# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_mo_xlb301_0m
_database_code_depnum_ccdc_archive 'CCDC 1917425'
loop_
_audit_author_name
_audit_author_address
'Xiaonian Li'
;Yunnan University
China
;
_audit_update_record             
;
2019-05-21 deposited with the CCDC.	2020-01-10 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         'C18 H16 O4'
_chemical_formula_sum            'C18 H16 O4'
_chemical_formula_weight         296.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   9.7263(8)
_cell_length_b                   11.8883(10)
_cell_length_c                   24.935(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2883.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      30.97

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   0.4903
_exptl_transmission_factor_max   0.5649
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.360
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30553
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.633
_diffrn_reflns_theta_max         31.234
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4416
_reflns_number_gt                3759
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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_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)+(0.0593P)²+1.2533P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4416
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.94283(8) 0.60424(6) 0.45593(3) 0.01798(17) Uani 1 1 d . . . . .
H1 H 0.9348(16) 0.5337(14) 0.4411(6) 0.027 Uiso 1 1 d . U . . .
O2 O 0.40655(9) 0.10059(7) 0.59176(3) 0.02113(18) Uani 1 1 d . . . . .
O3 O 0.30506(9) 0.62989(7) 0.72038(3) 0.02221(18) Uani 1 1 d . . . . .
O4 O 0.40319(8) 0.79160(6) 0.69344(3) 0.01724(17) Uani 1 1 d . . . . .
C1 C 0.84883(10) 0.61846(8) 0.49553(4) 0.01313(19) Uani 1 1 d . . . . .
C2 C 0.76629(11) 0.53050(8) 0.51404(4) 0.01487(19) Uani 1 1 d . . . . .
H16 H 0.7763 0.4574 0.4991 0.018 Uiso 1 1 calc R U . . .
C3 C 0.66981(11) 0.54926(8) 0.55404(4) 0.0154(2) Uani 1 1 d . . . . .
H3 H 0.6141 0.4888 0.5661 0.018 Uiso 1 1 calc R U . . .
C4 C 0.65331(11) 0.65658(8) 0.57696(4) 0.01341(19) Uani 1 1 d . . . . .
C5 C 0.55665(11) 0.68712(8) 0.61941(4) 0.01385(19) Uani 1 1 d . . . . .
H6 H 0.5488 0.7658 0.6254 0.017 Uiso 1 1 calc R U . . .
C6 C 0.47646(10) 0.62362(8) 0.65165(4) 0.01292(19) Uani 1 1 d . . . . .
C7 C 0.46875(10) 0.49825(8) 0.64988(4) 0.01239(18) Uani 1 1 d . . . . .
C8 C 0.37567(11) 0.44561(9) 0.61545(4) 0.0169(2) Uani 1 1 d . . . . .
H12 H 0.3114 0.4896 0.5959 0.020 Uiso 1 1 calc R U . . .
C9 C 0.37613(11) 0.32948(9) 0.60952(4) 0.0167(2) Uani 1 1 d . . . . .
H11 H 0.3138 0.2946 0.5853 0.020 Uiso 1 1 calc R U . . .
C10 C 0.46793(10) 0.26405(8) 0.63901(4) 0.01285(18) Uani 1 1 d . . . . .
C11 C 0.47251(11) 0.14069(8) 0.62911(4) 0.01448(19) Uani 1 1 d . . . . .
C12 C 0.55981(12) 0.06674(9) 0.66413(5) 0.0209(2) Uani 1 1 d . . . . .
H2 H 0.5406 -0.0124 0.6560 0.031 Uiso 1 1 calc R U . . .
H10 H 0.5386 0.0817 0.7019 0.031 Uiso 1 1 calc R U . . .
H9 H 0.6571 0.0826 0.6574 0.031 Uiso 1 1 calc R U . . .
C13 C 0.73765(11) 0.74343(8) 0.55742(4) 0.01477(19) Uani 1 1 d . . . . .
H4 H 0.7277 0.8169 0.5719 0.018 Uiso 1 1 calc R U . . .
C14 C 0.83469(11) 0.72548(8) 0.51778(4) 0.0153(2) Uani 1 1 d . . . . .
H5 H 0.8913 0.7856 0.5058 0.018 Uiso 1 1 calc R U . . .
C15 C 0.55668(11) 0.31601(8) 0.67537(4) 0.01489(19) Uani 1 1 d . . . . .
H8 H 0.6169 0.2716 0.6966 0.018 Uiso 1 1 calc R U . . .
C16 C 0.55738(11) 0.43284(8) 0.68070(4) 0.01462(19) Uani 1 1 d . . . . .
H7 H 0.6184 0.4678 0.7054 0.018 Uiso 1 1 calc R U . . .
C17 C 0.38604(11) 0.67927(8) 0.69179(4) 0.01407(19) Uani 1 1 d . . . . .
C18 C 0.31561(11) 0.85111(9) 0.73028(4) 0.0182(2) Uani 1 1 d . . . . .
H15 H 0.2194 0.8314 0.7233 0.027 Uiso 1 1 calc R U . . .
H14 H 0.3282 0.9323 0.7255 0.027 Uiso 1 1 calc R U . . .
H13 H 0.3395 0.8302 0.7671 0.027 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 C1 1.3564(12) . ?
O1 H1 0.920(17) . ?
O2 C11 1.2274(13) . ?
O3 C17 1.2136(13) . ?
O4 C17 1.3464(12) . ?
O4 C18 1.4388(12) . ?
C1 C14 1.3948(13) . ?
C1 C2 1.3967(14) . ?
C2 C3 1.3876(14) . ?
C2 H16 0.9500 . ?
C3 C4 1.4072(13) . ?
C3 H3 0.9500 . ?
C4 C13 1.4058(14) . ?
C4 C5 1.4615(14) . ?
C5 C6 1.3506(14) . ?
C5 H6 0.9500 . ?
C6 C17 1.4878(14) . ?
C6 C7 1.4930(13) . ?
C7 C16 1.3923(14) . ?
C7 C8 1.3957(14) . ?
C8 C9 1.3885(14) . ?
C8 H12 0.9500 . ?
C9 C10 1.3940(14) . ?
C9 H11 0.9500 . ?
C10 C15 1.3959(14) . ?
C10 C11 1.4877(13) . ?
C11 C12 1.5021(15) . ?
C12 H2 0.9800 . ?
C12 H10 0.9800 . ?
C12 H9 0.9800 . ?
C13 C14 1.3833(14) . ?
C13 H4 0.9500 . ?
C14 H5 0.9500 . ?
C15 C16 1.3952(13) . ?
C15 H8 0.9500 . ?
C16 H7 0.9500 . ?
C18 H15 0.9800 . ?
C18 H14 0.9800 . ?
C18 H13 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
C1 O1 H1 110.4(10) . . ?
C17 O4 C18 115.71(8) . . ?
O1 C1 C14 118.01(9) . . ?
O1 C1 C2 122.32(9) . . ?
C14 C1 C2 119.67(9) . . ?
C3 C2 C1 120.38(9) . . ?
C3 C2 H16 119.8 . . ?
C1 C2 H16 119.8 . . ?
C2 C3 C4 120.99(9) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C13 C4 C3 117.30(9) . . ?
C13 C4 C5 116.35(9) . . ?
C3 C4 C5 126.35(9) . . ?
C6 C5 C4 131.58(9) . . ?
C6 C5 H6 114.2 . . ?
C4 C5 H6 114.2 . . ?
C5 C6 C17 119.56(9) . . ?
C5 C6 C7 124.71(9) . . ?
C17 C6 C7 115.73(8) . . ?
C16 C7 C8 119.38(9) . . ?
C16 C7 C6 120.68(9) . . ?
C8 C7 C6 119.90(9) . . ?
C9 C8 C7 120.62(9) . . ?
C9 C8 H12 119.7 . . ?
C7 C8 H12 119.7 . . ?
C8 C9 C10 120.04(9) . . ?
C8 C9 H11 120.0 . . ?
C10 C9 H11 120.0 . . ?
C9 C10 C15 119.46(9) . . ?
C9 C10 C11 118.79(9) . . ?
C15 C10 C11 121.70(9) . . ?
O2 C11 C10 119.55(9) . . ?
O2 C11 C12 120.61(9) . . ?
C10 C11 C12 119.83(9) . . ?
C11 C12 H2 109.5 . . ?
C11 C12 H10 109.5 . . ?
H2 C12 H10 109.5 . . ?
C11 C12 H9 109.5 . . ?
H2 C12 H9 109.5 . . ?
H10 C12 H9 109.5 . . ?
C14 C13 C4 122.17(9) . . ?
C14 C13 H4 118.9 . . ?
C4 C13 H4 118.9 . . ?
C13 C14 C1 119.48(9) . . ?
C13 C14 H5 120.3 . . ?
C1 C14 H5 120.3 . . ?
C16 C15 C10 120.36(9) . . ?
C16 C15 H8 119.8 . . ?
C10 C15 H8 119.8 . . ?
C7 C16 C15 120.03(9) . . ?
C7 C16 H7 120.0 . . ?
C15 C16 H7 120.0 . . ?
O3 C17 O4 122.84(9) . . ?
O3 C17 C6 124.31(9) . . ?
O4 C17 C6 112.84(9) . . ?
O4 C18 H15 109.5 . . ?
O4 C18 H14 109.5 . . ?
H15 C18 H14 109.5 . . ?
O4 C18 H13 109.5 . . ?
H15 C18 H13 109.5 . . ?
H14 C18 H13 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
O1 C1 C2 C3 -178.92(10) . . . . ?
C14 C1 C2 C3 0.50(15) . . . . ?
C1 C2 C3 C4 -0.28(16) . . . . ?
C2 C3 C4 C13 0.40(15) . . . . ?
C2 C3 C4 C5 -179.53(10) . . . . ?
C13 C4 C5 C6 -169.50(11) . . . . ?
C3 C4 C5 C6 10.44(18) . . . . ?
C4 C5 C6 C17 -179.65(10) . . . . ?
C4 C5 C6 C7 -0.68(18) . . . . ?
C5 C6 C7 C16 89.40(13) . . . . ?
C17 C6 C7 C16 -91.59(12) . . . . ?
C5 C6 C7 C8 -88.02(13) . . . . ?
C17 C6 C7 C8 90.98(12) . . . . ?
C16 C7 C8 C9 -3.63(16) . . . . ?
C6 C7 C8 C9 173.83(10) . . . . ?
C7 C8 C9 C10 1.51(16) . . . . ?
C8 C9 C10 C15 1.55(16) . . . . ?
C8 C9 C10 C11 -175.93(10) . . . . ?
C9 C10 C11 O2 7.44(15) . . . . ?
C15 C10 C11 O2 -169.97(10) . . . . ?
C9 C10 C11 C12 -173.77(10) . . . . ?
C15 C10 C11 C12 8.81(15) . . . . ?
C3 C4 C13 C14 -0.79(15) . . . . ?
C5 C4 C13 C14 179.15(10) . . . . ?
C4 C13 C14 C1 1.03(16) . . . . ?
O1 C1 C14 C13 178.58(9) . . . . ?
C2 C1 C14 C13 -0.87(15) . . . . ?
C9 C10 C15 C16 -2.48(15) . . . . ?
C11 C10 C15 C16 174.92(10) . . . . ?
C8 C7 C16 C15 2.68(15) . . . . ?
C6 C7 C16 C15 -174.75(9) . . . . ?
C10 C15 C16 C7 0.35(16) . . . . ?
C18 O4 C17 O3 -2.00(15) . . . . ?
C18 O4 C17 C6 178.11(9) . . . . ?
C5 C6 C17 O3 175.75(10) . . . . ?
C7 C6 C17 O3 -3.31(15) . . . . ?
C5 C6 C17 O4 -4.35(14) . . . . ?
C7 C6 C17 O4 176.59(8) . . . . ?

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
O1 H1 O2 0.920(17) 1.816(17) 2.7328(11) 174.9(15) 2_556
O1 H1 O2 0.920(17) 1.816(17) 2.7328(11) 174.9(15) 2_556
O1 H1 O2 0.920(17) 1.816(17) 2.7328(11) 174.9(15) 2_556
O1 H1 O2 0.920(17) 1.816(17) 2.7328(11) 174.9(15) 2_556
O1 H1 O2 0.920(17) 1.816(17) 2.7328(11) 174.9(15) 2_556
O1 H1 O2 0.920(17) 1.816(17) 2.7328(11) 174.9(15) 2_556
O1 H1 O2 0.920(17) 1.816(17) 2.7328(11) 174.9(15) 2_556
O1 H1 O2 0.920(17) 1.816(17) 2.7328(11) 174.9(15) 2_556

_refine_diff_density_max         0.550
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.056

