# 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_1125
_database_code_depnum_ccdc_archive 'CCDC 1046964'
_audit_update_record             
;
2015-02-03 deposited with the CCDC.
2015-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Br N O4'
_chemical_formula_sum            'C20 H16 Br N O4'
_chemical_formula_weight         414.25

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           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                   9.7918(15)
_cell_length_b                   10.8744(17)
_cell_length_c                   17.136(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1824.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6123
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      24.88

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    2.278
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            13399
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.56
_reflns_number_total             3383
_reflns_number_gt                2992
_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)+(0.0423P)²+0.0026P] 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       ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.007(8)
_refine_ls_number_reflns         3383
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0742
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 -0.06620(4) 0.41961(3) -0.158595(18) 0.07053(14) Uani 1 1 d . . .
O2 O -0.07372(18) 0.01911(15) 0.29834(9) 0.0402(4) Uani 1 1 d . . .
C12 C -0.0595(2) 0.1274(2) 0.14838(13) 0.0334(5) Uani 1 1 d . . .
C18 C -0.0643(3) 0.3279(2) -0.06445(14) 0.0447(6) Uani 1 1 d . . .
C3 C 0.0587(2) 0.0674(2) 0.27361(13) 0.0352(5) Uani 1 1 d . . .
C15 C -0.0574(2) 0.1941(2) 0.07338(13) 0.0341(5) Uani 1 1 d . . .
C4 C 0.1299(2) 0.1119(2) 0.34616(14) 0.0373(5) Uani 1 1 d . . .
C19 C -0.0008(3) 0.3774(3) -0.00012(18) 0.0500(7) Uani 1 1 d . . .
H19 H 0.0385 0.4552 -0.0024 0.060 Uiso 1 1 calc R . .
O1 O 0.12681(18) -0.11233(16) 0.19419(11) 0.0491(5) Uani 1 1 d . . .
O3 O -0.2644(2) -0.0715(2) 0.26418(12) 0.0623(6) Uani 1 1 d . . .
C2 C 0.1474(2) -0.0452(2) 0.25005(15) 0.0377(6) Uani 1 1 d . . .
C14 C -0.1695(3) -0.0093(2) 0.24355(16) 0.0422(6) Uani 1 1 d . . .
N1 N 0.2457(2) -0.05881(18) 0.30397(13) 0.0412(5) Uani 1 1 d . . .
C17 C -0.1231(3) 0.2128(3) -0.06210(15) 0.0453(6) Uani 1 1 d . . .
H17 H -0.1644 0.1799 -0.1063 0.054 Uiso 1 1 calc R . .
C13 C -0.1554(2) 0.0440(2) 0.16567(15) 0.0394(5) Uani 1 1 d . . .
H13 H -0.2153 0.0191 0.1267 0.047 Uiso 1 1 calc R . .
C11 C 0.0441(2) 0.1626(2) 0.20946(13) 0.0359(5) Uani 1 1 d . . .
H11A H 0.0174 0.2404 0.2326 0.043 Uiso 1 1 calc R . .
H11B H 0.1320 0.1743 0.1845 0.043 Uiso 1 1 calc R . .
O4 O 0.1464(3) 0.3245(2) 0.50645(13) 0.0731(7) Uani 1 1 d . . .
C20 C 0.0038(3) 0.3093(2) 0.06830(16) 0.0449(6) Uani 1 1 d . . .
H20 H 0.0486 0.3412 0.1116 0.054 Uiso 1 1 calc R . .
C5 C 0.2380(3) 0.0324(2) 0.36250(15) 0.0415(6) Uani 1 1 d . . .
C16 C -0.1198(3) 0.1470(2) 0.00708(15) 0.0418(6) Uani 1 1 d . . .
H16 H -0.1602 0.0697 0.0091 0.050 Uiso 1 1 calc R . .
C1 C 0.3464(3) -0.1569(3) 0.3026(2) 0.0562(7) Uani 1 1 d . . .
H1A H 0.3310 -0.2083 0.2580 0.084 Uiso 1 1 calc R . .
H1B H 0.3385 -0.2052 0.3493 0.084 Uiso 1 1 calc R . .
H1C H 0.4364 -0.1221 0.2997 0.084 Uiso 1 1 calc R . .
C9 C 0.1012(3) 0.2093(2) 0.39377(15) 0.0454(6) Uani 1 1 d . . .
H9 H 0.0308 0.2637 0.3821 0.054 Uiso 1 1 calc R . .
C8 C 0.1820(3) 0.2245(3) 0.46137(16) 0.0527(7) Uani 1 1 d . . .
C7 C 0.2860(3) 0.1440(3) 0.47778(19) 0.0625(8) Uani 1 1 d . . .
H7 H 0.3372 0.1544 0.5230 0.075 Uiso 1 1 calc R . .
C6 C 0.3159(3) 0.0471(3) 0.42758(18) 0.0593(8) Uani 1 1 d . . .
H6 H 0.3875 -0.0064 0.4383 0.071 Uiso 1 1 calc R . .
C10 C 0.1976(6) 0.3296(5) 0.5828(2) 0.1151(19) Uani 1 1 d . . .
H10A H 0.1611 0.2625 0.6126 0.173 Uiso 1 1 calc R . .
H10B H 0.1713 0.4060 0.6065 0.173 Uiso 1 1 calc R . .
H10C H 0.2954 0.3238 0.5816 0.173 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 C18 1.897(2) . ?
O2 C14 1.363(3) . ?
O2 C3 1.462(3) . ?
C12 C13 1.338(3) . ?
C12 C15 1.476(3) . ?
C12 C11 1.507(3) . ?
C18 C19 1.375(4) . ?
C18 C17 1.378(4) . ?
C3 C4 1.505(3) . ?
C3 C11 1.517(3) . ?
C3 C2 1.555(3) . ?
C15 C16 1.387(3) . ?
C15 C20 1.391(3) . ?
C4 C9 1.366(3) . ?
C4 C5 1.395(3) . ?
C19 C20 1.388(4) . ?
O1 C2 1.221(3) . ?
O3 C14 1.203(3) . ?
C2 N1 1.343(3) . ?
C14 C13 1.462(4) . ?
N1 C5 1.412(3) . ?
N1 C1 1.453(3) . ?
C17 C16 1.385(4) . ?
O4 C8 1.379(3) . ?
O4 C10 1.402(4) . ?
C5 C6 1.361(4) . ?
C9 C8 1.413(4) . ?
C8 C7 1.372(4) . ?
C7 C6 1.391(4) . ?

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
C14 O2 C3 119.49(18) . . ?
C13 C12 C15 122.4(2) . . ?
C13 C12 C11 119.4(2) . . ?
C15 C12 C11 118.1(2) . . ?
C19 C18 C17 121.4(2) . . ?
C19 C18 Br1 118.7(2) . . ?
C17 C18 Br1 119.9(2) . . ?
O2 C3 C4 106.68(18) . . ?
O2 C3 C11 111.81(18) . . ?
C4 C3 C11 115.03(18) . . ?
O2 C3 C2 106.70(17) . . ?
C4 C3 C2 102.05(18) . . ?
C11 C3 C2 113.72(19) . . ?
C16 C15 C20 118.0(2) . . ?
C16 C15 C12 121.7(2) . . ?
C20 C15 C12 120.2(2) . . ?
C9 C4 C5 121.1(2) . . ?
C9 C4 C3 130.3(2) . . ?
C5 C4 C3 108.5(2) . . ?
C18 C19 C20 118.9(2) . . ?
O1 C2 N1 126.3(2) . . ?
O1 C2 C3 125.6(2) . . ?
N1 C2 C3 108.0(2) . . ?
O3 C14 O2 117.2(2) . . ?
O3 C14 C13 124.4(2) . . ?
O2 C14 C13 118.3(2) . . ?
C2 N1 C5 111.86(19) . . ?
C2 N1 C1 123.8(2) . . ?
C5 N1 C1 124.3(2) . . ?
C18 C17 C16 119.0(2) . . ?
C12 C13 C14 122.5(2) . . ?
C12 C11 C3 113.16(19) . . ?
C8 O4 C10 117.6(3) . . ?
C19 C20 C15 121.3(3) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 N1 129.4(2) . . ?
C4 C5 N1 109.5(2) . . ?
C17 C16 C15 121.4(2) . . ?
C4 C9 C8 117.7(2) . . ?
C7 C8 O4 125.2(3) . . ?
C7 C8 C9 120.6(3) . . ?
O4 C8 C9 114.2(2) . . ?
C8 C7 C6 120.8(3) . . ?
C5 C6 C7 118.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.56
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.045
