# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1425909'
_audit_update_record             
;
2015-10-22 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;











_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H26 Br2 O4'
_chemical_formula_weight         682.39

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   5.6288(11)
_cell_length_b                   12.578(3)
_cell_length_c                   41.669(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2950.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5189
_cell_measurement_theta_min      0.98
_cell_measurement_theta_max      25.00

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    2.788
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_max  0.0000
_exptl_absorpt_correction_T_min  0.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       dtprofit.ref
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30944
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         0.98
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5189
_reflns_number_gt                4767
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+15.0000P] 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       ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.044(18)
_refine_ls_number_reflns         5189
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.1646
_refine_ls_wR_factor_gt          0.1496
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.0754(2) 0.01230(7) 0.01481(2) 0.0748(3) Uani 1 1 d . . .
Br2 Br -0.1119(2) 0.19332(8) -0.47191(2) 0.0734(3) Uani 1 1 d . . .
O1 O -0.4746(11) 0.3240(5) -0.09739(14) 0.0662(17) Uani 1 1 d . . .
O2 O -0.0748(10) 0.4784(4) -0.26434(11) 0.0468(12) Uani 1 1 d . . .
O3 O -0.0141(13) 0.4180(4) -0.31403(13) 0.071(2) Uani 1 1 d . . .
O4 O 0.3505(10) 0.5491(6) -0.36564(14) 0.0651(17) Uani 1 1 d . . .
C1 C -0.3182(15) 0.1600(7) -0.0559(2) 0.055(2) Uani 1 1 d . . .
H1A H -0.4630 0.1488 -0.0660 0.065 Uiso 1 1 calc R . .
C2 C -0.2460(16) 0.0920(7) -0.03206(19) 0.057(2) Uani 1 1 d . . .
H2A H -0.3415 0.0351 -0.0260 0.068 Uiso 1 1 calc R . .
C3 C -0.0291(14) 0.1090(6) -0.01711(16) 0.0458(18) Uani 1 1 d . . .
C4 C 0.1073(14) 0.1931(6) -0.02485(16) 0.0454(16) Uani 1 1 d . . .
H4A H 0.2473 0.2054 -0.0136 0.054 Uiso 1 1 calc R . .
C5 C 0.0424(15) 0.2613(6) -0.04922(17) 0.0453(18) Uani 1 1 d . . .
H5A H 0.1426 0.3167 -0.0551 0.054 Uiso 1 1 calc R . .
C6 C -0.1745(14) 0.2471(6) -0.06508(16) 0.0431(19) Uani 1 1 d . . .
C7 C -0.2606(15) 0.3201(8) -0.09075(19) 0.053(2) Uani 1 1 d . . .
C8 C -0.0755(17) 0.3798(6) -0.10772(17) 0.052(2) Uani 1 1 d . . .
H8A H 0.0783 0.3542 -0.1050 0.063 Uiso 1 1 calc R . .
C9 C -0.0958(16) 0.4676(6) -0.12694(16) 0.0498(19) Uani 1 1 d . . .
H9A H 0.0408 0.4824 -0.1387 0.060 Uiso 1 1 calc R . .
C10 C -0.2911(14) 0.5437(7) -0.13279(17) 0.0468(19) Uani 1 1 d . . .
C11 C -0.4664(16) 0.5640(7) -0.1105(2) 0.059(2) Uani 1 1 d . . .
H11A H -0.4674 0.5262 -0.0913 0.071 Uiso 1 1 calc R . .
C12 C -0.6409(17) 0.6393(7) -0.1160(2) 0.061(2) Uani 1 1 d . . .
H12A H -0.7580 0.6504 -0.1006 0.073 Uiso 1 1 calc R . .
C13 C -0.6441(18) 0.6984(7) -0.1441(2) 0.063(2) Uani 1 1 d . . .
H13A H -0.7604 0.7497 -0.1474 0.076 Uiso 1 1 calc R . .
C14 C -0.4708(15) 0.6798(7) -0.16711(19) 0.055(2) Uani 1 1 d . . .
H14A H -0.4704 0.7195 -0.1859 0.067 Uiso 1 1 calc R . .
C15 C -0.2954(14) 0.6014(7) -0.16232(18) 0.0460(18) Uani 1 1 d . . .
C16 C -0.1245(16) 0.5816(5) -0.18773(15) 0.0431(17) Uani 1 1 d . . .
H16A H 0.0299 0.5648 -0.1816 0.052 Uiso 1 1 calc R . .
C17 C -0.1703(13) 0.5855(5) -0.21910(17) 0.0389(17) Uani 1 1 d . . .
H17A H -0.3239 0.6013 -0.2258 0.047 Uiso 1 1 calc R . .
C18 C 0.0176(14) 0.5652(6) -0.24402(17) 0.0445(18) Uani 1 1 d . . .
H18A H 0.1638 0.5416 -0.2334 0.053 Uiso 1 1 calc R . .
C19 C 0.0763(14) 0.6545(6) -0.26762(15) 0.0433(17) Uani 1 1 d . . .
H19A H 0.2134 0.6956 -0.2601 0.052 Uiso 1 1 calc R . .
C20 C -0.1238(13) 0.7275(5) -0.27735(16) 0.0387(16) Uani 1 1 d . . .
C21 C -0.2656(14) 0.7912(6) -0.25810(18) 0.0448(18) Uani 1 1 d . . .
H21A H -0.2413 0.7932 -0.2360 0.054 Uiso 1 1 calc R . .
C22 C -0.4412(15) 0.8512(5) -0.27177(19) 0.0480(19) Uani 1 1 d . . .
H22A H -0.5366 0.8941 -0.2589 0.058 Uiso 1 1 calc R . .
C23 C -0.4782(15) 0.8484(6) -0.3049(2) 0.0502(19) Uani 1 1 d . . .
H23A H -0.6028 0.8869 -0.3138 0.060 Uiso 1 1 calc R . .
C24 C -0.3335(12) 0.7895(6) -0.32453(18) 0.0428(17) Uani 1 1 d . . .
H24A H -0.3548 0.7902 -0.3467 0.051 Uiso 1 1 calc R . .
C25 C -0.1542(13) 0.7289(6) -0.31070(17) 0.0417(17) Uani 1 1 d . . .
C26 C 0.0358(12) 0.6615(6) -0.32672(16) 0.0408(17) Uani 1 1 d . . .
H26A H 0.1619 0.7095 -0.3340 0.049 Uiso 1 1 calc R . .
C27 C 0.1365(14) 0.5947(6) -0.29888(16) 0.0455(18) Uani 1 1 d . . .
H27A H 0.3087 0.5857 -0.3011 0.055 Uiso 1 1 calc R . .
C28 C 0.0160(15) 0.4889(7) -0.29474(18) 0.053(2) Uani 1 1 d . . .
C29 C -0.0552(13) 0.5996(6) -0.35652(16) 0.0428(17) Uani 1 1 d . . .
H29A H -0.1811 0.5514 -0.3501 0.051 Uiso 1 1 calc R . .
H29B H -0.1202 0.6492 -0.3720 0.051 Uiso 1 1 calc R . .
C30 C 0.1448(14) 0.5368(7) -0.37190(17) 0.0484(19) Uani 1 1 d . . .
C31 C 0.0721(13) 0.4533(6) -0.39617(16) 0.0423(17) Uani 1 1 d . . .
C32 C -0.1413(14) 0.4558(6) -0.41238(18) 0.0493(19) Uani 1 1 d . . .
H32A H -0.2525 0.5081 -0.4075 0.059 Uiso 1 1 calc R . .
C33 C -0.1916(15) 0.3806(7) -0.43593(18) 0.052(2) Uani 1 1 d . . .
H33A H -0.3330 0.3842 -0.4474 0.062 Uiso 1 1 calc R . .
C34 C -0.0306(15) 0.3008(7) -0.44209(18) 0.053(2) Uani 1 1 d . . .
C35 C 0.1821(15) 0.2972(7) -0.42587(19) 0.055(2) Uani 1 1 d . . .
H35A H 0.2923 0.2441 -0.4304 0.066 Uiso 1 1 calc R . .
C36 C 0.2299(15) 0.3720(8) -0.40313(19) 0.056(2) Uani 1 1 d . . .
H36A H 0.3727 0.3684 -0.3920 0.067 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 C3 1.896(8) . ?
Br2 C34 1.892(9) . ?
O1 C7 1.237(9) . ?
O2 C28 1.373(9) . ?
O2 C18 1.476(9) . ?
O3 C28 1.212(10) . ?
O4 C30 1.197(9) . ?
C1 C2 1.371(12) . ?
C1 C6 1.414(11) . ?
C1 H1A 0.9300 . ?
C2 C3 1.387(11) . ?
C2 H2A 0.9300 . ?
C3 C4 1.347(10) . ?
C4 C5 1.378(10) . ?
C4 H4A 0.9300 . ?
C5 C6 1.400(11) . ?
C5 H5A 0.9300 . ?
C6 C7 1.491(11) . ?
C7 C8 1.466(12) . ?
C8 C9 1.369(11) . ?
C8 H8A 0.9300 . ?
C9 C10 1.477(12) . ?
C9 H9A 0.9300 . ?
C10 C11 1.378(11) . ?
C10 C15 1.429(11) . ?
C11 C12 1.384(13) . ?
C11 H11A 0.9300 . ?
C12 C13 1.385(13) . ?
C12 H12A 0.9300 . ?
C13 C14 1.388(12) . ?
C13 H13A 0.9300 . ?
C14 C15 1.410(11) . ?
C14 H14A 0.9300 . ?
C15 C16 1.452(11) . ?
C16 C17 1.334(9) . ?
C16 H16A 0.9300 . ?
C17 C18 1.504(10) . ?
C17 H17A 0.9300 . ?
C18 C19 1.529(10) . ?
C18 H18A 0.9800 . ?
C19 C20 1.509(10) . ?
C19 C27 1.542(10) . ?
C19 H19A 0.9800 . ?
C20 C21 1.387(11) . ?
C20 C25 1.400(10) . ?
C21 C22 1.368(11) . ?
C21 H21A 0.9300 . ?
C22 C23 1.398(11) . ?
C22 H22A 0.9300 . ?
C23 C24 1.370(11) . ?
C23 H23A 0.9300 . ?
C24 C25 1.390(10) . ?
C24 H24A 0.9300 . ?
C25 C26 1.519(10) . ?
C26 C27 1.540(9) . ?
C26 C29 1.552(10) . ?
C26 H26A 0.9800 . ?
C27 C28 1.504(11) . ?
C27 H27A 0.9800 . ?
C29 C30 1.517(10) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.514(11) . ?
C31 C32 1.378(11) . ?
C31 C36 1.385(11) . ?
C32 C33 1.392(11) . ?
C32 H32A 0.9300 . ?
C33 C34 1.377(11) . ?
C33 H33A 0.9300 . ?
C34 C35 1.376(11) . ?
C35 C36 1.362(12) . ?
C35 H35A 0.9300 . ?
C36 H36A 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
C28 O2 C18 109.1(6) . . ?
C2 C1 C6 120.7(8) . . ?
C2 C1 H1A 119.7 . . ?
C6 C1 H1A 119.7 . . ?
C3 C2 C1 119.3(8) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C4 C3 C2 121.0(7) . . ?
C4 C3 Br1 119.7(6) . . ?
C2 C3 Br1 119.3(6) . . ?
C3 C4 C5 120.9(8) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 C6 120.0(7) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 C1 118.0(7) . . ?
C5 C6 C7 122.9(7) . . ?
C1 C6 C7 119.1(7) . . ?
O1 C7 C8 124.3(8) . . ?
O1 C7 C6 120.1(8) . . ?
C8 C7 C6 115.5(7) . . ?
C9 C8 C7 129.5(9) . . ?
C9 C8 H8A 115.3 . . ?
C7 C8 H8A 115.3 . . ?
C8 C9 C10 132.9(8) . . ?
C8 C9 H9A 113.5 . . ?
C10 C9 H9A 113.5 . . ?
C11 C10 C15 118.3(8) . . ?
C11 C10 C9 122.8(7) . . ?
C15 C10 C9 118.9(7) . . ?
C12 C11 C10 121.6(8) . . ?
C12 C11 H11A 119.2 . . ?
C10 C11 H11A 119.2 . . ?
C13 C12 C11 121.1(8) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C12 C13 C14 118.9(9) . . ?
C12 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
C13 C14 C15 120.8(8) . . ?
C13 C14 H14A 119.6 . . ?
C15 C14 H14A 119.6 . . ?
C14 C15 C10 119.3(7) . . ?
C14 C15 C16 118.7(7) . . ?
C10 C15 C16 122.0(7) . . ?
C17 C16 C15 125.5(8) . . ?
C17 C16 H16A 117.3 . . ?
C15 C16 H16A 117.3 . . ?
C16 C17 C18 122.3(7) . . ?
C16 C17 H17A 118.8 . . ?
C18 C17 H17A 118.8 . . ?
O2 C18 C17 105.9(6) . . ?
O2 C18 C19 104.5(5) . . ?
C17 C18 C19 118.1(6) . . ?
O2 C18 H18A 109.3 . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
C20 C19 C18 117.3(6) . . ?
C20 C19 C27 103.5(5) . . ?
C18 C19 C27 103.4(6) . . ?
C20 C19 H19A 110.7 . . ?
C18 C19 H19A 110.7 . . ?
C27 C19 H19A 110.7 . . ?
C21 C20 C25 119.8(7) . . ?
C21 C20 C19 128.8(6) . . ?
C25 C20 C19 111.4(6) . . ?
C20 C21 C22 119.6(7) . . ?
C20 C21 H21A 120.2 . . ?
C22 C21 H21A 120.2 . . ?
C21 C22 C23 120.3(7) . . ?
C21 C22 H22A 119.8 . . ?
C23 C22 H22A 119.8 . . ?
C24 C23 C22 121.0(7) . . ?
C24 C23 H23A 119.5 . . ?
C22 C23 H23A 119.5 . . ?
C23 C24 C25 118.7(7) . . ?
C23 C24 H24A 120.6 . . ?
C25 C24 H24A 120.6 . . ?
C20 C25 C24 120.4(7) . . ?
C20 C25 C26 110.1(6) . . ?
C24 C25 C26 129.4(7) . . ?
C25 C26 C27 103.4(6) . . ?
C25 C26 C29 113.5(6) . . ?
C27 C26 C29 116.8(6) . . ?
C25 C26 H26A 107.5 . . ?
C27 C26 H26A 107.5 . . ?
C29 C26 H26A 107.5 . . ?
C28 C27 C19 103.6(6) . . ?
C28 C27 C26 113.7(6) . . ?
C19 C27 C26 106.8(6) . . ?
C28 C27 H27A 110.8 . . ?
C19 C27 H27A 110.8 . . ?
C26 C27 H27A 110.8 . . ?
O3 C28 O2 119.3(8) . . ?
O3 C28 C27 129.7(7) . . ?
O2 C28 C27 111.1(7) . . ?
C30 C29 C26 110.7(6) . . ?
C30 C29 H29A 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
O4 C30 C31 119.8(7) . . ?
O4 C30 C29 123.9(8) . . ?
C31 C30 C29 116.3(7) . . ?
C32 C31 C36 118.2(7) . . ?
C32 C31 C30 123.2(7) . . ?
C36 C31 C30 118.6(7) . . ?
C31 C32 C33 120.5(7) . . ?
C31 C32 H32A 119.8 . . ?
C33 C32 H32A 119.8 . . ?
C34 C33 C32 119.5(8) . . ?
C34 C33 H33A 120.2 . . ?
C32 C33 H33A 120.2 . . ?
C33 C34 C35 120.4(8) . . ?
C33 C34 Br2 119.0(6) . . ?
C35 C34 Br2 120.6(7) . . ?
C36 C35 C34 119.4(8) . . ?
C36 C35 H35A 120.3 . . ?
C34 C35 H35A 120.3 . . ?
C35 C36 C31 121.9(8) . . ?
C35 C36 H36A 119.0 . . ?
C31 C36 H36A 119.0 . . ?

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
C6 C1 C2 C3 -0.3(12) . . . . ?
C1 C2 C3 C4 2.3(11) . . . . ?
C1 C2 C3 Br1 -177.9(6) . . . . ?
C2 C3 C4 C5 -4.0(11) . . . . ?
Br1 C3 C4 C5 176.3(6) . . . . ?
C3 C4 C5 C6 3.7(11) . . . . ?
C4 C5 C6 C1 -1.6(11) . . . . ?
C4 C5 C6 C7 177.5(7) . . . . ?
C2 C1 C6 C5 0.0(11) . . . . ?
C2 C1 C6 C7 -179.2(7) . . . . ?
C5 C6 C7 O1 -158.9(8) . . . . ?
C1 C6 C7 O1 20.3(12) . . . . ?
C5 C6 C7 C8 24.1(11) . . . . ?
C1 C6 C7 C8 -156.7(7) . . . . ?
O1 C7 C8 C9 19.0(14) . . . . ?
C6 C7 C8 C9 -164.2(7) . . . . ?
C7 C8 C9 C10 12.9(14) . . . . ?
C8 C9 C10 C11 26.0(13) . . . . ?
C8 C9 C10 C15 -156.0(8) . . . . ?
C15 C10 C11 C12 -1.0(12) . . . . ?
C9 C10 C11 C12 176.9(8) . . . . ?
C10 C11 C12 C13 -0.9(13) . . . . ?
C11 C12 C13 C14 1.1(13) . . . . ?
C12 C13 C14 C15 0.6(12) . . . . ?
C13 C14 C15 C10 -2.5(11) . . . . ?
C13 C14 C15 C16 177.3(8) . . . . ?
C11 C10 C15 C14 2.7(11) . . . . ?
C9 C10 C15 C14 -175.3(7) . . . . ?
C11 C10 C15 C16 -177.1(7) . . . . ?
C9 C10 C15 C16 4.9(11) . . . . ?
C14 C15 C16 C17 -35.8(11) . . . . ?
C10 C15 C16 C17 144.0(8) . . . . ?
C15 C16 C17 C18 179.2(7) . . . . ?
C28 O2 C18 C17 150.8(6) . . . . ?
C28 O2 C18 C19 25.4(8) . . . . ?
C16 C17 C18 O2 124.2(7) . . . . ?
C16 C17 C18 C19 -119.2(8) . . . . ?
O2 C18 C19 C20 84.5(7) . . . . ?
C17 C18 C19 C20 -32.8(9) . . . . ?
O2 C18 C19 C27 -28.7(7) . . . . ?
C17 C18 C19 C27 -146.0(6) . . . . ?
C18 C19 C20 C21 58.8(10) . . . . ?
C27 C19 C20 C21 172.0(7) . . . . ?
C18 C19 C20 C25 -123.3(7) . . . . ?
C27 C19 C20 C25 -10.1(8) . . . . ?
C25 C20 C21 C22 3.0(10) . . . . ?
C19 C20 C21 C22 -179.2(7) . . . . ?
C20 C21 C22 C23 0.0(11) . . . . ?
C21 C22 C23 C24 -2.9(12) . . . . ?
C22 C23 C24 C25 2.6(11) . . . . ?
C21 C20 C25 C24 -3.3(10) . . . . ?
C19 C20 C25 C24 178.5(6) . . . . ?
C21 C20 C25 C26 174.5(6) . . . . ?
C19 C20 C25 C26 -3.7(8) . . . . ?
C23 C24 C25 C20 0.5(10) . . . . ?
C23 C24 C25 C26 -176.8(7) . . . . ?
C20 C25 C26 C27 15.8(8) . . . . ?
C24 C25 C26 C27 -166.7(7) . . . . ?
C20 C25 C26 C29 143.3(6) . . . . ?
C24 C25 C26 C29 -39.1(10) . . . . ?
C20 C19 C27 C28 -100.8(6) . . . . ?
C18 C19 C27 C28 22.0(7) . . . . ?
C20 C19 C27 C26 19.6(7) . . . . ?
C18 C19 C27 C26 142.4(6) . . . . ?
C25 C26 C27 C28 92.1(7) . . . . ?
C29 C26 C27 C28 -33.4(9) . . . . ?
C25 C26 C27 C19 -21.6(7) . . . . ?
C29 C26 C27 C19 -147.1(6) . . . . ?
C18 O2 C28 O3 170.7(7) . . . . ?
C18 O2 C28 C27 -11.2(8) . . . . ?
C19 C27 C28 O3 170.3(9) . . . . ?
C26 C27 C28 O3 54.8(11) . . . . ?
C19 C27 C28 O2 -7.5(8) . . . . ?
C26 C27 C28 O2 -123.1(7) . . . . ?
C25 C26 C29 C30 178.2(6) . . . . ?
C27 C26 C29 C30 -61.5(8) . . . . ?
C26 C29 C30 O4 -13.0(11) . . . . ?
C26 C29 C30 C31 166.2(6) . . . . ?
O4 C30 C31 C32 -158.3(8) . . . . ?
C29 C30 C31 C32 22.5(10) . . . . ?
O4 C30 C31 C36 19.8(11) . . . . ?
C29 C30 C31 C36 -159.3(7) . . . . ?
C36 C31 C32 C33 -2.3(11) . . . . ?
C30 C31 C32 C33 175.8(7) . . . . ?
C31 C32 C33 C34 2.6(12) . . . . ?
C32 C33 C34 C35 -2.1(12) . . . . ?
C32 C33 C34 Br2 175.4(6) . . . . ?
C33 C34 C35 C36 1.4(13) . . . . ?
Br2 C34 C35 C36 -176.1(6) . . . . ?
C34 C35 C36 C31 -1.2(13) . . . . ?
C32 C31 C36 C35 1.7(12) . . . . ?
C30 C31 C36 C35 -176.6(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.705
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.152
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1425910'
_audit_update_record             
;
2015-09-18 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H28 O4'
_chemical_formula_sum            'C36 H28 O4'
_chemical_formula_weight         524.58

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.2630(12)
_cell_length_b                   12.8186(16)
_cell_length_c                   22.369(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2656.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1794
_cell_measurement_theta_min      30.10
_cell_measurement_theta_max      78.00

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.673
_shelx_estimated_absorpt_T_min   0.794
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            22581
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         6.204
_diffrn_reflns_theta_max         77.852
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5505
_reflns_number_gt                5386
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_max     0.965
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_refine_special_details          
; 
    ENTER TEXT OF LETTER 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+0.3595P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2301 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5505
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0703
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47065(13) 0.49561(9) 0.44656(5) 0.0369(3) Uani 1 1 d . . . . .
O2 O 0.35609(13) 0.39928(11) 0.37892(5) 0.0459(3) Uani 1 1 d . . . . .
O3 O -0.12859(14) 0.68337(11) 0.48065(6) 0.0521(3) Uani 1 1 d . . . . .
O4 O 0.34384(14) 0.12513(11) 0.39337(5) 0.0458(3) Uani 1 1 d . . . . .
C1 C 0.43820(17) 0.40306(13) 0.42053(6) 0.0325(3) Uani 1 1 d . . . . .
C2 C 0.51449(16) 0.31392(11) 0.45188(6) 0.0290(3) Uani 1 1 d . . . . .
H2 H 0.4451 0.2737 0.4772 0.035 Uiso 1 1 calc R U . . .
C3 C 0.60053(16) 0.23906(11) 0.41021(6) 0.0293(3) Uani 1 1 d . . . . .
H3 H 0.6094 0.1706 0.4314 0.035 Uiso 1 1 calc R U . . .
C4 C 0.74981(16) 0.28885(11) 0.40926(6) 0.0290(3) Uani 1 1 d . . . . .
C5 C 0.76428(16) 0.36167(11) 0.45508(6) 0.0275(3) Uani 1 1 d . . . . .
C6 C 0.89396(17) 0.41478(12) 0.46369(7) 0.0322(3) Uani 1 1 d . . . . .
H6 H 0.9036 0.4639 0.4952 0.039 Uiso 1 1 calc R U . . .
C7 C 1.00879(18) 0.39487(13) 0.42553(8) 0.0369(3) Uani 1 1 d . . . . .
H7 H 1.0974 0.4311 0.4307 0.044 Uiso 1 1 calc R U . . .
C8 C 0.99480(18) 0.32209(13) 0.37978(8) 0.0381(4) Uani 1 1 d . . . . .
H8 H 1.0742 0.3087 0.3540 0.046 Uiso 1 1 calc R U . . .
C9 C 0.86574(18) 0.26873(12) 0.37146(7) 0.0351(3) Uani 1 1 d . . . . .
H9 H 0.8568 0.2189 0.3402 0.042 Uiso 1 1 calc R U . . .
C10 C 0.62662(16) 0.37021(11) 0.49127(6) 0.0284(3) Uani 1 1 d . . . . .
H10 H 0.6367 0.3359 0.5312 0.034 Uiso 1 1 calc R U . . .
C11 C 0.56703(18) 0.48275(12) 0.49716(6) 0.0323(3) Uani 1 1 d . . . . .
H11 H 0.6487 0.5334 0.4935 0.039 Uiso 1 1 calc R U . . .
C12 C 0.48883(19) 0.50234(13) 0.55500(7) 0.0357(3) Uani 1 1 d . . . . .
H12 H 0.5470 0.5136 0.5894 0.043 Uiso 1 1 calc R U . . .
C13 C 0.34732(18) 0.50551(12) 0.56298(7) 0.0327(3) Uani 1 1 d . . . . .
H13 H 0.2882 0.4954 0.5288 0.039 Uiso 1 1 calc R U . . .
C14 C 0.27362(18) 0.52340(11) 0.62075(7) 0.0328(3) Uani 1 1 d . . . . .
C15 C 0.13227(18) 0.56437(11) 0.62454(7) 0.0332(3) Uani 1 1 d . . . . .
C16 C 0.0655(2) 0.57108(13) 0.68073(7) 0.0400(4) Uani 1 1 d . . . . .
H16 H -0.0312 0.5953 0.6831 0.048 Uiso 1 1 calc R U . . .
C17 C 0.1362(2) 0.54349(14) 0.73257(8) 0.0459(4) Uani 1 1 d . . . . .
H17 H 0.0892 0.5497 0.7701 0.055 Uiso 1 1 calc R U . . .
C18 C 0.2766(2) 0.50655(15) 0.72935(7) 0.0445(4) Uani 1 1 d . . . . .
H18 H 0.3271 0.4889 0.7649 0.053 Uiso 1 1 calc R U . . .
C19 C 0.3431(2) 0.49542(13) 0.67423(7) 0.0390(4) Uani 1 1 d . . . . .
H19 H 0.4383 0.4681 0.6726 0.047 Uiso 1 1 calc R U . . .
C20 C 0.04829(18) 0.60238(12) 0.57314(7) 0.0346(3) Uani 1 1 d . . . . .
H20 H -0.0530 0.5911 0.5745 0.042 Uiso 1 1 calc R U . . .
C21 C 0.09935(18) 0.65098(13) 0.52488(7) 0.0366(3) Uani 1 1 d . . . . .
H21 H 0.1995 0.6664 0.5225 0.044 Uiso 1 1 calc R U . . .
C22 C 0.00338(19) 0.68157(12) 0.47482(8) 0.0369(3) Uani 1 1 d . . . . .
C23 C 0.07174(19) 0.70600(12) 0.41611(7) 0.0352(3) Uani 1 1 d . . . . .
C24 C -0.0116(2) 0.75202(14) 0.37155(8) 0.0436(4) Uani 1 1 d . . . . .
H24 H -0.1093 0.7698 0.3795 0.052 Uiso 1 1 calc R U . . .
C25 C 0.0465(3) 0.77214(16) 0.31577(9) 0.0525(5) Uani 1 1 d . . . . .
H25 H -0.0110 0.8039 0.2857 0.063 Uiso 1 1 calc R U . . .
C26 C 0.1880(3) 0.74601(18) 0.30384(9) 0.0546(5) Uani 1 1 d . . . . .
H26 H 0.2283 0.7605 0.2657 0.065 Uiso 1 1 calc R U . . .
C27 C 0.2710(3) 0.6989(2) 0.34723(10) 0.0594(5) Uani 1 1 d . . . . .
H27 H 0.3678 0.6794 0.3386 0.071 Uiso 1 1 calc R U . . .
C28 C 0.2140(2) 0.67981(16) 0.40327(8) 0.0472(4) Uani 1 1 d . . . . .
H28 H 0.2724 0.6486 0.4332 0.057 Uiso 1 1 calc R U . . .
C29 C 0.53984(17) 0.21699(12) 0.34804(6) 0.0312(3) Uani 1 1 d . . . . .
H29A H 0.5235 0.2843 0.3275 0.037 Uiso 1 1 calc R U . . .
H29B H 0.6132 0.1780 0.3248 0.037 Uiso 1 1 calc R U . . .
C30 C 0.39984(17) 0.15539(12) 0.34733(7) 0.0317(3) Uani 1 1 d . . . . .
C31 C 0.33770(16) 0.12641(12) 0.28780(7) 0.0311(3) Uani 1 1 d . . . . .
C32 C 0.23613(19) 0.04626(15) 0.28505(8) 0.0406(4) Uani 1 1 d . . . . .
H32 H 0.2023 0.0151 0.3210 0.049 Uiso 1 1 calc R U . . .
C33 C 0.1842(2) 0.01161(16) 0.23056(9) 0.0468(4) Uani 1 1 d . . . . .
H33 H 0.1155 -0.0434 0.2292 0.056 Uiso 1 1 calc R U . . .
C34 C 0.2318(2) 0.05668(16) 0.17818(8) 0.0466(4) Uani 1 1 d . . . . .
H34 H 0.1963 0.0327 0.1408 0.056 Uiso 1 1 calc R U . . .
C35 C 0.3313(2) 0.13667(16) 0.18029(8) 0.0476(4) Uani 1 1 d . . . . .
H35 H 0.3638 0.1680 0.1442 0.057 Uiso 1 1 calc R U . . .
C36 C 0.38418(19) 0.17152(13) 0.23476(7) 0.0376(3) Uani 1 1 d . . . . .
H36 H 0.4527 0.2267 0.2358 0.045 Uiso 1 1 calc R U . . .


_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
O1 C1 1.355(2) . ?
O1 C11 1.4509(19) . ?
O2 C1 1.2031(19) . ?
O3 C22 1.230(2) . ?
O4 C30 1.2166(19) . ?
C1 C2 1.516(2) . ?
C2 C10 1.541(2) . ?
C2 C3 1.557(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.523(2) . ?
C3 C29 1.5266(19) . ?
C3 H3 1.0000 . ?
C4 C9 1.391(2) . ?
C4 C5 1.393(2) . ?
C5 C6 1.394(2) . ?
C5 C10 1.514(2) . ?
C6 C7 1.387(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.550(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.504(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.323(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.479(2) . ?
C13 H13 0.9500 . ?
C14 C19 1.405(2) . ?
C14 C15 1.413(2) . ?
C15 C16 1.404(2) . ?
C15 C20 1.471(2) . ?
C16 C17 1.378(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.333(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.482(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.491(2) . ?
C23 C28 1.390(3) . ?
C23 C24 1.392(2) . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.379(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.378(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.382(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.518(2) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.497(2) . ?
C31 C36 1.388(2) . ?
C31 C32 1.394(2) . ?
C32 C33 1.384(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.379(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.379(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.387(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?

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
C1 O1 C11 111.85(12) . . ?
O2 C1 O1 120.52(15) . . ?
O2 C1 C2 128.50(15) . . ?
O1 C1 C2 110.96(12) . . ?
C1 C2 C10 103.05(12) . . ?
C1 C2 C3 115.23(11) . . ?
C10 C2 C3 106.60(12) . . ?
C1 C2 H2 110.5 . . ?
C10 C2 H2 110.5 . . ?
C3 C2 H2 110.5 . . ?
C4 C3 C29 113.53(12) . . ?
C4 C3 C2 102.40(12) . . ?
C29 C3 C2 118.11(13) . . ?
C4 C3 H3 107.4 . . ?
C29 C3 H3 107.4 . . ?
C2 C3 H3 107.4 . . ?
C9 C4 C5 119.83(14) . . ?
C9 C4 C3 129.17(13) . . ?
C5 C4 C3 110.97(13) . . ?
C4 C5 C6 120.79(14) . . ?
C4 C5 C10 111.15(13) . . ?
C6 C5 C10 128.05(13) . . ?
C7 C6 C5 119.06(14) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 120.30(15) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.59(15) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C4 119.42(14) . . ?
C8 C9 H9 120.3 . . ?
C4 C9 H9 120.3 . . ?
C5 C10 C2 103.18(11) . . ?
C5 C10 C11 114.36(12) . . ?
C2 C10 C11 104.13(12) . . ?
C5 C10 H10 111.5 . . ?
C2 C10 H10 111.5 . . ?
C11 C10 H10 111.5 . . ?
O1 C11 C12 110.84(13) . . ?
O1 C11 C10 104.99(11) . . ?
C12 C11 C10 113.58(13) . . ?
O1 C11 H11 109.1 . . ?
C12 C11 H11 109.1 . . ?
C10 C11 H11 109.1 . . ?
C13 C12 C11 126.75(15) . . ?
C13 C12 H12 116.6 . . ?
C11 C12 H12 116.6 . . ?
C12 C13 C14 125.43(15) . . ?
C12 C13 H13 117.3 . . ?
C14 C13 H13 117.3 . . ?
C19 C14 C15 117.91(15) . . ?
C19 C14 C13 119.53(15) . . ?
C15 C14 C13 122.52(14) . . ?
C16 C15 C14 119.00(15) . . ?
C16 C15 C20 116.52(15) . . ?
C14 C15 C20 124.47(14) . . ?
C17 C16 C15 121.89(17) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 119.34(16) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 119.91(17) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 121.86(18) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 119.1 . . ?
C21 C20 C15 126.88(15) . . ?
C21 C20 H20 116.6 . . ?
C15 C20 H20 116.6 . . ?
C20 C21 C22 121.50(16) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.3 . . ?
O3 C22 C21 121.40(16) . . ?
O3 C22 C23 120.77(16) . . ?
C21 C22 C23 117.78(14) . . ?
C28 C23 C24 118.71(16) . . ?
C28 C23 C22 122.26(15) . . ?
C24 C23 C22 118.95(16) . . ?
C25 C24 C23 120.60(18) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C26 C25 C24 119.95(18) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C27 C26 C25 120.05(19) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 120.2(2) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C23 120.47(18) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
C30 C29 C3 114.86(12) . . ?
C30 C29 H29A 108.6 . . ?
C3 C29 H29A 108.6 . . ?
C30 C29 H29B 108.6 . . ?
C3 C29 H29B 108.6 . . ?
H29A C29 H29B 107.5 . . ?
O4 C30 C31 120.65(14) . . ?
O4 C30 C29 121.41(14) . . ?
C31 C30 C29 117.81(12) . . ?
C36 C31 C32 118.59(14) . . ?
C36 C31 C30 122.50(14) . . ?
C32 C31 C30 118.77(14) . . ?
C33 C32 C31 120.66(16) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C34 C33 C32 120.18(17) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 119.75(16) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C34 C35 C36 120.35(17) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C31 120.47(15) . . ?
C35 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O1 C1 O2 177.86(13) . . . . ?
C11 O1 C1 C2 -0.76(17) . . . . ?
O2 C1 C2 C10 168.31(15) . . . . ?
O1 C1 C2 C10 -13.22(15) . . . . ?
O2 C1 C2 C3 52.6(2) . . . . ?
O1 C1 C2 C3 -128.91(13) . . . . ?
C1 C2 C3 C4 90.61(15) . . . . ?
C10 C2 C3 C4 -23.03(14) . . . . ?
C1 C2 C3 C29 -34.90(19) . . . . ?
C10 C2 C3 C29 -148.54(12) . . . . ?
C29 C3 C4 C9 -38.5(2) . . . . ?
C2 C3 C4 C9 -166.96(15) . . . . ?
C29 C3 C4 C5 143.39(13) . . . . ?
C2 C3 C4 C5 14.94(15) . . . . ?
C9 C4 C5 C6 -0.1(2) . . . . ?
C3 C4 C5 C6 178.19(13) . . . . ?
C9 C4 C5 C10 -179.10(13) . . . . ?
C3 C4 C5 C10 -0.80(16) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C10 C5 C6 C7 179.39(14) . . . . ?
C5 C6 C7 C8 -0.7(2) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 C4 0.2(2) . . . . ?
C5 C4 C9 C8 -0.3(2) . . . . ?
C3 C4 C9 C8 -178.22(15) . . . . ?
C4 C5 C10 C2 -13.90(15) . . . . ?
C6 C5 C10 C2 167.21(14) . . . . ?
C4 C5 C10 C11 -126.31(13) . . . . ?
C6 C5 C10 C11 54.79(19) . . . . ?
C1 C2 C10 C5 -98.99(12) . . . . ?
C3 C2 C10 C5 22.73(14) . . . . ?
C1 C2 C10 C11 20.73(14) . . . . ?
C3 C2 C10 C11 142.45(11) . . . . ?
C1 O1 C11 C12 -108.59(14) . . . . ?
C1 O1 C11 C10 14.43(16) . . . . ?
C5 C10 C11 O1 90.17(14) . . . . ?
C2 C10 C11 O1 -21.67(14) . . . . ?
C5 C10 C11 C12 -148.59(13) . . . . ?
C2 C10 C11 C12 99.56(14) . . . . ?
O1 C11 C12 C13 15.9(2) . . . . ?
C10 C11 C12 C13 -102.1(2) . . . . ?
C11 C12 C13 C14 179.01(14) . . . . ?
C12 C13 C14 C19 -26.9(2) . . . . ?
C12 C13 C14 C15 155.53(17) . . . . ?
C19 C14 C15 C16 -2.7(2) . . . . ?
C13 C14 C15 C16 174.86(14) . . . . ?
C19 C14 C15 C20 176.60(15) . . . . ?
C13 C14 C15 C20 -5.8(2) . . . . ?
C14 C15 C16 C17 3.1(2) . . . . ?
C20 C15 C16 C17 -176.27(15) . . . . ?
C15 C16 C17 C18 -1.0(3) . . . . ?
C16 C17 C18 C19 -1.5(3) . . . . ?
C17 C18 C19 C14 1.8(3) . . . . ?
C15 C14 C19 C18 0.3(2) . . . . ?
C13 C14 C19 C18 -177.32(15) . . . . ?
C16 C15 C20 C21 144.81(16) . . . . ?
C14 C15 C20 C21 -34.5(2) . . . . ?
C15 C20 C21 C22 177.43(14) . . . . ?
C20 C21 C22 O3 15.3(3) . . . . ?
C20 C21 C22 C23 -162.24(15) . . . . ?
O3 C22 C23 C28 -163.31(18) . . . . ?
C21 C22 C23 C28 14.2(2) . . . . ?
O3 C22 C23 C24 13.5(2) . . . . ?
C21 C22 C23 C24 -168.99(15) . . . . ?
C28 C23 C24 C25 -0.6(3) . . . . ?
C22 C23 C24 C25 -177.50(16) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C24 C25 C26 C27 0.7(3) . . . . ?
C25 C26 C27 C28 -1.5(4) . . . . ?
C26 C27 C28 C23 1.3(4) . . . . ?
C24 C23 C28 C27 -0.2(3) . . . . ?
C22 C23 C28 C27 176.59(19) . . . . ?
C4 C3 C29 C30 172.79(12) . . . . ?
C2 C3 C29 C30 -67.33(17) . . . . ?
C3 C29 C30 O4 -1.3(2) . . . . ?
C3 C29 C30 C31 -177.13(13) . . . . ?
O4 C30 C31 C36 169.99(17) . . . . ?
C29 C30 C31 C36 -14.2(2) . . . . ?
O4 C30 C31 C32 -14.3(2) . . . . ?
C29 C30 C31 C32 161.51(15) . . . . ?
C36 C31 C32 C33 0.8(3) . . . . ?
C30 C31 C32 C33 -175.05(17) . . . . ?
C31 C32 C33 C34 -0.4(3) . . . . ?
C32 C33 C34 C35 -0.1(3) . . . . ?
C33 C34 C35 C36 0.4(3) . . . . ?
C34 C35 C36 C31 0.0(3) . . . . ?
C32 C31 C36 C35 -0.6(3) . . . . ?
C30 C31 C36 C35 175.10(16) . . . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.027



####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1432669'
_audit_update_record             
;
2015-10-22 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Br2 O4'
_chemical_formula_sum            'C36 H26 Br2 O4'
_chemical_formula_weight         682.39

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   5.5911(18)
_cell_length_b                   13.004(4)
_cell_length_c                   40.623(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2953.4(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    6388
_cell_measurement_theta_min      2.01
_cell_measurement_theta_max      27.85

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.785
_shelx_estimated_absorpt_T_min   0.469
_shelx_estimated_absorpt_T_max   0.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.558
_exptl_absorpt_correction_T_max  0.846
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn70 CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            23050
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         1.860
_diffrn_reflns_theta_max         27.859
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6972
_reflns_number_gt                5148
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.995

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
; 
    ENTER TEXT OF LETTER 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0232P)²] 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       0.0047(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1554 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.013(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6972
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0701
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_restrained_S_all      0.931
_refine_ls_shift/su_max          0.002
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.07345(10) 0.50039(3) 0.49461(2) 0.03755(14) Uani 1 1 d . . . . .
Br2 Br 0.56166(11) 0.24556(4) 0.96859(2) 0.04315(16) Uani 1 1 d . . . . .
O1 O 0.4056(5) -0.02271(19) 0.75979(6) 0.0266(7) Uani 1 1 d . . . . .
O2 O 0.5224(6) 0.0316(2) 0.80939(7) 0.0355(8) Uani 1 1 d . . . . .
O3 O 0.5441(6) 0.1244(2) 0.59256(7) 0.0272(7) Uani 1 1 d . . . . .
O4 O 0.9726(6) -0.0894(2) 0.85190(8) 0.0383(8) Uani 1 1 d . . . . .
C1 C 0.4782(8) -0.1007(3) 0.73574(9) 0.0236(10) Uani 1 1 d . . . . .
H1 H 0.6089 -0.0715 0.7218 0.028 Uiso 1 1 calc R U . . .
C2 C 0.5833(8) -0.1886(3) 0.75683(9) 0.0216(9) Uani 1 1 d . . . . .
H2 H 0.7166 -0.2242 0.7450 0.026 Uiso 1 1 calc R U . . .
C3 C 0.6763(8) -0.1320(3) 0.78779(10) 0.0242(10) Uani 1 1 d . . . . .
H3 H 0.8511 -0.1173 0.7857 0.029 Uiso 1 1 calc R U . . .
C4 C 0.5340(8) -0.0329(3) 0.78821(10) 0.0277(10) Uani 1 1 d . . . . .
C5 C 0.6277(7) -0.2033(3) 0.81784(9) 0.0220(10) Uani 1 1 d . . . . .
H5 H 0.7725 -0.2471 0.8214 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4291(8) -0.2714(3) 0.80531(9) 0.0201(9) Uani 1 1 d . . . . .
C7 C 0.4072(7) -0.2657(3) 0.77106(9) 0.0198(9) Uani 1 1 d . . . . .
C8 C 0.2438(7) -0.3275(3) 0.75463(10) 0.0222(10) Uani 1 1 d . . . . .
H8 H 0.2357 -0.3264 0.7313 0.027 Uiso 1 1 calc R U . . .
C9 C 0.0922(9) -0.3909(3) 0.77255(10) 0.0266(10) Uani 1 1 d . . . . .
H9 H -0.0247 -0.4312 0.7615 0.032 Uiso 1 1 calc R U . . .
C10 C 0.1117(8) -0.3953(3) 0.80671(11) 0.0283(11) Uani 1 1 d . . . . .
H10 H 0.0064 -0.4384 0.8188 0.034 Uiso 1 1 calc R U . . .
C11 C 0.2826(8) -0.3377(3) 0.82335(10) 0.0251(10) Uani 1 1 d . . . . .
H11 H 0.2994 -0.3433 0.8466 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2694(8) -0.1245(3) 0.71418(10) 0.0221(10) Uani 1 1 d . . . . .
H12 H 0.1241 -0.1458 0.7242 0.027 Uiso 1 1 calc R U . . .
C13 C 0.2777(8) -0.1170(3) 0.68143(10) 0.0200(9) Uani 1 1 d . . . . .
H13 H 0.4207 -0.0918 0.6717 0.024 Uiso 1 1 calc R U . . .
C14 C 0.0776(8) -0.1457(3) 0.65922(9) 0.0219(9) Uani 1 1 d . . . . .
C15 C -0.0742(8) -0.2265(3) 0.66806(9) 0.0241(9) Uani 1 1 d . . . . .
H15 H -0.0421 -0.2647 0.6875 0.029 Uiso 1 1 calc R U . . .
C16 C -0.2710(8) -0.2519(4) 0.64889(10) 0.0277(10) Uani 1 1 d . . . . .
H16 H -0.3735 -0.3067 0.6553 0.033 Uiso 1 1 calc R U . . .
C17 C -0.3176(8) -0.1964(3) 0.62015(11) 0.0276(11) Uani 1 1 d . . . . .
H17 H -0.4536 -0.2127 0.6071 0.033 Uiso 1 1 calc R U . . .
C18 C -0.1667(8) -0.1180(3) 0.61061(11) 0.0255(10) Uani 1 1 d . . . . .
H18 H -0.1991 -0.0815 0.5909 0.031 Uiso 1 1 calc R U . . .
C19 C 0.0350(8) -0.0910(3) 0.62963(9) 0.0209(9) Uani 1 1 d . . . . .
C20 C 0.1969(7) -0.0100(3) 0.61813(9) 0.0219(9) Uani 1 1 d . . . . .
H20 H 0.3557 -0.0116 0.6264 0.026 Uiso 1 1 calc R U . . .
C21 C 0.1441(8) 0.0656(3) 0.59724(10) 0.0222(10) Uani 1 1 d . . . . .
H21 H -0.0156 0.0737 0.5897 0.027 Uiso 1 1 calc R U . . .
C22 C 0.3319(8) 0.1369(3) 0.58574(10) 0.0230(10) Uani 1 1 d . . . . .
C23 C 0.2610(8) 0.2251(3) 0.56370(9) 0.0206(9) Uani 1 1 d . . . . .
C24 C 0.0428(8) 0.2747(3) 0.56666(9) 0.0248(10) Uani 1 1 d . . . . .
H24 H -0.0710 0.2518 0.5824 0.030 Uiso 1 1 calc R U . . .
C25 C -0.0092(8) 0.3581(3) 0.54649(10) 0.0252(10) Uani 1 1 d . . . . .
H25 H -0.1574 0.3932 0.5487 0.030 Uiso 1 1 calc R U . . .
C26 C 0.1543(8) 0.3899(3) 0.52332(10) 0.0263(11) Uani 1 1 d . . . . .
C27 C 0.3721(8) 0.3409(3) 0.51952(10) 0.0246(10) Uani 1 1 d . . . . .
H27 H 0.4827 0.3633 0.5033 0.029 Uiso 1 1 calc R U . . .
C28 C 0.4261(8) 0.2586(3) 0.53981(9) 0.0208(8) Uani 1 1 d . . . . .
H28 H 0.5754 0.2244 0.5376 0.025 Uiso 1 1 calc R U . . .
C29 C 0.5692(8) -0.1495(3) 0.85040(9) 0.0215(9) Uani 1 1 d . . . . .
H29A H 0.4228 -0.1076 0.8475 0.026 Uiso 1 1 calc R U . . .
H29B H 0.5358 -0.2021 0.8674 0.026 Uiso 1 1 calc R U . . .
C30 C 0.7696(8) -0.0809(3) 0.86224(10) 0.0247(10) Uani 1 1 d . . . . .
C31 C 0.7123(7) -0.0021(4) 0.88797(9) 0.0211(9) Uani 1 1 d . . . . .
C32 C 0.8816(8) 0.0745(3) 0.89466(10) 0.0275(11) Uani 1 1 d . . . . .
H32 H 1.0277 0.0759 0.8827 0.033 Uiso 1 1 calc R U . . .
C33 C 0.8381(8) 0.1485(3) 0.91854(11) 0.0300(11) Uani 1 1 d . . . . .
H33 H 0.9514 0.2014 0.9227 0.036 Uiso 1 1 calc R U . . .
C34 C 0.6279(8) 0.1439(3) 0.93609(10) 0.0267(11) Uani 1 1 d . . . . .
C35 C 0.4578(9) 0.0699(3) 0.93042(10) 0.0279(10) Uani 1 1 d . . . . .
H35 H 0.3144 0.0684 0.9429 0.033 Uiso 1 1 calc R U . . .
C36 C 0.4999(7) -0.0033(3) 0.90582(9) 0.0247(10) Uani 1 1 d . . . . .
H36 H 0.3826 -0.0543 0.9013 0.030 Uiso 1 1 calc R U . . .


_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 C26 1.905(4) . ?
Br2 C34 1.905(4) . ?
O1 C4 1.366(5) . ?
O1 C1 1.466(4) . ?
O2 C4 1.203(5) . ?
O3 C22 1.229(5) . ?
O4 C30 1.216(5) . ?
C1 C12 1.492(6) . ?
C1 C2 1.545(5) . ?
C1 H1 1.0000 . ?
C2 C7 1.520(6) . ?
C2 C3 1.547(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.515(6) . ?
C3 C5 1.557(6) . ?
C3 H3 1.0000 . ?
C5 C6 1.509(6) . ?
C5 C29 1.532(5) . ?
C5 H5 1.0000 . ?
C6 C11 1.397(5) . ?
C6 C7 1.399(5) . ?
C7 C8 1.388(5) . ?
C8 C9 1.388(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(6) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.335(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.485(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.398(6) . ?
C14 C19 1.417(5) . ?
C15 C16 1.388(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.397(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.411(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.465(6) . ?
C20 C21 1.332(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.477(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.508(6) . ?
C23 C24 1.386(6) . ?
C23 C28 1.408(5) . ?
C24 C25 1.390(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.376(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.383(6) . ?
C27 C28 1.384(5) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.511(6) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.498(6) . ?
C31 C36 1.391(5) . ?
C31 C32 1.401(6) . ?
C32 C33 1.388(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.376(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.372(6) . ?
C35 C36 1.400(5) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?

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 O1 C1 110.5(3) . . ?
O1 C1 C12 108.5(3) . . ?
O1 C1 C2 104.3(3) . . ?
C12 C1 C2 118.1(3) . . ?
O1 C1 H1 108.5 . . ?
C12 C1 H1 108.5 . . ?
C2 C1 H1 108.5 . . ?
C7 C2 C1 116.9(4) . . ?
C7 C2 C3 102.8(3) . . ?
C1 C2 C3 103.1(3) . . ?
C7 C2 H2 111.1 . . ?
C1 C2 H2 111.1 . . ?
C3 C2 H2 111.1 . . ?
C4 C3 C2 103.7(3) . . ?
C4 C3 C5 114.0(3) . . ?
C2 C3 C5 107.2(3) . . ?
C4 C3 H3 110.5 . . ?
C2 C3 H3 110.5 . . ?
C5 C3 H3 110.5 . . ?
O2 C4 O1 120.6(4) . . ?
O2 C4 C3 129.0(4) . . ?
O1 C4 C3 110.4(4) . . ?
C6 C5 C29 113.7(3) . . ?
C6 C5 C3 102.3(3) . . ?
C29 C5 C3 116.2(3) . . ?
C6 C5 H5 108.1 . . ?
C29 C5 H5 108.1 . . ?
C3 C5 H5 108.1 . . ?
C11 C6 C7 120.2(4) . . ?
C11 C6 C5 128.1(3) . . ?
C7 C6 C5 111.6(3) . . ?
C8 C7 C6 120.4(4) . . ?
C8 C7 C2 128.7(3) . . ?
C6 C7 C2 110.9(3) . . ?
C7 C8 C9 119.6(4) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 119.9(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 121.1(4) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C6 118.7(4) . . ?
C10 C11 H11 120.6 . . ?
C6 C11 H11 120.6 . . ?
C13 C12 C1 122.9(4) . . ?
C13 C12 H12 118.6 . . ?
C1 C12 H12 118.6 . . ?
C12 C13 C14 124.1(4) . . ?
C12 C13 H13 117.9 . . ?
C14 C13 H13 117.9 . . ?
C15 C14 C19 119.6(4) . . ?
C15 C14 C13 119.4(4) . . ?
C19 C14 C13 121.1(4) . . ?
C16 C15 C14 121.1(4) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.6(4) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 120.2(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 121.3(4) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C14 118.3(4) . . ?
C18 C19 C20 119.9(4) . . ?
C14 C19 C20 121.8(4) . . ?
C21 C20 C19 126.6(4) . . ?
C21 C20 H20 116.7 . . ?
C19 C20 H20 116.7 . . ?
C20 C21 C22 120.5(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
O3 C22 C21 122.1(4) . . ?
O3 C22 C23 119.2(4) . . ?
C21 C22 C23 118.6(4) . . ?
C24 C23 C28 119.6(4) . . ?
C24 C23 C22 122.3(4) . . ?
C28 C23 C22 118.2(4) . . ?
C23 C24 C25 119.7(4) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C26 C25 C24 119.9(4) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 121.5(4) . . ?
C25 C26 Br1 119.2(3) . . ?
C27 C26 Br1 119.2(3) . . ?
C26 C27 C28 118.8(4) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
C27 C28 C23 120.4(4) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
C30 C29 C5 112.7(4) . . ?
C30 C29 H29A 109.0 . . ?
C5 C29 H29A 109.0 . . ?
C30 C29 H29B 109.0 . . ?
C5 C29 H29B 109.0 . . ?
H29A C29 H29B 107.8 . . ?
O4 C30 C31 120.2(4) . . ?
O4 C30 C29 121.9(4) . . ?
C31 C30 C29 117.9(4) . . ?
C36 C31 C32 118.9(4) . . ?
C36 C31 C30 122.6(4) . . ?
C32 C31 C30 118.5(4) . . ?
C33 C32 C31 120.7(4) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C34 C33 C32 118.8(4) . . ?
C34 C33 H33 120.6 . . ?
C32 C33 H33 120.6 . . ?
C35 C34 C33 122.4(4) . . ?
C35 C34 Br2 117.9(3) . . ?
C33 C34 Br2 119.6(4) . . ?
C34 C35 C36 118.7(4) . . ?
C34 C35 H35 120.7 . . ?
C36 C35 H35 120.7 . . ?
C31 C36 C35 120.5(4) . . ?
C31 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O1 C1 C12 150.9(3) . . . . ?
C4 O1 C1 C2 24.2(4) . . . . ?
O1 C1 C2 C7 84.1(4) . . . . ?
C12 C1 C2 C7 -36.4(5) . . . . ?
O1 C1 C2 C3 -27.9(4) . . . . ?
C12 C1 C2 C3 -148.4(4) . . . . ?
C7 C2 C3 C4 -100.0(4) . . . . ?
C1 C2 C3 C4 22.0(4) . . . . ?
C7 C2 C3 C5 20.9(4) . . . . ?
C1 C2 C3 C5 142.9(3) . . . . ?
C1 O1 C4 O2 170.6(4) . . . . ?
C1 O1 C4 C3 -10.0(5) . . . . ?
C2 C3 C4 O2 170.9(4) . . . . ?
C5 C3 C4 O2 54.6(6) . . . . ?
C2 C3 C4 O1 -8.4(4) . . . . ?
C5 C3 C4 O1 -124.7(4) . . . . ?
C4 C3 C5 C6 91.9(4) . . . . ?
C2 C3 C5 C6 -22.3(4) . . . . ?
C4 C3 C5 C29 -32.6(5) . . . . ?
C2 C3 C5 C29 -146.8(4) . . . . ?
C29 C5 C6 C11 -40.9(6) . . . . ?
C3 C5 C6 C11 -167.1(4) . . . . ?
C29 C5 C6 C7 141.7(4) . . . . ?
C3 C5 C6 C7 15.5(4) . . . . ?
C11 C6 C7 C8 -1.5(6) . . . . ?
C5 C6 C7 C8 176.1(4) . . . . ?
C11 C6 C7 C2 179.8(4) . . . . ?
C5 C6 C7 C2 -2.6(5) . . . . ?
C1 C2 C7 C8 57.6(6) . . . . ?
C3 C2 C7 C8 169.8(4) . . . . ?
C1 C2 C7 C6 -123.7(4) . . . . ?
C3 C2 C7 C6 -11.6(4) . . . . ?
C6 C7 C8 C9 3.6(6) . . . . ?
C2 C7 C8 C9 -177.8(4) . . . . ?
C7 C8 C9 C10 -2.7(6) . . . . ?
C8 C9 C10 C11 -0.5(7) . . . . ?
C9 C10 C11 C6 2.7(6) . . . . ?
C7 C6 C11 C10 -1.7(6) . . . . ?
C5 C6 C11 C10 -178.9(4) . . . . ?
O1 C1 C12 C13 124.5(4) . . . . ?
C2 C1 C12 C13 -117.1(5) . . . . ?
C1 C12 C13 C14 176.4(4) . . . . ?
C12 C13 C14 C15 -32.7(6) . . . . ?
C12 C13 C14 C19 145.9(4) . . . . ?
C19 C14 C15 C16 -2.2(6) . . . . ?
C13 C14 C15 C16 176.4(4) . . . . ?
C14 C15 C16 C17 0.5(6) . . . . ?
C15 C16 C17 C18 1.1(6) . . . . ?
C16 C17 C18 C19 -0.9(6) . . . . ?
C17 C18 C19 C14 -0.9(6) . . . . ?
C17 C18 C19 C20 177.6(4) . . . . ?
C15 C14 C19 C18 2.4(6) . . . . ?
C13 C14 C19 C18 -176.2(4) . . . . ?
C15 C14 C19 C20 -176.1(4) . . . . ?
C13 C14 C19 C20 5.3(6) . . . . ?
C18 C19 C20 C21 23.2(6) . . . . ?
C14 C19 C20 C21 -158.3(4) . . . . ?
C19 C20 C21 C22 -174.9(4) . . . . ?
C20 C21 C22 O3 6.3(6) . . . . ?
C20 C21 C22 C23 -176.4(4) . . . . ?
O3 C22 C23 C24 -148.8(4) . . . . ?
C21 C22 C23 C24 33.8(6) . . . . ?
O3 C22 C23 C28 29.9(6) . . . . ?
C21 C22 C23 C28 -147.4(4) . . . . ?
C28 C23 C24 C25 -1.2(6) . . . . ?
C22 C23 C24 C25 177.5(4) . . . . ?
C23 C24 C25 C26 1.1(6) . . . . ?
C24 C25 C26 C27 -0.2(6) . . . . ?
C24 C25 C26 Br1 177.1(3) . . . . ?
C25 C26 C27 C28 -0.6(6) . . . . ?
Br1 C26 C27 C28 -177.9(3) . . . . ?
C26 C27 C28 C23 0.5(6) . . . . ?
C24 C23 C28 C27 0.5(6) . . . . ?
C22 C23 C28 C27 -178.4(3) . . . . ?
C6 C5 C29 C30 -179.4(3) . . . . ?
C3 C5 C29 C30 -60.9(5) . . . . ?
C5 C29 C30 O4 -18.2(6) . . . . ?
C5 C29 C30 C31 163.1(4) . . . . ?
O4 C30 C31 C36 -165.5(4) . . . . ?
C29 C30 C31 C36 13.3(6) . . . . ?
O4 C30 C31 C32 13.3(6) . . . . ?
C29 C30 C31 C32 -167.9(4) . . . . ?
C36 C31 C32 C33 -0.4(6) . . . . ?
C30 C31 C32 C33 -179.2(4) . . . . ?
C31 C32 C33 C34 1.5(6) . . . . ?
C32 C33 C34 C35 -1.3(7) . . . . ?
C32 C33 C34 Br2 -179.1(3) . . . . ?
C33 C34 C35 C36 -0.1(6) . . . . ?
Br2 C34 C35 C36 177.8(3) . . . . ?
C32 C31 C36 C35 -1.0(6) . . . . ?
C30 C31 C36 C35 177.8(4) . . . . ?
C34 C35 C36 C31 1.2(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C21 H21 O3 0.95 2.55 3.446(5) 157.0 1_455
C29 H29A O4 0.99 2.53 3.426(6) 149.8 1_455

_refine_diff_density_max         0.485
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.075

_shelxl_version_number           2014-1



