# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_exp_2478
_database_code_depnum_ccdc_archive 'CCDC 1040577'
_audit_update_record             
;
2014-12-20 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_audit_creation_date             2014-10-28
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        '(R)-glycyfuranocoumarin A'
_chemical_formula_moiety         'C21 H20 O6'
_chemical_formula_sum            'C21 H20 O6'
_chemical_formula_weight         368.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   9.3372(5)
_cell_length_b                   9.6286(3)
_cell_length_c                   19.5494(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1757.57(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3013
_cell_measurement_temperature    104.3
_cell_measurement_theta_max      70.7440
_cell_measurement_theta_min      4.5184
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5776
_diffrn_reflns_theta_full        70.91
_diffrn_reflns_theta_max         70.91
_diffrn_reflns_theta_min         4.52
_diffrn_ambient_temperature      104.3
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega   45.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   62.0000 -156.0000 59

#__ type_ start__ end____ width___ exp.time_
  3 omega  -28.00   51.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -60.0000  -96.0000 79

#__ type_ start__ end____ width___ exp.time_
  4 omega   18.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000 -180.0000 88

#__ type_ start__ end____ width___ exp.time_
  5 omega   85.00  110.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -168.0000  117.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   58.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   52.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   41.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
  9 omega  103.00  143.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  115.0000   -8.0000 40

#__ type_ start__ end____ width___ exp.time_
 10 omega  151.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   91.00  164.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 73

#__ type_ start__ end____ width___ exp.time_
 12 omega   79.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 65

#__ type_ start__ end____ width___ exp.time_
 13 omega  100.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 74

#__ type_ start__ end____ width___ exp.time_
 14 omega   79.00  132.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 53
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0833466000
_diffrn_orient_matrix_UB_12      0.0945668000
_diffrn_orient_matrix_UB_13      -0.0495836000
_diffrn_orient_matrix_UB_21      0.0858750000
_diffrn_orient_matrix_UB_22      0.1264403000
_diffrn_orient_matrix_UB_23      0.0255430000
_diffrn_orient_matrix_UB_31      0.1136253000
_diffrn_orient_matrix_UB_32      -0.0259927000
_diffrn_orient_matrix_UB_33      -0.0555890000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3166
_reflns_number_total             3325
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(16)
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0488P)²+0.3601P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0879
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
O3 O -0.59243(12) -0.46730(13) -0.09304(6) 0.0189(3) Uani 1 1 d . . .
O1 O -0.72376(12) -0.54547(13) 0.13374(6) 0.0201(3) Uani 1 1 d . . .
C14 C -0.4970(2) -0.43197(17) -0.14412(8) 0.0187(4) Uani 1 1 d . . .
O2 O -0.25695(13) -0.36047(15) 0.08162(6) 0.0236(3) Uani 1 1 d . . .
O4 O -0.53797(14) -0.44984(13) -0.20207(6) 0.0237(3) Uani 1 1 d . . .
C13 C -0.35722(19) -0.37758(17) -0.12403(9) 0.0179(4) Uani 1 1 d . . .
C12 C -0.32447(18) -0.36966(18) -0.05655(9) 0.0173(3) Uani 1 1 d . . .
H12 H -0.2345 -0.3374 -0.0437 0.021 Uiso 1 1 calc R . .
C9 C -0.39141(18) -0.40504(18) 0.06650(9) 0.0189(4) Uani 1 1 d . . .
C11 C -0.55957(18) -0.45756(18) -0.02443(8) 0.0168(3) Uani 1 1 d . . .
C6 C -0.66133(18) -0.49953(18) 0.02265(8) 0.0168(3) Uani 1 1 d . . .
C7 C -0.62183(18) -0.49226(18) 0.09073(9) 0.0181(3) Uani 1 1 d . . .
O5 O -0.41154(13) -0.17178(13) -0.22086(6) 0.0209(3) Uani 1 1 d . . .
H5 H -0.4165 -0.1093 -0.2493 0.031 Uiso 1 1 calc R . .
O6 O 0.03944(14) -0.23096(14) -0.32992(7) 0.0269(3) Uani 1 1 d . . .
H6 H 0.1066 -0.2857 -0.3314 0.040 Uiso 1 1 calc R . .
C3 C -0.80728(19) -0.56914(18) 0.01682(9) 0.0179(4) Uani 1 1 d . . .
C1 C -0.85532(18) -0.5575(2) 0.09317(9) 0.0214(4) Uani 1 1 d . . .
H1 H -0.9095 -0.4710 0.0984 0.026 Uiso 1 1 calc R . .
C19 C -0.01975(19) -0.37129(19) -0.23135(9) 0.0218(4) Uani 1 1 d . . .
H19 H 0.0689 -0.4153 -0.2325 0.026 Uiso 1 1 calc R . .
C16 C -0.28364(18) -0.23711(18) -0.22674(8) 0.0176(3) Uani 1 1 d . . .
C8 C -0.49114(19) -0.44411(18) 0.11486(8) 0.0196(4) Uani 1 1 d . . .
H8 H -0.4717 -0.4385 0.1614 0.024 Uiso 1 1 calc R . .
C10 C -0.42424(19) -0.40953(17) -0.00447(9) 0.0179(4) Uani 1 1 d . . .
C15 C -0.25334(18) -0.34104(18) -0.17846(8) 0.0179(4) Uani 1 1 d . . .
C17 C -0.18482(19) -0.20302(18) -0.27716(9) 0.0195(4) Uani 1 1 d . . .
H17 H -0.2067 -0.1355 -0.3095 0.023 Uiso 1 1 calc R . .
C18 C -0.05357(18) -0.26991(18) -0.27907(9) 0.0201(4) Uani 1 1 d . . .
C2 C -0.9434(2) -0.6738(2) 0.12313(10) 0.0345(5) Uani 1 1 d . . .
H2A H -0.9608 -0.6557 0.1707 0.052 Uiso 1 1 calc R . .
H2B H -0.8925 -0.7599 0.1184 0.052 Uiso 1 1 calc R . .
H2C H -1.0332 -0.6799 0.0993 0.052 Uiso 1 1 calc R . .
C20 C -0.12007(19) -0.40606(18) -0.18200(8) 0.0194(4) Uani 1 1 d . . .
H20 H -0.0979 -0.4748 -0.1503 0.023 Uiso 1 1 calc R . .
C4 C -0.91317(18) -0.4923(2) -0.02910(9) 0.0232(4) Uani 1 1 d . . .
H4A H -0.8801 -0.4954 -0.0756 0.035 Uiso 1 1 calc R . .
H4B H -0.9205 -0.3973 -0.0145 0.035 Uiso 1 1 calc R . .
H4C H -1.0055 -0.5358 -0.0261 0.035 Uiso 1 1 calc R . .
C21 C -0.2175(2) -0.3631(2) 0.15281(9) 0.0263(4) Uani 1 1 d . . .
H21A H -0.2770 -0.2995 0.1778 0.039 Uiso 1 1 calc R . .
H21B H -0.1190 -0.3363 0.1575 0.039 Uiso 1 1 calc R . .
H21C H -0.2304 -0.4552 0.1705 0.039 Uiso 1 1 calc R . .
C5 C -0.7894(2) -0.71915(19) -0.00740(10) 0.0245(4) Uani 1 1 d . . .
H5A H -0.7290 -0.7685 0.0240 0.037 Uiso 1 1 calc R . .
H5B H -0.7466 -0.7198 -0.0520 0.037 Uiso 1 1 calc R . .
H5C H -0.8815 -0.7633 -0.0094 0.037 Uiso 1 1 calc R . .


_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
O3 C14 1.381(2) . ?
O3 C11 1.3793(19) . ?
O1 C7 1.369(2) . ?
O1 C1 1.467(2) . ?
C14 O4 1.208(2) . ?
C14 C13 1.460(2) . ?
O2 C9 1.359(2) . ?
O2 C21 1.440(2) . ?
C13 C12 1.356(2) . ?
C13 C15 1.482(2) . ?
C12 H12 0.9300 . ?
C12 C10 1.432(2) . ?
C9 C8 1.379(2) . ?
C9 C10 1.422(2) . ?
C11 C6 1.383(2) . ?
C11 C10 1.401(2) . ?
C6 C7 1.383(2) . ?
C6 C3 1.523(2) . ?
C7 C8 1.388(2) . ?
O5 H5 0.8200 . ?
O5 C16 1.355(2) . ?
O6 H6 0.8200 . ?
O6 C18 1.372(2) . ?
C3 C1 1.562(2) . ?
C3 C4 1.527(2) . ?
C3 C5 1.529(2) . ?
C1 H1 0.9800 . ?
C1 C2 1.508(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.387(3) . ?
C19 C20 1.386(2) . ?
C16 C15 1.404(3) . ?
C16 C17 1.390(2) . ?
C8 H8 0.9300 . ?
C15 C20 1.395(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C20 H20 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

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
C11 O3 C14 122.88(13) . . ?
C7 O1 C1 106.24(12) . . ?
O3 C14 C13 118.08(14) . . ?
O4 C14 O3 115.99(16) . . ?
O4 C14 C13 125.93(16) . . ?
C9 O2 C21 116.15(14) . . ?
C14 C13 C15 118.48(14) . . ?
C12 C13 C14 118.91(15) . . ?
C12 C13 C15 122.50(16) . . ?
C13 C12 H12 119.0 . . ?
C13 C12 C10 121.98(16) . . ?
C10 C12 H12 119.0 . . ?
O2 C9 C8 124.10(15) . . ?
O2 C9 C10 114.89(15) . . ?
C8 C9 C10 121.01(16) . . ?
O3 C11 C6 118.33(15) . . ?
O3 C11 C10 119.60(15) . . ?
C6 C11 C10 122.06(15) . . ?
C11 C6 C3 133.91(15) . . ?
C7 C6 C11 116.26(15) . . ?
C7 C6 C3 109.45(14) . . ?
O1 C7 C6 112.74(14) . . ?
O1 C7 C8 121.83(15) . . ?
C6 C7 C8 125.34(16) . . ?
C16 O5 H5 109.5 . . ?
C18 O6 H6 109.5 . . ?
C6 C3 C1 98.85(13) . . ?
C6 C3 C4 114.21(15) . . ?
C6 C3 C5 109.96(14) . . ?
C4 C3 C1 109.95(14) . . ?
C4 C3 C5 110.27(15) . . ?
C5 C3 C1 113.24(14) . . ?
O1 C1 C3 106.37(13) . . ?
O1 C1 H1 108.0 . . ?
O1 C1 C2 107.80(14) . . ?
C3 C1 H1 108.0 . . ?
C2 C1 C3 118.33(16) . . ?
C2 C1 H1 108.0 . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C20 C19 C18 118.98(16) . . ?
O5 C16 C15 116.84(15) . . ?
O5 C16 C17 122.40(15) . . ?
C17 C16 C15 120.75(16) . . ?
C9 C8 C7 116.86(15) . . ?
C9 C8 H8 121.6 . . ?
C7 C8 H8 121.6 . . ?
C9 C10 C12 123.05(16) . . ?
C11 C10 C12 118.50(15) . . ?
C11 C10 C9 118.44(15) . . ?
C16 C15 C13 121.32(15) . . ?
C20 C15 C13 120.87(15) . . ?
C20 C15 C16 117.79(16) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.79(16) . . ?
C18 C17 H17 120.1 . . ?
O6 C18 C19 122.38(16) . . ?
O6 C18 C17 116.90(16) . . ?
C17 C18 C19 120.72(16) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C19 C20 C15 121.96(16) . . ?
C19 C20 H20 119.0 . . ?
C15 C20 H20 119.0 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

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
O3 C14 C13 C12 2.9(2) . . . . ?
O3 C14 C13 C15 179.24(15) . . . . ?
O3 C11 C6 C7 177.90(15) . . . . ?
O3 C11 C6 C3 6.0(3) . . . . ?
O3 C11 C10 C12 1.0(2) . . . . ?
O3 C11 C10 C9 -177.86(15) . . . . ?
O1 C7 C8 C9 174.02(16) . . . . ?
C14 O3 C11 C6 -178.07(15) . . . . ?
C14 O3 C11 C10 0.2(2) . . . . ?
C14 C13 C12 C10 -1.7(2) . . . . ?
C14 C13 C15 C16 61.9(2) . . . . ?
C14 C13 C15 C20 -120.10(18) . . . . ?
O2 C9 C8 C7 -177.57(16) . . . . ?
O2 C9 C10 C12 -0.3(3) . . . . ?
O2 C9 C10 C11 178.47(15) . . . . ?
O4 C14 C13 C12 -176.92(17) . . . . ?
O4 C14 C13 C15 -0.5(3) . . . . ?
C13 C12 C10 C9 178.60(17) . . . . ?
C13 C12 C10 C11 -0.2(3) . . . . ?
C13 C15 C20 C19 -178.37(16) . . . . ?
C12 C13 C15 C16 -121.81(19) . . . . ?
C12 C13 C15 C20 56.2(2) . . . . ?
C11 O3 C14 O4 177.65(15) . . . . ?
C11 O3 C14 C13 -2.2(2) . . . . ?
C11 C6 C7 O1 -175.25(15) . . . . ?
C11 C6 C7 C8 1.4(3) . . . . ?
C11 C6 C3 C1 -172.12(19) . . . . ?
C11 C6 C3 C4 -55.5(3) . . . . ?
C11 C6 C3 C5 69.1(2) . . . . ?
C6 C11 C10 C12 179.25(16) . . . . ?
C6 C11 C10 C9 0.4(3) . . . . ?
C6 C7 C8 C9 -2.3(3) . . . . ?
C6 C3 C1 O1 -23.70(17) . . . . ?
C6 C3 C1 C2 -145.06(17) . . . . ?
C7 O1 C1 C3 24.53(18) . . . . ?
C7 O1 C1 C2 152.39(15) . . . . ?
C7 C6 C3 C1 15.53(18) . . . . ?
C7 C6 C3 C4 132.18(16) . . . . ?
C7 C6 C3 C5 -103.25(16) . . . . ?
O5 C16 C15 C13 0.4(2) . . . . ?
O5 C16 C15 C20 -177.67(14) . . . . ?
O5 C16 C17 C18 177.60(15) . . . . ?
C3 C6 C7 O1 -1.4(2) . . . . ?
C3 C6 C7 C8 175.26(16) . . . . ?
C1 O1 C7 C6 -14.84(19) . . . . ?
C1 O1 C7 C8 168.37(16) . . . . ?
C16 C15 C20 C19 -0.3(2) . . . . ?
C16 C17 C18 O6 -179.68(16) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C8 C9 C10 C12 179.82(16) . . . . ?
C8 C9 C10 C11 -1.4(3) . . . . ?
C10 C9 C8 C7 2.2(3) . . . . ?
C10 C11 C6 C7 -0.4(2) . . . . ?
C10 C11 C6 C3 -172.31(18) . . . . ?
C15 C13 C12 C10 -177.94(16) . . . . ?
C15 C16 C17 C18 -1.4(3) . . . . ?
C17 C16 C15 C13 179.45(16) . . . . ?
C17 C16 C15 C20 1.4(2) . . . . ?
C18 C19 C20 C15 -0.7(3) . . . . ?
C20 C19 C18 O6 -179.25(16) . . . . ?
C20 C19 C18 C17 0.7(3) . . . . ?
C4 C3 C1 O1 -143.58(14) . . . . ?
C4 C3 C1 C2 95.07(19) . . . . ?
C21 O2 C9 C8 3.6(3) . . . . ?
C21 O2 C9 C10 -176.23(16) . . . . ?
C5 C3 C1 O1 92.58(17) . . . . ?
C5 C3 C1 C2 -28.8(2) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol-water'
_chemical_compound_source        'Glycyrrhiza uralensis'
####################################################################### 
# 
# 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_exp_2695
_database_code_depnum_ccdc_archive 'CCDC 1040660'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_audit_creation_date             2014-12-17
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        '(S)-glycyfuranocoumarin A'
_chemical_formula_moiety         'C21 H20 O6'
_chemical_formula_sum            'C21 H20 O6'
_chemical_formula_weight         368.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   9.3355(3)
_cell_length_b                   9.6307(3)
_cell_length_c                   19.5386(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1756.67(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2985
_cell_measurement_temperature    100.8
_cell_measurement_theta_max      70.7787
_cell_measurement_theta_min      4.5245
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5784
_diffrn_reflns_theta_full        70.88
_diffrn_reflns_theta_max         70.88
_diffrn_reflns_theta_min         4.53
_diffrn_ambient_temperature      100.8
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -28.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000  111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00   13.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000  111.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega   20.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   50.0000  152.0000 85

#__ type_ start__ end____ width___ exp.time_
  4 omega  -15.00   56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -37.0000 -150.0000 71

#__ type_ start__ end____ width___ exp.time_
  5 omega  -31.00   48.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -37.0000  -60.0000 79

#__ type_ start__ end____ width___ exp.time_
  6 omega   96.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
  7 omega   49.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 49

#__ type_ start__ end____ width___ exp.time_
  8 omega   43.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
  9 omega   72.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  126.00  152.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega  115.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 62

#__ type_ start__ end____ width___ exp.time_
 12 omega   57.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -180.0000 88
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0147193000
_diffrn_orient_matrix_UB_12      0.0187685000
_diffrn_orient_matrix_UB_13      -0.0779402000
_diffrn_orient_matrix_UB_21      -0.1290990000
_diffrn_orient_matrix_UB_22      -0.0967275000
_diffrn_orient_matrix_UB_23      -0.0112705000
_diffrn_orient_matrix_UB_31      -0.1016366000
_diffrn_orient_matrix_UB_32      0.1262814000
_diffrn_orient_matrix_UB_33      0.0028805000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3179
_reflns_number_total             3321
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(16)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0471P)²+0.3385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0908
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
O2 O -0.40753(12) -0.96719(13) -0.09310(6) 0.0154(3) Uani 1 1 d . . .
O6 O -1.03984(14) -0.73089(14) -0.32993(7) 0.0230(3) Uani 1 1 d . . .
H6 H -1.1112 -0.7840 -0.3297 0.034 Uiso 1 1 calc R . .
O4 O -0.74300(13) -0.86040(14) 0.08173(6) 0.0202(3) Uani 1 1 d . . .
O3 O -0.46191(14) -0.94967(13) -0.20219(6) 0.0206(3) Uani 1 1 d . . .
C6 C -0.60892(19) -0.90458(18) 0.06660(9) 0.0156(3) Uani 1 1 d . . .
O1 O -0.27630(13) -1.04530(13) 0.13383(6) 0.0166(3) Uani 1 1 d . . .
C5 C -0.5088(2) -0.94413(18) 0.11488(8) 0.0166(4) Uani 1 1 d . . .
H5 H -0.5286 -0.9386 0.1625 0.020 Uiso 1 1 calc R . .
C18 C -0.81510(19) -0.70299(18) -0.27726(9) 0.0166(4) Uani 1 1 d . . .
H18 H -0.7926 -0.6342 -0.3104 0.020 Uiso 1 1 calc R . .
O5 O -0.58831(13) -0.67164(13) -0.22076(7) 0.0178(3) Uani 1 1 d . . .
H5A H -0.5848 -0.6049 -0.2484 0.027 Uiso 1 1 calc R . .
C17 C -0.71615(18) -0.73681(18) -0.22681(9) 0.0140(3) Uani 1 1 d . . .
C20 C -0.98042(19) -0.87141(19) -0.23135(9) 0.0186(4) Uani 1 1 d . . .
H20 H -1.0709 -0.9165 -0.2325 0.022 Uiso 1 1 calc R . .
C7 C -0.5758(2) -0.90951(17) -0.00456(9) 0.0142(3) Uani 1 1 d . . .
C8 C -0.44028(19) -0.95745(17) -0.02432(9) 0.0137(3) Uani 1 1 d . . .
C1 C -0.14447(18) -1.0573(2) 0.09316(9) 0.0177(4) Uani 1 1 d . . .
H1 H -0.0890 -0.9692 0.0985 0.021 Uiso 1 1 calc R . .
C10 C -0.64280(19) -0.87750(17) -0.12407(9) 0.0153(4) Uani 1 1 d . . .
C9 C -0.67567(19) -0.86935(17) -0.05643(9) 0.0145(3) Uani 1 1 d . . .
H9 H -0.7674 -0.8361 -0.0433 0.017 Uiso 1 1 calc R . .
C2 C -0.19283(19) -1.06895(18) 0.01692(9) 0.0145(4) Uani 1 1 d . . .
C11 C -0.5032(2) -0.93157(17) -0.14401(9) 0.0156(4) Uani 1 1 d . . .
C21 C -0.87966(19) -0.90590(18) -0.18183(9) 0.0170(4) Uani 1 1 d . . .
H21 H -0.9023 -0.9759 -0.1493 0.020 Uiso 1 1 calc R . .
C4 C -0.37826(19) -0.99214(18) 0.09083(9) 0.0154(4) Uani 1 1 d . . .
C15 C -0.7827(2) -0.8632(2) 0.15283(9) 0.0230(4) Uani 1 1 d . . .
H15A H -0.7205 -0.8001 0.1787 0.035 Uiso 1 1 calc R . .
H15B H -0.7720 -0.9578 0.1706 0.035 Uiso 1 1 calc R . .
H15C H -0.8826 -0.8336 0.1577 0.035 Uiso 1 1 calc R . .
C3 C -0.33832(18) -0.99942(17) 0.02267(9) 0.0139(3) Uani 1 1 d . . .
C12 C -0.0568(2) -1.1740(2) 0.12316(10) 0.0307(5) Uani 1 1 d . . .
H12A H -0.1105 -1.2611 0.1197 0.046 Uiso 1 1 calc R . .
H12B H -0.0363 -1.1541 0.1714 0.046 Uiso 1 1 calc R . .
H12C H 0.0334 -1.1826 0.0979 0.046 Uiso 1 1 calc R . .
C14 C -0.08658(18) -0.9922(2) -0.02913(9) 0.0200(4) Uani 1 1 d . . .
H14A H 0.0078 -1.0361 -0.0256 0.030 Uiso 1 1 calc R . .
H14B H -0.0797 -0.8950 -0.0146 0.030 Uiso 1 1 calc R . .
H14C H -0.1198 -0.9962 -0.0767 0.030 Uiso 1 1 calc R . .
C16 C -0.74644(18) -0.84092(18) -0.17840(9) 0.0144(3) Uani 1 1 d . . .
C13 C -0.2104(2) -1.21971(19) -0.00744(10) 0.0208(4) Uani 1 1 d . . .
H13A H -0.2745 -1.2694 0.0238 0.031 Uiso 1 1 calc R . .
H13B H -0.1166 -1.2655 -0.0080 0.031 Uiso 1 1 calc R . .
H13C H -0.2511 -1.2204 -0.0537 0.031 Uiso 1 1 calc R . .
C19 C -0.94650(18) -0.76968(18) -0.27922(9) 0.0168(4) 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
O2 C8 1.381(2) . ?
O2 C11 1.380(2) . ?
O6 H6 0.8400 . ?
O6 C19 1.371(2) . ?
O4 C6 1.355(2) . ?
O4 C15 1.438(2) . ?
O3 C11 1.213(2) . ?
C6 C5 1.382(2) . ?
C6 C7 1.425(2) . ?
O1 C1 1.470(2) . ?
O1 C4 1.369(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.385(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.390(2) . ?
C18 C19 1.385(2) . ?
O5 H5A 0.8400 . ?
O5 C17 1.354(2) . ?
C17 C16 1.407(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(3) . ?
C20 C19 1.391(3) . ?
C7 C8 1.401(2) . ?
C7 C9 1.430(2) . ?
C8 C3 1.383(2) . ?
C1 H1 1.0000 . ?
C1 C2 1.561(2) . ?
C1 C12 1.509(3) . ?
C10 C9 1.359(3) . ?
C10 C11 1.456(2) . ?
C10 C16 1.479(2) . ?
C9 H9 0.9500 . ?
C2 C3 1.518(2) . ?
C2 C14 1.530(2) . ?
C2 C13 1.537(2) . ?
C21 H21 0.9500 . ?
C21 C16 1.394(2) . ?
C4 C3 1.385(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 C8 122.74(13) . . ?
C19 O6 H6 109.5 . . ?
C6 O4 C15 116.29(14) . . ?
O4 C6 C5 124.25(16) . . ?
O4 C6 C7 115.07(15) . . ?
C5 C6 C7 120.68(16) . . ?
C4 O1 C1 106.25(13) . . ?
C6 C5 H5 121.5 . . ?
C6 C5 C4 117.10(16) . . ?
C4 C5 H5 121.5 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C19 C18 C17 119.97(17) . . ?
C17 O5 H5A 109.5 . . ?
C18 C17 C16 120.68(16) . . ?
O5 C17 C18 122.64(15) . . ?
O5 C17 C16 116.68(15) . . ?
C21 C20 H20 120.6 . . ?
C21 C20 C19 118.84(16) . . ?
C19 C20 H20 120.6 . . ?
C6 C7 C9 122.76(16) . . ?
C8 C7 C6 118.40(15) . . ?
C8 C7 C9 118.84(16) . . ?
O2 C8 C7 119.36(15) . . ?
O2 C8 C3 118.27(15) . . ?
C3 C8 C7 122.34(15) . . ?
O1 C1 H1 108.1 . . ?
O1 C1 C2 106.24(13) . . ?
O1 C1 C12 107.64(15) . . ?
C2 C1 H1 108.1 . . ?
C12 C1 H1 108.1 . . ?
C12 C1 C2 118.32(16) . . ?
C9 C10 C11 118.87(16) . . ?
C9 C10 C16 122.45(16) . . ?
C11 C10 C16 118.59(15) . . ?
C7 C9 H9 119.1 . . ?
C10 C9 C7 121.76(16) . . ?
C10 C9 H9 119.1 . . ?
C3 C2 C1 99.00(13) . . ?
C3 C2 C14 114.23(15) . . ?
C3 C2 C13 110.15(14) . . ?
C14 C2 C1 109.83(14) . . ?
C14 C2 C13 110.09(15) . . ?
C13 C2 C1 113.21(15) . . ?
O2 C11 C10 118.37(14) . . ?
O3 C11 O2 115.71(16) . . ?
O3 C11 C10 125.92(16) . . ?
C20 C21 H21 119.0 . . ?
C20 C21 C16 122.01(16) . . ?
C16 C21 H21 119.0 . . ?
O1 C4 C5 121.88(16) . . ?
O1 C4 C3 112.59(15) . . ?
C3 C4 C5 125.45(16) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C3 C2 134.06(16) . . ?
C8 C3 C4 116.00(16) . . ?
C4 C3 C2 109.54(15) . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C14 H14A 109.5 . . ?
C2 C14 H14B 109.5 . . ?
C2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 C16 C10 121.38(15) . . ?
C21 C16 C17 117.83(16) . . ?
C21 C16 C10 120.75(15) . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O6 C19 C18 117.15(16) . . ?
O6 C19 C20 122.21(16) . . ?
C18 C19 C20 120.64(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C8 C3 C2 -6.1(3) . . . . ?
O2 C8 C3 C4 -177.82(15) . . . . ?
O4 C6 C5 C4 177.46(16) . . . . ?
O4 C6 C7 C8 -178.45(15) . . . . ?
O4 C6 C7 C9 0.7(2) . . . . ?
C6 C5 C4 O1 -174.18(16) . . . . ?
C6 C5 C4 C3 2.3(3) . . . . ?
C6 C7 C8 O2 177.99(15) . . . . ?
C6 C7 C8 C3 -0.2(2) . . . . ?
C6 C7 C9 C10 -178.67(16) . . . . ?
O1 C1 C2 C3 23.80(17) . . . . ?
O1 C1 C2 C14 143.72(14) . . . . ?
O1 C1 C2 C13 -92.77(17) . . . . ?
O1 C4 C3 C8 175.25(15) . . . . ?
O1 C4 C3 C2 1.53(19) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C5 C6 C7 C9 -179.84(16) . . . . ?
C5 C4 C3 C8 -1.5(3) . . . . ?
C5 C4 C3 C2 -175.20(16) . . . . ?
C18 C17 C16 C10 -179.54(16) . . . . ?
C18 C17 C16 C21 -1.6(2) . . . . ?
O5 C17 C16 C10 -0.4(2) . . . . ?
O5 C17 C16 C21 177.54(14) . . . . ?
C17 C18 C19 O6 179.52(16) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C20 C21 C16 C17 0.5(2) . . . . ?
C20 C21 C16 C10 178.51(17) . . . . ?
C7 C6 C5 C4 -1.9(3) . . . . ?
C7 C8 C3 C2 172.14(17) . . . . ?
C7 C8 C3 C4 0.4(2) . . . . ?
C8 O2 C11 O3 -177.63(15) . . . . ?
C8 O2 C11 C10 1.9(2) . . . . ?
C8 C7 C9 C10 0.5(2) . . . . ?
C1 O1 C4 C5 -168.37(15) . . . . ?
C1 O1 C4 C3 14.77(19) . . . . ?
C1 C2 C3 C8 172.15(19) . . . . ?
C1 C2 C3 C4 -15.71(17) . . . . ?
C9 C7 C8 O2 -1.2(2) . . . . ?
C9 C7 C8 C3 -179.39(16) . . . . ?
C9 C10 C11 O2 -2.6(2) . . . . ?
C9 C10 C11 O3 176.94(17) . . . . ?
C9 C10 C16 C17 121.69(19) . . . . ?
C9 C10 C16 C21 -56.2(2) . . . . ?
C11 O2 C8 C7 0.0(2) . . . . ?
C11 O2 C8 C3 178.20(15) . . . . ?
C11 C10 C9 C7 1.4(2) . . . . ?
C11 C10 C16 C17 -61.8(2) . . . . ?
C11 C10 C16 C21 120.26(18) . . . . ?
C21 C20 C19 O6 179.45(16) . . . . ?
C21 C20 C19 C18 -0.5(3) . . . . ?
C4 O1 C1 C2 -24.54(18) . . . . ?
C4 O1 C1 C12 -152.21(15) . . . . ?
C15 O4 C6 C5 -3.5(3) . . . . ?
C15 O4 C6 C7 175.97(15) . . . . ?
C12 C1 C2 C3 144.83(16) . . . . ?
C12 C1 C2 C14 -95.25(19) . . . . ?
C12 C1 C2 C13 28.3(2) . . . . ?
C14 C2 C3 C8 55.5(3) . . . . ?
C14 C2 C3 C4 -132.32(16) . . . . ?
C16 C10 C9 C7 177.87(16) . . . . ?
C16 C10 C11 O2 -179.20(15) . . . . ?
C16 C10 C11 O3 0.3(3) . . . . ?
C13 C2 C3 C8 -69.0(2) . . . . ?
C13 C2 C3 C4 103.18(16) . . . . ?
C19 C18 C17 O5 -177.48(15) . . . . ?
C19 C18 C17 C16 1.6(3) . . . . ?
C19 C20 C21 C16 0.5(3) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol-water'
_chemical_compound_source        'Glycyrrhiza uralensis'
####################################################################### 
# 
# 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_exp_3566
_database_code_depnum_ccdc_archive 'CCDC 1040681'
_audit_update_record             
;
2015-04-09 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_audit_creation_date             2015-01-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        'Glycyfuranocoumarin A'
_chemical_formula_moiety         'C21 H20 O6'
_chemical_formula_sum            'C21 H20 O6'
_chemical_formula_weight         368.37
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H20O6
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   9.33933(18)
_cell_length_b                   19.7504(4)
_cell_length_c                   9.61969(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1774.40(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13045
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      73.8230
_cell_measurement_theta_min      4.4440
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       lamellar
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            29236
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.758
_diffrn_reflns_theta_min         4.477
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -120.00  -37.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -19.0000 -150.0000 83

#__ type_ start__ end____ width___ exp.time_
  2 omega  -34.00    5.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -19.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega    7.00   53.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6056  -99.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega   65.00   98.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -45.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
  5 omega  117.00  172.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   45.0000   30.0000 55

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00   84.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00  135.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -77.0000  120.0000 95

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00   87.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
  9 omega -115.00  -11.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -57.0000  120.0000 104

#__ type_ start__ end____ width___ exp.time_
 10 omega -115.00  -11.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -57.0000    0.0000 104

#__ type_ start__ end____ width___ exp.time_
 11 omega   80.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   45.0000  -30.0000 98

#__ type_ start__ end____ width___ exp.time_
 12 omega   77.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   30.0000 -150.0000 101

#__ type_ start__ end____ width___ exp.time_
 13 omega   77.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   30.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
 14 omega   23.00  109.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -94.0000  -60.0000 86

#__ type_ start__ end____ width___ exp.time_
 15 omega   55.00  129.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6056 -178.0000   30.0000 74

#__ type_ start__ end____ width___ exp.time_
 16 omega   57.00  131.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6056  178.0000  -90.0000 74

#__ type_ start__ end____ width___ exp.time_
 17 omega   77.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000  -90.0000 101

#__ type_ start__ end____ width___ exp.time_
 18 omega   77.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
 19 omega   80.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   45.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
 20 omega   23.00  109.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -94.0000   60.0000 86

#__ type_ start__ end____ width___ exp.time_
 21 omega -119.00   -7.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -77.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
 22 omega -119.00   -7.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -77.0000   60.0000 112

#__ type_ start__ end____ width___ exp.time_
 23 omega   74.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000  -30.0000 104

#__ type_ start__ end____ width___ exp.time_
 24 omega   77.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000   60.0000 101

#__ type_ start__ end____ width___ exp.time_
 25 omega   77.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
 26 omega   74.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000 -150.0000 104

#__ type_ start__ end____ width___ exp.time_
 27 omega  -50.00   35.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056   38.0000   30.0000 85

#__ type_ start__ end____ width___ exp.time_
 28 omega -119.00   -7.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -77.0000  -30.0000 112

#__ type_ start__ end____ width___ exp.time_
 29 omega   23.00  109.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -94.0000 -120.0000 86

#__ type_ start__ end____ width___ exp.time_
 30 omega   77.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000  150.0000 101

#__ type_ start__ end____ width___ exp.time_
 31 omega   74.00  167.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000 -180.0000 93

#__ type_ start__ end____ width___ exp.time_
 32 omega   74.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000   90.0000 104
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0503187000
_diffrn_orient_matrix_UB_12      0.0491283000
_diffrn_orient_matrix_UB_13      0.1145403000
_diffrn_orient_matrix_UB_21      -0.1072844000
_diffrn_orient_matrix_UB_22      -0.0534591000
_diffrn_orient_matrix_UB_23      0.0521085000
_diffrn_orient_matrix_UB_31      0.1148472000
_diffrn_orient_matrix_UB_32      -0.0284219000
_diffrn_orient_matrix_UB_33      0.0990588000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3367
_reflns_number_total             3570
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1382 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(6)
_refine_ls_extinction_coef       0.0036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3570
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.2077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0763
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H) groups
2. Others
 Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C7A)=Sof(H7A)=Sof(C19A)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(C7)=Sof(H7)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C20)=Sof(H20A)=
 Sof(H20B)=Sof(H20C)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C7(H7), C7A(H7A)
3.b Me refined with riding coordinates:
 C21(H21A,H21B,H21C), C21(H21D,H21E,H21F)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C14(H14), C16(H16), C17(H17)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C19A(H19D,H19E,
 H19F), C20A(H20D,H20E,H20F)
3.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8816(2) 0.62879(9) 0.36509(18) 0.0293(4) Uani 1 1 d . . . . .
C2 C 0.9134(2) 0.69544(9) 0.37732(19) 0.0297(4) Uani 1 1 d . . . . .
H2 H 1.0042 0.7082 0.4133 0.036 Uiso 1 1 calc R . . . .
C3 C 0.8146(2) 0.74701(9) 0.33788(18) 0.0284(4) Uani 1 1 d . . . . .
C4 C 0.8465(2) 0.81724(9) 0.34707(19) 0.0310(4) Uani 1 1 d . . . . .
C5 C 0.7479(2) 0.86530(9) 0.3061(2) 0.0318(4) Uani 1 1 d . . . . .
H5 H 0.7672 0.9124 0.3143 0.038 Uiso 1 1 calc R . . . .
C6 C 0.6194(2) 0.84179(9) 0.2525(2) 0.0313(4) Uani 1 1 d . . . . .
C7 C 0.3879(3) 0.84520(15) 0.1910(4) 0.0332(10) Uani 0.651(8) 1 d . . P A 1
H7 H 0.3372 0.8490 0.2822 0.040 Uiso 0.651(8) 1 calc R . P A 1
C8 C 0.4352(2) 0.76940(9) 0.1711(2) 0.0321(4) Uani 1 1 d . . . . .
C9 C 0.5809(2) 0.77441(10) 0.2411(2) 0.0311(4) Uani 1 1 d . . . . .
C10 C 0.6811(2) 0.72768(9) 0.28583(19) 0.0282(4) Uani 1 1 d . . . . .
C11 C 0.7433(2) 0.60919(9) 0.30926(18) 0.0303(4) Uani 1 1 d . . . . .
C12 C 0.9865(2) 0.57489(9) 0.40091(19) 0.0299(4) Uani 1 1 d . . . . .
C13 C 0.95901(19) 0.52755(9) 0.50570(19) 0.0288(4) Uani 1 1 d . . . . .
C14 C 1.0594(2) 0.47835(10) 0.5397(2) 0.0326(4) Uani 1 1 d . . . . .
H14 H 1.0385 0.4457 0.6093 0.039 Uiso 1 1 calc R . . . .
C15 C 1.1898(2) 0.47714(10) 0.47178(19) 0.0328(4) Uani 1 1 d . . . . .
C16 C 1.2207(2) 0.52371(10) 0.3682(2) 0.0360(4) Uani 1 1 d . . . . .
H16 H 1.3102 0.5226 0.3213 0.043 Uiso 1 1 calc R . . . .
C17 C 1.1183(2) 0.57209(10) 0.3340(2) 0.0335(4) Uani 1 1 d . . . . .
H17 H 1.1390 0.6041 0.2630 0.040 Uiso 1 1 calc R . . . .
C18 C 1.0201(2) 0.90203(10) 0.3955(3) 0.0447(5) Uani 1 1 d . . . . .
H18A H 1.0107 0.9203 0.3013 0.067 Uiso 1 1 calc GR . . . .
H18B H 1.1197 0.9062 0.4263 0.067 Uiso 1 1 calc GR . . . .
H18C H 0.9578 0.9274 0.4588 0.067 Uiso 1 1 calc GR . . . .
C19 C 0.4552(5) 0.7467(3) 0.0269(4) 0.0416(10) Uani 0.651(8) 1 d . . P A 1
H19A H 0.3625 0.7459 -0.0207 0.062 Uiso 0.651(8) 1 calc GR . P A 1
H19B H 0.4966 0.7011 0.0266 0.062 Uiso 0.651(8) 1 calc GR . P A 1
H19C H 0.5199 0.7779 -0.0214 0.062 Uiso 0.651(8) 1 calc GR . P A 1
C20 C 0.3299(6) 0.7239(3) 0.2518(6) 0.0389(11) Uani 0.651(8) 1 d . . P A 1
H20A H 0.3287 0.7375 0.3498 0.058 Uiso 0.651(8) 1 calc GR . P A 1
H20B H 0.3604 0.6766 0.2443 0.058 Uiso 0.651(8) 1 calc GR . P A 1
H20C H 0.2336 0.7289 0.2125 0.058 Uiso 0.651(8) 1 calc GR . P A 1
C21 C 0.2938(3) 0.87566(12) 0.0806(3) 0.0588(7) Uani 1 1 d . . . . .
H21A H 0.2048 0.8496 0.0737 0.088 Uiso 0.651(8) 1 calc R . P A 1
H21B H 0.2716 0.9227 0.1050 0.088 Uiso 0.651(8) 1 calc R . P A 1
H21C H 0.3438 0.8745 -0.0090 0.088 Uiso 0.651(8) 1 calc R . P A 1
H21D H 0.2317 0.8495 0.0185 0.088 Uiso 0.349(8) 1 calc R . P A 2
H21E H 0.2464 0.8815 0.1706 0.088 Uiso 0.349(8) 1 calc R . P A 2
H21F H 0.3127 0.9201 0.0394 0.088 Uiso 0.349(8) 1 calc R . P A 2
C7A C 0.4221(7) 0.8415(3) 0.0992(8) 0.0347(19) Uani 0.349(8) 1 d . . P A 2
H7A H 0.4712 0.8389 0.0070 0.042 Uiso 0.349(8) 1 calc R . P A 2
C19A C 0.4219(11) 0.7164(4) 0.0407(9) 0.045(2) Uani 0.349(8) 1 d . . P A 2
H19D H 0.3338 0.7257 -0.0112 0.067 Uiso 0.349(8) 1 calc GR . P A 2
H19E H 0.4193 0.6699 0.0763 0.067 Uiso 0.349(8) 1 calc GR . P A 2
H19F H 0.5046 0.7219 -0.0209 0.067 Uiso 0.349(8) 1 calc GR . P A 2
C20A C 0.3196(11) 0.7543(6) 0.2697(11) 0.046(2) Uani 0.349(8) 1 d . . P A 2
H20D H 0.3113 0.7913 0.3370 0.069 Uiso 0.349(8) 1 calc GR . P A 2
H20E H 0.3412 0.7120 0.3188 0.069 Uiso 0.349(8) 1 calc GR . P A 2
H20F H 0.2291 0.7494 0.2191 0.069 Uiso 0.349(8) 1 calc GR . P A 2
O1 O 0.51901(14) 0.88471(7) 0.19903(16) 0.0360(3) Uani 1 1 d . . . . .
O2 O 0.64845(14) 0.65980(6) 0.27372(14) 0.0318(3) Uani 1 1 d . . . . .
O3 O 0.70180(17) 0.55172(6) 0.28959(15) 0.0401(3) Uani 1 1 d . . . . .
O4 O 0.97897(15) 0.83191(7) 0.39578(16) 0.0397(3) Uani 1 1 d . . . . .
O5 O 0.83178(14) 0.53255(7) 0.57244(14) 0.0351(3) Uani 1 1 d . . . . .
H5A H 0.8283 0.5038 0.6367 0.053 Uiso 1 1 calc GR . . . .
O6 O 1.28555(16) 0.42834(8) 0.51183(16) 0.0441(4) Uani 1 1 d . . . . .
H6 H 1.3574 0.4294 0.4593 0.066 Uiso 1 1 calc GR . . . .


_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 1.355(2) . ?
C1 C11 1.452(3) . ?
C1 C12 1.487(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.425(3) . ?
C3 C4 1.421(2) . ?
C3 C10 1.397(3) . ?
C4 C5 1.380(3) . ?
C4 O4 1.354(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(3) . ?
C6 C9 1.383(3) . ?
C6 O1 1.365(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.572(4) . ?
C7 C21 1.505(4) . ?
C7 O1 1.454(3) . ?
C8 C9 1.522(3) . ?
C8 C19 1.470(5) . ?
C8 C20 1.541(6) . ?
C8 C7A 1.587(6) . ?
C8 C19A 1.638(9) . ?
C8 C20A 1.468(10) . ?
C9 C10 1.383(3) . ?
C10 O2 1.380(2) . ?
C11 O2 1.378(2) . ?
C11 O3 1.214(2) . ?
C12 C13 1.399(3) . ?
C12 C17 1.390(3) . ?
C13 C14 1.389(3) . ?
C13 O5 1.354(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(3) . ?
C15 C16 1.387(3) . ?
C15 O6 1.370(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(3) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 O4 1.437(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 H21D 0.9800 . ?
C21 H21E 0.9800 . ?
C21 H21F 0.9800 . ?
C21 C7A 1.387(6) . ?
C7A H7A 1.0000 . ?
C7A O1 1.571(6) . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
O5 H5A 0.8400 . ?
O6 H6 0.8400 . ?

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 C11 119.10(17) . . ?
C2 C1 C12 122.09(17) . . ?
C11 C1 C12 118.75(16) . . ?
C1 C2 H2 119.0 . . ?
C1 C2 C3 121.97(18) . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 123.03(18) . . ?
C10 C3 C2 118.54(16) . . ?
C10 C3 C4 118.42(16) . . ?
C5 C4 C3 120.91(17) . . ?
O4 C4 C3 114.95(16) . . ?
O4 C4 C5 124.13(16) . . ?
C4 C5 H5 121.5 . . ?
C4 C5 C6 116.96(17) . . ?
C6 C5 H5 121.5 . . ?
C9 C6 C5 125.23(18) . . ?
O1 C6 C5 121.80(17) . . ?
O1 C6 C9 112.91(16) . . ?
C8 C7 H7 108.2 . . ?
C21 C7 H7 108.2 . . ?
C21 C7 C8 117.3(3) . . ?
O1 C7 H7 108.2 . . ?
O1 C7 C8 106.3(2) . . ?
O1 C7 C21 108.3(2) . . ?
C9 C8 C7 97.76(17) . . ?
C9 C8 C20 112.7(2) . . ?
C9 C8 C7A 101.7(2) . . ?
C9 C8 C19A 116.6(4) . . ?
C19 C8 C7 116.2(3) . . ?
C19 C8 C9 108.9(2) . . ?
C19 C8 C20 112.2(3) . . ?
C20 C8 C7 108.3(2) . . ?
C7A C8 C19A 103.5(4) . . ?
C20A C8 C9 112.6(4) . . ?
C20A C8 C7A 114.1(5) . . ?
C20A C8 C19A 108.0(5) . . ?
C6 C9 C8 109.28(16) . . ?
C10 C9 C6 116.21(17) . . ?
C10 C9 C8 134.39(17) . . ?
C9 C10 C3 122.21(16) . . ?
O2 C10 C3 119.53(16) . . ?
O2 C10 C9 118.22(16) . . ?
O2 C11 C1 118.04(15) . . ?
O3 C11 C1 126.21(18) . . ?
O3 C11 O2 115.75(17) . . ?
C13 C12 C1 121.65(17) . . ?
C17 C12 C1 120.28(17) . . ?
C17 C12 C13 118.02(17) . . ?
C14 C13 C12 120.89(17) . . ?
O5 C13 C12 117.00(16) . . ?
O5 C13 C14 122.11(16) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.70(18) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.75(17) . . ?
O6 C15 C14 117.02(17) . . ?
O6 C15 C16 122.23(18) . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.87(18) . . ?
C17 C16 H16 120.6 . . ?
C12 C17 C16 121.75(18) . . ?
C12 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C8 C20 H20A 109.5 . . ?
C8 C20 H20B 109.5 . . ?
C8 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 C21 H21A 109.5 . . ?
C7 C21 H21B 109.5 . . ?
C7 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H21D C21 H21E 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
C7A C21 H21D 109.5 . . ?
C7A C21 H21E 109.5 . . ?
C7A C21 H21F 109.5 . . ?
C8 C7A H7A 107.8 . . ?
C21 C7A C8 124.0(5) . . ?
C21 C7A H7A 107.8 . . ?
C21 C7A O1 108.2(4) . . ?
O1 C7A C8 100.2(4) . . ?
O1 C7A H7A 107.8 . . ?
C8 C19A H19D 109.5 . . ?
C8 C19A H19E 109.5 . . ?
C8 C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C8 C20A H20D 109.5 . . ?
C8 C20A H20E 109.5 . . ?
C8 C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C6 O1 C7 105.37(16) . . ?
C6 O1 C7A 106.8(2) . . ?
C11 O2 C10 122.81(14) . . ?
C4 O4 C18 116.72(15) . . ?
C13 O5 H5A 109.5 . . ?
C15 O6 H6 109.5 . . ?

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
C18 H18B O5 0.98 2.32 3.200(2) 148.8 3_566
O5 H5A O3 0.84 1.86 2.6893(18) 171.3 2_665
O6 H6 O1 0.84 2.11 2.862(2) 149.5 4_745

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/water'
_chemical_compound_source        'Glycyrrhiza uralensis'
