# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sgm_sc_76_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 Br O4'
_chemical_formula_sum            'C21 H19 Br O4'
_chemical_formula_weight         415.27
_chemical_absolute_configuration ad

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           trigonal
_symmetry_space_group_name_H-M   P3(2)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   11.7082(7)
_cell_length_b                   11.7082(7)
_cell_length_c                   11.9217(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1415.30(15)
_cell_formula_units_Z            3
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      24.47

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.41
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636
_exptl_absorpt_coefficient_mu    2.201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4118
_exptl_absorpt_correction_T_max  0.4656
_exptl_absorpt_process_details   'Bruker 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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32442
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         33.61
_reflns_number_total             7324
_reflns_number_gt                4525
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0294P)²+0.0586P] 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       0.0174(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.011(5)
_refine_ls_number_reflns         7324
_refine_ls_number_parameters     238
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0730
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.003
_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 1.45887(2) 0.43736(3) -0.16295(3) 0.07388(10) Uani 1 1 d . . .
O1 O 0.54074(16) -0.11408(18) -0.06218(12) 0.0666(4) Uani 1 1 d . . .
O2 O 0.46499(13) -0.20789(14) 0.10406(12) 0.0555(3) Uani 1 1 d . . .
O3 O 0.72173(19) -0.17891(17) 0.25343(14) 0.0703(4) Uani 1 1 d . . .
O4 O 0.67512(16) -0.28193(14) 0.08808(14) 0.0604(4) Uani 1 1 d . . .
C1 C 0.72214(17) 0.04533(18) 0.16874(14) 0.0417(4) Uani 1 1 d . . .
H1 H 0.7055 0.0143 0.2466 0.050 Uiso 1 1 calc R . .
C2 C 0.69498(17) -0.07222(17) 0.08889(15) 0.0384(3) Uani 1 1 d . . .
C3 C 0.80858(17) -0.01248(16) 0.00324(15) 0.0433(4) Uani 1 1 d . . .
H3A H 0.8392 -0.0737 -0.0136 0.052 Uiso 1 1 calc R . .
H3B H 0.7808 0.0101 -0.0659 0.052 Uiso 1 1 calc R . .
C4 C 0.91494(17) 0.10922(17) 0.06003(14) 0.0392(3) Uani 1 1 d . . .
C5 C 0.86772(17) 0.13715(19) 0.15202(16) 0.0442(4) Uani 1 1 d . . .
H5 H 0.9195 0.2061 0.2005 0.053 Uiso 1 1 calc R . .
C6 C 0.56009(18) -0.13286(18) 0.03262(16) 0.0440(4) Uani 1 1 d . . .
C7 C 0.3308(2) -0.2634(3) 0.0650(3) 0.0795(7) Uani 1 1 d . . .
H7A H 0.3094 -0.1946 0.0576 0.119 Uiso 1 1 calc R . .
H7B H 0.2720 -0.3277 0.1180 0.119 Uiso 1 1 calc R . .
H7C H 0.3218 -0.3049 -0.0064 0.119 Uiso 1 1 calc R . .
C8 C 0.69958(17) -0.18170(18) 0.15604(16) 0.0453(4) Uani 1 1 d . . .
C9 C 0.6636(3) -0.3981(2) 0.1425(3) 0.0770(7) Uani 1 1 d . . .
H9A H 0.7301 -0.3716 0.1994 0.115 Uiso 1 1 calc R . .
H9B H 0.6750 -0.4518 0.0879 0.115 Uiso 1 1 calc R . .
H9C H 0.5779 -0.4476 0.1762 0.115 Uiso 1 1 calc R . .
C10 C 1.04751(17) 0.18748(18) 0.00934(15) 0.0412(4) Uani 1 1 d . . .
C11 C 1.14607(19) 0.30243(19) 0.05856(16) 0.0478(4) Uani 1 1 d . . .
H11 H 1.1297 0.3300 0.1268 0.057 Uiso 1 1 calc R . .
C12 C 1.2677(2) 0.3765(2) 0.00822(19) 0.0535(5) Uani 1 1 d . . .
H12 H 1.3330 0.4524 0.0428 0.064 Uiso 1 1 calc R . .
C13 C 1.29137(18) 0.3372(2) -0.09333(17) 0.0516(4) Uani 1 1 d . . .
C14 C 1.1960(2) 0.2255(2) -0.14603(18) 0.0574(5) Uani 1 1 d . . .
H14 H 1.2124 0.2010 -0.2157 0.069 Uiso 1 1 calc R . .
C15 C 1.0750(2) 0.1500(2) -0.09371(19) 0.0533(4) Uani 1 1 d . . .
H15 H 1.0110 0.0731 -0.1280 0.064 Uiso 1 1 calc R . .
C16 C 0.64104(17) 0.11025(17) 0.14083(14) 0.0395(3) Uani 1 1 d . . .
C17 C 0.51624(19) 0.0624(2) 0.18720(16) 0.0516(4) Uani 1 1 d . . .
H17 H 0.4847 -0.0057 0.2395 0.062 Uiso 1 1 calc R . .
C18 C 0.4386(2) 0.1160(3) 0.1556(2) 0.0639(6) Uani 1 1 d . . .
H18 H 0.3545 0.0821 0.1855 0.077 Uiso 1 1 calc R . .
C19 C 0.4848(2) 0.2183(3) 0.0809(2) 0.0658(6) Uani 1 1 d . . .
H19 H 0.4328 0.2545 0.0609 0.079 Uiso 1 1 calc R . .
C20 C 0.6077(2) 0.2668(2) 0.0359(2) 0.0633(6) Uani 1 1 d . . .
H20 H 0.6392 0.3361 -0.0151 0.076 Uiso 1 1 calc R . .
C21 C 0.68534(19) 0.21380(18) 0.06534(17) 0.0488(4) Uani 1 1 d . . .
H21 H 0.7689 0.2482 0.0340 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
Br1 C13 1.9001(19) . ?
O1 C6 1.194(2) . ?
O2 C6 1.326(2) . ?
O2 C7 1.444(3) . ?
O3 C8 1.187(2) . ?
O4 C8 1.334(3) . ?
O4 C9 1.451(3) . ?
C1 C5 1.506(3) . ?
C1 C16 1.520(2) . ?
C1 C2 1.570(2) . ?
C1 H1 0.9800 . ?
C2 C6 1.525(3) . ?
C2 C8 1.535(2) . ?
C2 C3 1.540(2) . ?
C3 C4 1.505(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.340(3) . ?
C4 C10 1.480(2) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.391(3) . ?
C10 C15 1.395(3) . ?
C11 C12 1.380(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(3) . ?
C14 C15 1.388(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.386(3) . ?
C16 C17 1.391(2) . ?
C17 C18 1.391(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.365(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(3) . ?
C20 H20 0.9300 . ?
C21 H21 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
C6 O2 C7 117.08(18) . . ?
C8 O4 C9 115.6(2) . . ?
C5 C1 C16 112.39(14) . . ?
C5 C1 C2 101.91(13) . . ?
C16 C1 C2 113.72(13) . . ?
C5 C1 H1 109.5 . . ?
C16 C1 H1 109.5 . . ?
C2 C1 H1 109.5 . . ?
C6 C2 C8 107.53(14) . . ?
C6 C2 C3 112.21(15) . . ?
C8 C2 C3 110.01(14) . . ?
C6 C2 C1 112.55(13) . . ?
C8 C2 C1 109.85(14) . . ?
C3 C2 C1 104.69(13) . . ?
C4 C3 C2 104.46(14) . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C5 C4 C10 128.01(16) . . ?
C5 C4 C3 110.62(16) . . ?
C10 C4 C3 121.17(15) . . ?
C4 C5 C1 113.07(16) . . ?
C4 C5 H5 123.5 . . ?
C1 C5 H5 123.5 . . ?
O1 C6 O2 123.78(18) . . ?
O1 C6 C2 125.30(18) . . ?
O2 C6 C2 110.90(15) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C8 O4 124.49(17) . . ?
O3 C8 C2 125.87(18) . . ?
O4 C8 C2 109.64(16) . . ?
O4 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 117.74(17) . . ?
C11 C10 C4 122.18(16) . . ?
C15 C10 C4 120.01(16) . . ?
C12 C11 C10 121.39(18) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 119.39(19) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 121.20(19) . . ?
C12 C13 Br1 119.85(16) . . ?
C14 C13 Br1 118.95(16) . . ?
C13 C14 C15 119.0(2) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C10 121.2(2) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C21 C16 C17 117.96(17) . . ?
C21 C16 C1 121.70(15) . . ?
C17 C16 C1 120.27(16) . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 119.5(2) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.5(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 121.12(19) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?

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
C5 C1 C2 C6 -144.28(15) . . . . ?
C16 C1 C2 C6 -23.1(2) . . . . ?
C5 C1 C2 C8 95.94(15) . . . . ?
C16 C1 C2 C8 -142.87(15) . . . . ?
C5 C1 C2 C3 -22.14(16) . . . . ?
C16 C1 C2 C3 99.05(17) . . . . ?
C6 C2 C3 C4 143.23(14) . . . . ?
C8 C2 C3 C4 -97.11(16) . . . . ?
C1 C2 C3 C4 20.86(17) . . . . ?
C2 C3 C4 C5 -11.60(19) . . . . ?
C2 C3 C4 C10 173.27(14) . . . . ?
C10 C4 C5 C1 171.34(15) . . . . ?
C3 C4 C5 C1 -3.4(2) . . . . ?
C16 C1 C5 C4 -105.72(17) . . . . ?
C2 C1 C5 C4 16.38(18) . . . . ?
C7 O2 C6 O1 -3.4(3) . . . . ?
C7 O2 C6 C2 175.13(18) . . . . ?
C8 C2 C6 O1 -136.3(2) . . . . ?
C3 C2 C6 O1 -15.2(3) . . . . ?
C1 C2 C6 O1 102.6(2) . . . . ?
C8 C2 C6 O2 45.24(19) . . . . ?
C3 C2 C6 O2 166.35(14) . . . . ?
C1 C2 C6 O2 -75.87(18) . . . . ?
C9 O4 C8 O3 6.0(3) . . . . ?
C9 O4 C8 C2 -174.20(17) . . . . ?
C6 C2 C8 O3 -123.6(2) . . . . ?
C3 C2 C8 O3 113.9(2) . . . . ?
C1 C2 C8 O3 -0.8(3) . . . . ?
C6 C2 C8 O4 56.58(19) . . . . ?
C3 C2 C8 O4 -65.89(19) . . . . ?
C1 C2 C8 O4 179.37(14) . . . . ?
C5 C4 C10 C11 3.8(3) . . . . ?
C3 C4 C10 C11 178.02(16) . . . . ?
C5 C4 C10 C15 -173.18(18) . . . . ?
C3 C4 C10 C15 1.0(2) . . . . ?
C15 C10 C11 C12 -0.8(3) . . . . ?
C4 C10 C11 C12 -177.81(16) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C11 C12 C13 Br1 -179.43(14) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
Br1 C13 C14 C15 178.05(16) . . . . ?
C13 C14 C15 C10 1.8(3) . . . . ?
C11 C10 C15 C14 -0.7(3) . . . . ?
C4 C10 C15 C14 176.45(18) . . . . ?
C5 C1 C16 C21 26.2(2) . . . . ?
C2 C1 C16 C21 -88.9(2) . . . . ?
C5 C1 C16 C17 -156.79(16) . . . . ?
C2 C1 C16 C17 88.1(2) . . . . ?
C21 C16 C17 C18 1.5(3) . . . . ?
C1 C16 C17 C18 -175.56(18) . . . . ?
C16 C17 C18 C19 -1.6(3) . . . . ?
C17 C18 C19 C20 0.9(4) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
C19 C20 C21 C16 0.2(3) . . . . ?
C17 C16 C21 C20 -0.8(3) . . . . ?
C1 C16 C21 C20 176.20(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        33.61
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.038
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_database_code_depnum_ccdc_archive 'CCDC 1013561'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sgm_sd_87

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 O8'
_chemical_formula_sum            'C20 H22 O8'
_chemical_formula_weight         390.38
_chemical_absolute_configuration unk

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   C2

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

_cell_length_a                   20.4540(10)
_cell_length_b                   7.1698(3)
_cell_length_c                   15.6356(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.607(6)
_cell_angle_gamma                90.00
_cell_volume                     1952.84(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3331
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      20.40

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9609
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_process_details   'Bruker 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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11890
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3508
_reflns_number_gt                2708
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0428P)²+0.2804P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.2(12)
_refine_ls_number_reflns         3508
_refine_ls_number_parameters     257
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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 0.41283(11) -0.1764(3) 0.50961(14) 0.0547(5) Uani 1 1 d . . .
O2 O 0.33673(13) -0.3958(3) 0.52079(17) 0.0702(6) Uani 1 1 d . . .
O3 O 0.29173(13) 0.1010(3) 0.15238(15) 0.0652(6) Uani 1 1 d . . .
O4 O 0.22514(11) -0.1646(3) 0.10754(13) 0.0552(5) Uani 1 1 d . . .
O5 O 0.32552(12) -0.4529(3) 0.31005(17) 0.0690(6) Uani 1 1 d . . .
O6 O 0.39791(11) -0.3047(3) 0.26391(16) 0.0626(6) Uani 1 1 d . . .
O7 O 0.00143(13) 0.5545(3) 0.11818(18) 0.0811(7) Uani 1 1 d . . .
O8 O -0.07138(11) 0.3052(3) 0.04463(15) 0.0637(6) Uani 1 1 d . . .
C1 C 0.37302(14) -0.0007(4) 0.45345(19) 0.0438(7) Uani 1 1 d . . .
C2 C 0.37364(15) 0.0145(4) 0.35774(19) 0.0468(7) Uani 1 1 d . . .
H2A H 0.4235 -0.0208 0.3696 0.056 Uiso 1 1 calc R . .
H2B H 0.3628 0.1416 0.3329 0.056 Uiso 1 1 calc R . .
C3 C 0.31114(14) -0.1185(4) 0.28070(19) 0.0405(7) Uani 1 1 d . . .
C4 C 0.25002(13) -0.1284(4) 0.31246(19) 0.0420(7) Uani 1 1 d . . .
H4 H 0.2292 -0.2553 0.3006 0.050 Uiso 1 1 calc R . .
C5 C 0.29621(15) -0.0915(4) 0.4262(2) 0.0419(7) Uani 1 1 d . . .
H5 H 0.2679 -0.0262 0.4519 0.050 Uiso 1 1 calc R . .
C6 C 0.34544(18) -0.2511(4) 0.4905(2) 0.0516(7) Uani 1 1 d . . .
C7 C 0.40359(17) 0.1665(4) 0.5214(2) 0.0531(8) Uani 1 1 d . . .
H7A H 0.3729 0.2742 0.4848 0.064 Uiso 1 1 calc R . .
H7B H 0.4556 0.1898 0.5378 0.064 Uiso 1 1 calc R . .
C8 C 0.4042(2) 0.1503(6) 0.6183(2) 0.0827(11) Uani 1 1 d . . .
H8A H 0.3531 0.1258 0.6034 0.124 Uiso 1 1 calc R . .
H8B H 0.4225 0.2648 0.6553 0.124 Uiso 1 1 calc R . .
H8C H 0.4375 0.0498 0.6578 0.124 Uiso 1 1 calc R . .
C9 C 0.27660(16) -0.0446(5) 0.1744(2) 0.0475(7) Uani 1 1 d . . .
C10 C 0.18094(19) -0.1026(5) 0.0046(2) 0.0686(10) Uani 1 1 d . . .
H10A H 0.1684 0.0270 0.0027 0.103 Uiso 1 1 calc R . .
H10B H 0.1345 -0.1743 -0.0310 0.103 Uiso 1 1 calc R . .
H10C H 0.2105 -0.1193 -0.0265 0.103 Uiso 1 1 calc R . .
C11 C 0.34405(16) -0.3124(4) 0.2867(2) 0.0461(7) Uani 1 1 d . . .
C12 C 0.4398(2) -0.4762(5) 0.2760(3) 0.0861(12) Uani 1 1 d . . .
H12A H 0.4659 -0.5149 0.3450 0.129 Uiso 1 1 calc R . .
H12B H 0.4767 -0.4552 0.2566 0.129 Uiso 1 1 calc R . .
H12C H 0.4046 -0.5718 0.2343 0.129 Uiso 1 1 calc R . .
C13 C 0.18398(14) 0.0082(4) 0.25770(18) 0.0414(7) Uani 1 1 d . . .
C14 C 0.19347(16) 0.2002(4) 0.2760(2) 0.0507(8) Uani 1 1 d . . .
H14 H 0.2419 0.2474 0.3219 0.061 Uiso 1 1 calc R . .
C15 C 0.13227(15) 0.3201(4) 0.22716(19) 0.0500(7) Uani 1 1 d . . .
H15 H 0.1397 0.4472 0.2407 0.060 Uiso 1 1 calc R . .
C16 C 0.05950(15) 0.2540(4) 0.1579(2) 0.0448(7) Uani 1 1 d . . .
C17 C 0.04993(15) 0.0641(4) 0.1388(2) 0.0479(7) Uani 1 1 d . . .
H17 H 0.0015 0.0176 0.0925 0.057 Uiso 1 1 calc R . .
C18 C 0.11088(15) -0.0564(4) 0.1872(2) 0.0449(7) Uani 1 1 d . . .
H18 H 0.1032 -0.1832 0.1727 0.054 Uiso 1 1 calc R . .
C19 C -0.00418(17) 0.3889(5) 0.1070(2) 0.0511(8) Uani 1 1 d . . .
C20 C -0.13629(16) 0.4287(6) -0.0106(3) 0.0788(12) Uani 1 1 d . . .
H20A H -0.1482 0.4868 0.0349 0.118 Uiso 1 1 calc R . .
H20B H -0.1798 0.3585 -0.0599 0.118 Uiso 1 1 calc R . .
H20C H -0.1239 0.5230 -0.0435 0.118 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 C6 1.358(4) . ?
O1 C1 1.508(3) . ?
O2 C6 1.192(4) . ?
O3 C9 1.190(4) . ?
O4 C9 1.337(3) . ?
O4 C10 1.443(3) . ?
O5 C11 1.198(3) . ?
O6 C11 1.325(3) . ?
O6 C12 1.454(4) . ?
O7 C19 1.197(4) . ?
O8 C19 1.340(3) . ?
O8 C20 1.446(4) . ?
C1 C7 1.504(4) . ?
C1 C2 1.507(4) . ?
C1 C5 1.540(4) . ?
C2 C3 1.543(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C9 1.521(4) . ?
C3 C11 1.526(4) . ?
C3 C4 1.570(4) . ?
C4 C13 1.518(3) . ?
C4 C5 1.537(4) . ?
C4 H4 0.9800 . ?
C5 C6 1.507(4) . ?
C5 H5 0.9800 . ?
C7 C8 1.513(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.392(3) . ?
C13 C14 1.399(4) . ?
C14 C15 1.373(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(4) . ?
C16 C19 1.476(4) . ?
C17 C18 1.373(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
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
C6 O1 C1 91.44(19) . . ?
C9 O4 C10 116.8(2) . . ?
C11 O6 C12 116.5(3) . . ?
C19 O8 C20 115.5(3) . . ?
C7 C1 C2 115.3(2) . . ?
C7 C1 O1 110.9(2) . . ?
C2 C1 O1 110.8(2) . . ?
C7 C1 C5 121.3(2) . . ?
C2 C1 C5 107.1(2) . . ?
O1 C1 C5 88.22(19) . . ?
C1 C2 C3 107.2(2) . . ?
C1 C2 H2A 110.3 . . ?
C3 C2 H2A 110.3 . . ?
C1 C2 H2B 110.3 . . ?
C3 C2 H2B 110.3 . . ?
H2A C2 H2B 108.5 . . ?
C9 C3 C11 108.8(2) . . ?
C9 C3 C2 111.0(2) . . ?
C11 C3 C2 110.9(2) . . ?
C9 C3 C4 111.8(2) . . ?
C11 C3 C4 109.8(2) . . ?
C2 C3 C4 104.61(19) . . ?
C13 C4 C5 111.5(2) . . ?
C13 C4 C3 114.4(2) . . ?
C5 C4 C3 104.44(19) . . ?
C13 C4 H4 108.8 . . ?
C5 C4 H4 108.8 . . ?
C3 C4 H4 108.8 . . ?
C6 C5 C4 115.6(2) . . ?
C6 C5 C1 84.7(2) . . ?
C4 C5 C1 108.2(2) . . ?
C6 C5 H5 114.8 . . ?
C4 C5 H5 114.8 . . ?
C1 C5 H5 114.8 . . ?
O2 C6 O1 127.0(3) . . ?
O2 C6 C5 137.6(3) . . ?
O1 C6 C5 95.4(2) . . ?
C1 C7 C8 115.4(3) . . ?
C1 C7 H7A 108.4 . . ?
C8 C7 H7A 108.4 . . ?
C1 C7 H7B 108.4 . . ?
C8 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 O4 123.8(3) . . ?
O3 C9 C3 125.4(3) . . ?
O4 C9 C3 110.8(2) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C11 O6 123.9(3) . . ?
O5 C11 C3 125.8(3) . . ?
O6 C11 C3 110.3(3) . . ?
O6 C12 H12A 109.5 . . ?
O6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 117.8(3) . . ?
C18 C13 C4 120.0(2) . . ?
C14 C13 C4 122.2(2) . . ?
C15 C14 C13 120.9(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.9(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 118.5(3) . . ?
C17 C16 C19 122.9(3) . . ?
C15 C16 C19 118.7(3) . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C13 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
O7 C19 O8 122.3(3) . . ?
O7 C19 C16 125.5(3) . . ?
O8 C19 C16 112.2(3) . . ?
O8 C20 H20A 109.5 . . ?
O8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O8 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 O1 C1 C7 119.4(2) . . . . ?
C6 O1 C1 C2 -111.1(2) . . . . ?
C6 O1 C1 C5 -3.5(2) . . . . ?
C7 C1 C2 C3 -155.5(2) . . . . ?
O1 C1 C2 C3 77.5(3) . . . . ?
C5 C1 C2 C3 -17.2(3) . . . . ?
C1 C2 C3 C9 148.9(2) . . . . ?
C1 C2 C3 C11 -90.0(3) . . . . ?
C1 C2 C3 C4 28.2(3) . . . . ?
C9 C3 C4 C13 -25.9(3) . . . . ?
C11 C3 C4 C13 -146.7(2) . . . . ?
C2 C3 C4 C13 94.3(2) . . . . ?
C9 C3 C4 C5 -148.1(2) . . . . ?
C11 C3 C4 C5 91.1(2) . . . . ?
C2 C3 C4 C5 -27.9(3) . . . . ?
C13 C4 C5 C6 161.0(2) . . . . ?
C3 C4 C5 C6 -75.0(3) . . . . ?
C13 C4 C5 C1 -106.1(2) . . . . ?
C3 C4 C5 C1 17.9(3) . . . . ?
C7 C1 C5 C6 -110.3(3) . . . . ?
C2 C1 C5 C6 114.4(2) . . . . ?
O1 C1 C5 C6 3.19(19) . . . . ?
C7 C1 C5 C4 134.4(2) . . . . ?
C2 C1 C5 C4 -0.8(3) . . . . ?
O1 C1 C5 C4 -112.1(2) . . . . ?
C1 O1 C6 O2 -175.6(3) . . . . ?
C1 O1 C6 C5 3.6(2) . . . . ?
C4 C5 C6 O2 -76.8(5) . . . . ?
C1 C5 C6 O2 175.5(4) . . . . ?
C4 C5 C6 O1 104.2(2) . . . . ?
C1 C5 C6 O1 -3.6(2) . . . . ?
C2 C1 C7 C8 -179.0(3) . . . . ?
O1 C1 C7 C8 -52.0(3) . . . . ?
C5 C1 C7 C8 49.1(4) . . . . ?
C10 O4 C9 O3 -6.3(4) . . . . ?
C10 O4 C9 C3 172.7(2) . . . . ?
C11 C3 C9 O3 -126.3(3) . . . . ?
C2 C3 C9 O3 -4.1(4) . . . . ?
C4 C3 C9 O3 112.3(3) . . . . ?
C11 C3 C9 O4 54.7(3) . . . . ?
C2 C3 C9 O4 177.0(2) . . . . ?
C4 C3 C9 O4 -66.6(3) . . . . ?
C12 O6 C11 O5 -4.8(4) . . . . ?
C12 O6 C11 C3 174.2(2) . . . . ?
C9 C3 C11 O5 -121.2(3) . . . . ?
C2 C3 C11 O5 116.5(3) . . . . ?
C4 C3 C11 O5 1.4(4) . . . . ?
C9 C3 C11 O6 59.9(3) . . . . ?
C2 C3 C11 O6 -62.4(3) . . . . ?
C4 C3 C11 O6 -177.5(2) . . . . ?
C5 C4 C13 C18 -132.4(2) . . . . ?
C3 C4 C13 C18 109.3(3) . . . . ?
C5 C4 C13 C14 47.0(3) . . . . ?
C3 C4 C13 C14 -71.3(3) . . . . ?
C18 C13 C14 C15 1.1(4) . . . . ?
C4 C13 C14 C15 -178.4(2) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C14 C15 C16 C19 -179.6(3) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C19 C16 C17 C18 179.4(3) . . . . ?
C16 C17 C18 C13 0.7(4) . . . . ?
C14 C13 C18 C17 -1.2(4) . . . . ?
C4 C13 C18 C17 178.2(2) . . . . ?
C20 O8 C19 O7 1.8(4) . . . . ?
C20 O8 C19 C16 -178.1(3) . . . . ?
C17 C16 C19 O7 -177.3(3) . . . . ?
C15 C16 C19 O7 2.0(5) . . . . ?
C17 C16 C19 O8 2.5(4) . . . . ?
C15 C16 C19 O8 -178.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.041
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate-light petroleum ether'
_database_code_depnum_ccdc_archive 'CCDC 1021576'
