# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_tompkinmr609
#TrackingRef 'tom_all4.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 O4'
_chemical_formula_weight         308.32

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   9.5528(6)
_cell_length_b                   10.1091(5)
_cell_length_c                   16.1660(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.844(5)
_cell_angle_gamma                90.00
_cell_volume                     1509.05(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1921
_cell_measurement_theta_min      3.0193
_cell_measurement_theta_max      29.3630


_exptl_crystal_description       'chip cut from larger block'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_min  0.99644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7058
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3293
_reflns_number_gt                2293
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2σ(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)+(0.0280P)²+0.2636P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3293
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.16858(17) -0.41719(12) 0.42433(9) 0.0402(4) Uani 1 1 d . . .
O2 O 1.18169(14) -0.00379(11) 0.55567(8) 0.0254(3) Uani 1 1 d . . .
O3 O 1.23804(14) -0.23924(12) 0.36621(8) 0.0274(3) Uani 1 1 d . . .
O4 O 1.11489(13) -0.00400(11) 0.41592(7) 0.0205(3) Uani 1 1 d . . .
C1 C 1.13730(19) -0.21615(16) 0.49038(11) 0.0208(4) Uani 1 1 d . . .
C2 C 1.1775(2) -0.28000(18) 0.57887(12) 0.0277(5) Uani 1 1 d . . .
H2A H 1.2273 -0.3667 0.5847 0.033 Uiso 1 1 calc R . .
H2B H 1.2091 -0.2209 0.6290 0.033 Uiso 1 1 calc R . .
C3 C 1.0244(2) -0.27636(17) 0.53197(12) 0.0261(4) Uani 1 1 d . . .
H3A H 0.9602 -0.2148 0.5526 0.031 Uiso 1 1 calc R . .
H3B H 0.9784 -0.3607 0.5083 0.031 Uiso 1 1 calc R . .
C4 C 1.1760(2) -0.29871(18) 0.42374(12) 0.0251(4) Uani 1 1 d . . .
C5 C 1.14731(19) -0.06896(17) 0.49102(12) 0.0204(4) Uani 1 1 d . . .
C6 C 1.16444(19) -0.13951(16) 0.30603(11) 0.0202(4) Uani 1 1 d . . .
H6 H 1.2377 -0.0702 0.3031 0.024 Uiso 1 1 calc R . .
C7 C 1.04533(19) -0.07197(16) 0.33750(11) 0.0182(4) Uani 1 1 d . . .
H7 H 0.9760 -0.1395 0.3488 0.022 Uiso 1 1 calc R . .
C8 C 1.11494(19) -0.19996(16) 0.21804(11) 0.0205(4) Uani 1 1 d . . .
C9 C 1.1351(2) -0.13082(18) 0.14819(12) 0.0300(5) Uani 1 1 d . . .
H9 H 1.1774 -0.0452 0.1561 0.036 Uiso 1 1 calc R . .
C10 C 1.0945(2) -0.1847(2) 0.06695(13) 0.0374(5) Uani 1 1 d . . .
H10 H 1.1087 -0.1361 0.0194 0.045 Uiso 1 1 calc R . .
C11 C 1.0336(2) -0.3090(2) 0.05497(13) 0.0369(5) Uani 1 1 d . . .
H11 H 1.0061 -0.3465 -0.0007 0.044 Uiso 1 1 calc R . .
C12 C 1.0124(2) -0.37911(19) 0.12430(13) 0.0305(5) Uani 1 1 d . . .
H12 H 0.9700 -0.4647 0.1160 0.037 Uiso 1 1 calc R . .
C13 C 1.0528(2) -0.32524(17) 0.20539(12) 0.0248(4) Uani 1 1 d . . .
H13 H 1.0380 -0.3739 0.2527 0.030 Uiso 1 1 calc R . .
C14 C 0.9648(2) 0.03125(16) 0.27650(11) 0.0181(4) Uani 1 1 d . . .
C15 C 0.8209(2) 0.01163(16) 0.23351(11) 0.0219(4) Uani 1 1 d . . .
H15 H 0.7721 -0.0658 0.2443 0.026 Uiso 1 1 calc R . .
C16 C 0.7476(2) 0.10415(18) 0.17485(12) 0.0283(5) Uani 1 1 d . . .
H16 H 0.6494 0.0895 0.1451 0.034 Uiso 1 1 calc R . .
C17 C 0.8177(2) 0.21742(18) 0.15979(12) 0.0292(5) Uani 1 1 d . . .
H17 H 0.7684 0.2806 0.1192 0.035 Uiso 1 1 calc R . .
C18 C 0.9602(2) 0.23856(19) 0.20406(13) 0.0335(5) Uani 1 1 d . . .
H18 H 1.0078 0.3175 0.1946 0.040 Uiso 1 1 calc R . .
C19 C 1.0344(2) 0.14616(17) 0.26195(13) 0.0279(5) Uani 1 1 d . . .
H19 H 1.1325 0.1612 0.2917 0.034 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.200(2) . ?
O2 C5 1.207(2) . ?
O3 C4 1.364(2) . ?
O3 C6 1.452(2) . ?
O4 C5 1.345(2) . ?
O4 C7 1.4454(19) . ?
C1 C4 1.482(3) . ?
C1 C5 1.491(2) . ?
C1 C2 1.526(2) . ?
C1 C3 1.535(3) . ?
C2 C3 1.465(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C6 C8 1.508(2) . ?
C6 C7 1.522(2) . ?
C6 H6 1.0000 . ?
C7 C14 1.505(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.383(2) . ?
C8 C13 1.392(2) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.386(2) . ?
C14 C19 1.388(2) . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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
C4 O3 C6 122.86(14) . . ?
C5 O4 C7 120.50(13) . . ?
C4 C1 C5 122.66(16) . . ?
C4 C1 C2 113.16(14) . . ?
C5 C1 C2 114.54(15) . . ?
C4 C1 C3 115.39(15) . . ?
C5 C1 C3 116.33(15) . . ?
C2 C1 C3 57.19(12) . . ?
C3 C2 C1 61.71(12) . . ?
C3 C2 H2A 117.6 . . ?
C1 C2 H2A 117.6 . . ?
C3 C2 H2B 117.6 . . ?
C1 C2 H2B 117.6 . . ?
H2A C2 H2B 114.7 . . ?
C2 C3 C1 61.09(12) . . ?
C2 C3 H3A 117.7 . . ?
C1 C3 H3A 117.7 . . ?
C2 C3 H3B 117.7 . . ?
C1 C3 H3B 117.7 . . ?
H3A C3 H3B 114.8 . . ?
O1 C4 O3 118.81(17) . . ?
O1 C4 C1 122.02(17) . . ?
O3 C4 C1 118.69(15) . . ?
O2 C5 O4 117.62(15) . . ?
O2 C5 C1 123.59(16) . . ?
O4 C5 C1 118.78(15) . . ?
O3 C6 C8 109.37(13) . . ?
O3 C6 C7 111.27(14) . . ?
C8 C6 C7 114.60(14) . . ?
O3 C6 H6 107.1 . . ?
C8 C6 H6 107.1 . . ?
C7 C6 H6 107.1 . . ?
O4 C7 C14 106.75(13) . . ?
O4 C7 C6 106.94(14) . . ?
C14 C7 C6 113.12(14) . . ?
O4 C7 H7 110.0 . . ?
C14 C7 H7 110.0 . . ?
C6 C7 H7 110.0 . . ?
C9 C8 C13 118.91(17) . . ?
C9 C8 C6 119.32(16) . . ?
C13 C8 C6 121.75(16) . . ?
C10 C9 C8 120.84(18) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.91(19) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.83(19) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.27(18) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 120.23(18) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C15 C14 C19 119.41(16) . . ?
C15 C14 C7 120.28(15) . . ?
C19 C14 C7 120.30(16) . . ?
C14 C15 C16 120.53(17) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 119.86(18) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 119.67(18) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 120.77(18) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C14 119.73(18) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?

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
C4 C1 C2 C3 -106.21(17) . . . . ?
C5 C1 C2 C3 106.61(18) . . . . ?
C4 C1 C3 C2 102.24(17) . . . . ?
C5 C1 C3 C2 -103.43(18) . . . . ?
C6 O3 C4 O1 124.59(19) . . . . ?
C6 O3 C4 C1 -63.2(2) . . . . ?
C5 C1 C4 O1 179.36(18) . . . . ?
C2 C1 C4 O1 35.2(3) . . . . ?
C3 C1 C4 O1 -28.1(3) . . . . ?
C5 C1 C4 O3 7.4(3) . . . . ?
C2 C1 C4 O3 -136.76(17) . . . . ?
C3 C1 C4 O3 159.93(16) . . . . ?
C7 O4 C5 O2 -167.42(15) . . . . ?
C7 O4 C5 C1 11.8(2) . . . . ?
C4 C1 C5 O2 -144.99(18) . . . . ?
C2 C1 C5 O2 -1.3(3) . . . . ?
C3 C1 C5 O2 62.7(2) . . . . ?
C4 C1 C5 O4 35.8(3) . . . . ?
C2 C1 C5 O4 179.53(15) . . . . ?
C3 C1 C5 O4 -116.49(18) . . . . ?
C4 O3 C6 C8 -104.49(18) . . . . ?
C4 O3 C6 C7 23.1(2) . . . . ?
C5 O4 C7 C14 154.50(15) . . . . ?
C5 O4 C7 C6 -84.15(18) . . . . ?
O3 C6 C7 O4 63.46(17) . . . . ?
C8 C6 C7 O4 -171.82(13) . . . . ?
O3 C6 C7 C14 -179.31(13) . . . . ?
C8 C6 C7 C14 -54.58(19) . . . . ?
O3 C6 C8 C9 -135.95(17) . . . . ?
C7 C6 C8 C9 98.3(2) . . . . ?
O3 C6 C8 C13 42.3(2) . . . . ?
C7 C6 C8 C13 -83.4(2) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
C6 C8 C9 C10 178.27(18) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C8 0.0(3) . . . . ?
C9 C8 C13 C12 0.1(3) . . . . ?
C6 C8 C13 C12 -178.15(17) . . . . ?
O4 C7 C14 C15 -130.43(16) . . . . ?
C6 C7 C14 C15 112.22(18) . . . . ?
O4 C7 C14 C19 50.4(2) . . . . ?
C6 C7 C14 C19 -67.0(2) . . . . ?
C19 C14 C15 C16 1.6(3) . . . . ?
C7 C14 C15 C16 -177.60(16) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C16 C17 C18 C19 1.4(3) . . . . ?
C17 C18 C19 C14 -0.6(3) . . . . ?
C15 C14 C19 C18 -0.9(3) . . . . ?
C7 C14 C19 C18 178.28(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 936075'
#######################################################################
#
#                 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_tomk_mr787dmonop
#TrackingRef 'tom_all4.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O5'
_chemical_formula_weight         326.33

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   10.7552(7)
_cell_length_b                   10.1502(7)
_cell_length_c                   14.9906(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.447(5)
_cell_angle_gamma                90.00
_cell_volume                     1633.52(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4182
_cell_measurement_theta_min      3.1230
_cell_measurement_theta_max      28.8308


_exptl_crystal_description       'cut from mass'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_min  0.47216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13349
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3678
_reflns_number_gt                2463
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2σ(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)+(0.0467P)²+0.0354P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3678
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.85665(12) 0.72858(13) 0.74680(7) 0.0330(3) Uani 1 1 d . . .
O2 O 0.81922(10) 0.64777(12) 0.58064(7) 0.0269(3) Uani 1 1 d . . .
O3 O 0.64010(11) 0.54178(14) 0.54435(8) 0.0428(4) Uani 1 1 d . . .
O4 O 0.92704(11) 0.46047(12) 0.69757(7) 0.0347(3) Uani 1 1 d . . .
O5 O 0.99678(12) 0.29620(13) 0.61450(8) 0.0373(3) Uani 1 1 d . . .
C1 C 0.82758(15) 0.82776(17) 0.68068(10) 0.0269(4) Uani 1 1 d . . .
H1 H 0.9063 0.8649 0.6587 0.032 Uiso 1 1 calc R . .
C2 C 0.75003(15) 0.76564(17) 0.60289(9) 0.0252(4) Uani 1 1 d . . .
H2 H 0.6671 0.7391 0.6238 0.030 Uiso 1 1 calc R . .
C3 C 0.75433(16) 0.93553(18) 0.72282(10) 0.0282(4) Uani 1 1 d . . .
C4 C 0.77447(18) 1.06653(19) 0.70171(11) 0.0358(5) Uani 1 1 d . . .
H4 H 0.8383 1.0885 0.6632 0.043 Uiso 1 1 calc R . .
C5 C 0.70316(19) 1.1655(2) 0.73584(12) 0.0437(5) Uani 1 1 d . . .
H5 H 0.7171 1.2548 0.7201 0.052 Uiso 1 1 calc R . .
C6 C 0.61149(18) 1.1342(2) 0.79288(11) 0.0437(5) Uani 1 1 d . . .
H6 H 0.5618 1.2019 0.8162 0.052 Uiso 1 1 calc R . .
C7 C 0.59192(17) 1.0044(2) 0.81614(11) 0.0408(5) Uani 1 1 d . . .
H7 H 0.5297 0.9832 0.8562 0.049 Uiso 1 1 calc R . .
C8 C 0.66288(16) 0.9047(2) 0.78112(10) 0.0347(4) Uani 1 1 d . . .
H8 H 0.6489 0.8155 0.7970 0.042 Uiso 1 1 calc R . .
C9 C 0.73042(15) 0.85156(18) 0.52119(10) 0.0277(4) Uani 1 1 d . . .
C10 C 0.82995(17) 0.90852(19) 0.48085(10) 0.0344(4) Uani 1 1 d . . .
H10 H 0.9122 0.8973 0.5064 0.041 Uiso 1 1 calc R . .
C11 C 0.8097(2) 0.9818(2) 0.40317(11) 0.0432(5) Uani 1 1 d . . .
H11 H 0.8781 1.0213 0.3762 0.052 Uiso 1 1 calc R . .
C12 C 0.6919(2) 0.9975(2) 0.36526(11) 0.0481(6) Uani 1 1 d . . .
H12 H 0.6789 1.0469 0.3117 0.058 Uiso 1 1 calc R . .
C13 C 0.5925(2) 0.9422(2) 0.40430(12) 0.0490(6) Uani 1 1 d . . .
H13 H 0.5106 0.9543 0.3783 0.059 Uiso 1 1 calc R . .
C14 C 0.61178(17) 0.8684(2) 0.48198(11) 0.0381(5) Uani 1 1 d . . .
H14 H 0.5428 0.8291 0.5084 0.046 Uiso 1 1 calc R . .
C15 C 0.75085(16) 0.53970(18) 0.55862(10) 0.0269(4) Uani 1 1 d . . .
C16 C 0.83190(15) 0.42188(18) 0.55177(10) 0.0266(4) Uani 1 1 d . . .
C17 C 0.86424(16) 0.38280(19) 0.45762(10) 0.0324(4) Uani 1 1 d . . .
H17A H 0.8320 0.4390 0.4074 0.039 Uiso 1 1 calc R . .
H17B H 0.9476 0.3444 0.4502 0.039 Uiso 1 1 calc R . .
C18 C 0.77377(17) 0.30293(19) 0.50396(10) 0.0353(4) Uani 1 1 d . . .
H18A H 0.8006 0.2145 0.5253 0.042 Uiso 1 1 calc R . .
H18B H 0.6851 0.3091 0.4826 0.042 Uiso 1 1 calc R . .
C19 C 0.92313(15) 0.39729(18) 0.62842(10) 0.0274(4) Uani 1 1 d . . .
H1H H 0.8824(18) 0.657(2) 0.7229(12) 0.052(7) Uiso 1 1 d . . .
H2H H 1.051(2) 0.281(3) 0.6655(15) 0.087(8) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4339(19) . ?
O1 H1H 0.86(2) . ?
O2 C15 1.350(2) . ?
O2 C2 1.4582(19) . ?
O3 C15 1.1977(19) . ?
O4 C19 1.2174(19) . ?
O5 C19 1.321(2) . ?
O5 H2H 0.95(2) . ?
C1 C3 1.509(2) . ?
C1 C2 1.528(2) . ?
C1 H1 1.0000 . ?
C2 C9 1.508(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.387(3) . ?
C3 C8 1.390(2) . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.383(2) . ?
C9 C10 1.387(2) . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.366(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.370(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.487(2) . ?
C16 C19 1.487(2) . ?
C16 C18 1.519(2) . ?
C16 C17 1.526(2) . ?
C17 C18 1.472(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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
C1 O1 H1H 111.5(13) . . ?
C15 O2 C2 116.39(12) . . ?
C19 O5 H2H 110.1(15) . . ?
O1 C1 C3 108.50(12) . . ?
O1 C1 C2 108.91(14) . . ?
C3 C1 C2 110.11(13) . . ?
O1 C1 H1 109.8 . . ?
C3 C1 H1 109.8 . . ?
C2 C1 H1 109.8 . . ?
O2 C2 C9 109.71(12) . . ?
O2 C2 C1 104.50(12) . . ?
C9 C2 C1 115.11(14) . . ?
O2 C2 H2 109.1 . . ?
C9 C2 H2 109.1 . . ?
C1 C2 H2 109.1 . . ?
C4 C3 C8 119.05(17) . . ?
C4 C3 C1 120.47(15) . . ?
C8 C3 C1 120.45(17) . . ?
C5 C4 C3 121.02(17) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 120.06(19) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 120.24(18) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 119.93(19) . . ?
C7 C8 H8 120.0 . . ?
C3 C8 H8 120.0 . . ?
C14 C9 C10 118.67(16) . . ?
C14 C9 C2 119.81(15) . . ?
C10 C9 C2 121.41(15) . . ?
C9 C10 C11 120.18(18) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.45(19) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.16(18) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 119.88(19) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C9 C14 C13 120.67(19) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
O3 C15 O2 123.40(17) . . ?
O3 C15 C16 125.64(17) . . ?
O2 C15 C16 110.93(14) . . ?
C19 C16 C15 116.36(14) . . ?
C19 C16 C18 117.71(15) . . ?
C15 C16 C18 116.45(14) . . ?
C19 C16 C17 119.65(14) . . ?
C15 C16 C17 116.11(14) . . ?
C18 C16 C17 57.82(11) . . ?
C18 C17 C16 60.85(10) . . ?
C18 C17 H17A 117.7 . . ?
C16 C17 H17A 117.7 . . ?
C18 C17 H17B 117.7 . . ?
C16 C17 H17B 117.7 . . ?
H17A C17 H17B 114.8 . . ?
C17 C18 C16 61.32(11) . . ?
C17 C18 H18A 117.6 . . ?
C16 C18 H18A 117.6 . . ?
C17 C18 H18B 117.6 . . ?
C16 C18 H18B 117.6 . . ?
H18A C18 H18B 114.7 . . ?
O4 C19 O5 123.61(15) . . ?
O4 C19 C16 123.86(16) . . ?
O5 C19 C16 112.49(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 O2 C2 C9 -95.02(16) . . . . ?
C15 O2 C2 C1 141.04(13) . . . . ?
O1 C1 C2 O2 -49.72(16) . . . . ?
C3 C1 C2 O2 -168.57(13) . . . . ?
O1 C1 C2 C9 -170.11(13) . . . . ?
C3 C1 C2 C9 71.04(17) . . . . ?
O1 C1 C3 C4 141.46(15) . . . . ?
C2 C1 C3 C4 -99.43(18) . . . . ?
O1 C1 C3 C8 -40.63(19) . . . . ?
C2 C1 C3 C8 78.48(18) . . . . ?
C8 C3 C4 C5 -1.7(3) . . . . ?
C1 C3 C4 C5 176.26(15) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C6 C7 C8 C3 0.3(3) . . . . ?
C4 C3 C8 C7 1.0(2) . . . . ?
C1 C3 C8 C7 -176.90(14) . . . . ?
O2 C2 C9 C14 112.08(17) . . . . ?
C1 C2 C9 C14 -130.43(17) . . . . ?
O2 C2 C9 C10 -64.1(2) . . . . ?
C1 C2 C9 C10 53.4(2) . . . . ?
C14 C9 C10 C11 0.6(3) . . . . ?
C2 C9 C10 C11 176.81(16) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C10 C9 C14 C13 -0.7(3) . . . . ?
C2 C9 C14 C13 -177.00(17) . . . . ?
C12 C13 C14 C9 0.9(3) . . . . ?
C2 O2 C15 O3 11.0(2) . . . . ?
C2 O2 C15 C16 -170.92(11) . . . . ?
O3 C15 C16 C19 -131.81(17) . . . . ?
O2 C15 C16 C19 50.21(18) . . . . ?
O3 C15 C16 C18 13.9(2) . . . . ?
O2 C15 C16 C18 -164.09(12) . . . . ?
O3 C15 C16 C17 79.1(2) . . . . ?
O2 C15 C16 C17 -98.84(16) . . . . ?
C19 C16 C17 C18 105.91(18) . . . . ?
C15 C16 C17 C18 -106.12(17) . . . . ?
C19 C16 C18 C17 -109.25(16) . . . . ?
C15 C16 C18 C17 105.53(16) . . . . ?
C15 C16 C19 O4 6.4(2) . . . . ?
C18 C16 C19 O4 -138.81(18) . . . . ?
C17 C16 C19 O4 154.34(17) . . . . ?
C15 C16 C19 O5 -175.80(14) . . . . ?
C18 C16 C19 O5 38.9(2) . . . . ?
C17 C16 C19 O5 -27.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 936076'
#######################################################################
#
#                 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_tompkin_mr780d
#TrackingRef 'tom_all4.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O5'
_chemical_formula_weight         326.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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                   5.6981(7)
_cell_length_b                   8.6185(7)
_cell_length_c                   32.841(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1612.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    857
_cell_measurement_theta_min      5.1277
_cell_measurement_theta_max      73.0312

_exptl_absorpt_correction_T_min  0.6712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.804

_exptl_special_details           
;
Diffraction not from a single crystal.
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3829
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0712
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         5.31
_diffrn_reflns_theta_max         73.18
_reflns_number_total             2650
_reflns_number_gt                2185
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Flack parameter is ambiguous.

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 > 2σ(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)+(0.0771P)²+0.4923P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2650
_refine_ls_number_parameters     223
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1667
_refine_ls_wR_factor_gt          0.1561
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3699(5) 1.2819(3) 0.22803(9) 0.0417(7) Uani 1 1 d . . .
O2 O 0.1269(6) 1.0826(4) 0.23123(9) 0.0435(7) Uani 1 1 d D . .
H2H H 0.062(8) 1.032(5) 0.2516(10) 0.052 Uiso 1 1 d D . .
O3 O 0.1066(5) 0.9255(3) 0.29717(9) 0.0354(7) Uani 1 1 d . . .
O4 O 0.3545(5) 0.9836(3) 0.34800(8) 0.0312(6) Uani 1 1 d . . .
O5 O 0.6365(5) 0.7253(3) 0.35709(9) 0.0365(7) Uani 1 1 d D . .
H5H H 0.681(8) 0.743(5) 0.3316(6) 0.044 Uiso 1 1 d D . .
C1 C 0.2907(7) 1.1740(5) 0.24750(14) 0.0348(9) Uani 1 1 d . . .
C2 C 0.3756(7) 1.1366(4) 0.28912(12) 0.0272(8) Uani 1 1 d . . .
C3 C 0.4730(8) 1.2714(4) 0.31404(14) 0.0376(10) Uani 1 1 d . . .
H3A H 0.4622 1.3767 0.3021 0.045 Uiso 1 1 calc R . .
H3B H 0.4524 1.2674 0.3440 0.045 Uiso 1 1 calc R . .
C4 C 0.6405(7) 1.1626(5) 0.29564(14) 0.0350(9) Uani 1 1 d . . .
H4A H 0.7241 1.0902 0.3140 0.042 Uiso 1 1 calc R . .
H4B H 0.7338 1.1995 0.2721 0.042 Uiso 1 1 calc R . .
C5 C 0.2646(6) 1.0042(4) 0.31128(12) 0.0275(8) Uani 1 1 d . . .
C6 C 0.2679(7) 0.8532(4) 0.37197(12) 0.0278(8) Uani 1 1 d . . .
H6 H 0.0947 0.8432 0.3678 0.033 Uiso 1 1 calc R . .
C7 C 0.3899(7) 0.7040(4) 0.35648(13) 0.0318(9) Uani 1 1 d . . .
H7 H 0.3410 0.6870 0.3276 0.038 Uiso 1 1 calc R . .
C8 C 0.3156(7) 0.8899(4) 0.41596(12) 0.0275(8) Uani 1 1 d . . .
C9 C 0.5239(7) 0.9620(4) 0.42805(12) 0.0293(8) Uani 1 1 d . . .
H9 H 0.6405 0.9864 0.4084 0.035 Uiso 1 1 calc R . .
C10 C 0.5603(7) 0.9977(4) 0.46861(13) 0.0344(9) Uani 1 1 d . . .
H10 H 0.7026 1.0463 0.4767 0.041 Uiso 1 1 calc R . .
C11 C 0.3920(7) 0.9634(4) 0.49756(13) 0.0346(9) Uani 1 1 d . . .
H11 H 0.4170 0.9901 0.5253 0.041 Uiso 1 1 calc R . .
C12 C 0.1869(7) 0.8898(4) 0.48587(13) 0.0346(10) Uani 1 1 d . . .
H12 H 0.0722 0.8633 0.5057 0.041 Uiso 1 1 calc R . .
C13 C 0.1492(7) 0.8550(4) 0.44514(12) 0.0299(8) Uani 1 1 d . . .
H13 H 0.0068 0.8064 0.4372 0.036 Uiso 1 1 calc R . .
C14 C 0.3170(7) 0.5633(4) 0.38087(13) 0.0314(9) Uani 1 1 d . . .
C15 C 0.4581(7) 0.5061(4) 0.41148(12) 0.0344(9) Uani 1 1 d . . .
H15 H 0.6015 0.5568 0.4178 0.041 Uiso 1 1 calc R . .
C16 C 0.3920(8) 0.3755(4) 0.43298(14) 0.0381(10) Uani 1 1 d . . .
H16 H 0.4915 0.3364 0.4538 0.046 Uiso 1 1 calc R . .
C17 C 0.1822(8) 0.3010(4) 0.42452(14) 0.0389(10) Uani 1 1 d . . .
H17 H 0.1381 0.2108 0.4393 0.047 Uiso 1 1 calc R . .
C18 C 0.0381(7) 0.3594(5) 0.39451(14) 0.0387(10) Uani 1 1 d . . .
H18 H -0.1064 0.3091 0.3887 0.046 Uiso 1 1 calc R . .
C19 C 0.1022(7) 0.4911(5) 0.37268(14) 0.0352(9) Uani 1 1 d . . .
H19 H 0.0007 0.5317 0.3523 0.042 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.216(5) . ?
O2 C1 1.333(5) . ?
O2 H2H 0.879(10) . ?
O3 C5 1.219(5) . ?
O4 C5 1.322(5) . ?
O4 C6 1.458(4) . ?
O5 C7 1.417(5) . ?
O5 H5H 0.887(10) . ?
C1 C2 1.485(6) . ?
C2 C5 1.494(5) . ?
C2 C3 1.526(5) . ?
C2 C4 1.541(5) . ?
C3 C4 1.468(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 C8 1.504(6) . ?
C6 C7 1.547(5) . ?
C6 H6 1.0000 . ?
C7 C14 1.512(5) . ?
C7 H7 1.0000 . ?
C8 C13 1.381(5) . ?
C8 C9 1.397(5) . ?
C9 C10 1.383(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.378(6) . ?
C14 C19 1.399(5) . ?
C15 C16 1.381(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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
C1 O2 H2H 106(3) . . ?
C5 O4 C6 117.7(3) . . ?
C7 O5 H5H 107(3) . . ?
O1 C1 O2 120.0(4) . . ?
O1 C1 C2 122.0(4) . . ?
O2 C1 C2 118.0(4) . . ?
C1 C2 C5 118.4(3) . . ?
C1 C2 C3 116.6(3) . . ?
C5 C2 C3 118.3(3) . . ?
C1 C2 C4 114.6(4) . . ?
C5 C2 C4 117.3(3) . . ?
C3 C2 C4 57.2(3) . . ?
C4 C3 C2 61.9(3) . . ?
C4 C3 H3A 117.6 . . ?
C2 C3 H3A 117.6 . . ?
C4 C3 H3B 117.6 . . ?
C2 C3 H3B 117.6 . . ?
H3A C3 H3B 114.7 . . ?
C3 C4 C2 60.9(3) . . ?
C3 C4 H4A 117.7 . . ?
C2 C4 H4A 117.7 . . ?
C3 C4 H4B 117.7 . . ?
C2 C4 H4B 117.7 . . ?
H4A C4 H4B 114.8 . . ?
O3 C5 O4 123.9(4) . . ?
O3 C5 C2 123.6(3) . . ?
O4 C5 C2 112.5(3) . . ?
O4 C6 C8 107.2(3) . . ?
O4 C6 C7 108.1(3) . . ?
C8 C6 C7 114.2(3) . . ?
O4 C6 H6 109.1 . . ?
C8 C6 H6 109.1 . . ?
C7 C6 H6 109.1 . . ?
O5 C7 C14 111.6(3) . . ?
O5 C7 C6 109.5(3) . . ?
C14 C7 C6 111.6(3) . . ?
O5 C7 H7 108.0 . . ?
C14 C7 H7 108.0 . . ?
C6 C7 H7 108.0 . . ?
C13 C8 C9 118.9(4) . . ?
C13 C8 C6 119.8(4) . . ?
C9 C8 C6 121.3(4) . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.5(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 119.8(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C8 C13 C12 121.1(4) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C19 119.4(4) . . ?
C15 C14 C7 120.9(4) . . ?
C19 C14 C7 119.7(4) . . ?
C14 C15 C16 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 120.7(4) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 119.2(4) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 120.7(4) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 119.6(4) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C5 178.5(3) . . . . ?
O2 C1 C2 C5 -3.1(5) . . . . ?
O1 C1 C2 C3 27.7(6) . . . . ?
O2 C1 C2 C3 -153.9(4) . . . . ?
O1 C1 C2 C4 -36.4(5) . . . . ?
O2 C1 C2 C4 142.0(4) . . . . ?
C1 C2 C3 C4 -103.3(4) . . . . ?
C5 C2 C3 C4 105.8(4) . . . . ?
C1 C2 C4 C3 106.9(4) . . . . ?
C5 C2 C4 C3 -107.6(4) . . . . ?
C6 O4 C5 O3 3.6(5) . . . . ?
C6 O4 C5 C2 -177.3(3) . . . . ?
C1 C2 C5 O3 -0.5(5) . . . . ?
C3 C2 C5 O3 149.8(4) . . . . ?
C4 C2 C5 O3 -144.6(4) . . . . ?
C1 C2 C5 O4 -179.6(3) . . . . ?
C3 C2 C5 O4 -29.3(4) . . . . ?
C4 C2 C5 O4 36.3(5) . . . . ?
C5 O4 C6 C8 -157.4(3) . . . . ?
C5 O4 C6 C7 79.1(4) . . . . ?
O4 C6 C7 O5 53.6(4) . . . . ?
C8 C6 C7 O5 -65.5(4) . . . . ?
O4 C6 C7 C14 177.8(3) . . . . ?
C8 C6 C7 C14 58.6(4) . . . . ?
O4 C6 C8 C13 139.2(3) . . . . ?
C7 C6 C8 C13 -101.1(4) . . . . ?
O4 C6 C8 C9 -39.4(4) . . . . ?
C7 C6 C8 C9 80.2(4) . . . . ?
C13 C8 C9 C10 -0.3(5) . . . . ?
C6 C8 C9 C10 178.4(3) . . . . ?
C8 C9 C10 C11 -0.2(5) . . . . ?
C9 C10 C11 C12 1.2(6) . . . . ?
C10 C11 C12 C13 -1.7(6) . . . . ?
C9 C8 C13 C12 -0.3(5) . . . . ?
C6 C8 C13 C12 -179.0(3) . . . . ?
C11 C12 C13 C8 1.3(6) . . . . ?
O5 C7 C14 C15 23.5(5) . . . . ?
C6 C7 C14 C15 -99.4(4) . . . . ?
O5 C7 C14 C19 -157.3(4) . . . . ?
C6 C7 C14 C19 79.8(5) . . . . ?
C19 C14 C15 C16 2.2(6) . . . . ?
C7 C14 C15 C16 -178.6(4) . . . . ?
C14 C15 C16 C17 -0.8(6) . . . . ?
C15 C16 C17 C18 -0.5(6) . . . . ?
C16 C17 C18 C19 0.3(6) . . . . ?
C17 C18 C19 C14 1.1(6) . . . . ?
C15 C14 C19 C18 -2.3(6) . . . . ?
C7 C14 C19 C18 178.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        70.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.060

#===END



_database_code_depnum_ccdc_archive 'CCDC 936077'
#######################################################################
#
#                 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_tomp_miker
#TrackingRef 'tom_all4.cif'

#----MR780-C

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 O4'
_chemical_formula_weight         308.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   13.4714(4)
_cell_length_b                   5.8443(2)
_cell_length_c                   19.1637(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.276(3)
_cell_angle_gamma                90.00
_cell_volume                     1468.45(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2538
_cell_measurement_theta_min      4.5421
_cell_measurement_theta_max      72.9276


_exptl_crystal_description       bar
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_min  0.75651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
mounted in oil on loop
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6142
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.74
_diffrn_reflns_theta_max         73.08
_reflns_number_total             2878
_reflns_number_gt                2434
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2σ(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)+(0.0535P)²+0.6002P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2878
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.13109(8) 0.07233(18) 0.11866(6) 0.0205(3) Uani 1 1 d . . .
O2 O 0.09309(8) -0.20024(19) 0.23350(6) 0.0210(3) Uani 1 1 d . . .
O3 O 0.01122(9) 0.3338(2) 0.09266(7) 0.0277(3) Uani 1 1 d . . .
O4 O -0.06705(8) -0.21012(19) 0.23861(6) 0.0232(3) Uani 1 1 d . . .
C1 C 0.14870(12) -0.1724(3) 0.11889(8) 0.0191(3) Uani 1 1 d . . .
H1 H 0.0859 -0.2478 0.0901 0.023 Uiso 1 1 calc R . .
C2 C 0.03399(12) 0.1438(3) 0.11463(8) 0.0202(3) Uani 1 1 d . . .
C3 C -0.03778(12) -0.0222(3) 0.13623(8) 0.0192(3) Uani 1 1 d . . .
C4 C -0.00580(11) -0.1533(2) 0.20498(8) 0.0178(3) Uani 1 1 d . . .
C5 C 0.16971(12) -0.2673(3) 0.19548(8) 0.0199(3) Uani 1 1 d . . .
H5 H 0.1679 -0.4380 0.1918 0.024 Uiso 1 1 calc R . .
C6 C -0.11098(12) -0.1512(3) 0.07537(9) 0.0248(4) Uani 1 1 d . . .
H6A H -0.1053 -0.1215 0.0256 0.030 Uiso 1 1 calc R . .
H6B H -0.1299 -0.3099 0.0849 0.030 Uiso 1 1 calc R . .
C7 C -0.14963(12) 0.0369(3) 0.11420(9) 0.0247(4) Uani 1 1 d . . .
H7A H -0.1931 -0.0055 0.1474 0.030 Uiso 1 1 calc R . .
H7B H -0.1685 0.1826 0.0882 0.030 Uiso 1 1 calc R . .
C8 C 0.23512(12) -0.2152(3) 0.08242(8) 0.0202(3) Uani 1 1 d . . .
C9 C 0.31136(13) -0.0537(3) 0.08313(9) 0.0244(4) Uani 1 1 d . . .
H9 H 0.3116 0.0852 0.1089 0.029 Uiso 1 1 calc R . .
C10 C 0.38691(13) -0.0953(3) 0.04631(9) 0.0274(4) Uani 1 1 d . . .
H10 H 0.4384 0.0160 0.0466 0.033 Uiso 1 1 calc R . .
C11 C 0.38766(12) -0.2989(3) 0.00892(9) 0.0260(4) Uani 1 1 d . . .
H11 H 0.4390 -0.3261 -0.0168 0.031 Uiso 1 1 calc R . .
C12 C 0.31319(13) -0.4619(3) 0.00934(9) 0.0252(4) Uani 1 1 d . . .
H12 H 0.3142 -0.6023 -0.0154 0.030 Uiso 1 1 calc R . .
C13 C 0.23694(12) -0.4206(3) 0.04593(8) 0.0225(3) Uani 1 1 d . . .
H13 H 0.1860 -0.5329 0.0460 0.027 Uiso 1 1 calc R . .
C14 C 0.27141(12) -0.2023(3) 0.24335(8) 0.0203(3) Uani 1 1 d . . .
C15 C 0.28540(13) 0.0053(3) 0.28015(9) 0.0248(4) Uani 1 1 d . . .
H15 H 0.2306 0.1111 0.2748 0.030 Uiso 1 1 calc R . .
C16 C 0.37947(13) 0.0571(3) 0.32455(9) 0.0284(4) Uani 1 1 d . . .
H16 H 0.3889 0.1988 0.3495 0.034 Uiso 1 1 calc R . .
C17 C 0.45991(13) -0.0967(3) 0.33280(9) 0.0293(4) Uani 1 1 d . . .
H17 H 0.5241 -0.0606 0.3633 0.035 Uiso 1 1 calc R . .
C18 C 0.44609(13) -0.3024(3) 0.29637(9) 0.0305(4) Uani 1 1 d . . .
H18 H 0.5010 -0.4080 0.3018 0.037 Uiso 1 1 calc R . .
C19 C 0.35229(13) -0.3553(3) 0.25193(9) 0.0260(4) Uani 1 1 d . . .
H19 H 0.3433 -0.4972 0.2271 0.031 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3582(19) . ?
O1 C1 1.4497(18) . ?
O2 C4 1.3468(18) . ?
O2 C5 1.4475(18) . ?
O3 C2 1.202(2) . ?
O4 C4 1.2043(19) . ?
C1 C8 1.510(2) . ?
C1 C5 1.533(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.494(2) . ?
C3 C4 1.499(2) . ?
C3 C7 1.509(2) . ?
C3 C6 1.540(2) . ?
C5 C14 1.512(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.487(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.392(2) . ?
C8 C9 1.393(2) . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.390(2) . ?
C14 C15 1.394(2) . ?
C15 C16 1.388(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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
C2 O1 C1 117.28(12) . . ?
C4 O2 C5 127.16(12) . . ?
O1 C1 C8 107.77(12) . . ?
O1 C1 C5 110.72(12) . . ?
C8 C1 C5 112.99(12) . . ?
O1 C1 H1 108.4 . . ?
C8 C1 H1 108.4 . . ?
C5 C1 H1 108.4 . . ?
O3 C2 O1 117.97(14) . . ?
O3 C2 C3 124.58(15) . . ?
O1 C2 C3 117.44(13) . . ?
C2 C3 C4 120.13(13) . . ?
C2 C3 C7 116.24(14) . . ?
C4 C3 C7 115.47(13) . . ?
C2 C3 C6 116.77(13) . . ?
C4 C3 C6 114.83(13) . . ?
C7 C3 C6 58.37(11) . . ?
O4 C4 O2 117.53(14) . . ?
O4 C4 C3 121.14(14) . . ?
O2 C4 C3 121.22(13) . . ?
O2 C5 C14 106.15(12) . . ?
O2 C5 C1 112.81(12) . . ?
C14 C5 C1 115.62(13) . . ?
O2 C5 H5 107.3 . . ?
C14 C5 H5 107.3 . . ?
C1 C5 H5 107.3 . . ?
C7 C6 C3 59.74(10) . . ?
C7 C6 H6A 117.8 . . ?
C3 C6 H6A 117.8 . . ?
C7 C6 H6B 117.8 . . ?
C3 C6 H6B 117.8 . . ?
H6A C6 H6B 114.9 . . ?
C6 C7 C3 61.88(10) . . ?
C6 C7 H7A 117.6 . . ?
C3 C7 H7A 117.6 . . ?
C6 C7 H7B 117.6 . . ?
C3 C7 H7B 117.6 . . ?
H7A C7 H7B 114.7 . . ?
C13 C8 C9 119.41(15) . . ?
C13 C8 C1 118.68(14) . . ?
C9 C8 C1 121.90(14) . . ?
C10 C9 C8 120.16(16) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.34(16) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.65(15) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.22(16) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.19(15) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C19 C14 C15 119.25(15) . . ?
C19 C14 C5 119.14(15) . . ?
C15 C14 C5 121.60(14) . . ?
C16 C15 C14 119.90(16) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.47(17) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 119.66(16) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.14(16) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.57(16) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?

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
C2 O1 C1 C8 148.23(13) . . . . ?
C2 O1 C1 C5 -87.73(15) . . . . ?
C1 O1 C2 O3 -157.63(14) . . . . ?
C1 O1 C2 C3 20.91(19) . . . . ?
O3 C2 C3 C4 -133.90(17) . . . . ?
O1 C2 C3 C4 47.7(2) . . . . ?
O3 C2 C3 C7 13.3(2) . . . . ?
O1 C2 C3 C7 -165.17(13) . . . . ?
O3 C2 C3 C6 79.3(2) . . . . ?
O1 C2 C3 C6 -99.13(17) . . . . ?
C5 O2 C4 O4 143.89(15) . . . . ?
C5 O2 C4 C3 -39.9(2) . . . . ?
C2 C3 C4 O4 148.97(15) . . . . ?
C7 C3 C4 O4 1.6(2) . . . . ?
C6 C3 C4 O4 -63.6(2) . . . . ?
C2 C3 C4 O2 -27.1(2) . . . . ?
C7 C3 C4 O2 -174.52(13) . . . . ?
C6 C3 C4 O2 120.30(15) . . . . ?
C4 O2 C5 C14 156.34(14) . . . . ?
C4 O2 C5 C1 28.7(2) . . . . ?
O1 C1 C5 O2 51.41(16) . . . . ?
C8 C1 C5 O2 172.40(12) . . . . ?
O1 C1 C5 C14 -71.03(17) . . . . ?
C8 C1 C5 C14 49.96(18) . . . . ?
C2 C3 C6 C7 -105.72(16) . . . . ?
C4 C3 C6 C7 105.75(15) . . . . ?
C2 C3 C7 C6 106.63(15) . . . . ?
C4 C3 C7 C6 -104.65(15) . . . . ?
O1 C1 C8 C13 -150.11(14) . . . . ?
C5 C1 C8 C13 87.23(17) . . . . ?
O1 C1 C8 C9 28.57(19) . . . . ?
C5 C1 C8 C9 -94.09(17) . . . . ?
C13 C8 C9 C10 1.6(2) . . . . ?
C1 C8 C9 C10 -177.12(15) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C13 1.1(2) . . . . ?
C11 C12 C13 C8 -0.1(2) . . . . ?
C9 C8 C13 C12 -1.3(2) . . . . ?
C1 C8 C13 C12 177.45(15) . . . . ?
O2 C5 C14 C19 136.59(14) . . . . ?
C1 C5 C14 C19 -97.50(17) . . . . ?
O2 C5 C14 C15 -42.13(19) . . . . ?
C1 C5 C14 C15 83.78(18) . . . . ?
C19 C14 C15 C16 0.2(2) . . . . ?
C5 C14 C15 C16 178.91(15) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C17 C18 C19 C14 0.2(3) . . . . ?
C15 C14 C19 C18 -0.2(2) . . . . ?
C5 C14 C19 C18 -178.95(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        70.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 936074'
