# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z
_database_code_depnum_ccdc_archive 'CCDC 1410542'
_audit_update_record             
;
2015-07-04 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 Br O5'
_chemical_formula_weight         421.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   12.3928(5)
_cell_length_b                   8.3243(4)
_cell_length_c                   18.5364(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.8880(10)
_cell_angle_gamma                90.00
_cell_volume                     1902.15(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    2.188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6000
_exptl_absorpt_correction_T_max  0.7948
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21474
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3340
_reflns_number_gt                2430
_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)+(0.0412P)²+1.5082P] 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         3340
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0965
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.13067(3) 0.23826(5) 0.107137(19) 0.06516(16) Uani 1 1 d . . .
O1 O 0.7629(2) 0.5982(3) 0.18656(13) 0.0666(7) Uani 1 1 d . . .
O2 O 0.65932(19) 0.5605(3) 0.08331(13) 0.0610(6) Uani 1 1 d . . .
O3 O 0.66442(15) 0.3005(3) -0.01983(10) 0.0482(5) Uani 1 1 d . . .
O4 O 1.04385(17) 0.2193(3) -0.04792(11) 0.0648(7) Uani 1 1 d . . .
O5 O 0.77906(17) 0.3448(3) 0.27734(10) 0.0539(6) Uani 1 1 d . . .
H5B H 0.7692 0.4406 0.2687 0.081 Uiso 1 1 calc R . .
C1 C 0.5771(2) 0.1241(4) 0.09861(16) 0.0436(7) Uani 1 1 d . . .
H1A H 0.6236 0.0813 0.0673 0.052 Uiso 1 1 calc R . .
C2 C 0.4762(3) 0.0556(4) 0.10232(18) 0.0542(8) Uani 1 1 d . . .
H2A H 0.4553 -0.0325 0.0733 0.065 Uiso 1 1 calc R . .
C3 C 0.4069(3) 0.1163(5) 0.1482(2) 0.0614(10) Uani 1 1 d . . .
H3A H 0.3392 0.0694 0.1506 0.074 Uiso 1 1 calc R . .
C4 C 0.4374(3) 0.2462(5) 0.1907(2) 0.0617(10) Uani 1 1 d . . .
H4A H 0.3906 0.2874 0.2222 0.074 Uiso 1 1 calc R . .
C5 C 0.5385(3) 0.3167(4) 0.18681(17) 0.0499(8) Uani 1 1 d . . .
H5A H 0.5584 0.4059 0.2153 0.060 Uiso 1 1 calc R . .
C6 C 0.6096(2) 0.2554(3) 0.14087(15) 0.0357(6) Uani 1 1 d . . .
C7 C 0.7236(2) 0.3253(3) 0.14318(14) 0.0356(6) Uani 1 1 d . . .
C8 C 0.7945(2) 0.2832(3) 0.08251(14) 0.0352(6) Uani 1 1 d . . .
C9 C 0.7700(2) 0.2807(3) 0.00776(15) 0.0383(7) Uani 1 1 d . . .
C10 C 0.8520(2) 0.2562(4) -0.03678(15) 0.0453(7) Uani 1 1 d . . .
H10A H 0.8349 0.2499 -0.0867 0.054 Uiso 1 1 calc R . .
C11 C 0.9593(2) 0.2409(4) -0.00760(15) 0.0448(7) Uani 1 1 d . . .
C12 C 0.9838(2) 0.2495(4) 0.06676(16) 0.0445(7) Uani 1 1 d . . .
C13 C 0.9024(2) 0.2690(3) 0.11138(14) 0.0381(6) Uani 1 1 d . . .
C14 C 0.9141(2) 0.2883(4) 0.19234(15) 0.0467(8) Uani 1 1 d . . .
H14A H 0.9408 0.3945 0.2063 0.056 Uiso 1 1 calc R . .
H14B H 0.9631 0.2084 0.2154 0.056 Uiso 1 1 calc R . .
C15 C 0.7983(2) 0.2636(4) 0.21252(14) 0.0411(7) Uani 1 1 d . . .
C16 C 0.7785(3) 0.0877(4) 0.22682(16) 0.0529(8) Uani 1 1 d . . .
H16A H 0.8244 0.0538 0.2690 0.079 Uiso 1 1 calc R . .
H16B H 0.7946 0.0253 0.1857 0.079 Uiso 1 1 calc R . .
H16C H 0.7039 0.0722 0.2349 0.079 Uiso 1 1 calc R . .
C17 C 0.7181(2) 0.5094(4) 0.14231(16) 0.0432(7) Uani 1 1 d . . .
C18 C 0.6572(4) 0.7320(4) 0.0703(3) 0.0795(12) Uani 1 1 d . . .
H18A H 0.6122 0.7545 0.0262 0.119 Uiso 1 1 calc R . .
H18B H 0.7295 0.7696 0.0662 0.119 Uiso 1 1 calc R . .
H18C H 0.6284 0.7856 0.1100 0.119 Uiso 1 1 calc R . .
C19 C 0.6435(3) 0.3761(5) -0.08852(18) 0.0662(10) Uani 1 1 d . . .
H19A H 0.5666 0.3829 -0.1014 0.099 Uiso 1 1 calc R . .
H19B H 0.6758 0.3143 -0.1244 0.099 Uiso 1 1 calc R . .
H19C H 0.6741 0.4822 -0.0862 0.099 Uiso 1 1 calc R . .
C20 C 1.0211(3) 0.2160(5) -0.12382(19) 0.0749(12) Uani 1 1 d . . .
H20A H 1.0873 0.2011 -0.1457 0.112 Uiso 1 1 calc R . .
H20B H 0.9882 0.3157 -0.1401 0.112 Uiso 1 1 calc R . .
H20C H 0.9724 0.1291 -0.1374 0.112 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 1.898(3) . ?
O1 C17 1.198(4) . ?
O2 C17 1.321(4) . ?
O2 C18 1.447(4) . ?
O3 C9 1.365(3) . ?
O3 C19 1.420(3) . ?
O4 C11 1.360(3) . ?
O4 C20 1.406(4) . ?
O5 C15 1.420(3) . ?
O5 H5B 0.8200 . ?
C1 C6 1.380(4) . ?
C1 C2 1.383(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.366(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.368(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.392(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.384(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.525(4) . ?
C7 C17 1.534(4) . ?
C7 C8 1.536(4) . ?
C7 C15 1.590(4) . ?
C8 C9 1.388(4) . ?
C8 C13 1.394(4) . ?
C9 C10 1.389(4) . ?
C10 C11 1.388(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.383(4) . ?
C12 C13 1.378(4) . ?
C13 C14 1.501(4) . ?
C14 C15 1.533(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.513(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C17 O2 C18 117.0(3) . . ?
C9 O3 C19 118.0(2) . . ?
C11 O4 C20 117.8(3) . . ?
C15 O5 H5B 109.5 . . ?
C6 C1 C2 120.7(3) . . ?
C6 C1 H1A 119.6 . . ?
C2 C1 H1A 119.6 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C1 C6 C5 118.3(3) . . ?
C1 C6 C7 122.2(2) . . ?
C5 C6 C7 119.3(3) . . ?
C6 C7 C17 109.9(2) . . ?
C6 C7 C8 119.4(2) . . ?
C17 C7 C8 104.4(2) . . ?
C6 C7 C15 111.1(2) . . ?
C17 C7 C15 110.7(2) . . ?
C8 C7 C15 100.9(2) . . ?
C9 C8 C13 119.0(2) . . ?
C9 C8 C7 130.6(2) . . ?
C13 C8 C7 109.6(2) . . ?
O3 C9 C8 118.4(2) . . ?
O3 C9 C10 121.8(2) . . ?
C8 C9 C10 119.8(3) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
O4 C11 C12 116.8(3) . . ?
O4 C11 C10 124.0(3) . . ?
C12 C11 C10 119.2(3) . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 Br1 120.0(2) . . ?
C11 C12 Br1 119.7(2) . . ?
C12 C13 C8 120.8(2) . . ?
C12 C13 C14 127.7(3) . . ?
C8 C13 C14 111.4(2) . . ?
C13 C14 C15 103.5(2) . . ?
C13 C14 H14A 111.1 . . ?
C15 C14 H14A 111.1 . . ?
C13 C14 H14B 111.1 . . ?
C15 C14 H14B 111.1 . . ?
H14A C14 H14B 109.0 . . ?
O5 C15 C16 105.5(2) . . ?
O5 C15 C14 112.7(2) . . ?
C16 C15 C14 110.2(2) . . ?
O5 C15 C7 113.3(2) . . ?
C16 C15 C7 111.3(2) . . ?
C14 C15 C7 104.0(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 O2 123.0(3) . . ?
O1 C17 C7 126.3(3) . . ?
O2 C17 C7 110.6(3) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 -0.3(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C2 C1 C6 C7 174.6(3) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C4 C5 C6 C7 -174.2(3) . . . . ?
C1 C6 C7 C17 138.3(3) . . . . ?
C5 C6 C7 C17 -47.1(3) . . . . ?
C1 C6 C7 C8 17.9(4) . . . . ?
C5 C6 C7 C8 -167.5(3) . . . . ?
C1 C6 C7 C15 -98.9(3) . . . . ?
C5 C6 C7 C15 75.7(3) . . . . ?
C6 C7 C8 C9 45.9(4) . . . . ?
C17 C7 C8 C9 -77.3(4) . . . . ?
C15 C7 C8 C9 167.9(3) . . . . ?
C6 C7 C8 C13 -144.0(3) . . . . ?
C17 C7 C8 C13 92.9(3) . . . . ?
C15 C7 C8 C13 -22.0(3) . . . . ?
C19 O3 C9 C8 149.1(3) . . . . ?
C19 O3 C9 C10 -31.8(4) . . . . ?
C13 C8 C9 O3 -177.7(3) . . . . ?
C7 C8 C9 O3 -8.3(5) . . . . ?
C13 C8 C9 C10 3.2(4) . . . . ?
C7 C8 C9 C10 172.6(3) . . . . ?
O3 C9 C10 C11 178.1(3) . . . . ?
C8 C9 C10 C11 -2.7(5) . . . . ?
C20 O4 C11 C12 -177.8(3) . . . . ?
C20 O4 C11 C10 1.5(5) . . . . ?
C9 C10 C11 O4 -178.9(3) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
O4 C11 C12 C13 -179.1(3) . . . . ?
C10 C11 C12 C13 1.5(5) . . . . ?
O4 C11 C12 Br1 2.1(4) . . . . ?
C10 C11 C12 Br1 -177.2(2) . . . . ?
C11 C12 C13 C8 -1.1(5) . . . . ?
Br1 C12 C13 C8 177.7(2) . . . . ?
C11 C12 C13 C14 -176.9(3) . . . . ?
Br1 C12 C13 C14 1.9(4) . . . . ?
C9 C8 C13 C12 -1.3(4) . . . . ?
C7 C8 C13 C12 -172.7(3) . . . . ?
C9 C8 C13 C14 175.2(3) . . . . ?
C7 C8 C13 C14 3.7(3) . . . . ?
C12 C13 C14 C15 -166.7(3) . . . . ?
C8 C13 C14 C15 17.2(3) . . . . ?
C13 C14 C15 O5 -153.0(2) . . . . ?
C13 C14 C15 C16 89.4(3) . . . . ?
C13 C14 C15 C7 -29.9(3) . . . . ?
C6 C7 C15 O5 -78.3(3) . . . . ?
C17 C7 C15 O5 44.1(3) . . . . ?
C8 C7 C15 O5 154.1(2) . . . . ?
C6 C7 C15 C16 40.4(3) . . . . ?
C17 C7 C15 C16 162.8(2) . . . . ?
C8 C7 C15 C16 -87.2(3) . . . . ?
C6 C7 C15 C14 159.0(2) . . . . ?
C17 C7 C15 C14 -78.6(3) . . . . ?
C8 C7 C15 C14 31.4(3) . . . . ?
C18 O2 C17 O1 4.7(5) . . . . ?
C18 O2 C17 C7 -172.8(3) . . . . ?
C6 C7 C17 O1 123.3(3) . . . . ?
C8 C7 C17 O1 -107.6(3) . . . . ?
C15 C7 C17 O1 0.2(4) . . . . ?
C6 C7 C17 O2 -59.2(3) . . . . ?
C8 C7 C17 O2 69.9(3) . . . . ?
C15 C7 C17 O2 177.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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 1410543'
_audit_update_record             
;
2015-07-04 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 Br O5'
_chemical_formula_weight         435.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   9.2166(3)
_cell_length_b                   9.0685(3)
_cell_length_c                   23.2491(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.0800(10)
_cell_angle_gamma                90.00
_cell_volume                     1918.83(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    2.172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5169
_exptl_absorpt_correction_T_max  0.7961
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19351
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3374
_reflns_number_gt                2534
_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)+(0.1807P)²+1.8389P] 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         3374
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0928
_refine_ls_wR_factor_ref         0.2745
_refine_ls_wR_factor_gt          0.2416
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.142
_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 0.40949(8) 0.55082(8) 0.21379(3) 0.0507(4) Uani 1 1 d . . .
O1 O 0.9900(7) 0.2367(7) 0.0501(3) 0.078(2) Uani 1 1 d . . .
O2 O 0.9354(5) 0.4362(5) 0.0965(3) 0.0454(12) Uani 1 1 d . . .
O3 O 0.9675(4) 0.2353(5) 0.19074(19) 0.0437(12) Uani 1 1 d . . .
O4 O 0.6568(6) 0.4389(4) 0.0266(2) 0.0474(13) Uani 1 1 d . . .
H4A H 0.7365 0.4677 0.0436 0.071 Uiso 1 1 calc R . .
O5 O 0.6633(6) 0.5010(6) 0.3052(2) 0.0470(12) Uani 1 1 d . . .
C1 C 0.7305(6) 0.3097(6) 0.1486(2) 0.0266(12) Uani 1 1 d . . .
C2 C 0.8416(6) 0.3045(6) 0.1976(3) 0.0315(13) Uani 1 1 d . . .
C3 C 0.8209(6) 0.3649(7) 0.2503(3) 0.0345(14) Uani 1 1 d . . .
H3A H 0.8949 0.3584 0.2824 0.041 Uiso 1 1 calc R . .
C4 C 0.6900(7) 0.4350(6) 0.2554(3) 0.0343(14) Uani 1 1 d . . .
C5 C 0.5836(7) 0.4421(6) 0.2067(3) 0.0317(13) Uani 1 1 d . . .
C6 C 0.5973(6) 0.3747(6) 0.1549(2) 0.0288(12) Uani 1 1 d . . .
C7 C 0.4680(7) 0.3692(7) 0.1060(3) 0.0414(16) Uani 1 1 d . . .
H7A H 0.3812 0.3397 0.1218 0.050 Uiso 1 1 calc R . .
H7B H 0.4506 0.4675 0.0899 0.050 Uiso 1 1 calc R . .
C8 C 0.4895(7) 0.2655(7) 0.0581(3) 0.0424(16) Uani 1 1 d . . .
H8A H 0.4132 0.2827 0.0250 0.051 Uiso 1 1 calc R . .
H8B H 0.4792 0.1651 0.0713 0.051 Uiso 1 1 calc R . .
C9 C 0.6394(7) 0.2827(7) 0.0388(3) 0.0359(14) Uani 1 1 d . . .
C10 C 0.7641(6) 0.2387(6) 0.0912(2) 0.0276(13) Uani 1 1 d . . .
C11 C 0.7641(6) 0.0662(6) 0.0984(2) 0.0275(13) Uani 1 1 d . . .
C12 C 0.6830(7) 0.0039(7) 0.1372(3) 0.0332(13) Uani 1 1 d . . .
H12A H 0.6333 0.0651 0.1596 0.040 Uiso 1 1 calc R . .
C13 C 0.6736(8) -0.1483(8) 0.1436(3) 0.0461(17) Uani 1 1 d . . .
H13A H 0.6164 -0.1873 0.1695 0.055 Uiso 1 1 calc R . .
C14 C 0.7476(9) -0.2406(8) 0.1122(3) 0.053(2) Uani 1 1 d . . .
H14A H 0.7444 -0.3423 0.1171 0.064 Uiso 1 1 calc R . .
C15 C 0.8274(8) -0.1791(8) 0.0727(3) 0.0512(19) Uani 1 1 d . . .
H15A H 0.8756 -0.2410 0.0500 0.061 Uiso 1 1 calc R . .
C16 C 0.8376(8) -0.0278(7) 0.0659(3) 0.0438(17) Uani 1 1 d . . .
H16A H 0.8937 0.0106 0.0396 0.053 Uiso 1 1 calc R . .
C17 C 0.6506(9) 0.2003(8) -0.0162(3) 0.0514(19) Uani 1 1 d . . .
H17A H 0.5727 0.2307 -0.0462 0.077 Uiso 1 1 calc R . .
H17B H 0.6428 0.0964 -0.0094 0.077 Uiso 1 1 calc R . .
H17C H 0.7436 0.2212 -0.0281 0.077 Uiso 1 1 calc R . .
C18 C 0.9086(7) 0.2975(8) 0.0774(3) 0.0391(15) Uani 1 1 d . . .
C19 C 1.0736(9) 0.4985(11) 0.0859(5) 0.064(2) Uani 1 1 d . . .
H19A H 1.0827 0.5975 0.1006 0.096 Uiso 1 1 calc R . .
H19B H 1.0761 0.4993 0.0447 0.096 Uiso 1 1 calc R . .
H19C H 1.1534 0.4399 0.1052 0.096 Uiso 1 1 calc R . .
C20 C 1.0960(8) 0.2611(10) 0.2324(4) 0.066(2) Uani 1 1 d . . .
H20A H 1.1764 0.2050 0.2220 0.099 Uiso 1 1 calc R . .
H20B H 1.0782 0.2316 0.2703 0.099 Uiso 1 1 calc R . .
H20C H 1.1201 0.3642 0.2329 0.099 Uiso 1 1 calc R . .
C21 C 0.7651(11) 0.4821(11) 0.3571(3) 0.061(2) Uani 1 1 d . . .
H21A H 0.7314 0.5348 0.3883 0.091 Uiso 1 1 calc R . .
H21B H 0.8593 0.5195 0.3515 0.091 Uiso 1 1 calc R . .
H21C H 0.7735 0.3792 0.3667 0.091 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 C5 1.913(6) . ?
O1 C18 1.192(8) . ?
O2 C18 1.344(8) . ?
O2 C19 1.450(9) . ?
O3 C2 1.351(7) . ?
O3 C20 1.426(8) . ?
O4 C9 1.458(8) . ?
O4 H4A 0.8200 . ?
O5 C4 1.360(8) . ?
O5 C21 1.417(10) . ?
C1 C6 1.390(8) . ?
C1 C2 1.408(8) . ?
C1 C10 1.555(8) . ?
C2 C3 1.381(8) . ?
C3 C4 1.385(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.377(9) . ?
C5 C6 1.374(9) . ?
C6 C7 1.512(8) . ?
C7 C8 1.493(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.527(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C17 1.498(9) . ?
C9 C10 1.588(8) . ?
C10 C18 1.516(9) . ?
C10 C11 1.573(7) . ?
C11 C12 1.380(9) . ?
C11 C16 1.385(9) . ?
C12 C13 1.393(10) . ?
C12 H12A 0.9300 . ?
C13 C14 1.363(11) . ?
C13 H13A 0.9300 . ?
C14 C15 1.381(11) . ?
C14 H14A 0.9300 . ?
C15 C16 1.386(10) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C18 O2 C19 115.4(6) . . ?
C2 O3 C20 118.7(5) . . ?
C9 O4 H4A 109.5 . . ?
C4 O5 C21 119.2(6) . . ?
C6 C1 C2 118.0(5) . . ?
C6 C1 C10 124.3(5) . . ?
C2 C1 C10 117.6(5) . . ?
O3 C2 C3 122.1(5) . . ?
O3 C2 C1 116.6(5) . . ?
C3 C2 C1 121.4(5) . . ?
C2 C3 C4 120.1(5) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
O5 C4 C5 118.6(6) . . ?
O5 C4 C3 123.5(6) . . ?
C5 C4 C3 117.9(6) . . ?
C6 C5 C4 123.2(6) . . ?
C6 C5 Br1 119.9(5) . . ?
C4 C5 Br1 116.8(5) . . ?
C5 C6 C1 119.0(5) . . ?
C5 C6 C7 120.2(5) . . ?
C1 C6 C7 120.8(5) . . ?
C8 C7 C6 113.5(5) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C9 112.8(5) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
O4 C9 C17 107.0(5) . . ?
O4 C9 C8 106.8(5) . . ?
C17 C9 C8 112.8(6) . . ?
O4 C9 C10 107.8(5) . . ?
C17 C9 C10 113.0(5) . . ?
C8 C9 C10 109.1(5) . . ?
C18 C10 C1 109.7(5) . . ?
C18 C10 C11 112.8(5) . . ?
C1 C10 C11 108.5(5) . . ?
C18 C10 C9 107.6(5) . . ?
C1 C10 C9 109.6(4) . . ?
C11 C10 C9 108.7(4) . . ?
C12 C11 C16 117.8(6) . . ?
C12 C11 C10 119.1(5) . . ?
C16 C11 C10 123.1(6) . . ?
C11 C12 C13 121.7(6) . . ?
C11 C12 H12A 119.2 . . ?
C13 C12 H12A 119.2 . . ?
C14 C13 C12 120.4(7) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 118.2(6) . . ?
C13 C14 H14A 120.9 . . ?
C15 C14 H14A 120.9 . . ?
C14 C15 C16 121.9(7) . . ?
C14 C15 H15A 119.1 . . ?
C16 C15 H15A 119.1 . . ?
C11 C16 C15 120.0(7) . . ?
C11 C16 H16A 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 O2 120.7(6) . . ?
O1 C18 C10 126.7(6) . . ?
O2 C18 C10 112.4(5) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C20 O3 C2 C3 -18.4(9) . . . . ?
C20 O3 C2 C1 162.8(6) . . . . ?
C6 C1 C2 O3 177.3(5) . . . . ?
C10 C1 C2 O3 -1.2(8) . . . . ?
C6 C1 C2 C3 -1.4(9) . . . . ?
C10 C1 C2 C3 -180.0(5) . . . . ?
O3 C2 C3 C4 180.0(6) . . . . ?
C1 C2 C3 C4 -1.3(9) . . . . ?
C21 O5 C4 C5 173.7(7) . . . . ?
C21 O5 C4 C3 -8.6(10) . . . . ?
C2 C3 C4 O5 -177.8(6) . . . . ?
C2 C3 C4 C5 -0.1(9) . . . . ?
O5 C4 C5 C6 -177.6(5) . . . . ?
C3 C4 C5 C6 4.6(9) . . . . ?
O5 C4 C5 Br1 1.8(7) . . . . ?
C3 C4 C5 Br1 -176.0(4) . . . . ?
C4 C5 C6 C1 -7.4(9) . . . . ?
Br1 C5 C6 C1 173.2(4) . . . . ?
C4 C5 C6 C7 171.5(6) . . . . ?
Br1 C5 C6 C7 -7.9(8) . . . . ?
C2 C1 C6 C5 5.6(8) . . . . ?
C10 C1 C6 C5 -176.0(5) . . . . ?
C2 C1 C6 C7 -173.3(5) . . . . ?
C10 C1 C6 C7 5.2(9) . . . . ?
C5 C6 C7 C8 -167.4(6) . . . . ?
C1 C6 C7 C8 11.4(9) . . . . ?
C6 C7 C8 C9 -46.7(8) . . . . ?
C7 C8 C9 O4 -51.8(6) . . . . ?
C7 C8 C9 C17 -169.1(5) . . . . ?
C7 C8 C9 C10 64.5(7) . . . . ?
C6 C1 C10 C18 130.4(6) . . . . ?
C2 C1 C10 C18 -51.2(7) . . . . ?
C6 C1 C10 C11 -106.1(6) . . . . ?
C2 C1 C10 C11 72.4(6) . . . . ?
C6 C1 C10 C9 12.4(8) . . . . ?
C2 C1 C10 C9 -169.1(5) . . . . ?
O4 C9 C10 C18 -48.4(6) . . . . ?
C17 C9 C10 C18 69.7(7) . . . . ?
C8 C9 C10 C18 -164.0(5) . . . . ?
O4 C9 C10 C1 70.8(6) . . . . ?
C17 C9 C10 C1 -171.1(6) . . . . ?
C8 C9 C10 C1 -44.8(6) . . . . ?
O4 C9 C10 C11 -170.8(5) . . . . ?
C17 C9 C10 C11 -52.7(7) . . . . ?
C8 C9 C10 C11 73.6(6) . . . . ?
C18 C10 C11 C12 147.5(5) . . . . ?
C1 C10 C11 C12 25.8(7) . . . . ?
C9 C10 C11 C12 -93.3(6) . . . . ?
C18 C10 C11 C16 -35.1(8) . . . . ?
C1 C10 C11 C16 -156.8(6) . . . . ?
C9 C10 C11 C16 84.1(7) . . . . ?
C16 C11 C12 C13 -0.4(9) . . . . ?
C10 C11 C12 C13 177.1(5) . . . . ?
C11 C12 C13 C14 1.3(10) . . . . ?
C12 C13 C14 C15 -2.2(10) . . . . ?
C13 C14 C15 C16 2.2(11) . . . . ?
C12 C11 C16 C15 0.4(10) . . . . ?
C10 C11 C16 C15 -177.0(6) . . . . ?
C14 C15 C16 C11 -1.3(12) . . . . ?
C19 O2 C18 O1 -4.9(10) . . . . ?
C19 O2 C18 C10 178.7(6) . . . . ?
C1 C10 C18 O1 153.3(7) . . . . ?
C11 C10 C18 O1 32.3(9) . . . . ?
C9 C10 C18 O1 -87.6(8) . . . . ?
C1 C10 C18 O2 -30.7(7) . . . . ?
C11 C10 C18 O2 -151.7(5) . . . . ?
C9 C10 C18 O2 88.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.821
_refine_diff_density_min         -0.824
_refine_diff_density_rms         0.209
