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

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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 O5'
_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
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   13.861(3)
_cell_length_b                   9.623(2)
_cell_length_c                   17.30(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 128.57(5)
_cell_angle_gamma                90.00
_cell_volume                     1804(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2423
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.3

_exptl_crystal_description       Acicular
_exptl_crystal_colour            Colourless'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.9828
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_process_details   
;
R. H. Blessing Acta Crystallogr., Sect. A, 1995, 51, 33-38
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13363
_diffrn_reflns_av_R_equivalents  0.1511
_diffrn_reflns_av_sigmaI/netI    0.1509
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         26.25
_reflns_number_total             3588
_reflns_number_gt                1013
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0771P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0056(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3588
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1493
_refine_ls_R_factor_gt           0.0708
_refine_ls_wR_factor_ref         0.2013
_refine_ls_wR_factor_gt          0.1590
_refine_ls_goodness_of_fit_ref   0.759
_refine_ls_restrained_S_all      0.759
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3677(3) 0.2042(3) -0.1004(2) 0.0537(9) Uani 1 1 d . . .
C2 C 0.4944(3) 0.1828(3) -0.0337(2) 0.0567(9) Uani 1 1 d . . .
H2 H 0.5327 0.1299 -0.0526 0.068 Uiso 1 1 calc R . .
C3 C 0.5671(3) 0.2406(3) 0.0637(2) 0.0517(9) Uani 1 1 d . . .
C4 C 0.5079(3) 0.3214(3) 0.0941(2) 0.0480(8) Uani 1 1 d . . .
C5 C 0.3773(3) 0.3440(3) 0.0242(2) 0.0525(9) Uani 1 1 d . . .
C6 C 0.3084(3) 0.2861(3) -0.0730(2) 0.0567(9) Uani 1 1 d . . .
H6 H 0.2240 0.3025 -0.1186 0.068 Uiso 1 1 calc R . .
C7 C 0.5782(3) 0.3744(3) 0.2004(2) 0.0484(8) Uani 1 1 d . . .
C8 C 0.6358(3) 0.2788(4) 0.2794(2) 0.0586(10) Uani 1 1 d . . .
H8 H 0.6335 0.1841 0.2675 0.070 Uiso 1 1 calc R . .
C9 C 0.6969(3) 0.3282(4) 0.3764(3) 0.0734(12) Uani 1 1 d . . .
H9 H 0.7341 0.2650 0.4284 0.088 Uiso 1 1 calc R . .
C10 C 0.7026(3) 0.4693(5) 0.3960(3) 0.0798(12) Uani 1 1 d . . .
H10 H 0.7434 0.5004 0.4604 0.096 Uiso 1 1 calc R . .
C11 C 0.6465(3) 0.5637(4) 0.3179(3) 0.0761(12) Uani 1 1 d . . .
H11 H 0.6504 0.6584 0.3304 0.091 Uiso 1 1 calc R . .
C12 C 0.5840(3) 0.5167(4) 0.2202(2) 0.0623(10) Uani 1 1 d . . .
H12 H 0.5464 0.5804 0.1686 0.075 Uiso 1 1 calc R . .
C13 C 0.2972(3) 0.1410(4) -0.2040(2) 0.0604(10) Uani 1 1 d . . .
C14 C 0.0941(4) 0.1052(5) -0.3616(3) 0.0918(14) Uani 1 1 d . . .
H14A H 0.1433 0.0476 -0.3713 0.110 Uiso 1 1 calc R . .
H14B H 0.0314 0.0471 -0.3693 0.110 Uiso 1 1 calc R . .
C15 C 0.0347(5) 0.2168(5) -0.4361(3) 0.144(2) Uani 1 1 d . . .
H15B H -0.0228 0.1770 -0.5008 0.216 Uiso 1 1 calc R . .
H15A H 0.0965 0.2680 -0.4330 0.216 Uiso 1 1 calc R . .
H15C H -0.0082 0.2782 -0.4231 0.216 Uiso 1 1 calc R . .
C16 C 0.7057(3) 0.2191(4) 0.1264(3) 0.0607(10) Uani 1 1 d . . .
C17 C 0.9064(3) 0.3170(5) 0.2482(3) 0.1075(16) Uani 1 1 d . . .
H17B H 0.9323 0.2305 0.2849 0.129 Uiso 1 1 calc R . .
H17A H 0.9330 0.3160 0.2079 0.129 Uiso 1 1 calc R . .
C18 C 0.9634(4) 0.4333(6) 0.3166(4) 0.156(2) Uani 1 1 d . . .
H18A H 1.0515 0.4268 0.3562 0.234 Uiso 1 1 calc R . .
H18B H 0.9404 0.4312 0.3587 0.234 Uiso 1 1 calc R . .
H18C H 0.9358 0.5189 0.2801 0.234 Uiso 1 1 calc R . .
C19 C 0.3045(3) 0.4240(4) 0.0481(3) 0.0668(10) Uani 1 1 d . . .
H19 H 0.3434 0.4434 0.1143 0.080 Uiso 1 1 calc R . .
O13A O 0.1740(2) 0.1656(3) -0.26084(17) 0.0775(8) Uani 1 1 d . . .
O13B O 0.3465(2) 0.0748(3) -0.23136(17) 0.0839(9) Uani 1 1 d . . .
O16A O 0.7709(2) 0.3289(3) 0.1841(2) 0.0825(9) Uani 1 1 d . . .
O16B O 0.7521(2) 0.1141(3) 0.12196(19) 0.0895(10) Uani 1 1 d . . .
O19 O 0.1986(2) 0.4648(3) -0.01305(18) 0.1114(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.390(5) . ?
C1 C6 1.417(4) . ?
C1 C13 1.533(5) . ?
C2 C3 1.431(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.447(4) . ?
C3 C16 1.520(5) . ?
C4 C5 1.434(5) . ?
C4 C7 1.535(5) . ?
C5 C6 1.431(5) . ?
C5 C19 1.518(4) . ?
C6 H6 0.9300 . ?
C7 C12 1.402(4) . ?
C7 C8 1.410(4) . ?
C8 C9 1.410(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.390(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.409(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 O13B 1.225(4) . ?
C13 O13A 1.358(4) . ?
C14 C15 1.473(5) . ?
C14 O13A 1.482(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15B 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O16B 1.226(4) . ?
C16 O16A 1.343(4) . ?
C17 C18 1.453(5) . ?
C17 O16A 1.475(4) . ?
C17 H17B 0.9700 . ?
C17 H17A 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O19 1.222(4) . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.0(3) . . ?
C2 C1 C13 117.8(3) . . ?
C6 C1 C13 122.1(3) . . ?
C1 C2 C3 121.2(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 C16 115.8(3) . . ?
C4 C3 C16 124.3(3) . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 C7 119.0(3) . . ?
C3 C4 C7 122.2(3) . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 C19 116.6(3) . . ?
C4 C5 C19 123.4(3) . . ?
C1 C6 C5 120.6(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C12 C7 C8 119.3(3) . . ?
C12 C7 C4 120.9(3) . . ?
C8 C7 C4 119.8(3) . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 119.2(4) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 120.5(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 120.3(3) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
O13B C13 O13A 124.2(3) . . ?
O13B C13 C1 123.7(3) . . ?
O13A C13 C1 112.1(3) . . ?
C15 C14 O13A 110.1(4) . . ?
C15 C14 H14A 109.6 . . ?
O13A C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
O13A C14 H14B 109.6 . . ?
H14A C14 H14B 108.2 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15A 109.5 . . ?
H15B C15 H15A 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
O16B C16 O16A 124.0(4) . . ?
O16B C16 C3 123.1(3) . . ?
O16A C16 C3 112.9(3) . . ?
C18 C17 O16A 110.1(4) . . ?
C18 C17 H17B 109.6 . . ?
O16A C17 H17B 109.6 . . ?
C18 C17 H17A 109.6 . . ?
O16A C17 H17A 109.6 . . ?
H17B C17 H17A 108.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O19 C19 C5 124.8(3) . . ?
O19 C19 H19 117.6 . . ?
C5 C19 H19 117.6 . . ?
C13 O13A C14 117.7(3) . . ?
C16 O16A C17 116.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.9(5) . . . . ?
C13 C1 C2 C3 178.8(3) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C1 C2 C3 C16 -175.3(3) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C16 C3 C4 C5 174.2(3) . . . . ?
C2 C3 C4 C7 174.0(3) . . . . ?
C16 C3 C4 C7 -10.3(5) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C7 C4 C5 C6 -175.1(3) . . . . ?
C3 C4 C5 C19 178.5(3) . . . . ?
C7 C4 C5 C19 2.9(5) . . . . ?
C2 C1 C6 C5 -1.9(5) . . . . ?
C13 C1 C6 C5 -179.7(3) . . . . ?
C4 C5 C6 C1 1.2(5) . . . . ?
C19 C5 C6 C1 -176.9(3) . . . . ?
C5 C4 C7 C12 -62.9(4) . . . . ?
C3 C4 C7 C12 121.6(3) . . . . ?
C5 C4 C7 C8 115.8(3) . . . . ?
C3 C4 C7 C8 -59.7(4) . . . . ?
C12 C7 C8 C9 0.7(5) . . . . ?
C4 C7 C8 C9 -178.0(3) . . . . ?
C7 C8 C9 C10 -0.7(5) . . . . ?
C8 C9 C10 C11 0.1(6) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C8 C7 C12 C11 -0.1(5) . . . . ?
C4 C7 C12 C11 178.6(3) . . . . ?
C10 C11 C12 C7 -0.5(5) . . . . ?
C2 C1 C13 O13B -1.1(5) . . . . ?
C6 C1 C13 O13B 176.7(3) . . . . ?
C2 C1 C13 O13A 178.1(3) . . . . ?
C6 C1 C13 O13A -4.1(5) . . . . ?
C2 C3 C16 O16B -34.5(5) . . . . ?
C4 C3 C16 O16B 149.6(3) . . . . ?
C2 C3 C16 O16A 143.2(3) . . . . ?
C4 C3 C16 O16A -32.6(4) . . . . ?
C6 C5 C19 O19 -14.7(5) . . . . ?
C4 C5 C19 O19 167.2(4) . . . . ?
O13B C13 O13A C14 1.6(5) . . . . ?
C1 C13 O13A C14 -177.6(3) . . . . ?
C15 C14 O13A C13 -116.1(4) . . . . ?
O16B C16 O16A C17 -2.7(5) . . . . ?
C3 C16 O16A C17 179.6(3) . . . . ?
C18 C17 O16A C16 -171.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.25
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.058

# start Validation Reply Form
_vrf_PLAT026_datam               
;
PROBLEM: Ratio Observed/Unique Reflections too low
RESPONSE: Poor crystal quality with lots of diffused scattering
;
# end Validation Reply Form
_database_code_depnum_ccdc_archive 'CCDC 989389'
