# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_bo3350
_database_code_depnum_ccdc_archive 'CCDC 1040622'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 Br2 N3 O5'
_chemical_formula_weight         551.20

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.958(2)
_cell_length_b                   10.5456(8)
_cell_length_c                   11.151(4)
_cell_angle_alpha                72.1(2)
_cell_angle_beta                 84.9(2)
_cell_angle_gamma                69.76(17)
_cell_volume                     1045.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    1419
_cell_measurement_theta_min      2.764
_cell_measurement_theta_max      31.502

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548
_exptl_absorpt_coefficient_mu    3.917
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.2399
_exptl_absorpt_correction_T_max  0.3580
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15675
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         31.52
_reflns_number_total             6855
_reflns_number_gt                4789
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0419P)²+0.1160P] where P=(Fo²+2Fc²)/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_number_reflns         6855
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1050
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.70116(3) 0.71582(3) -0.06280(3) 0.04120(9) Uani 1 1 d . . .
Br2 Br 1.11250(3) 0.47643(3) 0.33199(3) 0.04217(9) Uani 1 1 d . . .
O1 O 0.7021(2) 0.4168(2) 0.00227(17) 0.0378(4) Uani 1 1 d . . .
O2 O 0.59393(17) 0.30077(17) 0.32774(16) 0.0274(4) Uani 1 1 d . . .
O3 O 0.6857(2) 0.3938(2) 0.4442(2) 0.0420(5) Uani 1 1 d . . .
O4 O 0.9908(3) 0.1522(2) -0.0387(2) 0.0517(6) Uani 1 1 d . . .
O5 O 0.8085(3) 0.1326(3) -0.1155(2) 0.0769(8) Uani 1 1 d . . .
N1 N 0.79987(19) -0.04200(19) 0.51373(17) 0.0214(4) Uani 1 1 d . . .
N2 N 0.68605(19) 0.08155(19) 0.49093(18) 0.0216(4) Uani 1 1 d . . .
N3 N 0.8688(3) 0.1473(3) -0.0321(2) 0.0480(6) Uani 1 1 d . . .
C1 C 0.7982(2) 0.4237(3) 0.0797(2) 0.0261(5) Uani 1 1 d . . .
C2 C 0.8117(2) 0.5550(3) 0.0628(2) 0.0295(5) Uani 1 1 d . . .
C3 C 0.9058(2) 0.5712(3) 0.1363(2) 0.0296(5) Uani 1 1 d . . .
H3 H 0.9145 0.6612 0.1240 0.036 Uiso 1 1 calc R . .
C4 C 0.9871(2) 0.4535(3) 0.2281(2) 0.0264(5) Uani 1 1 d . . .
C5 C 0.9776(2) 0.3217(2) 0.2450(2) 0.0241(5) Uani 1 1 d . . .
H5 H 1.0359 0.2416 0.3070 0.029 Uiso 1 1 calc R . .
C6 C 0.8824(2) 0.3063(2) 0.1710(2) 0.0238(5) Uani 1 1 d . . .
C7 C 0.8741(3) 0.1586(3) 0.1912(2) 0.0260(5) Uani 1 1 d . . .
H7 H 0.9734 0.0928 0.1867 0.031 Uiso 1 1 calc R . .
C8 C 0.7830(3) 0.1597(3) 0.0857(2) 0.0360(6) Uani 1 1 d . . .
H8 H 0.7467 0.0782 0.1170 0.043 Uiso 1 1 calc R . .
C9 C 0.6570(3) 0.2950(3) 0.0470(3) 0.0426(7) Uani 1 1 d . . .
H9A H 0.6011 0.2917 -0.0203 0.051 Uiso 1 1 calc R . .
H9B H 0.5940 0.3035 0.1201 0.051 Uiso 1 1 calc R . .
C10 C 1.0093(3) -0.1474(3) 0.3990(2) 0.0282(5) Uani 1 1 d . . .
H10A H 1.0929 -0.1177 0.3955 0.034 Uiso 1 1 calc R . .
H10B H 1.0033 -0.1718 0.3222 0.034 Uiso 1 1 calc R . .
H10C H 1.0186 -0.2302 0.4725 0.034 Uiso 1 1 calc R . .
C11 C 0.8773(2) -0.0298(2) 0.4096(2) 0.0211(4) Uani 1 1 d . . .
C12 C 0.8163(2) 0.1034(2) 0.3180(2) 0.0218(4) Uani 1 1 d . . .
C13 C 0.6957(2) 0.1701(2) 0.3754(2) 0.0236(5) Uani 1 1 d . . .
C14 C 0.6009(3) 0.4117(2) 0.3673(2) 0.0304(5) Uani 1 1 d . . .
C15 C 0.4909(3) 0.5457(3) 0.2981(3) 0.0431(7) Uani 1 1 d . . .
H15A H 0.4733 0.6157 0.3438 0.052 Uiso 1 1 calc R . .
H15B H 0.4018 0.5282 0.2912 0.052 Uiso 1 1 calc R . .
H15C H 0.5249 0.5817 0.2135 0.052 Uiso 1 1 calc R . .
C16 C 0.5809(2) 0.1049(2) 0.5844(2) 0.0226(4) Uani 1 1 d . . .
C17 C 0.6240(3) 0.0532(2) 0.7098(2) 0.0278(5) Uani 1 1 d . . .
H17 H 0.7222 0.0044 0.7330 0.033 Uiso 1 1 calc R . .
C18 C 0.5204(3) 0.0741(3) 0.8018(3) 0.0339(6) Uani 1 1 d . . .
H18 H 0.5484 0.0374 0.8884 0.041 Uiso 1 1 calc R . .
C19 C 0.3793(3) 0.1471(3) 0.7685(3) 0.0352(6) Uani 1 1 d . . .
H19 H 0.3102 0.1624 0.8317 0.042 Uiso 1 1 calc R . .
C20 C 0.3373(3) 0.1983(3) 0.6432(3) 0.0350(6) Uani 1 1 d . . .
H20 H 0.2393 0.2489 0.6204 0.042 Uiso 1 1 calc R . .
C21 C 0.4375(3) 0.1764(3) 0.5500(3) 0.0294(5) Uani 1 1 d . . .
H21 H 0.4084 0.2099 0.4638 0.035 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
Br1 C2 1.891(7) . ?
Br2 C4 1.897(4) . ?
O1 C1 1.379(4) . ?
O1 C9 1.437(4) . ?
O2 C13 1.374(5) . ?
O2 C14 1.395(3) . ?
O3 C14 1.186(4) . ?
O4 N3 1.229(3) . ?
O5 N3 1.226(4) . ?
N1 C11 1.333(4) . ?
N1 N2 1.369(4) . ?
N2 C13 1.357(5) . ?
N2 C16 1.424(4) . ?
N3 C8 1.517(5) . ?
C1 C6 1.390(6) . ?
C1 C2 1.391(4) . ?
C2 C3 1.382(4) . ?
C3 C4 1.384(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(3) . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.534(3) . ?
C7 C12 1.501(4) . ?
C7 C8 1.542(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.509(6) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.488(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.423(5) . ?
C12 C13 1.379(4) . ?
C14 C15 1.484(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.384(4) . ?
C16 C21 1.389(4) . ?
C17 C18 1.399(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.369(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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
C1 O1 C9 115.4(3) . . ?
C13 O2 C14 117.5(2) . . ?
C11 N1 N2 105.6(3) . . ?
C13 N2 N1 110.6(3) . . ?
C13 N2 C16 128.9(2) . . ?
N1 N2 C16 120.5(3) . . ?
O5 N3 O4 124.6(3) . . ?
O5 N3 C8 115.8(3) . . ?
O4 N3 C8 119.6(3) . . ?
O1 C1 C6 123.1(3) . . ?
O1 C1 C2 117.5(3) . . ?
C6 C1 C2 119.3(3) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 Br1 118.5(2) . . ?
C1 C2 Br1 120.2(2) . . ?
C2 C3 C4 118.6(3) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 Br2 120.2(3) . . ?
C3 C4 Br2 118.7(2) . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 C7 121.3(3) . . ?
C5 C6 C7 118.9(3) . . ?
C12 C7 C6 112.0(3) . . ?
C12 C7 C8 110.4(2) . . ?
C6 C7 C8 110.7(3) . . ?
C12 C7 H7 107.9 . . ?
C6 C7 H7 107.9 . . ?
C8 C7 H7 107.9 . . ?
C9 C8 N3 106.7(3) . . ?
C9 C8 C7 111.6(3) . . ?
N3 C8 C7 111.9(2) . . ?
C9 C8 H8 108.8 . . ?
N3 C8 H8 108.8 . . ?
C7 C8 H8 108.8 . . ?
O1 C9 C8 111.6(2) . . ?
O1 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
O1 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 111.5(3) . . ?
N1 C11 C10 120.7(3) . . ?
C12 C11 C10 127.8(3) . . ?
C13 C12 C11 103.7(3) . . ?
C13 C12 C7 128.7(3) . . ?
C11 C12 C7 127.6(3) . . ?
N2 C13 O2 122.7(3) . . ?
N2 C13 C12 108.6(3) . . ?
O2 C13 C12 128.6(3) . . ?
O3 C14 O2 121.9(3) . . ?
O3 C14 C15 128.5(3) . . ?
O2 C14 C15 109.6(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 120.8(3) . . ?
C17 C16 N2 118.8(2) . . ?
C21 C16 N2 120.4(3) . . ?
C16 C17 C18 118.8(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 119.2(3) . . ?
C16 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?

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
C11 N1 N2 C13 -1.6(2) . . . . ?
C11 N1 N2 C16 -179.52(19) . . . . ?
C9 O1 C1 C6 20.5(3) . . . . ?
C9 O1 C1 C2 -160.7(2) . . . . ?
O1 C1 C2 C3 -179.9(2) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
O1 C1 C2 Br1 -0.1(3) . . . . ?
C6 C1 C2 Br1 178.79(17) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
Br1 C2 C3 C4 -179.84(17) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C2 C3 C4 Br2 -178.33(17) . . . . ?
C3 C4 C5 C6 -1.6(4) . . . . ?
Br2 C4 C5 C6 178.11(17) . . . . ?
O1 C1 C6 C5 179.6(2) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
O1 C1 C6 C7 0.3(4) . . . . ?
C2 C1 C6 C7 -178.5(2) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 179.8(2) . . . . ?
C1 C6 C7 C12 -114.4(3) . . . . ?
C5 C6 C7 C12 66.3(3) . . . . ?
C1 C6 C7 C8 9.2(3) . . . . ?
C5 C6 C7 C8 -170.1(2) . . . . ?
O5 N3 C8 C9 -64.9(4) . . . . ?
O4 N3 C8 C9 115.1(3) . . . . ?
O5 N3 C8 C7 172.7(3) . . . . ?
O4 N3 C8 C7 -7.3(4) . . . . ?
C12 C7 C8 C9 87.0(3) . . . . ?
C6 C7 C8 C9 -37.5(3) . . . . ?
C12 C7 C8 N3 -153.4(2) . . . . ?
C6 C7 C8 N3 82.1(3) . . . . ?
C1 O1 C9 C8 -50.1(4) . . . . ?
N3 C8 C9 O1 -63.3(3) . . . . ?
C7 C8 C9 O1 59.3(3) . . . . ?
N2 N1 C11 C12 1.1(2) . . . . ?
N2 N1 C11 C10 -178.52(19) . . . . ?
N1 C11 C12 C13 -0.2(2) . . . . ?
C10 C11 C12 C13 179.4(2) . . . . ?
N1 C11 C12 C7 177.8(2) . . . . ?
C10 C11 C12 C7 -2.6(4) . . . . ?
C6 C7 C12 C13 48.9(3) . . . . ?
C8 C7 C12 C13 -74.9(3) . . . . ?
C6 C7 C12 C11 -128.6(3) . . . . ?
C8 C7 C12 C11 107.6(3) . . . . ?
N1 N2 C13 O2 178.92(19) . . . . ?
C16 N2 C13 O2 -3.4(4) . . . . ?
N1 N2 C13 C12 1.6(3) . . . . ?
C16 N2 C13 C12 179.2(2) . . . . ?
C14 O2 C13 N2 81.0(3) . . . . ?
C14 O2 C13 C12 -102.2(3) . . . . ?
C11 C12 C13 N2 -0.8(2) . . . . ?
C7 C12 C13 N2 -178.8(2) . . . . ?
C11 C12 C13 O2 -178.0(2) . . . . ?
C7 C12 C13 O2 4.1(4) . . . . ?
C13 O2 C14 O3 -4.1(4) . . . . ?
C13 O2 C14 C15 175.2(2) . . . . ?
C13 N2 C16 C17 -141.5(3) . . . . ?
N1 N2 C16 C17 36.0(3) . . . . ?
C13 N2 C16 C21 39.5(4) . . . . ?
N1 N2 C16 C21 -143.1(3) . . . . ?
C21 C16 C17 C18 0.0(4) . . . . ?
N2 C16 C17 C18 -179.0(2) . . . . ?
C16 C17 C18 C19 -1.4(4) . . . . ?
C17 C18 C19 C20 1.4(4) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C17 C16 C21 C20 1.3(4) . . . . ?
N2 C16 C21 C20 -179.7(2) . . . . ?
C19 C20 C21 C16 -1.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        31.52
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.324
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.093

