# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_dbr34

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H26 Br N O5'
_chemical_formula_weight         548.42
_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 0.0181 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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   9.2088(3)
_cell_length_b                   11.1545(3)
_cell_length_c                   13.3119(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.479(3)
_cell_angle_gamma                90.00
_cell_volume                     1311.23(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4338
_cell_measurement_theta_min      3.4597
_cell_measurement_theta_max      71.4676

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
_exptl_absorpt_coefficient_mu    2.458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.27133
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8482
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         71.60
_reflns_number_total             4989
_reflns_number_gt                4549
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd. 2007)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd. 2007)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd. 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX6a (McArdle,1995), PLATON (Spek,2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0873P)^2^+0.4972P] where P=(Fo^2^+2Fc^2^)/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   -0.025(18)
_refine_ls_number_reflns         4989
_refine_ls_number_parameters     328
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   0.819
_refine_ls_restrained_S_all      0.819
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.002

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 -0.22342(4) 0.14225(4) -0.09415(3) 0.07514(15) Uani 1 1 d . . .
C4 C 0.0832(3) 0.1498(4) 0.0298(2) 0.0510(6) Uani 1 1 d . . .
H4 H 0.0582 0.0806 0.0602 0.061 Uiso 1 1 calc R . .
C7 C 0.3509(3) 0.1274(3) 0.1449(2) 0.0444(6) Uani 1 1 d . . .
H7 H 0.3063 0.1053 0.2010 0.053 Uiso 1 1 calc R . .
O1 O 0.4010(2) 0.3550(2) 0.04706(18) 0.0550(5) Uani 1 1 d . . .
C2 C 0.0077(4) 0.3109(3) -0.0951(3) 0.0559(8) Uani 1 1 d . . .
H2 H -0.0668 0.3480 -0.1481 0.067 Uiso 1 1 calc R . .
C3 C -0.0246(3) 0.2084(3) -0.0476(3) 0.0535(7) Uani 1 1 d . . .
C6 C 0.2620(3) 0.2992(3) 0.0165(2) 0.0471(6) Uani 1 1 d . . .
C5 C 0.2306(3) 0.1951(3) 0.0625(2) 0.0448(6) Uani 1 1 d . . .
C1 C 0.1524(4) 0.3574(3) -0.0628(3) 0.0548(7) Uani 1 1 d . . .
H1 H 0.1767 0.4267 -0.0934 0.066 Uiso 1 1 calc R . .
O2 O 0.6969(3) 0.0748(3) 0.20788(19) 0.0649(6) Uani 1 1 d . . .
C8 C 0.3923(4) 0.0108(3) 0.0989(2) 0.0558(7) Uani 1 1 d . . .
H8A H 0.3027 -0.0201 0.0481 0.067 Uiso 1 1 calc R . .
H8B H 0.4667 0.0286 0.0620 0.067 Uiso 1 1 calc R . .
N1 N 0.6745(3) 0.1771(2) 0.35526(18) 0.0462(6) Uani 1 1 d . . .
C13 C 0.5678(3) 0.2594(3) 0.3749(2) 0.0437(6) Uani 1 1 d . . .
C10 C 0.6324(3) 0.1438(4) 0.2495(2) 0.0478(6) Uani 1 1 d . . .
C12 C 0.4870(3) 0.2129(3) 0.1938(2) 0.0434(6) Uani 1 1 d . . .
O3 O 0.8290(2) 0.1513(3) 0.52148(16) 0.0632(6) Uani 1 1 d . . .
O4 O 0.9134(3) 0.1199(4) 0.38152(19) 0.0793(10) Uani 1 1 d . . .
C19 C 0.8123(3) 0.1461(4) 0.4296(2) 0.0473(6) Uani 1 1 d . . .
O5 O 0.4443(5) -0.0842(3) 0.2654(3) 0.0925(10) Uani 1 1 d . . .
C18 C 0.5638(4) 0.3109(3) 0.4688(2) 0.0549(7) Uani 1 1 d . . .
H18 H 0.6340 0.2900 0.5315 0.066 Uiso 1 1 calc R . .
C16 C 0.3465(4) 0.4250(3) 0.3730(3) 0.0604(8) Uani 1 1 d . . .
H16 H 0.2728 0.4821 0.3727 0.072 Uiso 1 1 calc R . .
C9 C 0.4546(5) -0.0843(4) 0.1789(3) 0.0692(10) Uani 1 1 d . . .
H9 H 0.5052 -0.1482 0.1591 0.083 Uiso 1 1 calc R . .
C21 C 1.1567(5) 0.1608(8) 0.5084(5) 0.118(2) Uani 1 1 d . . .
H21A H 1.1180 0.1711 0.5676 0.177 Uiso 1 1 calc R . .
H21B H 1.1511 0.2355 0.4718 0.177 Uiso 1 1 calc R . .
H21C H 1.2602 0.1348 0.5319 0.177 Uiso 1 1 calc R . .
C17 C 0.4519(4) 0.3947(4) 0.4660(3) 0.0626(9) Uani 1 1 d . . .
H17 H 0.4475 0.4312 0.5279 0.075 Uiso 1 1 calc R . .
C15 C 0.3501(4) 0.3704(3) 0.2799(3) 0.0504(7) Uani 1 1 d . . .
H15 H 0.2788 0.3901 0.2172 0.061 Uiso 1 1 calc R . .
C14 C 0.4599(3) 0.2875(3) 0.2817(2) 0.0421(6) Uani 1 1 d . . .
C20 C 1.0627(4) 0.0670(5) 0.4352(3) 0.0721(11) Uani 1 1 d . . .
C22 C 0.5270(3) 0.2859(3) 0.1057(2) 0.0496(7) Uani 1 1 d . . .
H22 H 0.5551 0.2295 0.0579 0.060 Uiso 1 1 calc R . .
C23 C 0.6563(4) 0.3730(4) 0.1458(2) 0.0561(8) Uani 1 1 d . . .
C24 C 0.6314(5) 0.4874(4) 0.1759(3) 0.0667(10) Uani 1 1 d . . .
H24 H 0.5335 0.5114 0.1729 0.080 Uiso 1 1 calc R . .
C25 C 0.8023(4) 0.3383(5) 0.1521(3) 0.0791(12) Uani 1 1 d . . .
H25 H 0.8211 0.2611 0.1324 0.095 Uiso 1 1 calc R . .
C11 C 1.1262(7) 0.0436(9) 0.3456(5) 0.151(4) Uani 1 1 d . . .
H11A H 1.0970 0.1071 0.2953 0.227 Uiso 1 1 calc R . .
H11B H 1.0878 -0.0313 0.3133 0.227 Uiso 1 1 calc R . .
H11C H 1.2346 0.0398 0.3708 0.227 Uiso 1 1 calc R . .
C1A C 1.0464(7) -0.0417(5) 0.4971(6) 0.1087(19) Uani 1 1 d . . .
H1AA H 0.9874 -0.1010 0.4510 0.163 Uiso 1 1 calc R . .
H1AB H 0.9966 -0.0199 0.5488 0.163 Uiso 1 1 calc R . .
H1AC H 1.1448 -0.0737 0.5313 0.163 Uiso 1 1 calc R . .
C26 C 0.7502(6) 0.5674(5) 0.2106(3) 0.0837(13) Uani 1 1 d . . .
H26 H 0.7316 0.6450 0.2293 0.100 Uiso 1 1 calc R . .
C27 C 0.8942(6) 0.5323(7) 0.2174(4) 0.104(2) Uani 1 1 d . . .
H27 H 0.9745 0.5852 0.2420 0.124 Uiso 1 1 calc R . .
C28 C 0.9204(5) 0.4176(8) 0.1877(5) 0.104(2) Uani 1 1 d . . .
H28 H 1.0186 0.3936 0.1917 0.125 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.04177(18) 0.0748(2) 0.0958(3) -0.0057(2) -0.00161(15) -0.0089(2)
C4 0.0436(14) 0.0535(16) 0.0544(15) -0.0032(16) 0.0115(11) -0.0035(16)
C7 0.0408(13) 0.0520(17) 0.0391(12) -0.0021(12) 0.0092(10) 0.0007(14)
O1 0.0393(11) 0.0687(14) 0.0508(11) 0.0128(10) 0.0029(9) -0.0074(10)
C2 0.0438(16) 0.0598(18) 0.0556(17) -0.0005(14) 0.0003(13) 0.0052(14)
C3 0.0344(14) 0.0573(18) 0.0623(18) -0.0094(14) 0.0028(13) -0.0022(13)
C6 0.0376(14) 0.0590(17) 0.0431(14) -0.0022(12) 0.0089(11) -0.0014(12)
C5 0.0397(15) 0.0546(15) 0.0395(13) -0.0034(12) 0.0100(11) 0.0018(12)
C1 0.0458(17) 0.0604(19) 0.0527(17) 0.0033(14) 0.0051(13) 0.0003(14)
O2 0.0497(13) 0.0833(16) 0.0583(13) -0.0157(12) 0.0099(10) 0.0208(12)
C8 0.0518(18) 0.0631(18) 0.0468(16) -0.0072(14) 0.0050(13) 0.0034(15)
N1 0.0378(12) 0.0592(16) 0.0418(12) 0.0018(9) 0.0117(10) 0.0042(10)
C13 0.0326(13) 0.0544(15) 0.0443(14) -0.0014(12) 0.0110(11) -0.0035(12)
C10 0.0402(13) 0.0576(14) 0.0457(13) -0.0020(17) 0.0124(10) 0.0000(18)
C12 0.0367(14) 0.0536(16) 0.0401(14) 0.0000(12) 0.0112(11) 0.0049(12)
O3 0.0534(11) 0.0882(17) 0.0440(11) 0.0075(13) 0.0074(8) 0.0102(15)
O4 0.0448(12) 0.141(3) 0.0520(12) 0.0158(16) 0.0130(9) 0.0290(16)
C19 0.0374(12) 0.0562(14) 0.0475(14) 0.0073(16) 0.0109(10) 0.0022(17)
O5 0.116(3) 0.089(2) 0.068(2) 0.0181(16) 0.0188(19) 0.022(2)
C18 0.0460(17) 0.074(2) 0.0423(14) -0.0080(14) 0.0079(12) -0.0025(15)
C16 0.0504(18) 0.066(2) 0.066(2) -0.0092(16) 0.0181(16) 0.0094(15)
C9 0.072(2) 0.058(2) 0.068(2) -0.0043(16) 0.0043(19) 0.0070(18)
C21 0.051(2) 0.139(6) 0.151(5) 0.019(5) 0.006(3) 0.000(3)
C17 0.061(2) 0.080(2) 0.0515(18) -0.0221(17) 0.0224(14) -0.0015(17)
C15 0.0395(15) 0.0599(18) 0.0511(16) 0.0005(13) 0.0117(12) 0.0039(13)
C14 0.0372(14) 0.0511(15) 0.0385(13) -0.0012(11) 0.0117(11) -0.0034(11)
C20 0.0467(19) 0.103(3) 0.067(2) 0.019(2) 0.0160(16) 0.026(2)
C22 0.0396(15) 0.0682(19) 0.0414(14) 0.0027(13) 0.0122(12) 0.0017(13)
C23 0.0400(16) 0.087(2) 0.0409(15) 0.0088(15) 0.0104(12) -0.0080(15)
C24 0.055(2) 0.085(3) 0.0564(19) 0.0082(18) 0.0100(16) -0.0163(18)
C25 0.0428(19) 0.125(4) 0.071(2) 0.012(2) 0.0194(17) -0.005(2)
C11 0.092(4) 0.277(11) 0.095(4) 0.013(5) 0.045(3) 0.084(6)
C1A 0.111(4) 0.079(3) 0.144(5) 0.019(3) 0.048(4) 0.035(3)
C26 0.083(3) 0.099(3) 0.061(2) 0.004(2) 0.008(2) -0.036(3)
C27 0.065(3) 0.162(6) 0.072(3) 0.021(3) 0.000(2) -0.055(4)
C28 0.040(2) 0.177(6) 0.095(4) 0.018(4) 0.017(2) -0.020(3)

_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 C3 1.907(3) . ?
C4 C3 1.377(5) . ?
C4 C5 1.397(4) . ?
C7 C5 1.520(4) . ?
C7 C8 1.531(5) . ?
C7 C12 1.562(4) . ?
O1 C6 1.378(4) . ?
O1 C22 1.426(4) . ?
C2 C3 1.379(5) . ?
C2 C1 1.381(5) . ?
C6 C5 1.380(5) . ?
C6 C1 1.396(4) . ?
O2 C10 1.199(4) . ?
C8 C9 1.498(5) . ?
N1 C10 1.400(4) . ?
N1 C19 1.413(3) . ?
N1 C13 1.422(4) . ?
C13 C18 1.386(4) . ?
C13 C14 1.388(4) . ?
C10 C12 1.541(4) . ?
C12 C14 1.513(4) . ?
C12 C22 1.556(4) . ?
O3 C19 1.190(3) . ?
O4 C19 1.304(4) . ?
O4 C20 1.480(4) . ?
O5 C9 1.182(5) . ?
C18 C17 1.384(5) . ?
C16 C17 1.381(5) . ?
C16 C15 1.391(5) . ?
C21 C20 1.521(9) . ?
C15 C14 1.365(4) . ?
C20 C11 1.492(7) . ?
C20 C1A 1.498(7) . ?
C22 C23 1.512(5) . ?
C23 C24 1.376(6) . ?
C23 C25 1.379(5) . ?
C24 C26 1.385(6) . ?
C25 C28 1.377(8) . ?
C26 C27 1.361(8) . ?
C27 C28 1.381(9) . ?

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
C3 C4 C5 119.5(4) . . ?
C5 C7 C8 110.3(2) . . ?
C5 C7 C12 109.3(3) . . ?
C8 C7 C12 115.0(2) . . ?
C6 O1 C22 117.4(2) . . ?
C3 C2 C1 118.9(3) . . ?
C4 C3 C2 122.2(3) . . ?
C4 C3 Br1 118.8(3) . . ?
C2 C3 Br1 118.9(3) . . ?
O1 C6 C5 122.9(3) . . ?
O1 C6 C1 115.1(3) . . ?
C5 C6 C1 122.0(3) . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 C7 122.5(3) . . ?
C4 C5 C7 119.3(3) . . ?
C2 C1 C6 119.2(3) . . ?
C9 C8 C7 113.9(3) . . ?
C10 N1 C19 125.2(3) . . ?
C10 N1 C13 110.3(2) . . ?
C19 N1 C13 124.0(2) . . ?
C18 C13 C14 121.1(3) . . ?
C18 C13 N1 129.1(3) . . ?
C14 C13 N1 109.8(2) . . ?
O2 C10 N1 127.1(3) . . ?
O2 C10 C12 125.1(3) . . ?
N1 C10 C12 107.9(3) . . ?
C14 C12 C10 102.4(2) . . ?
C14 C12 C22 114.9(3) . . ?
C10 C12 C22 105.4(2) . . ?
C14 C12 C7 111.6(2) . . ?
C10 C12 C7 112.3(3) . . ?
C22 C12 C7 109.9(2) . . ?
C19 O4 C20 123.2(3) . . ?
O3 C19 O4 127.9(3) . . ?
O3 C19 N1 122.5(3) . . ?
O4 C19 N1 109.6(2) . . ?
C17 C18 C13 117.8(3) . . ?
C17 C16 C15 120.2(3) . . ?
O5 C9 C8 124.9(4) . . ?
C16 C17 C18 121.2(3) . . ?
C14 C15 C16 119.1(3) . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 C12 130.0(3) . . ?
C13 C14 C12 109.5(3) . . ?
O4 C20 C11 101.8(3) . . ?
O4 C20 C1A 111.3(4) . . ?
C11 C20 C1A 114.9(6) . . ?
O4 C20 C21 108.5(4) . . ?
C11 C20 C21 110.6(5) . . ?
C1A C20 C21 109.3(5) . . ?
O1 C22 C23 106.4(3) . . ?
O1 C22 C12 111.4(2) . . ?
C23 C22 C12 113.7(2) . . ?
C24 C23 C25 118.9(4) . . ?
C24 C23 C22 121.3(3) . . ?
C25 C23 C22 119.8(4) . . ?
C23 C24 C26 120.9(4) . . ?
C23 C25 C28 120.1(6) . . ?
C27 C26 C24 120.0(6) . . ?
C26 C27 C28 119.6(5) . . ?
C27 C28 C25 120.6(5) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        71.60
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 937954'