# 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.
#
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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
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_p21

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 Br N O5'
_chemical_formula_weight         382.21
_chemical_absolute_configuration none

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   7.907(8)
_cell_length_b                   8.093(8)
_cell_length_c                   12.534(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.397(9)
_cell_angle_gamma                90.00
_cell_volume                     786.2(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1510
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      23.20

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5820
_exptl_absorpt_correction_T_max  0.6774
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5648
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0893
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2877
_reflns_number_gt                2032
_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^)+(0.0469P)^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    constr
_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   0.029(15)
_refine_ls_number_reflns         2877
_refine_ls_number_parameters     211
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
Br1 Br 1.18606(8) 0.45895(13) 0.95018(5) 0.0796(3) Uani 1 1 d . . .
C1 C 0.2594(7) 0.6534(6) 0.5088(4) 0.0348(12) Uani 1 1 d . . .
C2 C 0.4260(7) 0.5831(7) 0.5722(4) 0.0375(13) Uani 1 1 d . . .
H2A H 0.5218 0.6337 0.5466 0.045 Uiso 1 1 calc R . .
H2B H 0.4290 0.4654 0.5580 0.045 Uiso 1 1 calc R . .
C3 C 0.4500(7) 0.6108(6) 0.6970(4) 0.0346(13) Uani 1 1 d . . .
H3 H 0.3720 0.5359 0.7254 0.041 Uiso 1 1 calc R . .
C4 C 0.3947(7) 0.7861(6) 0.7129(4) 0.0337(12) Uani 1 1 d . . .
C5 C 0.4217(8) 0.8797(7) 0.8190(4) 0.0396(14) Uani 1 1 d . . .
H5A H 0.5429 0.8823 0.8532 0.048 Uiso 1 1 calc R . .
H5B H 0.3571 0.8295 0.8687 0.048 Uiso 1 1 calc R . .
C6 C 0.3545(8) 1.0547(7) 0.7867(5) 0.0427(15) Uani 1 1 d . . .
H6A H 0.2713 1.0892 0.8296 0.051 Uiso 1 1 calc R . .
H6B H 0.4486 1.1337 0.7968 0.051 Uiso 1 1 calc R . .
C7 C 0.2712(7) 1.0406(6) 0.6686(4) 0.0327(13) Uani 1 1 d . . .
C8 C 0.3073(7) 0.8776(6) 0.6329(4) 0.0322(13) Uani 1 1 d . . .
C9 C 0.6332(7) 0.5767(6) 0.7571(4) 0.0350(13) Uani 1 1 d . . .
C10 C 0.6578(8) 0.5013(8) 0.8573(4) 0.0498(17) Uani 1 1 d . . .
H10 H 0.5614 0.4734 0.8857 0.060 Uiso 1 1 calc R . .
C11 C 0.8202(7) 0.4647(11) 0.9181(4) 0.0596(16) Uani 1 1 d . . .
H11 H 0.8344 0.4133 0.9856 0.072 Uiso 1 1 calc R . .
C12 C 0.9609(8) 0.5092(7) 0.8725(5) 0.0481(16) Uani 1 1 d . . .
C13 C 0.9417(8) 0.5847(8) 0.7739(5) 0.0508(16) Uani 1 1 d . . .
H13 H 1.0374 0.6136 0.7450 0.061 Uiso 1 1 calc R . .
C14 C 0.7772(7) 0.6174(7) 0.7178(5) 0.0462(15) Uani 1 1 d . . .
H14 H 0.7635 0.6692 0.6504 0.055 Uiso 1 1 calc R . .
C15 C 0.2605(8) 0.6447(7) 0.3885(5) 0.0405(14) Uani 1 1 d . . .
C16 C 0.1226(9) 0.5372(10) 0.2199(4) 0.069(2) Uani 1 1 d . . .
H16A H 0.1072 0.6476 0.1917 0.104 Uiso 1 1 calc R . .
H16B H 0.0243 0.4712 0.1886 0.104 Uiso 1 1 calc R . .
H16C H 0.2247 0.4901 0.2017 0.104 Uiso 1 1 calc R . .
N1 N 0.1868(6) 1.1480(5) 0.6052(4) 0.0409(12) Uani 1 1 d . . .
O1 O 0.1189(5) 0.5756(4) 0.5399(3) 0.0385(9) Uani 1 1 d . . .
H1 H 0.1200 0.5949 0.6042 0.058 Uiso 1 1 calc R . .
O2 O 0.2472(5) 0.8298(4) 0.5272(3) 0.0361(9) Uani 1 1 d . . .
O3 O 0.3598(7) 0.7153(6) 0.3462(4) 0.0668(13) Uani 1 1 d . . .
O4 O 0.1401(5) 0.5409(5) 0.3372(3) 0.0504(11) Uani 1 1 d . . .
O5 O 0.1673(6) 1.2944(4) 0.6666(3) 0.0517(11) Uani 1 1 d . . .
H5 H 0.1792 1.3763 0.6302 0.078 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 0.0420(4) 0.1450(8) 0.0459(4) -0.0012(5) -0.0058(3) 0.0302(5)
C1 0.031(3) 0.037(3) 0.035(3) -0.004(3) 0.003(2) -0.002(2)
C2 0.031(3) 0.039(3) 0.041(3) -0.001(3) 0.003(3) 0.012(2)
C3 0.029(3) 0.036(3) 0.036(3) 0.002(3) 0.001(2) -0.001(2)
C4 0.029(3) 0.041(3) 0.031(3) -0.005(3) 0.004(2) 0.001(2)
C5 0.042(3) 0.047(3) 0.030(3) -0.002(3) 0.007(3) -0.001(3)
C6 0.047(4) 0.040(3) 0.038(3) -0.004(3) 0.000(3) -0.001(3)
C7 0.031(3) 0.032(3) 0.035(3) -0.003(2) 0.004(3) -0.003(2)
C8 0.029(3) 0.036(3) 0.031(3) -0.004(2) 0.006(2) 0.004(2)
C9 0.032(3) 0.033(3) 0.037(3) -0.003(3) 0.001(2) 0.009(2)
C10 0.040(3) 0.073(5) 0.040(3) 0.008(3) 0.016(3) 0.007(3)
C11 0.042(3) 0.096(5) 0.037(3) 0.014(4) -0.001(3) 0.020(4)
C12 0.039(3) 0.066(4) 0.034(3) -0.008(3) -0.004(3) 0.014(3)
C13 0.039(4) 0.073(4) 0.041(4) 0.008(3) 0.008(3) 0.006(3)
C14 0.038(4) 0.057(4) 0.042(3) 0.019(3) 0.003(3) 0.002(3)
C15 0.040(3) 0.039(3) 0.045(4) -0.009(3) 0.014(3) 0.004(3)
C16 0.062(5) 0.115(6) 0.030(3) -0.028(4) 0.004(3) -0.007(4)
N1 0.045(3) 0.028(2) 0.048(3) -0.002(2) 0.005(2) 0.001(2)
O1 0.040(2) 0.042(2) 0.030(2) 0.0030(18) -0.0006(17) 0.0017(18)
O2 0.046(2) 0.034(2) 0.0254(19) -0.0036(16) 0.0012(17) 0.0053(17)
O3 0.082(4) 0.079(3) 0.044(3) -0.003(2) 0.024(3) -0.021(3)
O4 0.043(3) 0.071(3) 0.037(2) -0.024(2) 0.0077(19) -0.012(2)
O5 0.075(3) 0.028(2) 0.049(3) -0.0057(19) 0.006(2) 0.003(2)

_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 C12 1.897(6) . ?
C1 O1 1.398(7) . ?
C1 O2 1.453(7) . ?
C1 C2 1.508(7) . ?
C1 C15 1.512(8) . ?
C2 C3 1.554(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.509(7) . ?
C3 C9 1.520(7) . ?
C3 H3 0.9800 . ?
C4 C8 1.325(7) . ?
C4 C5 1.508(7) . ?
C5 C6 1.539(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.501(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N1 1.273(7) . ?
C7 C8 1.440(7) . ?
C8 O2 1.372(6) . ?
C9 C14 1.367(8) . ?
C9 C10 1.376(7) . ?
C10 C11 1.389(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(8) . ?
C13 C14 1.376(8) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O3 1.179(7) . ?
C15 O4 1.335(7) . ?
C16 O4 1.449(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 O5 1.437(6) . ?
O1 H1 0.8200 . ?
O5 H5 0.8200 . ?

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
O1 C1 O2 108.5(4) . . ?
O1 C1 C2 110.1(4) . . ?
O2 C1 C2 111.5(4) . . ?
O1 C1 C15 114.7(4) . . ?
O2 C1 C15 102.5(4) . . ?
C2 C1 C15 109.4(4) . . ?
C1 C2 C3 113.3(4) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C9 112.2(4) . . ?
C4 C3 C2 106.7(4) . . ?
C9 C3 C2 112.8(4) . . ?
C4 C3 H3 108.3 . . ?
C9 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
C8 C4 C5 110.4(5) . . ?
C8 C4 C3 123.2(5) . . ?
C5 C4 C3 126.4(5) . . ?
C4 C5 C6 104.4(5) . . ?
C4 C5 H5A 110.9 . . ?
C6 C5 H5A 110.9 . . ?
C4 C5 H5B 110.9 . . ?
C6 C5 H5B 110.9 . . ?
H5A C5 H5B 108.9 . . ?
C7 C6 C5 104.5(4) . . ?
C7 C6 H6A 110.8 . . ?
C5 C6 H6A 110.8 . . ?
C7 C6 H6B 110.8 . . ?
C5 C6 H6B 110.8 . . ?
H6A C6 H6B 108.9 . . ?
N1 C7 C8 122.9(5) . . ?
N1 C7 C6 129.5(5) . . ?
C8 C7 C6 107.5(5) . . ?
C4 C8 O2 127.1(5) . . ?
C4 C8 C7 112.5(5) . . ?
O2 C8 C7 120.4(5) . . ?
C14 C9 C10 117.2(5) . . ?
C14 C9 C3 123.9(5) . . ?
C10 C9 C3 118.8(5) . . ?
C9 C10 C11 123.0(5) . . ?
C9 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C10 C11 C12 116.5(5) . . ?
C10 C11 H11 121.8 . . ?
C12 C11 H11 121.8 . . ?
C13 C12 C11 122.2(6) . . ?
C13 C12 Br1 119.2(5) . . ?
C11 C12 Br1 118.5(4) . . ?
C12 C13 C14 118.4(6) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C9 C14 C13 122.7(5) . . ?
C9 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
O3 C15 O4 124.2(5) . . ?
O3 C15 C1 124.2(5) . . ?
O4 C15 C1 111.5(5) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 N1 O5 109.1(4) . . ?
C1 O1 H1 109.5 . . ?
C8 O2 C1 114.1(4) . . ?
C15 O4 C16 114.7(5) . . ?
N1 O5 H5 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -62.0(6) . . . . ?
O2 C1 C2 C3 58.4(6) . . . . ?
C15 C1 C2 C3 171.1(4) . . . . ?
C1 C2 C3 C4 -42.9(6) . . . . ?
C1 C2 C3 C9 -166.5(5) . . . . ?
C9 C3 C4 C8 137.6(5) . . . . ?
C2 C3 C4 C8 13.7(7) . . . . ?
C9 C3 C4 C5 -45.2(7) . . . . ?
C2 C3 C4 C5 -169.2(5) . . . . ?
C8 C4 C5 C6 -7.0(6) . . . . ?
C3 C4 C5 C6 175.5(5) . . . . ?
C4 C5 C6 C7 8.1(6) . . . . ?
C5 C6 C7 N1 175.2(6) . . . . ?
C5 C6 C7 C8 -6.8(6) . . . . ?
C5 C4 C8 O2 -174.6(5) . . . . ?
C3 C4 C8 O2 3.0(9) . . . . ?
C5 C4 C8 C7 2.9(6) . . . . ?
C3 C4 C8 C7 -179.6(5) . . . . ?
N1 C7 C8 C4 -179.1(5) . . . . ?
C6 C7 C8 C4 2.7(6) . . . . ?
N1 C7 C8 O2 -1.5(8) . . . . ?
C6 C7 C8 O2 -179.7(5) . . . . ?
C4 C3 C9 C14 -82.0(7) . . . . ?
C2 C3 C9 C14 38.5(7) . . . . ?
C4 C3 C9 C10 97.6(6) . . . . ?
C2 C3 C9 C10 -141.9(5) . . . . ?
C14 C9 C10 C11 -0.5(9) . . . . ?
C3 C9 C10 C11 179.8(6) . . . . ?
C9 C10 C11 C12 0.2(10) . . . . ?
C10 C11 C12 C13 0.1(10) . . . . ?
C10 C11 C12 Br1 -178.8(5) . . . . ?
C11 C12 C13 C14 -0.2(9) . . . . ?
Br1 C12 C13 C14 178.8(5) . . . . ?
C10 C9 C14 C13 0.5(9) . . . . ?
C3 C9 C14 C13 -179.9(5) . . . . ?
C12 C13 C14 C9 -0.2(9) . . . . ?
O1 C1 C15 O3 173.0(6) . . . . ?
O2 C1 C15 O3 55.6(7) . . . . ?
C2 C1 C15 O3 -62.8(7) . . . . ?
O1 C1 C15 O4 -10.0(6) . . . . ?
O2 C1 C15 O4 -127.4(4) . . . . ?
C2 C1 C15 O4 114.2(5) . . . . ?
C8 C7 N1 O5 177.7(5) . . . . ?
C6 C7 N1 O5 -4.5(8) . . . . ?
C4 C8 O2 C1 10.4(7) . . . . ?
C7 C8 O2 C1 -166.9(5) . . . . ?
O1 C1 O2 C8 81.4(5) . . . . ?
C2 C1 O2 C8 -39.9(6) . . . . ?
C15 C1 O2 C8 -156.8(4) . . . . ?
O3 C15 O4 C16 -8.3(8) . . . . ?
C1 C15 O4 C16 174.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.073
_database_code_depnum_ccdc_archive 'CCDC 931435'