# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
_publ_author_address
N.Kuhnert
'Laboratory of Analytical and Organic Chemistry, School of Engineering and Science, Jacobs University Bremen, Bremen, Germany.'
H.F.Nour
'Laboratory of Analytical and Organic Chemistry, School of Engineering and Science, Jacobs University Bremen, Bremen, Germany.'
M.F.Matei
'Laboratory of Analytical and Organic Chemistry, School of Engineering and Science, Jacobs University Bremen, Bremen, Germany.'
B.S.Bassil
'Laboratory of Inorganic Chemistry, School of Engineering and Science, Jacobs University Bremen, Germany. '
_publ_contact_author_address     
'Laboratory of Analytical and Organic Chemistry, School of Engineering and Science, Jacobs University Bremen, Bremen, Germany.'
_publ_contact_author_email       n.kuhnert@jacobs-university.de
_publ_contact_author_fax         '+49 421 200 3229'
_publ_contact_author_phone       '+49 421 200 3120'
_publ_contact_author_name        'Nikolai Kuhnert'

data_nk4
_database_code_depnum_ccdc_archive 'CCDC 779417'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H34 Br2 N4 O6'
_chemical_formula_weight         682.41

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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8543(6)
_cell_length_b                   9.3193(7)
_cell_length_c                   10.5343(6)
_cell_angle_alpha                95.589(4)
_cell_angle_beta                 110.786(2)
_cell_angle_gamma                95.620(4)
_cell_volume                     710.15(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      26.33

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          1.00
_exptl_crystal_size_min          1.00
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    3.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    5.806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0681
_exptl_absorpt_correction_T_max  0.0454
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38893
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         26.37
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_reflns_number_total             2900
_reflns_number_gt                2631
_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 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^)+(0.0700P)^2^+0.0000P] 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_number_reflns         2900
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          2.404
_refine_ls_shift/su_mean         0.023
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.072

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
C1 C 0.4061(3) 0.1110(2) 0.6337(2) 0.0304(8) Uani 0.82(2) 1 d P . .
H1C1 H 0.537(4) 0.125(3) 0.695(3) 0.057(13) Uiso 0.89(9) 1 d P . .
C2 C 0.3549(3) 0.14701(19) 0.4926(2) 0.0258(7) Uani 0.83(2) 1 d P . .
C3 C 0.1768(3) 0.0965(2) 0.3995(2) 0.0297(8) Uani 0.82(2) 1 d P . .
H1C3 H 0.094(4) 0.045(2) 0.432(2) 0.036(11) Uiso 0.84(8) 1 d P . .
C4 C 0.1249(3) 0.1124(2) 0.2628(2) 0.0328(8) Uani 0.85(2) 1 d P . .
H1C4 H -0.012(4) 0.075(3) 0.197(3) 0.062(12) Uiso 1.00(9) 1 d . . .
C5 C 0.2557(3) 0.18082(19) 0.22015(19) 0.0283(7) Uani 0.84(2) 1 d P . .
C6 C 0.4328(3) 0.23478(19) 0.3090(2) 0.0296(7) Uani 0.89(2) 1 d P . .
H1C6 H 0.520(3) 0.289(2) 0.273(2) 0.015(8) Uiso 0.77(7) 1 d P . .
C7 C 0.4848(2) 0.21947(18) 0.44723(19) 0.0232(7) Uani 0.81(2) 1 d P . .
C8 C 0.6787(3) 0.3987(2) 0.6429(2) 0.0277(8) Uani 0.83(2) 1 d P . .
H2C8 H 0.674(3) 0.484(3) 0.603(2) 0.010(10) Uiso 0.64(7) 1 d P . .
H1C8 H 0.577(4) 0.381(2) 0.675(2) 0.040(10) Uiso 0.90(8) 1 d P . .
C9 C 0.8601(3) 0.4145(3) 0.7631(2) 0.0306(9) Uani 0.83(2) 1 d P . .
H2C9 H 0.879(3) 0.503(3) 0.822(3) 0.044(11) Uiso 0.94(9) 1 d P . .
H1C9 H 0.860(3) 0.325(3) 0.814(3) 0.057(12) Uiso 1.00(9) 1 d P . .
C10 C 0.9947(3) 0.3077(2) 0.6047(2) 0.0333(9) Uani 0.84(2) 1 d P . .
H2C0 H 1.094(4) 0.333(3) 0.575(3) 0.058(12) Uiso 1.00(9) 1 d . . .
H1C0 H 1.009(4) 0.210(3) 0.644(3) 0.064(13) Uiso 1.00(10) 1 d . . .
C11 C 0.8108(3) 0.2964(2) 0.4888(2) 0.0288(9) Uani 0.80(2) 1 d P . .
H2CA H 0.804(3) 0.390(3) 0.444(3) 0.021(10) Uiso 0.71(7) 1 d P . .
H1CA H 0.801(3) 0.223(3) 0.417(3) 0.039(10) Uiso 0.91(8) 1 d P . .
C12 C 1.1840(2) 0.49268(19) 0.79122(19) 0.0237(7) Uani 0.81(2) 1 d P . .
C13 C 1.3594(3) 0.6613(2) 0.9912(2) 0.0305(9) Uani 0.81(2) 1 d P . .
H2CC H 1.360(4) 0.628(3) 1.089(3) 0.077(14) Uiso 1.00(10) 1 d . . .
H1CC H 1.457(4) 0.632(3) 0.966(3) 0.043(11) Uiso 0.84(8) 1 d P . .
C14 C 1.3471(4) 0.8205(3) 0.9918(3) 0.0379(11) Uani 0.78(2) 1 d P . .
H3CD H 1.334(4) 0.845(3) 0.898(4) 0.039(13) Uiso 0.71(9) 1 d P . .
H2CD H 1.478(4) 0.882(3) 1.069(3) 0.083(16) Uiso 1.00(10) 1 d . . .
H1CD H 1.246(4) 0.845(3) 1.022(3) 0.067(13) Uiso 1.00(9) 1 d . . .
O1 O 1.18426(19) 0.57761(16) 0.90177(15) 0.0369(6) Uani 0.83(2) 1 d P . .
O2 O 1.31904(19) 0.48193(16) 0.76254(15) 0.0358(6) Uani 0.84(2) 1 d P . .
O3 O 0.2966(2) 0.06051(16) 0.67985(16) 0.0405(6) Uani 0.85(2) 1 d P . .
N1 N 0.6634(2) 0.27209(16) 0.54304(16) 0.0245(5) Uani 0.83(2) 1 d P . .
N2 N 1.0123(2) 0.42367(17) 0.71376(17) 0.0279(6) Uani 0.83(2) 1 d P . .
Br1 Br 0.18705(3) 0.20398(2) 0.032347(19) 0.03569(11) Uani 0.80(2) 1 d P . .

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
C1 0.0295(13) 0.0266(11) 0.0340(13) 0.0038(8) 0.0109(10) 0.0023(8)
C2 0.0236(11) 0.0221(10) 0.0310(11) 0.0001(7) 0.0099(8) 0.0038(7)
C3 0.0240(12) 0.0266(11) 0.0366(13) -0.0011(8) 0.0115(9) -0.0007(8)
C4 0.0226(11) 0.0350(11) 0.0357(12) -0.0014(8) 0.0076(9) -0.0001(8)
C5 0.0277(11) 0.0290(10) 0.0264(11) 0.0001(7) 0.0084(8) 0.0058(7)
C6 0.0262(11) 0.0291(10) 0.0327(11) 0.0012(7) 0.0107(8) 0.0033(7)
C7 0.0186(10) 0.0190(9) 0.0296(11) -0.0010(7) 0.0068(8) 0.0045(6)
C8 0.0222(11) 0.0264(12) 0.0320(12) -0.0033(8) 0.0091(8) 0.0023(7)
C9 0.0207(11) 0.0398(14) 0.0287(12) -0.0049(9) 0.0100(8) -0.0012(8)
C10 0.0204(12) 0.0350(13) 0.0404(14) -0.0081(8) 0.0102(9) 0.0028(8)
C11 0.0205(11) 0.0359(14) 0.0276(12) -0.0074(8) 0.0103(8) -0.0010(8)
C12 0.0203(10) 0.0248(10) 0.0232(10) 0.0054(7) 0.0045(7) 0.0020(7)
C13 0.0189(12) 0.0369(12) 0.0275(13) -0.0024(8) 0.0025(8) -0.0039(8)
C14 0.0300(15) 0.0362(14) 0.0400(17) 0.0021(10) 0.0063(10) -0.0017(9)
O1 0.0226(8) 0.0458(9) 0.0347(9) -0.0113(6) 0.0085(6) -0.0061(6)
O2 0.0208(8) 0.0486(10) 0.0349(9) -0.0004(6) 0.0091(6) 0.0018(6)
O3 0.0391(10) 0.0452(9) 0.0411(10) 0.0094(7) 0.0197(7) 0.0015(7)
N1 0.0174(8) 0.0270(9) 0.0269(9) -0.0021(6) 0.0074(6) 0.0011(6)
N2 0.0190(9) 0.0321(9) 0.0298(10) -0.0047(6) 0.0089(7) -0.0012(6)
Br1 0.02767(15) 0.04816(16) 0.02538(15) 0.00364(9) 0.00406(10) 0.00169(9)

_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
C1 O3 1.208(3) . ?
C1 C2 1.477(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.414(3) . ?
C3 C4 1.379(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.382(3) . ?
C5 Br1 1.8974(19) . ?
C6 C7 1.392(3) . ?
C7 N1 1.411(2) . ?
C8 N1 1.468(2) . ?
C8 C9 1.515(3) . ?
C9 N2 1.462(2) . ?
C10 N2 1.457(2) . ?
C10 C11 1.511(3) . ?
C11 N1 1.470(3) . ?
C12 O2 1.212(2) . ?
C12 O1 1.342(2) . ?
C12 N2 1.358(2) . ?
C13 O1 1.455(2) . ?
C13 C14 1.496(3) . ?

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
O3 C1 C2 123.8(2) . . ?
C3 C2 C7 119.65(19) . . ?
C3 C2 C1 118.24(18) . . ?
C7 C2 C1 121.89(17) . . ?
C4 C3 C2 121.5(2) . . ?
C3 C4 C5 117.74(19) . . ?
C6 C5 C4 122.78(18) . . ?
C6 C5 Br1 118.79(15) . . ?
C4 C5 Br1 118.42(15) . . ?
C5 C6 C7 119.44(18) . . ?
C6 C7 N1 122.19(17) . . ?
C6 C7 C2 118.83(17) . . ?
N1 C7 C2 118.98(17) . . ?
N1 C8 C9 110.13(16) . . ?
N2 C9 C8 109.79(17) . . ?
N2 C10 C11 110.59(16) . . ?
N1 C11 C10 109.00(19) . . ?
O2 C12 O1 124.24(17) . . ?
O2 C12 N2 124.41(18) . . ?
O1 C12 N2 111.34(16) . . ?
O1 C13 C14 109.60(18) . . ?
C12 O1 C13 116.79(16) . . ?
C7 N1 C8 116.02(14) . . ?
C7 N1 C11 117.13(16) . . ?
C8 N1 C11 108.82(15) . . ?
C12 N2 C10 117.71(16) . . ?
C12 N2 C9 123.11(16) . . ?
C10 N2 C9 114.52(16) . . ?