# Electronic Supplementary Material (ESI) for ChemComm.
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1479561'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 O3'
_chemical_formula_weight         356.40

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   11.8870(4)
_cell_length_b                   10.4572(4)
_cell_length_c                   14.8193(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.3600(10)
_cell_angle_gamma                90.00
_cell_volume                     1812.08(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9683
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_process_details   sadabs

_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_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20389
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3189
_reflns_number_gt                2553
_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)+(0.0665P)²+3.1826P] 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         3189
_refine_ls_number_parameters     244
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.1809
_refine_ls_wR_factor_gt          0.1698
_refine_ls_goodness_of_fit_ref   1.058
_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
O1 O 0.20957(18) 0.2757(2) -0.33467(14) 0.0376(6) Uani 1 1 d . . .
O2 O 0.0597(2) 0.1484(2) -0.33255(14) 0.0423(6) Uani 1 1 d . . .
O3 O 0.36706(19) 0.6366(2) 0.01399(15) 0.0383(6) Uani 1 1 d . . .
C1 C 0.1557(3) 0.2128(3) -0.1868(2) 0.0333(7) Uani 1 1 d . . .
C2 C 0.0334(3) 0.2136(3) -0.1635(2) 0.0341(7) Uani 1 1 d . . .
C3 C -0.0437(3) 0.3079(4) -0.1738(2) 0.0418(8) Uani 1 1 d . . .
H3A H -0.0270 0.3885 -0.1978 0.050 Uiso 1 1 calc R . .
C4 C -0.1473(3) 0.2852(4) -0.1490(2) 0.0430(8) Uani 1 1 d . . .
H4A H -0.2026 0.3518 -0.1570 0.052 Uiso 1 1 calc R . .
C5 C -0.1751(3) 0.1709(4) -0.1132(2) 0.0419(8) Uani 1 1 d . . .
H5A H -0.2480 0.1588 -0.0966 0.050 Uiso 1 1 calc R . .
C6 C -0.0924(3) 0.0703(3) -0.1013(2) 0.0435(8) Uani 1 1 d U . .
H6A H -0.1078 -0.0102 -0.0764 0.052 Uiso 1 1 calc R . .
C7 C 0.0143(3) 0.0969(3) -0.1286(2) 0.0336(7) Uani 1 1 d U . .
C8 C 0.1141(3) 0.0150(3) -0.1241(2) 0.0375(8) Uani 1 1 d . . .
H8A H 0.1198 -0.0709 -0.1028 0.045 Uiso 1 1 calc R . .
C9 C 0.1957(3) 0.0790(3) -0.1543(2) 0.0306(6) Uani 1 1 d U . .
C10 C 0.3152(3) 0.0289(3) -0.1566(2) 0.0380(7) Uani 1 1 d U . .
C11 C 0.3542(3) -0.0836(3) -0.1151(3) 0.0487(9) Uani 1 1 d . . .
H11A H 0.3042 -0.1320 -0.0850 0.058 Uiso 1 1 calc R . .
C12 C 0.4587(4) -0.1280(4) -0.1152(3) 0.0592(11) Uani 1 1 d . . .
H12A H 0.4816 -0.2068 -0.0855 0.071 Uiso 1 1 calc R . .
C13 C 0.5337(3) -0.0621(4) -0.1572(3) 0.0497(10) Uani 1 1 d . . .
H13A H 0.6080 -0.0958 -0.1569 0.060 Uiso 1 1 calc R . .
C14 C 0.5033(3) 0.0519(3) -0.2000(2) 0.0414(8) Uani 1 1 d . . .
H14A H 0.5558 0.0975 -0.2292 0.050 Uiso 1 1 calc R . .
C15 C 0.3915(3) 0.1011(3) -0.1998(2) 0.0398(7) Uani 1 1 d U . .
H15A H 0.3686 0.1808 -0.2281 0.048 Uiso 1 1 calc R . .
C16 C 0.2261(2) 0.3216(3) -0.1365(2) 0.0286(7) Uani 1 1 d . . .
C17 C 0.2828(2) 0.3046(3) -0.0468(2) 0.0278(6) Uani 1 1 d . . .
H17A H 0.2893 0.2210 -0.0213 0.033 Uiso 1 1 calc R . .
C18 C 0.3300(2) 0.4069(3) 0.0061(2) 0.0277(6) Uani 1 1 d . . .
H18A H 0.3677 0.3936 0.0675 0.033 Uiso 1 1 calc R . .
C19 C 0.3220(2) 0.5291(3) -0.0313(2) 0.0267(6) Uani 1 1 d . . .
C20 C 0.2660(3) 0.5467(3) -0.1208(2) 0.0333(7) Uani 1 1 d . . .
H20A H 0.2599 0.6301 -0.1465 0.040 Uiso 1 1 calc R . .
C21 C 0.2191(3) 0.4448(3) -0.1725(2) 0.0333(7) Uani 1 1 d . . .
H21A H 0.1813 0.4585 -0.2339 0.040 Uiso 1 1 calc R . .
C22 C 0.1485(3) 0.2179(3) -0.2926(2) 0.0316(7) Uani 1 1 d . . .
C23 C 0.0365(3) 0.1476(3) -0.4312(2) 0.0385(8) Uani 1 1 d . . .
H23A H -0.0302 0.0934 -0.4529 0.058 Uiso 1 1 calc R . .
H23B H 0.1030 0.1139 -0.4540 0.058 Uiso 1 1 calc R . .
H23C H 0.0207 0.2350 -0.4539 0.058 Uiso 1 1 calc R . .
C24 C 0.4308(3) 0.6204(3) 0.1041(2) 0.0395(8) Uani 1 1 d . . .
H24A H 0.4580 0.7039 0.1291 0.059 Uiso 1 1 calc R . .
H24B H 0.4965 0.5646 0.1019 0.059 Uiso 1 1 calc R . .
H24C H 0.3820 0.5817 0.1433 0.059 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
O1 C22 1.201(4) . ?
O2 C22 1.330(4) . ?
O2 C23 1.438(4) . ?
O3 C19 1.368(3) . ?
O3 C24 1.422(4) . ?
C1 C16 1.524(4) . ?
C1 C9 1.527(4) . ?
C1 C2 1.554(4) . ?
C1 C22 1.556(4) . ?
C2 C3 1.336(5) . ?
C2 C7 1.360(5) . ?
C3 C4 1.367(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.373(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.428(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.426(5) . ?
C6 H6A 0.9500 . ?
C7 C8 1.456(4) . ?
C8 C9 1.321(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.520(4) . ?
C10 C11 1.369(5) . ?
C10 C15 1.419(5) . ?
C11 C12 1.326(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.363(6) . ?
C12 H12A 0.9500 . ?
C13 C14 1.368(5) . ?
C13 H13A 0.9500 . ?
C14 C15 1.425(5) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C17 1.390(4) . ?
C16 C21 1.392(4) . ?
C17 C18 1.384(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.388(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.386(4) . ?
C20 C21 1.371(4) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C22 O2 C23 116.6(2) . . ?
C19 O3 C24 117.3(2) . . ?
C16 C1 C9 114.6(2) . . ?
C16 C1 C2 109.9(2) . . ?
C9 C1 C2 100.7(2) . . ?
C16 C1 C22 113.1(2) . . ?
C9 C1 C22 107.8(2) . . ?
C2 C1 C22 109.9(2) . . ?
C3 C2 C7 123.2(3) . . ?
C3 C2 C1 128.9(3) . . ?
C7 C2 C1 107.9(3) . . ?
C2 C3 C4 118.3(3) . . ?
C2 C3 H3A 120.9 . . ?
C4 C3 H3A 120.9 . . ?
C3 C4 C5 123.1(3) . . ?
C3 C4 H4A 118.5 . . ?
C5 C4 H4A 118.5 . . ?
C4 C5 C6 118.7(3) . . ?
C4 C5 H5A 120.6 . . ?
C6 C5 H5A 120.6 . . ?
C5 C6 C7 116.7(3) . . ?
C5 C6 H6A 121.7 . . ?
C7 C6 H6A 121.7 . . ?
C2 C7 C6 120.0(3) . . ?
C2 C7 C8 110.8(3) . . ?
C6 C7 C8 129.2(3) . . ?
C9 C8 C7 109.2(3) . . ?
C9 C8 H8A 125.4 . . ?
C7 C8 H8A 125.4 . . ?
C8 C9 C10 125.3(3) . . ?
C8 C9 C1 111.4(3) . . ?
C10 C9 C1 123.3(3) . . ?
C11 C10 C15 117.9(3) . . ?
C11 C10 C9 122.0(3) . . ?
C15 C10 C9 120.1(3) . . ?
C12 C11 C10 122.8(4) . . ?
C12 C11 H11A 118.6 . . ?
C10 C11 H11A 118.6 . . ?
C11 C12 C13 120.9(4) . . ?
C11 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13A 119.6 . . ?
C14 C13 H13A 119.6 . . ?
C13 C14 C15 118.9(3) . . ?
C13 C14 H14A 120.6 . . ?
C15 C14 H14A 120.6 . . ?
C10 C15 C14 118.7(3) . . ?
C10 C15 H15A 120.6 . . ?
C14 C15 H15A 120.6 . . ?
C17 C16 C21 118.1(3) . . ?
C17 C16 C1 120.1(3) . . ?
C21 C16 C1 120.9(3) . . ?
C18 C17 C16 121.4(3) . . ?
C18 C17 H17A 119.3 . . ?
C16 C17 H17A 119.3 . . ?
C17 C18 C19 119.6(3) . . ?
C17 C18 H18A 120.2 . . ?
C19 C18 H18A 120.2 . . ?
O3 C19 C20 116.0(3) . . ?
O3 C19 C18 124.6(3) . . ?
C20 C19 C18 119.4(3) . . ?
C21 C20 C19 120.6(3) . . ?
C21 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
C20 C21 C16 121.0(3) . . ?
C20 C21 H21A 119.5 . . ?
C16 C21 H21A 119.5 . . ?
O1 C22 O2 123.3(3) . . ?
O1 C22 C1 127.7(3) . . ?
O2 C22 C1 109.0(2) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
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 . . ?

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
C16 C1 C2 C3 56.5(4) . . . . ?
C9 C1 C2 C3 177.8(3) . . . . ?
C22 C1 C2 C3 -68.6(4) . . . . ?
C16 C1 C2 C7 -123.4(3) . . . . ?
C9 C1 C2 C7 -2.1(3) . . . . ?
C22 C1 C2 C7 111.4(3) . . . . ?
C7 C2 C3 C4 -0.8(5) . . . . ?
C1 C2 C3 C4 179.3(3) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C7 -0.3(5) . . . . ?
C3 C2 C7 C6 0.2(5) . . . . ?
C1 C2 C7 C6 -179.8(3) . . . . ?
C3 C2 C7 C8 -179.0(3) . . . . ?
C1 C2 C7 C8 0.9(3) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
C5 C6 C7 C8 179.4(3) . . . . ?
C2 C7 C8 C9 0.9(4) . . . . ?
C6 C7 C8 C9 -178.3(3) . . . . ?
C7 C8 C9 C10 177.1(3) . . . . ?
C7 C8 C9 C1 -2.4(4) . . . . ?
C16 C1 C9 C8 120.7(3) . . . . ?
C2 C1 C9 C8 2.8(3) . . . . ?
C22 C1 C9 C8 -112.4(3) . . . . ?
C16 C1 C9 C10 -58.8(4) . . . . ?
C2 C1 C9 C10 -176.7(3) . . . . ?
C22 C1 C9 C10 68.2(3) . . . . ?
C8 C9 C10 C11 -9.0(5) . . . . ?
C1 C9 C10 C11 170.4(3) . . . . ?
C8 C9 C10 C15 173.1(3) . . . . ?
C1 C9 C10 C15 -7.5(4) . . . . ?
C15 C10 C11 C12 -1.1(5) . . . . ?
C9 C10 C11 C12 -179.0(3) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 0.4(6) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C11 C10 C15 C14 1.5(4) . . . . ?
C9 C10 C15 C14 179.5(3) . . . . ?
C13 C14 C15 C10 -1.0(5) . . . . ?
C9 C1 C16 C17 -27.5(4) . . . . ?
C2 C1 C16 C17 85.0(3) . . . . ?
C22 C1 C16 C17 -151.7(3) . . . . ?
C9 C1 C16 C21 163.7(3) . . . . ?
C2 C1 C16 C21 -83.7(3) . . . . ?
C22 C1 C16 C21 39.5(4) . . . . ?
C21 C16 C17 C18 0.8(4) . . . . ?
C1 C16 C17 C18 -168.3(3) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C24 O3 C19 C20 -176.4(3) . . . . ?
C24 O3 C19 C18 3.0(4) . . . . ?
C17 C18 C19 O3 -178.9(3) . . . . ?
C17 C18 C19 C20 0.5(4) . . . . ?
O3 C19 C20 C21 179.1(3) . . . . ?
C18 C19 C20 C21 -0.3(4) . . . . ?
C19 C20 C21 C16 0.3(5) . . . . ?
C17 C16 C21 C20 -0.5(5) . . . . ?
C1 C16 C21 C20 168.4(3) . . . . ?
C23 O2 C22 O1 -1.8(5) . . . . ?
C23 O2 C22 C1 176.9(3) . . . . ?
C16 C1 C22 O1 18.2(5) . . . . ?
C9 C1 C22 O1 -109.7(4) . . . . ?
C2 C1 C22 O1 141.4(3) . . . . ?
C16 C1 C22 O2 -160.5(3) . . . . ?
C9 C1 C22 O2 71.7(3) . . . . ?
C2 C1 C22 O2 -37.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1479562'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 O4'
_chemical_formula_weight         372.40

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   12.6203(7)
_cell_length_b                   10.0898(6)
_cell_length_c                   15.4768(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.857(2)
_cell_angle_gamma                90.00
_cell_volume                     1886.08(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8545
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.89

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9586
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21282
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3311
_reflns_number_gt                2789
_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)+(0.0450P)²+0.5231P] 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       0.0046(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3311
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
O1 O 0.44231(11) 0.38795(13) 0.20993(8) 0.0702(4) Uani 1 1 d . . .
O2 O 0.41350(10) 0.40188(10) 0.34424(8) 0.0549(3) Uani 1 1 d . . .
O3 O 0.43915(8) 0.66565(11) 0.15044(7) 0.0509(3) Uani 1 1 d . . .
O4 O 0.92462(9) 0.45262(12) 0.56844(7) 0.0600(3) Uani 1 1 d . . .
C1 C 0.74188(12) 0.62273(16) 0.22804(10) 0.0458(4) Uani 1 1 d . . .
H1A H 0.7586 0.6762 0.2792 0.055 Uiso 1 1 calc R . .
C2 C 0.82582(13) 0.57761(17) 0.19476(11) 0.0533(4) Uani 1 1 d . . .
H2A H 0.8989 0.5998 0.2243 0.064 Uiso 1 1 calc R . .
C3 C 0.80233(14) 0.50041(18) 0.11868(12) 0.0589(4) Uani 1 1 d . . .
H3A H 0.8591 0.4710 0.0964 0.071 Uiso 1 1 calc R . .
C4 C 0.69425(15) 0.46670(18) 0.07548(12) 0.0615(5) Uani 1 1 d . . .
H4A H 0.6779 0.4150 0.0235 0.074 Uiso 1 1 calc R . .
C5 C 0.61017(13) 0.50933(16) 0.10902(10) 0.0500(4) Uani 1 1 d . . .
H5A H 0.5375 0.4848 0.0801 0.060 Uiso 1 1 calc R . .
C6 C 0.63299(11) 0.58856(13) 0.18547(9) 0.0386(3) Uani 1 1 d . . .
C7 C 0.54028(11) 0.63560(14) 0.21958(9) 0.0378(3) Uani 1 1 d . . .
C8 C 0.49770(12) 0.77217(15) 0.20915(10) 0.0452(4) Uani 1 1 d . . .
H8A H 0.5355 0.8426 0.1860 0.054 Uiso 1 1 calc R . .
C9 C 0.44607(11) 0.79813(14) 0.28148(10) 0.0432(3) Uani 1 1 d . . .
C10 C 0.39323(14) 0.91181(15) 0.29766(12) 0.0555(4) Uani 1 1 d . . .
H10A H 0.3893 0.9868 0.2619 0.067 Uiso 1 1 calc R . .
C11 C 0.34663(15) 0.91135(17) 0.36789(14) 0.0647(5) Uani 1 1 d . . .
H11A H 0.3110 0.9868 0.3799 0.078 Uiso 1 1 calc R . .
C12 C 0.35238(15) 0.79980(17) 0.42060(14) 0.0637(5) Uani 1 1 d . . .
H12A H 0.3209 0.8014 0.4680 0.076 Uiso 1 1 calc R . .
C13 C 0.40418(13) 0.68529(15) 0.40427(11) 0.0516(4) Uani 1 1 d . . .
H13A H 0.4070 0.6102 0.4397 0.062 Uiso 1 1 calc R . .
C14 C 0.45164(11) 0.68532(13) 0.33405(10) 0.0400(3) Uani 1 1 d . . .
C15 C 0.51720(11) 0.57507(13) 0.30477(9) 0.0362(3) Uani 1 1 d . . .
C16 C 0.62527(11) 0.54054(13) 0.37723(9) 0.0350(3) Uani 1 1 d . . .
C17 C 0.67649(12) 0.62745(14) 0.44584(10) 0.0441(4) Uani 1 1 d . . .
H17A H 0.6433 0.7085 0.4501 0.053 Uiso 1 1 calc R . .
C18 C 0.77591(13) 0.59568(16) 0.50792(10) 0.0512(4) Uani 1 1 d . . .
H18A H 0.8090 0.6557 0.5533 0.061 Uiso 1 1 calc R . .
C19 C 0.82687(11) 0.47576(15) 0.50344(9) 0.0431(3) Uani 1 1 d . . .
C20 C 0.77798(12) 0.38837(14) 0.43507(10) 0.0429(3) Uani 1 1 d . . .
H20A H 0.8116 0.3076 0.4307 0.051 Uiso 1 1 calc R . .
C21 C 0.67853(12) 0.42169(14) 0.37309(10) 0.0421(3) Uani 1 1 d . . .
H21A H 0.6463 0.3623 0.3270 0.050 Uiso 1 1 calc R . .
C22 C 0.97784(14) 0.32894(19) 0.56429(12) 0.0636(5) Uani 1 1 d . . .
H22A H 1.0453 0.3239 0.6129 0.095 Uiso 1 1 calc R . .
H22B H 0.9943 0.3221 0.5077 0.095 Uiso 1 1 calc R . .
H22C H 0.9297 0.2577 0.5695 0.095 Uiso 1 1 calc R . .
C23 C 0.45214(11) 0.44637(14) 0.27865(10) 0.0417(3) Uani 1 1 d . . .
C24 C 0.36859(16) 0.26952(17) 0.33290(14) 0.0683(5) Uani 1 1 d . . .
H24A H 0.3429 0.2470 0.3837 0.102 Uiso 1 1 calc R . .
H24B H 0.4250 0.2081 0.3289 0.102 Uiso 1 1 calc R . .
H24C H 0.3079 0.2653 0.2786 0.102 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
O1 C23 1.1906(17) . ?
O2 C23 1.3255(18) . ?
O2 C24 1.4414(19) . ?
O3 C7 1.4401(15) . ?
O3 C8 1.4620(18) . ?
O4 C19 1.3670(17) . ?
O4 C22 1.427(2) . ?
C1 C2 1.383(2) . ?
C1 C6 1.384(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.371(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.376(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.378(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.387(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.4937(19) . ?
C7 C8 1.471(2) . ?
C7 C15 1.5553(19) . ?
C8 C9 1.473(2) . ?
C8 H8A 0.9800 . ?
C9 C10 1.386(2) . ?
C9 C14 1.389(2) . ?
C10 C11 1.378(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.380(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.386(2) . ?
C12 H12A 0.9300 . ?
C13 C14 1.385(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.5313(18) . ?
C15 C23 1.5268(19) . ?
C15 C16 1.5337(18) . ?
C16 C17 1.3842(19) . ?
C16 C21 1.3852(19) . ?
C17 C18 1.379(2) . ?
C17 H17A 0.9300 . ?
C18 C19 1.381(2) . ?
C18 H18A 0.9300 . ?
C19 C20 1.378(2) . ?
C20 C21 1.382(2) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C23 O2 C24 116.07(12) . . ?
C7 O3 C8 60.90(9) . . ?
C19 O4 C22 116.89(12) . . ?
C2 C1 C6 120.18(14) . . ?
C2 C1 H1A 119.9 . . ?
C6 C1 H1A 119.9 . . ?
C3 C2 C1 120.60(15) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 119.65(15) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 C5 120.19(16) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 120.59(15) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C1 C6 C5 118.78(13) . . ?
C1 C6 C7 121.59(12) . . ?
C5 C6 C7 119.62(13) . . ?
O3 C7 C8 60.29(9) . . ?
O3 C7 C6 114.87(11) . . ?
C8 C7 C6 123.89(12) . . ?
O3 C7 C15 111.66(11) . . ?
C8 C7 C15 107.98(11) . . ?
C6 C7 C15 122.23(11) . . ?
O3 C8 C7 58.81(8) . . ?
O3 C8 C9 110.35(12) . . ?
C7 C8 C9 108.14(12) . . ?
O3 C8 H8A 121.2 . . ?
C7 C8 H8A 121.2 . . ?
C9 C8 H8A 121.2 . . ?
C10 C9 C14 121.18(14) . . ?
C10 C9 C8 128.81(14) . . ?
C14 C9 C8 109.95(12) . . ?
C11 C10 C9 118.53(15) . . ?
C11 C10 H10A 120.7 . . ?
C9 C10 H10A 120.7 . . ?
C10 C11 C12 120.53(15) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C11 C12 C13 121.26(16) . . ?
C11 C12 H12A 119.4 . . ?
C13 C12 H12A 119.4 . . ?
C14 C13 C12 118.49(15) . . ?
C14 C13 H13A 120.8 . . ?
C12 C13 H13A 120.8 . . ?
C13 C14 C9 120.00(13) . . ?
C13 C14 C15 128.76(13) . . ?
C9 C14 C15 111.21(12) . . ?
C23 C15 C14 113.64(11) . . ?
C23 C15 C16 107.24(11) . . ?
C14 C15 C16 113.00(11) . . ?
C23 C15 C7 109.15(11) . . ?
C14 C15 C7 102.46(11) . . ?
C16 C15 C7 111.32(10) . . ?
C17 C16 C21 117.32(13) . . ?
C17 C16 C15 122.38(12) . . ?
C21 C16 C15 120.22(12) . . ?
C18 C17 C16 121.03(13) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C17 C18 C19 120.76(14) . . ?
C17 C18 H18A 119.6 . . ?
C19 C18 H18A 119.6 . . ?
O4 C19 C20 124.28(13) . . ?
O4 C19 C18 116.53(13) . . ?
C20 C19 C18 119.19(13) . . ?
C19 C20 C21 119.44(13) . . ?
C19 C20 H20A 120.3 . . ?
C21 C20 H20A 120.3 . . ?
C20 C21 C16 122.25(13) . . ?
C20 C21 H21A 118.9 . . ?
C16 C21 H21A 118.9 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 C23 O2 123.39(14) . . ?
O1 C23 C15 124.49(14) . . ?
O2 C23 C15 111.98(12) . . ?
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 . . ?

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 1.0(2) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C2 C1 C6 C5 -0.4(2) . . . . ?
C2 C1 C6 C7 -179.98(14) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C4 C5 C6 C7 178.88(15) . . . . ?
C8 O3 C7 C6 -116.30(14) . . . . ?
C8 O3 C7 C15 98.96(13) . . . . ?
C1 C6 C7 O3 143.91(13) . . . . ?
C5 C6 C7 O3 -35.70(18) . . . . ?
C1 C6 C7 C8 74.20(18) . . . . ?
C5 C6 C7 C8 -105.42(16) . . . . ?
C1 C6 C7 C15 -75.45(18) . . . . ?
C5 C6 C7 C15 104.93(15) . . . . ?
C7 O3 C8 C9 -99.41(13) . . . . ?
C6 C7 C8 O3 101.54(14) . . . . ?
C15 C7 C8 O3 -105.16(11) . . . . ?
O3 C7 C8 C9 103.27(12) . . . . ?
C6 C7 C8 C9 -155.19(12) . . . . ?
C15 C7 C8 C9 -1.89(15) . . . . ?
O3 C8 C9 C10 -115.97(16) . . . . ?
C7 C8 C9 C10 -178.60(15) . . . . ?
O3 C8 C9 C14 61.06(15) . . . . ?
C7 C8 C9 C14 -1.57(16) . . . . ?
C14 C9 C10 C11 0.5(2) . . . . ?
C8 C9 C10 C11 177.24(16) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C9 -0.4(2) . . . . ?
C12 C13 C14 C15 177.19(15) . . . . ?
C10 C9 C14 C13 -0.2(2) . . . . ?
C8 C9 C14 C13 -177.50(13) . . . . ?
C10 C9 C14 C15 -178.20(13) . . . . ?
C8 C9 C14 C15 4.51(16) . . . . ?
C13 C14 C15 C23 59.26(19) . . . . ?
C9 C14 C15 C23 -122.97(13) . . . . ?
C13 C14 C15 C16 -63.24(18) . . . . ?
C9 C14 C15 C16 114.53(13) . . . . ?
C13 C14 C15 C7 176.87(14) . . . . ?
C9 C14 C15 C7 -5.36(15) . . . . ?
O3 C7 C15 C23 60.57(14) . . . . ?
C8 C7 C15 C23 124.99(12) . . . . ?
C6 C7 C15 C23 -81.18(15) . . . . ?
O3 C7 C15 C14 -60.19(13) . . . . ?
C8 C7 C15 C14 4.22(14) . . . . ?
C6 C7 C15 C14 158.06(12) . . . . ?
O3 C7 C15 C16 178.75(10) . . . . ?
C8 C7 C15 C16 -116.83(12) . . . . ?
C6 C7 C15 C16 37.01(17) . . . . ?
C23 C15 C16 C17 -147.30(13) . . . . ?
C14 C15 C16 C17 -21.30(18) . . . . ?
C7 C15 C16 C17 93.36(15) . . . . ?
C23 C15 C16 C21 36.11(16) . . . . ?
C14 C15 C16 C21 162.11(12) . . . . ?
C7 C15 C16 C21 -83.22(15) . . . . ?
C21 C16 C17 C18 -0.7(2) . . . . ?
C15 C16 C17 C18 -177.39(13) . . . . ?
C16 C17 C18 C19 -0.3(2) . . . . ?
C22 O4 C19 C20 -0.4(2) . . . . ?
C22 O4 C19 C18 -179.99(15) . . . . ?
C17 C18 C19 O4 -179.37(14) . . . . ?
C17 C18 C19 C20 1.0(2) . . . . ?
O4 C19 C20 C21 179.66(14) . . . . ?
C18 C19 C20 C21 -0.7(2) . . . . ?
C19 C20 C21 C16 -0.3(2) . . . . ?
C17 C16 C21 C20 1.0(2) . . . . ?
C15 C16 C21 C20 177.73(13) . . . . ?
C24 O2 C23 O1 6.8(2) . . . . ?
C24 O2 C23 C15 -169.11(13) . . . . ?
C14 C15 C23 O1 128.66(16) . . . . ?
C16 C15 C23 O1 -105.72(17) . . . . ?
C7 C15 C23 O1 15.00(19) . . . . ?
C14 C15 C23 O2 -55.50(16) . . . . ?
C16 C15 C23 O2 70.12(14) . . . . ?
C7 C15 C23 O2 -169.17(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.028
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1479563'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 Br2 O4'
_chemical_formula_weight         516.18

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.0971(3)
_cell_length_b                   11.2035(4)
_cell_length_c                   12.1077(4)
_cell_angle_alpha                87.7950(10)
_cell_angle_beta                 71.1220(10)
_cell_angle_gamma                74.2330(10)
_cell_volume                     998.70(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5540
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      26.07

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    4.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3547
_exptl_absorpt_correction_T_max  0.5107
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11808
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3513
_reflns_number_gt                3041
_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)+(0.0365P)²+0.7247P] 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         3513
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0780
_refine_ls_wR_factor_gt          0.0742
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.37186(4) 0.87554(3) 0.83693(3) 0.05927(12) Uani 1 1 d . . .
Br2 Br -0.43922(5) 1.13761(4) 0.52844(3) 0.06560(13) Uani 1 1 d . . .
O1 O -0.2596(3) 1.32857(18) 0.92967(16) 0.0488(5) Uani 1 1 d . . .
O2 O -0.2338(3) 1.45163(16) 0.78007(16) 0.0417(4) Uani 1 1 d . . .
O3 O 0.0244(3) 0.78378(18) 0.94398(19) 0.0539(5) Uani 1 1 d . . .
H3A H 0.1035 0.7788 0.9737 0.081 Uiso 1 1 calc R . .
O4 O -0.3715(2) 1.11037(17) 0.81349(16) 0.0396(4) Uani 1 1 d . . .
C1 C -0.3369(3) 1.2012(2) 0.7276(2) 0.0334(5) Uani 1 1 d . . .
C2 C -0.2595(3) 1.1364(2) 0.6031(2) 0.0375(6) Uani 1 1 d . . .
H2A H -0.1991 1.0493 0.6103 0.045 Uiso 1 1 calc R . .
C3 C -0.1158(3) 1.1959(2) 0.5356(2) 0.0346(6) Uani 1 1 d . . .
C4 C -0.0345(4) 1.1942(3) 0.4160(2) 0.0456(7) Uani 1 1 d . . .
H4A H -0.0727 1.1565 0.3653 0.055 Uiso 1 1 calc R . .
C5 C 0.1040(5) 1.2494(3) 0.3736(3) 0.0565(8) Uani 1 1 d . . .
H5A H 0.1604 1.2483 0.2933 0.068 Uiso 1 1 calc R . .
C6 C 0.1613(4) 1.3067(3) 0.4480(3) 0.0551(8) Uani 1 1 d . . .
H6A H 0.2551 1.3438 0.4173 0.066 Uiso 1 1 calc R . .
C7 C 0.0794(4) 1.3090(3) 0.5685(2) 0.0425(6) Uani 1 1 d . . .
H7A H 0.1169 1.3475 0.6190 0.051 Uiso 1 1 calc R . .
C8 C -0.0593(3) 1.2526(2) 0.6113(2) 0.0321(5) Uani 1 1 d . . .
C9 C -0.1619(3) 1.2350(2) 0.7364(2) 0.0302(5) Uani 1 1 d . . .
C10 C -0.0776(3) 1.1150(2) 0.7837(2) 0.0318(5) Uani 1 1 d . . .
C11 C 0.0957(3) 1.0640(2) 0.7870(2) 0.0345(6) Uani 1 1 d . . .
H11A H 0.1861 1.1039 0.7557 0.041 Uiso 1 1 calc R . .
C12 C 0.1314(4) 0.9516(2) 0.8385(2) 0.0380(6) Uani 1 1 d . . .
C13 C -0.0026(4) 0.8925(2) 0.8899(2) 0.0387(6) Uani 1 1 d . . .
C14 C -0.1769(4) 0.9429(2) 0.8841(2) 0.0388(6) Uani 1 1 d . . .
H14A H -0.2682 0.9039 0.9161 0.047 Uiso 1 1 calc R . .
C15 C -0.2085(3) 1.0521(2) 0.8293(2) 0.0346(6) Uani 1 1 d . . .
C16 C -0.5051(3) 1.3086(2) 0.7487(2) 0.0356(6) Uani 1 1 d . . .
C17 C -0.6629(4) 1.3092(3) 0.8391(3) 0.0453(7) Uani 1 1 d . . .
H17A H -0.6662 1.2426 0.8873 0.054 Uiso 1 1 calc R . .
C18 C -0.8159(4) 1.4091(3) 0.8578(3) 0.0574(8) Uani 1 1 d . . .
H18A H -0.9214 1.4091 0.9186 0.069 Uiso 1 1 calc R . .
C19 C -0.8133(4) 1.5072(3) 0.7879(3) 0.0617(9) Uani 1 1 d . . .
H19A H -0.9163 1.5741 0.8015 0.074 Uiso 1 1 calc R . .
C20 C -0.6580(5) 1.5074(3) 0.6972(3) 0.0619(9) Uani 1 1 d . . .
H20A H -0.6559 1.5743 0.6495 0.074 Uiso 1 1 calc R . .
C21 C -0.5052(4) 1.4079(3) 0.6773(3) 0.0506(7) Uani 1 1 d . . .
H21A H -0.4013 1.4077 0.6150 0.061 Uiso 1 1 calc R . .
C22 C -0.2203(3) 1.3425(2) 0.8268(2) 0.0318(5) Uani 1 1 d . . .
C23 C -0.3245(5) 1.5582(3) 0.8619(3) 0.0614(9) Uani 1 1 d . . .
H23A H -0.3269 1.6329 0.8201 0.092 Uiso 1 1 calc R . .
H23B H -0.2602 1.5567 0.9163 0.092 Uiso 1 1 calc R . .
H23C H -0.4464 1.5558 0.9035 0.092 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.896(3) . ?
Br2 C2 1.943(2) . ?
O1 C22 1.197(3) . ?
O2 C22 1.320(3) . ?
O2 C23 1.446(3) . ?
O3 C13 1.359(3) . ?
O3 H3A 0.8200 . ?
O4 C15 1.374(3) . ?
O4 C1 1.442(3) . ?
C1 C16 1.509(3) . ?
C1 C2 1.555(4) . ?
C1 C9 1.599(3) . ?
C2 C3 1.494(4) . ?
C2 H2A 0.9800 . ?
C3 C4 1.381(4) . ?
C3 C8 1.388(4) . ?
C4 C5 1.372(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.384(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.392(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.383(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.509(3) . ?
C9 C10 1.515(3) . ?
C9 C22 1.526(3) . ?
C10 C11 1.377(3) . ?
C10 C15 1.387(4) . ?
C11 C12 1.384(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.387(4) . ?
C13 C14 1.395(4) . ?
C14 C15 1.371(4) . ?
C14 H14A 0.9300 . ?
C16 C21 1.383(4) . ?
C16 C17 1.386(4) . ?
C17 C18 1.387(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.361(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.377(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.382(4) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C22 O2 C23 115.5(2) . . ?
C13 O3 H3A 109.5 . . ?
C15 O4 C1 106.76(18) . . ?
O4 C1 C16 109.8(2) . . ?
O4 C1 C2 109.4(2) . . ?
C16 C1 C2 115.2(2) . . ?
O4 C1 C9 105.44(18) . . ?
C16 C1 C9 115.6(2) . . ?
C2 C1 C9 100.62(19) . . ?
C3 C2 C1 105.3(2) . . ?
C3 C2 Br2 114.04(18) . . ?
C1 C2 Br2 115.09(17) . . ?
C3 C2 H2A 107.3 . . ?
C1 C2 H2A 107.3 . . ?
Br2 C2 H2A 107.3 . . ?
C4 C3 C8 120.8(2) . . ?
C4 C3 C2 128.9(2) . . ?
C8 C3 C2 110.2(2) . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4A 120.7 . . ?
C3 C4 H4A 120.7 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6A 119.9 . . ?
C7 C6 H6A 119.9 . . ?
C8 C7 C6 118.4(3) . . ?
C8 C7 H7A 120.8 . . ?
C6 C7 H7A 120.8 . . ?
C7 C8 C3 120.6(2) . . ?
C7 C8 C9 129.1(2) . . ?
C3 C8 C9 110.2(2) . . ?
C8 C9 C10 114.0(2) . . ?
C8 C9 C22 118.6(2) . . ?
C10 C9 C22 110.1(2) . . ?
C8 C9 C1 103.53(19) . . ?
C10 C9 C1 98.56(19) . . ?
C22 C9 C1 109.75(19) . . ?
C11 C10 C15 119.6(2) . . ?
C11 C10 C9 131.6(2) . . ?
C15 C10 C9 108.8(2) . . ?
C10 C11 C12 118.1(2) . . ?
C10 C11 H11A 121.0 . . ?
C12 C11 H11A 121.0 . . ?
C11 C12 C13 122.1(2) . . ?
C11 C12 Br1 118.8(2) . . ?
C13 C12 Br1 119.1(2) . . ?
O3 C13 C12 124.4(3) . . ?
O3 C13 C14 115.9(3) . . ?
C12 C13 C14 119.6(2) . . ?
C15 C14 C13 117.5(3) . . ?
C15 C14 H14A 121.3 . . ?
C13 C14 H14A 121.3 . . ?
C14 C15 O4 124.0(2) . . ?
C14 C15 C10 123.0(2) . . ?
O4 C15 C10 113.1(2) . . ?
C21 C16 C17 118.7(3) . . ?
C21 C16 C1 120.5(2) . . ?
C17 C16 C1 120.8(2) . . ?
C18 C17 C16 120.0(3) . . ?
C18 C17 H17A 120.0 . . ?
C16 C17 H17A 120.0 . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18A 119.7 . . ?
C17 C18 H18A 119.7 . . ?
C18 C19 C20 119.9(3) . . ?
C18 C19 H19A 120.0 . . ?
C20 C19 H19A 120.0 . . ?
C19 C20 C21 119.9(3) . . ?
C19 C20 H20A 120.0 . . ?
C21 C20 H20A 120.0 . . ?
C20 C21 C16 120.8(3) . . ?
C20 C21 H21A 119.6 . . ?
C16 C21 H21A 119.6 . . ?
O1 C22 O2 124.1(2) . . ?
O1 C22 C9 122.8(2) . . ?
O2 C22 C9 112.9(2) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C15 O4 C1 C16 -150.8(2) . . . . ?
C15 O4 C1 C2 81.9(2) . . . . ?
C15 O4 C1 C9 -25.6(2) . . . . ?
O4 C1 C2 C3 -140.6(2) . . . . ?
C16 C1 C2 C3 95.2(2) . . . . ?
C9 C1 C2 C3 -29.9(2) . . . . ?
O4 C1 C2 Br2 92.9(2) . . . . ?
C16 C1 C2 Br2 -31.3(3) . . . . ?
C9 C1 C2 Br2 -156.38(16) . . . . ?
C1 C2 C3 C4 -163.5(3) . . . . ?
Br2 C2 C3 C4 -36.4(4) . . . . ?
C1 C2 C3 C8 20.1(3) . . . . ?
Br2 C2 C3 C8 147.19(18) . . . . ?
C8 C3 C4 C5 0.2(4) . . . . ?
C2 C3 C4 C5 -175.8(3) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C8 0.2(5) . . . . ?
C6 C7 C8 C3 -0.5(4) . . . . ?
C6 C7 C8 C9 175.9(3) . . . . ?
C4 C3 C8 C7 0.3(4) . . . . ?
C2 C3 C8 C7 177.0(2) . . . . ?
C4 C3 C8 C9 -176.7(2) . . . . ?
C2 C3 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C10 -90.1(3) . . . . ?
C3 C8 C9 C10 86.6(3) . . . . ?
C7 C8 C9 C22 42.2(4) . . . . ?
C3 C8 C9 C22 -141.2(2) . . . . ?
C7 C8 C9 C1 164.0(3) . . . . ?
C3 C8 C9 C1 -19.4(3) . . . . ?
O4 C1 C9 C8 143.24(19) . . . . ?
C16 C1 C9 C8 -95.3(2) . . . . ?
C2 C1 C9 C8 29.5(2) . . . . ?
O4 C1 C9 C10 25.9(2) . . . . ?
C16 C1 C9 C10 147.4(2) . . . . ?
C2 C1 C9 C10 -87.8(2) . . . . ?
O4 C1 C9 C22 -89.1(2) . . . . ?
C16 C1 C9 C22 32.3(3) . . . . ?
C2 C1 C9 C22 157.1(2) . . . . ?
C8 C9 C10 C11 53.0(4) . . . . ?
C22 C9 C10 C11 -83.2(3) . . . . ?
C1 C9 C10 C11 162.0(3) . . . . ?
C8 C9 C10 C15 -126.8(2) . . . . ?
C22 C9 C10 C15 97.0(2) . . . . ?
C1 C9 C10 C15 -17.8(2) . . . . ?
C15 C10 C11 C12 -1.2(4) . . . . ?
C9 C10 C11 C12 179.0(2) . . . . ?
C10 C11 C12 C13 -2.5(4) . . . . ?
C10 C11 C12 Br1 176.79(18) . . . . ?
C11 C12 C13 O3 -178.4(2) . . . . ?
Br1 C12 C13 O3 2.4(4) . . . . ?
C11 C12 C13 C14 4.0(4) . . . . ?
Br1 C12 C13 C14 -175.29(19) . . . . ?
O3 C13 C14 C15 -179.5(2) . . . . ?
C12 C13 C14 C15 -1.7(4) . . . . ?
C13 C14 C15 O4 177.8(2) . . . . ?
C13 C14 C15 C10 -2.1(4) . . . . ?
C1 O4 C15 C14 -165.1(2) . . . . ?
C1 O4 C15 C10 14.7(3) . . . . ?
C11 C10 C15 C14 3.6(4) . . . . ?
C9 C10 C15 C14 -176.6(2) . . . . ?
C11 C10 C15 O4 -176.3(2) . . . . ?
C9 C10 C15 O4 3.5(3) . . . . ?
O4 C1 C16 C21 179.9(2) . . . . ?
C2 C1 C16 C21 -56.0(3) . . . . ?
C9 C1 C16 C21 60.9(3) . . . . ?
O4 C1 C16 C17 -0.8(3) . . . . ?
C2 C1 C16 C17 123.2(3) . . . . ?
C9 C1 C16 C17 -119.9(3) . . . . ?
C21 C16 C17 C18 -1.1(4) . . . . ?
C1 C16 C17 C18 179.6(3) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C17 C18 C19 C20 0.5(5) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
C19 C20 C21 C16 -1.2(5) . . . . ?
C17 C16 C21 C20 1.7(4) . . . . ?
C1 C16 C21 C20 -179.0(3) . . . . ?
C23 O2 C22 O1 -8.4(4) . . . . ?
C23 O2 C22 C9 167.5(2) . . . . ?
C8 C9 C22 O1 -160.6(2) . . . . ?
C10 C9 C22 O1 -26.7(3) . . . . ?
C1 C9 C22 O1 80.8(3) . . . . ?
C8 C9 C22 O2 23.5(3) . . . . ?
C10 C9 C22 O2 157.4(2) . . . . ?
C1 C9 C22 O2 -95.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.055
