# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 850811'
_audit_update_record             
;
2011-10-26 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;
#TrackingRef '21gl.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 N2 O4'
_chemical_formula_sum            'C26 H24 N2 O4'
_chemical_formula_weight         428.47

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'

_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                   9.7172(19)
_cell_length_b                   11.762(2)
_cell_length_c                   19.840(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.84(3)
_cell_angle_gamma                90.00
_cell_volume                     2234.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2895
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.89

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   '(Jacobson, 1998)'

_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  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17496
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.20
_reflns_number_total             4025
_reflns_number_gt                2489
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97

_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)+(0.0815P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4025
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1482
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
C1 C 0.6405(2) 0.03474(16) 0.34024(9) 0.0482(5) Uani 1 1 d . . .
C2 C 0.6743(3) 0.11431(18) 0.29475(11) 0.0619(6) Uani 1 1 d . . .
H2 H 0.6064 0.1391 0.2589 0.074 Uiso 1 1 calc R . .
C3 C 0.8082(3) 0.1575(2) 0.30199(14) 0.0778(7) Uani 1 1 d . . .
H3 H 0.8301 0.2101 0.2705 0.093 Uiso 1 1 calc R . .
C4 C 0.9085(3) 0.1237(2) 0.35485(15) 0.0813(8) Uani 1 1 d . . .
H4 H 0.9983 0.1534 0.3596 0.098 Uiso 1 1 calc R . .
C5 C 0.8760(3) 0.0458(2) 0.40078(12) 0.0749(7) Uani 1 1 d . . .
H5 H 0.9439 0.0232 0.4372 0.090 Uiso 1 1 calc R . .
C6 C 0.7428(2) 0.0002(2) 0.39368(11) 0.0619(6) Uani 1 1 d . . .
H6 H 0.7221 -0.0537 0.4248 0.074 Uiso 1 1 calc R . .
C7 C 0.3253(2) -0.00433(15) 0.22174(9) 0.0467(5) Uani 1 1 d . . .
C8 C 0.4041(3) -0.05567(17) 0.17834(10) 0.0593(6) Uani 1 1 d . . .
H8 H 0.5008 -0.0590 0.1902 0.071 Uiso 1 1 calc R . .
C9 C 0.3382(3) -0.1019(2) 0.11722(11) 0.0748(8) Uani 1 1 d . . .
H9 H 0.3911 -0.1370 0.0883 0.090 Uiso 1 1 calc R . .
C10 C 0.1959(4) -0.0967(2) 0.09884(12) 0.0825(8) Uani 1 1 d . . .
H10 H 0.1528 -0.1272 0.0573 0.099 Uiso 1 1 calc R . .
C11 C 0.1170(3) -0.0463(2) 0.14161(12) 0.0763(7) Uani 1 1 d . . .
H11 H 0.0204 -0.0427 0.1291 0.092 Uiso 1 1 calc R . .
C12 C 0.1814(2) -0.00075(17) 0.20371(11) 0.0581(6) Uani 1 1 d . . .
H12 H 0.1278 0.0321 0.2331 0.070 Uiso 1 1 calc R . .
C13 C 0.3581(2) -0.12911(16) 0.40053(9) 0.0487(5) Uani 1 1 d . . .
C14 C 0.3957(3) -0.23802(17) 0.38342(12) 0.0673(7) Uani 1 1 d . . .
H14 H 0.4784 -0.2489 0.3667 0.081 Uiso 1 1 calc R . .
C15 C 0.3121(3) -0.3298(2) 0.39097(12) 0.0850(9) Uani 1 1 d . . .
H15 H 0.3382 -0.4021 0.3790 0.102 Uiso 1 1 calc R . .
C16 C 0.1902(3) -0.3150(3) 0.41615(12) 0.0911(9) Uani 1 1 d . . .
H16 H 0.1336 -0.3770 0.4214 0.109 Uiso 1 1 calc R . .
C17 C 0.1528(3) -0.2085(3) 0.43337(14) 0.0886(9) Uani 1 1 d . . .
H17 H 0.0711 -0.1984 0.4511 0.106 Uiso 1 1 calc R . .
C18 C 0.2346(3) -0.1160(2) 0.42485(11) 0.0672(6) Uani 1 1 d . . .
H18 H 0.2061 -0.0438 0.4356 0.081 Uiso 1 1 calc R . .
C19 C 0.4975(2) -0.02138(16) 0.33075(9) 0.0452(5) Uani 1 1 d . . .
H19 H 0.5055 -0.0963 0.3102 0.054 Uiso 1 1 calc R . .
C20 C 0.3365(2) 0.13796(15) 0.31216(9) 0.0436(5) Uani 1 1 d . . .
C21 C 0.3554(2) 0.15591(15) 0.38034(9) 0.0460(5) Uani 1 1 d . . .
C22 C 0.4318(2) 0.06984(15) 0.42907(9) 0.0490(5) Uani 1 1 d . . .
H22A H 0.5221 0.1006 0.4491 0.059 Uiso 1 1 calc R . .
H22B H 0.3794 0.0568 0.4658 0.059 Uiso 1 1 calc R . .
C23 C 0.2714(2) 0.22455(16) 0.26070(10) 0.0477(5) Uani 1 1 d . . .
C24 C 0.0810(3) 0.3422(2) 0.22374(13) 0.0884(9) Uani 1 1 d . . .
H24A H 0.1261 0.4119 0.2402 0.133 Uiso 1 1 calc R . .
H24B H -0.0170 0.3472 0.2253 0.133 Uiso 1 1 calc R . .
H24C H 0.0939 0.3293 0.1774 0.133 Uiso 1 1 calc R . .
C25 C 0.3156(2) 0.26407(18) 0.40850(11) 0.0561(6) Uani 1 1 d . . .
C26 C 0.2636(4) 0.3511(2) 0.50893(14) 0.1252(14) Uani 1 1 d . . .
H26A H 0.3314 0.4091 0.5053 0.188 Uiso 1 1 calc R . .
H26B H 0.2644 0.3337 0.5563 0.188 Uiso 1 1 calc R . .
H26C H 0.1724 0.3776 0.4886 0.188 Uiso 1 1 calc R . .
N1 N 0.39140(17) 0.04413(13) 0.28423(7) 0.0460(4) Uani 1 1 d . . .
N2 N 0.45241(18) -0.03839(13) 0.39658(7) 0.0471(4) Uani 1 1 d . . .
O1 O 0.33368(16) 0.26380(12) 0.21892(8) 0.0631(4) Uani 1 1 d . . .
O2 O 0.14117(16) 0.24921(11) 0.26615(7) 0.0592(4) Uani 1 1 d . . .
O3 O 0.2991(2) 0.35420(13) 0.37999(8) 0.0805(6) Uani 1 1 d . . .
O4 O 0.2975(2) 0.24963(13) 0.47353(8) 0.0874(6) 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
C1 C2 1.378(3) . ?
C1 C6 1.385(3) . ?
C1 C19 1.521(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.383(3) . ?
C7 C8 1.385(3) . ?
C7 N1 1.415(2) . ?
C8 C9 1.382(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.376(3) . ?
C13 C14 1.390(3) . ?
C13 N2 1.418(2) . ?
C14 C15 1.374(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 N2 1.461(2) . ?
C19 N1 1.477(2) . ?
C19 H19 0.9800 . ?
C20 C21 1.350(2) . ?
C20 N1 1.383(2) . ?
C20 C23 1.503(3) . ?
C21 C25 1.468(3) . ?
C21 C22 1.505(3) . ?
C22 N2 1.456(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 O1 1.199(2) . ?
C23 O2 1.321(2) . ?
C24 O2 1.441(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O3 1.199(2) . ?
C25 O4 1.342(2) . ?
C26 O4 1.451(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
C2 C1 C6 118.7(2) . . ?
C2 C1 C19 121.92(19) . . ?
C6 C1 C19 119.23(18) . . ?
C1 C2 C3 120.5(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.0(2) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C12 C7 C8 119.63(19) . . ?
C12 C7 N1 120.12(18) . . ?
C8 C7 N1 120.2(2) . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C7 C12 C11 119.9(2) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C18 C13 C14 118.0(2) . . ?
C18 C13 N2 123.09(18) . . ?
C14 C13 N2 118.73(19) . . ?
C15 C14 C13 120.8(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.4(2) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 120.7(2) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
N2 C19 N1 110.25(15) . . ?
N2 C19 C1 110.86(16) . . ?
N1 C19 C1 112.09(15) . . ?
N2 C19 H19 107.8 . . ?
N1 C19 H19 107.8 . . ?
C1 C19 H19 107.8 . . ?
C21 C20 N1 122.04(17) . . ?
C21 C20 C23 122.97(17) . . ?
N1 C20 C23 114.52(15) . . ?
C20 C21 C25 121.14(17) . . ?
C20 C21 C22 120.41(16) . . ?
C25 C21 C22 118.15(16) . . ?
N2 C22 C21 113.19(15) . . ?
N2 C22 H22A 108.9 . . ?
C21 C22 H22A 108.9 . . ?
N2 C22 H22B 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.8 . . ?
O1 C23 O2 125.15(18) . . ?
O1 C23 C20 121.85(19) . . ?
O2 C23 C20 112.99(16) . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C25 O4 122.43(18) . . ?
O3 C25 C21 127.54(18) . . ?
O4 C25 C21 110.03(17) . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C20 N1 C7 121.60(16) . . ?
C20 N1 C19 116.23(14) . . ?
C7 N1 C19 120.07(15) . . ?
C13 N2 C22 119.63(15) . . ?
C13 N2 C19 116.63(15) . . ?
C22 N2 C19 111.16(14) . . ?
C23 O2 C24 114.68(16) . . ?
C25 O4 C26 116.04(18) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1011037'
_audit_update_record             
;
2014-06-29 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 N2 O4'
_chemical_formula_sum            'C26 H24 N2 O4'
_chemical_formula_weight         428.47

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   9.5910(15)
_cell_length_b                   14.916(2)
_cell_length_c                   15.744(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.790(2)
_cell_angle_gamma                90.00
_cell_volume                     2251.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5300
_cell_measurement_theta_min      1.26
_cell_measurement_theta_max      28.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_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 area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12137
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4377
_reflns_number_gt                2459
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX-II (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-XP (Bruker, 2004)'
_computing_publication_material  'SHELXTL (Bruker, 2004)'

_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)+(0.1126P)²+0.8143P] 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         4377
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.2363
_refine_ls_wR_factor_gt          0.1944
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
C1 C 0.4001(4) 0.7139(2) -0.1302(2) 0.0744(10) Uani 1 1 d . . .
H1 H 0.3068 0.7038 -0.1450 0.089 Uiso 1 1 calc R . .
C2 C 0.5035(5) 0.6818(3) -0.1817(3) 0.0963(13) Uani 1 1 d . . .
H2 H 0.4794 0.6498 -0.2307 0.116 Uiso 1 1 calc R . .
C3 C 0.6403(6) 0.6969(3) -0.1608(4) 0.1036(15) Uani 1 1 d . . .
H3 H 0.7095 0.6754 -0.1955 0.124 Uiso 1 1 calc R . .
C4 C 0.6754(4) 0.7433(3) -0.0891(3) 0.0995(14) Uani 1 1 d . . .
H4 H 0.7690 0.7532 -0.0749 0.119 Uiso 1 1 calc R . .
C5 C 0.5743(4) 0.7760(2) -0.0369(3) 0.0767(10) Uani 1 1 d . . .
H5 H 0.5997 0.8081 0.0117 0.092 Uiso 1 1 calc R . .
C6 C 0.4351(3) 0.76071(19) -0.05738(19) 0.0529(7) Uani 1 1 d . . .
C7 C 0.4267(3) 0.8507(2) 0.1604(2) 0.0596(8) Uani 1 1 d . . .
H7 H 0.4355 0.7915 0.1428 0.071 Uiso 1 1 calc R . .
C8 C 0.4704(4) 0.8751(3) 0.2423(2) 0.0721(10) Uani 1 1 d . . .
H8 H 0.5080 0.8323 0.2793 0.087 Uiso 1 1 calc R . .
C9 C 0.4581(4) 0.9624(3) 0.2684(3) 0.0848(12) Uani 1 1 d . . .
H9 H 0.4875 0.9787 0.3231 0.102 Uiso 1 1 calc R . .
C10 C 0.4024(4) 1.0256(3) 0.2139(3) 0.0904(13) Uani 1 1 d . . .
H10 H 0.3937 1.0847 0.2319 0.109 Uiso 1 1 calc R . .
C11 C 0.3593(4) 1.0020(2) 0.1328(2) 0.0747(10) Uani 1 1 d . . .
H11 H 0.3224 1.0455 0.0963 0.090 Uiso 1 1 calc R . .
C12 C 0.3701(3) 0.9141(2) 0.1048(2) 0.0561(8) Uani 1 1 d . . .
C13 C 0.3234(3) 0.89198(18) 0.01439(18) 0.0501(7) Uani 1 1 d . . .
H13 H 0.3863 0.9227 -0.0239 0.060 Uiso 1 1 calc R . .
C14 C 0.2187(3) 0.9811(2) -0.1466(2) 0.0668(9) Uani 1 1 d . . .
H14 H 0.2969 1.0116 -0.1255 0.080 Uiso 1 1 calc R . .
C15 C 0.1800(4) 0.9896(3) -0.2311(2) 0.0797(11) Uani 1 1 d . . .
H15 H 0.2328 1.0253 -0.2663 0.096 Uiso 1 1 calc R . .
C16 C 0.0654(4) 0.9462(3) -0.2638(2) 0.0781(10) Uani 1 1 d . . .
H16 H 0.0391 0.9524 -0.3209 0.094 Uiso 1 1 calc R . .
C17 C -0.0106(4) 0.8932(3) -0.2111(3) 0.0775(10) Uani 1 1 d . . .
H17 H -0.0889 0.8633 -0.2328 0.093 Uiso 1 1 calc R . .
C18 C 0.0277(4) 0.8835(2) -0.1258(2) 0.0683(9) Uani 1 1 d . . .
H18 H -0.0247 0.8468 -0.0912 0.082 Uiso 1 1 calc R . .
C19 C 0.1428(3) 0.92767(18) -0.09203(19) 0.0505(7) Uani 1 1 d . . .
C20 C 0.0837(3) 0.88108(19) 0.05302(19) 0.0543(7) Uani 1 1 d . . .
H20A H -0.0111 0.8944 0.0338 0.065 Uiso 1 1 calc R . .
H20B H 0.0970 0.9048 0.1101 0.065 Uiso 1 1 calc R . .
C21 C 0.1044(3) 0.78094(19) 0.05484(18) 0.0508(7) Uani 1 1 d . . .
C22 C 0.2209(3) 0.74352(18) 0.02322(18) 0.0497(7) Uani 1 1 d . . .
C23 C 0.2520(5) 0.6438(3) 0.0268(3) 0.0829(12) Uani 1 1 d . . .
C24 C 0.2253(7) 0.4983(3) -0.0053(4) 0.180(3) Uani 1 1 d . . .
H24A H 0.2369 0.4649 -0.0568 0.270 Uiso 1 1 calc R . .
H24B H 0.1548 0.4703 0.0276 0.270 Uiso 1 1 calc R . .
H24C H 0.3119 0.4993 0.0269 0.270 Uiso 1 1 calc R . .
C25 C 0.0019(3) 0.7232(2) 0.0947(2) 0.0586(8) Uani 1 1 d . . .
C26 C -0.2194(4) 0.7182(3) 0.1559(3) 0.0914(13) Uani 1 1 d . . .
H26A H -0.2578 0.6731 0.1185 0.137 Uiso 1 1 calc R . .
H26B H -0.2923 0.7577 0.1731 0.137 Uiso 1 1 calc R . .
H26C H -0.1771 0.6901 0.2052 0.137 Uiso 1 1 calc R . .
N1 N 0.1820(2) 0.92504(15) -0.00374(15) 0.0511(6) Uani 1 1 d . . .
N2 N 0.3307(2) 0.79476(15) -0.00374(15) 0.0500(6) Uani 1 1 d . . .
O1 O -0.1150(2) 0.76913(16) 0.11202(15) 0.0739(7) Uani 1 1 d . . .
O2 O 0.0151(3) 0.64558(16) 0.11233(17) 0.0863(8) Uani 1 1 d . . .
O3 O 0.1797(3) 0.59721(17) -0.02788(19) 0.0968(9) Uani 1 1 d . . .
O4 O 0.3404(4) 0.6147(2) 0.0755(2) 0.1148(12) 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
C1 C6 1.375(4) . ?
C1 C2 1.385(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.361(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(5) . ?
C5 H5 0.9300 . ?
C6 N2 1.424(4) . ?
C7 C8 1.393(4) . ?
C7 C12 1.388(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.516(4) . ?
C13 N1 1.463(4) . ?
C13 N2 1.480(3) . ?
C13 H13 0.9800 . ?
C14 C15 1.377(4) . ?
C14 C19 1.393(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(4) . ?
C18 H18 0.9300 . ?
C19 N1 1.429(4) . ?
C20 N1 1.473(4) . ?
C20 C21 1.507(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.358(4) . ?
C21 C25 1.462(4) . ?
C22 N2 1.378(4) . ?
C22 C23 1.517(5) . ?
C23 O4 1.207(5) . ?
C23 O3 1.292(5) . ?
C24 O3 1.577(6) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O2 1.197(4) . ?
C25 O1 1.349(4) . ?
C26 O1 1.449(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
C6 C1 C2 120.2(4) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.8(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 N2 121.2(3) . . ?
C5 C6 N2 119.7(3) . . ?
C8 C7 C12 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
C12 C7 H7 119.8 . . ?
C9 C8 C7 120.0(4) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.0(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 120.3(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 120.9(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C7 118.4(3) . . ?
C11 C12 C13 118.8(3) . . ?
C7 C12 C13 122.8(3) . . ?
N1 C13 N2 110.0(2) . . ?
N1 C13 C12 110.8(2) . . ?
N2 C13 C12 112.4(2) . . ?
N1 C13 H13 107.9 . . ?
N2 C13 H13 107.9 . . ?
C12 C13 H13 107.9 . . ?
C15 C14 C19 121.3(3) . . ?
C15 C14 H14 119.4 . . ?
C19 C14 H14 119.4 . . ?
C16 C15 C14 120.7(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 118.8(3) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C18 121.1(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C14 117.6(3) . . ?
C18 C19 N1 123.0(3) . . ?
C14 C19 N1 119.2(3) . . ?
N1 C20 C21 111.5(2) . . ?
N1 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
N1 C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 C25 119.2(3) . . ?
C22 C21 C20 120.6(3) . . ?
C25 C21 C20 120.1(3) . . ?
C21 C22 N2 122.0(3) . . ?
C21 C22 C23 123.5(3) . . ?
N2 C22 C23 113.8(3) . . ?
O4 C23 O3 125.6(4) . . ?
O4 C23 C22 120.7(4) . . ?
O3 C23 C22 113.7(4) . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O2 C25 O1 121.8(3) . . ?
O2 C25 C21 127.0(3) . . ?
O1 C25 C21 111.2(3) . . ?
O1 C26 H26A 109.5 . . ?
O1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C19 N1 C13 114.4(2) . . ?
C19 N1 C20 116.6(2) . . ?
C13 N1 C20 109.8(2) . . ?
C22 N2 C6 122.9(2) . . ?
C22 N2 C13 116.3(2) . . ?
C6 N2 C13 120.1(2) . . ?
C25 O1 C26 114.9(3) . . ?
C23 O3 C24 102.4(4) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_zhu8curt
_database_code_depnum_ccdc_archive 'CCDC 1011038'
_audit_update_record             
;
2014-06-29 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;
_audit_creation_date             2014-01-27
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H22 Br2 N2 O4'
_chemical_formula_sum            'C26 H22 Br2 N2 O4'
_chemical_formula_weight         586.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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

_space_group_IT_number           2

_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   10.6774(5)
_cell_length_b                   10.7451(7)
_cell_length_c                   12.3472(7)
_cell_angle_alpha                107.453(6)
_cell_angle_beta                 103.856(5)
_cell_angle_gamma                103.585(5)
_cell_volume                     1238.02(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4241
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      71.4020
_cell_measurement_theta_min      9.6020
_exptl_absorpt_coefficient_mu    4.445
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6997
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.00
_diffrn_reflns_theta_min         9.63
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean 15.9578
_diffrn_measured_fraction_theta_full 0.9848
_diffrn_measured_fraction_theta_max 0.5570
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   39.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -38.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
  2 omega -112.00  -19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.0000  125.0000   60.0000 93

#__ type_ start__ end____ width___ exp.time_
  3 omega   34.00  124.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       55.0000   57.0000   90.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega   11.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       55.0000  -38.0000 -180.0000 59

#__ type_ start__ end____ width___ exp.time_
  5 omega  -13.00   74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       55.0000  -57.0000  -60.0000 87

#__ type_ start__ end____ width___ exp.time_
  6 omega   29.00  126.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       55.0000   38.0000 -150.0000 97

#__ type_ start__ end____ width___ exp.time_
  7 omega   37.00   63.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -25.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   78.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   25.0000    0.0000 100

#__ type_ start__ end____ width___ exp.time_
  9 omega   37.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -25.0000  -30.0000 34

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -38.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
 11 omega   42.00   80.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -50.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   65.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -38.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   74.00  128.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -92.0000  150.0000 54

#__ type_ start__ end____ width___ exp.time_
 14 omega   81.00  166.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   25.0000  -90.0000 85

#__ type_ start__ end____ width___ exp.time_
 15 omega   54.00  146.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -92.0000  -60.0000 92

#__ type_ start__ end____ width___ exp.time_
 16 omega   39.00   78.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000 -111.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
 17 omega   41.00   66.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -38.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   43.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -92.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   82.00  148.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -92.0000   30.0000 66

#__ type_ start__ end____ width___ exp.time_
 20 omega   44.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -25.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 21 omega   37.00   62.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -25.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega   45.00   72.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000  -50.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 23 omega   38.00   73.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000 -111.0000 -120.0000 35
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0595732000
_diffrn_orient_matrix_UB_12      0.0956612000
_diffrn_orient_matrix_UB_13      0.0768814000
_diffrn_orient_matrix_UB_21      0.0605610000
_diffrn_orient_matrix_UB_22      0.1159570000
_diffrn_orient_matrix_UB_23      -0.0406008000
_diffrn_orient_matrix_UB_31      -0.1326171000
_diffrn_orient_matrix_UB_32      -0.0526599000
_diffrn_orient_matrix_UB_33      -0.1081603000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35
_diffrn_source_power             1.75
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3750
_reflns_number_total             4276
_reflns_odcompleteness_completeness 98.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007). 40, 609-613'
_refine_diff_density_max         0.995
_refine_diff_density_min         -1.274
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0912P)²+0.8458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1591
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.26495(6) -0.07610(6) 0.09000(6) 0.1030(3) Uani 1 1 d . . .
Br2 Br 0.15352(5) 0.82650(6) 0.41583(8) 0.1134(3) Uani 1 1 d . . .
O1 O 0.6813(3) 0.8525(2) 0.2364(2) 0.0640(6) Uani 1 1 d . . .
O2 O 0.5705(3) 0.6433(2) 0.0890(2) 0.0595(6) Uani 1 1 d . . .
O3 O 0.9214(4) 0.5079(4) 0.1382(3) 0.0922(10) Uani 1 1 d . . .
O4 O 0.8518(3) 0.6844(3) 0.1229(3) 0.0724(7) Uani 1 1 d . . .
N1 N 0.7277(3) 0.4711(3) 0.3888(3) 0.0511(6) Uani 1 1 d . . .
C2 C 0.6981(3) 0.5928(3) 0.4500(3) 0.0483(6) Uani 1 1 d . . .
H2 H 0.6252 0.5631 0.4814 0.058 Uiso 1 1 calc R . .
N3 N 0.6466(3) 0.6558(3) 0.3646(2) 0.0475(6) Uani 1 1 d . . .
C4 C 0.7006(3) 0.6509(3) 0.2739(3) 0.0458(6) Uani 1 1 d . . .
C5 C 0.7939(3) 0.5874(3) 0.2583(3) 0.0497(7) Uani 1 1 d . . .
C6 C 0.8330(3) 0.5080(4) 0.3348(3) 0.0543(7) Uani 1 1 d . . .
H6A H 0.8438 0.4245 0.2858 0.065 Uiso 1 1 calc R . .
H6B H 0.9198 0.5636 0.3982 0.065 Uiso 1 1 calc R . .
C11 C 0.6165(3) 0.3478(3) 0.3168(3) 0.0509(7) Uani 1 1 d . . .
C12 C 0.6448(4) 0.2268(4) 0.2660(4) 0.0627(8) Uani 1 1 d . . .
H12 H 0.7351 0.2305 0.2779 0.075 Uiso 1 1 calc R . .
C13 C 0.5412(5) 0.1023(4) 0.1986(4) 0.0704(10) Uani 1 1 d . . .
H13 H 0.5616 0.0231 0.1646 0.084 Uiso 1 1 calc R . .
C14 C 0.4077(4) 0.0961(4) 0.1820(4) 0.0652(9) Uani 1 1 d . . .
C15 C 0.3760(4) 0.2124(4) 0.2320(3) 0.0603(8) Uani 1 1 d . . .
H15 H 0.2854 0.2068 0.2217 0.072 Uiso 1 1 calc R . .
C16 C 0.4799(3) 0.3377(4) 0.2977(3) 0.0542(7) Uani 1 1 d . . .
H16 H 0.4582 0.4166 0.3298 0.065 Uiso 1 1 calc R . .
C21 C 0.8232(3) 0.6944(4) 0.5574(3) 0.0519(7) Uani 1 1 d . . .
C22 C 0.8738(4) 0.6514(4) 0.6491(3) 0.0623(9) Uani 1 1 d . . .
H22 H 0.8340 0.5612 0.6418 0.075 Uiso 1 1 calc R . .
C23 C 0.9825(4) 0.7409(5) 0.7511(3) 0.0746(11) Uani 1 1 d . . .
H23 H 1.0143 0.7113 0.8126 0.090 Uiso 1 1 calc R . .
C24 C 1.0441(5) 0.8744(6) 0.7619(4) 0.0832(13) Uani 1 1 d . . .
H24 H 1.1172 0.9350 0.8305 0.100 Uiso 1 1 calc R . .
C25 C 0.9967(5) 0.9170(5) 0.6705(5) 0.0813(12) Uani 1 1 d . . .
H25 H 1.0384 1.0064 0.6769 0.098 Uiso 1 1 calc R . .
C26 C 0.8863(4) 0.8268(4) 0.5682(4) 0.0637(8) Uani 1 1 d . . .
H26 H 0.8550 0.8565 0.5066 0.076 Uiso 1 1 calc R . .
C31 C 0.5303(3) 0.6992(3) 0.3713(3) 0.0466(6) Uani 1 1 d . . .
C32 C 0.5398(4) 0.7982(4) 0.4779(3) 0.0544(7) Uani 1 1 d . . .
H32 H 0.6220 0.8386 0.5418 0.065 Uiso 1 1 calc R . .
C33 C 0.4277(4) 0.8373(4) 0.4902(4) 0.0626(8) Uani 1 1 d . . .
H33 H 0.4339 0.9037 0.5617 0.075 Uiso 1 1 calc R . .
C34 C 0.3078(4) 0.7765(4) 0.3950(4) 0.0626(9) Uani 1 1 d . . .
C35 C 0.2964(4) 0.6799(4) 0.2867(4) 0.0659(9) Uani 1 1 d . . .
H35 H 0.2149 0.6422 0.2222 0.079 Uiso 1 1 calc R . .
C36 C 0.4084(4) 0.6407(4) 0.2762(3) 0.0583(8) Uani 1 1 d . . .
H36 H 0.4018 0.5743 0.2046 0.070 Uiso 1 1 calc R . .
C40 C 0.6524(3) 0.7296(3) 0.1984(3) 0.0479(6) Uani 1 1 d . . .
C41 C 0.5161(6) 0.7061(5) 0.0089(4) 0.0861(14) Uani 1 1 d . . .
H41A H 0.4543 0.7482 0.0375 0.129 Uiso 1 1 calc R . .
H41B H 0.4681 0.6366 -0.0705 0.129 Uiso 1 1 calc R . .
H41C H 0.5896 0.7752 0.0063 0.129 Uiso 1 1 calc R . .
C50 C 0.8605(4) 0.5859(4) 0.1677(3) 0.0594(8) Uani 1 1 d . . .
C51 C 0.9081(6) 0.6854(7) 0.0286(5) 0.0978(16) Uani 1 1 d . . .
H51A H 1.0055 0.7082 0.0598 0.147 Uiso 1 1 calc R . .
H51B H 0.8870 0.7529 -0.0021 0.147 Uiso 1 1 calc R . .
H51C H 0.8694 0.5956 -0.0352 0.147 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 C14 1.903(4) . ?
Br2 C34 1.898(3) . ?
O1 C40 1.195(4) . ?
O2 C40 1.323(4) . ?
O2 C41 1.442(5) . ?
O3 C50 1.202(5) . ?
O4 C50 1.344(5) . ?
O4 C51 1.434(5) . ?
N1 C2 1.448(4) . ?
N1 C6 1.474(4) . ?
N1 C11 1.416(5) . ?
C2 N3 1.482(4) . ?
C2 C21 1.527(5) . ?
N3 C4 1.370(4) . ?
N3 C31 1.437(4) . ?
C4 C5 1.352(4) . ?
C4 C40 1.516(4) . ?
C5 C6 1.502(5) . ?
C5 C50 1.461(4) . ?
C11 C12 1.401(5) . ?
C11 C16 1.393(5) . ?
C12 C13 1.379(6) . ?
C13 C14 1.373(6) . ?
C14 C15 1.376(6) . ?
C15 C16 1.383(5) . ?
C21 C22 1.387(5) . ?
C21 C26 1.375(5) . ?
C22 C23 1.381(6) . ?
C23 C24 1.382(7) . ?
C24 C25 1.372(7) . ?
C25 C26 1.392(6) . ?
C31 C32 1.386(5) . ?
C31 C36 1.382(5) . ?
C32 C33 1.384(5) . ?
C33 C34 1.369(6) . ?
C34 C35 1.382(6) . ?
C35 C36 1.379(5) . ?

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
C40 O2 C41 115.9(3) . . ?
C50 O4 C51 117.0(4) . . ?
C2 N1 C6 110.2(2) . . ?
C11 N1 C2 118.1(3) . . ?
C11 N1 C6 116.0(3) . . ?
N1 C2 N3 110.8(2) . . ?
N1 C2 C21 110.4(3) . . ?
N3 C2 C21 112.8(3) . . ?
C4 N3 C2 117.5(2) . . ?
C4 N3 C31 123.8(2) . . ?
C31 N3 C2 118.0(2) . . ?
N3 C4 C40 113.9(3) . . ?
C5 C4 N3 122.3(3) . . ?
C5 C4 C40 123.6(3) . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 C50 124.6(3) . . ?
C50 C5 C6 115.2(3) . . ?
N1 C6 C5 110.7(3) . . ?
C12 C11 N1 118.4(3) . . ?
C16 C11 N1 124.0(3) . . ?
C16 C11 C12 117.6(3) . . ?
C13 C12 C11 121.3(3) . . ?
C14 C13 C12 119.5(4) . . ?
C13 C14 Br1 119.5(3) . . ?
C13 C14 C15 120.9(4) . . ?
C15 C14 Br1 119.7(3) . . ?
C14 C15 C16 119.5(3) . . ?
C15 C16 C11 121.2(3) . . ?
C22 C21 C2 118.3(3) . . ?
C26 C21 C2 123.1(3) . . ?
C26 C21 C22 118.6(3) . . ?
C23 C22 C21 120.9(4) . . ?
C22 C23 C24 120.0(4) . . ?
C25 C24 C23 119.5(4) . . ?
C24 C25 C26 120.3(5) . . ?
C21 C26 C25 120.6(4) . . ?
C32 C31 N3 118.7(3) . . ?
C36 C31 N3 121.7(3) . . ?
C36 C31 C32 119.5(3) . . ?
C33 C32 C31 120.5(3) . . ?
C34 C33 C32 118.7(3) . . ?
C33 C34 Br2 118.0(3) . . ?
C33 C34 C35 122.0(3) . . ?
C35 C34 Br2 120.0(3) . . ?
C36 C35 C34 118.7(4) . . ?
C35 C36 C31 120.6(3) . . ?
O1 C40 O2 125.8(3) . . ?
O1 C40 C4 123.4(3) . . ?
O2 C40 C4 110.7(3) . . ?
O3 C50 O4 122.6(3) . . ?
O3 C50 C5 123.9(3) . . ?
O4 C50 C5 113.4(3) . . ?

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
Br1 C14 C15 C16 -179.3(3) . . . . ?
Br2 C34 C35 C36 -176.9(3) . . . . ?
N1 C2 N3 C4 -35.4(4) . . . . ?
N1 C2 N3 C31 135.6(3) . . . . ?
N1 C2 C21 C22 -61.1(4) . . . . ?
N1 C2 C21 C26 120.0(3) . . . . ?
N1 C11 C12 C13 177.6(3) . . . . ?
N1 C11 C16 C15 -176.2(3) . . . . ?
C2 N1 C6 C5 -52.1(4) . . . . ?
C2 N1 C11 C12 -174.4(3) . . . . ?
C2 N1 C11 C16 2.4(4) . . . . ?
C2 N3 C4 C5 2.3(5) . . . . ?
C2 N3 C4 C40 -174.4(3) . . . . ?
C2 N3 C31 C32 59.9(4) . . . . ?
C2 N3 C31 C36 -117.3(3) . . . . ?
C2 C21 C22 C23 -176.9(3) . . . . ?
C2 C21 C26 C25 177.4(4) . . . . ?
N3 C2 C21 C22 174.4(3) . . . . ?
N3 C2 C21 C26 -4.5(4) . . . . ?
N3 C4 C5 C6 5.4(5) . . . . ?
N3 C4 C5 C50 -176.3(3) . . . . ?
N3 C4 C40 O1 67.0(4) . . . . ?
N3 C4 C40 O2 -110.1(3) . . . . ?
N3 C31 C32 C33 -176.5(3) . . . . ?
N3 C31 C36 C35 177.2(3) . . . . ?
C4 N3 C31 C32 -129.7(3) . . . . ?
C4 N3 C31 C36 53.1(4) . . . . ?
C4 C5 C6 N1 19.8(4) . . . . ?
C4 C5 C50 O3 -164.5(4) . . . . ?
C4 C5 C50 O4 17.9(5) . . . . ?
C5 C4 C40 O1 -109.6(4) . . . . ?
C5 C4 C40 O2 73.3(4) . . . . ?
C6 N1 C2 N3 60.3(3) . . . . ?
C6 N1 C2 C21 -65.4(3) . . . . ?
C6 N1 C11 C12 51.3(4) . . . . ?
C6 N1 C11 C16 -131.9(3) . . . . ?
C6 C5 C50 O3 13.9(6) . . . . ?
C6 C5 C50 O4 -163.8(3) . . . . ?
C11 N1 C2 N3 -76.4(3) . . . . ?
C11 N1 C2 C21 158.0(3) . . . . ?
C11 N1 C6 C5 85.5(3) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C12 C11 C16 C15 0.6(5) . . . . ?
C12 C13 C14 Br1 -179.5(3) . . . . ?
C12 C13 C14 C15 -0.1(6) . . . . ?
C13 C14 C15 C16 1.3(6) . . . . ?
C14 C15 C16 C11 -1.5(5) . . . . ?
C16 C11 C12 C13 0.6(5) . . . . ?
C21 C2 N3 C4 88.9(3) . . . . ?
C21 C2 N3 C31 -100.1(3) . . . . ?
C21 C22 C23 C24 -1.3(6) . . . . ?
C22 C21 C26 C25 -1.6(6) . . . . ?
C22 C23 C24 C25 -0.2(7) . . . . ?
C23 C24 C25 C26 0.7(7) . . . . ?
C24 C25 C26 C21 0.2(7) . . . . ?
C26 C21 C22 C23 2.1(5) . . . . ?
C31 N3 C4 C5 -168.1(3) . . . . ?
C31 N3 C4 C40 15.2(4) . . . . ?
C31 C32 C33 C34 0.0(5) . . . . ?
C32 C31 C36 C35 0.0(5) . . . . ?
C32 C33 C34 Br2 177.6(3) . . . . ?
C32 C33 C34 C35 -1.5(6) . . . . ?
C33 C34 C35 C36 2.3(6) . . . . ?
C34 C35 C36 C31 -1.5(6) . . . . ?
C36 C31 C32 C33 0.8(5) . . . . ?
C40 C4 C5 C6 -178.2(3) . . . . ?
C40 C4 C5 C50 0.1(5) . . . . ?
C41 O2 C40 O1 2.1(5) . . . . ?
C41 O2 C40 C4 179.1(3) . . . . ?
C50 C5 C6 N1 -158.6(3) . . . . ?
C51 O4 C50 O3 5.6(6) . . . . ?
C51 O4 C50 C5 -176.7(4) . . . . ?

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1011039'
_audit_update_record             
;
2014-06-29 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 Br2 N2 O4'
_chemical_formula_weight         586.28

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   12.571(3)
_cell_length_b                   13.241(3)
_cell_length_c                   15.845(3)
_cell_angle_alpha                87.14(3)
_cell_angle_beta                 76.74(3)
_cell_angle_gamma                74.96(3)
_cell_volume                     2479.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    3.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4372
_exptl_absorpt_correction_T_max  0.5043
_exptl_absorpt_process_details   'Higashi, T. (1995)'

_exptl_special_details           
; 
Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan.
;

_diffrn_ambient_temperature      298(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_reflns_number            11988
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_sigmaI/netI    0.1777
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         25.00
_reflns_number_total             8381
_reflns_number_gt                4046
_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)+(0.0000P)²+54.5871P] 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       0.0217(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8381
_refine_ls_number_parameters     596
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1918
_refine_ls_R_factor_gt           0.1112
_refine_ls_wR_factor_ref         0.2485
_refine_ls_wR_factor_gt          0.2164
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.014
_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 0.17113(10) 0.32837(9) 0.28536(8) 0.0587(4) Uani 1 1 d . . .
Br2 Br 0.03661(11) 0.83879(11) -0.16489(8) 0.0776(4) Uani 1 1 d . . .
Br3 Br 0.45762(9) 1.14591(9) 0.21128(7) 0.0546(3) Uani 1 1 d . . .
Br4 Br 0.34968(11) 0.68529(12) 0.64927(8) 0.0774(5) Uani 1 1 d . . .
O1 O 0.6323(5) 0.8520(5) -0.0094(4) 0.046(2) Uani 1 1 d . . .
O2 O 0.6984(6) 0.6977(6) 0.0469(5) 0.062(2) Uani 1 1 d . . .
O3 O 0.5932(5) 0.5310(5) 0.0752(4) 0.046(2) Uani 1 1 d . . .
O4 O 0.5840(6) 0.5840(6) 0.2092(4) 0.059(2) Uani 1 1 d . . .
O5 O 0.8731(5) 0.9512(5) 0.4213(4) 0.0415(19) Uani 1 1 d . . .
O6 O 0.9682(6) 0.9137(5) 0.2829(4) 0.058(2) Uani 1 1 d . . .
O7 O 1.0456(5) 0.6424(5) 0.5030(4) 0.0438(19) Uani 1 1 d . . .
O8 O 1.0655(5) 0.7915(5) 0.4367(4) 0.049(2) Uani 1 1 d . . .
N1 N 0.3614(6) 0.7036(5) 0.1738(5) 0.0340(11) Uani 1 1 d . . .
N2 N 0.2967(6) 0.8701(5) 0.1085(5) 0.0340(11) Uani 1 1 d . . .
N3 N 0.7970(6) 0.6121(5) 0.3793(5) 0.0340(11) Uani 1 1 d . . .
N4 N 0.8055(6) 0.7771(5) 0.3142(5) 0.0340(11) Uani 1 1 d . . .
C1 C 0.4701(7) 0.6973(7) 0.1254(6) 0.031(2) Uani 1 1 d . . .
C2 C 0.4990(7) 0.7770(7) 0.0818(6) 0.035(3) Uani 1 1 d . . .
C3 C 0.4124(8) 0.8818(7) 0.0806(7) 0.041(3) Uani 1 1 d . . .
H3A H 0.4239 0.9309 0.1190 0.049 Uiso 1 1 calc R . .
H3B H 0.4233 0.9099 0.0225 0.049 Uiso 1 1 calc R . .
C4 C 0.2831(8) 0.8106(7) 0.1882(6) 0.039(3) Uani 1 1 d . . .
H4A H 0.2054 0.8032 0.2032 0.047 Uiso 1 1 calc R . .
C5 C 0.6185(8) 0.7700(8) 0.0384(6) 0.039(3) Uani 1 1 d . . .
C6 C 0.7472(8) 0.8503(9) -0.0551(7) 0.059(4) Uani 1 1 d . . .
H6A H 0.7471 0.9134 -0.0875 0.089 Uiso 1 1 calc R . .
H6B H 0.7766 0.7911 -0.0939 0.089 Uiso 1 1 calc R . .
H6C H 0.7937 0.8451 -0.0139 0.089 Uiso 1 1 calc R . .
C7 C 0.5576(8) 0.5982(7) 0.1421(6) 0.037(3) Uani 1 1 d . . .
C8 C 0.6788(11) 0.4389(9) 0.0881(8) 0.078(5) Uani 1 1 d . . .
H8A H 0.7005 0.3941 0.0379 0.117 Uiso 1 1 calc R . .
H8B H 0.6492 0.4021 0.1380 0.117 Uiso 1 1 calc R . .
H8C H 0.7435 0.4590 0.0969 0.117 Uiso 1 1 calc R . .
C9 C 0.3014(8) 0.8666(7) 0.2627(6) 0.038(3) Uani 1 1 d . . .
C10 C 0.2288(9) 0.9673(8) 0.2838(7) 0.055(3) Uani 1 1 d . . .
H10A H 0.1748 0.9963 0.2519 0.066 Uiso 1 1 calc R . .
C11 C 0.2387(11) 1.0225(9) 0.3523(8) 0.072(4) Uani 1 1 d . . .
H11A H 0.1901 1.0883 0.3673 0.086 Uiso 1 1 calc R . .
C12 C 0.3196(11) 0.9810(10) 0.3983(8) 0.076(4) Uani 1 1 d . . .
H12A H 0.3280 1.0199 0.4425 0.091 Uiso 1 1 calc R . .
C13 C 0.3888(10) 0.8811(10) 0.3791(7) 0.068(4) Uani 1 1 d . . .
H13A H 0.4415 0.8519 0.4119 0.082 Uiso 1 1 calc R . .
C14 C 0.3793(8) 0.8249(9) 0.3111(6) 0.050(3) Uani 1 1 d . . .
H14A H 0.4264 0.7582 0.2982 0.060 Uiso 1 1 calc R . .
C15 C 0.3215(8) 0.6134(7) 0.1992(6) 0.037(3) Uani 1 1 d . . .
C16 C 0.2552(8) 0.6100(8) 0.2819(6) 0.045(3) Uani 1 1 d . . .
H16A H 0.2398 0.6656 0.3201 0.053 Uiso 1 1 calc R . .
C17 C 0.2116(8) 0.5241(7) 0.3081(6) 0.044(3) Uani 1 1 d . . .
H17A H 0.1671 0.5214 0.3634 0.052 Uiso 1 1 calc R . .
C18 C 0.2361(7) 0.4446(7) 0.2504(7) 0.040(3) Uani 1 1 d . . .
C19 C 0.3025(8) 0.4450(8) 0.1684(6) 0.048(3) Uani 1 1 d . . .
H19A H 0.3188 0.3885 0.1309 0.058 Uiso 1 1 calc R . .
C20 C 0.3444(8) 0.5309(8) 0.1429(6) 0.041(3) Uani 1 1 d . . .
H20A H 0.3885 0.5330 0.0873 0.049 Uiso 1 1 calc R . .
C21 C 0.2400(8) 0.8567(7) 0.0440(6) 0.033(3) Uani 1 1 d . . .
C22 C 0.2941(9) 0.8331(8) -0.0408(6) 0.049(3) Uani 1 1 d . . .
H22A H 0.3724 0.8191 -0.0574 0.059 Uiso 1 1 calc R . .
C23 C 0.2317(9) 0.8302(8) -0.1015(7) 0.052(3) Uani 1 1 d . . .
H23A H 0.2684 0.8182 -0.1595 0.062 Uiso 1 1 calc R . .
C24 C 0.1181(8) 0.8446(7) -0.0782(6) 0.044(3) Uani 1 1 d . . .
C25 C 0.0629(8) 0.8649(8) 0.0068(6) 0.049(3) Uani 1 1 d . . .
H25A H -0.0152 0.8751 0.0226 0.059 Uiso 1 1 calc R . .
C26 C 0.1213(8) 0.8704(8) 0.0681(7) 0.049(3) Uani 1 1 d . . .
H26A H 0.0834 0.8831 0.1258 0.059 Uiso 1 1 calc R . .
C27 C 0.8803(7) 0.7892(7) 0.3615(6) 0.029(2) Uani 1 1 d . . .
C28 C 0.9301(7) 0.7080(7) 0.4067(6) 0.034(3) Uani 1 1 d . . .
C29 C 0.9002(7) 0.6044(6) 0.4107(6) 0.030(2) Uani 1 1 d . . .
H29A H 0.9624 0.5533 0.3757 0.036 Uiso 1 1 calc R . .
H29B H 0.8893 0.5803 0.4701 0.036 Uiso 1 1 calc R . .
C30 C 0.7967(8) 0.6711(7) 0.2999(6) 0.035(3) Uani 1 1 d . . .
H30A H 0.7244 0.6769 0.2841 0.042 Uiso 1 1 calc R . .
C31 C 0.9144(7) 0.8916(7) 0.3495(6) 0.031(2) Uani 1 1 d . . .
C32 C 0.9054(10) 1.0495(8) 0.4160(8) 0.066(4) Uani 1 1 d . . .
H32A H 0.8727 1.0872 0.4699 0.100 Uiso 1 1 calc R . .
H32B H 0.8786 1.0906 0.3699 0.100 Uiso 1 1 calc R . .
H32C H 0.9862 1.0357 0.4047 0.100 Uiso 1 1 calc R . .
C33 C 1.0204(7) 0.7215(6) 0.4487(5) 0.027(2) Uani 1 1 d . . .
C34 C 1.1321(9) 0.6495(9) 0.5488(7) 0.070(3) Uani 1 1 d . . .
H34A H 1.1453 0.5904 0.5861 0.105 Uiso 1 1 calc R . .
H34B H 1.1068 0.7128 0.5829 0.105 Uiso 1 1 calc R . .
H34C H 1.2010 0.6501 0.5075 0.105 Uiso 1 1 calc R . .
C35 C 0.8923(7) 0.6149(7) 0.2251(6) 0.033(3) Uani 1 1 d . . .
C36 C 0.8956(9) 0.5117(8) 0.2067(7) 0.049(3) Uani 1 1 d . . .
H36A H 0.8425 0.4800 0.2403 0.059 Uiso 1 1 calc R . .
C37 C 0.9769(10) 0.4563(9) 0.1391(7) 0.063(4) Uani 1 1 d . . .
H37A H 0.9783 0.3878 0.1272 0.075 Uiso 1 1 calc R . .
C38 C 1.0553(10) 0.5030(9) 0.0899(7) 0.063(4) Uani 1 1 d . . .
H38A H 1.1103 0.4664 0.0444 0.075 Uiso 1 1 calc R . .
C39 C 1.0520(9) 0.6041(9) 0.1081(7) 0.061(4) Uani 1 1 d . . .
H39A H 1.1058 0.6351 0.0746 0.073 Uiso 1 1 calc R . .
C40 C 0.9711(8) 0.6612(8) 0.1747(6) 0.047(3) Uani 1 1 d . . .
H40A H 0.9698 0.7300 0.1854 0.057 Uiso 1 1 calc R . .
C41 C 0.7254(7) 0.8656(7) 0.2895(5) 0.029(2) Uani 1 1 d . . .
C42 C 0.6665(8) 0.9449(7) 0.3481(6) 0.038(3) Uani 1 1 d . . .
H42A H 0.6788 0.9411 0.4040 0.045 Uiso 1 1 calc R . .
C43 C 0.5891(8) 1.0306(8) 0.3247(6) 0.044(3) Uani 1 1 d . . .
H43A H 0.5510 1.0852 0.3638 0.053 Uiso 1 1 calc R . .
C44 C 0.5700(7) 1.0331(7) 0.2425(6) 0.036(3) Uani 1 1 d . . .
C45 C 0.6269(8) 0.9540(7) 0.1821(6) 0.039(3) Uani 1 1 d . . .
H45A H 0.6130 0.9565 0.1267 0.047 Uiso 1 1 calc R . .
C46 C 0.7052(8) 0.8713(7) 0.2075(6) 0.039(3) Uani 1 1 d . . .
H46A H 0.7455 0.8177 0.1680 0.047 Uiso 1 1 calc R . .
C47 C 0.6920(7) 0.6364(7) 0.4423(6) 0.033(2) Uani 1 1 d . . .
C48 C 0.6823(8) 0.6679(8) 0.5261(6) 0.044(3) Uani 1 1 d . . .
H48A H 0.7443 0.6804 0.5424 0.052 Uiso 1 1 calc R . .
C49 C 0.5782(9) 0.6812(9) 0.5869(7) 0.059(4) Uani 1 1 d . . .
H49A H 0.5723 0.7018 0.6434 0.070 Uiso 1 1 calc R . .
C50 C 0.4883(8) 0.6646(8) 0.5643(7) 0.046(3) Uani 1 1 d . . .
C51 C 0.4970(8) 0.6318(8) 0.4821(7) 0.046(3) Uani 1 1 d . . .
H51A H 0.4349 0.6182 0.4669 0.055 Uiso 1 1 calc R . .
C52 C 0.5992(8) 0.6188(8) 0.4209(6) 0.042(3) Uani 1 1 d . . .
H52A H 0.6040 0.5978 0.3647 0.050 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 1.924(10) . ?
Br2 C24 1.907(11) . ?
Br3 C44 1.903(9) . ?
Br4 C50 1.907(9) . ?
O1 C5 1.318(11) . ?
O1 C6 1.455(11) . ?
O2 C5 1.222(11) . ?
O3 C7 1.336(11) . ?
O3 C8 1.443(12) . ?
O4 C7 1.176(11) . ?
O5 C31 1.338(10) . ?
O5 C32 1.454(12) . ?
O6 C31 1.184(11) . ?
O7 C33 1.343(10) . ?
O7 C34 1.464(12) . ?
O8 C33 1.192(10) . ?
N1 C1 1.390(11) . ?
N1 C15 1.417(12) . ?
N1 C4 1.495(11) . ?
N2 C21 1.414(12) . ?
N2 C4 1.455(12) . ?
N2 C3 1.467(12) . ?
N3 C47 1.432(11) . ?
N3 C30 1.448(11) . ?
N3 C29 1.470(11) . ?
N4 C27 1.372(12) . ?
N4 C41 1.436(10) . ?
N4 C30 1.469(11) . ?
C1 C2 1.317(13) . ?
C1 C7 1.534(12) . ?
C2 C5 1.482(12) . ?
C2 C3 1.527(12) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.516(14) . ?
C4 H4A 0.9800 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.370(14) . ?
C9 C10 1.413(13) . ?
C10 C11 1.385(16) . ?
C10 H10A 0.9300 . ?
C11 C12 1.370(18) . ?
C11 H11A 0.9300 . ?
C12 C13 1.385(16) . ?
C12 H12A 0.9300 . ?
C13 C14 1.383(15) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C20 1.373(13) . ?
C15 C16 1.388(13) . ?
C16 C17 1.392(14) . ?
C16 H16A 0.9300 . ?
C17 C18 1.356(13) . ?
C17 H17A 0.9300 . ?
C18 C19 1.374(13) . ?
C19 C20 1.380(14) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 C22 1.370(12) . ?
C21 C26 1.419(13) . ?
C22 C23 1.380(15) . ?
C22 H22A 0.9300 . ?
C23 C24 1.355(14) . ?
C23 H23A 0.9300 . ?
C24 C25 1.370(13) . ?
C25 C26 1.361(15) . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9300 . ?
C27 C28 1.357(12) . ?
C27 C31 1.516(13) . ?
C28 C33 1.492(13) . ?
C28 C29 1.508(13) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C35 1.540(12) . ?
C30 H30A 0.9800 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C40 1.378(13) . ?
C35 C36 1.400(13) . ?
C36 C37 1.384(14) . ?
C36 H36A 0.9300 . ?
C37 C38 1.371(16) . ?
C37 H37A 0.9300 . ?
C38 C39 1.371(16) . ?
C38 H38A 0.9300 . ?
C39 C40 1.382(14) . ?
C39 H39A 0.9300 . ?
C40 H40A 0.9300 . ?
C41 C46 1.374(13) . ?
C41 C42 1.377(12) . ?
C42 C43 1.386(12) . ?
C42 H42A 0.9300 . ?
C43 C44 1.375(13) . ?
C43 H43A 0.9300 . ?
C44 C45 1.387(12) . ?
C45 C46 1.382(12) . ?
C45 H45A 0.9300 . ?
C46 H46A 0.9300 . ?
C47 C52 1.364(14) . ?
C47 C48 1.380(13) . ?
C48 C49 1.411(14) . ?
C48 H48A 0.9300 . ?
C49 C50 1.333(15) . ?
C49 H49A 0.9300 . ?
C50 C51 1.364(14) . ?
C51 C52 1.397(13) . ?
C51 H51A 0.9300 . ?
C52 H52A 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
C5 O1 C6 116.7(7) . . ?
C7 O3 C8 113.7(8) . . ?
C31 O5 C32 114.8(7) . . ?
C33 O7 C34 114.5(8) . . ?
C1 N1 C15 122.2(7) . . ?
C1 N1 C4 116.4(7) . . ?
C15 N1 C4 120.9(7) . . ?
C21 N2 C4 119.5(8) . . ?
C21 N2 C3 118.2(7) . . ?
C4 N2 C3 111.0(7) . . ?
C47 N3 C30 114.8(7) . . ?
C47 N3 C29 117.1(7) . . ?
C30 N3 C29 112.0(7) . . ?
C27 N4 C41 121.3(7) . . ?
C27 N4 C30 118.7(7) . . ?
C41 N4 C30 119.3(8) . . ?
C2 C1 N1 122.7(8) . . ?
C2 C1 C7 122.5(8) . . ?
N1 C1 C7 113.7(7) . . ?
C1 C2 C5 120.7(8) . . ?
C1 C2 C3 121.0(8) . . ?
C5 C2 C3 118.1(8) . . ?
N2 C3 C2 111.2(7) . . ?
N2 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N2 C4 N1 109.8(7) . . ?
N2 C4 C9 111.5(8) . . ?
N1 C4 C9 111.4(8) . . ?
N2 C4 H4A 108.0 . . ?
N1 C4 H4A 108.0 . . ?
C9 C4 H4A 108.0 . . ?
O2 C5 O1 121.9(9) . . ?
O2 C5 C2 124.6(9) . . ?
O1 C5 C2 113.4(8) . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 C7 O3 125.7(9) . . ?
O4 C7 C1 121.5(8) . . ?
O3 C7 C1 112.6(8) . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 119.3(10) . . ?
C14 C9 C4 124.7(8) . . ?
C10 C9 C4 116.0(9) . . ?
C11 C10 C9 119.4(11) . . ?
C11 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
C12 C11 C10 120.5(11) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
C11 C12 C13 120.1(12) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C12 C13 C14 120.0(11) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C9 C14 C13 120.7(10) . . ?
C9 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C20 C15 C16 119.5(9) . . ?
C20 C15 N1 121.4(8) . . ?
C16 C15 N1 119.1(8) . . ?
C15 C16 C17 120.7(9) . . ?
C15 C16 H16A 119.6 . . ?
C17 C16 H16A 119.7 . . ?
C18 C17 C16 117.8(9) . . ?
C18 C17 H17A 121.1 . . ?
C16 C17 H17A 121.1 . . ?
C17 C18 C19 122.9(10) . . ?
C17 C18 Br1 117.7(7) . . ?
C19 C18 Br1 119.3(8) . . ?
C18 C19 C20 118.7(9) . . ?
C18 C19 H19A 120.7 . . ?
C20 C19 H19A 120.7 . . ?
C15 C20 C19 120.4(9) . . ?
C15 C20 H20A 119.8 . . ?
C19 C20 H20A 119.8 . . ?
C22 C21 N2 123.2(9) . . ?
C22 C21 C26 118.6(10) . . ?
N2 C21 C26 118.3(8) . . ?
C21 C22 C23 119.7(10) . . ?
C21 C22 H22A 120.1 . . ?
C23 C22 H22A 120.1 . . ?
C24 C23 C22 121.3(10) . . ?
C24 C23 H23A 119.3 . . ?
C22 C23 H23A 119.3 . . ?
C23 C24 C25 119.8(10) . . ?
C23 C24 Br2 119.4(8) . . ?
C25 C24 Br2 120.8(8) . . ?
C26 C25 C24 120.5(10) . . ?
C26 C25 H25A 119.7 . . ?
C24 C25 H25A 119.7 . . ?
C25 C26 C21 119.9(9) . . ?
C25 C26 H26A 120.0 . . ?
C21 C26 H26A 120.0 . . ?
C28 C27 N4 120.5(8) . . ?
C28 C27 C31 123.1(8) . . ?
N4 C27 C31 115.9(7) . . ?
C27 C28 C33 118.3(9) . . ?
C27 C28 C29 121.3(8) . . ?
C33 C28 C29 120.3(8) . . ?
N3 C29 C28 111.9(7) . . ?
N3 C29 H29A 109.2 . . ?
C28 C29 H29A 109.2 . . ?
N3 C29 H29B 109.2 . . ?
C28 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
N3 C30 N4 109.7(7) . . ?
N3 C30 C35 111.1(7) . . ?
N4 C30 C35 111.3(7) . . ?
N3 C30 H30A 108.2 . . ?
N4 C30 H30A 108.2 . . ?
C35 C30 H30A 108.2 . . ?
O6 C31 O5 126.6(9) . . ?
O6 C31 C27 122.0(8) . . ?
O5 C31 C27 111.4(7) . . ?
O5 C32 H32A 109.5 . . ?
O5 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O5 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O8 C33 O7 123.5(9) . . ?
O8 C33 C28 126.1(8) . . ?
O7 C33 C28 110.3(8) . . ?
O7 C34 H34A 109.5 . . ?
O7 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O7 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C40 C35 C36 119.0(8) . . ?
C40 C35 C30 124.0(8) . . ?
C36 C35 C30 117.0(8) . . ?
C37 C36 C35 120.8(10) . . ?
C37 C36 H36A 119.6 . . ?
C35 C36 H36A 119.6 . . ?
C38 C37 C36 119.5(11) . . ?
C38 C37 H37A 120.2 . . ?
C36 C37 H37A 120.2 . . ?
C37 C38 C39 119.6(10) . . ?
C37 C38 H38A 120.2 . . ?
C39 C38 H38A 120.2 . . ?
C38 C39 C40 121.9(11) . . ?
C38 C39 H39A 119.1 . . ?
C40 C39 H39A 119.1 . . ?
C35 C40 C39 119.2(10) . . ?
C35 C40 H40A 120.4 . . ?
C39 C40 H40A 120.4 . . ?
C46 C41 C42 119.2(8) . . ?
C46 C41 N4 120.5(7) . . ?
C42 C41 N4 120.3(8) . . ?
C41 C42 C43 120.6(9) . . ?
C41 C42 H42A 119.7 . . ?
C43 C42 H42A 119.7 . . ?
C44 C43 C42 118.7(8) . . ?
C44 C43 H43A 120.7 . . ?
C42 C43 H43A 120.7 . . ?
C43 C44 C45 122.2(8) . . ?
C43 C44 Br3 119.3(7) . . ?
C45 C44 Br3 118.4(7) . . ?
C46 C45 C44 117.2(9) . . ?
C46 C45 H45A 121.4 . . ?
C44 C45 H45A 121.4 . . ?
C41 C46 C45 122.1(8) . . ?
C41 C46 H46A 118.9 . . ?
C45 C46 H46A 118.9 . . ?
C52 C47 C48 118.3(8) . . ?
C52 C47 N3 118.4(8) . . ?
C48 C47 N3 123.0(8) . . ?
C47 C48 C49 119.9(9) . . ?
C47 C48 H48A 120.1 . . ?
C49 C48 H48A 120.1 . . ?
C50 C49 C48 120.8(10) . . ?
C50 C49 H49A 119.6 . . ?
C48 C49 H49A 119.6 . . ?
C49 C50 C51 120.0(9) . . ?
C49 C50 Br4 118.7(8) . . ?
C51 C50 Br4 121.3(7) . . ?
C50 C51 C52 120.1(9) . . ?
C50 C51 H51A 120.0 . . ?
C52 C51 H51A 120.0 . . ?
C47 C52 C51 120.9(9) . . ?
C47 C52 H52A 119.5 . . ?
C51 C52 H52A 119.5 . . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.111
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1011040'
_audit_update_record             
;
2014-06-29 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 Br2 N2 O4'
_chemical_formula_weight         586.28

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   'Pbca '

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'
'-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                   11.755(3)
_cell_length_b                   20.780(5)
_cell_length_c                   21.031(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5137(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1553
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      17.60

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2352
_exptl_absorpt_coefficient_mu    3.189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4284
_exptl_absorpt_correction_T_max  0.5027
_exptl_absorpt_process_details   'Higashi, T. (1995)'

_exptl_special_details           
; 
Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan.
;

_diffrn_ambient_temperature      298(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_reflns_number            24299
_diffrn_reflns_av_R_equivalents  0.1231
_diffrn_reflns_av_sigmaI/netI    0.1043
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         24.80
_reflns_number_total             4426
_reflns_number_gt                1904
_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)+(0.0479P)²+2.5345P] 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         4426
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1609
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1446
_refine_ls_wR_factor_gt          0.1063
_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 -0.42613(7) 0.11734(4) 0.26808(4) 0.0928(3) Uani 1 1 d . . .
Br2 Br -0.14587(8) 0.45547(4) 0.34843(5) 0.1164(4) Uani 1 1 d . . .
N1 N -0.0557(4) 0.1024(2) 0.4703(2) 0.0445(12) Uani 1 1 d . . .
C7 C -0.0305(5) 0.1659(2) 0.4984(3) 0.0431(15) Uani 1 1 d . . .
H7 H -0.1030 0.1884 0.5043 0.052 Uiso 1 1 calc R . .
O3 O 0.3402(4) 0.1045(2) 0.4028(2) 0.0806(15) Uani 1 1 d . . .
N2 N 0.0386(4) 0.2042(2) 0.4541(2) 0.0431(12) Uani 1 1 d . . .
O1 O 0.2618(4) 0.2605(2) 0.4297(2) 0.0673(13) Uani 1 1 d . . .
C2 C -0.3326(6) 0.1265(3) 0.3920(4) 0.0627(19) Uani 1 1 d . . .
H2 H -0.4061 0.1382 0.4035 0.075 Uiso 1 1 calc R . .
C8 C 0.0245(5) 0.1587(3) 0.5632(3) 0.0489(16) Uani 1 1 d . . .
C23 C 0.2186(5) 0.2188(3) 0.3986(3) 0.0518(17) Uani 1 1 d . . .
C14 C -0.0055(5) 0.2627(3) 0.4291(3) 0.0459(15) Uani 1 1 d . . .
C4 C -0.1396(6) 0.1054(3) 0.4215(3) 0.0467(15) Uani 1 1 d . . .
C3 C -0.2490(6) 0.1231(3) 0.4374(3) 0.0586(17) Uani 1 1 d . . .
H3 H -0.2664 0.1328 0.4795 0.070 Uiso 1 1 calc R . .
C20 C 0.1292(5) 0.1729(3) 0.4255(2) 0.0427(15) Uani 1 1 d . . .
C15 C -0.0482(5) 0.3089(3) 0.4693(3) 0.0590(18) Uani 1 1 d . . .
H15 H -0.0488 0.3017 0.5129 0.071 Uiso 1 1 calc R . .
C13 C -0.0182(6) 0.1133(3) 0.6055(3) 0.0580(17) Uani 1 1 d . . .
H13 H -0.0761 0.0856 0.5928 0.070 Uiso 1 1 calc R . .
C22 C 0.0504(5) 0.0669(3) 0.4574(3) 0.0517(16) Uani 1 1 d . . .
H22A H 0.0342 0.0316 0.4286 0.062 Uiso 1 1 calc R . .
H22B H 0.0787 0.0488 0.4968 0.062 Uiso 1 1 calc R . .
C18 C -0.0479(6) 0.3314(3) 0.3400(3) 0.069(2) Uani 1 1 d . . .
H18 H -0.0477 0.3389 0.2964 0.083 Uiso 1 1 calc R . .
O4 O 0.2329(4) 0.0157(2) 0.3976(3) 0.1013(18) Uani 1 1 d . . .
C1 C -0.3088(6) 0.1128(3) 0.3304(3) 0.0573(17) Uani 1 1 d . . .
C21 C 0.1416(5) 0.1090(3) 0.4284(3) 0.0467(15) Uani 1 1 d . . .
C19 C -0.0075(5) 0.2737(3) 0.3644(3) 0.0568(17) Uani 1 1 d . . .
H19 H 0.0186 0.2421 0.3368 0.068 Uiso 1 1 calc R . .
C24 C 0.3293(6) 0.2464(3) 0.3097(3) 0.078(2) Uani 1 1 d . . .
H24A H 0.3144 0.2911 0.3176 0.117 Uiso 1 1 calc R . .
H24B H 0.3328 0.2390 0.2647 0.117 Uiso 1 1 calc R . .
H24C H 0.4006 0.2347 0.3288 0.117 Uiso 1 1 calc R . .
C10 C 0.1518(6) 0.1974(4) 0.6447(4) 0.076(2) Uani 1 1 d . . .
H10 H 0.2077 0.2260 0.6581 0.092 Uiso 1 1 calc R . .
C25 C 0.2485(7) 0.0790(4) 0.4086(3) 0.0628(19) Uani 1 1 d . . .
C5 C -0.1162(6) 0.0906(3) 0.3584(3) 0.0615(18) Uani 1 1 d . . .
H5 H -0.0430 0.0784 0.3466 0.074 Uiso 1 1 calc R . .
C9 C 0.1096(5) 0.2007(3) 0.5835(3) 0.0590(18) Uani 1 1 d . . .
H9 H 0.1383 0.2313 0.5555 0.071 Uiso 1 1 calc R . .
C11 C 0.1105(7) 0.1516(4) 0.6854(4) 0.084(2) Uani 1 1 d . . .
H11 H 0.1399 0.1489 0.7264 0.101 Uiso 1 1 calc R . .
C12 C 0.0259(7) 0.1092(3) 0.6669(3) 0.075(2) Uani 1 1 d . . .
H12 H -0.0013 0.0783 0.6951 0.090 Uiso 1 1 calc R . .
C16 C -0.0904(6) 0.3660(3) 0.4451(4) 0.072(2) Uani 1 1 d . . .
H16 H -0.1204 0.3969 0.4723 0.087 Uiso 1 1 calc R . .
C17 C -0.0881(6) 0.3770(3) 0.3814(4) 0.069(2) Uani 1 1 d . . .
C6 C -0.2020(7) 0.0942(3) 0.3127(3) 0.068(2) Uani 1 1 d . . .
H6 H -0.1866 0.0839 0.2705 0.081 Uiso 1 1 calc R . .
C26 C 0.3368(7) -0.0196(4) 0.3807(6) 0.165(5) Uani 1 1 d . . .
H26A H 0.3558 -0.0112 0.3371 0.248 Uiso 1 1 calc R . .
H26B H 0.3243 -0.0649 0.3864 0.248 Uiso 1 1 calc R . .
H26C H 0.3981 -0.0059 0.4076 0.248 Uiso 1 1 calc R . .
O2 O 0.2388(3) 0.20774(18) 0.3371(2) 0.0593(12) 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 C1 1.905(6) . ?
Br2 C17 1.898(7) . ?
N1 C4 1.426(7) . ?
N1 C22 1.474(6) . ?
N1 C7 1.475(6) . ?
C7 N2 1.470(6) . ?
C7 C8 1.516(7) . ?
C7 H7 0.9800 . ?
O3 C25 1.208(7) . ?
N2 C20 1.386(6) . ?
N2 C14 1.422(7) . ?
O1 C23 1.199(6) . ?
C2 C1 1.354(8) . ?
C2 C3 1.373(8) . ?
C2 H2 0.9300 . ?
C8 C13 1.390(8) . ?
C8 C9 1.395(8) . ?
C23 O2 1.334(7) . ?
C23 C20 1.527(8) . ?
C14 C15 1.375(7) . ?
C14 C19 1.379(7) . ?
C4 C3 1.379(8) . ?
C4 C5 1.390(7) . ?
C3 H3 0.9300 . ?
C20 C21 1.339(7) . ?
C15 C16 1.384(8) . ?
C15 H15 0.9300 . ?
C13 C12 1.394(8) . ?
C13 H13 0.9300 . ?
C22 C21 1.510(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C18 C17 1.372(9) . ?
C18 C19 1.387(8) . ?
C18 H18 0.9300 . ?
O4 C25 1.347(7) . ?
O4 C26 1.468(8) . ?
C1 C6 1.367(8) . ?
C21 C25 1.464(9) . ?
C19 H19 0.9300 . ?
C24 O2 1.453(6) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C10 C11 1.369(9) . ?
C10 C9 1.380(8) . ?
C10 H10 0.9300 . ?
C5 C6 1.396(8) . ?
C5 H5 0.9300 . ?
C9 H9 0.9300 . ?
C11 C12 1.384(10) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C16 C17 1.358(9) . ?
C16 H16 0.9300 . ?
C6 H6 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
C4 N1 C22 118.3(5) . . ?
C4 N1 C7 112.9(4) . . ?
C22 N1 C7 110.6(4) . . ?
N2 C7 N1 110.0(4) . . ?
N2 C7 C8 112.8(5) . . ?
N1 C7 C8 110.9(5) . . ?
N2 C7 H7 107.6 . . ?
N1 C7 H7 107.6 . . ?
C8 C7 H7 107.6 . . ?
C20 N2 C14 121.3(5) . . ?
C20 N2 C7 116.5(4) . . ?
C14 N2 C7 119.8(5) . . ?
C1 C2 C3 120.4(6) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C13 C8 C9 119.2(6) . . ?
C13 C8 C7 119.2(6) . . ?
C9 C8 C7 121.3(6) . . ?
O1 C23 O2 125.3(6) . . ?
O1 C23 C20 122.7(6) . . ?
O2 C23 C20 112.0(5) . . ?
C15 C14 C19 119.0(6) . . ?
C15 C14 N2 120.1(6) . . ?
C19 C14 N2 120.9(5) . . ?
C3 C4 C5 118.4(6) . . ?
C3 C4 N1 118.8(5) . . ?
C5 C4 N1 122.7(6) . . ?
C2 C3 C4 120.8(6) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C21 C20 N2 122.0(5) . . ?
C21 C20 C23 124.2(5) . . ?
N2 C20 C23 113.4(5) . . ?
C14 C15 C16 120.2(6) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C8 C13 C12 120.0(7) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
N1 C22 C21 112.7(4) . . ?
N1 C22 H22A 109.1 . . ?
C21 C22 H22A 109.1 . . ?
N1 C22 H22B 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C17 C18 C19 118.6(7) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C25 O4 C26 114.6(6) . . ?
C2 C1 C6 120.7(6) . . ?
C2 C1 Br1 119.9(6) . . ?
C6 C1 Br1 119.4(5) . . ?
C20 C21 C25 120.2(6) . . ?
C20 C21 C22 121.0(5) . . ?
C25 C21 C22 118.6(5) . . ?
C14 C19 C18 121.0(6) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C11 C10 C9 119.3(7) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
O3 C25 O4 122.2(7) . . ?
O3 C25 C21 127.5(7) . . ?
O4 C25 C21 110.3(6) . . ?
C4 C5 C6 120.2(6) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C10 C9 C8 120.8(6) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C10 C11 C12 121.4(7) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C13 119.3(7) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C17 C16 C15 120.0(6) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 121.2(6) . . ?
C16 C17 Br2 119.8(6) . . ?
C18 C17 Br2 119.0(6) . . ?
C1 C6 C5 119.4(6) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 O2 C24 114.8(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C7 N2 -74.6(6) . . . . ?
C22 N1 C7 N2 60.5(6) . . . . ?
C4 N1 C7 C8 159.9(5) . . . . ?
C22 N1 C7 C8 -65.0(6) . . . . ?
N1 C7 N2 C20 -45.3(6) . . . . ?
C8 C7 N2 C20 79.1(6) . . . . ?
N1 C7 N2 C14 117.2(5) . . . . ?
C8 C7 N2 C14 -118.4(5) . . . . ?
N2 C7 C8 C13 -166.8(5) . . . . ?
N1 C7 C8 C13 -42.8(7) . . . . ?
N2 C7 C8 C9 19.5(8) . . . . ?
N1 C7 C8 C9 143.4(5) . . . . ?
C20 N2 C14 C15 -146.3(6) . . . . ?
C7 N2 C14 C15 52.0(7) . . . . ?
C20 N2 C14 C19 34.5(8) . . . . ?
C7 N2 C14 C19 -127.2(6) . . . . ?
C22 N1 C4 C3 163.2(5) . . . . ?
C7 N1 C4 C3 -65.5(7) . . . . ?
C22 N1 C4 C5 -16.1(8) . . . . ?
C7 N1 C4 C5 115.2(6) . . . . ?
C1 C2 C3 C4 -0.3(9) . . . . ?
C5 C4 C3 C2 -0.5(9) . . . . ?
N1 C4 C3 C2 -179.9(5) . . . . ?
C14 N2 C20 C21 -150.4(5) . . . . ?
C7 N2 C20 C21 11.9(8) . . . . ?
C14 N2 C20 C23 36.9(7) . . . . ?
C7 N2 C20 C23 -160.8(5) . . . . ?
O1 C23 C20 C21 -119.5(7) . . . . ?
O2 C23 C20 C21 62.3(7) . . . . ?
O1 C23 C20 N2 53.0(8) . . . . ?
O2 C23 C20 N2 -125.1(5) . . . . ?
C19 C14 C15 C16 -1.3(9) . . . . ?
N2 C14 C15 C16 179.6(5) . . . . ?
C9 C8 C13 C12 -1.4(9) . . . . ?
C7 C8 C13 C12 -175.3(5) . . . . ?
C4 N1 C22 C21 89.5(6) . . . . ?
C7 N1 C22 C21 -42.9(6) . . . . ?
C3 C2 C1 C6 1.3(10) . . . . ?
C3 C2 C1 Br1 179.7(4) . . . . ?
N2 C20 C21 C25 -168.2(5) . . . . ?
C23 C20 C21 C25 3.7(9) . . . . ?
N2 C20 C21 C22 6.5(9) . . . . ?
C23 C20 C21 C22 178.4(5) . . . . ?
N1 C22 C21 C20 9.9(8) . . . . ?
N1 C22 C21 C25 -175.3(5) . . . . ?
C15 C14 C19 C18 2.4(9) . . . . ?
N2 C14 C19 C18 -178.4(5) . . . . ?
C17 C18 C19 C14 -1.3(10) . . . . ?
C26 O4 C25 O3 2.3(11) . . . . ?
C26 O4 C25 C21 -176.8(7) . . . . ?
C20 C21 C25 O3 18.7(11) . . . . ?
C22 C21 C25 O3 -156.1(7) . . . . ?
C20 C21 C25 O4 -162.2(6) . . . . ?
C22 C21 C25 O4 23.0(8) . . . . ?
C3 C4 C5 C6 0.4(9) . . . . ?
N1 C4 C5 C6 179.7(5) . . . . ?
C11 C10 C9 C8 1.0(10) . . . . ?
C13 C8 C9 C10 0.3(9) . . . . ?
C7 C8 C9 C10 174.1(6) . . . . ?
C9 C10 C11 C12 -1.1(11) . . . . ?
C10 C11 C12 C13 0.0(11) . . . . ?
C8 C13 C12 C11 1.3(10) . . . . ?
C14 C15 C16 C17 -1.0(10) . . . . ?
C15 C16 C17 C18 2.2(11) . . . . ?
C15 C16 C17 Br2 -179.9(5) . . . . ?
C19 C18 C17 C16 -1.1(10) . . . . ?
C19 C18 C17 Br2 -179.0(5) . . . . ?
C2 C1 C6 C5 -1.5(10) . . . . ?
Br1 C1 C6 C5 -179.8(4) . . . . ?
C4 C5 C6 C1 0.6(9) . . . . ?
O1 C23 O2 C24 6.4(9) . . . . ?
C20 C23 O2 C24 -175.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.80
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.070
