# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1584589'
_audit_update_record             
;
2017-11-08 deposited with the CCDC.
2018-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H23 Br F N3 O4'
_chemical_formula_weight         600.43

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                   9.608(4)
_cell_length_b                   9.984(5)
_cell_length_c                   28.090(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2695(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9621
_cell_measurement_theta_min      2.241
_cell_measurement_theta_max      26.553

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224
_exptl_absorpt_coefficient_mu    1.575
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6494
_exptl_absorpt_correction_T_max  0.8335
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
__diffrn_radiation_source        '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_decay_%        ?
_diffrn_reflns_number            36796
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4741
_reflns_number_gt                4364
_reflns_threshold_expression     >2sigma(I)

__computing_data_collection      'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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
_chemical_absolute_configuration s
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0680P)²+3.9519P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    'riding mode'
_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   0.040(13)
_refine_ls_number_reflns         4741
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
F1 F 1.2437(3) 0.6081(4) 0.73866(12) 0.0756(10) Uani 1 1 d . . .
C6 C 1.5565(4) 0.7723(4) 0.57904(15) 0.0353(9) Uani 1 1 d . . .
C8 C 1.3611(4) 1.0539(4) 0.57613(15) 0.0362(9) Uani 1 1 d . . .
C9 C 1.4064(4) 0.7998(4) 0.59274(15) 0.0335(9) Uani 1 1 d . . .
H9A H 1.3494 0.7863 0.5642 0.040 Uiso 1 1 calc R . .
C10 C 0.9965(5) 0.7919(5) 0.66945(16) 0.0446(10) Uani 1 1 d . . .
H10A H 0.9935 0.8495 0.6434 0.053 Uiso 1 1 calc R . .
C11 C 1.3740(4) 0.9415(4) 0.61198(14) 0.0313(8) Uani 1 1 d . . .
C12 C 1.3503(4) 0.7050(4) 0.63155(15) 0.0364(9) Uani 1 1 d . . .
C13 C 1.1239(4) 0.7451(4) 0.68475(15) 0.0359(9) Uani 1 1 d . . .
C14 C 1.4444(4) 1.1588(4) 0.59053(16) 0.0380(9) Uani 1 1 d . . .
C15 C 1.8123(5) 1.1257(5) 0.61860(18) 0.0494(11) Uani 1 1 d . . .
H15A H 1.7605 1.0521 0.6088 0.059 Uiso 1 1 calc R . .
C16 C 1.7585(5) 0.6273(6) 0.58036(19) 0.0566(12) Uani 1 1 d . . .
H16A H 1.8015 0.5494 0.5910 0.068 Uiso 1 1 calc R . .
C17 C 1.6235(5) 0.6589(4) 0.59492(17) 0.0444(11) Uani 1 1 d . . .
C18 C 1.1214(5) 0.6555(5) 0.72299(17) 0.0489(12) Uani 1 1 d . . .
C21 C 1.8275(5) 0.7135(6) 0.54996(19) 0.0601(14) Uani 1 1 d . . .
H21A H 1.9181 0.6944 0.5404 0.072 Uiso 1 1 calc R . .
C22 C 1.7498(4) 1.2245(4) 0.64558(16) 0.0392(10) Uani 1 1 d . . .
C23 C 1.6268(5) 0.8557(5) 0.54751(15) 0.0435(10) Uani 1 1 d . . .
H23A H 1.5824 0.9313 0.5355 0.052 Uiso 1 1 calc R . .
C24 C 1.9518(5) 1.1352(6) 0.60602(19) 0.0589(13) Uani 1 1 d . . .
H24A H 1.9925 1.0685 0.5876 0.071 Uiso 1 1 calc R . .
C25 C 1.4853(4) 0.9980(4) 0.64639(14) 0.0316(8) Uani 1 1 d . . .
C26 C 1.2611(4) 0.7964(4) 0.66530(14) 0.0341(9) Uani 1 1 d . . .
H26A H 1.3196 0.8204 0.6925 0.041 Uiso 1 1 calc R . .
C27 C 1.2853(5) 1.0625(5) 0.53497(16) 0.0496(11) Uani 1 1 d . . .
H27A H 1.2293 0.9916 0.5253 0.059 Uiso 1 1 calc R . .
C29 C 2.0295(6) 1.2420(6) 0.6206(3) 0.0703(17) Uani 1 1 d . . .
H29A H 2.1228 1.2489 0.6121 0.084 Uiso 1 1 calc R . .
C30 C 1.4534(6) 1.2769(5) 0.5649(2) 0.0566(13) Uani 1 1 d . . .
H30A H 1.5087 1.3480 0.5750 0.068 Uiso 1 1 calc R . .
C31 C 0.8740(5) 0.7566(5) 0.69119(18) 0.0525(12) Uani 1 1 d . . .
H31A H 0.7896 0.7915 0.6807 0.063 Uiso 1 1 calc R . .
C32 C 1.7626(5) 0.8275(5) 0.53371(18) 0.0519(12) Uani 1 1 d . . .
H32A H 1.8096 0.8857 0.5135 0.062 Uiso 1 1 calc R . .
C33 C 1.9678(6) 1.3388(7) 0.6478(3) 0.090(2) Uani 1 1 d . . .
H33A H 2.0201 1.4115 0.6582 0.108 Uiso 1 1 calc R . .
C34 C 1.2933(7) 1.1782(6) 0.5081(2) 0.0716(16) Uani 1 1 d . . .
H34A H 1.2436 1.1852 0.4798 0.086 Uiso 1 1 calc R . .
C35 C 1.8292(6) 1.3301(5) 0.6602(3) 0.0688(17) Uani 1 1 d . . .
H35A H 1.7893 1.3971 0.6787 0.083 Uiso 1 1 calc R . .
C38 C 1.5991(5) 1.2155(5) 0.66144(18) 0.0454(11) Uani 1 1 d . . .
H38A H 1.5968 1.1855 0.6943 0.054 Uiso 1 1 calc R . .
H38B H 1.5587 1.3045 0.6604 0.054 Uiso 1 1 calc R . .
C39 C 1.3754(7) 1.2836(6) 0.5234(2) 0.0719(17) Uani 1 1 d . . .
H39A H 1.3785 1.3614 0.5052 0.086 Uiso 1 1 calc R . .
C40 C 1.4667(5) 0.6339(5) 0.65783(17) 0.0470(11) Uani 1 1 d . . .
H40A H 1.5173 0.6982 0.6770 0.056 Uiso 1 1 calc R . .
H40B H 1.4271 0.5674 0.6791 0.056 Uiso 1 1 calc R . .
N1 N 1.2426(3) 0.9161(3) 0.63670(12) 0.0336(7) Uani 1 1 d . . .
H1A H 1.1681 0.9634 0.6347 0.040 Uiso 1 1 calc R . .
N2 N 1.5135(3) 1.1266(3) 0.63314(12) 0.0368(7) Uani 1 1 d . . .
N3 N 1.2540(4) 0.5997(4) 0.60946(17) 0.0552(11) Uani 1 1 d . . .
O1 O 1.1760(5) 0.6350(5) 0.57803(16) 0.0869(14) Uani 1 1 d . . .
O2 O 1.2558(5) 0.4874(4) 0.6267(2) 0.0931(16) Uani 1 1 d . . .
O4 O 1.5605(4) 0.5700(3) 0.62574(14) 0.0574(9) Uani 1 1 d . . .
O5 O 1.5342(3) 0.9429(3) 0.68130(11) 0.0450(7) Uani 1 1 d . . .
Br1 Br 0.71089(6) 0.61744(9) 0.75926(2) 0.0954(3) Uani 1 1 d . . .
C3 C 0.8788(5) 0.6689(6) 0.72868(16) 0.0513(12) Uani 1 1 d . . .
C4 C 1.0017(6) 0.6168(6) 0.74486(17) 0.0614(14) Uani 1 1 d . . .
H4A H 1.0034 0.5566 0.7701 0.074 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
F1 C18 1.341(5) . ?
C6 C17 1.377(6) . ?
C6 C23 1.391(6) . ?
C6 C9 1.517(6) . ?
C8 C14 1.379(6) . ?
C8 C27 1.369(6) . ?
C8 C11 1.513(6) . ?
C9 C12 1.541(6) . ?
C9 C11 1.546(5) . ?
C10 C31 1.372(6) . ?
C10 C13 1.379(6) . ?
C11 N1 1.463(5) . ?
C11 C25 1.548(5) . ?
C12 C40 1.517(6) . ?
C12 N3 1.532(5) . ?
C12 C26 1.570(6) . ?
C13 C18 1.398(6) . ?
C13 C26 1.516(6) . ?
C14 C30 1.385(6) . ?
C14 N2 1.406(6) . ?
C15 C22 1.382(6) . ?
C15 C24 1.389(7) . ?
C16 C21 1.382(8) . ?
C16 C17 1.397(6) . ?
C17 O4 1.379(6) . ?
C18 C4 1.360(7) . ?
C21 C32 1.376(8) . ?
C22 C35 1.364(6) . ?
C22 C38 1.518(6) . ?
C23 C32 1.390(7) . ?
C24 C29 1.364(8) . ?
C25 O5 1.219(5) . ?
C25 N2 1.363(5) . ?
C26 N1 1.451(5) . ?
C27 C34 1.383(8) . ?
C29 C33 1.367(9) . ?
C30 C39 1.388(9) . ?
C31 C3 1.370(7) . ?
C33 C35 1.379(8) . ?
C34 C39 1.384(9) . ?
C38 N2 1.448(5) . ?
C40 O4 1.426(5) . ?
N3 O1 1.211(6) . ?
N3 O2 1.222(6) . ?
Br1 C3 1.899(4) . ?
C3 C4 1.368(7) . ?

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
C17 C6 C23 118.1(4) . . ?
C17 C6 C9 120.7(4) . . ?
C23 C6 C9 121.0(4) . . ?
C14 C8 C27 120.6(4) . . ?
C14 C8 C11 108.7(4) . . ?
C27 C8 C11 130.7(4) . . ?
C6 C9 C12 113.6(4) . . ?
C6 C9 C11 116.4(3) . . ?
C12 C9 C11 104.1(3) . . ?
C31 C10 C13 122.4(4) . . ?
N1 C11 C8 112.0(3) . . ?
N1 C11 C25 111.3(3) . . ?
C8 C11 C25 101.6(3) . . ?
N1 C11 C9 100.4(3) . . ?
C8 C11 C9 117.6(3) . . ?
C25 C11 C9 114.4(3) . . ?
C40 C12 C9 112.0(3) . . ?
C40 C12 N3 108.7(4) . . ?
C9 C12 N3 110.2(3) . . ?
C40 C12 C26 112.4(4) . . ?
C9 C12 C26 105.2(3) . . ?
N3 C12 C26 108.3(3) . . ?
C10 C13 C18 116.2(4) . . ?
C10 C13 C26 123.0(4) . . ?
C18 C13 C26 120.5(4) . . ?
C8 C14 C30 122.1(4) . . ?
C8 C14 N2 110.5(4) . . ?
C30 C14 N2 127.4(4) . . ?
C22 C15 C24 120.7(5) . . ?
C21 C16 C17 119.1(5) . . ?
O4 C17 C6 121.8(4) . . ?
O4 C17 C16 116.5(4) . . ?
C6 C17 C16 121.7(5) . . ?
F1 C18 C4 119.5(4) . . ?
F1 C18 C13 117.6(4) . . ?
C4 C18 C13 122.9(4) . . ?
C16 C21 C32 120.2(5) . . ?
C35 C22 C15 118.3(4) . . ?
C35 C22 C38 119.4(4) . . ?
C15 C22 C38 122.3(4) . . ?
C6 C23 C32 120.8(5) . . ?
C29 C24 C15 120.3(5) . . ?
O5 C25 N2 124.6(4) . . ?
O5 C25 C11 127.2(3) . . ?
N2 C25 C11 108.1(3) . . ?
N1 C26 C13 111.8(3) . . ?
N1 C26 C12 102.2(3) . . ?
C13 C26 C12 119.8(3) . . ?
C34 C27 C8 119.0(5) . . ?
C24 C29 C33 118.9(5) . . ?
C14 C30 C39 116.3(5) . . ?
C10 C31 C3 118.5(4) . . ?
C21 C32 C23 120.1(5) . . ?
C29 C33 C35 121.0(5) . . ?
C27 C34 C39 119.8(5) . . ?
C22 C35 C33 120.8(5) . . ?
N2 C38 C22 114.6(4) . . ?
C30 C39 C34 122.2(5) . . ?
O4 C40 C12 111.6(4) . . ?
C26 N1 C11 107.5(3) . . ?
C25 N2 C14 110.7(3) . . ?
C25 N2 C38 122.7(4) . . ?
C14 N2 C38 126.5(4) . . ?
O1 N3 O2 124.4(5) . . ?
O1 N3 C12 118.0(4) . . ?
O2 N3 C12 117.5(5) . . ?
C17 O4 C40 112.7(3) . . ?
C4 C3 C31 121.9(4) . . ?
C4 C3 Br1 118.7(4) . . ?
C31 C3 Br1 119.5(4) . . ?
C18 C4 C3 118.1(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.153
_refine_diff_density_min         -1.323
_refine_diff_density_rms         0.072
