# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  data retrieval see:
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H27 Br N2 O5'
_chemical_formula_weight         551.43
_chemical_absolute_configuration ad

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   'P4(3)2(1)2 '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   12.3183(11)
_cell_length_b                   12.3183(11)
_cell_length_c                   36.329(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5512.6(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'transparent white'
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2272
_exptl_absorpt_coefficient_mu    1.530
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5728
_exptl_absorpt_correction_T_max  0.6403
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30708
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4864
_reflns_number_gt                3552
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0680P)²+1.9710P] 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   0.002(12)
_refine_ls_number_reflns         4864
_refine_ls_number_parameters     325
_refine_ls_number_restraints     684
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.067
_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 0.41072(7) 0.69458(6) 0.09804(2) 0.1211(4) Uani 1 1 d . . .
O1 O 0.4744(2) 1.2438(2) 0.13675(7) 0.0452(6) Uani 1 1 d . . .
O2 O 0.7084(3) 1.1096(4) 0.02623(9) 0.0878(11) Uani 1 1 d . . .
O3 O 0.8229(3) 0.9880(4) 0.04137(10) 0.1012(14) Uani 1 1 d . . .
O4 O 0.3512(2) 1.1444(3) 0.19373(10) 0.0715(9) Uani 1 1 d . . .
O5 O 0.4302(2) 0.9800(2) 0.19889(8) 0.0621(8) Uani 1 1 d . . .
C1 C 0.5450(3) 1.1931(3) 0.15194(9) 0.0357(7) Uani 1 1 d U . .
C2 C 0.6649(3) 1.1892(3) 0.14013(10) 0.0370(7) Uani 1 1 d U . .
C3 C 0.7152(3) 1.1203(3) 0.16991(10) 0.0392(8) Uani 1 1 d U . .
C4 C 0.8231(3) 1.0977(3) 0.17727(11) 0.0453(8) Uani 1 1 d U . .
H4A H 0.8782 1.1272 0.1629 0.054 Uiso 1 1 calc R . .
C5 C 0.8465(3) 1.0301(4) 0.20646(12) 0.0562(10) Uani 1 1 d U . .
H5A H 0.9185 1.0144 0.2120 0.067 Uiso 1 1 calc R . .
C6 C 0.7652(4) 0.9856(4) 0.22755(13) 0.0621(11) Uani 1 1 d U . .
H6A H 0.7836 0.9385 0.2466 0.075 Uiso 1 1 calc R . .
C7 C 0.6568(4) 1.0086(4) 0.22132(11) 0.0558(10) Uani 1 1 d U . .
H7A H 0.6021 0.9792 0.2359 0.067 Uiso 1 1 calc R . .
C8 C 0.6340(3) 1.0780(3) 0.19216(10) 0.0416(8) Uani 1 1 d U . .
C9 C 0.7106(3) 1.3043(3) 0.13567(10) 0.0418(8) Uani 1 1 d U . .
H9A H 0.7884 1.2989 0.1319 0.050 Uiso 1 1 calc R . .
H9B H 0.6797 1.3358 0.1135 0.050 Uiso 1 1 calc R . .
C10 C 0.6902(3) 1.3813(3) 0.16720(11) 0.0490(9) Uani 1 1 d U . .
C11 C 0.6176(4) 1.4650(4) 0.16272(14) 0.0706(11) Uani 1 1 d U . .
H11A H 0.5792 1.4714 0.1408 0.085 Uiso 1 1 calc R . .
C12 C 0.6009(5) 1.5408(5) 0.19105(17) 0.0913(15) Uani 1 1 d U . .
H12A H 0.5513 1.5971 0.1880 0.110 Uiso 1 1 calc R . .
C13 C 0.6576(5) 1.5313(5) 0.22277(17) 0.0943(15) Uani 1 1 d U . .
H13A H 0.6471 1.5819 0.2414 0.113 Uiso 1 1 calc R . .
C14 C 0.7302(5) 1.4486(5) 0.22791(15) 0.0891(14) Uani 1 1 d U . .
H14A H 0.7682 1.4429 0.2499 0.107 Uiso 1 1 calc R . .
C15 C 0.7469(4) 1.3731(4) 0.19988(13) 0.0625(10) Uani 1 1 d U . .
H15A H 0.7963 1.3169 0.2032 0.075 Uiso 1 1 calc R . .
C16 C 0.6615(3) 1.1290(3) 0.10145(10) 0.0377(8) Uani 1 1 d U . .
H16A H 0.6222 1.1769 0.0845 0.045 Uiso 1 1 calc R . .
C17 C 0.5997(3) 1.0227(3) 0.10235(10) 0.0416(8) Uani 1 1 d U . .
C18 C 0.6443(4) 0.9284(3) 0.11658(11) 0.0515(9) Uani 1 1 d U . .
H18A H 0.7136 0.9305 0.1267 0.062 Uiso 1 1 calc R . .
C19 C 0.5875(4) 0.8302(4) 0.11617(13) 0.0643(11) Uani 1 1 d U . .
H19A H 0.6182 0.7673 0.1258 0.077 Uiso 1 1 calc R . .
C20 C 0.4856(4) 0.8291(4) 0.10128(13) 0.0631(11) Uani 1 1 d U . .
C21 C 0.4379(4) 0.9202(4) 0.08796(13) 0.0638(11) Uani 1 1 d U . .
H21A H 0.3676 0.9179 0.0787 0.077 Uiso 1 1 calc R . .
C22 C 0.4958(3) 1.0168(4) 0.08839(10) 0.0511(9) Uani 1 1 d U . .
H22A H 0.4636 1.0793 0.0790 0.061 Uiso 1 1 calc R . .
C23 C 0.7748(3) 1.1153(3) 0.08582(10) 0.0436(8) Uani 1 1 d U . .
H23A H 0.8105 1.1854 0.0845 0.052 Uiso 1 1 calc R . .
H23B H 0.8172 1.0686 0.1018 0.052 Uiso 1 1 calc R . .
C24 C 0.4268(3) 1.0860(3) 0.19222(11) 0.0467(9) Uani 1 1 d U . .
C25 C 0.3309(4) 0.9194(4) 0.21071(14) 0.0694(13) Uani 1 1 d U . .
C26 C 0.2435(5) 0.9326(5) 0.18307(18) 0.1009(19) Uani 1 1 d U . .
H26A H 0.2188 1.0064 0.1831 0.151 Uiso 1 1 calc R . .
H26B H 0.1842 0.8852 0.1891 0.151 Uiso 1 1 calc R . .
H26C H 0.2710 0.9145 0.1591 0.151 Uiso 1 1 calc R . .
C27 C 0.3715(6) 0.8014(5) 0.20932(18) 0.1038(19) Uani 1 1 d U . .
H27A H 0.3140 0.7534 0.2166 0.156 Uiso 1 1 calc R . .
H27B H 0.4319 0.7930 0.2258 0.156 Uiso 1 1 calc R . .
H27C H 0.3939 0.7842 0.1847 0.156 Uiso 1 1 calc R . .
C28 C 0.3049(6) 0.9532(6) 0.24826(17) 0.118(2) Uani 1 1 d U . .
H28A H 0.2810 1.0274 0.2481 0.178 Uiso 1 1 calc R . .
H28B H 0.3684 0.9466 0.2634 0.178 Uiso 1 1 calc R . .
H28C H 0.2483 0.9078 0.2579 0.178 Uiso 1 1 calc R . .
N1 N 0.5315(2) 1.1208(3) 0.18096(8) 0.0397(7) Uani 1 1 d . . .
N2 N 0.7684(3) 1.0664(3) 0.04808(11) 0.0595(9) Uani 1 1 d . . .


_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 C20 1.900(4) . ?
O1 C1 1.204(4) . ?
O2 N2 1.209(5) . ?
O3 N2 1.200(5) . ?
O4 C24 1.177(5) . ?
O5 C24 1.328(5) . ?
O5 C25 1.496(5) . ?
C1 N1 1.390(4) . ?
C1 C2 1.539(5) . ?
C2 C3 1.508(5) . ?
C2 C9 1.534(5) . ?
C2 C16 1.590(5) . ?
C3 C8 1.388(5) . ?
C3 C4 1.384(5) . ?
C4 C5 1.379(6) . ?
C5 C6 1.375(6) . ?
C6 C7 1.383(6) . ?
C7 C8 1.390(5) . ?
C8 N1 1.427(5) . ?
C9 C10 1.508(5) . ?
C10 C15 1.380(6) . ?
C10 C11 1.375(6) . ?
C11 C12 1.405(7) . ?
C12 C13 1.353(8) . ?
C13 C14 1.368(9) . ?
C14 C15 1.395(7) . ?
C16 C17 1.515(5) . ?
C16 C23 1.516(5) . ?
C17 C18 1.384(5) . ?
C17 C22 1.379(5) . ?
C18 C19 1.397(6) . ?
C19 C20 1.367(7) . ?
C20 C21 1.356(7) . ?
C21 C22 1.388(6) . ?
C23 N2 1.500(5) . ?
C24 N1 1.420(5) . ?
C25 C28 1.462(8) . ?
C25 C26 1.480(7) . ?
C25 C27 1.538(8) . ?

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
C24 O5 C25 121.1(4) . . ?
O1 C1 N1 126.4(3) . . ?
O1 C1 C2 125.6(3) . . ?
N1 C1 C2 107.8(3) . . ?
C3 C2 C9 116.5(3) . . ?
C3 C2 C1 102.2(3) . . ?
C9 C2 C1 110.6(3) . . ?
C3 C2 C16 112.5(3) . . ?
C9 C2 C16 110.4(3) . . ?
C1 C2 C16 103.6(3) . . ?
C8 C3 C4 120.3(3) . . ?
C8 C3 C2 109.5(3) . . ?
C4 C3 C2 130.2(4) . . ?
C3 C4 C5 118.1(4) . . ?
C6 C5 C4 121.1(4) . . ?
C5 C6 C7 122.0(4) . . ?
C8 C7 C6 116.5(4) . . ?
C3 C8 C7 121.9(4) . . ?
C3 C8 N1 109.4(3) . . ?
C7 C8 N1 128.6(4) . . ?
C10 C9 C2 116.1(3) . . ?
C15 C10 C11 119.1(4) . . ?
C15 C10 C9 121.6(4) . . ?
C11 C10 C9 119.3(4) . . ?
C10 C11 C12 120.5(5) . . ?
C13 C12 C11 119.4(5) . . ?
C14 C13 C12 121.3(5) . . ?
C13 C14 C15 119.6(6) . . ?
C10 C15 C14 120.3(5) . . ?
C17 C16 C23 112.0(3) . . ?
C17 C16 C2 113.4(3) . . ?
C23 C16 C2 111.0(3) . . ?
C18 C17 C22 117.5(4) . . ?
C18 C17 C16 122.3(3) . . ?
C22 C17 C16 120.2(4) . . ?
C17 C18 C19 121.6(4) . . ?
C18 C19 C20 118.2(4) . . ?
C21 C20 C19 122.0(4) . . ?
C21 C20 Br1 119.3(4) . . ?
C19 C20 Br1 118.6(4) . . ?
C20 C21 C22 118.9(4) . . ?
C21 C22 C17 121.7(4) . . ?
N2 C23 C16 109.8(3) . . ?
O4 C24 O5 128.1(4) . . ?
O4 C24 N1 123.2(4) . . ?
O5 C24 N1 108.7(4) . . ?
C28 C25 C26 116.3(6) . . ?
C28 C25 O5 107.7(4) . . ?
C26 C25 O5 110.2(4) . . ?
C28 C25 C27 111.8(5) . . ?
C26 C25 C27 108.5(5) . . ?
O5 C25 C27 101.3(4) . . ?
C1 N1 C8 110.3(3) . . ?
C1 N1 C24 121.3(3) . . ?
C8 N1 C24 127.6(3) . . ?
O3 N2 O2 124.3(4) . . ?
O3 N2 C23 118.7(4) . . ?
O2 N2 C23 117.1(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         0.470
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 990860'
