# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1500848'
_audit_update_record             
;
2016-08-24 deposited with the CCDC.
2016-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        PBDK1
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 Br N O5'
_chemical_formula_weight         398.25

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                   5.2286(5)
_cell_length_b                   8.3500(6)
_cell_length_c                   20.2441(18)
_cell_angle_alpha                79.956(7)
_cell_angle_beta                 89.888(8)
_cell_angle_gamma                81.369(7)
_cell_volume                     860.17(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    1658
_cell_measurement_theta_min      2.8631
_cell_measurement_theta_max      29.1573

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    2.416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4852
_exptl_absorpt_correction_T_max  0.5213
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7194
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0707
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3460
_reflns_number_gt                2261
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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)+(0.0630P)²+0.0000P] 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_number_reflns         3460
_refine_ls_number_parameters     232
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1487
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.024
_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 0.17889(9) 0.17127(6) 0.12976(2) 0.0683(2) Uani 1 1 d . . .
O3 O 0.1077(6) 0.3576(4) 0.36939(14) 0.0564(8) Uani 1 1 d . . .
O2 O 1.1388(6) -0.1514(4) 0.41932(14) 0.0553(8) Uani 1 1 d D . .
O1 O 1.4547(6) -0.3270(4) 0.36221(15) 0.0567(8) Uani 1 1 d D . .
N1 N 1.3478(7) -0.3946(4) 0.13827(16) 0.0459(8) Uani 1 1 d . . .
O4 O 1.5809(8) -0.2996(6) 0.01241(19) 0.1036(15) Uani 1 1 d . . .
H4 H 1.6345 -0.2473 -0.0215 0.124 Uiso 1 1 calc R . .
O5 O 0.7400(7) 0.9217(5) 0.1500(2) 0.0837(11) Uani 1 1 d D . .
C6 C 1.3034(8) -0.2858(5) 0.3096(2) 0.0455(10) Uani 1 1 d . . .
C3 C 1.6239(8) -0.4720(5) 0.2558(2) 0.0536(11) Uani 1 1 d . . .
H3 H 1.7194 -0.4992 0.2959 0.064 Uiso 1 1 calc R . .
C4 C 1.3980(7) -0.3603(5) 0.25083(19) 0.0415(9) Uani 1 1 d . . .
C11 C 0.3809(8) 0.1818(5) 0.3137(2) 0.0493(10) Uani 1 1 d . . .
H11 H 0.2713 0.2176 0.2762 0.059 Uiso 1 1 calc R . .
C7 C 1.0743(8) -0.1797(5) 0.3081(2) 0.0456(10) Uani 1 1 d . . .
H7 H 0.9692 -0.1543 0.2695 0.055 Uiso 1 1 calc R . .
C8 C 0.9990(8) -0.1096(5) 0.3647(2) 0.0439(10) Uani 1 1 d . . .
C5 C 1.2646(8) -0.3243(5) 0.1906(2) 0.0462(10) Uani 1 1 d . . .
H5 H 1.1125 -0.2491 0.1859 0.055 Uiso 1 1 calc R . .
C9 C 0.7636(8) 0.0113(5) 0.36625(19) 0.0425(9) Uani 1 1 d . . .
C12 C 0.3244(8) 0.2430(5) 0.3720(2) 0.0451(10) Uani 1 1 d . . .
C14 C 0.7024(9) 0.0733(5) 0.4244(2) 0.0492(10) Uani 1 1 d . . .
H14 H 0.8105 0.0364 0.4621 0.059 Uiso 1 1 calc R . .
C13 C 0.4860(8) 0.1882(5) 0.4281(2) 0.0515(11) Uani 1 1 d . . .
H13 H 0.4491 0.2283 0.4677 0.062 Uiso 1 1 calc R . .
C1 C 1.5678(9) -0.5049(5) 0.1436(2) 0.0546(11) Uani 1 1 d . . .
H1A H 1.6223 -0.5543 0.1072 0.066 Uiso 1 1 calc R . .
C15 C 0.0365(10) 0.4173(6) 0.4296(2) 0.0627(13) Uani 1 1 d . . .
H15A H -0.1189 0.4960 0.4214 0.094 Uiso 1 1 calc R . .
H15B H 0.1733 0.4690 0.4441 0.094 Uiso 1 1 calc R . .
H15C H 0.0072 0.3272 0.4638 0.094 Uiso 1 1 calc R . .
C16 C 1.2048(9) -0.3463(6) 0.0730(2) 0.0609(13) Uani 1 1 d . . .
H16A H 1.0277 -0.2997 0.0802 0.073 Uiso 1 1 calc R . .
H16B H 1.2008 -0.4431 0.0527 0.073 Uiso 1 1 calc R . .
C10 C 0.5980(8) 0.0682(5) 0.3107(2) 0.0471(10) Uani 1 1 d . . .
H10 H 0.6348 0.0288 0.2710 0.057 Uiso 1 1 calc R . .
C17 C 1.3308(10) -0.2221(7) 0.0261(2) 0.0707(14) Uani 1 1 d . . .
H17A H 1.2288 -0.1855 -0.0152 0.085 Uiso 1 1 calc R . .
H17B H 1.3439 -0.1272 0.0468 0.085 Uiso 1 1 calc R . .
C2 C 1.7085(9) -0.5436(6) 0.2014(2) 0.0587(12) Uani 1 1 d . . .
H2A H 1.8614 -0.6179 0.2048 0.070 Uiso 1 1 calc R . .
H2 H 1.266(14) -0.213(11) 0.406(5) 0.070 Uiso 0.49(8) 1 d PD A 2
H1 H 1.398(19) -0.282(12) 0.395(4) 0.070 Uiso 0.51(8) 1 d PD A 1
H5A H 0.838(9) 0.994(5) 0.140(3) 0.088 Uiso 1 1 d D . .
H5B H 0.582(5) 0.965(7) 0.143(3) 0.088 Uiso 1 1 d D . .

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 0.0645(4) 0.0717(4) 0.0674(4) -0.0204(2) 0.0090(2) 0.0032(3)
O3 0.063(2) 0.0484(18) 0.0544(19) -0.0158(13) 0.0033(14) 0.0095(15)
O2 0.062(2) 0.056(2) 0.0438(18) -0.0137(14) -0.0043(15) 0.0090(16)
O1 0.059(2) 0.055(2) 0.052(2) -0.0138(15) -0.0024(16) 0.0093(15)
N1 0.050(2) 0.042(2) 0.044(2) -0.0121(15) 0.0058(16) 0.0008(16)
O4 0.094(3) 0.114(4) 0.082(3) 0.017(2) 0.029(2) 0.011(3)
O5 0.064(3) 0.065(3) 0.113(3) -0.003(2) -0.008(2) 0.007(2)
C6 0.049(3) 0.037(2) 0.049(3) -0.0063(17) 0.000(2) -0.0038(19)
C3 0.054(3) 0.052(3) 0.049(3) -0.004(2) 0.004(2) 0.006(2)
C4 0.044(2) 0.034(2) 0.044(2) -0.0046(16) 0.0060(18) -0.0012(18)
C11 0.057(3) 0.049(3) 0.039(2) -0.0098(18) -0.0033(19) 0.003(2)
C7 0.047(2) 0.042(2) 0.046(2) -0.0128(17) 0.0002(18) 0.0047(19)
C8 0.051(3) 0.037(2) 0.044(2) -0.0074(17) 0.0017(19) -0.0076(19)
C5 0.047(2) 0.038(2) 0.053(3) -0.0125(18) 0.0077(19) 0.0033(18)
C9 0.050(2) 0.037(2) 0.041(2) -0.0084(16) 0.0037(18) -0.0032(18)
C12 0.047(2) 0.035(2) 0.050(3) -0.0052(17) 0.0028(19) -0.0005(18)
C14 0.060(3) 0.047(3) 0.040(2) -0.0109(18) -0.0041(19) -0.001(2)
C13 0.060(3) 0.048(3) 0.048(3) -0.0194(19) 0.004(2) 0.001(2)
C1 0.059(3) 0.046(3) 0.059(3) -0.016(2) 0.015(2) -0.001(2)
C15 0.067(3) 0.056(3) 0.063(3) -0.019(2) 0.012(2) 0.008(2)
C16 0.061(3) 0.068(3) 0.054(3) -0.023(2) -0.005(2) 0.005(3)
C10 0.059(3) 0.045(2) 0.038(2) -0.0128(17) 0.0031(19) -0.002(2)
C17 0.087(4) 0.067(3) 0.052(3) -0.010(2) 0.002(3) 0.007(3)
C2 0.058(3) 0.048(3) 0.063(3) -0.006(2) 0.010(2) 0.009(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
O3 C12 1.364(5) . ?
O3 C15 1.423(5) . ?
O2 C8 1.293(5) . ?
O1 C6 1.293(5) . ?
N1 C5 1.340(5) . ?
N1 C1 1.353(5) . ?
N1 C16 1.482(5) . ?
O4 C17 1.418(6) . ?
C6 C7 1.376(5) . ?
C6 C4 1.487(5) . ?
C3 C2 1.383(6) . ?
C3 C4 1.383(5) . ?
C4 C5 1.370(6) . ?
C11 C10 1.374(5) . ?
C11 C12 1.380(5) . ?
C7 C8 1.405(5) . ?
C8 C9 1.474(5) . ?
C9 C14 1.385(5) . ?
C9 C10 1.390(5) . ?
C12 C13 1.386(5) . ?
C14 C13 1.381(6) . ?
C1 C2 1.347(6) . ?
C16 C17 1.507(7) . ?

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
C12 O3 C15 117.4(3) . . ?
C5 N1 C1 120.6(4) . . ?
C5 N1 C16 120.0(3) . . ?
C1 N1 C16 119.4(3) . . ?
O1 C6 C7 122.4(4) . . ?
O1 C6 C4 114.8(3) . . ?
C7 C6 C4 122.8(4) . . ?
C2 C3 C4 120.4(4) . . ?
C5 C4 C3 117.5(4) . . ?
C5 C4 C6 121.9(3) . . ?
C3 C4 C6 120.6(4) . . ?
C10 C11 C12 120.4(4) . . ?
C6 C7 C8 120.1(4) . . ?
O2 C8 C7 119.9(4) . . ?
O2 C8 C9 116.6(3) . . ?
C7 C8 C9 123.6(4) . . ?
N1 C5 C4 121.6(4) . . ?
C14 C9 C10 117.7(4) . . ?
C14 C9 C8 119.9(4) . . ?
C10 C9 C8 122.4(3) . . ?
O3 C12 C11 115.9(4) . . ?
O3 C12 C13 124.2(4) . . ?
C11 C12 C13 119.8(4) . . ?
C13 C14 C9 122.0(4) . . ?
C14 C13 C12 119.0(4) . . ?
C2 C1 N1 120.4(4) . . ?
N1 C16 C17 110.9(4) . . ?
C11 C10 C9 120.9(4) . . ?
O4 C17 C16 107.6(4) . . ?
C1 C2 C3 119.5(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 Br1 0.82 2.42 3.213(4) 163.5 2_755
O2 H2 O1 0.85(2) 1.64(4) 2.464(4) 163(10) .
O1 H1 O2 0.85(2) 1.74(7) 2.464(4) 143(10) .
O5 H5A Br1 0.846(19) 2.47(2) 3.303(4) 169(5) 1_665
O5 H5B Br1 0.852(19) 2.50(3) 3.315(4) 161(5) 1_565

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.079
