# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_ap_ak_610_0m
_database_code_depnum_ccdc_archive 'CCDC 1412850'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2015-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H17 Br N2 O3'
_chemical_formula_weight         546.38

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   7.643(3)
_cell_length_b                   20.832(7)
_cell_length_c                   15.360(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.066(4)
_cell_angle_gamma                90.00
_cell_volume                     2415.0(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1108
_exptl_absorpt_coefficient_mu    1.740
_exptl_absorpt_correction_type   ?
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17197
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         26.53
_reflns_number_total             4680
_reflns_number_gt                3251
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0534P)²+0.5761P] 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         4680
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.80321(5) 0.081579(15) 0.88437(2) 0.08097(16) Uani 1 1 d . . .
O1 O 0.4523(3) 0.36768(10) 1.09370(12) 0.0667(5) Uani 1 1 d . . .
O2 O 0.0891(3) 0.23049(9) 0.90557(11) 0.0613(5) Uani 1 1 d . . .
O3 O -0.0109(3) 0.34016(10) 1.07577(13) 0.0732(6) Uani 1 1 d . . .
N1 N 0.2734(3) 0.42018(9) 0.79347(13) 0.0493(5) Uani 1 1 d . . .
N2 N 0.3984(3) 0.37492(10) 0.78647(14) 0.0538(5) Uani 1 1 d . . .
C1 C 0.3694(5) 0.18316(19) 1.2225(2) 0.0850(11) Uani 1 1 d . . .
H1 H 0.4173 0.1692 1.2787 0.102 Uiso 1 1 calc R . .
C2 C 0.4106(4) 0.24323(16) 1.19624(18) 0.0685(8) Uani 1 1 d . . .
H2 H 0.4871 0.2699 1.2330 0.082 Uiso 1 1 calc R . .
C3 C 0.3338(3) 0.26282(13) 1.11259(15) 0.0507(6) Uani 1 1 d . . .
C4 C 0.3505(3) 0.32499(12) 1.06974(15) 0.0479(6) Uani 1 1 d . . .
C5 C 0.2108(3) 0.32616(11) 0.98423(15) 0.0432(6) Uani 1 1 d . . .
C6 C 0.2695(3) 0.35639(11) 0.90620(15) 0.0438(6) Uani 1 1 d . . .
C7 C 0.1896(3) 0.40935(11) 0.86466(15) 0.0417(5) Uani 1 1 d . . .
C8 C 0.2577(3) 0.47299(12) 0.73363(16) 0.0494(6) Uani 1 1 d . . .
C9 C 0.2892(4) 0.53393(12) 0.7658(2) 0.0567(7) Uani 1 1 d . . .
H9 H 0.3226 0.5404 0.8260 0.068 Uiso 1 1 calc R . .
C10 C 0.2719(4) 0.58521(15) 0.7100(3) 0.0734(9) Uani 1 1 d . . .
H10 H 0.2919 0.6266 0.7321 0.088 Uiso 1 1 calc R . .
C11 C 0.2258(5) 0.57584(19) 0.6229(3) 0.0842(11) Uani 1 1 d . . .
H11 H 0.2123 0.6111 0.5853 0.101 Uiso 1 1 calc R . .
C12 C 0.6844(3) 0.16154(13) 0.87533(19) 0.0553(7) Uani 1 1 d . . .
C13 C 0.5917(4) 0.18000(13) 0.79549(18) 0.0582(7) Uani 1 1 d . . .
H13 H 0.5900 0.1542 0.7460 0.070 Uiso 1 1 calc R . .
C14 C 0.5013(4) 0.23733(13) 0.78976(18) 0.0563(7) Uani 1 1 d . . .
H14 H 0.4374 0.2499 0.7359 0.068 Uiso 1 1 calc R . .
C15 C 0.5033(3) 0.27655(12) 0.86217(17) 0.0494(6) Uani 1 1 d . . .
C16 C 0.6023(4) 0.25755(13) 0.94122(19) 0.0582(7) Uani 1 1 d . . .
H16 H 0.6087 0.2841 0.9903 0.070 Uiso 1 1 calc R . .
C17 C 0.6919(4) 0.19972(14) 0.94822(19) 0.0610(7) Uani 1 1 d . . .
H17 H 0.7564 0.1869 1.0018 0.073 Uiso 1 1 calc R . .
C18 C 0.3953(3) 0.33608(12) 0.85436(16) 0.0477(6) Uani 1 1 d . . .
C19 C 0.2232(3) 0.22210(12) 1.05750(16) 0.0480(6) Uani 1 1 d . . .
C20 C 0.1843(4) 0.16120(14) 1.08373(19) 0.0651(8) Uani 1 1 d . . .
H20 H 0.1113 0.1338 1.0465 0.078 Uiso 1 1 calc R . .
C21 C 0.2591(5) 0.14262(17) 1.1682(2) 0.0839(10) Uani 1 1 d . . .
H21 H 0.2342 0.1021 1.1885 0.101 Uiso 1 1 calc R . .
C22 C 0.1621(3) 0.25416(12) 0.97286(15) 0.0449(6) Uani 1 1 d . . .
C23 C 0.0447(3) 0.35943(12) 1.01099(15) 0.0472(6) Uani 1 1 d . . .
C24 C -0.0438(3) 0.41121(11) 0.95601(15) 0.0420(5) Uani 1 1 d . . .
C25 C 0.0254(3) 0.43780(11) 0.88439(14) 0.0400(5) Uani 1 1 d . . .
C26 C -0.0737(3) 0.48473(11) 0.83402(16) 0.0470(6) Uani 1 1 d . . .
H26 H -0.0311 0.5025 0.7859 0.056 Uiso 1 1 calc R . .
C27 C -0.2334(3) 0.50507(13) 0.85438(17) 0.0541(6) Uani 1 1 d . . .
H27 H -0.2973 0.5365 0.8200 0.065 Uiso 1 1 calc R . .
C28 C -0.3001(4) 0.47931(13) 0.92538(17) 0.0572(7) Uani 1 1 d . . .
H28 H -0.4080 0.4935 0.9390 0.069 Uiso 1 1 calc R . .
C29 C -0.2062(3) 0.43272(12) 0.97551(16) 0.0503(6) Uani 1 1 d . . .
H29 H -0.2512 0.4152 1.0231 0.060 Uiso 1 1 calc R . .
C30 C 0.2143(5) 0.46227(18) 0.6449(2) 0.0765(9) Uani 1 1 d . . .
H30 H 0.1958 0.4209 0.6225 0.092 Uiso 1 1 calc R . .
C31 C 0.1986(5) 0.5162(2) 0.5887(2) 0.0940(12) Uani 1 1 d . . .
H31 H 0.1695 0.5107 0.5281 0.113 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 C12 1.892(3) . ?
O1 C4 1.201(3) . ?
O2 C22 1.200(3) . ?
O3 C23 1.210(3) . ?
N1 N2 1.359(3) . ?
N1 C7 1.370(3) . ?
N1 C8 1.426(3) . ?
N2 C18 1.323(3) . ?
C1 C2 1.367(5) . ?
C1 C21 1.378(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(3) . ?
C2 H2 0.9300 . ?
C3 C19 1.387(4) . ?
C3 C4 1.467(4) . ?
C4 C5 1.557(3) . ?
C5 C6 1.485(3) . ?
C5 C22 1.549(3) . ?
C5 C23 1.557(3) . ?
C6 C7 1.369(3) . ?
C6 C18 1.407(3) . ?
C7 C25 1.462(3) . ?
C8 C30 1.369(4) . ?
C8 C9 1.370(4) . ?
C9 C10 1.363(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.343(5) . ?
C10 H10 0.9300 . ?
C11 C31 1.352(5) . ?
C11 H11 0.9300 . ?
C12 C17 1.367(4) . ?
C12 C13 1.371(4) . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(4) . ?
C15 C18 1.484(3) . ?
C16 C17 1.381(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C19 C20 1.378(4) . ?
C19 C22 1.471(3) . ?
C20 C21 1.388(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C23 C24 1.468(3) . ?
C24 C29 1.396(3) . ?
C24 C25 1.407(3) . ?
C25 C26 1.394(3) . ?
C26 C27 1.373(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.383(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.369(4) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 C31 1.410(5) . ?
C30 H30 0.9300 . ?
C31 H31 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
N2 N1 C7 111.82(19) . . ?
N2 N1 C8 118.21(19) . . ?
C7 N1 C8 129.7(2) . . ?
C18 N2 N1 105.19(19) . . ?
C2 C1 C21 122.0(3) . . ?
C2 C1 H1 119.0 . . ?
C21 C1 H1 119.0 . . ?
C1 C2 C3 117.3(3) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C2 C3 C19 120.9(3) . . ?
C2 C3 C4 128.4(3) . . ?
C19 C3 C4 110.7(2) . . ?
O1 C4 C3 127.9(2) . . ?
O1 C4 C5 124.9(2) . . ?
C3 C4 C5 107.2(2) . . ?
C6 C5 C22 114.68(19) . . ?
C6 C5 C4 115.7(2) . . ?
C22 C5 C4 101.57(19) . . ?
C6 C5 C23 112.77(19) . . ?
C22 C5 C23 105.64(19) . . ?
C4 C5 C23 105.28(18) . . ?
C7 C6 C18 105.8(2) . . ?
C7 C6 C5 123.3(2) . . ?
C18 C6 C5 130.5(2) . . ?
C6 C7 N1 105.9(2) . . ?
C6 C7 C25 124.4(2) . . ?
N1 C7 C25 128.5(2) . . ?
C30 C8 C9 120.7(3) . . ?
C30 C8 N1 119.9(3) . . ?
C9 C8 N1 119.4(2) . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C31 121.3(3) . . ?
C10 C11 H11 119.3 . . ?
C31 C11 H11 119.3 . . ?
C17 C12 C13 121.2(3) . . ?
C17 C12 Br1 119.6(2) . . ?
C13 C12 Br1 119.1(2) . . ?
C12 C13 C14 119.0(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C15 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C16 118.3(2) . . ?
C14 C15 C18 119.7(2) . . ?
C16 C15 C18 122.0(2) . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C12 C17 C16 119.2(3) . . ?
C12 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
N2 C18 C6 111.1(2) . . ?
N2 C18 C15 119.7(2) . . ?
C6 C18 C15 128.8(2) . . ?
C20 C19 C3 121.6(2) . . ?
C20 C19 C22 128.6(3) . . ?
C3 C19 C22 109.8(2) . . ?
C19 C20 C21 117.0(3) . . ?
C19 C20 H20 121.5 . . ?
C21 C20 H20 121.5 . . ?
C1 C21 C20 121.2(3) . . ?
C1 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
O2 C22 C19 127.9(2) . . ?
O2 C22 C5 124.4(2) . . ?
C19 C22 C5 107.6(2) . . ?
O3 C23 C24 121.8(2) . . ?
O3 C23 C5 118.4(2) . . ?
C24 C23 C5 119.7(2) . . ?
C29 C24 C25 119.9(2) . . ?
C29 C24 C23 117.2(2) . . ?
C25 C24 C23 122.9(2) . . ?
C26 C25 C24 118.1(2) . . ?
C26 C25 C7 125.3(2) . . ?
C24 C25 C7 116.3(2) . . ?
C27 C26 C25 121.0(2) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 120.7(2) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C29 C28 C27 119.5(2) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C28 C29 C24 120.8(2) . . ?
C28 C29 H29 119.6 . . ?
C24 C29 H29 119.6 . . ?
C8 C30 C31 117.6(3) . . ?
C8 C30 H30 121.2 . . ?
C31 C30 H30 121.2 . . ?
C11 C31 C30 120.1(3) . . ?
C11 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        26.53
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.042
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_ashis1
_database_code_depnum_ccdc_archive 'CCDC 1415047'
_audit_update_record             
;
2015-07-24 deposited with the CCDC.
2015-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H19 Br2 N2 O4'
_chemical_formula_weight         643.30

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   14.759(3)
_cell_length_b                   11.832(2)
_cell_length_c                   19.609(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 128.850(3)
_cell_angle_gamma                90.00
_cell_volume                     2666.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1284
_exptl_absorpt_coefficient_mu    3.080
_exptl_absorpt_correction_type   ?
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9973
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_sigmaI/netI    0.1380
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         24.10
_reflns_number_total             3656
_reflns_number_gt                1663
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0641P)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         3656
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1667
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1684
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_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 1.07561(10) 0.82900(9) 1.00368(8) 0.1015(5) Uani 1 1 d . . .
Br2 Br 0.86705(10) -0.18356(9) 0.67210(8) 0.0943(5) Uani 1 1 d . . .
O1 O 0.5604(5) 0.4930(4) 0.6956(3) 0.0433(15) Uani 1 1 d . . .
H1 H 0.5369 0.5379 0.7132 0.065 Uiso 1 1 calc R . .
O2 O 0.5782(5) 0.1319(5) 0.7903(4) 0.0544(17) Uani 1 1 d . . .
O3 O 0.5746(5) 0.3179(5) 0.5581(4) 0.0673(19) Uani 1 1 d . . .
O4 O 0.3768(5) 0.3163(5) 0.6734(4) 0.0547(16) Uani 1 1 d . . .
N1 N 0.7552(6) 0.4366(6) 0.7867(4) 0.0438(18) Uani 1 1 d . . .
N2 N 0.8016(6) 0.3398(6) 0.7808(4) 0.0475(19) Uani 1 1 d . . .
C1 C 0.1683(10) 0.4778(9) 0.4126(7) 0.081(3) Uani 1 1 d . . .
H1A H 0.0954 0.5115 0.3816 0.097 Uiso 1 1 calc R . .
C2 C 0.2163(9) 0.4253(8) 0.4912(7) 0.066(3) Uani 1 1 d . . .
H2 H 0.1759 0.4213 0.5131 0.079 Uiso 1 1 calc R . .
C3 C 0.3250(8) 0.3790(7) 0.5364(6) 0.048(2) Uani 1 1 d . . .
C4 C 0.3959(7) 0.3235(6) 0.6209(6) 0.043(2) Uani 1 1 d . . .
C5 C 0.5047(6) 0.2754(6) 0.6392(5) 0.037(2) Uani 1 1 d . . .
H5 H 0.4929 0.1936 0.6294 0.044 Uiso 1 1 calc R . .
C6 C 0.6166(7) 0.2925(6) 0.7329(5) 0.038(2) Uani 1 1 d . . .
C7 C 0.6412(7) 0.4189(7) 0.7640(6) 0.039(2) Uani 1 1 d . . .
C8 C 0.8297(7) 0.5299(8) 0.8340(5) 0.046(2) Uani 1 1 d . . .
C9 C 0.9470(8) 0.5127(7) 0.8887(6) 0.050(2) Uani 1 1 d . . .
H9 H 0.9772 0.4418 0.8927 0.060 Uiso 1 1 calc R . .
C10 C 1.0208(8) 0.6022(8) 0.9381(6) 0.061(3) Uani 1 1 d . . .
H10 H 1.1007 0.5902 0.9765 0.074 Uiso 1 1 calc R . .
C11 C 0.9780(8) 0.7081(7) 0.9315(6) 0.052(2) Uani 1 1 d . . .
C12 C 0.8231(8) -0.0470(7) 0.6949(5) 0.049(2) Uani 1 1 d . . .
C13 C 0.8788(8) 0.0526(8) 0.7074(6) 0.058(3) Uani 1 1 d . . .
H13 H 0.9392 0.0541 0.7043 0.070 Uiso 1 1 calc R . .
C14 C 0.8467(7) 0.1493(7) 0.7243(5) 0.050(2) Uani 1 1 d . . .
H14 H 0.8855 0.2163 0.7328 0.060 Uiso 1 1 calc R . .
C15 C 0.7568(7) 0.1497(7) 0.7289(5) 0.043(2) Uani 1 1 d . . .
C16 C 0.6988(8) 0.0491(8) 0.7146(6) 0.062(3) Uani 1 1 d . . .
H16 H 0.6380 0.0481 0.7171 0.075 Uiso 1 1 calc R . .
C17 C 0.7306(9) -0.0508(7) 0.6964(6) 0.065(3) Uani 1 1 d . . .
H17 H 0.6908 -0.1179 0.6856 0.078 Uiso 1 1 calc R . .
C18 C 0.7277(7) 0.2570(7) 0.7485(5) 0.038(2) Uani 1 1 d . . .
C19 C 0.7857(8) 0.6370(8) 0.8223(6) 0.053(3) Uani 1 1 d . . .
H19 H 0.7062 0.6500 0.7806 0.064 Uiso 1 1 calc R . .
C20 C 0.8602(8) 0.7253(7) 0.8727(6) 0.056(3) Uani 1 1 d . . .
H20 H 0.8301 0.7970 0.8666 0.067 Uiso 1 1 calc R . .
C21 C 0.6432(6) 0.4210(7) 0.8415(5) 0.039(2) Uani 1 1 d . . .
C22 C 0.6272(6) 0.3147(8) 0.8607(5) 0.042(2) Uani 1 1 d . . .
C23 C 0.6045(7) 0.2316(8) 0.7965(6) 0.044(2) Uani 1 1 d . . .
C24 C 0.4991(8) 0.3249(7) 0.5640(6) 0.051(2) Uani 1 1 d . . .
C25 C 0.3845(8) 0.3797(7) 0.5032(6) 0.046(2) Uani 1 1 d . . .
C26 C 0.2279(10) 0.4806(8) 0.3800(6) 0.074(3) Uani 1 1 d . . .
H26 H 0.1943 0.5160 0.3267 0.089 Uiso 1 1 calc R . .
C27 C 0.3373(9) 0.4316(8) 0.4250(7) 0.063(3) Uani 1 1 d . . .
H27 H 0.3772 0.4342 0.4027 0.076 Uiso 1 1 calc R . .
C28 C 0.6236(7) 0.2937(8) 0.9297(6) 0.059(3) Uani 1 1 d . . .
H28 H 0.6106 0.2216 0.9409 0.071 Uiso 1 1 calc R . .
C29 C 0.6403(8) 0.3849(10) 0.9796(6) 0.069(3) Uani 1 1 d . . .
H29 H 0.6400 0.3743 1.0265 0.083 Uiso 1 1 calc R . .
C30 C 0.6575(7) 0.4920(10) 0.9618(6) 0.064(3) Uani 1 1 d . . .
H30 H 0.6691 0.5519 0.9972 0.077 Uiso 1 1 calc R . .
C31 C 0.6577(7) 0.5123(7) 0.8919(6) 0.046(2) Uani 1 1 d . . .
H31 H 0.6674 0.5850 0.8794 0.056 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 C11 1.889(8) . ?
Br2 C12 1.895(7) . ?
O1 C7 1.408(9) . ?
O1 H1 0.8200 . ?
O2 C23 1.223(9) . ?
O3 C24 1.193(9) . ?
O4 C4 1.230(9) . ?
N1 N2 1.376(8) . ?
N1 C8 1.417(10) . ?
N1 C7 1.460(9) . ?
N2 C18 1.298(9) . ?
C1 C26 1.374(12) . ?
C1 C2 1.375(11) . ?
C1 H1A 0.9300 . ?
C2 C3 1.369(11) . ?
C2 H2 0.9300 . ?
C3 C25 1.384(11) . ?
C3 C4 1.447(11) . ?
C4 C5 1.519(10) . ?
C5 C6 1.528(10) . ?
C5 C24 1.541(11) . ?
C5 H5 0.9800 . ?
C6 C18 1.525(10) . ?
C6 C23 1.546(10) . ?
C6 C7 1.569(10) . ?
C7 C21 1.503(10) . ?
C8 C9 1.364(11) . ?
C8 C19 1.376(10) . ?
C9 C10 1.387(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(11) . ?
C10 H10 0.9300 . ?
C11 C20 1.371(11) . ?
C12 C13 1.369(11) . ?
C12 C17 1.384(11) . ?
C13 C14 1.356(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.388(10) . ?
C15 C18 1.468(10) . ?
C16 C17 1.398(10) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C19 C20 1.383(11) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.375(10) . ?
C21 C31 1.386(10) . ?
C22 C28 1.409(10) . ?
C22 C23 1.462(11) . ?
C24 C25 1.474(12) . ?
C25 C27 1.368(11) . ?
C26 C27 1.391(12) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.371(11) . ?
C28 H28 0.9300 . ?
C29 C30 1.379(11) . ?
C29 H29 0.9300 . ?
C30 C31 1.395(10) . ?
C30 H30 0.9300 . ?
C31 H31 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 O1 H1 109.5 . . ?
N2 N1 C8 118.7(7) . . ?
N2 N1 C7 113.2(6) . . ?
C8 N1 C7 125.7(7) . . ?
C18 N2 N1 111.0(7) . . ?
C26 C1 C2 120.1(10) . . ?
C26 C1 H1A 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C3 C2 C1 118.5(9) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C25 121.6(9) . . ?
C2 C3 C4 129.5(9) . . ?
C25 C3 C4 108.9(9) . . ?
O4 C4 C3 127.5(8) . . ?
O4 C4 C5 122.7(8) . . ?
C3 C4 C5 109.8(8) . . ?
C4 C5 C6 114.8(7) . . ?
C4 C5 C24 102.5(7) . . ?
C6 C5 C24 117.9(6) . . ?
C4 C5 H5 107.0 . . ?
C6 C5 H5 107.0 . . ?
C24 C5 H5 107.0 . . ?
C18 C6 C5 114.8(6) . . ?
C18 C6 C23 111.3(6) . . ?
C5 C6 C23 108.9(6) . . ?
C18 C6 C7 103.1(6) . . ?
C5 C6 C7 113.9(6) . . ?
C23 C6 C7 104.3(6) . . ?
O1 C7 N1 109.1(6) . . ?
O1 C7 C21 114.8(6) . . ?
N1 C7 C21 113.7(7) . . ?
O1 C7 C6 111.9(7) . . ?
N1 C7 C6 101.4(6) . . ?
C21 C7 C6 105.2(6) . . ?
C9 C8 C19 120.1(9) . . ?
C9 C8 N1 118.6(8) . . ?
C19 C8 N1 121.2(8) . . ?
C8 C9 C10 119.2(8) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 121.2(9) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C20 C11 C10 118.8(8) . . ?
C20 C11 Br1 119.1(7) . . ?
C10 C11 Br1 122.1(7) . . ?
C13 C12 C17 120.9(8) . . ?
C13 C12 Br2 121.4(7) . . ?
C17 C12 Br2 117.7(7) . . ?
C14 C13 C12 120.5(9) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 121.0(8) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C16 118.6(8) . . ?
C14 C15 C18 118.1(8) . . ?
C16 C15 C18 123.3(8) . . ?
C15 C16 C17 120.9(8) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C12 C17 C16 118.1(8) . . ?
C12 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
N2 C18 C15 119.1(7) . . ?
N2 C18 C6 111.0(7) . . ?
C15 C18 C6 129.8(8) . . ?
C8 C19 C20 119.7(9) . . ?
C8 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C11 C20 C19 120.6(8) . . ?
C11 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C31 119.6(8) . . ?
C22 C21 C7 111.4(8) . . ?
C31 C21 C7 129.1(8) . . ?
C21 C22 C28 122.8(9) . . ?
C21 C22 C23 111.4(8) . . ?
C28 C22 C23 125.6(9) . . ?
O2 C23 C22 128.5(8) . . ?
O2 C23 C6 124.0(8) . . ?
C22 C23 C6 107.6(7) . . ?
O3 C24 C25 128.3(9) . . ?
O3 C24 C5 125.0(8) . . ?
C25 C24 C5 106.7(7) . . ?
C27 C25 C3 120.2(9) . . ?
C27 C25 C24 128.6(9) . . ?
C3 C25 C24 111.2(8) . . ?
C1 C26 C27 121.5(9) . . ?
C1 C26 H26 119.3 . . ?
C27 C26 H26 119.3 . . ?
C25 C27 C26 118.1(9) . . ?
C25 C27 H27 121.0 . . ?
C26 C27 H27 121.0 . . ?
C29 C28 C22 116.6(9) . . ?
C29 C28 H28 121.7 . . ?
C22 C28 H28 121.7 . . ?
C28 C29 C30 121.5(9) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
C29 C30 C31 121.4(9) . . ?
C29 C30 H30 119.3 . . ?
C31 C30 H30 119.3 . . ?
C21 C31 C30 118.2(9) . . ?
C21 C31 H31 120.9 . . ?
C30 C31 H31 120.9 . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        24.10
_diffrn_measured_fraction_theta_full 0.863
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.083
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# 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_ak1
_audit_block_doi                 10.5517/cc1k4y6v
_database_code_depnum_ccdc_archive 'CCDC 1434717'
_audit_update_record             
;
2015-11-02 deposited with the CCDC.
2015-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H16 Br2 N2 O3'
_chemical_formula_sum            'C31 H17 Br2 N2 O3'
_chemical_formula_weight         625.29

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   32.432(2)
_cell_length_b                   10.9492(8)
_cell_length_c                   15.6699(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.385(2)
_cell_angle_gamma                90.00
_cell_volume                     5107.4(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3487
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      19.70

_exptl_crystal_description       needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2488
_exptl_absorpt_coefficient_mu    3.212
_exptl_absorpt_correction_type   ?
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18868
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         20.91
_reflns_number_total             2686
_reflns_number_gt                2079
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0595P)²+12.4317P] 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         2686
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 0.04774(3) -0.03866(8) 0.18758(5) 0.1038(4) Uani 1 1 d . . .
Br2 Br 0.19030(3) 0.06415(6) 0.84420(5) 0.0830(3) Uani 1 1 d . . .
O1 O 0.05291(13) 0.5538(4) 0.7367(3) 0.0672(11) Uani 1 1 d . . .
O2 O 0.14029(13) 0.5944(4) 0.6526(3) 0.0652(11) Uani 1 1 d . . .
O3 O 0.12677(14) 0.3272(3) 0.8744(2) 0.0632(11) Uani 1 1 d . . .
N1 N 0.10890(14) 0.1989(4) 0.5671(3) 0.0423(11) Uani 1 1 d . . .
N2 N 0.15311(14) 0.1872(4) 0.6240(3) 0.0446(11) Uani 1 1 d . . .
C1 C 0.06716(19) 0.0352(6) 0.3071(4) 0.0599(17) Uani 1 1 d . . .
C2 C 0.06294(18) 0.1592(5) 0.3127(4) 0.0537(15) Uani 1 1 d . . .
H2 H 0.0508 0.2062 0.2591 0.064 Uiso 1 1 calc R . .
C3 C 0.07687(18) 0.2128(5) 0.3987(3) 0.0488(14) Uani 1 1 d . . .
H3 H 0.0751 0.2970 0.4037 0.059 Uiso 1 1 calc R . .
C4 C 0.09351(16) 0.1414(5) 0.4775(3) 0.0421(13) Uani 1 1 d . . .
C5 C 0.08796(17) 0.2867(4) 0.5982(3) 0.0370(12) Uani 1 1 d . . .
C6 C 0.12114(17) 0.3357(4) 0.6769(3) 0.0393(12) Uani 1 1 d . . .
C7 C 0.11319(17) 0.4376(4) 0.7295(3) 0.0409(13) Uani 1 1 d . . .
C8 C 0.13141(18) 0.4191(5) 0.8372(3) 0.0438(13) Uani 1 1 d . . .
C9 C 0.15416(17) 0.5325(5) 0.8817(3) 0.0424(13) Uani 1 1 d . . .
C10 C 0.17160(19) 0.5622(5) 0.9750(4) 0.0535(15) Uani 1 1 d . . .
H10 H 0.1694 0.5090 1.0193 0.064 Uiso 1 1 calc R . .
C11 C 0.19239(19) 0.6740(6) 0.9996(4) 0.0653(17) Uani 1 1 d . . .
H11 H 0.2047 0.6964 1.0620 0.078 Uiso 1 1 calc R . .
C12 C 0.16007(18) 0.2702(5) 0.6909(3) 0.0424(13) Uani 1 1 d . . .
C13 C 0.20567(17) 0.2856(5) 0.7663(3) 0.0460(14) Uani 1 1 d . . .
C14 C 0.22373(19) 0.2023(5) 0.8378(4) 0.0574(15) Uani 1 1 d . . .
C15 C 0.2651(2) 0.2216(7) 0.9092(4) 0.077(2) Uani 1 1 d . . .
H15 H 0.2763 0.1653 0.9574 0.093 Uiso 1 1 calc R . .
C16 C 0.2896(2) 0.3232(8) 0.9092(5) 0.085(2) Uani 1 1 d . . .
H16 H 0.3177 0.3351 0.9567 0.102 Uiso 1 1 calc R . .
C17 C 0.2728(2) 0.4072(7) 0.8396(5) 0.079(2) Uani 1 1 d . . .
H17 H 0.2893 0.4768 0.8400 0.094 Uiso 1 1 calc R . .
C18 C 0.23109(19) 0.3885(6) 0.7683(4) 0.0610(16) Uani 1 1 d . . .
H18 H 0.2199 0.4459 0.7209 0.073 Uiso 1 1 calc R . .
C19 C 0.06314(18) 0.4718(5) 0.6966(4) 0.0454(14) Uani 1 1 d . . .
C20 C 0.02922(17) 0.4045(5) 0.6186(3) 0.0395(13) Uani 1 1 d . . .
C21 C -0.0153(2) 0.4302(5) 0.5986(4) 0.0530(15) Uani 1 1 d . . .
H21 H -0.0224 0.4900 0.6326 0.064 Uiso 1 1 calc R . .
C22 C -0.04919(19) 0.3690(6) 0.5293(4) 0.0583(16) Uani 1 1 d . . .
H22 H -0.0791 0.3872 0.5161 0.070 Uiso 1 1 calc R . .
C23 C -0.0381(2) 0.2797(6) 0.4796(4) 0.0573(16) Uani 1 1 d . . .
H23 H -0.0608 0.2377 0.4327 0.069 Uiso 1 1 calc R . .
C24 C 0.00597(18) 0.2522(5) 0.4983(3) 0.0463(14) Uani 1 1 d . . .
H24 H 0.0127 0.1915 0.4644 0.056 Uiso 1 1 calc R . .
C25 C 0.04051(16) 0.3143(4) 0.5675(3) 0.0373(12) Uani 1 1 d . . .
C26 C 0.1954(2) 0.7536(6) 0.9342(5) 0.0693(18) Uani 1 1 d . . .
H26 H 0.2093 0.8289 0.9532 0.083 Uiso 1 1 calc R . .
C27 C 0.17826(19) 0.7237(5) 0.8411(4) 0.0596(16) Uani 1 1 d . . .
H27 H 0.1804 0.7771 0.7970 0.072 Uiso 1 1 calc R . .
C28 C 0.15786(17) 0.6122(5) 0.8162(3) 0.0463(14) Uani 1 1 d . . .
C29 C 0.13751(17) 0.5571(5) 0.7219(4) 0.0457(14) Uani 1 1 d . . .
C30 C 0.09736(18) 0.0171(5) 0.4719(4) 0.0532(15) Uani 1 1 d . . .
H30 H 0.1086 -0.0306 0.5253 0.064 Uiso 1 1 calc R . .
C31 C 0.0840(2) -0.0359(5) 0.3844(4) 0.0650(17) Uani 1 1 d . . .
H31 H 0.0866 -0.1198 0.3788 0.078 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 1.903(5) . ?
Br2 C14 1.887(6) . ?
O1 C19 1.215(6) . ?
O2 C29 1.196(6) . ?
O3 C8 1.202(6) . ?
N1 N2 1.361(5) . ?
N1 C5 1.372(6) . ?
N1 C4 1.436(6) . ?
N2 C12 1.337(6) . ?
C1 C31 1.359(8) . ?
C1 C2 1.370(8) . ?
C2 C3 1.370(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(7) . ?
C3 H3 0.9300 . ?
C4 C30 1.373(7) . ?
C5 C6 1.383(6) . ?
C5 C25 1.451(7) . ?
C6 C12 1.391(7) . ?
C6 C7 1.470(7) . ?
C7 C19 1.542(7) . ?
C7 C29 1.556(7) . ?
C7 C8 1.565(7) . ?
C8 C9 1.471(7) . ?
C9 C10 1.381(7) . ?
C9 C28 1.388(7) . ?
C10 C11 1.377(8) . ?
C10 H10 0.9300 . ?
C11 C26 1.378(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.492(7) . ?
C13 C14 1.381(7) . ?
C13 C18 1.389(8) . ?
C14 C15 1.380(8) . ?
C15 C16 1.368(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(8) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.476(7) . ?
C20 C21 1.378(7) . ?
C20 C25 1.408(7) . ?
C21 C22 1.376(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.384(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.373(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.389(7) . ?
C24 H24 0.9300 . ?
C26 C27 1.378(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.370(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.486(7) . ?
C30 C31 1.390(7) . ?
C30 H30 0.9300 . ?
C31 H31 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
N2 N1 C5 112.0(4) . . ?
N2 N1 C4 117.8(4) . . ?
C5 N1 C4 128.7(4) . . ?
C12 N2 N1 104.8(4) . . ?
C31 C1 C2 121.7(5) . . ?
C31 C1 Br1 119.5(4) . . ?
C2 C1 Br1 118.8(4) . . ?
C3 C2 C1 119.0(5) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.8(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C30 C4 C3 121.2(5) . . ?
C30 C4 N1 119.5(4) . . ?
C3 C4 N1 119.3(4) . . ?
N1 C5 C6 105.6(4) . . ?
N1 C5 C25 129.6(4) . . ?
C6 C5 C25 124.2(4) . . ?
C5 C6 C12 106.1(4) . . ?
C5 C6 C7 123.2(5) . . ?
C12 C6 C7 130.7(5) . . ?
C6 C7 C19 113.1(4) . . ?
C6 C7 C29 112.9(4) . . ?
C19 C7 C29 105.6(4) . . ?
C6 C7 C8 115.6(4) . . ?
C19 C7 C8 106.8(4) . . ?
C29 C7 C8 101.8(4) . . ?
O3 C8 C9 127.8(5) . . ?
O3 C8 C7 124.4(5) . . ?
C9 C8 C7 107.8(4) . . ?
C10 C9 C28 121.1(5) . . ?
C10 C9 C8 128.2(5) . . ?
C28 C9 C8 110.8(4) . . ?
C9 C10 C11 117.1(5) . . ?
C9 C10 H10 121.5 . . ?
C11 C10 H10 121.5 . . ?
C26 C11 C10 121.7(5) . . ?
C26 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
N2 C12 C6 111.5(4) . . ?
N2 C12 C13 120.3(5) . . ?
C6 C12 C13 128.3(5) . . ?
C14 C13 C18 117.4(5) . . ?
C14 C13 C12 122.4(5) . . ?
C18 C13 C12 120.2(5) . . ?
C15 C14 C13 121.3(6) . . ?
C15 C14 Br2 118.3(5) . . ?
C13 C14 Br2 120.3(4) . . ?
C16 C15 C14 120.1(6) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.0(6) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.8(6) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 121.3(6) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
O1 C19 C20 122.0(5) . . ?
O1 C19 C7 118.3(5) . . ?
C20 C19 C7 119.7(5) . . ?
C21 C20 C25 119.9(5) . . ?
C21 C20 C19 117.1(5) . . ?
C25 C20 C19 123.0(5) . . ?
C22 C21 C20 121.1(5) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 118.9(5) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C24 C23 C22 121.1(5) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 120.5(5) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C20 118.4(5) . . ?
C24 C25 C5 125.3(5) . . ?
C20 C25 C5 116.0(4) . . ?
C11 C26 C27 121.2(6) . . ?
C11 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C28 C27 C26 117.4(5) . . ?
C28 C27 H27 121.3 . . ?
C26 C27 H27 121.3 . . ?
C27 C28 C9 121.5(5) . . ?
C27 C28 C29 128.3(5) . . ?
C9 C28 C29 110.2(5) . . ?
O2 C29 C28 126.9(5) . . ?
O2 C29 C7 125.4(5) . . ?
C28 C29 C7 107.7(4) . . ?
C4 C30 C31 118.5(5) . . ?
C4 C30 H30 120.8 . . ?
C31 C30 H30 120.8 . . ?
C1 C31 C30 119.8(5) . . ?
C1 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        20.91
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.060
_atom_sites_special_details      
;
The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.052
;
