# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_664
_database_code_depnum_ccdc_archive 'CCDC 2031697'
loop_
_audit_author_name
_audit_author_address
weihongbo
;North West Agriculture and Forestry University
China
;
_audit_update_record             
;
2020-09-13 deposited with the CCDC.	2020-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 O5'
_chemical_formula_sum            'C17 H16 O5'
_chemical_formula_weight         300.30

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'

_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.
;

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

_cell_length_a                   9.5125(9)
_cell_length_b                   10.2643(10)
_cell_length_c                   14.9575(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1460.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      4.65
_cell_measurement_theta_max      72.05

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.838
_shelx_estimated_absorpt_T_min   0.850
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26596
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.226
_diffrn_reflns_theta_max         72.126
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2874
_reflns_number_gt                2643
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.999

_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.
;

_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.0728P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1047 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2874
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0817
_refine_ls_wR_factor_gt          0.0795
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_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
O1 O 0.19889(13) 0.16357(13) 0.68047(9) 0.0543(3) Uani 1 1 d . . . . .
O2 O 0.39856(16) 0.57351(13) 0.62293(11) 0.0664(4) Uani 1 1 d . . . . .
O3 O 0.43078(17) 0.51098(15) 0.41879(10) 0.0719(4) Uani 1 1 d . . . . .
O4 O 0.71907(14) 0.44182(15) 0.54945(11) 0.0650(4) Uani 1 1 d . . . . .
O5 O 0.64850(16) 0.63482(14) 0.49631(11) 0.0661(4) Uani 1 1 d . . . . .
C1 C 0.5660(2) 0.0896(2) 0.62614(15) 0.0575(5) Uani 1 1 d . . . . .
H1A H 0.647847 0.130122 0.606575 0.069 Uiso 1 1 calc R U . . .
C2 C 0.5683(3) -0.0418(2) 0.64510(15) 0.0662(6) Uani 1 1 d . . . . .
H2A H 0.651025 -0.088976 0.638079 0.079 Uiso 1 1 calc R U . . .
C3 C 0.4480(3) -0.10322(19) 0.67448(15) 0.0674(6) Uani 1 1 d . . . . .
H3A H 0.449127 -0.192196 0.686206 0.081 Uiso 1 1 calc R U . . .
C4 C 0.3264(2) -0.0329(2) 0.68645(14) 0.0597(5) Uani 1 1 d . . . . .
H4A H 0.245286 -0.073393 0.707247 0.072 Uiso 1 1 calc R U . . .
C5 C 0.32643(19) 0.09932(17) 0.66705(12) 0.0464(4) Uani 1 1 d . . . . .
C6 C 0.19615(18) 0.29552(18) 0.67251(12) 0.0452(4) Uani 1 1 d . . . . .
C7 C 0.0588(2) 0.3507(2) 0.70318(14) 0.0573(5) Uani 1 1 d . . . . .
H7A H 0.057615 0.355045 0.767958 0.069 Uiso 1 1 calc R U . . .
H7B H -0.017156 0.294007 0.684275 0.069 Uiso 1 1 calc R U . . .
C8 C 0.0362(2) 0.4851(2) 0.66519(17) 0.0683(6) Uani 1 1 d . . . . .
H8A H -0.045279 0.524573 0.693210 0.082 Uiso 1 1 calc R U . . .
H8B H 0.017996 0.478646 0.601534 0.082 Uiso 1 1 calc R U . . .
C9 C 0.1638(2) 0.5703(2) 0.68071(17) 0.0667(6) Uani 1 1 d . . . . .
H9A H 0.173732 0.586657 0.744264 0.080 Uiso 1 1 calc R U . . .
H9B H 0.149798 0.653439 0.651197 0.080 Uiso 1 1 calc R U . . .
C10 C 0.2975(2) 0.50833(18) 0.64586(12) 0.0521(4) Uani 1 1 d . . . . .
C11 C 0.30468(18) 0.36589(17) 0.64220(11) 0.0422(4) Uani 1 1 d . . . . .
C12 C 0.43995(17) 0.30528(16) 0.61006(11) 0.0406(3) Uani 1 1 d . . . . .
H12A H 0.518284 0.349529 0.639876 0.049 Uiso 1 1 calc R U . . .
C13 C 0.44430(18) 0.16264(17) 0.63560(11) 0.0433(4) Uani 1 1 d . . . . .
C14 C 0.45990(18) 0.31951(18) 0.50777(12) 0.0472(4) Uani 1 1 d . . . . .
H14A H 0.533896 0.260455 0.489094 0.057 Uiso 1 1 calc R U . . .
H14B H 0.373907 0.291871 0.478529 0.057 Uiso 1 1 calc R U . . .
C15 C 0.49594(18) 0.45385(19) 0.47514(11) 0.0485(4) Uani 1 1 d . . . . .
C16 C 0.63456(19) 0.50961(18) 0.51251(13) 0.0510(4) Uani 1 1 d . . . . .
C17 C 0.7766(3) 0.6931(2) 0.53129(19) 0.0820(7) Uani 1 1 d . . . . .
H17A H 0.778402 0.784130 0.516608 0.123 Uiso 1 1 calc R U . . .
H17B H 0.779078 0.682861 0.595063 0.123 Uiso 1 1 calc R U . . .
H17C H 0.856721 0.650767 0.505277 0.123 Uiso 1 1 calc R U . . .


_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
O1 C6 1.360(2) . ?
O1 C5 1.395(2) . ?
O2 C10 1.220(2) . ?
O3 C15 1.199(2) . ?
O4 C16 1.198(2) . ?
O5 C16 1.315(2) . ?
O5 C17 1.455(3) . ?
C1 C2 1.378(3) . ?
C1 C13 1.387(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.378(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.388(3) . ?
C4 H4A 0.9300 . ?
C5 C13 1.379(3) . ?
C6 C11 1.339(2) . ?
C6 C7 1.496(2) . ?
C7 C8 1.507(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.514(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.515(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.465(2) . ?
C11 C12 1.508(2) . ?
C12 C13 1.514(2) . ?
C12 C14 1.549(2) . ?
C12 H12A 0.9800 . ?
C14 C15 1.502(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.542(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C6 O1 C5 118.35(14) . . ?
C16 O5 C17 114.85(18) . . ?
C2 C1 C13 121.4(2) . . ?
C2 C1 H1A 119.3 . . ?
C13 C1 H1A 119.3 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C4 C3 C2 119.98(18) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C13 C5 C4 122.18(18) . . ?
C13 C5 O1 122.23(15) . . ?
C4 C5 O1 115.59(17) . . ?
C11 C6 O1 123.51(16) . . ?
C11 C6 C7 124.94(17) . . ?
O1 C6 C7 111.54(16) . . ?
C6 C7 C8 110.82(16) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C9 110.89(19) . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 C10 112.21(18) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
O2 C10 C11 120.02(17) . . ?
O2 C10 C9 121.86(17) . . ?
C11 C10 C9 118.10(17) . . ?
C6 C11 C10 119.34(16) . . ?
C6 C11 C12 122.91(16) . . ?
C10 C11 C12 117.60(16) . . ?
C11 C12 C13 109.99(14) . . ?
C11 C12 C14 112.37(14) . . ?
C13 C12 C14 109.70(14) . . ?
C11 C12 H12A 108.2 . . ?
C13 C12 H12A 108.2 . . ?
C14 C12 H12A 108.2 . . ?
C5 C13 C1 117.31(16) . . ?
C5 C13 C12 121.32(15) . . ?
C1 C13 C12 121.34(17) . . ?
C15 C14 C12 115.82(14) . . ?
C15 C14 H14A 108.3 . . ?
C12 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
C12 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
O3 C15 C14 123.99(18) . . ?
O3 C15 C16 121.01(18) . . ?
C14 C15 C16 114.70(15) . . ?
O4 C16 O5 125.81(19) . . ?
O4 C16 C15 121.69(17) . . ?
O5 C16 C15 112.47(16) . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C13 C1 C2 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C13 0.4(3) . . . . ?
C3 C4 C5 O1 179.67(18) . . . . ?
C6 O1 C5 C13 -8.1(2) . . . . ?
C6 O1 C5 C4 172.62(17) . . . . ?
C5 O1 C6 C11 8.2(3) . . . . ?
C5 O1 C6 C7 -170.77(15) . . . . ?
C11 C6 C7 C8 21.1(3) . . . . ?
O1 C6 C7 C8 -159.95(17) . . . . ?
C6 C7 C8 C9 -50.0(2) . . . . ?
C7 C8 C9 C10 54.0(3) . . . . ?
C8 C9 C10 O2 153.8(2) . . . . ?
C8 C9 C10 C11 -27.7(3) . . . . ?
O1 C6 C11 C10 -172.92(17) . . . . ?
C7 C6 C11 C10 5.9(3) . . . . ?
O1 C6 C11 C12 2.6(3) . . . . ?
C7 C6 C11 C12 -178.57(17) . . . . ?
O2 C10 C11 C6 176.08(18) . . . . ?
C9 C10 C11 C6 -2.4(3) . . . . ?
O2 C10 C11 C12 0.4(3) . . . . ?
C9 C10 C11 C12 -178.16(17) . . . . ?
C6 C11 C12 C13 -11.9(2) . . . . ?
C10 C11 C12 C13 163.62(15) . . . . ?
C6 C11 C12 C14 110.59(19) . . . . ?
C10 C11 C12 C14 -73.9(2) . . . . ?
C4 C5 C13 C1 -1.8(3) . . . . ?
O1 C5 C13 C1 179.00(17) . . . . ?
C4 C5 C13 C12 176.62(17) . . . . ?
O1 C5 C13 C12 -2.6(3) . . . . ?
C2 C1 C13 C5 1.7(3) . . . . ?
C2 C1 C13 C12 -176.70(18) . . . . ?
C11 C12 C13 C5 11.7(2) . . . . ?
C14 C12 C13 C5 -112.36(17) . . . . ?
C11 C12 C13 C1 -169.94(16) . . . . ?
C14 C12 C13 C1 66.0(2) . . . . ?
C11 C12 C14 C15 72.81(19) . . . . ?
C13 C12 C14 C15 -164.50(15) . . . . ?
C12 C14 C15 O3 -125.51(19) . . . . ?
C12 C14 C15 C16 60.7(2) . . . . ?
C17 O5 C16 O4 -3.0(3) . . . . ?
C17 O5 C16 C15 179.11(17) . . . . ?
O3 C15 C16 O4 -159.73(19) . . . . ?
C14 C15 C16 O4 14.3(2) . . . . ?
O3 C15 C16 O5 18.2(2) . . . . ?
C14 C15 C16 O5 -167.78(16) . . . . ?

_refine_diff_density_max         0.136
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.028



