# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cd213338
_database_code_depnum_ccdc_archive 'CCDC 1024512'
_audit_update_record             
;
2014-09-16 deposited with the CCDC.
2015-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 Br N O5'
_chemical_formula_weight         396.23

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.6023(6)
_cell_length_b                   7.8736(7)
_cell_length_c                   32.754(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1702.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2407
_cell_measurement_theta_min      4.975
_cell_measurement_theta_max      48.699

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.113
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    2.441
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0895
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10165
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3348
_reflns_number_gt                2523
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0594P)²+0.1495P] where P=(Fo²+2Fc²)/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   0.016(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3348
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.21864(10) 0.63595(8) 0.225162(13) 0.0974(3) Uani 1 1 d . . .
N1 N -0.3601(5) 0.3002(4) 0.40984(12) 0.0524(8) Uani 1 1 d . . .
O1 O 0.3319(4) 0.6556(4) 0.43781(8) 0.0517(6) Uani 1 1 d . . .
O2 O -0.4332(5) 0.3167(5) 0.37620(12) 0.0935(12) Uani 1 1 d . . .
O3 O -0.4438(4) 0.2230(4) 0.43697(11) 0.0709(9) Uani 1 1 d . . .
O4 O -0.0697(5) 0.9793(4) 0.42423(10) 0.0746(10) Uani 1 1 d . . .
O5 O 0.1305(4) 0.8550(3) 0.37937(7) 0.0519(6) Uani 1 1 d . . .
C1 C 0.1647(5) 0.5934(4) 0.44110(9) 0.0347(7) Uani 1 1 d . . .
C2 C -0.0316(5) 0.6774(4) 0.42776(9) 0.0303(7) Uani 1 1 d . . .
C3 C -0.1473(5) 0.5564(4) 0.39706(9) 0.0306(7) Uani 1 1 d . . .
H3 H -0.2875 0.5968 0.3956 0.037 Uiso 1 1 calc R . .
C4 C -0.1531(5) 0.3780(4) 0.41672(10) 0.0354(7) Uani 1 1 d . . .
H4 H -0.0539 0.3072 0.4024 0.042 Uiso 1 1 calc R . .
C5 C -0.0952(5) 0.3799(5) 0.46135(11) 0.0414(8) Uani 1 1 d . . .
H5 H -0.1173 0.2682 0.4738 0.050 Uiso 1 1 calc R . .
C6 C 0.1288(5) 0.4269(5) 0.46221(12) 0.0440(9) Uani 1 1 d . . .
H6A H 0.1743 0.4346 0.4903 0.053 Uiso 1 1 calc R . .
H6B H 0.2068 0.3386 0.4488 0.053 Uiso 1 1 calc R . .
C7 C -0.1630(5) 0.6915(4) 0.46645(10) 0.0403(8) Uani 1 1 d . . .
H7A H -0.0918 0.7583 0.4868 0.048 Uiso 1 1 calc R . .
H7B H -0.2881 0.7501 0.4599 0.048 Uiso 1 1 calc R . .
C8 C -0.2126(6) 0.5166(5) 0.48421(10) 0.0467(9) Uani 1 1 d . . .
H8A H -0.1768 0.5138 0.5129 0.056 Uiso 1 1 calc R . .
H8B H -0.3567 0.4950 0.4819 0.056 Uiso 1 1 calc R . .
C9 C -0.0653(5) 0.5570(4) 0.35418(10) 0.0359(8) Uani 1 1 d . . .
C10 C 0.1242(5) 0.4909(4) 0.34479(11) 0.0417(8) Uani 1 1 d . . .
H10 H 0.1970 0.4333 0.3648 0.050 Uiso 1 1 calc R . .
C11 C 0.2069(6) 0.5098(5) 0.30596(11) 0.0530(9) Uani 1 1 d . . .
H11 H 0.3340 0.4653 0.3000 0.064 Uiso 1 1 calc R . .
C12 C 0.0998(7) 0.5936(5) 0.27703(11) 0.0580(11) Uani 1 1 d . . .
C13 C -0.0913(7) 0.6529(6) 0.28434(11) 0.0620(11) Uani 1 1 d . . .
H13 H -0.1658 0.7041 0.2636 0.074 Uiso 1 1 calc R . .
C14 C -0.1722(6) 0.6355(5) 0.32313(11) 0.0512(9) Uani 1 1 d . . .
H14 H -0.3011 0.6776 0.3284 0.061 Uiso 1 1 calc R . .
C15 C 0.0054(5) 0.8544(5) 0.41034(10) 0.0377(7) Uani 1 1 d . . .
C16 C 0.1796(7) 1.0174(5) 0.36165(12) 0.0576(10) Uani 1 1 d . . .
H16A H 0.2376 1.0915 0.3822 0.069 Uiso 1 1 calc R . .
H16B H 0.0581 1.0707 0.3510 0.069 Uiso 1 1 calc R . .
C17 C 0.3248(10) 0.9895(7) 0.32878(18) 0.106(2) Uani 1 1 d . . .
H17A H 0.4466 0.9412 0.3398 0.160 Uiso 1 1 calc R . .
H17B H 0.3555 1.0959 0.3159 0.160 Uiso 1 1 calc R . .
H17C H 0.2677 0.9131 0.3090 0.160 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 C12 1.901(4) . ?
N1 O2 1.210(4) . ?
N1 O3 1.210(4) . ?
N1 C4 1.515(4) . ?
O1 C1 1.213(4) . ?
O4 C15 1.191(4) . ?
O5 C15 1.308(4) . ?
O5 C16 1.441(4) . ?
C1 C6 1.501(5) . ?
C1 C2 1.519(5) . ?
C2 C15 1.526(5) . ?
C2 C7 1.540(4) . ?
C2 C3 1.582(4) . ?
C3 C9 1.505(4) . ?
C3 C4 1.545(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.511(5) . ?
C4 H4 0.9800 . ?
C5 C8 1.523(5) . ?
C5 C6 1.524(5) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.531(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.384(5) . ?
C9 C10 1.390(5) . ?
C10 C11 1.392(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.354(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(6) . ?
C13 C14 1.385(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C16 C17 1.458(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
O2 N1 O3 122.7(4) . . ?
O2 N1 C4 116.8(3) . . ?
O3 N1 C4 120.4(3) . . ?
C15 O5 C16 117.2(3) . . ?
O1 C1 C6 122.5(3) . . ?
O1 C1 C2 125.1(3) . . ?
C6 C1 C2 112.2(3) . . ?
C1 C2 C15 111.6(3) . . ?
C1 C2 C7 106.0(2) . . ?
C15 C2 C7 109.4(3) . . ?
C1 C2 C3 109.4(3) . . ?
C15 C2 C3 112.9(2) . . ?
C7 C2 C3 107.1(2) . . ?
C9 C3 C4 113.6(2) . . ?
C9 C3 C2 114.7(3) . . ?
C4 C3 C2 107.1(2) . . ?
C9 C3 H3 107.0 . . ?
C4 C3 H3 107.0 . . ?
C2 C3 H3 107.0 . . ?
C5 C4 N1 112.1(3) . . ?
C5 C4 C3 112.8(3) . . ?
N1 C4 C3 109.1(3) . . ?
C5 C4 H4 107.5 . . ?
N1 C4 H4 107.5 . . ?
C3 C4 H4 107.5 . . ?
C4 C5 C8 110.7(3) . . ?
C4 C5 C6 105.4(3) . . ?
C8 C5 C6 108.3(3) . . ?
C4 C5 H5 110.8 . . ?
C8 C5 H5 110.8 . . ?
C6 C5 H5 110.8 . . ?
C1 C6 C5 110.9(3) . . ?
C1 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C2 111.6(3) . . ?
C8 C7 H7A 109.3 . . ?
C2 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C2 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C5 C8 C7 109.9(3) . . ?
C5 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C5 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C14 C9 C10 117.6(3) . . ?
C14 C9 C3 120.3(3) . . ?
C10 C9 C3 122.0(3) . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 119.1(4) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 121.7(4) . . ?
C11 C12 Br1 119.7(3) . . ?
C13 C12 Br1 118.5(3) . . ?
C12 C13 C14 118.9(4) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C9 C14 C13 121.5(4) . . ?
C9 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
O4 C15 O5 123.8(3) . . ?
O4 C15 C2 123.0(3) . . ?
O5 C15 C2 113.2(3) . . ?
O5 C16 C17 108.2(3) . . ?
O5 C16 H16A 110.1 . . ?
C17 C16 H16A 110.1 . . ?
O5 C16 H16B 110.1 . . ?
C17 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 C15 -1.4(4) . . . . ?
C6 C1 C2 C15 174.1(3) . . . . ?
O1 C1 C2 C7 -120.5(3) . . . . ?
C6 C1 C2 C7 55.1(3) . . . . ?
O1 C1 C2 C3 124.3(3) . . . . ?
C6 C1 C2 C3 -60.1(3) . . . . ?
C1 C2 C3 C9 -78.2(3) . . . . ?
C15 C2 C3 C9 46.9(4) . . . . ?
C7 C2 C3 C9 167.4(3) . . . . ?
C1 C2 C3 C4 48.9(3) . . . . ?
C15 C2 C3 C4 173.9(3) . . . . ?
C7 C2 C3 C4 -65.6(3) . . . . ?
O2 N1 C4 C5 168.8(4) . . . . ?
O3 N1 C4 C5 -12.5(4) . . . . ?
O2 N1 C4 C3 43.1(4) . . . . ?
O3 N1 C4 C3 -138.2(3) . . . . ?
C9 C3 C4 C5 141.0(3) . . . . ?
C2 C3 C4 C5 13.3(3) . . . . ?
C9 C3 C4 N1 -93.7(3) . . . . ?
C2 C3 C4 N1 138.6(3) . . . . ?
N1 C4 C5 C8 -74.4(4) . . . . ?
C3 C4 C5 C8 49.3(4) . . . . ?
N1 C4 C5 C6 168.8(3) . . . . ?
C3 C4 C5 C6 -67.5(3) . . . . ?
O1 C1 C6 C5 -179.5(3) . . . . ?
C2 C1 C6 C5 4.8(4) . . . . ?
C4 C5 C6 C1 56.9(4) . . . . ?
C8 C5 C6 C1 -61.6(4) . . . . ?
C1 C2 C7 C8 -61.9(3) . . . . ?
C15 C2 C7 C8 177.6(3) . . . . ?
C3 C2 C7 C8 54.8(3) . . . . ?
C4 C5 C8 C7 -61.1(4) . . . . ?
C6 C5 C8 C7 54.0(4) . . . . ?
C2 C7 C8 C5 7.0(4) . . . . ?
C4 C3 C9 C14 129.0(3) . . . . ?
C2 C3 C9 C14 -107.3(4) . . . . ?
C4 C3 C9 C10 -55.8(4) . . . . ?
C2 C3 C9 C10 67.9(4) . . . . ?
C14 C9 C10 C11 2.7(5) . . . . ?
C3 C9 C10 C11 -172.7(3) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C10 C11 C12 C13 -3.3(6) . . . . ?
C10 C11 C12 Br1 175.1(3) . . . . ?
C11 C12 C13 C14 4.0(6) . . . . ?
Br1 C12 C13 C14 -174.5(3) . . . . ?
C10 C9 C14 C13 -2.0(6) . . . . ?
C3 C9 C14 C13 173.4(3) . . . . ?
C12 C13 C14 C9 -1.2(6) . . . . ?
C16 O5 C15 O4 0.4(5) . . . . ?
C16 O5 C15 C2 -178.2(3) . . . . ?
C1 C2 C15 O4 -121.2(4) . . . . ?
C7 C2 C15 O4 -4.2(4) . . . . ?
C3 C2 C15 O4 115.0(4) . . . . ?
C1 C2 C15 O5 57.5(4) . . . . ?
C7 C2 C15 O5 174.4(3) . . . . ?
C3 C2 C15 O5 -66.3(3) . . . . ?
C15 O5 C16 C17 178.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.056
