# 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_ch132

_audit_creation_date             2014-03-05T16:56:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H18 O4'
_chemical_formula_sum            'C13 H18 O4'
_chemical_formula_weight         238.27
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   I4(1)/a
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_Int_Tables_number      88
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z'
'-y+3/4, x+1/4, z+1/4'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'x, y-1/2, -z'
'y-3/4, -x-1/4, -z-1/4'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   23.3014(13)
_cell_length_b                   23.3014(13)
_cell_length_c                   8.5463(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4640.3(5)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.35
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.059
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2048
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.9796
_exptl_absorpt_correction_T_max  0.9941

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_number            65194
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             2369
_reflns_number_gt                2105
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0461P)²+4.5409P] 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_number_reflns         2369
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.66538(5) 0.09648(5) 0.63963(13) 0.0128(2) Uani 1 1 d . . .
H1 H 0.6896 0.0652 0.6852 0.015 Uiso 1 1 calc R . .
C2 C 0.70207(5) 0.14247(5) 0.55357(13) 0.0136(2) Uani 1 1 d . . .
H2 H 0.7438 0.1362 0.5744 0.016 Uiso 1 1 calc R . .
C3 C 0.68437(5) 0.20292(5) 0.60182(15) 0.0163(3) Uani 1 1 d . . .
H3A H 0.7013 0.2119 0.7052 0.02 Uiso 1 1 calc R . .
H3B H 0.6998 0.2308 0.5252 0.02 Uiso 1 1 calc R . .
C4 C 0.61959(5) 0.20942(5) 0.61078(13) 0.0145(2) Uani 1 1 d . . .
C5 C 0.58860(5) 0.15505(5) 0.66214(13) 0.0127(2) Uani 1 1 d . . .
C7 C 0.53321(5) 0.16246(5) 0.75313(14) 0.0161(3) Uani 1 1 d . . .
H7A H 0.5092 0.1934 0.7079 0.019 Uiso 1 1 calc R . .
H7B H 0.5409 0.1712 0.8645 0.019 Uiso 1 1 calc R . .
C8 C 0.50445(5) 0.10367(5) 0.73455(15) 0.0191(3) Uani 1 1 d . . .
H8A H 0.5221 0.0749 0.805 0.023 Uiso 1 1 calc R . .
H8B H 0.4628 0.106 0.7569 0.023 Uiso 1 1 calc R . .
C9 C 0.51533(5) 0.08857(6) 0.56261(15) 0.0197(3) Uani 1 1 d . . .
H9A H 0.4845 0.1044 0.4955 0.024 Uiso 1 1 calc R . .
H9B H 0.5165 0.0464 0.5484 0.024 Uiso 1 1 calc R . .
C10 C 0.57405(5) 0.11564(5) 0.51948(13) 0.0127(2) Uani 1 1 d . . .
H10 H 0.5707 0.1389 0.4215 0.015 Uiso 1 1 calc R . .
C11 C 0.62568(5) 0.07414(5) 0.50913(13) 0.0117(2) Uani 1 1 d . . .
H11 H 0.6142 0.0332 0.5258 0.014 Uiso 1 1 calc R . .
C12 C 0.66341(5) 0.08169(5) 0.36493(13) 0.0120(2) Uani 1 1 d . . .
C16 C 0.63556(5) 0.08288(5) 0.20488(14) 0.0163(3) Uani 1 1 d . . .
H16A H 0.6654 0.09 0.1247 0.02 Uiso 1 1 calc R . .
H16B H 0.6078 0.115 0.2006 0.02 Uiso 1 1 calc R . .
C17 C 0.60468(6) 0.02712(6) 0.16686(16) 0.0248(3) Uani 1 1 d . . .
H17A H 0.6328 -0.004 0.1578 0.037 Uiso 1 1 calc R . .
H17B H 0.584 0.0313 0.0677 0.037 Uiso 1 1 calc R . .
H17C H 0.5774 0.0182 0.2506 0.037 Uiso 1 1 calc R . .
O6 O 0.62899(3) 0.12217(3) 0.75385(9) 0.01382(19) Uani 1 1 d . . .
O13 O 0.68988(3) 0.13606(3) 0.38889(9) 0.01333(19) Uani 1 1 d . . .
O14 O 0.59485(4) 0.25356(4) 0.57970(11) 0.0222(2) Uani 1 1 d . . .
O15 O 0.70557(3) 0.03698(3) 0.37472(10) 0.01407(19) Uani 1 1 d . . .
H15 H 0.7277(8) 0.0394(7) 0.296(2) 0.033(5) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O6 1.4249(13) . ?
C1 C11 1.5398(15) . ?
C1 C2 1.5557(16) . ?
C1 H1 1 . ?
C2 O13 1.4435(14) . ?
C2 C3 1.5246(16) . ?
C2 H2 1 . ?
C3 C4 1.5191(16) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 O14 1.2086(15) . ?
C4 C5 1.5228(16) . ?
C5 O6 1.4448(14) . ?
C5 C7 1.5166(16) . ?
C5 C10 1.5636(15) . ?
C7 C8 1.5333(16) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.5321(17) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.5511(16) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.5459(15) . ?
C10 H10 1 . ?
C11 C12 1.5241(15) . ?
C11 H11 1 . ?
C12 O13 1.4239(13) . ?
C12 O15 1.4343(13) . ?
C12 C16 1.5142(15) . ?
C16 C17 1.5205(18) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
O15 H15 0.85(2) . ?

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
O6 C1 C11 106.30(9) . . ?
O6 C1 C2 111.19(9) . . ?
C11 C1 C2 102.75(9) . . ?
O6 C1 H1 112 . . ?
C11 C1 H1 112 . . ?
C2 C1 H1 112 . . ?
O13 C2 C3 107.81(9) . . ?
O13 C2 C1 106.35(9) . . ?
C3 C2 C1 111.09(9) . . ?
O13 C2 H2 110.5 . . ?
C3 C2 H2 110.5 . . ?
C1 C2 H2 110.5 . . ?
C4 C3 C2 112.00(9) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O14 C4 C3 123.21(11) . . ?
O14 C4 C5 123.03(11) . . ?
C3 C4 C5 113.76(10) . . ?
O6 C5 C7 109.67(9) . . ?
O6 C5 C4 106.77(9) . . ?
C7 C5 C4 117.17(10) . . ?
O6 C5 C10 104.64(9) . . ?
C7 C5 C10 106.39(9) . . ?
C4 C5 C10 111.51(9) . . ?
C5 C7 C8 102.54(9) . . ?
C5 C7 H7A 111.3 . . ?
C8 C7 H7A 111.3 . . ?
C5 C7 H7B 111.3 . . ?
C8 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
C9 C8 C7 103.42(10) . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109 . . ?
C8 C9 C10 106.29(10) . . ?
C8 C9 H9A 110.5 . . ?
C10 C9 H9A 110.5 . . ?
C8 C9 H9B 110.5 . . ?
C10 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C11 C10 C9 116.47(10) . . ?
C11 C10 C5 104.08(9) . . ?
C9 C10 C5 104.17(9) . . ?
C11 C10 H10 110.6 . . ?
C9 C10 H10 110.6 . . ?
C5 C10 H10 110.6 . . ?
C12 C11 C1 101.54(9) . . ?
C12 C11 C10 115.02(9) . . ?
C1 C11 C10 102.40(9) . . ?
C12 C11 H11 112.3 . . ?
C1 C11 H11 112.3 . . ?
C10 C11 H11 112.3 . . ?
O13 C12 O15 109.96(9) . . ?
O13 C12 C16 107.41(9) . . ?
O15 C12 C16 111.07(9) . . ?
O13 C12 C11 103.67(8) . . ?
O15 C12 C11 105.32(9) . . ?
C16 C12 C11 119.03(9) . . ?
C12 C16 C17 112.34(10) . . ?
C12 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
C12 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 O6 C5 103.82(8) . . ?
C12 O13 C2 108.51(8) . . ?
C12 O15 H15 108.7(12) . . ?

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
O6 C1 C2 O13 -123.40(9) . . . . ?
C11 C1 C2 O13 -10.04(11) . . . . ?
O6 C1 C2 C3 -6.34(13) . . . . ?
C11 C1 C2 C3 107.01(10) . . . . ?
O13 C2 C3 C4 73.50(12) . . . . ?
C1 C2 C3 C4 -42.66(13) . . . . ?
C2 C3 C4 O14 -147.02(12) . . . . ?
C2 C3 C4 C5 32.80(14) . . . . ?
O14 C4 C5 O6 -154.41(11) . . . . ?
C3 C4 C5 O6 25.77(12) . . . . ?
O14 C4 C5 C7 -31.05(16) . . . . ?
C3 C4 C5 C7 149.12(10) . . . . ?
O14 C4 C5 C10 91.85(13) . . . . ?
C3 C4 C5 C10 -87.97(12) . . . . ?
O6 C5 C7 C8 -77.05(11) . . . . ?
C4 C5 C7 C8 161.08(10) . . . . ?
C10 C5 C7 C8 35.58(12) . . . . ?
C5 C7 C8 C9 -41.68(12) . . . . ?
C7 C8 C9 C10 32.27(12) . . . . ?
C8 C9 C10 C11 103.61(11) . . . . ?
C8 C9 C10 C5 -10.34(12) . . . . ?
O6 C5 C10 C11 -22.16(11) . . . . ?
C7 C5 C10 C11 -138.23(9) . . . . ?
C4 C5 C10 C11 92.90(11) . . . . ?
O6 C5 C10 C9 100.33(10) . . . . ?
C7 C5 C10 C9 -15.73(12) . . . . ?
C4 C5 C10 C9 -144.61(10) . . . . ?
O6 C1 C11 C12 147.45(9) . . . . ?
C2 C1 C11 C12 30.55(10) . . . . ?
O6 C1 C11 C10 28.31(11) . . . . ?
C2 C1 C11 C10 -88.58(10) . . . . ?
C9 C10 C11 C12 133.61(10) . . . . ?
C5 C10 C11 C12 -112.38(10) . . . . ?
C9 C10 C11 C1 -117.20(10) . . . . ?
C5 C10 C11 C1 -3.20(11) . . . . ?
C1 C11 C12 O13 -41.55(10) . . . . ?
C10 C11 C12 O13 68.15(11) . . . . ?
C1 C11 C12 O15 73.96(10) . . . . ?
C10 C11 C12 O15 -176.34(9) . . . . ?
C1 C11 C12 C16 -160.70(10) . . . . ?
C10 C11 C12 C16 -51.00(14) . . . . ?
O13 C12 C16 C17 -178.90(9) . . . . ?
O15 C12 C16 C17 60.82(12) . . . . ?
C11 C12 C16 C17 -61.70(13) . . . . ?
C11 C1 O6 C5 -43.85(10) . . . . ?
C2 C1 O6 C5 67.26(11) . . . . ?
C7 C5 O6 C1 154.47(9) . . . . ?
C4 C5 O6 C1 -77.64(10) . . . . ?
C10 C5 O6 C1 40.70(10) . . . . ?
O15 C12 O13 C2 -75.38(10) . . . . ?
C16 C12 O13 C2 163.64(9) . . . . ?
C11 C12 O13 C2 36.80(11) . . . . ?
C3 C2 O13 C12 -135.76(9) . . . . ?
C1 C2 O13 C12 -16.53(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O15 H15 O15 0.85(2) 2.01(2) 2.8624(8) 173.8(17) 8_554
C11 H11 O13 1 2.38 3.3304(14) 158.3 3_545

_database_code_depnum_ccdc_archive 'CCDC 1003498'
#######################################################################
#
#                 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_ch126

_audit_creation_date             2014-02-24T08:09:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            
'Simanis/Mitchell   bis-ether from hexanes evaporation'
_chemical_formula_moiety         'C11 H14 O3'
_chemical_formula_sum            'C11 H14 O3'
_chemical_formula_weight         194.22
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.1815(2)
_cell_length_b                   8.0509(2)
_cell_length_c                   15.9570(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     922.59(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.69
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.085
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.9836
_exptl_absorpt_correction_T_max  0.9915

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0087
_diffrn_reflns_number            27583
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         26.77
_diffrn_reflns_theta_full        26.77
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             1161
_reflns_number_gt                1112
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0442P)²+0.2919P] 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_number_reflns         1161
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0752
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.4174(2) 0.1926(2) 0.29147(10) 0.0148(3) Uani 1 1 d . . .
H1 H 0.5236 0.207 0.2516 0.018 Uiso 1 1 calc R . .
C2 C 0.2533(3) 0.3109(2) 0.27061(10) 0.0169(3) Uani 1 1 d . . .
H2 H 0.274 0.3666 0.2154 0.02 Uiso 1 1 calc R . .
C3 C 0.0683(3) 0.2174(2) 0.27066(10) 0.0192(4) Uani 1 1 d . . .
H3A H -0.0361 0.2977 0.2715 0.023 Uiso 1 1 calc R . .
H3B H 0.0577 0.15 0.219 0.023 Uiso 1 1 calc R . .
C4 C 0.0569(2) 0.1051(2) 0.34687(10) 0.0151(3) Uani 1 1 d . . .
C5 C 0.2397(2) 0.0200(2) 0.36875(9) 0.0118(3) Uani 1 1 d . . .
C7 C 0.2226(2) -0.1568(2) 0.40314(9) 0.0151(3) Uani 1 1 d . . .
H7A H 0.2913 -0.2362 0.3672 0.018 Uiso 1 1 calc R . .
H7B H 0.0904 -0.1913 0.4059 0.018 Uiso 1 1 calc R . .
C8 C 0.3082(2) -0.1500(2) 0.49116(10) 0.0174(3) Uani 1 1 d . . .
H8A H 0.2124 -0.1238 0.5338 0.021 Uiso 1 1 calc R . .
H8B H 0.3681 -0.2569 0.5058 0.021 Uiso 1 1 calc R . .
C9 C 0.4528(2) -0.0104(2) 0.48503(10) 0.0176(3) Uani 1 1 d . . .
H9A H 0.5662 -0.0484 0.4555 0.021 Uiso 1 1 calc R . .
H9B H 0.4878 0.031 0.5413 0.021 Uiso 1 1 calc R . .
C10 C 0.3503(2) 0.12367(19) 0.43445(9) 0.0121(3) Uani 1 1 d . . .
H10 H 0.2635 0.1879 0.4712 0.015 Uiso 1 1 calc R . .
C11 C 0.4714(2) 0.2417(2) 0.38153(10) 0.0136(3) Uani 1 1 d . . .
H11 H 0.6074 0.2267 0.3926 0.016 Uiso 1 1 calc R . .
C12 C 0.4128(2) 0.4227(2) 0.38543(10) 0.0163(3) Uani 1 1 d . . .
H12A H 0.3899 0.4572 0.4441 0.02 Uiso 1 1 calc R . .
H12B H 0.5102 0.4952 0.3612 0.02 Uiso 1 1 calc R . .
O6 O 0.35554(16) 0.02355(14) 0.29511(7) 0.0145(3) Uani 1 1 d . . .
O13 O 0.24442(18) 0.43218(14) 0.33703(7) 0.0192(3) Uani 1 1 d . . .
O14 O -0.08264(17) 0.08593(17) 0.38840(8) 0.0235(3) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O6 1.4329(19) . ?
C1 C11 1.540(2) . ?
C1 C2 1.551(2) . ?
C1 H1 1 . ?
C2 O13 1.4425(19) . ?
C2 C3 1.527(3) . ?
C2 H2 1 . ?
C3 C4 1.517(2) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 O14 1.211(2) . ?
C4 C5 1.522(2) . ?
C5 O6 1.4402(18) . ?
C5 C7 1.531(2) . ?
C5 C10 1.558(2) . ?
C7 C8 1.534(2) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.533(2) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.536(2) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.540(2) . ?
C10 H10 1 . ?
C11 C12 1.518(2) . ?
C11 H11 1 . ?
C12 O13 1.437(2) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?

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
O6 C1 C11 106.50(12) . . ?
O6 C1 C2 110.88(13) . . ?
C11 C1 C2 103.53(12) . . ?
O6 C1 H1 111.8 . . ?
C11 C1 H1 111.8 . . ?
C2 C1 H1 111.8 . . ?
O13 C2 C3 107.16(14) . . ?
O13 C2 C1 106.93(12) . . ?
C3 C2 C1 110.98(13) . . ?
O13 C2 H2 110.5 . . ?
C3 C2 H2 110.5 . . ?
C1 C2 H2 110.5 . . ?
C4 C3 C2 109.94(13) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
O14 C4 C3 124.00(15) . . ?
O14 C4 C5 122.05(14) . . ?
C3 C4 C5 113.93(14) . . ?
O6 C5 C4 107.60(12) . . ?
O6 C5 C7 110.92(12) . . ?
C4 C5 C7 115.61(14) . . ?
O6 C5 C10 104.12(13) . . ?
C4 C5 C10 110.69(12) . . ?
C7 C5 C10 107.32(12) . . ?
C5 C7 C8 105.24(13) . . ?
C5 C7 H7A 110.7 . . ?
C8 C7 H7A 110.7 . . ?
C5 C7 H7B 110.7 . . ?
C8 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C9 C8 C7 103.84(13) . . ?
C9 C8 H8A 111 . . ?
C7 C8 H8A 111 . . ?
C9 C8 H8B 111 . . ?
C7 C8 H8B 111 . . ?
H8A C8 H8B 109 . . ?
C8 C9 C10 102.96(13) . . ?
C8 C9 H9A 111.2 . . ?
C10 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
C10 C9 H9B 111.2 . . ?
H9A C9 H9B 109.1 . . ?
C9 C10 C11 116.83(13) . . ?
C9 C10 C5 102.80(13) . . ?
C11 C10 C5 104.45(12) . . ?
C9 C10 H10 110.7 . . ?
C11 C10 H10 110.7 . . ?
C5 C10 H10 110.7 . . ?
C12 C11 C1 102.40(13) . . ?
C12 C11 C10 114.41(13) . . ?
C1 C11 C10 102.18(12) . . ?
C12 C11 H11 112.3 . . ?
C1 C11 H11 112.3 . . ?
C10 C11 H11 112.3 . . ?
O13 C12 C11 105.19(13) . . ?
O13 C12 H12A 110.7 . . ?
C11 C12 H12A 110.7 . . ?
O13 C12 H12B 110.7 . . ?
C11 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
C1 O6 C5 103.35(11) . . ?
C12 O13 C2 108.79(12) . . ?

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
O6 C1 C2 O13 123.68(14) . . . . ?
C11 C1 C2 O13 9.83(16) . . . . ?
O6 C1 C2 C3 7.12(17) . . . . ?
C11 C1 C2 C3 -106.73(14) . . . . ?
O13 C2 C3 C4 -71.24(16) . . . . ?
C1 C2 C3 C4 45.18(17) . . . . ?
C2 C3 C4 O14 139.46(17) . . . . ?
C2 C3 C4 C5 -39.10(19) . . . . ?
O14 C4 C5 O6 161.57(14) . . . . ?
C3 C4 C5 O6 -19.84(17) . . . . ?
O14 C4 C5 C7 37.0(2) . . . . ?
C3 C4 C5 C7 -144.41(13) . . . . ?
O14 C4 C5 C10 -85.27(19) . . . . ?
C3 C4 C5 C10 93.32(15) . . . . ?
O6 C5 C7 C8 117.85(13) . . . . ?
C4 C5 C7 C8 -119.32(14) . . . . ?
C10 C5 C7 C8 4.72(16) . . . . ?
C5 C7 C8 C9 -28.71(16) . . . . ?
C7 C8 C9 C10 42.14(16) . . . . ?
C8 C9 C10 C11 -152.07(13) . . . . ?
C8 C9 C10 C5 -38.39(15) . . . . ?
O6 C5 C10 C9 -96.79(13) . . . . ?
C4 C5 C10 C9 147.85(13) . . . . ?
C7 C5 C10 C9 20.86(16) . . . . ?
O6 C5 C10 C11 25.65(15) . . . . ?
C4 C5 C10 C11 -89.70(15) . . . . ?
C7 C5 C10 C11 143.31(13) . . . . ?
O6 C1 C11 C12 -144.60(12) . . . . ?
C2 C1 C11 C12 -27.62(15) . . . . ?
O6 C1 C11 C10 -25.88(16) . . . . ?
C2 C1 C11 C10 91.09(14) . . . . ?
C9 C10 C11 C12 -137.55(15) . . . . ?
C5 C10 C11 C12 109.70(15) . . . . ?
C9 C10 C11 C1 112.62(15) . . . . ?
C5 C10 C11 C1 -0.13(15) . . . . ?
C1 C11 C12 O13 36.65(15) . . . . ?
C10 C11 C12 O13 -73.05(16) . . . . ?
C11 C1 O6 C5 43.53(15) . . . . ?
C2 C1 O6 C5 -68.44(15) . . . . ?
C4 C5 O6 C1 75.03(14) . . . . ?
C7 C5 O6 C1 -157.62(13) . . . . ?
C10 C5 O6 C1 -42.48(14) . . . . ?
C11 C12 O13 C2 -31.80(16) . . . . ?
C3 C2 O13 C12 132.46(13) . . . . ?
C1 C2 O13 C12 13.40(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 O14 1 2.5 3.441(2) 157 1_655

_database_code_depnum_ccdc_archive 'CCDC 1003499'
#######################################################################
#
#                 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_ch123

_audit_creation_date             2014-02-11T14:39:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Lactone 4D  Simanis/Mitchell'
_chemical_formula_moiety         'C11 H12 O4'
_chemical_formula_sum            'C11 H12 O4'
_chemical_formula_weight         208.21
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.8981(3)
_cell_length_b                   9.1977(2)
_cell_length_c                   8.6578(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.9810(10)
_cell_angle_gamma                90
_cell_volume                     938.29(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.36
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_F_000             440
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.9736
_exptl_absorpt_correction_T_max  0.9866

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0066
_diffrn_reflns_number            25425
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             1922
_reflns_number_gt                1837
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0388P)²+0.4962P] 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_number_reflns         1922
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.16670(9) 0.88124(12) 0.87924(13) 0.0168(2) Uani 1 1 d . . .
H1 H 0.1138 0.7967 0.8795 0.02 Uiso 1 1 calc R . .
C2 C 0.19793(9) 0.94754(12) 1.04411(13) 0.0175(2) Uani 1 1 d . . .
H2 H 0.1805 0.8768 1.1252 0.021 Uiso 1 1 calc R . .
C3 C 0.32267(10) 0.99096(13) 1.07405(13) 0.0189(3) Uani 1 1 d . . .
H3A H 0.3338 1.063 1.1598 0.023 Uiso 1 1 calc R . .
H3B H 0.369 0.9043 1.1077 0.023 Uiso 1 1 calc R . .
C4 C 0.36300(9) 1.05516(12) 0.93083(13) 0.0160(2) Uani 1 1 d . . .
C5 C 0.31412(9) 0.98209(12) 0.77838(13) 0.0155(2) Uani 1 1 d . . .
C7 C 0.39568(10) 0.96317(14) 0.65880(14) 0.0224(3) Uani 1 1 d . . .
H7A H 0.4269 0.8633 0.6631 0.027 Uiso 1 1 calc R . .
H7B H 0.4594 1.0329 0.6789 0.027 Uiso 1 1 calc R . .
C8 C 0.32511(11) 0.99268(14) 0.49819(14) 0.0239(3) Uani 1 1 d . . .
H8A H 0.3503 1.0838 0.4526 0.029 Uiso 1 1 calc R . .
H8B H 0.3335 0.9117 0.4254 0.029 Uiso 1 1 calc R . .
C9 C 0.20150(11) 1.00585(13) 0.52787(13) 0.0223(3) Uani 1 1 d . . .
H9A H 0.1633 0.91 0.5177 0.027 Uiso 1 1 calc R . .
H9B H 0.1591 1.0744 0.4531 0.027 Uiso 1 1 calc R . .
C10 C 0.20831(9) 1.06336(12) 0.69554(12) 0.0158(2) Uani 1 1 d . . .
H10 H 0.2174 1.1714 0.7013 0.019 Uiso 1 1 calc R . .
C11 C 0.11138(9) 1.00913(12) 0.78225(13) 0.0164(2) Uani 1 1 d . . .
H11 H 0.0439 0.9771 0.7081 0.02 Uiso 1 1 calc R . .
C12 C 0.07888(9) 1.11485(12) 0.90127(14) 0.0172(2) Uani 1 1 d . . .
O6 O 0.26738(7) 0.84359(8) 0.81560(9) 0.0178(2) Uani 1 1 d . . .
O13 O 0.12733(7) 1.07700(9) 1.04686(9) 0.0194(2) Uani 1 1 d . . .
O14 O 0.42735(7) 1.15749(9) 0.93538(10) 0.0222(2) Uani 1 1 d . . .
O15 O 0.01877(7) 1.22004(9) 0.88034(10) 0.0232(2) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O6 1.4289(13) . ?
C1 C11 1.5390(15) . ?
C1 C2 1.5493(15) . ?
C1 H1 1 . ?
C2 O13 1.4593(13) . ?
C2 C3 1.5240(15) . ?
C2 H2 1 . ?
C3 C4 1.5105(16) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 O14 1.2105(14) . ?
C4 C5 1.5227(15) . ?
C5 O6 1.4442(13) . ?
C5 C7 1.5240(15) . ?
C5 C10 1.5516(15) . ?
C7 C8 1.5453(17) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.5326(18) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.5365(15) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.5436(15) . ?
C10 H10 1 . ?
C11 C12 1.5058(16) . ?
C11 H11 1 . ?
C12 O15 1.2019(14) . ?
C12 O13 1.3567(14) . ?
C12 O13 3.1050(13) 3_577 ?
O13 C12 3.1050(13) 3_577 ?

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
O6 C1 C11 107.02(9) . . ?
O6 C1 C2 110.12(8) . . ?
C11 C1 C2 103.39(9) . . ?
O6 C1 H1 112 . . ?
C11 C1 H1 112 . . ?
C2 C1 H1 112 . . ?
O13 C2 C3 109.43(9) . . ?
O13 C2 C1 105.74(8) . . ?
C3 C2 C1 111.30(9) . . ?
O13 C2 H2 110.1 . . ?
C3 C2 H2 110.1 . . ?
C1 C2 H2 110.1 . . ?
C4 C3 C2 112.07(9) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O14 C4 C3 123.29(10) . . ?
O14 C4 C5 122.35(10) . . ?
C3 C4 C5 114.35(10) . . ?
O6 C5 C4 107.97(9) . . ?
O6 C5 C7 110.61(9) . . ?
C4 C5 C7 115.89(10) . . ?
O6 C5 C10 102.42(8) . . ?
C4 C5 C10 112.07(9) . . ?
C7 C5 C10 107.05(9) . . ?
C5 C7 C8 105.88(10) . . ?
C5 C7 H7A 110.6 . . ?
C8 C7 H7A 110.6 . . ?
C5 C7 H7B 110.6 . . ?
C8 C7 H7B 110.6 . . ?
H7A C7 H7B 108.7 . . ?
C9 C8 C7 106.09(9) . . ?
C9 C8 H8A 110.5 . . ?
C7 C8 H8A 110.5 . . ?
C9 C8 H8B 110.5 . . ?
C7 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C8 C9 C10 105.05(9) . . ?
C8 C9 H9A 110.7 . . ?
C10 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
C10 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C9 C10 C11 113.79(9) . . ?
C9 C10 C5 101.76(9) . . ?
C11 C10 C5 103.45(8) . . ?
C9 C10 H10 112.3 . . ?
C11 C10 H10 112.3 . . ?
C5 C10 H10 112.3 . . ?
C12 C11 C1 104.55(9) . . ?
C12 C11 C10 113.85(9) . . ?
C1 C11 C10 102.74(9) . . ?
C12 C11 H11 111.7 . . ?
C1 C11 H11 111.7 . . ?
C10 C11 H11 111.7 . . ?
O15 C12 O13 120.92(11) . . ?
O15 C12 C11 128.36(11) . . ?
O13 C12 C11 110.71(9) . . ?
O15 C12 O13 90.78(7) . 3_577 ?
O13 C12 O13 87.83(6) . 3_577 ?
C11 C12 O13 90.87(6) . 3_577 ?
C1 O6 C5 103.99(8) . . ?
C12 O13 C2 111.44(8) . . ?
C12 O13 C12 92.17(6) . 3_577 ?
C2 O13 C12 90.40(6) . 3_577 ?

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
O6 C1 C2 O13 133.84(9) . . . . ?
C11 C1 C2 O13 19.79(11) . . . . ?
O6 C1 C2 C3 15.11(12) . . . . ?
C11 C1 C2 C3 -98.95(10) . . . . ?
O13 C2 C3 C4 -78.02(11) . . . . ?
C1 C2 C3 C4 38.48(13) . . . . ?
C2 C3 C4 O14 140.73(11) . . . . ?
C2 C3 C4 C5 -38.18(13) . . . . ?
O14 C4 C5 O6 164.66(10) . . . . ?
C3 C4 C5 O6 -16.42(12) . . . . ?
O14 C4 C5 C7 39.99(15) . . . . ?
C3 C4 C5 C7 -141.09(10) . . . . ?
O14 C4 C5 C10 -83.28(13) . . . . ?
C3 C4 C5 C10 95.64(11) . . . . ?
O6 C5 C7 C8 95.19(11) . . . . ?
C4 C5 C7 C8 -141.52(10) . . . . ?
C10 C5 C7 C8 -15.66(12) . . . . ?
C5 C7 C8 C9 -8.03(13) . . . . ?
C7 C8 C9 C10 28.89(12) . . . . ?
C8 C9 C10 C11 -148.13(9) . . . . ?
C8 C9 C10 C5 -37.56(11) . . . . ?
O6 C5 C10 C9 -83.50(10) . . . . ?
C4 C5 C10 C9 161.01(9) . . . . ?
C7 C5 C10 C9 32.90(11) . . . . ?
O6 C5 C10 C11 34.75(10) . . . . ?
C4 C5 C10 C11 -80.73(11) . . . . ?
C7 C5 C10 C11 151.15(9) . . . . ?
O6 C1 C11 C12 -135.09(9) . . . . ?
C2 C1 C11 C12 -18.82(11) . . . . ?
O6 C1 C11 C10 -15.95(11) . . . . ?
C2 C1 C11 C10 100.32(9) . . . . ?
C9 C10 C11 C12 -149.46(10) . . . . ?
C5 C10 C11 C12 101.00(10) . . . . ?
C9 C10 C11 C1 98.11(10) . . . . ?
C5 C10 C11 C1 -11.43(10) . . . . ?
C1 C11 C12 O15 -167.91(11) . . . . ?
C10 C11 C12 O15 80.75(14) . . . . ?
C1 C11 C12 O13 11.78(12) . . . . ?
C10 C11 C12 O13 -99.56(11) . . . . ?
C1 C11 C12 O13 -76.23(7) . . . 3_577 ?
C10 C11 C12 O13 172.43(8) . . . 3_577 ?
C11 C1 O6 C5 39.31(10) . . . . ?
C2 C1 O6 C5 -72.41(10) . . . . ?
C4 C5 O6 C1 72.60(10) . . . . ?
C7 C5 O6 C1 -159.63(9) . . . . ?
C10 C5 O6 C1 -45.82(10) . . . . ?
O15 C12 O13 C2 -179.11(10) . . . . ?
C11 C12 O13 C2 1.17(12) . . . . ?
O13 C12 O13 C2 91.28(8) 3_577 . . . ?
O15 C12 O13 C12 89.61(10) . . . 3_577 ?
C11 C12 O13 C12 -90.11(8) . . . 3_577 ?
O13 C12 O13 C12 0 3_577 . . 3_577 ?
C3 C2 O13 C12 106.36(10) . . . . ?
C1 C2 O13 C12 -13.60(11) . . . . ?
C3 C2 O13 C12 -161.15(8) . . . 3_577 ?
C1 C2 O13 C12 78.88(8) . . . 3_577 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 O15 1 2.56 3.2930(14) 129.6 2_546
C2 H2 O15 1 2.53 3.1496(14) 120.1 3_577
C3 H3B O14 0.99 2.57 3.2840(14) 129.4 3_677
C8 H8A O14 0.99 2.56 3.5089(15) 160 4_585
C9 H9B O15 0.99 2.54 3.4559(15) 153.2 4_585

_database_code_depnum_ccdc_archive 'CCDC 1003500'
#######################################################################
#
#                 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_cgh0142_0ma

_audit_creation_date             2014-05-15T15:07:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H22 O5'
_chemical_formula_sum            'C19 H22 O5'
_chemical_formula_weight         330.37
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Pc
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_Int_Tables_number      7
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   16.831(4)
_cell_length_b                   8.3170(19)
_cell_length_c                   11.555(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.853(4)
_cell_angle_gamma                90
_cell_volume                     1588.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4018
_cell_measurement_theta_min      2.4642
_cell_measurement_theta_max      25.9136
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.041
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.9765
_exptl_absorpt_correction_T_max  0.9960

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_number            14746
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.23
_diffrn_reflns_theta_max         25.82
_diffrn_reflns_theta_full        25.82
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             3040
_reflns_number_gt                2804
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_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, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0393P)²+0.3197P] 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_number_reflns         3040
_refine_ls_number_parameters     435
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0656
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.51903(13) 0.7227(2) 0.25133(19) 0.0163(4) Uani 1 1 d . . .
H1 H 0.5347 0.739 0.3384 0.02 Uiso 1 1 calc R . .
C2 C 0.47214(13) 0.8699(3) 0.1886(2) 0.0189(5) Uani 1 1 d . . .
H2 H 0.4743 0.9624 0.2445 0.023 Uiso 1 1 calc R . .
C3 C 0.50681(14) 0.9186(3) 0.0807(2) 0.0194(5) Uani 1 1 d . . .
H3A H 0.4684 0.9919 0.0309 0.023 Uiso 1 1 calc R . .
H3B H 0.5581 0.9777 0.1067 0.023 Uiso 1 1 calc R . .
C4 C 0.52237(14) 0.7745(3) 0.0085(2) 0.0175(5) Uani 1 1 d . . .
C5 C 0.55144(13) 0.6270(2) 0.08285(18) 0.0156(4) Uani 1 1 d . . .
C7 C 0.61025(14) 0.5136(3) 0.0405(2) 0.0199(5) Uani 1 1 d . . .
H7A H 0.6665 0.5533 0.0624 0.024 Uiso 1 1 calc R . .
H7B H 0.5966 0.4988 -0.046 0.024 Uiso 1 1 calc R . .
C8 C 0.59844(15) 0.3571(3) 0.1057(2) 0.0224(5) Uani 1 1 d . . .
H8A H 0.6187 0.2635 0.067 0.027 Uiso 1 1 calc R . .
H8B H 0.627 0.3619 0.1888 0.027 Uiso 1 1 calc R . .
C9 C 0.50675(14) 0.3465(3) 0.0981(2) 0.0200(5) Uani 1 1 d . . .
H9A H 0.4938 0.2846 0.1654 0.024 Uiso 1 1 calc R . .
H9B H 0.4807 0.2936 0.0239 0.024 Uiso 1 1 calc R . .
C10 C 0.47742(13) 0.5225(2) 0.10177(18) 0.0153(4) Uani 1 1 d . . .
H10 H 0.4302 0.542 0.0366 0.018 Uiso 1 1 calc R . .
C11 C 0.45841(13) 0.5834(2) 0.22013(18) 0.0155(4) Uani 1 1 d . . .
H11 H 0.465 0.498 0.2821 0.019 Uiso 1 1 calc R . .
C12 C 0.37742(14) 0.6679(3) 0.20523(19) 0.0170(4) Uani 1 1 d . . .
H12 H 0.3344 0.603 0.1543 0.02 Uiso 1 1 calc R . .
C16 C 0.27823(14) 0.7463(3) 0.3168(2) 0.0202(5) Uani 1 1 d . . .
H16A H 0.2386 0.6807 0.2624 0.024 Uiso 1 1 calc R . .
H16B H 0.2732 0.8595 0.2899 0.024 Uiso 1 1 calc R . .
C17 C 0.26252(14) 0.7336(3) 0.4401(2) 0.0183(5) Uani 1 1 d . . .
C18 C 0.20661(14) 0.6241(3) 0.4687(2) 0.0198(5) Uani 1 1 d . . .
H18 H 0.1756 0.5602 0.4085 0.024 Uiso 1 1 calc R . .
C19 C 0.19573(14) 0.6072(3) 0.5845(2) 0.0194(5) Uani 1 1 d . . .
H19 H 0.1564 0.5344 0.6028 0.023 Uiso 1 1 calc R . .
C20 C 0.24268(13) 0.6974(3) 0.67328(19) 0.0174(4) Uani 1 1 d . . .
C21 C 0.29789(14) 0.8087(3) 0.6461(2) 0.0202(5) Uani 1 1 d . . .
H21 H 0.3294 0.8717 0.7064 0.024 Uiso 1 1 calc R . .
C22 C 0.30643(14) 0.8267(3) 0.5298(2) 0.0216(5) Uani 1 1 d . . .
H22 H 0.3433 0.9046 0.5109 0.026 Uiso 1 1 calc R . .
C24 C 0.28655(16) 0.7368(3) 0.8807(2) 0.0260(5) Uani 1 1 d . . .
H24A H 0.3413 0.7012 0.8755 0.039 Uiso 1 1 calc R . .
H24B H 0.2735 0.7014 0.9558 0.039 Uiso 1 1 calc R . .
H24C H 0.2838 0.8544 0.8759 0.039 Uiso 1 1 calc R . .
C31 C 0.79652(14) 0.7807(3) 0.5609(2) 0.0177(5) Uani 1 1 d . . .
H31 H 0.7825 0.7597 0.6399 0.021 Uiso 1 1 calc R . .
C32 C 0.84081(14) 0.6358(3) 0.5161(2) 0.0199(5) Uani 1 1 d . . .
H32 H 0.8385 0.5399 0.5675 0.024 Uiso 1 1 calc R . .
C33 C 0.80317(14) 0.5961(3) 0.3887(2) 0.0223(5) Uani 1 1 d . . .
H33A H 0.8404 0.5253 0.3552 0.027 Uiso 1 1 calc R . .
H33B H 0.7521 0.5365 0.3872 0.027 Uiso 1 1 calc R . .
C34 C 0.78581(14) 0.7455(3) 0.3126(2) 0.0196(5) Uani 1 1 d . . .
C35 C 0.76098(13) 0.8894(2) 0.37869(19) 0.0166(4) Uani 1 1 d . . .
C37 C 0.70173(14) 1.0105(3) 0.3133(2) 0.0219(5) Uani 1 1 d . . .
H37A H 0.6452 0.973 0.3062 0.026 Uiso 1 1 calc R . .
H37B H 0.7129 1.0325 0.2337 0.026 Uiso 1 1 calc R . .
C38 C 0.71801(15) 1.1593(3) 0.3929(2) 0.0228(5) Uani 1 1 d . . .
H38A H 0.6963 1.2577 0.3501 0.027 Uiso 1 1 calc R . .
H38B H 0.6937 1.1472 0.464 0.027 Uiso 1 1 calc R . .
C39 C 0.81021(14) 1.1645(3) 0.4250(2) 0.0199(5) Uani 1 1 d . . .
H39A H 0.8279 1.2234 0.4999 0.024 Uiso 1 1 calc R . .
H39B H 0.8331 1.2183 0.3622 0.024 Uiso 1 1 calc R . .
C40 C 0.83779(13) 0.9874(3) 0.43808(18) 0.0161(4) Uani 1 1 d . . .
H40 H 0.8835 0.9683 0.3957 0.019 Uiso 1 1 calc R . .
C41 C 0.85815(13) 0.9189(3) 0.56444(19) 0.0164(4) Uani 1 1 d . . .
H41 H 0.8532 1.0013 0.6258 0.02 Uiso 1 1 calc R . .
C42 C 0.93809(14) 0.8312(3) 0.58963(18) 0.0178(5) Uani 1 1 d . . .
H42 H 0.9816 0.8966 0.5643 0.021 Uiso 1 1 calc R . .
C46 C 1.03702(14) 0.7457(3) 0.7547(2) 0.0201(5) Uani 1 1 d . . .
H46A H 1.0765 0.8112 0.7216 0.024 Uiso 1 1 calc R . .
H46B H 1.0423 0.6322 0.7313 0.024 Uiso 1 1 calc R . .
C47 C 1.05268(14) 0.7602(3) 0.8866(2) 0.0183(5) Uani 1 1 d . . .
C48 C 1.10796(14) 0.8710(3) 0.9452(2) 0.0195(5) Uani 1 1 d . . .
H48 H 1.1391 0.9338 0.9015 0.023 Uiso 1 1 calc R . .
C49 C 1.11829(14) 0.8914(3) 1.0661(2) 0.0203(5) Uani 1 1 d . . .
H49 H 1.1573 0.9656 1.1051 0.024 Uiso 1 1 calc R . .
C50 C 1.07132(14) 0.8028(3) 1.13016(19) 0.0175(5) Uani 1 1 d . . .
C51 C 1.01676(14) 0.6896(3) 1.0739(2) 0.0198(5) Uani 1 1 d . . .
H51 H 0.9854 0.6273 1.1175 0.024 Uiso 1 1 calc R . .
C52 C 1.00870(14) 0.6688(3) 0.9529(2) 0.0198(5) Uani 1 1 d . . .
H52 H 0.9721 0.5899 0.9145 0.024 Uiso 1 1 calc R . .
C54 C 1.02688(16) 0.7685(3) 1.3131(2) 0.0266(5) Uani 1 1 d . . .
H54A H 0.9722 0.8036 1.2774 0.04 Uiso 1 1 calc R . .
H54B H 1.0398 0.8054 1.395 0.04 Uiso 1 1 calc R . .
H54C H 1.0297 0.6508 1.3111 0.04 Uiso 1 1 calc R . .
O6 O 0.58684(9) 0.68358(18) 0.19924(13) 0.0165(3) Uani 1 1 d . . .
O13 O 0.38943(9) 0.81733(17) 0.14959(13) 0.0189(3) Uani 1 1 d . . .
O14 O 0.51138(11) 0.77402(19) -0.09836(14) 0.0247(4) Uani 1 1 d . . .
O15 O 0.35941(9) 0.68818(19) 0.31830(13) 0.0196(3) Uani 1 1 d . . .
O23 O 0.22970(10) 0.66871(19) 0.78534(14) 0.0226(4) Uani 1 1 d . . .
O36 O 0.72781(9) 0.82648(18) 0.47550(13) 0.0183(3) Uani 1 1 d . . .
O43 O 0.92387(9) 0.68561(18) 0.52227(14) 0.0201(3) Uani 1 1 d . . .
O44 O 0.79372(11) 0.7507(2) 0.21039(15) 0.0282(4) Uani 1 1 d . . .
O45 O 0.95589(9) 0.80258(19) 0.71165(13) 0.0204(3) Uani 1 1 d . . .
O53 O 1.08369(10) 0.8349(2) 1.24862(14) 0.0235(4) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O6 1.425(3) . ?
C1 C11 1.541(3) . ?
C1 C2 1.560(3) . ?
C1 H1 1 . ?
C2 O13 1.448(3) . ?
C2 C3 1.527(3) . ?
C2 H2 1 . ?
C3 C4 1.512(3) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 O14 1.213(3) . ?
C4 C5 1.524(3) . ?
C5 O6 1.443(2) . ?
C5 C7 1.513(3) . ?
C5 C10 1.568(3) . ?
C7 C8 1.536(3) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.532(3) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.548(3) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.547(3) . ?
C10 H10 1 . ?
C11 C12 1.515(3) . ?
C11 H11 1 . ?
C12 O15 1.406(3) . ?
C12 O13 1.431(3) . ?
C12 H12 1 . ?
C16 O15 1.446(3) . ?
C16 C17 1.501(3) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C22 1.389(3) . ?
C17 C18 1.394(3) . ?
C18 C19 1.391(3) . ?
C18 H18 0.95 . ?
C19 C20 1.391(3) . ?
C19 H19 0.95 . ?
C20 O23 1.374(3) . ?
C20 C21 1.389(3) . ?
C21 C22 1.387(3) . ?
C21 H21 0.95 . ?
C22 H22 0.95 . ?
C24 O23 1.433(3) . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
C31 O36 1.423(3) . ?
C31 C41 1.544(3) . ?
C31 C32 1.556(3) . ?
C31 H31 1 . ?
C32 O43 1.447(3) . ?
C32 C33 1.525(3) . ?
C32 H32 1 . ?
C33 C34 1.518(3) . ?
C33 H33A 0.99 . ?
C33 H33B 0.99 . ?
C34 O44 1.214(3) . ?
C34 C35 1.520(3) . ?
C35 O36 1.439(3) . ?
C35 C37 1.515(3) . ?
C35 C40 1.573(3) . ?
C37 C38 1.535(3) . ?
C37 H37A 0.99 . ?
C37 H37B 0.99 . ?
C38 C39 1.527(3) . ?
C38 H38A 0.99 . ?
C38 H38B 0.99 . ?
C39 C40 1.543(3) . ?
C39 H39A 0.99 . ?
C39 H39B 0.99 . ?
C40 C41 1.544(3) . ?
C40 H40 1 . ?
C41 C42 1.510(3) . ?
C41 H41 1 . ?
C42 O45 1.405(3) . ?
C42 O43 1.435(3) . ?
C42 H42 1 . ?
C46 O45 1.443(3) . ?
C46 C47 1.501(3) . ?
C46 H46A 0.99 . ?
C46 H46B 0.99 . ?
C47 C52 1.388(3) . ?
C47 C48 1.392(3) . ?
C48 C49 1.386(3) . ?
C48 H48 0.95 . ?
C49 C50 1.391(3) . ?
C49 H49 0.95 . ?
C50 O53 1.371(3) . ?
C50 C51 1.388(3) . ?
C51 C52 1.390(3) . ?
C51 H51 0.95 . ?
C52 H52 0.95 . ?
C54 O53 1.429(3) . ?
C54 H54A 0.98 . ?
C54 H54B 0.98 . ?
C54 H54C 0.98 . ?

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
O6 C1 C11 106.10(16) . . ?
O6 C1 C2 111.01(17) . . ?
C11 C1 C2 103.11(17) . . ?
O6 C1 H1 112 . . ?
C11 C1 H1 112 . . ?
C2 C1 H1 112 . . ?
O13 C2 C3 108.59(17) . . ?
O13 C2 C1 106.27(16) . . ?
C3 C2 C1 110.47(18) . . ?
O13 C2 H2 110.5 . . ?
C3 C2 H2 110.5 . . ?
C1 C2 H2 110.5 . . ?
C4 C3 C2 111.91(18) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O14 C4 C3 123.7(2) . . ?
O14 C4 C5 122.9(2) . . ?
C3 C4 C5 113.40(19) . . ?
O6 C5 C7 108.90(17) . . ?
O6 C5 C4 107.18(16) . . ?
C7 C5 C4 118.61(19) . . ?
O6 C5 C10 104.50(16) . . ?
C7 C5 C10 106.58(16) . . ?
C4 C5 C10 110.21(17) . . ?
C5 C7 C8 102.50(18) . . ?
C5 C7 H7A 111.3 . . ?
C8 C7 H7A 111.3 . . ?
C5 C7 H7B 111.3 . . ?
C8 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
C9 C8 C7 104.03(18) . . ?
C9 C8 H8A 110.9 . . ?
C7 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 109 . . ?
C8 C9 C10 105.50(18) . . ?
C8 C9 H9A 110.6 . . ?
C10 C9 H9A 110.6 . . ?
C8 C9 H9B 110.6 . . ?
C10 C9 H9B 110.6 . . ?
H9A C9 H9B 108.8 . . ?
C11 C10 C9 116.97(18) . . ?
C11 C10 C5 104.13(16) . . ?
C9 C10 C5 104.74(17) . . ?
C11 C10 H10 110.2 . . ?
C9 C10 H10 110.2 . . ?
C5 C10 H10 110.2 . . ?
C12 C11 C1 102.69(17) . . ?
C12 C11 C10 112.51(17) . . ?
C1 C11 C10 102.40(16) . . ?
C12 C11 H11 112.8 . . ?
C1 C11 H11 112.8 . . ?
C10 C11 H11 112.8 . . ?
O15 C12 O13 112.76(17) . . ?
O15 C12 C11 107.28(17) . . ?
O13 C12 C11 104.72(16) . . ?
O15 C12 H12 110.6 . . ?
O13 C12 H12 110.6 . . ?
C11 C12 H12 110.6 . . ?
O15 C16 C17 107.46(18) . . ?
O15 C16 H16A 110.2 . . ?
C17 C16 H16A 110.2 . . ?
O15 C16 H16B 110.2 . . ?
C17 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C22 C17 C18 118.4(2) . . ?
C22 C17 C16 120.3(2) . . ?
C18 C17 C16 121.2(2) . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 119.7(2) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
O23 C20 C21 124.10(19) . . ?
O23 C20 C19 115.6(2) . . ?
C21 C20 C19 120.3(2) . . ?
C22 C21 C20 119.1(2) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C17 121.7(2) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
O23 C24 H24A 109.5 . . ?
O23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O36 C31 C41 105.87(16) . . ?
O36 C31 C32 110.75(18) . . ?
C41 C31 C32 102.93(18) . . ?
O36 C31 H31 112.2 . . ?
C41 C31 H31 112.2 . . ?
C32 C31 H31 112.2 . . ?
O43 C32 C33 109.37(19) . . ?
O43 C32 C31 106.33(17) . . ?
C33 C32 C31 110.55(18) . . ?
O43 C32 H32 110.2 . . ?
C33 C32 H32 110.2 . . ?
C31 C32 H32 110.2 . . ?
C34 C33 C32 112.39(18) . . ?
C34 C33 H33A 109.1 . . ?
C32 C33 H33A 109.1 . . ?
C34 C33 H33B 109.1 . . ?
C32 C33 H33B 109.1 . . ?
H33A C33 H33B 107.9 . . ?
O44 C34 C33 123.3(2) . . ?
O44 C34 C35 123.4(2) . . ?
C33 C34 C35 113.27(19) . . ?
O36 C35 C37 108.29(18) . . ?
O36 C35 C34 106.72(17) . . ?
C37 C35 C34 119.37(19) . . ?
O36 C35 C40 104.86(16) . . ?
C37 C35 C40 106.42(17) . . ?
C34 C35 C40 110.26(18) . . ?
C35 C37 C38 102.16(17) . . ?
C35 C37 H37A 111.3 . . ?
C38 C37 H37A 111.3 . . ?
C35 C37 H37B 111.3 . . ?
C38 C37 H37B 111.3 . . ?
H37A C37 H37B 109.2 . . ?
C39 C38 C37 103.14(19) . . ?
C39 C38 H38A 111.1 . . ?
C37 C38 H38A 111.1 . . ?
C39 C38 H38B 111.1 . . ?
C37 C38 H38B 111.1 . . ?
H38A C38 H38B 109.1 . . ?
C38 C39 C40 105.67(17) . . ?
C38 C39 H39A 110.6 . . ?
C40 C39 H39A 110.6 . . ?
C38 C39 H39B 110.6 . . ?
C40 C39 H39B 110.6 . . ?
H39A C39 H39B 108.7 . . ?
C39 C40 C41 116.97(19) . . ?
C39 C40 C35 104.17(17) . . ?
C41 C40 C35 103.84(17) . . ?
C39 C40 H40 110.5 . . ?
C41 C40 H40 110.5 . . ?
C35 C40 H40 110.5 . . ?
C42 C41 C31 102.43(17) . . ?
C42 C41 C40 113.05(18) . . ?
C31 C41 C40 102.77(17) . . ?
C42 C41 H41 112.6 . . ?
C31 C41 H41 112.6 . . ?
C40 C41 H41 112.6 . . ?
O45 C42 O43 112.55(17) . . ?
O45 C42 C41 106.80(17) . . ?
O43 C42 C41 104.57(16) . . ?
O45 C42 H42 110.9 . . ?
O43 C42 H42 110.9 . . ?
C41 C42 H42 110.9 . . ?
O45 C46 C47 107.32(18) . . ?
O45 C46 H46A 110.3 . . ?
C47 C46 H46A 110.3 . . ?
O45 C46 H46B 110.3 . . ?
C47 C46 H46B 110.3 . . ?
H46A C46 H46B 108.5 . . ?
C52 C47 C48 118.1(2) . . ?
C52 C47 C46 120.4(2) . . ?
C48 C47 C46 121.4(2) . . ?
C49 C48 C47 121.1(2) . . ?
C49 C48 H48 119.4 . . ?
C47 C48 H48 119.4 . . ?
C48 C49 C50 119.7(2) . . ?
C48 C49 H49 120.2 . . ?
C50 C49 H49 120.2 . . ?
O53 C50 C51 124.2(2) . . ?
O53 C50 C49 115.7(2) . . ?
C51 C50 C49 120.1(2) . . ?
C50 C51 C52 119.1(2) . . ?
C50 C51 H51 120.4 . . ?
C52 C51 H51 120.4 . . ?
C47 C52 C51 121.7(2) . . ?
C47 C52 H52 119.1 . . ?
C51 C52 H52 119.1 . . ?
O53 C54 H54A 109.5 . . ?
O53 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
O53 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C1 O6 C5 104.18(15) . . ?
C12 O13 C2 109.35(15) . . ?
C12 O15 C16 113.42(17) . . ?
C20 O23 C24 117.01(18) . . ?
C31 O36 C35 104.62(16) . . ?
C42 O43 C32 109.22(16) . . ?
C42 O45 C46 114.26(17) . . ?
C50 O53 C54 117.03(19) . . ?

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
O6 C1 C2 O13 123.83(18) . . . . ?
C11 C1 C2 O13 10.6(2) . . . . ?
O6 C1 C2 C3 6.2(2) . . . . ?
C11 C1 C2 C3 -107.01(19) . . . . ?
O13 C2 C3 C4 -71.8(2) . . . . ?
C1 C2 C3 C4 44.3(2) . . . . ?
C2 C3 C4 O14 142.7(2) . . . . ?
C2 C3 C4 C5 -35.8(3) . . . . ?
O14 C4 C5 O6 158.3(2) . . . . ?
C3 C4 C5 O6 -23.1(2) . . . . ?
O14 C4 C5 C7 34.6(3) . . . . ?
C3 C4 C5 C7 -146.81(19) . . . . ?
O14 C4 C5 C10 -88.5(3) . . . . ?
C3 C4 C5 C10 90.0(2) . . . . ?
O6 C5 C7 C8 78.6(2) . . . . ?
C4 C5 C7 C8 -158.52(19) . . . . ?
C10 C5 C7 C8 -33.6(2) . . . . ?
C5 C7 C8 C9 41.3(2) . . . . ?
C7 C8 C9 C10 -33.3(2) . . . . ?
C8 C9 C10 C11 -102.3(2) . . . . ?
C8 C9 C10 C5 12.3(2) . . . . ?
O6 C5 C10 C11 21.5(2) . . . . ?
C7 C5 C10 C11 136.72(17) . . . . ?
C4 C5 C10 C11 -93.3(2) . . . . ?
O6 C5 C10 C9 -101.85(18) . . . . ?
C7 C5 C10 C9 13.4(2) . . . . ?
C4 C5 C10 C9 143.30(19) . . . . ?
O6 C1 C11 C12 -145.51(16) . . . . ?
C2 C1 C11 C12 -28.8(2) . . . . ?
O6 C1 C11 C10 -28.7(2) . . . . ?
C2 C1 C11 C10 88.08(19) . . . . ?
C9 C10 C11 C12 -131.6(2) . . . . ?
C5 C10 C11 C12 113.37(18) . . . . ?
C9 C10 C11 C1 118.8(2) . . . . ?
C5 C10 C11 C1 3.8(2) . . . . ?
C1 C11 C12 O15 -82.37(19) . . . . ?
C10 C11 C12 O15 168.26(17) . . . . ?
C1 C11 C12 O13 37.7(2) . . . . ?
C10 C11 C12 O13 -71.7(2) . . . . ?
O15 C16 C17 C22 65.4(3) . . . . ?
O15 C16 C17 C18 -111.7(2) . . . . ?
C22 C17 C18 C19 -0.7(3) . . . . ?
C16 C17 C18 C19 176.5(2) . . . . ?
C17 C18 C19 C20 -1.8(3) . . . . ?
C18 C19 C20 O23 -177.82(19) . . . . ?
C18 C19 C20 C21 2.6(3) . . . . ?
O23 C20 C21 C22 179.5(2) . . . . ?
C19 C20 C21 C22 -1.0(3) . . . . ?
C20 C21 C22 C17 -1.5(3) . . . . ?
C18 C17 C22 C21 2.3(3) . . . . ?
C16 C17 C22 C21 -174.8(2) . . . . ?
O36 C31 C32 O43 124.60(18) . . . . ?
C41 C31 C32 O43 11.8(2) . . . . ?
O36 C31 C32 C33 6.0(2) . . . . ?
C41 C31 C32 C33 -106.8(2) . . . . ?
O43 C32 C33 C34 -73.1(2) . . . . ?
C31 C32 C33 C34 43.6(3) . . . . ?
C32 C33 C34 O44 143.4(2) . . . . ?
C32 C33 C34 C35 -34.2(3) . . . . ?
O44 C34 C35 O36 157.9(2) . . . . ?
C33 C34 C35 O36 -24.5(2) . . . . ?
O44 C34 C35 C37 34.8(3) . . . . ?
C33 C34 C35 C37 -147.6(2) . . . . ?
O44 C34 C35 C40 -88.8(3) . . . . ?
C33 C34 C35 C40 88.8(2) . . . . ?
O36 C35 C37 C38 78.4(2) . . . . ?
C34 C35 C37 C38 -159.4(2) . . . . ?
C40 C35 C37 C38 -33.9(2) . . . . ?
C35 C37 C38 C39 43.2(2) . . . . ?
C37 C38 C39 C40 -36.3(2) . . . . ?
C38 C39 C40 C41 -98.8(2) . . . . ?
C38 C39 C40 C35 15.1(2) . . . . ?
O36 C35 C40 C39 -102.72(18) . . . . ?
C37 C35 C40 C39 11.9(2) . . . . ?
C34 C35 C40 C39 142.75(19) . . . . ?
O36 C35 C40 C41 20.2(2) . . . . ?
C37 C35 C40 C41 134.87(18) . . . . ?
C34 C35 C40 C41 -94.3(2) . . . . ?
O36 C31 C41 C42 -146.38(17) . . . . ?
C32 C31 C41 C42 -30.1(2) . . . . ?
O36 C31 C41 C40 -28.9(2) . . . . ?
C32 C31 C41 C40 87.38(19) . . . . ?
C39 C40 C41 C42 -131.5(2) . . . . ?
C35 C40 C41 C42 114.42(19) . . . . ?
C39 C40 C41 C31 118.9(2) . . . . ?
C35 C40 C41 C31 4.8(2) . . . . ?
C31 C41 C42 O45 -80.99(19) . . . . ?
C40 C41 C42 O45 169.14(17) . . . . ?
C31 C41 C42 O43 38.5(2) . . . . ?
C40 C41 C42 O43 -71.4(2) . . . . ?
O45 C46 C47 C52 64.9(3) . . . . ?
O45 C46 C47 C48 -111.5(2) . . . . ?
C52 C47 C48 C49 -0.8(3) . . . . ?
C46 C47 C48 C49 175.7(2) . . . . ?
C47 C48 C49 C50 -1.7(3) . . . . ?
C48 C49 C50 O53 -177.82(19) . . . . ?
C48 C49 C50 C51 2.7(3) . . . . ?
O53 C50 C51 C52 179.3(2) . . . . ?
C49 C50 C51 C52 -1.3(3) . . . . ?
C48 C47 C52 C51 2.2(3) . . . . ?
C46 C47 C52 C51 -174.3(2) . . . . ?
C50 C51 C52 C47 -1.2(3) . . . . ?
C11 C1 O6 C5 43.99(19) . . . . ?
C2 C1 O6 C5 -67.33(19) . . . . ?
C7 C5 O6 C1 -153.98(17) . . . . ?
C4 C5 O6 C1 76.6(2) . . . . ?
C10 C5 O6 C1 -40.40(18) . . . . ?
O15 C12 O13 C2 84.0(2) . . . . ?
C11 C12 O13 C2 -32.3(2) . . . . ?
C3 C2 O13 C12 132.08(17) . . . . ?
C1 C2 O13 C12 13.2(2) . . . . ?
O13 C12 O15 C16 73.8(2) . . . . ?
C11 C12 O15 C16 -171.46(17) . . . . ?
C17 C16 O15 C12 169.93(17) . . . . ?
C21 C20 O23 C24 -11.6(3) . . . . ?
C19 C20 O23 C24 168.9(2) . . . . ?
C41 C31 O36 C35 43.4(2) . . . . ?
C32 C31 O36 C35 -67.5(2) . . . . ?
C37 C35 O36 C31 -152.74(17) . . . . ?
C34 C35 O36 C31 77.6(2) . . . . ?
C40 C35 O36 C31 -39.43(19) . . . . ?
O45 C42 O43 C32 83.2(2) . . . . ?
C41 C42 O43 C32 -32.4(2) . . . . ?
C33 C32 O43 C42 131.81(18) . . . . ?
C31 C32 O43 C42 12.4(2) . . . . ?
O43 C42 O45 C46 76.5(2) . . . . ?
C41 C42 O45 C46 -169.32(17) . . . . ?
C47 C46 O45 C42 166.32(18) . . . . ?
C51 C50 O53 C54 -11.6(3) . . . . ?
C49 C50 O53 C54 168.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8A O36 0.99 2.4 3.251(3) 143.1 2_564
C41 H41 O44 1 2.57 3.501(3) 155.6 2_575

_database_code_depnum_ccdc_archive 'CCDC 1003501'
#######################################################################
#
#                 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_ch134

_audit_creation_date             2014-03-06T08:55:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H20 O4'
_chemical_formula_sum            'C18 H20 O4'
_chemical_formula_weight         300.34
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.8857(3)
_cell_length_b                   7.1169(2)
_cell_length_c                   10.7398(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.306(2)
_cell_angle_gamma                90
_cell_volume                     754.35(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      2.7233
_cell_measurement_theta_max      26.7069
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.106
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.9725
_exptl_absorpt_correction_T_max  0.9902

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_av_unetI/netI     0.012
_diffrn_reflns_number            21489
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.9
_diffrn_reflns_theta_max         26.71
_diffrn_reflns_theta_full        26.71
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             3190
_reflns_number_gt                3128
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0426P)²+0.1575P] 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_number_reflns         3190
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0703
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.033

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.17385(11) 0.71022(16) 0.61627(10) 0.0146(2) Uani 1 1 d . . .
H1 H 0.0986 0.6182 0.6254 0.018 Uiso 1 1 calc R . .
C2 C 0.13349(11) 0.86883(17) 0.52200(10) 0.0153(2) Uani 1 1 d . . .
H2 H 0.0338 0.8651 0.5003 0.018 Uiso 1 1 calc R . .
C3 C 0.17434(12) 1.06179(17) 0.57469(11) 0.0179(2) Uani 1 1 d . . .
H3A H 0.1729 1.1547 0.506 0.021 Uiso 1 1 calc R . .
H3B H 0.1078 1.1024 0.6347 0.021 Uiso 1 1 calc R . .
C4 C 0.31480(12) 1.05686(16) 0.63974(11) 0.0159(2) Uani 1 1 d . . .
C5 C 0.34869(11) 0.87416(17) 0.70683(10) 0.0148(2) Uani 1 1 d . . .
C7 C 0.44047(12) 0.88223(19) 0.82482(11) 0.0196(2) Uani 1 1 d . . .
H7A H 0.3887 0.9142 0.8981 0.024 Uiso 1 1 calc R . .
H7B H 0.5138 0.9754 0.8171 0.024 Uiso 1 1 calc R . .
C8 C 0.49711(13) 0.6826(2) 0.83482(12) 0.0248(3) Uani 1 1 d . . .
H8A H 0.4303 0.5956 0.8688 0.03 Uiso 1 1 calc R . .
H8B H 0.5815 0.6791 0.889 0.03 Uiso 1 1 calc R . .
C9 C 0.52503(13) 0.63087(19) 0.69969(12) 0.0230(3) Uani 1 1 d . . .
H9A H 0.517 0.4935 0.6868 0.028 Uiso 1 1 calc R . .
H9B H 0.6174 0.6707 0.68 0.028 Uiso 1 1 calc R . .
C10 C 0.41696(12) 0.73649(16) 0.61617(11) 0.0152(2) Uani 1 1 d . . .
H10 H 0.4611 0.8084 0.5496 0.018 Uiso 1 1 calc R . .
C11 C 0.29709(11) 0.61949(16) 0.55895(10) 0.0146(2) Uani 1 1 d . . .
H11 H 0.3059 0.4827 0.579 0.018 Uiso 1 1 calc R . .
C12 C 0.26943(12) 0.65525(17) 0.42084(10) 0.0155(2) Uani 1 1 d . . .
H12 H 0.3554 0.6529 0.3761 0.019 Uiso 1 1 calc R . .
C16 C 0.17042(11) 0.47826(18) 0.24869(11) 0.0164(2) Uani 1 1 d . . .
C17 C 0.13408(12) 0.29735(18) 0.21185(11) 0.0182(2) Uani 1 1 d . . .
H17 H 0.116 0.2051 0.2726 0.022 Uiso 1 1 calc R . .
C18 C 0.12422(12) 0.25162(19) 0.08589(12) 0.0203(3) Uani 1 1 d . . .
H18 H 0.0991 0.1277 0.0611 0.024 Uiso 1 1 calc R . .
C19 C 0.15074(12) 0.3849(2) -0.00453(11) 0.0201(3) Uani 1 1 d . . .
C20 C 0.18628(12) 0.56546(18) 0.03432(11) 0.0205(3) Uani 1 1 d . . .
H20 H 0.2042 0.6578 -0.0264 0.025 Uiso 1 1 calc R . .
C21 C 0.19632(12) 0.61452(18) 0.16034(11) 0.0185(2) Uani 1 1 d . . .
H21 H 0.2204 0.7387 0.1853 0.022 Uiso 1 1 calc R . .
C22 C 0.14104(15) 0.3329(2) -0.14124(11) 0.0287(3) Uani 1 1 d . . .
H22A H 0.1418 0.1957 -0.1497 0.043 Uiso 1 1 calc R . .
H22B H 0.2184 0.3861 -0.1822 0.043 Uiso 1 1 calc R . .
H22C H 0.0567 0.383 -0.1805 0.043 Uiso 1 1 calc R . .
O6 O 0.22219(8) 0.78580(12) 0.73320(7) 0.01583(18) Uani 1 1 d . . .
O13 O 0.20786(8) 0.83450(12) 0.41208(7) 0.01797(18) Uani 1 1 d . . .
O14 O 0.39475(9) 1.18500(13) 0.63542(9) 0.0231(2) Uani 1 1 d . . .
O15 O 0.17939(8) 0.51056(13) 0.37627(7) 0.01780(18) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O6 1.4232(13) . ?
C1 C11 1.5384(16) . ?
C1 C2 1.5530(16) . ?
C1 H1 1 . ?
C2 O13 1.4470(13) . ?
C2 C3 1.5306(16) . ?
C2 H2 1 . ?
C3 C4 1.5184(16) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 O14 1.2095(15) . ?
C4 C5 1.5147(16) . ?
C5 O6 1.4423(13) . ?
C5 C7 1.5164(15) . ?
C5 C10 1.5618(16) . ?
C7 C8 1.5287(19) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C9 1.5376(19) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.5494(16) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.5464(15) . ?
C10 H10 1 . ?
C11 C12 1.5142(15) . ?
C11 H11 1 . ?
C12 O13 1.4143(14) . ?
C12 O15 1.4257(14) . ?
C12 H12 1 . ?
C16 O15 1.3871(13) . ?
C16 C17 1.3881(18) . ?
C16 C21 1.3908(17) . ?
C17 C18 1.3893(16) . ?
C17 H17 0.95 . ?
C18 C19 1.3932(19) . ?
C18 H18 0.95 . ?
C19 C20 1.3899(18) . ?
C19 C22 1.5119(16) . ?
C20 C21 1.3957(16) . ?
C20 H20 0.95 . ?
C21 H21 0.95 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?

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
O6 C1 C11 106.17(9) . . ?
O6 C1 C2 111.17(9) . . ?
C11 C1 C2 102.93(9) . . ?
O6 C1 H1 112 . . ?
C11 C1 H1 112 . . ?
C2 C1 H1 112 . . ?
O13 C2 C3 108.51(9) . . ?
O13 C2 C1 106.59(9) . . ?
C3 C2 C1 111.02(9) . . ?
O13 C2 H2 110.2 . . ?
C3 C2 H2 110.2 . . ?
C1 C2 H2 110.2 . . ?
C4 C3 C2 111.36(9) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108 . . ?
O14 C4 C5 122.58(11) . . ?
O14 C4 C3 123.18(11) . . ?
C5 C4 C3 114.21(10) . . ?
O6 C5 C4 107.29(9) . . ?
O6 C5 C7 109.65(9) . . ?
C4 C5 C7 118.05(10) . . ?
O6 C5 C10 105.05(9) . . ?
C4 C5 C10 109.49(9) . . ?
C7 C5 C10 106.59(9) . . ?
C5 C7 C8 102.86(10) . . ?
C5 C7 H7A 111.2 . . ?
C8 C7 H7A 111.2 . . ?
C5 C7 H7B 111.2 . . ?
C8 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?
C7 C8 C9 103.95(10) . . ?
C7 C8 H8A 111 . . ?
C9 C8 H8A 111 . . ?
C7 C8 H8B 111 . . ?
C9 C8 H8B 111 . . ?
H8A C8 H8B 109 . . ?
C8 C9 C10 105.96(10) . . ?
C8 C9 H9A 110.5 . . ?
C10 C9 H9A 110.5 . . ?
C8 C9 H9B 110.5 . . ?
C10 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C11 C10 C9 117.12(10) . . ?
C11 C10 C5 103.70(9) . . ?
C9 C10 C5 104.58(9) . . ?
C11 C10 H10 110.3 . . ?
C9 C10 H10 110.3 . . ?
C5 C10 H10 110.3 . . ?
C12 C11 C1 102.65(9) . . ?
C12 C11 C10 112.94(9) . . ?
C1 C11 C10 102.79(9) . . ?
C12 C11 H11 112.5 . . ?
C1 C11 H11 112.5 . . ?
C10 C11 H11 112.5 . . ?
O13 C12 O15 111.79(9) . . ?
O13 C12 C11 105.63(9) . . ?
O15 C12 C11 106.34(9) . . ?
O13 C12 H12 111 . . ?
O15 C12 H12 111 . . ?
C11 C12 H12 111 . . ?
O15 C16 C17 115.85(11) . . ?
O15 C16 C21 123.68(11) . . ?
C17 C16 C21 120.47(11) . . ?
C16 C17 C18 119.82(12) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 120.91(12) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 118.34(11) . . ?
C20 C19 C22 121.26(12) . . ?
C18 C19 C22 120.41(12) . . ?
C19 C20 C21 121.67(12) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C16 C21 C20 118.79(12) . . ?
C16 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 O6 C5 104.02(8) . . ?
C12 O13 C2 109.57(9) . . ?
C16 O15 C12 117.03(9) . . ?

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
O6 C1 C2 O13 125.58(10) . . . . ?
C11 C1 C2 O13 12.30(11) . . . . ?
O6 C1 C2 C3 7.59(13) . . . . ?
C11 C1 C2 C3 -105.69(10) . . . . ?
O13 C2 C3 C4 -74.35(11) . . . . ?
C1 C2 C3 C4 42.48(13) . . . . ?
C2 C3 C4 O14 142.95(11) . . . . ?
C2 C3 C4 C5 -34.83(13) . . . . ?
O14 C4 C5 O6 159.21(10) . . . . ?
C3 C4 C5 O6 -23.00(12) . . . . ?
O14 C4 C5 C7 34.82(16) . . . . ?
C3 C4 C5 C7 -147.39(10) . . . . ?
O14 C4 C5 C10 -87.30(13) . . . . ?
C3 C4 C5 C10 90.49(11) . . . . ?
O6 C5 C7 C8 78.97(11) . . . . ?
C4 C5 C7 C8 -157.82(10) . . . . ?
C10 C5 C7 C8 -34.23(12) . . . . ?
C5 C7 C8 C9 40.44(12) . . . . ?
C7 C8 C9 C10 -31.51(12) . . . . ?
C8 C9 C10 C11 -103.76(12) . . . . ?
C8 C9 C10 C5 10.33(12) . . . . ?
O6 C5 C10 C11 21.76(11) . . . . ?
C4 C5 C10 C11 -93.18(10) . . . . ?
C7 C5 C10 C11 138.07(10) . . . . ?
O6 C5 C10 C9 -101.49(10) . . . . ?
C4 C5 C10 C9 143.57(10) . . . . ?
C7 C5 C10 C9 14.83(12) . . . . ?
O6 C1 C11 C12 -145.50(9) . . . . ?
C2 C1 C11 C12 -28.61(11) . . . . ?
O6 C1 C11 C10 -28.08(11) . . . . ?
C2 C1 C11 C10 88.82(10) . . . . ?
C9 C10 C11 C12 -132.19(11) . . . . ?
C5 C10 C11 C12 113.23(10) . . . . ?
C9 C10 C11 C1 117.93(11) . . . . ?
C5 C10 C11 C1 3.35(11) . . . . ?
C1 C11 C12 O13 36.15(11) . . . . ?
C10 C11 C12 O13 -73.81(11) . . . . ?
C1 C11 C12 O15 -82.78(10) . . . . ?
C10 C11 C12 O15 167.26(9) . . . . ?
O15 C16 C17 C18 -179.22(10) . . . . ?
C21 C16 C17 C18 0.37(17) . . . . ?
C16 C17 C18 C19 0.18(18) . . . . ?
C17 C18 C19 C20 -0.51(18) . . . . ?
C17 C18 C19 C22 179.38(11) . . . . ?
C18 C19 C20 C21 0.29(18) . . . . ?
C22 C19 C20 C21 -179.59(11) . . . . ?
O15 C16 C21 C20 178.97(10) . . . . ?
C17 C16 C21 C20 -0.58(17) . . . . ?
C19 C20 C21 C16 0.25(18) . . . . ?
C11 C1 O6 C5 43.26(11) . . . . ?
C2 C1 O6 C5 -67.98(11) . . . . ?
C4 C5 O6 C1 76.19(10) . . . . ?
C7 C5 O6 C1 -154.46(9) . . . . ?
C10 C5 O6 C1 -40.26(11) . . . . ?
O15 C12 O13 C2 85.72(11) . . . . ?
C11 C12 O13 C2 -29.53(11) . . . . ?
C3 C2 O13 C12 130.06(9) . . . . ?
C1 C2 O13 C12 10.42(12) . . . . ?
C17 C16 O15 C12 152.92(10) . . . . ?
C21 C16 O15 C12 -26.65(16) . . . . ?
O13 C12 O15 C16 83.92(12) . . . . ?
C11 C12 O15 C16 -161.27(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9A O14 0.99 2.55 3.4788(16) 156 1_545
C11 H11 O14 1 2.36 3.3282(15) 163 1_545
C12 H12 O14 1 2.49 3.4150(14) 153.5 2_646

_database_code_depnum_ccdc_archive 'CCDC 1003502'
#######################################################################
#
#                 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_ch104

_audit_creation_date             2013-07-10T13:25:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H22 O5'
_chemical_formula_sum            'C24 H22 O5'
_chemical_formula_weight         390.42
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.2563(4)
_cell_length_b                   12.5278(7)
_cell_length_c                   18.4201(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.169(3)
_cell_angle_gamma                90
_cell_volume                     1900.21(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9220
_cell_measurement_theta_min      2.2172
_cell_measurement_theta_max      26.7289
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.9761
_exptl_absorpt_correction_T_max  0.9859

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0091
_diffrn_reflns_number            55053
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         26.74
_diffrn_reflns_theta_full        26.74
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             4036
_reflns_number_gt                3767
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0519P)²+1.1890P] 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_number_reflns         4036
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.38750(16) 0.94614(10) 0.33570(7) 0.0171(3) Uani 1 1 d . . .
H1 H 0.4489 0.8792 0.3349 0.021 Uiso 1 1 calc R . .
C2 C 0.43926(16) 1.01524(12) 0.40339(7) 0.0219(3) Uani 1 1 d . . .
H2 H 0.5374 0.9861 0.4293 0.026 Uiso 1 1 calc R . .
C3 C 0.46535(18) 1.13130(12) 0.38220(8) 0.0270(3) Uani 1 1 d . . .
H3A H 0.4695 1.1757 0.4254 0.032 Uiso 1 1 calc R . .
H3B H 0.5682 1.1381 0.3603 0.032 Uiso 1 1 calc R . .
C4 C 0.32906(18) 1.16897(11) 0.32881(8) 0.0245(3) Uani 1 1 d . . .
C5 C 0.27218(16) 1.08490(11) 0.27327(7) 0.0187(3) Uani 1 1 d . . .
C6 C 0.22224(17) 1.12376(12) 0.19686(8) 0.0239(3) Uani 1 1 d . . .
H6A H 0.3165 1.1395 0.1702 0.029 Uiso 1 1 calc R . .
H6B H 0.1548 1.1871 0.198 0.029 Uiso 1 1 calc R . .
C7 C 0.12636(18) 1.02911(12) 0.16303(8) 0.0251(3) Uani 1 1 d . . .
H7A H 0.0526 1.0523 0.1227 0.03 Uiso 1 1 calc R . .
H7B H 0.199 0.9755 0.1457 0.03 Uiso 1 1 calc R . .
C8 C 0.03227(17) 0.98501(12) 0.22514(7) 0.0236(3) Uani 1 1 d . . .
H8A H 0.0255 0.9078 0.2221 0.028 Uiso 1 1 calc R . .
H8B H -0.0771 1.0138 0.2223 0.028 Uiso 1 1 calc R . .
C9 C 0.12581(15) 1.01903(10) 0.29764(7) 0.0173(3) Uani 1 1 d . . .
H9 H 0.0571 1.0625 0.3272 0.021 Uiso 1 1 calc R . .
C10 C 0.20555(15) 0.92687(10) 0.34274(7) 0.0162(3) Uani 1 1 d . . .
H10 H 0.1702 0.8567 0.3243 0.019 Uiso 1 1 calc R . .
C14 C 0.18731(16) 0.93861(10) 0.42368(7) 0.0171(3) Uani 1 1 d . . .
H14 H 0.0778 0.9629 0.4328 0.021 Uiso 1 1 calc R . .
C16 C 0.16593(16) 0.81862(11) 0.52256(7) 0.0186(3) Uani 1 1 d . . .
C18 C 0.17795(15) 0.70486(11) 0.54474(7) 0.0178(3) Uani 1 1 d . . .
C19 C 0.26350(17) 0.63032(11) 0.50623(7) 0.0202(3) Uani 1 1 d . . .
H19 H 0.3185 0.6521 0.4665 0.024 Uiso 1 1 calc R . .
C20 C 0.26687(17) 0.52410(11) 0.52692(7) 0.0203(3) Uani 1 1 d . . .
H20 H 0.3253 0.4753 0.5012 0.024 Uiso 1 1 calc R . .
C21 C 0.18349(16) 0.48899(11) 0.58608(7) 0.0177(3) Uani 1 1 d . . .
C22 C 0.09808(16) 0.56435(11) 0.62433(7) 0.0199(3) Uani 1 1 d . . .
H22 H 0.0419 0.5426 0.6637 0.024 Uiso 1 1 calc R . .
C23 C 0.09618(16) 0.67112(11) 0.60424(7) 0.0205(3) Uani 1 1 d . . .
H23 H 0.0401 0.7204 0.6306 0.025 Uiso 1 1 calc R . .
C24 C 0.18838(15) 0.37494(11) 0.60776(7) 0.0183(3) Uani 1 1 d . . .
C25 C 0.20329(17) 0.29400(11) 0.55624(8) 0.0224(3) Uani 1 1 d . . .
H25 H 0.2085 0.3118 0.5074 0.027 Uiso 1 1 calc R . .
C26 C 0.21036(17) 0.18730(12) 0.57719(9) 0.0268(3) Uani 1 1 d . . .
H26 H 0.2188 0.1344 0.5422 0.032 Uiso 1 1 calc R . .
C27 C 0.20501(17) 0.15944(11) 0.64937(9) 0.0258(3) Uani 1 1 d . . .
H27 H 0.2114 0.0881 0.6632 0.031 Uiso 1 1 calc R . .
C28 C 0.18992(17) 0.23875(12) 0.70160(8) 0.0244(3) Uani 1 1 d . . .
H28 H 0.1866 0.2204 0.7504 0.029 Uiso 1 1 calc R . .
C29 C 0.17992(16) 0.34516(11) 0.68072(7) 0.0209(3) Uani 1 1 d . . .
H29 H 0.1674 0.3975 0.7157 0.025 Uiso 1 1 calc R . .
O11 O 0.26792(16) 1.25668(9) 0.33029(7) 0.0376(3) Uani 1 1 d . . .
O12 O 0.39985(11) 1.00694(7) 0.27100(5) 0.0180(2) Uani 1 1 d . . .
O13 O 0.30398(12) 1.01289(8) 0.44942(5) 0.0221(2) Uani 1 1 d . . .
O15 O 0.22009(12) 0.83424(7) 0.45565(5) 0.0192(2) Uani 1 1 d . . .
O17 O 0.11258(13) 0.88912(8) 0.55850(5) 0.0250(2) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O12 1.4243(15) . ?
C1 C10 1.5363(17) . ?
C1 C2 1.5523(18) . ?
C1 H1 0.98 . ?
C2 O13 1.4508(16) . ?
C2 C3 1.525(2) . ?
C2 H2 0.98 . ?
C3 C4 1.515(2) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4 O11 1.2104(19) . ?
C4 C5 1.5188(19) . ?
C5 O12 1.4398(16) . ?
C5 C6 1.5177(18) . ?
C5 C9 1.5562(18) . ?
C6 C7 1.533(2) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.5319(18) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.5528(18) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.5418(17) . ?
C9 H9 0.98 . ?
C10 C14 1.5166(17) . ?
C10 H10 0.98 . ?
C14 O13 1.3972(16) . ?
C14 O15 1.4513(15) . ?
C14 H14 0.98 . ?
C16 O17 1.2061(16) . ?
C16 O15 1.3555(15) . ?
C16 C18 1.4840(18) . ?
C18 C23 1.3940(18) . ?
C18 C19 1.3953(18) . ?
C19 C20 1.3840(19) . ?
C19 H19 0.93 . ?
C20 C21 1.4014(18) . ?
C20 H20 0.93 . ?
C21 C22 1.3991(18) . ?
C21 C24 1.4832(18) . ?
C22 C23 1.3875(19) . ?
C22 H22 0.93 . ?
C23 H23 0.93 . ?
C24 C25 1.4003(19) . ?
C24 C29 1.4014(19) . ?
C25 C26 1.391(2) . ?
C25 H25 0.93 . ?
C26 C27 1.378(2) . ?
C26 H26 0.93 . ?
C27 C28 1.395(2) . ?
C27 H27 0.93 . ?
C28 C29 1.3882(19) . ?
C28 H28 0.93 . ?
C29 H29 0.93 . ?

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
O12 C1 C10 106.53(10) . . ?
O12 C1 C2 109.97(11) . . ?
C10 C1 C2 103.51(10) . . ?
O12 C1 H1 112.1 . . ?
C10 C1 H1 112.1 . . ?
C2 C1 H1 112.1 . . ?
O13 C2 C3 107.34(11) . . ?
O13 C2 C1 106.22(10) . . ?
C3 C2 C1 111.21(11) . . ?
O13 C2 H2 110.6 . . ?
C3 C2 H2 110.6 . . ?
C1 C2 H2 110.6 . . ?
C4 C3 C2 110.56(11) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
O11 C4 C3 124.03(14) . . ?
O11 C4 C5 122.39(14) . . ?
C3 C4 C5 113.57(12) . . ?
O12 C5 C6 109.92(11) . . ?
O12 C5 C4 107.39(11) . . ?
C6 C5 C4 116.88(12) . . ?
O12 C5 C9 103.54(10) . . ?
C6 C5 C9 105.86(11) . . ?
C4 C5 C9 112.46(11) . . ?
C5 C6 C7 103.08(11) . . ?
C5 C6 H6A 111.1 . . ?
C7 C6 H6A 111.1 . . ?
C5 C6 H6B 111.1 . . ?
C7 C6 H6B 111.1 . . ?
H6A C6 H6B 109.1 . . ?
C8 C7 C6 104.50(11) . . ?
C8 C7 H7A 110.9 . . ?
C6 C7 H7A 110.9 . . ?
C8 C7 H7B 110.9 . . ?
C6 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C7 C8 C9 107.20(11) . . ?
C7 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
C7 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?
C10 C9 C8 115.09(11) . . ?
C10 C9 C5 104.03(10) . . ?
C8 C9 C5 104.22(10) . . ?
C10 C9 H9 111 . . ?
C8 C9 H9 111 . . ?
C5 C9 H9 111 . . ?
C14 C10 C1 103.61(10) . . ?
C14 C10 C9 112.83(10) . . ?
C1 C10 C9 102.63(10) . . ?
C14 C10 H10 112.3 . . ?
C1 C10 H10 112.3 . . ?
C9 C10 H10 112.3 . . ?
O13 C14 O15 111.02(10) . . ?
O13 C14 C10 106.43(10) . . ?
O15 C14 C10 106.41(10) . . ?
O13 C14 H14 110.9 . . ?
O15 C14 H14 110.9 . . ?
C10 C14 H14 110.9 . . ?
O17 C16 O15 123.45(12) . . ?
O17 C16 C18 124.88(12) . . ?
O15 C16 C18 111.66(11) . . ?
C23 C18 C19 119.26(12) . . ?
C23 C18 C16 118.76(12) . . ?
C19 C18 C16 121.93(12) . . ?
C20 C19 C18 120.28(12) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.98(12) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 118.28(12) . . ?
C22 C21 C24 121.29(12) . . ?
C20 C21 C24 120.43(12) . . ?
C23 C22 C21 120.83(12) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C18 120.35(12) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?
C25 C24 C29 118.04(13) . . ?
C25 C24 C21 121.14(12) . . ?
C29 C24 C21 120.82(12) . . ?
C26 C25 C24 120.78(13) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C27 C26 C25 120.48(14) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 119.71(13) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C29 C28 C27 119.96(13) . . ?
C29 C28 H28 120 . . ?
C27 C28 H28 120 . . ?
C28 C29 C24 121.02(13) . . ?
C28 C29 H29 119.5 . . ?
C24 C29 H29 119.5 . . ?
C1 O12 C5 103.97(9) . . ?
C14 O13 C2 110.88(10) . . ?
C16 O15 C14 115.77(10) . . ?

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
O12 C1 C2 O13 124.36(11) . . . . ?
C10 C1 C2 O13 10.86(13) . . . . ?
O12 C1 C2 C3 7.88(15) . . . . ?
C10 C1 C2 C3 -105.62(12) . . . . ?
O13 C2 C3 C4 -71.33(14) . . . . ?
C1 C2 C3 C4 44.47(15) . . . . ?
C2 C3 C4 O11 140.24(15) . . . . ?
C2 C3 C4 C5 -38.49(16) . . . . ?
O11 C4 C5 O12 161.41(13) . . . . ?
C3 C4 C5 O12 -19.84(15) . . . . ?
O11 C4 C5 C6 37.4(2) . . . . ?
C3 C4 C5 C6 -143.83(12) . . . . ?
O11 C4 C5 C9 -85.33(17) . . . . ?
C3 C4 C5 C9 93.42(14) . . . . ?
O12 C5 C6 C7 73.76(13) . . . . ?
C4 C5 C6 C7 -163.56(12) . . . . ?
C9 C5 C6 C7 -37.46(14) . . . . ?
C5 C6 C7 C8 37.66(14) . . . . ?
C6 C7 C8 C9 -23.85(15) . . . . ?
C7 C8 C9 C10 -112.22(13) . . . . ?
C7 C8 C9 C5 1.03(14) . . . . ?
O12 C5 C9 C10 27.86(12) . . . . ?
C6 C5 C9 C10 143.50(11) . . . . ?
C4 C5 C9 C10 -87.74(13) . . . . ?
O12 C5 C9 C8 -93.09(11) . . . . ?
C6 C5 C9 C8 22.56(13) . . . . ?
C4 C5 C9 C8 151.31(12) . . . . ?
O12 C1 C10 C14 -140.80(10) . . . . ?
C2 C1 C10 C14 -24.84(12) . . . . ?
O12 C1 C10 C9 -23.19(12) . . . . ?
C2 C1 C10 C9 92.78(11) . . . . ?
C8 C9 C10 C14 -138.88(11) . . . . ?
C5 C9 C10 C14 107.76(12) . . . . ?
C8 C9 C10 C1 110.26(12) . . . . ?
C5 C9 C10 C1 -3.10(12) . . . . ?
C1 C10 C14 O13 31.26(12) . . . . ?
C9 C10 C14 O13 -78.99(13) . . . . ?
C1 C10 C14 O15 -87.21(11) . . . . ?
C9 C10 C14 O15 162.54(10) . . . . ?
O17 C16 C18 C23 12.6(2) . . . . ?
O15 C16 C18 C23 -166.34(12) . . . . ?
O17 C16 C18 C19 -169.80(14) . . . . ?
O15 C16 C18 C19 11.26(18) . . . . ?
C23 C18 C19 C20 0.1(2) . . . . ?
C16 C18 C19 C20 -177.54(12) . . . . ?
C18 C19 C20 C21 0.7(2) . . . . ?
C19 C20 C21 C22 -0.7(2) . . . . ?
C19 C20 C21 C24 -179.89(12) . . . . ?
C20 C21 C22 C23 -0.1(2) . . . . ?
C24 C21 C22 C23 179.07(12) . . . . ?
C21 C22 C23 C18 0.9(2) . . . . ?
C19 C18 C23 C22 -0.9(2) . . . . ?
C16 C18 C23 C22 176.81(12) . . . . ?
C22 C21 C24 C25 150.05(13) . . . . ?
C20 C21 C24 C25 -30.82(19) . . . . ?
C22 C21 C24 C29 -30.64(19) . . . . ?
C20 C21 C24 C29 148.50(13) . . . . ?
C29 C24 C25 C26 -0.4(2) . . . . ?
C21 C24 C25 C26 178.98(13) . . . . ?
C24 C25 C26 C27 -0.9(2) . . . . ?
C25 C26 C27 C28 1.0(2) . . . . ?
C26 C27 C28 C29 0.2(2) . . . . ?
C27 C28 C29 C24 -1.4(2) . . . . ?
C25 C24 C29 C28 1.5(2) . . . . ?
C21 C24 C29 C28 -177.82(13) . . . . ?
C10 C1 O12 C5 42.40(12) . . . . ?
C2 C1 O12 C5 -69.14(12) . . . . ?
C6 C5 O12 C1 -156.09(11) . . . . ?
C4 C5 O12 C1 75.78(12) . . . . ?
C9 C5 O12 C1 -43.37(12) . . . . ?
O15 C14 O13 C2 89.92(12) . . . . ?
C10 C14 O13 C2 -25.48(13) . . . . ?
C3 C2 O13 C14 127.97(11) . . . . ?
C1 C2 O13 C14 8.91(14) . . . . ?
O17 C16 O15 C14 -9.34(19) . . . . ?
C18 C16 O15 C14 169.61(10) . . . . ?
O13 C14 O15 C16 82.93(13) . . . . ?
C10 C14 O15 C16 -161.66(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C26 H26 O13 0.93 2.43 3.3430(17) 166.6 1_545
C14 H14 O17 0.98 2.44 3.3188(16) 148.5 3_576
C2 H2 O13 0.98 2.51 3.3366(17) 142.3 3_676
C22 H22 O12 0.93 2.45 3.3791(15) 177.1 4_576

_database_code_depnum_ccdc_archive 'CCDC 1003601'
