# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1411039'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 Br N O4'
_chemical_formula_sum            'C18 H16 Br N O4'
_chemical_formula_weight         390.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.528(3)
_cell_length_b                   7.509(2)
_cell_length_c                   11.706(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.729(7)
_cell_angle_gamma                90
_cell_volume                     825.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3353
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.50

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.512
_shelx_estimated_absorpt_T_min   0.608
_shelx_estimated_absorpt_T_max   0.689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.564
_exptl_absorpt_correction_T_max  0.668
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            11465
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.765
_diffrn_reflns_theta_max         28.754
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4145
_reflns_number_gt                3674
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_max     0.934
_reflns_Friedel_fraction_full    0.973

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_refine_special_details          
; 
    ENTER TEXT OF LETTER 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0069P)²] 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_abs_structure_details 
; 
 Flack x determined using 1510 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.002(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4145
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.0368
_refine_ls_wR_factor_gt          0.0366
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_restrained_S_all      0.874
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.09782(2) 0.28668(4) -0.06925(2) 0.02184(6) Uani 1 1 d . . . . .
O1 O 0.41338(15) 0.2688(3) 0.17556(12) 0.0172(4) Uani 1 1 d . . . . .
O2 O 0.56480(16) 0.3052(4) 0.47305(12) 0.0237(4) Uani 1 1 d . . . . .
O3 O 0.1355(2) 0.0455(3) 0.47307(16) 0.0355(5) Uani 1 1 d . . . . .
O4 O 0.12000(19) -0.1740(2) 0.35235(16) 0.0323(5) Uani 1 1 d . . . . .
N1 N 0.1692(2) -0.0313(3) 0.39010(18) 0.0213(5) Uani 1 1 d . . . . .
C1 C 0.5369(3) 0.1733(3) 0.1855(2) 0.0176(5) Uani 1 1 d . . . . .
C2 C 0.6163(3) 0.1703(3) 0.2963(2) 0.0181(5) Uani 1 1 d . . . . .
C3 C 0.7449(3) 0.0765(4) 0.3185(2) 0.0257(6) Uani 1 1 d . . . . .
H3 H 0.8011 0.0748 0.3938 0.031 Uiso 1 1 calc R U . . .
C4 C 0.7870(3) -0.0127(3) 0.2282(3) 0.0262(6) Uani 1 1 d . . . . .
H4 H 0.8729 -0.0795 0.2416 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7076(3) -0.0078(4) 0.1180(3) 0.0303(7) Uani 1 1 d . . . . .
H5 H 0.7410 -0.0703 0.0572 0.036 Uiso 1 1 calc R U . . .
C6 C 0.5807(3) 0.0856(4) 0.0936(2) 0.0272(6) Uani 1 1 d . . . . .
H6 H 0.5265 0.0894 0.0176 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5374(2) 0.2727(5) 0.36968(17) 0.0165(5) Uani 1 1 d . . . . .
C8 C 0.4012(2) 0.3372(3) 0.29099(19) 0.0152(5) Uani 1 1 d . . . . .
C9 C 0.2706(2) 0.2541(3) 0.33144(18) 0.0149(6) Uani 1 1 d . . . . .
H9 H 0.2743 0.2919 0.4138 0.018 Uiso 1 1 calc R U . . .
C10 C 0.2816(3) 0.0508(3) 0.3326(2) 0.0159(5) Uani 1 1 d . . . . .
H10A H 0.2717 0.0065 0.2520 0.019 Uiso 1 1 calc R U . . .
H10B H 0.3766 0.0148 0.3742 0.019 Uiso 1 1 calc R U . . .
C11 C 0.3915(3) 0.5400(3) 0.2858(2) 0.0195(5) Uani 1 1 d . . . . .
H11A H 0.3130 0.5740 0.2229 0.023 Uiso 1 1 calc R U . . .
H11B H 0.3668 0.5840 0.3596 0.023 Uiso 1 1 calc R U . . .
C12 C 0.5267(3) 0.6321(3) 0.2652(2) 0.0249(6) Uani 1 1 d . . . . .
H12A H 0.5082 0.7596 0.2526 0.030 Uiso 1 1 calc R U . . .
H12B H 0.5579 0.5807 0.1968 0.030 Uiso 1 1 calc R U . . .
H12C H 0.6013 0.6157 0.3331 0.030 Uiso 1 1 calc R U . . .
C13 C 0.1283(2) 0.3179(3) 0.26541(18) 0.0140(6) Uani 1 1 d . . . . .
C14 C 0.0856(2) 0.2775(5) 0.14829(16) 0.0145(4) Uani 1 1 d . . . . .
H14 H 0.1454 0.2086 0.1082 0.017 Uiso 1 1 calc R U . . .
C15 C -0.0442(3) 0.3384(3) 0.09109(19) 0.0164(5) Uani 1 1 d . . . . .
C16 C -0.1342(3) 0.4381(3) 0.1464(2) 0.0195(5) Uani 1 1 d . . . . .
H16 H -0.2230 0.4788 0.1055 0.023 Uiso 1 1 calc R U . . .
C17 C -0.0926(3) 0.4775(3) 0.2625(2) 0.0212(6) Uani 1 1 d . . . . .
H17 H -0.1531 0.5458 0.3022 0.025 Uiso 1 1 calc R U . . .
C18 C 0.0381(3) 0.4172(3) 0.3216(2) 0.0187(5) Uani 1 1 d . . . . .
H18 H 0.0656 0.4445 0.4015 0.022 Uiso 1 1 calc R U . . .


_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 C15 1.900(2) . ?
O1 C1 1.366(3) . ?
O1 C8 1.469(3) . ?
O2 C7 1.219(2) . ?
O3 N1 1.218(3) . ?
O4 N1 1.222(3) . ?
N1 C10 1.491(3) . ?
C1 C6 1.385(3) . ?
C1 C2 1.387(3) . ?
C2 C3 1.399(3) . ?
C2 C7 1.454(4) . ?
C3 C4 1.368(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.537(3) . ?
C8 C11 1.526(3) . ?
C8 C9 1.536(3) . ?
C9 C13 1.520(3) . ?
C9 C10 1.530(3) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.517(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.385(3) . ?
C13 C14 1.396(3) . ?
C14 C15 1.381(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(3) . ?
C16 C17 1.382(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(3) . ?
C17 H17 0.9500 . ?
C18 H18 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 C8 107.86(16) . . ?
O3 N1 O4 124.5(2) . . ?
O3 N1 C10 118.1(2) . . ?
O4 N1 C10 117.4(2) . . ?
O1 C1 C6 123.5(2) . . ?
O1 C1 C2 114.4(2) . . ?
C6 C1 C2 122.1(2) . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 C7 106.8(2) . . ?
C3 C2 C7 132.9(2) . . ?
C4 C3 C2 117.7(3) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 121.8(3) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 116.6(3) . . ?
C1 C6 H6 121.7 . . ?
C5 C6 H6 121.7 . . ?
O2 C7 C2 130.3(2) . . ?
O2 C7 C8 123.3(2) . . ?
C2 C7 C8 106.35(18) . . ?
O1 C8 C11 109.02(19) . . ?
O1 C8 C9 109.61(17) . . ?
C11 C8 C9 111.79(19) . . ?
O1 C8 C7 104.53(18) . . ?
C11 C8 C7 112.2(2) . . ?
C9 C8 C7 109.43(18) . . ?
C13 C9 C10 111.87(19) . . ?
C13 C9 C8 114.48(19) . . ?
C10 C9 C8 110.51(18) . . ?
C13 C9 H9 106.5 . . ?
C10 C9 H9 106.5 . . ?
C8 C9 H9 106.5 . . ?
N1 C10 C9 111.29(19) . . ?
N1 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
N1 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C8 114.5(2) . . ?
C12 C11 H11A 108.6 . . ?
C8 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C8 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 118.8(2) . . ?
C18 C13 C9 120.0(2) . . ?
C14 C13 C9 121.2(2) . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 121.9(2) . . ?
C16 C15 Br1 119.33(18) . . ?
C14 C15 Br1 118.74(18) . . ?
C15 C16 C17 118.7(2) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C18 120.1(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.9(2) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?

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
C8 O1 C1 C6 178.3(2) . . . . ?
C8 O1 C1 C2 -1.6(3) . . . . ?
O1 C1 C2 C3 179.7(2) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
O1 C1 C2 C7 0.9(3) . . . . ?
C6 C1 C2 C7 -179.0(2) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C7 C2 C3 C4 177.5(3) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
O1 C1 C6 C5 -179.0(2) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C1 C2 C7 O2 179.4(3) . . . . ?
C3 C2 C7 O2 0.7(6) . . . . ?
C1 C2 C7 C8 0.2(3) . . . . ?
C3 C2 C7 C8 -178.4(3) . . . . ?
C1 O1 C8 C11 121.7(2) . . . . ?
C1 O1 C8 C9 -115.7(2) . . . . ?
C1 O1 C8 C7 1.5(3) . . . . ?
O2 C7 C8 O1 179.7(3) . . . . ?
C2 C7 C8 O1 -1.0(3) . . . . ?
O2 C7 C8 C11 61.7(4) . . . . ?
C2 C7 C8 C11 -119.0(2) . . . . ?
O2 C7 C8 C9 -63.0(4) . . . . ?
C2 C7 C8 C9 116.3(2) . . . . ?
O1 C8 C9 C13 -69.9(2) . . . . ?
C11 C8 C9 C13 51.1(3) . . . . ?
C7 C8 C9 C13 176.0(2) . . . . ?
O1 C8 C9 C10 57.5(2) . . . . ?
C11 C8 C9 C10 178.46(19) . . . . ?
C7 C8 C9 C10 -56.6(2) . . . . ?
O3 N1 C10 C9 -36.3(3) . . . . ?
O4 N1 C10 C9 145.7(2) . . . . ?
C13 C9 C10 N1 -60.8(2) . . . . ?
C8 C9 C10 N1 170.41(17) . . . . ?
O1 C8 C11 C12 -68.0(2) . . . . ?
C9 C8 C11 C12 170.7(2) . . . . ?
C7 C8 C11 C12 47.3(3) . . . . ?
C10 C9 C13 C18 119.3(2) . . . . ?
C8 C9 C13 C18 -114.0(2) . . . . ?
C10 C9 C13 C14 -60.3(3) . . . . ?
C8 C9 C13 C14 66.4(3) . . . . ?
C18 C13 C14 C15 0.6(4) . . . . ?
C9 C13 C14 C15 -179.8(2) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C13 C14 C15 Br1 178.5(2) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
Br1 C15 C16 C17 -178.79(19) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C14 C13 C18 C17 -0.6(4) . . . . ?
C9 C13 C18 C17 179.8(2) . . . . ?
C16 C17 C18 C13 0.3(4) . . . . ?

_refine_diff_density_max         0.581
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.047

