# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_ww
_database_code_depnum_ccdc_archive 'CCDC 1429312'
_audit_update_record             
;
2015-10-03 deposited with the CCDC.
2016-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 Br2 N2 O'
_chemical_formula_weight         406.08

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Pc

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

_cell_length_a                   8.0468(7)
_cell_length_b                   12.1197(10)
_cell_length_c                   7.5388(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.03
_cell_angle_gamma                90.00
_cell_volume                     735.10(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    5.513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3755
_exptl_absorpt_correction_T_max  0.4082
_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  ?
_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            9209
_diffrn_reflns_av_R_equivalents  0.1065
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2595
_reflns_number_gt                2537
_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)+(0.1026P)²+1.9783P] 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   0.90(3)
_refine_ls_number_reflns         2595
_refine_ls_number_parameters     191
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1553
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.021
_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 0.42308(13) 0.09155(6) 0.75407(13) 0.0507(2) Uani 1 1 d . A 1
Br2 Br -0.02037(11) 0.44445(9) 0.82170(12) 0.0589(2) Uani 1 1 d . A 1
O1 O 0.5081(6) 0.1435(5) 0.3627(8) 0.0422(14) Uani 1 1 d . A 1
N1 N 0.5886(8) 0.4880(6) 0.5536(9) 0.0397(15) Uani 1 1 d . A 1
N2 N 0.6373(8) 0.2667(6) 0.5402(10) 0.0387(15) Uani 1 1 d . A 1
H2A H 0.7313 0.2921 0.5778 0.046 Uiso 1 1 calc R A 1
C1 C 0.3111(10) 0.4665(7) 0.6823(11) 0.0374(18) Uani 1 1 d . A 1
C2 C 0.1895(9) 0.3920(7) 0.7447(12) 0.0388(17) Uani 1 1 d . A 1
C3 C 0.2210(10) 0.2825(6) 0.7566(11) 0.0383(17) Uani 1 1 d . A 1
H3A H 0.1409 0.2353 0.8014 0.046 Uiso 1 1 calc R A 1
C4 C 0.3765(11) 0.2391(7) 0.7008(10) 0.0387(18) Uani 1 1 d . A 1
C5 C 0.4902(10) 0.3057(6) 0.6167(10) 0.0340(16) Uani 1 1 d . A 1
C6 C 0.4615(10) 0.4229(6) 0.6161(10) 0.0333(16) Uani 1 1 d . A 1
C7 C 0.5676(13) 0.5934(7) 0.5580(14) 0.047(2) Uani 1 1 d . A 1
H7A H 0.6521 0.6380 0.5154 0.057 Uiso 1 1 calc R A 1
C8 C 0.4243(13) 0.6452(7) 0.6234(12) 0.047(2) Uani 1 1 d . A 1
H8A H 0.4170 0.7218 0.6260 0.057 Uiso 1 1 calc R A 1
C9 C 0.2964(13) 0.5822(7) 0.6829(13) 0.046(2) Uani 1 1 d . A 1
H9A H 0.2001 0.6154 0.7235 0.055 Uiso 1 1 calc R A 1
C10 C 0.6349(9) 0.1898(6) 0.4079(11) 0.0345(17) Uani 1 1 d . A 1
C11 C 0.7969(9) 0.1664(6) 0.3197(12) 0.0350(16) Uani 1 1 d . A 1
C12 C 0.7928(12) 0.1191(8) 0.1539(13) 0.047(2) Uani 1 1 d . A 1
H12A H 0.6914 0.1033 0.0985 0.056 Uiso 1 1 calc R A 1
C13 C 0.9406(15) 0.0946(8) 0.0689(14) 0.056(3) Uani 1 1 d . A 1
H13A H 0.9376 0.0648 -0.0447 0.067 Uiso 1 1 calc R A 1
C14 C 1.0911(12) 0.1146(9) 0.1526(15) 0.055(3) Uani 1 1 d . A 1
H14A H 1.1897 0.0966 0.0970 0.066 Uiso 1 1 calc R A 1
C15 C 1.0948(10) 0.1611(8) 0.3176(16) 0.052(2) Uani 1 1 d . A 1
H15A H 1.1963 0.1749 0.3742 0.062 Uiso 1 1 calc R A 1
C16 C 0.9486(10) 0.1877(7) 0.4011(12) 0.046(2) Uani 1 1 d . A 1
H16A H 0.9524 0.2201 0.5130 0.055 Uiso 1 1 calc R A 1


_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 C4 1.870(8) . ?
Br2 C2 1.905(7) . ?
O1 C10 1.209(9) . ?
N1 C7 1.289(12) . ?
N1 C6 1.380(11) . ?
N2 C10 1.365(11) . ?
N2 C5 1.408(10) . ?
N2 H2A 0.8600 . ?
C1 C9 1.406(12) . ?
C1 C2 1.419(12) . ?
C1 C6 1.420(11) . ?
C2 C3 1.354(12) . ?
C3 C4 1.427(11) . ?
C3 H3A 0.9300 . ?
C4 C5 1.383(12) . ?
C5 C6 1.439(10) . ?
C7 C8 1.410(14) . ?
C7 H7A 0.9300 . ?
C8 C9 1.364(15) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
C10 C11 1.501(10) . ?
C11 C12 1.375(13) . ?
C11 C16 1.381(12) . ?
C12 C13 1.392(14) . ?
C12 H12A 0.9300 . ?
C13 C14 1.376(17) . ?
C13 H13A 0.9300 . ?
C14 C15 1.365(17) . ?
C14 H14A 0.9300 . ?
C15 C16 1.383(12) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?

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
C7 N1 C6 117.3(7) . . ?
C10 N2 C5 121.9(6) . . ?
C10 N2 H2A 119.1 . . ?
C5 N2 H2A 119.1 . . ?
C9 C1 C2 125.1(8) . . ?
C9 C1 C6 116.4(8) . . ?
C2 C1 C6 118.5(7) . . ?
C3 C2 C1 121.1(7) . . ?
C3 C2 Br2 118.2(6) . . ?
C1 C2 Br2 120.6(6) . . ?
C2 C3 C4 120.4(7) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 120.7(7) . . ?
C5 C4 Br1 121.7(6) . . ?
C3 C4 Br1 117.6(6) . . ?
C4 C5 N2 124.1(7) . . ?
C4 C5 C6 118.1(7) . . ?
N2 C5 C6 117.8(7) . . ?
N1 C6 C1 123.3(7) . . ?
N1 C6 C5 116.4(7) . . ?
C1 C6 C5 120.3(7) . . ?
N1 C7 C8 124.0(9) . . ?
N1 C7 H7A 118.0 . . ?
C8 C7 H7A 118.0 . . ?
C9 C8 C7 119.5(8) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C8 C9 C1 119.5(9) . . ?
C8 C9 H9A 120.2 . . ?
C1 C9 H9A 120.2 . . ?
O1 C10 N2 121.6(7) . . ?
O1 C10 C11 121.5(7) . . ?
N2 C10 C11 116.9(6) . . ?
C12 C11 C16 119.2(7) . . ?
C12 C11 C10 118.4(7) . . ?
C16 C11 C10 122.4(8) . . ?
C11 C12 C13 120.0(9) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C14 C13 C12 120.2(9) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C15 C14 C13 119.6(9) . . ?
C15 C14 H14A 120.2 . . ?
C13 C14 H14A 120.2 . . ?
C14 C15 C16 120.4(9) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C11 C16 C15 120.4(9) . . ?
C11 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?

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
C9 C1 C2 C3 -172.9(9) . . . . ?
C6 C1 C2 C3 6.0(13) . . . . ?
C9 C1 C2 Br2 4.9(12) . . . . ?
C6 C1 C2 Br2 -176.2(6) . . . . ?
C1 C2 C3 C4 -2.1(13) . . . . ?
Br2 C2 C3 C4 -179.9(6) . . . . ?
C2 C3 C4 C5 -6.9(12) . . . . ?
C2 C3 C4 Br1 170.7(7) . . . . ?
C3 C4 C5 N2 -172.5(7) . . . . ?
Br1 C4 C5 N2 10.0(11) . . . . ?
C3 C4 C5 C6 11.2(11) . . . . ?
Br1 C4 C5 C6 -166.2(6) . . . . ?
C10 N2 C5 C4 59.2(11) . . . . ?
C10 N2 C5 C6 -124.5(8) . . . . ?
C7 N1 C6 C1 0.6(12) . . . . ?
C7 N1 C6 C5 -177.6(8) . . . . ?
C9 C1 C6 N1 -0.4(12) . . . . ?
C2 C1 C6 N1 -179.5(7) . . . . ?
C9 C1 C6 C5 177.7(8) . . . . ?
C2 C1 C6 C5 -1.4(11) . . . . ?
C4 C5 C6 N1 171.1(7) . . . . ?
N2 C5 C6 N1 -5.4(10) . . . . ?
C4 C5 C6 C1 -7.1(11) . . . . ?
N2 C5 C6 C1 176.4(7) . . . . ?
C6 N1 C7 C8 0.4(13) . . . . ?
N1 C7 C8 C9 -1.6(15) . . . . ?
C7 C8 C9 C1 1.6(14) . . . . ?
C2 C1 C9 C8 178.3(9) . . . . ?
C6 C1 C9 C8 -0.7(13) . . . . ?
C5 N2 C10 O1 -7.6(12) . . . . ?
C5 N2 C10 C11 171.7(7) . . . . ?
O1 C10 C11 C12 20.0(12) . . . . ?
N2 C10 C11 C12 -159.3(8) . . . . ?
O1 C10 C11 C16 -158.0(8) . . . . ?
N2 C10 C11 C16 22.8(11) . . . . ?
C16 C11 C12 C13 -1.0(13) . . . . ?
C10 C11 C12 C13 -179.1(8) . . . . ?
C11 C12 C13 C14 2.0(14) . . . . ?
C12 C13 C14 C15 -1.6(15) . . . . ?
C13 C14 C15 C16 0.2(16) . . . . ?
C12 C11 C16 C15 -0.4(12) . . . . ?
C10 C11 C16 C15 177.6(8) . . . . ?
C14 C15 C16 C11 0.8(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.979
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.114
