# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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 1519677'
_audit_update_record             
;
2016-11-28 deposited with the CCDC.
2017-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.45 H2.91 Br0.18 N0.18 O0.91'
_chemical_formula_weight         76.04

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           ?
_symmetry_space_group_name_H-M   ?

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                   10.415(2)
_cell_length_b                   11.469(2)
_cell_length_c                   15.047(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1797.4(6)
_cell_formula_units_Z            22
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    2.317
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7478
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_sigmaI/netI    0.0608
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3106
_reflns_number_gt                3036
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0779P)²+5.1134P] 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   0.035(14)
_refine_ls_number_reflns         3106
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1249
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_restrained_S_all      0.885
_refine_ls_shift/su_max          0.201
_refine_ls_shift/su_mean         0.036

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 -0.02311(5) 0.65341(4) 0.11213(4) 0.03390(18) Uani 1 1 d . . .
O4 O 0.2819(3) 0.9945(3) -0.0210(2) 0.0216(7) Uani 1 1 d . . .
N1 N 0.2150(4) 1.2040(3) 0.1189(3) 0.0212(8) Uani 1 1 d . . .
O5 O 0.4822(3) 1.0918(3) 0.3584(2) 0.0240(7) Uani 1 1 d . . .
C19 C 0.4054(5) 1.1995(4) 0.0236(3) 0.0238(10) Uani 1 1 d . . .
H19A H 0.4751 1.1533 0.0012 0.036 Uiso 1 1 calc R . .
H19B H 0.4386 1.2697 0.0496 0.036 Uiso 1 1 calc R . .
H19C H 0.3483 1.2190 -0.0242 0.036 Uiso 1 1 calc R . .
C15 C 0.2787(4) 1.0164(4) 0.0577(3) 0.0169(9) Uani 1 1 d . . .
C18 C 0.2225(4) 0.9358(4) 0.1245(3) 0.0155(9) Uani 1 1 d . . .
O6 O 0.4319(3) 0.9025(3) 0.3442(2) 0.0248(7) Uani 1 1 d . . .
O2 O 0.1094(3) 1.1712(3) 0.0940(3) 0.0321(8) Uani 1 1 d . . .
C6 C 0.3275(4) 1.0493(4) 0.2504(3) 0.0150(8) Uani 1 1 d . . .
H6 H 0.2738 1.1098 0.2774 0.018 Uiso 1 1 calc R . .
C5 C 0.1467(4) 0.8443(4) 0.0930(3) 0.0206(9) Uani 1 1 d . . .
H5 H 0.1401 0.8294 0.0325 0.025 Uiso 1 1 calc R . .
C13 C 0.5434(4) 0.9255(4) 0.1437(3) 0.0192(9) Uani 1 1 d . . .
H13 H 0.4683 0.8817 0.1434 0.023 Uiso 1 1 calc R . .
C1 C 0.0815(4) 0.7763(4) 0.1543(3) 0.0239(10) Uani 1 1 d . . .
C4 C 0.2381(4) 0.9558(4) 0.2152(3) 0.0166(9) Uani 1 1 d . . .
C7 C 0.4126(4) 1.1099(4) 0.1789(3) 0.0168(9) Uani 1 1 d . . .
H7 H 0.4360 1.1867 0.2023 0.020 Uiso 1 1 calc R . .
C3 C 0.1688(4) 0.8865(4) 0.2746(3) 0.0205(10) Uani 1 1 d . . .
H3 H 0.1763 0.8997 0.3353 0.025 Uiso 1 1 calc R . .
C9 C 0.6508(5) 1.1090(4) 0.1571(4) 0.0292(12) Uani 1 1 d . . .
H9 H 0.6481 1.1893 0.1657 0.035 Uiso 1 1 calc R . .
C17 C 0.4171(4) 1.0037(4) 0.3229(3) 0.0164(9) Uani 1 1 d . . .
C2 C 0.0890(5) 0.7985(4) 0.2443(3) 0.0236(10) Uani 1 1 d . . .
H2A H 0.0408 0.7547 0.2843 0.028 Uiso 1 1 calc R . .
C12 C 0.6607(5) 0.8717(4) 0.1288(3) 0.0251(10) Uani 1 1 d . . .
H12 H 0.6634 0.7917 0.1186 0.030 Uiso 1 1 calc R . .
C8 C 0.5382(4) 1.0454(4) 0.1589(3) 0.0169(8) Uani 1 1 d . . .
O1 O 0.2337(4) 1.2937(3) 0.1605(3) 0.0391(10) Uani 1 1 d . . .
C14 C 0.3328(4) 1.1307(4) 0.0936(3) 0.0179(9) Uani 1 1 d . . .
C16 C 0.5826(6) 1.0597(5) 0.4200(4) 0.0382(14) Uani 1 1 d . . .
H16A H 0.5469 1.0130 0.4669 0.057 Uiso 1 1 calc R . .
H16B H 0.6202 1.1288 0.4448 0.057 Uiso 1 1 calc R . .
H16C H 0.6473 1.0158 0.3893 0.057 Uiso 1 1 calc R . .
C10 C 0.7680(5) 1.0544(5) 0.1425(5) 0.0408(15) Uani 1 1 d . . .
H10 H 0.8432 1.0981 0.1419 0.049 Uiso 1 1 calc R . .
C11 C 0.7733(5) 0.9350(5) 0.1289(4) 0.0281(11) Uani 1 1 d . . .
H11 H 0.8518 0.8980 0.1200 0.034 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 C1 1.891(5) . ?
O4 C15 1.210(6) . ?
N1 O2 1.220(5) . ?
N1 O1 1.219(5) . ?
N1 C14 1.536(5) . ?
O5 C17 1.329(6) . ?
O5 C16 1.445(6) . ?
C19 C14 1.517(6) . ?
C15 C18 1.486(6) . ?
C15 C14 1.526(6) . ?
C18 C4 1.394(7) . ?
C18 C5 1.396(6) . ?
O6 C17 1.214(6) . ?
C6 C4 1.516(6) . ?
C6 C17 1.527(6) . ?
C6 C7 1.558(6) . ?
C5 C1 1.385(7) . ?
C13 C12 1.387(6) . ?
C13 C8 1.395(6) . ?
C1 C2 1.381(7) . ?
C4 C3 1.397(7) . ?
C7 C8 1.532(6) . ?
C7 C14 1.548(6) . ?
C3 C2 1.385(7) . ?
C9 C10 1.390(7) . ?
C9 C8 1.381(7) . ?
C12 C11 1.380(7) . ?
C10 C11 1.386(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
O2 N1 O1 124.2(4) . . ?
O2 N1 C14 118.3(3) . . ?
O1 N1 C14 117.5(4) . . ?
C17 O5 C16 115.7(4) . . ?
O4 C15 C18 122.9(4) . . ?
O4 C15 C14 121.0(4) . . ?
C18 C15 C14 116.1(4) . . ?
C4 C18 C5 121.4(4) . . ?
C4 C18 C15 121.0(4) . . ?
C5 C18 C15 117.4(4) . . ?
C4 C6 C17 112.5(4) . . ?
C4 C6 C7 115.1(4) . . ?
C17 C6 C7 107.4(4) . . ?
C1 C5 C18 118.4(4) . . ?
C12 C13 C8 120.0(4) . . ?
C2 C1 C5 121.4(5) . . ?
C2 C1 Br1 119.9(4) . . ?
C5 C1 Br1 118.6(4) . . ?
C18 C4 C3 118.2(4) . . ?
C18 C4 C6 122.0(4) . . ?
C3 C4 C6 119.8(4) . . ?
C8 C7 C14 111.8(4) . . ?
C8 C7 C6 113.9(4) . . ?
C14 C7 C6 109.6(3) . . ?
C4 C3 C2 121.0(4) . . ?
C10 C9 C8 120.7(4) . . ?
O6 C17 O5 123.7(4) . . ?
O6 C17 C6 126.4(4) . . ?
O5 C17 C6 109.8(4) . . ?
C1 C2 C3 119.4(4) . . ?
C13 C12 C11 121.0(4) . . ?
C13 C8 C9 119.0(4) . . ?
C13 C8 C7 122.8(4) . . ?
C9 C8 C7 118.2(4) . . ?
C15 C14 C19 112.6(4) . . ?
C15 C14 N1 105.3(3) . . ?
C19 C14 N1 106.5(4) . . ?
C15 C14 C7 111.1(4) . . ?
C19 C14 C7 112.8(4) . . ?
N1 C14 C7 108.0(4) . . ?
C9 C10 C11 120.3(5) . . ?
C10 C11 C12 119.1(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
O4 C15 C18 C4 170.1(4) . . . . ?
C14 C15 C18 C4 -10.2(6) . . . . ?
O4 C15 C18 C5 -14.1(6) . . . . ?
C14 C15 C18 C5 165.7(4) . . . . ?
C4 C18 C5 C1 3.1(7) . . . . ?
C15 C18 C5 C1 -172.7(4) . . . . ?
C18 C5 C1 C2 0.9(7) . . . . ?
C18 C5 C1 Br1 179.2(3) . . . . ?
C5 C18 C4 C3 -4.3(6) . . . . ?
C15 C18 C4 C3 171.4(4) . . . . ?
C5 C18 C4 C6 175.5(4) . . . . ?
C15 C18 C4 C6 -8.8(6) . . . . ?
C17 C6 C4 C18 -130.8(4) . . . . ?
C7 C6 C4 C18 -7.4(6) . . . . ?
C17 C6 C4 C3 49.1(5) . . . . ?
C7 C6 C4 C3 172.4(4) . . . . ?
C4 C6 C7 C8 -86.0(5) . . . . ?
C17 C6 C7 C8 40.1(5) . . . . ?
C4 C6 C7 C14 40.0(5) . . . . ?
C17 C6 C7 C14 166.1(4) . . . . ?
C18 C4 C3 C2 1.5(7) . . . . ?
C6 C4 C3 C2 -178.3(4) . . . . ?
C16 O5 C17 O6 5.4(7) . . . . ?
C16 O5 C17 C6 -172.4(4) . . . . ?
C4 C6 C17 O6 9.7(6) . . . . ?
C7 C6 C17 O6 -117.9(5) . . . . ?
C4 C6 C17 O5 -172.7(4) . . . . ?
C7 C6 C17 O5 59.7(4) . . . . ?
C5 C1 C2 C3 -3.6(7) . . . . ?
Br1 C1 C2 C3 178.2(4) . . . . ?
C4 C3 C2 C1 2.3(7) . . . . ?
C8 C13 C12 C11 0.1(7) . . . . ?
C12 C13 C8 C9 1.4(7) . . . . ?
C12 C13 C8 C7 -177.9(4) . . . . ?
C10 C9 C8 C13 -1.6(8) . . . . ?
C10 C9 C8 C7 177.7(5) . . . . ?
C14 C7 C8 C13 -77.8(5) . . . . ?
C6 C7 C8 C13 47.1(6) . . . . ?
C14 C7 C8 C9 102.9(5) . . . . ?
C6 C7 C8 C9 -132.2(5) . . . . ?
O4 C15 C14 C19 -8.7(6) . . . . ?
C18 C15 C14 C19 171.6(4) . . . . ?
O4 C15 C14 N1 107.0(5) . . . . ?
C18 C15 C14 N1 -72.7(4) . . . . ?
O4 C15 C14 C7 -136.3(4) . . . . ?
C18 C15 C14 C7 43.9(5) . . . . ?
O2 N1 C14 C15 -11.8(5) . . . . ?
O1 N1 C14 C15 170.4(4) . . . . ?
O2 N1 C14 C19 108.0(5) . . . . ?
O1 N1 C14 C19 -69.8(5) . . . . ?
O2 N1 C14 C7 -130.5(4) . . . . ?
O1 N1 C14 C7 51.6(5) . . . . ?
C8 C7 C14 C15 69.6(4) . . . . ?
C6 C7 C14 C15 -57.7(5) . . . . ?
C8 C7 C14 C19 -58.0(5) . . . . ?
C6 C7 C14 C19 174.7(4) . . . . ?
C8 C7 C14 N1 -175.5(3) . . . . ?
C6 C7 C14 N1 57.2(4) . . . . ?
C8 C9 C10 C11 0.5(10) . . . . ?
C9 C10 C11 C12 0.9(9) . . . . ?
C13 C12 C11 C10 -1.2(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.136
