# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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.
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data_mk660_1_vesely_org

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H25 Br O5'
_chemical_formula_sum            'C25 H25 Br O5'
_chemical_formula_weight         485.36
_chemical_compound_source        'synthesized by the authors'
_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           triclinic
_symmetry_space_group_name_H-M   'P 1'
_symmetry_space_group_name_Hall  'P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   6.4597(4)
_cell_length_b                   9.7895(6)
_cell_length_c                   10.0741(5)
_cell_angle_alpha                70.729(2)
_cell_angle_beta                 76.156(2)
_cell_angle_gamma                79.307(2)
_cell_volume                     579.93(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5789
_cell_measurement_theta_min      2.2189
_cell_measurement_theta_max      27.3398

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             250
_exptl_absorpt_coefficient_mu    1.805
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.5129
_exptl_absorpt_correction_T_max  0.7324


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10226
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         27.49
_reflns_number_total             5195
_reflns_number_gt                4911
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker Instrument Service v2012.12.0.0'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0199P)²+0.1248P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_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   -0.005(4)
_refine_ls_number_reflns         5195
_refine_ls_number_parameters     284
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0517
_refine_ls_wR_factor_gt          0.0506
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.044
_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 -0.120830(16) -0.353904(15) 0.720377(15) 0.04074(7) Uani 1 1 d . . .
C1 C 0.4684(3) -0.0469(2) 0.0947(2) 0.0184(4) Uani 1 1 d . . .
C2 C 0.2984(3) 0.08952(17) 0.05659(18) 0.0167(3) Uani 1 1 d . . .
C3 C 0.1300(3) 0.03479(18) 0.00523(19) 0.0193(3) Uani 1 1 d . . .
H3A H -0.0090 0.0326 0.0733 0.023 Uiso 1 1 calc R . .
H3B H 0.1074 0.0989 -0.0905 0.023 Uiso 1 1 calc R . .
C4 C 0.2228(3) -0.11629(18) -0.00072(17) 0.0178(3) Uani 1 1 d . . .
C5 C 0.1418(3) -0.20795(19) -0.05078(19) 0.0233(4) Uani 1 1 d . . .
H5 H 0.0155 -0.1767 -0.0905 0.028 Uiso 1 1 calc R . .
C6 C 0.2497(3) -0.3458(2) -0.0414(2) 0.0275(4) Uani 1 1 d . . .
H6 H 0.1974 -0.4089 -0.0766 0.033 Uiso 1 1 calc R . .
C7 C 0.4330(3) -0.3941(2) 0.0185(2) 0.0284(4) Uani 1 1 d . . .
H7 H 0.5014 -0.4904 0.0261 0.034 Uiso 1 1 calc R . .
C8 C 0.5166(3) -0.3031(2) 0.0670(2) 0.0244(4) Uani 1 1 d . . .
H8 H 0.6428 -0.3345 0.1067 0.029 Uiso 1 1 calc R . .
C9 C 0.4088(3) -0.16393(18) 0.05538(18) 0.0191(3) Uani 1 1 d . . .
C10 C 0.4281(3) 0.20118(19) -0.06481(19) 0.0215(4) Uani 1 1 d . . .
C11 C 0.2217(3) 0.14550(18) 0.18951(17) 0.0174(3) Uani 1 1 d . . .
H11 H 0.3537 0.1678 0.2100 0.021 Uiso 1 1 calc R . .
C12 C 0.0710(3) 0.28625(18) 0.16728(19) 0.0206(4) Uani 1 1 d . . .
C13 C -0.0602(4) 0.3348(2) 0.0745(2) 0.0351(5) Uani 1 1 d . . .
H13A H -0.1476 0.4254 0.0679 0.042 Uiso 1 1 calc R . .
H13B H -0.0670 0.2791 0.0146 0.042 Uiso 1 1 calc R . .
C14 C 0.1317(3) 0.02752(18) 0.32258(18) 0.0179(3) Uani 1 1 d . . .
C15 C -0.0747(3) -0.0105(2) 0.34636(19) 0.0224(4) Uani 1 1 d . . .
H15 H -0.1671 0.0426 0.2814 0.027 Uiso 1 1 calc R . .
C16 C -0.1465(3) -0.1246(2) 0.4637(2) 0.0245(4) Uani 1 1 d . . .
H16 H -0.2858 -0.1515 0.4774 0.029 Uiso 1 1 calc R . .
C17 C -0.0155(3) -0.1990(2) 0.56031(19) 0.0250(4) Uani 1 1 d . . .
C18 C 0.1861(3) -0.1608(2) 0.5434(2) 0.0297(4) Uani 1 1 d . . .
H18 H 0.2740 -0.2107 0.6121 0.036 Uiso 1 1 calc R . .
C19 C 0.2584(3) -0.0483(2) 0.4242(2) 0.0249(4) Uani 1 1 d . . .
H19 H 0.3979 -0.0221 0.4115 0.030 Uiso 1 1 calc R . .
C20 C 0.0825(3) 0.3733(2) 0.2619(2) 0.0232(4) Uani 1 1 d . . .
C21 C 0.5730(3) 0.2603(2) -0.32448(19) 0.0295(4) Uani 1 1 d . . .
C22 C 0.4749(4) 0.4179(2) -0.3610(3) 0.0438(6) Uani 1 1 d . . .
H22A H 0.3222 0.4230 -0.3618 0.066 Uiso 1 1 calc R . .
H22B H 0.5485 0.4721 -0.4557 0.066 Uiso 1 1 calc R . .
H22C H 0.4904 0.4606 -0.2890 0.066 Uiso 1 1 calc R . .
C23 C 0.8065(3) 0.2410(3) -0.3117(2) 0.0417(5) Uani 1 1 d . . .
H23A H 0.8205 0.2878 -0.2425 0.063 Uiso 1 1 calc R . .
H23B H 0.8929 0.2858 -0.4053 0.063 Uiso 1 1 calc R . .
H23C H 0.8569 0.1368 -0.2789 0.063 Uiso 1 1 calc R . .
C24 C 0.5431(4) 0.1889(3) -0.4303(2) 0.0490(6) Uani 1 1 d . . .
H24A H 0.6014 0.0859 -0.4021 0.074 Uiso 1 1 calc R . .
H24B H 0.6188 0.2380 -0.5264 0.074 Uiso 1 1 calc R . .
H24C H 0.3898 0.1968 -0.4309 0.074 Uiso 1 1 calc R . .
C25 C -0.0401(4) 0.5907(2) 0.3236(2) 0.0361(5) Uani 1 1 d . . .
H25A H -0.0581 0.5402 0.4267 0.054 Uiso 1 1 calc R . .
H25B H -0.1501 0.6747 0.3061 0.054 Uiso 1 1 calc R . .
H25C H 0.1026 0.6240 0.2884 0.054 Uiso 1 1 calc R . .
O1 O 0.6216(2) -0.04993(16) 0.14539(17) 0.0270(3) Uani 1 1 d . . .
O2 O 0.5090(2) 0.29305(15) -0.04712(15) 0.0333(3) Uani 1 1 d . . .
O3 O 0.4463(2) 0.17494(14) -0.18886(13) 0.0256(3) Uani 1 1 d . . .
O4 O 0.2084(3) 0.34114(17) 0.34045(18) 0.0397(4) Uani 1 1 d . . .
O5 O -0.0614(2) 0.49217(14) 0.24948(15) 0.0301(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C17 1.8992(17) . ?
C1 O1 1.209(2) . ?
C1 C9 1.467(2) . ?
C1 C2 1.568(2) . ?
C2 C10 1.536(2) . ?
C2 C11 1.551(2) . ?
C2 C3 1.551(2) . ?
C3 C4 1.504(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C9 1.387(2) . ?
C4 C5 1.390(2) . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.391(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(3) . ?
C8 H8 0.9500 . ?
C10 O2 1.199(2) . ?
C10 O3 1.331(2) . ?
C11 C12 1.516(2) . ?
C11 C14 1.524(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.325(3) . ?
C12 C20 1.494(3) . ?
C13 H13A 0.9500 . ?
C13 H13B 0.9500 . ?
C14 C19 1.394(3) . ?
C14 C15 1.395(2) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(3) . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 O4 1.198(2) . ?
C20 O5 1.339(2) . ?
C21 O3 1.483(2) . ?
C21 C22 1.514(3) . ?
C21 C23 1.516(3) . ?
C21 C24 1.517(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 O5 1.442(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
O1 C1 C9 127.81(18) . . ?
O1 C1 C2 124.28(17) . . ?
C9 C1 C2 107.90(14) . . ?
C10 C2 C11 109.45(13) . . ?
C10 C2 C3 112.83(14) . . ?
C11 C2 C3 117.93(14) . . ?
C10 C2 C1 103.45(14) . . ?
C11 C2 C1 107.77(13) . . ?
C3 C2 C1 104.12(13) . . ?
C4 C3 C2 105.29(14) . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C9 C4 C5 119.70(16) . . ?
C9 C4 C3 112.30(14) . . ?
C5 C4 C3 127.98(16) . . ?
C6 C5 C4 118.37(17) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C7 121.59(17) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 120.48(18) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 117.58(17) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 H8 121.2 . . ?
C4 C9 C8 122.23(15) . . ?
C4 C9 C1 109.91(15) . . ?
C8 C9 C1 127.85(16) . . ?
O2 C10 O3 125.85(16) . . ?
O2 C10 C2 124.11(16) . . ?
O3 C10 C2 109.95(14) . . ?
C12 C11 C14 111.62(13) . . ?
C12 C11 C2 115.02(13) . . ?
C14 C11 C2 111.96(13) . . ?
C12 C11 H11 105.8 . . ?
C14 C11 H11 105.8 . . ?
C2 C11 H11 105.8 . . ?
C13 C12 C20 120.31(17) . . ?
C13 C12 C11 126.34(16) . . ?
C20 C12 C11 113.34(15) . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C19 C14 C15 117.81(16) . . ?
C19 C14 C11 119.91(15) . . ?
C15 C14 C11 122.26(15) . . ?
C16 C15 C14 120.76(16) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 119.81(17) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 121.04(17) . . ?
C16 C17 Br1 118.46(14) . . ?
C18 C17 Br1 120.48(14) . . ?
C17 C18 C19 118.81(17) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C18 C19 C14 121.69(17) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
O4 C20 O5 123.04(18) . . ?
O4 C20 C12 123.72(18) . . ?
O5 C20 C12 113.23(16) . . ?
O3 C21 C22 109.44(16) . . ?
O3 C21 C23 109.70(15) . . ?
C22 C21 C23 113.21(19) . . ?
O3 C21 C24 101.66(16) . . ?
C22 C21 C24 110.82(19) . . ?
C23 C21 C24 111.39(19) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C25 H25A 109.5 . . ?
O5 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O5 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C10 O3 C21 122.35(14) . . ?
C20 O5 C25 115.80(16) . . ?

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
O1 C1 C2 C10 65.4(2) . . . . ?
C9 C1 C2 C10 -113.53(15) . . . . ?
O1 C1 C2 C11 -50.5(2) . . . . ?
C9 C1 C2 C11 130.61(14) . . . . ?
O1 C1 C2 C3 -176.46(19) . . . . ?
C9 C1 C2 C3 4.60(18) . . . . ?
C10 C2 C3 C4 104.81(16) . . . . ?
C11 C2 C3 C4 -125.98(15) . . . . ?
C1 C2 C3 C4 -6.67(17) . . . . ?
C2 C3 C4 C9 6.96(19) . . . . ?
C2 C3 C4 C5 -174.64(16) . . . . ?
C9 C4 C5 C6 0.7(2) . . . . ?
C3 C4 C5 C6 -177.61(17) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C5 C6 C7 C8 -1.9(3) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C5 C4 C9 C8 -1.6(3) . . . . ?
C3 C4 C9 C8 176.93(16) . . . . ?
C5 C4 C9 C1 177.34(15) . . . . ?
C3 C4 C9 C1 -4.1(2) . . . . ?
C7 C8 C9 C4 0.8(3) . . . . ?
C7 C8 C9 C1 -177.97(18) . . . . ?
O1 C1 C9 C4 -179.4(2) . . . . ?
C2 C1 C9 C4 -0.5(2) . . . . ?
O1 C1 C9 C8 -0.5(3) . . . . ?
C2 C1 C9 C8 178.37(17) . . . . ?
C11 C2 C10 O2 19.7(2) . . . . ?
C3 C2 C10 O2 153.19(18) . . . . ?
C1 C2 C10 O2 -94.9(2) . . . . ?
C11 C2 C10 O3 -163.70(13) . . . . ?
C3 C2 C10 O3 -30.2(2) . . . . ?
C1 C2 C10 O3 81.64(17) . . . . ?
C10 C2 C11 C12 62.73(18) . . . . ?
C3 C2 C11 C12 -68.04(19) . . . . ?
C1 C2 C11 C12 174.58(13) . . . . ?
C10 C2 C11 C14 -168.46(14) . . . . ?
C3 C2 C11 C14 60.77(18) . . . . ?
C1 C2 C11 C14 -56.61(17) . . . . ?
C14 C11 C12 C13 -101.9(2) . . . . ?
C2 C11 C12 C13 27.0(3) . . . . ?
C14 C11 C12 C20 78.74(18) . . . . ?
C2 C11 C12 C20 -152.29(15) . . . . ?
C12 C11 C14 C19 -129.29(17) . . . . ?
C2 C11 C14 C19 100.14(19) . . . . ?
C12 C11 C14 C15 51.9(2) . . . . ?
C2 C11 C14 C15 -78.70(19) . . . . ?
C19 C14 C15 C16 -3.1(3) . . . . ?
C11 C14 C15 C16 175.74(17) . . . . ?
C14 C15 C16 C17 1.9(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C15 C16 C17 Br1 179.57(15) . . . . ?
C16 C17 C18 C19 -2.0(3) . . . . ?
Br1 C17 C18 C19 179.23(16) . . . . ?
C17 C18 C19 C14 0.6(3) . . . . ?
C15 C14 C19 C18 1.9(3) . . . . ?
C11 C14 C19 C18 -177.02(17) . . . . ?
C13 C12 C20 O4 -174.4(2) . . . . ?
C11 C12 C20 O4 5.0(3) . . . . ?
C13 C12 C20 O5 5.2(3) . . . . ?
C11 C12 C20 O5 -175.47(15) . . . . ?
O2 C10 O3 C21 -0.3(3) . . . . ?
C2 C10 O3 C21 -176.76(15) . . . . ?
C22 C21 O3 C10 -62.8(2) . . . . ?
C23 C21 O3 C10 61.9(2) . . . . ?
C24 C21 O3 C10 179.91(17) . . . . ?
O4 C20 O5 C25 7.4(3) . . . . ?
C12 C20 O5 C25 -172.18(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.039
#===END
_database_code_depnum_ccdc_archive 'CCDC 953269'
#######################################################################
#
#                 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_jv_mk867_1_org

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 O4'
_chemical_formula_sum            'C24 H26 O4'
_chemical_formula_weight         378.45
_chemical_compound_source        'synthesized by the authors'
_chemical_absolute_configuration syn


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   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   9.6739(3)
_cell_length_b                   8.7077(3)
_cell_length_c                   12.2435(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.6610(10)
_cell_angle_gamma                90.00
_cell_volume                     1016.73(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8722
_cell_measurement_theta_min      2.8845
_cell_measurement_theta_max      27.4748

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9611
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15240
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4680
_reflns_number_gt                4263
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker Instrument Service v2012.12.0.0'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_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)+(0.0496P)²+0.1266P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_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   -0.5(8)
_refine_ls_number_reflns         4680
_refine_ls_number_parameters     257
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.31972(16) 0.81473(18) 0.11278(13) 0.0330(3) Uani 1 1 d . . .
C2 C 0.41726(16) 0.69258(17) 0.08244(11) 0.0304(3) Uani 1 1 d . . .
H2 H 0.3619 0.5954 0.0693 0.037 Uiso 1 1 calc R . .
C3 C 0.53394(15) 0.66497(16) 0.18417(11) 0.0251(3) Uani 1 1 d . . .
H3 H 0.5966 0.5830 0.1626 0.030 Uiso 1 1 calc R . .
C4 C 0.46469(13) 0.59841(16) 0.27998(11) 0.0244(3) Uani 1 1 d . . .
C5 C 0.31199(15) 0.65764(18) 0.27335(12) 0.0296(3) Uani 1 1 d . . .
H5 H 0.2931 0.6721 0.3505 0.036 Uiso 1 1 calc R . .
C6 C 0.21977(15) 0.5297(2) 0.21982(12) 0.0330(3) Uani 1 1 d . . .
C7 C 0.07820(17) 0.5357(3) 0.17584(15) 0.0463(4) Uani 1 1 d . . .
H7 H 0.0259 0.6274 0.1794 0.056 Uiso 1 1 calc R . .
C8 C 0.0147(2) 0.4041(3) 0.12648(16) 0.0569(6) Uani 1 1 d . . .
H8 H -0.0820 0.4060 0.0950 0.068 Uiso 1 1 calc R . .
C9 C 0.0902(2) 0.2719(3) 0.12291(15) 0.0548(5) Uani 1 1 d . . .
H9 H 0.0449 0.1832 0.0886 0.066 Uiso 1 1 calc R . .
C10 C 0.2314(2) 0.2644(2) 0.16829(14) 0.0434(4) Uani 1 1 d . . .
H10 H 0.2826 0.1716 0.1663 0.052 Uiso 1 1 calc R . .
C11 C 0.29618(16) 0.39579(19) 0.21673(12) 0.0329(3) Uani 1 1 d . . .
C12 C 0.44652(16) 0.41991(17) 0.26895(13) 0.0302(3) Uani 1 1 d . . .
H12A H 0.5105 0.3769 0.2216 0.036 Uiso 1 1 calc R . .
H12B H 0.4665 0.3701 0.3426 0.036 Uiso 1 1 calc R . .
C13 C 0.55329(14) 0.62738(16) 0.39320(11) 0.0260(3) Uani 1 1 d . . .
C14 C 0.62416(14) 0.80772(17) 0.21150(11) 0.0274(3) Uani 1 1 d . . .
C15 C 0.59110(16) 0.92725(17) 0.27844(12) 0.0304(3) Uani 1 1 d . . .
H15 H 0.5070 0.9225 0.3087 0.036 Uiso 1 1 calc R . .
C16 C 0.67948(18) 1.05337(19) 0.30157(14) 0.0392(4) Uani 1 1 d . . .
H16 H 0.6564 1.1327 0.3487 0.047 Uiso 1 1 calc R . .
C17 C 0.80047(19) 1.0636(2) 0.25625(16) 0.0462(4) Uani 1 1 d . . .
H17 H 0.8606 1.1499 0.2717 0.055 Uiso 1 1 calc R . .
C18 C 0.83349(18) 0.9475(2) 0.18826(17) 0.0480(5) Uani 1 1 d . . .
H18 H 0.9162 0.9547 0.1563 0.058 Uiso 1 1 calc R . .
C19 C 0.74693(17) 0.8206(2) 0.16636(14) 0.0379(4) Uani 1 1 d . . .
H19 H 0.7714 0.7412 0.1199 0.046 Uiso 1 1 calc R . .
C20 C 0.79882(16) 0.6037(2) 0.48675(13) 0.0358(3) Uani 1 1 d . . .
C21 C 0.7712(3) 0.4918(4) 0.5739(2) 0.1055(14) Uani 1 1 d . . .
H21A H 0.6815 0.5165 0.5969 0.158 Uiso 1 1 calc R . .
H21B H 0.8467 0.4984 0.6380 0.158 Uiso 1 1 calc R . .
H21C H 0.7674 0.3874 0.5436 0.158 Uiso 1 1 calc R . .
C22 C 0.8085(2) 0.7660(2) 0.52799(18) 0.0526(5) Uani 1 1 d . . .
H22A H 0.8204 0.8353 0.4672 0.079 Uiso 1 1 calc R . .
H22B H 0.8890 0.7761 0.5879 0.079 Uiso 1 1 calc R . .
H22C H 0.7224 0.7928 0.5559 0.079 Uiso 1 1 calc R . .
C23 C 0.9271(2) 0.5664(4) 0.4373(2) 0.0883(10) Uani 1 1 d . . .
H23A H 0.9198 0.4612 0.4083 0.133 Uiso 1 1 calc R . .
H23B H 1.0107 0.5753 0.4944 0.133 Uiso 1 1 calc R . .
H23C H 0.9342 0.6382 0.3769 0.133 Uiso 1 1 calc R . .
C24 C 0.4695(2) 0.7305(2) -0.02340(13) 0.0458(4) Uani 1 1 d . . .
H24A H 0.3894 0.7458 -0.0830 0.069 Uiso 1 1 calc R . .
H24B H 0.5273 0.6457 -0.0430 0.069 Uiso 1 1 calc R . .
H24C H 0.5257 0.8246 -0.0132 0.069 Uiso 1 1 calc R . .
O1 O 0.28217(11) 0.80128(13) 0.21360(9) 0.0357(3) Uani 1 1 d . . .
O2 O 0.27885(13) 0.92365(14) 0.05626(11) 0.0475(3) Uani 1 1 d . . .
O3 O 0.50808(12) 0.67156(17) 0.47366(9) 0.0445(3) Uani 1 1 d . . .
O4 O 0.68537(10) 0.58918(12) 0.38942(8) 0.0292(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.201(2) . ?
C1 O1 1.349(2) . ?
C1 C2 1.509(2) . ?
C2 C24 1.504(2) . ?
C2 C3 1.5528(19) . ?
C2 H2 1.0000 . ?
C3 C14 1.523(2) . ?
C3 C4 1.5571(18) . ?
C3 H3 1.0000 . ?
C4 C13 1.5235(18) . ?
C4 C5 1.5539(19) . ?
C4 C12 1.567(2) . ?
C5 O1 1.4533(19) . ?
C5 C6 1.507(2) . ?
C5 H5 1.0000 . ?
C6 C11 1.385(2) . ?
C6 C7 1.386(2) . ?
C7 C8 1.389(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.369(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.502(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O3 1.2060(17) . ?
C13 O4 1.3285(17) . ?
C14 C15 1.395(2) . ?
C14 C19 1.396(2) . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.381(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 O4 1.4838(17) . ?
C20 C22 1.499(3) . ?
C20 C21 1.502(3) . ?
C20 C23 1.505(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
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
O2 C1 O1 118.85(15) . . ?
O2 C1 C2 125.00(16) . . ?
O1 C1 C2 116.08(13) . . ?
C24 C2 C1 111.81(14) . . ?
C24 C2 C3 114.90(13) . . ?
C1 C2 C3 108.18(11) . . ?
C24 C2 H2 107.2 . . ?
C1 C2 H2 107.2 . . ?
C3 C2 H2 107.2 . . ?
C14 C3 C2 111.25(11) . . ?
C14 C3 C4 116.19(11) . . ?
C2 C3 C4 108.37(11) . . ?
C14 C3 H3 106.8 . . ?
C2 C3 H3 106.8 . . ?
C4 C3 H3 106.8 . . ?
C13 C4 C5 112.17(11) . . ?
C13 C4 C3 112.11(11) . . ?
C5 C4 C3 111.26(11) . . ?
C13 C4 C12 106.28(11) . . ?
C5 C4 C12 103.46(11) . . ?
C3 C4 C12 111.12(11) . . ?
O1 C5 C6 111.37(12) . . ?
O1 C5 C4 114.75(12) . . ?
C6 C5 C4 105.41(12) . . ?
O1 C5 H5 108.4 . . ?
C6 C5 H5 108.4 . . ?
C4 C5 H5 108.4 . . ?
C11 C6 C7 121.22(16) . . ?
C11 C6 C5 110.77(13) . . ?
C7 C6 C5 128.00(16) . . ?
C6 C7 C8 118.3(2) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
C9 C8 C7 120.54(17) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.44(18) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C11 118.40(19) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C6 C11 C10 120.06(15) . . ?
C6 C11 C12 110.72(13) . . ?
C10 C11 C12 129.21(16) . . ?
C11 C12 C4 105.19(12) . . ?
C11 C12 H12A 110.7 . . ?
C4 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
C4 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
O3 C13 O4 126.23(13) . . ?
O3 C13 C4 124.77(12) . . ?
O4 C13 C4 108.93(11) . . ?
C15 C14 C19 117.83(15) . . ?
C15 C14 C3 123.95(12) . . ?
C19 C14 C3 118.22(14) . . ?
C16 C15 C14 120.99(15) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 120.19(16) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 119.53(16) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 120.48(16) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.96(17) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
O4 C20 C22 110.30(13) . . ?
O4 C20 C21 108.63(14) . . ?
C22 C20 C21 112.4(2) . . ?
O4 C20 C23 101.95(14) . . ?
C22 C20 C23 109.29(19) . . ?
C21 C20 C23 113.7(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C2 C24 H24A 109.5 . . ?
C2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 O1 C5 118.30(11) . . ?
C13 O4 C20 122.46(11) . . ?

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
O2 C1 C2 C24 5.4(2) . . . . ?
O1 C1 C2 C24 -171.55(13) . . . . ?
O2 C1 C2 C3 132.93(15) . . . . ?
O1 C1 C2 C3 -44.04(17) . . . . ?
C24 C2 C3 C14 61.36(17) . . . . ?
C1 C2 C3 C14 -64.35(15) . . . . ?
C24 C2 C3 C4 -169.73(13) . . . . ?
C1 C2 C3 C4 64.56(15) . . . . ?
C14 C3 C4 C13 -30.66(16) . . . . ?
C2 C3 C4 C13 -156.74(11) . . . . ?
C14 C3 C4 C5 95.85(13) . . . . ?
C2 C3 C4 C5 -30.23(15) . . . . ?
C14 C3 C4 C12 -149.44(12) . . . . ?
C2 C3 C4 C12 84.48(14) . . . . ?
C13 C4 C5 O1 103.15(13) . . . . ?
C3 C4 C5 O1 -23.33(16) . . . . ?
C12 C4 C5 O1 -142.71(12) . . . . ?
C13 C4 C5 C6 -133.95(12) . . . . ?
C3 C4 C5 C6 99.57(13) . . . . ?
C12 C4 C5 C6 -19.81(14) . . . . ?
O1 C5 C6 C11 137.67(12) . . . . ?
C4 C5 C6 C11 12.63(16) . . . . ?
O1 C5 C6 C7 -41.2(2) . . . . ?
C4 C5 C6 C7 -166.27(16) . . . . ?
C11 C6 C7 C8 -1.1(2) . . . . ?
C5 C6 C7 C8 177.68(15) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C7 C6 C11 C10 0.4(2) . . . . ?
C5 C6 C11 C10 -178.55(13) . . . . ?
C7 C6 C11 C12 179.65(15) . . . . ?
C5 C6 C11 C12 0.67(17) . . . . ?
C9 C10 C11 C6 0.5(2) . . . . ?
C9 C10 C11 C12 -178.51(15) . . . . ?
C6 C11 C12 C4 -13.55(16) . . . . ?
C10 C11 C12 C4 165.57(15) . . . . ?
C13 C4 C12 C11 138.49(11) . . . . ?
C5 C4 C12 C11 20.19(14) . . . . ?
C3 C4 C12 C11 -99.29(13) . . . . ?
C5 C4 C13 O3 9.5(2) . . . . ?
C3 C4 C13 O3 135.50(15) . . . . ?
C12 C4 C13 O3 -102.90(17) . . . . ?
C5 C4 C13 O4 -173.44(12) . . . . ?
C3 C4 C13 O4 -47.42(15) . . . . ?
C12 C4 C13 O4 74.17(14) . . . . ?
C2 C3 C14 C15 85.99(16) . . . . ?
C4 C3 C14 C15 -38.63(18) . . . . ?
C2 C3 C14 C19 -93.55(15) . . . . ?
C4 C3 C14 C19 141.84(13) . . . . ?
C19 C14 C15 C16 -1.5(2) . . . . ?
C3 C14 C15 C16 178.93(13) . . . . ?
C14 C15 C16 C17 1.4(2) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C17 C18 C19 C14 0.5(3) . . . . ?
C15 C14 C19 C18 0.6(2) . . . . ?
C3 C14 C19 C18 -179.88(14) . . . . ?
O2 C1 O1 C5 169.85(13) . . . . ?
C2 C1 O1 C5 -12.98(18) . . . . ?
C6 C5 O1 C1 -70.34(16) . . . . ?
C4 C5 O1 C1 49.29(16) . . . . ?
O3 C13 O4 C20 -2.9(2) . . . . ?
C4 C13 O4 C20 -179.96(12) . . . . ?
C22 C20 O4 C13 -57.25(18) . . . . ?
C21 C20 O4 C13 66.4(2) . . . . ?
C23 C20 O4 C13 -173.25(19) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.032
#===END
_database_code_depnum_ccdc_archive 'CCDC 953270'
