# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_0184_160513_kms_d_uvag_0m
_database_code_depnum_ccdc_archive 'CCDC 1040209'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 O7'
_chemical_formula_sum            'C21 H20 O7'
_chemical_formula_weight         384.37
_chemical_absolute_configuration rm
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2   '

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

_cell_length_a                   27.206(5)
_cell_length_b                   6.873(5)
_cell_length_c                   10.231(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 92.155(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1911.7(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4209
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      1.334
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7663
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2662
_reflns_number_gt                2514
_reflns_threshold_expression     >2σ(I)

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 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)+(0.0886P)²+0.1096P] 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     SHELXL
_refine_ls_extinction_coef       0.0035(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(11)
_refine_ls_number_reflns         2662
_refine_ls_number_parameters     266
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_restrained_S_all      1.195
_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
C1 C 0.83836(9) 0.3810(4) 0.9681(2) 0.0360(6) Uani 1 1 d . . .
C2 C 0.85366(8) 0.5811(4) 0.9262(2) 0.0366(6) Uani 1 1 d . . .
H2 H 0.8521 0.5817 0.8303 0.044 Uiso 1 1 calc R . .
C3 C 0.90648(8) 0.6260(4) 0.9684(2) 0.0340(5) Uani 1 1 d . . .
H3 H 0.9121 0.7665 0.9626 0.041 Uiso 1 1 calc R . .
C4 C 0.91773(7) 0.5582(4) 1.1081(2) 0.0302(5) Uani 1 1 d . . .
H4 H 0.8938 0.6160 1.1658 0.036 Uiso 1 1 calc R . .
C5 C 0.91337(8) 0.3405(4) 1.1134(2) 0.0324(5) Uani 1 1 d . . .
H5 H 0.9410 0.2805 1.0694 0.039 Uiso 1 1 calc R . .
C6 C 0.86551(8) 0.2718(4) 1.0512(2) 0.0381(6) Uani 1 1 d . . .
H6 H 0.8543 0.1480 1.0714 0.046 Uiso 1 1 calc R . .
C7 C 0.78913(9) 0.3107(5) 0.9178(2) 0.0501(7) Uani 1 1 d . . .
H7A H 0.7838 0.1778 0.9459 0.060 Uiso 1 1 calc R . .
H7B H 0.7633 0.3916 0.9516 0.060 Uiso 1 1 calc R . .
C8 C 0.74392(9) 0.3161(4) 0.7146(2) 0.0396(6) Uani 1 1 d . . .
C9 C 0.74701(9) 0.3248(4) 0.5705(2) 0.0395(6) Uani 1 1 d . . .
C10 C 0.70371(11) 0.3329(4) 0.4944(3) 0.0506(7) Uani 1 1 d . . .
H10 H 0.6735 0.3350 0.5342 0.061 Uiso 1 1 calc R . .
C11 C 0.70537(12) 0.3377(5) 0.3600(3) 0.0591(8) Uani 1 1 d . . .
H11 H 0.6763 0.3434 0.3094 0.071 Uiso 1 1 calc R . .
C12 C 0.74937(14) 0.3343(5) 0.3012(3) 0.0618(9) Uani 1 1 d . . .
H12 H 0.7502 0.3360 0.2105 0.074 Uiso 1 1 calc R . .
C13 C 0.79285(12) 0.3283(5) 0.3759(3) 0.0596(8) Uani 1 1 d . . .
H13 H 0.8229 0.3278 0.3352 0.072 Uiso 1 1 calc R . .
C14 C 0.79170(10) 0.3230(5) 0.5104(3) 0.0496(7) Uani 1 1 d . . .
H14 H 0.8209 0.3183 0.5606 0.060 Uiso 1 1 calc R . .
C15 C 0.92977(8) 0.1091(4) 1.2829(2) 0.0368(5) Uani 1 1 d . . .
C16 C 0.93133(9) 0.0718(4) 1.4265(2) 0.0419(6) Uani 1 1 d . . .
C17 C 0.92879(12) 0.2218(5) 1.5150(3) 0.0595(8) Uani 1 1 d . . .
H17 H 0.9261 0.3496 1.4859 0.071 Uiso 1 1 calc R . .
C18 C 0.93024(16) 0.1812(7) 1.6488(3) 0.0772(10) Uani 1 1 d . . .
H18 H 0.9281 0.2817 1.7092 0.093 Uiso 1 1 calc R . .
C19 C 0.93475(14) -0.0063(7) 1.6903(3) 0.0763(11) Uani 1 1 d . . .
H19 H 0.9364 -0.0324 1.7795 0.092 Uiso 1 1 calc R . .
C20 C 0.93686(14) -0.1551(7) 1.6047(4) 0.0770(11) Uani 1 1 d . . .
H20 H 0.9392 -0.2824 1.6351 0.092 Uiso 1 1 calc R . .
C21 C 0.93556(12) -0.1176(5) 1.4707(3) 0.0581(8) Uani 1 1 d . . .
H21 H 0.9375 -0.2196 1.4113 0.070 Uiso 1 1 calc R . .
O2 O 0.82029(7) 0.7265(3) 0.96714(18) 0.0515(5) Uani 1 1 d D . .
O3 O 0.93635(6) 0.5287(3) 0.87855(16) 0.0473(5) Uani 1 1 d D . .
O4 O 0.96617(6) 0.6142(3) 1.15223(17) 0.0392(4) Uani 1 1 d D . .
O5 O 0.91538(6) 0.2879(2) 1.25237(14) 0.0373(4) Uani 1 1 d . . .
O6 O 0.78823(6) 0.3208(3) 0.77587(14) 0.0446(5) Uani 1 1 d . . .
O7 O 0.70588(6) 0.3043(4) 0.77156(17) 0.0595(6) Uani 1 1 d . . .
O8 O 0.94022(8) -0.0107(3) 1.20117(18) 0.0566(5) Uani 1 1 d . . .
H3' H 0.9686(7) 0.569(6) 0.897(3) 0.063(9) Uiso 1 1 d D . .
H4' H 0.9661(13) 0.751(2) 1.159(4) 0.087(12) Uiso 1 1 d D . .
H2' H 0.8184(14) 0.722(6) 1.0580(15) 0.090(12) Uiso 1 1 d 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
C1 C6 1.336(4) . ?
C1 C7 1.497(3) . ?
C1 C2 1.504(4) . ?
C2 O2 1.424(3) . ?
C2 C3 1.517(3) . ?
C2 H2 0.9800 . ?
C3 O3 1.417(3) . ?
C3 C4 1.524(3) . ?
C3 H3 0.9800 . ?
C4 O4 1.430(3) . ?
C4 C5 1.502(4) . ?
C4 H4 0.9800 . ?
C5 O5 1.466(3) . ?
C5 C6 1.504(3) . ?
C5 H5 0.9800 . ?
C6 H6 0.9300 . ?
C7 O6 1.453(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O7 1.209(3) . ?
C8 O6 1.338(3) . ?
C8 C9 1.481(3) . ?
C9 C14 1.383(4) . ?
C9 C10 1.389(4) . ?
C10 C11 1.377(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.360(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O8 1.215(3) . ?
C15 O5 1.323(3) . ?
C15 C16 1.490(3) . ?
C16 C17 1.376(4) . ?
C16 C21 1.382(4) . ?
C17 C18 1.396(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.361(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.348(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.395(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
O2 H2' 0.933(15) . ?
O3 H3' 0.934(14) . ?
O4 H4' 0.946(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C7 120.2(3) . . ?
C6 C1 C2 122.9(2) . . ?
C7 C1 C2 116.8(2) . . ?
O2 C2 C1 111.82(19) . . ?
O2 C2 C3 112.4(2) . . ?
C1 C2 C3 112.0(2) . . ?
O2 C2 H2 106.7 . . ?
C1 C2 H2 106.7 . . ?
C3 C2 H2 106.7 . . ?
O3 C3 C2 106.26(18) . . ?
O3 C3 C4 111.38(19) . . ?
C2 C3 C4 111.07(17) . . ?
O3 C3 H3 109.4 . . ?
C2 C3 H3 109.4 . . ?
C4 C3 H3 109.4 . . ?
O4 C4 C5 109.26(18) . . ?
O4 C4 C3 111.36(18) . . ?
C5 C4 C3 108.94(18) . . ?
O4 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
O5 C5 C4 106.27(18) . . ?
O5 C5 C6 109.45(19) . . ?
C4 C5 C6 111.47(19) . . ?
O5 C5 H5 109.9 . . ?
C4 C5 H5 109.9 . . ?
C6 C5 H5 109.9 . . ?
C1 C6 C5 122.8(2) . . ?
C1 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
O6 C7 C1 108.03(19) . . ?
O6 C7 H7A 110.1 . . ?
C1 C7 H7A 110.1 . . ?
O6 C7 H7B 110.1 . . ?
C1 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
O7 C8 O6 123.2(2) . . ?
O7 C8 C9 124.3(2) . . ?
O6 C8 C9 112.4(2) . . ?
C14 C9 C10 119.5(3) . . ?
C14 C9 C8 121.7(2) . . ?
C10 C9 C8 118.8(2) . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
O8 C15 O5 122.8(2) . . ?
O8 C15 C16 124.3(2) . . ?
O5 C15 C16 112.9(2) . . ?
C17 C16 C21 119.7(3) . . ?
C17 C16 C15 121.3(2) . . ?
C21 C16 C15 118.9(2) . . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 119.6(4) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 121.4(3) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 119.9(4) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C16 C21 C20 119.7(3) . . ?
C16 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C2 O2 H2' 109(3) . . ?
C3 O3 H3' 106(2) . . ?
C4 O4 H4' 107(2) . . ?
C15 O5 C5 117.23(18) . . ?
C8 O6 C7 116.61(18) . . ?

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 O2 -116.6(3) . . . . ?
C7 C1 C2 O2 60.2(3) . . . . ?
C6 C1 C2 C3 10.6(3) . . . . ?
C7 C1 C2 C3 -172.6(2) . . . . ?
O2 C2 C3 O3 -154.76(19) . . . . ?
C1 C2 C3 O3 78.4(2) . . . . ?
O2 C2 C3 C4 84.0(2) . . . . ?
C1 C2 C3 C4 -42.9(3) . . . . ?
O3 C3 C4 O4 66.5(3) . . . . ?
C2 C3 C4 O4 -175.24(18) . . . . ?
O3 C3 C4 C5 -54.1(2) . . . . ?
C2 C3 C4 C5 64.2(2) . . . . ?
O4 C4 C5 O5 68.5(2) . . . . ?
C3 C4 C5 O5 -169.66(16) . . . . ?
O4 C4 C5 C6 -172.35(17) . . . . ?
C3 C4 C5 C6 -50.5(2) . . . . ?
C7 C1 C6 C5 -175.1(2) . . . . ?
C2 C1 C6 C5 1.6(4) . . . . ?
O5 C5 C6 C1 136.5(2) . . . . ?
C4 C5 C6 C1 19.2(3) . . . . ?
C6 C1 C7 O6 -127.0(3) . . . . ?
C2 C1 C7 O6 56.1(3) . . . . ?
O7 C8 C9 C14 -174.9(3) . . . . ?
O6 C8 C9 C14 4.5(4) . . . . ?
O7 C8 C9 C10 4.4(4) . . . . ?
O6 C8 C9 C10 -176.2(2) . . . . ?
C14 C9 C10 C11 0.4(4) . . . . ?
C8 C9 C10 C11 -178.9(3) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C13 -0.8(5) . . . . ?
C11 C12 C13 C14 0.9(5) . . . . ?
C12 C13 C14 C9 -0.3(5) . . . . ?
C10 C9 C14 C13 -0.3(4) . . . . ?
C8 C9 C14 C13 179.0(3) . . . . ?
O8 C15 C16 C17 166.8(3) . . . . ?
O5 C15 C16 C17 -13.6(3) . . . . ?
O8 C15 C16 C21 -13.1(4) . . . . ?
O5 C15 C16 C21 166.5(3) . . . . ?
C21 C16 C17 C18 -0.3(5) . . . . ?
C15 C16 C17 C18 179.8(3) . . . . ?
C16 C17 C18 C19 0.8(6) . . . . ?
C17 C18 C19 C20 -1.4(7) . . . . ?
C18 C19 C20 C21 1.5(6) . . . . ?
C17 C16 C21 C20 0.5(5) . . . . ?
C15 C16 C21 C20 -179.7(3) . . . . ?
C19 C20 C21 C16 -1.0(5) . . . . ?
O8 C15 O5 C5 -1.4(3) . . . . ?
C16 C15 O5 C5 179.02(18) . . . . ?
C4 C5 O5 C15 -156.38(19) . . . . ?
C6 C5 O5 C15 83.1(2) . . . . ?
O7 C8 O6 C7 0.1(4) . . . . ?
C9 C8 O6 C7 -179.3(2) . . . . ?
C1 C7 O6 C8 -162.1(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
O3 H3' O4 0.934(14) 1.889(19) 2.746(2) 151(3) 2_757
O4 H4' O8 0.946(15) 1.84(2) 2.724(3) 155(3) 1_565
O2 H2' O7 0.933(15) 1.97(2) 2.843(3) 155(4) 4_657

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.068
