# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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. 
# 
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data_1215-2
_database_code_depnum_ccdc_archive 'CCDC 1888891'
loop_
_audit_author_name
_audit_author_address
'Xuexiu Xia'
;Soochow University
China
;
_audit_update_record             
;
2019-01-05 deposited with the CCDC.	2019-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 O3'
_chemical_formula_weight         254.27

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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   31.6601(8)
_cell_length_b                   5.7080(2)
_cell_length_c                   15.2031(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.639(2)
_cell_angle_gamma                90
_cell_volume                     2535.75(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      68.19
_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    ?
_exptl_crystal_F_000             1110
_exptl_transmission_factor_min   0.6483
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.40
_exptl_absorpt_coefficient_mu    ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      120(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            21056
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.025
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4614
_reflns_number_gt                4333
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.991

_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-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0728P)²+1.9830P] 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 1815 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(8)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4614
_refine_ls_number_parameters     345
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O2 O 0.40580(8) 0.8631(4) 0.01779(15) 0.0294(5) Uani 1 1 d . . . . .
O1 O 0.39888(7) 0.8690(4) 0.28330(14) 0.0286(5) Uani 1 1 d . . . . .
O5 O 0.40511(8) 0.3763(4) 0.51799(15) 0.0298(5) Uani 1 1 d . . . . .
O4 O 0.39683(8) 0.3718(4) 0.78157(15) 0.0311(5) Uani 1 1 d . . . . .
O3 O 0.32885(8) 1.1903(4) 0.20816(17) 0.0342(5) Uani 1 1 d . . . . .
O6 O 0.32677(9) 0.6815(5) 0.7323(2) 0.0438(6) Uani 1 1 d . . . . .
C2 C 0.42650(10) 0.6779(6) 0.0750(2) 0.0234(6) Uani 1 1 d . . . . .
C18 C 0.42467(10) 0.1875(6) 0.5742(2) 0.0242(6) Uani 1 1 d . . . . .
C19 C 0.45144(11) 0.0214(6) 0.5533(2) 0.0295(7) Uani 1 1 d . . . . .
H19 H 0.4574 0.0350 0.4969 0.035 Uiso 1 1 calc R U . . .
C23 C 0.41536(10) 0.1666(6) 0.6571(2) 0.0231(6) Uani 1 1 d . . . . .
C27 C 0.26753(11) 0.4113(6) 0.6462(2) 0.0287(7) Uani 1 1 d . . . . .
C1 C 0.41951(10) 0.6652(6) 0.1609(2) 0.0230(6) Uani 1 1 d . . . . .
C11 C 0.26988(11) 0.9069(6) 0.1414(2) 0.0267(7) Uani 1 1 d . . . . .
C3 C 0.45221(11) 0.5082(6) 0.0531(2) 0.0295(7) Uani 1 1 d . . . . .
H3 H 0.4566 0.5160 -0.0052 0.035 Uiso 1 1 calc R U . . .
C12 C 0.24011(11) 1.0660(7) 0.0778(2) 0.0339(7) Uani 1 1 d . . . . .
H12 H 0.2512 1.2132 0.0668 0.041 Uiso 1 1 calc R U . . .
C22 C 0.43318(10) -0.0244(6) 0.7164(2) 0.0260(6) Uani 1 1 d . . . . .
H22 H 0.4266 -0.0418 0.7720 0.031 Uiso 1 1 calc R U . . .
C24 C 0.38883(10) 0.3513(6) 0.6823(2) 0.0245(6) Uani 1 1 d . . . . .
H24 H 0.3851 0.5024 0.6469 0.029 Uiso 1 1 calc R U . . .
C5 C 0.46450(10) 0.3097(6) 0.2008(2) 0.0304(7) Uani 1 1 d . . . . .
H5 H 0.4774 0.1839 0.2437 0.036 Uiso 1 1 calc R U . . .
C21 C 0.46024(10) -0.1904(6) 0.6967(2) 0.0295(7) Uani 1 1 d . . . . .
H21 H 0.4722 -0.3195 0.7383 0.035 Uiso 1 1 calc R U . . .
C8 C 0.39353(10) 0.8538(6) 0.1854(2) 0.0248(6) Uani 1 1 d . . . . .
H8 H 0.3914 1.0064 0.1516 0.030 Uiso 1 1 calc R U . . .
C6L C 0.43836(10) 0.4788(6) 0.2219(2) 0.0277(7) Uani 1 1 d . . . . .
H6L H 0.4333 0.4666 0.2794 0.033 Uiso 1 1 calc R U . . .
C28 C 0.23410(11) 0.5722(7) 0.6425(2) 0.0330(7) Uani 1 1 d . . . . .
H28 H 0.2427 0.7162 0.6761 0.040 Uiso 1 1 calc R U . . .
C4 C 0.47156(11) 0.3258(6) 0.1171(2) 0.0319(7) Uani 1 1 d . . . . .
H4 H 0.4898 0.2116 0.1028 0.038 Uiso 1 1 calc R U . . .
C31 C 0.20858(13) 0.1521(7) 0.5454(2) 0.0388(8) Uani 1 1 d . . . . .
H31 H 0.1998 0.0076 0.5123 0.047 Uiso 1 1 calc R U . . .
C20 C 0.46952(11) -0.1650(6) 0.6153(3) 0.0323(7) Uani 1 1 d . . . . .
H20 H 0.4885 -0.2763 0.6017 0.039 Uiso 1 1 calc R U . . .
C26 C 0.31584(12) 0.4814(6) 0.7021(2) 0.0342(8) Uani 1 1 d . . . . .
C13 C 0.19410(12) 1.0087(7) 0.0306(3) 0.0383(8) Uani 1 1 d . . . . .
H13 H 0.1739 1.1156 -0.0136 0.046 Uiso 1 1 calc R U . . .
C16 C 0.25356(11) 0.6916(7) 0.1579(2) 0.0302(7) Uani 1 1 d . . . . .
H16 H 0.2739 0.5814 0.2001 0.036 Uiso 1 1 calc R U . . .
C10 C 0.31837(11) 0.9854(6) 0.1912(2) 0.0282(7) Uani 1 1 d . . . . .
C9 C 0.35499(10) 0.7995(6) 0.2158(2) 0.0271(7) Uani 1 1 d . . . . .
H9 H 0.3456 0.6320 0.2155 0.033 Uiso 1 1 calc R U . . .
C7 C 0.41483(13) 0.8934(7) -0.0668(2) 0.0350(8) Uani 1 1 d . . . . .
H7A H 0.4480 0.8960 -0.0501 0.053 Uiso 1 1 calc R U . . .
H7B H 0.4015 1.0415 -0.0975 0.053 Uiso 1 1 calc R U . . .
H7C H 0.4012 0.7633 -0.1107 0.053 Uiso 1 1 calc R U . . .
C15 C 0.20729(12) 0.6393(7) 0.1122(3) 0.0374(8) Uani 1 1 d . . . . .
H15 H 0.1959 0.4950 0.1251 0.045 Uiso 1 1 calc R U . . .
C17 C 0.41577(13) 0.4126(7) 0.4354(2) 0.0370(8) Uani 1 1 d . . . . .
H17A H 0.4490 0.4264 0.4549 0.056 Uiso 1 1 calc R U . . .
H17B H 0.4010 0.5566 0.4030 0.056 Uiso 1 1 calc R U . . .
H17C H 0.4046 0.2794 0.3919 0.056 Uiso 1 1 calc R U . . .
C25 C 0.35281(11) 0.2979(6) 0.7191(2) 0.0314(7) Uani 1 1 d . . . . .
H25 H 0.3444 0.1299 0.7217 0.038 Uiso 1 1 calc R U . . .
C32 C 0.25451(12) 0.1995(7) 0.5979(2) 0.0345(8) Uani 1 1 d . . . . .
H32 H 0.2771 0.0870 0.6007 0.041 Uiso 1 1 calc R U . . .
C29 C 0.18837(12) 0.5254(7) 0.5905(3) 0.0383(8) Uani 1 1 d . . . . .
H29 H 0.1657 0.6369 0.5885 0.046 Uiso 1 1 calc R U . . .
C14 C 0.17779(12) 0.7949(7) 0.0482(3) 0.0383(8) Uani 1 1 d . . . . .
H14 H 0.1464 0.7559 0.0162 0.046 Uiso 1 1 calc R U . . .
C30 C 0.17556(12) 0.3164(7) 0.5414(3) 0.0385(8) Uani 1 1 d . . . . .
H30 H 0.1442 0.2852 0.5049 0.046 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
O2 C2 1.365(4) . ?
O2 C7 1.431(4) . ?
O1 C9 1.430(4) . ?
O1 C8 1.435(3) . ?
O5 C18 1.367(4) . ?
O5 C17 1.435(4) . ?
O4 C25 1.415(4) . ?
O4 C24 1.435(4) . ?
O3 C10 1.216(4) . ?
O6 C26 1.230(5) . ?
C2 C3 1.385(5) . ?
C2 C1 1.409(4) . ?
C18 C19 1.387(5) . ?
C18 C23 1.406(4) . ?
C19 C20 1.390(5) . ?
C19 H19 0.9500 . ?
C23 C22 1.389(4) . ?
C23 C24 1.487(4) . ?
C27 C28 1.386(5) . ?
C27 C32 1.392(5) . ?
C27 C26 1.490(5) . ?
C1 C6L 1.386(4) . ?
C1 C8 1.486(4) . ?
C11 C16 1.393(5) . ?
C11 C12 1.395(5) . ?
C11 C10 1.496(4) . ?
C3 C4 1.395(5) . ?
C3 H3 0.9500 . ?
C12 C13 1.393(5) . ?
C12 H12 0.9500 . ?
C22 C21 1.385(5) . ?
C22 H22 0.9500 . ?
C24 C25 1.482(4) . ?
C24 H24 1.0000 . ?
C5 C4 1.377(5) . ?
C5 C6L 1.387(5) . ?
C5 H5 0.9500 . ?
C21 C20 1.384(5) . ?
C21 H21 0.9500 . ?
C8 C9 1.494(4) . ?
C8 H8 1.0000 . ?
C6L H6L 0.9500 . ?
C28 C29 1.383(5) . ?
C28 H28 0.9500 . ?
C4 H4 0.9500 . ?
C31 C30 1.388(5) . ?
C31 C32 1.390(5) . ?
C31 H31 0.9500 . ?
C20 H20 0.9500 . ?
C26 C25 1.517(5) . ?
C13 C14 1.390(6) . ?
C13 H13 0.9500 . ?
C16 C15 1.391(5) . ?
C16 H16 0.9500 . ?
C10 C9 1.509(4) . ?
C9 H9 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C15 C14 1.381(5) . ?
C15 H15 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C25 H25 1.0000 . ?
C32 H32 0.9500 . ?
C29 C30 1.383(6) . ?
C29 H29 0.9500 . ?
C14 H14 0.9500 . ?
C30 H30 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C7 116.9(2) . . ?
C9 O1 C8 62.89(19) . . ?
C18 O5 C17 117.3(3) . . ?
C25 O4 C24 62.6(2) . . ?
O2 C2 C3 124.8(3) . . ?
O2 C2 C1 115.0(3) . . ?
C3 C2 C1 120.2(3) . . ?
O5 C18 C19 124.5(3) . . ?
O5 C18 C23 115.2(3) . . ?
C19 C18 C23 120.3(3) . . ?
C18 C19 C20 119.8(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C22 C23 C18 118.4(3) . . ?
C22 C23 C24 121.2(3) . . ?
C18 C23 C24 120.4(3) . . ?
C28 C27 C32 119.2(3) . . ?
C28 C27 C26 116.5(3) . . ?
C32 C27 C26 124.3(3) . . ?
C6L C1 C2 118.6(3) . . ?
C6L C1 C8 121.7(3) . . ?
C2 C1 C8 119.6(3) . . ?
C16 C11 C12 120.1(3) . . ?
C16 C11 C10 123.5(3) . . ?
C12 C11 C10 116.4(3) . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C21 C22 C23 121.8(3) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
O4 C24 C25 58.02(19) . . ?
O4 C24 C23 116.1(2) . . ?
C25 C24 C23 123.0(3) . . ?
O4 C24 H24 115.7 . . ?
C25 C24 H24 115.7 . . ?
C23 C24 H24 115.7 . . ?
C4 C5 C6L 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6L C5 H5 120.3 . . ?
C22 C21 C20 118.9(3) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
O1 C8 C1 116.6(2) . . ?
O1 C8 C9 58.37(18) . . ?
C1 C8 C9 121.6(3) . . ?
O1 C8 H8 115.9 . . ?
C1 C8 H8 115.9 . . ?
C9 C8 H8 115.9 . . ?
C5 C6L C1 121.4(3) . . ?
C5 C6L H6L 119.3 . . ?
C1 C6L H6L 119.3 . . ?
C29 C28 C27 120.7(3) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C30 C31 C32 119.8(3) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
O6 C26 C27 122.8(3) . . ?
O6 C26 C25 119.3(3) . . ?
C27 C26 C25 117.9(3) . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C16 C11 119.4(3) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?
O3 C10 C11 122.6(3) . . ?
O3 C10 C9 120.2(3) . . ?
C11 C10 C9 117.1(3) . . ?
O1 C9 C8 58.74(18) . . ?
O1 C9 C10 115.1(3) . . ?
C8 C9 C10 114.7(3) . . ?
O1 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
C10 C9 H9 118.2 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
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 . . ?
O4 C25 C24 59.33(19) . . ?
O4 C25 C26 113.8(3) . . ?
C24 C25 C26 116.7(3) . . ?
O4 C25 H25 117.9 . . ?
C24 C25 H25 117.9 . . ?
C26 C25 H25 117.9 . . ?
C31 C32 C27 120.3(3) . . ?
C31 C32 H32 119.9 . . ?
C27 C32 H32 119.9 . . ?
C28 C29 C30 120.0(3) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C29 C30 C31 120.0(3) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?

_refine_diff_density_max         0.746
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.046

