# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1l
_audit_block_doi                 10.5517/cc1jmg1n
_database_code_depnum_ccdc_archive 'CCDC 1418871'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18 Br Cl N2 O3'
_chemical_formula_sum            'C26 H18 Br Cl N2 O3'
_chemical_formula_weight         521.78

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'
Cl Cl 0.1484 0.1585 '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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2855(14)
_cell_length_b                   11.4402(17)
_cell_length_c                   12.5128(19)
_cell_angle_alpha                115.765(4)
_cell_angle_beta                 103.676(4)
_cell_angle_gamma                97.062(5)
_cell_volume                     1123.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6919
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.57

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    1.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.570
_exptl_absorpt_correction_T_max  0.693
_exptl_absorpt_process_details   sadabs

_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_reflns_number            16973
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         27.52
_reflns_number_total             5086
_reflns_number_gt                3514
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.0560P)²+0.8196P] 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_number_reflns         5086
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1392
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.80885(6) 0.33366(6) 1.00825(4) 0.1072(2) Uani 1 1 d . . .
C1 C 0.0841(3) 0.4617(3) 0.6406(3) 0.0445(6) Uani 1 1 d . . .
C2 C -0.0845(4) 0.3973(3) 0.5821(3) 0.0545(8) Uani 1 1 d . . .
H2A H -0.1283 0.4163 0.5148 0.065 Uiso 1 1 calc R . .
H2B H -0.1367 0.4294 0.6439 0.065 Uiso 1 1 calc R . .
C3 C -0.0980(3) 0.2479(3) 0.5318(3) 0.0494(7) Uani 1 1 d . . .
H3A H -0.1311 0.2176 0.5855 0.059 Uiso 1 1 calc R . .
H3B H -0.1717 0.1971 0.4478 0.059 Uiso 1 1 calc R . .
C4 C 0.0934(3) 0.2232(2) 0.4187(2) 0.0352(5) Uani 1 1 d . . .
H4 H 0.0616 0.2951 0.4043 0.042 Uiso 1 1 calc R . .
C5 C 0.0141(3) 0.0914(3) 0.3015(2) 0.0370(6) Uani 1 1 d . . .
C6 C -0.0035(3) -0.0306(3) 0.3028(3) 0.0505(7) Uani 1 1 d . . .
H6 H 0.0299 -0.0320 0.3783 0.061 Uiso 1 1 calc R . .
C7 C -0.0706(4) -0.1500(3) 0.1915(3) 0.0614(9) Uani 1 1 d . . .
H7 H -0.0788 -0.2316 0.1919 0.074 Uiso 1 1 calc R . .
C8 C -0.1248(3) -0.1475(3) 0.0813(3) 0.0559(8) Uani 1 1 d . . .
C9 C -0.1144(3) -0.0286(3) 0.0780(3) 0.0541(8) Uani 1 1 d . . .
H9 H -0.1542 -0.0282 0.0027 0.065 Uiso 1 1 calc R . .
C10 C -0.0442(3) 0.0906(3) 0.1882(3) 0.0447(6) Uani 1 1 d . . .
H10 H -0.0359 0.1716 0.1865 0.054 Uiso 1 1 calc R . .
C11 C 0.3425(3) 0.3162(2) 0.3955(2) 0.0359(5) Uani 1 1 d . . .
C12 C 0.4236(3) 0.2217(3) 0.3271(2) 0.0380(6) Uani 1 1 d . . .
C13 C 0.5003(3) 0.2287(3) 0.2461(3) 0.0483(7) Uani 1 1 d . . .
H13 H 0.5052 0.2993 0.2277 0.058 Uiso 1 1 calc R . .
C14 C 0.5687(4) 0.1267(4) 0.1944(3) 0.0621(9) Uani 1 1 d . . .
H14 H 0.6199 0.1280 0.1392 0.075 Uiso 1 1 calc R . .
C15 C 0.5626(4) 0.0225(3) 0.2229(3) 0.0641(9) Uani 1 1 d . . .
H15 H 0.6096 -0.0448 0.1862 0.077 Uiso 1 1 calc R . .
C16 C 0.4885(3) 0.0155(3) 0.3046(3) 0.0512(7) Uani 1 1 d . . .
H16 H 0.4859 -0.0543 0.3241 0.061 Uiso 1 1 calc R . .
C17 C 0.4181(3) 0.1169(2) 0.3564(2) 0.0381(6) Uani 1 1 d . . .
C18 C 0.3347(3) 0.1360(2) 0.4478(2) 0.0365(5) Uani 1 1 d . . .
C19 C 0.2728(3) 0.2605(2) 0.4690(2) 0.0339(5) Uani 1 1 d . . .
C20 C 0.3074(3) 0.3696(2) 0.6092(2) 0.0364(5) Uani 1 1 d . . .
H20 H 0.3411 0.4579 0.6161 0.044 Uiso 1 1 calc R . .
C21 C 0.4287(3) 0.3580(2) 0.7063(2) 0.0380(6) Uani 1 1 d . . .
C22 C 0.4006(4) 0.3531(3) 0.8078(3) 0.0569(8) Uani 1 1 d . . .
H22 H 0.3040 0.3553 0.8163 0.068 Uiso 1 1 calc R . .
C23 C 0.5132(4) 0.3451(4) 0.8974(3) 0.0659(9) Uani 1 1 d . . .
H23 H 0.4921 0.3406 0.9647 0.079 Uiso 1 1 calc R . .
C24 C 0.6552(4) 0.3438(3) 0.8857(3) 0.0570(8) Uani 1 1 d . . .
C25 C 0.6875(4) 0.3503(3) 0.7863(3) 0.0564(8) Uani 1 1 d . . .
H25 H 0.7848 0.3494 0.7790 0.068 Uiso 1 1 calc R . .
C26 C 0.5746(3) 0.3580(3) 0.6978(3) 0.0493(7) Uani 1 1 d . . .
H26 H 0.5966 0.3633 0.6311 0.059 Uiso 1 1 calc R . .
Cl2 Cl -0.20936(11) -0.29945(10) -0.05788(10) 0.0895(4) Uani 1 1 d . . .
N1 N 0.0569(2) 0.2302(2) 0.5303(2) 0.0381(5) Uani 1 1 d . . .
N2 N 0.1572(2) 0.3598(2) 0.6274(2) 0.0387(5) Uani 1 1 d . . .
O1 O 0.1500(3) 0.5804(2) 0.6933(2) 0.0601(6) Uani 1 1 d . . .
O2 O 0.3314(2) 0.42051(19) 0.3957(2) 0.0518(5) Uani 1 1 d . . .
O3 O 0.3175(2) 0.06620(19) 0.49599(19) 0.0486(5) Uani 1 1 d . . .


_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 C24 1.887(3) . ?
C1 O1 1.216(3) . ?
C1 N2 1.389(3) . ?
C1 C2 1.495(4) . ?
C2 C3 1.519(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.480(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.485(3) . ?
C4 C5 1.504(4) . ?
C4 C19 1.565(3) . ?
C4 H4 0.9800 . ?
C5 C10 1.389(4) . ?
C5 C6 1.393(4) . ?
C6 C7 1.385(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(5) . ?
C8 Cl2 1.748(3) . ?
C9 C10 1.381(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O2 1.209(3) . ?
C11 C12 1.473(4) . ?
C11 C19 1.537(3) . ?
C12 C13 1.392(4) . ?
C12 C17 1.397(4) . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.483(4) . ?
C18 O3 1.208(3) . ?
C18 C19 1.542(3) . ?
C19 C20 1.571(3) . ?
C20 N2 1.463(3) . ?
C20 C21 1.514(4) . ?
C20 H20 0.9800 . ?
C21 C22 1.378(4) . ?
C21 C26 1.384(4) . ?
C22 C23 1.385(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.361(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.376(5) . ?
C25 C26 1.376(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N1 N2 1.450(3) . ?

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
O1 C1 N2 124.3(3) . . ?
O1 C1 C2 128.4(3) . . ?
N2 C1 C2 107.2(2) . . ?
C1 C2 C3 104.7(2) . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
N1 C3 C2 106.1(2) . . ?
N1 C3 H3A 110.5 . . ?
C2 C3 H3A 110.5 . . ?
N1 C3 H3B 110.5 . . ?
C2 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
N1 C4 C5 113.3(2) . . ?
N1 C4 C19 100.69(19) . . ?
C5 C4 C19 117.2(2) . . ?
N1 C4 H4 108.4 . . ?
C5 C4 H4 108.4 . . ?
C19 C4 H4 108.4 . . ?
C10 C5 C6 118.7(3) . . ?
C10 C5 C4 119.3(2) . . ?
C6 C5 C4 122.1(2) . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 121.3(3) . . ?
C7 C8 Cl2 119.0(3) . . ?
C9 C8 Cl2 119.7(3) . . ?
C8 C9 C10 119.1(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C5 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
O2 C11 C12 127.0(2) . . ?
O2 C11 C19 124.7(2) . . ?
C12 C11 C19 108.4(2) . . ?
C13 C12 C17 121.4(2) . . ?
C13 C12 C11 128.7(2) . . ?
C17 C12 C11 109.9(2) . . ?
C14 C13 C12 117.3(3) . . ?
C14 C13 H13 121.4 . . ?
C12 C13 H13 121.4 . . ?
C13 C14 C15 121.3(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 121.9(3) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 117.3(3) . . ?
C15 C16 H16 121.3 . . ?
C17 C16 H16 121.3 . . ?
C16 C17 C12 120.8(3) . . ?
C16 C17 C18 128.6(2) . . ?
C12 C17 C18 110.5(2) . . ?
O3 C18 C17 126.3(2) . . ?
O3 C18 C19 126.3(2) . . ?
C17 C18 C19 107.4(2) . . ?
C11 C19 C18 103.5(2) . . ?
C11 C19 C4 111.18(19) . . ?
C18 C19 C4 111.97(19) . . ?
C11 C19 C20 112.41(19) . . ?
C18 C19 C20 116.5(2) . . ?
C4 C19 C20 101.58(19) . . ?
N2 C20 C21 113.2(2) . . ?
N2 C20 C19 103.89(19) . . ?
C21 C20 C19 116.0(2) . . ?
N2 C20 H20 107.8 . . ?
C21 C20 H20 107.8 . . ?
C19 C20 H20 107.8 . . ?
C22 C21 C26 118.0(3) . . ?
C22 C21 C20 121.8(2) . . ?
C26 C21 C20 120.1(2) . . ?
C21 C22 C23 121.4(3) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 119.3(3) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 120.8(3) . . ?
C23 C24 Br1 119.2(2) . . ?
C25 C24 Br1 120.0(2) . . ?
C24 C25 C26 119.4(3) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C25 C26 C21 121.2(3) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
N2 N1 C3 103.1(2) . . ?
N2 N1 C4 100.67(18) . . ?
C3 N1 C4 114.3(2) . . ?
C1 N2 N1 111.0(2) . . ?
C1 N2 C20 120.4(2) . . ?
N1 N2 C20 108.12(18) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.806
_refine_diff_density_min         -1.027
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_1m
_audit_block_doi                 10.5517/cc1jmg2p
_database_code_depnum_ccdc_archive 'CCDC 1418872'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H21 Br N2 O4'
_chemical_formula_sum            'C27 H21 Br N2 O4'
_chemical_formula_weight         517.37

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   14.34(2)
_cell_length_b                   8.417(11)
_cell_length_c                   20.37(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.82(8)
_cell_angle_gamma                90.00
_cell_volume                     2298(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2272
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      20.99

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    1.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_T_max  0.711
_exptl_absorpt_process_details   sadabs

_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_reflns_number            19654
_diffrn_reflns_av_R_equivalents  0.4630
_diffrn_reflns_av_sigmaI/netI    0.2467
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4015
_reflns_number_gt                1817
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.0254P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0081(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4015
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1930
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.1912
_refine_ls_wR_factor_gt          0.1534
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_restrained_S_all      0.889
_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 0.39834(5) 0.28807(11) -0.28589(4) 0.0895(5) Uani 1 1 d . . .
C1 C 0.9521(4) 0.6417(7) 0.0449(3) 0.0410(15) Uani 1 1 d . . .
C2 C 0.9177(4) 0.7356(7) -0.0211(3) 0.0442(16) Uani 1 1 d . . .
H2A H 0.9538 0.7049 -0.0514 0.053 Uiso 1 1 calc R . .
H2B H 0.9275 0.8483 -0.0112 0.053 Uiso 1 1 calc R . .
C3 C 0.8073(4) 0.6967(7) -0.0553(3) 0.0546(18) Uani 1 1 d . . .
H3A H 0.7681 0.7935 -0.0641 0.066 Uiso 1 1 calc R . .
H3B H 0.7948 0.6429 -0.0997 0.066 Uiso 1 1 calc R . .
C4 C 0.7674(4) 0.4207(6) -0.0253(3) 0.0375(14) Uani 1 1 d . . .
H4 H 0.8248 0.3888 -0.0377 0.045 Uiso 1 1 calc R . .
C5 C 0.6755(3) 0.3906(7) -0.0874(3) 0.0361(14) Uani 1 1 d . . .
C6 C 0.6833(4) 0.2952(7) -0.1404(3) 0.0532(18) Uani 1 1 d . . .
H6 H 0.7447 0.2506 -0.1356 0.064 Uiso 1 1 calc R . .
C7 C 0.6028(4) 0.2649(8) -0.1997(3) 0.063(2) Uani 1 1 d . . .
H7 H 0.6094 0.2027 -0.2355 0.076 Uiso 1 1 calc R . .
C8 C 0.5118(4) 0.3281(8) -0.2055(3) 0.0501(16) Uani 1 1 d . . .
C9 C 0.5015(4) 0.4197(7) -0.1543(3) 0.0467(16) Uani 1 1 d . . .
H9 H 0.4394 0.4616 -0.1591 0.056 Uiso 1 1 calc R . .
C10 C 0.5820(4) 0.4512(7) -0.0954(3) 0.0428(15) Uani 1 1 d . . .
H10 H 0.5743 0.5140 -0.0602 0.051 Uiso 1 1 calc R . .
C11 C 0.6860(4) 0.3574(7) 0.0658(3) 0.0400(15) Uani 1 1 d . . .
C12 C 0.6516(4) 0.1929(7) 0.0729(3) 0.0397(15) Uani 1 1 d . . .
C13 C 0.5723(4) 0.1443(8) 0.0908(3) 0.0532(17) Uani 1 1 d . . .
H13 H 0.5307 0.2182 0.1005 0.064 Uiso 1 1 calc R . .
C14 C 0.5556(5) -0.0170(8) 0.0940(4) 0.063(2) Uani 1 1 d . . .
H14 H 0.5034 -0.0526 0.1072 0.075 Uiso 1 1 calc R . .
C15 C 0.6169(5) -0.1263(8) 0.0774(4) 0.0637(19) Uani 1 1 d . . .
H15 H 0.6030 -0.2342 0.0775 0.076 Uiso 1 1 calc R . .
C16 C 0.6971(4) -0.0780(8) 0.0611(3) 0.0549(17) Uani 1 1 d . . .
H16 H 0.7391 -0.1521 0.0520 0.066 Uiso 1 1 calc R . .
C17 C 0.7147(4) 0.0836(7) 0.0584(3) 0.0419(15) Uani 1 1 d . . .
C18 C 0.7959(4) 0.1658(7) 0.0436(3) 0.0470(16) Uani 1 1 d . . .
C19 C 0.7792(3) 0.3442(6) 0.0454(3) 0.0358(14) Uani 1 1 d . . .
C20 C 0.8698(4) 0.4396(7) 0.0949(3) 0.0408(15) Uani 1 1 d . . .
H20 H 0.9301 0.3811 0.0975 0.049 Uiso 1 1 calc R . .
C21 C 0.8732(4) 0.4614(7) 0.1683(3) 0.0397(15) Uani 1 1 d . . .
C22 C 0.8636(4) 0.6099(7) 0.1961(3) 0.0444(15) Uani 1 1 d . . .
H22 H 0.8525 0.7002 0.1681 0.053 Uiso 1 1 calc R . .
C23 C 0.8706(4) 0.6217(8) 0.2645(3) 0.0536(17) Uani 1 1 d . . .
C24 C 0.8444(6) 0.9038(9) 0.2567(4) 0.081(2) Uani 1 1 d . . .
H24A H 0.8895 0.9140 0.2317 0.122 Uiso 1 1 calc R . .
H24B H 0.8520 0.9934 0.2873 0.122 Uiso 1 1 calc R . .
H24C H 0.7770 0.9000 0.2239 0.122 Uiso 1 1 calc R . .
C25 C 0.8886(5) 0.4871(10) 0.3068(3) 0.069(2) Uani 1 1 d . . .
H25 H 0.8944 0.4955 0.3536 0.083 Uiso 1 1 calc R . .
C26 C 0.8979(5) 0.3423(9) 0.2793(3) 0.070(2) Uani 1 1 d . . .
H26 H 0.9089 0.2518 0.3072 0.084 Uiso 1 1 calc R . .
C27 C 0.8911(4) 0.3306(8) 0.2118(3) 0.0556(18) Uani 1 1 d . . .
H27 H 0.8987 0.2315 0.1940 0.067 Uiso 1 1 calc R . .
N1 N 0.8690(3) 0.5864(5) 0.0567(2) 0.0370(12) Uani 1 1 d . . .
N2 N 0.7795(3) 0.5916(5) -0.0059(2) 0.0410(12) Uani 1 1 d . . .
O1 O 1.0366(3) 0.6177(5) 0.0843(2) 0.0523(11) Uani 1 1 d . . .
O2 O 0.8658(3) 0.1054(5) 0.0329(2) 0.0656(13) Uani 1 1 d . . .
O3 O 0.6469(3) 0.4777(5) 0.0757(2) 0.0514(11) Uani 1 1 d . . .
O4 O 0.8658(4) 0.7626(6) 0.2969(2) 0.0757(15) Uani 1 1 d . . .


_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 C8 1.884(6) . ?
C1 O1 1.209(6) . ?
C1 N1 1.377(7) . ?
C1 C2 1.485(8) . ?
C2 C3 1.521(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N2 1.496(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.486(7) . ?
C4 C5 1.489(7) . ?
C4 C19 1.532(8) . ?
C4 H4 0.9800 . ?
C5 C6 1.380(8) . ?
C5 C10 1.388(7) . ?
C6 C7 1.365(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.347(8) . ?
C9 C10 1.363(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O3 1.208(6) . ?
C11 C12 1.494(8) . ?
C11 C19 1.537(8) . ?
C12 C13 1.375(8) . ?
C12 C17 1.394(8) . ?
C13 C14 1.384(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.395(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.474(8) . ?
C18 O2 1.212(7) . ?
C18 C19 1.523(8) . ?
C19 C20 1.555(7) . ?
C20 N1 1.459(7) . ?
C20 C21 1.489(8) . ?
C20 H20 0.9800 . ?
C21 C27 1.379(8) . ?
C21 C22 1.400(8) . ?
C22 C23 1.365(8) . ?
C22 H22 0.9300 . ?
C23 O4 1.371(8) . ?
C23 C25 1.390(9) . ?
C24 O4 1.414(8) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.367(9) . ?
C25 H25 0.9300 . ?
C26 C27 1.347(9) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
N1 N2 1.454(6) . ?

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
O1 C1 N1 123.6(5) . . ?
O1 C1 C2 128.4(5) . . ?
N1 C1 C2 108.0(5) . . ?
C1 C2 C3 104.8(5) . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
N2 C3 C2 107.6(5) . . ?
N2 C3 H3A 110.2 . . ?
C2 C3 H3A 110.2 . . ?
N2 C3 H3B 110.2 . . ?
C2 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
N2 C4 C5 112.0(4) . . ?
N2 C4 C19 101.2(4) . . ?
C5 C4 C19 119.7(4) . . ?
N2 C4 H4 107.8 . . ?
C5 C4 H4 107.8 . . ?
C19 C4 H4 107.8 . . ?
C6 C5 C10 117.7(5) . . ?
C6 C5 C4 118.0(5) . . ?
C10 C5 C4 124.3(5) . . ?
C7 C6 C5 121.5(5) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 118.8(6) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C8 C7 121.1(5) . . ?
C9 C8 Br1 118.5(5) . . ?
C7 C8 Br1 120.4(5) . . ?
C8 C9 C10 120.0(5) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C5 120.8(5) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
O3 C11 C12 124.9(5) . . ?
O3 C11 C19 127.2(5) . . ?
C12 C11 C19 107.9(5) . . ?
C13 C12 C17 121.4(6) . . ?
C13 C12 C11 129.3(6) . . ?
C17 C12 C11 109.3(5) . . ?
C12 C13 C14 118.5(6) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C13 C14 C15 120.0(6) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 121.3(6) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 118.8(6) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C12 119.8(5) . . ?
C16 C17 C18 129.6(6) . . ?
C12 C17 C18 110.6(5) . . ?
O2 C18 C17 127.1(6) . . ?
O2 C18 C19 124.4(6) . . ?
C17 C18 C19 108.4(5) . . ?
C18 C19 C4 110.9(4) . . ?
C18 C19 C11 103.7(5) . . ?
C4 C19 C11 114.1(4) . . ?
C18 C19 C20 115.0(4) . . ?
C4 C19 C20 100.4(4) . . ?
C11 C19 C20 113.2(4) . . ?
N1 C20 C21 115.0(5) . . ?
N1 C20 C19 104.2(4) . . ?
C21 C20 C19 115.8(5) . . ?
N1 C20 H20 107.1 . . ?
C21 C20 H20 107.1 . . ?
C19 C20 H20 107.1 . . ?
C27 C21 C22 118.4(6) . . ?
C27 C21 C20 118.6(6) . . ?
C22 C21 C20 122.9(5) . . ?
C23 C22 C21 119.8(6) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 O4 123.8(6) . . ?
C22 C23 C25 120.2(6) . . ?
O4 C23 C25 116.0(6) . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C23 119.8(6) . . ?
C26 C25 H25 120.1 . . ?
C23 C25 H25 120.1 . . ?
C27 C26 C25 120.1(6) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C21 121.8(6) . . ?
C26 C27 H27 119.1 . . ?
C21 C27 H27 119.1 . . ?
C1 N1 N2 112.7(4) . . ?
C1 N1 C20 122.4(4) . . ?
N2 N1 C20 109.3(4) . . ?
N1 N2 C4 100.8(4) . . ?
N1 N2 C3 104.1(4) . . ?
C4 N2 C3 115.3(5) . . ?
C23 O4 C24 119.1(5) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.095
