Uiso d . . D 1 . .
C C1 0.7367(3) 0.2446(3) 0.6942(2) 0.0350(7) Uani d . . . 1 . .
N N1 0.8365(3) 0.3087(3) 0.6916(2) 0.0397(6) Uani d . . D 1 . .
O O1 0.7968(3) 0.1595(2) 0.85893(17) 0.0518(6) Uani d . . . 1 . .
F F1 0.8268(2) 0.21543(19) 0.51376(13) 0.0556(5) Uani d . . . 1 . .
F F2 0.9250(2) 0.0422(2) 0.60760(15) 0.0623(6) Uani d . . . 1 . .
C C2 0.5758(3) 0.3624(3) 0.6893(2) 0.0354(7) Uani d . . . 1 . .
H H2 0.5647 0.3616 0.6181 0.042 Uiso calc U . R 1 . .
O O2 0.6785(3) 0.0728(2) 0.78353(16) 0.0470(6) Uani d . . . 1 . .
F F3 0.7028(2) 0.1038(2) 0.58141(14) 0.0576(5) Uani d . . . 1 . .
C C3 0.5939(3) 0.4951(3) 0.7014(2) 0.0349(7) Uani d . . . 1 . .
O O3 0.6191(2) 0.5001(2) 0.87971(16) 0.0483(6) Uani d . . . 1 . .
O O4 0.5049(3) 0.6213(2) 0.55214(17) 0.0555(6) Uani d . . . 1 . .
C C4 0.7625(3) 0.4473(3) 0.6524(2) 0.0383(7) Uani d . . . 1 . .
H H4 0.7724 0.4371 0.5782 0.046 Uiso calc U . R 1 . .
C C6 0.7409(3) 0.1547(3) 0.7897(2) 0.0380(7) Uani d . . . 1 . .
C C5 0.7963(4) 0.1508(3) 0.5995(2) 0.0449(8) Uani d . . . 1 . .
C C9 0.4425(3) 0.3461(3) 0.7559(2) 0.0376(7) Uani d . . . 1 . .
C C8 0.5791(5) -0.0830(5) 0.8495(4) 0.0799(13) Uani d . . . 1 . .
H H8A 0.4805 -0.0142 0.8462 0.12 Uiso calc U . R 1 . .
H H8B 0.5728 -0.1447 0.9041 0.12 Uiso calc U . R 1 . .
H H8C 0.6244 -0.1329 0.7853 0.12 Uiso calc U . R 1 . .
C C7 0.6714(4) -0.0168(4) 0.8696(3) 0.0604(10) Uani d . . . 1 . .
H H7A 0.626 0.0356 0.9337 0.073 Uiso calc U . R 1 . .
H H7B 0.771 -0.0851 0.8743 0.073 Uiso calc U . R 1 . .
C C10 0.3550(4) 0.3109(3) 0.7081(3) 0.0469(8) Uani d . . . 1 . .
H H10 0.3761 0.3032 0.6367 0.056 Uiso calc U . R 1 . .
C C11 0.2374(4) 0.2871(4) 0.7641(3) 0.0550(9) Uani d . . . 1 . .
H H11 0.1818 0.2612 0.7308 0.066 Uiso calc U . R 1 . .
C C12 0.2032(4) 0.3018(3) 0.8689(3) 0.0476(8) Uani d . . . 1 . .
C C13 0.2852(4) 0.3395(4) 0.9191(3) 0.0492(9) Uani d . . . 1 . .
H H13 0.2602 0.3514 0.9903 0.059 Uiso calc U . R 1 . .
C C14 0.4053(4) 0.3593(3) 0.8623(2) 0.0456(8) Uani d . . . 1 . .
H H14 0.4627 0.3821 0.8963 0.055 Uiso calc U . R 1 . .
C C15 0.5498(3) 0.5512(3) 0.8114(2) 0.0390(7) Uani d . . . 1 . .
C C16 0.4136(3) 0.6809(3) 0.8188(2) 0.0392(7) Uani d . . . 1 . .
C C17 0.3230(4) 0.7592(4) 0.9059(3) 0.0520(9) Uani d . . . 1 . .
H H17 0.342 0.7311 0.9712 0.062 Uiso calc U . R 1 . .
C C18 0.2045(4) 0.8794(4) 0.8918(3) 0.0640(11) Uani d . . . 1 . .
H H18 0.1417 0.9336 0.949 0.077 Uiso calc U . R 1 . .
C C19 0.1755(4) 0.9228(4) 0.7947(3) 0.0662(11) Uani d . . . 1 . .
H H19 0.095 1.0059 0.7879 0.079 Uiso calc U . R 1 . .
C C20 0.2649(4) 0.8439(4) 0.7079(3) 0.0551(9) Uani d . . . 1 . .
H H20 0.2461 0.8728 0.6426 0.066 Uiso calc U . R 1 . .
C C21 0.3829(3) 0.7210(3) 0.7216(2) 0.0411(8) Uani d . . . 1 . .
C C22 0.4926(3) 0.6153(3) 0.6446(2) 0.0392(7) Uani d . . . 1 . .
C C23 0.8312(3) 0.5411(3) 0.6644(2) 0.0422(8) Uani d . . . 1 . .
C C24 0.8901(4) 0.5421(4) 0.7483(3) 0.0532(9) Uani d . . . 1 . .
H H24 0.886 0.4835 0.8025 0.064 Uiso calc U . R 1 . .
C C25 0.9555(4) 0.6294(4) 0.7529(3) 0.0651(11) Uani d . . . 1 . .
H H25 0.9963 0.6279 0.8095 0.078 Uiso calc U . R 1 . .
C C26 0.9600(5) 0.7173(4) 0.6746(4) 0.0705(12) Uani d . . . 1 . .
H H26 1.0042 0.7754 0.6777 0.085 Uiso calc U . R 1 . .
C C27 0.8999(5) 0.7203(4) 0.5920(4) 0.0772(13) Uani d . . . 1 . .
H H27 0.9011 0.782 0.5396 0.093 Uiso calc U . R 1 . .
C C28 0.8373(4) 0.6320(4) 0.5857(3) 0.0616(10) Uani d . . . 1 . .
H H28 0.7986 0.6332 0.5281 0.074 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C12 . 1.897(3) ?
C1 N1 . 1.454(4) ?
C1 C5 . 1.527(4) ?
C1 C6 . 1.536(4) ?
C1 C2 . 1.585(4) ?
N1 C4 . 1.470(4) ?
N1 H1 . 0.869(17) ?
O1 C6 . 1.197(4) ?
F1 C5 . 1.342(3) ?
F2 C5 . 1.342(4) ?
C2 C9 . 1.522(4) ?
C2 C3 . 1.557(4) ?
C2 H2 . 0.98 ?
O2 C6 . 1.316(4) ?
O2 C7 . 1.453(4) ?
F3 C5 . 1.328(4) ?
C3 C15 . 1.528(4) ?
C3 C22 . 1.529(4) ?
C3 C4 . 1.555(4) ?
O3 C15 . 1.219(4) ?
O4 C22 . 1.209(3) ?
C4 C23 . 1.500(4) ?
C4 H4 . 0.98 ?
C9 C14 . 1.386(4) ?
C9 C10 . 1.386(4) ?
C8 C7 . 1.483(5) ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C10 C11 . 1.379(4) ?
C10 H10 . 0.93 ?
C11 C12 . 1.367(5) ?
C11 H11 . 0.93 ?
C12 C13 . 1.376(5) ?
C13 C14 . 1.382(4) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C15 C16 . 1.471(4) ?
C16 C17 . 1.387(4) ?
C16 C21 . 1.388(4) ?
C17 C18 . 1.368(5) ?
C17 H17 . 0.93 ?
C18 C19 . 1.387(5) ?
C18 H18 . 0.93 ?
C19 C20 . 1.384(5) ?
C19 H19 . 0.93 ?
C20 C21 . 1.381(5) ?
C20 H20 . 0.93 ?
C21 C22 . 1.479(4) ?
C23 C24 . 1.380(5) ?
C23 C28 . 1.392(5) ?
C24 C25 . 1.387(5) ?
C24 H24 . 0.93 ?
C25 C26 . 1.364(6) ?
C25 H25 . 0.93 ?
C26 C27 . 1.359(6) ?
C26 H26 . 0.93 ?
C27 C28 . 1.381(5) ?
C27 H27 . 0.93 ?
C28 H28 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C5 . . 107.6(2) ?
N1 C1 C6 . . 109.6(2) ?
C5 C1 C6 . . 107.6(2) ?
N1 C1 C2 . . 107.6(2) ?
C5 C1 C2 . . 110.0(2) ?
C6 C1 C2 . . 114.2(2) ?
C1 N1 C4 . . 106.5(2) ?
C1 N1 H1 . . 107.(2) ?
C4 N1 H1 . . 107.(2) ?
C9 C2 C3 . . 118.9(2) ?
C9 C2 C1 . . 116.9(2) ?
C3 C2 C1 . . 103.1(2) ?
C9 C2 H2 . . 105.6 ?
C3 C2 H2 . . 105.6 ?
C1 C2 H2 . . 105.6 ?
C6 O2 C7 . . 117.6(3) ?
C15 C3 C22 . . 102.8(2) ?
C15 C3 C4 . . 114.0(2) ?
C22 C3 C4 . . 112.4(2) ?
C15 C3 C2 . . 115.3(2) ?
C22 C3 C2 . . 112.0(2) ?
C4 C3 C2 . . 100.8(2) ?
N1 C4 C23 . . 114.8(3) ?
N1 C4 C3 . . 104.5(2) ?
C23 C4 C3 . . 117.2(2) ?
N1 C4 H4 . . 106.5 ?
C23 C4 H4 . . 106.5 ?
C3 C4 H4 . . 106.5 ?
O1 C6 O2 . . 125.8(3) ?
O1 C6 C1 . . 122.9(3) ?
O2 C6 C1 . . 111.2(3) ?
F3 C5 F2 . . 107.6(3) ?
F3 C5 F1 . . 105.9(3) ?
F2 C5 F1 . . 106.3(2) ?
F3 C5 C1 . . 114.4(3) ?
F2 C5 C1 . . 110.9(3) ?
F1 C5 C1 . . 111.3(3) ?
C14 C9 C10 . . 117.4(3) ?
C14 C9 C2 . . 124.2(3) ?
C10 C9 C2 . . 118.4(3) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O2 C7 C8 . . 106.5(3) ?
O2 C7 H7A . . 110.4 ?
C8 C7 H7A . . 110.4 ?
O2 C7 H7B . . 110.4 ?
C8 C7 H7B . . 110.4 ?
H7A C7 H7B . . 108.6 ?
C11 C10 C9 . . 121.5(3) ?
C11 C10 H10 . . 119.3 ?
C9 C10 H10 . . 119.3 ?
C12 C11 C10 . . 119.7(3) ?
C12 C11 H11 . . 120.2 ?
C10 C11 H11 . . 120.2 ?
C11 C12 C13 . . 120.6(3) ?
C11 C12 Br1 . . 120.3(3) ?
C13 C12 Br1 . . 119.0(3) ?
C12 C13 C14 . . 119.1(3) ?
C12 C13 H13 . . 120.5 ?
C14 C13 H13 . . 120.5 ?
C13 C14 C9 . . 121.7(3) ?
C13 C14 H14 . . 119.1 ?
C9 C14 H14 . . 119.1 ?
O3 C15 C16 . . 126.0(3) ?
O3 C15 C3 . . 125.8(3) ?
C16 C15 C3 . . 108.2(3) ?
C17 C16 C21 . . 121.3(3) ?
C17 C16 C15 . . 128.7(3) ?
C21 C16 C15 . . 110.0(3) ?
C18 C17 C16 . . 117.4(3) ?
C18 C17 H17 . . 121.3 ?
C16 C17 H17 . . 121.3 ?
C17 C18 C19 . . 121.8(3) ?
C17 C18 H18 . . 119.1 ?
C19 C18 H18 . . 119.1 ?
C20 C19 C18 . . 120.8(4) ?
C20 C19 H19 . . 119.6 ?
C18 C19 H19 . . 119.6 ?
C21 C20 C19 . . 117.7(3) ?
C21 C20 H20 . . 121.2 ?
C19 C20 H20 . . 121.2 ?
C20 C21 C16 . . 120.9(3) ?
C20 C21 C22 . . 129.5(3) ?
C16 C21 C22 . . 109.6(3) ?
O4 C22 C21 . . 127.1(3) ?
O4 C22 C3 . . 124.6(3) ?
C21 C22 C3 . . 108.3(2) ?
C24 C23 C28 . . 117.8(3) ?
C24 C23 C4 . . 124.1(3) ?
C28 C23 C4 . . 118.1(3) ?
C23 C24 C25 . . 120.9(3) ?
C23 C24 H24 . . 119.5 ?
C25 C24 H24 . . 119.5 ?
C26 C25 C24 . . 120.0(4) ?
C26 C25 H25 . . 120.0 ?
C24 C25 H25 . . 120.0 ?
C27 C26 C25 . . 120.3(4) ?
C27 C26 H26 . . 119.9 ?
C25 C26 H26 . . 119.9 ?
C26 C27 C28 . . 120.2(4) ?
C26 C27 H27 . . 119.9 ?
C28 C27 H27 . . 119.9 ?
C27 C28 C23 . . 120.8(4) ?
C27 C28 H28 . . 119.6 ?
C23 C28 H28 . . 119.6 ?




_publcif_funding_html            
;
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
